Pyrazole derivatives, method of preparing them and pharmaceutical compositions in which they are present
AssigneeSanofi
InventorsFrancis Barth, Pierre Casellas, Christian Congy, Serge Martinez, Murielle Rinaldi, Gilles Anne-Archard
Life of this patent
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Abstract
The present invention relates to compounds of the formula: ##STR1## These compounds are useful in pharmaceuticals in which cannabis is known to be involved.
Claims30
A compound of the formula ##STR317## in which g.sub.2, g.sub.3, g.sub.4, g.sub.5 and g.sub.6 and w.sub.2, w.sub.3, w.sub.4, w.sub.5 and w.sub.6 are identical or different and are independently hydrogen, a chlorine or bromine atom, a (C.sub.1 -C.sub.3)-alkyl, a (C.sub.1 -C.sub.3)-alkoxy, a trifluoromethyl or a nitro group and g.sub.4 is optionally a phenyl group;
- R.sub.4 is hydrogen or a (C.sub.1 -C.sub.3)-alkyl;
- X is either a direct bond or a group --(CH.sub.2).sub.x --N(R.sub.3)--, in which R.sub.3 is hydrogen or a (C.sub.1 -C.sub.3)-alkyl and x is zero or one;
- and,
- R is
- a group --NR.sub.1 R.sub.2 in which R.sub.1 and R.sub.2 are independently a (C.sub.1 -C.sub.6)-alkyl;
- an optionally-substituted non-aromatic (C.sub.3 -C.sub.15) carbocyclic radical;
- an amino (C.sub.1 -C.sub.4) alkyl group in which the amino is optionally disubstituted by a (C.sub.1 -C.sub.3)-alkyl;
- a cycloalkyl-(C.sub.1 -C.sub.3) alkyl in which the cycloalkyl is C.sub.3 -C.sub.12 ;
- a phenyl which is unsubstituted or monosubstituted or polysubstituted by a halogen, by a (C.sub.1 -C.sub.5)-alkyl or by a (C.sub.1 -C.sub.5)-alkoxy;
- a phenyl (C.sub.1 -C.sub.3)-alkyl;
- a diphenyl-(C.sub.1 -C.sub.3)-alkyl;
- a naphthyl;
- an anthracenyl;
- a saturated 5- to 8-membered heterocyclic radical which is unsubstituted or substituted by a (C.sub.1 -C.sub.3)- alkyl, by a hydroxyl or by a benzyl group;
- a 1-adamantylmethyl;
- an aromatic heterocycle unsubstituted, mono- or polysubstituted by a halogen, a (C.sub.1 -C.sub.5)-alkyl, a (C.sub.1 -C.sub.5)-alkoxy;
- a (C.sub.1 -C.sub.3)-alkyl substituted by an aromatic heterocycle unsubstituted or mono- or polysubstituted by a halogen, a (C.sub.1 -C.sub.5) alkyl, a (C.sub.1 -C.sub.5)-alkoxy, or else R.sub.1 is hydrogen and R.sub.2 is as defined above, or else R.sub.1 and R.sub.2, together with the nitrogen atom to which they are bonded,form a saturated 5- to 8-membered heterocyclic radical, said heterocyclic radical being other than morpholine when w.sub.2, w.sub.3, w.sub.4, w.sub.5 and w.sub.6 and g.sub.2, g.sub.3, g.sub.4, g.sub.5 and g.sub.6 are all hydrogen;
- a group R.sub.2 as defined above when X is --(CH.sub.2).sub.x N(R.sub.3)--;
- or
- a group R.sub.5 when X is a direct bond, R.sub.5 being a (C.sub.1 -C.sub.3)-alkyl;
- a (C.sub.3 -C.sub.12)-cycloalkyl which is unsubstituted or substituted by a (C.sub.1 -C.sub.5)-alkyl;
- a phenyl-(C.sub.1 -C.sub.3)-alkyl which is unsubstituted or substituted by a halogen or by a (C.sub.1 -C.sub.5)-alkyl;
- a cycloalkyl-(C.sub.1 -C.sub.3)-alkyl in which the cycloalkyl is C.sub.3 -C.sub.12 and is unsubstituted or substituted by a (C.sub.1 -C.sub.5)-alkyl;
- or a 2-norbornylmethyl;
- or one of its salts.
A compound which is N-piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-pyrazole-3 -carboxamide, or one of its salts or solvates thereof.
A pharmaceutical composition according to claim 29 which is in the form of a dosage unit.
Dependencies are inferred from the claim text.