Hydroxydecenoic acid compounds for promoting desquamation/epidermal renewal of the skin and/or combating skin aging

Abstract

10-Hydroxy-2-decenoic acid and derivatives thereof are well suited for promoting desquamation and/or stimulating epidermal renewal and/or combating intrinsic/extrinsic aging of the skin of a candidate individual in need of such treatment, by administering thereto, for such period of time as required to elicit the desired response, an effective amount of at least one of said 10-hydroxy-2-decenoic acid or derivative thereof.

What is claimed is:  
     
         1 . A regime/regimen for promoting desquamation and/or stimulating epidermal renewal and/or combating intrinsic aging of the skin of a candidate individual in need of such treatment, comprising administering thereto, for such period of time as required to elicit the desired response, an effective amount of at least one compound having the structural formula (I):  
       
         
           
           
               
               
           
         
         in which R 1  is a radical or an atom selected from among a hydrogen atom, an —NR′R″ radical, wherein R′ and R″, which may be identical or different, are each a hydrogen atom, a C 1 -C 4  alkyl radical, a C 3 -C 4  alkenyl radical, or a cyclopentyl radical or cyclohexyl radical, with the proviso that R′ and R″ may together form a heterocycle with the nitrogen atom from which they depend, and with the further proviso that the —NR′R″ radical may be the residue of an amino acid or glucosamine, an —OR 3  radical, wherein R 3  is a radical or an atom selected from among a hydrogen atom, a linear or branched C 1  to C 18  alkyl radical, a linear or branched C 2  to C 18  alkenyl radical, or a linear or branched C 1  to C 18  perfluoroalkyl radical, with the proviso that the alkyl or alkenyl radicals may be substituted by one or more hydroxyl and/or amino and/or aminoalkyl groups, or substituted by a carboxylic acid functional group or a linear or branched C 1 -C 18  alkyl carboxylate functional group, an aryl radical or an aralkyl radical optionally substituted by a linear or branched C 1 -C 18  alkyl radical, by —CO—R′″ acyl radicals, or by —OR′″ alkoxy radicals, wherein R′″ represents a hydrogen atom, a hydroxyl radical, or a linear or branched C 1 -C 18  alkyl radical; R 2  is a radical or an atom selected from among a hydrogen atom, a linear or branched C 1  to C 18  alkyl radical, a linear or branched C 2  to C 18  alkenyl radical, a linear or branched C 1  to C 18  perfluoroalkyl radical, a C 1 -C 8  mono- or polyhydroxyalkyl radical, a cyclopentyl or cyclohexyl radical, a tetrahydropyranyl radical, a radical having the following formula (II):  
         
           
             
             
                 
                 
             
           
         
         wherein R 4  is a linear or branched C 1 -C 18  alkyl radical, a C 1 -C 8  monohydroxyalkyl radical, a C 3 -C 6  polyhydroxyalkyl radical having from 2 to 5 hydroxyl groups, an —NR′R″ radical, wherein R′ and R″, which may be identical or different, are each a hydrogen atom, a C 1 -C 4  alkyl radical, a C 3 -C 4  alkenyl radical or a cyclopentyl radical or a cyclohexyl radical, with the proviso that R′ and R″ may together form a heterocycle with the nitrogen atom from which they depend, and with the further proviso that the —NR′R″ radical may be the residue of an amino acid or glucosamine, an aralkyl radical or an aryl radical optionally substituted by one or more linear or branched C 1 -C 18  alkyl radicals, or by a —CO—R′″ acyl radical or by an —OR′″ alkoxy radical, wherein R′″ is as defined above, and the corresponding salts, isomers and stereoisomers thereof; with the further proviso that, if R 2  is a hydrogen atom, then R 3  cannot be an N,N-dimethylaminoethyl group or a radical of the formula:  
         
           
             
             
                 
                 
             
           
         
         wherein X and Y, which are identical, are each a hydrogen atom or a radical:  
         
           
             
             
                 
                 
             
           
         
         or wherein X is a hydrogen atom and Y is a radical:  
         
           
             
             
                 
                 
             
           
         
         or wherein X is a radical:  
         
           
             
             
                 
                 
             
           
         
         and Y is:  
         
           
             
             
                 
                 
             
           
         
       
     
     
         2 . The regime/regimen as defined by  claim 1 , comprising administering to said candidate individual an alkali or alkaline earth metal salt, or zinc, magnesium or strontium salt, or amine or quaternary ammonium salt of said at least one compound having the structural formula (I).  
     
