Ciba-Geigy Corporation

Fujisawa Pharmaceutical Company, Ltd.

Riccardo Scartazzini

Hans Bickel

Bruno Fechtig

Karoly Kocsis

Karl Heusler

Heinrich H Peter

Peter Schneider

Hansuli Wehrli

Karl Schaffner

Beat Muller

Gottfried Sedelmeier

Rene Wiederkehr

The invention concerns 7-amino-ceph-3-em-4-carboxylic acid compounds of the formula ##STR1## wherein R.sub.1.sup.a represents hydrogen or an amino protective group R.sub.1.sup.A and R.sub.1.sup.b represent hydrogen or an acyl group AC, or R.sub.1.sup.A and R.sub.1.sup.b together denote a bivalent amino protective group, and R.sub.2 represents hydrogen or an organic radical R.sub.2.sup.A which together with the --C(.dbd.O)--O-- grouping forms a protected carboxyl group, or salts such compounds which possess salt-forming groups; these compounds have antibiotic properties.

8-oxo-5-thia-1-azabicyclo(4,2,0)oct-2-ene compounds

The invention concerns 7.beta.-amino-cepham-3-one-4-carboxylic acid compounds, particularly esters thereof, and the N-substituted, especially N-acylated derivatives of such compounds. They can be used as intermediates, for example, for the manufacture of the corresponding enol ethers and esters, as well as the corresponding 3-unsubstituted 7.beta.-amino-3-cephem-4-carboxylic acid compounds, which show outstanding pharmacological effects.

Ceph-3-one compounds and process for their manufacture

Cephem and cepham derivatives

6-Amino-penam compounds, having an antimicrobial action, of the formula ##STR1## in which R.sub.1 is an azaoligocycloalkyl radical which is bonded via the ring nitrogen atom and contains at least one endo-bridge atom and a total of 7 to 12 ring atoms and can contain a double bond and/or, if desired, as a further ring hetero-atom, an oxygen atom, or a nitrogen atom which can link the radical X.sub.1, where X.sub.1 is hydrogen or lower alkyl, and/or, if desired, free, esterified or etherified hydroxyl which is bonded to a ring carbon atom, and in which R.sub.2 is free carboxyl or carboxyl esterified by a physiologically detachable group, and salts of such compounds, processes for their preparation, pharmaceutical preparations which contain these compounds, including mixtures of these compounds with other antimicrobial, especially antibacterial and/or antiviral, active ingredients and/or additional substances or substance mixtures which alleviate the symptoms in the case of infections, the use of the novel compounds of the formula I and their salts, and of the novel substance mixtures, for combating micro-organisms and the preparation of corresponding medicaments by non-chemical means.

6-Azaoligocycloalkylmethyleneaminopenam compounds

Process for the preparation of cepham and cephem compounds

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

The invention relates to a novel advantageous process for the production of compounds of the formula ##STR1## wherein n is 1, R.sub.1.sup.a is hydrogen or an amino protective group R.sub.1.sup.A, R.sub.1.sup.b is hydrogen or an acyl group Ac, or R.sub.1.sup.a and R.sub.1.sup.b together are a bivalent amino protective group, R.sub.2 is hydroxyl or a radical which, together with the carbonyl grouping --C(.dbd.O)--, forms a protected carboxyl group, and the group of the formula --N(R.sub.3.sup.a) (R.sub.3.sup.b) is a secondary or tertiary amino group, or a salt thereof with salt-forming groups. The process comprises reaction of the corresponding 3-amino compounds with borohydrides in the presence of acids.

Process for the production of 7

The invention concerns 7-amino-ceph-3-em-4-carboxylic acid compounds of the formula ##STR1## wherein R.sub.1.sup.a represents hydrogen or an amino protective group R.sub.1.sup.A and R.sub.1.sup.b represent hydrogen or an acyl group Ac, or R.sub.1.sup.A and R.sub.1.sup.b together denote a bivalent amino protective group, and R.sub.2 represents hydrogen or an organic radical R.sub.2.sup.A which together with the --C(.dbd.O)--O-- grouping forms a protected carboxyl group, or salts such compounds which possess salt-forming groups; these compounds have antibiotic properties.

8-Oxo-5-thia-1-azabicyclo(4,2,0)oct-2-ene compounds

The invention relates to the novel crystalline hydrochloride and the crystalline hydrobromide of 7.beta.-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carbo xylic acid pivaloyloxymethyl ester, a process for the production thereof, and pharmaceutical preparations that contain these compounds.

Crystalline salts

The invention relates to O-substituted 7.beta.-amino-3-cephem-3-ol-4-carboxylic acid compounds of the formula ##STR1## wherein R.sub.1.sup.a represents hydrogen or an amino protective group R.sub.1.sup.A and R.sub.1.sup.b represents hydrogen or an acyl group Ac, or R.sub.1.sup.a and R.sub.1.sup.b together represent a bivalent amino protective group, R.sub.2 represents hydroxyl or a radical R.sub.2.sup.A which together with the carbonyl grouping --C(.dbd.O)-- forms a protected carboxyl group and R.sub.3 represents an optionally substituted hydrocarbon radical or an acyl group, and to 1-oxides of 3-cephem compounds of the formula I, and also to the corresponding 2-cephem compounds of the formula ##STR2## wherein R.sub.1.sup.a, R.sub.1.sup.b, R.sub.2 and R.sub.3 have the abovementioned meanings, or salts of such compounds with salt-forming groups. 3-Cephem compound of the formula IA, particularly those, in which R.sub.1.sup.a represents an acyl group, R.sub.1.sup.b is hydrogen and R.sub.2 is hydroxy exhibit pronounced antimicrobial effects, the others, and particularly the 1-oxides of these 3-cephem compounds and the corresponding 2-cephem compounds are useful as intermediates.

Process for preparing cephalosporin ethers

Cepham compounds

Cephalosporin compounds with terminal aminocarboxylic acid groupings and

The invention relates to aminothiazolacetamido-3-cephem-4-carboxylic acid compounds of the formula ##STR1## in which the index n represents an integer of 1 to 4,

7-Thiazolyl-acetamido-cephem derivatives with terminal aminocarboxylic

Process for the production of 7.beta.-substituted 3-hydroxycepham-4-carboxylic acid compounds of the formula ##STR1## in which R.sub.1.sup.a represents hydrogen or an amino-protecting group R.sub.1.sup.A, and

Growing community of inventors

Allschwil, Switzerland

Riccardo Scartazzini