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AssigneeCiba-Geigy Corporation
InventorsIvan Ernest, Jacques Gosteli, Robert B. Woodward
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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.
An ylide compound of the formula ##STR30## wherein R.sub.1.sup.A represents an acyl group of the formula ##STR31## in which (1) R.sub.a is phenyl, 4-hydroxyphenyl or 1,4-cyclohexadienyl, R.sub.b is hydrogen, amino or amino which is protected by halogenated lower alkoxycarbonyl or phenyl lower alkoxycarbonyl which is unsubstituted or mono-substituted by lower alkoxy or nitro and R.sub.c is hydrogen, or in which (2) R.sub.a is phenoxy and R.sub.b and R.sub.c represent hydrogen, R.sub.1.sup.b is hydrogen or R.sub.1.sup.A and R.sub.1.sup.b together represent phthaloyl, R.sub.2.sup.A is lower alkoxy, 2-halogeno-lower alkoxy, 2-lower alkenyloxy, diphenylmethoxy which is unsubstituted or disubstituted by lower alkoxy, 4-methoxybenzyloxy, nitrobenzyloxy or pentachlorophenoxy, R.sub.3 is hydrogen, lower alkyl, lower alkoxy-lower alkyl, lower alkanoyloxy-lower alkyl, phenyl which is unsubstituted or monosubstituted by nitro or amino, or benzyl, and X.sub.1 denotes a triphenylphosphoranylidene or a tri-lower alkyl-phosphoranylidene radical.
Dependencies are inferred from the claim text.