3-Sulphonyloxy-vinyl cephalosporin derivs. - are intermediate for antibacterial heterocyclyl-thio-vinyl cephalosporin(s)

摘要

7-R1NH 3-RR3C=CH- 4-R2OOC-ceph-2 or 3-em derivs. and their 1-oxides of formula (I) are new, (where R1 is (a) a 2-R6NH-thiazol-4-yl-C(=N-OR5)-CO- gp. (Gp.A); (b) H or (c) benzhydryl, trityl, R7-CO-, -COOR8 or (Z)2P(O)- or the group R1-NH is replaced by a methyleneamino gp. in which the methylene gp. is substd. by dialkylamino or aryl (which may be substd. by one or more methoxy or nitro groups); R5 is H, alkyl, vinyl, cyanomethyl or an oxime protecting gp. -CR'R'-COOR"; R1 groups independently are H or alkyl or together are 2-3C alkylene; R" is H or an acid protecting gp.; R6 is H or an amino-protecting group, R7 is phenalkyl or phenoxyalkyl; R8 is branched, un-substd. alkyl or straight or branched substd. alkyl, substd. by phenyl (opt. substd. by alkyl, nitro or phenyl) or vinyl; Z is phenyl or -OZ'; Z' is alkyl, 2,2,2-trichloroethyl, phenyl or benzyl (the last two gps. opt. substd. by halo, alkyl, alkoxy or nitro) or the two Z' gps. together form a 2-3-alkylene gp.; R2 is H or an acid protecting gp.; R is phenyl opt. substd., a 5-6 membered heterocyclic having a single heteroatom (e.g. 2- or 3-pyridyl, 2- or 3- thienyl or 2- or 3-furyl opt. substd., 1-5C alkyl, benzyl opt. substd., 5-6-membered aromatic heterocyclic-methyl (e.g. 2 or 3 pyridyl, furyl or thienyl-methyl), 3-6C cycloalkyl or 5-6 membered O or S heterocyclyl; R3 is R4-SO2-O; R4 is alkyl, trihalomethyl or phenyl opt. substd.; n is 0 or 1. With the condition that when n is O the product is a bicyclo-oct-2-or 3-ene and when n is 1, the product is a bicyclo-oct-2-ene. Alkyl radicals are 1-4C opt. branched unless specifically specified. (I) are intermediates for known antibacterials.