.beta.-lactamase inhibitors and process for their preparation

Details .beta.-lactamase inhibitors and process for their preparation .beta.-lactamase inhibitors and process for their preparation

C - Chemistry, Metallurgy

07

D

260/299, 204/91.

C07D 498/04 (2006.01) C07D 503/00 (2006.01)

Patent

CA 1064039

ABSTRACT OF THE DISCLOSURE Isoclavulanic acid and derivatives of it are dis- closed which have .beta.-lactamase inhibitory and antibacterial properties, the preferred compounds being of the formula Image (I) wherein R is hydrogen or Image wherein n is 0 or an integer from 1 to 6; R1 is a hydrogen or a phenol or phenoxy group and R2 is a hydrogen or halogen atom or a C1-4 alkyl, C1-4 alkoxy, -CO2R3 group where R3 is a hydro- carbon group of 1-8 carbon atoms or Image ; or pharmaceutically acceptable salts thereof of the group of sodium, potassium, calcium, magnesium and aluminum; or pharmaceutically acceptable esters thereof of the formula . Image wherein A is a hydrocarbon group of 1 to 9 carbon atoms or a hydrocarbon group of 1 to 9 carbon atoms substituted by one or more halogen, lower alkyl, lower acyl, lower etherified or acylated hydroxy groups. These compounds are prepared by isomerization of clavulanic acid or derivatives, for example in the presence of a transition metal catalyst and hydrogen, or by ultra-violet irradiation.

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