2-.beta.-alkenyl penam sulfones as .beta.-lactamase inhibitors

C - Chemistry – Metallurgy – 07 – D

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Details

C07D 499/86 (2006.01) A61K 31/43 (2006.01) A61K 31/44 (2006.01) A61K 31/545 (2006.01) C07D 499/00 (2006.01)

Patent

CA 2129564

The present invention is concerned with penam derivatives, in particular it is concerned with 2.beta.-alkenyl-penam derivatives of the general formula Image wherein one of R1 and R2 signifies -COR4, -CN, -CH2R5, halogen, -CH=CHR6 or Q and the other signifies hydrogen or lower alkyl or both together signify a .gamma.-lactam ring, R3 signifies hydrogen, lower alkyl, aryl-alkyl, allyl or a residue which is cleavable in vivo, R4 signifies hydrogen, lower alkyl, lower alkoxy, benzyloxy, amino, lower alkylamino or lower alkyl-lower alkoxyamino, R5 signifies hydroxy, -OCONHR7, -OCONH2 or a five- or six- membered hetero-aromatic ring which contains N,S and/or O and which is linked via a nitrogen atom, R6 signifies -CN or CHO, R7 signifies -COCH2Cl, Q signifies a five- or six-membered hetero-aromatic ring which contains N, S and/or O and n signifies 0, 1 or 2, as well as pharmaceutically compatible salts of these compounds. These compounds are good .beta.-lactamase inhibitors. They can be used for the prevention or treatment of bacterial infections, optionally together with a .beta.-lactam antibiotic.

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