     
         3 . The regime/regimen as defined by  claim 1 , comprising administering to said candidate individual a salt of an inorganic or organic acid of said at least one compound having the sructural formula (I).  
     
     
         4 . The regime/regimen as defined by  claim 3 , comprising administering to said candidate individual, an amine hydrochloride, hydrobromide or citrate of said at least one compound having the structural formula (I).  
     
     
         5 . The regime/regimen as defined by  claim 1 , for promoting desquamation of the skin of a candidate individual in need of such treatment, comprising administering thereto, for such period of time as required to elicit the desired response, a desquamation-effective amount of at least one 10-hydroxy-2-decenoic acid compound having the structural formula (I).  
     
     
         6 . The regime/regimen as defined by  claim 1 , for stimulating renewal of the epidermal skin of a candidate individual in need of such treatment, comprising administering thereto, for such period of time as required to elicit the desired response, an epidermal renewal-effective amount of at least one 10-hydroxy-2-decenoic acid compound having the structural formula (I).  
     
     
         7 . The regime/regimen as defined by  claim 1 , for combating intrinsic and for extrinsic aging of the skin of a candidate individual in need of such treatment, comprising administering thereto, for such period of time as required to elicit the desired response, a skin aging combating-effective amount of at least one 10-hydroxy-2-decenoic acid compound having the structural formula (I).  
     
     
         8 . The regime/regimen as defined by  claim 1 , wherein formula (I), R 1  is an —OR 3  radical, in which R 3  is a hydrogen atom, a carboxymethyl group, a 1′-carboxyethyl group, a 1′-carboxyheptyl group, a 2′-carboxy-phenyl group, or a 2′-carboxy-4′-octanoylphenyl group.  
     
     
         9 . The regime/regimen as defined by  claim 1 , wherein formula (I), R 2  is a hydrogen atom, a 2′-hydroxyethyl group, a 2′, 3′-dihydroxypropyl group, a 2′-hydroxypropyl group or a —CO—R 4  group in, which R 4  is a hydroxymethyl group, a 1′-hydroxyethyl group, a 1′-hydroxyheptyl group, a 2′-hydroxyphenyl group, or a 2′-hydroxy-4′-octanoylphenyl group.  
     
     
         10 . The regime/regimen as defined by  claim 1 , wherein formula (I), R 1  is the —OH radical and R 2  is a hydrogen atom, a 2′-hydroxyethyl group, a 2′, 3′-dihydroxypropyl group, or a 2′-hydroxypropyl group.  
     
     
         11 . The regime/regimen as defined by  claim 1 , wherein formula (I), R 2  is a hydrogen atom, R 1  is an —NR′R″ group, in which R′ is a hydrogen atom, and R″ is a C 1 -C 6  mono- or polyhydroxy group.  
     
     
         12 . The regime/regimen as defined by  claim 1 , wherein formula (I), R 2  is a hydrogen atom and R 1  is the —OR 3  radical, in which R 3  is a carboxymethyl group, a 1′-carboxyethyl group, a 1′-carboxyheptyl group, a 2′-carboxyphenyl group, or a 2′-carboxy-4′-octanoyl-phenyl group.  
     
     
         13 . The regime/regimen as defined by  claim 1 , wherein formula (I), R 2  is the —CO—R 4  group and R 4  is a hydroxymethyl group, a 1′-hydroxyethyl group, a 1′-hydroxyheptyl group, a 2′-hydroxyphenyl group, or a 2′-hydroxy-4′-octanoyl-phenyl group.  
     
     
         14 . A cosmetic/dermatological composition of matter suited for promoting desquamation and/or stimulating epidermal renewal and/or combating intrinsic/extrinsic aging of the skin of a candidate individual in need of such treatment, comprising an effective amount of at least one 10-hydroxy-2-decenoic acid compound having the structural formula (I), formulated into a cosmetically/dermatologically acceptable vehicle, diluent or carrier therefor.  
     
     
         15 . The cosmetic/dermatological composition as defined by  claim 14 , comprising a topically applicable, cosmetically/dermatologically acceptable vehicle, diluent or carrier.  
     
     
         16 . The cosmetic/dermatological composition as defined by  claim 14 , comprising from 0.001% to 20% by weight of said at least one 10-hydroxy-2-decenoic acid compound having the structural formula (I).  
     
