US2019241498A1PendingUtilityA1

Resveratrol esters

59
Assignee: COLE RES & DESIGN LLCPriority: Dec 24, 2015Filed: Sep 7, 2018Published: Aug 8, 2019
Est. expiryDec 24, 2035(~9.4 yrs left)· nominal 20-yr term from priority
C07C 69/40A61P 17/02C07C 67/08C07C 229/08C07C 229/36C07C 69/42
59
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Claims

Abstract

Salts of resveratrol esters are also included.

Claims

exact text as granted — not AI-modified
1 . A resveratrol ester having the following structure: 
       
         
           
           
               
               
           
         
         wherein R 1 , R 2  and R 3  are H or 
       
       
         
           
           
               
               
           
         
         each R 4  is independently a carbon chain of 2 to 4 carbon atoms comprising a terminal carboxylic acid moiety, a carbon chain of 1 to 5 carbon atoms comprising an amine moiety, —(CH 2 ) 3 (NH)(R 6 ), or 
       
       
         
           
           
               
               
           
         
         R 5  is a carbon chain of 3 or 4 carbon atoms having a terminal carboxylic acid moiety or a natural amino acid side chain, 
         R 6  is —(CO)(CH 2 ) n (CO)(OH) and where n is 1 or 2, and 
         at least one of R 1 , R 2  and R 3  is 
       
       
         
           
           
               
               
           
         
         and salts thereof. 
       
     
     
         2 . The resveratrol ester of  claim 1 , wherein R 4  is the carbon chain of 2 to 4 carbon atoms comprising the terminal carboxylic acid moiety, and salts thereof. 
     
     
         3 . The resveratrol ester of  claim 1 , wherein R 4  is the carbon chain of 1 to 5 carbon atoms comprising the amine moiety, and salts thereof. 
     
     
         4 . The resveratrol ester of  claim 1 , wherein R 4  is 
       
         
           
           
               
               
           
         
       
       and R 5  is the carbon chain of 3 or 4 carbon atoms having the terminal carboxylic acid moiety, and salts thereof. 
     
     
         5 . The resveratrol ester of  claim 2 , wherein R 4  is selected from the group consisting of —(CH 2 )(CO)(OH), —(CH 2 ) 2 (CO)(OH), and —(CH 2 ) 3 (CO)(OH). 
     
     
         6 . The resveratrol ester of  claim 5 , wherein R 4  is —(CH 2 ) 3 (CO)(OH). 
     
     
         7 . The resveratrol ester of  claim 2 , wherein R 1 , R 2  and R 3  are 
       
         
           
           
               
               
           
         
       
     
     
         8 . The resveratrol ester of  claim 7 , wherein R 4  is selected from the group consisting of —(CH 2 )(CO)(OH), —(CH 2 ) 2 (CO)(OH), and —(CH 2 ) 3 (CO)(OH). 
     
     
         9 . The resveratrol ester of  claim 8 , wherein R 4  is —(CH 2 ) 3 (CO)(OH). 
     
     
         10 . The resveratrol ester of  claim 3 , wherein R 4  is selected from the group consisting of —(NH 2 )CHCH 3 , —CH(NH 2 )CH(CH 3 ) 2 , —CH(NH 2 )CH 2 CH(CH 3 ) 2 , —CH(NH 2 )CH(CH 3 )CH 2 CH 3 , —CH 2 NH 2 , —(CH 2 ) 3 (C 6 H 4 )NH 2 , —(CH 2 ) 3 NH 2  and —(CH 2 ) 5 NH 2 . 
     
     
         11 . The resveratrol ester of  claim 10 , wherein R 4  is —CH(NH 2 )CH(CH 3 ) 2 . 
     
     
         12 . The resveratrol ester of  claim 3 , wherein R 1 , R 2  and R 3  are 
       
         
           
           
               
               
           
         
       
     
     
         13 . The resveratrol ester of  claim 12 , wherein R 4  is selected from the group consisting of —(NH 2 )CHCH 3 , —CH(NH 2 )CH(CH 3 ) 2 , —CH(NH 2 )CH 2 CH(CH 3 ) 2 , —CH(NH 2 )CH(CH 3 )CH 2 CH 3 , —CH 2 NH 2 , —(CH 2 ) 3 (C 6 H 4 )NH 2 , —(CH 2 ) 3 NH 2  and —(CH 2 ) 5 NH 2 . 
     
     
         14 . The resveratrol ester of  claim 13 , wherein R 4  is —CH(NH 2 )CH(CH 3 ) 2 . 
     
     
         15 . A method of making the resveratrol ester of  claim 1 , comprising:
 forming the resveratrol ester from resveratrol.   
     
     
         16 . A composition, comprising:
 the resveratrol ester of  claim 2 , and   a pharmaceutically acceptable carrier.   
     
     
         17 . (canceled) 
     
     
         18 . A resveratrol ester selected from the group consisting of resveratrol hemimalonate, resveratrol hemisuccinate, resveratrol hemiglutarate, resveratrol 2-aminopropanoate, resveratrol 2-amino-3-methylbutanoate, resveratrol 2-amino-4-methylpentanoate, resveratrol 2-amino-3-methylpentanoate, resveratrol aminoethanoate, resveratrol 4-(4-aminophenyl)-butyrate, resveratrol 4-amino-butyrate, and resveratrol 6-amino-hexanoate. 
     
     
         19 . The resveratrol ester of  claim 18 , wherein the resveratrol ester is resveratrol hemiglutarate. 
     
     
         20 . The resveratrol ester of  claim 19 , wherein the resveratrol hemiglutarate is resveratrol trihemiglutarate. 
     
     
         21 . (canceled) 
     
     
         22 . A method of reducing scar formation, comprising:
 administering an effective amount of the composition of  claim 16 , to a patient in need thereof.   
     
     
         23 . (canceled) 
     
     
         24 . (canceled)

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