US 4,125,611 A · 3-Heterocyclic thiomethyl 7-methoxy-7 substituted acetamido cephalosporins

Abstract

A cephalosporin of the formula (I): ##STR1## wherein A is a mono- or polycyclic heteroaromatic ring containing at least one nitrogen atom as a hetero atom, which may be unsubstituted or substituted; R is a phenyl group which may be unsubstituted or substituted, a thienyl group, a furyl group, a cyclohexadienyl group or a cyclohexenyl group; X is an acetoxy group, a pyridinium group which may be unsubstituted or substituted with a methyl or carbamoyl group, a group of the formula: ##STR2## in which R.sub.1 and R.sub.2, which may be the same or different, each is a hydrogen atom or a (C.sub.1 - C.sub.4) alkyl group, or a group of the formula: -S-Het in which Het is a heterocyclic ring containing 1 to 5 oxygen, nitrogen and sulfur atoms as a hetero atom, in which the heterocyclic ring system may be either polycyclic or 5- or 6-membered monocyclic and may be unsubstituted or substituted; and M is a hydrogen atom or a biologically active carboxyl-protecting group, or is an anionic charge only when X is a pyridinium group; and the pharmaceutically acceptable salts thereof, which are useful as antimicrobial agents and prepared by the reaction of a compound of the formula (II): ho--a--cooh (ii) wherein A is as defined above, or a reactive derivative thereof, with a compound of the formula (III): ##STR3## wherein R, M and X are as defined above, or a derivative thereof.

Claims14

Dependent claims

A cephalosporin of the formula (I):

##STR175## wherein A is a heteroaromatic ring selected from the group consisting of quinoline, isoquinoline, cinnoline, naphthyridine, quinoxaline, pyrazolopyridine, pyridopyrazine, thiazolopyrimidine, pyridopyrimidine, pyrimidinopyridazine, thienopyridine, thiazolopyridine, pyridine, pyrimidine, pyridazine, triazine, and pyrazine, each of which may be substituted with one or two substituents selected from the group consisting of halogen, (C.sub.1 -C.sub.4)alkyl, (C.sub.1 - C.sub.4)alkoxy, (C.sub.2 - C.sub.5)alkanoyl, (C.sub.2 - C.sub.5)alkoxycarbonyl, (C.sub.1 - C.sub.4)alkylthio, mercapto, hydroxy, (C.sub.2 - C.sub.5)alkoxymethyl, cyano, nitro, (C.sub.1 - C.sub.4)alkylsulfonyl, phenylsulfonyl, sulfamoyl, carbamoyl, phenyloxycarbonylamino, acetoacetylamino, (C.sub.1 - C.sub.4)alkylamino, di-(C.sub.1 - C.sub.4)alkylamino, halo-(C.sub.1 - C.sub.4)alkyl, (C.sub.2 - C.sub.5)alkenyl, phenyl, (C.sub.3 - C.sub.6)cycloalkyl, (C.sub.4 - C.sub.6)cycloalkylene, piperazino, piperidino, pyrrolidino, and morpholino;
R is a phenyl group which may be unsubstituted or substituted with up to three chemically compatible substituents selected from the group consisting of nitro, di-(C.sub.1 - C.sub.4)alkylamino, (C.sub.2 - C.sub.5)alkanoylamino, (C.sub.1 - C.sub.4)alkylsulfonamino, amino hydroxy, (C.sub.2 - C.sub.5)alkanoyloxy, (C.sub.1 - C.sub.4)alkyl, (C.sub.1 - C.sub.4)alkoxy, chloro, bromo, fluoro, iodo, trifluoromethyl, hydroxymethyl, ureido or sulfamyl;
a thienyl group;
a furyl group;
a cyclohexadienyl group or a cyclohexenyl group;
X is
-S-Het
in which Het is tetrazolyl, thiadiazolyl, triazolyl, oxadiazolyl, pyridazinyl, tetrazolo-[4,5-b]pyridazinyl, pyridazino[3,2-c]-S-triazolyl or pyridazino-[2,1-c]-S-triazolyl, each of which may be unsubstituted or substituted with 1 or 2 substituents selected from the group consisting of (C.sub.1 - C.sub.4)alkyl, (C.sub.1 - C.sub.4)alkoxy, hydroxy, mercapto, hydroxymethyl, aminomethyl and methylamino;
and M is a hydrogen atom or a biologically active carbonyl-protecting group, and the non-toxic pharmaceutically acceptable salts thereof.

6 more elements

Dependencies are inferred from the claim text.

3-Heterocyclic thiomethyl 7-methoxy-7 substituted acetamido cephalosporins

Life of this patent

3-Heterocyclic thiomethyl 7-methoxy-7 substituted acetamido cephalosporins

Life of this patent

Abstract

Claims14