GB1438800A - Cephalosporin derivatives and preparation thereof - Google Patents

Abstract

1438800 Cephem compounds FUJISAWA PHARMACEUTICAL CO Ltd 22 June 1973 [27 June 1972 (3) 29 June 1972 (2)] 29901/73 Heading C2C Novel cephem compounds having the general Formula (II) wherein R is a substituted or unsubstituted benzoyl group or an acyl group of formula (in which X is -CO- or-SO 2 ; R 1 , R 2 and R 3 are each hydrogen or halogen or an organic group, and R 4 is an aralkyl group), and Y is an azido group or the residue of an optionally substituted thiol group, are prepared by reacting Cephalosporin C in a cephalosporin C-containing fermentation broth produced by cultivation of a cephalosporin C producing microorganism, (a) with an N-acylating agent capable of introducng a group of formula R above into the 5-amino group of the 7-side chain to give an intermediate compound of Formula (III) and reacting the compound (III) with an appropriate strongly nucleophilic reactant (e.g. an appropriate thiol or sodium hydrazoate) to give the compound (II); (b) with a strongly nucleophilic reactant to give an intermediate compound of Fromula (IV) wherein Y is as defined above, and reacting the compound (IV) with an N-acylating agent capable of introducing a group R above into the 5-amino group to give the compound (II). The inventive compounds (II) may be converted into the corresponding 7-amino derivatives, of Formula (I) by reaction with a silylating agent, reacting the product with an imino-halogenating agent, reacting the resulting imide halide with an imino-etherification agent, and hydrolyzing the thus produced imino ether to give the said compound (I).