GB1377647A - Acyloxymethyl esters of alpha-ureidocyclohexadienylalkylene- penicillins - Google Patents

Abstract

1377647 Penicillins and cephalosporins E R SQUIBB & SONS Inc 22 Oct 1971 [26 Oct 1970 (4)] 49243/71 Heading C2C The invention comprises novel penicillins and cephalosporins of Formula I wherein R represents hydrogen, C 1 -C 7 alkyl or C 1-7 alkoxy, n represents 0, 1, 2, 3 or 4; B represents hydrogen or the group -CONH 2 and Z represents the Groups II or III wherein R is C 1 -C 7 alkyl, monocyclic carbocyclic aryl or monocyclic carbocyclic aralkyl wherein the alkyl group has up to 7 carbon atoms and X is hydrogen, C 1-7 alkoxy, C 1-7 alkanoyloxy, aroyloxy or aralkanoyloxy (the aryl and aralkyl portions of these last two being the same as defined for R<SP>1</SP>), the cation of a nitrogen base or a quaternary ammonium radical. A process for preparing compounds of Formula I comprises reacting a 1,4-cyclohexadienyl-alkanoic acid or Formula IV or an N-acylating functional derivative thereof, with a penicillin or cephalosporin reactant of Formula V wherein Z<SP>1</SP> has the Formula VI or VII wherein A is a carboxylic acid group or a salt thereof or the ester group and when the group A of the reactant is a carboxylic acid group or a salt thereof, further reacting with a halomethyl ester of formula wherein X<SP>1</SP> is halogen. Pharmaceutical compositions containing at least one of the penicillins and cephalosporins of Formula I as active ingredients have been prepared.