Neue Cephalosporinderivate und ihr Herstellungsverfahren

摘要

1,271,018. Pyrrolo - thiazine derivatives. ROUSSEL-UCLAF. 27 June, 1969 [27 June, 1968], No. 47790/71. Divided out of 1,271,013. Heading C2C. The invention comprises novel threo or erythro (or mixtures thereof) pyrrolo-thiazine derivatives of the formulµ in which R1 is H or unsubstituted or substituted aryl, R is alkyl or aralkyl and Y is imido or acylamino, and the preparation thereof. The γ- lactams of 2-(α-R-oxycarbonyl-α-γ-methyl)-5- aminomethyl - 2,3 - dihydro - 1,3 - thiazine - 4- carboxylic acids (VIII) are obtained by reacting the corresponding 1-R1-2,3-dioxo-4-mercaptomethylpyrrolidines with enamines of the formula The γ-lactams of 2-(α-R-oxycarbonyl-α-aminomethyl) - 5 - aminomethyl - 2,3 - dihydro - 1,3- thiazine-4-carboxylic acids (VIIIa) are prepared by reacting compounds of Formula VIII above with hydrazine or subjecting said compounds to acid hydrolysis or hydrogenolysis. Hydrolysis of the resulting compounds gives the γ- lactams of 2 - (α - carboxy - α - aminomethyl)- 5 - aminomethyl - 2,3 - dihydro - 1,3 - thiazine- 4-carboxylic acids (IX) which on reaction with a tritylation agent give the γ-lactams of 2-(α- carboxy - α - tritylaminomethyl) - 5 - aminomethyl - 2,3 - dihydro - 1,3 - thiazine - 4 - carboxylic acids (IXa). The three isomers of the latter compound may be obtained by isomerization of the erythro isomers by treatment with alkaline reagents.