PYRIMIDINE DERIVATIVES

Description

BACKGROUND

[0001] Angiogenesis is a physiological process of growing new blood vessels from pre-existing vessels. It takes place in a healthy subject to heal wounds, i.e., restoring blood flow to tissues after injury or insult.

[0002] Excessive blood vessel growth may be triggered by certain pathological conditions such as cancer, age-related macular degeneration, rheumatoid arthritis, and psoriasis. As a result, new blood vessels feed diseased tissues and destroy normal tissues. In cancer, new blood vessels also allow tumor cells to escape into the circulation and lodge in other organs.

[0003] Vascular endothelial growth factor (VEGF), a homodimeric glycoprotein, and its receptors, e.g., kinase insert domain receptor (KDR), constitute an important angiogenic pathway. Studies have shown that inhibition of KDR resulted in endothelial cell apoptosis and, thus, suppression of angiogenesis. See Rubin M. Tuder, Chest, 2000; 117: 281. KDR inhibitors are therefore potential candidates for treating angiogenesis-related diseases.

SUMMARY

[0004] This invention is based on the discovery that a number of pyrimidine compounds inhibit the activity of KDR.

[0005] One aspect of this invention features pyrimidine compounds of the following formula (I):

in which each of X is O or NH; Y is NH; Z is CR', wherein R' is H, halo, or alkyl; V, U, and T together represent

each of R₁, R₃, R₄, and R₆, independently, is H, halo, nitro, amino, cyano, hydroxy, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, heteroaryl, alkoxy, alkylthio, alkylcarbonyl, carboxy, alkoxycarbonyl, carbonylamino, sulfonylamino, aminocarbonyl, or aminosulfonyl; R₂ is H, halo, nitro, amino, hydroxy, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, heteroaryl, alkoxy, alkylthio, alkylcarbonyl, carboxy, alkoxycarbonyl, carbonylamino, sulfonylamino, aminocarbonyl, or aminosulfonyl; R₅ is alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl; and R₇ is alkyl.

[0006] Referring to formula (I), one subset of the compounds features that R₁, R₂, R₃, and R₄ is H and R₅ is aryl or heteroaryl, optionally substituted with halo, nitro, amino, cyano, hydroxy, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, heteroaryl, alkoxy, alkylthio, alkylcarbonyl, carboxy, alkoxycarbonyl, sulfonyl, carbonylamino, sulfonylamino, aminocarbonyl, or aminosulfonyl. Another subset features that X is O or NH; Y is NH; V, U, and T together represent

in which R₆ can be H and R₇ can be methyl; or Z is CR', in which R' is H, halo, or alkyl.

[0007] The term "alkyl" herein refers to a straight or branched hydrocarbon, containing 1-10 carbon atoms. Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, and t-butyl. The term "alkoxy" refers to an -O-alkyl.

[0008] The term "aryl" refers to a 6-carbon monocyclic, 10-carbon bicyclic, 14-carbon tricyclic aromatic ring system wherein each ring may have 1 to 4 substituents. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, and anthracenyl.

[0009] The term "cycloalkyl" refers to a saturated and partially unsaturated cyclic hydrocarbon group having 3 to 12 carbons. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cycloheptyl, and cyclooctyl.

[0010] The term "heteroaryl" refers to an aromatic 5-8 membered monocyclic, 8-12 membered bicyclic, or 11-14 membered tricyclic ring system having one or more heteroatoms (such as O, N, or S). Examples of heteroaryl groups include pyridyl, furyl, imidazolyl, benzimidazolyl, pyrimidinyl, thienyl, quinolinyl, indolyl, and thiazolyl. The term "heteroaralkyl" refers to an alkyl group substituted with a heteroaryl group.

[0011] The term "heterocycloalkyl" refers to a nonaromatic 5-8 membered monocyclic, 8-12 membered bicyclic, or 11-14 membered tricyclic ring system having one or more heteroatoms (such as O, N, or S). Examples of heterocycloalkyl groups include, but are not limited to, piperazinyl, pyrrolidinyl, dioxanyl, morpholinyl, and tetrahydrofuranyl. Heterocycloalkyl can be a saccharide ring, e.g., glucosyl.

[0012] Alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and alkoxy mentioned herein include both substituted and unsubstituted moieties. Substituents are selected from halo, hydroxyl, amino, cyano, nitro, mercapto, alkoxycarbonyl, amido, carboxy, alkanesulfonyl, alkylcarbonyl, carbamido, carbamyl, carboxyl, thioureido, thiocyanato, sulfonamido, alkyl, alkenyl, alkynyl, alkyloxy, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, in which alkyl, alkenyl, alkynyl, alkyloxy, aryl, heteroaryl cycloalkyl, and heterocycloalkyl may further substituted.

[0013] The pyrimidine compounds described above include their pharmaceutically acceptable salts, hydrate and prodrug, if applicable.

[0014] Another aspect of this invention features a compound of formula (I) for use in a method of treating an angiogenesis-related disorder (e.g., cancer or age-related macular degeneration). The method includes administering to a subject having such a disorder an effective amount of one or more of the above-described pyrimidine compounds.

[0015] Also disclosed herein is a method of inhibiting the activity of kinase insert domain receptor by contacting the receptor with an effective amount of a pyrimidine compound of formula (II):

in which R₁ is H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, or heteroaryl; each of R₂ and R₃, independently, is H, halogen, nitro, amino, CN, hydroxy, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, heteroaryl, alkoxy, alkylcarbonyl, carboxy, or alkoxycarbonyl; each of X and Y, independently, is O, S, or NR₄, wherein R₄ is H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, heteroaryl, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, or aminosulfonyl; and Ar is aryl or heteroaryl.

[0016] Referring to formula (II), one subset of the compounds features that Ar is indolyl, indazolyl, benzoimidazolyl, or benzoxazolyl; X is O or NH and Y is NH; or R₁ is aryl or heteroaryl, optionally substituted with halo, nitro, amino, cyano, hydroxy, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, heteroaryl, alkoxy, alkylthio, alkylcarbonyl, carboxy, alkoxycarbonyl, sulfonyl, carbonylamino, sulfonylamino, aminocarbonyl, or aminosulfonyl.

[0017] Exemplary compounds 1-317 are shown in the Detailed Description section below. Compounds 18, 26, 27, 41, 45-47, 51, 60, 64, 74-76, 85, 88, 96, 98-100, 103, 110, 113, 114, 120, 123, 125-129, 131, 140-142, 147, 149, 151, 153, 155, 159-161, 171, 174, 176-178, 180, 182, 184, 204, 206, 207, 209, 210, 213, 215, 217, 222, 231-233, 235, 237, 238-240, 246-250, 254, 256, 259, 261, 262, 268, 270, 273-275, 277, 279, 281, 300, 306-308 and 310-317 are provided as comparative examples.

[0018] Also disclosed herein is a method of inhibiting angiogenesis, or treating age-related macular degeneration, by administrating to a subject in need thereof an effective amount of a pyrimidine compound of formula (II) as described above.

[0019] Also within the scope of this invention are (1) a composition containing one or more of the pyrimidine compounds of formula (I) described above and a pharmaceutically acceptable carrier for use in treating an angiogenesis-related disorder (e.g., such cancer or age-related macular degeneration) and (2) use of one or more of the pyrimidine compounds of formula (I) for the manufacture of a medicament for treating the disorder.

[0020] The details of one or more embodiments of the invention are set forth in the description below. Other features, objects and advantages of the invention will be apparent from the description and from the claims.

DETAILED DESCRIPTION

[0021] The compounds described above can be synthesized from commercially available starting materials by methods well known in the art. As an example, one can replace leaving groups (e.g., chloride, p-TsO, MeS, or MeSO₂) at the active N2, N4-positions of a suitable pyrimidine compound with nucleophilic groups such as amino or hydroxyl via, e.g., Buchwald-Hartwig coupling reaction. The replacement can be first effected either at the N2 position or the N4 position.

[0022] The compounds thus obtained can be further modified at their peripheral positions to provide the desired compounds.

[0023] Synthetic chemistry transformations useful in synthesizing desirable pyrimidine compounds are described, for example, in R. Larock, Comprehensive Organic Transformations, VCH Publishers (1989); T.W. Greene and P.G.M. Wuts, Protective Groups in Organic Synthesis, 3rd Ed., John Wiley and Sons (1999); L. Fieser and M. Fieser, Fieser and Fieser's Reagents for Organic Synthesis, John Wiley and Sons (1994); and L. Paquette, ed., Encyclopedia of Reagents for Organic Synthesis, John Wiley and Sons (1995) and subsequent editions thereof

[0024] Before use, the compounds can be purified by column chromatography, high performance liquid chromatography, crystallization, or other suitable methods.

[0025] The pyrimidine compounds described above, when contacting with KDR, inhibit this receptor's activity. An effective amount of one or more of these compounds can be therefore used to inhibit angiogenesis and treat a subject having an angiogenesis-related disorder.

[0026] The term "an effective amount" refers to the amount of a pyrimidine compound that is required to confer the intended effect in the subject. Effective amounts may vary, as recognized by those skilled in the art, depending on route of administration, excipient usage, and the possibility of co-usage with other agents. The term "treating" refers to administering one or more of the above-described pyrimidine compounds to a subject that has an angiogenesis-related disorder, or has a symptom of the disorder, or has a predisposition toward the disorder, with the purpose to cure, heal, alleviate, relieve, alter, remedy, ameliorate, improve, or affect the disorder, the symptoms of the disorder, or the predisposition toward the disorder.

[0027] To practice this method, a composition having one or more of the pyrimidine compounds of this invention can be administered orally, parenterally, by inhalation spray, or via an implanted reservoir. The term "parenteral" as used herein includes subcutaneous, intracutaneous, intravenous, intramuscular, intraarticular, intraarterial, intrasynovial, intrasternal, intrathecal, intralesional and intracranial injection or infusion techniques.

[0028] An oral composition can be any orally acceptable dosage form including, but not limited to, tablets, capsules, emulsions and aqueous suspensions, dispersions and solutions. Commonly used carriers for tablets include lactose and corn starch. Lubricating agents, such as magnesium stearate, are also typically added to tablets. For oral administration in a capsule form, useful diluents include lactose and dried corn starch. When aqueous suspensions or emulsions are administered orally, the active ingredient can be suspended or dissolved in an oily phase combined with emulsifying or suspending agents. If desired, certain sweetening, flavoring, or coloring agents can be added.

[0029] A sterile injectable composition (e.g., aqueous or oleaginous suspension) can be formulated according to techniques known in the art using suitable dispersing or wetting agents (such as, for example, Tween 80) and suspending agents. The sterile injectable preparation can also be a sterile injectable solution or suspension in a nontoxic parenterally acceptable diluent or solvent, for example, as a solution in 1,3-butanediol. Among the acceptable vehicles and solvents that can be employed are mannitol, water, Ringer's solution and isotonic sodium chloride solution. In addition, sterile, fixed oils are conventionally employed as a solvent or suspending medium (e.g., synthetic mono- or di-glycerides). Fatty acids, such as oleic acid and its glyceride derivatives are useful in the preparation of injectables, as are natural pharmaceutically-acceptable oils, such as olive oil or castor oil, especially in their polyoxyethylated versions. These oil solutions or suspensions can also contain a long-chain alcohol diluent or dispersant, or carboxymethyl cellulose or similar dispersing agents.

[0030] An inhalation composition can be prepared according to techniques well known in the art of pharmaceutical formulation and can be prepared as solutions in saline, employing benzyl alcohol or other suitable preservatives, absorption promoters to enhance bioavailability, fluorocarbons, and/or other solubilizing or dispersing agents known in the art.

[0031] A topical composition can be formulated in form of oil, cream, lotion, ointment and the like. Suitable carriers for the composition include vegetable or mineral oils, white petrolatum (white soft paraffin), branched chain fats or oils, animal fats and high molecular weight alcohols (greater than C12). The preferred carriers are those in which the active ingredient is soluble. Emulsifiers, stabilizers, humectants and antioxidants may also be included as well as agents imparting color or fragrance, if desired. Additionally, transdermal penetration enhancers may be employed in these topical formulations. Examples of such enhancers can be found in U.S. Patents 3,989,816 and 4,444,762. Creams are preferably formulated from a mixture of mineral oil, self-emulsifying beeswax and water in which mixture the active ingredient, dissolved in a small amount of an oil, such as almond oil, is admixed. An example of such a cream is one which includes about 40 parts water, about 20 parts beeswax, about 40 parts mineral oil and about 1 part almond oil. Ointments may be formulated by mixing a solution of the active ingredient in a vegetable oil, such as almond oil, with warm soft paraffin and allowing the mixture to cool. An example of such an ointment is one which includes about 30% by weight almond and about 70% by weight white soft paraffin.

[0032] A carrier in a pharmaceutical composition must be "acceptable" in the sense that it is compatible with active ingredients of the formulation (and preferably, capable of stabilizing it) and not deleterious to the subject to be treated. For example, solubilizing agents, such as cyclodextrins (which form specific, more soluble complexes with one or more of active pyrimidine compounds of the extract), can be utilized as pharmaceutical excipients for delivery of the active ingredients. Examples of other carriers include colloidal silicon dioxide, magnesium stearate, cellulose, sodium lauryl sulfate, and D&C Yellow # 10.

[0033] Suitable in vitro assays can be used to preliminarily evaluate the efficacy of the above-described pyrimidine compounds in inhibiting the activity of KDR or inhibiting the activity of VEGF. The compounds can further be examined for its efficacy in treating an angiogenesis-related disorder by in vivo assays. For example, the compounds can be administered to an animal (e.g., a mouse model) having cancer and its therapeutic effects are then accessed. Based on the results, an appropriate dosage range and administration route can also be determined.

[0034] Without further elaboration, it is believed that the above description has adequately enabled the present invention. The following specific examples are, therefore, to be construed as merely illustrative, and not limitative of the remainder of the disclosure in any way whatsoever.

Example 1: Synthesis of N4-(2-methyl-1H-indol-5-yl)-N2-phenylpyrimidine-2,4-diamine (Compound 1)

[0035] 

[0036] Et₃N (1 mmol) was added to a solution of 2,4-dichloropyrimidine (1 mmol) and 5-amino-2-methylindole (1 mmol) in 5 ml EtOH. The reaction mixture was refluxed for 5 hours. After removal of the solvent in vacuo and addition of H₂O, the mixture was extracted with EtOAc. The organic layers were combined, washed with saturated NaCl solution, dried over anhydrous Na₂SO₄, and concentrated in vacuo. The resulting residue was purified by column chromatography to give N-(2-chloropyrimidin-4-yl)-2-methyl-1H-indol-5-amine in a yield of 80%.

[0037] N-(2-chloropyrimidin-4-yl)-2-methyl-1H-indol-5-amine(0.1 mmol) and aniline (0.1 mmol) were dissolved in 0.5ml DMF. To this was added p-TsOH monohydrate (0.2 mmol). The reaction mixture was stirred at 60°C for 5 hours, diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and brine sequentially, dried over anhydrous Na₂SO₄, and concentrated. The resulting residue was purified by column chromatography to provide the title product in a yield of 85%.

[0038] ¹H NMR (CD₃OD, 400 MHz): δ 7.831 (d, J=6.0Hz, 1H), 7.633 (t, J=8.0-7.6Hz, 3H), 7.262 (t, J=8.4-7.6 Hz, 3H), 7.064 (d, J=6.8 Hz, 1H), 6.995 ((t, J=7.6-7.2 Hz,1H), 6.133 (t, J=6.4-2.0 Hz, 2H), 2.439 (s,3H); MS (m/e): 384.2 (M+1).

Example 2-283: Synthesis of Compounds 2-283

[0039] Compounds 2-283 were each synthesized in a manner similar to that described in Example 1.

