Novel resorcinol derivatives for skin

Abstract

New 4-substituted resorcinol derivatives of general formula I and/or B and process for synthesizing same, cosmetic compositions and methods of using same, particularly for skin lightening: Wherein X 1 and/or X 2 represents hydrogen (H), linear or branched, saturated or unsaturated C 1 -C 12 alkyl, alkenyl, or acyl groups. Preferably, X 1 and/or X 2 represents hydrogen (H); linear or branched, saturated or unsaturated C 1 -C 12 alkyl or acyl groups; R 1 represents hydrogen (H), linear or branched, cyclic or acyclic, saturated or unsaturated C 1 -C 12 alkyl, alkenyl, cycloalkyl, or cycloalkenyl group. Preferably, R 1 represents hydrogen (H) or a C 1 alkyl group (i.e, methyl group). More preferably, R 1 represents hydrogen; n represents 0, 1. When n=0, the ring is a cyclopentyl with or without one heteroatom from O, N or S and/or with or without one double bond. When n=1, the ring is a cyclohexyl with or without one heteroatom from O, N or S and/or with or without one double bond; and m represents an integer between 1 and 6.

1 . A compound of general formula I:  
     
       
         
         
             
             
         
       
     
     Wherein 
 X 1  and X 2  are independently represented as hydrogen (H), linear or branched, saturated or unsaturated C 1 -C 12  alkyl, alkenyl, or acyl groups;  
 R 1 =hydrogen (H), linear or branched, cyclic or acyclic, saturated or unsaturated C 1 -C 12  alkyl, alkenyl, cycloalkyl, or cycloalkenyl group;  
 n=0, 1; and  
 when n=0, the ring is cyclopentyl with or without one heteroatom from O, N or S and/or with or without one double bond; or  
 when n=1, the ring is cyclohexyl with or without one heteroatom from O, N or S and/or with or without one double bond; and  
 m is an integer between 1 and 6,  
 with the proviso that X 1  and X 2  are not simultaneously hydrogen.  
 
   
   
       2 . A compound of general formula B:  
     
       
         
         
             
             
         
       
     
     Wherein 
 X 1  and X 2  are independently represented as hydrogen (H), linear or branched, saturated or unsaturated C 1 -C 12  alkyl, alkenyl, or acyl groups;  
 R 1 =linear or branched, cyclic or acyclic, saturated or unsaturated C 1 -C 12  alkyl, alkenyl, cycloalkyl, or cycloalkenyl group;  
 n=0, 1; and  
 when n=0, the ring is cyclopentyl with or without one heteroatom from O, N or S and/or with or without one double bond; or  
 when n=1 the ring is cyclohexyl with or without one heteroatom from O, N or S and/or with or without one double bond.  
 
   
   
       3 . A cosmetic method of skin lightening comprising applying to the skin a compound according to  claim 1 .  
   
   
       4 . (canceled)  
   
   
       5 . A cosmetic method of skin lightening comprising applying to the skin a compound according to  claim 1 .  
   
   
       6 . A cosmetic composition comprising: 
 (a) 4-substituted resorcinol derivative of general formula B according to  claim 1;  and    (b) a cosmetically acceptable carrier.    
   
   
       7 . The composition of  claim 6 , further comprising an organic sunscreen selected from the group consisting of Benzophenone-3, Benzophenone-4, Benzophenone-8, DEA, Methoxycinnamate, Ethyl dihydroxypropyl-PABA, Glyceryl PABA, Homosalate, Methyl anthranilate, Octocrylene, Octyl dimethyl PABA, Octyl methoxycinnamate (PARSOL MCX), Octyl salicylate, PABA, 2-Phenylbenzimidazole-5-sulphonic acid, TEA salicylate, 3-(4-methylbenzylidene)-camphor, Benzophenone-1, Benzophenone-2, Benzophenone-6, Benzophenone-12, 4-Isopropyl dibenzoyl methane, Butyl methoxy dibenzoyl methane (PARSOL 1789), Etocrylene, and mixtures thereof.  
   
   
       8 . The composition of  claim 6 , wherein said 4-substituted resorcinol derivative is present in an amount of about 0.1 wt. % to about 5 wt. %.  
   
   
       9 . The composition of  claim 1 , wherein the 4-substituted resorcinol is selected from the group consisting of 4-cyclopentyl methyl resorcinols, 4-cyclohexyl methyl resorcinols, and mixtures thereof.  
   
   
       10 . The cosmetic composition of  claim 6 , further comprising a skin benefit agent selected from the group consisting of alpha-hydroxy acids and esters, beta-hydroxy acids and esters, polyhydroxy acids and esters, kojic acid and esters, ferulic acid and ferulate derivatives, vanillic acid and esters, dioic acids and esters, retinol, retinal, retinyl esters, hydroquinone, t-butyl hydroquinone, mulberry extract, licorice extract, resorcinol derivatives, and mixtures thereof.  
   
   
       11 . The cosmetic composition of  claim 7 , wherein said organic sunscreen is present in an amount of about 1 wt % to about 10 wt % of said cosmetic composition; and 
 wherein the weight ratio of said organic sunscreen to said 4-substituted resorcinol derivative is about 10000:1 to about 1:10000.    
   
   
       12 . The cosmetic composition according to  claim 10  wherein said skin benefit agent is selected from the group consisting of alpha-hydroxy acids, beta-hydroxy acids, polyhydroxy acids, hydroquinone, t-butyl hydroquinone, 4-substituted resorcinol derivatives, and mixtures thereof.  
   
   
       13 . A cosmetic method of skin lightening comprising applying to skin the composition of  claim 6 .  
   
   
       14 . A cosmetic method of skin lightening comprising applying to skin the composition of  claim 9 .  
   
   
       15 . A process for synthesizing a compound of general formula II, comprising:  
     
       
         
         
             
             
         
       
     
     Wherein a, b, c, d represent reaction steps, reagents and conditions: 
 (a) cycloalkylcarbonyl derivative, ZnCl 2 , organic solvent;  
 (b) acetic anhydride, triethylamine;  
 (c) hydrogen, catalyst, acidic conditions;  
 (d) aqueous acid hydrolysis; and  
 wherein  
 R 1 =hydrogen (H), linear or branched, cyclic or acyclic, saturated or unsaturated C 1 -C 12  alkyl, alkenyl, cycloalkyl, or cycloalkenyl group;  
 n 0, 1; and  
 when n=0, the ring is cyclopentyl with or without one heteroatom from O, N or S and/or with or without one double bond; or  
 when n=1, the ring is cyclohexyl with or without one heteroatom from O, N or S and/or with or without one double bond; and 
 m is an integer between 1 and 6.