Ligand inhibitors of the RAR receptors, process for preparing same and therapeutic/cosmetic applications thereof

1. A biaryl compound having the structural formula:

wherein

R 13 is a hydroxyl, alkoxy, monoalkylamino or dialkylamino group;

R 14 is a hydrogen atom, a hydroxyl group or amino group;

and the para-position of the benzene ring bonded to the 1,2,3,4-tetrahydro-1,1,4,4-terramethylnaphthalene is optionally substituted with a linear or branched alkyl radical having from 1 to 6 carbon atoms, an alkoxy radical, a monoalkylamino radical, a dialkylamino radical or a halogen atom,

or a salt, isomer or mixture thereof.

2. The biaryl compound as defined by claim 1 , wherein the bond represented by the dashed line is a double bond.

3. The biaryl compound as defined by claim 1 , wherein the bond represented by the dashed line is a triple bond.

4. The biaryl compound as defined by claim 1 , wherein the para-position of the benzene ring bonded to the 1,2,3,4-tetrahydro-1,1,4,4-terramethylnaphthalene is optionally substituted with an alkyl, alkyl amino or alkyloxy group.

5. A salt of the biaryl compound (I) as defined by claim 1 .

6. An alkali or alkaline-earth or zinc or organic amine salt of the biaryl compound (I) as defined by claim 1 .

7. The biaryl compound as defined by claim 1 , containing at least one alkyl radical selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl and hexyl radicals.

8. The biaryl compound as defined by claim 1 , containing at least one fluorine, chlorine and/or bromine atom.

9. The biaryl compound as defined by claim 1 , containing at least one alkoxy radical selected from the group consisting of methoxy, ethoxy, propyloxy, isopropoxy, butoxy, tert-butoxy, pentoxy and hexyloxy radicals.

10. The biaryl compound as defined by claim 1 , selected from the group consisting of:

4-[3-Hydroxy-3-(5,5,8,8-tetramethyl-4-p-tolyl-5,6,7,8-tetrahydro-2-naphthyl)-1-propynyl]benzoic acid,

4-{3-[4-(4-tert-Butylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-hydroxy-1-propynyl}benzoic acid,

4-{(E)-3-[4-(4-tert-Butylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-oxopropenyl}benzoic acid,

4-[(E)-3-Oxo-3-(5,5,8,8-tetramethyl-4-p-tolyl-5,6,7,8-tetrahydro-2-naphthyl)propenyl]benzoic acid,

4-[(E)-3-Hydroxy-3-(5,5,8,8-tetramethyl-4-p-tolyl-5,6,7,8-tetrahydro-2-naphthyl)propenyl]benzoic acid;

4-{(E)-3-[4-(4-tert-Butylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-hydroxyprapenyl}-2-hydroxybenzoic acid,

4-{(E)-3-[4-(4-tert-Butylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-oxopropenyl}-2-hydroxybenzoic acid,

4-{3-[4-(4-tert-Butylphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-hydroxy-1-propynyl}-2-hydroxybenzoic acid,

2-Hydroxy-4-[(E)-3-hydroxy-3-(5,5,8,8-tetramethyl-4-p-tolyl-5,6,7,8-tetrahydro-2-naphthyl)propenyl]benzoic acid,

2-Hydroxy-4-[(E)-3-oxo-3-(5,5,8,8-tetramethyl-4-p-tolyl-5,6,7,8-tetrahydro-2-naphthyl)propenyl]benzoic acid,

2-Hydroxy-4-[3-hydroxy-3-(5,5,8,8-tetramethyl-4-p-tolyl-5,6,7,8-tetrahydro-2-naphthyl)-1-propynyl]benzoic acid,

4-{(E)-3-[4-(4-Dimethylaminophenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-hydroxypropenyt}benzoic acid,

4-{(E)-3-[4-(4-Dimethylaminophenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-oxopropenyl}benzoic acid,

4-{3-[4-(4-Dimethylaminophenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-hydroxy-1-propynyl}benzoic acid,

4-{(E)-3-[4-(4-Dimethylaminophenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-hydroxypropenyl}-2-hydroxybenzoic acid,

4-{(E)-3-[4-(4-Dimethylaminophenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-oxopropenyl}-2-hydroxybenzoic acid,

4-{3-[4-(4-Dimethylaminophenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-hydroxy-1-propynyl}-2-hydroxybenzoic acid,

4-{(E)-3-[4-(4-Diethylaminophenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-hydroxypropenyl}benzoic acid,

4-{(E)-3-[4-(4-Diethylaminophenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-oxopropenyl}benzoic acid,

4-{3-[4-(4-Diethylaminophenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-hydroxy-1-propynyl}benzoic acid,

4-{(E)-3-[4-(4-Diethylaminophenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-hydroxypropenyl}-2-hydroxybenzoic acid,

4-{(E)-3-[4-(4-Diethylaminophenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-oxopropenyl}-2-hydroxybenzoic acid,

4-{3-[4-(4-Diethylaminophenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-hydroxy-1-propynyl}-2-hydroxybenzoic acid,

4-{(E)-3-[4-(4-Methoxyphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-hydroxypropenyl}benzoic acid,

4-{(E)-3-[4-(4-Methoxyphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-oxopropenyl}benzoic acid,

4-{3-[4-(4-Methoxyphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-hydroxy-1-propynyl}benzoic acid,

4-{(E)-3-[4-(4-Methoxyphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-hydroxypropenyl}-2-hydroxybenzoic acid,

4-{(E)-3-[4-(4-Methoxyphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-oxopropenyl}-2-hydroxybenzoic acid,

4-{3-[4-(4-Methoxyphenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-3-hydroxy-1-propynyl}-2-hydroxybenzoic acid,

and mixtures thereof.

11. A pharmaceutical composition comprising a therapeutically effective amount of at least one biaryl compound as defined by claim 1 , or salt or isomer thereof, formulated into a physiologically acceptable medium therefor.

12. The pharmaceutical composition as defined by claim 11 , said at least one biaryl compound, or salt or isomer, comprising from 0.001% to 10% by weight thereof.

13. The pharmaceutical composition as defined by claim 11 , said at least one biaryl compound, or salt or isomer, comprising from 0.01% to 1% by weight thereof.

14. A cosmetic composition comprising a cosmetic effective amount of at least one biaryl compound as defined by claim 1 , or salt or isomer thereof, formulated into a cosmetically acceptable medium therefor.

15. The cosmetic composition as defined by claim 14 , said at least one biaryl compound, or salt or isomer, comprising from 0.001% to 3% by weight thereof.

16. The pharmaceutical composition as defined by claim 11 , formulated as a paste, an ointment, a cream, a milk, a pomade, a powder, an impregnated pad, a syndet, a gel, a spray, a mousse, a stick, a shampoo, microspheres, nanospheres, lipid or polymer vesicles, a controlled release patch, a syrup, tablets, capsules, granules, an emulsion, or a dragee.