Compound	Name/Structure	1H NMR (400 MHz, δ ppm) / MS
2	N2-(3-ethynylphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):7.848 (d, J=6.8 Hz, 1H), 7.730 (s, 1H), 7.704 (d, J=8.0 Hz, 1H), 7.507 (s, 1H), 7.275 (d, J=8.0 Hz, 1H), 7.200 (t, J=8.0 Hz, 1H), 7.093-7.036 (m, 2H), 6.639 (m,2H), 2.425 (s,3H); MS (m/e): 340.4 (M+1)
3	N2-(3-bromophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):7.879 (s, 1H), 7.784 (d, J=6.0 Hz, 1H), 7.437 (br, 1H), 7.373 (s, 1H), 7.255 (d, J=8.8 Hz, 1H), 7.079 (br, 2H), 6.968 (d, J=8.4 Hz, 1H), 6.133 (s, 1H), 6.041 (d, J=6.4 Hz, 1H), 2.400 (s, 3H); MS(m/e): 394.3 (M)
4	N2-(3-fluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):7.923( s, 1H), 7.759(d, J=6.0 Hz, 1H), 7.641(d, J=8.0 Hz, 1H), 7.397( s, 1H), 7.247 (d, J=8.4 Hz, 1H), 7.179-7.053 (m, 1H), 6.963(d, J=8.4 Hz, 1H), 6.575(t, J=8.0 Hz, 1H), 6.125(s, 1H), 6.044(d, J=6.0 Hz, 1H), 2.395 (s, 3H); MS(m/e): 334.2 (M+1)
5	N2-(3-chlorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):7.838 (d, J=6.8 Hz, 1H), 7.746 (s, 1H), 7.526 (br, 2H), 7.298 (d, J=8.4 Hz, 1H), 7.212 (t, J=8.0 Hz, 1H), 7.102 (d, J=8.4 Hz, 1H), 7.001 (d, J=8.0 Hz, 1H), 6.217 (d, J=6.0 Hz, 1H), 6.133 (s, 1H), 2.436 (s, 3H); MS(m/e): 350.2 (M+1)
6	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(trifluoromethyl)phenyl) pyrimidine-2,4-diamine	(CD3OD):8.045 (d, J=7.2Hz, 1H), 7.788 (d, J=6.0Hz, 2H), 7.529 (s, 1H), 7.366 (d, J=6.8 Hz, 1H), 7.276 (d, J=8.4 Hz, 1H), 7.228 (d, J=7.2 Hz, 1H), 7.083 (d, J=1.2 Hz, 1H),6.190((d, J=6.4 Hz,1H),6.115(s,1H), 2.440(s,3H). MS(m/e): 384.2(M+1)
7	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(methylsulfonyl)phenyl)pyrimidine-2,4-diamine	(CD3OD):11.471(s, 1H), 9.461 (s, 1H), 9.364(s, 1H), 8.441 (s, 1H), 8.236 (s, 1H), 7.988 (d, J=5.6 Hz, 1H), 7.396 (M,, 5H), 7.303 (d, J=8.4 Hz,1H), 6.255(d, J=5.6 Hz, 1H), 3.111 (s, 3H), 2.456 (s, 3H).MS(m/e): 393.2 (M+1)
8	N2-(3-methoxylphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):8.050(s,1H), 7.943( d, J=6.0 Hz, 1H), 7.440-7.362(m, 3H), 7.293 (s, 1H), 7.223(t, J=8.0 Hz, 2H), 7.122 (d, J=7.6 Hz, 1H), 7.0211 (d, J=6.8 Hz, 1H), 6.808(s, 1H), 6.680 (d, J=6.4 Hz, 1H), 6.222(s, 1H), 6.068(d, J=5.6 Hz, 1H), 3.790(s,3H), 2.472(s,3H); MS(m/e): 345.9 (M+1)
9	ethyl 1-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidine-4-carboxylate	(CD3OD):8.019(s,1H), 7.889( d, J=5.6 Hz, 1H), 7.554(s, 1H), 7.399(d, J=8.0 Hz, 1H), 7.328( d, J=8.4 Hz, 1H), 7.278( t,J=8.0 Hz, 1H), 7.101( d, J=8.0 Hz, 1H), 7.002( d, J=7.2 Hz, 1H), 6.180(d, J=6.0 Hz, 1H), 6.141 (s, 1H), 4.166( q, J=7.2 Hz, 1H), 3.586(s, 2H), 2.973-2.943(m, 2H), 2.462(s, 3H), 2.316(br, 1H), 2.089(m, 2H), 1.939-1.885(m, 2H), 1.741-1.653(m, 2H), 1.272(t, J=7.2Hz, 2H); MS(m/e): 485.4 (M+1)
10	N2,N4-bis(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):7.675( d, J=6.4 Hz, 1H), 7.625(s, 1H), 7.577(br, 1H), 7.266-7.219 (m, 2H), 7.068-7.051 (m, 1H), 6.116 (d, J=6.0 Hz, 1H), 6.072 (s, 1H), 6.014 (s, 1H), 2.435 (s, 3H), 2.425 (s, 3H); MS(m/e): 369.3 (M+1)
11	N2-(1H-indazol-5-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):12.385(s, 1H), 10.928(s, 1H), 9.120(s, 1H), 9.003(s, 1H), 8.259(s, 1H), 7.920( d, J=6.0 Hz, 1H), 7.758(s, 1H), 7.667(s, 1H), 7.541 (d, J=8.8 Hz, 2H), 7.399 (d, J=8.8 Hz, 1H), 7.242 (d, J=8.8 Hz, 1H), 7.151(d, J=8.8 Hz, 1H), 6.142 (d, J=6.0 Hz, 1H), 6.017 (s, 1H), 2.389 (s, 3H). MS(m/e): 356.3 (M+1)
12	N2-(1H-benzo[d]imidazol-5-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):10.853(s,1H), 9.033(s,1H), 8.956(s,1H), 8.077(br, 2H), 7.925( d, J=6.0 Hz, 1H), 7.736(s, 1H), 7.533(d, J=8.0 Hz, 1H), 7.444( d, J=8.8 Hz, 1H), 7.214-7.144(m, 2H), 6.131(d, J=6.0 Hz, 1H), 6.020 (s, 1H), 2.372(s,3H); MS(m/e): 356.3 (M+1)
13	N2-(2-methoxyphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):8.496(s,1H), 8.002( d, J=6.0 Hz, 2H), 7.446( s, 1H), 7.047 (dd, J=8.8 Hz, J=2.4 Hz, 1H), 6.981-6.957 (m, 2H), 6.913-6.771 (m, 1H), 6.889 (s, 1H), 6.243 (s, 1H), 6.083(d, J=6.0Hz, 1H), 3.910(s, 3H), 2.490 (s, 3H). MS(m/e): 346.2 (M+1)
14	N2-(2-chlorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):8.385( d, J=6.0 Hz, 1H), 7.914( s, 1H), 7.849(s, 1H), 7.325 (d, J=7.6 Hz, 1H), 7.237 (d, J=8.4 Hz, 1H),7.182(t, J=7.6 Hz, 1H), 6.945-6.870(m, 2H), 6.119(s, 1H), 6.070(d, J=6.0 Hz, 1H), 2.397 (s, 3H);MS(m/e): 350.1 (M+1)
15	N2-(2-bromophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):10.860(s, 1H), 9.204(s, 1H), 8.140 (d, J=8.4 Hz, 1H), 7.916 (d, J=5.6 Hz, 2H), 7.651 (d, J=7.6 Hz, 2H), 7.334 (t, J=7.6 Hz, 1H), 7.184 (d, J=8.8 Hz, 1H), 7.038 (br, 2H), 6.192 (d, J=6.0 Hz, 1H), 6.012 (s, 1H), 2.369 (s, 3H); MS(m/e): 394.3 (M)
16	N2-(4-fluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):10.889(s, 1H), 9.256 (s, 1H), 9.245 (s, 1H), 7.966 (d, J=5.6 Hz, 1H), 7.752 (m, J=8.4-3.6Hz, 2H), 7.236(d, J=5.4 Hz 1H),7.133(m, J=8.4-3.6 Hz, 3H), 6.086 (d, J=5.6 Hz, 1H), 6.050(s,1H),2.402 (s, 3H);MS(m/e):334.2 (M+1)
17	methyl 2-(4-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)acetate	(CD3OD):10.907(s, 1H), 9.132(s, 1H), 9.015(s, 1H), 7.914(s, 1H), 7.713(d, J=6Hz, 1H), 7.498(d, J=6.8Hz, 1H), 7.217(d, J=7.2Hz, 1H), 7.127(m, 4H), 6.149(d, J=6Hz, 1H), 6.067(s, 1H), 2.384(s, 3H), 2.272(s, 3H), 1.288(s, 2H). MS(m/e): 387.2 (M+1)
18	N4-(2-methyl-1H-indol-5-yl)-N2-(4-phenoxyphenyl)pyrimidine-2,4-diamine	(CD3OD):10.855(s, 1H), 9.098(s, 1H), 9.065(s, 1H), 7.909(d, J=5.6Hz, 1H), 7.786(d, J=8Hz, 2H), 7.365(t, J=7.6Hz, 2H), 7.346(s, 1H), 7.201(d, J=8.8Hz, 1H), 7.086(m, 2H), 6.962(d, 8Hz, 2H), 6.895(d, J=8Hz, 2H), 6.137(d, J=5.6Hz, 1H), 6.021(s, 1H), 2.331(s, 3H). MS(mle): 407.5 (M+1)
19	N2-(4-methoxyphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):11.097(s, 1H), 9.479(s, 1H), 9.243(s, 1H), 8.090(d, J=6Hz, 1H), 7.923(s, 1H), 7.822(m, 2H), 7.420(d, 8.8Hz, 1H), 7.307(s, 1H), 7.025(d, J=8.8Hz, 2H), 6.340(m, 1H), 6.265(s, 1H), 3.941(s, 3H), 2.591(s, 3H); MS(m/e): 345.4 (M+1)
20	N4-(2-methyl-1H-indol-5-yl)-N2-(4-(2-morpholinoethoxy)phenyl) pyrimidine-2,4-diamine	(CD3OD):10.899(s, 1H), 9.074(s, 1H), 8.823(s, 1H), 7.869(d, J=6Hz, 1H), 7.713(s, 1H), 7.621(d, J=8.8Hz, 2H), 7.200(d, J=8.4Hz, 1H), 7.080(s, 1H), 6.784(m, 2H), 6.101(d, J=5.6Hz, 1H), 6.025(s, 1H), 4.034(t, J=5.6Hz, 2H), 3.585(t, J=4.8Hz, 4H), 2.679(t, J=5.6Hz, 2H), 2.475(t, J=6.4Hz, 4H), 2.375(s, 3H);MS: 444.5 (M+1)
21	N2-(3,4-difluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):11.234(s, 1H), 9.886 (s, 1H), 9.754 (s, 1H), 7.966 (d, J=5.6 Hz, 2H), 7.752 (s, 1H), 7.393(m, J=8.4-3.6 Hz, 3H),7.133(d, J=5.6 Hz, 1H), 6.251 (d, J=4.5 Hz, 1H), 6.1.9(s,1H), 2.402 (s, 3H);MS(m/e):352.2 (M+1)
22	N2-(3,5-dimethylphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):10.863(s, 1H), 9.051(s, 1H), 8.841(s, 1H), 7.905(d, J=6Hz, 1H), 7.633(s, 1H), 7.361(s, 1H), 7.207(m 2H), 6.507(s, 1H), 6.118(d, J=5.6Hz, 1H), 6.032(s, 2H), 2.370(s, 3H), 2.171(s, 6H); MS(m/e): 343.4 (M+1).
23	2-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)ethanol	(CD3OD):7.939(d, J=8.0Hz,1H), 6.923 (d, J=6.8Hz, 2H), 6.437 (s, 1H), 6.328 (d, J=7.6 Hz, 2H), 6.218 (s, 1H),6.231(d, J=5.6 Hz,1H),5.726(d, J=7.2 Hz,1H), 3.735(t, J=7.2-6.4Hz,3H),3.225(t, J=6.8-5.6Hz,3H),2.247 (s, 3H); MS(mle): 384.1(M+1)
24	N4-(2-methyl-1H-indol-5-yl)-N2-(2-morpholinoethyl)pyrimidine-2,4-diamine	(CD3OD):7.796 (d, J=6.0Hz, 1H), 7.497 (s, 1H), 7.246 (d, J=8.8 Hz, 1H), 7.076 (d, J=2.8 Hz, 1H),6.148(s,1H),5.625(d, J=4.8 Hz,1H), 3.760(m, J=3.2-2.8 Hz, 4H),3.165(t, J=3.2-2.4,2H), 2.619(t, J=2.0-0.8Hz,2H), 2.447(m, J=2.0-1.2Hz,4H),2.317(s,3H). MS(m/e): 353.2(M+1)
25	N-cyclopropyl-2-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)acetamide	(DMSO-d6,): 7.920 (d, J=5.6 Hz, 1H), 7.700 (m, 2H), 7.546 (s, 1H), 7.220 (d, J=8.0 Hz, 1H), 7.120 (m, 2H), 6.778 (d, J=8.0 Hz, 1H), 6.200 (d, J=6.0 Hz, 1H), 6.066 (s, 1H), 3.027 ( s, 2H), 2.593 (m, 1H), 2.380 ( s, 3H), 0.608 (m,2H), 0.404 (m, 2H). MS (m/e): 413.5 (M+1).
26	N2-(3-(2-(dimethylamino)ethylsulfonyl)phenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):8.237 (s, 1H), 8.042 (d, J=6.8 Hz 1H), 7.867 (d, J=6.0 Hz, 1H), 7.477 (s, 1H), 7.465 (br, 2H), 7.253 (d, J=8.8 Hz, 1H), 7.028(d, J=8.0 Hz 1H), 6.141(d, J=5.6 Hz 1H), 6.088 (s, 1H), 3.230 (t, J=7.6 Hz , 2H), 2.666 (t, J=7.2 Hz , 2H), 2.409 (s, 3H), 2.165 (s, 6H);MS: 451.4 (M+1).
27	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(1-(methylsulfonyl)piperidin-4-yloxy)phenyl)pyrimidine-2,4-diamine	(DMSO-d6): 10.976 (s, 1 H), 9.240 (s, 1 H), 9.036 (s, 1 H), 7.054-8.014 (m, 7H), 6.401-6.564 (m, 1H), 6.114-6.278 (m, 1H), 6.012-6.073 (m, 1H), 4.224-4.383 (m, 1H), 3.110-3.209 (m, 2H), 2.770-2.886 (m, 2H), 2.370 (s,3H), 1.806-1.970 (m, 2H), 1.578-1.712 (m, 1H); MS (m/e): 493.5 (M+1)
28	N-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)methanesulfonamide	(CD3OD):7.856 (d, J=6.0 Hz, 1H), 7.652 (s, 1H), 7.543 (s, 1H), 7.432 (dd, J=8.4 Hz, 1H), 7.271 (d, J=8.4 Hz, 1H), 7.196 (t, J=8.0 Hz, 1H), 6.882 (dd, J=8.0Hz, 2H), 6.130 (d, J=6.0 Hz, 2H), 2.440 (s, 3H), 2.172 (s, 3H); MS (m/e): 409.3 (M+1)
29	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(2-morpholinoethoxy) phenyl) pyrimidine-2,4-diamine	(DMSO-d6): δ10.825 (s, 1H), 9.023 (s,1H), 8.986 (s, 1H), 7.927 (d, J=5.6Hz, 1H), 7.703 (s,1H), 7.429 (s,1H), 7.351 (d, J=2.4Hz, 1H), 7.208 (d, J=8.8Hz, 1H), 7.076 (m,J=8Hz, 2H), 6.469 (dd, J=8, 2.4Hz, 1H), 6.118 (d, J=2Hz, 1H), 6.057 (s, 1H), 3.933 (t, J=5.6Hz, 2H), 3.551 (t, J=4.8Hz, 4H), 2.591 (t, J=5.6Hz, 2H), 2.401(t, J=4.8Hz, 4H), 2.379 (s, 3H); MS (m/e): 444.5 (M+1).
30	N2-(3-(3-(dimethylamino) propoxy)phenyl)-N4-(2-met-hyl- H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):10.836(s, 1H), 9.021(s, 1H), 8.983(s, 1H), 7.926(d, J=6Hz, 1H), 7.691(s,1H), 7.419(s,1H), 7.345(d, J=8.4Hz, 1H), 7.212(d, J=8.4Hz, 1H), 7.079(m, 2H), 6.444(dd, J=8, 2.4Hz, 1H), 6.118(d, J=6Hz, 1H), 6.062(s, 1H), 3.835(t, J=6Hz, 2H), 2.317(s, 3H), 2.318(t, J=7.2Hz, 2H), 2.154(s, 6H), 1.767(t, J=7.2Hz, 2H); MS(m/e): 416.5 (M+1).
31		(CD3OD):10.902(s, 1H), 9.087(s, 1H), 8.986(s, 1H), 7.917(d, J=4Hz, 1H), 7.683(s, 1H), 7.405(m, 2H), 7.227(m, 1H), 7.104(m, 1H), 6.458(d, J=8Hz, 1H), 6.141(s, 1H), 6.050(m, 2H), 5.594(m, 1H), 3.873(t, J=5.6Hz, 2H), 3.653(t, J=6Hz, 2H), 2.376(s, 3H); MS(m/e): 375.4 (M+1)
	2-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino) phenoxy)ethanol
32	2-(2-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethanol	(CD3OD):10.851 (s, 1H), 9.117 (s, 1H), 8.431 (d, J=8.0 Hz 1H), 7.938 (d, J=6.0 Hz, 1H), 7.869 (s, 1H), 7.689 (br, 1H), 7.228 (d, J=8.8 Hz, 1H), 6.983-7.053 (m, 2H), 6.836-6.923 (m, 2H), 6.147 (d, J=6.0 Hz 1H), 6.079 (s, 1H), 5.137 (t, J=5.6 Hz 1H), 4.061 (q, J=11.2 Hz , 1.2 Hz 2H), 3.767 (q, J=9.6 Hz ,5.6 Hz 2H), 2.389 (s, 3H); MS(m/e): 376.3 (M+1).
33	N4-(2-methyl-1H-indol-5-yl)-N2-(2-(2-morpholinoethoxy)phenyl) pyrimidine-2,4-diamine	(CD3OD):10.845 (s, 1H), 9.112 (s, 1H), 8.377 (d, J=7.6 Hz 1H), 7.935 (d, J=6.0 Hz, 1H), 7.823 (s, 1H), 7.647 (br, 1H), 7.219 (d, J=8.8 Hz, 1H), 7.061 (d, J=8 Hz ,2H), 6.889-6.950 (m, 2H), 6.147 (d, J=6.0 Hz 1H), 6.074 (s, 1H), 4.182 (t, J=6.0 Hz 2H), 3.592 (t, J=4.8 Hz, 4H), 2.692 (t, J=5.2 Hz, 2H), 2.471 (br, 4H), 2.388(s, 3H); MS(m/e): 445.3 (M+1).
34	N-methyl-3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzamide	(DMSO-d6): δ 11.015 (s, 1H), 10.776 (s, 1H), 10.593 (s, 1H), 8.493 (d,J=4Hz, 1H), 7.938 (m, 2H), 7.803 (d, J=2Hz, 1H), 7.651 (m, 2H), 7.374 (m, 1H), 7.210 (m,2H), 6.467 (m 1H), 6.046 (s, 1H), 2.779 (d, 4.4Hz, 3H), 2.379 (s, 3H); MS (m/e): 373.4 (M+1).
35	3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-(2-(piperidin-1-yl)ethyl)benzamide	(CD3OD):10.832(s, 1H), 9.156(s, 1H), 9.056(s, 1H), 8.157(s, 1H), 8.054(s, 1H), 7.946(m, 2H), 7.700(b, 1H), 7.319(m, 2H), 7.199(m, 2H), 6.159(s, 1H), 6.052(s, 1H), 3.180(t, J=5.6Hz, 2H), 2.378(s, 3H), 1.480(s, 6H), 1.372(s, 4H), 1.229(s, 2H). MS(m/e): 469.6 (M+1)
36	N-(2-(dimethylamino)ethyl)-3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzamide	(CD3OD):10.846(s, 1H), 9.149(s, 1H), 9.077(s, 1H), 8.181(t, J=5.6Hz, 1H), 8.036(m, 2H), 7.934(m, 1H), 7.706(b, 1H),
		7.340(m, 1H), 7.270(m, 1H), 7.203(m, 1H), 7.137(m, 1H), 6.160(d, J=5.6Hz, 1H), 6.054(s, 1H), 3.313(t, J=6.4Hz, 2H), 3.175(t, J=5.6Hz, 2H), 2.376(s, 3H), 2.175(s, 6H).MS(m/e): 429.5 (M+1)
37	N2-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(DMSO-d6): δ 12.354 (s,1H), 10.911 ( s, 1H), 8.985 (br, 2H), 7.901 (s, 1H), 7.599 (br, 2H), 7.259 (d, J=8.4 Hz, 1H), 7.037 (s, 1H), 6.941-6.913 (m, 2H), 6.099 (br, 2H), 3.787 (s, 3H), 2.493 (s,3H); MS (m/e): 412.8 (M+1).
38	N-(3-ethynylphenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine	(CD3OD): 8.190(d, J=6.0 Hz, 1H), 8.098(s, 1H), 7.612(s, 1H), 7.489( d, J=8.0 Hz, 1H), 7.339-7.284(m, 2H), 7.053(t, J=8.4 Hz, 1H), 6.937(dd,J=8.4Hz, 2.0Hz, 2H), 6.294(d, J=6.0Hz, 2H), 6.262(s, 1H), 2.495(s,3H); MS(m/e): 341.1 (M+1)
39	N-(4-methoxyphenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine	(CD3OD): 8.198( d, J=6.4 Hz, 1H), 7.974(s, 1H), 7.363-7.283(m, 2H), 6.935(m, 2H), 6.742( t, J=8.4 Hz, 1H), 6.260( s, 1H), 6.200( d, J=5.6 Hz, 1H), 3.771(s, 3H), 2.493(s, 3H). MS(m/e): 347.2 (M+1).
41	4-(2-methyl-1H-indol-5-yloxy)-N-(4-phenoxyphenyl)pyrimidin-2-amine	(CD3OD): 8.201 (d, J=5.6Hz, 1H), 7.373 (m, J=8.8-5.2Hz, 4H), 7.188 (d, J=2.0Hz, 1H), 7.081 (t, J=7.2-6.8 Hz, 1H), 6.989 (d, J=3.2 Hz, 2H), 6.890 (d, J=8.4 Hz, J=2.0 Hz, 1H), 6.644 (d, J=9.2 Hz, 2H),6.323(d, J=6.4 Hz,1H),6.137(s,1H), 2.376(s,3H). MS(m/e): 409.3(M+1).
42	N-(3-methoxyphenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine	(CD3OD): 8.236( d, J=5.2 Hz, 1H), 7.983(s, 1H), 7.314-7.283(m, 2H), 7.239(br, 1H),
		7.063( t, J=8.0 Hz, 1H), 6.981( d, J=8.0 Hz, 1H), 6.981( dd, J=8.8 Hz, 2.0Hz, 1H), 6.528( d, J=8.0 Hz, 1H), 6.278-6.253(m, 1H), 3.571 (s, 1H), 2.493(s, 3H). MS(m/e): 347.2 (M+1).
43	4-(2-methyl-1H-indol-5-yloxy)-N-(3- (3-(thiomorpholino-1',1'-dioxide)propoxy)phenyl)pyrimidin-2-amine	(CD3OD):8.298(s,1H), 7.996(d, J=5.6 Hz, 1H), 7.3 85 (d, J=8.4Hz, 1H), 7.197 (t, J=8.0 Hz, 1H), 7.094(d, J=8.4 Hz, 2H), 6.791(s,1H), 6.543 (d, J=8.0 Hz, 1H), 6.333(s, 1H), 5.995 (d, J=6.0 Hz, 1H), 5.321 (s,1H), 3.974(t, J=5.6 Hz, 1H), 3.077(m, 8H), 2.699(t, J=6.8Hz, 1H),2.468(s, 3H),1.926(t, J=6.8 Hz, 2H);
44	N-methyl-3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzamide	(DMSO-d6): 11.130 (s,1H), 9.631 (s, 1H), 8.324(d, J=4.2Hz, 1H), 8.309 (s, 1H), 7.994 (s, 1H), 7.741 (s, 1H), 7.308 (d, J=9.2 Hz, 1H), 7.219 (d, J=1.6 Hz, 1H), 7.052 (t, J=2.0-0.8 Hz, 2H), 6.932 (m,1H), 6.272 (d, J=3.6 Hz, 1H), 6.140 (d, J=4.2 Hz,1H), 5.249 (s,1H), 2.801 (s,3H), 2.437 (s,3H), 2.401(m,2H); MS (m/e): 374.3(M+1)
45	trifluoro-N-(4-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)methanesulfonamide	(DMSO-d6): 11.248 (s,1H), 9.304 (s, 1H), 9.153(s, 1H), 7.960(s,1H), 7.913(d, J=6.0Hz, 1H), 7.543 (d, J=4.4Hz,2H), 7.132 (d, J=8.4Hz, 1H), 7.063 (m,1H), 6.910 (t, J=3.6 Hz, 2H), 6.217 (s,1H), 6.106 (t, J=1.6-2.4 Hz, 1H), 2.411(s,3H) MS (m/e): 464.4(M+1)
46	(S)-4-(2-methyl-1H-indol-5-yloxy)-N-(3-(pyrrolidin-3-yloxy)phenyl)pyrimidin-2-amine	(DMSO-d6): 11.122 (s, 1 H), 9.515 (s, 1 H), 8.306 (d, J=5.6 Hz, 1H), 7.156-7.332 (m, 4H), 6.951 (t, J=8.0 Hz, 1H), 6.827 (dd, J=8.4 Hz, 2.0 Hz, 1H ), 6.427 (dd, J=8.4 Hz, 2.0 Hz, 1H), 6.267 (d, J=6.0 Hz, 1H), 6.139 (s, 1H), 6.639 (m,2H), 4.652-4.711 (m, 1H), 2.964-3.154 (m, 4H), 2.401 (s,3H), 1.958-1.993 (m, 1H), 1.825-1.898(m, 1H); MS (m/e): 402.4 (M+1)
47		(CDCl3) : 8.290 (d, 1H), 8.115 (s, 1H), 7.994 (s, 1H), 7.504 (d, J=8, 1H), 7.409 (m, 2H), 7.247 (d, J=8, 1H), 6.958 (m, J=10.8), 6.403 (d, J=5.6, 1H), 6.254 (s, 1H). 2.505 (s, 3H), 2.478 (d, J=5.6, 3H).MS (m/e): 410.1 (M+1)
	methyl-3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzenesulfonamide
48	N-(4-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)methanesulfonamide	(CD3OD):11.204(s, 1H),9.120 (s, 1H), 8.837 (s, 1H), 7.959(d, J=5.6Hz,1H), 7.791 (d, J=6.8Hz, 2H), 7.144(s,1H), 7.026 (d, J=7.6 Hz, 2H), 6.922(d, J=7.2 Hz,1H),6.210 (s, 1H),6.115(s, 1H), 4.007(s,3H),2.405 (s, 3H); MS(m/e): 358.2(M+1).
49	2-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)-N-(2-morpholinoethyl)acetamide	(CD3OD):11.211(s, 1H), 8.935 (s, 1H), 8.760 (s, 1H), 7.959(t, J=8.8-5.6Hz,2H), 7.376 (s, 1H), 7.276 (d, J=7.6 Hz, 1H), 7.120(t, J=8.8-4.4Hz, H), 6.896(t, J=8.0 Hz,2H),6.403 (t, J=2.0-1.6 Hz, 1H),6.205(s, 1H), 6.004 (s, 1H), 3.560(s,3H),2.405 (s, 3H); MS(m/e): 364.2(M+1).
50	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(2-(methylsulfonyl)ethoxy)phenyl)pyrimidin -2-amine	(CD3OD):8.345 (s, 1H), 8.049 (s, 1H). 7.915 (d, J=6.0 Hz, 1H), 7.826 (s, 1H), 7.58(d, J=8.8Hz,1 H), 7.535(m, J=7.2-6.8Hz, 1H), 7.433(d, J=7.6 Hz,2H), 7.103(d, J=7.6 Hz,1H),6.241(s, 1H), 2.460 (s, 3H); MS(m/e): 402.2(M+1).
51	N-methyl(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl) methanesulfonamide	11.217(s, 1H), 8.998 (s, 1H), 8.789 (s, 1H), 7.947 (d, J=5.6 Hz, 1H), 7.595(m, J=7.8-1.6Hz, 2H), 7.133(d, J=8.0Hz,2H), 7.000,(s, 1H),6.721(d, J=2.8Hz,1H),6.211(s,1H), 6.021 (s, 1H), 2.403(s,3H), 2.346 (s, 3H);MS(m/e): 380.2(M+1).
52	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-fluorophenyl) pyrimidine-2,4-diamine	(CD3OD):11.234(s, 1H), 9.256 (s, 1H), 8.898 (s, 1H), 7.966 (d, J=5.6 Hz, 1H), 7.752 (d, J=8.4 Hz, 1H), 7.393(t, J=8.4 Hz,1H),7.133(m, J=8.4-3.6 Hz, 3H), 6.612 (t, J=7.6-1.2 Hz, 1H), 6.239(s,1H),6.050(s,1H),2.402 (s, 3H); MS(m/e): 352.2(M+1).
53	N2-(3-chlorophenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):11.221(s, 1H),8.965 (s, 1H). 8.775 (s, 1H), 7.927 (d, J=6.0 Hz, 1H), 7.619 (d, J=8.0 Hz, 2H), 7.128(m, J=8.0-7.6 Hz,2H),6.958(d, J=7.8 Hz, 2H), 6.210 (s, 1H), 2.411 (s, 3H); MS(m/e):368.2(m/e) (M+1).
54	2-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzonitrile	(CD3OD): 11.248(s, 1H), 9.412 (s, 1H), 8.959 (s, 1H), 8.208 (s, 1H), 7.936(d, J=7.2 Hz, 1H), 7.562(d, J=5.6 Hz,1H),7.287(s, 2H), 7.164 (d, J=8.4Hz, 2H),6.233(s,1H) ,6.075(s,1H), 2.399 (s, 3H); MS(m/e): 359.2(M+1).
55	N2-(3,5-dimethylphenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):11.200(s, 1H), 8.806 (s, 1H), 8.745 (s, 1H), 7.911 (d, J=6.0 Hz, 1H), 7.216(s, 2 H) 7.117(t, J=8.8-7.8 Hz, 2H), 6.396(s, 1H),6.181(s, 1H), 6.010 (s, 1H), 2.381 (s, 3H);1.985(s,6H); MS(m/e): 362.3(M+1).
56	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(2-(trifluoromethyl) phenyl)pyrimidine-2,4-diamine	(CD3OD):11.211(s, 1H), 8.898 (s, 1H), 8.209 (s, 1H), 7.939 (t, J=9.6-6.0 Hz, 2H), 7.270(t, J=8.4-1.6Hz.1 H) 7.126(s, 2H), 6.998(m, J=2.0-1.2 Hm2H),6.225(s, 1H), 6.035 (s, 1H), 2.402 (s, 3H);MS(m/e): 402.2(M+1).
57	N2-(2-chlorophenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	(CD3OD):11.231(s, 1H), 8.922 (s, 1H), 8.143 (d, J=8.0 Hz ,1H), 7.936 (s, J=5.6 Hz, 1H), 7.790 (s, 1H), 7.424(d, J=8.4 Hz,1H),7.101(m, J=8.4-7.2 Hz, 2H), 6.993 (t, J=8.8-7.2 Hz, 1H), 6.216 (s, 1H), 6.093 (m, J=7.2-10.0 Hz, 1H), 4.043(s, J=7.8 Hz,1H),2.402 (s, 3H); MS(m/e): 368.2 (M+1).
59	N4-(4-fluoro-2-methy]-1H-indol-5-yl)-N2-(4-methoxyphenyl) pyrimidine-2,4-diamine	11.222(s, 1H), 8.796 (s, 1H), 8.729 (s, 1H), (CD3OD):7.959(s,1H), 7.892 (d, J=5.6 Hz, 1H), 7.547(d, J=8.8Hz,2 H) 7.075(s, 1H), 6.646(d, J=7.6 Hz,2H),6.222(s, 1H), 5.567 (s, 1H), 3.658(s,3H),2.406 (s, 3H); MS(m/e): 402.2(M+1).
60	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(4-phenoxyphenyl) pyrimidine-2,4-diamine	(CD3OD):11.190(s, 1H), 9.046(s, 1H), 8.801(s,1H), 7.959(s,1H), 7.931(d, J=6.0Hz,1H), 7.681 (d, J=7.2 Hz,2H), 7.361(t, J=8.0-7.6 Hz, 2H), 7.114(m, J=8.4-7.2Hz,3H),6.903(d, J=8.0 Hz, 2H), 6.755 (d, J=7.2Hz, 2H),6.179(s,1H), 6.024(s, 1H), 2.338 (s, 3H). MS(m/e): 426.2(M+1).
61	2-(1-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)ethanol	(CD3OD): 7.932(s,1H), 7.885(d, J=5.6Hz, 1H), 7.331(m, 1H), 7.204(m, 3H), 7.103(t, J=7.2Hz, 1H), 6.958(d, J=7.6Hz, 1H), 6.251(s,1H), 6.176(m,1H), 3.603-3.572(m, 4H), 3.068-3.041(m, 2H), 2.454(s,3H), (m, 2H),2.197(br, 2H), 1.783-1.750(m, 2H),1.563(br, 2H), 1.477(m, 2H), 1.311-1.275(m, 2H). MS(m/e):475.4(M+1)
62	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(3-(methylsulfonyl)propoxy)phenyl)pyrimidi ne-2,4-diamine	(DMSO-d6): 7.932 (d, J=6.0 Hz, 1H), 7.399 (s, 1H),7.393 (d, J=6.8 Hz, 1H), 7.099 (m,2H), 6.97 (m,1H), 6.416 (d, J=8.0 Hz, 1H), 6.207 (s,1H), 6.088( s,1H), 3.84 (m, 2H), 3.196 (m, 2H), 3.010( s, 3H), 2.400 (s, 3H), 2.014(m, 2H).
		MS (m/e): 470.5 (M+1).
63	2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethanol	(DMSO-d6): 7.938 (d, J=6.0 Hz, 1H), 7.347 (m, 2H), 7.104 (m, 2H), 6.950 (m, 1H), 6.410 (d, J=8.0 Hz, 1H), 6.206 (s, 1H), 6.088( s,1H), 3.788 (m, 2H), 3.630 (m, 2H), 2.401 (s, 3H). MS (m/e): 394.4 (M+1).
64	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(piperidin-3-yloxy)phenyl)pyrimidine-2,4-diamine	(DMSO-d6): 11.241 (s,1H), 8.966 (s, 1H), 8.789 (s, 1H), 7.929 (d, J=5.6 Hz, 1H), 7.378 (s, 1H), 7.267 (d, J=7.6 Hz, 1H),7.120-7.053 (m, 2H), 6.964 (m,1H), 6.380 (d, J=8.0 Hz, 1H) 6.207 (s,1H) ,6.010 (s,1H), 4.010 (s, 1H),3.710 (m,1H);3.554 (s,2H). 3.362 (m,2H). 2.506 (s,3H)2.401(m,2H) 1.234(m,2H),MS (m/e): 433.2 (M+1)
65	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-((1-(methylsulfonyl)piperidin-4-yl)methoxy)phenyl)pyrimidine-2,4-diamine	(CD3OD):8.021 (d, J=5.6 Hz, 1H), 7.418 (s, 1H), 7.220-7.051 (m, 3H), 6.998 (m,1H), 6.612 (d, J=7.4 Hz, 1H) 6.267 (s,1H) ,5.800 (d, J=5.6 Hz ,1H), 3.960 (d, J=5.2 Hz ,2H), 3.810 (m,2H); 3.362 (m,2H) . 2.826 (s,3H), 2.506 (s,3H)1.556 (m,2H), 1.452 (m,1H)1.234 (m,2H)
66	1-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-ol	(CD3OD):8.247 (d, J=5.6 Hz, 1H), 7.378 (s, 1H), 7.160-7.108 (m, 2H), 6.956 (t, J=8.0 Hz, 1H), 6.895-6.825 (m, 2H), 6.450 (d, J=5.6 Hz, 1H), 6.247 (s, 1H), 3.031 (s,1H), 2.690-2.663 (m, 2H), 2.455 (s,3H), 2.069-2.042 (m, 2H), 1.815-1.716 (m, 2H), 1.562-1.483 (m, 2H); MS (m/e): 448.5 (M+1)
67	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(methylsulfonyl)phenyl)pyrimidin-2-amine	(CD3OD):8.292 (d, J=5.6 Hz, 1H), 8.005 (s, 1H), 7.691 (d, J=7.2 Hz, 1H), 7.341 (d, J=7.2 Hz, 1H), 7.102 (d, J=8.8 Hz, 1H), 7.013 (t, J=7.2 Hz, 1H), 6.849 (t, J=8.0Hz, 1H), 6.482 (d, J=5.6 Hz, 1H), 6.221 (s, 1H), 2.900 (s, 3H), 2.432 (s, 3H); MS (m/e): 413.4 (M+1)
68	N-cyclopropyl-2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)acetamide	(DMSO-d6): 7.947 (m, 2H), 7.298 (m, 2H), 7.154 (d, J=8.4 Hz, 1H), 6.947 (m, 1H), 6.755 (m, 1H), 6.775 (d, J=8.0 Hz, 1H). 6.441 (d, J=5.6 Hz, 1H), 6.240 (s, 1H), 3.027 ( s, 2H ), 2.593 (m, 1H), 2.499 ( s, 3H), 0.596 (m,2H), 0.390 (m, 2H). MS (m/e): 432.5 (M+1)
69	(E)-3-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)-N-methylacrylamide	(DMSO-d6) : 11.550 ( s, 1H ) ,9.791 (s, 1H), 8.385 (d, J=5.2, 1H), 8.114 (d, J=4.8, 1H), 7.432 (d, J=7.2, 2H), 7.214 (d, J=10, 1H), 7.184 (d, J=3.2, 1H), 7.083 (d, J=8, 2H), 6.942 (m, J=16, 1H), 6.533 (d, J=5.6, 1H, 6.402 (d, J=15.6), 6.253 (s, 1H), 2.687 (d, J=4.8, 3H), 2.440 (s, 3H).MS (m/e): 418.2 (M+1)
70	3-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)-N,N-dimethylpropanamide	( DMSO-d6 ) : 11.397 (s, 1H), 9.420 (s, 1H), 8.334 (d, J=5.6, 1H), 7.290(s, 1H), 7.241 (d, J=7.2, 1H), 7.152 (d, J=8.8, 1H), 6.919 (m, J=15.2, 1H), 6.803 (m, J=15.6, 1H), 6.652 (d, J=6.8, 1H), 6.451 (d, J=5.6, 1H), 6.218 (s, 1H), 2.860 (s, 3H), 2.795 (s, 3H), 2.449 (m, J=14.8, 2H), 2.399 (s, 3H), 2.338 (m, J=14.8, 2H).MS (m/e): 434.2 (M+1)
71	N-methyl-3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzamide	MS (m/e): 372.4 (M)
72	N2-(2-fluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 350.1 (M+1)
73	3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzonitrile	MS (m/e): 341.2(M+1)
74	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(methylthio)phenyl)pyrimidine-2,4-diamine	MS (m/e): 362.3 (M+1)
75	N,N-dimethyl-3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzenesulfonamide	MS (m/e): 423.5 (M+1)
76	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(morpholinosulfonyl)phenyl)pyrimidine-2,4-diamine	MS (m/e): 465.4 (M+1)
77	N2-(3,4-dimethoxyphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 376.3(M+1)
78	N2-(4-chlorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 350.3 (M+1)
