Pyrrolidine and thiazolidine derivatives, their preparation and

Details Pyrrolidine and thiazolidine derivatives, their preparation and Pyrrolidine and thiazolidine derivatives, their preparation and

1995-06-07

1997-06-10

Gerstl, Robert

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

548200, C07D22710, A61K 3140

Patent

active

056376022

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION OF THE INVENTION

The present invention relates to derivatives of formula: ##STR2## their salts, their preparation and the medications containing them.
In formula (I), sulphur atom, R.sub.1 denotes a pyridyl radical optionally substituted by one or more alkyl radicals, furyl optionally substituted by one or more alkyl radicals, thienyl optionally substituted by one or more alkyl radicals, quinolyl optionally substituted by one or more alkyl radicals, naphthyl optionally substituted by one or more alkyl radicals, indolyl optionally substituted by one or more alkyl radicals or phenyl optionally substituted by one or more substituents chosen from halogen atoms and alkyl, alkoxy, hydroxyl, nitro, amino, monoalkylamino, dialkylamino, alkoxycarbonyl, --CO--NR.sub.7 R.sub.8, --NH--CO--CH.sub.3, trifluoromethyl or trifluoromethoxy radicals, and R.sub.5 denotes a hydrogen atom, R.sub.5 denotes a phenyl radical, hydrogen atom, cycloalkylalkoxycarbonyl, --CONR.sub.9 R.sub.10 or phenyl radical optionally substituted by one or more substituents chosen from alkyl, alkoxy or hydroxyl radicals, substituted by one or more substituents chosen from the radicals -alk-SO.sub.2 H, --SO.sub.2 --NH--CO--R.sub.11, --B(OH).sub.2, --SO.sub.2 --NH--SO.sub.2 --R.sub.11, --CO--NH--CO--R.sub.11, --CO--NH--SO.sub.2 --R.sub.11, --C(NH.sub.2).dbd.NOH, --SO.sub.2 --NH--R.sub.12, --CO--NH--R.sub.12, ##STR3## and optionally by one or more substituents chosen from halogen atoms and alkyl, alkoxy, alkylthio, trifluoromethyl, carboxyl, alkoxycarbonyl, hydroxyl, nitro, amino, acyl, cyano, sulphamoyl, carbamoyl, hydroxyiminoalkyl, alkoxyiminoalkyl, hydroxyaminocarbonyl, alkoxyaminocarbonyl, 5-tetrazolyl, 5-tetrazolylalkyl, trifluoromethylsulphonamido, alkylsulphinyl, mono- or polyhydroxyalkyl, sulpho, -alk-O--CO-alk, -alk-COOX, -alk-O-alk, -alk'-COOX, --O-alk-COOX, --CH.dbd.CH--COOX, --CO--COOX, -alk-SO.sub.3 H (in salt form), --CH.dbd.CH-alk', --C(.dbd.NOH)--COOX, --S-alk-COOX, --SO-alk-COOX, --SO.sub.2 -alk-COOX, --O--CH.sub.2 -alk'-COOX, --CX.dbd.N--O-alk-COOX, -alk-N(OH)--CO-alk or 2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl radicals, optionally substituted by one or more substituents chosen from halogen atoms and alkyl, alkoxy and alkylthio radicals, substituted by one or more substituents chosen from halogen atoms and alkyl, alkoxy and alkylthio radicals, are attached form a saturated or unsaturated mono- or polycyclic heterocyclic ring containing 4 to 9 carbon atoms and one or more heteroatoms (O, N) and optionally substituted by one or more alkyl radicals, phenylalkyl or phenyl radical optionally substituted by one or more substituents chosen from halogen atoms and alkyl, alkoxy and alkylthio radicals, phenyl radical optionally substituted by one or more substituents chosen from halogen atoms and alkyl, alkoxy and alkylthio radicals, are attached form a saturated or unsaturated mono- or polycyclic heterocyclic ring containing 4 to 9 carbon atoms and one or more heteroatoms (O, N, S) and optionally substituted by one or more alkyl radicals, optionally substituted by one or more substituents chosen from cyano, alkoxy, nitro and amino radicals and halogen atoms, radical.
In the above definitions and those which will be cited below, unless stated otherwise, the alkyl, alkylene and alkoxy radicals and the alkyl, alkylene and alkoxy parts contain 1 to 4 carbon atoms as a straight or branched chain, the acyl radicals or parts contain 2 to 4 carbon atoms and the cycloalkyl radicals and parts contain 3 to 6 carbon atoms.
When R.sub.7 and R.sub.8 with the nitrogen atom to which they are attached form a heterocyclic ring, the latter is preferably a piperidino ring optionally substituted by one or more alkyl radicals or a 1,2,3,4-tetrahydroquinoline ring.
When R.sub.9 and R.sub.10 with the nitrogen atom to which they are attached form a heterocyclic ring, the latter is preferably a piperidino, 1-perhydroazepinyl, 1,2,3,6-tetrahydro-1-pyridyl, 1,2,3,4-tetrahydro-1-quinolyl, 1-pyrrolidinyl, 1,2,3,4-tetrahydro-2-isoquinolyl, thiomorpholino or 1-in

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