The present invention relates to a novel heterocyclic compound.

Since causal factor of schizophrenia as well as of bipolar disorder, mood disorders and emotional disorders is heterogeneous, it is desirable that a drug has multiple pharmacological effects so as to develop wide treatment spectrum.

WO2004/026B69A1 discloses that a carbostyril derivative represented by the general formula: (wherein A' represents -(CH₂)_mCH₂-, -(CH₂)_mO-, etc. ; m represents an integer of 1 to 4; and R^A represents a hydrogen atom, a C_1-4 alkyl group which may be substituted with 1 to 3 fluorine atoms, etc.) has D₂ receptor antagonist activity and serotonin 2A (5-HT_2A) receptor antagonist activity and it is effective for treatment of schizophrenia and other central nervous system disorders).

However, there is no description in WO2004/026864A1 that carbostyril derivatives described in the document have D₂ -receptor partial agonist activity, 5'-HT_2A receptor antagonist activity, α₁ receptor antagonist activity and serotonin uptake inhibitory activity together and have a wide treatment spectrum.

WO 2005/019215 A1 discloses the compounds represented by the following formula: (wherein A is -(CH₂)_mCH₂-_, -(CH₂)_mO- or the like; m is an integer of 2 to 5; D is N, C or the like; Z and Q are independently N, C or CH, provided that at least one of Z and Q is N; X and Y are independently C, N or the like, and the bond between X and Y is a single or double bond; R¹ is hydrogen, (C₁-C₃)alkyl group or the like; R⁴, R⁵, R⁶ and R⁷ each represents hydrogen, alkyl group or the like; and G represents a group of monocyclic or bicyclic compound), which bind to dopamine D₂ receptors. WO 2005/019215 A1 teaches that some compounds disclosed therein have an activity as partial agonists of D₂ receptors or an activity as antagonists of D₂ receptors, and may be effective for the treatment of schizophrenia and other central nervous system.

However, WO 2005/019215 A1 does not specifically disclose the compounds of the present invention.

An object of the present invention is to provide an antipsychotic drug which has a wider treatment spectrum, less side effects and excellent tolerability and safety as compared with well-known typical and atypical antipsychotic drugs.

The present inventors have conducted intensive studies on the above-described problem and consequently succeeded in synthesizing a novel compound which has dopamine D₂ receptor partial agonist activity (D₂ receptor partial agonist activity), serotonin 5-HT_2A receptor antagonist activity (5-HT_2A receptor antagonist activity) and adrenalin α₁ receptor antagonist activity (α₁ receptor antagonist activity) and further has serotonin uptake inhibitory effect (or serotonin reuptake inhibitory effect) together in addition to these effects. The present invention has been completed based on this finding.

There is provided a heterocyclic compound or a salt thereof represented by the formula (1): where R² represents a hydrogen atom or a lower alkyl group;
A represents a lower alkylene group or a lower alkenylene group; and
R¹ represents
an aromatic group selected from a phenyl group, a naphthyl group, a dihydroindenyl group and a tetrahydronaphthyl group;
wherein at least one group selected from the group consisting of the groups (1) to (66) below may be present as a substituent on the aromatic group represented by R¹:

1. (1) a lower alkyl group,
2. (2) a lower alkenyl group,
3. (3) a halogen substituted lower alkyl group,
4. (4) a lower alkoxy group,
5. (5) an aryloxy group,
6. (6) a lower alkylthio group,
7. (7) a halogen substituted lower alkoxy group,
8. (8) a hydroxy group,
9. (9) a protected hydroxy group,
10. (10) a hydroxy lower alkyl group,
11. (11) a protected hydroxy lower alkyl group,
12. (12) a halogen atom,
13. (13) a cyano group,
14. (14) an aryl group,
15. (15) a nitro group,
16. (16) an amino group,
17. (17) an amino group having a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, a carbamoyl group, a lower alkyl carbamoyl group, an amino lower alkanoyl group, a lower alkanoylamino lower alkanoyl group and a lower alkoxy carbonylamino lower alkanoyl group as a substituent,
18. (18) a lower alkanoyl group,
19. (19) an arylsulfonyl group that may have a lower alkyl group(s) on the aryl group,
20. (20) a carboxy group,
21. (21) a lower alkoxycarbonyl group,
22. (22) a carboxy lower alkyl group,
23. (23) a lower alkoxycarbonyl lower alkyl group,
24. (24) a lower alkanoylamino lower alkanoyl group,
25. (25) a carboxy lower alkenyl group,
26. (26) a lower alkoxycarbonyl lower alkenyl group,
27. (27) a carbamoyl lower alkenyl group that may have a group(s) selected from the group consisting of a lower alkyl group and a halogen substituted lower alkyl group as a substituent,
28. (28) a carbamoyl group that may have a group(s) selected from the group consisting of the groups (i) to (lxxviii) below as a substituent:
    1. (i) a lower alkyl group,
    2. (ii) a lower alkoxy group,
    3. (iii) a hydroxy lower alkyl group,
    4. (iv) a lower alkoxy lower alkyl group,
    5. (v) an aryloxy lower alkyl group,
    6. (vi) a halogen substituted lower alkyl group,
    7. (vii) an amino lower alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, an aroyl group and a carbamoyl group,
    8. (viii) a cyclo C3-C8 alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a hydroxy group, a lower alkoxycarbonyl group and a phenyl lower alkoxy group as a substituent,
    9. (ix) a cyclo C3-C8 alkyl substituted lower alkyl group,
    10. (x) a lower alkenyl group,
    11. (xi) a carbamoyl lower alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, phenyl group that may have a lower alkyl group(s) and a phenyl group(s) that may have a lower alkoxy group(s) as a substituent,
    12. (xii) a lower alkoxycarbonyl lower alkyl group,
    13. (xiii) a furyl lower alkyl group (that may have a lower alkyl group(s) as a substituent) on the furyl group,
    14. (xiv) a tetrahydrofuryl lower alkyl group,
    15. (xv) a 1,3-dioxolanyl lower alkyl group,
    16. (xvi) a tetrahydropyranyl lower alkyl group,
    17. (xvii) a pyrrolyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the pyrrolyl group),
    18. (xviii) a lower alkyl group substituted with a dihydropyrazolyl group that may have an oxo group(s),
    19. (xix) a pyrazolyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the pyrazolyl group),
    20. (xx) an imidazolyl lower alkyl group,
    21. (xxi) a pyridyl lower alkyl group,
    22. (xxii) a pyrazinyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the pyrazinyl group),
    23. (xxiii) a pyrrolidinyl lower alkyl group (that may have a group(s) selected from the group consisting of an oxo group(s) and a lower alkyl group as a substituent on the pyrrolidinyl group),
    24. (xxiv) a piperidyl lower alkyl group (that may have a group(s) selected from the group consisting of a benzoyl group and a lower alkanoyl group as a substituent on the piperidyl group),
    25. (xxv) a piperazinyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the piperazinyl group),
    26. (xxvi) a morpholinyl lower alkyl group,
    27. (xxvii) a thienyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the thienyl group),
    28. (xxviii) a thiazolyl lower alkyl group,
    29. (xxix) a dihydrobenzofuryl lower alkyl group,
    30. (xxx) a benzopyranyl lower alkyl group (that may have an oxo group(s) as a substituent on the benzopyranyl group),
    31. (xxxi) a benzimidazolyl lower alkyl group,
    32. (xxxii) an indolyl lower alkyl group that may have a lower alkoxycarbonyl group(s) on the lower alkyl group),
    33. (xxxiii) an imidazolyl lower alkyl group that has a substituent(s) selected from the group consisting of a carbamoyl group and a lower alkoxycarbonyl group on the lower alkyl group,
    34. (xxxiv) a pyridyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxy group and a lower alkylthio lower alkyl group as a substituent,
    35. (xxxv) a pyrrolidinyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group and an aroyl group as a substituent,
    36. (xxxvi) a piperidyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group and an aroyl group that may have a group(s) selected from the group consisting of a lower alkyl group and a halogen atom as a substituent,
    37. (xxxvii) a tetrahydrofuryl group that may have an oxo group(s),
    38. (xxxviii) a hexahydroazepinyl group that may have an oxo group(s),
    39. (xxxix) a pyrazolyl group that may have a group(s) selected from the group consisting of a lower alkyl group, an aryl group and a furyl group as a substituent,
    40. (xl) a thiazolyl group,
    41. (xli) a thiadiazolyl group that may have a lower alkyl group(s),
    42. (xlii) an isoxazolyl group that may have a lower alkyl group(s),
    43. (xliii) an indazolyl group,
    44. (xliv) an indolyl group,
    45. (xlv) a tetrahydrobenzothiazolyl group,
    46. (xlvi) a tetrahydroquinolyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen atom and an oxo group as a substituent,
    47. (xlvii) a quinolyl group that may have a lower alkyl group(s),
    48. (xlviii) a benzodioxolyl lower alkyl group,
    49. (xlix) an aryl group that may have a group(s) as a substituent, selected from the group consisting of a halogen atom; a lower alkyl group; a lower alkoxy group; a halogen substituted lower alkyl group; a halogen substituted lower alkoxy group; a lower alkenyl group; an amino group that may have a group(s) selected from the group consisting of a lower alkanoyl group, a lower alkyl sulfonyl group, a lower alkyl group and an aryl group; a sulfamoyl group; a lower alkylthio group; a lower alkanoyl group; a lower alkoxycarbonyl group; a pyrrolyl group; a lower alkynyl group; a cyano group; a nitro group; an aryloxy group; an aryl lower alkoxy group; a hydroxy group; a hydroxy lower alkyl group; a carbamoyl group that may have a group(s) selected from the group consisting of a lower alkyl group and an aryl group; a pyrazolyl group; a pyrrolidinyl group that may have an oxo group(s); an oxazolyl group; an imidazolyl group that may have a lower alkyl group(s); a dihydrofuryl group that may have an oxo group(s); a thiazolidinyl lower alkyl group that may have an oxo group(s); an imidazolyl lower alkanoyl group and a piperidinylcarbonyl group,
    50. (l) a cyano lower alkyl group,
    51. (li) a dihydroquinolyl group that may have a group(s) selected from the group consisting of a lower alkyl group and an oxo group,
    52. (lii) a halogen substituted lower alkylamino group,
    53. (liii) a lower alkylthio lower alkyl group,
    54. (liv) an amidino group that may have a lower alkyl group(s),
    55. (lv) an amidino lower alkyl group,
    56. (lvi) a lower alkenyloxy lower alkyl group,
    57. (lvii) an arylamino group that may have a substituent(s) selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen substituted lower alkyl group and a halogen substituted lower alkoxy group, on the aryl group,
    58. (lviii) an aryl lower alkenyl group,
    59. (lix) a pyridylamino group that may have a lower alkyl group(s),
    60. (lx) an aryl lower alkyl group (that may have on the aryl group and/or the lower alkyl group a group(s) selected from the group consisting of a halogen atom, a lower alkyl group, a halogen substituted lower alkyl group, a halogen substituted lower alkoxy group, a lower alkoxy group, a carbamoyl group and a lower alkoxycarbonyl group as a substituent),
    61. (lxi) a lower alkynyl group,
    62. (lxii) an aryloxy lower alkyl group (that may have as a substituent on the aryl group a group(s) selected from the group consisting of a lower alkoxy group; a carbamoyl group that may have a group(s) selected from the group consisting of a lower alkoxy group and a lower alkyl group; and a pyrrolidinyl group that may have an oxo group(s)),
    63. (lxiii) an isoxazolidinyl group that may have an oxo group(s),
    64. (lxiv) a dihydroindenyl group,
    65. (lxv) an aryl lower alkoxy lower alkyl group,
    66. (lxvi) a tetrahydropyranyl group,
    67. (lxvii) an azetidinyl group that may have a group(s) selected from the group consisting of a lower alkanoyl group and an aroyl group,
    68. (lxviii) an azetidinyl lower alkyl group that may have a group(s) selected from the group consisting of a lower alkanoyl group and aroyl group,
    69. (lxix) a tetrazolyl group,
    70. (lxx) an indolinyl group that may have an oxo group(s),
    71. (lxxi) a triazolyl group that may have a group(s) selected from the group consisting of a lower alkyl group and a lower alkylthio group,
    72. (lxxii) an imidazolyl group that may have a carbamoyl group(s),
    73. (lxxiii) an oxazolyl group that may have a lower alkyl group(s),
    74. (lxxiv) an isothiazolyl group that may have a lower alkyl group(s),
    75. (lxxv) a benzimidazolyl group,
    76. (lxxvi) a dihydrobenzothiazolyl group that may have an oxo group(s),
    77. (lxxvii) a thienyl group that may have a lower alkoxycarbonyl group(s), and
    78. (lxxviii) an oxazolyl lower alkyl group that may have a lower alkyl group(s)
29. (29) an amino lower alkyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a halogen substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, an aryl group, an aryl lower alkyl group, an aroyl group and an amino substituted alkyl group (that may have a lower alkyl group(s) as a substituent on the amino group) on the amino group,
30. (30) a lower alkyl group substituted with a carbamoyl group that may have a group(s) selected from the group consisting of a lower alkyl group and a halogen substituted lower alkyl group,
31. (31) a thiocarbamoyl group that may have a lower alkyl group(s),
32. (32) a sulfamoyl group,
33. (33) an oxazolidinyl group that may have an oxo group(s),
34. (34) an imidazolidinyl group that may have a substituent(s) selected from the group consisting of an oxo group and a lower alkyl group,
35. (35) a pyrrolidinyl group that may have an oxo group(s),
36. (36) an imidazolyl group,
37. (37) a triazolyl group,
38. (38) an isoxazolyl group,
39. (39) a piperidyl group that may have a substituent(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, an arylsulfonyl group, an oxo group, a hydroxy group, and an amino group that may have a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group and a lower alkanoylamino lower alkanoyl group,
40. (40) a piperidylcarbonyl group that may have a substituent(s) selected from the group consisting of a lower alkyl group, a hydroxy group, a hydroxy lower alkyl group, a lower alkanoyl group, a carboxy lower alkyl group, a lower alkyl carbamoyl lower alkyl group, a carbamoyl group, a lower alkoxy group, a carboxy group, a lower alkoxycarbonyl group, an amino group (on which 1 to 2 groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group and an aroyl group may be present), a piperidyl group (on which a group(s) selected from the group consisting of a lower alkanoyl group, a lower alkoxycarbonyl group and an aroyl group may be present), piperazinyl group (on which a lower alkyl group(s) may be present as a substituent), a 1,4-dioxa-8-azaspiro[4.5]decyl group, a morpholinyl group, a hexahydro-1,4-diazepinyl group (on which a lower alkyl group(s) may be present as a substituent), a pyridyl group, a pyridyloxy group, a pyridyl lower alkoxy group, a tetrahydroquinolyl group (on which an oxo group(s) may be present), a benzodioxolyl group, an aryl lower alkoxy group (that may have a group(s) selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkoxy group and a halogen substituted lower alkoxy group on the aryl group), an aryl group (on which a group(s) selected from the group consisting of a halogen atom, a lower alkoxy group, a hydroxy group may be present), an aryloxy group (that may have on the aryl group a group(s) selected from the group consisting of a cyano group, a halogen atom, a lower alkyl group, a lower alkoxy group and a halogen substituted lower alkyl group), an aryl lower alkyl group (that may have on the aryl group a group(s) selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkoxy group and a halogen substituted lower alkyl group), and an aroyl group (that may have on the aryl group a group(s) selected from the group consisting of a halogen atom and a lower alkoxy group),
41. (41) a pyrrolidinylcarbonyl group that may have a group as a substituent, selected from the group consisting of a hydroxy lower alkyl group, a carbamoyl group, a hydroxy group, an amino group (that may have on the amino group a group(s) selected from the group consisting of a lower alkyl group, a lower alkanoyl group and an aroyl group), a morpholinyl lower alkyl group, a pyrrolidinyl lower alkyl group, a piperidyl lower alkyl group, a piperazinyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the piperazinyl group), an amino lower alkyl group (that may have a lower alkyl group(s) as a substituent on the amino group), an aryloxy group (that may have a halogen substituted lower alkoxy group(s) on the aryl group), an aryloxy lower alkyl group (that may have a halogen substituted lower alkoxy group(s) on the aryl group) and a tetrahydroquinolyl group (on which an oxo group(s) may be present),
42. (42) a piperazinylcarbonyl group that may have a group(s) as a substituent, selected from the group consisting of a lower alkyl group, a cyclo C3-C8 alkyl group, a lower alkanoyl group, a hydroxy lower alkyl group, a lower alkoxy lower alkyl group, a lower alkoxycarbonyl group, an amino lower alkyl group (that may have a lower alkyl group(s) as a substituent on the amino group), a piperidyl lower alkyl group (that may have a lower alkyl group(s) as a substituent on the piperidyl group), a morpholinyl lower alkyl group, a pyrrolidinyl lower alkyl group, a 1,3-dioxolanyl lower alkyl group, a tetrahydrofuryl lower alkyl group, a pyridyl lower alkyl group (that may have a phenyl group(s) as a substituent on the lower alkyl group), an imidazolyl lower alkyl group, a furyl lower alkyl group, a pyrrolidinylcarbonyl lower alkyl group, a piperidyl group that may have a lower alkyl group(s) as a substituent, pyridyl group (that may have on the pyridyl group a group(s) selected from the group consisting of a lower alkyl group, a cyano group and a halogen substituted lower alkyl group as a substituent), a thieno[2,3-b]pyridyl group, an aryl group (on which a group(s) selected from the group consisting of a halogen atom and a lower alkyl group may be present), an aroyl group, a furyl carbonyl group, an aryl lower alkoxycarbonyl group and an oxo group,
43. (43) a hexahydroazepinylcarbonyl group,
44. (44) a hexahydro-1,4-diazepinylcarbonyl group that may have a substituent(s) selected from the group consisting of a lower alkyl group and a pyridyl group,
45. (45) a dihydropyrrolylcarbonyl group that may have a lower alkyl group(s),
46. (46) a thiomorpholinylcarbonyl group,
47. (47) a morpholinylcarbonyl group that may have a group(s) selected from the group consisting of a lower alkyl group, a piperidyl lower alkyl group and an aryl group,
48. (48) a thiazolidinyl carbonyl group that may have an aryl group(s) that may have a group(s) selected from the group consisting of a lower alkoxy group and a cyano group,
49. (49) an azabicyclo[3.2.2]nonylcarbonyl group,
50. (50) an 8-azabicyclo[3.2.1]octylcarbonyl group that may have a halogen substituted or unsubstituted aryloxy group(s),
51. (51) an indolinylcarbonyl group,
52. (52) a tetrahydroquinolylcarbonyl group,
53. (53) a tetrahydropyrido[3.4-b]indolylcarbonyl group,
54. (54) a morpholinyl lower alkyl group,
55. (55) a piperazinyl lower alkyl group that may have a lower alkyl group(s) on the piperazinyl group,
56. (56) a morpholinylcarbonyl lower alkyl group,
57. (57) a piperazinylcarbonyl lower alkyl group that may have a lower alkyl group(s) on the piperazinyl group,
58. (58) an oxo group,
59. (59) an amino lower alkoxy group (that may have a lower alkyl group(s) on the amino group),
60. (60) a lower alkoxy lower alkoxy group,
61. (61) a piperazinyl group that may have a group(s) selected from the group consisting of an oxo group, a lower alkyl group, a lower alkanoyl group and a lower alkoxycarbonyl group,
62. (62) a morpholinyl group,
63. (63) a 1,3,8-triazaspiro[4.5]decanylcarbonyl group that may have a group(s) selected from the group consisting of an oxo group and an aryl group,
64. (64) a tetrahydropyridylcarbonyl group that may have a pyridyl group(s),
65. (65) an imidazolidinylcarbonyl group that may have a thioxo group(s), and
66. (66) a 1,4-dioxa-8-azaspiro[4.5]decanyl group.

The present invention also provides a pharmaceutical composition comprising a heterocyclic compound of the general formula (1) or a salt thereof according to the present invention, as an active ingredient and a pharmaceutically acceptable carrier.

The heterocyclic compound of the general formula (1) and the pharmaceutical composition according to the present invention can be used as a pharmaceutical composition for treating or preventing central nervous system disorders selected from the group consisting of schizophrenia; refractory, intractable or chronic schizophrenia; emotional disturbance; psychotic disorder; mood disorder; bipolar I type disorder; bipolar II type disorder; depression; endogenous; = depression; major depression; melancholy and refractory depression; dysthymic disorder; cyclothymic disorder; panic attack; panic disorder; agoraphobia; social phobia; obsessive-compulsive disorder; post-traumatic stress disorder; generalized anxiety disorder; acute stress disorder; hysteria; somatization disorder; conversion disorder; pain.disorder; hypochondriasis; factitious disorder; dissociative disorder; sexual dysfunction; sexual desire disorder; sexual arousal disorder; erectile dysfunction; anorexia nervosa; bulimia nervosa; sleep disorder; adjustment disorder; alcohol abuse; alcohol intoxication; drug addiction; stimulant intoxication; narcotism; anhedonia; iatrogenic anhedonia; anhedonia of a psychic or mental cause; anhedonia associated with depression; anhedonia associated with schizophrenia; delirium; cognitive impairment; cognitive impairment associated with Alzheimer's disease, Parkinson's disease and other neurodegenerative diseases; cognitive impairment caused by Alzheimer's disease; Parkinson's disease and associated neurodegenerative diseases; cognitive impairment of schizophrenia; cognitive impairment caused by refractory, intractable or chronic schizophrenia; vomiting; motion sickness; obesity; migraine; pain (ache); mental retardation; autism disorder (autism); Tourette's disorder; tic disorder; attention-deficit/hyperactivity disorder; conduct disorder; and Down's syndrome.

The present invention provides a process for producing a pharmaceutical composition comprising mixing a heterocyclic compound represented by the formula (1) or a salt thereof with a pharmaceutically acceptable carrier.

The present invention provides use of a heterocyclic compound represented by the formula (1) or a salt thereof as a drug.

Specifically provided is of a heterocyclic compound represented by the formula (1) or a salt thereof, as a dopamine D₂ receptor partial agonist and/or serotonin 5-HT_2A receptor antagonist and/or an adrenaline α₁ receptor antagonist and/or a serotonin uptake inhibitor (or a serotonin reuptake inhibitor).

The present invention provides a process for producing a heterocyclic compound represented by the formula (1): [wherein R₁, R₂ and A are the same as defined in claim 1] or a salt thereof, characterized by comprising a reaction of a compound represented by the formula:

        R₁-O-A-X₁

[wherein R₁ and A are the same as defined above, and X₁ represents a halogen atom or a group which causes a substitution reaction the same as in a halogen atom] or a salt thereof with a compound represented by the formula: [wherein R₂ is the same as defined above] or a salt thereof.

Specific examples of each of the groups shown in the general formula (1) are as follows.

Specific examples of each of the groups shown in the general formula are as follows.

The lower alkyl group is a linear or branched alkyl group having 1 to 6 carbon atoms. Specific examples thereof include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, n-pentyl group, 1-ethylpropyl group, isopentyl group, neo-pentyl group, n-hexyl group, 1,2,2-trimethylpropyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, isohexyl group, and 3-methylpentyl group.

The lower alkylene group is a linear or branched alkylene group having 1 to 6 carbon atoms. Specific examples thereof include a methylene group, ethylene group, trimethylene group, 2-methyltrimethylene group, 2,2-dimethylethylene group, 2,2-dimethyltrimethylene group, 1-methyltrimethylene group, methylmethylene group, ethylmethylene group, tetramethylene group, pentamethylene group, and hexamethylene group.

The lower alkenylene group is a linear or branched alkenylene group having 1 to 3 double bonds and 2 to 6 carbon atoms. Specific examples thereof include a vinylene group, 1-propenylene group, 1-methyl-1-propenylene group, 2-methyl-1-propenylene group, 2-propenylene group, 2-butenylene group, 1-butenylene group, 3-butenylene group, 2-pentenylene group, 1-pentenylene group, 3-pentenylene group, 4-pentenylene group, 1,3-butadienylene group, 1,3-pentadienylene group, 2-penten-4-ynylene group, 2-hexenylene group, 1-hexenylene group, 5-hexenylene group, 3-hexenylene group, 4-hexenylene group, 3,3-dimethyl-1-propenylene group, 2-ethyl-1-propenylene group, 1,3;5-hexatrienylene group, 1,3-hexadienylene group, and 1,4-hexadienylene group.

The lower alkenyl group is a linear or branched alkenyl group having 1 to 3 double bonds and 2 to 6 carbon atoms, including both a trans and cis-configurations. Specific examples thereof include a vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-propenyl group, 2-methyl-1-propenyl group, 2-methyl-2-propenyl group, 2-propenyl group, 2-butenyl group, 1-butenyl group, 3-butenyl group, 2-pentenyl group, 1-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1,3-butadienyl group, 1,3-pentadienyl group, 2-penten-4-yl group, 2-hexenyl group, 1-hexenyl group, 5-hexenyl group, 3-hexenyl group, 4-hexenyl group, 3,3-dimethyl-1-propenyl group, 2-ethyl-1-propenyl group, 1,3,5-hexatrienyl group, 1,3-hexadienyl group, and 1,4-hexadienyl group.

Examples of the halogen atom include a fluorine atom, chlorine atom, bromine atom and iodine atom.

Examples of the halogen substituted lower alkyl group include a lower alkyl group as illustrated above substituted with 1 to 7, more preferably, 1 to 3 halogen atoms. Specific examples thereof include a fluoromethyl group, difluoromethyl group, trifluoromethyl group, chloromethyl group, dichloromethyl group, trichloromethyl group, bromomethyl group, dibromomethyl group, dichlorofluoromethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, 2-fluoroethyl group, 2-chloroethyl group, 3,3,3-trifluoropropyl group, heptafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, heptafluoroisopropyl group, 3-chloropropyl group, 2-chloropropyl group, 3-bromopropyl group, 4,4,4-trifluorobutyl group, 4,4,4,3,3-pentafluorobutyl group, 4-chlorobutyl group, 4-bromobutyl group, 2-chlorobutyl group, 5,5,5-trifluoropentyl group, 5-chloropentyl group, 6,6,6-trifluorohexyl group, 6-chlorohexyl group, and perfluorohexyl group.

The lower alkoxy group is a linear or branched alkoxy group having 1 to 6 carbon atoms. Specific examples thereof include a methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group, isopentyloxy group, neopentyloxy group, n-hexyloxy group, isohexyloxy group, and 3-methylpentyloxy group.

Examples of the aryl group include a phenyl group, substituted phenyl group, biphenyl group, substituted biphenyl group, naphthyl group, and substituted naphthyl group. Examples of the substituent for an aryl group include a lower alkyl group as illustrated above (a linear or branched lower alkyl group having 1 to 6 carbon atoms), a halogen atom as illustrated above, and an amino group. On the aryl group, 1 to 7, preferably 1 to 5, more preferably, 1 to 2 substituents of at least one type of these may be present. Specific examples of the aryl group may include a phenyl group, (2-, 3-, or 4-)biphenyl group, (1- or 2-)naphthyl group, (2-, 3-, or 4-)methylphenyl group, (2-, 3-, or 4-)ethylphenyl group, (2-, 3-, or 4-)n-propylphenyl group, (2-, 3-, or 4-)n-butylphenyl group, (2-, 3-, or 4-)n-pentylphenyl group, (2-, 3-, or 4-)n-hexylphenyl group, (2-, 3-, or 4-)isobutylphenyl group, (2-, 3-, or 4-)tert-butylphenyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)methyl-2-biphenyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)methyl-3-biphenyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)methyl-4-biphenyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)ethyl-2-biphenyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-) ethyl-3-biphenyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)ethyl-4-biphenyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-propyl-2-biphenyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 9'-, 5'-, -or 6'-)n-propyl-3-biphenyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-propyl-4-biphenyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-butyl-2-biphenyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 9'-, 5'-, or 6'-)n-butyl-3-biphenyl group, (2-, 3-, 5-, 6-, 2'-, 3'-4'-, 5'-, or 6'-)n-butyl-4-biphenyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-pentyl-2-biphenyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-pentyl-3-biphenyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-pentyl-4-biphenyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-hexyl-2-biphenyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-hexyl-3-biphenyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-hexyl-4-biphenyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)isobutyl-2-biphenyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)isobutyl-3-biphenyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)isobutyl-4-biphenyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)tert-butyl-2-biphenyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)tert-butyl-3-biphenyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)tert-butyl-4-biphenyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)methyl-1-naphthyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)methyl-2-naphthyl group, (2-, '3-, 4-, 5-, 6-, 7-, or 8-)ethyl-1-naphthyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)ethyl-2-naphthyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-propyl-1-naphthyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-propyl-2-naphthyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-butyl-1-naphthyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-butyl-2-naphthyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-pentyl-1-naphthyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-pentyl-2-naphthyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-) n-hexyl-1-naphthyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-hexyl-2-naphthyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)isobutyl-1-naphthyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)isobutyl-2-naphthyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)tert-butyl-1-naphthyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)tert-butyl-2-naphthyl group, (2-, 3-, or 4-)chlorophenyl group, (2-, 3-, or 4-)fluorophenyl group, (2-, 3-, or 4-)bromophenyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)chloro-1-naphthyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)chloro-2-naphthyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)fluoro-1-naphthyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)fluoro-2-naphthyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)bromo-1-naphthyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)bromo-2-naphthyl group, (2-, 3-, or 4-)aminophenyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)amino-1-naphthyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)amino-2-naphthyl group, 2,3-dimethylphenyl group, 3,4-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,4,6-trimethylphenyl group, 3,4,5-trimethylphenyl group, 2,3,4,5-tetraethylphenyl group, pentamethylphenyl group, 2,4-dimethyl-1-naphthyl group, 2,3-dimethyl-1-naphthyl group, 3,9-dimethyl-1-naphthyl group, 3,5,7-triethylnaphthyl group, 3,4,5,7-tetramethyl-1-naphthyl group, 2,3,4,5,7-pentamethyl-1-naphthyl group, 2,3,4,5,6,7-hexaethyl-1-naphthyl group, heptamethyl-1-naphthyl group, 2,3-diaminophenyl group, 2,4,6-triaminophenyl group, and 2-methyl-5-chloro-1-naphthyl group.

Examples of the aryloxy group include a phenyloxy group, substituted phenyloxy group, biphenyloxy group, substituted biphenyloxy group, naphthyloxy group, and substituted naphthyloxy group. Examples of the substituent for an aryloxy group include a lower alkyl group as illustrated above a linear or branched alkyl group having 1 to 6 carbon atoms), a halogen atom as illustrated above, and an amino group. On the aryl group, 1 to 7, preferably 1 to 5, more preferably, 1 to 2 substituents of at least one type of these may be present. Specific examples of the aryloxy groups include a phenyloxy group, (2-, 3-, or 4-)biphenyloxy group, (1- or 2-) naphthyloxy group, (2-, 3-, or 4-)methylphenyloxy group, (2-, 3-, or 4-)ethylphenyloxy group, (2-, 3-, or 4-)n-propylphenyloxy group, (2-, 3-, or 4-)n-butylphenyloxy group, (2-, 3-, or 4-)n-pentylphenyloxy group, (2-, 3-, or 4-)n-hexylphenyloxy group, (2-, 3-, or 4-)isobutylphenyloxy group, (2-, 3-, or 4-)tert-butylphenyloxy group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)methyl-2-biphenyloxy group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)methyl-3-biphenyloxy group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)methyl-4-biphenyloxy group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)ethyl-2-biphenyloxy group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)ethyl-3-biphenyloxy group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)ethyl-4-biphenyloxy group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-propyl-2-biphenyloxy group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-propyl-3-biphenyloxy group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-propyl-4-biphenyloxy group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-butyl-2-biphenyloxy group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-butyl-3-biphenyloxy group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-butyl-4-biphenyloxy group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-pentyl-2-biphenyloxy group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-pentyl-3-biphenyloxy group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-pentyl-4-biphenyloxy group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-hexyl-2-biphenyloxy group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-hexyl-3-biphenyloxy group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-hexyl-4-biphenyloxy group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-) isobutyl-2-biphenyloxy group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)isobutyl-3-biphenyloxy group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)isobutyl-4-biphenyloxy group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)tert-butyl-2-biphenyloxy group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)tert-butyl-3-biphenyloxy group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)tert-butyl-4-biphenyloxy group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)methyl-1-naphthyloxy group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)methyl-2-naphthyloxy group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)ethyl-1-naphthyloxy group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)ethyl-2-naphthyloxy group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-propyl -1-naphthyloxy group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-propyl-2-naphthyloxy group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-butyl-1-naphthyloxy group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-butyl-2-naphthyloxy group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-pentyl-1-naphthyloxy group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-pentyl-2-naphthyloxy group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-hexyl-1-naphthyloxy group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-hexyl-2-naphthyloxy group, (2-, 3-, 9-, 5-, 6-, 7-, or 8-) isobutyl-1-naphthyloxy group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)isobutyl-2-naphthyloxy group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)tert-butyl-1-naphthyloxy group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)tert-butyl-2-naphthyloxy group, (2-, 3-, or 4-)chlorophenyloxy group, (2-, 3-, or 4-)fluorophenyloxy group, (2-, 3-, or 4-)bromophenyloxy group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-) chloro-1-naphthyloxy group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)chloro-2-naphthyloxy group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)fluoro-1-naphthyloxy group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)fluoro-2-naphthyloxy group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)bromo-1-naphthyloxy group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)bromo-2-naphthyloxy group, (2-, 3-, or 4-)aminophenyloxy group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)amino-1-naphthyloxy group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)amino-2-naphthyloxy group, 2,3-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6-dimethylphenyloxy group, 2,9,6-trimethylphenyloxy group, 3,4,5-trimethylphenyloxy group, 2,3,4,5-tetraethylphenyloxy group, pentamethylphenyloxy group, 2,4-dimethyl-1-naphthyloxy group, 2,3-dimethyl-1-naphthyloxy group, 3,4-dimethyl-1-naphthyloxy group, 3,5,7-triethyl-1-naphthyloxy group, 3,4,5,7-tetramethyl-1-naphthyloxy group, 2,3,4,5,7-pentamethyl-1-naphthyloxy group, 2,3,4,5,6,7-hexaethyl-1-naphthyloxy group, heptamethyl-1-naphthyloxy group, 2,3-diaminophenyloxy group, 2,4,6-triaminophenyloxy group, and 2-methyl-5-chloro-1-naphthyloxy group.

The lower alkylthio group is a linear or branched alkylthio group having 1 to 6 carbon atoms. Specific examples thereof include a methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, tert-butylthio group, n-pentylthio group, and n-hexylthio group.

Examples of the halogen-substituted lower alkoxy group include a lower alkoxy group as illustrated above substituted with 1 to 7, preferably, 1 to 3 halogen atoms. Specific examples thereof include a fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, chloromethoxy group, dichloromethoxy group, trichloromethoxy group, bromomethoxy group, dibromomethoxy group, dichlorofluoromethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, 2-chloroethoxy group, 3,3,3-trifluoropropoxy group, heptafluoropropoxy group, heptafluoroisopropoxy group, 3-chloropropoxy group, 2-chloropropoxy group, 3-bromopropoxy group, 4,4,4-trifluorobutoxy group, 4,4,4,3,3-pentafluorobutoxy group, 4-chlorobutoxy group, 4-bromobutoxy group, 2-chlorobutoxy group, 5,5,5-trifluoropentoxy group, 5-chloropentoxy group, 6,6,6-trifluorohexyloxy group, and 6-chlorohexyloxy group.

Examples of the protecting group of a hydroxy group include a linear or branched alkyl group having 1 to 6 carbon atoms, a lower alkanoyl group (a linear or branched alkanoyl group having 1 to 6 carbon atoms), and a phenyl lower alkyl group whose lower alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms.

Examples of the hydroxy group protected include a methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group, isopentyloxy group, neopentyloxy group, n-hexyloxy group, isohexyloxy group, 3-methylpentyloxy group, lower alkanoyloxy group and phenyl lower alkoxy group. Specific examples include a formyloxy group, acetyloxy group, propionyloxy group, butyryloxy group, isobutyryloxy group, pentanoyloxy group, tert-butylcarbonyloxy group, hexanoyloxy group, benzyloxy group, 2-phenylethoxy group, 1-phenylethoxy group, 3-phenylpropoxy group, 4-phenylbutoxy group, 5-phenylpentyloxy group, 6-phenylhexyloxy group, 1,1-dimethyl-2-phenylethoxy group, and 2-methyl-3-phenylpropoxy group.

Examples of the hydroxy lower alkyl group include a lower alkyl group as illustrated above having 1 to 5, preferably 1 to 3 hydroxy groups (a linear or branched alkyl group having 1 to 6 carbon atoms). Specific examples thereof include a hydroxymethyl group, 2-hydroxyethyl group, 1-hydroxyethyl group, 3-hydroxypropyl group, 2,3-dihydroxypropyl group, 4-hydroxybutyl group, 3,4-dihydroxybutyl group, 1,1-dimethyl-2-hydroxyethyl group, 5-hydroxypentyl group, 6-hydroxyhexyl group, 3,3-dimethyl-3-hydroxypropyl group, 2-methyl-3-hydroxypropyl group, 2,3,4-trihydroxybutyl group, and perhydroxyhexyl group.

Example of a protecting group of a hydroxy lower alkyl group include a linear or branched alkyl group having 1 to 6 carbon atoms, a lower alkanoyl group (a linear or branched alkanoyl group having 1 to 6 carbon atoms), and a phenyl lower alkyl group whose lower alkyl moiety is a linear or branched alkyl group having 1 to 6 carbon atoms.

Examples of the hydroxy lower alkyl group protected include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 5, preferably 1 to 3 protected hydroxy groups as illustrated above (preferably a lower alkoxy group, lower alkanoyloxy group or phenyl lower alkoxy group). Specific examples thereof include a methoxymethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-n-propoxyethyl group, 2-isopropoxyethyl group, 2-n-butoxyethyl group, 2-isobutoxyethyl group, 2-tert-butoxyethyl group, 2-sec-butoxyethyl group, 2-n-pentyloxyethyl group, 2-isopentyloxyethyl group, 2-neopentyloxyethyl group, 2-n-hexyloxyethyl group, 2-isohexyloxyethyl group, 2-(3-methylpentyloxy)ethyl group, 2-formyloxyethyl group, 2-acetyloxyethyl group, 2-propionyloxyethyl group, 2-butyryloxyethyl group, 2-isobutyryloxyethyl group, 2-pentanoyloxyethyl group, 2-tert-butylcarbonyloxyethyl group, 2-hexanoyloxyethyl group, 2-benzyloxyethyl group, 2-(2-phenylethoxy)ethyl group, 2-(1-phenylethoxy)ethyl group, 2-(3-phenylpropoxy)ethyl group, 2-(4-phenylbutoxy)ethyl group, 2-(5-phenylpentyloxy)ethyl group, 2-(6-phenylhexyloxy)ethyl group, 2-(1,1-dimethyl-2-phenylethoxy)ethyl group, 2-(2-methyl-3-phenylpropoxy)ethyl group, 3-ethoxypropyl group, 2,3-diethoxypropyl group, 4-ethoxybutyl group, 3,4-diethoxybutyl group, 1,1-dimethyl-2-ethoxyethyl group, 5-ethoxypentyl group, 6-ethoxyhexyl group, 3,3-dimethyl-3-ethoxypropyl group, 2-methyl-3-ethoxypropyl group, and 2,3,4-triethoxybutyl group.

The lower alkanoyl group is a linear or branched alkanoyl group having 1 to 6 carbon atoms. Specific examples thereof include a formyl group, acetyl group, propionyl group, butyryl group, isobutyryl group, pentanoyl group, tert-butylcarbonyl group, and hexanoyl group.

The lower alkoxycarbonyl group is a linear or branched alkoxycarbonyl group whose lower alkoxy moiety is one as illustrated above, and has 1 to 6 carbon atoms. Specific examples thereof include a methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, isobutoxy carbonyl group, tert-butoxycarbonyl group, sec-butoxycarbonyl group, n-pentyloxycarbonyl group, neopentyloxy group, n-hexyloxycarbonyl group, isohexyloxycarbonyl group, and 3-methylpentyloxycarbonyl group.

The lower alkylsulfonyl group is a linear or branched alkylsulfonyl group whose lower alkyl moiety is one as illustrated above, and has 1 to 6 carbon atoms. Specific examples thereof include a methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropylsulfonyl group, n-butylsulfonyl group, isobutylsulfonyl group, tert-butylsulfonyl group, sec-butylsulfonyl group, n-pentylsulfonyl group, isopentylsulfonyl group, neopentylsulfonyl group, n-hexylsulfonyl group, isohexylsulfonyl group, and 3-methylpentylsulfonyl group.

The lower alkylcarbamoyl group is a carbamoyl group having 1 to 2 lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms) as a substituent(s). Specific examples thereof include a N-methylcarbamoyl group, N,N-dimethylcarbamoyl group, N-ethylcarbamoyl group, N,N-diethylcarbamoyl group, N-n-propylcarbamoyl group, N-n-butylcarbamoyl group, N-n-pentylcarbamoyl group, N-n-hexylcarbamoyl group, N-isobutylcarbamoyl group, N-tert-butylcarbamoyl group, and N,N-di-n-propylcarbamoyl group.

Examples of the aminoalkanoyl group include a lower alkanoyl group as illustrated above (a linear or branched alkanoyl group having 1 to 6 carbon atoms) having 1 to 3 (preferably 1) amino groups. Specific examples thereof include an aminoacetyl group, 3-aminopropionyl group, 4-aminobutyryl group, 3,4-diaminobutyryl group, 3,3-dimethyl-3-aminopropionyl group, 4-aminobutyryl group and 5-aminovaleryl group.

Examples of the lower alkanoyl amino lower alkanoyl group include a lower alkanoyl group as illustrated above (a linear or branched alkanoyl group having 1 to 6 carbon atoms) whose lower alkanoyl moiety has 1 to 3 (preferably 1) lower alkanoylamino groups as illustrated above. Specific examples thereof include an N-formylaminoacetyl group, N-acetylaminoacetyl group, N-propionylaminoacetyl group, 3-(N-acetylamino)propionyl group, 4-(N-acetylamino)butyryl group, 3,4-di(N-acetylamino)butyryl group, 3,3-dimethyl-3-(N-propinylamino)propionyl group, 4-(N-formylamino)butyryl group, and 5-(N-acetylamino)valeryl group.

Examples of the lower alkoxy carbonylamino lower alkanoyl group include a lower alkanoyl group as illustrated above (a linear or branched alkanoyl group having 1 to 6 carbon atoms) whose lower alkoxycarbonyl moiety has 1 to 3 (preferably 1) lower alkoxy carbonylamino groups as illustrated above. Specific examples thereof include an N-methoxycarbonylaminoacetyl group, N-ethoxycarbonylaminoacetyl group, N-tert-butoxycarbonylaminoacetyl group, 3-(N-methoxycarbonylamino)propionyl group, 4-(N-acetylamino)butyryl group, 3,4-di(N-acetylamino)butyryl group, 3,3-dimethyl-3-(N-propinylamino)propionyl group, 4-(N-formylamino)butyryl group and 5-(N-acetylamino)valeryl group. Examples of the amino group having, as a substituent, a group selected from the group consisting of a lower alkyl group, lower alkanoyl group, lower alkoxycarbonyl group, lower alkylsulfonyl group, carbamoyl group, lower alkylcarbamoyl group, amino lower alkanoyl group, lower alkanoylamino lower alkanoyl group, and lower alkoxycarbonylamino lower alkanoyl group include an amino group having, as a substituent, 1 to 2 groups selected from the group consisting of
a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a lower alkanoyl group as illustrated above (preferably a linear or branched alkanoyl group having 1 to 6 carbon atoms);
a lower alkoxycarbonyl group as illustrated above ;
a lower alkylsulfonyl group as illustrated above (a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms);
a carbamoyl group;
a lower alkylcarbamoyl group as illustrated above (preferably a carbamoyl group having, as a substituent, 1 to 2 lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms)); an amino lower alkanoyl group as illustrated above; a lower alkanoylamino lower alkanoyl group as illustrated above; and a lower alkoxycarbonylamino lower alkanoyl group as illustrated above. Specific examples thereof include an amino group, N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N-n-propylamino group, N-isopropylamino group, N-formylamino group, N-acetylamino group, N-tert-butoxycarbonylamino group, N-methoxycarbonylamino group, N-methylsulfonylamino group, N-ethylsulfonylamino group, N-methyl-N-acetylamino group, N-methyl-N-methoxycarbonylamino group, N-[N,N-dimethylcarbamoyl]amino group, N-carbamoylamino group, N-[N-methylcarbamoyl]amino group, N-[N,N-diethylcarbamoyl]amino group, N-(aminoacetyl]amino group, N-[[N-formylamino]acetyl]amino group, N-[[N-acetylamino]acetyl]amino group, N-([N-methoxycarbonylamino]acetyl]amino group, and N-[(N-tert-butoxycarbonylamino]acetyl]amino group.

Examples of the arylsulfonyl group that may have a lower alkyl group on an aryl group include an arylsulfonyl group whose aryl moiety is phenyl, biphenyl, naphthyl or the like and on which 1 to 7, preferably 1 to 5, more preferably, 1 to 2 linear or branched alkyl groups having 1 to 6 carbon atoms. Specific examples of the arylsulfonyl group that may have a lower alkyl group on an aryl group include a phenylsulfonyl group, (2-, 3-, or 4-)biphenylsulfonyl group, (1- or 2-)naphthylsulfonyl group, (2-, 3-, or 4-)methylphenylsulfonyl group, (2-, 3-, or 4-)ethylphenylsulfonyl group, (2-, 3-, or 4-)n-propylphenylsulfonyl group, (2-, 3-, or 4-)n-butylphenylsulfonyl group, (2-, 3-, or 4-)n-pentylphenylsulfonyl group, (2-, 3-, or 4-)n-hexylphenylsulfonyl group, (2-, 3-, or 4-)isobutylphenylsulfonyl group, (2-, 3-, or 4-)tert-butylphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 9'-, 5'-, or 6'-)methyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)methyl-3-biphenylsulfonyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)methyl-4-biphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)ethyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)ethyl-3-biphenylsulfonyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)methyl-4-biphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-propyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-propyl-3-biphenylsulfonyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-propyl-4-biphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-butyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-butyl-3-biphenylsulfonyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-butyl-4-biphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-pentyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-pentyl-3-biphenylsulfonyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-) n-pentyl-4-biphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-hexyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-hexyl-3-biphenylsulfonyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-hexyl-4-biphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)isobutyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)isobutyl-3-biphenylsulfonyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)isobutyl-4-biphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)tert-butyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)tert-butyl-3-biphenylsulfonyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)tert-butyl-4-biphenylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)methyl-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)methyl-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)ethyl-l-naphthylsulfonyl croup, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)ethyl-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-propyl-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-propyl-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-butyl-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-butyl-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-) n-pentyl-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-pentyl-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-hexyl-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-hexyl-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)isobutyl-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)isobutyl-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)tert-butyl-1-naphthylsulfonyl group, (1-, 3-, 9-, 5-, 6-, 7-, or 8-)tert-butyl-2-naphthylsulfonyl group, 2,3-dimethylphenylsulfonyl group, 3,4-dimethylphenylsulfonyl group, 2,4-dimethylphenylsulfonyl group, 2,5-dimethylphenylsulfonyl group, 2,6-dimethylphenylsulfonyl group, 2,4,6-trimethylphenylsulfonyl group, 3,4,5-trimethylphenylsulfonyl group, 2,3,4,5-tetraethylphenylsulfonyl group, pentamethylphenylsulfonyl group, 2,4-dimethyl-1-naphthylsulfonyl group, 2,3-dimethyl-l-naphthylsulfonyl group, 3,4-dimethyl-1-naphthylsulfonyl group, 3,5,7-triethyl-1-naphthylsulfonyl group, 3,4,5,7-tetramethyl-1-naphthylsulfonyl group, 2,3,4,5,7-pentamethyl-1-naphthylsulfonyl group, 2,3,4,5,6,7-hexaethyl-1-naphthylsulfonyl group, and heptamethyl-1-naphthylsulfonyl group.

Examples of a carboxyl lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 3 (preferably 1) carboxyl groups. Specific examples thereof include carboxymethyl group, 2-carboxyethyl group, 1-carboxyethyl group, 1-carboxy-l-methylethyl group, 3-carboxypropyl group, 2,3-dicarboxypropyl group, 4-carboxybutyl group, 3,4-dicarboxybutyl group, 1,1-dimethyl-2-carboxyethyl group, 5-carboxypentyl group, 6-carboxyhexyl group, 3,3-dimethyl-3-carboxypropyl group, 2-methyl-3-carboxypropyl group, and 2,3,4-tricarboxybutyl group.

Examples of a lower alkoxycarbonyl lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 3 (preferably 1 to 2) lower alkoxycarbonyl groups as illustrated above. Specific examples thereof include a methoxycarbonylmethyl group, ethoxycarbonylmethyl group, 1-methoxycarbonylethyl group, 2-methoxycarbonyletnyl group, 2-ethoxycarbonylethyl group, 1-ethoxycarbonylethyl group, 3-methoxycarbonylpropyl group, 3-ethoxycarbonylpropyl group, 4-ethoxycarbonylbutyl group, 5-isopropoxycarbonylpentyl group, 6-n-propoxycarbonylhexyl group, 1,1-dimethyl-2-n-butoxycarbonylethyl group, 1-methyl-1-methoxycarbonylethyl group, 2-methyl-1-methoxycarbonylpropyl group, 2-methyl-3-tert-butoxycarbonylpropyl group, 3-methyl-1-methoxycarbonylbutyl group, diethoxycarbonylmethyl group, 1,2-diethoxycarbonylethyl group, 2-n-pentyloxycarbonylethyl group, and n-hexyloxycarbonylmethyl group.

Examples of the carbamoyl lower alkyl group that may have a group, as a substituent, selected from the group consisting of a lower alkyl group, a phenyl group that may have a lower alkyl group and a phenyl group that may have a lower alkoxy group include a, lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 3 (preferably 1 to 2) carbamoyl groups. The carbamoyl moiety may have 1 to 2 groups selected from the group consisting of a phenyl group that may have 1 to 3 (preferably 1) lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms) and a phenyl group that may have 1 to 3 (preferably 1) lower alkoxy groups as illustrated above (linear or branched alkoxy groups having 1 to 6 carbon atoms). Specific examples of the carbamoyl lower alkyl group include a carbamoylmethyl group, dicarbamoylmethyl group, 2-carbamoylethyl group, 1-carbamoylethyl group, 1-carbamoyl-2-methylpropyl group, 3-carbamoylpropyl group, 4-carbamoylbutyl group, 5-carbamoylpentyl group, 6-carbamoylhexyl group, 1,1-dimethyl-2-carbamoylethyl group, 2-methyl-3-carbamoylpropyl group, N-methylcarbamoylmethyl group, N,N-dimethylcarbamoylmethyl group, N-methyl-N-ethylcarbamoylmethyl group, N-methylcarbamoylmethyl group, 2-(N-methylcarbamoyl)ethyl group, 2-(N-ethylcarbamoyl)ethyl group, N-phenylcarbamoylmethyl group, N-(2-methoxyphenyl)carbamoylmethyl group, and N-(4-methylphenyl)carbamoylmethyl group.

Examples of the carboxyl lower alkenyl group include a lower alkenyl group as illustrated above having 1 to 3, preferably 1, carboxyl groups and including both trans and cis configurations ( a linear or branched alkenyl group having 1 to 3 double bonds and 2 to 6 carbon atoms). Specific examples thereof include a 2-carboxyethenyl group, 3-carboxy-2-propenyl group, 4-carboxy-2-butenyl group, 4-carboxy-3-butenyl group, 4-carboxy-1,3-butadienyl group, 5-carboxy-1,3,5-hexatrienyl group, 5-carboxy-2,4-hexadienyl group, 5-carboxy-3-pentenyl group, and 3-carboxy-1-propenyl group.

Examples of the lower alkoxycarbonyl lower alkenyl group include a lower alkenyl group as illustrated above (a linear or branched alkenyl group having 1 to 3 double bonds and 2 to 6 carbon atoms) having 1 to 3 lower alkoxycarbonyl groups as illustrated above and including both trans and cis configurations. Specific example of the lower alkoxycarbonyl lower alkenyl group include a 2-methoxycarbonylethenyl group, 2-ethoxycarbonylethenyl group, 1-ethoxycarbonylethenyl group, 3-methoxycarbonyl-2-propenyl group, 3-ethoxycarbonyl-2-propenyl group, 4-ethoxycarbonyl-2-butenyl group, 4-ethoxycarbonyl-1,3-buthadienyl group, 5-isopropoxycarbonyl-3-pentenyl group, 6-n-propoxycarbonyl-1,3,5-hexatrienyl group, 1,1-dimethyl-2-n-butoxycarbonylethenyl group, 2-methyl-3-tert-butoxycarbonyl-2-propenyl group, and 2-n-pentyloxycarbonylethenyl group.

Examples of the carbamoyl lower alkenyl group include a lower alkenyl group as illustrated above (a linear or branched alkenyl group having 2 to 6 carbon atoms and 1 to 3 double bonds) having 1 to 3, preferably 1, carbamoyl groups- Specific examples thereof include a 2-carbamoylethenyl group, 3-carbamoyl-2-propenyl group, 4-carbamoyl-2-butenyl group, 4-carbamoyl-3-butenyl group, 4-carbamoyl-1,3-butadienyl group, 5-carbamoyl-1,3,5-hexatrienyl group, 5-carbamoyl-2,4-hexadienyl group, 5-carbamoyl-3-pentenyl group, and 3-carbamoyl-1-propenyl group.

Examples of the carbamoyl lower alkenyl group that may have, as a substituent, a group selected from the group consisting of a lower alkyl group and a halogen-substituted lower alkyl group include a lower alkenyl group as illustrated above (a linear or branched alkenyl group having 1 to 3 double bonds and 2 to 6 carbon atoms) having 1 to 3, preferably 1 carbamoyl group that may have, on the carbamoyl group, 1 to 2 substituents selected from the group consisting of a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms); and a halogen-substituted lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms preferably having 1 to 7, more preferably 1 to 3 substituents of halogen atoms). Specific examples thereof include a 2-carbamoylethenyl group, 2-(N-methylcarbamoyl)ethenyl group, 2-(N-ethylcarbamoyl)ethenyl group, 2-(N,N-dimethylcarbamoyl)ethenyl group, and 2-[N-(2,2,2-trifluoroethyl)carbamoyl]ethenyl group.

Examples of the lower alkoxy lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 3, preferably 1, lower alkoxy groups as illustrated above (a linear or branched alkoxy group having 1 to 6 carbon atoms). Specific examples thereof include a methoxymethyl group, 2-methoxyethyl group, 1-ethoxyethyl group, 2-ethoxyethyl group, 2-isobutoxyethyl group, 2,2-dimethoxyethyl group, 2-methoxy-1-methylethyl group, 2-methoxy-1-ethylethyl group, 3-methoxypropyl group, 3-ethoxypropyl group, 2-isopropoxyethyl group, 3-isopropoxypropyl group, 3-n-butoxypropyl group, 4-n-propoxybutyl group, 1-methyl-3-isobutoxy propyl group, 1,1-dimethyl-2-n-pentyloxyethyl group, 5-n-hexyloxypentyl group, 6-methoxyhexyl group, 1-ethoxyisopropyl group, and 2-methyl-3-methoxypropyl group.

Examples of the aryloxy lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 3, preferably 1 aryloxy groups whose aryl moiety is phenyl, biphenyl, naphthyl or the like. Examples of a substituent for an aryl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms), a halogen atom as illustrated above, and an amino group. One to seven substituents of at least one type of these may be present on an aryl ring. Specific examples of the aryloxy lower alkyl include a phenoxymethyl group, 2-phenoxyethyl group, 2-[(1- or 2-)naphthyloxy]ethyl group, 2-[(2-, 3-, or 4-)methylphenoxy]ethyl group, 2-[(2-, 3-, or 4-)ethylphenoxy]ethyl group, 2-[(2-, 3-, or 4-)n-propylphenoxy]ethyl group, 2-[(2-, 3-, or 4-)n-butylphenoxy]ethyl group, 2-[(2-, 3-, or 4-)n-pentylphenoxy]ethyl group, 2-[(2-, 3-, or 4-)n-hexylphenoxy]ethyl group, 2-[(2-, 3-, or 4-)isobutylphenoxy]ethyl group, 2-[(2-, 3-, or 4-)tert-butylphenoxy]ethyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)methyl-1-naphthyloxy]ethyl group, 2-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)methyl-2-naphthyloxy)ethyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)ethyl-1-naphthyloxy)ethyl group, 2-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)ethyl-2-naphthyloxy]ethyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-propyl-1-naphthyloxy]ethyl group, 2-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-propyl-2-naphthyloxy]ethyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-butyl-l-naphthyloxy]ethyl group, 2-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-butyl-2-naphthyloxy]ethyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-pentyl-l-naphthyloxy]ethyl group, 2-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-pentyl-2-naphthyloxy]ethyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-hexyl-l-naphthyloxy]ethyl group, 2-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-hexyl-2-naphthyloxylethyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)isobutyl-l-naphthyloxy]ethyl group, 2-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)isobutyl-2-naphthyloxy]ethyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)tert-butyl-1-naphthyloxy]ethyl group, 2-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)tert-butyl-2-naphthyloxy]ethyl group, 2-[(2-, 3-, or 4-)chlorophenoxy]ethyl group, 2-[(2-, 3-, or 4-)fluorophenoxy]ethyl group, 2-[(2-, 3-, or 4-)bromophenoxy]ethyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)chloro-1-naptithyloxy]ethyl group, 2-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)chloro-2-naphthyloxy]ethyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)fluoro-1-naphthyloxy]ethyl group, 2-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)fluoro-2-naphthyloxy]ethyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)bromo-1-naphthyloxy]ethyl group, 2-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)bromo-2-naphthyloxy] ethyl group, 2-[(2-, 3-, or 4-)aminophenoxy]ethyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)amino-1-naphthyloxy]ethyl group, 2-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)amino-2-naphthyloxy]ethyl group, 2-(2,3-dimethylphenoxy)ethyl group, 2-(3,4-dimethylphenoxy)ethyl group, 2-(2,4-dimethylphenoxy)ethyl group, 2-(2,5-dimethylphenoxy)ethyl group, 2-(2,6-dimethylphenoxy)ethyl group, 2-(2,4,6-trimethylphenoxy)ethyl group, 2-(3,4,5-trimethylphenoxy)ethyl group, 2-(2,3,4,5-tetraethylphenoxy)ethyl group, 2-(pentamethylphenoxy)ethyl group, 2-(2,4-dimethyl-1-naphthyloxy)ethyl group, 2-(2,3-dimethyl-1-naphthyloxy)ethyl group, 2-(3,4-dimethyl-1-naphthyloxy)ethyl group, 2-(3,5,7-triethyl-1-naphthyloxy)ethyl group, 2-(3,4,5,7-tetramethyl-1-naphthyloxy)ethyl group, 2-(2,3,9,5,7-pentamethyl-1-naphthyloxy)ethyl group, 2-(2,3,4,5,6,7-hexaethyl-1-naphthyloxy)ethyl group, 2-(heptamethyl-1-naphthyloxy)ethyl group, 2-(2,3-diaminophenoxy)ethyl group, 2-(2,4,6-triaminophenoxy)ethyl group, 2-(2-methyl-5-chloro-1-naphthyl)ethyl group, 3-phenoxypropyl group, 2,3-diphenoxypropyl group, 4-phenoxybutyl group, 3,4-diphenoxybutyl group, 1,1-dimethyl-2-phenoxyethyl group, 5-phenoxypentyl group, 6-phenoxyhexyl group, 3,3-dimethyl-3-phenoxypropyl group, 2-methyl-3-phenoxypropyl group, and 2,3,4-triphenoxybutyl group, 3-[(1- or 2-)naphthyloxy]propyl group, 2,3-di[(1- or 2-)naphthyloxy]propyl group, 4-[(1- or 2-)naphthyloxy]butyl group, 3,4-di[(1- or 2-)naphthyloxy]butyl group, 1,1-dimethyl-2-[(1- or 2-)naphthyloxy]ethyl group, 5-[(1- or 2-)naphthyloxy]pentyl group, 6-[(1- or 2-)naphthyloxy]hexyl group, 3,3-dimethyl-3-[(1- or 2-)naphthyloxy]propyl group, 2-methyl-3-[(1- or 2-)naphthyloxy]propyl group, and 2,3,4-tri[(1- or 2-)naphthyloxy]butyl group.