79	N2-(2,4-difluozophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 352.2 (M+1)
80	N2-(3-chloro-2-fluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 368.3 (M+1)
81	N2-(1H-indol-4-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 355.3(M+1)
82	N2-(4-(3-(dimethylamino)propoxy)phenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 417.4(M+1)
83	2-(4-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethanol	MS (m/e): 376.3(M+1)
84	N2-(3-chloro-4-fluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e):368.3 (M+1)
85	N2-(benzo[d][1,3]dioxol-5-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 360.3 (M+1)
86	(1-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)methanol	MS (m/e): 443.4 (M+1)
87	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 521.2(M)
88	3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-propylbenzenesulfonamide	MS (m/e): 437.3 (M+1)
89	N2-(2-chloro-4-fluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 368.1(M+1)
90	2-chloro-4-fluoro-5-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol	MS (m/e): 384.3(M+1)
91	N2-(4-chloro-2-tluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 368.3(M+1)
92	N2-(3-(2-(dimethylamino)ethoxy)phenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 403.4 (M+1)
93	N2-(2-methyl-1H-indol-5-yl)-N4-(3-(3-(methylsulfonyl)propoxy)phenyl)pyrimidi ne-2,4-diamine	MS (m/e): 452.3(M+1)
94	2-(1-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)ethanol	MS (m/e): 457.4 (M+1)
95	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(piperidin-4-ylmethoxy)phenyl)pyrimidine-2,4-diamine	MS (m/e):429.4 (M+1)
96	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(piperidin-3-yloxy)phenyl)pyrimidine-2,4-diamine	MS (m/e):416.4 (M+1)
97	1-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-ol	MS (m/e): 429.4(M+1)
98	(S)-N4-(2-methyl-1H-indol-5-yl)-N2-(3-(pyrrolidin-3-yloxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 401.4(M+1)
99	(S)-N4-(2-methyl-1H-indol-5-yl)-N2-(3-(1-(methylsulfonyl)pyrrolidin-3-yloxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 479.5(M+1)
100	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(piperidin-4-yloxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 415.5 (M+1)
101	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(3-(4-(methylsulfonyl)piperazin-1-yl)propoxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 536.6 (M+1)
102	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(3-morpholinopropoxy)phenyl) pyrimidine-2,4-diamine	MS (m/e): 459.6 (M+1)
103	(R)-N4-(2-methyl-1H-indol-5-yl)-N2-(3-(1-(methylsulfonyl)pyrrolidin-3-yloxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 479.5 (M+1)
104	(E)-N,N-dimethyl-3-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)acrylamide	MS (m/e): 413.2(M+1)
105	4-(4-fluoro-2-methyl-1H-indol-5-yl)-N-(3- (3-(thiomorpholino-1',1'-dioxide)propoxy)phenyl)pyrimidin-2-amine	MS (m/e): 507.5(M+1)
106	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(2-(methylamino)ethoxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 389.5(M+1)
107	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3- (3-(thiomorpholino-1'-oxide) propoxy) phenyl) pyrimidin-2-amine	MS (m/e): 491.5 (M+1)
108	N-(2-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethyl)methanesulfonam ide	MS (m/e): 453.4 (M+1)
109	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(3-thiomorpholinopropoxy) phenyl)pyrimidine-2,4-diamine	MS (m/e): 475.5(M+1)
110	trifluoro-N-(4-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino) phenyl)methanesulfonamide	MS (m/e): 463.4 (M+1)
111	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(2-thiomorpholinoethoxy) phenyl)pyrimidine-2,4-diamine	MS (m/e): 461.4 (M+1)
112	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(2-pyrrolidinethoxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 429.4(M+1)
113	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(2-morpholinoethylsulfonyl) phenyl)pyrimidine-2,4-diamine	MS (m/e): 493.1 (M+1)
114	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(2-(pyrrolidin-1-yl) ethylsulfonyl)phenyl)pyrimidine-2,4-diamine	MS (m/e): 477.1(M+1)
115	N4-(2-methyl-1H-indol-5-yl)-N2-(3-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)pyrimidine-2,4-diamine	MS (m/e): 492.4(M+1)
116	2-(4-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperazin-1-yl)ethanol	MS (m/e): 458.5 (M+1)
117	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(methylsulfonylmethyl)phenyl)pyrimidine -2,4-diamine	MS (m/e): 408.3 (M+1)
118	N,N-dimethyl-3-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)propanamide	MS (m/e): 415.5(M+1)
119	(E)-N-methyl-3-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)acrylamide	MS (m/e): 399.2(M+1)
120	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(tetrahydro-2H-pyran-4-yloxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 416.4 (M+1)
121	N2-(3-(2-aminoethoxy)phenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 375.3(M+1)
122	N-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino) benzyl)methanesulfonamide	MS (m/e): 423.4(M+1)
123	N-(2-hydroxyethyl)-3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzamide	MS (m/e): 403.2(M+1)
124	N-methyl-3-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)propanamide	MS (m/e): 401.2 (M+1)
125	3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-(2-(methylamino)-2-oxoethyl)benzamide	MS (m/e): 430.2 (M+1)
126	3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-(2-morpholinoethyl)benzamide	MS (m/e):472.3 (M+1)
127	3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-(2-(piperidin-1-yl)ethyl)benzamide	MS (m/e): 470.1 (M+1)
128	trifluoro-N-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-yl amino)phenyl)methanesulfonamide	MS (m/e): 463.0 (M+1)
129	N-(2-methoxyethyl)-3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzamide	MS (m/e): 417.2(M+1)
130	N-(4-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-yl amino)phenyl)methanesulfonamide	MS (m/e): 409.1 (M+1)
131	2-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)-N-(2-morpholinoethyl)acetamide	MS (m/e): 493.1 (M+1)
132	N2-(6-methoxypyridin-3-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 347.4(M+1)
133	2-methyl-N-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-yl)-1H-indol-5-amine	MS (m/e): 370.3 (M+1)
134	N-(3-(3-(dimethylamino)propoxy)phenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine	MS (m/e): 418.4(M+1)
135	2-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy)ethanol	MS (m/e): 377.4(M+1)
136	N-(3-(2-(dimethylamino)ethoxy)phenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine	MS (m/e): 404.4(M+1)
137	N-cyclopropyl-2-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)acetamide	MS (m/e):414.4 (M+1)
138	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(3-(methylsulfonyl)propoxy)phenyl)pyrimidi n-2-amine	MS (m/e): 453.4 (M+1)
139	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(piperidin-4-ylmethoxy)phenyl)pyrimidin-2-amine	MS (m/e): 448.2 (M+1)
140	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(piperidin-3-yloxy)phenyl)pyrimidin-2-amine	MS (m/e): 416.2 (M+1)
141	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(piperidin-4-yloxy)phenyl)pyrimidin-2-amine	MS (m/e): 416.4 (M+1)
142	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(1-(methylsulfonyl)piperidin-4-yloxy)phenyl)pyrimidin-2-amine	MS (m/e): 494.5 (M+1)
143	1-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-ol	MS (m/e): 430.4 (M+1)
144	(1-(3-(4-(2-mcthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)methanol	MS (m/e): 444.4 (M+1)
145	2-(1-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)ethanol	MS (m/e): 458.5(M+1)
146	N-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl) methanesulfonamide	MS (m/e): 409.12 (M+1)
147	(S)-4-(2-methyl-1H-indol-5-yloxy)-N-(3-(1-(methylsulfonyl)pyrrolidin-3-yloxy)phenyl)pyrimidin-2-amine	MS (m/e): 480.5(M+1)
148	(E)-N,N-dimethyl-3-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)acrylamide	MS (m/e): 414.5 (M+1)
149	3-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino) phenyl)-1-morpholinopropan-1-one	MS (m/e): 458.5(M+1)
150	N-(3-(2-methoxyethoxy)phenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine	MS (m/e): 391.0 (M+1)
151	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(morpholinosulfonyl)phenyl)pyrimidin-2-amine	MS (m/e): 465.1 (M+1)
152	N-(2-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy)ethyl)methanesulfonam ide	MS (m/e): 454.2 (M+1)
153	(R)-4-(2-methyl-1H-indol-5-yloxy)-N-(3-(1-(methylsulfonyl)pyrrolidin-3-yloxy)phenyl)pyrimidin-2-amine	MS (m/e): 480.5(M+1)
154	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(2-morpholinoethoxy)phenyl)pyrimidin-2-amine	MS (m/e): 446.4 (M+1)
155	N-(2-(dimethylamino)ethyl)-3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzamide	MS (m/e): 431.4 (M+1)
156	N-(3-(2-methoxyethoxy)phenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine	MS (m/e): 391.3 (M+1)
157	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(morpholinomethyl)phenyl)pyrimidin-2-amine	MS (m/e): 416.4(M+1)
158	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(3-thiomorpholinopropoxy)phenyl)pyrimidin -2-amine	MS (m/e): 476.5 (M+1)
159	N-(3-(2-(dimethylamino)ethylsulfonyl)phenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine	MS (m/e): 452.4(M+1)
160	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(2-morpholinoethylsulfonyl)phenyl)pyrimidi n-2-amine	MS (m/e): 494.4(M+1)
161	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(2-(pyrrolidin-1-yl) ethylsulfonyl)phenyl)pyrimidin-2-amine	MS (m/e): 478.4 (M+1)
162	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(2-thiomorpholinoethoxy)phenyl)pyrimidin-2-amine	MS (m/e):462.4 (M+1)
163	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(2-(pyrrolidin-1-yl)ethoxy)phenyl)pyrimidin-2-amine	MS (m/e): 430.3 (M+1)
164	4-(2-methyl-1H-indol-5-yloxy)-N-(3-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)pyrimidin-2-amine	MS (m/e): 493.5 (M+1)
165	2-(4-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperazin-1-yl)ethanol	MS (m/e): 459.5(M+1)
166	4-(2-methyl-1H-indol-5-yloxy)-N-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)pyrimidin-2-amine	MS (m/e): 431.3(M+1)
167	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(methylsulfonylmethyl)phenyl)pyrimidin-2-amine	MS (m/e): 409.4 (M+1)
168	tert-butyl 4-(2-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy)ethyl)piperazine-1-carboxylate	MS (m/e): 545.4(M+1)
169	N,N-dimethyl-3-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino))phenyl)propanamide	MS (m/e): 416.5 (M+1)
170	(E)-N-methyl-3-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)acrylamide	MS (m/e): 400.2 (M+1)
171	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(tetrahydro-2H-pyran-4-yloxy)phenyl)pyrimidin-2-amine	MS (m/e): 416.18(M+1)
172	N-(3-(2-aminoethoxy)phenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine	MS (m/e): 3763(M+1)
173	N-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)methanesulfonamide	MS (m/e): 424.4 (M+1)
174	N-(2-hydroxyethyl)-3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzamide	MS (m/e):404.1 (M+1)
175	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(2-(piperazin-1-yl)ethoxy)phenyl)pyrimidin-2-amine	MS (m/e): 444.5 (M)
176	3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)-N-(2-(methylamino)-2-oxoethyl)benzamide	MS (m/e): 431.2 (M+1)
177	3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)-N-(2-morpholinoethyl)benzamide	MS (m/e): 473.0 (M+1)
178	3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)-N-(2-(piperidin-1-yl)ethyl)benzamide	MS (m/e): 471.4 (M+1)
179	N-methyl-3-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino))phenyl)propanamide	MS (m/e): 402.2 (M+1)
180	N-(2-methoxyethyl)-3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzamide	MS(m/e):418.1 (M+1)
181	N-(4-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)methanesulfonamide	MS (m/e): 410.2 (M+1)
182	2-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)-N-(2-morpholinoethyl)acetamide	MS (m/e): 487.1(M+1)
183	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(2-(methylsulfonyl)ethoxy)phenyl)pyrimidin-2-amine	MS (m/e): 439.2 (M+1)
184	N-methyl(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)methanesulfonamide	MS (m/e): 424.4 (M+1)
185	N-(6-methoxypyridin-3-yl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-Amine	MS (m/e):348.2 (M+1)
186	methyl 2-(4-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)acetate	MS (m/e):406.2 (M+1)
187	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(2-methoxyphenyl)pyrimidine-2,4-diamine	MS (m/e): 364.2 (M+1)
188	N2-(3-bromophenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e):412.3 (M+1)
189	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(methylsulfonyl) phenyl)pyrimidine-2,4-diamine	MS (m/e): 412.3(M+1)
190	3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzonitrile	MS (m/e): 359.3 (M+1)
191	N2-(2-chloro-4-fluorophenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 386.2 (M+1)
192	N-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)methanesulfonamide	MS (m/e): 427.3(M+1)
193	N2-(3,4-difluorophenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 370.2(M+1)
194	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(2-morpholinoethoxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 463.4 (M+1)
195	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)phenyl)pyrimidine-2,4-diamine	MS (m/e):540.3 (M+1)
196	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(2-(2-morpholinoethoxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 462.3 (M)
197	N2-(3-(3-(dimethylamino)propoxy)phenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 435.4 (M+1)
198	N-cyclopropyl-2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)acetamide	MS (m/e): 431.4(M+1)
199	N-(2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-yl amino) phenoxy)ethyl)methanesulfonamide	MS (m/e): 471.4 (M+1)
200	2-(2-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethanol	MS (m/e): 394.4 (M+1)
201	N2-(3-(2-(dimethylamino)ethoxy)phenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 421.4(M+1)
202	(1-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)methanol	MS (m/e): 461.5(M+1)
203	3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-methylbenzamide	MS (m/e): 391.3(M+1)
204	trifluoro-N-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)methanesulfonamide	MS (m/e): 481.3(M+1)
205	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(piperidin-4-ylmethoxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 446.22(M+1)
206	(E)-3-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)-1-morpholinoprop-2-en-1-one	MS (m/e): 473.5 (M+1)
207	trifluoro-N-(4-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)methanesulfonamide	MS (m/e):481.3 (M+1)
208	N-(5-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)pyridin-2-yl)acetamide	MS (m/e): 392.4 (M+1)
209	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(morpholinosulfonyl) phenyl)pyrimidine-2,4-Diamine	MS (m/e):483.5 (M+1)
210	3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-methylbenzenesulfonamide	MS (m/e): 427.1(M+1)
211	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine	MS (m/e):408.4 (M+1)
212	4-(4-fluoro-2-methyl-1H-indol-5-yl)-N-(3-(3-(thiomorpholino-1',1'-dioxide)propoxy)phenyl)pyrimidin-2-amine	MS (m/e): 525.5(M+1)
213	N-(2-(dimethylamino)ethyl)-3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzamide	MS (m/e): 448.5 (M+1)
214	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(2-(methylamino)ethoxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 407.5(M+1)
215	(E)-3-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)-1-morpholinoprop-2-en-1-one	MS (m/e): 473.1(M+1)
216	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(3-thiomorpholinopropoxy)phenyl)pyrimidin e-2,4-diamine	MS (m/e): 493.5(M+1)
217	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(2-morpholino ethylsulfonyl)phenyl)pyrimidine-2,4-diamine	MS (m/e): 511.4(M+1)
218	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(2-thiomorpholino ethoxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 479.4 (M+1)
219	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(2-(pyrrolidin-1-yl)ethoxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 447.4 (M+1)
220	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)pyrimidine-2,4-diamine	MS (m/e): 510.4(M+1)
221	2-(4-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperazin-1-yl)ethanol	MS (m/e): 474.7 (M-1)
222	3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino) phenylmethanesulfonate	MS (m/e): 428.4(M+1)
223	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(methylsulfonylmethyl) phenyl)pyrimidine-2,4-diamine	MS (m/e): 426.4(M+1)
224	tert-butyl 4-(2-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-yl amino)phenoxy)ethyl)piperazine-1-carboxylate	MS (m/e): 544.4(M+1)
225	tert-butyl 4-(2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethyl)piperazine-1-carboxylate	MS (m/e): 562.3 (M+1)
226	3-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino))phenyl)-N,N-dimethylpropanamide	MS (m/e): 433.4 (M+1)
227	(E)-3-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)-N-methylacrylamide	MS (m/e): 417.2 (M+1)
228	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)pyrimidine-2,4-diamine	MS (m/e): 448.4 (M+1)
229	N2-(3-(2-aminoethoxy)phenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 393.2 (M+1)
230	N-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)methanesulfonamide	MS (m/e): 441.4 (M+1)
231	3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-(2-hydroxyethyl)benzamide	MS (m/e): 421.2 (M+1)
232	3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-(2-morpholinoethyl)benzamide	MS (m/e): 490.1 (M+1)
233	3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-(2-(piperidin-1-yl)ethyl)benzamide	MS (m/e): 488.4 (M+1)
234	3-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)-N-methylpropanamide	MS (m/e): 419.2 (M+1)
235	3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-(2-methoxyethyl)benzamide	MS (m/e): 435.2(M+1)
236	N-(4-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-yl amino)phenyl)methanesulfonamide	MS (m/e):427.2 (M+1)
237	2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)-N-(2-morpholinoethyl)acetamide	MS (m/e): 504.1(M+1)
238	3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-(2-(methylamino)-2-oxoethyl)benzamide	MS (m/e): 448.2 (M+1)
239	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(tetrahydro-2H-pyran-4-yloxy)phenyl)pyrimidine-2,4-diamine	MS (m/e):434.4 (M+1)
240	1-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)sulphonyl -methylamine	MS (m/e): 441.4(M+1)
241	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(6-methoxypyridin-3-yl)pyrimidine-2,4-diamine	MS (m/e): 365.4 (M+1)
242	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(2-morpholinoethoxy) phenyl)pyrimidin-2-amine	MS (m/e): 464.4 (M+1)
243	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(3-morpholino propoxy)phenyl)pyrimidin-2-amine	MS (m/e):478.4 (M+1)
244	2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy)ethanol	MS (m/e): 395.4 (M+1)
245	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(3-(thiomorpholino-1',1'-dioxide) propoxy)phenyl)pyrimidin-2-amine	MS (m/e): 526.7 (M+1)
246	(R)-4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(pyrrolidin-3-yloxy)phenyl)pyrimidin-2-amine	MS (m/e): 420.5 (M+1)
247	(S)-4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(pyrrolidin-3-yloxy)phenyl)pyrimidin-2-amine	MS (m/e):420.5 (M+1)
248	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(1-(methylsulfonyl)piperidin-4-yloxy)phenyl)pyrimidin-2-amine	MS (m/e): 512.4 (M+1)
249	(R)-4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(1-(methylsulfonyl)pyrrolidin-3-yloxy)phenyl)pyrimidin-2-amine	MS (m/e): 498.4(M+1)
250	N-(2-(dimethylamino)ethyl)-3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzamide	MS (m/e): 448.5(M+1)
251	(1-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)methanol	MS (m/e):462.4 (M+1)
252	2-(1-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)ethanol	MS (m/e): 476.5(M+1)
253	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(2-(methylamino)ethoxy) phenyl)pyrimidin-2-amine	MS (m/e): 408.4 (M+1)
254	(E)-3-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)-1-morpholinoprop-2-en-1-one	MS (m/e): 474.5(M+1)
255	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(morpholino methyl)phenyl)pyrimidin-2-amine	MS (m/e):434.5 (M+1)
256	(S)-4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(1-(methylsulfonyl)pyrrolidin-3-yloxy)phenyl)pyrimidin-2-amine	MS (m/e): 498.4 (M+1)
257	3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)-N-methylbenzamide	MS (m/e): 392.4 (M+1)
258	N-(2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy) ethyl)methanesulfonamide	MS (m/e): 472.4 (M+1)
259	trifluoro-N-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-yl amino) phenyl)methanesulfonamide	MS (m/e): 482.3(M+1)
260	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(3-thiomorpholinopropoxy) phenyl)pyrimidin-2-amine	MS (m/e): 494.5 (M+1)
261	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(2-(pyrrolidin-1-yl)ethylsulfonyl) phenyl)pyrimidin-2-amine	MS (m/e): 496.4 (M+1)
262	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(2-morpholinoethylsulfonyl) phenyl)pyrimidin-2-amine	MS (m/e): 512.4 (M+1)
263	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(2-thiomorpholinoethoxy) phenyl)pyrimidin-2-amine	MS (m/e): 480.4(M+1)
264	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(2-(pyrrolidin-1-yl)ethoxy)phenyl)pyrimidin-2-amine	MS (m/e): 448.4 (M+1)
265	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)pyrimidin-2-amine	MS (m/e):511.4 (M+1)
266	2-(4-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl) piperazin-1-yl)ethanol	MS (m/e): 477.5(M+1)
267	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-((tetrahydro-2H-pyran-4-yl)methoxy) phenyl) pyrimidin-2-amine	MS (m/e): 449.4 (M+1)
268	trifluoro-N-(4-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy) pyrimidin-2-ylamino) phenyl)methanesulfonamide	MS (m/e): 482.3 (M+1)
269	tert-butyl 4-(2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-yiamino)phenoxy)ethyl)piperazine-1-carboxylate	MS (m/e):563.4 (M+1)
270	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(tetrahydro-2H-pyran-4-yloxy)phenyl)pyrimidin-2-amine	MS (m/e):435.4 (M+1)
271	N-(3-(2-aminoethoxy)phenyl)-4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine	MS (m/e):394.4 (M+1)
272	N-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-yl amino)benzyl)methanesulfonamide	MS (m/e): 442.4(M+1)
273	3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)-N-(2-hydroxyethyl)benzamide	MS (m/e): 422.1 (M+1)
274	3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)-N-(2-(methylamino)-2-oxoethyl)benzamide	MS (m/e): 449.5 (M+1)
275	3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)-N-(2-morpholinoethyl)benzamide	MS (m/e): 491.1 (M+1)
276	N-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-yl amino) phenyl)methanesulfonamide	MS (m/e): 428.1 (M+1)
277	3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)-N-(2-(piperidin-1-yl)ethyl)benzamide	MS (m/e): 489.1 (M+1)
278	3-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)-N-methylpropanamide	MS (m/e): 420.2 (M+1)
279	3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)-N-(2-methoxyethyl)benzamide	MS (m/e):436.1 (M+1)
280	N-(4-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-yl amino) phenyl)methanesulfonamide	MS (m/e): 428.1(M+1)
281	2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)-N-(2-morpholinoethyl)acetamide	MS (m/e): 505.1(M+1)
282	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(2-(methylsulfonyl) ethoxy)phenyl)pyrimidin-2-amine	MS (m/e): 457.2 (M+1)
283	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(6-methoxypyridin-3-yl)pyrimidin-2-amine	MS (m/e): 366.4 (M+1)

