GB1302917A - - Google Patents

Abstract

1302917 Penicillin esters LOVENS KEMISKE FABRIK PRODUKTIONSAKTIESELSKAB 14 July 1971 [14 July 1970] 34195/70 Heading C2A Novel penicillanic esters having the Formula I and acid-addition salts thereof, wherein the asterisk indicates an asymmetric carbon atom and A is a substituted or unsubstituted straight or branched alkyl radical, are prepared by either (a) reacting an α-substituted (1,4-cyclohexadienyl)acetamido penicillanic acid derivative of Formula II with a compound of Formula III wherein A is as above, R is an amino group, a protected amino group or an azido group, and - COOY and X-CH 2 -are radicals capable of reacting with elimination of XY to form the group: -COO-CH 2 -; or (b) reacting an N- acylating derivative of an α-R-substituted (1,4- cyclohexadienyljacetic acid with a penicillanic acid ester of Formula VI where R and A have the aforesaid meanings, and X<SP>1</SP>is H, or a tri-(C 1 -C 5 )-alkylsilyl group; in each case to give a compound of Formula IV and if necessary (c) converting the group R in compound IV to an amino group. The group A is preferably a C 1 -C 8 alkyl radical which may be substituted by C 1 -C 4 alkoxy or alkylthio, halo C 1 -C 4 alkyl, halogen, or nitro groups. The group Y may be hydrogen, or an alkali metal or tertiary ammonium cation, and X may be halogen, or alkyl- or arylsulphonyloxy. Pharmaceutical compositions having antibiotic activity comprise a penicillin ester of Formula I or a non-toxic salt thereof together with a pharmaceutically acceptable diluent or carrier.