GB1134237A - Penicillins - Google Patents

Abstract

1,134,237. Penicillins. BEECHAM GROUP Ltd. 11 July, 1967 [12 July, 1966], No. 31197/66. Heading C2A. The invention comprises α-phenylsulphonamido penicillins of Formula (I) and non-toxic salts thereof, wherein R is an alkyl, aryl or heterocyclic group, any of which may be substituted with other groups; Z is H, Y is H and X is carboxy; or X is H and Z and Y together form a carbonyl group linking the phenyl group with the amino group. Typical compounds are sodium 6-[D - α - saccharimidophenyl acetamido] penicillanate, disodium 6- [D - α - (p - carboxyphenylsulphonamido) phenyl acetamido] penicillanate and disodium 6 - [α - (m - carboxy phenylsulphonamido)- α - 2- thienyl acetamido] penicillanate. Penicillins of Formula (I) wherein Z is H, Y is H and X is carboxy are prepared by reacting an α-amino penicillin of Formula (III) wherein R has the above meaning, with a sulphonyl chloride of Formula (IV) Penicillins of Formula (I) wherein X is H and Z and Y together represent a carbonyl group linking the phenyl ring with the amino group, are prepared by reacting the α-aminopenicillin of Formula (III) with an N-(alkoxy carbonyl) amide of Formula (V) wherein R<SP>1</SP> is C 1-5 alkyl. Alternatively these compounds may be prepared by acylating 6- aminopenicillanic acid or a salt thereof, with a reactive derivative of an α-phenylsulphonamido carboxylic acid of Formula (II) wherein R has the above meaning. The penicillins have antibacterial properties and may be used as nutritional supplements in animal feeds.