Ciba-geigy Corporation

Karoly Kocsis

Hans Bickel

Bruno Fechtig

Heinrich H Peter

Riccardo Scartazzini

Peter Schneider

Hansuli Wehrli

Hans Bikel

Acylamido-3-cephem-4-carboxylic acid compounds of the formula ##STR1## in which the index n represents an integer of from 1 to 4,

Compounds with terminal aminocarboxylic acid grouping

Compounds of the formula ##STR1## in which the index n represents an integer of from 1 to 4,

Cephem compounds having a terminal aminocarboxylic acid grouping and

Cephalosporin compounds with terminal aminocarboxylic acid groupings and

Compounds of the formula ##STR1## wherein R.sub.1 denotes optionally substituted phenyl, thienyl, furyl or 1,4-cyclohexadienyl, R.sub.2 represents a free carboxyl group or an esterified carboxyl group which can be split physiologically, R.sub.3 represents hydrogen, lower alkoxy or an optionally substituted methyl group and B represents an optionally substitued six-membered ring with 1 to 3 ring nitrogen atoms, which is bonded to the carbonyl group --C(.dbd.O)-- by one of its carbon atoms, the nitrogen atoms of a monocyclic six-membered ring having 2 nitrogen atoms being either adjacent or separated by two ring carbon atoms, and the salts of such compounds which have a salt-forming group, including the inner salts, for example the 7.beta.-[D(-)-.alpha.-(3,5-Dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-c arboxamido)-phenylacetamido]-cephalosporanic acid, have antibiotic activity.

Cephalosporins having an .alpha.-acylaminoacetic acid side chain

6-Acylamino-penam-3-carboxylic acids and 7-acylamino-3-cephem-4-carboxylic acids in which the acyl group has the formula ##STR1## in which R.sub.1 is hydrogen, R.sub.2 is optionally substituted phenyl, thienyl or furyl or R.sub.1 and R.sub.2 together are optionally substituted cycloalkyl, n and m independently of one another represent 0 or 1 and B represents an optionally substituted 2,6-dioxo- or 2,6-dithioxo-1,2,3,6-tetrahydro-pyrimidyl, 2-thioxo-6-oxo-1,2,3,6-tetrahydropyrimidyl, 2,6-dihydroxy- or 2,6-dimercapto-pyrimidyl, 2-mercapto-6-hydroxy-pyrimidyl, 2,6-diaminopyrimidyl, 2-amino-6-hydroxy-pyrimidyl or 2,6-dihalogenopyrimidyl radical, these radicals being bonded in the 4- or 5-position.

Derivatives of penam-3-carboxylic acid and a pharmaceutical composition

Compounds of the formula ##STR1## wherein R.sub.1 denotes optionally substituted phenyl, thienyl, furyl or 1,4-cyclohexadienyl, R.sub.2 represents a free carboxyl group or an esterified carboxyl group which can be split physiologically, R.sub.3 represents hydrogen, lower alkoxy or an optionally substituted methyl group and B represents an optionally substituted six-membered ring with 1 to 3 ring nitrogen atoms, which is bonded to the carbonyl group --C(.dbd.O)-- by one of its carbon atoms, the nitrogen atoms of a monocyclic six-membered ring having 2 nitrogen atoms being either adjacent or separated by two ring carbon atoms, and the salts of such compounds which have a salt-forming group, including the inner salts, for example the 7.beta.-[D(-)-.alpha.-(3,5-Dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-c arboxamido)-phenylacetamido]-cephalosporanic acid, have antibiotic activity.

6-Acylamino-penam-3-carboxylic acids and 7-acylamino-3-cephem-4-carboxylic acids in which the acyl group has the formula ##STR1## in which R.sub.1 is hydrogen, R.sub.2 is optionally substituted phenyl, thienyl or furyl, or R.sub.1 and R.sub.2 together are optionally substituted cycloalkyl, and B is a radical which is bonded via a sulphur atom or is bonded to oxygen or sulphur with the interposition of an optionally substituted CH.sub.2 -group.

