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US 5,846,980 AGranted
N-(benzhydryloxyalkyl)-4-(carboxy/carbamoyl methyl)-piperidine derivatives as antidepressants
AssigneeCooperation Pharmaceutique Francaise
InventorsYoussef El Ahmad, Pierre-Yves Fiez-Vandal, Elisabeth Laurent, Philippe Maillet, Roland Ollivier
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Abstract
The invention relates to substituted nitrogenous heterocycles derivatives of general formula (I) ##STR1## in the racemic or optically pure form and/or in the form of cis/trans isomers, their pharmaceutically acceptable salts, and their use for preparing drugs having psychrotropic activity, especially antidepressant activity.
Claims14
Substituted nitrogenous heterocycle compounds of formula (I) ##STR27## in which:
- R.sup.1 and R.sup.2 which are identical or different, represent a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.6 alkoxy group or a trifluoromethyl group,
- m is an integer between 0 and 2,
- A is a C.sub.2 -C.sub.8 alkylene chain or a C.sub.2 -C.sub.8 alkenylene chain,
- the heterocyclic unit of general formula Q:
- ##STR28## in which R.sup.9 represents
- a unit --OZ.sub.1 in which Z.sub.1 represents hydrogen, a C.sub.1 -C.sub.12 alkyl, a C.sub.3 -C.sub.7 cycloalkyl, a C.sub.1 -C.sub.12 alkyl which is substituted by one or a plurality of optionally esterified alcohol functional groups or a C.sub.1 -C.sub.12 alkyl substituted by an --N(RaRb) group in which Ra and Rb, independently of one another, represent hydrogen or a C.sub.1 -C.sub.4 alkyl group or alternatively Ra and Rb, together with the nitrogen atom to which they are bonded, form a 5- to 7-membered heterocycle optionally containing a second heteroatom,
- a unit --OM in which M is an alkali metal, alkaline earth metal or ammonium cation,
- a unit --N(Z.sub.2 Z.sub.3) in which Z.sub.2 and Z.sub.3, independently of one another, represent a hydrogen atom, a C.sub.1 -C.sub.12 alkyl, a C.sub.3 -C.sub.7 cycloalkyl, a C.sub.1 -C.sub.12 alkyl substituted by an --N(RaRb) group in which Ra and Rb are as defined above or a C.sub.1 -C.sub.12 alkyl substituted by one or a plurality of optionally esterified alcohol functional groups or alternatively Z.sub.2 and Z.sub.3, together with the nitrogen atom to which they are bonded, form a 5- to 7-membered heterocycle optionally containing a second heteroatom,
- represents one of the groups Q.sup.1 or Q.sup.2 defined below:
- Q.sup.1 when R.sup.7 and R.sup.8 are hydrogen atoms, ##STR29## Q.sup.2 when R.sup.7 and R.sup.8 form a double bond, ##STR30## and R.sup.3, R.sup.4, R.sup.5 and R.sup.6, are identical or different, represent a hydrogen atom or a C.sub.1 -C.sub.8, alkyl, or alternatively the pairs of radicals R.sup.3 -R.sup.4, R.sup.5 -R.sup.6 and R.sup.3 -R.sup.5 form a 5- to 7-membered ring or heterocycle, provided that:
- when m is 1, A is --(CH.sub.2).sub.2 -, R.sup.9 can not be OH, OC.sub.1-6 alkyl or OM;
- when m is 1, A is --(CH.sub.2).sub.3 -, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 can not all be hydrogen;
- in a racemic or optically pure form and/or in the form of cis/trans isomers, and their pharmaceutically acceptable salts.
10 more elements
A method for treatment of humans for depression comprising administering a theraputically amount of a substituted nitrogenous heterocycle compound of formula (I) ##STR31## in which:
- R.sup.1 and R.sup.2 which are identical or different, represent a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group a C.sub.1 -C.sub.6 alkoxy group or a trifluoromethyl group,
- m is an integer between 0 and 2,
- A is a C.sub.2 -C.sub.8 alkylene chain or a C.sub.2 -C.sub.8 alkenylene chain,
- the heterocyclic unit of general formula Q:
- ##STR32## in which R.sup.9 represents
- a unit --OZ.sub.1 in which Z.sub.1 represents hydrogen, a C.sub.1 -C.sub.12 alkyl, a C.sub.3 -C.sub.7 cycloalkyl, a C.sub.1 -C.sub.12 alkyl which is substituted by one or a plurality of optionally esterified alcohol functional groups or a C.sub.1 -C.sub.12 alkyl substituted by an --N(RaRb) group in which Ra. and Rb, independently of one another, represent hydrogen or a C.sub.1 -C.sub.4 alkyl group or alternatively Ra and Rb, together with the nitrogen atom to which they are bonded, form a 5- to 7-membered heterocycle optionally containing a second heteroatom,
- a unit --OM in which M is an alkali metal, alkalinre earth metal or ammonium cation,
- a unit --N(Z.sub.2 Z.sub.3) in which Z.sub.2 and Z.sub.3, independently of one another, represent a hydrogen atom, a C.sub.1 -C.sub.12 alkyl, a C.sub.3 -C.sub.7 cycloalkyl, a C.sub.1 -C.sub.12 alkyl substituted by an --N(RaRb) group in which Ra and Rb are as defined above or a C.sub.1 -C.sub.12 alkyl substituted by one or a plurality of optionally esterified alcohol functional groups or alternatively Z.sub.2 and Z.sub.3, together with the nitrogen atom to which they are bonded, form a 5- to 7-membered heterocycle optionally containing a second heteroatom,
- represents one of the groups Q.sup.1 or Q.sup.2 defined below:
- Q.sup.1 when R.sup.7 and R.sup.8 are hydrogen atoms, ##STR33## Q.sup.2 when R.sup.7 and R.sup.8 form a double bond, ##STR34## and R.sup.3, R.sup.4, R.sup.5 and R.sup.6, are identical or different, and represent a hydrogen atom or a C.sub.1 -C.sub.8 alkyl, or alternatively, the pairs of radicals R.sup.3 -R.sup.4, R.sup.5 -R.sup.6 and R.sup.3 -R.sup.5 form a 5- to 7-membered ring or heterocycle, with the proviso that, when m is 1, A is --(CH.sub.2).sub.2 -, R.sup.9 can not be OH, OC.sub.1-6 alkyl or OM;
- when m is 1, A is --(CH.sub.2).sub.3 -, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 can not all be hydrogen;
- in racemic or optically pure form and/or in the form of cis/trans isomers.
9 more elements
Dependencies are inferred from the claim text.