     
         17 . The cosmetic/dermatological composition as defined by  claim 16 , comprising from 0.01% to 5% by weight of said at least one 10-hydroxy-2-decenoic acid compound having the structural formula (I).  
     
     
         18 . The cosmetic/dermatological composition as defined by  claim 14 , comprising an oil-in-water emulsion.  
     
     
         19 . The cosmetic/dermatological composition as defined by  claim 14 , comprising a water-in-oil emulsion.  
     
     
         20 . The cosmetic/dermatological composition as defined by  claim 14 , comprising a solution, dispersion, lotion, serum, milk, suspension, gel, cream gel, cream, microcapsules, microparticles, or vesicular dispersion.  
     
     
         21 . The cosmetic/dermatological composition as defined by  claim 14 , comprising a shampoo, hair setting or treating lotion, hair styling cream or gel, hair dyeing formulation, hair structuring lotion, or permanent wave formulation.  
     
     
         22 . The cosmetic/dermatological composition as defined by  claim 14 , comprising an aerosol, foam, soap, capsules, granules, or tablets.  
     
     
         23 . The cosmetic/dermatological composition as defined by  claim 14 , further comprising at least one cosmetically acceptable additive or adjuvant.  
     
     
         24 . The cosmetic/dermatological composition as defined by  claim 23 , said at least one additive or adjuvant comprising a hydrophilic or lipophilic gelling agent, hydrophilic or lipophilic active agent, preservative, antioxidizing agent, odor absorber, solvent, filler, fragrance, UV-screening agent, colorant, protein or hydrolysate thereof, urea, amino acid, polyol, sugar or derivative thereof, vitamin, plant extract, fatty acid, ceramide, essential oil, salicylic acid or derivative thereof, hydroxy acid, or mixture thereof.  
     
     
         25 . The cosmetic/dermatological composition as defined by  claim 14 , further comprising a therapeutically effective amount of at least one other active agent selected from the group consisting of a hair regrowth and/or hair loss retarding active agent, active agent which varies cutaneous pigmentation and/or proliferation and/or differentiation, antibacterial agent, antiparasitic agent, anti-fungal agent, anti-inflammatory agent, antipruriginous agent, anaesthetic, antiviral agent, keratolytic agent, anti-free-radical agent, anti-seborrhoeic agent, antidandruff agent, antiacne agent, and plant, marine or bacterial extract.  
     
     
         26 . A 10-hydroxy-2-decenoic acid compound having the structural formula (I′):  
       
         
           
           
               
               
           
         
         in which R′ 1  is a hydrogen atom, a radical of the formula:  
         
           
             
             
                 
                 
             
           
         
         a radical of the formula:  
         
           
             
             
                 
                 
             
           
         
         a radical of the formula:  
         
           
             
             
                 
                 
             
           
         
         wherein R′ 5 , R′ 6 , R′ 7 , R′ 8 , R′ 9  and R′ 10  are as defined below; R′ 2  is a hydrogen atom, a radical of the formula:  
         
           
             
             
                 
                 
             
           
         
         a radical of the formula:  
         
           
             
             
                 
                 
             
           
         
         a radical of the formula:  
         
           
             
             
                 
                 
             
           
         
         R′ 5  is a hydrogen atom, a —CH 3  radical or a —C 6 H 13  radical; R′ 6  is a —COOH radical, a —CO 2 —CH 2 —CH 3  radical, a —CH 2 OH radical or a hydroxyl radical; R′ 7  is an —OH radical, a radical of the formula:  
         
           
             
             
                 
                 
             
           
         
         or a radical of the formula:  
         
           
             
             
                 
                 
             
           
         
         R′ 8  is an —OH radical or a radical of the formula:  
         
           
             
             
                 
                 
             
           
         
         R′ 9  is a radical of the formula:  
         
           
             
             
                 
                 
             
           
         
         R′ 10  is a radical of the formula:  
         
           
             
             
                 
                 
             
           
         
         or a radical of the formula:  
         
           
             
             
                 
                 
             
           
         
         with the proviso that, when R′ 1  is a hydrogen atom, then R′ 2  cannot be a hydrogen atom, and that, when R′ 7  is a radical of the formula:  
         
           
             
             
                 
                 
             
           
         
         then R′ 8  cannot be a radical of the formula:  
         
           
             
             
                 
                 
             
           
         
         and the salts, isomers and stereoisomers thereof.