NOVEL a-LIPOIC ACID DERIVATIVES AND APPLICATIONS THEREOF

Abstract

Provided are novel α-lipoic acid derivatives represented by the following formula (I), which have a tyrosinase inhibiting activity, a melanin production suppressing activity and an elastase inhibiting activity. (In the formula, M denotes a metal, and A denotes an amino acid which is bound via N.)

1 . An N-(6,8-dimercaptooctanoyl)amino acid metal chelate compound represented by the following formula (I), 
     
       
         
         
             
             
         
       
       wherein M denotes a zinc, and A denotes an amino acid which is bound via the amino acid nitrogen; or a pharmacologically acceptable salt thereof, wherein the amino acid is selected from the group consisting of aminomethylcyclohexanoic acid, anthranilic acid, aminoethanesulfonic acid, glycine, alanine, valine, leucine, isoleucine, serine, threonine, tyrosine, cysteine, methionine, aspartic acid, asparagine, glutamic acid, glutamine, arginine, lysine, histidine, phenylalanine, tryptophan, β-alanine, γ-amino-n-butyric acid, carnitine, 5-aminolevulinic acid, 5-aminovaleric acid, and 6-aminohexanoic acid. 
     
   
   
       2 . (The N-(6,8-dimercaptooctanoyl)amino acid metal chelate compound of  claim 1 , wherein the N-(6,8-dimercaptooctanoyl)amino acid metal chelate compound is selected from the group consisting of N-(6,8-dimercaptooctanoyl) aminoethanesulfonic acid zinc chelate, N-(6,8-dimercaptooctanoyl)glycine zinc chelate, N-(6,8-dimercaptooctanoyl)aspartic acid zinc chelate, N-(6,8-dimercaptooctanoyl)-6-aminohexanoic acid zinc chelate, N-(6,8-dimercaptooctanoyl)-γ-amino-n-butyric acid zinc chelate, N-(6,8-dimercaptooctanoyl)phenylalanine zinc chelate, N-(6,8-dimercaptooctanoyl)-anthranilic acid zinc-chelate, N-(6,8-dimercaptooctanoyl)methionine zinc chelate, and N-(6,8-dimercaptooctanoyl)cysteine zinc chelate. 
   
   
       3 . A composition comprising a pharmaceutically acceptable vehicle or a cream base; and
 an N-(6,8-dimercaptooctanoyl)amino acid metal chelate compound represented by the following formula (I),   
     
       
         
         
             
             
         
       
     
     wherein M denotes a zinc, and A denotes an amino acid which is bound via the amino acid nitrogen; or a pharmacologically acceptable salt thereof, wherein the amino acid is selected from the group consisting of aminomethylcyclohexanoic acid, anthranilic acid, aminoethanesulfonic acid, glycine, alanine, valine, leucine, isoleucine, serine, threonine, tyrosine, cysteine, methionine, aspartic acid, asparagine, glutamic acid, glutamine, arginine, lysine, histidine, phenylalanine, tryptophan, β-alanine, γ-amino-n-butyric acid, carnitine, 5-aminolevulinic acid, 5-aminovaleric acid, and 6-aminohexanoic acid. 
   
   
       4 . The composition of  claim 3  comprising a cream base; and wherein the composition is a cosmetic preparation. 
   
   
       5 . The N-(6,8-dimercaptooctanoyl)amino acid metal chelate compound of  claim 1 , wherein the N-(6,8-dimercaptooctanoyl)amino acid metal chelate compound is selected from the group consisting of N-(6,8-dimercaptooctanoyl)-6-aminohexanoic acid zinc chelate, N-(6,8-dimercaptooctanoyl)aminoethanesulfonic acid zinc chelate and N-(6,8-dimercaptooctanoyl) phenylalanine zinc chelate. 
   
   
       6 . The N-(6,8-dimercaptooctanoyl)amino sulfonic acid metal chelate of  claim 1 , wherein the N-(6,8-dimercaptooctanoyl)amino sulfonic acid metal chelate compound is N-(6,8-dimercaptooctanoyl) aminoethanesulfonic acid zinc chelate. 
   
   
       7 . An N-(6,8-dimercaptooctanoyl)amino sulfonic acid metal chelate compound represented by the following formula (I), 
     
       
         
         
             
             
         
       
     
     wherein M denotes a zinc, and A denotes an aminoethanesulfonic acid which is bound via the amino sulfonic acid nitrogen; or a pharmacologically acceptable salt thereof.