Examples of the amino lower alkyl group that may have a group selected from the group consisting of a lower alkyl group, lower alkanoyl group, aroyl group and carbamoyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 5 (preferably 1) amino groups that may have 1 to 2 groups selected from the group consisting of a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms), lower alkanoyl group as illustrated above (a linear or branched alkanoyl group having 1 to 6 carbon atoms), aroyl group as illustrated above (preferably benzoyl group) as illustrated above and carbamoyl group. Specific examples of the amino lower alkyl group include an aminomethyl group, 2-aminoethyl group, 1-aminoethyl group, 3-aminopropyl group, 4-aminobutyl group, 5-aminopentyl group, 6-aminohexyl group, 1,1-dimethyl-2-aminoethyl group, 2-methyl-3-aminopropyl group, N,N-dimethylaminomethyl group, N-methyl-N-ethylaminomethyl group, N-methylaminomethyl group, 2-(N-methylamino)ethyl group, 1-methyl-2-(N,N-dimethylamino)ethyl group, 1-methyl-2-(N,N-diethylamino)ethyl group, 2-(N,N-dimethylamino)ethyl group, 2-(N,N-diethylamino)ethyl group, 2-(N,N-diisopropylamino)ethyl group, 3-(N,N-dimethylamino)propyl group, 3-(N,N-diethylamino)propyl group, 2-(N-acetylamino)ethyl group, 2-(N-methyl-N-acetylamino)ethyl group, 2-(N-methyl-N-n-butyrylamino)ethyl group, 2-(N-methyl-N-benzoylamino)ethyl group, and 2-.(N-carbamoylamino)ethyl group.

Examples of the cyclo C3-C8 alkyl group include a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, and cyclooctyl group.

Examples of the cyclo C3-C8 alkyl group that may have a group, as a substituent, selected from the group consisting of a lower alkyl group, hydroxy group, lower alkoxy carbonyl group and phenyl lower alkoxy group include a cyclo C3-C8 alkyl group that may have 1 to 3 (preferably 1) groups, as a substituent(s), selected from the group consisting of
a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a hydroxy group;
a lower alkoxy carbonyl group as illustrated above ; and
a lower alkoxy group (a linear or branched alkoxy group having 1 to 6 carbon atoms) having 1 to 3 (preferably 1) phenyl groups. Specific examples thereof include a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, 1-methylcyclopropyl group, 1-methylcyclopentyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 4-hydroxycyclohexyl group, 4-methoxycarbonylcyclohexyl group, 2-benzyloxypentyl group, and 2-benzyloxyhexyl group.

Example of the cyclo C3-C8 alkyl substituted lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 3, preferably 1 cyclo C3-C8 alkyl group as illustrated above. Specific examples thereof include a cyclopropylmethyl group, cyclohexylmethyl group, 2-cyclopropylethyl group, 1-cyclobutylethyl group, cyclopentylmethyl group, 3-cyclopentylpropyl group, 4-cyclohexylbutyl group, 5-cycloheptylpentyl group, 6-cyclooctylhexyl group, 1,1-dimethyl-2-cyclohexylethyl group, and 2-methyl-3-cyclopropylpropyl group.

Examples of the furyl lower alkyl group (that may have a substituent of a lower alkyl group on the furyl group) include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) furyl groups on which 1 to 3 (preferably 1 to 2) lower alkyl groups as illustrated above ( linear or branched alkyl groups having 1 to 6 carbon atoms) may be present as a substituent. Specific examples thereof include a [(2- or 3-)furyl]methyl group, 2-[(2- or 3-)furyl]ethyl group, 1-[(2- or 3-)furyl]ethyl group, 3-[(2- or 3-)furyl]propyl group, 4-[(2- or 3-)furyl]butyl group, 5-[(2- or 3-)furyl]pentyl group, 6-[(2- or 3-)furyl]hexyl group, 1,1-dimethyl-2-[(2- or 3-)furyl]ethyl group, 2-methyl-3-[(2- or 3-)furyl]propyl group, [5-ethyl-(2-, 3-, or 4-)furyl]methyl group, [5-methyl-(2-, 3-, or 4-)furyl]methyl group, [2-n-propyl-(3-. 4-, or 5-)furyl]methyl group, [3-tert-butyl-(2-, 4-, or 5-)furyl]methyl group, [4-n-pentyl-(2-, 3-, or 5-)furyl]methyl group, [2-n-hexyl-(3-, 4-, or 5-)furyl]methyl group, [2,5-dimethyl-(3- or 4-)furyl]methyl group, [2,5-diethyl-(3- or 4-)furyl]methyl group, and [2,4,5-triethyl-3-furyl]methyl group.

Examples of the tetrahydrofuryl lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) tetrahydrofuryl groups. Specific examples thereof include a (2- or 3-)(2,3,4,5-tetrahydrofuryl)methyl group, 2-[(2- or 3-)(2,3,4,5-tetrahydrofuryl)]ethyl group, 1-[(2- or 3-)(2,3,4,5-tetrahydrofuryl)]ethyl group, 3-[(2- or 3-)(2,3,4,5-tetrahydrofuryl)]propyl group, 2,3-di[(2- or 3-)(2,3,4,5-tetrahydrofuryl)]propyl group, 4-[(2- or 3-)(2,3,4,5-tetrahydrofuryl)]butyl group, 3,4-di[(2- or 3-)(2;3,4,5-tetrahydrofuryl)]butyl group, 1,1-dimethyl-2-[(2- or 3-)(2,3,4,5-tetrahydrofuryl)]ethyl group, 5-[(2- or 3-)(2,3,4,5-tetrahydrofuryl)]pentyl group, 6-[(2- or 3-)(2,3,4,5-tetrahydrofuryl)]hexyl group, 3,3-dimethyl-3-[(2- or 3-)(2,3,4,5-tetrahydrofuryl)]propyl group, 2-methyl-3-[(2- or 3-)(2,3,4,5-tetrahydrofuryl)lpropyl group, and 2,3,4-tri[(2- or 3-) (2,3,4,5-tetrahydrofuryl)]butyl group.

Examples of a 1,3-dioxolanyi lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) 1,3-dioxolanyl groups. Specific examples thereof include a [(2- or 4-)1,3-dioxolanyl]methyl group, 2-[(2- or 4-)1,3-dioxolanyl]ethyl group, 1-[(2- or 4-)1,3-dioxolanyl]ethyl group, 3-[(2- or 4-)1,3-dioxolanyl]propyl group, 4-[(2- or 4-)1,3-dioxolanyl]butyl group, 1,1-dimethyl-2-[(2- or 4-)1,3-dioxolanyl]ethyl group, 5-[(2- or 4-)1,3-dioxolanyl]pentyl group, 6-[(2- or 4-)1,3-dioxolanyl]hexyl group, 1-[(2- or 4-)1,3-dioxolanyl]isopropyl group, and 2-methyl-3-[(1-, 2-, or 4-)imidazolyl]propyl group.

Examples of the tetrahydropyranyl lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) tetrahydropyranyl groups. Specific examples thereof include a [(2-, 3-, or 4-)tetrahydropyranyl]methyl group, 2-[(2-, 3-, or 4-)tetrahydropyranyl]ethyl group, 1-[(2-, 3-, or 4-)tetrahydropyranyl]ethyl group, 3-[(2-, 3-, or 4-)tetrahydropyranyl]propyl group, 4-[(2-, 3-, or 4-)tetrahydropyranyl]butyl group, 1,1-dimethyl-2-[(2-, 3-, or 4-)tetrahydropyranyl]ethyl group, 5-[(2-, 3-, or 4-)tetrahydropyranyl]pentyl group, 6-[(2-, 3-, or 4-)tetrahydropyranyl]hexyl group, 1-[(2-, 3-, or 4-)tetrahydropyranyl]isopropyl group, and 2-methyl-3-[(2-, 3-, or 4-)tetrahydropyranyl]propyl group.

Examples of the pyrrolyl lower alkyl group (that may have a substituent of a lower alkyl group on the pyrrolyl group) include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) pyrrolyl groups on which 1 to 3 (preferably 1 to 2) lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms) may be present as a substituent(s). Specific examples thereof include a [(1-, 2-, or 3-)pyrrolyl]methyl group, 2-[(1-, 2-, or 3-)pyrrolyl]ethyl group, 1-[(1-, 2-, or 3-)pyrrolyl]ethyl group, 3-[(1-, 2-, or 3-)pyrrolyl]propyl group, 4-[(1-, 2-, or 3-)pyrrolyl]butyl group, 1,1-dimethyl-2-[(1-, 2-, or 3-)pyrrolyl]ethyl group, 5-[(1-, 2-, or 3-)pyrrolyl]pentyl group, 6-[(1-, 2-, or 3-)pyrrolyl]hexyl group, 1-[(1-, 2-, or 3-)pyrrolyl]isopropyl group, 2-methyl-3-[(1-, 2-, or 3-)pyrrolyl]propyl group, [1-methyl-(2- or 3-)pyrrolyl]methyl group, [1-ethyl-(2- or 3-)pyrrolyl]methyl group, [1-n-propyl-(2- or 3-)pyrrolyl]methyl group, [1-n-butyl-(2- or 3-)pyrrolyl]methyl group, [1-n-pentyl-(2- or 3-)pyrrolyl]methyl group, [1-n-hexyl-(2- or 3-)pyrrolyl]methyl group, 2-[5-methyl-(1-, 2-, 3-, or 4-)pyrrolyl]ethyl group, 1-[1-ethyl-(2- or 3-)pyrrolyl]ethyl group, 3-[1-ethyl-(2- or 3-)pyrrolyl]propyl group, 4-[1-n-propyl-(2- or 3-)pyrrolyl]butyl group, 5-[1-n-butyl-(2- or 3-)pyrrolyl]pentyl group, 6-[1-n-pentyl-(2- or 3-)pyrrolyl]hexyl group, [1,5-dimethyl-(2-, 3-, or 4-)pyrrolyl]methyl group, [1,3,5-trimethyl-2-pyrrolyl]methyl group, and [1,2,4-trimethyl-3-pyrrolyl]methyl group.

Examples of the lower alkyl group substituted with a dihydropyrazolyl group that may have an oxo group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having a 2,3-dihydropyrazolyl group or 4,5-dihydropyrazolyl group as a dihydropyrazolyl group, on which an oxo group may be present. Specific examples thereof include a 3-(2,3- or 4,5-)dihydropyrazolylmethyl group, 2-[4-(2,3- or 4,5-)dihydropyrazolyl]ethyl group, 1-[5-(2,3- or 4,5-)dihydropyrazolyl]ethyl group, 3-[3-(2,3- or 4,5-)dihydropyrazolyl]propyl group, 4-[4-(2,3- or 4,5-)dihydropyrazolyl]butyl group, 5-[1-(2,3- or 4,5-)dihydropyrazolyl]pentyl group, 6-[5-(2,3- or 4,5-)dihydropyrazolyl]hexyl group, 2-methyl-3-[1-(2,3-or 4,5-)dihydropyrazolyl]propyl group, 1,1-dimethyl-2-[3-(2,3- or 4,5-)dihydropyrazolyl]ethyl group, 5-oxo-4-(4,5-dihydropyrazolyl)methyl group, 2-[5-oxo-4-(4,5-dihydropyrazolyl)]ethyl group, and 3-[5-oxo-4-(4,5-dihydropyrazolyl)]propyl group.

Examples of the pyrazolyl lower alkyl group (that may have a substituent of a lower alkyl group on the pyrazolyl group) include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) pyrazolyl groups, on which 1 to 3 (preferably 1 to 2) lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms) may be present as a substituent(s). Specific examples thereof include a 3-pyrazolylmethyl group, 2-(4-pyrazolyl)ethyl group, 2-(1-pyrazolyl)ethyl group, 1-(5-pyrazolyl)ethyl group, 3-(3-pyrazolyl)propyl group, 4-(4-pyrazolyl)butyl group, 5-(1-pyrazolyl)pentyl group, 6-(5-pyrazolyl)hexyl group, 2-methyl-3-(1-pyrazolyl)propyl group, 1,1-dimethyl=2-(3-pyrazolyl)ethyl group, 1-methyl-3-pyrazolylmethyl group, 1-ethyl-3-pyrazolylmethyl group, 1-n-propyl-3-pyrazolylmethyl group, 1-n-butyl-3-pyrazolylmethyl group, 1-n-pentyl-3-pyrazolylmethyl group, 1-methyl-4-pyrazolylmethyl group, 5-methyl-3-pyrazolylmethyl group, 1-ethyl-4-pyrazolylmethyl group, 1-n-propyl-4-pyrazolylmethyl group, 1-n-butyl-4-pyrazolylmethyl group, 1-n-hexyl-4-pyrazolylmethyl group, 3-methyl-1-pyrazolylmethyl group, 3-ethyl-1-pyrazolylmethyl group, 3-n-propyl-1-pyrazolylmethyl group, 3-n-butyl-l-pyrazolylmethyl group, 1,5-dimethyl-3-pyrazolylmethyl group, 3,5-dimethyl-4-pyrazolylmethyl group, 3,4-dimethyl-l-pyrazolylmethyl group, 1,3-dimethyl-5-pyrazolylmethyl group, 3,4-diethyl-1-pyrazolylmethyl group, 3,4-di-n-propyl-1-pyrazolylmethyl group, 3,4-di-n-butyl-1-pyrazolylmethyl group, 1,3,5-trimethyl-4-pyrazolylmethyl group, 3,4,5-trimethyl-1-pyrazolylmethyl group, 3,4,5-triethyl-1-pyrazolylmethyl group, 3,4,5-tri-n-propyl-1-pyrazolylmethyl group, 3,4,5-tri-n-butyl-l-pyrazolylmethyl group, 1-methyl-5-pyrazolylmethyl group, 1-ethyl-5-pyrazolylmethyl group, 1-n-propyl-5-pyrazolylmethyl group, 1-n-butyl-5-pyrazolylmethyl group, 2-(3-pyrazolyl)ethyl group, 3-(3-pyrazolyl)propyl group, 4-(3-pyrazolyl)butyl group, 5-(3-pyrazolyl)pentyl group, 6-(3-pyrazolyl)hexyl group, 2-(1-(4-chlorophenyl)-3-pyrazolyl)ethyl group, 3-(1-methyl-3-pyrazolyl)propyl group, 3-(3-methyl-4-pyrazolyl)propyl group, 3-(5-methyl-4-pyrazolyl)propyl group, 3-(1,5-dimethyl-3-pyrazolyl)propyl group, 3-(1-ethyl-3-pyrazolyl)propyl group, 3-(1-n-propyl-3-pyrazolyl)propyl group, 3-(1-n-butyl-3-pyrazolyl)propyl group, 4-(1-methyl-3-pyrazolyl)butyl group, 4-(1-ethyl-3-pyrazolyl)butyl group, 4-(1-n-propyl-3-pyrazolyl)butyl group, 4-(1-n-butyl-3-pyrazolyl)butyl group, 5-(1-methyl-3-pyrazolyl)pentyl group, 5-(1-ethyl-3-pyrazolyl)pentyl group, 5-(1-n-propyl-3-pyrazolyl)pentyl group, 5-(1-n-butyl-3-pyrazolyl)pentyl group, 6-(1-methyl-3-pyrazolyl)hexyl group, 6-(1-ethyl-3-pyrazolyl)hexyl group, 6-(1-n-propyl-3-pyrazolyl)hexyl group, and 6-[1-(3-butyl)-3-pyrazolyl]hexyl group.

Examples of the imidazolyl lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) imidazolyl groups. Specific examples thereof include a [(1-, 2-, 4- or 5-)imidazolyl]methyl group, 2-[(1-, 2-, 4- or 5-)imidazolyl]ethyl group, 1-[(1-, 2-, 4- or 5-)imidazolyl]ethyl group, 3-[(1-, 2-, 4- or 5-)imidazolyl]propyl group, 4-[(1-, 2-, 4- or 5-)imidazolyl]butyl group, 1,1-dimethyl-2-[(1-, 2-, 4-or 5-)imidazolyl]ethyl group, 5-[(1-, 2-, 4- or 5-)imidazolyl]pentyl group, 6-[(1-, 2-, 4- or 5-)imidazolyl]hexyl group, 1-[(1-, 2-, 4- or 5-)imidazolyl]isopropyl group, and 2-methyl-3-[(1-, 2-, 4- or 5-)imidazolyl]propyl group.

Examples of the pyridyl lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) pyridyl groups. Specific examples thereof include a (2-, 3- or 4-)pyridylmethyl group, 2-[(2-, 3- or 4-)pyridyl]methyl group, 1-[(2-, 3- or 4-)pyridyl]ethyl group, 3-[(2-, 3-or 4-)pyridyl]propyl group, 4-[(2-, 3- or 4-)pyridyl]butyl group, 1,1-dimethyl-2-[(2-, 3- or 4-)pyridyl]ethyl group, 5-[(2-, 3- or 4-)pyridyl]pentyl group, 6-[(2-, 3- or 4-)pyridyl]hexyl group, 1-[(2-, 3-or 4-)pyridyl]isopropyl group, 2-methyl-3-[(2-, 3- or 4-)pyridyl]propyl group.

Examples of the pyrazinyl lower alkyl group (a lower alkyl group may be present as a substituent on the pyrazinyl group) include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) pyrazinyl groups on which 1 to 3 (preferably 1) lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms) may be present as a substituent(s). Specific examples thereof include a 2-pyrazinylmethyl group, 2-(2-pyrazinyl)ethyl group, 1-(2-pyrazinyl)ethyl group, 3-(2-pyrazinyl)propyl group, 4-(2-pyrazinyl)butyl group, 5-(2-pyrazinyl)pentyl group, 6-(2-pyrazinyl)hexyl group, 3-methyl-3-(2-pyrazinyl)propyl group; 1,1-dimethyl-2-(2-pyrazinyl)ethyl group, 3-methyl-2-pyrazinylmethyl group, 3-ethyl-2-pyrazinylmethyl group, 3-n-propyl-2-pyrazinylmethyl group, 3-n-butyl-2-pyrazinylmethyl group, 3-n-pentyl-2-pyrazinylmethyl group, 5-methyl-2-pyrazinylmethyl group, 5-ethyl-2-pyrazinylmethyl group, 5-n-propyl-2-pyrazinylnethyl group, 5-n-butyl-2-pyrazinylmethyl group, 6-methyl-2-pyrazinylmethyl group, 6-ethyl-2-pyrazinylmethyl group; 6-n-propyl-2-pyrazinylmethyl group, 6-n-butyl-2-pyrazinylmethyl group, 3,5-dimethyl-2-pyrazinylmethyl group, 3,5-diethyl-2-pyrazinylmethyl group, 3,5-di-n-propyl-2-pyrazinylmethyl group, 3,5-di-n-butyl-2-pyrazinylmethyl group, 2-(5-methyl-2-pyrazinyl)ethyl group, 2-(5-ethyl-2-pyrazinyl)ethyl group, 2-(5-n-propyl-2-pyrazinyl)ethyl group, 2-(5-n-butyl-2-pyrazinyl)ethyl group, 3-(5-methyl-2-pyrazinyl)propyl group, 3-(5-ethyl-2-pyrazinyl)propyl group, 3-(5-n-propyl-2-pyrazinyl)propyl group, 3-(5-n-butyl-2-pyrazinyl)propyl group, 4-(5-methyl-2-pyrazinyl)butyl group, 4-(5-ethyl-2-pyrazinyl)butyl group, 4-(5-n-propyl-2-pyrazinyl)butyl group, 4-(5-n-butyl-2-pyrazinyl)butyl group, 5-(5-methyl-2-pyrazinyl)pentyl group, 5-(5-ethyl-2-pyrazinyl)pentyl group, 5-(5-n-propyl-2-pyrazinyl)pentyl group, 5-(5-n-butyl-2-pyrazinyl)pentyl group, 6-(5-methyl-2-pyrazinyl)hexyl group, 6-(5-ethyl-2-pyrazinyl)hexyl group, 6-(5-n-propyl-2-pyrazinyl)hexyl group, and 6-(5-n-butyl-2-pyrazinyl)hexyl group.

Examples of the pyrrolidinyl lower alkyl group (a group selected from the group consisting of an oxo group and a lower alkyl group may be present as a substituent on the pyrrolidinyl group) include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) pyrrolidinyle groups, on which 1 to 3 (preferably 1) groups selected from the group consisting of an oxo group and a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) may be present as a substituent(s). Specific examples thereof include a [(1-, 2-, or 3-)pyrrolidinyl]methyl group, 2-[(1-, 2-, or 3-)pyrrolidinyl]ethyl group, 1-[(1-, 2-, or 3-)pyrrolidinyl]ethyl group, 3-[(1-, 2-, or 3-)pyrrolidinyl]propyl group, 4-[(1-, 2-, or 3-)pyrrolidinyl]butyl group, 5-[(1-, 2-, or 3-)pyrrolidinyl]pentyl group, 6-[(1-, 2-,' or 3-)pyrrolidinyl]hexyl group, 1-methyl-2-[(1-, 2-, or 3-)pyrrolidinyl]ethyl group, 1,1-dimethyl-2-[(1-, 2-, or 3-)pyrrolidinyl]ethyl group, 2-methyl-3-[(1-, 2-, or 3-)pyrrolidinyl)propyl group, 1-methyl-(2- or 3-)pyrrolidinylmethyl group, 1-ethyl-(2- or 3-)pyrrolidinylmethyl group, 1-n-propyl-(2- or 3-)pyrrolidinylmethyl group, 1-n-butyl-(2- or 3-)pyrrolidinylmethyl group, 1-n-pentyl-(2- or 3-)pyrrolidinylmethyl group, 1-n-hexyl-(2- or 3-)pyrrolidinylmethyl group, 2-methyl-1-pyrrolidinylmethyl group, 2-ethyl-1-pyrrolidinylmethyl group, 2-n-propyl-1-pyrrolidinylmethyl group, 2-n-butyl-1-pyrrolidinylmethyl group, 2-n-pentyl-1-pyrrolidinylmethyl group, 2-n-hexyl-1-pyrrolidinylmethyl group, 3-methyl-2-pyrrolidinylmethyl group, 3-ethyl-2-pyrrolidinylmethyl group, 3-n-propyl-2-pyrrolidinylmethyl group, 3-n-butyl-2-pyrrolidinylmethyl group, 1,5-dimethyl-(2- or 3-)pyrrolidinylmethyl group, 1,5-di-ethyl-(2- or 3-)pyrrolidinylmethyl group, 1,5-di-n-propyl-(2- or 3-)pyrrolidinylmethyl group, 1,5-di-n-butyl-(2- or 3-)pyrrolidinylmethyl group, 1,4,5-triethyl-(2- or 3-)pyrrolidinylmethyl group, 1,4,5-tri-n-propyl-(2- or 3-)pyrrolidinylmethyl group, 1,4,5-tri-n-butyl-(2- or 3-)pyrrolidinylmethyl group, 3-[2-oxo-(1-pyrrolidinyl)propyl]group, 3-(5-oxo-(2-, 3-, or 4-)pyrrolidinyl]propyl group, and 3-[1-methyl-5-oxo-(2-, 3-, or 4-)pyrrolidinyl]propyl group.

Examples of the piperidyl lower alkyl group (that may have as a substituent on the piperidyl group, a group selected from the group consisting of a benzoyl group and a lower alkanoyl group) include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) piperidyl groups having 1 to 3 (preferably 1) groups, as a substituent(s), selected from the group consisting of a benzoyl group and a lower alkanoyl group as illustrated above (preferably a linear or branched alkyl group having 1 to 6 carbon atoms) on the piperidyl group(s). Specific examples thereof include a (1-, 2-, 3-, or 4-)piperidylmethyl group, 2-[(1-, 2-, 3-, or 4-)piperidyl]ethyl group; 2-[1-benzoyl-(2-, 3-, or 4-)piperidyl]ethyl group, 2-[1-acetyl-(2-, 3-, or 4-)piperidyl]ethyl group, 2-[1-butyryl-(2-, 3-, or 4-)piperidyl]ethyl group, 1-[(1-, 2-, 3-, or 9-)piperidyl]ethyl group, 3-[(1-, 2-, 3-, or 4-)piperidyl]propyl group, 4-[(1-, 2-, 3-, or 4-)piperidyl]butyl group, 1,1-dimethyl-2-[(1-, 2-, 3-, or 4-)piperidyl]ethyl group, 5-[(1-, 2-, 3-, or 4-)piperidyl]pentyl group, 6-[(1-, 2-, 3-, or 4-)piperidyl]hexyl group, 1-[(1-, 2-, 3-, or 4-)piperidyl]isopropyl group, and 2-methyl-3-[(1-, 2-, 3-, or 4-)piperidyl]propyl group.

Examples of the piperazinyl lower alkyl group (that may have a lower alkyl group as a substituent on the piperazinyl group) include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) piperazinyl groups, on which 1 to 3 (preferably 1) lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms) may be present as a substituent(s). Specific examples thereof include a 1-piperazinylmethyl group, 2-piperazinylmethyl group, 2-(1-piperazinyl)ethyl group, 2-(2-piperazinyl)ethyl group, 1-(1-piperazinyl)ethyl group, 1-(2-piperazinyl)ethyl group, 3-(1-piperazinyl)propyl group, 3-(2-piperazinyl)propyl group, 4-(1-piperazinyl)butyl group, 4-(2-piperazinyl)butyl group, 2-(4-ethyl-2-piperazinyl)ethyl group, 1-(4-n-propyl-2-piperazinyl)ethyl group, 2-(4-n-butyl-2-piperazinyl)ethyl group, 2-(4-n-pentyl-2-piperazinyl)ethyl group, 1-(4-n-hexyl-2-piperazinyl)ethyl group, 2-(5-methyl-2-piperazinyl)ethyl group, 1-(5-ethyl-2-piperazinyl)ethyl group, 2-(5-n-propyl-2-piperazinyl)ethyl group, 1-(5-n-butyl-2-piperazinyl)ethyl group, 2-(5-n-pentyl-2-piperazinyl)ethyl group, 1-(5-n-hexyl-2-piperazinyl)ethyl group, 2-(6-methyl-2-piperazinyl)ethyl group, 1-(6-ethyl-2-piperazinyl)ethyl group, 2-(6-n-propyl-2-piperazinyl)ethyl group, 1-(6-n-butyl-2-piperazinyl)ethyl group, 2-(6-n-pentyl-2-piperazinyl)ethyl group, 2-(6-n-hexyl-2-piperazinyl)ethyl group, 3-(2-methyl-1-piperazinyl)propyl group, 3-(2-ethyl-1-piperazinyl)propyl group, 3-(2-n-propyl-1-piperazinyl)propyl group, 3-(2-n-butyl-1-piperazinyl)propyl group, 3-(2-n-pentyl-1-piperazinyl)propyl group, 3-(2-n-hexyl-1-piperazinyl)propyl group, 3-(3-methyl-1-piperazinyl)propyl group, 3-(3-ethyl-1-piperazinyl)propyl group, 3-(3-n-propyl-1-piperazinyl)propyl group, 3-(3-n-butyl-1-piperazinyl)propyl group, 3-(3-n-pentyl-1-piperazinyl)propyl group, 3-(3-n-hexyl-1-piperazinyl)propyl group, 3-(4-methyl-1-piperazinyl)propyl group, 3-(4-ethyl-1-piperazinyl)propyl group, 3-(4-n-propyl-1-piperazinyl)propyl group, 3-(4-n-butyl-1-piperazinyl)propyl group, 3-(4-n-pentyl-1-piperazinyl)propyl group, 6-(5-n-butyl-2-piperazinyl)hexyl group, 6-(5-n-pentyl-2-piperazinyl)hexyl group, 6-(5-n-hexyl-2-piperazinyl)hexyl group, 6-(6-methyl-2-piperazinyl)hexyl group, 6-(6-ethyl-2-piperazinyl)hexyl group, 6-(6-n-propyl-2-piperazinyl)hexyl group, 6-(6-n-butyl-2-piperazinyl)hexyl group, 6-(6-n-pentyl-2-piperazinyl)hexyl group, 6-(6-n-hexyl-2-piperazinyl)hexyl group, 2,3-dimethyl-1-piperazinylmethyl group, 3,3-dimethyl-1-piperazinylmethyl group, and 2-(1,3,4-trimethyl-2-piperazinyl)ethyl group.

Examples of the morpholinyl lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) morpholinyl groups. Specific examples thereof include a 2-morpholinylmethyl group, 3-morpholinylmethyl group, 4-morpholinylmethyl group, 2-(2-morpholinyl)ethyl group, 2-(3-morpholinyl)ethyl group, 2-(4-morpholinyl)ethyl group, 1-(2-morpholinyl)ethyl group, 1-(3-morpholinyl)ethyl group, 1-(4-morpholinyl)ethyl group, 3-(2-morpholinyl)propyl group, 3-(3-morpholinyl)propyl group, 3-(4-morpholinyl)propyl group, 4-(2-morpholinyl)butyl group, 4-(3-morpholinyl)butyl group, 4-(4-morpholinyl)butyl group, 5-(2-morpholinyl)pentyl group, 5-(3-morpholinyl)pentyl group, 5-(4-morpholinyl)pentyl group, 6-(2-morpholinyl)hexyl group, 6-(3-morpholinyl)hexyl group, 6-(4-morpholinyl)hexyl group, 3-methyl-3-(2-morpholinyl)propyl group, 3-methyl-3-(3-morpholinyl)propyl group, 3-methyl-3-(4-morpholinyl)propyl group, 1,1-dimethyl-2-(2-mcrpholinyl)ethyl group, 1,1-dimethyl-2-(3-morpholinyl)ethyl group, and 1,1-dimethyl-2-(4-morpholinyl)ethyl group.

Example of a thienyl lower alkyl group (that may have a lower alkyl group as a substituent on the thienyl group) include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) thienyl groups, on which 1 to 3 (preferably 1) lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms) may be present as a substituent(s). Specific examples thereof include a (2- or 3-)thienylmethyl group, 2-[(2- or 3-)thienyl]ethyl group, 1-[(2- or 3-)thienyl]ethyl group, 3-[(2- or 3-)thienyl]propyl group, 4-[(2- or 3-)thienyl]butyl group, 5-[(2- or 3-)thienyl]pentyl group, 6-[(2- or 3-)thienyl]hexyl group, 1,1-dimethyl-2-[(2- or 3-)thienyl]ethyl group, 2-methyl-3-[(2- or 3-)thienyl]propyl group, 3-methyl-(2-, 4-, or 5-)-thienylmethyl group, [5-methyl-(2, 3- or 4-)thienyl]methyl group, [4-ethyl-(2- or 3-)thienyl]methyl group, [5-n-propyl-(2, 3- or 4-)thienyl]methyl group, [3-n-butyl-(2-, 4-, or 5-)-thienyl]]]methyl group, [4,5-dimethyl-(2- or 3-)thienyl]methyl group, (3,4,5-trimethyl-2-thienyl)methyl group, 2-[3-methyl-(2-, 4-, or 5-)-thienyl]ethyl group, 1-[4-n-pentyl-(2- or 3-)thienyl]ethyl group, 3-[3-hexyl-2-thienyl]propyl group, 4-[4,5-dimethyl-(2- or 3-)thienyl]butyl group, 5-(2,4,5-trimethyl-3-thienyl)pentyl group, and 6-[5-ethyl-(2-, 3-, or 4-)thienyl]hexyl group.

Examples of the thiazolyl group include a (2-, 4- or 5-) thiazolyl group.

Examples of the thiazolyl lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) thiazolyl groups. Specific examples thereof include a (2-, 4-, or 5-)thiazolylmethyl group, 2-[(2-, 4-, or 5-)thiazolyl)ethyl group, 1-[(2-, 4-, or 5-)thiazolyl]ethyl group, 3-[(2-, 4-, or 5-)thiazolyl]propyl group, 4-[(2-, 4-, or 5-)thiazolyl]butyl group, 5-[(2-, 4-, or 5-)thiazolyl)]pentyl group, 6-[(2-, 4-, or 5-)thiazolyl)]hexyl group, 1,1-dimethyl-2-[(2-, 4-, or 5-)thiazolyl]ethyl group, and [2-methyl-3-[(2-, 4-, or 5-)thiazolyl]propyl group.

Examples of the dihydrobenzofuryl group include a 2,3-dihydro-(2-, 3-, 4-, 5-, 6- or 7-)benzofuryl group.

Examples of the dihydrobenzofuryl lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) dihydrobenzofuryl groups. Specific examples thereof include a 2,3-dihydro-4-benzofurylmethyl group, 2-(2,3-dihydro-4-benzofuryl)ethyl group, 3-(2,3-dihydro-4-benzofuryl)propyl group, 4-(2,3-dihydro-4-benzofuryl)butyl group, 5-(2,3-dihydro-4-benzofuryl)pentyl group, 6-(2,3-dihydro-4-benzofuryl)hexyl group, 2,3-dihydro-5-benzofurylmethyl group, 2-(2,3-dihydro-5-benzofuryl)ethyl group, 3-(2,3-dihydro-5-benzofuryl)propyl group, 4-(2,3-dihydro-5-benzofuryl)butyl group, 2,3-dihydro-6-benzofurylmethyl group, 2-(2,3-dihydro-6-benzofuryl)ethyl group, 3-(2,3-dihydro-6-benzofuryl)propyl group, 4-(2,3-dihydro-6-benzofuryl)butyl group, 5-(2,3-dihydro-6-benzofuryl)pentyl group, 2,3-dihydro-7-benzofurylmethyl group, 2,3-dihydro-7-benzofurylethyl group, 3-(2,3-dihydro-7-benzofuryl)propyl group, 4-(2,3-dihydro-7-benzofuryl)butyl group, and 6-(2,3-dihydro-7-benzofuryl)hexyl group.

Examples of the benzopyranyl lower alkyl group (that may have an oxo group as a substituent on the benzopyranyl group) include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) benzopyranyl groups on which an oxo group may be present as a substituent. Specific examples thereof include a (4H-1-benzopyran-2-yl)methyl group, 2-(4H-1-benzopyran-2-yl)ethyl group, 3-(4H-1-benzopyran-2-yl)propyl group, 4-(4H-1-benzopyran-2-yl)butyl group, 5-(4H-1-benzopyran-2-yl)pentyl group, 6-(4H-1-benzopyran-2-yl)hexyl group, (4H-1-benzopyran-3-yl)methyl group, 2-(4H-1-benzopyran-3-yl)ethyl group, 3-(4H-1-benzopyran-3-yl)propyl group, 4-(4H-1-benzopyran-3-yl)butyl group, 5-(4H-1-benzopyran-3-yl)pentyl group, 6-(4H-1-benzopyran-3-yl)hexyl group, (4H-1-benzopyran-4-yl)methyl group, 2-(4H-1-benzopyran-4-yl)ethyl group, 3-(4H-1-benzopyran-4-yl)propyl group, 4-(4H-1-benzopyran-4-yl)butyl group, 5-(4H-1-benzopyran-4-yl)pentyl group, 6-(4H-1-benzopyran-4-yl)hexyl group, (2H-1-benzopyran-2-yl)methyl group, 2-(2H-1-benzopyran-2-yl)ethyl group, 3-(2H-1-benzopyran-2-yl)propyl group, 4-(2H-1-benzopyran-2-yl)butyl group, 5-(2H-1-benzopyran-2-yl)pentyl group, 6-(2H-1-benzopyran-2-yl)hexyl group, (2H-1-benzopyran-3-yl)methyl group, 2-(2H-l-benzopyran-3-yl)ethyl group, 3-(2H-1-benzopyran-3-yl)propyl group, 4-(2H-1-benzopyran-3-yl)butyl group, 5-(2H-1-benzopyran-3-yl)pentyl group, 6-(2H-1-benzopyran-3-yl)hexyl group, (2H-l-benzopyran-4-yl)methyl group, 2-(2H-1-benzopyran-4-yl)ethyl group, 3-(2H-1-benzopyran-4-yl)propyl group, 4-(2H-1-benzopyran-4-yl)butyl group, 5-(2H-1-benzopyran-4-yl)pentyl group, 6-(2H-1-benzopyran-4-yl)hexyl group, (1H-2-benzopyran-1-yl)methyl group, 2-(1H-2-benzopyran-1-yl)ethyl group, 3-(1H-2-benzopyran-1-yl)propyl group, 4-(1H-2-benzopyran-1-yl)butyl group, 5-(1H-2-benzopyran-1-yl)pentyl group, 6-(1H-2-benzopyran-1-yl)hexyl group, (1H-2-benzopyran-3-yl)methyl group, 2-(1H-2-benzopyran-3-yl)ethyl group, 3-(1H-2-benzopyran-3-yl)propyl group, 4-(1H-2-benzopyran-3-yl)butyl group, 5-(1H-2-benzopyran-3-yl)pentyl group, 6-(1H-2-benzopyran-3-yl)hexyl group, (1H-2-benzopyran-3-yl)methyl group, 2-(1H-2-benzopyran-4-yl)ethyl group, 3-(1H-2-benzopyran-4-yl)propyl group, 4-(1H-2-benzopyran-4-yl)butyl group, 5-(1H-2-benzopyran-4-yl)pentyl group, 6-(1H-2-benzopyran-4-yl)hexyl group, (4-oxo-4H-1-benzopyran-2-yl)methyl group, 2-(4-oxo-4H-1-benzopyran-2-yl)ethyl group, 3-(4-oxo-4H-1-benzopyran-2-yl)propyl group, 4-(4-oxo-4H-1-benzopyran-2-yl)butyl group, 5-(4-oxo-4H-1-benzopyran-2-yl)pentyl group, 6-(4-oxo-4H-1-benzopyran-2-yl)hexyl group, (9-oxo-4H-1-benzopyran-3-yl)methyl group, 2-(4-oxo-4H-1-benzopyran-3-yl)ethyl group, 3-(4-oxo-4H-1-benzopyran-3-yl)propyl group, 4-(4-oxo-4H-1-benzopyran-3-yl)butyl group, 5-(4-oxo-4H-1-benzopyran-3-yl)pentyl group, 6-(4-oxo-4H-1-benzopyran-3-yl)hexyl group, (4-oxo-4H-1-benzopyran-4-yl)methyl group, (2-oxo-2H-1-benzopyran-3-yl)methyl group, 2-(2-oxo-2H-1-benzopyran-3-yl)ethyl group, 3-(2-oxo-2H-1-benzopyran-3-yl)propyl group, 4-(2-oxo-2H-1-benzopyran-3-yl)butyl group, 5-(2-oxo-2H-1-benzopyran-3-yl)pentyl group, 6-(2-oxo-2H-1-benzopyran-3-yl)hexyl group, (2-oxo-2H-1-benzopyran-4-yl)methyl group, 2-(2-oxo-2H-1-benzopyran-4-yl)ethyl group, 3-(2-oxo-2H-1-benzopyran-4-yl)propyl group, 4-(2-oxo-2H-1-benzopyran-4-yl)butyl group, 5-(2-oxo-2H-1-benzopyran-4-yl)pentyl group, 6-(2-oxo-2H-1-benzopyran-4-yl)hexyl group, (1-oxo-1H-2-benzopyran-3-yl)methyl group, 2-(1-oxo-1H-2-benzopyran-3-yl)ethyl group, 3-(1-oxo-1H-2-benzopyran-3-yl)propyl group, 4-(1-oxo-1H-2-benzopyran-3-yl)butyl group, 5-(1-oxo-1H-2-benzopyran-3-yl)pentyl group, 6-(1-oxo-1H-2-benzopyran-3-yl)hexyl group, (1-oxo-1H-2-benzopyran-4-yl)methyl group, 2-(1-oxo-1H-2-benzopyran-4-yl)ethyl group, 3-(1-oxo-1H-2-benzopyran-4-yl)propyl group, 4-(1-oxo-1H-2-benzopyran-4-yl)butyl group, 5-(1-oxo-1H-2-benzopyran-4-yl)pentyl group, and 6-(1-oxo-1H-2-benzopyran-4-yl)hexyl group.

Examples of the benzimidazolyl lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) benzimidazolyl groups. Specific examples thereof include a 1-benzimidazolylmethyl group; 2-(1-benzimidazolyl)ethyl group, 3-(1-benzimidazolyl)propyl group, 4-(1-benzimidazolyl)butyl group, 5-(1-benzimidazolyl)pentyl group, 6-(1-benzimidazolyl)hexyl group, 2-benzimidazolylmethyl group, 2-(2-benzimidazolyl)ethyl group, 3-(2-benzimidazolyl)propyl group, 4-(2-benzimidazolyl)butyl group, 5-(2-benzimidazolyl)pentyl group, and 6-(2-benzimidazolyl)hexyl group.

Examples of the indolyl lower alkyl group that may have a lower alkoxycarbonyl group on the lower alkyl group include a lower alkyl group (a linear or branched alkyl group having 1 to 6 carbon atoms) as illustrated above that may have 1 to 3 (preferably 1) lower alkoxycarbonyl groups as illustrated above that may have 1 to 2 (preferably 1) indolyl groups.
Specific examples thereof include an indol(-1-, -2-,-3-, -4-, -5-, -6-, or -7-)ylmethyl group, 2-indol(-1-, -2-, -3-, -4-, -5-, -6-, or -7-)ylethyl group, 3-indol(-1-, -2-, -3-, -4-, -5-, -6-, or -7-)ylpropyl group, 4-indol(-1-, -2-, -3-, -4-, -5-, -6-, or -7-)ylbutyl group, 5-indol(-1-, -2-, -3-, -4-, -5-, -6-, or -7-)ylpentyl group, 6-indol-1-, -2-, -3-, -4-, -5-, -6-, or -7-)ylhexyl group, 3-methyl-3-indol(-1-, -2-, -3-, -4-, -5-, -6-, or -7-)ylpropyl group, 1,1-dimethyl-2-indol(-1-, -2-, -3-, -4-, -5-, -6-, or-7-)ylethyl group, and 1-methoxycarbonyl-2-indol(-1-,-2-, -3-, -4-, -5-, -6-, or -7-)ylethyl group.

Examples of the imidazolyl lower alkyl group having an substituent selected from the group consisting of a carbamoyl group and a lower alkoxycarbonyl group on the lower alkyl group include an imidazolyl lower alkyl group having a 1 to 3, preferably 1, substituents selected from the group consisting of a carbamoyl group and a lower alkoxycarbonyl group as illustrated above on the alkyl group whose lower alkyl moiety is the same as that illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms). Specific examples thereof include a carbamoyl-[(1-, 2-, 4-, or 5-)imidazolyl]methyl group, methoxycarbonyl-[(1-, 2-, 4-, or 5-)imidazolyl]methyl group, ethoxycarbonyl-[(1-, 2-, 4-, or 5-)imidazolyl]methyl group, n-butoxycarbonyl-[(1-, 2-, 4-, or 5-)imidazolyl]methyl group, isobutoxycarbonyl-[(1-, 2-, 4-, or 5-)imidazolyl]methyl group, tert-butoxycarbonyl-[(1-, 2-, 4-, or 5-)imidazolyl]methyl group, sec-butoxycarbonyl-[(1-, 2-, 4-, or 5-)imidazolyl]methyl group, n-pentyloxycarbonyl-[(1-, 2-, 4-, or 5-)imidazolyl]methyl group, neopentyloxy-[(1-, 2-, 4-, or 5-)imidazolyl]methyl group, n-hexyloxycarbonyl-[(1-, 2-, 4-, or 5-)imidazolyl]methyl group, isohexyloxycarbonyl-[(1-, 2-, 4-, or 5-)imidazolyl]methyl group, 3-methylpentyloxycarbonyl-[(1-, 2-, 4-, or 5-)imidazolyl]methyl group, 1-carbamoyl-2-[(1-, 2-, 4-, or 5-)imidazolyl]ethyl group, 1-methoxycarbonyl-2-[(1-, 2-, 4-, or 5-)imidazolyl]ethyl group, 1,1-dimethoxycarbonyl-2-[(1-, 2-, 4-, or 5-)imidazolyl]ethyl group, 1,1-dicarbamoyl-2-[(1-,2-, 4-, or 5-)imidazolyl]ethyl group, 2-carbamoyl-1-[(1-, 2-, 4-, or 5-)imidazolyl]ethyl group, 2-methoxycarbonyl-3-[(1-, 2-, 4-, or 5-)imidazolyl]propyl group, 2-carbamoyl-4-[(1-, 2-, 4-, or 5-)imidazolyl]butyl group, 1-methyl-l-carbamoylmethyl-2-[(1-, 2-, 4-, or 5-)imidazolyl]ethyl group, 2-methoxycarbonyl-5-[(1-, 2-, 4-, or 5-)imidazolyl]pentyl group, 3-carbamoyl-6-[(1-, 2-, 4-, or 5-)imidazolyl]hexyl group, 2-methoxycarbonyl-1-[(1-, 2-, 4-, or 5-)imidazolyl]isopropyl group, and 2-carbamoylmethyl-3-[(1-, 2-, 4-, or 5-)imidazolyl]propyl group.

Examples of the pyridyl group that may have a group selected from the group consisting of a lower alkyl group, lower alkoxy group, and lower alkylthio lower alkyl group, as a substituent include a pyridyl group that may have 1 to 4 (preferably 1) groups, as a substituent(s), which are selected from the group consisting of a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms), a lower alkoxy group as illustrated above (a linear or branched alkoxy group having 1 to 6 carbon atoms), and a lower alkylthio lower alkyl group in which the two lower alkyl moieties each are composed of a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms). Specific examples thereof include a 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 4-methyl-2-pyridyl group, 5-methyl-2-pyridyl group, 5-ethyl-3-pyridyl group, 2-n-propyl-3-pyridyl group, 4-n-butyl-2-pyridyl group, 4-tert-butyl-2-pyridyl group, 5-n-pentyl-3-pyridyl group, 4-n-hexyl-2-pyridyl group, 4-methoxy-2-pyridyl group, 5-methoxy-2-pyridyl group, 2-methylthiomethyl-3-pyridyl group, 5-ethylthiomethyl-2-pyridyl group, 4-n-propylthiomethyl-2-pyridyl group, 3-n-butylthiomethyl-2-pyridyl group, 5-n-pentylthiomethyl-3-pyridyl group, 4-n-hexylthiomethyl-3-pyridyl group, 2-(2-methylthioethyl)-3-pyridyl group, 2-(3-methylthiopropyl)-4-pyridyl group, 3-(4-methylthiobutyl)-4-pyridyl group, 3-(5-methylthiopentyl)-2-pyridyl group, 4-(6-methylthiohexyl)-2-pyridyl group, 3,4-dimethyl-2-pyridyl group, 2,4,6-triethyl-3-pyridyl group, 2,3,5,6-tetramethyl-4-pyridyl group, and 2-methyl-3-methylthiomethyl-4-pyridyl group.

Examples of the pyrrolidinyl group that may have a group selected from the group consisting of a lower alkyl group, lower alkoxycarbonyl group, lower alkanoyl group, and aroyl group as a substituent include a pyrrolidinyl group that may have 1 to 3, preferably 1 group, as a substituent(s), which is selected from the group consisting of a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms), a lower alkoxycarbonyl group as illustrated above a lower alkanoyl group as described above (a linear or branched alkanoyl group having 1 to 6 carbon atoms), and an aroyl group (preferably a benzoyl group). Specific examples thereof include a pyrrolidin-1-yl group, pyrrolidin-2-yl group, pyrrolidin-3-yl group, 1-methylpyrrolidin-3-yl group, 2-ethylpyrrolidin-3-yl group, 3-n-propylpyrrolidin-3-yl group, 4-n-butylpyrrolidin-3-yl group, 1-tert-butylpyrrolidin-3-yl group, 5-n-pentylpyrrolidin-3-yl group, 1-n-hexylpyrrolidin-2-yl group, 2-methoxycarbonyl-2-yl group, 3-ethoxycarbonylpyrrolidin-2-yl group, 1-tert-butoxycarbonylpyrrolidin-3-yl group, 4-propoxycarbonylpyrrolidin-2-yl group, 5-butoxycarbonylpyrrolidin-2-yl group, 1-pentoxycarbonyl-2-yl group, 2-hexyloxycarbonylpyrrolidin-2-yl group, 1,3-dimethoxycarbonylpyrrolidin-2-yl group, 3,4,5-triethylpyrrolidin-2-yl group, 2,3,4,5-tetramethylpyrrolidin-1-yl group, 2,4-dimethoxycarbonylpyrrolidin-1-yl group, 3,4,5-triethoxycarbonylpyrrolidin-1-yl group, 2-methyl-4-methoxycarbonylpyrrolidin-1-yl group, 1-benzoylpyrrolidin-3-yl group, 1-acetyipyrrolidin-3-yl group, and 1-butyrylpyrrolidin-3-yl group.

Examples of the piperidyl group that may have a group as a substituent selected from the group consisting of a lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, and an aroyl group that may have a group selected from the group consisting of a lower alkyl group and a halogen atom include a piperidyl group that may have 1 to 5 (preferably 1 to 4) groups, as a substituent(s), which are selected from the group consisting of
a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a lower alkoxy group as illustrated above (a linear or branched alkoxy group having 1 to 6 carbon atoms);
a lower alkanoyl group as illustrated above ( a linear or branched alkanoyl group having 1 to 6 carbon atoms); and
an aroyl group that may have 1 to 3 groups (preferably 1 group) selected from the group consisting of a lower alkyl group as illustrated above and a halogen atom as illustrated above (preferably a benzoyl group). Specific examples thereof include a 1-piperidyl group, 2-piperidyl group, 3-piperidyl group, 4-piperidyl group, 1-methyl-4-piperidyl group, 2-ethyl-4-piperidyl group, 3-n-propyl-4-piperidyl group, 4-n-butyl-4-piperidyl group, 1-n-pentyl-4-piperidyl group, 2-n-hexyl-4-piperidyl group, 1-methoxycarbonyl-4-piperidyl group, 1-ethoxycarbonyl-4-piperidyl group, 4-n-propoxycarbonyl-4-piperidyl group, 5-n-butoxycarbonyl-4-piperidyl group, 1-tert-butoxycarbonyl-4-piperidyl group, 1-formyl-4-piperidyl group, 1-acetyl-4-piperidyl group, 1-butyryl-4-piperidyl group, 1-butyryl-3-piperidyl group, 2-propionyl-4-piperidyl group, 3-butyryl-4-piperidyl group, 4-isobutyryl-4-piperidyl group, 1-n-pentanoyl-4-piperidyl group, 2-tert-butylcarbonyl-4-piperidyl group, 3-n-hexanoyl-4-piperidyl group, 1-benzoyl-4-piperidyl group, 1-benzoyl-3-piperidyl group, 1-(2-, 3-, or 4-chlorobenzoyl)-4-piperidyl group, 1-(2-, 3-, or 4-fluorobenzoyl)-4-piperidyl group, 1-(2-, 3-, or 4-methylbenzoyl)-4-piperidyl group, 2,6-dimethyl-4-piperidyl group, 2,4,6-trimethyl-3-piperidyl group, 2,2,6,6-tetramethyl-4-piperidyl group, and 2,2,4,4,6-pentamethyl-3-piperidyl group.

Examples of the tetrahydrofuryl group that may have an oxo group include a 2-tetrahydrofuryl group, 3-tetrahydrofuryl group, 3-oxo-2-tetrahydrofuryl group, 4-oxo-2-tetrahydrofuryl group, 5-oxo-2-tetrahydrofuryl group, 2-oxo-3-tetrahydrofuryl group, 4-oxo-3-tetrahydrofuryl group, and 5-oxo-4-tetrahydrofuryl group.

Examples of the hexahydroazepinyl group that may have an oxo group include 2-hexahydroazepinyl group, 3-hexahydroazepinyl group, 4-hexahydroazepinyl group, 2-oxo-3-hexahydroazepinyl group, 3-oxo-2-hexahydroazepinyl group, 4-oxo-2-hexahydroazepinyl group, 5-oxo-2-hexahydroazepinyl-group, and 6-oxo-2-hexahydroazepinyl group.

Examples of the pyrazolyl group that may have a group selected from the group consisting of a lower alkyl group, aryl group, and furyl group as a substituent include a pyrazolyl group that may have 1 to 3 (preferably 1 to 2) groups, as a substituent(s), which are selected from the group consisting of
a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
an aryl group as illustrated above and a furyl group. Specific examples thereof include a 1-pyrazolyl group, 3-pyrazolyl group, 4-pyrazolyl group, 1-methyl-5-pyrazolyl group, 1-ethyl-5-pyrazolyl group, 3-n-propyl-5-pyrazolyl group, 4-n-butyl-5-pyrazolyl group, 1-tert-butyl-4-pyrazolyl group, 1-n-pentyl-4-pyrazolyl group, 3-n-hexyl-4-pyrazolyl group, 3-phenyl-5-pyrazolyl group, 1-(2-naphthyl)-3-pyrazolyl group, 4-(2-methylphenyl)-3-pyrazolyl group, 5-(3-ethylphenyl)-3-pyrazolyl group, 1-(4-n-propylphenyl)-4-pyrazolyl group, 3-(2-n-butylphenyl)-4-pyrazolyl group, 5-(3-n-pentylphenyl)-4-pyrazolyl group, 1-(4-n-hexylphenyl)-5-pyrazolyl group, 3-(2-isobutylphenyl)-5-pyrazolyl group, 4-(3-tert-butylphenyl)-5-pyrazolyl group, 3-(2-chlorophenyl)-1-pyrazolyl group, 4-(3-fluorophenyl)-1-pyrazolyl group, 5-(4-bromophenyl)-1-pyrazolyl group, 1-(2-aminophenyl)-3-pyrazolyl group, 4-(2,3-dimethylphenyl)-3-pyrazolyl group, 5-(3,4,5-trimethylphenyl)-3-pyrazolyl group, 1-(2,3-diaminophenyl)-4-pyrazolyl group, 3-(2-furyl)-5-pyrazolyl group, 1,3-dimethyl-5-pyrazolyl group, 1,3,4-triethyl-5-pyrazolyl group, 1,3,5-trimethyl-4-pyrazolyl group, and 1-methyl-3-phenyl-5-pyrazolyl group.

Examples of the thiadiazolyl group include a 1,2,3-thiadiazolyl group, 1,2,4-thiadiazolyl group, 1,2,5-thiadiazolyl group or 1,3,4-thiadiazolyl group.

Examples of the thiadiazolyl group that may have a lower alkyl group include a thiadiazolyl group as illustrated above that may have 1 to 3, preferably 1, lower alkyl groups as illustrated above ( linear or branched alkyl groups having 1 to 6 carbon atoms). Specific examples thereof include a 4- or 5-(1, 2, 3-thiadiazolyl) group, 3- or 5-(1, 2, 4-thiadiazolyl) group, 3-(1. 2, 5-thiadiazolyl) group, 2-(1, 3, 4-thiadiazolyl) group, 5-methyl-1,3,4-thiadiazol-2-yl group, 4-ethyl-1,2,3-thiadiazol-5-yl group, 5-n-propyl-1,2,4-thiadiazol-3-yl group, 5-n-butyl-1,3,4-thiadiazol-2-yl group, 4-tert-butyl-1,2,3-thiadiazol-5-yl group, 5-n-pentyl-1,2,4-thiadiazol-3-yl group, and 5-n-hexyl-1,3,4-thiadiazol-2-yl group.

Examples of an isoxazolyl group that may have a lower alkyl group include an isoxazolyl group that may have 1 to 2 lower alkyl group as illustrated above (linear or branched alkyl group having 1 to 6 carbon atoms). Specific examples thereof include a 3-isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group, 3-methyl-5-isoxazolyl group, 4-ethyl-5-isoxazolyl group, 4-n-propyl-3-isoxazolyl group, 5-methyl-3-isoxazolyl group, 5-n-butyl-3-isoxazolyl group, 3-tert-butyl-4-isoxazolyl group, 5-n-pentyl-4-isoxazolyl group, 3-n-hexyl-5-isoxazolyl group, and 3,4-dimethyl-5-isoxazolyl group.

Examples of the indazolyl group include a (1-, 3-, 4-, 5-, 6- or 7-)indazolyl group.

Examples of the tetrahydrobenzothiazolyl group include a (2-, 4-, 5-, 6-, or 7-) (4,5,6,7-tetrahydrobenzothiazolyl) group.

Examples of the tetrahydroquinolyl group include a (1-, 2-, 4-, 5-, 6- or -8) (1, 2, 3, 4-tetrahydroquinolyl group.

