N-acetyglucosamine derivatives and use thereof

Abstract

The present invention relates to An N-acetylglucosamine derivative represented by the following formula (1), and a hyaluronic acid production promoting agent containing the same and a skin external preparation containing the same: wherein R 1 is a hydrogen atom or an alkyl group having 2 to 18 carbon atoms; R 2 , R 3 , and R 4 are hydrogen atoms or acyl groups having 2 to 18 carbon atoms and may be all the same or different from others; the steric structure at position 1 may be α or β; provided that R 1 , R 2 , R 3 , and R 4 must not be all hydrogen atoms. It is intended to provide an easily available hyaluronic acid production promoting agent and a skin external preparation whereby the production of hyaluronic acid can be promoted in the skin and thus the skin can be maintained in a vital and moist state so that it is expected that the human skin can be prevented from age.

1 . A method for promoting hyaluronic acid production in skin, comprising applying to the skin a composition comprising an N-acetylglucosamine derivative of formula (1): 
     
       
         
         
             
             
         
       
       wherein R 1  is a hydrogen atom or an alkyl group having 2 to 18 carbon atoms; R 2 , R 3 , and R 4  are hydrogen atoms or acyl groups having 2 to 18 carbon atoms and may be all the same or different from others; the steric structure at position 1 may be α or β; provided that R 1 , R 2 , R 3 , and R 4  must not be all hydrogen atoms. 
     
   
   
       2 . The method of  claim 1 , wherein the N-acetylglucosamine derivative of the formula (1) is an N-acetylglucosamine derivative of formula (2) or (3): 
     
       
         
         
             
             
         
       
       wherein R 5  is an alkyl group having 2 to 18 carbon atoms; R 6  is a hydrogen atom or an acetyl group; and the steric structure at position 1 may be α or β; or 
     
     
       
         
         
             
             
         
       
       wherein R 7  is a hydrogen atom or an alkyl group having 2 to 18 carbon atoms; R 8  is an acyl group having 2 to 18 carbon atoms; and the steric structure at position 1 may be α or β. 
     
   
   
       3 . The method of  claim 1 , wherein the N-acetylglucosamine derivative of the formula (1) is an N-acetylglucosamine derivative of formula (4): 
     
       
         
         
             
             
         
       
       wherein the steric structure at position 1 may be α or β. 
     
   
   
       4 . The method of  claim 1 , wherein the N-acetylglucosamine derivative of the formula (1) is an N-acetylglucosamine derivative of formula (5): 
     
       
         
         
             
             
         
       
       wherein the steric structure at position 1 may be α or β. 
     
   
   
       5 . The method of  claim 1 , wherein the N-acetylglucosamine derivative of the formula (1) is an N-acetylglucosamine derivative of formula (6): 
     
       
         
         
             
             
         
       
       wherein the steric structure at position 1 may be α or β. 
     
   
   
       6 . The method of  claim 1 , wherein the N-acetylglucosamine derivative of the formula (1) is an N-acetylglucosamine derivative of formula (7): 
     
       
         
         
             
             
         
       
       wherein the steric structure at position 1 may be α or β. 
     
   
   
       7 . The method of  claim 1 , wherein the N-acetylglucosamine derivative of the formula (1) is an N-acetylglucosamine derivative of formula (8): 
     
       
         
         
             
             
         
       
       wherein the steric structure at position 1 may be α or β. 
     
   
   
       8 . The method of  claim 1 , wherein the N-acetylglucosamine derivative of the formula (1) is an N-acetylglucosamine derivative of formula (9): 
     
       
         
         
             
             
         
       
       wherein the steric structure at position 1 may be α or β. 
     
   
   
       9 . The method of  claim 1 , wherein the N-acetylglucosamine derivative of the formula (1) is an N-acetylglucosamine derivative of formula (10): 
     
       
         
         
             
             
         
       
       wherein the steric structure at position 1 may be α or β. 
     
   
   
       10 . A method for promoting hyaluronic acid production in skin, comprising applying to the skin a composition comprising an N-acetylglucosamine derivative of formula (11): 
     
       
         
         
             
             
         
       
       wherein the steric structure at position 1 may be α or β. 
     
   
   
       11 . The method of  claim 1 , wherein the N-acetylglucosamine derivative of the formula (1) is an N-acetylglucosamine derivative of formula (12): 
     
       
         
         
             
             
         
       
       wherein the steric structure at position 1 may be α or β. 
     
   
   
       12 . The method of  claim 1 , wherein the N-acetylglucosamine derivative of the formula (1) is an N-acetylglucosamine derivative of formula (13): 
     
       
         
         
             
             
         
       
       wherein the steric structure at position 1 may be α or β. 
     
   
   
       13 . The method of  claim 1 , wherein the N-acetylglucosamine derivative of the formula (1) is an N-acetylglucosamine derivative of formula (14): 
     
       
         
         
             
             
         
       
       wherein the steric structure at position 1 may be α or β. 
     
   
   
       14 . A method for promoting hyaluronic acid production in skin, comprising applying to the skin a composition comprising is an N-acetylglucosamine derivative of formula (15): 
     
       
         
         
             
             
         
       
       wherein the steric structure at position 1 may be α or β. 
     
   
   
       15 . A method for promoting hyaluronic acid production in skin, comprising applying to the skin a composition comprising an N-acetylglucosamine derivative of formula (16): 
     
       
         
         
             
             
         
       
       wherein R 9  is an acyl group having 2 to 16 carbon atoms and the steric structure at position 1 may be α or β. 
     
   
   
       16 . The method of  claim 15 , wherein the N-acetylglucosamine derivative of the formula (16) is an N-acetylglucosamine derivative of formula (17): 
     
       
         
         
             
             
         
       
       wherein the steric structure at position 1 may be α or β. 
     
   
   
       17 . The method of  claim 1 , wherein the method is for retaining vital, elastic, and moist skin. 
   
   
       18 . The method of  claim 10 , wherein the method is for retaining vital, elastic, and moist skin. 
   
   
       19 . The method of  claim 14 , wherein the method is for retaining vital, elastic, and moist skin. 
   
   
       20 . The method of  claim 15 , wherein the method is for retaining vital, elastic, and moist skin.