6.beta.-substituted penicillanic acids as .beta.-lactamase...

C - Chemistry – Metallurgy – 07 – D

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C07D 499/00 (2006.01) A61K 31/43 (2006.01)

Patent

CA 2195430

A 6.beta.-substituted penicillanic acid of formula (XII) or a pharmaceutically acceptable salt or ester thereof, wherein A and B are each hydrogen wherein the carbon atoms to which A and B are attached are linked by a single bond, or A and B together form a bond, wherein the carbon atoms to which A and B are attached are linked by a double bond, R1 is selected from the group consisting of a) hydrogen, b) a pharmaceutically acceptable salt and c) a pharmaceutically acceptable group selected from the group consisting of C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, C3-10 cycloalkyl, C3-10 cycloalkenyl, allyl, aryl, aralkyl, aralkenyl, aralkynyl, heterocyclyl, heterocyclylalkyl, heterocyclylalkenyl, heterocyclylalkynyl and alkylheterocyclyl; wherein said group c) is unsubstituted or substituted with a substituent selected from the group consisting of fluoro, chloro, bromo, iodo, azido, nitro, monoalkyl substituted amino, dialkyl substituted amino, aryl substituted amino, alkanoylamino, arylcarbonylamino, cyano, hydroxy, alkoxy, aryloxy, alkanoyloxy, arylcarbonyloxy, mercapto, alkylthio, arylthio, alkanoylthio, arylcarbonylthio, oxyimino, alkoxyimino and carboxy, and n is an integer between 0 and 2.

Acide pénicillanique à substitution 6.beta. selon la formule (XII), ou sel ou ester pharmaceutiquement acceptable de celui-ci, dans lequel: A et B sont chacun de l'hydrogène, les atomes de carbone auxquels A et B sont attachés étant liés par une liaison simple, ou A et B forment ensemble une liaison, les atomes de carbone auxquels A et B sont attachés étant reliés par une double liaison, R1 est sélectionné dans le groupes comprenant a) l'hydrogène, b) un sel pharmaceutiquement acceptable et c) un groupe pharmaceutiquement acceptable sélectionné dans le groupe comprenant les groupes alkyle C¿1-10?, alcényle C¿2-10?, alcynyle C¿2-10?, cycloalkyle C¿3-10?, cycloalcényle C¿3-10?, allyle, aryle, aralkyle, aralcényle, aralcynyle, hétérocyclyle, hétérocyclylalkyle, hétérocyclylalcényle, hétérocyclylalcynyle et alkylhétérocyclyle. Ce groupe c) n'est pas substitué ou comporte une substitution par un groupe fluoro, chloro, bromo, iodo, azido, nitro, amino avec substitution par monoalkyle, alkanoylamino, arylcarbonylamino, cyano, hydroxy, alcoxy, aryloxy, alkanoyloxy, arylcarbonyloxy, mercapto, alkylthio, arylthio, alkanoylthio, arylcarbonylthio, oxyimino, alkoxyimino et carboxy, et n est un nombre entier compris entre 0 et 2.

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