GB1300692A - Cephalosporins and preparation thereof - Google Patents

Abstract

1300692 7 - (α - Sulphoacylamino) - cephalosporanic acids TAKEDA YAKUHIN KOGYO KK [trading as TAKEDA CHEMICAL INDUSTRIES Ltd] 19 April 1971 [11 Feb 1970 4 Feb 1971] 21428/71 Heading C2A Novel cephalosporins having the general Formula I wherein R is hydrogen, C 1 to C 6 alkyl or phenyl; M and M<SP>1</SP> are the same or different and each is hydrogen, an alkali metal or alkaline earth metal atom or the group HA where A is an organic amine; and X is acetoxy or a group of formula are prepared by reacting 7-aminocephalosporanic acid or a salt or readily decomposable ester thereof with an α-sulphocarboxylic acid of formula R.CH(SO 3 H).COOH or an N-acylating derivative thereof, and if necessary replacing an ester group in the product by M<SP>1</SP>. N-Acylating derivatives of the sulphocarboxylic acid may be an acid halide, anhydride, mixed anhydride, azide or activated ester, or the acid itself may be used preferably in the presence of a condensing agent. When a derivative of the acid is used, an organic or inorganic base is preferably included in the reaction mixture. The sulpho group may be protected, e.g. as a sulphonamide or sulphonate. Decomposable esters of the 7- aminocephalosporanic acid may be silyl or stannyl esters, the ester groups being replaced by hydrogen after the reaction by treating the product with water or an alkanol. The preparative process is preferably conducted in an organic or aqueous solvent at - 5‹ to + 40‹ C. Pharmaceutical compositions having antibiotic activity against Gram-positive and -negative micro-organisms comprise a cephalosporin of Formula I together with a pharmaceutically acceptable diluent or carrier.