Roussel Uclaf

Michel Vignau

Rene Heymes

Andre Lutz

Andre Pierdet

Novel oximes of the syn isomers of 7-[2-(2-amino-4-thiazolyl)-acetamido]ceph-3-eme-4-carboxylic acid compounds of the fomrula ##STR1## wherein B is --(CH.sub.2).sub.n' --R.sub.5, n' is an integer from 1 to 4, R.sub.5 is ##STR2## R.sub.6 and R.sub.7 are individually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and when taken together with the nitrogen to which they are attached are selected from the group consisting of phthalimido and 1-pyridinyl, R.sub.1 is selected from the group consisting of chloro, CH.sub.3 O--, alkyl and alkylthio of 1 to 5 carbon atoms, cycloalkyl of 3 to 5 carbon atoms, --CH.sub.2 --S--R.sub.12, acetoxymethyl, carbamoyloxymethyl and ##STR3## R.sub.12 is selected from the group consisting of 2-oxo-(3H)-thiazolin-4-yl-carbonyl, 3-methyl-1,2-oxazol-5-yl-carbonyl, acyl of an alkanoic acid of 2 to 4 carbon atoms and a nitrogen heterocycle, Alka is alkyl of 1 to 4 carbon atoms and A is selected from the group consisting of hydrogen, --NH.sub.4, alkali metal, alkaline earth metal, magnesium, a non-toxic, pharmaceutically acceptable organic amine and easily cleaved ester and their non-toxic, pharmaceutically acceptable acid addition salts; having antibacterial activity and novel intermediates therefore.

Oximes

Novel syn isomers of 7-(2-amino-4-thiazolyl)-acetamido-cephalosporanic acid compounds of the formula ##STR1## wherein R is selected from the group consisting of --(CH.sub.2).sub.n --S--R.sub.2, --CHF.sub.2 and --(CH.sub.2).sub.n --S--CN, R.sub.2 is selected from the group consisting of optionally protonated ##STR2## n is an integer from 1 to 4, R.sub.1 is selected from the group consisting of hydrogen, chlorine, methoxy, alkyl and alkylthio of 1 to 5 carbon atoms, cycloalkyl of 3 to 5 carbon atoms, azidomethyl, acetoxymethyl, carbamoyloxymethyl, ##STR3## and --CH.sub.2 --S--R', Alk is alkyl of 1 to 4 carbon atoms, R' is selected from the group consisting of an optionally substituted nitrogen containing heterocycle and an acyl of an aliphatic acid of 2 to 4 carbon atoms, A is selected from the group consisting of hydrogen and an easily cleavable ester and when R is --(CH.sub.2).sub.n --SR.sub.2, the COOA group may be the anion --COO-- and when R is --(CH.sub.2).sub.n --SCN or --CHF.sub.2, A may further be selected from the group consisting of an equivalent of an alkali metal, an alkaline earth metal, magnesium, --NH.sub.4 and a non-toxic, pharmaceutically acceptable organic amine and their non-toxic, pharmaceutically acceptable acid addition salts having antibiotic properties and a novel process and novel intermediates for their preparation.

7-(2-Amino-4-thiazolyl)-acetamido cephalosporanic acids

Novel syn isomers of 7-(2-amino-4-thiazolyl)-acetamido-cephalosporanic acid compounds of the formula ##STR1## wherein R is selected from the group consisting of --(CH.sub.2).sub.n --S--R.sub.2, --CHF.sub.2 and --(CH.sub.2).sub.n --S--CN, R.sub.2 is selected from the group consisting of optionally protonated ##STR2## n is an integer from 1 to 4, R.sub.1 is selected from the group consisting of hydrogen, chlorine, methoxy, alkyl and alkylthio of 1 to 5 carbon atoms, cycloalkyl of 3 to 5 carbon atoms, azidomethyl, acetoxymethyl, carbamoyloxymethyl, ##STR3## and --CH.sub.2 --S--R', Alk is alkyl of 1 to 4 carbon atoms, R' is selected from the group consisting of an optionally substituted nitrogen containing heterocycle and an acyl of an aliphatic acid of 2 to 4 carbon atoms, A is selected from the group consisting of hydrogen and an easily cleavable ester and when R is --(CH.sub.2).sub.n --SR.sub.2, the COOA group may be the anion --COO.sup.- and when R is --(CH.sub.2).sub.n --SCN or --CHF.sub.2, A may further be selected from the group consisting of an equivalent of an alkali metal, an alkaline earth metal, magnesium, --NH.sub.4 and a non-toxic, pharmaceutically acceptable organic amine and their non-toxic, pharmaceutically acceptable acid addition salts having antibiotic properties and a novel process and novel intermediates for their preparation.

Novel 7-(2-amino-4-thiazolyl)-acetamido-cephalosporanic acids

A compound of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and a group easily removable by acid hydrolysis or hydrogenolysis, R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and A is selected from the group consisting of hydrogen, alkali metal, an equivalent of alkaline earth metal and magnesium and an organic amine base having antibiotic properties and a process for their preparation and novel intermediates.

3-Carbamoyloxymethyl-7-(amino-4-thiazolyl-acetamido)-cephalosporanic

Novel haptenes of the formula ##SPC1## Wherein when X is hydrogen, Y is =N-O-(CH.sub.2).sub.a --COOH and a is a whole number of 1 to 12 and when ##EQU1## X is hemiterephthaloyloxy in the .alpha.- or .beta.-position and antigens prepared therefrom by condensation with beef serum albumin.

Novel haptenes and antigens

A novel liquid phase oxidation process using silver silicate as the oxidizing agent which is particularly adapted for oxidation of a hydroxy attached to a carbon atom to a carbonyl group.

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Neuilly-sur-Seine, France

Michel Vignau