Cycloalkylaminomethylpyrrolidine derivatives

C - Chemistry – Metallurgy – 07 – D

Patent

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C07D 401/04 (2006.01) A61K 31/47 (2006.01) A61K 31/695 (2006.01) C07D 405/14 (2006.01) C07F 7/10 (2006.01)

Patent

CA 2251927

A quinolone derivative represented by formula (I): (See formula I) wherein R1 represents a cycloalkyl group; R2 represents a hydrogen atom, an amino group, a hydroxyl group, a thiol group, a halogenomethyl group, an alkyl group, an alkenyl group, an alkynyl group, or an alkoxyl group; R3 represents an amino group, a halogenomethyl group, a halogenomethoxyl group, an alkyl group, an alkenyl group, an alkynyl group, or an alkoxyl group; R4 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R5 represents a cycloalkyl group having 3 to 6 carbon atoms; the above R1 to R5 may be substituted; X represents a halogen atom or a hydrogen atom; and Y represents a hydrogen atom, a phenyl group, an acetoxymethyl group, a pivaloyloxymethyl group, an ethoxycarbonyl group, a choline group, a dimethylaminoethyl group, a 5-indanyl group, a phthalidinyl group, a 5-alkyl-2- oxo-1,3-dioxol-4-ylmethyl group, a 3-acetoxy-2-oxobutyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxymethyl group having 2 to 7 carbon atoms, or a phenylalkyl group having 1 to 6 carbon atoms in the alkyl - 34 - moiety thereof, or a salt thereof. The compound exhibits high and broad antimicrobial activity against various bacteria including bacteria resistant to drugs and high safety. - 35 -

Cette invention concerne des composés représentés par la formule générale (I) ainsi que des sels de ces composés, qui donnent des dérivés de quinolone présentant d'une part une forte activité antibactérienne dirigée contre de nombreuses bactéries, même des bactéries résistantes et d'autre part, un haut niveau de sécurité. Dans la formule (I), R<1> est cycloalkyle, R<2> est hydrogène, amino, hydroxyle, mercapto, halogénométhyle, alkyle, alkényle, alkynyle ou alcoxy, R<3> est amino, halogénométhyle, halogénométoxy, alkyle, alkényle, alkynyle ou alcoxy, R<4> est hydrogène ou alkyle C1-C6, R<5> est cycloalkyle C3-C6, et X est halogéno ou hydrogène, à condition que ces substituants puissent être également substitués, et Y est hydrogène, phényle, acétoxyméthyle, pivaloyloxyméthyle, éthoxycarbonyle, choline, diméthylaminoéthyle, 5-indanyle, phthalidinyle, 5-alkyl-2-oxo-1,3-dioxol-4-ylméthyle, 3-acétoxy-2-oxobutyle, alkyle C1-C6, alcoxyméthyle C2-C7 ou phénylalkyle composé d'alkylène C1-C6 et de phényle.

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