7.alpha. Ureido cephem-4-carboxylic acid derivatives

The invention relates to compounds of the formula ##STR1## wherein R.sub.1 denotes optionally substituted phenyl, thienyl, furyl or 1,4-cyclohexadienyl, R.sub.2 represents a free carboxyl group or an esterified carboxyl group which can be split physiologically, R.sub.3 represents hydrogen, lower alkoxy or an optionally substituted methyl group, and B represents a monosubstituted or polysubstituted six-membered ring with 1 to 3 ring nitrogen atoms which is bonded to the carbonyl group --C(.dbd.O)-- by one of its ring carbon atoms, and the salts of such compounds which have salt-forming groups, which compounds possess antibiotic properties.

Cephalosporins having an .alpha.-acyloxyacetic acid side chain

Compounds of the formula ##STR1## wherein R.sub.1 denotes optionally substituted phenyl, thienyl, furyl or 1,4-cyclohexadienyl, R.sub.2 represents a free carboxyl group or an esterified carboxyl group which can be split physiologically, R.sub.3 represents hydrogen, lower akoxy or an optionally substituted methyl group and B represents an optionally substituted six-membered ring with 1 to 3 ring nitrogen atoms, which is bonded to the carbonyl group --C(.dbd.O)-- by one of its carbon atoms, the nitorgen atoms of a monocyclic six-membered ring having 2 nitrogen atoms being either adjacent or separated by two ring carbon atoms, and the salts of such compounds which have a salt-forming group, including the inner salts, for example the 7.beta.-[D(-)-.alpha.-(3,5-Dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbo xamido)-phenylacetamido]-cephalosporanic acid, have antibiotic activity.

6-Acylamino-penam-3-carboxylic acids and 7-acylamino-3-cephem-4-carboxylic acids in which the acyl group has the formula ##STR1## IN WHICH R.sub.1 is hydrogen, R.sub.2 is optionally substituted phenyl, thienyl or furyl or R.sub.1 and R.sub.2 together are optionally substituted cycloalkyl, n and m independently of one another represent 0 or 1 and B represents an optionally substituted 2,6-dioxo- or 2,6-dithioxo-1,2,3,6-tetrahydro-pyrimidyl, 2-thioxo-6-oxo-1,2,3,6-tetrahydropyrimidyl, 2,6-dihydroxy- or 2,6-dimercapto-pyrimidyl, 2-mercapto-6-hydroxy-pyrimidyl, 2,6-diaminopyrimidyl, 2-amino-6-hydroxy-pyrimidyl or 2,6-dihalogenopyrimidyl radical, these radicals being bonded in the 4- or 5-position.

6-Acylamino-penam-3-carboxylic and 7-acylamino-3-cephem-4-carboxylic

6-acylamino-penam-3-carboxylic acids and 7-acylamino-3-cephem-4-carboxylic acids in which the acyl group has the formula ##STR1## in which R.sub.1 is hydrogen, R.sub.2 is optionally substituted phenyl, thienyl or furyl or R.sub.1 and R.sub.2 together are optionally substituted cycloalkyl, and R is a radical which is linked through a carbon, oxygen, sulphur or nitrogen atom.

6-Acylamino-penam-3-carboxylic acids

6-Acylamino-penam-3-carboxylic acids and 7-acylamino-3-cephem-4-carboxylic acids in which the acyl group has the formula ##EQU1## in which R.sub.1 is hydrogen, R.sub.2 is optionally substituted phenyl, thienyl or furyl, or R.sub.1 and R.sub.2 together are optionally substituted cycloalkyl, and B is a radical which is bonded via a sulphur atom or is bonded to oxygen or sulphur with the interposition of an optionally substituted CH.sub.2 -group.

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Basel, Switzerland

Karoly Kocsis