Example of a tetrahydroquinolyl group that may have a group selected from the group consisting of a lower alkyl group, lower alkoxy group, halogen atom and oxo group as a substituent include a tetrahydroquinolyl group as illustrated above that may have 1 to 3 (preferably 1 to 2) groups; as a substituent(s), which are selected from the group consisting of
a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a lower alkoxy group as illustrated above (a linear or branched alkoxy group having 1 to 6 carbon atoms; a halogen atom; and
an oxo group. Specific examples thereof include a 1-(1,2,3,4-tetrahydroquinolyl) group, 2-(1,2,3,4-tetrahydroquinolyl) group, 3-(1,2,3,4-tetrahydroquinolyl) group, 4-(1,2,3,4-tetrahydroquinolyl) group, 5-(1,2,3,4-tetrahydroquinolyl) group, 6-(1,2,3,4-tetrahydroquinolyl) group, 7-(1,2,3,4-tetrahydroquinolyl) group, 8-(1,2,3,4-tetrahydroquinolyl) group, 2-methyl-3-(1,2,3,4-tetrahydroquinolyl) group, 3-ethyl-2-(1,2,3,4-tetrahydroquinolyl) group, 4-n-propyl-2-(1,2,3,4-tetrahydroquinolyl) group, 5-n-butyl-3-(1,2,3,4-tetrahydroquinolyl) group, 6-tert-butyl-3-(1,2,3,4-tetrahydroquinolyl) group, 7-n-pentyl-2-(1,2,3,4-tetrahydroquinolyl) group, 8-n-hexyl-2-(1,2,3,4-tetrahydroquinolyl) group, 2-methoxy-4-(1,2,3,4-tetrahydroquinolyl) group, 3-ethoxy-4-(1,2,3,4-tetrahydroquinolyl) group, 4-propoxy-5-(1,2,3,4-tetrahydroquinolyl) group, 5-butoxy-6-(1,2,3,4-tetrahydroquinolyl) group, 6-pentoxy-7-(1,2,3,4-tetrahydroquinolyl) group, 7-hexyloxy-8-(1,2,3,4-tetrahydroquinolyl) group, 4-oxo-3-(1,2,3,4-tetrahydroquinolyl) group, 2-oxo-(1-, 3-, 4-, 5-, 6-, 7-, or 8-)-(1,2,3,4-tetrahydroquinolyl) group, 2-oxo-8-methyl-(3-, 4-, 5-, 6-, or 7-)-(1,2,3,4-tetrahydroquinolyl) group, 2-oxo-8-methoxy-3-(1,2,3,4-tetrahydroquinolyl) group, 2-oxo-5-methoxy-(1-, 3-, 4-, 6-, 7-, or 8-)-(1,2,3,4-tetrahydroquinolyl) group, 2-oxo-8-fluoro-(3-, 4-, 5-, 6-, or 7-)-(1,2,3,4-tetrahydroquinolyl) group, and 2-oxo-6,8-dimethyl-3-(1,2,3,4-tetrahydroquinolyl) group.

Examples of the quinolyl group include a 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, and 8-quinolyl group. Examples of the quinolyl group that may have a lower alkyl group include a quinolyl group that may have 1 to 2 lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms). Specific examples thereof include a 2-, 3-, 4-, 5-, 6-, 7- or 8-quinolyl group, 2-methyl-6-quinolyl group, 4-ethyl-5-quinolyl group, 4-n-propyl-3-quinolyl group, 5-methyl-3-quinolyl group, 5-n-butyl-3-quinolyl group, 3-tert-butyl-4-quinolyl group, 5-n-pentyll-4-quinolyl group, 3-n-hexyl-5-quinolyl group and 3,4-dimethyl-5-quinolyl group.

Examples.of the benzodioxolyl lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 2 (preferably 1) benzodioxolyl groups. Specific examples thereof include a 2-, 4- or 5-(1,3-benzodioxolyl)methyl group, 2-(2-, 4- or 5-)(1,3-benzodioxolyl)ethyl group and 3-(2-, 4- or 5-)(1,3-benzodioxolyl) propyl group.

Examples of the aryl group that may have a group selected from the group consisting of a halogen atom; a lower alkyl group; a lower alkoxy group; a halogen substituted lower alkyl group; a halogen substituted lower alkoxy group; a lower alkenyl group; an amino group that may have a group selected from the group consisting of a lower alkylsulfonyl group, lower alkyl group, and aryl group; a sulfamoyl group; a lower alkylthio group; a lower alkanoyl group; a lower alkoxycarbonyl group; a pyrrolyl group; lower alkynyl group; cyano group, nitro group; aryloxy group; aryl lower alkoxy group; hydroxy group; hydroxy lower alkyl group; carbamoyl group that may have a group selected from the group consisting of a lower alkyl group and an aryl group; pyrazolyl group; pyrrolidinyl group that may have an oxo group; oxazolyl group; imidazolyl group that may have a lower alkyl group; dihydrofuryl group that may have an oxo group; thiazolidinyl lower alkyl group that may have an oxo group; imidazolyl lower alkanoyl group; and piperidinylcarbonyl group include an aryl group as illustrated above that may have 1 to 7, preferably 1 to 5, more preferably, 1 to 2 groups, as a substituent(s), which are selected from the group consisting of
a halogen atom as illustrated above;
a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a lower alkoxy group as illustrated above (a linear or branched alkoxy group having 1 to 6 carbon atoms);
a halogen substituted lower alkyl group as illustrated above (preferably a linear or branched alkyl group having 1 to 6 carbon atoms substituted with 1 to 7 halogen atoms);
a halogen substituted lower alkoxy group as illustrated above (preferably a linear or branched alkoxy group having 1 to 6 carbon atoms substituted with 1 to 7 halogen atoms);
a lower alkenyl group as illustrated above (
a linear or branched alkenyl group having 1 to 3 double bonds and 2 to 6 carbon atoms (including both trans and cis configurations));
an amino group having 1 to 2 lower alkanoyl groups as illustrated above, lower alkyl groups as illustrated above, and aryl groups as illustrated above;
a sulfamoyl group;
a lower alkylthio group whose lower alkyl moiety is a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a lower alkanoyl group as illustrated above (
a linear or branched alkanoyl group having 1 to 6 carbon atoms);
a lower alkoxycarbonyl group as illustrated above a pyrrolyl group; an alkynyl group as illustrated below; cyano group; nitro group; aryloxy group whose aryl moiety is as illustrated above; aryl lower alkoxy group whose aryl moiety and lower alkoxy moiety are as illustrated above; hydroxy group; a hydroxy lower alkyl group whose lower alkyl moiety is as illustrated above; a carbamoyl group that may have 1 to 2 groups selected from the group consisting of a lower alkyl group as illustrated above and aryl group as illustrated above; pyrazolyl group; pyrrolidinyl group that may have 1 to 2 (preferably 1) oxo groups; oxazolyl group; imidazolyl group that may have 1 to 3 (preferably 1 to 2) lower alkyl groups as illustrated above; dihydrofuryl group that may have 1 to 2 (preferably 1) oxo groups; thiazolidinyl group that may have 1 to 2 (preferably 1) oxo groups and having an lower alkyl moiety as illustrated above; imidazolyl lower alkanoyl group whose alkanoyl moiety is as illustrated above and piperidinylcarbonyl group. Specific examples thereof include a phenyl group, 1-naphthyl group, 2- naphthyl group, (2-, 3-, or 4-)biphenyl group, (2-, 3-, or 4-)chlorophenyl group, (2-, 3-, or 4-)fluorophenyl group, (2-, 3-, or 4-)bromophenyl group, (2-, 3-, or 4-)methylphenyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)ethyl-1-naphthyl group, (2-, 3-, or 4-)n-propylphenyl group, (2-, 3-, or 4-)n-butylphenyl group, (2-, 3-, or 4-)n-pentylphenyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-hexyl-1-naphthyl group, (2-, 3-, or 4-) isobutylphenyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)tert-butyl-1-naphthyl group, (2-, 3-, or 4-)methoxyphenyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)ethoxy-1-naphthyl group, (2-, 3-, or 4-)n-propoxyphenyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)isopropoxy-1-naphthyl group, (2-, 3-, or 4-)n-butoxyphenyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)isobutoxy-2-naphthyl group, (2-, 3-, or 4-)tert-butoxyphenyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)sec-butoxy-1-naphthyl group, (2-, 3-, or 4-)n-pentyloxyphenyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)isopentyloxy-1-naphthyl group, (2-, 3-, or 4-)neopentyloxyphenyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-hexyloxy-2-naphthyl group, (2-, 3-, or 4-) isohexyloxyphenyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)(3-methylpentyloxy)-1-naphthyl group, (2-, 3-, or 4-)chloromethylphenyl group, (2-, 3-, or 4-)trifluoromethylphenyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)fluoroethyl-1-naphthyl group, (2-, 3-, or 4-)(3-bromopropyl)phenyl group, (2-, 3-, or 4-)(4-chlorobutyl)phenyl group, (2-, 3-, or 4-)(5-fluoropentyl)phenyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)(6-bromohexyl)-1-naphthyl group, (2-, 3-, or 4-)(1,1-dimethyl-2-chloroethyl)phenyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)(2-methyl-3-fluoropropyl)-2-naphthyl group, (2-, 3-, or 4-)chloromethoxyphenyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)(2-fluoroethoxy)-1-naphthyl group, (2-, 3-, or 4-)(3-bromopropoxy)phenyl group, (2-, 3-, or 4-)(4-chlorobutoxy)phenyl group, (2-, 3-, or 9-)(5-fluoropentyloxy)phenyl group, (2-, 3-, or 4-)trifluoromethoxyphenyl group, 4-(6-bromohexyloxy)-1-naphthyl group, (2-, 3-, or 9-)(1,1-dimethyl-2-chloroethoxy)phenyl group, 7-(2-methyl-3-fluoropropoxy)-2-naphthyl group, 2-vinylphenyl group, 2-(1-methylvinyl)phenyl group, 2-(1-propenyl)-1-naphthyl group, (2-, 3-, or 4-)(1-methyl-1-propenyl)phenyl group, 3-(2-methyl-1-propenyl)-1-naphthyl group, (2-, 3-, or 9-)(1-propenyl)phenyl group, (2-, 3-, or 4-)(2-propenyl)phenyl group, 4-(2-butenyl)-1-naphthyl group, (2-, 3-, or 4-)(1-butenyl)phenyl group, 5-(3-butenyl)-1-naphthyl group, (2-, 3-, or 4-)(2-pentenyl) phenyl group, 6-(1-pentenyl)-1-naphthyl group, (2-, 3-, or 4-)(3-pentenyl)phenyl group, 7-(9-pentenyl)-1-naphthyl group, (2-, 3-, or 4-)(1,3-butadienyl)phenyl group, 8-(1,3-pentadienyl)-1-naphthyl group, (2-, 3-, or 4-)(2-penten-4-ynyl)phenyl group, 1-(2-hexenyl)-2-naphthyl group, 4-(1-hexenyl)phenyl group, a 3-(5-hexenyl)-2-naphthyl group, (2-, 3-, or 9-)(3-hexenyl) group, 4-(4-hexenyl)-2-naphthyl group, (2-, 3-, or 4-)(3,3-dimethyl-1-propenyl)phenyl group, 5-(2-ethyl-1-propenyl)-2-naphthyl group, 9-(1,3,5-hexatrienyl)phenyl group, 6-(1,3-hexadienyl)-2-naphthyl group, (2-, 3-, or 4-)(1,4-hexadienyl)phenyl group, (2-, 3-, or 4-)(N-formylamino)phenyl group, (2-, 3-, or 4-)(N-acetylamino)phenyl group, 7-(N-acetylamino)-2-naphthyl group, (2-, 3-, or 4-) (N-propionylamino) phenyl group, 8-(N-butyrylamino)-2-naphthyl group, (2-, 3-, or 4-)(N-isobutyrylamino)phenyl group, 2-(N-pentanoylamino)-1-naphthyl group, (2-, 3-, or 4-)(N-tert-butylcarbonylamino)phenyl group, 3-(N-hexanoylamino)-1-naphthyl group, (2-, 3-, or 9-)(N,N-diformylamino)phenyl group, 4-(N,N-diacetylamino)-1-naphthyl group, (2-, 3-, or 4-)(N,N-dimethylamino)phenyl group, (2-, 3-, or 4-)(N-phenylamino)phenyl group, (2-, 3-, or 4-)sulfamoylphenyl group, 5-sulfamoyl-1-naphthyl group, (2-, 3-, or 4-)methylthiophenyl group, 6-ethylthio-1-naphthyl group, (2-, 3-, or 4-)n-propylthiophenyl group, 7-isopropylthio-1-naphthyl group, (2-, 3-, or 4-)n-butylthiophenyl group, 8-tert-butylthio-1-naphthyl group, (2-, 3-, or 4-)n-pentylthiophenyl group, 1-n-hexylthio-2-naphthyl group, (2-, 3-, or 4-)(N-methyl(sulfonylamino)phenyl group, (2-, 3-, or 4-)formylphenyl group, (2-, 3-, or 4-)acetylphenyl group, (2-, 3-, or 4-)butyrylphenyl group, 3-acetyl-2-naphthyl group, (2-, 3-, or 4-)propionylphenyl group, 4-butyryl-2-naphthyl group, (2-, 3-, or 4-)isobutyrylphenyl group, 5-pentanoyl-2-naphthyl group, (2-, 3-, or 4-)cyanophenyl group, (2-, 3-, or 4-)methoxycarbonylphenyl group, (2-, 3-, or 4-)tert-butylcarbonylphenyl group, 6-hexanoyl-2-naphthyl group, (2-, 3-, or 4-)ethoxycarbonylphenyl group, 7-ethoxycarbonyl-2-naphthyl group, (2-, 3-, or 4-)n-propoxycarbonylphenyl group, 8-isopropoxycarbonyl-2-naphthyl group, (2-, 3-, or 4-)n-butoxycarbonylphenyl group, 2-isobutoxycarbonyl-1-naphthyl group, (2-, 3-, or 4-)tert-butoxycarbonylphenyl group, 3-sec-butoxycarbonyl-1-naphthyl group, (2-, 3-, or 4-)n-pentyloxycarbonylphenyl group, 4-neopentyloxy-1-naphthyl group, (2-, 3-, or 4-)n-hexyloxycarbonylphenyl group, 5-isohexyloxycarbonyl-1-naphthyl group, (2-, 3-, or 4-)(3-methylpentyloxycarbonyl)phenyl group, 6-(1-pyrrolyl)-1-naphthyl group, (2-, 3-, or 4-)(1-pyrrolyl)phenyl group, (2-, 3-, or 4-)ethynylphenyl group, (2-, 3-, or 4-)(N-methylcarbamoyl)phenyl group, (2-, 3-, or 9-)(N-phenylcarbamoyl)phenyl group, (2-, 3-, or 9-)(2-hydroxyethyl)phenyl group, (2-, 3-, or 4-)phenoxyphenyl group, (2-, 3-, or 4-)nitrophenyl group, (2-, 3-, or 4-)benzyloxyphenyl group, (2-, 3-, or 4-) hydroxyphenyl group, (2-, 3-, or 4-)(2-oxo,-2,5-dihydrofuran-9-yl)phenyl group, (2-, 3-, or 4-)(1-imidazolylacetyl)phenyl group, (2-, 3-, or 9-)(2,9-dioxothiazolidin-5-ylmethyl)phenyl group, (2-, 3-, or 9-)[(1-,2-, 3-, or 4-)piperidylcarbonyl]phenyl group, (2-, 3-, or 4-)[(1-,3-, 4-, or 5-)pyrazolyl]phenyl group, (2-, 3-, or 4-)[2-oxo-(1- or 3-)pyrrolidinyl]phenyl group, (2-, 3-, or 4-)[(2-, 4-, or 5-)oxazolyl]phenyl group, (2-, 3-, or 4-)(2-ethyl-4-methylimidazol-1-yl)phenyl group, (2-, 3-, or 4-)biphenyl group, 2,3-dimethoxyphenyl group, 2,4-dimethoxyphenyl group, 2,5-dimethoxyphenyl group, 2,6-dimethoxyphenyl group, 3,4-dimethoxyphenyl group, 3,5-dimethoxyphenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 3,4-dichlorophenyl group, 2-methoxy-5-chlorophenyl group, 2-methoxy-5-methylphenyl group, 2-methoxy-5-acetylaminophenyl group, 2-vinyl-4-methylphenyl group, 2-vinyl-5-ethylphenyl group, 2,6-disulfamoylphenyl group, 2,4,6-trimethoxyphenyl group, 3,9,5-triethoxyphenyl group, 2-vinyl-3,4,5-triethylphenyl group, pentamethoxyphenyl group, 2-vinylnaphthyl group, 2,3-dimethoxy-1-naphthyl group, 3,4-diethoxyphenyl group, 2-methoxy-5-methoxycarbonylphenyl group, 3,5-dimethoxycarbonylphenyl group, 3-chloro-4-hydroxyphenyl group, 2-chloro-5-(N-acetylamino)phenyl group, 2-chloro-5-cyanophenyl group, 2-chloro-5-carbamoylphenyl group, 2-methoxy-5-(N-acetylamino)phenyl group, 2-chloro-5-ethoxycarbonylphenyl group, 3,5,7-triethoxy-1-naphthyl group, 3,4,5,7-tetramethyl-1-naphthyl group, 2,3,4,5-tetramethyl-7-(N-pentaacetylamino)-1-naphthyl group, 2,3,4,5,6,7-hexaethoxy-1-naphthyl group, and heptamethoxy-1-naphthyl group.

Examples of the cyano lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having a single cyano group. Specific examples thereof include a cyanomethyl group, 2-cyanoethyl group, 1-cyanoethyl group, 3-cyanopropyl group, 4-cyanobutyl group, 1,1-dimethyl-2-cyanoethyl group, 5-cyanopentyl group, 6-cyanohexyl group, 1-cyanoisopropyl group, and 2-methyl-3-cyanopropyl group.

Examples of the lower alkanoylamino lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 3, preferably 1, amino groups which has 1 to 2 lower alkanoyl groups as illustrated above (a linear or branched alkanoyl group having 1 to 6 carbon atoms). Specific examples thereof include a 2-(N-formylamino)ethyl group, 2-(N-acetylamino)ethyl group, 2-(N-propionylamino)ethyl group, 2-(N-butyrylamino)ethyl group, 2-(N-isobutyrylamino)ethyl group, 2-(N-pentanoylamino)ethyl group, 2-(N-tert-butylcarbonylamino)ethyl group, 2-(N-hexanoylamino)ethyl group, N-acetylaminomethyl group, 1-(N-acetylamino)ethyl group, 3-(N-acetylamino)propyl group, 4-(N-acetylamino)butyl group, 5-(N-acetylamino)pentyl group, 6-(N-acetylamino)hexyl group, 1,1-dimethyl-2-(N-acetylamino)ethyl group, 2-methyl-3-(N-acetylamino)propyl group, and 2-(N,N-diacetylamino)ethyl group.

Examples of a halogen substituted lower alkylamino group include an amino group having 1 to 2 (preferably 1) halogen substituted lower alkyl groups as illustrated above (preferably a linear or branched halogen substituted alkyl group having 1 to 6 carbon atoms with 1 to 7 (preferably 1 to 3) halogen atoms). Specific examples thereof include an N-fluoromethylamino group, N-difluoromethylamino group, N-trifluoromethylamino group, N-chloromethylamino group, N-dichloromethylamino group, N-trichloromethylamino group, N-bromomethylaminogroup, N-dibromomethylamino group, N-dichlorofluoromethylamino group, N-2,2,2-trifluoroethylamino group, N-pentafluoroethylamino group, N-2-chloroethylamino group, N-3,3,3-trifluoropropylamino group, N-heptafluoropropylamino group, N-heptafluoroisopropylamino group, N-3-chloropropylamino group, N-2-chloropropylamino group, N-3-bromopropylamino group, N-4,4,4-trifluorobutylamino group, N-4,4,4,3,3-pentafluorobutylamino group, N-4-chlorobutylamino group, N-4-bromobutylamino group, N-2-chlorobutylamino group, N-5,5,5-trifluoropentylamino group, N-5-chloropentylamino group, N-6,6,6-trifluorohexylamino group, N-6-chlorohexylamino group, N-(1,1-dimethyl-2-chloroethyl)amino group, N-(2-methyl-3-fluoropropyl)amino group, and N,N-di(fluoromethyl)amino group.

Examples of the lower alkylthio lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 3 lower alkylthio groups whose alkyl moiety is a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms). Specific examples thereof include a 2-methylthioethyl group, 2-ethylthioethyl group, 2-n-propylthioethyl group, 2-n-butylthioethyl group, 2-tert-butylthioethyl group, 2-n-pentylthioethyl group, 2-n-hexylthioethyl group, methylthiomethyl group, 1-methylthioethyl group, 3-methylthiopropyl group, 4-methylthiobutyl group, 5-methylthiopentyl group, 6-methylthiohexyl group, 1,1-dimethyl-2-methylthioethyl group, 2-methyl-3-methylthiopropyl group, 2,2-diethylthioethyl group, and 2,2,2-triethylthioethyl group.

Examples of the amidino group that may have a lower alkyl group include an amidino group that may have 1 to 2 lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms). Specific examples thereof include an amidino group, N-methylamidino group, N-ethylamidino group, N-n-propylamidino group, N-n-butylamidino group, N-n-pentylamidino group, N-n-hexylamidino group, N-isopropylamidino group, N-tert-butylamidino group, N,N-dimethylamidino group, N,N'-dimethylamidino group, and N-methyl-N'-ethyl-amidino group.

Examples of the amidino lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 3 amidino groups. Specific examples thereof include an amidinomethyl group, 2-amidinoethyl group, 3-amidinopropyl group, 4-amidinobutyl group, 5-amidinopropyl group, 6-amidinohexyl group, 1-amidinoethyl group, 1,1-dimethyl-2-amidinoethyl group, 2-methyl-3-amidinopropyl group, 2,2-diamidinoethyl group, and 2,2,2-triamidinoethyl group.

Examples of the lower alkenyloxy group include a lower alkenyloxy group whose lower alkenyl moiety is one as illustrated above (a linear or branched alkenyloxy group having 1 to 3 double bonds and 2 to 6 carbon atoms). Specific examples thereof include a vinyloxy group, 1-propenyloxy group, 1-methyl-1-propenyloxy group, 2-methyl-1-propenyloxy group, 2-propenyloxy group, 2-butenyloxy group, 1-butenyloxy group, 3-butenyloxy group, 2-pentenyloxy group, 1-pentenyloxy group, 3-pentenyloxy group, 4-pentenyloxy group, 1,3-butadienyloxy group, 1, 3-pentadienyloxy group, 2-penten-4-ynyloxy group, 2-hexenyloxy group, 1-hexenyloxy group, 5-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 3,3-dimethyl-1-propenyloxy group, 2-ethyl-1-propenyloxy group, 1,3,5-hexatrienyloxy group, 1,3-hexadienyloxy group, and 1,4-hexadienyloxy group.

Examples of the lower alkenyloxy lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 3 lower alkenyloxy groups whose lower alkenyloxy moiety is a lower alkenyloxy group as illustrated above (a linear or branched alkenyl group having 2 to 6 carbon atoms and 1 to 3 double bonds). Specific examples thereof include a vinyloxymethyl group, 2-vinyloxyethyl group, 2-(1-propenyloxy)ethyl group, 2-(1-methyl-1-propenyloxy)ethyl group, 2-(2-methyl-1-propenyloxy)ethyl group, 2-(2-propenyloxy)ethyl group, 2-(2-butenyloxy)ethyl group, 2-(1-butenyloxy)ethyl group, 2-(3-butenyloxy)ethyl group, 2-(2-pentenyloxy)ethyl group, 2-(1-pentenyloxy)ethyl group, 2-(3-pentenyloxy) ethyl group, 2-(4-pentenyloxy)ethyl group, 2-(1,3-butadienyloxy)ethyl.group, 2-(1,3-pentadienyloxy)ethyl group, 2-(2-penten-4-ynyloxy)ethyl group, 2-(2-hexenyloxy)ethyl group, 2-(1-hexenyloxy)ethyl group, 2-(5-hexenyloxy)ethyl group, 2-(3-hexenyloxy)ethyl group, 2-(4-hexenyloxy)ethyl group, 2-(3,3-dimethyl-1-propenyloxy)ethyl group, 2-(2-ethyl-1-propenyloxy)ethyl group, 2-(1,3,5-hexatrienyloxy)ethyl group, 2-(1,3-hexadienyloxy)ethyl group, 2-(1,4-hexadienyloxy)ethyl group, 3-vinyloxypropyl group, 4-vinyloxybutyl group, 5-vinyloxypropyl group, 6-vinyloxyhexyl group, 1-vinyloxyethyl group, 1,1-dimethyl-2-vinyloxyethyl group, 2-methyl-3-vinyloxypropyl group, 2,2-divinyloxyethyl group, and 2,2,2-trivinyloxyethyl group.

Examples of the arylamino group that may have a substituent selected from the group consisting of a lower alkyl group, lower alkoxy group, halogen substituted lower alkyl group, and halogen substituted lower alkoxy group on the aryl group include
an amino group having 1 to 2 aryl groups as illustrated above that may have 1 to 7, preferably 1 to 5, more preferably 1 to 2 substituents, on the aryl group, which are selected from the group consisting of a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a lower alkoxy group as illustrated above (a linear or branched alkoxy group having 1 to 6 carbon atoms);
a halogen substituted alkyl group as illustrated above (preferably a linear or branched alkyl group having 1 to 6 carbon atoms with 1 to 7, preferably 1 to 3 halogen atoms); and
halogen substituted lower alkoxy group as illustrated above (a linear or branched alkoxy group having 1 to 6 carbon atoms with preferably 1 to 7, more preferably 1 to 3 halogen atoms). Specific examples thereof include an N-phenylamino group, N-2-naphthylamino group, N-(2-methylphenyl)amino group, N-(3-ethyl-1-naphthyl)amino group, N-(4-n-propylphenyl)amino group, N-(2-n-butyl-1-phenyl)amino group, N-(3-n-pentylphenyl)amino group, N-(4-n-hexyl-1-naphthyl)amino group, N-(2-isobutylphenyl) amino group, N-(3-tert-butyl-1-naphthyl)amino group, N-(2-methoxyphenyl)amino group, N-(3-ethoxy-1-naphthyl)amino group, N-(4-n-propoxyphenyl)amino group, N-(3-isopropoxy-1-naphthyl)amino group, N-(n-butoxyphenyl)amino group, N-(1-isobutoxy-2-naphthyl)amino group, N-(tert-butoxyphenyl)amino group, N-(5-sec-butoxy-1-naphthyl)amino group, N-(n-pentyloxyphenyl)amino group, N-(5-isopentyloxy-1-naphthyl)amino group, N-(1-neopentyloxyphenyl)amino group, N-(6-n-hexyloxy-2-naphthyl)amino group, N-(isohexyloxyphenyl)amino group, N-(3-methylpentyloxy-1-naphthyl)amino group, N-(2-trifluoromethylphenyl)amino group, N-(4-trifluoromethylphenyl)amino group, N-(2-chloromethylphenyl)amino group, N-[3-(2-fluoroethyl)-1-naphthyl]amino group, N-[4-(3-bromopropyl)phenyl]amino group, N-[2-(4-chlorobutyl)-1-phenyl]amino group, N-[3-(5-fluoropentyl)phenyl]amino group, N-[4-(6-bromohexyl)-1-naphthyl]amino group, N-[2-(1,1-dimethyl-2-chloroethyl)phenyl]amino group, N-[7-(2-methyl-3-fluoropropyl)-2-naphthyl]amino group, N-(2-chloromethoxyphenyl)amino group, N-(4-trifluoromethoxyphenyl)amino group, N-(3-(2-fluoroethoxy)-1-naphthyl)amino group, N-[4-(3-bromopropoxy)phenyl]amino group, N-[2-(4-chlorobutoxy)-1-phenyl]amino group, N-[3-(5-fluoropentyloxy)phenyl]amino group, N-[4-(6-bromohexyloxy)-1-naphthyl]amino group, N-[2-(1,1-dimethyl-2-chloroethoxy)phenyl]amino group, N-[7-(2-methyl-3-fluoropropoxy)-2-naphthyl]amino group, N-(2-chloromethoxyphenyl)amino group, N-[3-(2-fluoroethoxy)-1-naphthyl]amino group, N-[4-(3-bromopropoxy)phenyl]amino group, N-[2-(4-chlorobutoxy)-1-phenyl]amino group, N-[3-(5-fluoropentyloxy)phenyl]amino group, N-[4-(6-bromohexyloxy)-1-naphthyl]amino group, N-[2-(1,1-dimethyl-2-chloroethoxy)phenyl]amino group, N-[7-(2-methyl-3-fluoropropoxy)-2-naphthyl]amino group, and N,N-diphenylamino group.

Examples of the aryl lower alkenyl group include a lower alkenyl group as illustrated above having an aryl group as illustrated above (preferably a linear or branched alkenyl group having 1 to 3 aryl groups and 1 to 6 carbon atoms). Specific examples thereof include a 2-phenylethenyl group, 3-phenyl-2-propenyl group, 3-[(1- or 2-)naphthyl]-2-propenyl group, 4-[(2-,3-, or 4-)methylphenyl]-2-butenyl group, 4-[(2-, 3-, or 4-)ethylphenyl]-3-butenyl group, 4-[(2-, 3-, or 9-)n-propylphenyl]-1,3-butadienyl group, 5-[(2-, 3-, or 4-)n-butylphenyl]-1,3,5-hexatrienyl group, 5-[(2-, 3-, or 9-)n-pentylphenyl]-2,4-hexadienyl group, 5-[(2-, 3-, or 4-)n-hexylphenyl]-3-pentenyl group, 3-[(2-, 3-, or 4-)isobutylphenyl]-2-propenyl group, 2-[(2-, 3-, or 4-)tert-butylphenyl]phenyl group, 3-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)methyl-1-naphthyl]-2-propenyl group, 4-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)methyl-2-naphthyl]-2-butenyl group, 4-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)ethyl-1-naphthyl]-3-butenyl group, 4-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)ethyl-2-naphthyl]-1,3-butadienyl group, 5-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-propyl-1-naphthyl]-1,3,5-hexatrienyl group, 5-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-propyl-2-naphthyl]-2,4-hexadienyl group, 5-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-butyl-1-naphthyl]-3-pentenyl group, 3-[(1-,3-, 4-, 5-, 6-, 7-, or 8-)n-butyl-2-naphthyl]-2-propenyl group, 2-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-pentyl-1-naphthyl]ethenyl group, 3-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-pentyl-2-naphthyl]-2-propenyl group, 4-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-hexyl-1-naphthyl]-2-butenyl group, 4-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-hexyl-2-naphthyl]-3-butenyl group,4- [(2-, 3-, 4-, 5-, 6-, 7-, or 8-)isobutyl-1-naphthyl]-1,3-butadienyl group, 5-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)isobutyl-2-naphthyl]-1,3,5-hexatrienyl group, 5-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)tert-butyl-1-naphthyl]-2,4-hexadienyl group, 5-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)tert-butyl-2-naphthyl]-1,3,5-hexatrienyl group, 5-[(2-, 3-, or 4-)chlorophenyl group, (2-, 3-, or 4-)fluorophenyl]-2,4-hexadienyl group, 5-[(2-, 3-, or 4-)bromophenyl]-3-pentenyl group, 3-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-chloro-1-naphthyl]-2-propenyl group, 2-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)chloro-2-naphthyl]ethenyl group, 3-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)fluoro-1-naphthyl]-2-propenyl group, 4-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)fluoro-2-naphthyl]-2-butenyl group, 4-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)bromo-1-naphthyl]-3-butenyl group, 4-[(1-, 3-, 4-, 5-, 6-, 7-, or 8-)bromo-2-naphthyl]-1,3-butadienyl group, 5-[(2-, 3-, or 4-)aminophenyl]-1,3,5-hexatrienyl group, 5-[(2-, 3-, 4-, 5-, 6-, 7-, or 8-)amino-1-naphthyl]-2,4-hexadienyl group, 5-[(1-,3-, 4-, 5-, 6-, 7-, or 8-)amino-2-naphthyl]-3-pentenyl group, 3-(2,3-dimethylphenyl)-2-propenyl group, 2-(3,4-dimethylphenyl)vinyl group, 3-(2,4-dimethylphenyl)-2-propenyl group, 4-(2,5-dimethylphenyl)-2-butenyl group, 4-(2,6-dimethylphenyl)-3-butenyl group, 4-(2,4,6-trimethylphenyl)-1,3-butadienyl group, 5-(3,4,5-trimethylphenyl)-1,3,5-hexatrienyl group, 5-(2,3,4,5-tetraethylphenyl)-2,4-hexadienyl group, 5-(pentamethylphenyl)-3-pentenyl group, 3-(2-methylnaphthyl)-2-propenyl group, 2-(2,3-dimethylnaphthyl)ethenyl group, 3-(3,4-dimethylphenyl)-2-propenyl group, 4-(3,5,7-triethylnaphthyl)-2-butenyl group, 4-(3,4,5,7-tetramethylnaphthyl)-3-butenyl group, 4-(2,3,4,5,7-pentamethylnaphthyl)-1,3-butadienyl group, 5-(2,3,4,5,6,7-hexaethylnaphthyl)-1,3,5-hexatrienyl group, 5-(heptamethylnaphthyl)-2,4-hexadienyl group, 5-(2,3-diaminophenyl)-3-pentenyl group, 3-(2,4,6-triaminophenyl)-2-propenyl group, and 2-(2-methyl-5-chloronaphthyl)ethenyl group.

Examples of the pyridylamino group that may have a lower alkyl group include a pyridylamino group that may have 1 to 3, preferably 1 to 2 lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms), on the pyridyl group and/or amino group. Specific examples thereof include an N-(2-, 3-, or 4-)pyridylamino group, N-3-methyl-2-pyridylamino group, N-(4-methyl-2-pyridyl)amino group, N-(5-methyl-2-pyridyl)amino group, N-(6-methyl-2-pyridyl)amino group, N-(2-methyl-3-pyridyl)amino group, N-(4-methyl-3-pyridyl)amino group, N-(5-methyl-3-pyridyl)amino group, N-(6-methyl-3-pyridyl)amino group, N-(2-methyl-4-pyridyl)amino group, N-(3-methyl-4-pyridyl)amino group, N-(3-ethyl-2-pyridyl)amino group, N-(4-n-propyl-2-pyridyl)amino group, N-(5-n-propyl-2-pyridyl)amino group, N-(2-n-butyl-3-pyridyl)amino group, N-(4-n-pentyl-3-pyridyl)amino group, N-(5-n-hexyl-3-pyridyl)amino group, N-(2-isopropyl-4-pyridyl)amino group, N-(3-tert-butyl-4-pyridyl)amino group, N-(3-methyl-2-pyridyl)-N-methyl-amino group, and N-(2,4-diethyl-3-pyridyl)-N-methyl-amino group.
Examples of the aryl lower alkyl group (that may have a group selected from the group consisting of halogen atom, lower alkyl group, halogen substituted alkyl group, halogen substituted lower alkoxy group, lower alkoxy group, carbamoyl group, and lower alkoxycarbonyl group, as a substituent, on the aryl group and/or the lower alkyl group) include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 3 (preferably 1) aryl groups as illustrated above. Note that, on the aryl group and/or the alkyl moiety, there may be 1 to 7, preferably 1 to 5, more preferably, 1 to 2 substituents selected from the group consisting of
a halogen atom as illustrated above;
a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a halogen substituted lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms preferably substituted with 1 to 7 halogen atoms);
a lower alkoxy group as illustrated above (a linear or branched alkoxy group having 1 to 6 carbon atoms substituted with 1 to 7 halogen atoms);
a lower alkoxy group as illustrated above (a linear or branched alkoxy group having 1 to 6 carbon atoms);
a carbamoyl group; and
a lower alkoxy-carbonyl group as illustrated above. Specific examples of the aryl lower alkyl group (that may have a substituent selected from the group consisting of a halogen atom, lower alkyl group, halogen substituted lower alkyl group, halogen substituted lower alkoxy group, lower alkoxy group, carbamoyl group and lower alkoxycarbonyl group, on the aryl group and/or the lower alkyl group) include a benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-methyl-1-phenylethyl group, 1,1-dimethyl-2-phenylethyl group, 1,1-dimethyl-3-phenylpropyl group, (2-, 3-, or 4-)fluorobenzyl group, 2-[(2-, 3-, or 4-)fluorophenyl]ethyl group, 1-[(2-, 3-, or 4-)fluorophenyl]ethyl group, 1-[(2-, 3-, or 4-)fluorophenyl]propyl group, 2-[(2,6- or 3,5-)difluorophenyl]ethyl group, 1-(3,5-difluorophenyl)ethyl group, 1-(3,5-difluorophenyl)propyl group, (2-, 3-, or 4-)chlorobenzyl group, 2-[(2-, 3-,or 4-)chlorophenyl]ethyl group, 2-(3,4-dichlorophenyl)ethyl group, 1-(3-chlorophenyl)butyl group, 1-(4-chlorophenyl)butyl group, (2-, 3-, or 4-)trifluoromethylphenylbenzyl group, 1-[(2-, 3-, or 4-)trifluoromethylphenyl]ethyl group, 1-[(2-, 3-, or 4-)trifluoromethylphenyl]propyl group, (2-, 3-, or 4-)methylbenzyl group, 2-[(2- 3-, or 4-)methylphenyl]ethyl group, (2-, 3-, or 4-)trifluoromethoxybenzyl group, 1-[(2-, 3-, or 4-)trifluoromethylphenyl]ethyl group, (2-, 3-, or 4-)methoxybenzyl group, 2-[(2-, 3-, or 4-)methylphenyl]ethyl group, 1-[(2-, 3-, or 4-)methoxyphenyl]propyl group, (2-, 3-, or 4-)ethoxybenzyl group, (3,4- or 3,5-)dimethoxybenzyl group, (3,4- or 3,5-)di(n-butoxy)benzyl group, 2-[(3,5-or 3,4-)dimethoxyphenyl]ethyl group, 2-(2-ethoxyphenyl)ethyl group, 1-(4-methoxyphenyl)butyl group, 1-phenyl-1-methoxycarbonylmethyl group, 1-carbamoyl-2-phenylethyl group, 1-methoxycarbonyl-2-phenylethyl group, 2-methoxycarbonyl-2-phenylethyl group, 2-phenyl-2-hydroxyethyl group, 2-(4-hydroxyphenyl)-1-methoxycarbonylethyl group, 3-chloro-4-difluoromethoxyphenylmethyl group, and naphthylmethyl group.

Examples of the lower alkynyl group include a linear or branched alkynyl group having 2 to 6 carbon atoms. Specific examples thereof include an ethynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-pentynyl group, and 2-hexynyl group.

Examples of the aryloxy lower alkyl group (on the aryl group, a group selected from the group consisting of a lower alkoxy group; a carbamoyl group that may have a group selected from the group consisting of a lower alkoxy group and a lower alkyl group; and a pyrrolidinyl group that may have an oxo group, may be present, include an aryl lower alkyl group whose aryl moiety and lower alkyl group are as illustrated above. On the aryl group herein, 1 to 5 (preferably 1 to 2) groups selected from the group consisting of a lower alkoxy group as illustrated above; a carbamoyl group that may have 1 to 2 groups selected from the group consisting of a lower alkoxy group as illustrated above and a lower alkyl group as illustrated above; and oxo group may be present as a substituent(s). Specific examples thereof include a 2-[(2-, 3- or 4-)methoxyphenoxy]ethyl group, 2-[(2-, 3- or 4-)carbamoylphenoxy]ethyl group, 2-[(2-, 3- or 4-)(N-methyl-N-ethoxycarbamoyl)phenoxy]ethyl group and 2-[(2-, 3- or 4-)(2-oxo-1-pyrolidiny)phenoxy]ethyl group.

Examples of the isoxazolidinyl group that may have an oxo group include an isoxazolidinyl group that may have 1 to 2 (preferably 1) oxo groups. Specific examples thereof include a 3-oxoisooxazolidin-4- or 5-yl group and 3,5-dioxoisoxazolidin-4-yl group.

Examples of the dihydroindenyl group include a (1-, 2-, 4- or 5-)-1,2-dihydroindenyl group.

Examples of the aryl lower alkoxy lower alkyl group include an aryl lower alkoxy lower alkyl group whose aryl moiety, lower alkoxy moiety and lower alkyl group moiety are as illustrated above. Specific examples thereof include a benzyloxymethyl group, 2-benzyloxyethyl group and 2-benzyloxybutyl group.

Examples of the azetidinyl group that may have a group selected from the group consisting of a lower alkanoyl group and an aroyl group include an azetidinyl group that may have a 1 to 3 (preferably 1) groups selected from a lower alkanoyl group as illustrated above and an aroyl group as illustrated above. Specific examples thereof include a 2- or 3-azetinyl group, 1-acetyl-(2- or 3-)azetidinyl group, 1-butyryl-(2- or 3-)azetidinyl group and 1-benzoyl-(2- or 3-)azetidinyl group.

Examples of the azetidinyl lower alkyl group that may have a group selected from the group consisting of a lower alkanoyl group and an aroyl group include an azetidinyl lower alkyl group that may have 1 to 3 (preferable 1) groups selected from the group consisting of a lower alkanoyl group as illustrated above and an aroyl group as illustrated above and have a lower alkyl moiety as illustrated above. Specific examples thereof include a 2- or 3-azetidinylmethyl group, 2-(2- or 3-azetidinyl)ethyl group, 1-acetyl-(2-or 3-)azetidinylmethyl group, 1-butyryl-(2- or 3-)azetidinylmethyl group, 1-benzoyl-(2- or 3-)azetidinylmethyl group, 2-[1-acetyl-(2- or 3-)azetidinyl]ethyl group, 2-[1-butyryl-(2- or 3-)azetidinyl]ethyl group and 2-[1-benzoyl-(2- or 3-)azetidinyl]ethyl group.

Examples of the tetrazolyl group include a (1- or 5-)tetrazolyl group.

Examples of the indolinyl group that may have an oxo group include an indolinyl group that may have 1 to 2 (preferably 1) oxo groups. Specific examples thereof include a (1-,3-, 5-, 6-,7- or 8-)indolinyl group, 2-oxo-(1-,3-, 5-, 6-, 7- or 8-)indolinyl group and 2,3-dioxo-(1-,5-,6-, 7- or 8-)indolinyl group.

Examples of the triazolyl group include a 1,2,4,-triazolyl group and a 1,3,5,-triazolyl group.

Examples of the triazolyl group that may have a group selected from the group consisting of a lower alkyl group and a lower alkylthio group include a triazolyl group as illustrated above that may have 1 to 3 (more preferably 1 to 2) groups selected from the group consisting of a lower alkyl group as illustrated above and a lower alkylthio group as illustrated above. Specific examples thereof include a (1-, 3- or 5-)-1,2,4-triazolyl group, (1-, 2- or 5-)-1,3,5-triazolyl group, 1-methyl-5-methylthio-1,2,4-triazol-3-yl group and 1-methyl-5-methylthio-1,2,3-triazol-2-yl group.

Examples of the imidazolyl group that may have a carbamoyl group include an imidazolyl group that may have 1 to 2 (preferably 1) carbamoyl groups. Specific examples thereof include a (1-, 2-, 4- or 5-)imidazolyl group and a 4-carbamoyl-(1, 2- or 5-)imidazolyl group.

Examples of the oxazolyl group that may have a lower alkyl group include an oxazolyl group that may have 1 to 2 (preferably 1) lower alkyl groups as illustrated above. Specific examples thereof include a (2-, 3- or 4-)oxazolyl group and a 4-methyl-(2- or 3-)oxazolyl group.

Examples of the isothiazolyl group that may have a lower alkyl group include an isothiazolyl group that may have 1 to 2 (preferably 1) lower alkyl groups as illustrated above. Specific examples thereof include a (3-, 4- or 5-)isothiazolyl group and a (3- or 4-)methyl-2-isothiazolyl group.

Examples of the dihydrobenzothiazolyl group include a (1-,2-,4-, 5-, 6- or 7-)2,3-dihydrobenzothiazolyl group.

Examples of the dihydrobenzothiazolyl group that may have an oxo group include a dihydrobenzothiazolyl group that may have a single oxo group. Specific examples thereof include a (1-, 2-, 5-, 6-, 7- or 8-)2,3-dihydrobenzothiazolyl group and a 2-oxo-(1-,5-, 6-, 7- or 8-)2,3-dihydrobenzothiazolyl group.

Examples of the thienyl group that may have a lower alkoxycarbonyl group include a thienyl group that may have 1 to 2 (preferably 1) lower alkoxycarbonyl groups as illustrated above. Specific examples thereof include a (2- or 3-)thienyl group and a 3-methoxycarbonyl-2-thienyl group.

Examples of the oxazolyl lower alkyl group that may have a lower alkyl group include an oxazolyl lower alkyl group as illustrated above, whose alkyl group as illustrated above, having 1 to 3 (more preferably 1 to 2) lower alkyl groups as illustrated above on the oxazole ring. Specific examples thereof include a (2-, 4- or 5-)oxazolylmethyl group, 2-(2-, 4-or 5-)oxazolylmethyl group, [2-methyl-(4- or 5-)oxazolyl]methyl group and (2,5-dimethyl-4-oxazolyl)methyl group.

Examples of the amino lower alkyl group that may have a group, on the amino group, which is selected from the group consisting of a lower alkyl group, halogen substituted lower alkyl group, lower alkoxycarbonyl group, lower alkanoyl group, aryl group, aryl lower alkyl group, aroyl group, and amino substituted alkyl group (on the amino group of the amino substituted alkyl group, a lower alkyl group may be present as a substituent) include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 5, preferable 1 to 3, more preferably 1, amino groups. Note that, on the amino group, 1 to 2 substituents may be present which are selected from the group consisting of
a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a halogen substituted lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms with 1 to 13, preferably 1 to 7, more preferably 1 to 3 halogen atoms);
a lower alkoxy-carbonyl group as illustrated above ;
a lower alkanoyl group as illustrated above (
a linear or branched alkanoyl group having 1 to 6 carbon atoms);
an aryl group as illustrated above;
an aryl lower alkyl group as illustrated above;
an aroyl group as illustrated above; and a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) having 1 to 5, preferably 1 to 3, more preferably 1, amino groups (1 to 2 lower alkyl groups as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) may be present on the amino group, as a substituent(s)). Specific examples of the amino lower alkyl group that may have, on the amino group, a group selected from the group consisting of a lower alkyl group, halogen substituted lower alkyl group, lower alkoxycarbonyl group, lower alkanoyl group, aryl group, aryl lower alkyl group, aroyl group, and amino substituted alkyl group ((on the amino group of the amino substituted alkyl group, a lower alkyl group may be present as a substituent) include an N-methylaminomethyl group, N-ethylaminomethyl group, N-n-propylaminomethyl group, N,N-dimethylaminomethyl group, N,N-diethylaminomethyl group, N-methyl-N-n-propylaminomethyl group, N-methyl-N-ethylaminomethyl group, N-(2,2,2-trifluoroethyl)aminomethyl group, N-methyl-N-benzylaminomethyl group, N-phenylaminomethyl group, N-methyl-N-phenylaminomethyl group, N-formylaminomethyl group, N-methyl-N-acetylaminomethyl group, N-methyl-N-propionylaminomethyl group, N-(2-(N,N-diethylamino)ethyl)aminomethyl group, N-methyl-N-benzoylaminomethyl group, N-methylaminoethyl group, N-ethylaminoethyl group, N-(2,2,2-trifluoroethyl)aminoethyl group, N,N-dimethylaminoethyl group, N,N-diethylaminoethyl group, N-methyl-N-acetylaminoethyl group, N-methyl-N-benzoylaminoethyl group, N-methyl-N-propionylaminoethyl group, N-methyl-N-benzylaminoethyl group, and N-methyl-N-tert-butoxycarbonylaminoethyl group.

Examples of the lower alkyl group substituted with a carbamoyl group that may have a group selected from the group consisting of a lower alkyl group and a halogen substituted lower alkyl group include a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) and substituted with 1 to 3 (preferably 1) carbamoyl groups that may have 1 to 2 groups selected from the group consisting of
a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms); and
a halogen substituted lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms and 1 to 13, preferably 1 to 7, more preferably 1 to 3 halogen atoms). Specific examples thereof include a carbamoylmethyl group, 2-carbamoylethyl group, 1-carbamoylethyl group, 3-carbamoylpropyl group, 4-carbamoylbutyl group, 5-carbamoylpentyl group, 6-carbamoylhexyl group, 1,1-dimethyl-2-carbamoylethyl group, 2-methyl-3-carbamoylpropyl group, 1,2-dicarbamoylethyl group, 2,2-dicarbamoylethyl group, 1,2,3-tricarbamoylpropyl group, N-methylcarbamoylmethyl group, N-ethylcarbamoylmethyl group, 2-(N-n-propylcarbamoyl)ethyl group, 3-(N-n-butylcarbamoyl)propyl group, 4-(N-isobutylcarbamoyl)butyl group, 5-(N-tert-butylcarbamoyl)pentyl group, 6-(N-pentylcarbamoyl)hexyl group, N,N-dimethylcarbamoylmethyl group, N,N-diethylcarbamoylmethyl group, 2-(N-2-fluoroethylcarbamoyl)ethyl group, 3-(N-2-chloroethylcarbamoyl)propyl group, 4-(N-2-bromoethylcarbamoyl)butyl group, 2-(N-2,2-dichloroethylcarbamoyl)ethyl group, N-2,2,2-trifluoroethylcarbamoylmethyl group, and N-heptafluoropropylcarbamoylmethyl group.

Examples of the thiocarbamoyl group that may have a lower alkyl group include a thiocarbamoyl group that may have 1 to 2 lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms). Specific examples thereof include a thiocarbamoyl group, N-methyl-thiocarbamoyl group, N-ethyl-thiocarbamoyl group, N-n-propylthiocarbamoyl group, N-n-butyl-thiocarbamoyl group, N-n-pentyl-thiocarbamoyl group, N-n-hexyl-thiocarbamoyl group, N-isobutyl-thiocarbamoyl group, N-tert-butyl-thiocarbamoyl group, N,N-dimethyl-thiocarbamoyl group, and N-methyl-N-ethyl-thiocarbamoyl group.

Examples of the oxazolidinyl group that may have an oxo group include an oxazolidinyl group that may have 1 to 2 (preferably 1) oxo groups. Specific examples thereof include an oxazolidin-3-yl group, oxazolidin-4-yl group, oxazolidin-5-yl group, 2-oxo-oxazolidin-4-yl group, 2-oxo-oxazolidin-3-yl group, and 2-oxo-oxazolidin-5-yl group.

Examples of the imidazolidinyl group that may have a substituent selected from the group consisting of an oxo group and a lower alkyl group include an imidazolidinyl group that may have 1 to 3, preferably 1 to 2 substituents selected from the group consisting of oxo group and a lower alkyl group as illustrated above (preferably a linear or branched alkyl group having 1 to 6 carbon atoms). Specific examples thereof include an imidazolidin-1-yl group, imidazolidin-2-yl group, imidazolidin-4-yl group, 2-oxo-imidazolidin-1-yl group, 4-oxo-imidazolidin-1-yl group, 5-oxo-imidazolidin-1-yl group, 4-oxo-imidazolidin-2-yl group, 2-oxo-imidazolidin-4-yl group, 2-methyl-imidazolidin-1-yl group, 4-ethyl-imidazolidin-1-yl group, 5-n-propyl-imidazolidin-1-yl group, 4-n-butyl-imidazolidin-2-yl group, 2-n-pentyl-imidazolidin-4-yl group, 2-n-hexyl-imidazolidin-1-yl group, 4-isobutyl-imidazolidin-2-yl group, 2-tert-butyl-imidazolidin-4-yl group, 2-oxo-3-methyl-imidazolidin-1-yl group, and 2-oxo-3,4-dimethyl-imidazolidin-1-yl group.

Examples of the pyrrolidinyl group that may have an oxo group include a pyrrolidinyl group that may have 1 to 2 (preferably 1) oxo groups. Specific examples thereof include a (1-, 2- or 3-)pyrrolidinyl group, (2- or 3-)oxo-1-pyrrolidinyl group, (3-, 4- or 5-)oxo-2-pyrrolidinyl group, and (2-,4- or 5-)oxo-3-pyrrolidinyl group.

Examples of the imidazolyl group include a (1-,2-, 4- or -5)imidazolyl group.

Examples of the isoxazolyl group include a (3-, 4- or 5-)isoxazolyl group.

Examples of the arylsulfonyl group include an arylsulfonyl group whose aryl moiety is phenyl, biphenyl, substituted biphenyl, substituted phenyl, naphthyl and substituted naphthyl, and which may have, on the aryl moiety, 1 to 7, preferably 1 to 5, more preferably 1 to 2 linear or branched alkyl groups having 1 to 6 carbon atoms. Examples of the substituent such as phenyl, biphenyl and naphthyl include a linear or branched alkyl group having 1 to 6 carbon atoms, a halogen atom, an amino group and the like. One to seven, preferably 1 to 5, more preferably 1 to 2 substituents of at least one type of these may be present on the phenyl, biphenyl, naphthyl ring and the like. Specific Examples of the arylsulfonyl group that may have a lower alkyl group on the aryl group include a phenylsulfonyl group, (2-, 3-, or 4-)biphenylsulfonyl group, (1- or 2-)naphthylsulfonyl group, (2-, 3-, or 4-)methylphenylsulfonyl group, (2-, 3-, or 4-)ethylphenylsulfonyl group, (2-, 3-, or 4-)n-propylphenylsulfonyl group, (2-, 3-, or 4-)n-butylphenylsulfonyl group, (2-, 3-, or 4-)n-pentylphenylsulfonyl group, (2-, 3-, or 4-)n-hexylphenylsulfonyl group, (2-, 3-, or 4-)isobutylphenylsulfonyl group, (2-, 3-, or 4-)tert-butylphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)methyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)methyl-3-biphenylsulfonyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)methyl-4-biphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)ethyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)ethyl-3-biphenylsulfonyl group, (2-, 3-; 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)ethyl-4-biphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-propyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-propyl-3-biphenylsulfonyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-propyl-4-biphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-butyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-butyl-3-biphenylsulfonyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-butyl-4-biphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-pentyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-pentyl-3-biphenylsulfonyl group, (2-, 3-, 5-, 6-, 2'-, 3'- 4'-, 5'-, or 6'-)n-pentyl-4-biphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-hexyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-hexyl-3-biphenylsulfonyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)n-hexyl-4-biphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)isobutyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)isobutyl-3-biphenylsulfonyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)isobutyl-4-biphenylsulfonyl group, (3-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)tert-butyl-2-biphenylsulfonyl group, (2-, 4-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)tert-butyl-3-biphenylsulfonyl group, (2-, 3-, 5-, 6-, 2'-, 3'-, 4'-, 5'-, or 6'-)tert-butyl-4-biphenylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)methyl-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)methyl-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)ethyl-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)ethyl-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-propyl-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-propyl-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-butyl-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-butyl-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-pentyl-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-pentyl-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)n-hexyl-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)n-hexyl-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)isobutyl-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)isobutyl-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)tert-butyl-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)tert-butyl-2-naphthylsulfonyl group, (2-, 3-, or 4-)chlorophenylsulfonyl group, (2-, 3-, or 9-) fluorophenylsulfonyl group, (2-, 3-, or 4-)bromophenylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)chloro-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)chloro-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)fluoro-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)fluoro-2-naphthylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)bromo-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)bromo-2-naphthylsulfonyl group, (2-, 3-, or 4-)aminophenylsulfonyl group, (2-, 3-, 4-, 5-, 6-, 7-, or 8-)amino-1-naphthylsulfonyl group, (1-, 3-, 4-, 5-, 6-, 7-, or 8-)amino-2-naphthylsulfonyl group, 2,3-dimethylphenylsulfonyl group, 3,4-dimethylphenylsulfonyl group, 2,4-dimethylphenylsulfonyl group, 2,5-dimethylphenylsulfonyl group, 2,6-dimethylphenylsulfonyl group, 2,4,6-trimethylphenylsulfonyl group, 3,4,5-trimethylphenylsulfonyl group, 2,3,4,5-tetraethylphenylsulfonyl group, pentamethylphenylsulfonyl group, 2-methylnaphthylsulfonyl group, 2,3-dimethylnaphthylsulfonyl group, 3,4-dimethylphenylsulfonyl group, 3,5,7-triethylnaphthylsulfonyl group, 3,4,5,7-tetramethylnaphthylsulfonyl group, 2,3,4,5,7-pentamethylnaphthylsulfonyl group, 2,3,4,5,6,7-hexaethylnaphthylsulfonyl group, heptamethylnaphthylsulfonyl group, 2,3-diaminophenylsulfonyl group, 2,4,6-triaminophenylsulfonyl group, and 2-methyl-5-chloronaphthylsulfonyl group.

Examples of the piperidyl group that may have a substituent selected from the group consisting of a lower alkyl group; lower alkanoyl group; arylsulfonyl group; oxo group; hydroxy group and amino group that may have a group selected from the group consisting of a lower alkyl group, lower alkanoyl group, lower alkoxycarbonyl group and lower alkanoylamino lower alkanoyl group include a piperidyl group that may have 1 to 5, preferably 1 to 3, more preferably 1 substituent selected from the group consisting of
a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a lower alkanoyl group as illustrated above (
a linear or branched alkanoyl group having 1 to 6 carbon atoms); and
an arylsulfonyl group as illustrated above; an oxo group; a hydroxy group; and an amino group that may have 1 to 2 groups selected from the group consisting of a lower alkyl group as illustrated above, lower alkanoyl group as illustrated above, lower alkoxycarbonyl group as illustrated above and lower alkanoyl amino lower alkanoyl group as illustrated above. Specific examples thereof include a (1-, 2-, 3-, or 4-)piperidyl group, 1-methyl-9-piperidyl group, 2-ethyl-4-piperidyl group, 3-n-propyl-4-piperidyl group, 4-isopropyl-4-piperidyl group, 2-n-butyl-1-piperidyl group, 3-isobutyl-1-piperidyl group, 4-tert-butyl-1-piperidyl group, 1-sec-butyl-2-piperidyl group, 2-n-pentyl-2-piperidyl group, 3-(1-ethylpropyl)-2-piperidyl group, 4-iso-pentyl-2-piperidyl group, 5-neopentyl-2-piperidyl group, 6-n-hexyl-2-piperidyl group, 1-(1,2,2-trimethylpropyl)-3-piperidyl group, 2-(3,3-dimethylbutyl)-3-piperidyl group, 3-(2-ethylbutyl)-3-piperidyl group, 4-isohexyl-3-piperidyl group, 5-(3-methylpentyl group)-3-piperidyl group, 6-formyl-3-piperidyl group, 1-acetyl-4-piperidyl group, 2-propionyl-4-piperidyl group, 3-butyryl-4-piperidyl group, 4-isobutyryl-9-piperidyl group, 2-pentanoyl-1-piperidyl group, 3-tert-butylcarbonyl-1-piperidyl group, 4-hexanoyl-1-piperidyl group, 1-phenylsulfonyl-2-piperidyl group, 2-(2-biphenylsulfonyl)-2-piperidyl group, 3-(1-naphthylsulfonyl)-2-piperidyl group, 1-tosyl-4-piperidyl group, 4-(4-ethylphenylsulfonyl)-2-piperidyl group, 5-(2-n-propylphenylsulfonyl)-2-piperidyl group, 6-(3-n-butylphenylsulfonyl)-2-piperidyl group, 1-(4-n-pentylphenylsulfonyl)-3-piperidyl group, 2-(2-n-hexylphenylsulfonyl)-3-piperidyl, group, 3-(3-isobutylphenylsulfonyl)-3-piperidyl group, 4-(4-tert-butylphenylsulfonyl)-3-piperidyl group, 5-(2-chlorophenylsulfonyl)-3-piperidyl group, 6-(4-fluorophenylsulfonyl)-3-piperidyl group, 1-(3-bromophenylsulfonyl)-4-piperidyl group, 2-(2-aminophenylsulfonyl)-4-piperidyl group, 3-(2,3-dimethylphenylsulfonyl)-4-piperidyl group, 4-(3,4,5-trimethylphenylsulfonyl)-9-piperidyl group, 2-(2,3-diaminophenylsulfonyl)-1-piperidyl group, 4-oxo-1-piperidyl group, 2-oxo-3-piperidyl group, 4-hydroxy-1-piperidyl group, 2-hydroxy-3-piperidyl group, 4-amino-1-piperidyl group, 2-amino-4-piperidyl group, 4-methylamino-1-piperidyl group, 2-methylamino-4-piperidyl group, 4-ethylamino-1-piperidyl group, 2-ethylamino-4-piperidyl group, 2-dimethylamino-4-piperidyl group, 4-diethylamino-1-piperidyl group, 4-formylamino-1-piperidyl group, 4-acetylamino-1-piperidyl group, 9-(N-methyl-N-acetylamino)-1-piperidyl group, 4-(N-methyl-N-methoxycarbonylamino)-1-piperidyl group, 4-(N-metbyl-N-tert-butoxycarbonylamino)-1-piperidyl group, 4-[N-methyl-N-(N-acetylamino)acetylamino]-1-piperidyl group.

