GB896072A - Penicillin compounds - Google Patents

Abstract

Relates to compounds having the formula <FORM:0896072/IV (b)/1> and the pharmaceutically acceptable salts thereof wherein M is hydroxy, alkoxy containing 1 to 4 carbon atoms, amido, carboxymethylimido, carboxyethylimido or carboxyethylideneimido, R1 is methylene or ethylidene, R2 is cycloalkylene containing 4 to 6 carbon atoms, phenylene, 2,5-thienylene, 2-carboxy-3,4-thienylene, methylene or substituted methylene wherein the substituent is carboxy or halogen, alkylene containing 2 to 4 carbon atoms which may be unsaturated and substituted derivatives thereof wherein the substituent is hydroxy, carboxy, halogen or alkenoyloxy radical of a hydrocarbon carboxylic acid containing 1 to 4 carbon atoms. Typical compounds of the above formula are carboxymethylmercaptomethylmercaptomethylpenicillin, carboxymethylmercaptoethylmercaptomethylpenicillin, carboxymethylmercapto (a ,b - dimethyl) ethylmercaptomethyl penicillin, carboxymethylmercapto - trans - 1,2 - cyclohexyl - mercaptomethylpenicillin, carboxymethylmercaptoethylidenemercaptomethylpenicillin and carboxymethylmercapto - (b - hydroxy) - propylmercaptomethyl penicillin. The compounds may be prepared by reacting 6-amino-penicillanic acid with an acylating agent containing the group <FORM:0896072/IV (b)/2> such as a free acid halide or anhydride or a free acid in the presence of a carbodiimide.ALSO:Pharmaceutical preparations comprise a penicillin of the formula <FORM:0896072/VI/1> or a pharmaceutically acceptable salt thereof, wherein M is hydroxy, alkoxy containing 1 to 4 carbon atoms, amido, carboxymethylimido, carboxyethylimido, R1 is methylene or ethylidene, R2 is cycloalkylene containing 4 to 6 carbon atoms, phenylene, 2,5-thienylene, 2-carboxy-3,4-thienylene, methylene or substituted methylene wherein the substituent is carboxy or halogen, alkylene containing 2 to 4 carbon atoms which may be unsaturated and substituted derivatives thereof wherein the substituent is hydroxy, carboxy, halogen or alkenoyloxy radical of a hydrocarbon carboxylic acid containing 1 to 4 carbon atoms. The preparations may be in the form of tablets, capsules, elixirs or suspensions for oral administration or may be injected as sterile aqueous solutions.