Thiazolidine derivatives, their preparation and the medicaments

Details Thiazolidine derivatives, their preparation and the medicaments Thiazolidine derivatives, their preparation and the medicaments

1996-12-19

1997-11-11

Gerstl, Robert

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548200, C07K 5062

Patent

active

056866224

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to thiazolidine derivatives of formula: ##STR2## to their salts, to their preparation and to the medicaments containing them.
In formula (I), --(CH.sub.2).sub.n --CONRbRc, substituents chosen from halogen atoms and alkyl, alkoxy, hydroxyl, nitro, amino, monoalkylamino, dialkylamino, alkoxycarbonyl, trifluoromethyl and trifluoromethoxy radicals, 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, --alk--SO.sub.2 H, --SO.sub.2 --NH--CO--Rg, --SO.sub.2 --NH--SO.sub.2 --Rg, --CO--NH--CO--Rg, --CO--NH--SO.sub.2 --Rg, --B(OH).sub.2, --C(NH.sub.2).dbd.NOH, --SO.sub.2 --NH--Rh, --CO--NH--Rh, ##STR3## and 2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl radicals, Ra represents a hydrogen atom or an alkyl radical, which the phenyl ring is optionally substituted with one or more substituents chosen from halogen atoms and alkyl, alkoxy and alkylthio radicals or a phenyl radical optionally substituted with one or more substituents chosen from halogen atoms and alkyl, alkoxy and alkylthio radicals, or alternatively Rb and Rc form, with the nitrogen atom to which they are attached, a saturated or unsaturated mono- or polycyclic heterocycle containing 4 to 9 carbon atoms and one or more hetero atoms chosen from oxygen, nitrogen and sulphur and optionally substituted with one or more alkyl radicals, attached, a saturated or unsaturated mono- or polycyclic heterocycle containing 4 to 9 carbon atoms and one or more hetero atoms chosen from oxygen, nitrogen and sulphur and optionally substituted with one or more alkyl radicals, radical optionally substituted with one or more substituents chosen from cyano, alkoxy, nitro and amino radicals and halogen atoms, alkoxyalkylene radical.
In the above definitions or in those which will be mentioned below, except where otherwise mentioned, the alkyl, alkylene and alkoxy radicals and portions contain 1 to 4 carbon atoms in a straight or branched chain and the cycloalkyl radicals or portions contain 3 to 6 carbon atoms.
The compounds of formula (I) have isomeric forms. These isomers also form part of the invention.
When Rb and Rc or Re and Rf form, with the nitrogen atom to which they are attached, a saturated or unsaturated mono- or polycyclic heterocycle containing 4 to 9 carbon atoms and one or more hetero atoms chosen from oxygen, nitrogen and sulphur and optionally substituted with one or more alkyl radicals, this heterocycle is preferably a morpholinyl or thiomorpholinyl residue, a piperidyl residue optionally substituted with one or more alkyl radicals, or a pyrrolidinyl, 1,2,3,4-tetrahydroquinolyl or N-alkylpiperazinyl residue.
The compounds of formula (I) for which R.sub.1 represents a radical --(CH.sub.2)n--COORa, n is equal to 0 or 1, Ra represents an alkyl radical and R.sub.5 represents a phenyl radical optionally substituted with one or more substituents chosen from halogen atoms and alkyl, alkoxy, alkylthio, trifluoromethyl, alkoxycarbonyl, nitro, acyl, cyano, sulphamoyl, carbamoyl, alkoxyiminoalkyl, alkoxyaminocarbonyl, trifluoromethylsulphonamido, --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', --S--alk--COOX, --SO--alk--COOX, --SO.sub.2 --alk--COOX, --O--CH.sub.2 --alk'--COOX or --CX.dbd.N--O--alk--COOX radicals in which X is an alkyl or phenylalkyl radical may be prepared by the action of a derivative of formula: ##STR4##

REFERENCES:
Derwent Abstract of EP A 0527069. (1992).

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