GB1067965A - Penicillins, esters, amides and salts thereof - Google Patents

Abstract

The invention relates to penicillins of Formula I <FORM:1067965/C2/1> and non-toxic salts thereof, where R is hydrogen or an alkyl, aryl or heterocyclic group which may be substituted, R1 and R2 are the same or different and are each H or a C1- 5 alkyl and X is OH, C1- 5 alkoxy, amino or substituted amino group. Typical are sodium (a -sulphamoyl)-benzylpenicillin and (a -sulphamoyl)-benzylpenicillinamide. The penicillins are prepared by reacting 6-aminopenicillanic acid, a salt, ester or amide thereof, with a reactive derivative of a carboxylic acid of formula <FORM:1067965/C2/2> wherein R, R1 and R2 have the above meanings. Alternatively, a penicillin (free acid) of Formula I may be converted to a reactive form, e.g. acid halide and treated with ammonia or with the appropriate alcohol or amine. Phenyl a -sulphamoylacetic acid is prepared by reacting benzylsulphonamide with (CH3)2-CH.Mg.Cl, followed by treatment with solid CO2 and acidification with HCl. a - (N,N - dimethylsulphamoyl) - phenylacetic acid is prepared from N,N-dimethylbenzyl-sulphonamide and (CH3)2CH.Mg.Cl in a similar manner. Sulphamoyl acetic acid is prepared by treating chlorosulphonylacetic acid with NH3 in ether.