Example 284: Synthesis of 3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-yl amino)phenol (Compound 284):

[0040] 

[0041] A solution of N2-(3-methoxylphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine (0.1mmol) in 5ml CH₂Cl₂ was placed in an ice bath. To this was added BBr₃(0.5mmol). The reaction mixture was stirred overnight at room temperature, then poured into ice water, and extracted with ethyl acetate. The organic layer was washed sequentially with water and brine, dried over anhydrous Na₂SO₄, and concentrated. The residue was purified by column chromatography to provide the desired product in a yield of 83%.

[0042] ¹H NMR (DMSO-d₆, 400 MHz): δ 10.501 (s, 1H), 9.115 (s, 1H), 8.956 (s, 1H), 8.868 (s, 1H), 7.908 (d, J=6Hz, 1H), 7.716 (s,1H), 7.271 (d, J=8Hz, 1H), 7.210 (d, J=8.4Hz, 1H), 7.114 (d, J=8Hz, 1H) ,6.968 (t, J=8Hz, 1H), 6.322 (dd, J=8,1.6Hz, 1H), 6.097 (m, 2H), 2.377 (s, 3H); MS (m/e): 331.4 (M+1).

Examples 285-295: Syntheses of Compounds 285-295

[0043] Compounds 285-295 were each synthesized in a manner similar to that described in Example 284.

compound	Name	1H NMR (CD3OD, 400 MHz)/MS
285	4-(5-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-1H-pyrazol-3-yl)phenol	7.863 (d, J=6.0 Hz, 1H), 7.286 (d, J=8.8 Hz, 1H), 6.830 (br, 2H), 6.125-6.080(m, 4H), 5.558-5.527 (m, 2H), 2.415(s,3H); MS(m/e): 411.8 (M+1).
286	2-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol	7.791( d, J=6.0 Hz, 2H), 7.584( s, 1H), 7.047 (d, J=8.8 Hz, 1H), 7.063 (d, J=7.6 Hz, 1H),6.974(t, J=7.6 Hz, 1H), 6.882(d, J=8.0 Hz, 1H), 6.794(t, J=8.0Hz, 1H), 6.164(d, J=6.0 Hz, 1H), 6.124(s, 1H), 2.027 (s, 3H); MS(m/e): 332.2 (M+1).
287	4-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol	10.573(s, 1H), 9.162(s, 1H), 9.007(s, 1H), 8.985(s, 1H), 7.952(d, J=5.6Hz, 1H), 7.766(s, 1H), 7.301(d, J=8Hz, 1H), 7.262(d, J=8Hz, 1H), 7.123(d, J=8Hz, 1H) ,7.011(m, 1H), 6.332(dd, J=8,1.6Hz, 1H), 6.103(m, 2H), 2.391(s, 3H); MS(m/e): 331.4 (M+1)
289	4-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenol	8.133(d, J=6.0 Hz, 1H), 7.324(d, J=8.4 Hz, 1H), 7.225-7.183(m, 3H), 6.819 (dd, J=8.8 Hz, J=2.4 Hz, 1H), 6.533 (s, 1H), 6.530 (s, 1H), 6.213 (d,
		J=5.6 Hz, 1H), 6.172 (s, 1H), 2.428 (s, 3H); MS(m/e): 374.3 (M+1).
290	3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenol	8.179( d, J=6.0 Hz, 1H), 7.333( d, J=8.8 Hz, 1H), 7.193(s, 1H), 7.095(s, 1H), 6.953( d, J=7.2 Hz, 1H), 6.902( t, J=8.0 Hz, 1H), 6.831( d, J=8.8 Hz, 1H), 6.387( d, J=7.6 Hz, 1H), 6.244( d, J=6.0 Hz, 1H), 6.171 (s, 1H), 3.332 (s, 3H), 2.454 (s, 3H); MS(m/e): 333.2 (M+1).
291	2-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol	11.249(s, 1H), 8.943 (d, J=4.8 Hz, 1H), 7.920 (d, J=5.6 Hz,1H), 7.867 (m, J=6.4 Hz,2H), 7.128(d, J=8.0 Hz, 1H), 7.078(t, J=8.4-6.8 Hz,1H),6.797(s, 2H), 6.589 (s, 1H),6.217(s,1H) ,6.075(s,1H), 4.061(m, J=7.2-6.8 Hz,1H)2.406 (s, 3H); MS: 350.2(M+1).
292	4-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol	11.212(s, 1H), 8.845(s, 1H), 8.689(d, J=10.0Hz,1H), 7.868 (d, J=5.6 Hz,2H), 7.427(d, J=8.4 Hz, 2H), 7.107(t, J=8.4-6.4Hz, 1H),6.509(d, J=8.0 Hz, 2H), 6.208 (s, 1H),5.940(m, J=3.6-1.6 Hz,1H) , 4.060(m, J=7.2-6.8 Hz,1H),2.408 (s, 3H); MS(m/e): 350.2(M+1).
293	3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol	11.217(s, 1H), 9.069(s, 1H), 8.836(s,1H), 8.715(s,1H), 7.922(d, J=6.0Hz,1H), 7.224 (d,
		J=8.4 Hz,2H), 7.128(T, J=6.4-2.4 Hz, 2H), 6.839(t, J=8.4-6.4Hz,1H),6.268(d, J=1.6 Hz, 2H), 6.249 (s, 1H), 6.207 (s, 1H), 4.043(m, J=7.2-6.8 Hz,1H),2.400 (s, 3H); MS(m/e): 350.2(M+1).
294	3-(4-(4-methylbenzo[d]oxazol-6-ylamino)pyrimidin-2-ylamino) phenol	9.500 (s, 1H), 9.175 (s, 1H), 9.054 (s, 1H), 8.164 (s, 1H), 8.003 (d, J=6.0 Hz,1H), 7.569 (m, 2H), 7.230 (m, 2H), 6.996 (dd, 1H), 6.338 (d, J=8.0 Hz, 1H), 7.239 (d, J=6.0 Hz,1H), 2.607 (s, 3H). MS(m/e): 334.2 (M+1).
295	3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenol	MS (m/e): 351.4 (M+1)

Example 296 : Synthesis of N-(2-methoxypyrimidin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine (Compound 296):

[0044] 

[0045] The solution of 2-chloropyrimidin-4-amine (1mmol) and sodiumn methoxide (1.5mmol) in 10ml methanol was refluxed for 2h, after removing of solvent, the residue was dissolved in CH₂Cl₂ and washed with water, dried over anhydrous NaSO4, concentrated in vacuo to give 2-methoxypyrimidin-4-amine.