Examples of the piperidylcarbonyl group that may have a substituent selected from the group consisting of
a lower alkyl group, hydroxy group, hydroxy lower alkyl group, lower alkanoyl group, carboxy lower alkyl group, lower alkyl carbamoyl lower alkyl group, carbamoyl group, lower alkoxy group, carboxy group, lower alkoxycarbonyl group, amino group (on which 1 to 2. groups selected from the group consisting of a lower alkyl group, lower alkanoyl group, lower alkoxycarbonyl group and aroyl group may be present), piperidyl group (on which a group selected from the group consisting of a lower alkanoyl group, lower alkoxycarbonyl group and aroyl group may be present), piperazinyl group (on which a lower alkyl group may be present as a substituent), 1,4-dioxa-8-azasprio[4.5]decyl group, morpholinyl group, hexahydro-1,4-diazepinyl group (on which a lower alkyl group may be present as a substituent), pyridyl group, pyridyloxy group, pyridyl lower alkoxy group, tetrahydroquinolyl group (on which an oxo group may be present), benzodioxolyl group, aryl lower alkoxy group (that may have on the aryl group a group selected from the group consisting of a halogen atom, lower alkyl group, lower alkoxy group and halogen substituted lower alkoxy group), aryl group(on which a group selected from the group consisting of a halogen atom, lower alkoxy group and hydroxy group may be present), aryloxy group (that may have on the aryl group a group selected from the group consisting of a cyano group, halogen atom, lower alkyl group, lower alkoxy group and halogen substituted lower alkyl group), aryl lower alkyl group (that may have on the aryl group a group selected from the group consisting of a halogen atom, lower alkyl group, lower alkoxy group and halogen substituted lower alkyl group) and aroyl group (that may have on the aryl group a group selected from the group consisting of a halogen atom and a lower alkoxy group) include
a piperidylcarbonyl group that may have 1 to 3 (preferably 1) substituents, on the piperidyl group, selected from the group consisting of
a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a hydroxy group;
a hydroxy lower alkyl group as illustrated above (preferably a linear or branched alkyl group having 1 to 6 carbon atoms and having 1 to 3 hydroxy groups);
a lower alkanoyl group as illustrated above;
a carboxy lower alkyl group as illustrated above having a lower alkyl moiety as illustrated above;
a linear or branched alkyl group having 1 to 6 carbon atoms and substituted with a carbamoyl group having 1 to 2 lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms);
a carbamoyl group;
a lower alkoxy group as illustrated above (a linear or branched alkoxy group having 1 to 6 carbon atoms);
a carboxy group;
a lower alkoxycarbonyl group as illustrated
an amino group (on which 1 to 2 groups selected from the group consisting of a lower alkyl group as illustrated above, a lower alkanoyl group as illustrated above, lower alkoxycarbonyl group as illustrated above and aroyl group as illustrated above may be present);
a piperidyl group (on which 1 to 3 groups (preferably 1) selected from the group consisting of a lower alkanoyl group as illustrated above, lower alkoxycarbonyl group as illustrated above and aroyl group as illustrated above may be present);
a piperazinyl group (on which 1 to 3 lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms) may be present as a substituent(s));
a 1,4-dioxa-8-azasprio[4.5]decyl group;
a morpholinyl group;
a hexahydro-1,4-diazepinyl group (on which 1 to 3 lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms) may be present as a substituent(s));
a pyridyl group;
a pyridyloxy group;
a pyridyl lower alkoxy group having a lower alkoxy moiety as illustrated above;
a tetrahydroquinolyl group (on which 1 to 2 (preferably 1) oxo groups may be present);
a benzodioxolyl group (preferably benzo[1.3]dioxolyl group);
an aryl lower alkoxy group having an aryl moiety and lower alkoxy moiety as illustrated above (that may have on the aryl group 1 to 3 (preferably 1 to 2) groups selected from the group consisting of a halogen atom as illustrated above, lower alkyl group as illustrated above, lower alkoxy group as illustrated above and halogen substituted lower alkoxy group as illustrated above);
an aryl group as illustrated above (that may have on the aryl group 1 to 3 (preferably 1 to 2) groups selected from the group consisting of a halogen atom as illustrated above, lower alkoxy group as illustrated above and hydroxy group);
an aryloxy group having an aryl moiety as illustrated above (that may have on the aryl group 1 to 3 (preferably 1 to 2) groups selected from the group consisting of a cyano group, halogen atom, lower alkyl group as illustrated above, lower alkoxy group as illustrated above and halogen substituted lower alkyl group as illustrated above);
an aryl lower alkyl group having an aryl moiety and lower alkyl moiety as illustrated above (that may have on the aryl group 1 to 3 (preferably 1 to 2) groups selected from the group consisting of a halogen atom, lower alkyl group, lower alkoxy group and halogen substituted lower alkyl group); and
an aroyl group as illustrated above (that may have on the aryl group 1 to 3 (preferably 1 to 2) groups selected from the group consisting of a halogen atom as illustrated above and a lower alkoxy group as illustrated above). Specific examples thereof include a (1-, 2-, 3-, or 4-)piperidylcarbonyl group, (1-, 2-, 3-, or 4-)ethyl-4-piperidylcarbonyl group, (2-, 3-, or 4-)methyl-1-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)methyl-2-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)methyl-3-piperidylcarbonyl group, (1-, 2-, 3-, or 4-)methyl-4-piperidylcarbonyl group, (2-, 3-, or 4-)hydroxy-1-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)hydroxy-2-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)hydroxy-3-piperidylcarbonyl group, (1-, 2-, 3-, or 4-)hydroxy-4-piperidylcarbonyl group, (2-, 3-, or 4-)hydroxymethyl-1-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)hydroxymethyl-2-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)hydroxymethyl-3-piperidylcarbonyl group, (1-, 2-, 3-, or 4-)hydroxymethyl-4-piperidylcarbonyl group, (1-, 2-, 3-, or 4-)(2-hydroxyethyl)-4-piperidylcarbonyl group, (2-, 3-, or 4-)(N-ethyl-carbamoylmethyl)-1-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(N-ethyl-carbamoylmethyl)-2-piperidylcarbonyl group, (1-, 2-, 3-,4-, 5-, or 6-)(N-ethyl-carbamoylmethyl)-3-piperidylcarbonyl group, (1-, 2-, 3-, or 4-)N-ethyl-carbamoylmethyl-4-piperidylcarbonyl group, (2-, 3-, or 9-)carbamoyl-1-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)carbamoyl-2-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)carbamoyl-3-piperidylcarbonyl group, (1-, 2-, 3-, or 4-)carbamoyl-4-piperidylcarbonyl group, (2-, 3-, or 4-)carboxy-1-piperidylcarbonyl group, (2-, 3-, or 4-)carboxymethyl-1-piperidylcarbon group, (2-, 3-, or 4-)ethoxycarbonyl-1-piperidylcarbonyl group, (2-, 3-, or 4-)methoxy-1-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)methoxy-2-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)methoxy-3-piperidylcarbonyl group, (1-, 2-, 3-, or 9-)methoxy-9-piperidylcarbonyl group, 2-, 3-, or 4-)methoxycarbonyl-1-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)methoxycarbonyl-2-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)methoxycarbonyl-3-piperidylcarbonyl group, (1-, 2-, 3-, or 4-)methoxycarbonyl-4-piperidylcarbonyl group, (2-, 3-, or 4-)ethoxycarbonyl-1-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 5-)ethoxycarbonyl-2-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)ethoxycarbonyl-3-piperidylcarbonyl group, (1-, 2-, 3-, or 4-)ethoxycarbonyl-4-piperidylcarbonyl group, (2-, 3-, or 4-)acetylamino-1-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)acetylamino-2-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)acetylamino-3-piperidylcarbonyl group, (1-, 2-, 3-, or 4-) acetylamino-9-piperidylcarbonyl group, (2-, 3-, or 4-)tert-butoxycarbonylamino-1-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)tert-butoxycarbonylamino-2-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)tert-butoxycarbonylamino-3-piperidylcarbonyl group, (1-, 2-, 3-, or 4-)tert-butoxycarbonylamino-4-piperidylcarbonyl group, (2-, 3-, or 4-)butyrylamino-1-piperidylcarbonyl group, (2-, 3-, or 4-)benzoylamino-1-piperidylcarbonyl group, (2-, 3-, or 9-)(N-methyl-N-acetylamino)-1-piperidylcarbonyl group, (2-, 3-, or 9-)(N-methyl-N-butyrylamino)-1-piperidylcarbonyl group, (2-, 3-, or 9-)(N-methyl-N-tert-butoxycarbonylamino)-1-piperidylcarbonyl group, (2-, 3-, or 4-)(N-methyl-N-benzoylamino)-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(1-, 2-, 3-, or 4-)piperidyl]-1-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)[(1-, 2-, 3-, or 4-)piperidyl)-2-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)[(1-, 2-, 3-, or 4-)piperidyl]-3-piperidylcarbonyl group, (1-, 2-, 3-, or 4-)[(1-, 2-, 3-, or 4-)piperidyl]-4-piperidylcarbonyl group, (2-, 3-, or 4-)[1-acetyl-(2-, 3-, or 4-)piperidyl]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[1-butyryl-(2-, 3-, or 4-)piperidyl]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[1-tert-butoxycarbonyl-(2-, 3-, or 4-)piperidyl]-1-piperidylcarbonyl, groups, (2-, 3-, or 4-)[1-benzoyl-(2-,3-, or 4-)piperidyl]-1-piperidylcarbonyl group, (2-, 3-, or 4-)(1-piperazinyl)-1-piperidylcarbonyl group, (2-, 3-, or 4-)[1-(3,4-dimethylpiperazinyl)]-1-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)[1-(3,4-dimethylpiperazinyl)]-2-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)[1-(3,4-dimethylpiperazinyl)]-3-piperidylcarbonyl group, (1-, 2-, 3-, or 4-)[1-(3,4-dimethylpiperazinyl)]-4-piperidylcarbonyl group, (2-, 3-, or 4-)[1-(4-methylpiperazinyl)]-1-piperidylcarbonyl group, (1-, 3-, or 4-)[1-(4-methylpiperazinyl)]-2-piperidylcarbonyl group, (1-, 2-, or 4-)[1-(4-methylpiperazinyl)]-3-piperidylcarbonyl group, (1-, 2-, or 3-)[1-(4-methylpiperazinyl)]-4-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)morpholinyl]-1-piperidylcarbonyl group, (1-, 3-, or 4-)[(2-, 3-, or 4-)morpholinyl]-2-piperidylcarbonyl group, (1-, 2-, 4-, 5-, or 6-)[(2-, 3-, or 4-)morpholinyl]-3-piperidylcarbonyl group, (1-, 2-, or 3-)[(2-, 3-, or 4-)morpholinyl]-4-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, 6-, or 7-)(4-methyl-hexahydro-1,4-diazepinyl)-1-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(4-methyl-hexahydro-1,4-diazepinyl)-2-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(4-methyl-hexahydro-1,4-diazepinyl)-3-piperidylcarbonyl group, (1-, 2-, 3-, or 4-)(4-methyl-hexahydro-1,4-diazepinyl)-4-piperidylcarbonyl group, (2-, 3-, or 4-)(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-1-piperidylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-2-piperidylcarbonyl group, (1-,2-, 3-, 4-, 5-, or 6-)(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-3-piperidylcarbonyl group, (1-, 2-, 3-, or 4-)(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-4-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-,4-, or 5-)benzo[1.3]dioxolyl]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[2-oxo-(1-, 3-, 4-, 5-, 6-, 7-, or 8-)-1,2,3,4-tetrahydroquinolyl]-1-piperidylcarbonyl group, 4-[2-oxo-(1-,3-, 4-, 5-, 6-, 7-, or 8-)-1,2,3,9-tetrahydroquinolyl]-(2-or 3-methyl)-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)pyridyl]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-,3-, or 4-)pyridyloxy]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)pyridylmethoxy]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)fluorobenzyloxy]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)chlorobenzyloxy}-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)bromobenzyloxy]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)methylbenzyloxy]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)trifluoromethoxybenzyloxy]-1-piperidylcarbonyl group, (2-, 3-, or 4-)(3,4-dichlorobenzyloxy)-1-piperidylcarbonyl group, (2-, 3-, or 4-)(3,4-dimethoxybenzyloxy)-1-piperidylcarbonyl group, (2-, 3-, or 4-)(3-chloro-4-methoxybenzyloxy)-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-,3-, or 4-)fluorophenoxy]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)chlorophenoxy]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)cyanophenoxy]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-,3-, or 4-)methoxyphenoxy]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)methylphenoxy]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)trifluoromethoxyphenoxy]-1-piperidylcarbonyl group, (2-, 3-, or 4-)phenyl-1 piperidylcarbonyl group, 4-hydroxy-(2-, 3-, or 4-)phenyl-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)chlorophenyl]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)methoxyphenyl]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)hydroxyphenoxy]-1-piperidylcarbonyl group, 4-hydroxy-(2-, 3-, or 4-)phenyl-1-piperidylcarbonyl group, 4-ethoxycarbonyl-(2-, 3-, or 4-)phenyl-1-piperidylcarbonyl group, 4-hydroxy-(2-, 3-, or 4-)[(2-, 3-, or 4-)chlorophenyl]-1-piperidylcarbonyl group, (2-, 3-, or 4-)benzyl-1-piperidylcarbonyl group, (2-, 3-, or 4-) [(2-, 3-, or 4-)chlorobenzyl]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)methylbenzyl]-1-piperidylcarbonyl group, (2-, 3-, or 4-) [(2-, 3-, or 4-)methoxybenzyl]-1-piperidylcarbonyl group, (2-, 3-, or 4-) [(2-, 3-, or 4-)trifluoromethoxybenzyl]-1-piperidylcarbonyl group, 4-hydroxy-(2-, 3-, or 4--)benzyl-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)chlorobenzoyl]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)methoxybenzoyl]-1-piperidylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)fluorobenzoyl]-1-piperidylcarbonyl group, and (2-, 3-, or 4-)[(2-, 3-, or 4-)trifluoromethoxybenzyl]-1-piperidylcarbonyl group.

Examples of the pyrrolidinylcarbonyl group that may have a substituent selected from the group consisting of a hydroxy lower alkyl group, carbamoyl group; hydroxy group, amino group (that may have a group selected from the group consisting of a lower alkyl group, lower alkanoyl group, and aroyl group thereon) morpholinyl lower alkyl group, pyrrolidinyl lower alkyl group, piperidyl lower alkyl group, piperazinyl lower alkyl group (that may have a lower alkyl group thereon as a substituent), amino lower alkyl group (that may have a lower alkyl group thereon as a substituent) and aryl oxy group (that may have on the aryl group a halogen substituted lower alkoxy group), aryloxy lower alkyl group (on the aryl group, a halogen substituted lower alkoxy group may be present) and a tetrahydroquinolyl group (on which an oxo group may be present) include a pyrrolidinylcarbonyl group that may have 1 to 3 (preferably 1) substituents, on the pyrrolidinyl group, which are selected from the group consisting of
a lower alkyl group as illustrated above having 1 to 3 hydroxy groups (a linear or branched alkyl group having 1 to 6 carbon atoms);
a carbamoyl group;
a hydroxy group;
an amino group (that may have 1 to 2 groups selected from the group consisting of a lower alkyl group as illustrated above, a lower alkanoyl group as illustrated above, and an aroyl group as illustrated above);
a morpholinyl lower alkyl group whose lower alkyl moiety is one as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a pyrrolidinyl lower alkyl group whose lower alkyl moiety is one as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a piperidyl lower alkyl group whose lower alkyl moiety is one as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a piperazinyl lower alkyl group whose lower alkyl moiety is one as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) (1 to 3 (preferably 1) lower alkyl groups as illustrated above (linear or branched alkyls group having 1 to 6 carbon atoms) may be present on the piperazinyl group, as a substituent(s));
an amino lower alkyl group whose lower alkyl moiety is one as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) (1 to 2 lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms) may be present on the amino group, as a substituent(s)), aryloxy group having an aryl moiety as illustrated above (which may have on the aryl group, 1 to 3 (preferably 1) halogen substituted lower alkoxy groups), aryloxy lower alkyl group having an aryl moiety and lower alkyl moiety as illustrated above (which may have on the aryl group, 1 to 3 (preferably 1) halogen substituted lower alkoxy groups) and a tetrahydroquinolyl group (on which a single oxo group may be present). Specific examples thereof include a (1-, 2-, or 3-)pyrrolidinylcarbonyl group, (2- or 3-)hydroxymethyl-1-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)hydroxymethyl-2-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)hydroxymethyl-3-pyrrolidinylcarbonyl group, (2- or 3-)carbamoyl-1-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)carbamoyl-2-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)carbamoyl-3-pyrrolidinylcarbonyl group, (2-or 3-)hydroxy-1-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)hydroxy-2-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)hydroxy-3-pyrrolidinylcarbonyl group, (2- or 3-)amino-1-pyrrolidinylcarbonyl group, (2- or 3-)acetamido-1-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)acetamido-2-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)acetamido-3-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)butyrylamino-3-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)(N-methyl-N-acetylamino)-3-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)(N-methyl-N-butyrylamino)-3-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)benzoylamino-3-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)(N-methyl-N-benzoylamino)-3-pyrrolidinylcarbonyl group, (2- or 3-)[(2-, 3-, or 4-)morpholinylmethyl]-1-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)[(2-, 3-, or 4-)morpholinylmethyl]-2-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)[(2-, 3-, or 4-)morpholinylmethyl]-3-pyrrolidinylcarbonyl group, (2- or 3-) [(1-, 2-, or 3-)pyrrolidinylrnethyl]-1-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-) [(1-, 2-, or 3-)pyrrolidinylmethyl]]-2-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-) [(1-, 2-, or 3-)pyrrolidinylmethyl]]-3-pyrrolidinylcarbonyl group, (2- or 3-)[(1-, 2-, 3-, or 4-)piperidylmethyl]]-1-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)[(1-, 2-, 3-, or 4-)piperidylmethyl]]-2-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)[(1-, 2-, 3-, or 4-)piperidylmethyl)]-3-pyrrolidinylcarbonyl group, (2- or 3-)(4-methyl-1-piperazinylmethyl)-1-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)(4-methyl-1-piperazinylmethyl)-2-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)(4-methyl-1-piperazinylmethyl)-3-pyrrolidinylcarbonyl group, (2- or 3-)N,N-dimethylaminomethyl-1 pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)N,N-dimethylaminomethyl-2-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)N,N-dimethylaminomethyl-3-pyrrolidinylcarbonyl group, (2- or 3-)N,N-diethylaminomethyl-1-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)N,N-diethylaminomethyl-2-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)N,N-diethylaminomethyl-3-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)(4-trifluoromethoxyphenoxymethyl)- 3-pyrrolidinylcarbonyl group, (1-, 2-, 3-, 4-, or 5-)(4-trifluoromethoxyphenoxy)-3-pyrrolidinylcarbonyl group, and (1-, 3-, 4-, 5-, 6-, 7-, or 8-) (2-oxy-1, 2, 3, 4-tetrahydroquinolyl)-3-pyrrolidinylcarbonyl group.

Examples of a piperazinylcarbonyl group that may have a substituent selected from the group consisting of a lower alkyl group, cyclo C3-C8 alkyl group, lower alkanoyl group, hydroxy lower alkyl group, lower alkoxy lower alkyl group, lower alkoxycarbonyl group, amino lower alkyl group (a lower alkyl group may be present on the amino group, as a substituent), piperidyl lower alkyl group (a lower alkyl group may be present on the piperidyl group, as a substituent), morpholinyl lower alkyl group, pyrrolidinyl lower alkyl group, 1,3-dioxolanyl lower alkyl group, tetrahydrofuryl lower alkyl group, pyridyl lower alkyl group (a phenyl group may be present on the lower alkyl group as a substituent), imidazolyl lower alkyl group, furyl lower alkyl group, pyrrolidinyl carbonyl lower alkyl group, piperidyl group that may have a lower alkyl group as a substituent, pyridyl group (a substituent selected from the group consisting of a lower alkyl group, cyano group, and halogen substituted lower alkyl group may be present on the pyridyl group, as a substituent), thieno[2,3-c]pyridyl group aryl group (on which a group selected from the group consisting of a halogen atom and a lower alkyl group may be present), aroyl group, furyl lower alkyl group, aryl lower alkoxycarbonyl group and oxo group, include a piperazinylcarbonyl group that may have 1 to 3 (preferably 1) substituents, on the piperazinyl group, which are selected from the group consisting of a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a cyclo C3-C8 alkyl group as illustrated above;
a lower alkanoyl group as illustrated above (
a linear or branched alkanoyl group having 1 to 6 carbon atoms);
a hydroxy lower alkyl group as illustrated above (preferably a linear or branched alkyl group having 1 to 6 carbon atoms with 1 to 3 hydroxy groups);
a lower alkoxy lower alkyl group as illustrated above (preferably a linear or branched alkyl group having 1 to 6 carbon atoms and 1 to 3 lower alkoxy groups as illustrated above (linear or branched alkoxy groups having 1 to 6 carbon atoms));
a lower alkoxycarbonyl group as illustrated above ;
an amino lower alkyl group whose lower alkyl moiety is one as illustrated above, preferably a linear or branched alkyl group having 1 to 6 carbon atoms (1 to 2 lower alkyl groups as illustrated above (
linear or branched alkyl groups having 1 to 6 carbon atoms) may be present on the amino group, as substituent(s));
a piperidyl lower alkyl group whose lower alkyl moiety is one as illustrated above, preferably a linear or branched alkyl group having 1 to 6 carbon atoms (1 to 3 lower alkyl groups as illustrated above ( linear or branched alkyl groups having 1 to 6 carbon atoms) may be present on the piperidyl group as a substituent(s));
a morpholinyl lower alkyl group whose alkyl moiety is one as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a pyrrolidinyl lower alkyl group whose alkyl moiety is one as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a 1,3 dioxolanyl lower alkyl group whose lower alkyl moiety is one as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms)
a tetrahydrofuryl lower alkyl group whose lower alkyl moiety is one as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a pyridyl lower alkyl group whose lower alkyl moiety is one as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) (1 to 3 phenyl groups may be present on the alkyl group, as a substituent(s));
an imidazolyl lower alkyl group, whose lower alkyl moiety is one as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a furyl lower alkyl group, whose lower alkyl moiety is one as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a pyrrolidinyl carbonyl lower alkyl group, whose lower alkyl moiety is one as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms);
a piperidyl group that may have 1 to 3 lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms); a pyridyl group (1 to 3 groups (preferably 1) selected from the group consisting of a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms), cyano group, and halogen substituted lower alkyl group as illustrated above (preferably a linear or branched alkyl group having 1 to 6 carbon atoms substituted with 1 to 7 halogen atoms) may be present on the pyridyl group): a tieno[2,3-c]pyridyl group; aryl group as illustrated above (which may have on the aryl group 1 to 3 (preferably 1) groups selected from the group consisting of a halogen atom and a lower alkyl group), aroyl group as illustrated above, furyl lower alkyl group having a lower alkyl moiety as illustrated above, aryl lower alkoxy carbonyl group having an aryl moiety and lower alkoxy carbonyl moiety as illustrated above and oxo group. Specific examples thereof include a (1-or 2-)piperazinylcarbonyl group, (2-, 3-, or 4-)methyl-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)methyl-2-piperazinylcarbonyl group, (2-, 3-, or 4-)ethyl-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)ethyl-2-piperazinylcarbonyl group, (2-, 3-, or 4-)n-propyl-1-piperazinylcarbonyl group; (1-, 2-, 3-, 4-, 5-, or 6-)n-propyl-2-piperazinylcarbonyl group, (2-, 3-, or 4-)n-butyl-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)n-butyl-2-piperazinylcarbonyl group, (2-, 3-, or 4-1[(1-ethyl-n-propyl)]-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)[(1-ethyl-n-propyl)]-2-piperazinylcarbonyl group, (2-, 3-, or 4-)isopropyl-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)isopropyl-2-piperazinylcarbonyl group, (2-, 3-, or 4-)tert-butyl-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)tert-butyl-2-piperazinylcarbonyl group, (2-, 3-, or 4-)n-hexyl-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)n-hexyl-2-piperazinylcarbonyl group, (2-, 3-, or 4-)cyclopentyl-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)cyclopentyl-2-piperazinylcarbonyl group, (2-, 3-, or 4-)cycloheptyl-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)cycloheptyl-2-piperazinylcarbonyl group, (2-, 3-, or 4-)acetyl-1-piperazinylcarbonyl group, (2-, 3-, or 4-)butyryl-1-piperazinyl carbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)acetyl-2-piperazinylcarbonyl group, (2-, 3-, or 4-)(2-hydroxyethyl)-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(2-hydroxyethyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-)(2-methoxyethyl)-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(2-methoxyethyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-)(3-methoxypropyl)-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(3-methoxypropyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-)(4-methoxybutyl)-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(4-methoxybutyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-)ethoxycarbonyl-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)ethoxycarbonyl-2-piperazinylcarbonyl group, (2-, 3-, or 4-)tert-butoxycarbonyl-1-piperazinylcarbonyl group, (1-, 2-; 3-, 4-, 5-, or 6-)tert-butoxycarbonyl-2-piperazinylcarbonyl group, (2-, 3-, or 4-)methoxycarbonyl-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)methoxycarbonyl-2-piperazinylcarbonyl group, (2-, 3-, or 4-)[3-(N,N-dimethylamino)propyl]-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)[3-(N,N-dimethylamino)propyl]-2-piperazinylcarbonyl group, (2-, 3-, or 4-) [2-(N,N-dimethylamino)ethyl]-1-pipera2inylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(2-(N,N-dimethylamino)ethyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-)(2-(1-piperidyl)ethyl)-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-) (2- (1-piperidyl) ethyl) -2-piperazinylcarbonyl group, (2-, 3-, or 4-)[(1-methyl-3-piperidyl)methyl]-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)[(1-methyl-3-piperidyl)methyl]-2-piperazinylcarbonyl group, (2-, 3-, or 4-) [(1-methyl-4-piperidyl)methyl]-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)[(1-methyl-4-piperidyl)methyl]-2-piperazinylcarbonyl group, (2-, 3-, or 4-)[2-(4-morpholinyl)ethyl]-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)[2-(4-morpholinyl)ethyl]-2-piperazinylcarbonyl group, (2-, 3-, or 4-)[2-(1-pyrrolidinyl)ethyl]-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)[2-(1-pyrrolidinyl)ethyl]-2-piperazinylcarbonyl group, (2-, 3-, or 4-)[2-(1,3-dioxolanyl)methyl]-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)[2-(1,3-dioxolanyl)methyl]-2-piperazinylcarbonyl group, (2-, 3-, or 4-){2-[2-(1,3-dioxolanyl)]ethyl}-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(-2-[2-(1,3-dioxolanyl)]ethyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-)(2-tetrahydrofurylmethyl)-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(2-tetrahydrofurylmethyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-) (2-pyridylmethyl)-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-) (2-pyridylmethyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-)(3-pyridylmethyl)-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(3-pyridylmethyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-)(4-pyridylmethyl)-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-) (4-pyridylmethyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-)[2-(4-pyridyl)ethyl]-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)[2-(4-pyridyl)ethyl]-2-piperazinylcarbonyl group, (2-, 3-, or 4-)[2-(2-pyridyl)ethyl]-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)[2-(2-pyridyl)ethyl]-2-piperazinylcarbonyl group, (2-, 3-, or 4-)[2-phenyl-2-(4-pyridyl)ethyl]-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)[2-phenyl-2-(4-pyridyl)ethyl]-2-piperazinylcarbonyl group, (2-, 3-, or 4-)[2-(1-imidazolyl)ethyl]-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-) [2-(1-imidazolyl) ethyl] -2-piperazinylcarbonyl group, (2-, 3-, or z) (3-furylmethyl)-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(3-furylmethyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-)(1-pyrrolidinylcarbonylmethyl)-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(1-pyrrolidinylcarbonylmethyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-) (1-methyl-4-piperidyl)-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(1-methyl-4-piperidyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)pyridyl]-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(2-, 3-, or 4-pyridyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-)(3-cyano-2-pyridyl)-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(3-cyano-2-pyridyl)-2-piperazinylcarbonyl group, (2-3-, or 4-){4-methyl-2-pyridyl}-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(4-methyl-2-pyridyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-) (3-methyl-2-pyridyl)-1-piperazinylcarboriyl group, (1-, 2-, 3-, 4-, 5-, or 6-) 3-methyl-2-pyridyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-)(3-trifluoromethyl-2-pyridyl)-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)(3-trifluoromethyl-2-pyridyl)-2-piperazinylcarbonyl group, (2-, 3-, or 4-) [(2-, 3-, 4-, 5-, or 6-)thieno[2,3-c]pyridyl]-1-piperazinylcarbonyl group, (1-, 2-, 3-, 4-, 5-, or 6-)[(2-, 3-, 4-, 5-, or 6-)thieno[2,3-c]pyridyl]-2-piperazinylcarbonyl group, (2-, 3-, or 4-)phenyl-1-piperazinylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)chlorophenyl]-1-piperazinylcarbonyl group, (2-, 3-, or 4-)[(2-, 3-, or 4-)methylphenyl]-1-piperazinylcarbonyl group, 3-oxo-(2- or 4-)phenyl-1-piperazinylcarbonyl group, (2-, 3-, or 4-)benzolyl-1-piperazinylcarbonyl group, (2-, 3-, or 4-)[(2- or 3-)furylcarbonyl]-1-piperazinylcarbonyl group, and (2-, 3-, or 4-)benzyloxycarbonyl-l-piperazinylcarbonyl group.

Example of a hexahydroazepinylcarbonyl group include a (1-, 2-, 3- or 4-)hexahydroazepinylcarbonyl group.

Example of a hexahydro-1,4-diazepinylcarbonyl group that may have a substituent selected from the group consisting of a lower alkyl group and a pyridyl group include a hexahydro-1,4-diazepinylcarbonyl group that may have 1 to 3, preferably 1, substituents selected from the group consisting of a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) and a pyridyl group. Specific examples thereof include a (hexahydro-1,4-diazepin-(1-,2-, 5- or 6-)yl)carbonyl group, (4-methyl-hexahydro-1,4-diazepin-1-yl)carbonyl group, and (4-(4-pyridyl)-methyl-hexahydro-1,4-diazepin-1-yl)carbonyl group.

Example of a dihydropyrrolylcarbonyl group include a 2,3-dihydropyrrolylcarbonyl group and a 2, 5-dihydropyrrolylcarbonyl group.

Examples of the dihydropyrrolylcarbonyl group that may have a lower alkyl group include a dihydropyrrolylcarbonyl group as illustrated above that may have 1 to 4, preferably 1 to 2 lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms). Specific examples thereof include a (1-, 2- or 3-)(2,5-dihydropyrrolylcarbonyl) group, 2,5-dimethyl-1-(2,5-dihydropyrrolylcarbonyl) group, and 2,5-dimethyl-1-(2,3-dihydropyrrolylcarbonyl) group.

Examples of the thiomorpholinylcarbonyl group include a (2-, 3- or 4-)thiomorpholinylcarbonyl group.

Examples of the morpholinylcarbonyl group that may have a group selected from the group consisting of a lower alkyl group, and piperidyl lower alkyl group, and aryl group include a morpholinylcarbonyl group that may have 1 to 5 groups, more preferably 1 to 2 groups selected from the group consisting of a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) (on which 1 to 3 (preferably 1) piperidyl groups may be present as substituent(s)) an aryl group as described above. Specific examples thereof include a (2-, 3- or 4-)morpholinylcarbonyl group, 2,6-dimethyl-4-morpholinylcarbonyl group, 2-(1-piperidylmethyl)-4-morpholinylcarbonyl group, and 2-phenyl-4-morpholinylcarbonyl group.

Examples of the thiazolidinylcarbonyl group include a (2-, 3-, 4- or 5-) thiazolidinylcarbonyl group.

Examples of the thiazolidinylcarbonyl group that may have an aryl group that may have a group selected from the group consisting of a lower alkoxy group and a cyano group include a thiazolidinylcarbonyl group that may have 1 to 3 (preferably 1) aryl groups that may have 1 to 3 (preferably 1) groups selected from the group consisting of a lower alkoxy group and a cyano group as illustrated above. Specific examples thereof include a (2-, 3-, 4- or 5-)thiazolidinylcarbonyl group, (2-, 4- or 5-)[(2-, 3-or 4-)methoxyphenyl]-3-thiazolidinylcarbonyl group and (2-, 4- or 5-)[(2-, 3- or 4-)cyanophenyl]-3-thiazolidinylcarbonyl group.

Examples of the azabicyclo[3.2.2]nonylcarbonyl group include a 1-azabicyclo[3.2.2]non-(2-, 3-, 5-, or 6-)ylcarbonyl group, 2-azabicyclo[3.2.2]non-(1-, 2-, 3-, 4-, 5-, 6-or 7-)ylcarbonyl group, 3-azabicyclo[3.2.2]non-(1-, 2-, 3-, or 6-)ylcarbonyl group, and 6-azabicyclo[3.2.2]non-(1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-)ylcarbonyl group.

Examples of the azabicyclo[3.2.1]octylcarbonyl group that may have a halogen substituted or unsubstituted aryloxy group include an azabicyclo[3.2.1]octylcarbonyl group that may have 1 to 2 (preferably 1) halogen substituted aryl groups as illustrated above (preferably an aryl group that may be substituted with 1 to 3, preferably 1 halogen atom), or an azabicyclo[3.2.1]octylcarbonyl group that may have 1 to 2 (preferably 1) unsubstituted aryl groups as illustrated above. Specific examples thereof include a 1-azabicyclo[3.2.1]oct-(2-, 3-, 4-, 5-, 6-, 7-, or 8-)ylcarbonyl group, 2-azabicyclo[3.2.1]oct-(1-, 2-, 3-, 4-, 5-, 6-, 7-, or 8-)ylcarbonyl group, 3-azabicyclo[3.2.1]oct-(1-, 2-, 3-, 6-, or 8-)ylcarbonyl group, 6-azabicyclo[3.2.1]oct-(1-, 2-, 3-, 4-, 5-, 6-, 7-, .or 8-)ylcarbonyl group, 8-azabicyclo[3.2.1]oct-(1-, 2-, 3-, 6-, or 8-)ylcarbonyl group, 3-(phenyloxy)-1-azabicyclo[3.2.1]oct-2-ylcarbonyl group, 3-(2-biphenyloxy)-1-azabicyclo[3.2.1]oct-3-ylcarbonyl group, 3-(1-naphthyloxy)-1-azabicyclo[3.2.1]oct-4-ylcarbonyl group, 3-(3-methylphenyloxy)-1-azabicyclo[3.2.1]oct-5-ylcarbonyl group, 3-(4-ethylphenyloxy)-1-azabicyclo[3.2.1]oct-6-ylcarbonyl group, 3-(2-n-propylphenyloxy)-1-azabicyclo[3.2.1]oct-7-ylcarbonyl group, 3-(3-n-butylphenyloxy)-1-azabicyclo[3.2.1]oct-8-ylcarbonyl group, 3-(4-n-pentylphenyloxy)-2-azabicyclo[3.2.1]oct-1-ylcarbonyl group, 3-(2-n-hexylphenyloxy)-2-azabicyclo[3.2.1]oct-2-ylcarbonyl group, 3-(3-isobutylphenyloxy)-2-azabicyclo[3.2.1]oct-3-ylcarbonyl group, 3-(4-tert-butylphenyloxy)-2-azabicyclo[3.2.1]oct-4-ylcarbonyl group, 3-(2-chlorophenyloxy)-2-azabicyclo[3.2.1]oct-5-ylcarbonyl group, 3-(3-fluorophenyloxy)-8-aza-bicyclo[3.2.1]oct-8-ylcarbonyl group, 3-(3-bromophenyloxy)-2-azabicyclo[3.2.1]oct-6-ylcarbonyl group, 3-(2-aminophenyloxy)-2-azabicyclo[3.2.1]oct-7-ylcarbonyl group, 3-(2,3-dimethylphenyloxy)-2-azabicyclo[3.2.1]oct-8-ylcarbonyl group, 3-(3,4,5-trimethylphenyloxy)-8-azabicyclo[3.2.1]oct-1-ylcarbonyl group, and 3-(2,3-diaminophenyloxy)-8-azabicyclo[3.2.1]oct-2-ylcarbonyl group.

Examples of the indolinylcarbonyl group include a (1-, 2-, 3-, 4-, 5-, 6-, or 7-)indolinylcarbonyl group.

Examples of the tetrahydropyrido[3.4-b]indolylcarbonyl group include a (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-)(2-, 3-, 4-, 9-tetrahydropyrido(3.4-b]indolylcarbonyl) group.

Examples of the piperazinyl lower alkyl group that may have a lower alkyl group on the piperazinyl group include a piperazinyl lower alkyl group whose lower alkyl moiety is a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) and 1 to 7, preferably 1 to 5, more preferably 1, lower alkyl groups as illustrated above (linear or branched alkyl groups having 1 to 6 carbon atoms) may be present on the piperazinyl group. Specific examples thereof include a (1- or 2-)piperazinylmethyl group, 2-[(1- or 2-)piperazinyl]ethyl group, 1-[(1- or 2-)piperazinyl]ethyl group, 3-[(1- or 2-)piperazinyl]propyl group, 4-[(1- or 2-)piperazinyl]butyl group, 5-[(1- or 2-)piperazinyl]pentyl group, 6-[(1- or 2-)piperazinyl]hexyl group, 1,1-di.methyl-2-[(1- or 2-)piperazinyl]ethyl group, 2-methyl-3-[(1- or 2-)piperazinyl]propyl group, 4-methyl-1-piperazinylmethyl group, 2-(4-methyl-2-piperazinyl)ethyl group, 3-(2-ethyl-1 piperazinyl)propyl group, 4-(3-n-propyl-1-piperazinyl)butyl group, 5-(4-n-butyl-1-piperazinyl)pentyl group, 6-(1-n-pentyl-2-piperazinyl)hexyl group, 2-n-hexyl-2-piperazinylmethyl group, 2-(3-isobutyl-2-piperazinyl)ethyl group, and 3-(4-tert-butyl-2-piperazinyl)propyl group.

Examples of the morpholinylcarbonyl lower alkyl group include a morpholinylcarbonyl lower alkyl group whose lower alkyl moiety is a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms). Specific examples thereof include a 2-morpholinylcarbonylmethyl group, 3-morpholinylcarbonylmethyl group, 4-morpholinylcarbonylmethyl group, 2-(2-morpholinylcarbonyl)ethyl group, 2-(3-morpholinylcarbonyl)ethyl group, 2-(4-morpholinylcarbonyl)ethyl group, 1-(2-morpholinylcarbonyl)ethyl group, 1-(3-morpholinylcarbonyl)ethyl group, 1-(4-morpholinylcarbonyl)ethyl group, 3-(2-morpholinylcarbonyl)propyl group, 3-(3-morpholinylcarbonyl)propyl group, 3-(4-morpholinylcarbonyl)propyl group, 4-(2-morpholinylcarbonyl)butyl group, 4-(3-morpholinylcarbonyl)butyl group, 4-(4-morpholinylcarbonyl)butyl group, 5-(2-morpholinylcarbonyl)pentyl group, 5-(3-morpholinylcarbonyl)pentyl group, 5-(4-morpholinylcarbonyl)pentyl group, 6-(2-morpholinylcarbonyl)hexyl group, 6-(3-morpholinylcarbonyl)hexyl group, 6-(4-morpholinylcarbonyl)hexyl group, 3-methyl-3-(2-morpholinylcarbonyl)propyl group, 3-methyl-3-(3-morpholinylcarbonyl)propyl group, 3-methyl-3-(4-morpholinylcarbonyl)propyl group, 1,1-dimethyl-2-(2-morpholinylcarbonyl)ethyl group, 1,1-dimethyl-2-(3-morpholinylcarbonyl)ethyl group, and 1,1-dimethyl-2-(4-morpholinylcarbonyl)ethyl group.

Examples of the piperazinylcarbonyl lower alkyl group that may have a lower alkyl group on the piperazinyl group include a piperazinylcarbonyl lower alkyl group whose lower alkyl moiety is a lower alkyl group as illustrated above (a linear or branched alkyl group having 1 to 6 carbon atoms) and which may have 1 to 7, preferably 1 to 5, more preferably 1, lower alkyl groups as illustrated above (a linear or branched alkyl groups having 1 to 6 carbon atoms) on the piperazinyl group. Specific examples thereof include a (1- or 2-)piperazinylcarbonylmethyl group, 2-[(1- or 2-)piperazinylcarbonyl]ethyl group, 1-[(1- or 2-)piperazinylcarbonyl]ethyl group, 3-[(1- or 2-)piperazinylcarbonyl]propyl group, 4-[(1- or 2-)piperazinylcarbonyl]butyl group, 5-[(1- or 2-)piperazinylcarbonyl]pentyl group, 6-[(1- or 2-)piperazinylcarbonyl]hexyl group, 1,1-dimethyl-2-(1-or 2-)piperazinylcarbonyl]ethyl group, 2-methyl-3-[(1-or 2-)piperazinylcarbonyl]propyl group, 4-methyl-1-piperazinylcarbonylmethyl group, 2-(4-methyl-2-piperazinylcarbonyl)ethyl group, 3-(2-ethyl-1-piperazinylcarbonyl)propyl group, 4-(3-n-propyl-1-piperazinylcarbonyl)butyl group, 5-(4-n-butyl-1-piperazinylcarbonyl)pentyl group, 6-(1-n-pentyl-2-piperazinylcarbonyl)hexyl group, 2-n-hexyl-2-piperazinylcarbonylmethyl group, 2-(3-isobutyl-2-piperazinylcarbonyl)ethyl group, and 3-(4-tert-butyl-2-piperazinylcarbonyl)propyl group.

Examples of the amino lower alkoxy group (on the amino group, a lower alkyl group may be present) include a lower alkoxy group as illustrated above (a linear or branched alkoxy group having 1 to 6 carbon atoms) having 1 to 5 (preferably 1) amino groups that may have 1 to 2 lower alkyl groups as illustrated above. Specific examples thereof include an amino methoxy group, 2-amino ethoxy group, 1-aminoethoxy group, 3-aminopropoxy group, 4-aminobutoxy group, 5-aminopentoxy group, 6-aminohexyloxy group, 1,1-dimethyl-2-aminoethoxy group, N,N-dimethylaminomethoxy group, N-methyl-N-ethylaminomethoxy group, N-methylaminomethoxy group, 2-(N-methylamino)ethoxy group, 2-(N,N-dimethylamino)ethoxy group, 2-(N,N-diethylamino)ethoxy group, 2-(N,N-diisopropylamino)ethoxy group and 3-(N,N-dimethylamino)propoxy group.

Examples of the lower alkoxy lower alkoxy group include a lower alkoxy lower alkoxy group having a lower alkoxy moiety as illustrated above. Specific examples thereof include a methoxymethoxy group, 2-methoxyethoxy group, 1-ethoxyethoxy group, 2-ethoxyethoxy group, 2-isobutoxyethoxy group, 2,2-dimethtoxyethoxy group and 2-methoxy-1-methylethoxy group.

Examples of the piperazinyl group that may have a group selected from the group consisting of an oxo group, lower alkyl group, lower alkanoyl group and lower alkoxy carbonyl group include a piperazinyl group that may have a group 1 to 3 (1 to 2) groups selected from the group consisting of an oxo group, lower alkyl group as illustrated above, lower alkanoyl group as illustrated above and lower alkoxy carbonyl group as illustrated above. Specific examples thereof include a (1- or 2-)piperazinyl group, (2-, 3- or 4-)methyl-1-piperazinyl group, (1-, 2-, 3-, 4-, 5- or 6-)ethyl-2-piperazinyl group, (2-, 3- or 4-)ethyl-1-piperazinyl group, (1-, 2-, 3-, 4-, 5- or 6-)ethyl-2-piperazinyl group, (2-, 3- or 4-)n-propyl-l-piperazinyl group, (1-, 2-, 3-, 4-, 5- or 6-)n-propyl-2-piperazinyl group, (2-, 3- or 4-)formyl-l-piperazinyl group, (2-, 3- or 4-)acetyl-l-piperazinyl group, (2-, 3- or 4-)propionyl-1-piperazinyl group, (1-, 2-, 3-, 4-, 5- or 6-)propionyl-2-piperazinyl group, (2-, 3- or 4-)butyryl-1-piperazinyl group, (1-, 2-, 3-, 4-, 5- or 6-)butyryl-2-piperazinyl group, (2-, 3- or 4-)methoxycarbonyl-1-piperazinyl group, (2-, 3- or 4-)ethoxycarbonyl-1-piperazinyl group, (2-, 3- or 4-)tert-butoxycarbonyl-1-piperazinyl group, (2- or 3-)oxo-1-piperazinyl group, 2-oxo-(3-, 4-,S- or 6-)acetyl-1-piperazinyl group, 2-oxo-(3-, 4-, 5- or 6-)butyryl-1-piperazinyl group, 2-oxo-(3-, 4-, 5- or 6-)methoxycarbonyl-1-piperazinyl group and 2-oxo-(3-, 4-, 5- or 6-)methoxycarbonyl-1-piperazinyl group.

Examples of the 1,3,8-triazaspiro[4.5]decanylcarbonyl group that may have a group selected from the group consisting of an oxo group and an aryl group include a 1,3,8-triazaspiro[4.5]decanylcarbonyl group that may have 1 to 3 (1 to 2) groups selected from the group consisting of an oxo group and an aryl group as illustrated above. Specific examples thereof include a 1,3,8-triazaspiro[4.5]decanyl-(1, 2, 3, 4 or 8-)ylcarbonyl group, 1-phenyl-1,3,8-triazaspiro[4.5]decanyl-8-ylcarbonyl group and 1-phenyl-4-oxo-1,3,8-triazaspiro[4.5]decanyl-8-ylcarbonyl group.

Examples of the tetrahydropyridyl group included a (1-, 2-, 3-, 4-, 5- or 6-)-1,2,3,4-tetrahydropyridyl group and (1-, 2-, 3-, 4-, 5- or 6-)-1,2,3,6-tetrahydropyridyl group.

Examples of the tetrahydropyridylcarbonyl group that may have a pyridyl group include a tetrahydropyridylcarbonyl group as illustrated above that may have 1 to 3 (preferably 1) pyridyl groups. Specific examples thereof include a (2-, 3- or - 4)pyridyl-1,2,3,6-tetrahydropyridyl-1-ylcarbonyl group.

Examples of the imidazolidinylcarbonyl group that may have a thioxo group include an imidazolidinylcarbonyl group that may have 1 to 2 (preferably 1) thioxo groups. Specific examples thereof include a 2-thioxo-1-imidazolidinylcarbonyl group.

Examples of the tetrahydronaphthyl group include a (1- or 2-)-1,2,3,4-tetrahydronaphthyl group.

Examples of the saturated or unsaturated heteromonocyclic group having 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, oxygen atom and sulfur atom include a heteromonocyclic groups represented by (1) to (9) below.

1. (1) a saturated 3 to 8 (preferably 5 to 6) membered heteromonocyclic group having 1 to 4 (preferably 1 to 2) nitrogen atoms (for example, pyrrolidinyl group, imidazolidinyl group, piperidyl group, hexahydropyrimidinyl group, piperazinyl group, azepanyl group and azocanyl group);
2. (2) an unsaturated 3 to 8 (preferably 5 to 6) membered heteromonocyclic group having 1 to 4 (preferably 1 to 3) nitrogen atoms, for example, a pyrrolyl group, dihydropyrrolyl group such as 1H-2,5-dihydropyrolyl group, imidazolyl group (such as 1H-imidazolyl group), dihydroimidazolyl group (such as 1H-2,3-dihydroimidazolyl group), triazolyl group (such as 9H-1,2,4-trizaolyl group, 1H-1,2,3-trizaolyl group, and 2H-1,2,3-trizaolyl group), dihydrotriazolyl group (such as 1H-4,5-dihydro-1,2,4-triazolyl group), pyrazolyl group, pyridyl group, dihydropyridyl group (such as 1,2-dihydropyridyl group), pyrimidinyl group, dihydropyrimidinyl group (such as 1,6-dihydropyrimidinyl group), pyrazinyl group, dihydropyrazinyl group (such as 1,2-dihydropyrazinyl), pyridazinyl group, and tetrazolyl group (such as 1H-tetrazolyl group and 2H-tetrazolyl group);
3. (3) an unsaturated 3 to 8 (preferably 5 to 6) membered heteromonocyclic group having 1 to 2 (preferably 1) oxygen atoms and 1 to 3 (preferably 1 to 2) nitrogen atoms, for example, an oxazolyl group, isoxazolyl group, oxadiazolyl group (such as 1,2,4-oxadiazolyl group, 1,3,4-oxadiazolyl group and 1,2,5-oxadiazolyl group) and a saturated 3 to 8 (preferably 5 to 6) membered heteromonocyclic group having 1 to 2 (preferably 1) oxygen atoms and 1 to 3 (preferably 1 to 2) nitrogen atoms, for example an oxazolidinyl group, isoxazolidinyl group and morpholinyl group;
4. (4) an unsaturated 3 to 8 (preferably 5) membered heteromonocyclic group having 1 to 2 sulfur atoms and 1 to 3 nitrogen atoms, for example, a thiazolyl group, dihydrothiazolyl group (such as 2,3-dihydrothiazolyl group), isothiazolyl group, thiadiazolyl group (such as, 1,2,3-thiadiazolyl group, 1,2,4-thiadiazolyl group, 1,3,4-thiadiazolyl group, and 1,2,5-thiadiazolyl group) and dihydrothiazinyl group.
5. (5) a saturated 3 to 8 (preferably 5 to 6) membered heteromonocyclic group having 1 to 2 sulfur atoms and 1 to 3 nitrogen atoms, for example, a thiazolidinyl group;
6. (6) a saturated 3 to 8 (preferably 5 to 6) membered heteromonocyclic group having 1 to 2 oxygen atom, for example, a tetrahydrofuryl group and a tetrahydropyranyl group;
7. (7) an unsaturated 3 to 8 (preferably 5 to 6) membered heteromonocyclic group having 1 to 2 oxygen atoms, for example, a pyranyl group (such as 2H-pyranyl group);
8. (8) a saturated 3 to 8 (preferably 5 to 6) membered heteromonocyclic group having 1 to 2 sulfur atoms, for example, a tetrahydrothiofuryl group and a tetrahydrothiopyranyl group; and
9. (9) an unsaturated 3 to 8 (preferably 5 to 6) membered heteromonocyclic group having 1 to 2 sulfur atoms, for example, a thienyl group and a thiopyranyl group (such as 2H-thiopyranyl).

Of them, mention may be preferably made of a saturated or unsaturated heteromonocyclic group having a 1 to 2 hetero atoms selected from a nitrogen atom, oxygen atom and sulfur atom and selected from the group consisting of a pyrrolidinyl group, piperidyl group, pyrazolyl group, pyridyl group, pyrimidinyl group, pyrazinyl group, isoxazolyl group, thiazolyl group, pyranyl group and thienyl group; and further preferably made of a saturated or unsaturated heteromonocyclic group having a 1 to 2 nitrogen atoms and selected from the group a pyrrolidinyl group, piperidyl group, pyrazolyl group, pyridyl group, pyrimidinyl group and thiazolyl group.

Examples of the tetrahydroquinoxalinyl group include a (1-, 2-, 5- or 6-)-1,2,3,4-tetrahydroquinoxalinyl group and (1-, 2-, 5- or 6-)-5,6,7,8-tetrahydroquinoxalinyl group.

Examples of the tetrahydroquinazolinyl group include a (1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-)-1,2,3,4-tetrahydroquinazolinyl group and (1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-)-5,6,7,8-tetrahydroquinazolinyl group.

Examples of the dihydroquinazolinyl group include a (1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-) -3, 4-dihydroquinazolinyl group and (1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-)-1,2-dihydroquinazolinyl group.

Examples of the dihydrobenzimidazolyl group include a (1-, 2-, 4- or 5-)-2.3-dihydro-1H-benzimidazolyl group.

Examples of the tetrahydrobenzazepinyl group include a (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-)-2,3,4,5-tetrahydro-1H-benzo[b]azepinyl group and (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-)-2,3,4,5-tetrahydro-1H-benzo[c]azepinyl group.

Examples of the tetrahydrobenzodiazepinyl group include a (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-)-2,3,4,5-tetrahydro-1H-benzo[b][1.4]diazepinyl group and (1-, 2-, 3-, 4- 5-, 6-, 7-, 8- or 9-)-2,3,4,5-tetrahydro-1H-benzo[e][1.4]diazepinyl group.

Examples of the hexahydrobenzazocinyl group include a (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9-, or 10-)-1,2,3,4,5,6-tetrahydrobenzo[b]azocinyl group and (1-, 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-)-1, 2, 3, 4, 5, 6-hexahydrobenzo[c]azocinyl group.

Examples of the dihydrobenzoxazinyl group include a (2-, 3-, 4-, 5-, 6-, 7- or 8-)-3,4-dihydro-2H-benzo[b][1.4]oxazinyl group and (1-, 2-, 4-, 5-, 6-, 7- or 8-)-2,4-dihydro-1H-benzo[d][1.3]oxazinyl group.

Examples of the dihydrobenzoxazolyl group include a (2-, 3-, 4-, 5-, 6- or 7-)-2,3-dihydrobenzoxazolyl group.

Examples of the benzisoxazolyl group include a (3-, 4-, 5-, 6- or 7-)-benzo[d]-isoxazolyl group and (3-, 4-, 5-, 6- or 7-)-benzo[c]-isoxazolyl group.

Examples of the benzoxadiazolyl group include a (4- or 5-)-benzo[c][1.2.5]oxadiazolyl group.

Examples of the tetrahydrobenzoxazepinyl group include a (2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-)-2,3,4,5-tetrahydrobenzo[b][1.4]oxazepinyl group, (1-, 3-, 4-, 5-, 6-, 7-, 8- or 9-)-1,3,4,5-tetrahydrobenzo[e][1.3]oxazepinyl group and (2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-)-2,3,4,5-tetrahydrobenzo[f] [1.4]oxazepinyl group.

Examples of the dihydrobenzothiazinyl group include a (2-, 3-, 4-, 5-, 6-, 7- or 8-)-3,4-dihydro-2H-benzo[b] [1.4]thiazinyl group and (2-, 3-, 4-, 5-, 6-, 7- or 8-)-3,4-dihydro-2H-benzo[e][1.3]thiazinyl group.

Examples of the benzoxathiolyl group include a (2-, 4-, 5-, 6- or 7-)-benzo[d][1.3]oxathiolyl group, (3-, 4-, 5-, 6- or 7-)-3H-benzo[c][1.2]oxathiolyl group and,(3-, 4-, 5-, 6- or 7-)-3H-benzo[d][1.2]oxathiolyl group.

Examples of the dihydrobenzofuryl group include a (2-, 3-, 4-, 5-, 6- or 7-)-2,3-dihydrobenzofuryl group.

A heterocyclic compound (hereinafter referred to as a compound (1)) represented by the general formula (1) can be produced by various kinds of methods, for example, a method shown in the following reaction formula-1 or reaction formula 2. wherein R¹, R² and A are the same as defined above; and X¹ is a halogen atom or a group mediating the same substitution reaction as in a halogen atom.

Examples of the group mediating the same substitution reaction as in a halogen atom include a lower alkanesulfonyloxy group, arylsulfonyloxy group, and aralkylsulfonyloxy group.

A halogen atom represented by X¹ in the general formula (2) is a fluorine atom, chlorine atom, bromine atom and iodine atom.

Specific examples of the lower alkanesulfonyloxy group represented by X¹ include a linear or branched alkanesulfonyloxy group having 1 to 6 carbon atoms such as a methanesulfonyloxy group ethanesulfonyloxy group, isopropanesulfonyloxy group, n-propanesulfonyloxy group, n-butanesulfonyloxy group, tert-butanesulfonyloxy group, n-pentanesulfonyloxy group, and n-hexanesulfonyloxy group.

Specific examples of the arylsulfonyloxy group represented by X¹ include a phenylsulfonyloxy group and naphthylsulfonyloxy group that may have 1 to 3 substituents selected from the group consisting of a linear or branched alkyl group having 1 to 6 carbon atoms, a linear or branched alkoxy group having 1 to 6 carbon atoms, a nitro group, and a halogen atom, on the phenyl ring. Specific examples of the phenylsulfonyloxy group that may have a substituent include a phenylsulfonyloxy group, 4-methylphenylsulfonyloxy group, 2-methylphenylsulfonyloxy group, 4-nitrophenylsulfonyloxy group, 4-methoxyphenylsulfonyloxy group, 2-nitrophenylsulfonyloxy group, and 3-chlorophenylsulfonyloxy group. Specific examples of the naphthylsulfonyloxy group include α-naphthylsulfonyloxy group and β-naphthylsulfonyloxy group.

