GB847375A - A process for the production of derivatives of cephalosporin c - Google Patents

Abstract

The invention relates to condensation products of Cephalosporin C wherein a functional derivative of an organic acid radical is condensed with the amino group of Cephalosporin C. By functional derivative of an organic acid radical is meant a substance which is reactive with an amine to produce a condensation product resembling a condensation product obtainable or theoretically obtainable with the acid itself. Specified are dithio-acids, e.g. dithiophenylacetic acid, acid chlorides and acid anhydrides of aliphatic and aromatic carboxylic acids, acid azides, sulphonyl halides, isocyanates such as phenylisocyanates and isothiocyanates preffered are the functional derivatives of benzoic acidbenzene sulphonic acid, p-aminobenzene sulphonic acid, other mono-nuclear aromatic acids and organic-amino acids. Peptide linked products may be produced by using mixed anhydrides of carboxylic acids containing protected amino groups in which the amino group is substituted by e.g. a carboxymethyl radical or an acid of formula HX where X is an acid radical e.g. sulphate. The condensation is carried out at a pH of above 1.0 and below 11.0, and preferably below 10 or 5 DEG C., by adding the organic acid or the functional derivative thereof to the Cephalosphorin C dissolved in a weakly alkaline aqueous solution, e.g. of an alkali metal such as sodium e.g. sodium bicarbonate. In the Cephalosporin C residue forming part of the condensation produced, the acid groups may be present as such or may have their replaceable hydrogen atoms replaced by a salt forming substituent group, e.g. a metal. In the example, benzoyl-Cephalosporin C is produced by reacting Cephalosporin C sodium salt in solution in alkaline aqueous acetone at a pH below 1 and at a temperature of 0 DEG C. with a solution of benzoyl chloride. Specification 810,196 is referred to.