[0046] To a solution of 2-methoxypyrimidin-4-amine (0.1mmol) and N-(2-chloropyrimidin-4-yl)-2-methyl-1H-indol-5-amine (0.1mmol) in 3ml dioxide, CsCO₃ (0.2mmol), Pd(OAc)₂(10mmol%) and Xantphos(10mmol%) were added. The mixture was stirred under microwave irradiation at 200°C for 40mins. After cooling the solution was filtered and the filtrate was concentrated in vacuo, the residue was purified by column chromatography(C-18) to give N-(2-methoxypyrimidin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine(yield 48%).

[0047] ¹H NMR(DMSO-d6,400MHz): 10.839(s, 1 H), 9.718 (s, 1 H), 9.281 (s, 1 H), 8.162 (d, , J=6.0Hz, 1H), 8.032(m, 2H), 7.693 (s, 1H), 7.251 (d, , J=8.8Hz, 1H), 7.099 (d, , J=7.2 Hz, 1H), 6.300 (d, , J=6.0 Hz, 1H), 6.107 (s, 1H), 3.863 (s,3H), 2.383 (s, 3H); MS (m/e): 348.2 (M+1)

Example 297-299: Syntheses of Compounds 297-299

[0048] Compounds 297-299 were each synthesized in a manner similar to that described in Example 296.

compound	Name	1H NMR (DMSO-d6, 400 MHz)/MS
297	N-(2-methoxypyridin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	10.837(s, 1 H), 9.421 (s, 1 H), 9.144 (s, 1 H), 7.978 (d, J=6.0Hz, 1H ), 7.838(d, J=6.0Hz, 1H), 7.606 (s, 1H), 7.333-7.303 (m, 2H), 7.249 (d, J=8.4 Hz, 1H), 7.084 (d, J=8.0 Hz, 1H), 6.205(d, J=5.6 Hz, 1H), 6.088 (s, 1H), 3.775 (s,3H), 2.382 (s, 3H); MS (m/e): 347.2 (M+1)
298	N-(2-methoxypyridin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	11.258 (s, 1 H), 10.400 (br, 1 H), 9.036 (s, 1 H), 8.829 (s, 1 H), 8.509 (s, 1 H), 8.048 (d, J=8.4 Hz, 1H), 7.911 (d, J=5.6 Hz, 1H), 7.007-7.122 (m, 2H), 6.743 (dd, J=8.4 Hz, 1.6 Hz, 1H), 6.194 (s, 1H), 6.012 (br,1H), 3.166 (s, 3H), 2.397 (s,3H); MS (m/e): 428.1 (M+1)
299	N-(5-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)pyridin-2-yl)methanesulfonamide	MS (m/e): 411.4 (M+1)

Example 300: Synthesis of N-(2-(4-fluorophenoxy)pyrimidin-4-yl)-2-methyl-1H-indol-5-amine (Compound 300)

[0049] 

[0050] N-(2-chloropyrimidin-4-yl)-2-methyl-1H-indol-5-amine (0.1 mmol) and p-fluorophenol (0.1mmol) were dissolved in 0.5 ml DMF. To this was added K₂CO₃ (0.2mmol). After stirred at 60°C for 5 h, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine sequentially, dried by anhydrous Na₂SO₄, and concentrated. The resulting oil residue was purified by column chromatography to provide compound 300 in a yield of 76%.

[0051] ¹H NMR (DMSO-d6, 400 MHz): δ 10.802 (s, 1H), 9.491 (s, 1H), 7.990 (d, J=5.4 Hz 1H), 7.495 (s, 1H), 7.295 (m, J=8.4-3.6Hz, 4H), 7.236 (d, J=5.4 Hz 1H), 7.133 (d, J=5.6 Hz, 1H), 6.486 (d, J=5.6 Hz, 1H), 5.902 (s, 1H), 2.402 (s, 3H); MS (m/e): 335.1 (M+1).

Example 301-303: Syntheses of Compounds 301-303

[0052] Compounds 301-303 were prepared in a similar manner to that described in Example 300.

Compound	Name	1H NMR (CD3OD, 400 MHz)/MS
301	2-methyl-N-(2-(4-phenoxyphenoxy)pyrimidin-4-yl)-1H-indol-5-amine	11.190 (s, 1H), 9.046 (s, 1H), 7.959 (s,1H), 7.931 (d, J=6.0Hz, 1H), 7.681 (d, J=7.2 Hz, 2H), 7.361(t, J=8.0-7.6 Hz, 2H), 7.114 (m, J=8.4-7.2Hz,3H), 6.903 (d, J=8.0 Hz, 2H), 6.755 (d, J=7.2Hz, 2H), 6.179 (s,1H), 6.024 (s, 1H), 2.338 (s, 3H); MS(m/e): 409.2 (M+1)
302	N2-cyclopropyl-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	7.739 (d, J=6.4Hz, 1H), 7.593 (s, 1H), 7.252 (d, J=7.6 Hz, 1H), 7.119 (d, J=8.0 Hz, 1H), 6.009 (s,1H), 6.016 (d, J=6.0 Hz, 1H), 2.425(s, 3H), 0.784 (m, J=5.2-2.4, 2H), 0.626 (m, J=2.0-0.8Hz, 3H), 0.547 (m, J=2.0-1.2Hz, 3H). MS(m/e): 280.2(M+1)
303	N2-cyclohexyl-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine	MS (m/e): 322.3 (M+1)

Example 304: Synthesis of 5-(2-(3-methoxyphenoxy)pyrimidin-4-yloxy)-2-methyl-1H-indole (Compound 304):

[0053] 

[0054] To a solution of 2,4-dichloropyrimidine (1 mmol) and 5-hydroxy-2-methylindole (1 mmol) in 5ml EtOH was added Et₃N(1mmol). The reaction mixture was refluxed for 5 h. After removal of the solvent in vacuo and addition of H₂O, the mixture was extracted with EtOAc. The organic layers were combined, washed with a saturated NaCl aqueous solution, dried over anhydrous Na₂SO₄, and concentrated in vacuo. The resulting oil residue was purified by column chromatography to give 5-(2-chloropyrimidin-4-yloxy)-2-methyl-1H-indole in a yield of 75%.

[0055] 5-(2-Chloropyrimidin-4-yloxy)-2-methyl-1H-indole (0.1 mmol) and m-methoxyphenol (0.1 mmol) were dissolved in 0.5 ml DMF. K₂CO₃ (0.2 mmol) was then added. After the reaction mixture was stirred at 60°C for 5 h, it was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine sequentially, dried over anhydrous Na₂SO₄, and concentrated. The crude product was purified by column chromatography to provide compound 304 in a yield of 76%.

[0056] ¹H NMR (CD₃OD, 400 MHz): δ 8.303 (d, J=5.6 Hz, 1H), 8.084 (s, 1H), 7.305-7.262 (m, 3H), 6.908 (dd, J=8.8 Hz, J=2.4 Hz, 1H), 6.816-6.764 (m, 3H), 6.463 (d, J=5.6 Hz, 1H), 6.226 (s, 1H), 3.780 (s,3H), 2.465 (s, 3H); MS (m/e): 346.5 (M-1).

Example 305: Synthesis of 3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzonitrile (Compound 305)

[0057] 

[0058] To a solution of 2,4-dichloropyrimidine (1 mmol) and 5-Aminobenzimidazole (1 mmol) in 5ml EtOH, was added Et₃N(1mmol). The reaction mixture was refluxed for 5 hours. After removal of the solvent in vacua and addition of H₂O, the mixture was extracted with EtOAc. The organic layers were combined, washed with a saturated NaCl aqueous solution, dried over anhydrous Na₂SO₄, and concentrated in vacuo. The residue was purified by column chromatography to give N-(2-chloropyrimidin-4-yl)-1H-benzo[d]imidazol-5-amine in a yield of 80%.

[0059] N-(2-chloropyrimidin-4-yl)-1H-benzo[d]imidazol-5-amine (0.1 mmol), 3-aminobenzonitrile (0.1 mmol), and p-TsOH monohydrate (0.2 mmol) were dissolved in 0.5ml DMF. After the reaction mixture was stirred at 60°C for 5 h, it was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine sequentially, dried over anhydrous Na₂SO₄, and concentrated. The resulted oil was purified by column chromatography to provide compound 305 in a yield of 76%.

[0060] ¹H NMR (CD₃OD, 400 MHz): δ 8.178 (s, 1H), 7.942 (d, J=6.4Hz,2H), 7.825 (br, 1H), 7.633-7.603 (m, 2H), 7.469 (dd, J=8.8Hz, 5Hz, 1H), 7.212 (t, J=8.4 Hz, 1H), 7.075 (d, J=8.0Hz, 1H), 6.254 (d, J=6.0 Hz,1H), 3.345 (s, 1H); MS: 327.2 (M+1).

Example 306: Synthesis of N2-(3-methoxyphenyl)-N4-(2-methylbenzo[d]oxazol-6-yl) pyrimidine-2,4-diamine (Compound 306)

[0061] 

[0062] To a solution of 2,4-dichloropyrimidine (1 mmol) and 2-methyl-1,3-benzoxazol-5-amine (1 mmol) in 5ml EtOH was added Et₃N (1 mmol). The reaction mixture was refluxed for 5 h. After removal of the solvent in vacuo and addition of H₂O, the mixture was extracted with EtOAc. The organic layers were combined, washed with a saturated NaCl aqueous solution, dried over anhydrous Na₂SO₄, and concentrated in vacuo. The residue was purified by column chromatography to give N-(2-chloro pyrimidin-4-yl)-2-methylbenzo[d]oxazol-6-amine in a yield of 73%.

[0063] N-(2-chloropyrimidin-4-yl)-2-methylbenzo[d]oxazol-6-amine (0.1 mmol), 3-methoxyaniline (0.1 mmol), and p-TsOH monohydrate (0.2 mmol) were dissolved in 0.5ml DMF. After the reaction mixture was stirred at 60°C for 5 h, it was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine sequentially, dried over anhydrous Na₂SO₄, and concentrated. The resulting oil residue was purified by column chromatography to provide compound 306 in a yield of 82%.

[0064] ¹H NMR (DMSO-d6, 400 MHz): δ 9.431 (s, 1H), 9.158 (s, 1H), 8.136 (s, 1H), 8.022 (d, J=5.6 Hz,1H), 7.566 (d, J=8.8 Hz, 1H), 7.517 (d, J=8.8 Hz, 1H), 7.418 (s, 1H), 7.367 (d,J=8.0 Hz 1H), 7.126 (t, J=8.4 Hz, 1 H), 6.490 (m, 1H), 6.224 (d, J=5.2 Hz,1H), 3.674 (s, 3H), 2.609 (s, 3H); MS(m/e): 348.3 (M+1).

Example 307: Synthesis of N2-(3-ethynylphenyl)-N4-(2-methylbenzo[d]oxazol-6-yl) pyrimidine-2,4-diamine (Compound 307).

[0065] Compound 307 was synthesized in a similar manner to that described in Example 306.

[0066] ¹H NMR (DMSO-d6, 400 MHz): δ 9.566 (d, J=5.2 Hz, 1H), 9.309 (s, 1H), 8.099 (s, 1H), 8.038 (d, J=6.0 Hz, 1H), 7.917 (s, 1H), 7.805 (d, J=8.4 Hz, 1H), 7.574 (m, 2H), 7.231 (m, 1H), 6.996 (d, J=7.6 Hz, 1H), 7.278 (d, J=5.6 Hz,1H), 4.059 (s, 1H), 2.608 (s, 3H); MS(m/e): 342.2 (M+1).

Example 308: Synthesis of N2-(3-ethynylphenyl)-N4-(1H-indazol-6-yl)pyrimidine-2,4-diamine (Compound 308)

[0067] 

[0068] To a solution of 2,4-dichloropyrimidine (1 mmol) and 5-aminoindazole (1 mmol) dissolved in 5ml EtOH was added Et₃N (1 mmol). The reaction mixture was refluxed for 5 h. After removal of the solvent in vacuo and addition of H₂O, the mixture was extracted with EtOAc. The organic layers were combined, washed with a saturated NaCl aquesous solution, dried over anhydrous Na₂SO₄, and concentrated in vacuo. The resulted oil was purified by column chromatography to give N-(2-chloropyrimidin-4-yl)-1H-indazol-5-amine in a yield of 80%.

[0069] N-(2-chloropyrimidin-4-yl)-1H-indazol-5-amine (0.1 mmol), 3-ethnylaniline (0.1 mmol), and p-TsOH(0.2mmol, monohydrate) were dissolved in 0.5ml DMF. After the reaction mixture was stirred at 60°C for 5 h, it was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine sequentially, dried over anhydrous Na₂SO₄, and concentrated. The residue was purified by column chromatography to provide compound 308 in a yield of 74%.

[0070] ¹H NMR (DMSO-d₆, 400 MHz): δ 12.966 (brs, 1H), 9.344 (brs,1H), 9.234 (brs, 1H), 8.145 (s, 1H), 8.005 (m, 2H), 7.893 (s, 1H), 7.795 (d, 1H), 7.527 (d, J=8.8 Hz, 1H), 7.471 (d, J=8.8 Hz, 1H), 7.212 (t, 1H), 7.021 (d, 1H), 6.626 (d, 1H), 4.037 (s, 1H); MS (m/e): 327.2 (M+1).

Example 309: Synthesis of N2-(3-methoxylphenyl)-N4-(2-methyl-1H-indol-5-yl) pyrimidine-2,4-diamine (Compound 309)

[0071] 

[0072] 2,4-Dichloro-5-fluoropyrimidine (1 mmol) and 5-amino-2-methylindole (1.5 mmol) were dissolved in 3 ml CH₃OH and 9 ml H₂O. After the reaction mixture was stirred at room temperature for 1h, it was diluted with H₂O, acidified with 2N HCl, and sonicated. The reaction mixture was then filtered, washed with H₂O and dried to give N-(2-chloro-5-fluoropyrimidin-4-yl)-2-methyl-1H-indol-5-amine in a yield of 78%.

[0073] N-(2-chloro-5-fluoropyrimidin-4-yl)-2-methyl-1H-indol-5-amine (0.1 mmol), m-methoxyaniline (0.1mmol), p-TsOH monohydrate (0.2 mmol) were dissolved in 0.5 ml DMF. After the reaction mixture was stirred at 60°C for 5 h, it was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine sequentially, dried over anhydrous Na₂SO₄, and concentrated. The residue was purified by column chromatography to provide compound 309 in a yield of 60%.

[0074] ¹H NMR (CD₃OD, 400 MHz, δ ppm): 7.854 (d, J=4.0 Hz, 1H), 7.703 (d, J =1.6,1H), 7.248 (s, 2H), 7.177 (br, 2H), 7.054 (t,J=4.2 Hz, 2H), 6.942 (s, 2H), 3.506 (s, 3H), 2.235 (s, 3H); MS(m/e): 364.2 (M+1).

Example 310: Synthesis of 2-(3-methoxyphenylamino)-4-(2-methyl-1H-indol-5-ylamino) pyrimidine-5-carbonitrile (Compound 310)

[0075] 

[0076] 2-Methyl-2-thiopseudourea (5 mmol) and ethyl ethoxymethylenecyanoacetate (5 mmol) were dissolved in 20 ml EtOH. To this was added K₂CO₃, (10 mmol). After the mixture was refluxed for 48 h, it was cooled to room temperature and filtered. The solvent was concentrated in vacuo and purified by column chromatography to give 4-hydroxy-2-(methylthio) pyrimidine-5-carbonitrile in a yield of 65%.

[0077] 4-Hydroxy-2-(methylthio) pyrimidine-5-carbonitrile (3 mmol) and m-anisidine (3 mmol) in pentan-1-ol was refluxed for 40 h under nitrogen. The reaction mixture was concentrated in vacuo. The residue was washed with water and dried to afford 4-hydroxy-2-(3-methoxyphenylamino)pyrimidine-5-carbonitrile.

[0078] To a solution of 4-hydroxy-2-(3-methoxyphenylamino)pyrimidine-5-carbonitrile in POCl₃ was added DMF 0.5 ml. The solution was refluxed for 3 h. The reaction mixture was cooled to room temperature and poured into ice-water. The solution was adjusted to pH=8-9 by aqueous sodium carbonate solution and extracted with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous Na₂SO₄, concentrated in vacuo to afford 4-chloro-2-(3-methoxyphenylamino)pyrimidine-5-carbonitrile.

[0079] 4-Chloro-2-(3-methoxyphenylamino)pyrimidine-5-carbonitrile was converted to compound 310 in a similar manner to that described in Example 1.

[0080] ¹H NMR (DMSO-d6, 400 MHz): δ 10.925(s, 1H), 9.710 (d, J=11.2 Hz, 1H), 9.349 (d, J=10.4 Hz,1H), 8.441 (s, 1H), 7.474 (s, 1H), 7.252 (s, 1H), 7.223 (d, J=6.8 Hz, 1 H), 7.187 (s, 1H), 7.062 (m, J= 1H), 6.923 (d, J=2.0 Hz, 1H), 6.485 (t, 1H); 6.098 (s, 1H), 3.453 (s, 3H), 2.387 (s, 3H); MS(m/e): 371.2 (M+1).

Example 311-317: Syntheses of Compounds 311-317

[0081] Compounds 311-317 were prepared in a similar manner to that described in Example 310.

compound	Name/Structure	1HNMR(DMSO-d6,400Hz)/ MS
311	4-(2-methyl-1H-indol-5-ylamino)-2-(3-(3-morpholinopropoxy)phenylamino)pyrimid ine-5-carbonitrile	11.184 (s, 1H), 10.745 (s, 1H), 9.492 (s,1H), 8.396 (s, 1H), 7.322 (s, 1H), 7.292 (d, J=7.2, 1H), 7.147 (m, 1H), 6.919 (m, 1H), 6.815 (d, J=8.8, 1H), 6.416 (d, J=7.2, 1H), 6.261 (t, J=4.8, 1H), 6.129 (s, 1H), 3.447 (m, 2H), 3.547 (m, 4H), 2.398 (s, 3H), 2.337 (m, 6H), 1.747 (m, 2H).MS (m/e): 484.2 (M+1)
312	4-(2-methyl-1H-indol-5-yloxy)-2-(3-(3-morpholinopropoxy)phenylamino)pyrimid ine-5-carbonitrile	MS (m/e): 485.3 (M+1)
313	4-(2-methyl-1H-indol-5-ylamino)-2-(3-(2-morpholinoethoxy)phenylamino)pyrimidi ne-5-carbonitrile	MS (m/e): 470.5 (M+1)
314	4-(4-fluoro-2-methyl-1H-indol-5-ylamino)-2-(3-(trifluoromethyl)phenylamino) pyrimidine-5-carbonitrile	MS (m/e): 427.2 (M+1)
315	2-(3,4-dimethoxyphenylamino)-4-(2-methyl-1H-indol-5-ylamino)pyrimidinc-5-carbonitrile	MS (m/e): 401.4 (M+1)
316	4-(4-fluoro-2-methyl-1H-indol-5-ylamino)-2-(3-(2-morpholinoethoxy)phenylamino) pyrimidine-5-carbonitrile	MS (m/e): 488.5 (M+1)
317	2-(5-cyano-2-(3,4-dimethoxyphenylamino) pyrimidin-4-ylamino)benzamide	MS (m/e): 391.1 (M+1)

Example 318: KDR kinase activity assay using Z'-lyte kinase assay kit

[0082] Inhibition of kinase activity of a recombinant KDR catalytic domain (Invitrogen, Carlsbad, CA, U.S.A., Cat. PV3660) was determined using Z'-LYTE™ Tyrl Peptide assay kit (Invitrogen, Cat. PV3190) in a black 384-well plate (Thermo labsystems, Cambridge, U.K., Cat. 7805). The assay was performed according to the procedures recommended by the manufacturer.

[0083] Briefly, a test compound (10 mM stock in DMSO) was diluted to 1:4 with distilled water containing 8% DMSO. The solution was placed in a test well and three control wells (C1, C2, and C3) at 2.5 µl/well. Coumarin-fluorescein double-labeled peptide substrate was mixed with the KDR catalytic domain ("kinase"). 5 µl of the kinase/peptide mixture was added to each of the test, C1, and C2 wells, but not C3 (Final concentration: 0.3 µg/ml of Kinase, 2 µM of peptide). 5 µl of Phosphor-Tyrl peptide was added to the C3 well. 2.5 µl of 40 µM ATP was added to the test well and C2 well and 2.5 µl of 1.33 × kinase buffer (1×buffer: 50 mM HEPES, pH7.5, 0.01% Brij-35, 5 mM MgCl₂, 5 mM MnCl₂, and 1 mM EGTA) was added to the C1 and C3 wells. The plate was briefly spun at 1000 rpm to settle all solution down to the bottom of the wells and then sealed and shaken at 250 rpm and 25°C for 1 hour.

[0084] A development reagent was diluted to 1:128 according to the recommendation of the manufacturer. 5 µl of the diluted development reagent was added to each well. The plate was spun at 1000 rpm to settle all solution down to the wells, and then sealed and shaken at 250 rpm and 25°C for 1 hour.