Examples of the aralkylsulfonyloxy group represented by X¹ include a linear or branched alkylsulfonyloxy group having 1 to 6 carbon atoms and substituted with a phenyl group; and a linear or branched alkylsulfonyloxy group having 1 to 6 carbon atoms and substituted with a naphthyl group; both of which may have 1 to 3 substituents selected from the group consisting of a linear or branched alkyl group having 1 to 6 carbon atoms, a linear or branched alkoxy group having 1 to 6 carbon atoms, a nitro group and a halogen atom, on the phenyl ring.
Specific examples of the alkylsulfonyloxy group substituted with a phenyl group as mentioned above include a benzylsulfonyloxy group, 2-phenylethylsulfonyloxy group, 4-phenylbutylsulfonyloxy group, 2-methylbenzylsulfonyloxy group, 4-methoxybenzylsulfonyloxy group, 4-nitrobenzylsulfonyloxy group, and 3-chlorobenzylsulfonyloxy group. Specific examples of the alkylsulfonyloxy group substituted with a naphthyl group include an α-naphthylmethylsulfonyloxy group and β-naphthylmethylsulfonyloxy group.

The compound (1) can be produced by reacting a compound (hereinafter referred to as a compound (2)) represented by the general formula (2) and a compound (hereinafter referred to as a compound (3)) represented by the general formula (3).

This reaction is generally performed in a conventional solvent that may not negatively affect the reaction, such as water; an alcohol based solvent such as methanol, ethanol, isopropanol, n-butanol, trifluoroethanol, and ethylene glycol; a ketone based solvent such as acetone and methylethyl ketone; an ether based solvent such as tetrahydrofuran, dioxane, diethyl ether, and diglyme; an ester based solvent such as methyl acetate and ethyl acetate; a non-proton polar solvent such as acetonitrile, N,N-dimethylformamide, and dimethylsulfoxide; a halogenated hydrocarbon based solvent such as methylene chloride and ethylene chloride; or other organic solvents. Furthermore, the reaction can be performed in a solution mixture of these conventional solvents. The reaction is generally performed in the presence of an inorganic base such as an alkali metal (e.g., sodium and potassium), an alkaline metal hydrogen carbonate (e.g., lithium hydrogen carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate), alkali metal hydroxide (e.g., lithium hydroxide, sodium hydroxide, potassium hydroxide, and cesium hydroxide), alkali metal carbonate (e.g., lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate), alkali metal lower alkoxide (e.g., sodium methoxide and sodium ethoxide), and a hydride (e.g., sodium hydride and potassium hydride); or in the presence of an organic base such as a trialkylamine (e.g., trimethylamine, triethylamine, N-ethyl diisopropylamine), pyridine, quinoline, piperidine, imidazole, picoline, dimethylaminopyridine, dimethylaniline, N-methylmorpholine, 1,5-diazabicyclo[4.3.0]non-5-ene (DEN), 1,4-diazabicyclo[2.2.2]octane (DABCO), and 1,8-diazabicyclo[5.4.0]undecene-7 (DBU). When these bases take liquid form, they can be used as solvents.

These basic compounds may be used alone or in a mixture of two types or more.

A basic compound may be used in a molar amount, which is generally 0.5 to 10 times, preferably 0.5 to 6 times as large as that of the compound (2).

The reaction mentioned above may be performed, if necessary, with the addition of an alkaline metal iodide serving as an accelerator, such as potassium iodide and sodium iodide.

The ratio of a compound (2) to a compound (3) used in the reaction formula-1 may be at least about 0.5 times mole, preferably about 0.5-5 times by mole.

The reaction temperature is not particularly limited and may be generally performed under cool or heating conditions and preferably performed at a temperature from near room temperature to about 150°C for 1 to 30 hours.

The compound (2) serving as a starting material for a compound according to the present invention include a novel compound and can be produced by various methods, for example, a method represented by the following reaction formula-3.

The compound (3) serving as a starting material for a compound according to the present invention is a known compound or a compound that can be easily produced from a known compound.

A salt of a compound (2) in place of the compound (2) and a salt of a compound (3) in place of the compound (3) may be used. The salts of compounds (2) and (3) include acid-addition salts. These acid addition salts may be prepared by reacting a pharmaceutically acceptable acid with a compound (2) or (3). Examples of the acid used herein include inorganic acids such as sulfuric acid, nitric acid, hydrochloric acid, phosphoric acid, and hydrobromic acid; sulfonic acids such as p-toluene sulfonic acid, methane sulfonic acid, and ethane sulfonic acid; and organic acids such as acetic acid, oxalic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid, succinic acid, and benzoic acid.

Of the compounds (2), a compound having an acidic group can easily produce a salt by reacting with a pharmaceutically acceptable basic compound. Examples of such a basic compound include metal hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide, and calcium hydroxide; alkali metal carbonates or bicarbonates such as sodium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; and alkali metal alcoholates such as sodium methylate and potassium ethylate. wherein R¹, R² and A are the same as defined above; and X² is a hydroxy group, halogen atom or a group mediating the same substitution reaction as in a halogen atom.

Examples of the halogen atom represented by X² and the group mediating the same substitution reaction as in a halogen atom in connection with the general formula (4) are the same as mentioned above. The compound (1) can be produced by reacting a compound (hereinafter referred to as a compound (4)) represented by the general formula (4) and a compound (hereinafter referred to as a "compound (5)") represented by the general formula (5).

The reaction can be performed under the similar conditions as in reaction formula-1.

In the case of a compound (4) in which X² is a hydroxy group, the reaction can be performed in an appropriate solvent in the presence of an appropriate condensing agent.

This reaction is generally performed in a conventional solvent that may not negatively affect the reaction, such as water; an alcohol based solvent such as methanol, ethanol, isopropanol, n-butanol, trifluoroethanol, and ethylene glycol; a ketone based solvent such as acetone and methylethyl ketone; an ether based solvent such as tetrahydrofuran, dioxane, diethyl ether, and diglyme; an ester based solvent such as methyl acetate and ethyl acetate; a non-proton polar solvent such as acetonitrile, N,N-dimethylformamide, and dimethylsulfoxide; a halogenated hydrocarbon based solvent such as methylene chloride and ethylene chloride; or other organic solvents. Furthermore, as a solvent to be used herein, a solution mixture of these conventional solvents may be mentioned.

As the condensing agent, a mixture of an azocarboxylate such as diethyl azodicarboxylate and a phosphine compound such as triphenylphosphine may be mentioned.

The amount of the condensing agent used herein is generally at least equimolar, preferably equimolar to twice as large as that of a compound (4).

The ratio of a compound (4) to a compound (5) used in the reaction formula-2 may be generally at least equimole preferably about 2 times by mole.

The reaction temperature is not particularly limited and may generally be performed under cool or heating conditions, and preferably performed at a temperature from 0°C to about 150°C for 1 to 10 hours.

The compound (4) serving as a starting material for a compound according to the present invention is a known compound or a compound that can be easily produced from a known compound.

The compound (5) serving as a starting material for a compound according to the present invention include a novel compound and a compound that can be produced by various methods, for example, a method represented by the following reaction formula-4 or -5.

A salt of a compound (4) in place of the compound (4) and a salt of a compound (5) in place of the compound (5) may be used. As a preferable salt of a compound (4), the same salt as shown in a compound (2) may be mentioned. As a preferable salt of a compound (5), the same salt as shown in a compound (3) may be mentioned. wherein R¹, X¹ and A are the same as defined above; and X³ is a halogen atom or a group mediating the same substitution reaction as in a halogen atom.

Examples of the halogen atom represented by X³ and the group mediating the same substitution reaction as in a halogen atom in connection with the general formula (7) are the same as mentioned above.

The compound (2) can be produced by reacting a compound (hereinafter referred to as a compound (6)) represented by the general formula (6) and a compound (hereinafter referred to as a compound (7)) represented by the general formula (7).

The reaction can be performed under the similar conditions as in reaction formula-1.

The compounds (6) and (7) serving as starting materials for a compound according to the present invention are known compounds or compounds that can be easily produced from known compounds.

In place of a compound (6), a salt of the compound (6) may be used. As a preferable salt of a compound (6), the same salt as shown in a compound (2) may be mentioned. wherein R² and A are the same as defined above; and X⁴ is a halogen atom or a group mediating the same substitution reaction as in a halogen atom.

Examples of the halogen atom represented by X⁴ and the group mediating the same substitution reaction as in a halogen atom in connection with the general formula (8) are the same as mentioned above.

The compound (5) can be produced by reacting a compound (3) and a compound (hereinafter referred to as a compound (8)) represented by the general formula (8) .

The reaction can be performed under the similar conditions as in reaction formula-1.

The compound (8) serving as a starting material for a compound according to the present invention is a known compound or a compound that can be easily produced from a known compound.

In place of a compound (3), a salt of the compound (3) may be used. As a preferable salt of a compound (3), the same salts as above may be mentioned. wherein R² and A are the same as defined above; R⁴ is a lower alkanoyl group; and X⁴ is a halogen atom or a group mediating the same substitution reaction as in a halogen atom.

Examples of the lower alkanoyl group represented by R⁴ in the general formulas (9) and (10) are the same as mentioned above.

Furthermore, examples of the halogen atom represented by X⁴ and the group mediating the same substitution reaction as in a halogen atom in connection with the general formula (9) are the same as mentioned above.

A compound (hereinafter referred to as a compound (10)) represented by the general formula (10) can be produced by reacting a compound (3) and a compound (9).

The reaction can be performed under the similar conditions as in reaction formula-1.

The compound (9) serving as a starting material for a compound according to the present invention is a known compound or a compound that can be easily produced from a known compound.

In place of a compound (3), a salt of the compound (3) may be used. As a preferable salt of a compound (3), the same salts as above may be mentioned.

Subsequently, the compound (10) is subjected to a reaction for removing an acyl group to produce a compound (5).

As a preferable method of the reaction, a conventional reaction such as hydrolysis may be mentioned. The hydrolysis reaction may be preferably performed in the presence of a base or an acid including Lewis acid. Examples of the preferable base include inorganic salts such as an alkali metal (e.g., sodium and potassium), an alkaline metal hydrogen carbonate (e.g., lithium hydrogen carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate), an alkali metal hydroxide (e.g., lithium hydroxide, sodium hydroxide, potassium hydroxide, and cesium hydroxide), an alkali metal carbonate (e.g., lithium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate), an alkali metal lower alkoxide (e.g., sodium methoxide and sodium ethoxide), and hydrides (e.g., sodium hydride and potassium hydride); and organic bases such as a trialkylamine (e.g., trimethylamine, triethylamine, and N-ethyl diisopropylamine), pyridine, quinoline, piperidine, imidazole, picoline, dimethylaminopyridine, dimethylaniline, N-methylmorpholine, DBN, DABCO, and DBU. As a preferable acid, mention can be made of organic acids (such as formic acid, acetic acid, propionic acid, trichloroacetic acid, trifluoroacetic acid) and inorganic acids (such as hydrochloric acid, hydrobromic acid, sulfuric acid, hydrogen chloride, and hydrogen bromide). The removal reaction using a Lewis acid such as a trihaloacetic acid (e.g., trichloroacetic acid and trifluoroacetic acid) may be preferably performed in the presence of a cation-trapping agent (e.g., anisole and phenol).

This reaction is generally performed in a conventional solvent that may not negatively affect the reaction, such as water; an alcohol based solvent such as methanol, ethanol, isopropanol, n-butanol, trifluoroethanol, and ethylene glycol; a ketone based solvent such as acetone and methylethyl ketone; an ether based solvent such as tetrahydrofuran, dioxane, diethyl ether, and diglyme; an ester based solvent such as methyl acetate and ethyl acetate; a non-proton polar solvent such as acetonitrile, N,N-dimethylformamide, and dimethylsulfoxide; a halogenated hydrocarbon based solvent such as methylene chloride and ethylene chloride; or other organic solvents. Furthermore, the reaction may be performed in a solution mixture of these conventional solvents. Of them, ethanol is preferable. The reaction temperature is not particularly limited and may generally be performed under cool or heating conditions, and preferably performed at near room temperature to near a boiling point of the solvent to be used for 0.5 to 75 hours.

In place of -a compound (10), a salt of the compound (10) may be used. As a preferable salt of a compound (10), the same salt as shown in a compound (3) may be mentioned.

Furthermore, a compound (hereinafter referred to as a compound (5a)) where A of the compound (5) represents -CH₂A"- where A" represents-a C1 to C5 alkylene group can be produced by a method represented by the following reaction formula-6. wherein R² is the same as defined above; and R³ is a lower alkoxy group. A" represents a C1 to C5 alkylene group. The lower alkoxy group represented by R³ in the general formula (11) is the same as defined above.

Examples of the C1 to C5 alkylene group represented by A" in the general formulas (11) and (5a) include a linear or branched alkylene group having 1 to 5 carbon atoms such as methylene, ethylene, methyl methylene, trimethylene, tetramethylene, 1-methyl trimethylene, 2-methyl trimethylene, 3-methyl tetramethylene, pentamethylene, and 2,2-dimethyl trimethylene.

The compound (5a) can be produced by subjecting a compound (hereinafter referred to as a compound (11)) represented by the general formula (11) to a reducing reaction.

The reaction can be performed by the method shown in Reference Example 6 or a similar method thereof. The reaction also can be performed by a conventional method using a reducing agent.

As a preferable reducing agent, mention may be made of a hydride (such as lithium aluminum hydride, sodium borohydride, lithium borohydride, diborane, and sodium cyanoborohydride).

This reaction is generally performed in a conventional solvent that may not negatively affect the reaction, such as an alcohol based solvent such as methanol, ethanol, isopropanol, n-butanol, trifluoroethanol, and ethylene glycol; a ketone based solvent such as acetone and methylethyl ketone; an ether based solvent such as tetrahydrofuran, dioxane, diethyl ether, and diglyme; an ester based solvent such as methyl acetate and ethyl acetate; a non-proton polar solvent such as acetonitrile, N,N-dimethylformamide, and dimethylsulfoxide; a halogenated hydrocarbon based solvent such as methylene chloride and ethylene chloride; or other organic solvents. Furthermore, the reaction may be performed in a solution mixture of these conventional solvents. The reaction temperature is not particularly limited and may generally be performed under cool or heating conditions, and preferably performed at near room temperature to near a boiling point of the solvent to be used for 0.5 to 75 hours.

The compound (11) serving as a starting material for a compound according to the present invention is a known compound or a compound that can be easily produced from a known compound.

In place of a compound (11), a salt of the compound (11) may be used. As a preferable salt of a compound (11), the same salt as shown in a compound (2) may be mentioned.

Furthermore, a compound (hereinafter referred to as a compound (11a)) where A" of the compound (11) represents "-(CH₂)₂-" can be produced by a method represented by the following reaction formula-7. where R² and R³ are the same as defined above.

The compound (11a) can be produced by reacting a compound (3) and a compound (hereinafter referred to as a compound (12)) represented by the general formula (12).

The reaction can be performed by the method shown in Reference Example 5 or a similar method thereof. This reaction is generally performed in a conventional solvent that may not negatively affect the reaction, such as water, an alcohol based solvent such as methanol, ethanol, isopropanol, n-butanol, trifluoroethanol, and ethylene glycol; a ketone based solvent such as acetone and methylethyl ketone; an ether based solvent such as tetrahydrofuran, dioxane, diethyl ether, and diglyme; an ester based solvent such as methyl acetate and ethyl acetate; a non-proton polar solvent such as acetonitrile, N,N-dimethylformamide, and dimethylsulfoxide; a halogenated hydrocarbon based solvent such as methylene chloride and ethylene chloride; or other organic solvents. Furthermore, the reaction may be performed in a solution mixture of these conventional solvents. The reaction temperature is not particularly limited and may generally be performed under cool or heating conditions, and preferably performed at near room temperature to near a boiling point of the solvent to be used for 0.5 to 75 hours.

The compound (12) serving as a starting material for a compound according to the present invention is a known compound or a compound that can be easily produced from a known compound.

A salt of a compound (3) in place of the compound (3) and a salt of a compound (12) in place of the compound (12) may be used. As a preferable salt of a compound (3), the same salt as shown above may be mentioned. As a preferable salt of a compound (12), the same salt as shown in a compound (2) may be mentioned.

The object compound obtained by each of the above reaction formula may form a suitable salt. Such suitable salts include the preferable salts of compound (1) exemplified below.

The preferable salts of compound (1) are pharmacologically acceptable salts and examples include metal salts such as alkali metal salts (for example, sodium salt potassium salt, etc.), alkaline earth metal salts (for example, calcium salt, magnesium salt, etc.), salts of inorganic bases such as ammonium salt, alkaline metal carbonates (for example, lithium carbonate, potassium carbonate, sodium carbonate, cesium carbonate, etc.), alkaline metal hydrogen carbonates (for example, lithium hydrogen carbonate, sodium hydrogen carbonate, potassium bicarbonate, etc.), alkali metal hydroxides (for example, lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, etc.); for example, salts of organic bases such as tri(lower)alkylamine (for example, trimethylamine, triethylamine, N-ethyldiisopropylamine), pyridine, quinoline, piperidine, imidazole, picoline, dimethylaminopyridine, dimethylaniline, N-(lower)alkyl-morpholine (for example, N-methylmorpholine), 1,5-diazabicyclo[4.3.0]nonene-5 (DBN), 1,8-diazabicyclo[5.4.0]undecene-7 (DBU), 1,4-diazabicyclo[2.2.2] octane (DABCO); salts of inorganic acids such as hydrochloride, hydrobromide, hydroiodide, sulfate, nitrate, phosphate; salts of organic acids such as formate, acetate, propionate, oxalate, malonate, succinate, fumarate, maleate, lactate, malate, citrate, tartrate, carbonate, picrate, methanesulfonate, ethanesulfonate, p-toluenesulfonate, glutamate.

In addition, compounds in the form in which solvate (for example, hydrate, ethanolate, etc.) was added to the starting compounds and object compound shown in each of the reaction formulae are included in each of the general formulas. As a preferable solvate, hydrate can be mentioned.

Each of the object compounds obtained by each of the general formulas can be isolated and purified from the reaction mixture by, for example, subjecting the reaction mixture to isolation operation such as filtration, concentration and extraction after cooling to separate a crude reaction product followed by conventional purification operation such as column chromatography or recrystallization.

The compound represented by the general formula (1) of the present invention naturally encompasses isomers such as geometrical isomer, stereoisomer and enantiomer.

A compound and a salt thereof represented by the general formula (1) may be used in the form of general pharmaceutical preparation. The preparation may be prepared by use of a diluent or an excipient such as a filler, extending agent, binder, humectant, disintegrator, surfactant, and lubricant. As a pharmaceutical preparation, various forms can be selected depending upon the therapeutic purpose. Typical forms thereof include a tablet, pill, powder, liquid, suspension, emulsion, granule, encapsulate, suppository, and injection (liquid, suspension).

In forming a tablet, a wide variety of types of carriers conventionally known in the art may be used. Examples of the carrier that may be used include an excipient such as lactose, saccharose, sodium chloride, glucose, urea, starch, calcium carbonate, kaolin, crystalline cellulose, and silicate; a binder such as water, ethanol, propanol, simple syrup, glucose solution, starch solution, gelatine solution, carboxymethylcellulose, shellac, methyl cellulose, potassium phosphate, and polyvinylpyrrolidine; a disintegrator such as dried starch, sodium alginate, powdered agar, powdered laminaran, sodium hydrogen carbonate, calcium carbonate, polyoxyethylene sorbitan fatty acid ester, sodium lauryl sulfate, stearic acid monoglyceride, starch, and lactose; a disintegration suppressant such as saccharose, stearin, cocoa butter, and hydrogenated oil; a sorbefacient such as quaternary ammonium base and sodium lauryl sulfate; a humectant such as glycerin and starch; an adsorbing agent such as starch, lactose, kaolin, bentonite, and colloidal silica; and a lubricant such as refined talc, stearate, powdered boric acid, and polyethylene glycol. Furthermore, if necessary, a tablet may be coated with a general film. Examples of such a coated tablet include a sugar-coated tablet, gelatine encapsulated tablet, enteric-coated tablet, film coated tablet or double-layer tablet, and multi-layer tablet.

In forming a pill, a wide variety of types of carriers conventionally known in the art may be used. Examples of the carrier that may be used include an excipient such as glucose, lactose, starch, cacao butter, hardened vegetable oil, kaolin and talc; a binder such as powdered gum Arabic, powdered tragacanth, gelatine and ethanol; and a disintegrator such as laminaran and agar.

In forming a suppository, a wide variety of types of carriers conventionally known in the art may be used. Examples of the carrier that may be used include polyethylene glycol, cacao butter, higher alcohol, esters of a higher alcohol, gelatine, and semisynthetic glyceride.

A capsule is usually prepared by mixing an active ingredient compound with a carrier as illustrated above in accordance with a conventional method and filling the mixture in a hard gelatine capsule or a soft capsule.

In preparing an injection, a liquid agent, emulsion and suspension are preferably sterilized and isotonic with blood. When they are prepared into an injection, any diluent can be used as long as it is conventionally used as a diluent in the art. Examples of the diluent that may be used include water, ethyl alcohol, macrogol, propylene glycol, ethoxylated isostearyl alcohol, polyoxylated isostearyl alcohol, polyoxyethylene sorbitan fatty acid esters.

Note that, in this case, a pharmaceutical preparation may contain a salt, glucose or glycerin in a sufficient amount to prepare an isotonic solution. Alternatively, a general auxiliary solubilizer, buffer, soothing agent may be added. Furthermore, a pigment, preservative, aroma, flavor, sweetening agent and other medicinal substances may be added to a pharmaceutical preparation, if necessary.

The amount of a compound of the general formula (1) and a salt thereof to be contained in a pharmaceutical preparation according to the present invent is not particularly limited and appropriately selected from the wide range; however generally about 1 to 70 wt%, preferably about 1 to 30 wt% in a preparation composition.

A method of administrating a pharmaceutical preparation according to the present invention is not limited and administered by a method in accordance with the form of a preparation, the age, gender and other conditions of a patient, and severity of a disease. For example, in the case of a tablet, pill, liquid agent, suspension, emulsion, granule and capsule, it is perorally administrated. In addition, in the case of an injection, it is intravenously administered by itself or by mixing with a general replenisher such as glucose and amino acids, and, if necessary, it is solely administered intramuscularly, intracutaneously, subcutaneously or intraperitoneally. In the case of a suppository, it is administered into the rectum.

The dose of a pharmaceutical preparation according to the present invention is appropriately selected depending upon the dosage regimen (direction for use), age, gender and other conditions of a patient, and severity of a disease, etc.; however, the dose of an active ingredient compound may be generally and preferably set at about 0.1 to 10 mg/weight (kg) per day. It is desirable that an active ingredient compound be contained in the range of about 1 to 200 mg per dosage unit of a preparation.

A compound according to the present invention has a D₂ receptor partial agonist effect, 5-HT_2A receptor antagonist effect and serotonin uptake inhibitory effect.

The D₂ receptor partial agonist effect refers to an action which decelerates dopaminergic (DA) neurotransmission when it is enhanced, whereas accelerates dopaminergic (DA) neurotransmission when it is lowered. In this manner, the D₂ receptor partial agonist acts as a dopamine system stabilizer, which stabilizes DA neurotransmission into a normal state. By virtue of this effect, the compound of the present invention produces an excellent clinical improvement effect on symptoms caused by abnormal DA neurotransmission (acceleration or deceleration) without developing side effects. As the excellent clinical improvement effect, mention may be made of, effects of improving positive and negative symptoms, cognitive impairment and depressive symptom (see Michio Toru, Psychiatry, Vol. 46, page 855-864 (2004); Tetsuro Kikuchi and Hirose Takeshi, Brain Science, vol. 25, page 579-583 (2004); and Harrison, T. S. and Perry, C.M.: Drugs 64: 1715-1736, 2004).

5-HT_2A receptor antagonist effect refers to an action which reduces extrapyramidal side effects and develops a superior clinical response and more specifically effectively works for improving negative symptoms, cognitive impairment, depressive symptom, and insomnia (see Jun Ishigooka and Ken Inada: Japanese Journal of Clinical Psychopharmacology, vol. 4, page 1653-1664 (2001); Mitsukuni Murasaki: Japanese Journal of Clinical Psychopharmacology, vol. 1, page 5-22 (1998), and Meltzer, H. Y. et al.: Prog. Neuro-Psychopharmacol. Biol. Psychiatry 27: 1159-1172, 2003).

The serotonin uptake inhibitory effect is, for example, effective in improving depressive symptoms (see Mitsukuni Murasaki: Japanese Journal of Clinical Psychopharmacology, vol. 1, page 5-22 (1998)).

The compound of the present invention is excellent in all these three effects or significantly excellent in one or two effects of them.

In addition, some of the compounds according to the present invention has an α₁ receptor antagonist effect in addition to the effects mentioned above. The α₁ receptor antagonist effect is effective in improving positive symptoms of schizophrenia (see Svensson, T. H.: Prog. Neuro-Psychopharmacol. Biol. Psychiatry 27: 1145-1158, 2003)

Therefore, a compound of the present invention has a wide treatment spectrum for schizophrenia and other central nervous system disorder and possesses a superior clinical response.

Accordingly, a compound of the present invention is extremely effective for improving various kinds of disorders of the central nervous system such as schizophrenia; refractory, intractable or chronic schizophrenia; emotional disturbance; psychotic disorder; mood disorder; bipolar disorder (for example, bipolar Type-I disorder and bipolar Type-II disorder); depression, endogenous depression, major depression; melancholy and refractory depression; dysthymic disorder; cyclothymic disorder; anxiety disorder (for example, panic attack, panic disorder, agoraphobia, social phobia, obsessive-compulsive disorder, post-traumatic stress disorder, generalized anxiety disorder, and acute stress disorder); somatoform disorder (for example, hysteria, somatization disorder, conversion disorder, pain disorder, and hypochondriasis), factitious disorder; dissociative disorder; sexual disorder (for example, sexual dysfunction, sexual desire disorder, sexual arousal disorder, and erectile dysfunction); eating disorder (for example, anorexia nervosa and bulimia nervosa); sleep disorder; adjustment disorder; substance-related disorder (for example, alcohol abuse; alcohol intoxication; drug addiction, stimulant intoxication, and narcotism); anhedonia (for example, iatrogenic anhedonia, anhedonia of a psychic or mental cause, anhedonia associated with depression, and anhedonia associated with schizophrenia); delirium; cognitive impairment; cognitive impairment associated with Alzheimer's disease, Parkinson's disease and other neurodegenerative diseases; cognitive impairment caused by Alzheimer's disease; Parkinson's disease and associated neurodegenerative diseases; cognitive impairment of schizophrenia; cognitive impairment caused by refractory, intractable or chronic schizophrenia; vomiting; motion sickness; obesity; migraine; pain (ache); mental retardation; autism disorder (autism); Tourette's disorder; tic disorder; attention-deficit/hyperactivity disorder; conduct disorder; and Down's syndrome.

Furthermore, a compound of the present invention has few side effects, and excellent in tolerability and safety.

The starting compounds used in each of the above reaction formula may be suitable salt, the object compound obtained by each of the reaction may form a suitable salt. Such suitable salts include the preferable salts of compound (1) exemplified below.

The preferable salts of compound (1) aren pharmacologically acceptable salts and examples include metal salts such as alkali metal salts (for example, sodium salt potassium salt, etc.), alkaline earth metal salts (for example, calcium salt, magnesium salt, etc.), salts of inorganic bases such as ammonium salt, alkaline metal carbonates (for example, lithium carbonate, potassium carbonate, sodium carbonate, cesium carbonate, etc.), alkaline metal hydrogen carbonates (for example, lithium hydrogen carbonate, sodium hydrogen carbonate, potassium bicarbonate, etc.), alkali metal hydroxides (for example, lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, etc.); for example, salts of organic bases such as tri(lower)alkylamine (for example, trimethylamine, triethylamine, N-ethyldiisopropylamine), pyridine, quinoline, piperidine, imidazole, picoline, dimethylaminopyridine, dimethylaniline, N-(lower)alkyl-morpholine (for example, N-methylmorpholine), 1,5-diazabicyclo[4.3.0]nonene-5 (DBN), 1,8-diazabicyclo[5.4.0]undecene-7 (DBU), 1,4-diazabicyclo[2.2.2] octane (DABCO); salts of inorganic acids such as hydrochloride, hydrobromide, hydroiodide, sulfate, nitrate, phosphate; salts of organic acids such as formate, acetate, propionate, oxalate, malonate, succinate, fumarate, maleate, lactate, malate, citrate, tartrate, carbonate, picrate, methanesulfonate, ethanesulfonate, p-toluenesulfonate, glutamate.

In addition, compounds in the form in which solvate (for example, hydrate, ethanolate, etc.) was added to the starting compounds and object compound shown in each of the reaction formulae are included in each of the general formulas. As a preferable solvate, hydrate can be mentioned.

Each of the object compounds obtained by each of the general formulas can be isolated and purified from the reaction mixture by, for example, subjecting the reaction mixture to isolation operation such as filtration, concentration and extraction after cooling to separate a crude reaction product followed by conventional purification operation such as column chromatography or recrystallization.

The compound represented by the general formula (1) of the present invention naturally encompasses isomers such as geometrical isomer, stereoisomer and enantiomer.

The compound of the general formula (1) and a salt thereof can be used in a common form of pharmaceutical preparation. The pharmaceutical preparation is prepared by using usually used diluent or excipient such as filler, extending agent, binder, humectant, disintegrating agent, surfactant and lubricant. As for this pharmaceutical preparation, various forms can be selected depending on the purpose of treatment, and typical examples include a tablet, pill, powder, solution, suspension, emulsion, granule, capsule, suppository, and injection (solution, suspension).

For shaping in tablet form, various materials conventionally well known as carrier in the art can be widely used. As examples, excipient such as lactose, saccharose, sodium chloride, glucose, urea, starch, calcium carbonate, kaolin, crystalline cellulose, silicate; binder such as water, ethanol, propanol, simple syrup, glucose solution, starch liquid, gelatine solution, carboxymethylcellulose, shellac, methylcellulose, potassium phosphate, polyvinylpyrrolidone; disintegrating agent such as dried starch, sodium alginate, agar powder, laminaran powder, sodium hydrogen carbonate, calcium carbonate, polyoxyethylene sorbitan fatty acid ester, sodium lauryl sulfate, stearic acid monoglyceride, starch, lactose; disintegration preventing agent such as saccharose, stearin, cacao butter, hydrogenated oil; sorbefacient such as quaternary ammonium base, sodium lauryl sulfate; moisturizing agent such as glycerine, starch; absorbing agent such as starch, lactose, kaolin, bentonite, colloidal silica; lubricant such as purified talc, stearate, borate powder, polyethylene glycol can be used, for example. Furthermore, the tablet may be a tablet provided with conventional coating as required, for example, sugar-coated tablet, gelatine encapsulated tablet, enteric coating tablet, film coated tablet or double tablet, multilayer tablet.

For shaping in pill form, various materials conventionally well known as carrier in the art can be widely used. As examples, excipient such as glucose, lactose, starch, cacao butter, hydrogenated vegetable oil, kaolin, talc; binder such as powdered gum arabic, powdered tragacanth, gelatine, ethanol; disintegrating agent such as laminaran, agar can be used, for example.

For shaping in suppository form, various materials conventionally well known as carrier can be widely used. Examples thereof include polyethylene glycol, cacao butter, higher alcohol, esters of higher alcohol, gelatine, semisynthesized glyceride, for example.

A capsule is usually prepared according to a conventional method by mixing active ingredient compounds with various carrier exemplified above and filling them into a hard gelatin capsule, a soft capsule or the like.

When prepared as injection liquid, it is preferable that solution, emulsion and suspension are sterilized and isotonic to the blood and for forming in these modes, any of those conventionally used in the art as diluent can be used, and, for example, water, ethyl alcohol, macrogol, propylene glycol, ethoxylated isostearyl alcohol, polyoxylated isostearyl alcohol, polyoxyethylene sorbitan fatty acid ester, etc. can be used.

The pharmaceutical preparation may contain common salt, glucose or glycerine in an amount sufficient to prepare an isotonic solution in this case, and conventional solubilizer, buffer, soothing agent may be also added. Pigment, preservative, aromatic, flavor, sweetening and other pharmaceuticals may be further contained as required.

The amount of a compound of the general formula (1) or a salt thereof to be contained in the pharmaceutical preparation of the present invention is not particularly limited but usually about 1 to 70% by weight in the preparation composition is suitable and preferably about 1 to 30% by weight.

There is not limitation in particular in the way of administration of the pharmaceutical preparation of the present invention and may be administered by a method in accordance with specific form of the preparation, age, sex and the other conditions of a patient, severity of disease, etc. For example, in the case of tablet, pill, solution, suspension, emulsion, granule and capsule, it is orally administered. In the case of injection, it is intravenously administered alone or in a mixture with conventional replacement fluid such as glucose and amino acids, and if necessary, and the preparation alone may be also administered intramuscularly, intracutaneously, subcutaneously or interperitoneally. It is administered in rectum in the case of suppository.

Applied dose of the pharmaceutical preparation of the present invention is appropriately selected in accordance with dosage regimen, age, sex and the other conditions of a patient, severity of disease, etc., but it is suitable that the amount of the active ingredient compound is usually about 0.1 to 10 mg per 1 kg of body weight per day. In addition, it is desirable that the active ingredient compound is contained in the preparation of a dosage unit form in the range of about 1 to 200 mg.

The compound of the present invention has D₂ receptor partial agonist effect, 5-HT_2A receptor antagonist effect and serotonin uptake inhibitory effect (or serotonin uptake inhibitory effect).

The D₂ receptor partial agonist effect suppresses dopaminergic (DA) neurotransmission when it is enhanced, and accelerates the DA neurotransmission when it is lowered and thus has a function to stabilize the DA neurotransmission to a normal state (dopamine system stabilizer). According to this function, excellent clinically improving effect on the conditions based on the DA abnormal neurotransmission (enhancement and lowering), for example, improving effect on positive and negative symptoms, improving effect on cognitive impairment, improving effect on depressive symptom, etc. are developed without developing side effects (See Michio Toru: Seishin-Igaku (Psychiatry), Vol. 46, pp. 855-864 (2004), Tetsuro Kikuchi and Tsuyoshi Hirose: Nou-no-Kagaku (Brain Science), Vol. 25, pp. 579-583 (2003) and Harrison, T.S. and Perry, C.M.: Drugs 64: 1715-1736, 2004).

5-HT_2A receptor antagonist effect reduces extrapyramidal side effects, develops superior clinical effects, and is effective for improvement of negative symptoms, improvement of cognitive impairment, improvement of depression condition, improvement of insomnia, for example (See Jun Ishigooka and Ken Inada: Rinsho-Seishin-Yakuri (Japanese Journal of Clinical Psychopharmacology), Vol. 4, pp. 1653-1664 (2001), Mitsukuni Murasaki: Rinsho-Seishin-Yakuri (Japanese Journal of Clinical Psychopharmacology), Vol. 1, pp. 5-22 (1998), Puller, I.A. et al., Eur. J. Pharmacol., 407:39-46, 2000, and Meltzer, H.Y. et al, Prog. Neuro-Psychopharmacol. Biol. Psychiatry 27: 1159-1172, 2003).

Serotonin uptake inhibitory effect (or serotonin reuptake inhibitory effect) is effective for improving depressive symptoms, for example (See Mitsukuni Murasaki: Rinsho-Seishin-Yakuri (Japanese Journal of Clinical Psychopharmacology), Vol. 1, pp. 5-22 (1998)).

The compounds of the present invention are excellent in all of these three effects, or remarkably excellent in one or two of these effects.

In addition, some of the compounds of the present invention have α₁ receptor antagonist effect in addition to the above-described effects. The α₁ receptor antagonist effect is effective for improving positive symptoms of schizophrenia (See Svensson, T.H.: Prog. Neuro-Psychopharmacol. Biol. Psychiatry 27: 1145-1158, 2003).

Therefore, the compounds of the present invention have a wide treatment spectrum for and excellent clinical effect on schizophrenia and other central nervous system disorders.

Accordingly, the compounds of the present invention are extremely effective for the treatment or prevention of central nervous system disorders including the group consisting of schizophrenia; refractory, intractable or chronic schizophrenia; emotional disturbance: psychotic disorder; mood disorder; bipolar disorder (for example, bipolar I type disorder and bipolar II type disorder); depression; endogenous depression; major depression; melancholy and refractory depression; dysthymic disorder; cyclothymic disorder; anxiety disorder (for example, panic attack, panic disorder, agoraphobia, social phobia, obsessive-compulsive disorder, post-traumatic stress disorder, generalized anxiety disorder, acute stress disorder, etc.); somatoform disorder (for example, hysteria, somatization disorder, conversion disorder, pain disorder, hypochondriasis, etc.); factitious disorder; dissociative disorder; sexual disorder (for example, sexual dysfunction, sexual desire disorder, sexual arousal disorder, erectile dysfunction, etc.); eating disorder (for example, anorexia nervosa, bulimia nervosa, etc.); sleep disorder; adjustment disorder; substance-related disorder (for example, alcohol abuse, alcohol intoxication, drug addiction, stimulant intoxication, narcotism, etc.); anhedonia (for example, iatrogenic anhedonia, anhedonia of a psychic or mental cause, anhedonia associated with depression, anhedonia associated with schizophrenia, etc.); delirium; cognitive impairment; cognitive impairment associated with Alzheimer's disease, Parkinson's disease, and other neurodegenerative diseases; cognitive impairment caused by Alzheimer's disease, Parkinson's disease and associated neurodegenerative diseases; cognitive impairment of schizophrenia; cognitive impairment caused by refractory, intractable or chronic schizophrenia; vomiting; motion sickness; obesity; migraine; pain (ache); mental retardation; autism disorder (autism); Tourette's disorder; tic disorder; attention-deficit/hyperactivity disorder; conduct disorder; and Down's syndrome.

Furthermore, the compounds of the present invention have little or no side effects and they are excellent in safety and tolerability.

A preferable example of a desired compound (1) is as follows: where R² represents a hydrogen atom or a lower alkyl group;
A represents a lower alkylene group or a lower alkenylene group (preferably a lower alkylene group); and
R¹ represents a

• (II) an aromatic group selected from a phenyl group, naphthyl group, dihydroindenyl group and tetrahydronaphthyl group (more preferably a phenyl group);

1. (1) a lower alkyl group,
2. (2) a lower alkenyl group,
3. (3) a halogen substituted lower alkyl group,
4. (4) a lower alkoxy group,
5. (5) a phenoxy group,
6. (6) a lower alkylthio group,
7. (7) a halogen substituted lower alkoxy group,
8. (8) a hydroxy group,
9. (9) a phenyl lower alkoxy group,
10. (10) a hydroxy lower alkyl group,
11. (11) a lower alkoxy lower alkyl group,
12. (12) a halogen atom,
13. (13) a cyano group,
14. (14) a phenyl aryl group,
15. (15) a nitro group,
16. (16) an amino group,
17. (17) an amino group having 1 to 2 groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group, a lower alkylsulfonyl group, a carbamoyl group, a lower alkyl carbamoyl group, an amino lower alkanoyl group, a lower alkanoylamino lower alkanoyl group and a lower alkoxycarbonylamino lower alkanoyl group as a substituent(s) (more preferably an N-lower alkylamino group, N,N-di lower alkylamino group, N-lower alkanoylamino group, N-lower alkoxycarbonylamino group, N-lower alkylsulfonylamino group, N-lower alkyl-N-lower alkanoylamino group, N-lower alkyl-N-lower alkoxycarbonylamino group, N-[carbamoyl]amino group, N-[N-lower alkylcarbamoyl]amino group, N-[N,N-di lower alkylcarbamoyl]amino group, N-[amino lower alkanoyl]amino group, N-[[N-lower alkanoylamino] lower alkanoyl]amino group, or N-[[N-lower alkoxycarbonylamino] lower alkanoyl]amino group),
18. (18) a lower alkanoyl group,
19. (19) a phenyl sulfonyl group that may have a lower alkyl group on the phenyl group (more preferably a lower alkylphenylsulfonyl group),
20. (20) a carboxy group,
21. (21) a lower alkoxycarbonyl group,
22. (22) a carboxy lower alkyl group,
23. (23) a lower alkoxycarbonyl lower alkyl group,
24. (24) a lower alkanoylamino lower alkanoyl group,
25. (25) a carboxy lower alkenyl group,
26. (26) a lower alkoxycarbonyl lower alkenyl group,
27. (27) a carbamoyl lower alkenyl group that may have as a substituent(s) 1 to 2 groups selected from the group consisting of a lower alkyl group and a lower alkyl group substituted with 1 to 3 halogen atoms (more preferably a carbamoyl lower alkenyl group, an N-lower alkylcarbamoyl lower alkenyl group, an N,N-di lower alkylcarbamoyl lower alkenyl group or N-[a lower alkyl substituted with 1 to 3 halogen atoms] carbamoyl lower alkenyl),
28. (28) a carbamoyl group that may have 1 to 2 groups selected from the group consisting of the groups (i) to (lxxviii) below as a substituent(s):
    1. (i) a lower alkyl group,
    2. (ii) a lower alkoxy group,
    3. (iii) a hydroxy lower alkyl group,
    4. (iv) a lower alkoxy lower alkyl group,
    5. (v) an phenyloxy lower alkyl group,
    6. (vi) a halogen substituted lower alkyl group,
    7. (vii) an amino lower alkyl group that may have 1 to 2 groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a benzoyl group and a carbamoyl group (more preferably an N,N-di lower alkylamino lower alkyl group, an N-lower alkanoylamino lower alkyl group, an N-lower alkyl-N-lower alkanoylamino lower alkyl group, an N-lower alkyl-N-benzoylamino lower alkyl group, or an N-carbamoylamino lower alkyl group)
    8. (viii) a cyclo C3-C8 alkyl group that may have 1 to 3 groups (preferably 1 to 2 groups, and more preferably 1 group) selected from the group consisting of a lower alkyl group, a hydroxy group, a lower alkoxycarbonyl group and a phenyl lower alkoxy group as a substituent,
    9. (ix) a cyclo C3-C8 alkyl substituted lower alkyl group,
    10. (x) a lower-alkenyl group,
    11. (xi) a lower alkyl group having 1 to 2 carbamoyl groups which may have 1 to 2 groups (preferably 1 group) selected from the group consisting of a lower alkyl group, a phenyl group that may have a single lower alkyl group and a phenyl group that may have a single lower alkoxy group as a substituent(s) (more preferably a carbamoyl lower alkyl group, a dicarbamoyl lower alkyl group, an N-lower alkylcarbamoyl lower alkyl group, an N,N-di lower alkylcarbamoyl lower alkyl group, an N-[lower alkylphenyl]carbamoyl lower alkyl group, or an N-[lower alkoxyphenyl]carbamoyl lower alkyl group),
    12. (xii) a lower alkyl group having 1 to 2 lower alkoxycarbonyl groups,
    13. (xiii) a furyl lower alkyl group (that may have 1 to 2 lower alkyl groups as a substituent(s) on the furyl group),
    14. (xiv) a tetrahydrofuryl lower alkyl group,
    15. (xv) a 1,3-dioxolanyl lower alkyl group,
    16. (xvi) a tetrahydropyranyl lower alkyl group,
    17. (xvii) a pyrrolyl lower alkyl group (that may have 1 to 2 lower alkyl groups as a substituent(s) on the pyrrolyl group),
    18. (xviii) a dihydropyrazolyl lower alkyl group that may have a single oxo group,
    19. (xix) a pyrazolyl lower alkyl group (that may have 1 to 3 lower alkyl groups as a substituent(s) on the pyrazolyl group),
    20. (xx) an imidazolyl lower alkyl group,
    21. (xxi) a pyridyl lower alkyl group,
    22. (xxii) a pyrazinyl lower alkyl group (that may have 1 to 3 (preferably 1) lower alkyl groups as a substituent on the pyrazinyl group),
    23. (xxiii) a pyrrolidinyl lower alkyl group (that may have 1 to 2 groups selected from the group consisting of an oxo group and a lower alkyl group as a substituent(s) on the pyrrolidinyl group),
    24. (xxiv) a piperidyl lower alkyl group (that may have 1 to 3 groups (preferably 1 group) selected from the group consisting of a benzoyl group and a lower alkanoyl group as a substituent(s) on the piperidyl group),
    25. (xxv) a piperazinyl lower alkyl group (that may have 1 to 3 (preferably 1) lower alkyl groups as a substituent(s) on the piperazinyl group),
    26. (xxvi) a morpholinyl lower alkyl group,
    27. (xxvii) a thienyl lower alkyl group (that may have 1 to 3 (preferably 1) lower alkyl group as a substituent(s) on the thienyl group),
    28. (xxviii) a thiazolyl lower alkyl group,
    29. (xxix) a dihydrobenzofuryl lower alkyl group,
    30. (xxx) a benzopyranyl lower alkyl group (that may have a single oxo group as a substituent on the benzopyranyl group),
    31. (xxxi) a benzimidazolyl lower alkyl group,
    32. (xxxii) an indolyl lower alkyl group that may have 1 to 3 (preferably 1) lower alkoxycarbonyl groups on the lower alkyl group),
    33. (xxxiii) an imidazolyl lower alkyl group that has 1 to 3 substituents (preferably 1 substituent) selected from the group consisting of a carbamoyl group and a lower alkoxycarbonyl group on the lower alkyl group,
    34. (xxxiv) a pyridyl group that may have 1 to 3 groups (preferably 1 group) selected from the group consisting of a lower alkyl group, a lower alkoxy group and a lower alkylthio lower alkyl group as a substituent(s),
    35. (xxxv) a pyrrolidinyl group that may have 1 to 3 groups (preferably 1 group) selected from the group consisting of a lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group and a benzoyl group as a substituent,
    36. (xxxvi) a piperidyl group that may have 1 to 3 groups (preferably 1 group) selected from the group consisting of a lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group and a benzoyl group that may have 1 to 3 groups (preferably 1 group) selected from the group consisting of a lower alkyl group and a halogen atom on the phenyl group,
    37. (xxxvii) a tetrahydrofuryl group that may have a single oxo group,
    38. (xxxviii) a hexahydroazepinyl group that may have a single oxo group,
    39. (xxxix) a pyrazolyl group that may have 1 to 3 groups (preferably 1 group) selected from the group consisting of a lower alkyl group, a phenyl group and a furyl group as a substituent,
    40. (xl) a thiazolyl group,
    41. (xli) a thiadiazolyl group that may have 1 to 3 (preferably 1) lower alkyl groups,
    42. (xlii) an isoxazolyl group that may have 1 to 3 (preferably 1 to 2) lower alkyl groups,
    43. (xliii) an indazolyl group,
    44. (xliv) an indolyl group,
    45. (xlv) a tetrahydrobenzothiazolyl group,
    46. (xlvi) a tetrahydroquinolyl group that may have 1 to 3 (preferably 1 to 2) groups selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen atom and an oxo group as a substituent,
    47. (xlvii) a quinolyl group that may have 1 to 3 (preferably 1) lower alkyl groups,
    48. (xlviii) a benzodioxolyl lower alkyl group,
    49. (xlix) a phenyl group or naphthyl group that may have 1 to 3 groups as a substituent(s), selected from the group consisting of
        a halogen atom; a lower alkyl group; a lower alkoxy group; a halogen substituted lower alkyl group; a halogen substituted lower alkoxy group; a lower alkenyl group; an amino group that may have 1 to 2 groups selected from the group consisting of a lower alkanoyl group, a lower alkyl sulfonyl group, a lower alkyl group and an aryl group; a sulfamoyl group; a lower alkylthio group; a lower alkanoyl group; a lower alkoxycarbonyl group; a pyrrolyl group; a lower alkynyl group; a cyano group; a nitro group; a phenyloxy group; a phenyl lower alkoxy group; a hydroxy group; a hydroxy lower alkyl group; a carbamoyl group that may have a group selected from the group consisting of a lower alkyl group and a phenyl group; a pyrazolyl group; a pyrrolidinyl group that may have a single oxo group; an oxazolyl group; an imidazolyl group that may have 1 to 3 (preferably 1 to 2) lower alkyl groups; a dihydrofuryl group that may have a single oxo group; a thiazolidinyl lower alkyl group that may have two oxo groups; an imidazolyl lower alkanoyl group and a piperidinylcarbonyl group,
    50. (l) a cyano lower alkyl group,
    51. (li) a dihydroquinolyl group that may have 1 to 3 (more preferably 1 to 2) groups selected from the group consisting of a lower alkyl group and an oxo group,
    52. (lii) a halogen substituted lower alkylamino group,
    53. (liii) a lower alkylthio lower alkyl group,
    54. (liv) an amidino group that may have 1 to 2 lower alkyl groups,
    55. (lv) an amidino lower alkyl group,
    56. (lvi) a lower alkenyloxy lower alkyl group,
    57. (lvii) a phenyl amino group that may have 1 to 3 substituents (more preferably 1 substituent) selected from the group consisting of a lower alkyl group, a lower alkoxy group, a halogen substituted lower alkyl group and a halogen substituted lower alkoxy group on the phenyl group,
    58. (lviii) a phenyl lower alkenyl group,
    59. (lix) a pyridylamino group that may have 1 to 3 (more preferably 1 to 2) lower alkyl groups (more preferably N-lower alkyl-N-[lower alkylpyridyl]amino group),
    60. (lx) a phenyl lower alkyl group (that may have 1 to 3 groups (more preferably 1 to 2 groups) selected from the group consisting of a halogen atom, a lower alkyl group, a halogen substituted lower alkyl group, a halogen substituted lower alkoxy group, a lower alkoxy group, a carbamoyl group and a lower alkoxycarbonyl group as a substituent on the phenyl group and/or the lower alkyl group),
    61. (lxi) a lower alkynyl group,
    62. (lxii) a phenyloxy lower alkyl group (that may have as a substituent(s) on the phenyl group 1 to 3 groups (preferably 1 group) selected from the group consisting of a lower alkoxy group, an N-lower alkoxy-N-lower alkylcarbamoyl group and an oxopyrrolidinyl group),
    63. (lxiii) an isoxazolidinyl group that may have a single oxo group,
    64. (lxiv) a dihydroindenyl group,
    65. (lxv) a phenyl lower alkoxy lower alkyl group,
    66. (lxvi) a tetrahydropyranyl group,
    67. (lxvii) an azetidinyl group that may have 1 to 3 groups (more preferably 1 group) selected from the group consisting of a lower alkanoyl group and a benzoyl group,
    68. (lxviii) an azetidinyl lower alkyl group that may have 1 to 3 groups (more preferably 1 group) selected from the group consisting of a lower alkanoyl group and a benzoyl group,
    69. (lxix) a tetrazolyl group,
    70. (lxx) an indolinyl group that may have a single oxo group,
    71. (lxxi) a triazolyl group that may have 1 to 3 groups (more preferably 1 to 2 groups) selected from the group consisting of a lower alkyl group and a lower alkylthio group,
    72. (lxxii) an imidazolyl group that may have 1 to 3 (more preferably 1) carbamoyl groups,
    73. (lxxiii) an oxazolyl group that may have 1 to 3 (more preferably 1) lower alkyl groups,
    74. (lxxiv) an isothiazolyl group that may have 1 to 3 (more preferably 1) lower alkyl groups,
    75. (lxxv) a benzimidazolyl group,
    76. (lxxvi) a dihydrobenzothiazolyl group that may have a single oxo group,
    77. (lxxvii) a thienyl group that may have 1 to 3 (more preferably 1) lower alkoxycarbonyl groups, and
    78. (lxxviii) an oxazolyl lower alkyl group that may have 1 to 3 (more preferably 1 to 2) lower alkyl groups
29. (29) an amino lower alkyl group that may have 1 to 2 groups selected from the group consisting of a lower alkyl group, a halogen substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, a phenyl group, a phenyl lower alkyl group, a benzoyl group and an amino substituted alkyl group (that may have 1 to 2 (more preferably 2) lower alkyl groups as a substituent(s) on the amino group) on the amino group,
30. (30) a lower alkyl group substituted with a single carbamoyl group that may have 1 to 2 groups selected from the group consisting of a lower alkyl group and a halogen substituted lower alkyl group,
31. (31) a thiocarbamoyl group that may have 1 to 2 (more preferably 1) lower alkyl group,
32. (32) a sulfamoyl group,
33. (33) an oxazolidinyl group that may have a single oxo group (more preferably an oxazolidinyl group substituted with a single oxo group),
34. (34) an imidazolidinyl group that may have 1 to 2 substituents selected from the group consisting of an oxo group and a lower alkyl group,
35. (35) a pyrrolidinyl group that may have a single oxo group,
36. (36) an imidazolyl group,
37. (37) a triazolyl group,
38. (38) an isoxazolyl group,
39. (39) a piperidyl group that may have 1 to 3 (more preferably 1 to 2, and still more preferably 1) substituents selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkylphenylsulfonyl group, an oxo group, a hydroxy group, and amino group that may have 1 to 2 groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group and lower alkanoylamino lower alkanoyl group (more preferably a piperidyl group that may have 1 to 3 (more preferably 1 to 2, and still more preferably 1) substituents selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkylphenylsulfonyl group, an oxo group, a hydroxy group, an amino group, an N-lower alkylamino group, an N,N-di lower alkylamino group, an N-lower alkanoylamino group, an N-lower alkyl-N-lower alkoxycarbonylamino group, an N-lower alkyl-N-lower alkanoylamino group, and an N-lower alkanoylamino lower alkanoylamino group),
40. (40) a piperidylcarbonyl group that may have 1 to 3 (more preferably 1 to 2) substituents selected from the group consisting of a lower alkyl group, a hydroxy group, a hydroxy lower alkyl group, a lower alkanoyl group, a carboxy lower alkyl group, a lower alkyl carbamoyl lower alkyl group, a carbamoyl group, a lower alkoxy group, a carboxy group, a lower alkoxycarbonyl group, an amino group (on which 1 to 2 groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxycarbonyl group and a benzoyl group may be present), a piperidyl group (on which 1 to 3 groups (more preferably 1 group) selected from the group consisting of a lower alkanoyl group, a lower alkoxycarbonyl group and a benzoyl group may be present), a piperazinyl group (on which 1 to 3 (more preferably 1 to 2) lower alkyl groups may be present as a substituent), a 1,4-dioxa-8-azaspiro[4.5]decyl group, a morpholinyl group, a hexahydro-1,4-diazepinyl group (on which a single lower alkyl group may be present as a substituent), pyridyl group, pyridyloxy group, pyridyl lower alkoxy group, tetrahydroquinolyl group (on which a single oxo group may be present), benzodioxolyl group, phenyl lower alkoxy group (that may have 1 to 3 groups (more preferably 1 to 2 groups) selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkoxy group and a halogen substituted lower alkoxy group on the phenyl group), phenyl group (on which 1 to 3 groups (preferably 1 to 2 groups) selected from the group consisting of a halogen atom, a lower alkoxy group and a hydroxy group may be present), a phenyloxy group (that may have on the phenyl group 1 to 3 groups (preferably 1 to 2 groups) selected from the group consisting of a cyano group, a halogen atom, a lower alkyl group, a lower alkoxy group and a halogen substituted lower alkyl group), 4 phenyl lower alkyl group (that may have on the phenyl group 1 to 3 groups (more preferably 1 to 2 groups) selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkoxy group and a halogen substituted lower alkyl group), and a benzoyl group (that may have on the phenyl group 1 to 3 groups (more preferably 1 to 2 groups) selected from the group consisting of a halogen atom and a lower alkoxy group),
41. (41) a pyrrolidinylcarbonyl group that may have 1 to 3 (more preferably 1) groups as a substituent, selected from the group consisting of a hydroxy lower alkyl group, a carbamoyl group, a hydroxy group, an amino group (that may have on the amino group 1 to 2 groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group and a benzoyl group), morpholinyl lower alkyl group, a pyrrolidinyl lower alkyl group, a piperidyl lower alkyl group, a piperazinyl lower alkyl group (that may have a single lower alkyl group as a substituent on the piperazinyl group), an amino lower alkyl group (that may have 1 to 2 lower alkyl groups as a substituent on the amino group), phenyloxy group (that may have 1 to 3 (more preferably 1) halogen substituted lower alkoxy groups on the phenyl group), a phenyloxy lower alkyl group (that may have 1 to 3 (more preferably 1) halogen substituted lower alkoxy groups on the phenyl group) and a tetrahydroquinolyl group (on which an oxo group may be present),
42. (42) a piperazinylcarbonyl group that may have 1 to 3 groups (more preferably 1 to 2 groups), as a substituent, selected from the group consisting of a lower alkyl group, a cyclo C3-C8 alkyl group, a lower alkanoyl group, a hydroxy lower alkyl group, a lower alkoxy lower alkyl group, a lower alkoxycarbonyl group, an amino lower alkyl group (that may have 1 to 2 lower alkyl groups as a substituent on the amino group), piperidyl lower alkyl group (that may have 1 to 2 (more preferably 1) lower alkyl groups as a substituent(s) on the piperidyl group), a morpholinyl lower alkyl group, a pyrrolidinyl lower alkyl group, a 1,3-dioxolanyl lower alkyl group, a tetrahydrofuryl lower alkyl group, a pyridyl lower alkyl group (that may have 1 to 2 (more preferably 1) phenyl groups as a substituent(s) on the lower alkyl group), an imidazolyl lower alkyl group, a furyl lower alkyl group, a pyrrolidinylcarbonyl lower alkyl group, a piperidyl group that may have 1 to 2 (more preferably 1) lower alkyl groups as a substituent(s), a pyridyl group (that may have on the pyridyl group 1 to 3 groups (more preferably 1 group) selected from the group consisting of a lower alkyl group, a cyano group and a halogen substituted lower alkyl group as a substituent), a thieno[2,3-b]pyridyl group, a phenyl group (on which 1 to 3 groups (more preferably 1 group) selected from the group consisting of a halogen atom and a lower alkyl group may be present), a benzoyl group, a furyl carbonyl group, a phenyl lower alkoxycarbonyl group and an oxo group,
43. (43) a hexahydroazepinylcarbonyl group,
44. (44) a hexahydro-1,4-diazepinylcarbonyl group that may have 1 to 3 substituents (more preferably 1 substituent) selected from the group consisting of a lower alkyl group and a pyridyl group,
45. (45) a dihydropyrrolylcarbonyl group that may have 1 to 3 (more preferably 1 to 2) lower alkyl groups,
46. (46) a thiomorpholinylcarbonyl group,
47. (47) a morpholinylcarbonyl group that may have 1 to 3 groups (more preferably 1 group) selected from the group consisting of a lower alkyl group, a piperidyl lower alkyl group and a phenyl group,
48. (48) a thiazolidinyl carbonyl group that may have 1 to 3 (more preferably 1) phenyl groups that may have 1 to 3 groups (more preferably 1 group) selected from the group consisting of a lower alkoxy group and a cyano group,
49. (49) an azabicyclo[3.2.2]nonylcarbonyl group,
50. (50) an 8-azabicyclo[3.2.1]octylcarbonyl group that may have 1 to 3 (more preferably 1) halogen substituted or unsubstituted phenyloxy groups,
51. (51) an indolinylcarbonyl group,
52. (52) a tetrahydroquinolylcarbonyl group,
53. (53) a tetrahydropyrido[3.4-b]indolylcarbonyl group,
54. (54) a morpholinyl lower alkyl group,
55. (55) a piperazinyl lower alkyl group that may have 1 to 3 (more preferably 1) lower alkyl groups on the piperazinyl group,
56. (56) a morpholinylcarbonyl lower alkyl group,
57. (57) a piperazinylcarbonyl lower alkyl group that may have 1 to 3 (more preferably 1) lower alkyl groups on the piperazinyl group,
58. (58) an oxo group,
59. (59) an amino lower alkoxy group (that may have 1 to 2 (more preferably 2) lower alkyl groups on the amino group),
60. (60) a lower alkoxy lower alkoxy group,
61. (61) a piperazinyl group that may have 1 to 3 groups (more preferably 1 to 2 groups) selected from the group consisting of an oxo group, a lower alkyl group, a lower alkanoyl group and a lower alkoxycarbonyl group (more preferably, a piperazinyl group substituted with a single oxo group, a piperazinyl group substituted with a single lower alkyl group, a piperazinyl group substituted with a single lower alkanoyl group, a piperazinyl group substituted with a single oxo group and a single lower alkanoyl group, and a piperazinyl group substituted with a single oxo group and a single lower alkoxy carbonyl group),
62. (62) a morpholinyl group,
63. (63) a 1,3,8-triazaspiro[4.5]decanylcarbonyl group that may have 1 to 3 groups (more preferably 1 to 2 groups) selected from the group consisting of an oxo group and a phenyl group,
64. (64) a tetrahydropyridylcarbonyl group that may have 1 to 3 (more preferably 1) pyridyl groups,
65. (65) an imidazolidinylcarbonyl group that may have one thioxo group, and
66. (66) a 1,4-dioxa-8-azaspiro[4.5]decanyl group.

