Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-04-06
1996-10-08
Bond, Robert T.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
540509, A61K 3155, C07D24324
Patent
active
055631363
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION OF THE INVENTION
The present invention relates to derivatives of formula: ##STR3## their salts, their preparation and medicaments containing them.
In the formula (I) alkylthio, nitro, hydroxyl or cyano radical, in which R.sub.5 represents a hydrogen atom or an alkyl, alkoxycarbonyl or phenyl radical which is optionally substituted (by one or more substituents chosen from amongst halogen atoms and alkyl, alkoxy, alkylthio and nitro radicals) and R.sub.6 represents an alkoxy radical, a cycloalkoxy radical which is optionally substituted (by at least one alkyl radical), a cycloalkylalkoxy, phenylalkoxy, polyfluoroalkoxy or cinnamyloxy radical or an --NR.sub.7 R.sub.8 radical in which R.sub.7 and R.sub.8, which are identical or different, represent a hydrogen atom or an alkyl radical, a phenyl radical which is optionally substituted (by one or more substituents chosen from amongst halogen atoms and alkyl, alkoxy and alkylthio radicals), or a cycloalkylalkyl, cycloalkyl, indanyl or phenylalkyl radical or else R.sub.7 and R.sub.8, together with the nitrogen atom to which they are attached, form a saturated or unsaturated monocyclic or polycyclic heterocycle containing 4 to 9 carbon atoms and one or more hetero atoms (O, S, N) and optionally substituted by one or more alkyl, alkoxy, alkoxycarbonyl, dialkylcarbamoyl or phenyl radicals or by spiromonocyclic cyclic system formed by combination of an atom of the heterocycle with 4 to 5 other carbon atoms, one or more of the latter optionally being replaced by hetero atoms (O, S, N), substituents chosen from amongst -alk-SO.sub.3 H, -alk-PO.sub.3 H.sub.2, --CH.dbd.NOH, --CH.dbd.NO-alk-COOX, --S-alk-COOX, -SO-alk-COOX, --SO.sub.2 -alk-COOX, --CH.dbd.CH--COOX, -alk-CO--NHOH, --C(.dbd.NOH)--COOX, -alk-N(OH)--CO-alk, -alk-SO.sub.2 H, --CH.dbd.CH--SO.sub.3 H, --C(COOX).dbd.N--O-alk-COOX and tetrazolylalkyl radicals or a group of formula: ##STR4## or (b) a cyclic system of formula: ##STR5## in which R.sub.9 represents an .dbd.NOX, .dbd.NO-alk-COOX, .dbd.CH--COOX, -alk-COOX, -alk-SO.sub.2 H or -alk-SO.sub.3 H radical, R.sub.10 represents an oxygen or sulphur atom or a methylene or alkylimino radical and R.sub.11 represents a methylene or ethylene radical, substituted by one or more substituents chosen from amongst halogen atoms and alkyl, alkoxy, hydroxyl, carboxyl, nitro and --CO--NR.sub.6 radicals,
In the above definitions and those which will be mentioned below, unless stated otherwise the alkyl, alkylene and alkoxy radicals and the alkyl, alkylene and alkoxy portions contain 1 to 4 carbon atoms in a straight or branched chain, and the cycloalkyl radicals and portions contain 3 to 12 carbon atoms.
When R.sub.7 and R.sub.8, together with the nitrogen atom to which they are attached, form a heterocycle, 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, morpholino, thiomorpholino or 1-indolyl cyclic system, it being possible for these cyclic systems to be optionally substituted by one or more alkyl radicals.
The compounds of formula (I) comprise one or more asymmetric centers which give isomeric forms. The racemates and the enantiomers of these compounds are likewise a part of the invention.
The compounds of formula (I) can be prepared by reaction of a reactive derivative of carbamic acid, optionally obtained in situ by the action of a reactive derivative of carbonic acid chosen from amongst N,N'carbonyldiimidazole, phosgene, trichloromethyl chloroformate, bis(trichloromethyl) carbonate and p-nitrophenyl chloroformate on a derivative of formula: ##STR6## in which R.sub.1, R.sub.2 and R.sub.4 have the same meanings as in the formula (I), with a derivative of formula: R.sub.3 comprises a COOH, PO.sub.3 H.sub.2, SO.sub.2 H or SO.sub.3 H radical, a salt of such a compound.
This reaction is preferably carried out in an inert solvent such as tetrahydrofuran, dimethylformamide, a chlorinated solvent (chloroform or 1,2-dichloroethane, for example) or a
Capet Marc
Cotrel Claude
Dubroeuco Marie-Christine
Guyon Claude
Martin Jean-Paul
Bond Robert T.
Rhone-Poulenc Rorer S.A.
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