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US 4,900,728 AGranted
Novel 3-amino-2-oxo-azetidine-1-sulfonic acids
AssigneeRoussel Uclaf
InventorsRene Heymes, Alain Bonnet
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AssigneeRoussel Uclaf
InventorsRene Heymes, Alain Bonnet
Estimating the term…
Novel syn isomers of racemates and optical isomers of 3-amino-2-oxo-azetidine-1-sulfonic acids of the formula ##STR1## wherein R is selected from the group consisting of hydrogen linear or branched optionally substituted alkyl of 1 to 12 carbon atoms and optionally substituted alkenyl and alkynyl of 2 to 12 carbon atoms, R.sub.1 is --(CH.sub.2).sub.n --X, n is an integer from 1 to 4, X is selected from the group consisting of halogen, --CN, --OR', --SR.sub.1 ", azido, thiocyanate, isothiocyanate, and ##STR2## is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R" is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and a heterocycle and R' and R" are individiually selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and taken together with the nitrogen to which they are attached form a heterocycle and A.sup.1 is selected from the group consisting of hydrogen, and metal cations and their nontoxic, pharmaceutically acceptable acid addition salts, the wavy line indicating the cis form, trans form or cis trans forms having antibiotic properties.
A compound selected from the group consisting of syn isomers of racemates and optical isomers of 3-amino-2-oxo-azetidine-1-sulfonic acids of the formula ##STR61## wherein R is selected from the group consisting of hydrogen, linear or branched optionally mono-substituted alkyl of 1 to 12 carbon atoms and optionally substituted alkenyl and alkynyl of 2 to 12 carbon atoms, said optional substituent being selected from the group consisting of carboxy, pharmaceutically acceptable salified carboxy, alkoxycarbonyl of 2 to 7 carbon atoms, carbamoyl, dimethylcarbamoyl, amino, methylamino, ethylamino, dimethylamino, diethylamino, halogen, alkoxy and alkylthio of 1 to 7 carbon atoms, aryl, arylthio, cyano, tetrazolyl, pyridinyl, tetrazolythio and thiadiazolythio, the latter 4 being optionally substituted with alkyl of 1 to 7 carbon atoms, R.sub.1 is --(CH.sub.2).sub.n --X, n is an integer from 1 to 4, X is fluorine, and A.sup.1 is selected from the group consisting of hydrogen and pharmaceutically acceptable metal cations and their non-toxic, pharmaceutically acceptable acid addition salts, the wavy line indicating the cis form, trans form or cis trans forms.
Dependencies are inferred from the claim text.