In the general formula (1), R¹ is preferably a phenyl group. The ring of the phenyl group is preferably substituted with 1 to 3 groups selected from the group consisting of:

• (1) a lower alkyl group,
• (4) a lower alkoxy group,
• (10) a hydroxy lower alkyl group,
• (17) an amino group having 1 to 2 groups selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkoxy carbonyl group, a lower alkyl sulfonyl group, a carbamoyl group, a lower alkyl carbamoyl group, an amino lower alkanoyl group, a lower alkanoylamino lower alkanoyl group and a lower alkoxycarbonylamino lower alkanoyl group as a substituent(s),
• (21) a lower alkoxycarbonyl group,
• (28) a carbamoyl group that may have 1 to 2 substituents selected from the group consisting of the groups (i), (ii), (iv), (xii) and (xxi) below:
  • (i) a lower alkyl group,
  • (ii) a lower alkoxy group,
  • (iv) a lower alkoxy lower alkyl group,
  • (xii) a lower alkyl group having 1 to 2 lower alkylcarbonyl groups,
  • (xxi) a pyridyl lower alkyl group,
• (29) an amino lower alkyl group that may have 1 to 2 groups selected from the group consisting of a lower alkyl group, a halogen substituted lower alkyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, a phenyl group, a phenyl lower alkyl group, a benzoyl group and an amino substituted alkyl group (that may have 1 to 2 lower alkyl groups as a substituent(s) on the amino group) on the amino group,
• (30) a lower alkyl group substituted with a single carbamoyl group that may have 1 to 2 groups selected from the group consisting of a lower alkyl group and a halogen substituted lower alkyl group,
• (33) an oxazolidinyl group that may have a single oxo group,
• (34) an imidazolidinyl group that may have 1 to 2 substituents selected from the group consisting of an oxo group and a lower alkyl group,
• (35) a pyrrolidinyl group that may have a single oxo group,
• (36) an imidazolyl group,
• (39) a piperidyl group that may have a single substituent selected from the group consisting of a lower alkyl group, a lower alkanoyl group, a lower alkyl phenylsulfonyl group, an oxo group, a hydroxy group, an amino group, an N-lower alkylamino group, an N-N di-lower alkyl amino group, an N-lower alkanoylamino group, an N-lower alkyl-N-lower alkoxycarbonylamino group, an N-lower alkyl-N-lower alkanoylamino group, and an N-lower alkanoylamino lower alkanoylamino group,
• (61) a piperazinyl group that may have 1 to 2 groups selected from the group consisting of an oxo group, a lower alkyl group, a lower alkanoyl group and a lower alkoxy carbonyl group, and
• (62) a morpholinyl group.

Hereinbelow, the present invention will be further made clear with reference to Reference Examples, Examples and Pharmacological Experimental Examples and Preparation Examples.

A mixture consisting of 14.4 g of 4-bromobenzo[b]thiophene, 29.8 g of piperazine anhydride, 9.3 g of sodium t-butoxide, 0.65 g of (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP), 0.63 g of tris (dibenzylideneacetone) dipalladium (0) and 250 ml of toluene was refluxed with heating for one hour under a nitrogen atmosphere. Water was poured to the reaction solution, which was then extracted with ethyl acetate, washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane: methanol: 25% ammonia water = 100:10:1), to obtain 9.5 g of 1-benzo[b]thiophen-4-yl-piperazine in the form of yellow oil.

Then, 3.7 ml of concentrated hydrochloric acid was added to a methanol solution of 9.5 g of 1-benzo[b]thiophen-4-yl-piperazine, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the obtained residue and precipitated crystals were obtained by filtration. Recrystallization was performed from methanol to obtain 1-benzo[b]thiophen-4-yl-piperazine hydrochloride as colorless needle-like crystals.
Melting point 276-280°C
¹H-NMR (DMSO-d₆) δppm: 3.25-3.35 (8H, m), 6.94 (1H, d, J=7.6Hz), 7.30 (1H, dd, J=7.8Hz, J=7.8Hz), 7.51 (1H, d, J=5.5Hz), 7.68 (1H, d, J=8.1Hz), 7.73 (1H, d, J=5.5Hz), 9.35 (2H, brs).

The titled compound was obtained using tert-butyl 3-methylpiperazin-1-carboxylate and 4-bromobenzo[b]thiophene in the same manner as in Reference Example 1.
¹H -NMR (CDCl₃) δppm: 1.85-1.95 (3H, m , 1.50 (9H, s, 2.8-2.9 (1H, m), 3.15-3.35 (2H, m), 3.4-3.5 (1H, m), 3.5-3.65 (1H, m), 3.65-3.7 (1H, m), 3.7-3.9 (1H, m), 6.98 (1H, d, J = 7.5Hz), 7.29 (1H, dd, J = 8Hz, J=9Hz), 7.38 (1H, d, J = 5.5Hz), 7.61 (1H, d, J = 9Hz).

Trifluoroacetic acid (6 ml) was added to a solution of 1.22 g (3.7 mmol) of tert-butyl 4-benzo[b]thiophen-4-y-3-methylpiperazin-1-carboxylate in a dichloromethane solution (12 ml) and the mixture was stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure, and a 5% aqueous potassium carbonate solution was added to the residue and the resulting mixture was extracted with dichloromethane. The extraction solution with dichloromethane was dried over magnesium sulfate and thereafter concentrated under reduced pressure. To the residue obtained, concentrated hydrochloric acid (0.6 ml) and methanol (10 ml) were added and the resulting mixture was concentrated under reduced pressure. The obtained residue was subjected to recrystallization from acetonitrile to obtain 1-benzo[b]thiophen-4-yl-2-methylpiperazine dihydrochloride (0.98 g) as light brown powder.
¹H -NMR (DMSO-d₆) δppm: 0.92 (3H, d, J =6.5Hz), 2.8-3.6 (6H, m), 3.6-4.0 (1H, m), 5.3-6.8 (1H, m), 7.20 (1H, br), 7.38 (1H, dd, J = 8Hz, J=8Hz), 7.5-8.0 (3H, m), 9.4-10.1 (2H, m).

The titled compound was obtained using 2-methylpiperazine and 4-bromobenzo[b]thiophene in the same manner as in Reference Example 1.
¹H-NMR (DMSO-d₆) δppm: 1.34 (3H, d, J = 6.5Hz), 2.85-2.95 (1H, m), 3.05-3.15 (1H, m), 3.2-3.6 (6H, m), 6.97 (1H, d, J = 7.5Hz), 7.31 (1H, dd, J = 8Hz, J = 8Hz), 7.54 (1H, d, J = 5.5Hz), 7.69 (1H, d, J = 8Hz), 7.75 (1H, d, J = 5.5Hz), 9.2-9.3 (1H, m), 9.64 (1H, br).

5.05 g (19.8 mmol) of 1-benzo[b]thiophen-4-yl-piperazine hydrochloride was added to an aqueous solution of sodium hydroxide, and the mixture was extracted with dichloromethane. The extraction solution was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was dissolved in 50 ml of ethanol and ethyl acrylate (2.44 ml, 21.8 mmol) was added thereto, and then the reaction mixture was refluxed with heating for 4 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. Diisopropyl ether was added to the residue and insoluble matter precipitated was obtained by filtration, washed with diisopropyl ether, and dried to obtain ethyl 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propionate (5.26 g) as white powder.
¹H -NMR (CDCl₃) δppm: 1.28 (3H, t, J=7.0Hz), 2.50-2.63 (2H, m), 2.67-2.87 (6H, m), 3.11-3.24 (4H, m), 4.17 (2H, q, J=7.0Hz), 6.89 (1H, d, J=7.8Hz), 7.27 (1H, t, J=7.8Hz), 7.37-7.42 (2H, m), 7.55 (1H, d, J=7.8Hz).

Lithium aluminum hydride (1.18 g, 24.8 mmol) was added to a solution of 5.26 g (16.5 mmol) of ethyl 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propionate in a tetrahydrofuran (THF) solution (55 ml) under ice cooling, and the mixture was stirred at room temperature for 4 hours. To the reaction solution, water (1.2 ml), 15 % aqueous sodium hydroxide solution (1.2 ml), and water (3.6 ml) were added in this order and the mixture was stirred at room temperature. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 3:2 → ethyl acetate) and concentrated to dryness under reduced pressure to obtain 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propan-1-ol (0.23 g) as white powder.
¹H -NMR (CDCl₃) δppm: 1.75-1.85 (2H, m), 2.74 (2H, t, J=5.8 Hz), 2.75-2.85 (4H, m), 3.15-3.25 (4H, m), 3.85 (2H, t, J=5.3 Hz), 5.19 (1H, brs), 6.88 (1H, d, J=7.6 Hz), 7.27 (1H, dd, J=7.9 Hz, J=7.8 Hz), 7.39 (2H, s), 7.56 (1H, d, J=8.0 Hz).

1.0 g (3.9 mmol) of 1-benzo[b]thiophen-4-yl-piperazine hydrochloride was suspended in 20 ml of dimethylformamide (DMF), and potassium carbonate (1.3 g, 9.4 mmol) and 4-bromobutyl acetate (0.7 ml, 4.8 mmol) were added thereto. The reaction mixture was stirred at 80°C for 6 hours, cooled to room temperature, and water was added thereto, and extracted with ethyl acetate. The organic phase was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane: methanol = 30:1), and concentrated to dryness under reduced pressure to obtain 4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butyl acetate (0.72 g) as light yellow oil.
¹H -NMR (CDCl₃) δppm: 1.60-1.73 (4H, m), 2.07 (3H, s), 2.47 (2H, t, J=7.2Hz), 2.60-2.72 (4H, m), 3.17-3.22 (4H, m), 4.11 (2H, t, J=6.3Hz), 6.90 (1H, d, J=7.6Hz), 7.27 (1H, dd, J=7.6Hz, J=8.0Hz), 7.37-7.42 (2H, m), 7.55 (1H, d, J=8.0Hz).

Potassium carbonate (3.87 g, 28 mmol) was added to a solution of 7.76 g (23.3 mmol) of 4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butyl acetate in 90% methanol solution (150 ml). The solution mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution, which was then extracted with dichloromethane. The extraction solution was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (n-hexane : ethyl acetate = 2:1 → 1:1), and concentrated under reduced pressure to obtain 4-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)butan-1-ol (6.65 g) as colorless oil.
¹H -NMR (CDCl₃) δppm: 1.60-1.74 (4H, m), 2.50-2.55 (2H, m), 2.70-2.80 (4H, m), 3:20-3.30 (4H, m), 3.60-3.63 (2H, m), 6.2 (1H, brs), 6.90 (1H, d, J=7.6Hz), 7.27 (1H, dd, J=7.6Hz, J=8.0Hz), 7.39 (1H, s), 7.56 (1H, d, J=8.0Hz).

3.56 g (12.9 mmol) of 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propan-1-ol was suspended in 30 ml of dichloromethane, and carbon tetrachloride (30 ml) and triphenyl phosphine (4.06 g, 15.5 mmol) were added thereto. The mixture was refluxed with heating for 3 hours. The reaction solution was cooled to room temperature, then methanol and dichloromethane were added thereto to homogenize the mixture. Silica gel (30 g) was added to the solution, and the solvent was evaporated under reduced pressure. The obtained residue was loaded on silica gel column (300 g) and extracted with a solvent mixture of n-hexane : ethyl acetate = 2:1. The extraction solution was concentrated under reduced pressure to obtain 1-benzo[b]thiophen-4-yl-4-(3-chloropropyl)piperazine (2.36 g) as colorless oil.
¹H -NMR (CDCl₃) δppm: 1.95-2.10 (2H, m), 2.60 (2H, t, J=7.2 Hz), 2.65-2.75 (4H, m), 3.15-3.25 (4H, m), 3.65 (2H, t, J=6.6 Hz), 6.89 (1H, dd, J=7.6 Hz, J=0.7 Hz), 7.27 (1H, dd, J=7.9 Hz, J=7.8 Hz), 7.38 (1H, d, J=5.6 Hz), 7.41 (1H, d, J=5.7 Hz), 7.55 (1H, d, J=8.0 Hz).

Thionyl chloride (1.6 ml) was added dropwise to a methanol solution (20 ml) of 4-hydroxythiophene-2-carboxylic acid (1.1 g, 7.6 mmol) under ice cooling. The solution mixture was refluxed with heating for 5 hours. The reaction solution was cooled to room temperature, poured into ice water and extracted with ethyl acetate. The extraction solution with ethyl acetate was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 4:1) and concentrated/dried under reduced pressure to obtain methyl 4-hydroxythiophene-2-carboxylate (0.7 g) as white powder. ¹H-NMR (CDCl₃) δppm: 3.90 (3H, s), 5.50-6.60 (1H, br), 6.64 (1H, d, J=1.9 Hz), 7.43 (1H, d, J=1.8 Hz).

The titled compound was obtained using 6-hydroxypyrimidine-4-carboxylic acid in the same manner as in Reference Example 10.
¹H-NMR (CDCl₃) δppm: 1.29 (3H, t, J=7.0Hz), 4.29 (2H, q, J=7.0Hz), 6.87 (1H, d, J=1.0Hz), 8.27 (1H, d, J=1.0Hz), 10.54 (1H, br).

A diethyl ether solution (35 ml) of dimethyl acetylenedicarboxylate (5.0 g, 35 mmol) was cooled with a freezing medium (salt & ice). To this solution, a diethyl ether solution (15 ml) of methyl hydrazine (0.63 ml, 35 mmol) was added dropwise while maintaining the temperature at 0°C or less. After completion of dropwise addition, the solution was stirred at 0°C for one hour. The insoluble matter precipitated was obtained by filtration and washed with diethyl ether. The filter cake was heated to 130°C for 30 minutes and cooled to room temperature. Methanol was added to the cake, which was concentrated under reduced pressure. Ethyl acetate was added to the obtained residue and the residue was concentrated under reduced pressure. Ethyl acetate was added to the residue and the insoluble matter precipitated was obtained by filtration, washed with ethyl acetate, and dried to obtain methyl 5-hydroxy-1-methyl-1H-pyrazole-3-carboxylate (3.26 g) as light yellow powder.
¹H-NMR (DMSO-d₆) δppm: 3.58 (3H, s), 3.73 (3H, s), 5.77 (1H, s), 11.41 (1H, br).

Triethylamine (1.03 ml, 7.4 mmol) and isobutyl chloroformate (0.76 ml, 5.5 mmol) were added to an acetonitrile solution (12 ml) of 6-chloronicotinic acid (0.58 g, 3.6 mmol) under ice cooling and the mixture was stirred at 0°C for 30 minutes. To the solution mixture, 2,2,2-trifluoroethyl amine (0.88 ml, 11.2 mmol) was added and the mixture was stirred at room temperature for 10 minutes. Water was added to the reaction solution, which was then extracted with ethyl acetate. The extraction solution with ethyl acetate was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (n-hexane : ethyl acetate = 5:1 → 1:1). The purified product was concentrated under reduced pressure and diisopropyl ether and n-hexane were added. The insoluble matter precipitated was obtained by filtration and dried to obtain 6-chloro-N-(2,2,2-trifluoroethyl)nicotine amide (0.58 g) as light yellow powder.
¹H-NMR (CDCl₃) δppm: 4.15 (2H, dq, J=6.5Hz, 9.0Hz), 6.35 (1H, br), 7.46 (1H, dd, J=0.7Hz, J=8.5Hz), 8.11 (1H, dd, J=2.5Hz, J=8.5Hz), 8.77 (1H, dd, J=0.7Hz, J=2.5Hz).

1-hydroxybenzotriazole (0.53 g, 3.5 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (WSC) (0.67 g, 3.5 mmol) and 2,2,2-trifluoroethyl amine (0.51 ml. 6.35 mmol) were added to a dichloromethane solution (5 ml) of 4-chloropyridine-2-carboxylic acid (0.5 g, 3.17 mmol) and the mixture was stirred at room temperature for one hour. Water was added to the reaction solution, which was then extracted with ethyl acetate. The extraction solution with ethyl acetate was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 11:1 → 5:1). The purified product was concentrated to dryness under reduced pressure to obtain N-(2,2,2-trifluoroethyl)-4-chloropyridine-2-carboxamide (435 mg) as white powder. ¹H-NMR (CDCl₃) δppm: 4.13 (2H, dq, J=6.8Hz, 9.0Hz), 7.49 (1H, dd, J=2.1Hz, J=5.3Hz), 8.22 (1H, dd, J=0.4Hz, J=2.1Hz), 8.30 (1H, br), 8.49 (1H, dd, J=0.4Hz, J=5.3Hz).

1-hydroxybenzotriazole (0.56 g, 3.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (WSC) (0.7 g, 3.7 mmol) and ammonia water (28%, 0.5 ml)) were added to a dichloromethane solution (10 ml) of 2-chlorothiazole-4-carboxylic acid (0.5 g, 3.06 mmol) and the mixture was stirred at room temperature for 46 hours. Water was added to the reaction solution, which was then extracted with ethyl acetate. The extraction solution with ethyl acetate was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 3:5 → ethyl acetate). The purified product was concentrated to dryness under reduced pressure to obtain 2-chlorothiazole-4-carboxamide (475 mg) as white powder.
¹H-NMR (CDCl₃ δppm: 5.70 (1H, br), 7.01 (1H, br), 8.06 (1H, s).

The titled compound was obtained using 2-chlorothiazole-5-carboxylic acid in the same manner as in Reference Example 13.
²H-NMR (CDCl₃) δppm: 3.00 (3H, d, J=4.9Hz), 5.92 (1H, br), 7.84 (1H, br).

5% palladium carbon (1.5 g) were added to an ethanol solution (250 ml) of ethyl 2-(4-methoxy-2-nitrophenoxy)-2-methylpropionate (14.6 g, 51.6 mmol) to perform catalytic reduction at room temperature. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. Water was added to the obtained residue, which was then extracted with ethyl acetate. The extraction solution was dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 9:1). The purified product was concentrated to dryness under reduced pressure to obtain 6-methoxy-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (7.0 g) as white powder.
¹H-NMR (CDCl₃) δppm: 1.53 (6H, s), 3.78 (3H, s), 6.40 (1H, d, J=2.8Hz), 6.52 (1H, dd, J=2.8Hz, J=8.8Hz), 6.88 (1H, d, J=8.7Hz), 8.66 (1H, brs).

A dichloromethane solution (36 ml) of 2M boron tribromide was added dropwise to a dichloromethane solution of 6-methoxy-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (5.0 g, 26 mmol) under ice cooling and the mixture was stirred overnight. Water was added to the reaction solution to decompose the reagents excessively present. The reaction solution was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 2:1). The purified product was concentrated to dryness under reduced pressure to obtain 6-hydroxy-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one (4.02 g) as white powder.
¹H-NMR (DMSO-d₆) δppm: 1.34 (6H, s), 6.25-6.40 (2H, m), 6.70 (1H, d, J=8.5 Hz), 9.09 (1H, s), 10.41 (1H, brs).

The titled compound was obtained using 6-methoxy-2-methyl-4H-benzo[1,4]oxazin-3-one in the same manner as in Reference Example 18.
White powder
¹H-NMR (DMSO-d₆) δppm: 1.34 (3H, d, J=6.8 Hz), 9.46 (1H, q, J=6.8 Hz), 6.23-6.27 (1H, m), 6.33 (1H, d, J=2.7 Hz), 6.70 (1H, d, J=8.6 Hz), 9.11 (1H, s), 10.44 (1H, brs).

p-Toluenesulfonyl chloride (4.39 g, 23 mmol) was added to a pyridine solution (30 ml) of 4-(4-methoxyphenyl)piperidine (4.0 g, 21 mmol) and the mixture was stirred at room temperature overnight. Water was added to the solution mixture, which was then extracted with ethyl acetate. The organic phase was washed with hydrochloric acid and water, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 1:1). The purified product was concentrated to dryness under reduced pressure to obtain 4-(4-methoxyphenyl)-1-(toluene-4-sulfonyl)piperidine (4.8 g) as white powder. ¹H-NMR (CDCl₃) δppm: 1.60-1.90 (4H, m), 2.30-2.40 (3H, m), 2.46 (3H, s), 3.78 (3H, s), 3.90-3.95 (2H, m), 6.84 (2H, dd, J=1.9, J=6.8 Hz), 7.07 (2H, dd, J=1.9, J=6.8 Hz), 7.35 (2H, d, J=8.2 Hz), 7.68 (2H, d, J=8.2 Hz).

The titled compound was obtained using 4-(4-methoxyphenyl)-1-(toluene-4-sulfonyl)piperidine in the same manner as in Reference Example 18.
Brown powder
¹H-NMR (CDCl₃) δppm: 1.60-1.90 (4H, m), 2.30-2.50 (3H, m), 2.45 (3H, s), 3.90-3.95 (2H, m), 6.67 (1H, brs), 6.80 (2H, dd, J=1.9, J=6.8 Hz), 7.02 (2H, dd, J=1.8, J=6.9 Hz), 7.35 (2H, d, J=8.1 Hz), 7.68 (2H, d, J=8.1 Hz).

Sodium borohydride (0.28 g, 6.9 mmol) was added to a THF solution (30 ml) of 5-bromo-2-hydroxy-3-methoxybenzaldehyde (3.2 g 13.8 mmol) under ice cooling and the mixture was stirred at 0°c for 2 hours. Acetic acid was added to the reaction solution to set pH at 3. 10% hydrochloric acid was added to the reaction mixture, which was then extracted with ethyl acetate. The extracted material was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 5:1 → 1:1) and concentrated to dryness under reduced pressure to obtain 4-bromo-2-hydroxymethyl-6-methoxyphenol (3.23 g) as light yellow oil.
¹H-NMR (CDCl₃) δppm: 3.88 (3H, s), 4.71 (2H, s), 6.94 (1H, d, J=2.0Hz), 7.03 (1H, d, J=2.0Hz).

Ethyldiisopropylamine (3.01 ml, 17.1 mmol) and methoxymethylchloride (1.5 ml, 15.7 mmol) were added to a dichloromethane solution (30 ml) of 5-bromo-2-hydroxy-3-methoxybenzaldehyde (3.3 g, 14.3 mmol) under ice cooling, and the mixture was stirred at room temperature for 2 hours. The reaction solution was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 3:1 →11:9). The purified product was concentrated to dryness under reduced pressure to obtain 5-bromo-3-methoxy-2-methoxymethoxybenzaldehyde (4.2 g) as light yellow solid.
¹H-NMR (CDCl₃) δppm: 3.56 (3H, s), 3.89 (3H, s), 5.21 (2H, s), 7.23 (1H, d, J=2.5Hz), 7.56 (1H, d, J=2.5Hz), 10.39 (1H, s).

2-oxazolidinone (0.38 g, 4.36 mmol), dipalladium tris(dibenzylideneacetone) (0.17 g, 0.18 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (XANTPHOS)(0.32 g, 0.55 mmol) and cesium carbonate (1.66 g, 5.1 mmol) were added to a dioxane solution (20 ml) of 5-bromo-3-methoxy-2-methoxymethoxybenzaldehyde (1.0 g, 3.6 mmol) and the mixture was stirred at 100 °C for 24 hours under an argon atmosphere. The reaction solution was cooled to room temperature and ethyl acetate was added thereto. The mixture was filtrated by cerite. The filtrate was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 4:1 → 1:1). The purified product was concentrated under reduced pressure. Ethyl acetate and diisopropyl ether were added to the residue. The insoluble matter thus purified was obtained by filtration and dried to obtain 3-methoxy-2-methoxymethoxy-5-(2-oxo-oxazolidin-3-yl)benzaldehyde (0.5 g).as white powder.
¹H-NMR (CDCl₃) δppm: 3.57 (3H, s), 3.93 (3H, s), 4.06-4.12 (2H, m), 4.48-4.54 (2H, m), 5.21 (2H, s), 6.96 (1H, d, J=2.5Hz), 8.18 (1H, d, J=2.5Hz), 10.45 (1H, s).

3-Methoxy-2-methoxymethoxy-5-(2-oxo-oxazolidin-3-yl)benzaldehyde (0.5 g, 1.79 mmol) was dissolved in a solvent mixture of acetic acid (5 ml) and ethanol (5 ml) and 10% palladium carbon (0.05 g) was added thereto to perform catalytic reduction at 1 atm at 50°C for 4 hours. The reaction mixture was cooled to room temperature and filtrated by cerite.
The filtrate was concentrated under reduced pressure. The residue was dissolved in acetic acid (10 ml) and 10% palladium carbon (0.05 g) was added thereto to perform catalytic reduction at 1 atm at 50°C for 6 hours. The solvent was removed under reduced pressure to obtain 3-(3-methoxy-4-methoxymethoxy-5-methylphenyl)oxazolidin-2-one as a crude product, which was subjected to the next reaction as it was.
¹H-NMR (CE)Cl₃) δppm: 2.32 (3H, s), 3.56 (3H, s), 3.85 (3H, s), 3.98-4.06 (2H, m), 4.43-4.50 (2H, m), 5.05 (2H, s), 6.61 (1H, d, J=2.3Hz), 7.36 (1H, d, J=2.3Hz).

10% hydrochloric acid (5 ml) was added to a methanol solution (5 ml) of 3-(3-methoxy-4-methoxymethoxy-5-methylphenyl)oxazolidin-2-one (0.48 g, 1.79 mmol) and the mixture was stirred at 50°C for 10 minutes. Water was added to the reaction solution, which was extracted with ethyl acetate. The extracted material was dried over magnesium sulfate, and thereafter concentrated to dryness under reduced pressure to obtain 3-(4-hydroxy-3-methoxy-5-methylphenyl)oxazolidin-2-one (434 mg) as a light yellow powder.
¹H-NMR (CDCl₃) δppm: 2.26 (3H, s), 3.90 (3H, s), 4.02 (2H, dd, J=7.0Hz, J=8.5Hz), 4.46 (2H, dd, J=7.0Hz, J=8.5Hz), 5.55 (1H, br), 6.56 (1H, d, J=2.5Hz), 7.31 (1H, d, J=2.5Hz).

The titled compound was obtained using 6-bromo-8-methoxy-2,2-dimethyl-4H-benzo[1,3]dioxin and 2-pyrrolidone in the same manner as in Reference Example 25.
¹H-NMR (CDCl₃) δppm: 1.59 (6H, s), 2.09-2.21 (2H, m), 2.60 (2H, t, J=8.3Hz), 3.82 (2H, t, J=7.0Hz), 3.88 (3H, s), 4.83 (2H, s), 6.67 (1H, d, J=2.5Hz), 7.24 (1H, d, J=2.5Hz).

10% hydrochloric acid (4 ml) was added to a THF solution (7 ml) of 1-(8-methoxy-2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)pyrrolidin-2-one (0.36 g, 1.3 mmol) and the mixture was stirred at room temperature for 17 hours. Water was added to the reaction solution, which was then extracted with dichloromethane. The extracted material was dried over magnesium sulfate, concentrated under reduced pressure and purified by silica gel column chromatography (dichloromethane : methanol: = 300: 1 → 30:1). The purified product was concentrated to dryness under reduced pressure to obtain 1-(4-hydroxy-3-hydroxymethyl-5-methoxyphenyl)pyrrolidin-2-one (0.31 g) as light brown powder.
¹H-NMR (CDCl₃) δppm: 2.05-2.28 (3H, m), 2.26 (2H, t, J=7.5Hz), 3.84 (2H, t, J=7.0Hz), 3.91 (3H, s), 4.74 (2H, s), 5.90 (1H, br), 6.78 (1H, d, J=2.5Hz), 7.52 (1H, d, J=2.SHz).

The titled compound was obtained using 5-bromo-3-methoxy-2-methoxymethoxybenzaldehyde and 2-pyrrolidone in the same manner as Reference Example 25. ¹H-NMR (CDCl₃) δppm: 2.11-2.24 (2H, m), 2.63 (2H, t, J=8.3Hz), 3.56 (3H, s), 3.89 (2H, t, J=7.0Hz), 3.92 (3H, s), 5.21 (2H, s), 7.08 (1H, d, J=2.5Hz), 8.28 (1H, d, J=2.5Hz), 10.46 (1H, s).

3-methoxy-2-methoxymethoxy-5-(2-oxopyrrolidin-1-yl)benzaldehyde (0.72 g, 2.56 mmol) was dissolved in a solvent mixture of acetic acid (5 ml) and ethanol (7 ml) and 10% palladium carbon (70 mg) was added thereto to perform catalytic reduction at 50°C for 10 hours. The reaction solution was cooled to room temperature and filtrated by cerite. The filtered cake was concentrated under reduced pressure. The residue thus obtained was dissolved in dichloromethane (15 ml) and trifluoroacetic acid (2.0 ml, 25.6 mmol) and triethylsilane (2.0 ml, 12.8 mmol) were added thereto under ice cooling. The mixture was stirred at room temperature for 16 hours. The mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 5:1 → ethyl acetate). The purified product was concentrated under reduced pressure to obtain 1-(4-hydroxy-3-methoxy-5-methylphenyl)pyrrolidin-2-one (0.41 g) as light yellow oil.
¹H-NMR (CDCl₃) δppm: 2.17-2.25 (5H, m), 2.72 (2H, t, J=8.3Hz), 3.88 (2H, t, J=7.0Hz), 3.89 (3H, s), 6.66 (1H, d, J=2.5Hz), 7.15 (1H, d, J=2.5Hz).

Acetic anhydride (1.2 ml, 12 mmol) was added to a pyridine solution (4 ml) of 3,4-dihydroxy-5-methylbenzaldehyde (0.72 g, 4.7 mmol) and the mixture was stirred at 0°C for one hour. 10% hydrochloric acid was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was washed with an aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 5:1 → 3:1). The purified product was concentrated under reduced pressure to obtain 3,4-diacetoxy-5-methylbenzaldehyde (0.98 g) as light yellow oil.
¹H-NMR (CDCl₃) δppm: 2.29 (3H, s), 2.32 (3H, s), 2.35 (3H, s), 7.58 (1H, d, J=1.6Hz), 7.67 (1H, d, J=1.6Hz), 9.93 (1H, s).

The titled compound was obtained using 7-methoxymethoxy-1,4-dihydrobenzo[d][1,3]oxazin-2-one in the same manner as in Reference Example 26.
White powder
¹H-NMR (DMSO-d₆) δppm: 5.14 (2H, s), 6.35 (1H, d, J=2.2 Hz), 6.39 (1H, dd, J= 8.1, J=2.2 Hz), 6.97 (1H, d, J=8.1 Hz), 9.98 (1H, br-s).

2-aminomethyl-5-methoxyaniline (1.2 g, 7.9 mmol) and carbonyl diimidazole (1.53 g, 9.5 mmol) were added to THF (100 ml) and the mixture was stirred at room temperature overnight. The insoluble matter precipitated was obtained by filtration, washed with dichloromethane and water, dried to obtain 7-methoxy-3,4-dihydro-1H-quinazolin-2-one (1.11 g) as white powder.
¹H-NMR (DMSO-d₆) δppm: 3.68 (3H, s), 4.23 (2H, s), 6.35 (1H, d, J=2.5Hz), 6.42 (1H, dd, J=8.3Hz, J=2.5Hz), 6.96 (1H, d, J=8.3Hz), 8.90 (1H, brs).

The titled compound was obtained using 7-methoxy-3,4-dihydro-1H-quinazolin-2-one in the same manner as in Reference Example 18.
Light brown powder
¹H-NMR (DMSO-d₆) δppm: 4.18 (2H, brs), 6.75-6.85 (1H, m), 7.01 (1H, dd, J = 2.0 Hz, J=9.0Hz), 8.07 (1H, d, J = 9.0Hz), 8.87 (1H, brs), 9.48 (1H, brs), 13.21 (1H, brs).

Cesium carbonate (2.08 g, 6.4 mmol) and 1-bromo-3-chloropropane (1.6 ml) were added to a DMF solution (5 ml) of methyl 5-hydroxy-1-methyl-1H-pyrazole-3-carboxylate (0.83 g, 5.3 mmol) and the mixture was stirred at room temperature for 21 hours. Water was added to the reaction solution, which was then extracted with ethyl acetate. The organic phase was washed with water and dried over magnesium sulfate. The reaction solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 100:1 → 4:1). The purified product was concentrated to dryness under reduced pressure to obtain methyl 5-(3-chloropropoxy)-1-methyl-1H-pyrazole-3-carboxylate (1.17 g) as white solid.
¹H-NMR (CDCl₃) δppm: 2.21-2.32(2H, m), 3.72(2H, t, J=6.3Hz), 3.72(2H, s), 3.91(3H, s), 4.24(2H, t, J=5.8Hz), 6.10(1H, s).

The titled compound was obtained using 7-hydroxy-2H-1,4-benzoxazin-3(4H)-one and 1-bromo-3-chloropropane in the same manner as in Reference Example 35.
Light brown needle-like crystal (ethanol-n-hexane)
Melting point: 119-120°C

The compounds listed in the following Tables 1 to 12 were produced using appropriate starting substances in the same manners as in Reference Examples 1 to 36. Reference Exemple R1 R2 R3 R4 R5 NMR 37 -H -H -CONHC₂H₅ -H -H ¹H-NMR (CDCl₃) δppm: 1.25(3H, t, J=7.5Hz), 2.29-2.39 (2H, m), 3.43-3.54(2H, m), 3.61 (2H, t, J= 6.3Hz), 4.15 (2H, t, J = 5.8Hz), 5.99(1H, br), 6.89-6.95 (2H, m), 7.70-7.75 (2H, m) 38 -H -H -CONHC₃H₇ -H -H ¹H-NMR (CDCl₃) δppm: 0.99(3H, t, J=7.5Hz), 1.57-1.68(2H, m), 2.23-2.36 (2H, m), 3.37-3.45(2H, m), 3.61 (2H, t, J = 6.3Hz), 3.75(2H, t, J=6.3Hz), 4.12-4.18 (2H, m), 6.02(1H, br), 6.71-6.95 (2H, m), 7.71-7.75 (2H, m) Reference Example R1 R2 R3 R4 R5 NMR 39 -H -H -NO₂, -H -F ¹H-NMR (CDCl₃) δppm: 2.20-2.45 (2H, m), 3.70-3.80 (2H, m), 4.30-4.35 (2H, m), 7.07 (1H, dd. J=8.2, 8.9 Hz), 8.00 (1H, dd, J=2.7, 10.7 Hz), 8.07 (1H, dd, J=0.9, 9.0Hz). 40 -H -H -NH₂ -H -H ¹H-NMR (CDCl₃) δppm: 2.14-2.24 (2H, m), 3.26(2H, br), 3.73(2H, t, J=8.3Hz), 4.04(2H, t, J=5.8Hz,8.81-6.87(2H, m), 6.72-6.78(2H, m) 41 -H -H NHCO₂CH₃ -H -H ¹H-NMR (CDCl₃) δppm: 2.15-2.25 (2H, m 3.74 (2H, t, J = 6.3Hz), 3.76(3H, s), 4.09 (2H, t, J = 5.8Hz), 6.42(1H, br), 6.85 (2H, dd, J = 25, 8.8Hz), 7.21-7.33 (2H, m) 42 -H -H CH₂CON(C₂H₅)₂ -H -H ¹H-NMR (CDCl₃ ) δppm: 1.07-1.14(6H, m), 2.17-2.30 (2H, m), 3.26-3.42(4H, m), 3.63 (2H, s), 3.74 (2H, t, J = 6.3Hz), 4.09(2H, t, J=5.8Hz), 6.83-6.88 (2H, m), 7.14-7.19 (2H, m) 43 -H -H -H -NHCO₂CH₃ -H ¹H-NMR (CDCl₃) δppm: 2.28-2.37 (2H, m), 3.74(2H, t, J=8.5Hz), 3.77 (3H, s), 4.11(2H, t, J = 6.0Hz), 6.50-6.67(2H, m), 6.83(1H, dd, J=1.5Hz, 7.6Hz), 7.16-7.22 (2H, m) 44 -H -H -NHSO₂C₂H₅ -H -H ¹H-NMR (CDCl₃) δppm: 1.37 (3H, t, J=7.4 Hz), 2.15-2.30 (2H, m), 3.07 (2H, q, J=7.4 Hz), 3.75 (2H, t, J=6.3 Hz), 4.10 (2H, t, J=5.8 Hz), 6.41 (1H, brs), 6.88 (2H, dt J=8.9, 3.4 Hz), 7.19 (2H, dt, J=6.9, 3.4 Hz), 45 -H -H -NH₂ -H -OCH₃ ¹H-NMR (CDCl₃,) δppm: 2.15-2.30 (2H, m), 3.20-3.70 (2H, br), 3.75.3.95 (2H, m), 3.83(3H, s), 4.07 (2H, t, J=3 Hz), 6.24 (1H, dd, J=26, 8.4 Hz), 6.33 (1H, d, J=2.7 Hz), 6.77 (1H, d, J=8.4Hz). 46 -H -H -NHCO₇CH₃ -H -OCH₃ ¹H-NMR (CDCl₃) δppm: 2.20-2.30 (2H, m), 3.77 (3H, s), 3.86 (3H, s), 4.13 (2H, t, J=6.0 Hz), 6.55 (1H, brs), 6.73 (1H, dd, J=2.4, 8.6 Hz), 6.84 (1H, d, J=8.6 Hz), 7.20 (1H, brs). 47 -H -H -CONHC₂H₅ -H -H ¹H-NMR (CDCl₃) δppm: 1.23 (3H, t, J=7.3). Hz), 2.20-2.30 (2H, m), 3.40-3.50 (2H, m), 3.74 (2H, t, J=6.3 Hz), 4.14 (2H, t, J=5.8 Hz), 6.13 (1H, brs), 6.85-6.95 (2H, m), 7.70-7.75 (2H, m). 48 -H -H -NHCON(CH₃)₂ -H -H ¹H-NMR (CDCl₃) δppm: 2.15-2.25 (2H, m), 3.02 (6H, s), 3.74 (2H, t, J=6.4 Hz), 4.08 (2H, t, J=5.9 Hz), 6.20 (1H, brs), 6.84 (2H, dd, J=2.0, 8.8 Hz), 7.26 (2H, dd, J=21, 6.8 Hz). 49 -H -H -CO₂C₂H₅ -H -Cl ¹H-NMR (CDCl₃) δppm: 1.39(3H, t J=7.0Hz), 2.27-2.37 (2H, m), 3.81(2H, t J=6.8Hz), 4.25(2H, t, J=6.3Hz), 4.36(2H, q, J=7.0Hz), 6.86(1H, d, J=8.5Hz), 7.93(1H, dd, J=2.0Hz, 8.5Hz), 8.06(1H, d. J=2.0Hz) Reference Example R1 R2 R3 R4 R5 NMR 50 -H - H -CH₂CO₂C₂H₅ -H -Cl ¹H-NMR (CDCl₃) δppm: 1.26(3H, t, J=7.0Hz), 2.23-2.33 (2H, m), 3.52(2H, s), 3.80(2H, t, J=6.3Hz), 4.15(2H, q, J=7.0Hz), 6.90(1H, d, J=8.3Hz), 7.13(1H, dd, J=2.0Hz, 8.3Hz), 7.30(1H, d, J=2.0Hz) 51 -H -H -CH₂CONHCH₃ -H -H ¹H-NMR (CDCl₃) δppm: 2.19-2.29(2H, m), 2.76 (3H, d, J=4.8Hz), 3.52(2H, s), 3.76(2H, t, J=6.3Hz), 4.12(2H, t, J=5.8Hz), 5.35(1H, br), 6.86-6.92(2H, m), 7.13-7.18(2H, m) 52 -H -H -CH₂CH₂NHCH₃ -H -H ¹H-MMR (CDCl₃) δppm: 2.18-2.27 (2H, m), 2.43(2H, s), 2.72-2.83(4H, m), 3.71(3H, s), 3.75(4H, t, J=6.3Hz), 4.09(2H, t, J=5.8Hz), 6.83-6.86(2H, m), 7.10-7.14(2H, m) 53 -H -H -(CH₂)₂N(CH₃)CO₂C(CH₃)₃ -H -H ¹HNMR (CDCl₃) δppm: 1.42(9H,s), 2.17-2.27 (2H, m), 2.67-2.86(6H, m), 3.35-3.41 2H, m), 3.74(2H, t, J=6.3Hz), 4.09(2H, t, J=5.8Hz), 6.83(2H, d, J=8.5Hz), 7.00-7.16(2H, m) 54 -H -H -NH₂ -H -F ¹H-NMR (CDCl₃) δppm: 2.15-2.26 (2H, m), 3.54 (2H, brs), 3.76 (2H, t, J=6.4 Hz), 4.05-4.15 (2H, m), 6.35-6.40 (1H, m), 8.48 (1H, dd, J=0.9, 12.6 Hz), 8.82 (1H, dd, J=8.5, 8.5Hz). 55 -H -H NHCO₂CH₃ -H -F ¹H-NMR (CDCl₃) δppm: 2.20-2.30 (2H, m), 3.77 (2H, t, J=6.5 Hz), 3.77 (3H, s), 4.10-4.20 (2H, m), 6.57 (1H, brs), 6.85-7.00 (2H, m), 7.25-7.30 (1H, m). 56 -H -CH₂CO₂C₂H₅ -H -F ¹H-NMR (CDCl₃) δppm: 1.26(3H, t, J=7.0Hz), 2.21-2.30 (2H, m), 3.5382H, s), 3.77(2H, t, J=6.3Hz), 4.11-4.20(4H, m), 8.89-7.06(3H, m) 57 -H -H -CO₂C₂H₅ -H -Br ¹H-NMR (CDCl₃) δppm: 1.39(3H, t, J=7.0Hz), 2.27-2.37 (2H, m), 3.82(2H, t, J=6.3Hz), 4.24(2H, t, J=5.8Hz), 4.35(2H, q. J=7.0Hz), 6.92(1H, d, J=8.5Hz), 7.98(1H, dd, J=2.0H, 8.5Hz), 8.23(1H, d, J=2.0Hz) 58 -H -H -CHO -OCH₃ -H ¹H-NMR(CDCl₃) δppm: 2.23-2.34 (2H, m), 3.76(2H, t J=6.3Hz), 3.91(3H, s), 4.20(2H, t, J=5.8Hz), 6.46(1H, d, J=2.0Hz), 6.56(1H, dd, J=2.0Hz, 6.3Hz), 7.81(1H, d, J=8.3Hz), 10.29(1H, s) 59 -H -H -CO₂C₂H₅ -H -NO₂ ¹H-NMR (CDCl₃) δppm: 1.41(3H, t, J=7.0Hz), 2.26-2.40(2H, m). 3.81(2H, t J=6.3Hz), 4.32-4.44(4H, m), 7.15(1H, d, J=8.8Hz), 8.22(1H, dd. J=2.0Hz, 8.8Hz), 8.52(1H, d, J=2.0Hz) Reference Example R1 R2 R3 R4 R5 NMR 60 -H -H -CONHC₂H₅ -H -NO₂ ¹H-NMR (CCCl₃) δppm1.26 (3H, t J=7.3 Hz), 2.25-2.35 (2H, m).3.45-3.55(2H, m), 3.80 (2H, t, J=1 H₂), 4.30-4.35 (2H, m), 6.34 (1H, brs), 7.15 (1H, d=8.8 Hz), 8.04 (1H. dd, J=2.3, 8.8 Hz). 8.25 (1H. d, J=2.3 Hz). 61 -H -H -CONH₂ -OCH₃ -H ¹H-NMR (CDCl₃) δppm : 2.21-2.35 (2H, m ), 3.75( 2H, t, J=6.3Hz), 3.95(3H, s), 4.18( 2H, t, J=8.8Hz 5.67(1H, br), 6.51(1H, d, J=25Hz), 6.61(1H. dd, J=2.5Hz 8.8Hz), 7.59 (1H, br), 8.18 ( 1H, d, J=8.8Hz) 62 -H -H -CONHCH₃ -OCH₃ -H ¹H-NMR (CDCH) δppm: 2-20-2.30 (2H, m). 2.99(3H, d, J=5.0Hz), 3.75( 2H, t, J=6.3Hz). 3.94(3H, s), 4.17( 2H, t, J=6.0Hz). ), 6.49(1H, d J=2.5Hz)_. 6.60(1H. dd. J=2.5Hz, 8.8Hz). 7.70 (1H, br 8.19 (1H, d. J=8.8Hz) 63 -H -H -CONHC₂H₅ -OCH₃ -H ¹H-NMR (CDCl₃) δppm 1.23(3H, t, J=7.3Hz), 2.20-2.30 (2H,m ) 3.43-3.54(2H, m), 3.75( 2H. t, J=6.3Hz). 3.94(3H, s), 4.17( 2H. t, J=6.3Hz ), 6.49(1H, d, J=2.5Hz). 6.60(1H, dd, J=2.5Hz 8.8Hz). 7.70 (1H, br ), 8.18 (1H, d, J=8.8Hz) 64 -H -H -CONHCH₂CF₃ -OCH₃ -H ¹H-NMR (CDCl₃) δppm: 2.21-2.31 (2H, m ), 3.75( 2H, t, J=6.3Hz), 3.98(3H, s). 4.07-4.21( 4H, m ), 6.51(1H, d, J=5Hz), 6.62(1H, dd, J=2.5Hz, 8.8Hz), 8.09 (1H, br ), 8.18 (1H, d, J=8.8Hz ) 65 -H -H -CH=CHCO₂C₂H₅ -H -H ¹H-NMR (CDCl₃) δppm: 1.33(3H, t, ' J=7.0Hz), 2.20-2.30(2H, m), 3.73(2H, t, J=6.3Hz), d.15(2H, t, J=5.8Hz), 4.25(2H, q, J=7.0Hz), 8.31(1H. d, J= 18.0Hz), 8.88-8.93(2H. m), 7.44-7.50(2H, m), 7.64(1H, d, J=16.0Hz) 68 -F -H -H -CO₂C₂H₅ -H ¹H-NMR (CDCl₃) δppm:1.40(3H, t, J=7.0Hz), 2.25-2.34 (2H, m ), 3.78(2H, t, J=6.3Hz), 4.25(2H. J=5.8Hz), 4.37(2H, q, J=7.0Hz), 7.08-7.15(1H, m), 7.62-7.70(2H, m) 67 -H -H -CO₂H -CH₃ -H ¹H-NMR (CDCl₃) δppm: 221-231 (2H, m ), 2.64(3H, s), 3.75(2H, t, J=6.3Hz), 4.18(2H, t, J=5.8Hz), 6.77-8.81(2H, m), 8.06(1H, d, J=9.5H₂), 11.00(1 H, br) 68 -Cl -H -H -CO₂C₂H₅ -H ¹H-NMR (COCl₃ ) δppm: 1.40(3H, t, J=7.0Hz), 2.25-2.37 (2H. m ), 3.82(2H, t, J=6.3Hz),1.25(2H, t, J=5.8Hz), 4.38(2H. q, J=7.0Hz). 7.42(1H, d, J=8.5Hz). 7.56.7.62(2H. m) . 69 -CH₃ -H -H -CO₂C₂H₆ -H ¹H-NMR (CDCl₃, ) δppm: 1.39(3H, t, J=7.0Hz), 2.24-234 (2H, m ), 2.26(3H. s), 3.78(2H. t, J=6.3Hz). 4.19(2H. t, J=5.8Hz), 4.37(2H, q, J=7.0Hz). 7.19(1H, d, J=7.8Hz), 7.49(1H. d, J=1.5Hz), 7.57(1H, dd. J=1.5Hz, 7.8Hz) Reference Example R1 R2 R3 R4 R5 NMR 70 -H -H -CONH₂ -CH₃ -H ¹H-NMR (COCl₃) δppm: 2.16-2.29 (2H, m}, 2.51(3H, s), 3.75( 2H, t, J=6.3Hz), 4.14{ 2H, t, J=6.3Hz ), 6.53(2H, br), 6.71(2H, m), 7.45 (1H. d. J=8.3Hz ) 71 -H -H -CONRCH₃ -CH₃ -H ¹H-NMR (COCl₃) δppm: 2.18-2.28 (2H, m ), 2.45(3H, s), 298(33H, d, J=4.8Hz), 3.74( 2H, t, J=8.3Hz), 4.12( 2H, t, J=5.8Hz), 5.72(1H. br), 8.88-8.75(ZH, m), 7.32 ( 1H, d. J=8.3H ) 72 -H -H -CONHC₂H₃ -CH₃ -H ¹H-NMR (CDC% ) 8ppv: 1.24l3H, t, J=7.3Hz), 2.19-2.28 (2H, m ), 2.45(3H, s), 3.41-3.52(2H, m), 3.74(2H, t, J=6.3Hz), 4.12( 2H, t, J=6.0Hz ), 5.88(1H, br). 8.8843.75(2H, m), 7.32 (1H, d, J=8.3Hz ) 73 -CH₃ -H -CO₂C₂H₃ -H CH₃ ¹H-NMR (CDCl₃) δppm: 1.38(3H. t, J=7.0H₂). 2.21-2-28 (2H, m ), 2.31 (6H, s), 3.84(2H, t, J=6.3Hz), 3.93(2H. t, J=5.8Hz), 4.35(2H, t, J=7.0Hz), 7.72(2H, s) 74 -H -CO₂C₂H₅ -H -H -OCH₃ ¹H-NMR (COCl₃ ) δppm: 1.39(3H, t, J=7.1Hz). 2.26-2.38 (2H, m ), 3.78(2H, t, J=8.3Hz), 3.81(3H, s), 4.22(2H, t, J=5.8Hz), 4.36(2H, q, J=7.1Hx), 8.89(1H, d,J=8.3Hz), 7.58(1H, d, J=2.0Hz), 7.70 (1H, d, J=8.3Hz ) 75 -OCH₃ -H -CO₂C₂H₅ -H -OCH₃ ¹H-NMR (COCl₃ ) δppm 1.40(3H, t, J=7.0Hz), 2.13-2-23 (2H, m ), 3.85(2H, t, J=8.3Hz), 3.90(6H, s), 4.17(2H, t, J=5.8Hz), 4.38(2H, q, J=7.0Hz). 7.30(2H, s) 76 -CH₃ -H -CHO -H -OCH₃ ¹H-NMR (CDCl₃ δppm: 2.17-2.28 (2H, m ), 2.34(3H, s), 3.83(2H, t, J=6.3Hz). 3.91(3H, s), 4.18(2H, t, J=5.8Hz), 7.31(1H. s), 9.86(1H, s) 77 -CH₃ -H -CO₂H -H -OCH₃ ¹H-NMR (CDCl₃ ) δppm: 2.18-2.28 (2H, m ), 2.32(6H, s), 3.83(2H, t, J=3Hz), 3.90(3H, s), 4.16(2H, t, J=5.8Hz), 7.50(1H, d, J=2.0Hz), 7.80(1H, d, J=20Hz) 78 -CH₃ -H -CONH₂ -H -OCH₃ ¹H-NMR (CDCl₃) δppm: 217-2.27 (2H. m ), 2.30(3H, s), 3.83( 2H, t, J=3Hz), 3.89(3H, s), 4.12( 2H, t, J=5.8Hz ), 5.24-8.28(2H, br), 7.15(1H, d, J=20Hz), 7.32 (1H, d, J=2.0Hz ) 79 -CH₃ -H -CONHCH₃ -H -OCH₃ ¹H-NMR (CDCl₃) δppm 2.17-236 (2H, m ), 2.29(3H, s). 3.00(3H, d, J=5.0Hz), 3.83( 2H, t, J=8.3Hz), 3.88(3H, s), 4.10( 2H, t, J=5.8Hz), 8.06(1H, br), 7.08(1H, d, J=1.9Mz), 7.28 (1H, d. J=1.8Hz ) Reference Example R1 R2 R3 R4 R5 NMR 80 -CH₃ -H -CONHC₂H₅ -H -OCH₃ ¹H-NMR (CDCl₃) δppm 1.26(3H,t, J=7.3Hz), 2-17-2.28 (2H, m ), 2.30(3H, s), 3.43-3.54(2H, m). 3.83( 2H, t J=6.3Hz). 3.89(3H. s), 4.10(2H, t, J=5.8Hz ), 6.02(1H, br), 7.07(1H, d, J=20Hz), 7.28 ( 1H, d, J=2.0Hz ) 81 -CH₃ -H -NHCO₂C(CH₃)₃ -H -OCH₃ ¹H-NMR (CDCl₃) δppm 1.51(9H,s), 214-2.28 (2H, m ), 2.23(3H, s), 3.82(2H, t, J=6.3Mz). 3.83(3H. s). 3.98 (2H, t, J=5.8Hz ), 6.34(1H, br), 6.59(1H, d, J=2.5Hz), 7.01(1H, d, J=2.5Hz) 82 -CH₃ -H -NHCO₂CH₃ -H -OCH₃ ¹H-NMR (CDCl₃) δppm: 2.17-2.29 (2H, m ), 2.30(3H, s), 3.83(2H, t, J=8.3Hz), 3.88(6H, s), 4.13( 2H,1,J=5.8Hz), 7.44(1H, d, J=2.0Hz), 7.51 (1H, d. J=20Hz) 83 -CH₃ -H -CO₂CH₃ -H -OCH₃ ¹H-NMR (CDCl₃) δppm: 2.15-2.30 (2H, m), s). 3.89 (3H, s). 4.13 (2H, t, J=.9 Hz), 7.43 (1H, d, J=1.8 Hz), 7.50 (1H. d, J=1.4Hz). 84 -CH, -H -NH₂ 41 -OCH₃ H-NMR (CDCl₃ ) δppm: 2.14-2.22 (2H, m), 2.19(3H, 9), 3.47(2H, br), 3.82(2H, t, 1=5.3Hz). 3.95(2H, t, J=4.8Hz), 6.09-6.13(2H,m) 85 -CH₃ -H -HHCOCH₃ -H -OCH₂ ¹H-MMR(CDCl₃) δppm:2.11-2.28(2H,m), 2.15(3H, s), 2.24(3H. s), 3.82( 2H, t, J=6.3Hz), 3.83(3H, s), 4.01(2H, t, J=5.8Hz 6.66(1H, d, J=2.1 Hz), 7.02(1H, br), 7.23 (1H, d, J=2.1 Hz) 86 -CH₃ -H -CHO -H -OCOCH₃ ¹H-NMR (CDCl₃) δppm: 2.17-2.27(2H,m), 2.37(6H, s), 3.79(2H, t, J=5.6Hz), 4.11(2H, t, J=5.8Hz), 7.46(1H. d, J=2.0Hz), 7.62(1H, d, J=20Hz), 9.88(1H, s) 87 CH₃ -H -CO₂H -H -OCOCH₃ ¹H-NMR(CDCl₃) δppm: 2.16-2-26(2H.m), 2.35(3H, s). 2.38(3H. s), 3.79(2H, t, J=6.3Hz), 4.09(2H, t, J=5.8Hz), 7.67(1H, d, J=2.0Hz),7.84(1H,d,J=2.0Hz) 88 -OH -H -CONHCH₃ -H -CH₃ ¹H-NMR(CDCl₃) δppm :221-2.35(2H,m), 2.32(3H, s), 2.99(3H, d, J= 4.9Hz), 3.85(2H, t, J=6.3Hz), 4.05(2H, t, J=5.8Hz), 5.90(1H. br), 6.02(1H. br), 7.15(1H, d, J=1.8Hz), 7.20(1H, d, J=2.0Hz) 89 -CH₃ -H -CONHCH₃ -H -OC₂H₅ ¹H-NMR (CDCl₃ ) δppm: 1.46{3H, t, J=7.0Hz), 2.17-2.27 (2H, m), 2.28(3H, s), 2.99(3H, d, J=5.0Hz), 3.83(2H, t, J=6.3Hz). 4.08-4.15(4H, m 6.04(1H, br), 7.07(1H, d, J=1.8Hz), 7.25 (1H, d, J=1.8Hz) 90 -H -H -CO₂H -OCH₃ -H ¹H-NMR (CDCl₃ ) δppm: 2.22-232 (2H, m ), 3.75(2H. t, J=6.3Hz), 4.05(3H. s), 4.21( 2H, t, J=5.8Hz), 6.55(1H, d, J=2-5Hz). 8.86(1H, d, J=8.8Hz), 8.14(1H. d, J=8.8Hz), 10.43(1H, br) Reference Example R1 R2 R3 R4 R5 NMR 91 -H -H -H -H ¹H-NMR (COCl₃) δppm 22-2.3 (2H, m ), 3.77 ( 2H, 1 J = 6.3Hz ). 4.16 ( 2H, t, J = 5.8Hz ), 7.00 (2H, dd, J = 22, 6.7Hz ), 7.15-7.25 (2H, m 7.25-7.35 (2H, m ), 7.78 (1H,s). 92 -H -H -H -H H-NMR (CDCl₃) δppm: 2-26 (2H, t, J=6.1 Hz), 3.75 (2H, t, J=8.3 Hz 4.15 (2H,t, J=5.7 Hz), 7.00 (1H, dd, J=2.1, 6.9 Hz), 7.56 (1H, dd, J=2.2, 7.1 Hz), 8.07 (1H, s), 8.45(1H, s). 93 -H -H -H -H ¹H-NMR(CDCl₃) δppm:1.70.1.90 (4H, m), 2.10-2.40 (3H, m), 2.45 (3H. s), 3.553.75 (2H, m), 3.90-3.95 (2H, m), 4.05-4.15 (2H, m), 6.84 (2H, dd, J=1.9, 6.8 Hz), 7.06 (2H, dd. J=1.8, 6.9 Hz), 7.34 (2H, d, J=8.0 Hz), 7.68 (2H, d, J=8.2 Hz). 94 -CH, -H -H -OCH₃ ¹H-NmR(CDCl₃) δppm: 2.16-2.25 (2H,m), 2-28 (3H, s), 3.83(2H, t, J=8.3Hz), 3.8H(3H, s), 3.99-4.06( 4H, m 4.46(2H, dd, J= 6.3Hz, 8.8Hz), 6.81(1H, d, J=25Hz), 7.33 (1H, d, J=2.5Hz ) 95 -OCH₃ -H -H -CH₂OH ¹H-NMR (CDCl₃) δppm: 2.08-228 (2H, m ), 2.61(2H, t, J=7.8Hz), 3.7+3.87( 4H, m), 3.88(3H, s), 4.13(2H, t, J=5.5Hz ), 4.71(2H, d, t=5.8Hz), 6.85(1H, d, J=2.5Hz), 7.59 (1H, d, J=2.5Hz) 96 -CH₃ -H -H -OCH₃ ¹H-NMR(CDCl₃) δppm: 2.05-2-25 (4H, m ), 2.27(3H, s), 2.60(2H, t, J=8.3Hz), 3.79-3.89(42H. m), 3.86(3H, s),6.71(1H, d, J=2.5Hz), 7.37 (1H, d, J=2.5Hz ) Reference Example R1 R2 R3 R4 R5 NMR 97 -H -H -H -NO₂, -H ¹H-NMR (CDCl₃) δppm 1.93-211 (4H, m 3.59-3.70(2H, m), 4.00-4.13(2H, m), 720-724(1H, m), 7.43(1H, t, J=8.0Hz). 7.72(1H, t, J-2.3Hz), 7.80-7.84(1H, m) 98 -H -H -H -CN -H ¹H-NMR (CDCl₃) δppm 1.96-200 (4H, m ), 3.60-3.65 (2H, m), 3.99-4.14( 2H, m), 7.10-7.14 ( 2H, m ), 722-728 (1H, m), 7.34-7.40 (1H,m) R1-O-(CH2)3-Cl Reference Example R1 NMR 99 ¹H-NMR (CDCl₃) δppm: 2.20-2.30 (2H, m), 270-275 (2H, m), 3.07 (2H, t, J=5.8 Hz), 3.74 (2H, t, J=6.4 Hz). 7.15.7.20 (2H. m), 7.37 (1H, d. J=8.2 Hz). R1-O-(CH2)3-Cl Reference Example R1 NMR 100 ¹H-NMR (CDCl₃) δppm: 212 (2H, tt, J = 8.3, 6.3 Hz), 224 (2H, tt, J = 6.1, 6.1 Hz), 2.62(2H, t, J = 6.5 Hz), 2902(2H, t, J = 6.1 HZ), 3.74(2H, t, J = 6.3 Hz), 4.15 (2H, t J = 5.8 Hz), 7.05 (1H, dd, J =8.4, 2.8 Hz), 7.17 (1H, d, J = 8.4 Hz), 7.52 (1H, d, J = 28 Hz).

