Ciba-Geigy Corporation

Ivan Ernest

Jacques Gosteli

Robert B Woodward

Marc Lang

Wolfgang Frostl

Jaroslav Kalvoda

Andreas Von Sprecher

Andreas Beck

Alan J Main

The invention relates to azetidin-2-ones of the formula ##STR1## wherein R.sub.a represents hydroxy-lower alkyl, R.sub.1 represents hydrogen, an organic radical bonded by a carbon atom to the ring carbon atom or an etherified mercapto group, R.sub.2.sup.A together with the carbonyl group to which it is attached is a protected carboxyl group and Z' is oxygen, sulfhur or an optionally substituted methylidene group, functional groups in the radicals R.sub.a, R.sub.1 and Z' optionally being in protected form. The azetidinones are useful intermediates for the preparation of penem antibiotics.

6-substituted thia-aza compounds

The invention relates to 2-penem-3-carboxylic acid compounds of the formula ##STR1## in which R.sub.a represents an organic radical bonded by a carbon atom to the ring carbon atom, a free, etherified or esterified hydroxy or mercapto group or a halogen atom, R.sub.1 represents hydrogen, an organic radical bonded by a carbon atom to the ring carbon atom, or an etherified mercapto group, and R.sub.2 represents a hydroxy group or an R.sub.2.sup.A radical that together with the carbonyl grouping --C(.dbd.O)-- forms a protected carboxyl group, and to salts of such compounds with salt-forming groups, processes for the manufacture of such compounds, pharmaceutical preparations containing compounds of the formula I with pharmacological properties, and their use. The compounds have antibiotic activity.

6-substituted penem compounds

Novel asymmetric thioethers of the formula ##STR1## in which R.sup.1 represents a C.sub.1-3 -alkyl radical or a C.sub.1-3 -hydroxyalkyl radical of which the hydroxy group may be in esterified form,

Aliphatic thioethers

The present invention relates to an improved process for the manufacture of (3S)-3,4-trans-disubstituted azetidinones of the formula ##STR1## in which R.sub.1 represents hydrogen or lower alkyl,

Process for the manufacture of optically active azetidinones

2-Penem-3-carboxylic acid compounds of the formula ##STR1## in which R.sub.1 represents hydrogen, an organic radical bonded by a carbon atom to the ring carbon atom or an etherified mercapto group and

Monocyclic intermediates for thia-aza compounds with a .beta.-lactam ring

Azetidinone-4-disulfides as intermediates for thia-aza compounds with a

Thia-aza compounds with a .beta.-lactam ring

Process for preparing thia-aza compounds with a beta-lactam ring

Intermediates for thia-aza compounds with a .beta.-lactam ring

The invention relates to 6-amino-2-penem-3-carboxylic acid compounds of the formula ##STR1## in which R.sub.1.sup.a denotes hydrogen or an amino protective group R.sub.1.sup.A and R.sub.1.sup.b represents hydrogen or an acyl radical Ac, or in which R.sub.1.sup.a and R.sub.1.sup.b conjointly form a bivalent amino protective group, R.sub.2 denotes 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 hydrogen or an organic radical which is linked via a carbon atom to the ring carbon atom, and 1-oxides thereof, as well as salts of such compounds having salt-forming groups, which compounds possess antibiotic properties, processes for the manufacture of such compounds, and also pharmaceutical formulations containing compounds of the formula I with pharmacological properties, and the use thereof, either as antibiotics, preferably in the form of pharmaceutical formulations, or as intermediate products.

Bicyclic unsaturated thia-aza compounds and 4-acylthio azetidinone

The invention relates to 6-amino-2-penem-3-carboxylic acid compounds of the formula ##STR1## in which R.sub.1.sup.a denotes hydrogen or an amino protective group R.sub.1.sup.A and R.sub.1.sup.b represents hydrogen or an acyl radical Ac, or in which R.sub.1.sup.a and R.sub.1.sup.b conjointly form a bivalent amino protective group, R.sub.2 denotes hydroxyl or a radical R.sub.2.sup.A which, together with the carbonyl grouping --C(.dbd.0)--, forms a protected carboxyl group, and R.sub.3 represents hydrogen or an organic radical which is linked via a carbon atom to the ring carbon atom, and 1-oxides thereof, as well as salts of such compounds having salt-forming groups, which compounds possess antibiotic properties, processes for the manufacture of such compounds, and also pharmaceutical formulations containing compounds of the formula I with pharmacological properties, and the use thereof, either as antibiotics, preferably in the form of pharmaceutical formulations, or as intermediate products.

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Birsfelden, Switzerland

Ivan Ernest