Clavulanic acid derivatives

C - Chemistry – Metallurgy – 07 – D

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260/299, 260/385

C07D 497/18 (2006.01)

Patent

CA 1117948

ABSTRACT OF THE DISCLOSURE Compounds of the formula (II) are disclosed: Image (II) wherein A is a group such that CO2A is a carboxylic acid group or a salt or ester thereof; R1 is a hydrogen atom or a CO2R3, COR4 or OR5 group where R3 is a lower alkyl, lower alykenyl, lower alkyl aryl or aryl group, R4 is a lower alkyl, lower alkenyl, lower alkyl aryl or aryl group and R5 is a CO2R6, COR6 or SO2R6 group where R6 is a lower alkyl, lower alkenyl, lower alkyl aryl or aryl group; and R2 is a hydrogen atom or a CO2R7 or COR8 group where R7 is a lower alkyl, lower alkenyl, lower alkylaryl or aryl group and R8 is a lower alkyl, lower alkenyl, lower alkylaryl or aryl group; or when R1 is a COR4 group and R2 is a COR8 group, R4 and R8 may be joined so that the N(COR4) COR8 moiety is a 5-,6-, or 7-membered heterocyclic ring to which may be fused a phenyl ring optionally substituted by one or two lower alkyl or lower alkoxyl groups or fluorine or chlorine atoms; or when R1 is an OR5 group and R2 is a COR8 group, R5 and R8 may be joined so that the N(OR5) COR8 moiety is a 5-,6-, or 7-membered heterocyclic ring. Processes for preparation are also disclosed. The compounds of formula (II) have particular .beta.-lactamase inhibitory and antibacterial activity.

302012

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