US 4,489,072 A · Cephalosporins

Abstract

Novel cephalosporins which has attached to the exomethylene group at the 3-position of the cephem ring a substituted or unsubstituted aryl, acylamino, aromatic heterocyclic, triazolyl or tetrazolyl group, said aromatic heterocyclic group being attached through a carbon-carbon bond and said triazolyl or tetrazolyl group being attached through a carbon-nitrogen bond, and has the following group attached to the amino group at the 7-position: ##STR1## wherein A represents a group of the formula, --CH.sub.2 -- or a group of the formula ##STR2## in which R.sup.5 represents a hydrogen atom or an alkyl group, and the bond represents syn or anti isomer or their mixture; R.sup.3 represents a hydrogen or halogen atom; and R.sup.4 represents a hydrogen atom or an amino group which may be protected or substituted. These cephalosporins have a broad antibacterial spectrum, are stable against .beta.-lactamase produced by bacteria, have a low toxicity, and are well absorbed when administered orally or parenterally. This invention relates to such novel cephalosporins, processes for producing said cephalosporins, intermediates for producing said cephalosporins, and a process for producing said intermediates.

Claims30

Dependent claims

A cephalosporin represented by the following formula or a salt thereof:

##STR557## wherein R.sup.1 represents a hydrogen atom or a carboxyl-protecting group;
R.sup.2 represents a tetrazolyl group which may optionally be substituted by a substituent selected from the group consisting of halogen, alkyl, benzyl, phenethyl, 4-methylbenzyl, naphthylmethyl, phenyl, naphthyl, indanyl, alkenyl, hydroxyl, oxo, alkoxy, alkylthio, nitro, cyano, amino, alkylamino, dialkylamino, carboxylic acylamino, carboxylic acyl, carboxylic acyloxy, carboxylic acylalkyl, carboxyl, alkoxycarbonyl, carbamoyl, aminoalkyl, N-alkylaminoalkyl, N,N-dialkylaminoalkyl, hydroxyalkyl, hydroxyiminoalkyl, alkoxyalkyl, carboxyalkyl, alkoxycarbonylalkyl, benzyloxycarbonylalkyl, phenethyloxycarbonylalkyl, 4-methylbenzyloxycarbonylalkyl, naphthylmethyloxycarbonylalkyl, sulfoalkyl, sulfo, sulfamoylalkyl, sulfamoyl, carbamoylalkyl, carbamoylalkenyl, and N-hydroxycarbamoylalkyl, or a triazolyl group which may optionally be substituted by one or two substituents selected from the above-mentioned groups, said tetrazolyl or triazolyl group being attached to the exomethylene group at the 3-position of the cephem ring through a carbon-nitrogen bond;
R.sup.3 represents a hydrogen or halogen atom;
R.sup.4 represents a hydrogen atom or an amino group which may optionally be protected, or optionally substituted by at least one substituent selected from the group consisting of alkyl, alkenyl, cycloalkyl, phenyl, naphthyl, indanyl, benzyl, phenethyl, 4-methylbenzyl, naphthylmethyl, heterocyclic and heterocyclic alkyl wherein said heterocyclic is selected from the group consisting of furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, thiatriazolyl, oxatriazolyl, triazolyl, tetrazolyl, pyridyl, 3-(2-methyl-4-pyrrolinyl), 3-(4-pyrrolinyl), N-(methylpiperidinyl), quinolyl, phenazinyl, 1,3-benzodioxolanyl, benzofuryl, benzothienyl, benzoxazolyl, benzothiazolyl and coumarinyl;
A represents a group of the formula, --CH.sub.2 --, or a group of the formula, ##STR558## in which R.sup.5 represents a hydrogen atom or an alkyl group and the bond means that the compound may be a syn isomer or an anti-isomer or a mixture thereof;
and B represents a hydrogen atom or a lower alkoxy group.

3 more elements

Dependencies are inferred from the claim text.

Cephalosporins

Life of this patent

Cephalosporins

Life of this patent

Abstract

Claims30