Nutritional supplements and therapeutic compositions comprising (r)-3- hydroxybutyrate derivatives

Abstract

Novel compounds and compositions containing (R)-3-hydroxybutyrate derivatives are disclosed. The compounds and compositions can be used as nutritional supplements to increase physical performance and as therapeutics to ameliorate symptoms of medical conditions, particularly neurological conditions, such as Alzheimer's and similar conditions. Novel methods for making R-3-hydroxybutyrate derivatives also are disclosed. Exemplary methods employ a supercritical solvent, such as supercritical carbon dioxide, and employ a lipase catalyzed esterification or transesterification reaction to produce the (R)-3-hydroxybutyrate derivatives.

1 . A compound of Formula 3: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof, wherein: 
         R is selected from the group consisting of glycerol, glucose, galactose, mannitol, or sucrose; 
         m is 2, 3, 4, 5, 6, or 7; 
         n is 1, 2, 3, 4, 5, or 6; and 
         x is 3, 4, 5, 6, or 7. 
       
     
     
         2 . The compound of  claim 1 , wherein R is glycerol. 
     
     
         3 . The compound of  claim 2 , wherein:
 m is 2;   n is 3; and   x is 3.   
     
     
         4 . The compound of  claim 2 , wherein:
 m is 3;   n is 3; and   x is 3.   
     
     
         5 . The compound of  claim 1 , wherein R is glucose. 
     
     
         6 . The compound of  claim 5 , wherein:
 m is 5;   n is 1; and   x is 5.   
     
     
         7 . The compound of  claim 1 , wherein R is galactose. 
     
     
         8 . The compound of  claim 7 , wherein:
 m is 1;   n is 5; and   x is 5.   
     
     
         9 . The compound of  claim 7 , wherein:
 m is 4;   n is 3; and   x is 5.   
     
     
         10 . The compound of  claim 1 , wherein R is mannitol. 
     
     
         11 . The compound of  claim 10 , wherein:
 m is 6;   n is 2; and   x is 6.   
     
     
         12 . The compound of  claim 1 , wherein R is sucrose. 
     
     
         13 . The compound of  claim 12 , wherein:
 m is 7;   n is 1; and   x is 7.   
     
     
         14 . The compound of  claim 12 , wherein:
 m is 7;   n is 3; and   x is 7.   
     
     
         15 . The compound of  claim 12 , wherein:
 m is 1;   n is 6; and   x is 7.   
     
     
         16 . A pharmaceutical composition comprising a compound of  claim 1  and a pharmaceutically acceptable carrier.