Piperidine quinolyl propyl derivatives, preparation method...

C - Chemistry – Metallurgy – 07 – D

Patent

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C07D 401/06 (2006.01) A61K 31/4709 (2006.01) A61P 31/04 (2006.01) C07D 211/34 (2006.01) C07D 409/14 (2006.01)

Patent

CA 2503732

The invention concerns piperidine quinolyl derivatives of general formula (I), wherein: R¿1? is hydrogen or fluorine; R¿2? is carboxy, carboxymethyl or hydroxymethyl; R¿3? is alkyl substituted either by a phenylthio optionally substituted by halogen, hydroxy, alkyl, alkyloxy, trifluoromethyl, trifluoromethoxy, carboxy, alkoxycarbonyl, cyano or amino, or by cycloalkylthio (3 to 7 members) optionally substituted by halogen or trifluoromethyl, or heteroalkylthio (5 to 6 members and 1 to 4 heteroatoms, selected among N, O and S), optionally substituted by halogen, hydroxy, alkyl, alkyloxy, trifluoromethyl, trifluoromethoxy, carboxy, alkyloxycarbonyl, cyano or amino or R¿3? is propargyl substituted by phenyl, or heteroaryl such as defined above; R¿4? is alkyl, alkenyl-CH¿2?- or alkynyl-CH¿2?-, cycloalkyl or cycloalkyl alkyl, in their various isomeric separated or mixed forms, as well as their salts. The method also concerns a method for preparing said derivatives and compositions containing them. Said novel derivatives are potent antibacterial agents.

Dérivés de quinolyl pipéridine de formule générale (I) dans laquelle R1 est hydrogène ou fluor, R2 est carboxy, carboxyméthyle ou hydroxyméthyle, R3 est alcoyle substitué soit par phénylthio éventuellement substitué par halogène, hydroxy, alcoyle, alcoyloxy, trifluorométhyle, trifluorométhoxy, carboxy, alcoyloxycarbonyle cyano ou amino, soit par cycloalcoylthio (3 à 7 chaînons) éventuellement substitué par halogène ou trifluorométhyle, soit par hétéroarylthio (5 à 6 chaînons et 1 à 4 hétéroatomes) choisis parmi N, O et S), éventuellement substitué par halogène, hydroxy, alcoyle, alcoyloxy, trifluorométhyle, trifluorométhoxy, carboxy, alcoyloxycar-bonyle, cyano ou amino ou R3 est propargyle substitué par phényle, ou hétéroaryle tels que définis ci-dessus, R4 est alcoyle, alcényl-CH2- ou alcynyl-CH2-, cycloalcoyle ou cycloalcoyl alcoyle, sous leurs différentes formes isomères séparées ou en mélanges, ainsi que leurs sels, leur procédé et intermédiaires de préparation et les compositions les renfermant. Ces nouveaux dérivés sont de puissants agents antibactériens.

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