Patent Number: 6,294,668

Title: Vinylpyrrolidinone cephalosporin derivatives

Abstract: The present invention relates to cephalosporin derivatives of the generalformula##STR1##whereR.sup.1 is halogen, lower alkyl, phenyl, benzyl, styryl, naphthyl orheterocyclyl; the lower alkyl, phenyl, benzyl, styryl, naphthyl andheterocyclyl being optionally substituted by at least one of halogen,hydroxy, optionally substituted lower alkyl, optionally substituted loweralkoxy, optionally substituted phenyl, amino, lower alkylamino, di-loweralkylamino, carboxy, lower alkylcarboxy, carbamoyl or loweralkylcarbamoyl;R.sup.4, R.sup.5 independently are hydrogen, lower alkyl or phenyl;X is S, O, NH or CH.sub.2 ;n is 0,1 or 2;m is 0 or 1;s is 0 or 1;R.sup.2 is hydrogen, hydroxy, --CH.sub.2 --CONHR.sup.6, loweralkyl-Q.sub.r, cycloalkyl-Q.sub.r, lower alkoxy, lower alkenyl,cycloalkenyl-Q.sub.r, lower alkynyl, aralkyl-Q.sub.r, aryl-Q.sub.r,aryloxy, aralkoxy, a heterocyclic ring or a heterocyclyl-Q.sub.r, thelower alkyl, cycloalkyl, lower alkoxy, lower alkenyl, cycloalkenyl, loweralkynyl, aralkyl, aryl, aryloxy, aralkoxy and the heterocyclic ring may besubstituted with at least one group selected from carboxy, amino, nitro,cyano, --SO.sub.2 NHR.sup.6, optionally fluoro substituted lower alkyl,lower alkoxy, hydroxy, halogen, --CONR.sup.6 R.sup.7, --CH.sub.2CONR.sup.6 R.sup.7, --N(R.sup.7)COOR.sup.8, R.sup.7 CO--, R.sup.7 OCO--,R.sup.7 COO --, --C(R.sup.7 R.sup.9)CO.sub.2 R.sup.8, --C(R.sup.7R.sup.9)CONR.sup.7 R.sup.10, whereinR.sup.6 is hydrogen, lower alkyl, cycloalkyl or aryl;R.sup.7 and R.sup.9 are independently hydrogen or lower alkyl;R.sup.8 is hydrogen, lower alkyl, lower alkenyl or a carboxylic acidprotecting group; andR.sup.10 is hydrogen, .omega.hydroxy-alkyl, phenyl, naphthyl orheterocyclyl, the phenyl, naphthyl or heterocyclyl being unsubstituted orsubstituted with at least one of the groups of optionally protectedhydroxy, halogen, optionally substituted lower alkyl, optionally substituted lower alkoxy and/or cyano, orR.sup.7 and R.sup.10 form together group of formula##STR2##Q is --CHR--, --CO-- or --SO.sub.2 --;r is 0 or 1;R is hydrogen or lower alkyl; andR.sup.3 is hydroxy, --O.sup.-, lower-alkoxy, or --OM and M represents analkali metal;as well as readily hydrolyzable esters thereof, pharmaceutically acceptablesalts of said compounds and hydrates of the compounds of formula I and oftheir esters and salts, as well as the preparation of such compounds,their use for the treatment of infectious diseases and pharmaceuticalpreparations containing such compounds.

Inventors: Angehrn; Peter (Bockten, CH), Heinze-Krauss; Ingrid (Schliengen, DE), Richter; Hans G. F. (Grenzach-Wyhlen, DE)


International Classification:

Expiration Date: 09/25/2013