EP 1654252 A2 20060510 - SUBSTITUTED QUINOLINES SERVING AS ANTIMICROBIAL AGENTS
Title (en)
SUBSTITUTED QUINOLINES SERVING AS ANTIMICROBIAL AGENTS
Title (de)
SUBSTITUIERTE CHINOLINE, DIE ALS ANTIMIKROBIELLE MITTEL DIENEN
Title (fr)
QUINOLINES SUBSTITUEES COMME ANTIMICROBIENS
Publication
Application
Priority
- FR 2004002090 W 20040805
- FR 0309754 A 20030808
Abstract (en)
[origin: FR2858619A1] 4-Substituted quinoline derivatives (I) are new. 4-Substituted quinoline derivatives of formula (I) and their enantiomeric forms and/or diastereoisomeric forms, and/or syn and/or anti form, or their salts are new. [Image] X 1CR 1aor N; X 2CR 2aor N; X 3CR 3aor N; X 4CR 4aor N; X 5CR 5aor N; R 1a-R 4aH, halo, alkyl, cycloalkyl, phenyl, phenylthio, mono- or bicyclic heteroaryl(thio), OH, SH, alkyloxy, OCF 2, OCF 3, alkylthio, trifluoromethylthio, cycloalkyloxy, cycloalkylthio, acyl, acyloxy, acylthio, CN, carboxyl, alkoxycarbonyl, cycloalkoxycarbonyl, nitro, NR aR b, C(O)NR aR b, methylene substituted by F, OH, alkyloxy, alkylthio, cycloalkyloxy, cycloalkylthio, phenyl, mono- or bicyclic heteroaryl, carboxyl, alkyloxycarbonyl, cycloalkyloxycarbonyl, NR aR bor C(O)NR aR b, phenoxy, heterocyclyloxy or benzyloxy, heterocyclylmethyloxy; R 1as R 1a, plus difluoromethoxy, C m'F 2m'+1, SC m'F 2m'+1or OC m'F 2m'+1; R 5aas R 1a, plus trifluoroacetyl; m' : 1-6; R a, R bH, alkyl, cycloalkyl, phenyl, or mono- or bicyclic heteroaryl; or NR aR b5-6 membered heterocycle optionally containing another heteroatom selected from O, S (optionally oxidized to sulfinyl or sulfonyl) or N (optionally N-substituted by alkyl, phenyl or mono- or bicyclic heteroaryl); m : 0-2; n : 0 or 1; Y : CHR, C(O), CROH, CRNH 2, CRF or CF 2, provided that Y is not C(O) when m = 0; R : H or 1-6C alkyl; R 2R, CO 2R, CH 2CO 2R, CH 2CH 2CO 2R, C(O)NH 2, CH 2C(O)NH 2, CH 2CH 2C(O)NH 2, CH 2OH, CH 2CH 2OH, CH 2NH 2, CH 2CH 2NH 2or CH 2CH 2CH 2NH 2; R 3radical phenyl, mono- or bicyclic heteroaryl, alk-R 3', CR b1=CR c2R a1, OC=R d, CF 2phenyl or mono- or bicyclic -CF 2heteroaryl, phenyl, hydroxyalkyl, alkylthioalkyl, alkylsulfinylalkyl or alkylsulfonylalkyl; alk : alkylene R3' : H, halo, OH, alkyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, (di)alkylamino, cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylsulfinyl, cyclo alkylsulfonyl, cycloalkylamino, N-cycloalkyl-N-alkylamino, di(cycloalkyl)amino, acyl, cycloalkylcarbonyl, phenyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylamino, N-alkyl-N-phenylamino, N-cycloalkyl-N-phenylamino, -N-(phenyl) 2, phenylalkoxy, phenylalkylthio, phenylalkylsulfinyl, phenylalkylsulfonyl, phenylalkylamino, N-alkyl-N-phenylaminoalkyl, N-cyclo-alkyl-N-phenylalkylamino, benzoyl, mono- or bicyclic heteroaryl, heteroaryloxy, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, heteroarylamino, N-alkyl-N-heteroarylamino, N-cycloalkyl-N-heteroarylamino, heteroarylcarbonyl, heteroarylalkyloxy, heteroarylalkylthio, heteroarylalkylsulfinyl, heteroarylalkylsulfonyl, heteroarylalkylamino, N-alkyl-N-heteroarylaminoalkyl, N-cycloalkyl-N-heteroarylaminoalkyl, carboxyl, alkyloxycarbonyl, NR aR bor C(O)NR aR b; R a1phenyl, phenylalkyl, monocyclic or bicyclic heteroaryl or heteroarylalkyl, phenoxyalkyl, phenylthioalkyl, phenylsulfinylalkyl, phenylsulfonylalkyl, phenylaminoalkyl, N-alkyl-N-phenylaminoalkyl, heteroaryloxyalkyl, heteroarylthio-alkyl, heteroarylsulfinylalkyl, heteroarylsulfonylalkyl, heteroarylaminoalkyl, N-alkyl-N-heteroarylaminoalkyl, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, phenylthio, phenylsulfinyl or phenylsulfonyl; R b1, R c1H, alkyl or cycloalkyl; R dalkyl, phenyl, phenylalkyl, phenoxyalkyl, phenylthioalkyl, N-alkyl-N-phenylaminoalkyl, heteroaryl, heteroarylalkyl, heteroaryloxyalkyl, heteroarylthioalkyl, heteroarylaminoalkyl, N-alkyl-N-heteroarylaminoalkyl, (all heteroaryl are mono-cyclic or bicyclic); and R 4R, CHO, C(O)CH 3, CH 2CO 2H or C(O)CH 2NH 2; phenyl, benzyl, benzoyl or heteroaryl are optionally substituted on the ring by 1-4 halo, OH, alkyl, alkyloxy, alkoxyalkyl, haloalkyl, CF 3, OCF 3, trifluoromethylthio, carboxyl, alkyloxycarbonyl, CN, alkylamino or -NR aR b; alkyl or acyl radicals and portions contain 1-10C atoms and cycloalkyl radicals contain 3-6C atoms. Independent claims are also included for: (1) preparation of (I); (2) 4-substituted quinoline derivative of formula (II); and (3) substituted heteroaromatic compounds of formula (XI)-(XIV), provided that R 1is not H. [Image] ACTIVITY : Antibacterial; Respiratory-Gen. The antibacterial activity of (I) was assessed against S. pneumoniae.The results showed that the minimum inhibitory concentration value of (I) was 0.012-2 Microg/ml. MECHANISM OF ACTION : None given.
IPC 1-7
IPC 8 full level
A61P 31/04 (2006.01); C07D 401/12 (2006.01)
CPC (source: EP)
A61P 31/04 (2017.12); C07D 401/12 (2013.01)
Citation (search report)
See references of WO 2005016916A2
Designated contracting state (EPC)
AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PL PT RO SE SI SK TR
DOCDB simple family (publication)
FR 2858619 A1 20050211; FR 2858619 B1 20061222; CA 2535020 A1 20050224; EP 1654252 A2 20060510; JP 2007501777 A 20070201; WO 2005016916 A2 20050224; WO 2005016916 A3 20050929
DOCDB simple family (application)
FR 0309754 A 20030808; CA 2535020 A 20040805; EP 04786264 A 20040805; FR 2004002090 W 20040805; JP 2006522379 A 20040805