1-dethia-2-thia-cephalosporanic acids
AssigneeRoussel Uclaf
InventorsGermain Costerousse, Solange Gouin d'Ambrieres, Jean-Georges Teutsch
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AssigneeRoussel Uclaf
InventorsGermain Costerousse, Solange Gouin d'Ambrieres, Jean-Georges Teutsch
Estimating the term…
1-dethia-2-thia-cephalosporanic acids of the formula ##STR1## wherein R is selected from the group consisting of ##STR2## R.sub.b --NH--and ##STR3## R.sub.a is an organic radical R.sub.i and R.sub.j are individually selected from the group consisting of hydrogen, aliphatic, aromatic and heterocycle or taken together with the nitrogen atom form an optionally substituted heterocycle, R.sub.b is optionally substituted carbocyclic or heterocyclic aryl, R.sub.1B is --[CH.dbd.CH].sub.n1 --CH.sub.2 --S--R.sub.m, n.sub.1 is 0, 1 or 2, Rm is an unsaturated radical including a positively charged and doubly bonded nitrogen atom and bonded to the sulfur atom through a carbon atom, R.sub.4 is hydrogen or methoxy, n.sub.2 is 0, 1 or 2 and A is selected from the group consisting of hydrogen, alkali metal ion, or alkaline earth metal ion, magnesium ion, ammonium ion, an organic amine base and an ester group or --COOA is --COO.sup.- and their non-toxic, pharmaceutically acceptable acid addition salts, having antibiotic activity.
A compound selected from the group consisting of 1-dethia-2-thia-cephalosporanic acids of the formula ##STR37## wherein R' is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl and alkynyl of 2 to 6 carbon atoms, and cycloalkyl of 3 to 6 carbon atoms substituted or unsubstituted with at least one member of the group consisting of halogen, carboxy, salified carboxy, esterified carboxy, alkoxy, oxo, alkylthio, mercapto, hydroxy, amino, nitro, carbamoyl and cyano, n.sub.2 is 0, 1 or 2, R.sub.4 is hydrogen or methoxy, R.sub.1B is --(CH.dbd.CH).sub.n1 --CH.sub.2 --S--R.sub.m, n.sub.1 is 0, 1 or 2, R.sub.m is an unsaturated group including a positively charged and double bonded nitrogen atom, the said group being bonded to the sulfur atom through a carbon atom and selected from the group consisting of pyridyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinoleinyl, isoquinoleinyl, cinnolinyl, quanazolinyl, pyridino pyrimidinyl, dihydro- or tetrahydro-pyridyl, unsubstituted or substituted by at least one member selected from the group of alkyl of 1 to 4 carbon atoms, methoxy, ethoxy, halogen, carboxyalkyl, esterified carboxyalkyl, carbamoyl, thioacetylalkyl, thiocarbamoylalkyl, haloalkyl, cyanoalkyl and alkenyl of 2 to 4 carbon atoms Y is methine or nitrogen and A is selected from the group consisting of hydrogen, alkali metal ion, or alkaline earth metal ion, magnesium ion, ammonium ion, an organic amine base and an ester group or --COOA is --COO.sup.- and their non-toxic, pharmaceutically acceptable acid addition salts.
A composition of 6 claim wherein the active compound is selected from group consisting of (6S) (7S) (Z) 4-[[[7-[(2-amino-4-thiazolyl)-[(difluoromethoxy)imino]-acetamido]-2-carbox y-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-en-3-yl]-methyl]-thio]-1-methyl pyridinium in the form of an internal salt and its non-toxic, pharmaceutically acceptable acid addition salts.
Dependencies are inferred from the claim text.