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US 5,627,203 AGranted
Tricyclic oxime ethers
AssigneeAdir et Compagnie
InventorsSylvain Rault, Max Robba, Jean-Charles Lancelot, Herv e Prunier, Pierre Renard, Bruno Pfeiffer, B eatrice Guardiola-Lemaitre, Marie-Claire Rettori
Life of this patent
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Abstract
The present invention relates to compounds of formula (I): ##STR1## wherein A, x, y, R.sub.1, R.sub.2 and R.sub.3 are as defined in the description. The compounds are useful for treating diseases requiring a selective serotonin reuptake site and 5-HT.sub.2c or 5-HT.sub.3 ligand.
Claims11
A compound selected from those of formula (I):
- ##STR140## wherein R.sub.1 is selected from:
- hydrogen,
- alkyl,
- alkenyl,
- cycloalkyl,
- cycloalkyl in which the alkyl chain is straight or branched and has 1 to 4 carbon atoms inclusive,
- hydroxy,
- alkoxy,
- unsubstituted or substituted phenyl,
- unsubstituted of substituted phenylalkyl in which the alkyl chain is straight or branched and has 1 to 4 carbon atoms inclusive,
- unsubstituted or substituted phenoxy, and
- unsubstituted or substituted phenylalkoxy in which the alkyl chain is straight or branched and has 1 to 4 carbon atoms inclusive,
- or R.sub.1 forms with R.sub.2 and the chain ##STR141## carrying them a nitrogen-containing ring system having 5 to 8 ring members inclusive,
- R.sub.2 and R.sub.3 are each selected, independently of the other, from:
- hydrogen,
- alkyl,
- alkenyl,
- cycloalkyl,
- unsubstituted or substituted indanyl,
- cycloalkylalkyl in which the alkyl chain is straight or branched and has 1 to 4 carbon atoms inclusive,
- unsubstituted or substituted phenyl, and
- unsubstituted or substituted phenylalkyl in which the alkyl chain is straight or branched and has 1 to 4 carbon atoms inclusive,
- or R.sub.2 and R.sub.3 form together with the nitrogen atom carrying them a heterocyclic system selected from:
- ##STR142## wherein:
- m is 0, 1, 2, 3, or 4,
- n is 0, 1, or 2,
- Y' is selected from oxygen, sulfur and ##STR143## R.sub.4 being selected from:
- hydrogen,
- alkyl, and
- unsubstituted or substituted --(CH.sub.2).sub..sigma. -phenyl, wherein .sigma. is 0, 1, 2, 3, or 4,
- x and y are identical or different and are 0, 1, 2, 3, or 4,
- A represents:
- a group of formula (.alpha.):
- ##STR144## and thus forms with the heterocyclic system carrying it a thieno[2,3-d]pyrrolo[1,2-a]pyrrole of the formula (I.sub..alpha.):
- ##STR145## wherein R.sub.1, R.sub.2, R.sub.3, x, and y are as defined hereinbefore and R.sub.5 and R.sub.6, which are identical or different, each represents, independently of the other, a group selected from:
- hydrogen,
- alkyl,
- hydroxy,
- alkoxy,
- halogen,
- trifluoromethyl,
- alkoxycarbonyl,
- unsubstituted or substituted --(CH.sub.2).sub.p -phenyl wherein p is 0, 1, 2, 3, or 4, and
- unsubstituted or substituted --O--(CH.sub.2).sub.p' -phenyl wherein p' is 0, 1, 2, 3, or 4,
- a group of formula (.beta.):
- ##STR146## and thus forms with the heterocyclic system carrying it a thieno[3,2-d]pyrrolo[1,2-a]pyrrole of the formula (I.sub..beta.):
- ##STR147## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.5, R.sub.6, x and y are as defined hereinbefore,
- a group of formula (.gamma.):
- ##STR148## and thus forms with the heterocyclic system carrying it a pyrrolo[1,2-a]indole of the formula (I.gamma.):
- ##STR149## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.5, R.sub.6, x and y are as defined hereinbefore,
- their cis or trans isomers in respect of the oxime ether,
- their enantiomers or diastereoisomers, and
- their hydrates and/or pharmaceutically-acceptable addition salts with an acid or a base,
- it being understood, unless specified otherwise, that:
- the terms "alkyl" and "alkoxy" represent a straight-chain or branched group having 1 to 6 carbon atoms inclusive,
- the term "alkenyl" represents a straight-chain or branched unsaturated group having 2 to 6 carbon atoms inclusive,
- the term "cycloalkyl" represents a carbon ring system having 3 to 8 ring members inclusive,
- the expressions "substituted indanyl", "substituted phenyl", "substituted phenoxy", "substituted phenylalkyl", "substituted --(CH.sub.2).sub..sigma. -phenyl", "substituted --(CH.sub.2).sub.p -phenyl", substituted "--O--(CH.sub.2).sub.p' -phenyl" and "substituted phenylalkoxy" denote that the phenyl radical is substituted by one or more identical or different substituents selected from alkyl, alkoxy, hydroxy, halogen, trifluoromethyl, nitrile and nitro.
55 more elements
Dependencies are inferred from the claim text.