Methyl 5-(3-chloropropoxy)-1-methyl-1H-pyrazole-3-carboxylate (1.17g, 5.0 mmol), 1-benzo[b]thiophen-4-yl piperazine hydrochloride (1.35 g, 5.3 mmol), potassium carbonate (1.74, 12.6 mmol) and sodium iodide (0.75 g, 5.0 mmol) were added to DMF (12 ml), and the mixture was stirred at 80°C for 3 hours. The reaction solution was cooled to room temperature and water was added thereto, and then, extracted with ethyl acetate. The organic phase was washed with water and dried over magnesium sulfate. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 7:3 → dichloromethane : methanol =100:3). The purified product was concentrated under reduced pressure to obtain a light yellow oily substance (1.97 g). The oily substance was allowed to stand still at room temperature to obtain a solid substance, which was washed with diisopropyl ether and dried to obtain methyl 5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxyl-1-methyl-1H-pyrazole-3-carboxylate (1.49 g)
Melting point: 109.0-110.5°C
MS 414 (M⁺)

A 6N aqueous sodium hydroxide solution (2 ml) was added to an ethanol solution (10 ml) of methyl 5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1-methyl-1H-pyrazole-3-carboxylate (1.62 g, 3.9 mmol) and the mixture was stirred at room temperature for 4 days. Then, 6N hydrochloric acid (2 ml) was added to the reaction solution under ice cooling and the solution mixture was stirred. Dichloromethane was added to the reaction solution and the precipitate was obtained by filtration. The filtrate was separated and the organic phase was concentrated under reduced pressure. The filter cake and the residue were combined, washed with water and dried to obtain 5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1-methyl-1H-pyrazole-3-carboxylic acid (1.53 g) as white powder.
Melting point: 119.5-118.0°C

A DMF solution of 5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1-methyl-1H-pyrazole-3-carboxylic acid (0.3 g, 0.75 mmol) was cooled on ice and triethylamine (0.73 ml, 5.2 mmol), methylamine hydrochloride (0.3 g, 4.5 mmol) and diethylphosphorocyanidate (DEPC)(0.25 ml, 1.4 mmol) were added thereto, and then, the mixture was stirred at room temperature for 24 hours. To the reaction solution, triethylamine (0.73 ml, 5.2 mmol), methylamine hydrochloride (0.3 g, 4.5 mmol) and DEPC (0.25 ml, 1.4 mmol) were added and the mixture was stirred at room temperature for 4 days. Water was added to the reaction solution, which was then extracted with ethyl acetate. The extracted material was washed with water and dried over magnesium sulfate. The solution was concentrated under reduced pressure and the residue was purified by basic silica gel column chromatography (n-hexane : ethyl acetate = 5:1 → methyl acetate). The purified product was concentrated under reduced pressure and the residue was dissolved in ethyl acetate and a solution of 4N-hydrochloric acid/ethyl acetate was added thereto. The insoluble matter precipitated was obtained by filtration and dried to obtain N-methyl-5-[3-(4-benzo[b]thiophen-9-yl-piperazin-1-yl)propoxy]-1-methyl-1H-pyrazole-3-carboxamide hydrochloride (0.24 g) as white powder.
Melting point: 228.0-232.5°C (dec)

The titled compound was obtained using 5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1-methyl-1H-pyrazole-3-carboxylic acid and ammonium chloride in the same manner as in Example 3.
White powder (ethyl acetate-diisopropyl ether)
Melting point: 186:5-188.5°C

The titled compound was obtained using 4-(3-chloropropoxy)-3-methoxy-5,N-dimethylbenzamide and 1-benzo[b]thiophen-4-yl-piperazine hydrochloride in the same manner as in Example 1.
White powder (ethyl acetate-methanol)
Melting point: 141.5-142.5°C

Sodium hydride (55%, oily, 90 mg, 2.2 mmol) was added to a DMF solution (2 ml) of 3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propanol (0.2 g, 0.7 mmol) and N-methyl-2-chlorothiazole-4-carboxamide (0.26 g, 1.45 mmol) under ice cooling and the solution was stirred at 80°C for 1.5 hours. After the reaction solution was cooled to room temperature and water was added thereto, it was extracted with ethyl acetate. The extraction solution with ethyl acetate was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 5:1 → ethyl acetate). After the purified product was concentrated under reduced pressure, the residue was dissolved in ethyl acetate. A solution of 4N-hydrochloric acid/ethyl acetate was added to the solution and the insoluble matter precipitated was obtained by filtration and dried to obtain N-methyl-2-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]thiazole-4-carboxamide hydrochloride (0.24 g) as light yellow powder.
Melting point: 199.5-202.5°C

The titled compound was obtained using [4-(3-chloropropoxy)-3-methoxy-5-methylphenyl]-carbamic acid tert-butyl ester and 1-benzo[b]thiophen-4-yl-piperazine hydrochloride in the same manner as in Example 1.
Light brown oily substance
¹H-NMR (CDCl3) δppm : 1.51(9H, s), 1.95-2.10 (2H, m), 2.24(3H, s), 2.66-2.81(6H, m), 3.14-3.31(2H, m), 3.84(3H, s), 3.95(2H, t, J=6.3Hz), 6.36(1H, br), 6.60(1H, d, J=2.5Hz), 6.87-6.92(1H, m), 7.01 (1H, d, J=2.0Hz), 7.24-7.31(1H, m), 7.37-7.44(2H, m), 7.55(1H, d, J=8.0Hz)
MS 511(M+).

6N-hydrochloric acid (3 ml) was added to a methanol solution (10 ml) of {4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylphenyl}-carbamic acid tert-butyl ester (2.18 g, 4.3 mmol) and the mixture was stirred at room temperature overnight. After stirred at 60°C for 15 minutes, the mixture was cooled to room temperature and a 6N aqueous sodium hydroxide solution was added thereto to neutralize it. Dichloromethane was added to the reaction mixture, and the substance extracted with dichloromethane was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane : ethyl acetate = 3:2 → ethyl acetate). The purified product was concentrated to dryness under reduced pressure to obtain 4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylaniline (1.26 g) as light yellow solid
Melting point: 155.0-158.0°C
MS 411 (M⁺)

4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylaniline (0.9 g, 2.2 mmol) was added to.ethyl formate (10 ml) and refluxed with heating for 33 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (n-hexane : ethyl acetate = 5:1 → ethyl acetate). The purified product was concentrated under reduced pressure and a solution of 4N-hydrochloric acid/ethyl acetate was added to an ethyl acetate solution of the residue. The insoluble matter precipitated was obtained by filtration to obtain N-{4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylphenyl}formamide hydrochloride (0.3 g) as white powder.
Melting point: 247.5-253.0°C (dec)

A 6N aqueous sodium hydrochloride solution was added to N-{4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylphenyl formamide hydrochloride (0.23 g, 0.48 mmol) and the solution mixture was extracted with dichloromethane. The extraction solution with dichloromethane was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was dissolved in a tetrahydrofuran (THF) solution (5 ml) and lithium aluminum hydride (30 mg, 0.71 mmol) was added thereto under ice cooling and refluxed with heating for 15 minutes. The reaction solution was cooled on ice, and water (0.03 ml), 15 % aqueous sodium hydroxide solution (0.03 ml), and water (0.09 ml) were added to the reaction mixture in this order and stirred. Insoluble matter was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (n-hexane : ethyl acetate = 5:1 → 3:1) and concentrated under reduced pressure. A solution of 4N-hydrochloric acid/ethyl acetate was added to an ethyl acetate solution of the residue, and the insoluble matter precipitated was obtained by filtration to obtain N-methyl-4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxyl-3-methoxy-5-methylaniline hydrochloride (63 mg) as white powder.
Melting point: 239.5-294.0°C (dec)

The titled compound was obtained using 3-[4-(3-chloropropoxy)-3-methoxy-5-methylphenyl]oxazolidin-2-one and 1-benzo[b]thiophen-4-yl-piperazine hydrochloride in the same manner as in Example 1.
White powder (ethanol)
Melting point: 2.47.5-251.0°C (dec)

The titled compound was obtained using N-[4-(3-chloropropoxy)-3-methoxy-5-methylphenyl]acetamide and 1-benzo[b]thiophen-4-yl-piperazine hydrochloride in the same manner as in Example 1.
White powder (ethyl acetate-diisopropyl ether)
Melting point: 121.5-122.0°C

Sodium hydride (55%, oily, 0.06 g, 1.3 mmol) was added to a DMF solution (5 ml) of N-{4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylphenyl}acetamide (0.45 g, 0.99 mmol) under ice cooling and the mixture was stirred at 0°C for 15 minutes. Methyl iodide (0.07 ml, 1.1 mmol) was added to the reaction solution and the solution was stirred at 0°C for one hour. Further, sodium hydride (55% oily, 0.06 g, 1.3 mmol) and methyl iodide (0.07 ml, 1.1 mmol) were added to the reaction solution and the solution mixture was stirred at 0°C for 2 hours. Water was added to the reaction solution and extraction was performed with ethyl acetate. The extracted material was washed with water, and dried over magnesium sulfate. The reaction solution was concentrated under reduced pressure and the residue was purified by basic silica gel column chromatography (n-hexane : ethyl acetate = 5:1 → ethyl acetate). After the purified product was concentrated under reduced pressure, a solution of 4N-hydrochloric acid/ethyl acetate was added to an ethyl acetate solution of the residue. The insoluble matter precipitated was obtained by filtration to obtain N-{4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylphenyl}-N-methylacetamide hydrochloride (325 mg).
Melting point: 230.0-234.0°C (dec)

Formalin (37%, 0.29 ml, 3.9 mmol) and sodium cyanoborohydride (0.21 g, 3.1 mmol) were added to a methanol solution (6 ml) of 4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylaniline (0.32 g, 0.78 mmol) under ice cooling and the mixture was stirred at 0°C for 15 minutes. To the reaction solution, acetic acid (0.18 ml, 3.1 mmol) was added and the mixture was stirred at room temperature for one hour. An aqueous potassium carbonate solution was added to the reaction solution under ice cooling, and extraction was performed with ethyl acetate. The extracted material was dried over magnesium sulfate. The reaction solution was concentrated under reduced pressure, and the residue was purified by basic silica gel column chromatography (n-hexane :ethyl acetate = 11:1 → 3:1). The purified product was concentrated under reduced pressure. A solution of 4N-hydrochloric acid and ethyl acetate was added to an ethyl acetate solution of the residue and the insoluble matter precipitated was obtained by filtration to obtain 4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-N,N-dimethyl-3-methoxy-5-methylaniline hydrochloride (137 mg) as white powder.
Melting point: 234.5-240.5°C (dec)

The titled compound was obtained using methyl 4-(3-chloropropoxy)-3-methoxy-5-methylphenyl}carbamate and 1-benzo[b]thiophen-4-yl-piperazine hydrochloride in the same manner as in Example 1.
White powder (ethyl acetate)
Melting point: 230.0-235.5°C

The titled compound was obtained using methyl {4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methoxy-5-methylphenyl}carbamate hydrochloride and methyl iodide in the same manner as in Example 14.
White powder (ethyl acetate)
Melting point: 228.0-233.5°C

Lithium aluminum hydride (86 mg, 2.3 mmol) was suspended in THF (20 ml). To this solution, a THF solution (10 ml) of 6-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3,4-dihydro-2H-benzo[1,4]oxazin-3-one (0.8 g, 1.9 mmol) was added dropwise under an argon atmosphere. After completion of dropwise addition, the solution mixture was refluxed with heating for one hour. Water (0.1 ml), 15 % aqueous sodium hydroxide solution (0.1 ml), and water (0.3 ml) were added to the reaction mixture under ice cooling and stirred. Insoluble matter was removed by cerite filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane : methanol = 1:0 → 20:1) and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (10 ml) and a solution (0.34 ml) of 1N-hydrochloric acid/ethanol was added thereto and the mixture was stirred at room temperature for 15 minutes. The insoluble matter precipitated was obtained by filtration, washed with ethyl acetate, and dried to obtain 6-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3,4-dihydro-2H-benzo[1,4]oxazine hydrochloride (0.11 g) as white solid.
Melting point 207.9-208.8°C

Formalin (37%, 0.22 ml, 2.7 mmol) and MP-cyanoborohydride (2.41 mmol/g, 1.12 g, 2.7 mmol) were added to a methanol solution (15 ml) of 7-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3,4-dihydro-2H-benzo[1,4]oxazine (0.30 g, 0.67 mmol) and the mixture was stirred at room temperature overnight. The insoluble matter was removed by filtration and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane methanol = 1:0→ 50:1). The purified product was concentrated under reduced pressure and the residue was dissolved in ethyl acetate (15 ml) and a solution (0.64 ml) of 1N-hydrochloric acid/ethanol was added thereto. The mixture was stirred at room temperature for 15 minutes. The insoluble matter precipitated was obtained by filtration, washed with ethyl acetate, and dried to obtain 7-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-4-methyl-3,9-dihydro-2H-benzo[1,4]oxazine hydrochloride (0.23 g) as light brown solid.
Melting point; 248.1-249.6°C

A THF solution (20 ml) of 6-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methylquinazoline (0.25 g, 0.58 mmol) was cooled on ice. To this solution, a THF solution (5 ml) of lithium aluminum hydride (26 mg, 0.69 mmol) was added dropwise under an argon atmosphere. After completion of dropwise addition, the solution was stirred at room temperature for 20 minutes and refluxed with heating for one hour. Water (0.03 ml), 15 % aqueous sodium hydroxide solution (0.03 ml), and water (0.1 ml) were added to the reaction solution under ice cooling and stirred. Insoluble matter was removed by cerite filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (dichloromethane : methanol = 1:0 → 25:1). The purified product was concentrated under reduced pressure and the residue was dissolved in ethyl acetate (5 ml). To this, a solution (0.189 ml) of 1N-hydrochloric acid/ethanol was added and the mixture was stirred at room temperature for 15 minutes. The insoluble matter precipitated was obtained by filtration, washed with ethyl acetate, and dried to obtain 6-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methyl-1,2,3,4-tetrahydroquinazolin-4-ol hydrochloride (87 mg) as white solid.
MS: 438 (M⁺).

An eluting solution of dichloromethane/methanol (10:1) was passed through the column of the silica gel column chromatography. The obtained eluate was concentrated under reduced pressure and then the residue was dissolved in ethyl acetate (5 ml). To this, a solution (0.226 ml) of 1N-hydrochloric acid/ethanol was added and the mixture was stirred at room temperature for 15 minutes. The insoluble matter precipitated was obtained by filtration, washed with ethyl acetate, and dried to obtain 6-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-3-methyl-1,2,3,4-tetrahydroquinazoline hydrochloride (49 mg) as white solid.
Melting point: 203.1-204.4°C

Triethylsilane (1.14 ml, 7.14 mmol) was added to a trifluoroacetic acid solution (5 ml) of 5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-1H-indole (228 mg, 0.71 mmol) and the mixture was stirred at 50°C for 2 hours. The mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane, neutralized by a saturated aqueous solution of sodium hydrogen carbonate and separated. The organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate, water and a saturated saline solution in this order and concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (n-hexane : ethyl acetate = 5: 1 → 1:1). The purified product was concentrated under reduced pressure and the residue was added to ethyl acetate (5 ml) and a solution of 1N-hydrochloric acid/ethanol (0.10 ml) was added thereto and the mixture was stirred at room temperature for 15 minutes. The insoluble matter precipitated was obtained by filtration, washed with ethyl acetate, and dried to obtain 5-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-2,3-dihydro-1H-indole hydrochloride (32 mg) as white solid.
Melting point: 222.4-223.9°C

Compounds listed in the following Tables 12 to 131 were produced using appropriate starting substances in the same manners as in Reference Examples 1 to 36 or Examples 1 to 20 and 1051 to 1067.

