Heterocyclic compound for stimulating or inducing the growth of the hair or eyelashes and/or slowing down their loss composition comprising it and its uses

Abstract

The invention relates to a composition for caring for or making up keratinous fibers comprising a heterocyclic compound of formula (I) or of one of its salts: in which: Hy is a heterocycle of 4 to 7 atoms comprising a carbonyl functional group and/or a thiocarbonyl functional group and optionally being substituted and G, R 1 , R 2 and R 3 are defined in the description.

1 . A composition for caring for or making up keratinous fibers comprising a physiologically acceptable medium and an effective amount of at least one heterocyclic compound of formula (I) or of one of its salts, having the formula:  
       
         
           
           
               
               
           
         
       
       wherein: 
 Hy represents a heterocycle with 5 atoms comprising at least one carbonyl functional group and/or one thiocarbonyl functional group, the said heterocycle optionally being substituted by at least one substituent selected from the group consisting of saturated and unsaturated, linear and branched C 1 -C 20  alkyl radicals;  
 G represents O, S or NH; and  
 R 1 , R 2  and R 3  represent, independently of one another, hydrogen, halogen, OR 0 , SR 0 , NR 0 R 0 ′, COR 0 , CSR 0 , NR 0 CONR 0 ′R 0 ″, C(═NR 0 )R 0 ′, C(═NR 0 )NR 0 ′R 0 ″, NR 0 C(═NR 0 ′)NR 0 ″R 0 ′″, OCOR 0 , COSR 0 , SCOR 0 , CSNR 0 R 0 ′, NR 0 CSR 0 ′, NR 0 CSNR 0 ′R 0 ″, COOR 0 , CONR 0 R 0 ′, CF 3 , NO 2 , CN, NR 0 COR 0 ′, SO 2 R 0 ′, SO 2 NR 0 R 0 ′or NR 0 SO 2 R 0 ′, or a saturated or unsaturated, linear or branched C 1 -C 20  alkyl radical optionally substituted by R 0 , where R 0 , R 0 ′, R 0 ″ and R 0 ′″, which are identical or different, represent hydrogen or linear or branched C 1 -C 20  alkyl;  
 said compound of formula (I) being selected from the group consisting of:  
 (i) a compound having the formula (IIIa):  
                     
 wherein Z and Z′ are each 0; when Z and Z′ are the same as G, at least one of the R 2  and R 3  groups represents CF 3 ; and when Z and Z′ are different from G, at least one of the R 2  and R 3  groups represents CF 3  or COOR 0  wherein R 0  is H;  
 (ii) a compound having the formula (VI):  
                     
 or a salt thereof, wherein Z, Z′ and G independently represent O or S; and at least one of the R 2  and R 3  groups represents hydrogen, CN, CF 3 , NO 2 , OR 0 , COOR 0  or a saturated, linear or branched, C 1 -C 20  alkyl radical optionally substituted by OR 0  wherein R 0  is H or a saturated, linear or branched, C 1 -C 20  alkyl radical;  
 (iii) a compound having the formula (VII):  
                     
 or a salt thereof, wherein Z, Z′ and G independently represent O or S; R represents a saturated, linear or branched, C 1 -C 10  alkyl radical; and at least one of the R 2  and R 3  groups represents a saturated, linear or branched, C 1 -C 20 , alkyl radical, NO 2  or OR 0  wherein R 0  is H or a saturated, linear or branched, C 1 -C 20  alkyl radical; and  
 (iv) a compound selected from the group consisting of:  
                     
 
     
     
         2 . A composition according to  claim 1 , wherein the compound of formula (I) comprises a 1,3-thiazolidine-2,4-dione ring.  
     
     
         3 . A composition according to  claim 1 , having formula (VI), wherein at least one of the R 2  and R 3  groups represents hydrogen, CN, CF 3 , NO 2 , OR 0 , COOR 0  or a saturated, linear or branched, C 1 -C 10  alkyl radical optionally substituted by OR 0  wherein R 0  is H or a saturated, linear or branched, C 1 -C 10  alkyl radical.  
     
