NOUVEAUX COMPOSES CEPHEME UTILES COMME MEDICAMENTS

摘要

1360860 Cephalosporins CIBA-GEIGY AG 1 July 1971 [8 July 1970 3 Dec 1970] 30875/71 Heading C2A The invention relates to 7-N-Ra 1 -N-Rb 1 - amino - 3 - R - methyl - ceph - 2 - em - 4 - carboxylic acid compounds of Formula 1 wherein R represents a radical, possessing a hydrogen and being bonded via a carbon atom, of an organic C-nucleophilic compound, Ra 1 is hydrogen or an amino protective group Ra 1 , Rb 1 is hydrogen or an acyl group or Ra 1 and R 1 b together denote a bivalent amino protective group, and R 2 represents hydrogen or a radical Ra 2 which together with the -C(=O)-O- grouping forms a protected carboxyl group, or salts of such compounds which have saltforming groups. Also 7-N-Ra 1 -N-Rb 1 -amino-3- R - methyl - ceph - 3 - em - 4 - carboxylic acid compounds of Formula IV wherein R, Ra 1 , Rb 1 and Ra 2 are as defined above, with the exception of (i) compounds of Formula IV in which R denotes an unsubstituted or substituted pyrryl or indolyl radical or a dicarbonylmethyl radical, in which each of the carbonyl groups is part of an acyl radical or an esterified carboxyl group, or both together are part of a diacyl radical, Ra 1 represents hydrogen or an acyl radical Ac, Rb 1 denotes hydrogen and R 2 has the meaning given above, (ii) compounds of the Formula IV, wherein R denotes the 2,4-dihydroxyphenyl radical, a phenyl group with two hydroxy groups in adjacent positions and an ethyl group in the m- and p-position, respectively, to these hydroxy groups, the 2,4,6-trihydroxy - phenyl, 2 - hydroxy - 1 - naphthyl, dicarboxymethyl, carboxycarbonylmethyl radical, a dimethylamino-phenyl radical, the 1- oxido-2-picolyl or the 2-hydroxy-1-4-dioxo-1-4- dihydro-3-naphthyl radical, Ra 1 denotes the phenylacetyl radical and Rb 1 and R 2 denote hydrogen, (iii) compounds of the Formula IV, wherein R represents 2,4-dimethoxy-phenyl, Ra 1 denotes phenylacetyl, Rb 1 denotes hydrogen and R 2 is methyl, (iv) compounds of the Formula IV, wherein R represents 2-oxocyclohexyl, Ra 1 denotes hydrogen, 2-thienylacetyl,α- amino - phenylacetyl orα- (tert. - butyloxycarbonyl) - aminophenylacetyl, Rb 1 denotes hydrogen and R 2 represents diphenylmethyl, and (v) compounds of the Formula IV, wherein R denotes 2-oxo-cyclohexyl, Ra 1 represents 2- thienylacetyl orα-amino-phenylacetyl, Rb 1 represents hydrogen and R 2 represents hydrogen. The invention also relates to 1-oxides corresponding to the ceph-3-em compounds - of Formula IV but without the above restrictions on groupings present. Pharmaceutical compositions suitable for oral or parenteral administration may be prepared using the above compounds as the active ingredient. Processes for the preparation of the above cephalosporins are described.