In the following Tables, compounds with the physical properties, such as crystalline form, m.p. (melting point), salt, ¹H-NMR and MS (mass spectrum), were prepared actually. Example R1 Crystal form (Recrystalization solvent) Melting point (°C) Salt 21 White solid (Ethanol/ ethyl acetate) 251:1-253.6 Hydrochloride 22 White solid (Ethyl acetate) 249.8-2523 Hydrochloride Example R1 NMR Salt 23 ¹H-NMR (DMSO-d₆) δ ppm 220-2.30 (2H, m), 2.64 (2H. t, J=5.8 Hz), 3.01 (2H, t, J=5.5 Hz), 320-3.40 (6H, m), 3.53 (2H, d, J=123 Hz), 3.64 (2H, d J=11.2 Hz), 4.15 (2H, t, J=6.0 Hz), 6.95 (1H, d, J=7.7 Hz), 7.13 (1H, d, J=2.4 Hz), 7.25-7.35 (2H, m), 7.45-7.55 (2H, m), 7.69 (1H, d, J=8.0 Hz), 7.75 (1H, d, J=5.8 Hz), 11.12 (1H, brs). Hydrochloride Example R1 Crystal form (Recrystallization solvent) Melting point (°C) Salt 24 White solid (Ethanol/ethyl acetate) 2420-244.9 Hydrochloride Example R1 Crystal form (Recrystallization solvent) Melting point (°C) Salt 25 White powder (Ethyl acetate/ether) 198-201 Hydrochloride 26 White powder (Ethyl acetate/ether) 206-209 Hydrochloride Example R1 Crystal form (Recrystallization solvent) Melting point (°C) Salt 27 Light yellow powder (Ethyl acetate/isopropyl ether) 112.5-114.5 - 28 White powder (Ethyl acetate) 208.0-211.5 Hydrochloride Example R1 R2 n Crystal form (Recrystallization solvent) Melting point (°C) Salt 29 -H -C₂H₅ 3 White powder (Ethyl acetate) 218.5-222.0 (dec) Hydrochloride 30 -H -C₃H₇ 3 Light yellow powder (Ethyl acetate/isopropyl ether) 127.0-128.5 - 31 -H -CH₃ 3 Light yellow powder (Ethyl acetate/isopropyl ether) 151.0-154.5 - 32 -CH₃ -CH₃ 3 White powder (Ethyl acetate). 206.5-211.5 Hydrochloride 33 -C₂H₅ -C₂H₅ 3 White powder (Ethyl acetate) 205.5-209.0 Hydrochloride 34 -H -CH₂CF₃ 3 White powder (Ethyl acetate) 217.0 (dec) Hydrochloride 35 -H -CH₂CH₂N(C₂H₅)₂ 3 White powder (Ethyl acetate) 229.5-232.5 Dihydrochloride 36 -H -CH₂CH₂OCH₃ 3 White powder (Ethyl acetate) 218.5-221.0 Hydrochloride 37 -H -cyclo-C₃H₅ 3 White powder (Ethyl acetate/isopropyl ether) 185.5-167.0 - 38 -H -OH(CH₃), 3 White powder (Ethyl acetate/isopropyl ether) 131.5-1325 - 39 -H -H 3 White powder (Dichloromethane) 186.0-191.0 - 40 -H -(CH₂)₅OH 3 White solid (Ethanol) 202-203 Hydrochloride 41 -H 3 Light brown solid (Ethanol) 215-216 Hydrochloride 42 -H -C₂H₅ 4 White powder (Ethyl acetate) 198.0-199.5 Hydrochloride 43 -H -CH₂CF₃ 4 White powder (Ethyl acetate) 194.5-196.0 Hydrochloride 44 -H -H 4 White powder (2-propanol) 150.0-151.5 - 45 -H -CH₃ 4 White powder (Ethyl acetate) 154.0-156.0 - 46 -CH₃ -CH₃ 4 White powder (Ethyl acetate) 226.0 (dec) Hydrochloride Example R1 R2 NMR Salt 47 -H -CH₂CH₂OH ¹H-NMR (DMSO-d₆ ppm 2.1-22 (2H, m), 3.1-3.8 (14H. m), 4.17 (2H, t, J=5.7 Hz), 4.6-4.8 (1H, br), 6.9-7.1 (3H, m), 7.33 (1H, dd, J=7.9, 8.1 Hz), 7.51 (1H, d, J=5.5 Hz), 7.72 (1H, d, J=8.1 Hz), 7.78 (1H, d, J=5.5 Hz), 7.86 (2H, d, J=8.8 Hz), 8.2-8.3 (1H, br), 102-10.4 (1H, br). Hydrochloride Example R1 R2 R3 R4 R5 R6 Crystal form (Recrystallization solvent) Melting point (°C) Salt 48 -H -H -H -OCH₃ -CH₃ -CH, White powder (Ethyl acetate) 199.0-204.0 Hydrochloride 49 -OCH₃ -H -H -H -C₂H₅ -H White powder (Ethyl acetate/isopropyl ether) 162.0-163.0 - 50 -Cl -H -H -H -H -H White powder (Ethyl acetate/isopropyl ether) 154.0-155.5 - 51 -Cl -H -H -H -CH, -H White powder (Ethyl acetate/isopropyl ether) 145.0-148.0 - 52 -H -H -H -Cl -CH₃ -CH₃ White powder (Ethyl acetate) 213.0 (dec) Hydrochloride 53 -H -H -H -Cl -C₂H₅ -H White powder (Ethyl acetate) 211.0 (dec) Hydrochloride 54 -Cl -H -H -H -CH₂CF₃ -H White powder (Ethyl acetate/isopropyl ether) 128.5-131.0 - 55 -F -H -H -H -H -H White powder (Ethyl acetate/isopropyl ether) 153.5-156.0 - Example R1 R2 R3 R4 R5 R6 Crystal form (Recrystallization solvent) Melting point (°C) Salt 56 -H -H -H -F -CH₃ -H White powder (Ethyl acetate) 232.0 (dec) Hydrochloride 57 -H -H -H -F -CH₃ -CH₃ White powder (Ethyl acetate) 198.0-202.0 Hydrochloride 58 -H -H -H -F -C₂H₅ -H White powder (Ethyl acetate) 210.5-213.0 Hydrochloride 59 -F -H -H -H -CH₂CF₅ -H Light yellow powder (Ethyl acetate/isopropyl ether) 178.5-179.5 - 60 -CH₃ -H -H -H -H -H White powder (2-propanol) 178.5-180.0 - 61 -CH₃ -H -H -H -CH₃ -H White powder (2-propanol) 156.5-158.0 - 62 -H -H -H -CH₃ -CH₃ -CH₃ White powder (Ethyl acetate) 220.0-222.0 (dec) Hydrochloride 63 -CH₃ -H -H -H -C₂H₆ -H White powder (2-propanol) 140.5-143.0 - 64 -CH₃ -H -H -H -CH₂CF₃ -H White powder (2-propanol) 154.5-157.0 - 65 -OCH₃ -H -H -H -H -H White powder (2-propanol) 162.0-163.5 - Example R1 R2 R3 R4 R5 R6 Crystal form (Recrystallization solvent) Melting point (°C) Salt 66 -OCH₃ -H -H -H -CH₃ -H White powder (2-propanol) 180.5-182.0 - 67 -OCH₃ -H -H -H -CH₂CF₃ -H Light yellow powder (2-propenal) 144.5-148.0 - 68 -Cl -H -H -H -CH₂CH₂OCH₃ -H White powder 120-122 - 69 -H -H -H -F -CH₂CH₂OCH₃ -H White powder (Ethanol/ethyl acetate) 215.0-217.0 Hydrochloride 70 -CH₃ -H -H -H -CH₂CH₂OCH₃ -H White powder (Ethanol/hexane) 120.0-121.0 - 71 -H -H -H -OCH₃ -CH₂CH₂OCH₃ -H White powder (Ethanol/ethyl acetate) 194-188 Hydrochloride 72 -Br -H -H -H -H -H White powder (Ethyl acetate/isopropyl ether) 152.5-154.0 - 73 -Br -H -H -H -CH₃ -H White powder (Ethyl acetate/isopropyl ether) 148.0-150.0 - 74 -H -H -H -Br -CH₃ -CH₃ White powder (Ethyl acetate) 225.0 (dec) Hydrochloride 75 -H -H -H -Br -C₂H₅ -H Light yellow powder (Ethyl acetate) 214.5-220.5 (deo) Hydrochloride Example R1 R2 R3 R4 R5 R6 Crystal form (Recrystallization solvent) Melting point (°C) Salt 76 -H -H -H -Br CH₂CF₃, -H White powder (Ethyl acatate/isopropyl ether) 230.0-234.5 Hydrochloride 77 -CN -H -H -H -H -H White powder (Ethyl acetate) 182.0-185.0 - 78 -CN -H -H -H -CH₃ -H White powder (2-propenol) 177.5-181.5 - 79 -H -H -H -CN -CH₃ -CH₃ White powder (Ethyl acetate) 213.5-214.0 Hydrochloride 80 -CN -H -H -H -C₂H₅ -H White powder (2-propanol) 182.5-188.0 - 81 -H -H -H -CN CH₂CF₃ -H White powder (Ethyl acetate) 217.0-222.0 Hydrochloride 82 -H -Cl -H -H -H -H White powder (95% 2-propanol) 133.5-135.5 - 83 -H -Cl -H -H -CH₃ -H White powder (95% 2-propanol) 137.0-138.0 - 84 -H -H -Cl -H -CH₃ -CH₃ White powder (Ethyl acetate) 236.0 (dec) Hydrochloride 85 -H -H -Cl -H -C₂H₅ -H White powder (Ethyl acetate) 223.0-224.0 Hydrochloride Example R1 R2 R3 R4 R5 R6 Crystal form (Recrystallization solvent) Melting point (°C) Salt 86 -H -H -Cl -H -CH₂CF₃ -H White powder (Ethyl acetate) 210.5-218.0 Hydrochloride 87 -H -H -CF₃ -H -C₂H₅ -H White powder (Ethyl acetate) 212.0-219.5 Hydrochloride 88 -H -CF₃ -H -H -H -H White powder (Dichloromethene/isopropyl ether) 138.5-141.0 Hydrochloride 89 -H -H -CF₃ -H -CH₃ -H White powder (Ethyl acetate) 214.0-218.5 Hydrochloride 90 -H -H -CF₃ -H -CH₃ -CH₃ White powder (Ethyl acetate) 252.5 (dec) Hydrochloride 91 -H -H -CF₃ -H -CH₂CF₃ -H White powder (Ethyl acetate) 218.0-218.5 Hydrochloride 92 -H -OCH₃ -H -H -H -H White powder (2-propanol) 173.5-178.5 - Example R1 R2 R3 R4 R5 R6 NMR Salt 93 -N(CH₃)₂ -H -H -H -C₂H₈ -H ¹H-NMR (CDCl₃ ) δppm: 1.20-1.30 (3H, m), 2.10-2.20 (2H, m), 2.69 (2H, t, J=7.3 Hz), 2.70-2.75 (4H, m), 285 (6H, s). 3.20-3.25 (4H, m). 3.45-3.55 (2H, m), 4.10-4.20 (2H, m), 6.00 (1H, brs), 6.85-6.95 (2H, m). 7.25-7.30 (3H, m), 7.35-7.45 (2H, m). 7.56 (1H, d, J=8.1 Hz). - 94 -NHCOCH₃ -H -H -H -C₂H₅ -H ¹H-NMR (CDCl₃ δppm: 1.20-1.30 (3H, m), 2.05-2.15 (2H, m), 2.25 (3H, s), 2.65 (2H, t, J=7.1 Hz), 2.70-2.80 (4H, m), 3.20-3.25 (4H, m), 3.40-3.55 (2H, m), 4.21 (2H, t J=6.4 Hz), 6.22 (1H, brs), 6.81 (1H, d, J=7.7 Hz), 6.98 (1H, d, J=8.6 Hz), 7.25-7.30 (1H, m), 7.35-7.45 (2H, m), 7.56 (1H, d, J=8.0 Hz). 7.71 (1H, d, J=8.5 Hz), 7.82 (1H, brs), 8.70 (1H, s). - Example R1 R2 R3 R4 R5 R6 Crystal form (Recrystallization solvent) Melting point (°C) Salt 95 -H -H -OCH₃ -H -CH₃ -H White powder (2-propanol) 221.5-223.0 Hydrochloride 96 -H -H -OCH₃ -H -CH₃ -CH₃ White powder (Ethyl acetate) 207.5-215.0 Hydrochloride 97 -H -H -OCH₃ -H -C₂H₆ -H White powder (Ethyl acetate) 187.0-202.0 Hydrochloride 98 -H -H -OCH₃ -H -CH₂CF₃ -H White powder (Ethyl acetate) 219.0-227.0 Hydrochloride 99 -NO₂ -H -H -H -H -H Light yellow powder (Ethyl acetate/isopropyl ether) 157.5-181.0 - 100 -NO₂ -H -H -H -CH₃ -H Light yellow powder (Ethyl acetate/isopropyl ether) 157.5-161.5 - 101 -H -H -H -NO₂ -CH₂CF₃ -H Light yellow powder (Ethyl acetate) 217.5-219.5 (dec) Hydrochloride 102 -CF₃ -H -H -H -H -H White powder (95% 2-propanol) 163.5-185.5 - 103 -NH₂ -H -H -H -H -H White powder (Ethyl acetate/isopropyl ether) 172.5-173.0 - 104 -CF₃ -H -H -H -CH₃ -H White powder (95% 2-propanol) 158.5-162.0 - 105 -CF₃ -H -H -H -C₂H₅ -H White powder (95% 2-propanol) 146.5-148.5 - Example R1 R2 R3 R4 R5 R6 Crystal form (Recrystallization solvent) Melting point (°C) Salt 106 -CF₃ -H -H -H -CH₂CF₃ -H White powder (95% 2-propanol) 144.5-150.0 - 107 -NH₂ -H -H -H -CH₃ -H White powder (Ethyl ecetate/isopropyl ether) 124.0-125.5 - 108 -N(CH₂)₂ -H -H -H -H -H White powder (Ethyl acetate/isopropyl ether) 143.0-145.0 - 109 -H -H -H -N(CH₃)₂ -CH₃ -H White powder (Ethyl acetate) 219.0-223.0 Hydrochloride 110 -NH₂ -H -H -H -CH₂CF₃ -H White powder (Ethyl acetate/isopropyl ether) 125.0-128.0 - 111 -N(CH₃)₂ -H -H -H -CH₂CF₃ -H White powder (Ethyl acetate/Isopropyl ether) 147.5-148.5 - 112 -H -CH₃ -H -H -H -H White powder (95% 2-propanol) 150.5-152.5 - 113 -H -CH₃ -H -H -CH₃ -H White powder (95% 2-propanol) 138.0-139.0 - 114 -H -CH₃ -H -H -C₂H₈ -H White powder (95% 2-propanol) 137.5-139.0 - 115 -CH₃ -H -H -CH₃ -H -H White powder (95% 2-propenol) 187.0-188.0 - Example R1 R2 R3 R4 R5 R6 Crystal form (Recrystallization solvent) Melting point (°C) Salt 116 -CH₃ -H -H -CH₃ -CH₃ -H White powder (95% 2-propenol) 1525-154.5 - 117 -CH₃ -H -H -CH₃ -C₂H₃ -H White powder (95% 2-propanol) 184.0-185.5 - 118 -OCH₃ -H -H -OCH₃ -H -H White powder (Ethyl acetate/isopropyl ether) 147.5-148.0 - 119 -OCH₃ -H -H -OCH₃ -CH₃ -H White powder (Ethyl acetate) 233.0-237.5 (dec) Hydrochloride 120 -OCH₃ -H -H -OCH₃ -C₂H₃ -H White powder (Ethyl acetate/isopropyl ether) 145.5-147.5 - 121 -OC₂H₃ -H -H -CH₃ -CH₂ -H White powder (Ethanol/ethyl acetate) 186,5-188.0 Hydrochloride 122 -CH₂CH=CH₂ -H -H -OCH₃ -H -H (Ethyl acetate/isopropyl ether) 128.0-130.0 - 123 -C₃H₇ -H -H -OCH₃ -H -H (Ethyl acetate/isopropyl ether) 137.5-140,0 - 124 -OCH₃ -H -H -CH₂CH=CH₂ -CH₃ -H White powder (Ethyl acetate) 180.5-188.0 Hydrochloride 125 -OCH₃ -H -H -C₂H₇ -CH₃ -H White powder (Ethyl acetate) 188.5-192.0 Hydrochloride Example R1 R2 R3 R4 R5 R6 Crystal form (Recrystallization solvent) Melting point (°C) Salt 126 -CH₃ -H -H -OCH₃ -H -H White powder (Ethyl acetate/isopropyl ether) 158.0-157.0 - 127 -CH₃ -H -H -OCH₃ -CH₃ -H White powder (Ethyl acetate/methanol) 141.5-142.5 - 128 -OCH₃ -H -H -CH₃ -C₂H₅ -H White powder (Ethyl acetate) 220.5-224.5 Hydrochloride 129 -OCH₃ -H -H -CH₃ -CH₃ -OCH₃ White powder (Ethyl acetate) 223.0-227.5 Hydrochloride Example R1 R2 R3 R4 R5 R6 NMR Salt 130 -H -H -H -NO₂ -C₂H₅ -H 1H-NMR (CDCl3 ) δppm: 1.28 (3H, t, J=7.3 Hz), 2.05-2.15 (2H, m), 2.68 (2H, t, J=7.0 Hz), 2.73 (4H, brs), 3.19 (4H, brs). 3.45-3.55 (2H, m). 4.29 (2H, t, J=6.2 Hz), 6.14 (1H, brs), 6.90 (1H, d, J=7.8 Hz), 7.18 (1H, d, J=8.8 Hz), 7.25-7.30 (1H, m), 7.35-7.45 (2H, m), 7.55 (1H, d, J=8.1 Hz), 8.04 (1H, dd, J=2.3, 8.8 Hz), 8.23 (1H, d. J=2.2 Hz). - Example R1 R2 R3 R4 R5 Crystal form (Recrystallization solvent) Melting point (°C) Salt 131 -H -H -H -H White powder (Ethyl acetate) 234.5-238.0 Hydrochloride 132 -H -H -H -H White powder (Ethyl acetate) 244.0 (dec) Dihydrochloride 133 -H -H -H Cl White powder (Ethyl acetate) 218.5-222.0 Hydrochloride 134 -H -H -H -Cl White powder (Ethyl acetate) 255.0 (deo) Dihydrochloride 135 -H -H -H -F White powder (Ethyl acetate) 224.5-227.5 (dec) Hydrochloride 136 -H -H -H -F White powder (Ethyl acetate) 255.0 (dec) Dihydrochloride 137 -H -H -H -CH₃ White powder (Ethyl acetate) 236.0 (dec) Hydrochloride 138 -H -H -H -CH₃ White powder (Ethyl acetate) 255.5 (dec) Dihydrochloride 139 -H -H -H -OCH₃ White powder (Ethyl acetate) 228.0-228.0 (dec) Hydrochloride 140 -H -H -H -OCH₃ White powder (Ethyl acetate) 232.0 (dec) Dihydrochloride Example R1 R2 R3 R4 R5 R6 Crystal form (Recrystallization solvent) Melting point (°C) Salt 141 -H -H -H -H -H -H Light yellow powder (Ethyl acetate/isopropyl ether) 158.0-160.0 - 142 -H -H -H -H -H -CH₃ Light yellow powder (Ethyl acetate) 183.0-188.0 Hydrochloride 143 -H -H -H -H -CH₃ -CH₃ Light yellow powder (Ethyl acetate) 158.0-181.5 Hydrochloride 144 -H -H -H -H -H -C₂H₅ Light yellow powder (Ethyl acetate) 168.5-173.0 Hydrochloride 145 -H -H -H -H -H -CH₂CF₃ Light yellow powder (Ethyl acetate/isopropyl ether) 187.5-189.0 Hydrochloride 146 -F -H -H -H -H -H White powder (Ethyl acetate/isopropyl ether) 156.5-159.0 - 147 -F -H -H -H -H -CH₃ White powder (Ethyl acetate/isopropyl ether) 214.5-218.0 Hydrochloride 148 -F -H -H -H -H -C₂H₅ White powder (Ethyl acetate) 211.0-218.0 Hydrochloride 149 -Cl -H -H -H -H -H White powder (Ethyl ecetate/isopropyl ether) 139.0-140.5 - 150 -Cl -H -H -H -H -CH₃ White powder (Ethyl acetate) 218.6-222.5 Hydrochloride 151 -Cl -H -H -H -H -C₂H₅ White powder (Ethyl acetate) 247.0 (dec) Hydrochloride 152 -CH₃ -H -H -H -H -H White powder (Ethyl acetate/isopropyl ether) 128.5-130.0 - 153 -CH₃ -H -H -H -H -CH₃ White powder (Ethyl acetate/isopropyl other) 148.5-151.0 - 154 -CH₃ -N -H -H -H -C₂H₅ White powder (Ethyl acetate/isopropy) ether) 133.0-134.5 - 155 -OCH₃ -H -H -H -H -H White powder (Ethyl acetate) 155.5-160.0 - 156 -OCH₃ -H -H -H -H -CH₃ White powder (Ethyl acetate) 163.5-165.0 Hydrochloride Example R1 R2 R3 R4 R5 R6 Crystal form (Recrystallization solvent) Melting point (°C) Salt 157 -OCH₃ -H -H -H -H -C₂H₃ White powder (Ethyl acetate) 187.0-188.5 Hydrochloride 158 -OCH₃ -OCH₃ -H -H -H -H White powder (Ethyl acetate/isopropyl ether) 132.0-134.0 - 159 -OCH₃ -OCH₃ -H -H -H -CH₃ White powder (Ethyl acetate) 201.0-208.0 Hydrochloride 160 -OCH₃ -OCH₃ -H -H -H -C₂H₅ White powder (Ethyl acetate/isopropyl ether) 158.0-158.5 - Example R1 R2 R3 R4 R5 R6 Crystal form (Recrystallization solvent) Melting (°C) Salt 161 -H -H -H -H -C₂H₅ -H Light yellow powder (Ethyl acetate) point 228.0-241.0 (dec) Dihydrochloride 162 -H -H -H -H -C₃H₇ -H White powder (Ethyl acetate) 232.0-236.0 (dec) Dihydrochloride 163 -H -H -H -H -C₃H₇ -CH₃ White powder (Ethyl acetate) 210.0-222.0 (dec) Dihydrochloride 164 -H -H -H -H -CH₃ -H White powder (Ethyl acetate) 235.5 (dec) Dihydrochloride 165 -H -H -H -H -CH₃ -CH₃ White powder (Ethyl acetate) 257.5 (dec) Dihydrochloride 166 -H -H -H -H -C₂H₅ -C₂H₅ White powder (Ethyl acetate) 232.0 (dec) Dihydrochloride 167 -H -H -H -H -CH₂CF₃ -H White powder (Ethyl acetate) 238.5-240.5 (dec) Dihydrochloride 168 -H -H -H -H -CH₂CH₂N(C₂H₅)₂ -H White powder (Ethyl acetate) 209.5 (dec) Triydrochloride 169 -H -H -H -H -H -H Light yellow powder (Ethyl acetate) 245.5 (dec) Dihydrochloride 170 -H -H -H -H -CHO -H White powder (Ethyl acetate) 207.6-213.0 Hydrochloride 171 -H -H -H -H -COCH₃ -CH₃ White powder (Ethyl acetate) 188.5-201.0 Hydrochloride 172 -H -H -H -H -COC₂H₅ -CH₃ White powder (Ethyl acetate) 194.5-198.0 Hydrochloride 173 -H -H -H -H -COC₆H₅ -CH₃ White powder (Ethyl acetate) 192.5-195.5 Hydrochloride 174 -H -H -H -H -CH₂C₆H₅ -CH₃ White powder (Ethyl acetate) 236.5 (dec) Dihydrochloride 175 -H -H -H -H -C₂H₅ -H White powder (Ethyl acetate) 191.0-193.5 Dihydrochloride 176 -OCH₃ -H -H -H -CH₃ -CH₃ White powder (Ethyl acatate/isopropyl ether) 101.0-103.0 - 177 -H -H -H -H -C₆H₅ -CH₃ White powder (Ethyl acetate) 207.5-214.5 Triydrochloride 178 -H -H -H -Cl -CH₃ -CH₃ White powder (Ethyl acetate) 259.0 (dec) Dihydrochloride 179 -H -H -H -F -CH₃ -CH₃ White powder (Ethyl acetate) 247.0 (dec) Dihydrochloride 180 -H -H -H -F -CH₃ -H White powder (Ethyl acetate) 237.0 (dec) Dihydrochloride 181 -H -H -H -F -CH₃ -CONCH₃ White powder (Ethyl acetate) 198.0-199.0 Hydrochloride Example R1 R2 R3 R4 R5 R8 Crystal form (Recrystallization solvent) Melting point (°C) Salt 182 -H -H -H -CH₃ -CH₃ -C₂H₅ White powder (Ethyl acetate) 258.5 (dec) Dihydrochloride 183 -H -H -H -CH₃ -CH₃ -H White powder (Ethyl acetate) 254.5 (dec) Dihydrochloride 184 -H -H -H -CH₃ -CH₃ -CH₃ White powder (Ethyl acetate) 277.5 (dec) Dihydrochloride 185 -H -H -H -CH₃ -COCH₃ -CH₃ White powder (Ethyl acetate) 230.0-232.0 (dec) Hydrochloride 186 -OCH₃ -H -H -H -CH₃ -H White powder (Ethyl acetate) 239.5 (dec) Dihydrochloride 187 -H -H -H -OCH₃ -CH₃ -COCH₃ White powder (Ethyl acetate) 208.0-211.5 Hydrochloride Example R1 R2 R3 R4 R5 Crystal form (Re crystallization solvent) Melting point (°C) Salt 188 -H -H -H -H White powder (Ethyl acetate) 243.5 (dec) Dihydrochloride 189 -H -H -H -H White powder (Ethyl aoetate) 261.5 (dec) Dihydrochloride 190 -H -H -H -Cl White powder (Ethyl acetate) 249.0 (dec) Dihydrochloride 191 -H -H -H -Cl White powder (Ethyl acetate) 253.5 (dec) Triydrochloride 192 -H -H -H -F White powder (Ethyl acetate) 252.0 (dec) Dihydrochloride 193 -H -H -H -CH₃ White powder (Ethyl acetate) 242.0 (dec) Dihydrochloride Example R1 R2 R3 R4 R5 R6 Crystal form (Recrystallization solvent) Melting point (°C) Salt 194 -H -H -H -H -C₂H₃ -C₂H₈ Light yellow powder (Ethyl acetate) 179.0-183.5 Hydrochloride 195 -H -H -H -H -H -H White powder (Ethyl acetate/water) 150.0-154.5 - 196 -H -H -H -H -H -CH₃ White powder (Ethyl acetate) 198.0-207.0 Hydrochloride 197 -H -H -H -H -CH₃ -CH₃ White powder (Ethyl acetate/isopropyl ether) 128.0-129.5 - 198 -H -H -H -H -H -C₂H₃ White powder (Ethyl acetate/isopropyl ether) 1125-113.5 - 199 -H -H -H -H -CH₂CF₃ White powder (Ethyl acetate/isopropyl ether) 126.0-127.0 - 200 -Cl -H -H -H -H -H White powder (2-propanol) 161.5-166.0 - 201 -H -H -H -Cl -H -CH₃ White powder (Ethyl acetate) 194.5-197.0 Hydrochloride 202 -H -H -H -Cl -CH₃ -CH₃ White powder (Ethyl acetate) 197,5-201.0 Hydrochloride 203 -H -H -H -Cl -H -C₂H₅ White powder (Ethyl acetate) 227.5 (dec) Hydrochloride 204 -H -H -H -Cl -H -CH₂CF₃ (Ethyl acetate) 204.0-208.0 Hydrochloride 205 -OCH₃ -H -H -H -H -H White powder (Ethyl acetate/isopropyl ether) 129.0-130.0 - 206 -H -H -H -OCH₃ -H -CH₃ White powder (Ethyl acetate) 176.0-178.5 Hydrochloride 207 -H -H -H -OCH₃ -CH₃ -CH₃ White powder (Ethyl acetate) 188.5-192.0 Hydrochloride 208 -H -H -H -OCH₃ -H -C₃H₅ White powder (Ethyl acetate) 178.0-184.0 Hydrochloride 209 -H -H -H -OCH₃ -H -CH₂CF₃ Light yellow powder (Ethyl acetate) 187.5-192.0 Hydrochloride Example R1 R2 R3 R4 R5 R6 Crystal form (Recrystallization solvent) Melting point (°C) Salt 210 -F -H -H -H -H -H White powder (2-propanol) 148.5-150.0 - 211 -H -H -H -F -H -CH, White powder (Ethyl acetate) 191.0-193.0 Hydrochloride 212 -H -H -H -F -CH₃ -CH₃ White powder (Ethyl acetate) 192.5-197,0 Hydrochloride 213 -H -H -H -F -H -C₂H₃ White powder (Ethyl acetate) 218:0-220.5 Hydrochloride 214 -H -H -H -F -H -CH₂CF₃ Light yellow powder (Ethyl acetate) 197.0-202.0 Hydrochloride 215 -H -H -H -H -H -H White powder (Ethyl acetate/isopropyl ether) 149.5-150.5 - Example R1 R2 R3 R4 R5 Crystal form (Recrystallization solvent) Melting point (°C) Salt 216 -H -H -H -H White powder (Ethyl acetete/isopropyl ether) 130.5-131.5 - 217 -H -H -H -H White powder (Ethyl acetate) 227.5 (dec) Dihydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystallization solvent) Melting point (°C) Salt 218 -H -H -NHCOCH₃ -H -H White powder (Ethanol) 283.0-285.0 Hydrochloride 219 -H -H -NHCO₂CH₃ -H -H Light yellow powder (Ethyl acetate/isopropyl ether) 149.5-150.5. - 220 -H -H -NHSO₂C₂H₈ -H -H Light yellow powder (Ethanol/ethyl acetate) 174-176 Dihydrochloride 221 -H -H -NHC₂H₅ -H -H White powder (Ethyl acetate) 225 (dec) Hydrochloride 222 -H -H -N(CH₃)CO₂CH₉ -H -H White powder (Ethyl acetate) 196.0-2020 Hydrochloride 223 -H -H -N(CH₃)COCH₃ -H -H White powder (Ethanol) 246-247 Hydrochloride 224 -H -H -NH₂ -H -H White powder (Ethanol containing water) 266-271(dec) Hydrochloride 225 -H -H -NHCH₂ -H -H White powder (Ethenol) 264-266 Dihydrochloride 226 -H -H -N(CH₉)₂ -H -H White powder (Ethanol) 269-270 Dihydrochloride 227 -CH₃ -H -NH₂ -H -OCH₃ Light yellow solid (Ethyl acetate) 155.0-158.0 - 228 -OCH₃ -H -NHCON(CH₃)₂ -H -CH₃ White powder (Ethyl acetate) 208.0-210.0 Hydrochloride 229 -OCH₃ -H -NHCHO -H -CH₃ White powder (Ethyl acetate) 247.5-253.0 (dec) Hydrochloride 230 -OCH₃ -H -NHCO₂CH₃ -H -CH₃ White powder (Ethyl acetate) 230.0-235.5 Hydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystallization solvent) Melting point(°C) Salt 231 -H -H -H -H White powder (Ethyl aoetete/2-propenol) 154.5-158.5 - 232 -H -H -H -H White powder (2-propanol) 141.0-144.5 - 233 -OCH₃ -H -H -CH₃ White powder (Ethanol) 247.5-251.0 (dec) Hydrochloride 234 -CH₂OH -H -H -OCH₃ White powder (Ethanol) 144.0-145.0 Hydrochloride Example R1 R2 R3 R4 R5 NMR Salt 235 -H R2 -H -NHCH(CH₃)₂ -H -H ¹H-NMR (DMSO-d₆) δ ppm: 1.24 (6H, d, J = 6.5Hz), 2.2-2.4 (2H, m), 3.15-3.8 (12H, m), 4.15 (2H, t, J = 6Hz), 6.99 (1H, d J = 7.5Hz). 7.11 (2H, d, J = 9Hz), 7.33 (1H, dd, J = 8, 8Hz). 7.4-7.55 (3H, m), 7.71 (1H, d, J = 8Hz). 7.78 (1H, d, J = 5.5Hz), 10.87 (3H, br). Trihydrochloride 236 -OCH, -H -NHCO₂CH₃ -H -H ¹H-NMR (CDCl₃,) δ ppm: 2.00-2.15 (2H, m), 2.60-2.70 (2H, m). 2.73 (4H, brs), 3.20 (4H, brs), 3.77 (3H, s), 3.88 (3H, s), 4.10 (2H, t, J=6.6 Hz), 6.52 (1H, brs), 8.74 (1H, dd, J=2.5, 8.6 Hz), 6.87 (1H, d, J=8.6 Hz), 8.90 (1H, d, J=7.7 Hz), 7.19 (1H, brs). 7.28 (1H, dd. J=7.8, 7.8 Hz). 7.35-7.45 (2H, m), 7.55 (1H, d, J=7.8 Hz). - 237 -H -H -NHCON(CH₃)₂ -H -H ¹H-NMR (DMSO-d₈) δ ppm: 2.20-2.30 (2H, m), 2.91 (6H, s), 3.20-3.40 (6H, m), 3.55 (2H, d, J=12.4 Hz), 3.65 (2H, d. J=11.4 Hz), 4.05 (2H, t, J=6.0 Hz), 6.86 (2H, d. J=9:0 Hz). 6.98 (1H, d, J=7.6 Hz), 7.30-7.40 (3H, m), 7.50 (1H, d, J=5.5 Hz), 7.71 (1H, d, J=8.1 Hz), 7.78 (1H, d J=5.5 Hz), 8.18 (1H, brs), 11.05 (1H, brs). Dihydrochloride 238 -F -H -NHCO₂CH₃ -H -H ¹H-NMR (DMSO-d₈) δ ppm: 2.24 (2H, brs), 3.10-3.25 (2H, m), 3.30-3.50 (4H, m), 3.50-3.60 (2H, m), 3.66 (3H, s), 3.85-3.70 (2H, m), 4.13 (2H, t, J=5.9 Hz), 6.98 (1H, d. J=7.6 Hz). 7.10-7.20 (2H, m), 7.32 (1H, dd, J=7.9, 7.8 Hz), 7.40 (1H, d, J=13.3 Hz), 7.50 (1H, d, J=5.5 Hz), 7.71 (1H. d J=8.1 Hz), 7.77 (1H, d J=5.5 Hz), 9.69 (1H, brs), 10.58 (1H, brs). Hydrochloride Example R1 R2 R3 R4 R5 NMR Salt 239 -H -H -NHCONH₂ -H -H ¹H-NMR (CDCl₃) δ ppm: 1.95-2.10 (2H, m), 2.64 (2H. t. J=7.3 Hz), 2.70-2.75 (4H, m), 3.15-3.20 (4H, m), 4.03 (2H, t, J=6.3 Hz), 4.83 (2H, brs), 6.83 (1H, brs), 8.85-6.95 (3H, m), 7.20 (2H, d, J=8.6 Hz), 7.25-7.30 (1H, m), 7.35-7.45 (2H, m), 7.55 (1H, d. J=8.1 Hz). - 240 -H -H -NHCON(C₂H₃)₂ -H -H ¹H-NMR (DMSO-d₈) δ ppm: 1.06 (6H, t, J=7.0 Hz), 2.15-2.30 (2H, m), 3.20-3.45 (10H, m), 3.54 (2H, d, J=12 Hz), 3.64 (2H, d, J=12 Hz), 4.03 (2H, t, J=5.9 Hz). 6.84 (2H, d, J=8.9 Hz), 6.97 (1H, d J=7.7 Hz), 7.25-7.40 (3H, m), 7.49 (1H, d, J=5.6 Hz), 7.70 (1H, d, J=8.1 Hz), 7.78 (1H, d. J=5.6 Hz). 8.01 (1H, s), 10.95 (1H, s). Dihydrochloride 241 -H -H -H -H ¹H-NMR (DMSO-d₈) δ ppm: 2.05-2.10 (2H, m), 2.67 (2H, t, J=7.3 Hz)_. 278 (4H, brs), 3.22 (4H, brs), 4.11 (2H, t, J=6.3 Hz), 6.91 (1H, d, J=7.8 Hz), 7.01 (2H, d. J=8.9 Hz), 7.20 (2H, d, J=9.0 Hz), 7.25-7.35 (3H, m), 7.35-7.45 (2H, m), 7.58 (1H, d, J=8.0 Hz), 7.77 (1H, s), - 242 -H -H -H -H ¹H-NMR (CDCl₃) δ ppm: 2.05-2.15 (2H, m), 2.67 (2H, t, J=7.2 Hz), 2.75 (4H, brs), 3.21 (4H, brs). 4.12 (2H, t; J=6.3 Hz), 6.91 (1H, d. J=7.6 Hz), 7.00-7.05 (2H, m), 7.25-7.30 (1H, m), 7.35-7.45 (2H, m), 7.50-7.60 (3H, m), 8.08 (1H, s). 8.45 (1H, s). - Example R1 R2 R3 R4 R5 Crystal form (Recrystallization solvent) Melting point(°C) Salt 243 -H -H -CH₂CH₂N(C₂H₅)₂ -H -H White powder (Ethyl acetate) 224.0-232.0 (dec) Dihydrochloride 244 -H -H -H -NHCO₂CH₃ -H White powder (Ethyl acetate) 178.0-181.0 (dec) Hydrochloride 245 -H -H -CN -H -H Light yellow powder (Ethyl acetate/isopropyl ether) 105.5-107.0 - 246 -H -H -CO₂H -H -H White powder (Hydrochloric acid/acetio acid) 263.0 (dec) Hydrochloride 247 -H -H -CO₂CH₃ -H -OCH₃ White powder (Ethyl acetate) 242.0 (dec) Hydrochloride 248 -H -H -Br -H -H White powder (Ethyl acetate/isopropyl ether) 118.0-120.0 - 249 -OCH₃ -H -CO₂H -H -H White powder (Water) 121.0-124.5 - 250 -Cl -H -CO₂C₂H₅ -H -H Light yellow powder (Ethanol/isopropyl ether) 122.0-123.5 - 251 -H -H -CH₂CO₂CH₃ -H -H White powder (Ethyl acetate) 213.5-221.5 (dec) Hydrochloride 252 -H -H -CO₂C₂H₅ -H -F White powder (Ethyl acetate) 231.5-233.5 Hydrochloride . Example R1 R2 R3 R4 R5 Crystal form (Recrystallization solvent) Melting point(°C) Salt 253 -H -H -CO₂H -H -Cl White powder (Hydrochloric acid/acetic acid) 273.0 (dec) Hydrochloride 254 -H -H -CH₂CO₂H -H -H White powder (Hydrochlorio acid/acetio acid) 217.0-222.0 Hydrochloride 255 -H -H -CO₂H -H -F White powder (Hydrochlorio acid/acetio acid) 287.0 (dec) Hydrochloride 256 -H -H -CH₂CH₂NHCH₃ -H -H White powder (Ethyl acetate) 258.0 (dec) Dihydrochloride 257 -H -H -CH₂CH₂N(CH₃)₂ -H -H White powder (Ethyl acetate) 236.5 (dec) Dihydrochloride 258 -H -H -CH₂CH₂N(CH₃)COCH₃ -H -H White powder (Ethyl acetate) 215.0-217.0 Hydrochloride 259 -H -H -CH₂CH₂N(CH₃)COC₂H₅ -H -H White powder (Ethyl acetate) 211.0-217.0 Hydrochloride 260 -H -H -CH₂CH₂N(CH₃)COC₅H₅ -H -H White powder (Ethyl acetate) 210.5-212.0 Hydrochloride 261 -H -H -CH₂CH₂N(CH₃)CH₂C₆H₆ -H -H White powder (Ethyl acetate) 196.0-202.0 (dec) Dihydrochloride 262 -H -H -CH₂CH₂NHC₂H₅ -H -H White powder (Ethyl acetate/isopropyl ether) 230.0 (dec) Dihydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystallization solvent) Melting point(°C) Salt 263 -H -H - -CH₂CH₂NHCH₂CF₃ -H -H White powder (Ethyl acetate) 223.0 (dec) Dihydrochloride 264 -H -H -CH₂CO₂C₂H₅ -H -Cl White powder (Ethyl acetate) 225.0-228.5 Hydrochloride 265 -H -H -CH₂CO₂H - -H -Cl White powder (Hydrochloric acid/acetic acid) 208.0-209.5 Hydrochloride 266 -H -H -CH₂CO₂C₂H₅ -H -OCH₃ White powder (Ethyl acetate) 205.5-213.5 Hydrochloride 267 -CH₃ -H -CN -H -H Light yellow powder (Ethyl acetate/isopropyl ether) 105.5-106.0 - 268 -H -H -CH₂CO₂H -H -OCH₃ White powder (Hydrochloric acid/acetic acid) 198.5-201.0 Hydrochloride 269 -H -H -SO₂NH₂ -H -H White powder (Ethanol) 199.0-203.0 - 270 -H -H -CO₂H -H -CH₃ White powder (Hydrochloric acid/acetic acid) 280.0 (dec) Hydrochloride 271 -H -H -CH₂CO₂C₂H₅ -H -F White powder (Ethyl acetate) 220.5-224.0 Hydrochloride 272 -H -H -CH₂CO₂H -H -F White powder (Hydrochlorid acid/acetic acid) 181.5-184.5 Hydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystallization solvent) Melting point(°C) Salt 273 -H -H -CN -OCH₃ -H White powder (Ethyl acetate) 238.0 (dec) Hydrochloride 274 -H -H -CO₂C₂H₅, -H -Br White powder (Ethyl acetate) 237.5-242.5 (dec) Hydrochloride 275 -H -CN -H -H -H White powder (Ethyl acetate) 217.5-221.0 (dec) Hydrochloride 276 -H -H -CO₂H -H -Br White powder (Hydrochloric acid/acetic acid) 271.0 (dec) Hydrochloride 277 -H -H -H -CO₂H -H White powder (Hydrochlorio acid/acetic acid) 242.5-244.5 Hydrochloride 278 -H -H -H -H -CN White powder (Ethyl acetate) 221.5-226.0 Hydrochloride 279 -CN -H -CO₂C,₂H₅ -H -H White powder (Ethyl acetate/isopropyl ether) 128.5-130.0 - 280 -H -H -CO₂H -H -CN White powder (Dichloromethane/water) 271.0 (dec) Hydrochloride 281 -CONHC₂H₆ -H -H -H -H White powder (Ethyl acetate) 220.0-227.5 Hydrochloride 282 -H -H -CO₂C₂H₅ -CF₃ -H White powder (Ethyl acetate) 224.5-232.0 Hydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystallization solvent) Melting point(°C) Salt 283 -H -H -CO₂C₂H₅ -Cl -H White powder (Ethyl acetate) 218.5-218.0 Hydrochloride 284 -H -H -CO₂H -Cl -H White powder (Ethyl acetate) 259.0 (dec) Hydrochloride 285 -H -OCH₃ -CHO -H -H White powder (Ethyl acetate 2-propanol) 118.0-119.5 - 286 -H -H -CO₂H -CF₃ -H White powder (Water) 240.0 (dec) Hydrochloride 287 -H -H -CN -CH₃ -H White powder (Ethyl acetate) 230.0-237.0 Hydrochloride 288 -NO₂ -H -CO₂C₂H₃ -H -H Light yellow powder (Ethyl acetate/isopropyl ether) 113.0-114.0 - 289 -H -H -CHO -H -H White powder (Ethyl acetate) 102.5-105.5 - 290 -H -H -CO₂H -H -NO₂ White powder (Hydrochloric acid/acetic acid) 259.0 (dec) Dihydrochloride 291 -H -H -CH=CHCO₂H -H -H White powder (Hydrochloric acid/water) 265.0 (dec) Hydrochloride 292 -H -H -CO₂C₂H₆ -H -CF₃ White powder (Ethyl acetate) 211.5-221.0 Hydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystallization solvent) Melting point(°C) Salt 293 -H -H -CO₂H -H -CF₃ White powder (Ethyl acetate) 269.0 (dec) Hydrochloride 294 -H -CH₂CO₂C₂H₆ -H -H -H White powder (Ethyl acetate) 206.0-208.0 Hydrochloride 295 -H -H -CH=CHCONH₂ -H -H White powder (Ethyl acetate) 210.5-215.0 - 296 -H -CH₂CO₂H -H -H -H Light brown powder Ethyl acetate) 255.0 (dec) Hydrochloride 297 -H -H -CH=CHCONHCH₃ -H -H White powder (95%-2-propanol) 165.5-169.0 - 298 -H -H -CH=CHCON(CH₃)₂ -H -H White powder (95%-2-propanol) 130.5-131.5 - 299 -H -H -CH=CHCONHC₂H₆ -H -H White powder (95%-2-propanol) 158.0-159.0 - 300 -H -H -CH=CHCONHCH₂CF₃ -H -H White powder (95%-2-propanol) 177.5-180.0 - 301 -H -H -(CH₂)₂CO=C₂C₂H₅ -H -H White powder (Ethyl acetate) 235.0-237.5 Hydrochloride 302 -F -H -H -CO₂C₂H₅ -H White powder (Ethyl acetate) 218.5-224.0 Hydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystallization solvent) Melting point(°C) Salt 303 -H -H -CH₂CH₂CO₂H -H -H White powder (Hydrochloric acid/acetic acid) 240.0 (dec) Hydrochloride 304 -F -H -H -CO₂H -H White powder (Hydrochloric acid/acetic acid) 260.0 (dec) Hydrochloride 305 -Cl -H -H -CO₂C₂H₅ -H White powder (Ethyl acetate) 241.0-245.0 Hydrochloride 306 -Cl -H -H -CO₂H -H White powder (Hydrochloric acid/acetic acid) 268.0 (dec) Hydrochloride 307 -CH₃ -H -H -CO₂C₂H₅ -H White powder (Ethyl acetate) 238.0-242.0 (dec) Hydrochloride 308 -CH₃ -H -CO₂C₂H₅ -H -CH₃ White powder (isopropyl ether) 106.0-108.0 - 309 -CH₃ -H -H -CO₂H -H white powder (Hydrochloric acid/acetic acid) 256.5 (dec) Hydrochloride 310 -CH₃ -H -CO₂H -H -CH₃ White powder (Water) 252.5 (dec) Hydrochloride 311 -OCH₃ -OCH₃ -H -CO₂C₂H₅ -H White powder (Ethyl acetate) 225.0-234.0 Hydrochloride 312 -H -H -C(CH₃)₂CO₂CH₃ -H -H White powder (Ethyl acetate) 222.0-226.5 Hydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystallization solvent) Melting point(°C) Salt 313 -OCH₃ -H -H -CO₂C₂H₅ -H White powder (Ethyl acetate) 208.0-213.5 Hydrochloride 314 -H -H -C(CH₃)₂CO₂H -H -H White powder (Hydrochloric acid/acetio acid) 257.5 (dec) Hydrochloride 315 -H -H -CH₂CH₂CONH₂ -H -H Light yellow powder (95%-2-propanol) 167.5-170.0 - 316 -H -H -CH₂CH₂CONHCH₃ -H -H White powder (95%-2-propanol) 128.0-132.0 - 317 -OCH₃ -H -H -CO_2H -H White powder (Hydrochloric acid/water) 250.0 (dec) - Hydrochloride 318 -H -H -CH₂CH₂CONHC₂H₅ -H -H White powder (95%-2-propanol) 130.5-132.0 Hydrochloride 319 -H -CH₂CONH₂ -H -H -H White powder (Ethyl acetate/isopropyl ether) 132.5-134.0 Hydrochloride 320 -H -H -H -CH₂CONHCH₃ -H White powder (Ethyl acetate) 173.5-175.0 Hydrochloride 321 -OCH₃ -OCH₃ -H -CO₂H -H White powder (Water) 154.0-155.5 Hydrochloride 322 -OCH₃ -H -CO₂C₂H₅ -H -OCH₃ White powder (Ethyl acetate) 239.0-242.0 (dec) Hydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystallization solvent) Melting point(°C) Salt 323 -OCH₃ -H -CO₂H -H -OCH₃ White powder (Water) 191.0-196.0 - 324 -H -H -CSNHC₂H₅ -H -H Light yellow powder (Ethyl acetate/THF) 193.0-196.5 Dihydrochloride 325 -OCH₃ -H -COCH₃ -H -CH₃ White powder (Ethyl acetate) 243.0 (dec) Hydrochloride 326 -CH₂CH=CH₂ -H -CO₂H -H -OCH₃ White powder (Water) 97.0-102.0 - 327 -C,H, -H -CO₂H -H -OCH₃ White powder (Water) 145.5-150.5 - Example R1 R2 R3 R4 R5 Crystal form (Recrystallization solvent) Melting point(°C) Salt 328 -H -H -H -H White powder (Ethyl acetate/isopropyl ether) 112.5-113.5 - 329 -H -H -H -H White powder (Ethyl acetate/isopropyl ether) 112.0-113.0 - Example R1 R2 R3 R4 R5 NMR Salt 330 -H -H -F -H -H ¹H-NMR (DMSO-d₆) δ ppm: 2.15-2.30 (2H, m), 3.10-3.25 (2H, m), 3.25-3.60 (4H, m), 3.55-3.75 (4H, m), 4.10 (2H, t, J=6.0 Hz), 8.90-7.10 (4H, m), 7.25-7.40 (3H, m), 7.51 (1H, d, J=5.6 Hz), 7.72 (1H, d, J=8.3 Hz), 7.78 (1H, d, J=5.5 Hz), 10.12 (1H, brs). Hydrochloride 331 -H -H -H -H -H Hydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystalization solvent) Melting point (°C) Salt 332 -H -H -H -H -NHCOCH₃ Colorless needle-form crystal (Ethanol) 243.7 - 244.8 - Example R1 R2 R3 R4 R5 NMR Salt 333 -H -H -COCH₃ -H -OCH₃ ¹H-NMR (DMSO-d₈) δ ppm : 220-2.40 (2H, m), 2.53 (3H, s), 3.20-3.70 (10H, m), 3.83 (3H, s). 4.19 (2H, t, J=5.8 Hz). 6.96 (1H, d, J=7.5 Hz), 7.10 (1H, d, J=8.5 Hz), 7.31 (1H, t, J=7.8 Hz), 7.45-7.50 (2H, m), 7.62 (1H, dd, J=2.0, 8.4 Hz), 7.69 (1H, d, J=8.0 Hz), 7.76 (1H, d, J=5.5 Hz). 11.14 (1H, brs). Hydrochloride 334 -OCH₃ -H -H -H -OCH₃ Hydrochloride 335 -H -H -H -H ¹H-NMR (CDCl₃) δ ppm: 1.95-2.10 (6H, m), 2.60-2.75 (7H, m), 2.96 (2H, t, J=11.3 Hz). 3.21 (4H, brs), 3.55 (2H, d, J=12.4 Hz). 4.08 (2H, t, J=8.2 Hz), 6.80-6.95 (3H, m), 7.17 (2H, d, J=8.5 Hz), 7.25-7.35 (1H, m), 7.40 (1H, d, J=5.5 Hz), 7.43 (1H, d, J=5.6 Hz), 7.57 (1H, d, J=8.1 Hz). - 336 -H -H -H -H ¹H-NMR (CDCl₃) δ ppm: 1.55-1.65 (2H, m), 1.80-1.95 (2H, m), 2.00-2.10 (2H, m), 2.13 (3H, s). 2.55-2.75 (7H. m), 3.10-3.20 (6H. m), 3.83 (1H, d, J=13.7 Hz), 4.05 (2H, t, J=8.4 Hz), 4.78 (1H, d, J=13.3 Hz), 6.85-6.95 (3H, m), 7.11 (2H, d, J=8.8 Hz), 7.25-7.30 (1H, m), 7.39 (1H, d, J=5.6 Hz), 7.42 (1H, d, J=5.5 Hz). 7.55 (1H, d, J=8.1 Hz). - 337 -H -H -H -H ¹H-NMR (CDCl₃) δ ppm: 1.75-1.85 (4H, m), 2.00-2.10 (4H, m), 2.32 (3H. s). 2.35-2.45 (1H, m), 2.63 (2H, t, J=7.4 Hz). 2.73 (4H, brs), 2.96 (2H, d, J=11.5 Hz), 3.20 (4H, brs), 4.04 (2H, t, J=6.3 Hz), 6.85-6.95 (3H, m), 7.14 (2H, d, J=8.6 Hz), 7.25-7.30 (1H, m), 7.35-7.45 (2H, m), 7.55 (1H, d, J=8.1 Hz). - Example R1 R2 R3 R4 R5 NMR Salt 338 -H -H -F -H -H ¹H-NMR (DMSO-d₆) δ ppm: 3.10-3.25 (2H, m), 3.40-3.75 (8H, m), 4.40-4.45 (2H, m), 6.98 (1H, d, J=7.7 Hz), 7.00-7.25 (4H, m). 7.33 (1H, dd, J=7.9, 7.8 Hz), 7.50 (1H, d, J=5.6 Hz), 7.71 (1H, d J=8.0 Hz), 7.78 (1H, d, J=5.5 Hz), 10.37 (1H, brs). Hydrochloride 339 -H -H -H -H -H ¹H-NMR (DMSO-d₆) δ ppm: 3.10-3.35 (2H, m), 3.40-3.80 (8H, m). 4.48 (2H. t. J=4.8 Hz), 8.85-7.10 (4H, m), 7.25-7.40 (3H, m). 7.51 (1H, d, J=5.5 Hz), 7.71 (1H, d, J=8.1 Hz), 7.77 (1H, d, J=5.5 Hz), 10.80-11.20 (1H, br). Hydrochloride Example R1 R2 R3 R4 R5 NMR Salt 340 R1 -H -H -H -H -H ¹H-NMR (DMSO-d₆) δ ppm: 1.70-2.00 (4H, m), 3.10-3.40 (6H, m), 3.50-3.80 (4H, m), 4.03 (2H. t. J=5.9.Nz), 6.90-7.00 (5H, m), 7.25-7.40 (3H, m), 7.50 (1H. d, J=5.6 Hz), 7.71 (1H, d .1=8.0 Hz), 7.77 (1H, d, J=5.5 Hz), 10.59 (1H. brs) Hydrochloride 341 -H -H -F -H -H ¹H-NMR (DMSO-d₆) δ ppm: 1.75-1.95 (4H, m), 3.10-3.50 (8H. m), 3.50-3.65 (4H, m), 4.00 (2H. t, J=5.9 Hz), 8.90-7.00 (3H, m), 7.00-7.20 (2H, m), 7.32 (1H, dd, J=7.9, 7.8 Hz), 7.50 (1H, d, J=5.5 Hz). 7.71 (1H, d, J=8.0 Hz), 7.77 (1H, d, J=5.5 Hz), 10.40-10.80 (1H, br). Hydrochloride 342 -H -H -COCH₃ -H -OCH₃ ¹H-NMR (DMSO-d₆) δ ppm: 1.80-1.95 (4H, m). 2.52 (3H, s). 3.20-3.35 (6H, m). 3.50-3.85 (4H, m). 3.83 (3H, s), 4.00-4.15 (2H, m), 6.95 (1H, d, J=7.5 Hz), 7.08 (1H, d, J=8.5 Hz). 7.30 (1H, dd, J=7.8, 7.8 Hz), 7.40-7.50 (2H. m), 7.81 (1H. dd, J=1.9, 8.4 Hz). 7.69 (1H, d, J=8.1 Hz), 7.75 (1H, d, J=5.6 Hz), 11.0 (1H, brs). Hydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystallization solvent) Melting point(°C) Salt 343 -H -H NHCO₂CH₃ -H -H White powder (Ethyl acetate) 241.0 (dec) Hydrochloride 344 -H -H -H -NHCO₂CH₃ -H White powder (Ethyl acetate) 203.0-209.5 Hydrochloride 345 -H -H -CN -H -H White powder (Ethyl acetate) 220.0-223.0 (dec) Hydrochloride 346 -H -H -CO₂H -H -H White powder (Hydrochloric acid/acetic acid) 247.5-250.0 (dec) Hydrochloride 347 -H -CN -H -H -H White powder (Ethyl acetate) 196.0-198.5 Hydrochloride 348 -H -H -H -CO₂H -H White powder (Ethyl acetate) 255.5-258.5 Hydrochloride 349 -CN -H -H -H -H White powder (Ethyl acetate) 187.5-188.5 Hydrochloride 350 -H -H -H -CONHCH₂CF₃ -H White powder (Ethyl acetate/2-propanol) 137.0 (dec) Hydrochloride 351 -H -H -H -CONHC₂H₅ -H Light yellow powder (Ethyiecetate/2-propenol) 130.0-135.0 Hydrochloride 352 -H -H -H -H -CO₂H White powder (Dichloromethane/water) 192.0-197.0 Hydrochloride 353 -H -CONH₂ -H -H -H Light yellow powder (2-propanol) 148.0-151.0 - Example R1 R2 R3 R4 R5 Crystal form (Recrystallizatfon solvent) Melting point(°C) Salt 354 -H -H -H -CONHCH₃ -H Light yellow powder (Ethyl acetate) 234.0-239.0 Hydrochloride 355 -H -H -H -CON(CH₃)₂ -H Light yellow powder (Ethyl acetate) 135.0-141.5 Hydrochloride 356 -H -H -H -H -CONHC₂H₅ White powder (Ethyl acetate) 209.5-213.0 Hydrochloride Example R1 R2 R3 R4 R5 NMR Salt 357 -H -H -(CH₂)₂N(CH₃)CO₂C(CH₃)₃ -H -H ¹H-NMR (CDCl₃) δ ppm: 1.43(9H, s), 1.97-2.07 (2H, m), 284(2H, t J=7.5Hz), 2.69-2.87(6H, m), 2.81(3H, s), 3.15-3.27(4H, m), 3.38 (2H, t, J=7.5Hz), 4.04 (2H, t, J = 8.3Hz), 8.83-8.92 (3H, m), 7.02-7.15(2H, m), 7.28(1H, t, J=7.8Hz), 7.37-7.43 (2H, m), 7.55(1H, d, J=8.80Hz) - 358 -H -H -H -H ¹H-NMR (CDCl₃) δ ppm: 1.60-2.10 (6H, m), 2.30-2.40 (2H, m), 2.47 (3H, s), 2.60-2.70 (1H, m), 2.74 (4H, br), 2.85-3,00 (2H, m), 3.20 (4H, br), 3.90-4.10 (4H, m), 6.85-6.95 (2H, m), 7.07 (1H, d, J=8.8 Hz), 7.25-7.45 (3H, m), 7.56 (1H, d, J=8.0 Hz), 7.69 (2H, d, J=8.2 Hz). - 359 -H -H -H -H -CO₂H ¹H-NMR (DMSO-d₆) δ ppm : 2.20-2.43 (2H, m), 3.17-3.77 (10H, m), 4.30 (2H, t, J=8.0 Hz), 6.90-7.20 (2H, m), 7.30-7.40 (2H, m), 7.50-7.03 (1H, m), 7.70-7.79 (4H, m), 11.00 (1H, br), 12.71(1H, br). - 360 -OCH₃ -H -CO₂CH₃ -H -CH₃ ¹H-NMR (CDCl₃) δ ppm: 1.95-2.10 (2H, m), 2.31 (3H, s), 2.60-2.80 (6H, m), 3.10-3.30 (4H, m), 3.89 (6H, s), 4.10 (2H, t, J = 8.4Hz), 6.90 (1H, dd, J = 0.5, 7.6Hz), 7.27 (1H, dd, J = 7.8, 7.8Hz), 7.35-7.45 (3H, m), 7.50-7.60 (2H, m). - 361 -OCH₃ -H -CO₂H -H -CH₃ ¹H-NMR (DMSO-d₆) δ ppm : 1.90-2.05 (2H, m), 2.28 (3H, s), 2.55-3.30 (10H, m), 3.85 (3H, s), 4.03 (2H, t, J = 6.1Hz), 6.93 (1H, d, J = 7.6Hz), 7.29 (1H, dd, J = 7.8, 7.8Hz), 7.35-7.50 (3H, m), 7.65 (1H, d. J = 8.0Hz), 7.72 (1H, d, J = 5.5Hz), 11.50-13.50 (1H, br). - Example R1 R2 R3 R4 R5 NMR Salt 362 -CH₂CH=CH₂ -H -CO₂CH₃ -H -OCH₃ ¹H-NMR (CDCl₃) δ ppm: 1.98-2.09(2H, m), 2.70-2.83(6H, m), 3.13-3.30(4H, m), 3.45(2H, d, J=6.5Hz), 3.89(3H a), 4.10(2H, t, J=8.4Hz), 5.04-5.11(2H, m), 5.91-0.09(1H, m), 6.90(1H, d, J=7.5Hz), 7.24-7.31(1H. m), 7.38-7.44(2H, m), 7.47-7.57(3H, m). - 363 -C₃H₇ -H -CO₂CH₃ -H -OCH₃ ¹H-NMR (CDCl₃) δ ppm: 0.97(3H. t, J=7.3Hz), 1.52-1.74(2H, m), 1.93-2.13(2H, m), 2.57-2.85(6H, m), 3.07-3.30(4H, m), 3.89(6H, s), 4.09(2H, t, J=6.3Hz), 6.90(1H, d, J=7.5Hz), 7.24-7.31(1H, m), 7.38-7.45(3H, m), 7.52-7.57(2H, m). - Example R1 n Crystal form (Recrystallization solvent) Melting point(°C) Salt 364 3 White powder (Ethyl acetate) 1 28.0-1 38.5 Hydrochloride 365 3 White powder (Ethyl acetate) 130.0-136.0 Hydrochloride 366 3 White powder Fumarate Example R1 n Crystal form (Recrystallization solvent) Melting point(°C) Salt 367 3 White powder (Ethyl acetate) 151.5-158.5 Hydrochloride Example R1 R2 MS(M+1) 368 -H -cyclo-C₈H₁₁ 478 369 -CH₂CH(CH₃)₂ -CH₂CH(CH₃)₂ 508 370 -CH₂CH₂OH -CH₂CH₂OH 484 371 -CH₃ -CH₂CH₂N(CH₃)₂ 481 372 -CH₂CH₂OCH₃ -CH₂CH₂OCH₃ 512 373 -C₃H₇ -CH₂-cyclo-C₃H₅ 492 374 -CH₂CH=CH₂ -cyclo-C₅H₉ 504 375 -C₂H₃ -C₂H₅ 452 376 -H -C₄H₉ 452 377 -H -C(CH₃)₃ 452 378 -H -cyclo-C₇H₂₃ 492 379 -C₂H₅ -cyclo-C₆H₁₁ 506 380 -C₂H₅ -CH(CH₃)₂ 466 381 -H -CH₂CH(CH₃)₂ 452 382 -H -CH₂CH₂OCH₃ 454 383 -H -CH₂CH₂OC₂H₅ 488 384 -H -(CH₂)₃OC₂H₅ 482 385 -H -1-CH₃-CYCLOHEXYL 492 386 -H -CH₂-cyclo-C₃H₅ 450 387 -H -CH₂-cyclo-C₆H₁₁ 492 388 -H -CH₂CO₂CH₃ 468 389 -H -CH₂CONH₂ 453 390 -CH₃ -CH₂CO₂CH₃ 482 391 -H -CH₂CCH 434 392 -CH₃ -CH(CH₃)₂ 452 393 -H -(CH₂)₂CH(CH₃)₂ 466 394 -H -CH(CH₃)C(CH₃)₃ 480 395 -H -CH₂CH₂N(CH₃)₂ 467 396 -CH₃ -CH₂-cyclo-C₃H₅ 464 397 -H -CH₂CF₃ 478 398 -CH₃ -cyclo-C₆H₁₁ 492 399 -C₂H₅ -CH₂CH₂OH 468 400 -CH₂CH₂OH -cyclo-C₆H₁₁ 522 401 -H -cyclo-C₅H₉ 464 402 -H -3-PYRIDYL 473 403 -H -4-PYRIDYL 473 404 -CH₂CH₂OH -C₆H₅ 516 Example R1 R2 MS (M+1) 405 -H -C₆H₅ 435 406 -H -CH₂CH₂C(CH₃)₃ 468 407 -H -CH(C₂H₅)₂ 449 408 -H -CH₂CN 566 409 -H -(CH₂₎₃OCH₃ 523 410 -H -CH₂CH₂CN 523 411 -(CH₂)₃N(CH₃)₂ -(CH₂)₃N(CH₃)₂ 481 412 -CH₃ -(CH₂)₃N(C₂H₅)₂ 482 413 -C₂H₆ -(CH₂)₂N(C₂H₅)₂ 523 414 -H -(CH₂)₂NHCOCH₃ 481 415 -H -(CH₂)₅OH 495 416 -H -(CH₂)₂N(I-Pr)₂ 524 417 -H -(CH₂)₂N(CH₃)₂ 524 418 -H -(CH₂)₂N(C₂H₅)₂ 563 419 -CH₃ -(CH₂)₂CO₂C₂H₅ 509 420 -H -(CH₂)₄CO₂C₂H₅ 493 421 -cyclo-C₅H₉ -(CH₂)₂N(C₂H₅₎₂ 528 422 -CH₃ -(CH₂)₂N(C₂H₅)₂ 484 423 -H NHCH₂CF₃ 496 424 -H -CH₂CF₂CF₃ 482 425 -H -CH₂CH(OCH₃)₂ 442 426 -H -(CH₂)₃OCH(CH₃)₂ 467 427 -H -(CH₂)₂OCH(CH₃)₂ 470 428 -H -CH₂CH₂F 435 429 -H -CH₂CONHCH₃ 468 430 -H -CH₂CH₂SCH₃ 449 Example R1 R2 MS (M+1) 431 -H 510 432 -H 524 434 -H 495 435 -H 496 436 -H 482 437 -H 467 438 -H 466 439 -H 480 440 -H 568 441 -H 554 Example R1 R2 MS (M+1) 442 -H 496 443 -H 482 444 -H 468 445 -H 470 446 -H 450 447 -H 509 448 -H 481 449 -H 450 450 -H 478 Example R1 R2 MS (M+1) 451 -H 494 452 -H 492 453 -H 536 454 -CH₃ 516 455 -CH₃ 520 456 -H 551 457 -H 506 458 -H 502 459 -H 502 460 -H 502 Example R1 R2 MS (M+1) 461 -H 508 462 -H 506 463 -H 540 464 -H 554 465 -H 554 466 -H 487 467 -H 533 468 -CH₃ 515 469 -H 487 Example R1 R2 MS (M+1) 470 -H 487 471 -H 487 472 -C₂H₅ 529 473 -C₂H₅ 515 474 -H 501 475 -H 501 476 -H 501 477 -CH₃ 507 478 -CH₃ 535 479 -H 535 Example R1 R2 MS (M+1) 480 -H 551 481 -H 579 482 -H 479 483 -H 493 484 -H 507 485 -H 565 486 -H 465 487 -H 479 488 -H 493 489 -H 507 Example R1 R2 MS (M+1) 490 -H 507 491 -H 521 492 -H 507 493 -H 536 494 -H 507 495 -H 509 496 -H 523 497 -H 476 498 -H 490 499 -H 504 Example R1 R2 MS (M+1) 500 -H 476 501 -H 480 502 -H 480 503 -C₂H₅ 522 504 -H 494 505 -H 482 506 -H 496 507 -H 492 508 -H 506 509 -H 492 Example R1 R2 MS (M+1) 510 -H 508 511 -H 489 512 -H 503 513 -H 489 514 -H 490 515 -H 538 516 -H 528 517 -H 518 518 -H 518 519 -H 504 Example R1 R2 MS (M+1) 520 -H 520 521 -H 504 522 -H 533 523 -H 490 524 -H 479 525 -H 494 526 -H 491 527 -H 502 528 -H 528 529 -H 533 Example R1 R2 MS (M+1) 530 R1 512 531 -H 511 532 -H 539 533 -H 528 534 -H 523 535 -H 523 536 -H 555 537 -H 571 538 -H 555 539 -H 570 Example R1 MS (M+1) 540 -H 465 541 -C₄H₈ 521 542 -CH(C₂H₅)₂ 535 543 -CH(CH₃)₂ 507 544 -C(CH₃)₂ 535 545 -C₃H₇ 507 546 -C₂H₅ 493 547 -C₆H₁₃ 549 548 -cyclo-C₅H₉ 533 549 -cyclo-C₇H₁₃ 561 550 -CH₂CH₂OH 509 551 -CH₂CH₂OC₃ 523 552 -(CH₂)₃OCH₃ 537 553 -(CH₂)₄OCH₃ 551 554 -CO₂C₂H₅ 537 555 -CO₂C(CH₃)₃ 565 556 -COCH₃ 507 557 -(CH₂)₃N(CH₃)₂ 550 558 -CH₂CH₂N(CH₃)₂ 536 Example R1 MS (M+1) 559 576 560 578 561 562 562 551 563 565 564 549 565 576 566 576 567 576 568 556 569 556 Example R1 MS (M+1) 570 556 571 570 572 570 573 632 574 559 575 545 576 561 577 -4-PYRIDYL 542 578 -3-PYRIDYL 542 575 -2-PYRIDYL 542 580 567 581 556 582 556 Example R1 MS (M+1 ) 583 610 584 598 Example R1 MS (M+1) 585 450 586 480 587 493 588 466 589 507 590 549 591 507 592 533 593 547 594 562 595 535 Example R1 MS (M+1) 596 464 597 492 598 480 599 480 600 494 601 494 602 549 603 507 604 494 605 564 Example R1 MS (M+1) 606 536 607 536 608 536 609 521 610 578 611 547 612 576 613 562 614 549 615 576 616 522 Example R1 MS (M+1) 617 478 618 482 619 494 620 563 621 479 622 493 623 556 624 476 625 468 626 504 Example R1 MS (M+1) 627 600 628 498 629 512 630 551 Example R1 R2 MS (M+1) 631 -H -cyclo-C₆H₁₁ 522 632 -H -CH(CH₃)₂ 482 633 -H -C₄H₉ 496 634 -H -cyclo-C₃H₅ 480 635 -H -cyclo-C₇H₁₃ 536 636 -H -CH₂C₆H₅ 530 637 -H -C₃H₇ 482 638 -H -CH₂CH(CH₃)₂ 496 639 -H -CH₂CH₂OCH₃ 498 640 -H -CH₂CH₂OC₂H₅ 512 641 -H -(CH₂)₃OC₂H₅ 526 642 -H -1-CH₃-CYCLOHEXYL 536 643 -H -(CH₂)₂OC₆H₅ 560 644 -H -cyclo-C₅H₉ 508 645 -H -CH₂-cyclo-C₃H₅ 494 646 -H -CH₂-cyclo-C₆H₁₁ 536 647 -H -CH(CH₃)C₆H₅ 544 648 -H -(CH₂)₂C₆H₅ 544 649 -H -CH₂CO₂CH₃ 512 650 -H -CH₂CONH₂ 497 651 -H -CH₂CCH 478 652 -H -(CH₂)₂CH(CH₃)₂ 510 653 -H -CH(CH₃)C(CH₃)₃ 524 654 -H -CH₂C(CH₃)₃ 510 655 -CH₃ -cyclo-C₆H₁₁ 536 656 -C₂H₅ -C₂H₅ 496 657 -H -C(CH₃)₃ 496 658 -CH₃ -CH₂C₈H₅ 544 659 -C₂H₅ -CH(CH₃)₂ 510 660 -CH₃ -CH₂CO₂CH₃ 526 661 -CH₃ -CH(CH₃)₂ 496 662 -CH₃ -CH₂-cyclo-C₃H₅ 508 663 -H CH₂CF₃ 522 664 -H -CH(C₂H₅)₂ 510 Example R1 R2 MS (M+1) 665 -H -(CH₂)₃OCH₃ 512 666 -H -CH₂CH₂OH 484 667 -H -CH₂CN 479 668 -C₂H₅ -2-PYRIDYL 545 669 -H -3-PYRIDYL 517 670 -H -C₆H₅ 516 671 -H -(CH₂)₂NHCOCH₃ 525 672 -H -CH₂CH(C₂H₅)₂ 524 673 -H -CH₂CH(OCH₃)₂ 528 674 -H -(CH₂)3OCH(CH₃)₂ 540 675 -H -(CH₂)₂OCH(CH₃)₂ 526 676 -H -CH₂CH₂F 486 677 -H -CH₂CONHCH₃ 511 678 -H -CH₂CH₂SCH₃ 514 679 -H -CH₂CHF₂ 504 Example R1 MS (M+1) 680 -H 554 681 -H 568 682 -H 539 683 -H 598 684 -H 540 685 -H 526 686 -H 511 687 -H 494 688 -H 540 689 -H 612 690 -C₂H₅ 522 Example R1 R2 MS (M+1) 691 -H 526 692 -H 512 693 -H 514 694 -H 496 695 -H 494 696 -H 522 697 -H 538 698 -H 536 699 -H 580 700 -CH₃ 560 701 -CH₃ 544 Example R1 R2 MS (M+1) 702 -CH₃ 564 703 -H 562 704 -H 562 705 -H 584 706 -H 600 707 -H 572 708 -H 550 709 -H 546 710 -H 546 711 -H 546 712 -H 550 Example R1 R2 MS (M+1) 713 -H 550 714 -H 530 715 -H 558 716 -H 574 717 -H 576 718 -H 592 719 -H 581 720 -H 580 721 -H 576 722 -H 576 Example R1 R2 MS (M+1) 723 -H 560 724 -H 603 725 -H 576 726 -H 556 727 -H 558 728 -H 564 729 -H 564 730 -H 564 731 -H 572 732 -H 560 733 -H 560 Example R1 R2 MS (M+1) 734 -H 574 735 -H 574 736 -H 578 737 -H 598 738 -H 614 739 -H 574 740 -H 548 741 -H 590 742 -H 544 743 -H 562 744 -H 602 Example R1 R2 MS (M+1) 745 -H 588 746 -H 587 747 -H 560 748 -H 562 745 -H 574 750 -H 578 751 -H 558 752 -H 558 753 -H 578 754 -H 562 Example R1 R2 MS (M+1) 755 -H 590 756 -H 574 757 -H 830 758 -CH₃ 558 759 -CH₃ 588 760 -CH₃ 574 761 -H 598 762 -H 548 763 -H 598 764 -H 548 Example R1 R2 MS (M+1) 765 -H 566 766 -H 614 767 -H 562 768 -H 562 769 -H 562 770 -H 580 771 -H 612 772 -H 612 773 -H 612 Example R1 R2 MS (M+1) 774 -H 576 775 -H 576 776 -H 576 777 -H 594 778 -H 626 779 -H 626 780 -H 626 781 -H 566 782 -H 628 Example R1 R2 MS (M+1) 783 -H 602 784 -H 606 785 -C₂H₅ 584 786 -H 566 787 -H 580 788 -H 531 789 -H 531 790 -H 531 791 -H 545 792 -C₂H₅ 573 Example R1 R2 MS (M+1) 793 -C₂H₈ 559 794 -H 545 795 -H 545 796 -H 579 797 -CH₃ 675 798 -H 565 799 -H 551 800 -H 520 801 -H 534 802 -H 548 Example R1 R2 MS (M+1) 803 -H 520 804 -H 524 805 -H 524 806 -H 538 807 -H 526 808 -H 540 809 -H 536 810 -H 550 811 -H 536 812 -H 550 Example R1 R2 MS (M+1) 813 -H 533 814 -H 533 815 -H 562 816 -H 548 817 -H 548 818 -H 577 819 -H 592 820 -H 534 821 -H 537 822 -H 546 823 -H 556 Example R1 R2 MS (M+1) 824 -H 583 825 -H 598 826 -H 570 827 -H 572 828 -H 599 829 -H 615 830 -H 598 Example R1 R2 R3 R4 R5 MS (M+1) 831 -H -H -NHCOCH₃ -H -H 410 832 -H -NHCOCH₃ -H -H -H 410 833 -H -H -OCH₃ -H -H 383 834 -H -H -Cl -H -H 387 835 -H -H -CH₆ -H -H 367 836 -H -H -CF₃ -H -H 421 837 -H -H -OCF₃ -H -H 437 838 -H -H -SCH₃ -H -H 399 839 -H -H C₆H₅ -H -H 429 840 -H -H -OCH₂C₆H₅ -H -H 459 841 -H -H -NO₂ -H -H 398 842 -H -H -COCH₃ -H -H 395 843 -OCH₃ -OCH₃ -H -H -H 413 844 -OCH₃ -H -H -H -OCH₃ 413 845 -H -OCH₃ -OCH₃ -H -H 413 846 -H -CH₃ -H -H -H 367 847 -CH₃ -H -H -H -CH₃ 381 848 -F -H -H -H -H 371 849 -H -F -H -H -H 371 850 -H -H -F -H -H 371 851 -F -H -F -H -H 389 852 -H -F -H -H -H -F 389 853 -F -H -H -H -F 389 854 -F -H -H -CH₃ -H 385 855 -H -H -CH₂CO₂CH₃ -H -H 425 856 -CH₃ -H -COCH₃ -H -H 409 857 -H -OC₆H₅ -H -H -H 445 858 -H -H -H -H 420 859 -H -H -H -H 419 Example R1 MS (M+1) 860 407 861 393 862 407 863 407 864 421 865 421 866 419 867 419 868 428 Example R1 MS (M+1) 869 433 870 433 871 437 Example R1 R2 R3 R4 R5 Crystal form (Recrystalization solvent) Melting point (°C) salt 872 -OCH₃ -H -NHSO₂C₂H₅ -H -CH₃ White powder (Ethyl acetate) 235.5-237.5 Hydrochloride 873 -CH₃ -H -CONHCH₃ -H -OH White powder (Ethyl acetate) 246.5 (dec) Hydrochloride 874 -CH₃ -H -Br -H -OCH₃ White powder (Ethanol/ethyl acetate) 265.0 (dec) Hydrochloride 875 -OCH₃ -H -NHCOCH₂NHCO₂C (CH₃)₃ -H -CH₃ White powder (Ethyl acetate/ isopropyl ether) 140.5-142.5 - 876 -CH₃ -H -NHCOCH₂NH₂ -H -OCH₃ White powder (Methanol/water) 268.0 (dec) Dihydrochloride 877 -OCH₃ -H -NHCOCH₂NHCOCH₃ -H -CH₃ White powder (Ethyl acetate)/ isopropyl ether) 167.5-170.5 - 878 -OCH₃ -H -NHCOCH₂NHCO₂2H₃ -H -CH₃ White powder (Ethyl acetate)/ Isopropyl ether) 157.0-159.5 - 879 -CH₃ -H -NHCOCH₂NHCHO -H -OCH₃ White powder (Dichloromethane/water) 235.5 (dec) Hydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystalization solvent) Melting point (°C) salt 880 -CH₃ -H -CONHCH₃ -H -O(CH₂)₂N(CH₃)₂ White powder (Ethyl acetate) 235.5-240.5 (dec) Dihydrochloride 881 -CH₃ -H -CONHCH₃ -H -O(CH₂)₂OH₃, White powder (isopropyl alcohol/ isopropyl ether) 194.0-197.5 Hydrochloride 882 -CH₃ -H -CONHCH₃ -H -OCH₂CF₃ Light yellow powder (Ethyl acetate)/ Isopropyl ether) 156.0-157.5 Hydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystalization solvent) Melting point (°C) Salt 883 -H -H -H -H White powder (Ethyl acetate/ isopropyl ether) 114.0-115.5 - 884 -OCH₃ -H -H -CH₃ Whitepowder (Ethanol/ ethyl acetate) 245.0 (dec) Hydrochloride 885 -H -H -H -H White powder (Ethyl acetate) 217.0-224.5 (dec) Hydrochloride 886 -OCH₃ -H -H -CHO White powder (Ethanol) 218.0 (dec) Hydrochloride 887 -CCH₃ -H -H -CH₂OH White powder (Ethanol) 224.0-226.5 (dec) Hydrochloride 888 -OCH₃ -H -H -CH₂OCH₃ White powder (methanol) 224.0-226.0 Hydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystalization solvent) Melting point (°C) Salt 889 -OCH₃ -H -H -CH₂(CH₃)₂ White powder (Ethanol/other) 151.0-152.0 Difumarate 890 -OCH₃ -H -H -CH₃ Light yellow powder (Ethanol/water) 264.0 (dec) Hydrochloride 891 -OCH₃ -H -H -CH₃ Light yellow powder (Ethyl acetate/ Isopropyl ether) 143.5-151.0 - 892 -OCH₃ -H -H -CH₃ White powder (Ethyl acetate) 246.5-249.0 (dec) Hydrochloride 893 -OCH₃ -H -H -CH₃ Light yellow powder (Ethyl acetate) 234.0-240.0 (dec) Dihydrochloride 894 -OCH₃ -H -H -CH₃ White powder (Methenol/weter) 288.5 (dec) Dihydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystalization solvent) Melting point (°C) Salt 895 -OCH₃ -H -H -CH₃ White powder (Ethanol/water) 218.0-221.5 Hydrochloride 896 -OCH₃ -H -H -CH₃ White powder (Ethanol/ethyl acetate) 223.0-228.0 Hydrochloride 897 -OCH₃ -H -H -CH₃ White powder (Ethyl acetate/ isopropyl ether) 139. 5-142. - 898 -OCH₃ -H -H -CH₃ White powder (Ethyl acetate) 270. 0 (dec) Trihydrochloride 899 -OCll₃ -H -H -CH₃ White powder (Ethyl acetate) 257.0-261.0 0 (dec) Hydrochloride 900 -OCH₃ -H -H -CH₂OH White powder (Ethyl acetate) 217.5-221.0 0 Hydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystalization solvent) Melting point (°C) Salt 901 -OCH₃ -H -H -CH₃ White powder (Ethyl acetate) 250. 0 (dec) Hydrochloride 902 -OCH₃ -H -H -CHO Light yellow powder (Ethyl acetate) 225. 0 (dec) Hydrochloride 903 -OCH₃ -H -H -CH₂OH White powder (Ethyl acetate/ isopropyl ether) 128.0-130.0 - 904 -OCH₃ -H -H -CH₃ White powder. (Ethyl acetate) 246.0 (dec) Hydrochloride 905 -OCH₃ -H -H -CH₃ White powder (Ethyl acetate). 248.0-251.0 (dec) Dihydrochloride Example R1 R2 R3 R4 R5 NMR Salt 906 -NH₂ -H -CONHC₂H₅ -H -H ¹H-NMR (COCl₃) δ ppm: 1. 23 (3H, t, J=7. 4 Hz), 2. 00-2.15 (2H, m), 2. 67 (2H, t, J=7. 3 Hz) , 2.75 (4H, brs), 3.21 (4H. brs). 3.40-3. 50 (2H. m), 3. 50-4. 30 (2H, br), 4.13 (2H, t, J=6.5 Ht), 6.99 (1H, brs), 6.80 (1H, d, J=8.4 Hz), 6.90 (1H, d, J=7.8 Hz). 7.08 (1H, dd, J=2.1, 8.3 Hz). 1.19 (1H, d, J=2.1 Hz), 7.25-7.30 (1H, m), 7.35-7.45 (2H, m), 7.55 (1H, d, J=8.0 Hz). - Example R1 Crystal form (Recrystalization solvent) Melting point Melting point (°C) Salt 907 White powder (water) 203.0-210.0 - 908 White powder (Ethyl-acetate/ isopropyl ether) 167.0-169.0 - 909 White powder (Ethyl acetate) 138. 0-140.0 - Example. R1 Crystal form (Recrystalization solvent) Melting point (°C) Salt 910 White powder (Ethyl acetate/ isopropyl ether) 96.5-97.0 - 911 White powder, (acetic acid) 254.0 (dec) Dihydrochloride 912 White powder (Ethyl acetate/ isopropyl ether) 124.0-126.5 - 913 White powder (Ethanol/ethyl acetate) 181.5-183.5 - Example R1 R2 R3 R4 R5 NMR 914 -OCH₃ -H -NHCO₂C (CH₃) -H -CH₃ ¹H-NNR (CDCl₃) δ ppm: 1.51(9H, s) , 1. 95-2. 10 (2H. m), 2.24(3H, s), 2. 66-2.81(6H, m) , 3.14-3.3)(2H, m) , 3.84(3H, s), 3.95(2H, t, J=6.3Hz)_. 6.36(1H, br), 6.60(1H, d, J=2.5Hz), 6.87-6.92(1H, m). 7.01 (1H, d. J=2.0Hz). 7.24-7.31(1H, m) , 7.37-7.44(2H, m), 7.55(1H, d, J=8.0Hz) 915 -OCH₃ -H -I -H -CH₃ ¹H-MMR (CDCl₃) δ ppm: 1.92-2.10 (2H, m), 2.23(3H, s), 2.57-2.86(6H. m). 3.11-3.31(4H, m), 3.82(3H, s), 3.98(2N, t, J=6.4Hz), 6. 90 (1H, d, J=7.6Hz), 7.03(1H, d, J=2.0Hz) , 1.13(1H, d, J=1.6Hz), 7.22-7.34(1H m), 7.40 (1H. dd, J=5.5Hz, 9.3Hz), 7.55(1H, d; J=6.OHz). 916 -OCH₃ -H -NHCONH (CH₂) C I -H -CH₃ ¹H-NMR (CDCl₃) δ ppm: 1.94-2.13 (2H, m) , 2.26(3H, s) 2.60-2.90(6H.m), 3.12-3.33(4H, m), 3.49-3.76(4H, m), 3.83(3H,s), 3.97(2H, t, J=6.4Hz) , 5.22(1H, br), 6.25(1H, br), 6.59(1H, d, J=2.3Hz), 6.88(1H, d, J=2.3Hz), 8.91(1H, d, -J=7.4Hz), 7.21-7.33(1H, m), 7.41 (1H, dd, J=5.6Hz. 7.6Hz), 7.56(iH, d, 4=8,0Hz) . 917 -OCH₃ -H -NH(CH₂)₂NH₂ -H -CH₃ ¹H-NMR (CDCl₃) δ ppm: 1.91-2.08 (2H, m), 2.22(3H, s), 2.62-2.81(6H, m), 2. 95 (2H, t, J=5. 7Hz) , 3.08-3.27 (6H, m) , 3.80(3H, s), 3.91(2H. t, J=6.4Hz), 6.05(1H, d. J=2.6Hz), 6.10(1H, d, J=2.6Nz); 6.80(1H, d, J=7.5Hz) , 7: 20-7.32(1H, m), 7.34-7.46 (2H, m), 7.55(1H, d, J=8.0Hz). 918 -OCH₃, -H -NH (CH₂) NHCOCH₂Cl -H -CH₃ ¹H-NMR (CDCl₃) δ ppm: 1. 91-2.11 (2H, m), 2.23(3H, s), 2.60-2.84 (6H, m), 3.11-3.26(4H. m), 3.26-3.36 (2H, m) , 3.46-3.63 (2H, m), 3.81(3H, ₈), 3.91(2H, t, J=6.4Hz). 4.06(2H. s), 6.04(1H. d, J=2.5Hz). 6.10(1H. d, J=2.5Hz), 6.78-6.96 (2H, m), 7-.21-7. 33 (1H, m), 7.35-7.47 (2H, m), 7.55(1H. d. J=8.1Hz). Example R1 R2 R3 R4 R5 NMR 919 -OCH₃ -H -H -CH₂Cl ¹H-NMR (CDCl₃) δ ppm: 2. 00-2.17 (2H, m), 2.63-2.83(6H, m), 3.14-3.28(2H. m), 3.89(3H, s), 3.98-4.17(4H, m), 4.40-4.54(2H. m), 4.69(2H, m). 6.77(1H, d. J=2.5Hz), 6.91 (1H, d, J=2.5Hz), 7. 21-7.32(1H, m), 7.35-7.46(2H, m), 7.66(1H, d. J=9. 3Hz) 920 -OCH₃ -H -H -CH₃ ¹H-NMR (CDCl₃) δ ppm: 1.48(9H. s), 1.93-2.12 (2H, m), 2.26(3H, a), 2.60-2.86(6H, m), 2.95-312(4H, m), 3.14-3.31(4H, m), 3.60-3.67(4H, m) , 3.83(3H, s), 3.84(2H, t.J=6.3Hz). 6.33(1H, d, J=2.5Hz), 6.38(1H. d. J=2. 6Hz). 6.90(1H, d, J=7.5Hz). 7.19-7.33(1H. m), 7.41 (2H, dd, J=5. 5Hz. 9.3Hz). 7.65(1H. d, J=8.0Hz). 921 -OCH₃ -H -H -CH₃ ¹H-NMR (CDCl₃) δ ppm: 1.92-2.09 (2H, m), 2.26(3H, s), 2.61-2.81(6H, m), 2.98-3.12(8H. m), 3.14-3.25(4H, m), 3.83(3H, s), 3.94(2H. t, J=6. 4Hz), 6.33(1H. d. J=2.5Hz), 6.38(1H, d, J=2.5Hz), 6.90(1H. d, J=7.OHz), 7.20-7.93(1H, m), 7.34-7. 45 (2H, m), 7.55(1H, d, J=8.0Hz). 922 -OCH₃ -H -H -CH₃ ¹H-NMR (CDCl₃) δ ppm : 1.50(9H, s), 1.95-2.11 (2H, m) , 2. 27 (3H, s) , 2.59-2.82 (6H, m), 3.12-3.27(4H. m) , 3.63-3.81 (4H. m). 3.83(3H. s). 4.01(2H. t, J=6. 4Hz) , 4.24(2H, s), 6.61-8.71(2H, m), 6.90(1H, d, J=7.6Hz), 7. 21-7,33(1H, m), 7.41 (211, dd, J=5,6Hz, 9. 8Hz) , 7.65(1H, d. J=8.1Hz). 923 -OCH₃ -H -H -CHO ¹H-NMR (COCl₃) δ ppm: 1.49(9H. s), 1.96-2.12 (2H, m), 2.60-2.82(6H, m), 3.04-3.16 (4H, m). 3;16-3.28(4H. m), 3.52-3.64 (4H, m), 3.89(3H. s). 414(2H t. J=6.3Hz). 6.78(1H. d, J=2. 8Hz) , 6.86-6.96 (2H. m) , 7.20-7.33 (1H. m). 7.35-7.46 (2H, m). 7.55(1H. d, J=8.0Hz). 10.44(1H, s). 924 -OCH₃ -H -H -CHO ¹H-NMR (CDCl₃) δ ppm: 1.97-2.13 (2H, m) , 2.59-2.83(6H. m), 2.96-3.09(4H, m), 3.09-3.17(4H. m), 3.17-3. 28 (4H, m) , 3.89(3H, s) , 4.13(2H. t, J=6.5Hz). 6.79(1H, d, J=2.7Hz). 6.86-6.96 (2H, m), 7.20-7.34 (1H. m). 7. 36-7. 45 (2H, m), 7.55(1H. d. J=8.1Hz), 10.44(1H. s). Example R1 NMR 925 ¹H-NMR (CDCl₃) δ ppm: 2.01-2 20 (2H._., m), 2.62-2.87 (6H. m), 3.10-3.30 (4H, m), 3.99(3H. s), 4. 20 (2H, t, J=6.3Hz). 6.91 (1H. dd, J=0.7Hz. 7.6Hz). 7.20(1H. d. J=2. 6Hz), 7. 22-7. 34 (2H, m), 7.35-7.50 (3H. m), 7.55 (1H, d. J=8, Hz). 7.90(1H. d. J=8.1Hz), 8.030H. dd. J=1. 2Hz, 7. 3Hz) . 8.83(1H, d, J=9. 4Hz) . Example R1 MS(M+1) 926 -2-PYRIDYL 517 927 -3-PYRIDYL 517 928 -4-PYRIDYL 517 929 -2-FURYL 506 930 -2-THIENYL 522 931 -3-FURYL 505 932 -3-THENYL 522 933 -CH₃ 454 934 -C₂H₅ 468 935 -C₃H₇ 482 936 -CH(CH₃)₂ 482 937 -cyclo-C₃H₅ 480 938 -cyclo-C₅H₉ 508 939 -cyclo-C₆H₁₁ 522 940 -CH₂-cyclo-C₃H₃ 494 941 -CH₂-cyclo-C₆H₁₁ 536 942 -CH₂OCH₃ 484 943 -CH₂N(CH₃)₂ 497 944 -(CH₂)₃N(CH₃)₂ 525 945 <CH₂)₂N(C₂H₅)₂ 539 946 -CH₂NHCHO 497 947 -CH₂N(CH₂CH₂OH)₂ 557 948 -CH₂N(CH₃)CO₂C(CH₃)₃ 583 949 -(CH₂)₃NHCO₂C(CH₃)₃ 597 950 -CH₂NHCH₃ 483 951 -(CH₂)₃NH₂ 497 952 -CH₂NHCOCH₃ 511 Example R1 MS(M+1) 953 547 954 551 955 585 956 563 957 551 958 533 959 567 960 551 961 505 Example R1 MS(M+1) 962 556 963 551 964 519 965 535 966 518 967 532 968 523 969 534 970 590 Example R1 MS(M+1) 971 556 972 589 973 521 974 523 975 535 976 549 977 520 978 520 Example R1 MS(M+1) 979 520 980 521 981 521 982 565 983 579 984 523 985 541 986 510 987 524 Example R1 MS(M+1) 988 623 989 609 990 595 991 595 992 623 993 623 994 523 995 509 996 495 Example R1 MS(M+1) 997 495 998 523 999 523 Example R1 MS(M+1) 1000 545 1001 531 1002 531 1003 531 1004 536 1005 536 1006 522 1007 551 1008 543 Examples R1 MS(M+1) 1009 543 1010 563 1011 543 1012 556 1013 551 1014 532 1015 582 1016 520 1017 522 Example R1 MS(M+1) 1018 538 1019 532 1020 637 1021 651 1022 673 1023 537 1024 551 1025 573 Example R1 R2 R3 R4 R5 Crystal form (Recrystalization solvent) Melting Point (°C) Salt 1026 -CH₃ -H -H -OCH₃ White powder (Ethyl acetate) 230.0 (dec) Hydrochloride 1027 -CH₃ -H -H -OCH₃ 1028 -CH₃ -H -H -OCH₃ White powder (Ethyl acetate) 235.0 (dec) Hydrochloride 1029 -CH₃ -H -H -OCH₃ White powder (Ethyl acetate) 227.0 (dec) Hydrochloride 1030 -CH₃ -H -H -OCH₃ White powder (Ethyl acetate) 240.0 (dec) Hydrochloride 1031 -OCH₃ -H -H -CH₃ White powder (Ethyl acetate) 211.0-213.5 Hydrochloride Example R1 R2 R3 R4 R5 Crystal form (Recrystalization solvent) Melting Point (°C) Salt 1032 -OCH₃ -H -H -CH₃ White powder (Ethyl acetate) 207.5-210.0 Hydrochloride 1033 -OCH₃ -H -H -CH₃ White powder (Ethanol/ethyl acetate) 247.0 (dec) - 1034 -CH₃ -H -CONHCH, -H -OC₃H₇ White powder (Ethanol) 178.5-179.5 Hydrochloride 1035 -OCH₃ -H -H -CH₃ Hydrochloride 1036 -OCH₃ -H -H -CH₃ White powder (Ethyl acetate) 248.5-257.5 Hydrochloride Example R1 R2 R3 R4 R5 NMR Salt 1037 -CH₃ -H -H -OCH₃ ¹H-NMR (CDCl3) δ ppm : 1.38-1.85(4H, m), 1.88-2.11 (3H, m), 2.25(3H, s), 2.47(3H, s), 2.60-2.82(8H, m), 3,1 2-3.29(4H, m), 3.47-3.63(2H, m), 3.82(3H, s), 3.93(2H, t, J=6.4Hz), 8.34(1H, d, J=2.7Hz), 6.40(1H, d, J=2.7Hz), 8.80(1H, d, J=7.1Hz), 7.21 - 7.34(1H, m), 7.40 (2H, dd, J=5.5Hz, 9.9Hz), 7.55(1H, d, J=8.0Hz). - 1038 -CH₃ -H -H -OCH₃ ¹H-NMR (CDCl3) δ ppm: 1.48(6H, s), 1.67-1.92(4H, m), 1.95-2.11 (2H, m), 2.25(3H, s), 2.81-2.87(12H, m), 3.11-3.28(4H, m), 3.54-3.70(2H, m), 3.83(3H, s), 3.94(2H, t, J=8.3Hz), 8.34(1H, d, J=2.8Hz), 6.39(1H, d, J=2.6Hz), 6.90(1H, d, J=6.9Hz), 7.17- 7.34(1H, m), 7.35-7.47 (2H, m), 7.55(1H, d, J=8.0Hz). - 1039 -CH₃ -H -H -OCH₃ ¹H-NMR (CDCl3) δ ppm : 1.96-2.11(2H, m), 2.27(3H, s), 2.57(4H. t, J=6.0Hz), 2.84- 2.84(6H, m), 3.13-3.27(14H, m), 3.51(4H, t, J=6.0Hz), 3.84(3H, s), 3.96(2H, t, J=6.4Hz), 6.38(1H, d, J=2.7Hz), 8.20(1H, d, J=2.7Hz), 6.90(1H, d, J=7.5Hz), 7.21-7.32(1H, m). 7.40 (2H, dd, J=5.5Hz, 10.0Hz), 7.55(1H, d, J=8.1Hz). - 1040 -CH₃ -H -H -OCH₃ ¹H-NMR (CDCl3) δ ppm : 1.83-1.95 (4H, m), 1.95-2.10(2H, m), 2.25(3H, s), 2.81- 2.81(6H, m), 3.07-3.28(14H, m), 3.82(3H, s), 3.93(2H, t, J=6.5Hz), 6.30-6.43(2H. m), 6.90(1H, d, J=7.5Hz), 7.29-7.34(1H, m), 7.41 (2H, dd, J=6.0Hz, 10.0Hz), 7.55(1H, d, J=7.9Hz). - Example R1 R2 R3 R4 R5 Crystal form (Recrystalization solvent) Melting Point (°C) Salt 1041 -OCH₃ -H -CONH₂ -H -CH₃ White powder (Ethanol) 189.0-102.6 Hydrochloride 1042 -OCH₃ -H -CONHCH₃ -H -CH₃ White powder (Isopropyl alcohol/water) 165.5-167.0 - Example R1 MS(M+1) 1043 553 1044 525 1045 567 1046 499 1047 497 1048 543 1049 549 1050 559