     
         4 . A composition according to  claim 1 , having formula (VII), wherein at least one of the R 2  and R 3  groups represents a saturated, linear or branched, C 1 -C 10  alkyl radical, NO 2  or OR 0  wherein Ro is H or a saturated, linear or branched, C 1 -C 10  alkyl radical.  
     
     
         5 . A composition according to  claim 1 , wherein the salt of the compound of formula (I) is a salt selected from the group consisting of sodium salts, potassium salts, salts of zinc (Zn 2+ ), of calcium (Ca 2+ ), of copper (Cu 2+ ), of iron (Fe 2+ ), of strontium (Sr + ), of magnesium (Mg 2+ ), of manganese (Mn 2+ ), of ammonium, triethanolamine, monoethanolamine, diethanolamine, hexadecylamine, N,N,N′,N′-tetrakis(2-hydroxypropyl)ethylenediamine or tris(hydroxymethyl)-aminomethane salts, hydroxides, carbonates, halides, sulphates, phosphates and nitrates.  
     
     
         6 . A composition according to  claim 1 , wherein the compound of formula (I) is selected from the group consisting of:  
       
         
           
           
               
               
           
         
       
     
     
         7 . A composition according to  claim 1 , wherein the compound of formula (I) is present at a concentration ranging from 10 −3  to 10% with respect to the total weight of the composition.  
     
     
         8 . A composition according to  claim 7 , wherein the concentration of the compound of formula (I) ranges from 10 −2  to 2% with respect to the total weight of the composition.  
     
     
         9 . A composition according to  claim 1 , in the form of a cream or lotion for hair care, of a shampoo or conditioner, of a hair mascara or of a mascara for the eyelashes.  
     
     
         10 . A composition according to  claim 1 , in the form of an aqueous, alcoholic or aqueous/alcoholic solution or suspension.  
     
     
         11 . A composition according to  claim 1 , wherein the physiologically acceptable medium comprises other ingredients selected from the group consisting of solvents, thickeners, gelling agents, coloring materials which are soluble in the medium of the composition, fillers, pigments, antioxidants, preservatives, fragrances, electrolytes, neutralizing agents, film-forming polymers, UV blocking agents, and cosmetic and pharmaceutical active principles, and mixtures thereof, in addition to the compounds of formula (I).  
     
     
         12 . A composition according to  claim 1 , further comprising at least one additional active compound which promotes the regrowth and/or which limits the loss of keratinous fibers.  
     
     
         13 . A composition according to  claim 1 , further comprising at least one additional compound which promotes hair regrowth and/or limits hair loss selected from the group consisting of aminexil, 6-O-[(9Z,12Z)-octadeca-9,12-dienoyl]hexapyranose, potassium channel agonists, lipoxygenase inhibitors, bradykinin inhibitors, prostaglandins and their derivatives, prostaglandin receptor agonists or antagonists, nonprostanoic prostaglandin analogues, vasodilators, antiandrogens, cyclosporins and their analogues, antimicrobials, anti-inflammatories, retinoids, benzalkonium chloride, benzethonium chloride, phenol, estradiol, chlorpheniramine maleate, chlorophyllin derivatives, cholesterol, cysteine, methionine, menthol, peppermint oil, calcium panthotenate, panthenol, resorcinol, protein kinase C activators, glycosidase inhibitors, glycosaminoglycanase inhibitors, pyroglutamic acid esters, hexosaccharidic acid, acylhexosaccharic acid, aryl-substituted ethylenes, N-acylated amino acids, flavonoids, ascomycin derivatives and analogues, histamine antagonists, saponins, proteoglycanase inhibitors, estrogen agonists and antagonists, pseudopterins, cytokines and growth factor promoters, IL-1 and IL-6 inhibitors, IL-10 promoters, TNF inhibitors, vitamins, benzophenones, hydantoin, octopirox, retinoic acid, antipruritic agents, agents for combating parasites, antifungals, nicotinic acid esters, calcium antagonist agents, hormones, triterpenes, anti-androgen agents, steroidal and nonsteroidal inhibitors of 5α-reductases, FP receptor agonists, and their mixtures.  
     