[0085] 5 µl of a stop reagent was added to each well. The plate was spun at 1000 rpm to settle all solution down to the wells, and then sealed at 250 rpm and 25°C for 2 minutes. Emission of the solution at each well was measured by a VictorTM3 microplate reader at Excitation 400 nm/Emission 445 nm and 520 nm. The emission ratio and phosphorylation ("Phos.") percentage were calculated by the following equations:




where:

C_100% = Average Coumarin emission signal of the 100% Phos. Control

C_0% = Average Coumarin emission signal of the 0% Phos. Control

F_100% = Average Fluorescein emission signal of the 100% Phos. Control

F_0% = Average Fluorescein emission signal of the 0% Phos. Control

The inhibition ratio was calculated as follows:

[0086] The result showed that all of the tested compounds inhibited the activity of KDR. The IC₅₀ values ranged from 0.001 to 10 µM.

Other Embodiments

[0087] From the above description, one skilled in the art can easily ascertain the essential characteristics of the present invention, and can make various changes and modifications of the invention to adapt it to various usages and conditions. For example, compounds structurally analogous to the compounds of this invention can be made and used.

Claims

1. A compound of the following formula:

in which

X is O or NH;

Y is NH;

Z is CR', R' being H, halo, or alkyl;

V, U, and T together represent

each of R₁, R₃, R₄, and R₆, independently, is H, halo, nitro, amino, cyano, hydroxy, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, heteroaryl, alkoxy, alkylthio, alkylcarbonyl, carboxy, alkoxycarbonyl, carbonylamino, sulfonylamino, aminocarbonyl, or aminosulfonyl;

R₂ is H, halo, nitro, amino, hydroxy, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, heteroaryl, alkoxy, alkylthio, alkylcarbonyl, carboxy, alkoxycarbonyl, carbonylamino, sulfonylamino, aminocarbonyl, or aminosulfonyl;

R₅ is alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl; and

R₇ is alkyl;

wherein alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and alkoxy are optionally substituted with at least one group selected from halo, hydroxyl, amino, cyano, nitro, mercapto, alkoxycarbonyl, amido, carboxy, alkanesulfonyl, alkylcarbonyl, carbamido, carbamyl, carboxyl, thioureido, thiocyanato, sulfonamido, alkyl, alkenyl, alkynyl, alkyloxy, aryl, heteroaryl, cycloalkyl and heterocycloalkyl, in which alkyl, alkenyl, alkynyl, alkyloxy, aryl, heteroaryl, cycloalkyl, and heterocycloalkyl may further substituted;
or a pharmaceutically acceptable salt thereof

2. The compound or a pharmaceutically acceptable salt thereof of any preceding claim, wherein R₆ is H and R₇ is methyl.

3. The compound or a pharmaceutically acceptable salt thereof of any preceding claim, wherein R₅ is aryl or heteroaryl, optionally substituted with halo, nitro, amino, cyano, hydroxy, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, heteroaryl, alkoxy, alkylthio, alkylcarbonyl, carboxy, alkoxycarbonyl, sulfonyl, carbonylamino, sulfonylamino, aminocarbonyl, or aminosulfonyl.

4. The compound or a pharmaceutically acceptable salt thereof of claim 1,
wherein the compound is one of the following compounds:

Compound	Name/Structure
1	N4-(2-methyl-1H-indol-5-yl)-N2-phenylpyrimidine-2,4-diamine
2	N2-(3-ethynylphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
3	N2-(3-bromophenyl)-N4-(2-methyl-1H-indol-5 -yl)pyrimidine-2,4-diamine
4	N2-(3-fluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
5	N2-(3-chlorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
6	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(trifluoromethyl)phenyl) pyrimidine-2,4-diamine
7	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(methylsulfonyl)phenyl)pyrimidine-2,4-diamine
8	N2-(3-methoxylphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
9	ethyl 1-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidine-4-carboxylate
10	N2,N4-bis(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
11	N2-(1H-indazol-5-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
12	N2-(1H-benzo[d]imidazol-5-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
13	N2-(2-methoxyphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
14	N2-(2-chlorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
15	N2-(2-bromophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
16	N2-(4-fluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
17	methyl 2-(4-(4-(2-methyl-1H-indol-5-ylamino)pyirmidin-2-ylamino)phenyl)acetate
19	N2-(4-methoxyphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
20	N4-(2-methyl-1H-indol-5-yl)-N2-(4-(2-morpholinoethoxy)phenyl) pyrimidine-2,4-diamine
21	N2-(3,4-difluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
22	N2-(3,5-dimethylphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
23	2-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)ethanol
24	N4-(2-methyl-1H-indol-5-yl)-N2-(2-morpholinoethyl)pyrimidine-2,4-diamine
25	N-cyclopropyl-2-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)acetamide
28	N-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)methanesulfonamide
29	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(2-morpholinoethoxy) phenyl) pyrimidine-2,4-diamine
30	N2-(3-(3-(dimethylamino) propoxy)phenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4 diamine
31
	2-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino) phenoxy)ethanol
32	2-(2-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethanol
33	N4-(2-methyl-1H-indol-5-yl)-N2-(2-(2-morpholinoethoxy)phenyl) pyrimidine-2,4-diamine
34	N-methyl-3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzamide
35	3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-(2-(piperidin-1-yl)ethyl)benzamide
36	N-(2-(dimethylamino)ethyl)-3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzamide
37	N2-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
38	N-(3-ethynylphenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine
39	N-(4-methoxyphenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine
42	N-(3-methoxyphenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine
43	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(3-(thiomorpholino-1',1'-dioxide)propoxy)phenyl)pyrimidin-2-amine
44	N-methyl-3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzamide
48	N-(4-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)methanesulfonamide
49	2-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)-N-(2-morpholinoethyl)acetamide
50	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(2-(methylsulfonyl)ethoxy)phenyl)pyrimidin -2-amine
52	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-fluorophenyl) pyrimidine-2,4-diamine
53	N2-(3-chlorophenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
54	2-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzonitrile
55	N2-(3,5-dimethylphenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
56	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(2-(trifluoromethyl) phenyl)pyrimidine-2,4-diamine
57	N2-(2-chlorophenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
59	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(4-methoxyphenyl) pyrimidine-2,4-diamine
61	2-(1-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)ethanol
62	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(3-(methylsulfonyl)propoxy)phenyl)pyrimidi ne-2,4-diamine
63	2-(3-(4-(4-tluoro-2-methyl-1H-indol-5-ylainino)pyrimidin-2-ylamino)phenoxy)ethanol
65	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-((1-(methylsulfonyl)piperidin-4-yl)methoxy)phenyl)pyrimidine-2,4-diamine
66	1-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-ol
67	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(methylsulfonyl)phenyl)pyrimidin-2-amine
68	N-cyclopropyl-2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)acetamide
69	(E)-3-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)-N-methylacrylamide
70	3-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylainino)phenyl)-N,N-dimethylpropanamide
71	N-methyl-3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzamide
72	N2-(2-fluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
73	3-(4-(2-inethyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzonitrile
77	N2-(3,4-dimethoxyphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
78	N2-(4-chlorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
79	N2-(2,4-difluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
80	N2-(3-chloro-2-fluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
81	N2-(1H-indol-4-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
82	N2-(4-(3-(dimethylamino)propoxy)phenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
83	2-(4-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethanol
84	N2-(3-chloro-4-fluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
86	(1-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)methanol
87	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)phenyl)pyrimidine-2,4-diamine
89	N2-(2-chloro-4-fluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
90	2-chloro-4-fluoro-5-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol
91	N2-(4-chloro-2-fluorophenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
92	N2-(3-(2-(dimethylamino)ethoxy)phenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
93	N2-(2-methyl-1H-indol-5-yl)-N4-(3-(3-(methylsulfonyl)propoxy)phenyl)pyrimidi ne-2,4-diamine
94	2-(1-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)ethanol
95	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(piperidin-4-ylmethoxy)phenyl)pyrimidine-2,4-diamine
97	1-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-ol
101	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(3-(4-(methylsulfonyl)piperazin-1-yl)propoxy)phenyl)pyrimidine-2,4-diamine
102	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(3-morpholinopropoxy)phenyl) pyrimidine-2,4-diamine
104	(E)-N,N-dimethyl-3-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)acrylamide
105	4-(4-fluoro-2-methyl-1H-indol-5-yl)-N-(3-(3-(thiomorpholino-1',1'-dioxide)propoxy)phenyl)pyrimidin-2-amine
106	N4-(2-inethyl-1H-indol-5-yl)-N2-(3-(2-(methylamino)ethoxy)phenyl)pyrimidine-2,4-diamine
107	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3- (3-(thiomorpholino-1'-oxide) propoxy) phenyl) pyrimidin-2-amine
108	N-(2-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethyl)methanesulfonam ide
109	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(3-thiomorpholinopropoxy) phenyl)pyrimidine-2,4-diamine
111	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(2-thiomorpholinoethoxy) phenyl)pyrimidine-2,4-diamine
112	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(2-pyrrolidinethoxy)phenyl)pyrimidine-2,4-diamine
115	N4-(2-methyl-1H-indol-5-yl)-N2-(3-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)pyrimidine-2,4-diamine
116	2-(4-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperazin-1-yl)ethanol
117	N4-(2-methyl-1H-indol-5-yl)-N2-(3-(methylsulfonylmethyl)phenyl)pyrimidine -2,4-diamine
118	N,N-dimethyl-3-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)propanamide
119	(E)-N-methyl-3-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)acrylamide
121	N2-(3-(2-aminoethoxy)phenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
122	N-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino) benzyl)methanesulfonamide
124	N-methyl-3-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)propanamide
130	N-(4-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-yl amino)phenyl)methanesulfonamide
132	N2-(6-methoxypyridin-3-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
133	2-methyl-N-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-yl)-1H-indol-5-amine
134	N-(3-(3-(dimethylamino)propoxy)phenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine
135	2-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy)ethanol
136	N-(3-(2-(dimethylamino)ethoxy)phenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine
137	N-cyclopropyl-2-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)acetamide
138	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(3-(methylsulfonyl)propoxy)phenyl)pyrimidin-2-amine
139	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(piperidin-4-ylmethoxy)phenyl)pyrimidin-2-amine
143	1-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-ol
144	(1-(3(4-(2-methyl-1H-indol-5-yLoxy)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)methanol
145	2-(1-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)ethanol
146	N-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl) methanesulfonamide
148	(E)-N,N-dimethyl-3-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)acrylamide
150	N-(3-(2-methoxyethoxy)phenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine
152	N-(2-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy)ethyl)methanesulfonam ide
154	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(2-morpholinoethoxy)phenyl)pyrimidin-2-amine
156	N-(3-(2-methoxyethoxy)phenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine
157	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(morpholinomethyl)phenyl)pyrimidin-2-amine
158	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(3-thiomorpholinopropoxy)phenyl)pyrimidin-2-amine
162	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(2-thiomorpholinoethoxy)phenyl)pyrimidin-2-amine
163	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(2-(pyrrolidin-1-yl)ethoxy)phenyl)pyrimidin-2-amine
164	4-(2-methyl-1H-indol-5-yloxy)-N-(3-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)pyrimidin-2-amine
165	2-(4-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperazin-1-yl)ethanol
166	4-(2-methyl-1H-indol-5-yloxy)-N-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)pyrimidin-2-amine
167	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(methylsulfonylmethyl)phenyl)pyrimidin-2-amine
168	tert-butyl 4-(2-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy)ethyl)piperazine-1-carboxylate
169	N,N-dimethyl-3-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino))phenyl)propanamide
170	(E)-N-methyl-3-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)acrylamide
172	N-(3-(2-aminoethoxy)phenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine
173	N-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)methanesulfonamide
175	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(2-(piperazin-1-yl)ethoxy)phenyl)pyrimidin-2-amine
179	N-methyl-3-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino))phenyl)propanamide
181	N-(4-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)methanesulfonamide
183	4-(2-methyl-1H-indol-5-yloxy)-N-(3-(2-(methylsulfonyl)ethoxy)phenyl)pyrimidin -2-amine
185	N-(6-methoxypyridin-3-yl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-Amine
186	methyl 2-(4-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)acetate
187	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(2-methoxyphenyl)pyrimidine-2,4-diamine
188	N2-(3-bromophenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
189	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(methylsulfonyl) phenyl)pyrimidine-2,4-diamine
190	3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzonitrile
191	N2-(2-chloro-4-fluorophenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
192	N-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)methanesulfonamide
193	N2-(3,4-difluorophenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
194	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(2-morpholinoethoxy)phenyl)pyrimidine-2,4-diamine
195	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)phenyl)pyrimidine-2,4-diamine
196	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(2-(2-morpholinoethoxy)phenyl)pyrimidine-2,4-diamine
197	N2-(3-(3-(dimethylamino)propoxy)phenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
198	N-cyclopropyl-2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)acetamide
199	N-(2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-yl amino) phenoxy)ethyl)methanesulfonamide
200	2-(2-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethanol
201	N2-(3-(2-(dimethylamino)ethoxy)phenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
202	(1-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)methanol
203	3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-methylbenzamide
205	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(piperidin-4-ylmethoxy)phenyl)pyrimidine-2,4-diamine
208	N-(5-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)pyridin-2-yl)acetamide
211	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine
212	4-(4-fluoro-2-methyl-1H-indol-5-yl)-N-(3-(3-(thiomorpholino-1',1'-dioxide)propoxy)phenyl)pyrimidin-2-amine
214	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(2-(methylamino)ethoxy)phenyl)pyrimidine-2,4-diamine
216	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(3-thiomorpholinopropoxy)phenyl)pyrimidin e-2,4-diamine
218	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(2-thiomorpholino ethoxy)phenyl)pyrimidine-2,4-diamine
219	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(2-(pyrrolidin-1-yl)ethoxy)phenyl)pyrimidine-2,4-diamine
220	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)pyrimidine-2,4-diamine
221	2-(4-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperazin-1-yl)ethanol
223	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-(methylsulfonylmethyl) phenyl)pyrimidine-2,4-diamine
224	tert-butyl 4-(2-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-yl amino)phenoxy)ethyl)piperazine-1-carboxylate
225	tert-butyl 4-(2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethyl)piperazine-1-carboxylate
226	3-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino))phenyl)-N,N-dimethylpropanamide
227	(E)-3-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)-N-methylacrylamide
228	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)pyrimidine-2,4-diamine
229	N2-(3-(2-aminoethoxy)phenyl)-N4-(4-fluoro-2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
230	N-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)methanesulfonamide
234	3-(3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)-N-methylpropanamide
236	N-(4-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-yl amino)phenyl)methanesulfonamide
241	N4-(4-fluoro-2-methyl-1H-indol-5-yl)-N2-(6-methoxypyridin-3-yl)pyrimidine-2,4-diamine
242	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(2-morpholinoethoxy) phenyl)pyrimidin-2-amine
243	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(3-morpholino propoxy)phenyl)pyrimidin-2-amine
244	2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy)ethanol
245	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(3-(thiomorpholino-1',1'-dioxide) propoxy)phenyl)pyrimidin-2-amine
251	(1-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)methanol
252	2-(1-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)ethanol
253	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(2-(methylamino)ethoxy)phenyl)pyrimidin-2-amine
255	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(morpholino methyl)phenyl)pyrimidin-2-amine
257	3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)-N-methylbenzamide
258	N-(2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy) ethyl)methanesulfonamide
260	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(3-thiomorpholinopropoxy) phenyl)pyrimidin-2-amine
263	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(2-thiomorpholinoethoxy) phenyl)pyrimidin-2-amine
264	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(2-(pyrrolidin-1-yl)ethoxy)phenyl)pyrimidin-2-amine
265	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)pyrimidin-2-amine
266	2-(4-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl) piperazin-1-yl)ethanol
267	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-((tetrahydro-2H-pyran-4-yl)methoxy) phenyl) pyrimidin-2-amine
269	tert-butyl 4-(2-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy)ethyl)piperazine-1-carboxylate
271	N-(3-(2-aminoethoxy)phenyl)-4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-amine
272	N-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-yl amino)benzyl)methanesulfonamide
276	N-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-yl amino) phenyl)methanesulfonamide
278	3-(3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)-N-methylpropanamide
280	N-(4-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-yl amino) phenyl)methanesulfonamide
282	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(3-(2-(methylsulfonyl) ethoxy)phenyl)pyrimidin-2-amine
283	4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-N-(6-methoxypyridin-3-yl)pyrimidin-2-amine

compound	Name
284	3-(4-(2-inethyl-1H-indol-5-ylamino)pyrimidin-2-yl amino)phenol
285	4-(5-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-1H-pyrazol-3-yl)phenol
286	2-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol
287	4-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol
289	4-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenol
290	3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenol
291	2-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol
292	4-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol
293	3-(4-(4-fluoro-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol
294	3-(4-(2-methylbenzo[d]oxazol-6-ylamino)pyrimidin-2-ylamino) phenol
295	3-(4-(4-fluoro-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenol

compound	Name
296	N-(2-methoxypyrimidin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
297	N-(2-methoxypyridin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
298	N-(2-methoxypyridin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
299	N-(5-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)pyridin-2-yl)methanesulfonamide

Compound	Name
302	N2-cyclopropyl-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine
303	N2-cyclohexyl-N4-(2-methyl-1H-indol-5-yl)pyrimidine-2,4-diamine

compound	Name/Structure
305	3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzonitrile
309	N2-(3-methoxylphenyl)-N4-(2-methyl-1H-indol-5-yl) pyrimidine-2,4-diamine

5. Use of an effective amount of a compound or a pharmaceutically acceptable salt thereof of any of claims 1 to 4 in the manufacture of a medicament for treating an angiogenesis-related disorder.

6. The use of claim 5, wherein the angiogenesis-related disorder is cancer or age-related macular degeneration.

7. Use of an effective amount of a compound or a pharmaceutically acceptable salt thereof of any of claims 1 to 4 in the manufacture of a medicament for inhibiting angiogenesis in a subject.

8. A compound or a pharmaceutically acceptable salt thereof of any of claims 1 to 4 for use in treating an angiogenesis-related disorder.

9. The compound or a pharmaceutically acceptable salt thereof of claim 8, wherein the angiogenesis-related disorder is cancer or age-related macula degeneration.

10. A compound or a pharmaceutically acceptable salt thereof of any of claims 1 to 4 for use in inhibiting angiogenesis in a subject.

11. A non-therapeutic method of inhibiting the activity of kinase insert domain receptor comprising contacting the receptor with an effective amount of a compound or a pharmaceutically acceptable salt thereof of any of claims 1 to 4.

Ansprüche

1. Verbindung der folgenden Formel:

in der

X für O oder NH steht;

Y für NH steht;

Z für CR' steht, wobei R' für H, Halogen oder Alkyl steht;

V, U und T zusammen für

stehen,

R₁, R₃, R₄ und R₆ jeweils unabhängig für H, Halogen, Nitro, Amino, Cyano, Hydroxy, Alkyl, Alkenyl, Alkinyl, Aryl, Cycloalkyl, Heterocycloalkyl, Heteroaryl, Alkoxy, Alkylthio, Alkylcarbonyl, Carboxy, Alkoxycarbonyl, Carbonylamino, Sulfonylamino, Aminocarbonyl oder Aminosulfonyl stehen;

R₂ für H, Halogen, Nitro, Amino, Hydroxy, Alkyl, Alkenyl, Alkinyl, Aryl, Cycloalkyl, Heterocycloalkyl, Heteroaryl, Alkoxy, Alkylthio, Alkylcarbonyl, Carboxy, Alkoxycarbonyl, Carbonylamino, Sulfonylamino, Aminocarbonyl oder Aminosulfonyl steht;

R₅ für Alkyl, Cycloalkyl, Heterocycloalkyl, Aryl oder Heteroaryl steht; und

R₇ für Alkyl steht;

wobei Alkyl, Cycloalkyl, Heterocycloalkyl, Aryl, Heteroaryl und Alkoxy gegebenenfalls durch mindestens eine aus Halogen, Hydroxyl, Amino, Cyano, Nitro, Mercapto, Alkoxycarbonyl, Amido, Carboxy, Alkansulfonyl, Alkylcarbonyl, Carbamido, Carbamyl, Carboxyl, Thioureido, Thiocyanato, Sulfonamido, Alkyl, Alkenyl, Alkinyl, Alkyloxy, Aryl, Heteroaryl, Cycloalkyl und Heterocycloalkyl ausgewählte Gruppe substituiert sind, wobei Alkyl, Alkenyl, Alkinyl, Alkyloxy, Aryl, Heteroaryl, Cycloalkyl und Heterocycloalkyl weiter substituiert sein können;

oder ein pharmazeutisch unbedenkliches Salz davon.

2. Verbindung oder pharmazeutisch unbedenkliches Salz davon nach einem der vorhergehenden Ansprüche, wobei R₆ für H steht und R₇ für Methyl steht.

3. Verbindung oder pharmazeutisch unbedenkliches Salz davon nach einem der vorhergehenden Ansprüche, wobei R₅ für Aryl oder Heteroaryl, das gegebenenfalls durch Halogen, Nitro, Amino, Cyano, Hydroxy, Alkyl, Alkenyl, Alkinyl, Aryl, Cycloalkyl, Heterocycloalkyl, Heteroaryl, Alkoxy, Alkylthio, Alkylcarbonyl, Carboxy, Alkoxycarbonyl, Sulfonyl, Carbonylamino, Sulfonylamino, Aminocarbonyl oder Aminosulfonyl substituiert ist, steht.

4. Verbindung oder pharmazeutisch unbedenkliches Salz davon nach Anspruch 1, wobei es sich bei der Verbindung um eine der folgenden Verbindungen handelt:

Verbindung	Name/Struktur
1	N4-(2-Methyl-1H-indol-5-yl)-N2-phenylpyrimidin-2,4-diamin
2	N2-(3-Ethinylphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
3	N2-(3-Bromphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
4	N2-(3-Fluorphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
5	N2-(3-Chlorphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
6	N4-(2-Methyl-1H-indol-5-yl)-N2-(3-trifluormethyl)phenyl)-pyrimidin-2,4-diamin
7	N4-(2-Methyl-1H-indol-5-yl)-N2-(3-methylsulfonyl)phenyl)-pyrimidin-2,4-diamin
8	N2-(3-Methoxyphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
9	1-(3-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-carbonsäureethylester
10	N2,N4-Bis(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
11	N2-(1H-Indazol-5-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
12	N2-(1H-Benzo[d]imidazol-5-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
13	N2-(2-Methoxyphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
14	N2-(2-Chlorphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
15	N2-(2-Bromphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
16	N2-(4-Fluorphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
17	2-(4-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)essigsäure-methylester
19	N2-(4-Methoxyphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
20	N4-(2-Methyl-1H-indol-5-yl)-N2-(4-(2-morpholinoethoxy)phenyl)-pyrimidin-2,4-diamin
21	N2-(3,4-Difluorphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
22	N2-(3,5-Dimethylphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
23	2-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)ethanol
24	N4-(2-Methyl-1H-indol-5-yl)-N2-(2-morpholinoethyl)pyrimidin-2,4-diamin
25	N-Cyclopropyl-2-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)acetamid
28	N-(3-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)methansulfon-amid
29	N4-(2-Methyl-1H-indol-5-yl)-N2-(3-(2-morpholinoethoxy)phenyl)-pyrimidin-2,4-diamin
30	N2- (3- 3-(Dimethylamino)propoxy)phenyl) -N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
31	2-(3-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethanol
32	2-(2-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethanol
33	N4-(2-Methyl-1H-indol-5-yl)-N2-(2-(2-morpholinoethoxy)phenyl)-pyrimidin-2,4-diamin
34	N-Methyl-3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzamid
35	3-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-(2-(piperidin-1-yl)ethyl)benzamid
36	N-(2-(Dimethylamino)ethyl)-3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzamid
37	N2-(3-(4-Methoxyphenyl)-1H-pyrazol-5-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
38	N-(3-Ethinylphenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amin
39	N-(4-Methoxyphenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amin
42	N-(3-Methoxyphenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amin
43	4-(2-Methyl-1H-indol-5-yloxy)-N-(3-(3-(thiomorpholino-1',1'-dioxid)propoxy)phenyl)-pyrimidin-2-amin
44	N-Methyl-3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzamid
48	N-(4-(4-(2-Methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)methansulfonamid
49	2-(3-(4-(2-Methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)-N-(2-morpholinoethyl)acetamid
50	4-(2-Methyl-1H-indol-5-yloxy)-N-(3-(2-(methylsulfonyl)ethoxy)phenyl) pyrimidin-2-amin
52	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(3-fluorphenyl)pyrimidin-2,4-diamin
53	N2-(3-Chlorphenyl)-N4-(4-fluor-2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
54	2-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzonitril
55	N2-(3,5-Dimethylphenyl)-N4-(4-fluor-2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
56	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(2-(trifluormethyl)phenyl)-pyrimidin-2,4-diamin
57	N2-(2-Chlorphenyl)-N4-(4-fluor-2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
59	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(4-methoxyphenyl)pyrimidin-2,4-diamin
61	2-(1-(3-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)ethanol
62	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(3-(3-(methylsulfonyl)propoxy)phenyl)-pyrimidin-2,4-diamin
63	2-(3-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethanol
65	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(3-((1-(methylsulfonyl)piperidin-4-yl)methoxy)phenyl)pyrimidin-2,4-diamin
66	1-(3-(4-(4-Fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-ol
67	4-(4-Fluor-2-methyl-1H-indol-5-yloxy)-N-(3-(methylsulfonyl)phenyl)-pyrimidin-2-amin
68	N-Cyclopropyl-2-(3-(4-(4-fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)acetamid
69	(E)-3-(3-(4-(4-Fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)-N-methylacrylamid
70	3-(3-(4-(4-Fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)-N,N-dimethylpropanamid
71	N-Methyl-3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzamid
72	N2-(2-Fluorphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
73	3-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzonitril
77	N2-(3,4-Dimethoxyphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
78	N2-(4-Chlorphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
79	N2-(2,4-Difluorphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
80	N2-(3-Chlor-2-fluorphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
81	N2-(1H-Indol-4-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
82	N2-(4-(3-(Dimethylamino)propoxy)phenyl) -N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
83	2-(4-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethanol
84	N2-(3-Chlor-4-fluorphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
86	(1-(3-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)methanol
87	N4-(2-Methyl-1H-indol-5-yl)-N2-(3-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)phenyl)pyrimidin-2,4-diamin
89	N2-(2-Chlor-4-fluorphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
90	2-Chlor-4-fluor-5-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol
91	N2-(4-Chlor-2-fluorphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
92	N2- (3- (2-(Dimethylamino)ethoxy)phenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
93	N2-(2-Methyl-1H-indol-5-yl)-N4-(3-(3-(methylsulfonyl)-propoxy)phenyl)pyrimidin-2,4-diamin
94	2-(1-(3-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)ethanol
95	N4-(2-Methyl-1H-indol-5-yl)-N2-(3-(piperidin-4-ylmethoxy)phenyl)pyrimidin-2,4-diamin
97	1-(3-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-ol
101	N4-(2-Methyl-1H-indol-5-yl)-N2-(3-(3-(4-(methylsulfonyl)piperazin-1-yl)propoxy)phenyl)pyrimidin-2,4-diamin
102	N4-(2-Methyl-1H-indol-5-yl)-N2-(3-(3-morpholinopropoxy)-phenyl)pyrimidin-2,4-diamin
104	(E)-N,N-Dimethyl-3-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)acrylamid
105	4-(4-Fluor-2-methyl-1H-indol-5-yl)-N-(3-(3-(thiomorpholino-1',1'-dioxid)propoxy)phenyl)-pyrimidin-2-amin
106	N4-(2-Methyl-1H-indol-5-yl)-N2-(3-(2-(methylamino)ethoxy)-phenyl)pyrimidin-2,4-diamin
107	4-(4-Fluor-2-methyl-1H-indol-5-yloxy)-N-(3-(3-(thiomorpholino-1'-oxid)propoxy)phenyl)pyrimidin-2-amin
108	N-(2-(3-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethyl)methan-sulfonamid
109	N4-(2-Methyl-1H-indol-5-yl)-N2-(3-(3-thiomorpholinopropoxy)-phenyl)pyrimidin-2,4-diamin
111	N4-(2-Methyl-1H-indol-5-yl)-N2- (3- (2-thiomorpholinoethoxy)phenyl)-pyrimidin-2,4-diamin
112	N4-(2-Methyl-1H-indol-5-yl)-N2-(3-(2-pyrrolidinethoxy)phenyl)-pyrimidin-2,4-diamin
115	N4-(2-Methyl-1H-indol-5-yl)-N2-(3-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)pyrimidin-2,4-diamin
116	2-(4-(3-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperazin-1-yl)ethanol
117	N4-(2-Methyl-1H-indol-5-yl)-N2-(3-(methylsulfonylmethyl)phenyl)-pyrimidin-2,4-diamin
118	N,N-Dimethyl-3-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)propanamid
119	(E)-N-Methyl-3-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)acrylamid
121	N2-(3-(2-Aminoethoxy)phenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
122	N-(3-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)methan-sulfonamid
124	N-Methyl-3-(3-(4-(2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)propanamid
130	N-(4-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)methan-sulfonamid
132	N2-(6-Methoxypyridin-3-yl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
133	2-Methyl-N-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-yl)-1H-indol-5-amin
134	N- (3-(3-(Dimethylamino)propoxy)phenyl) -4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amin
135	2-(3-(4-(2-Methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy)ethanol
136	N- (3- (2-(Dimethylamino)ethoxy)phenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amin
137	N-Cyclopropyl-2-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)acetamid
138	4-(2-Methyl-1H-indol-5-yloxy)-N-(3-(3-(methylsulfonyl)-propoxy)phenyl)pyrimidin-2-amin
139	4-(2-Methyl-1H-indol-5-yloxy)-N-(3-(piperidin-4-ylmethoxy)phenyl)pyrimidin-2-amin
143	1-(3-(4-(2-Methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-ol
144	(1-(3-(4-(2-Methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)methanol
145	2-(1-(3-(4-(2-Methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)ethanol
146	N-(3-(4-(2-Methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)methansulfonamid
148	(E)-N,N-Dimethyl-3-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)acrylamid
150	N-(3-(2-Methoxyethoxy)phenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amin
152	N-(2-(3-(4-(2-Methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy)ethyl)methan-sulfonamid
154	4-(2-Methyl-1H-indol-5-yloxy)-N-(3-(2-morpholinoethoxy)phenyl)-pyrimidin-2-amin
156	N-(3-(2-Methoxyethoxy)phenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amin
157	4-(2-Methyl-1H-indol-5-yloxy)-N-(3-(morpholinomethyl)phenyl)-pyrimidin-2-amin
158	4-(2-Methyl-1H-indol-5-yloxy)-N-(3-(3-thiomorpholinopropoxy)phenyl)-pyrimidin-2-amin
162	4-(2-Methyl-1H-indol-5-yloxy)-N-(3-(2-thiomorpholinoethoxy)phenyl)-pyrimidin-2-amin
163	4-(2-Methyl-1H-indol-5-yloxy)-N-(3-(2-(pyrrolidin-1-yl)ethoxy)phenyl)pyrimidin-2-amin
164	4-(2-Methyl-1H-indol-5-yloxy)-N-(3-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)pyrimidin-2-amin
165	2-(4-(3-(4-(2-Methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperazin-1-yl)ethanol
166	4-(2-Methyl-1H-indol-5-yloxy)-N-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)pyrimidin-2-amin
167	4-(2-Methyl-1H-indol-5-yloxy)-N-(3-(methylsulfonylmethyl)phenyl)-pyrimidin-2-amin
168	4-(2-(3-(4-(2-Methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy)ethyl)-piperazin-1-carbonsäure-tert.-butylester
169	N,N-Dimethyl-3-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino))phenyl)propanamid
170	(E)-N-Methyl-3-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)acrylamid
172	N-(3-(2-Aminoethoxy)phenyl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amin
173	N-(3-(4-(2-Methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)methansulfon-amid
175	4-(2-Methyl-1H-indol-5-yloxy)-N-(3-(2-(piperazin-1-yl)ethoxy)phenyl)pyrimidin-2-amin
179	N-Methyl-3-(3-(4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino))phenyl)propanamid
181	N-(4-(4-(2-Methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)methansulfon-amid
183	4-(2-Methyl-1H-indol-5-yloxy)-N-(3-(2-(methylsulfonyl)-ethoxy)phenyl)pyrimidin-2-amin
185	N-(6-Methoxypyridin-3-yl)-4-(2-methyl-1H-indol-5-yloxy)pyrimidin-2-amin
186	2-(4-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)essigsäure-methylester
187	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(2-methoxyphenyl)pyrimidin-2,4-diamin
188	N2-(3-Bromphenyl)-N4-(4-fluor-2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
189	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(3-(methylsulfonyl)phenyl)-pyrimidin-2,4-diamin
190	3-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzonitril
191	N2-(2-Chlor-4-fluorphenyl)-N4-(4-fluor-2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
192	N-(3-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)methansulfon-amid
193	N2-(3,4-Difluorphenyl)-N4-(4-fluor-2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
194	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(3-(2-morpholinoethoxy)phenyl)-pyrimidin-2,4-diamin
195	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(3-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)phenyl)pyrimidin-2,4-diamin
196	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(2-(2-morpholinoethoxy)phenyl)-pyrimidin-2,4-diamin
197	N2-(3-(3-(Dimethylamino)propoxy)phenyl) -N4-(4-fluor-2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
198	N-Cyclopropyl-2-(3-(4-(4-fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)acetamid
199	N-(2-(3-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethyl)methan-sulfonamid
200	2-(2-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethanol
201	N2-(3-(2-(Dimethylamino)ethoxy)phenyl)-N4-(4-fluor-2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
202	(1-(3-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)methanol
203	3-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-methylbenzamid
205	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(3-(piperidin-4-ylmethoxy)phenyl)pyrimidin-2,4-diamin
208	N-(5-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)pyridin-2-yl)acetamid
211	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(3-(2-methoxyethoxy)phenyl)pyrimidin -2,4-diamin
212	4-(4-Fluor-2-methyl-1H-indol-5-yl)-N-(3-(3-(thiomorpholino-1',1'-dioxid)propoxy)phenyl)-pyrimidin-2-amin
214	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(3-(2-(methylamino)ethoxy)phenyl)-pyrimidin-2,4-diamin
216	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(3-(3-thiomorpholinopropoxy)phenyl)-pyrimidin-2,4-diamin
218	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(3-(2-thiomorpholinoethoxy)phenyl)-pyrimidin-2,4-diamin
219	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(3-(2-(pyrrolidin-1-yl)ethoxy)phenyl)pyrimidin-2,4-diamin
220	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(3-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)pyrimidin-2,4-diamin
221	2-(4-(3-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)piperazin-1-yl)ethanol
223	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(3-(methylsulfonylmethyl)phenyl)-pyrimidin-2,4-diamin
224	4-(2-(3-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethyl)-piperazin-1-carbonsäure-tert.-butylester
225	4-(2-(3-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenoxy)ethyl)-piperazin-1-carbonsäure-tert.-butylester
226	3-(3-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino))phenyl)-N,N-dimethylpropanamid
227	(E)-3-(3-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)-N-methylacrylamid
228	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)pyrimidin-2,4-diamin
229	N2-(3-(2-Aminoethoxy)phenyl)-N4-(4-fluor-2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
230	N-(3-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)methansulfon-amid
234	3-(3-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)-N-methylpropanamid
236	N-(4-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenyl)methansulfon-amid
241	N4-(4-Fluor-2-methyl-1H-indol-5-yl)-N2-(6-methoxypyridin-3-yl)pyrimidin-2,4-diamin
242	4-(4-Fluor-2-methyl-1H-indol-5-yloxy)-N-(3-(2-morpholinoethoxy)phenyl)-pyrimidin-2-amin
243	4-(4-Fluor-2-methyl-1H-indol-5-yloxy)-N-(3-(3-morpholinopropoxy)phenyl-pyrimidin-2-amin
244	2-(3-(4-(4-Fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy)ethanol
245	4-(4-Fluor-2-methyl-1H-indol-5-yloxy)-N-(3-(3-(thiomorpholino-1',1'-dioxid)propoxy)phenyl)-pyrimidin-2-amin
251	(1-(3-(4-(4-Fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)methanol
252	2-(1-(3-(4-(4-Fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperidin-4-yl)ethanol
253	4-(4-Fluor-2-methyl-1H-indol-5-yloxy)-N-(3-(2-(methylamino)ethoxy)phenyl)-pyrimidin-2-amin
255	4-(4-Fluor-2-methyl-1H-indol-5-yloxy)-N-(3-(morpholinomethyl)phenyl)-pyrimidin-2-amin
257	3-(4-(4-Fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)-N-methylbenzamid
258	N-(2-(3-(4-(4-Fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy)ethyl)methan-sulfonamid
260	4-(4-Fluor-2-methyl-1H-indol-5-yloxy)-N-(3-(3-thiomorpholinopropoxy)phenyl)-pyrimidin-2-amin
263	4-(4-Fluor-2-methyl-1H-indol-5-yloxy)-N-(3-(2-thiomorpholinoethoxy)phenyl)-pyrimidin-2-amin
264	4-(4-Fluor-2-methyl-1H-indol-5-yloxy)-N-(3-(2-(pyrrolidin-1-yl)ethoxy)phenyl)pyrimidin-2-amin
265	4-(4-Fluor-2-methyl-1H-indol-5-yloxy)-N-(3-((4-(methylsulfonyl)piperazin-1-yl)methyl)phenyl)pyrimidin-2-amin
266	2-(4-(3-(4-(4-Fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)piperazin-1-yl)ethanol
267	4-(4-Fluor-2-methyl-1H-indol-5-yloxy)-N-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)pyrimidin-2-amin
269	4-(2-(3-(4-(4-Fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenoxy)ethyl)-piperazin-1-carbonsäure-tert.-butylester
271	N-(3-(2-Aminoethoxy)phenyl)-4-(4-fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-amin
272	N-(3-(4-(4-Fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)methansulfon-amid
276	N-(3-(4-(4-Fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)methansulfon-amid
278	3-(3-(4-(4-Fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)-N-methylpropanamid
280	N-(4-(4-(4-Fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenyl)methan-sulfonamid
282	4-(4-Fluor-2-methyl-1H-indol-5-yloxy)-N-(3-(2-(methylsulfonyl)ethoxy)phenyl) pyrimidin-2-amin
283	4-(4-Fluor-2-methyl-1H-indol-5-yloxy)-N-(6-methoxypyridin-3-yl)pyrimidin-2-amin
284	3-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol
285	4-(5-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-1H-pyrazol-3-yl)phenol
286	2-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol
287	4-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol
289	4-(4-(2-Methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenol
290	3-(4-(2-Methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenol
291	2-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol
292	4-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol
293	3-(4-(4-Fluor-2-methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phenol
294	3-(4-(2-Methylbenzo[d]oxazol-6-ylamino)pyrimidin-2-ylamino)phenol
295	3-(4-(4-Fluor-2-methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phenol
296	N-(2-Methoxypyrimidin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
297	N-(2-Methoxypyridin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
298	N-(2-Methoxypyridin-4-yl)-N-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
299	N-(5-(4-(2-Methyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)pyridin-2-yl)methansulfonamid
302	N2-Cyclopropyl-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
303	N2-Cyclohexyl-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin
305	3-(4-(2-Methyl-1H-indol-5-ylamino)pyrimidin-2-ylamino-benzonitril
309	N2-(3-Methoxyphenyl)-N4-(2-methyl-1H-indol-5-yl)pyrimidin-2,4-diamin

5. Verwendung einer wirksamen Menge einer Verbindung oder eines pharmazeutisch unbedenklichen Salzes davon nach einem der Ansprüche 1 bis 4 bei der Herstellung eines Medikaments zur Behandlung einer mit Angiogenese in Zusammenhang stehenden Störung.

6. Verwendung nach Anspruch 5, wobei es sich bei der mit Angiogenese in Zusammenhang stehenden Störung um Krebs oder altersbedingte Makuladegeneration handelt.

7. Verwendung einer wirksamen Menge einer Verbindung oder eines pharmazeutisch unbedenklichen Salzes davon nach einem der Ansprüche 1 bis 4 bei der Herstellung eines Medikaments zur Inhibierung von Angiogenese bei einem Empfänger.

8. Verbindung oder pharmazeutisch unbedenkliches Salz davon nach einem der Ansprüche 1 bis 4 zur Verwendung bei der Behandlung einer mit Angiogenese in Zusammenhang stehenden Störung.

9. Verbindung oder pharmazeutisch unbedenkliches Salz davon nach Anspruch 8, wobei es sich bei der mit Angiogenese in Zusammenhang stehenden Störung um Krebs oder altersbedingte Makuladegeneration handelt.

10. Verbindung oder pharmazeutisch unbedenkliches Salz davon nach einem der Ansprüche 1 bis 4 zur Verwendung bei der Inhibierung von Angiogenese bei einem Empfänger.

11. Nichttherapeutisches Verfahren zur Inhibierung der Aktivität von Kinase-Insert-Domain-Rezeptor, bei dem man den Rezeptor mit einer wirksamen Menge einer Verbindung oder eines pharmazeutisch unbedenklichen Salzes davon nach einem der Ansprüche 1 bis 4 in Berührung bringt.

Revendications

1. Composé de formule suivante :

dans laquelle

X représente O ou NH ;

Y représente NH ;

Z représente CR', R' étant H, halogéno ou alkyle ;

V, U et T représentent conjointement

chaque R₁, R₃, R₄ et R₆, indépendamment, représente H, halogéno, nitro, amino, cyano, hydroxy, alkyle, alcényle, alcynyle, aryle, cycloalkyle, hétérocycloalkyle, hétéroaryle, alcoxy, alkylthio, alkylcarbonyle, carboxy, alcoxycarbonyle, carbonylamino, sulfonylamino, aminocarbonyle ou aminosulfonyle ;

R₂ représente H, halogéno, nitro, amino, hydroxy, alkyle, alcényle, alcynyle, aryle, cycloalkyle, hétérocycloalkyle, hétéroaryle, alcoxy, alkylthio, alkylcarbonyle, carboxy, alcoxycarbonyle, carbonylamino, sulfonylamino, aminocarbonyle ou aminosulfonyle ;

R₅ représente alkyle, cycloalkyle, hétérocycloalkyle, aryle ou hétéroaryle ; et

R₇ représente alkyle ;

alkyle, cycloalkyle, hétérocycloalkyle, aryle, hétéroaryle et alcoxy étant éventuellement substitués par au moins un groupe choisi parmi halogéno, hydroxyle, amino, cyano, nitro, mercapto, alcoxycarbonyle, amido, carboxy, alcanesulfonyle, alkylcarbonyle, carbamido, carbamyle, carboxyle, thiouréido, thiocyanato, sulfonamido, alkyle, alcényle, alcynyle, alkyloxy, aryle, hétéroaryle, cycloalkyle et hétérocycloalkyle, dans lesquels alkyle, alcényle, alcynyle, alkyloxy, aryle, hétéroaryle, cycloalkyle et hétérocycloalkyle peuvent être en outre encore substitués ;

ou un sel pharmaceutiquement acceptable de celui-ci.

2. Composé ou un sel pharmaceutiquement acceptable de celui-ci selon l'une quelconque des revendications précédentes, R₆ représentant H et R₇ représentant méthyle.

3. Composé ou un sel pharmaceutiquement acceptable de celui-ci selon l'une quelconque des revendications précédentes, R₅ représentant aryle ou hétéroaryle, éventuellement substitué par halogéno, nitro, amino, cyano, hydroxy, alkyle, alcényle, alcynyle, aryle, cycloalkyle, hétérocycloalkyle, hétéroaryle, alcoxy, alkylthio, alkylcarbonyle, carboxy, alcoxycarbonyle, sulfonyle, carbonylamino, sulfonylamino, aminocarbonyle ou aminosulfonyle.

4. Composé ou un sel pharmaceutiquement acceptable de celui-ci selon la revendication 1, le composé étant un des composés suivantes :

Composé	Nom/Structure
1	N4-(2-méthyl-1H-indol-5-yl)-N2-phénylpyrimidine-2,4-diamine
2	N2-(3-éthynylphényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
3	N2-(3-bromophényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
4	N2-(3-fluorophényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
5	N2-(3-chlorophényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
6	N4-(2-méthyl-1H-indol-5-yl)-N2-(3-trifluorométhyl)phényl)pyrimid ine-2,4-diamine
7	N4-(2-méthyl-1H-indol-5-yl)-N2-(3-méthylsulfonyl)phényl)pyrimidi ne-2,4-diamine
8	N2-(3-méthoxyphényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
9	1-(3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)pipéridine-4-carboxylate d'éthyle
10	N2,N4-bis(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
11	N2-(1H-indazol-5-yl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
12	N2-(1H-benzo[d]imidazol-5-yl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
13	N2-(2-méthoxyphényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
14	N2-(2-chlorophényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
15	N2-(2-bromophényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
16	N2-(4-fluorophényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
17	2-(4-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phényl)acétate de méthyle
19	N2-(4-méthoxyphényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
20	N4-(2-méthyl-1H-indol-5-yl)-N2-(4-(2-morpholinoéthoxy)phényl)pyrimi dine-2,4-diamine
21	N2-(3,4-difluorophényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
22	N2-(3,5-dimethylphényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
23	2-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)éthanol
24	N4-(2-méthyl-1H-indol-5-yl)-N2-(2-morpholinoéthyl)pyrimidine-2,4-diamine
25	N-cyclopropyl-2-(3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phényl)acétamide
28	N-(3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phényl)méthanesulfonam ide
29	N4-(2-méthyl-1H-indol-5-yl)-N2-(3-(2-morpholinoéthoxy)phényl)pyrimi dine-2,4-diamine
30	N2-(3-(3-(diméthylamino)propoxy)phényl) -N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
31	2-(3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénoxy)éthanol
32	2-(2-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénoxy)éthanol
33	N4-(2-méthyl-1H-indol-5-yl)-N2-(2-(2-morpholinoéthoxy)phényl)pyrimidine-2,4-diamine
34	N-méthyl-3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzamide
35	3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-(2-(pipéridin-1-yl)éthyl)benzamide
36	N-(2-(diméthylamino)éthyl)-3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzamide
37	N2-(3-(4-méthoxyphényl)-1H-pyrazol-5-yl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
38	N-(3-éthynylphényl)-4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-amine
39	N-(4-méthoxyphényl)-4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-amine
42	N-(3-méthoxyphényl)-4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-amine
43	4-(2-méthyl-1H-indol-5-yloxy)-N-(3-(3-(thiomorpholino-1',1'-dioxyde)propoxy)phényl)pyrimid in-2-amine
44	N-méthyl-3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzamide
48	N-(4-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phényl)méthanesulfonam ide
49	2-(3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phényl)-N-(2-morpholinoéthyl)acétamide
50	4-(2-méthyl-1H-indol-5-yloxy)-N-(3-(2-(méthylsulfonyl)éthoxy)phényl) pyrimidin-2-amine
52	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(3-fluorophényl)pyrimidine-2,4-diamine
53	N2-(3-chlorophényl)-N4-(4-fluoro-2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
54	2-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzonitrile
55	N2-(3,5-diméthylphényl)-N4-(4-fluoro-2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
56	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(2-(trifluorométhyl)phényl)pyrimidine-2,4-diamine
57	N2-(2-chlorophényl)-N4-(4-fluoro-2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
59	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(4-méthoxyphényl)pyrimidine-2,4-diamine
61	2-(1-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)pipéridin-4-yl)éthanol
62	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(3-(3-(méthylsulfonyl)propoxy)phényl )pyrimidine-2,4-diamine
63	2-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénoxy)éthanol
65	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(3-((1-(méthylsulfonyl)pipéridin-4-yl)méthoxy)phényl)pyrimidine-2,4-diamine
66	1-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)pipéridin-4-ol
67	4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)-N-(3-(méthylsulfonyl)phényl)pyrimid in-2-amine
68	N-cyclopropyl-2-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phényl)acétamide
69	(E)-3-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phényl)-N-méthylacrylamide
70	3-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phényl)-N,N-diméthylpropanamide
71	N-méthyl-3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzamide
72	N2-(2-fluorophényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
73	3-(4-(2-méthyl-1H-indol-5-ylammo)pyrimidin-2-ylamino)benzonitrile
77	N2-(3,4-diméthoxyphényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
78	N2-(4-chlorophényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
79	N2-(2,4-difluorophényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
80	N2-(3-chloro-2-fluorophényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
81	N2-(1H-indol-4-yl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
82	N2-(4-(3-(diméthylamino)propoxy)phényl) -N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
83	2-(4-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénoxy)éthanol
84	N2-(3-chloro-4-fluorophényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
86	(1-(3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)pipéridin-4-yl)méthanol
87	N4-(2-méthyl-1H-indol-5-yl)-N2-(3-(2-(4-(méthylsulfonyl)pipérazin-1-yl)éthoxy)phényl)pyrimidine-2,4-diamine
89	N2-(2-chloro-4-fluorophényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
90	2-chloro-4-fluoro-5-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénol
91	N2-(4-chloro-2-fluorophényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
92	N2-(3-(2-(diméthylamino)éthoxy)phényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
93	N2-(2-méthyl-1H-indol-5-yl)-N4-(3-(3-(méthylsulfonyl)propoxy)phényl )pyrimidine-2,4-diamine
94	2-(1-(3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)pipéridin-4-yl)éthanol
95	N4-(2-méthyl-1H-indol-5-yl)-N2-(3-(pipéridin-4-ylméthoxy)phényl)pyrimidine-2,4-diamine
97	1-(3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)pipéridin-4-ol
101	N4-(2-méthyl-1H-indol-5-yl)-N2-(3-(3-(4-(méthylsulfonyl)pipérazin-1-yl)propoxy)phényl)pyrimidine-2,4-diamine
102	N4-(2-méthyl-1H-indol-5-yl)-N2-(3-(3-morpholinopropoxy)phényl)pyrim idine-2,4-diamine
104	(E)-N,N-diméthyl-3-(3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phényl)acrylamide
105	4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N-(3-(3-(thiomorpholino-1',1'-dioxyde)propoxy)phényl)pyrimid in-2-amine
106	N4-(2-méthyl-1H-indol-5-yl)-N2-(3-(2-(méthylamino)éthoxy)phényl)pyr imidine-2,4-diamine
107	4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)-N-(3-(3-(thiomorpholino-1'-oxyde)propoxy)phényl)pyrimidin -2-amine
108	N-(2-(3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénoxy)éthyl)méthanes ulfonamide
109	N4-(2-méthyl-1H-indol-5-yl)-N2-(3-(3-thiomorpholinopropoxy)phényl)p yrimidine-2,4-diamine
111	N4-(2-méthyl-1H-indol-5-yl)-N2-(3-(2-thiomorpholinoéthoxy)phényl)py rimidine-2,4-diamine
112	N4-(2-méthyl-1H-indol-5-yl)-N2-(3-(2-pyrrolidinéthoxy)phényl)pyrimi dine-2,4-diamine
115	N4-(2-méthyl-1H-indol-5-yl)-N2-(3-((4-(méthylsulfonyl)pipérazin-1-yl)méthyl)phényl)pyrimidine-2,4-diamine
116	2-(4-(3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)pipérazin-1-yl)éthanol
117	N4-(2-méthyl-1H-indol-5-yl)-N2-(3-(méthylsulfonylméthyl)phényl)p yrimidine-2,4-diamine
118	N,N-diméthyl-3-(3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phényl)propanamide
119	(E)-N-méthyl-3-(3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phényl)acrylamide
121	N2-(3-(2-aminoéthoxy)phényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
122	N-(3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)méthanesulfonam ide
124	N-méthyl-3-(3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phényl)propanamide
130	N-(4-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phényl)méthanesulfonam ide
132	N2-(6-méthoxypyridin-3-yl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
133	2-méthyl-N-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-yl)-1H-indol-5-amine
134	N-(3-(3-(diméthylamino)propoxy)phényl) -4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-amine
135	2-(3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phénoxy)éthanol
136	N-(3-(2-(diméthylamino)éthoxy)phényl)-4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-amine
137	N-cyclopropyl-2-(3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phényl)acétamide
138	4-(2-méthyl-1H-indol-5-yloxy)-N-(3-(3-(méthylsulfonyl)propoxy)phényl)pyrimidin-2-amine
139	4-(2-méthyl-1H-indol-5-yloxy)-N-(3-(pipéridin-4-ylméthoxy)phényl)pyrimidin-2-amine
143	1-(3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)pipéridin-4-ol
144	(1-(3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)pipéridin-4-yl)méthanol
145	2-(1-(3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)pipéridin-4-yl)éthanol
146	N-(3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phényl)méthanesulfonam ide
148	(E)-N,N-diméthyl-3-(3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phényl)acrylamide
150	N-(3-(2-méthoxyéthoxy)phényl)-4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-amine
152	N-(2-(3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phénoxy)éthyl)méthanes ulfonamide
154	4-(2-méthyl-1H-indol-5-yloxy)-N-(3-(2-morpholinoéthoxy)phényl)pyrimi din-2-amine
156	N-(3-(2-méthoxyéthoxy)phényl)-4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-amine
157	4-(2-méthyl-1H-indol-5-yloxy)-N-(3-(morpholinométhyl)phényl)pyrim idin-2-amine
158	4-(2-méthyl-1H-indol-5-yloxy)-N-(3-(3-thiomorpholinopropoxy)phényl)p yrimidin-2-amine
162	4-(2-méthyl-1H-indol-5-yloxy)-N-(3-(2-thiomorpholinoéthoxy)phényl)py rimidin-2-amine
163	4-(2-méthyl-1H-indol-5-yloxy)-N-(3-(2-(pyrrolidin-1-yl)éthoxy)phényl)pyrimidin-2-amine
164	4-(2-méthyl-1H-indol-5-yloxy)-N-(3-((4-(méthylsulfonyl)pipérazin-1-yl)méthyl)phényl)pyrimidin-2-amine
165	2-(4-(3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)pipérazin-1-yl)éthanol
166	4-(2-méthyl-1H-indol-5-yloxy)-N-(3-((tétrahydro-2H-pyran-4-yl)méthoxy)phényl)pyrimidin-2-amine
167	4-(2-méthyl-1H-indol-5-yloxy)-N-(3-(méthylsulfonylméthyl)phényl)p yrimidin-2-amine
168	4-(2-(3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phénoxy)éthyl)pipérazi ne-1-carboxylate de tert-butyle
169	N,N-diméthyl-3-(3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino))phényl)propanamide
170	(E)-N-méthyl-3-(3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phényl)acrylamide
172	N-(3-(2-aminoéthoxy)phényl)-4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-amine
173	N-(3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)méthanesulfonam ide
175	4-(2-méthyl-1H-indol-5-yloxy)-N-(3-(2-(pipérazin-1-yl)éthoxy)phényl)pyrimidin-2-amine
179	N-méthyl-3-(3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino))phényl)propanamide
181	N-(4-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phényl)méthanesulfonam ide
183	4-(2-méthyl-1H-indol-5-yloxy)-N-(3-(2-(méthylsulfonyl)éthoxy)phényl) pyrimidin-2-amine
185	N-(6-méthoxypyridin-3-yl)-4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-amine
186	2-(4-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phényl)acétate de méthyle
187	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(2-méthoxyphényl)pyrimidine-2,4-diamine
188	N2-(3-bromophényl)-N4-(4-fluoro-2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
189	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(3-(méthylsulfonyl)phényl)pyrimid ine-2,4-diamine
190	3-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzonitrile
191	N2-(2-chloro-4-fluorophényl)-N4-(4-fluoro-2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
192	N-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phényl)méthanesulfonam ide
193	N2-(3,4-difluorophényl)-N4-(4-fluoro-2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
194	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(3-(2-morpholinoéthoxy)phényl)pyrimi dine-2,4-diamine
195	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(3-(2-(4-(méthylsulfonyl)pipérazin-1-yl)éthoxy)phényl)pyrimidine-2,4-diamine
196	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(2-(2-morpholinoéthoxy)phényl)pyrimi dine-2,4-diamine
197	N2-(3-(3-(diméthylamino)propoxy)phényl) -N4-(4-fluoro-2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
198	N-cyclopropyl-2-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phényl)acétamide
199	N-(2-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénoxy)éthyl)méthanes ulfonamide
200	2-(2-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénoxy)éthanol
201	N2-(3-(2-(diméthylamino)éthoxy)phényl)-N4-(4-fluoro-2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
202	(1-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)pipéridin-4-yl)méthanol
203	3-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-N-méthylbenzamide
205	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(3-(pipéridin-4-ylméthoxy)phényl)pyrimidine-2,4-diamine
208	N-(5-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)pyridin-2-yl)acétamide
211	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(3-(2-méthoxyéthoxy)phényl)pyrimidin e-2,4-diamine
212	4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N-(3-(3-(thiomorpholino-1',1'-dioxyde)propoxy)phényl)pyrimid in-2-amine
214	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(3-(2-(méthylamino)éthoxy)phényl)pyr imidine-2,4-diamine
216	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(3-(3-thiomorpholinopropoxy)phényl)p yrimidine-2,4-diamine
218	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(3-(2-thiomorpholinoéthoxy)phényl)py rimidine-2,4-diamine
219	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(3-(2-(pyrrolidin-1-yl)éthoxy)phényl)pyrimidine-2,4-diamine
220	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(3-((4-(méthylsulfonyl)pipérazin-1-yl)méthyl)phenyl)pyrimidine-2,4-diamine
221	2-(4-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)pipérazin-1-yl)éthanol
223	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(3-(méthylsulfonylméthyl)phényl)p yrimidine-2,4-diamine
224	4-(2-(3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénoxy)éthyl)pipérazi ne-1-carboxylate de tert-butyle
225	4-(2-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénoxy)éthyl)pipérazi ne-1-carboxylate de tert-butyle
226	3-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino))phényl)-N,N-diméthylpropanamide
227	(E)-3-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phényl)-N-méthylacrylamide
228	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(3-((tetrahydro-2H-pyran-4-yl)méthoxy)phényl)pyrimidine-2,4-diamine
229	N2-(3-(2-aminoéthoxy)phényl)-N4-(4-fluoro-2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
230	N-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)benzyl)méthanesulfonam ide
234	3-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phényl)-N-méthylpropanamide
236	N-(4-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phényl)méthanesulfonam ide
241	N4-(4-fluoro-2-méthyl-1H-indol-5-yl)-N2-(6-méthoxypyridin-3-yl)pyrimidine-2,4-diamine
242	4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)-N-(3-(2-morpholinoéthoxy)phényl)pyrimi din-2-amine
243	4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)-N-(3-(3-morpholinopropoxy)phényl)pyrim idin-2-amine
244	2-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phénoxy)éthanol
245	4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)-N-(3-(3-(thiomorpholino-1',1'-dioxyde)propoxy)phényl)pyrimid in-2-amine
251	(1-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)pipéridin-4-yl)méthanol
252	2-(1-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)pipéridin-4-yl)éthanol
253	4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)-N-(3-(2-(méthylamino)éthoxy)phényl)pyr imidin-2-amine
255	4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)-N-(3-(morpholinométhyl)phényl)pyrim idin-2-amine
257	3-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)-N-méthylbenzamide
258	N-(2-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phénoxy)éthyl)méthanes ulfonamide
260	4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)-N-(3-(3-thiomorpholinopropoxy)phényl)p yrimidin-2-amine
263	4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)-N-(3-(2-thiomorpholinoéthoxy)phényl)py rimidin-2-amine
264	4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)-N-(3-(2-(pyrrolidin-1-yl)éthoxy)phényl)pyrimidin-2-amine
265	4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)-N-(3-((4-(méthylsulfonyl)pipérazin-1-yl)méthyl)phényl)pyrimidin-2-amine
266	2-(4-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)pipérazin-1-yl)éthanol
267	4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)-N-3-((tétrahydro-2H-pyran-4-yl)méthoxy)phényl)pyrimidin-2-amine
269	4-(2-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phénoxy)éthyl)pipérazi ne-1-carboxylate de tert-butyle
271	N-(3-(2-aminoéthoxy)phényl)-4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-amine
272	N-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)benzyl)méthanesulfonam ide
276	N-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phényl)méthanesulfonam ide
278	3-(3-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phényl)-N-méthylpropanamide
280	N-(4-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phényl)méthanesulfonam ide
282	4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)-N-(3-(2-(méthylsulfonyl)éthoxy)phényl) pyrimidin-2-amine
283	4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)-N-(6-méthoxypyridin-3-yl)pyrimidin-2-amine
284	3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénol
285	4-(5-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)-1H-pyrazol-3-yl)phénol
286	2-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénol
287	4-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénol
289	4-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phénol
290	3-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phénol
291	2-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénol
292	4-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénol
293	3-(4-(4-fluoro-2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino)phénol
294	3-(4-(2-méthylbenzo[d]oxazol-6-ylamino)pyrimidin-2-ylamino)phénol
295	3-(4-(4-fluoro-2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)phénol
296	N-(2-méthoxypyrimidin-4-yl)-N-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
297	N-(2-méthoxypyridin-4-yl)-N-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
298	N-(2-méthoxypyridin-4-yl)-N-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
299	N-(5-(4-(2-méthyl-1H-indol-5-yloxy)pyrimidin-2-ylamino)pyridin-2-yl)méthanesulfonamide
302	N2-cyclopropyl-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
303	N2-cyclohexyl-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine
305	3-(4-(2-méthyl-1H-indol-5-ylamino)pyrimidin-2-ylamino-benzonitrile
309	N2-(3-méthoxyphényl)-N4-(2-méthyl-1H-indol-5-yl)pyrimidine-2,4-diamine

5. Utilisation d'une quantité efficace d'un composé ou d'un sel pharmaceutiquement acceptable de celui-ci selon l'une quelconque des revendications 1 à 4, dans la préparation d'un médicament destiné au traitement d'un trouble lié à l'angiogenèse.

6. Utilisation selon la revendication 5, le trouble lié à l'angiogenèse étant le cancer ou la dégénérescence maculaire liée à l'âge.

7. Utilisation d'une quantité efficace d'un composé ou d'un sel pharmaceutiquement acceptable de celui-ci selon l'une quelconque des revendications 1 à 4, dans la préparation d'un médicament destiné à l'inhibition de l'angiogenèse chez un sujet.

8. Composé ou un sel pharmaceutiquement acceptable de celui-ci selon l'une quelconque des revendications 1 à 4, destiné au traitement d'un trouble lié à l'angiogenèse.

9. Composé ou un sel pharmaceutiquement acceptable de celui-ci selon la revendication 8, le trouble lié à l'angiogenèse étant le cancer ou la dégénérescence maculaire liée à l'âge.

10. Composé ou un sel pharmaceutiquement acceptable de celui-ci selon l'une quelconque des revendications 1 à 4, destiné à l'inhibition de l'angiogenèse chez un sujet.

11. Procédé nonthérapeutique d'inhibition de l'activité du récepteur du domaine d'insertion de kinase comprenant la mise en contact du récepteur avec une quantité efficace d'un composé ou d'un sel pharmaceutiquement acceptable de celui-ci selon l'une quelconque des revendications précédentes.