Quinolylpropyl piperidine derivatives, process of their preparation and their use

摘要

1-Substituted 4-(3-(6-alkoxy-4-quinolinyl)-propyl)-piperidine derivatives (I) are new. Quinolinylpropyl-piperidine derivatives of formula (I), in the form of diastereomers or their mixtures, and their salts are new. [Image] R 1H, halo or OH; R' 1H; or may also be halo if R 1= halo; R 0H; or R 0+ R 1bond, in which case R' 1= H; R 2COOH, CH 2COOH, CH 2CH 2COOH or CH 2OH; R 3(i) 1-6C alkyl substituted by 1-3 groups selected from OH, halo, oxo, COOH, alkoxycarbonyl, alkoxy, alkylthio, Ph', SPh' or Ph'-alkylthio, cycloalkyl, cycloalkylthio, Het and -S-Het; (ii) propargyl substituted by Ph', cycloalkyl or Het; (iii) cinnamyl or (iv) 4-phenylbuten-3-yl; provided that if R 3CH 2OH, then R 3= (i) 1-6C alkyl substituted by SPh', cycloalkylthio or -S-Het; or (ii) propargyl substituted by Ph', cycloalkyl or Het; R 41-6C alkyl, (2-6C) alkenyl-CH 2O- or (2-6C) alkynyl-CH 2O-; Ph' : phenyl (optionally substituted by 1-3 of halo, OH, alkyl, alkoxy, CF 3, OCF 3, COOH, alkoxycarbonyl, CN or NH 2); Het : 5- or 6-membered aromatic heterocycle containing 1-4 of N, O and S as heteroatom(s) (optionally substituted by 1-3 of halo, OH, alkyl, alkoxy, CF 3, OCF 3, oxo, COOH, alkoxycarbonyl, CN or NH 2); unless specified otherwise alkyl moieties have 1-3C and cycloalkyl moieties 3-7C. An independent claim is included for the preparation for (I). ACTIVITY : Antibacterial. (I) are effective in vitro against methicillin-resistant Staphylococcus aureusAS5155 at 0.03-4 Microg/ml, Streptococcus pneumoniaeIP53146 at 0.12-8 Microg/ml, Enterococcus faeciumat 0.5-64 Microg/ml and Moxarella catharrhalisIPA152 at 0.25-32 Microg/ml; and in vivo against Staphylococcus aureusIP8203 in mice at 10-150 mg/kg s.c. (CD 50) or (in some cases) 20-150 mg/kg p.o. (No specific results for individual compounds are given). MECHANISM OF ACTION : None given.