GB1255034A - Penicillin esters - Google Patents

Abstract

1,255,034. Esters of penicillanic acids. BEECHAM GROUP Ltd. 5 Sept., 1969 [6 Sept., 1968], No. 42485/68. Heading C2A. Novel penicillin esters of an 8-hydroxyquinoline, having the general Formula I wherein R is a substituted or unsubstituted alkyl, aryl, aralkyl or heterocylic group and X, Y and Z are the same or different and are hydrogen or halogen or a C 1 -C 5 alkyl or substituted alkyl group, a C 1 -C 5 alkoxy group or a C 1 -C 5 acyl group, are prepared by treating an appropriate 8-hydroxy-quinoline with an esterifying derivative of a penicillin. Such derivatives may be the acid chloride, mixed anhydride, or the product of the reaction between the penicillin carboxyl group and a carbodiimide or carbonyldiimidazole; they are preferably prepared in situ in the reaction medium to which is subsequently added the 8-hydroxyquinoline. The 8-hydroxyquinolinyl penicillinates have anti-microbial activity; however if required the compounds of Formula I may be N- deacylated to the corresponding 6-APA ester and then re-acylated and the 8-hydroxyquinolinyl group removed, e.g. by mild alkaline hydrolysis or chelation with a copper or other heavy metal salt, to give a semi-synthetic penicillin.