GB1291681A - 6-amino-penicillanic acid derivatives and preparation thereof - Google Patents

Abstract

1291681 Benzotriazolyl penicillins MERCK PATENT GmbH 8 June 1971 19455/71 Headings C2A and C2C Novel penicillins of Formula I and salts thereof, wherein Z is R<SP>1</SP> is H, C 1 -C 4 alkyl or -COOR<SP>5</SP>, R<SP>2</SP> and R<SP>5</SP> are the same or different and each is H or C 1 -C 4 alkyl, and R<SP>3</SP> and R<SP>4</SP> are the same or different and each is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, OH, F, Cl, Br, I, CF 3 , NO 2 or NH 2 , are prepared by reacting 6-aminopenicillanic acid or a salt thereof with a benzotriazolyl fatty acid of formula (II) wherein Z, R<SP>1</SP> and R<SP>2</SP> are as defined above, or an N-acylating derivative thereof. Suitable, such derivatives are the acid halides, anhydrides or mixed anhydrides, azides and reactive esters, or the acid itself together with a condensing agent may be used. The reaction is conducted in a suitable solvent, arid the penicillin may be isolated from the reaction mixture as the free acid or its salt, e.g. with an alkali or alkaline earth metal, ammonia or an amine. When the penicillin has R<SP>3</SP> and/or R<SP>4</SP> as a nitro group, this group may be catalytically hydrogenated to give an amino group. The chlorides of 2-(1H-benzotriazolyl-(1))-propionic acid, 1H - benzotriazolyl - (1) - acetic acid and 5 - nitro - 2H - benzotriazolyl - (2) - acetic acid are prepared by treating the respective acids with PCl 5 or SO 2 Cl 2 . Pharmaceutical compositions having antibiotic activity against gram-positive and gramnegative bacteria comprise a penicillin of Formula I or a physiologically acceptable salt thereof, together with an inert pharmaceutically acceptable carrier or diluent.