     
         14 . A composition according to  claim 13 , wherein the additional compound is selected from the group consisting of aminexil, FP receptor agonists and vasodilators.  
     
     
         15 . A composition according to  claim 1 , further comprising another active principle selected from the group consisting of proteins, protein hydrolysates, amino acids, polyols, urea, allantoin, sugars, plant extracts, hydroxy acids, retinol, tocopherol, essential fatty acids, ceramides, essential oils, salicylic acid, 5-(n-octanoyl)salicylic acid, esters of hydroxy acids, and phospholipids.  
     
     
         16 . A composition according to  claim 13 , wherein the additional active compound is selected from the group consisting of aminexil, minoxidil, latanoprost, butaprost and travoprost.  
     
     
         17 . A compound having the formula (VI):  
       
         
           
           
               
               
           
         
       
       or a salt thereof, wherein Z, Z′ and G independently represent O or S; R 2  and R 3 , independently of each other, represent hydrogen, halogen, OR 0 , SR 0 , NR 0 R 0 ′, COR 0 , CSR 0 , NR 0 CONR 0 'R 0 ′, C(═NR 0 )R 0 ′, C(═NR 0 )NR 0 ″R 0 ″, NR 0 C(═NR 0 ′)NR 0 ″R 0 ′″, OCOR 0 , COSR 0 , SCOR 0 , CSNR 0 R 0 ′, NR 0 CSR 0 ′, NR 0 CSNR 0 ′R 0 ″, COOR 0 , CONR 0 R 0 ′, CF 3 , NO 2 , CN, NR 0 COR 0 ′, SO 2 R 0 ′, SO 2 NR 0 R 0 ′ or NR 0 SO 2 R 0 ′, or a saturated or unsaturated, linear or branched C 1 -C 20  alkyl radical optionally substituted by R 0 , where R 0 , R 0 ′, R 0 ″ and R 0 ′″, which are identical or different, represent hydrogen or linear or branched C 1 -C 20  alkyl; provided that at least one of the R 2  and R 3  groups represents hydrogen, CN, CF 3 , NO 2 , OR 0 , COOR 0  or a saturated, linear or branched, C 1 -C 20  alkyl radical optionally substituted by OR 0  wherein Ro is H or a saturated, linear or branched, C 1 -C 20  alkyl radical.  
     
     
         18 . A compound having the formula (VII):  
       
         
           
           
               
               
           
         
       
       or a salt thereof, wherein Z, Z′ and G independently represent O or S; R represents a saturated, linear or branched, C 1 -C 10  alkyl radical; R 2  and R 3  independently of each other, represent hydrogen, halogen, OR 0 , SR 0 , NR 0 R 0 ′, COR 0 , CSR 0 , NR 0 CONR 0 ′R 0 ″, C(═NR 0 )R 0 ′, C(═NR 0 )NR 0 ′R 0 ″, NR 0 C(═NR 0 ′)NR 0 ″R 0 ′″, OCOR 0 , COSR 0 , SCOR 0 , CSNR 0 R 0 ′, NR 0 CSR 0 ′, NR 0 CSNR 0 ′R 0 ″, COOR 0 , CONR 0 R 0 ′, CF 3 , NO 2 , CN, NR 0 COR 0 ′, SO 2 R 0 ′, SO 2 NR 0 R 0 ′ or NR 0 SO 2 R 0 ′, or a saturated or unsaturated, linear or branched C 1 -C 20  alkyl radical optionally substituted by R 0 , where R 0 , R 0 ′, R 0 ″ and R 0 ′″, which are identical or different, represent hydrogen or linear or branched C 1 -C 20  alkyl; provided that at least one of the R 2  and R 3  groups represents a saturated, linear or branched, C 1 -C 20  alkyl radical, NO 2  or OR 0  wherein R 0  is H or a saturated, linear or branched, C 1 -C 20  alkyl radical.  
     
     
         19 . A compound selected from the group consisting of: