Sanofi

Sanofi-aventis

Sanofi-synthelabo

Elf Sanofi

Societe Anonyme Sanofi

Murielle Rinaldi

Francis Barth

Christian Congy

Serge Martinez

Pierre Casellas

Didier Oustric

Patrick Gueule

Bernard Labeeuw

Joseph Millan

Malcolm R Bell

Thomas E D'Ambra

Claude Vernhet

Gilles Anne-Archard

Richard E Philion

Philippe Camus

Carole Guillaumont

Martine Vernhet

Martine Sarran

Fabienne Vasse

The subject of the invention is tricyclic derivatives of pyrazolecarboxylic acid of formula: in which Rrepresents a C-Ccarboxyl radical or an NRRgroup. The invention also relates to the method for preparing the compounds of formula (I), pharmaceutical compositions containing them. The compounds of formula (I) are active on cannabinoid CBreceptors.

Pyrazolecarboxylic acid tricyclic derivatives, preparation and pharmaceutical compositions containing same

A subject-matter of the present invention is compounds of formula:and their preparation and the pharmaceutical compositions comprising them. These compounds are agonists for CBcannabinoid receptors.

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Tricyclic derivatives of 1-benzylpyrazole-3-carboxylic acidwhich are antagonists of the cannabinoid CBreceptors; their method of preparation and pharmaceutical compositions containing them.

1-benzylpyrazole-3-carboxylic acid tricyclic derivatives as cannabinoid receptor antagonists

The subject of the invention is tricyclic derivatives of pyrazolecarboxylic acid of formula:in which Rrepresents a C-Ccarboxyl radical or an NRRgroup. The invention also relates to the method for preparing the compounds of formula (I), pharmaceutical compositions containing them. The compounds of formula (I) are active on cannabinoid CBreceptors.

N-Piperidino-5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazole-3-carboxamide and its salts and solvates are powerful antagonists of the CB cannabinoid receptors. They are prepared by reacting a functional derivative of 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethylpyrazole-3-carboxylic acid with 1-aminopiperidine, optionally followed by salification.

Pyrazolecarboxylic acid derivatives, their preparation, pharmaceutical compositions containing them

Pyrazole derivatives, method for preparing same, and pharmaceutical

The use of human CB.sub.2 receptor-specific agonists of formula (I) or (I') for preparing immunomodulating drugs is disclosed. In formulae (I) and (I'), R.sub.1 is a group selected from --CH.sub.2 CHR.sub.10 NR.sub.6 R.sub.11, --(CH.sub.2).sub.2 NR'.sub.6 R'.sub.11, --CHR.sub.9 CH.sub.2 NR'.sub.6 R'.sub.11, --(CH.sub.2).sub.n Z and --COR.sub.8 ; R'.sub.1 is a --CH.sub.2 CHR.sub.10 NR.sub.6 R.sub.11 or --(CH.sub.2).sub.2 NR'.sub.6 R'.sub.11 group; R.sub.2 and R'.sub.2 are hydrogen, halogen or C.sub.1-4 alkyl; R.sub.3 is hydrogen, C.sub.1-4 alkyl or a group selected from --CH.sub.2 CHR.sub.10 NR.sub.6 R.sub.11, --(CH.sub.2).sub.2 NR'.sub.6 R'.sub.11 and --COR.sub.8 ; R'.sub.3 is a .dbd.CR.sub.6 R.sub.8 group; R.sub.4 has one of the meanings given for R.sub.5 or is a --COR.sub.8 group; R.sub.5 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, a halogen atom, a CF.sub.3 group, an OCF.sub.3 group or C.sub.1-4 alkylthio; R'.sub.5 has one of the meanings given for R.sub.5 and is in the 5 or 6 position of the indene ring; R.sub.6 is hydrogen or C.sub.1-4 alkyl; R'.sub.6 is C.sub.1-4 alkyl; R.sub.7 has one of the meanings given for R.sub.5 or R.sub.7 and R.sub.9 together form a --Y--CH.sub.2 -- group attached to the indole ring in the 7 position by a group Y; R.sub.8 is phenyl substituted one to four times by a substituent selected from halogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; a polycyclic ring selected from naphth-1-yl, naphth-2-yl, 1,2,3,4-tetrahydronaphth-1-yl, 1,2,3,4-tetrahydronaphth-5-yl, anthryl, benzofuryl, benzothien-2-yl, benzothien-3-yl, 2-, 3-, 4- or 8-quinolyl, said polycyclic rings optionally being substituted once or twice by a substituent selected from C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, halogen, cyano, hydroxyl, trifluoromethyl and imidazol-1-yl; R.sub.10 and R.sub.11 together are a group selected from --CH.sub.2 --O--CH.sub.2 --CR.sub.12 R.sub.13 -- and --(CH.sub.2).sub.p --CR.sub.12 R.sub.13 --, wherein the carbon atom substituted by R.sub.12 and R.sub.13 is attached to the nitrogen atom; R'.sub.11 is C.sub.1-4 alkyl; or R'.sub.11 and R'.sub.6, taken together with the nitrogen atom to which they are attached, form a group selected from morpholin-4-yl, thiomorpholin-4-yl, piperidin-1-yl and pyrrolidin-1-yl; each of R.sub.12 and R.sub.13 is independently hydrogen or C.sub.1-4 alkyl; n is 2, 3, 4 or 5; p is 2 or 3; Z is a methyl group or a halogen atom; and Y is a methylene group or an oxygen atom.

CB.sub.2 Receptor agonist compounds

3-pyrazolecarboxamide derivatives having cannabinoid receptor affinity

The present invention relates to compounds of the formula: ##STR1## These compounds are useful in pharmaceuticals in which cannabis is known to be involved.

Pyrazole derivatives, method of preparing them and pharmaceutical

The present invention relates to novel pyrazole-3-carboxamide derivatives of the formula ##STR1## in which the substituents are as defined in the specification. The present invention further relates to a process for the preparation of these novel derivatives and to the pharmaceutical compositions in which they are present.

Pyrazole-3-carboxamide derivatives, process for their preparation and

The invention relates to new propenone oxime ethers, a method of preparing them and pharmaceutical compositions containing them. Said new propenone oxime ethers have the formula ##STR1## in which Ar and Ar' each independently denotes a phenyl group non-substituted, mono or polysubstituted, a 9-anthryl group or a naphthyl group, a pyridyl, thienyl or furyl group;

Intermediates useful in preparing propenone oxime ethers

The invention relates to new propenone oxime ethers, a method of preparing them and pharmaceutical compositions containing them. Said new propenone oxime ethers have the formula ##STR1## in which--Ar and Ar' each independentlyl denotes a phenyl group non-substituted, mono or polysubstituted, a 9-anthryl group or a naphthyl group, a pyridyl, thienyl or furyl group;

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Saint Georges d'Orques, France

Murielle Rinaldi