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US 5,686,622 AGranted
Thiazolidine derivatives, their preparation and the medicaments containing the same
AssigneeRhone-Poulenc Rorer S.A.
InventorsMarc Capet, Marie-Christine Dubroeucq, Claude Guyon, Franco Manfre
Life of this patent
Estimating the term…
Abstract
Thiazolidine derivatives of formula (I), in which R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined in the specification. The invention also concerns the salts of these derivatives, the preparation thereof and drugs containing same. ##STR1##
Claims12
A compound of formula (I):
- ##STR19## in which:
- R.sub.1 represents a --(CH.sub.2).sub.n --COORa or --(CH.sub.2).sub.n --CONRbRc radical;
- R.sub.2 represents a phenyl radical which may be substituted with one or more substituents selected from halogen atoms and alkyl, alkoxy, hydroxyl, nitro, amino, monoalkylamino, dialkylamino, alkoxycarbonyl, trifluoromethyl and trifluoromethoxy radicals;
- R.sub.3 represents a --COORd or --CONReRf radical;
- R.sub.4 represents a hydrogen atom or an alkyl radical;
- R.sub.5 represents a phenyl radical which may be substituted with one or more substituents selected 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, ##STR20## and 2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl radicals;
- Ra represents a hydrogen atom or an alkyl radical;
- Rb represents a hydrogen atom or an alkyl radical;
- Rc represents an alkyl or 5-tetrazolyl radical, a phenylalkyl radical in which the phenyl ring may be substituted with one or more substituents selected from halogen atoms and alkyl, alkoxy and alkylthio radicals or a phenyl radical which may be substituted with one or more substituents selected from halogen atoms and alkyl, alkoxy and alkylthio radicals;
- or Rb and Rc form, together 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 selected from oxygen, nitrogen and sulphur, and which may be substituted with one or more alkyl radicals;
- Rd represents an alkyl radical;
- Re represents a hydrogen atom or an alkyl radical;
- Rf represents an alkyl, cycloalkyl or cycloalkylalkyl radical;
- or Re and Rf form, together 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 selected from oxygen, nitrogen and sulphur, and which may be substituted with one or more alkyl radicals;
- Rg represents an alkyl, cycloalkyl or trifluoromethyl radical, or a phenyl radical which may be substituted with one or more substituents selected from cyano, alkoxy, nitro and amino radicals and halogen atoms;
- Rh represents a 5-tetrazolyl radical;
- Ri represents C.dbd.O or S.dbd.O;
- Rj represents O or C.dbd.O;
- n is equal to 0 or 1;
- X represents a hydrogen atom or an alkyl or phenylalkyl radical;
- alk represents an alkyl or alkylene radical;
- alk' represents a hydroxyalkyl, hydroxyalkylene, alkoxyalkyl or alkoxyalkylene radical;
- it being understood that the alkyl, alkylene and alkoxy radicals and portions of radicals contain 1 to 4 carbon atoms in a straight or branched chain and the cycloalkyl radicals or portions of radicals contain 3 to 6 carbon atoms;
- an isomer of a compound of formula (I) or a salt of a compound of formula (I).
21 more elements
A compound selected from:
- tert-butyl (2S,4S,5R)-5-methoxycarbonyl-3-{2-3-(3-methylphenyl)ureido!acetyl}-4-phen yl-2-thiazolidinecarboxylate,
- 3-{3-2-((2S,4S,5R)-2-tert-butoxycarbonyl-5-carboxy-4-phenyl-3-thiazolidiny l)-2-oxoethyl!ureido}phenylacetic acid,
- (S)-2-{3-{3-2-((2S,4S,5R)-2-tert-butoxycarbonyl-5-carboxy-4-phenyl-3-thiaz olidinyl)-2-oxoethyl!ureido}phenyl}propionic acid,
- tert-butyl (2S,4S,5R)-5-methoxycarbonyl-3-{2-3-(3-methylphenyl)ureido!-acetyl}-4-(2- fluorophenyl)-2-thiazolidinecarboxylate,
- (2S,4S,5R)-2-tert-butoxycarbonyl-3-{2-3-(3-methylphenyl)ureido!acetyl}-4-( 2-fluorophenyl)-5-thiazolidinecarboxylic acid, or a salt of one of said compounds.
2 more elements
Dependencies are inferred from the claim text.