Novel ketogenic compounds, compositions, methods and use thereof

Abstract

The present disclosure relates to compounds comprising β-hydroxybutyric acid, and a weakly basic polymer. The disclosure also includes methods for inducing nutritional ketosis comprising administering the compounds or compositions comprising the compounds to a mammal in need thereof.

Without prejudice or disclaimer, please amend the claims as follows: 
     
         1 . A compound, comprising:
 a) β-hydroxybutyric acid (BHB); and   b) an ingestible and non-digestible weakly basic polymer, comprising monomers having weak base functional groups.   
     
     
         2 . The compound according to  claim 1 , wherein the molar ratio of BHB to the weak base monomer is about 1:1. 
     
     
         3 . (canceled) 
     
     
         4 . (canceled) 
     
     
         5 . The compound of  claim 4 , wherein the BHB is D-BHB. 
     
     
         6 . The compound of  claim 1 , wherein the weakly basic polymer has a pKb of between about 4 to about 10.5. 
     
     
         7 . The compound of  claim 1 , wherein the weakly basic polymer is sodium-carboxymethylcellulose or chitosan. 
     
     
         8 . The compound of  claim 1  wherein the compound has the formula
   [(weakly basic monomer) + (BHB) − ] x    
 wherein x is an integer between about 2 and about 1000. 
 
     
     
         9 . The compound of  claim 1 , wherein the weakly basic polymer has the formula
   [(glucNH 2 ) n (glucNHAc) m ]   wherein   (glucNH 2 ) is a glucosamine residue,   (glucNHAc) is an N-acetylglucosamine residue;   “m” ranges from 0% to about 30% of the total residues;   “n” ranges from 70% to about 100% of the total residues;   wherein the total number of residues is between about 2 to about 1000.   
     
     
         10 . The compound of  claim 9 , wherein the polymer has a mass of between about 9 kD to about 300 kD. 
     
     
         11 . The compound of  claim 9 , wherein the compound has the structure: 
       
         
           
           
               
               
           
         
       
     
     
         12 . The compound of  claim 9 , wherein the weakly basic polymer has the formula
   [(glu(CH 2 CO 2 ) x M x [ n (glu) m ]   wherein   [glu(CH 2 CO 2 ) x M x ] are carboxymethyl glucose residues,   glu are glucose residues;   x=1 or 2 or 3 and M are cations with charge, +1 or +2 or +3;   “m” ranges from 0% to about 30% of the total residues;   “n” ranges from 70% to about 100% of the total residues;   wherein the total number of residues is between about 2 to about 1000.   
     
     
         13 . The compound of  claim 12 , wherein the polymer has a mass of between about 9 kD to about 300 kD. 
     
     
         14 . The compound of  claim 12 , wherein the compound has the structure 
       
         
           
           
               
               
           
         
       
     
     
         15 . The compound of  claim 1 , wherein the BHB has an intolerable taste and the compound is substantially free of the intolerable taste. 
     
     
         16 . The compound of  claim 15 , wherein the concentration of the BHB in a solution is at least about 1.0% (weight/volume). 
     
     
         17 . A hydrogel comprising,
 a) β-hydroxybutyric acid (BHB);   b) an ingestible and non-digestible weakly basic polymer, comprising monomers having weak base functional groups; and   c) water,   wherein the molar ratio of BHB to the weak base functional group is about 1:1.   
     
     
         18 . The hydrogel of  claim 15 , wherein the hydrogel further comprises additional ketogenic precursors. 
     
     
         19 . The hydrogel of  claim 17 , wherein the ketogenic precursor is poly-BHB, oligomers of BHB, 1,3-butanediol, and/or acetoacetic acid or esters thereof. 
     
     
         20 . The hydrogel of  claim 17 , further comprising additional BHB. 
     
     
         21 . The hydrogel of  claim 20 , wherein the ratio of BHB to weak base functional groups is greater than 1 to 1. 
     
     
         22 . (canceled) 
     
     
         23 . (canceled) 
     
     
         24 . The hydrogel of  claim 23 , wherein the ratio of BHB to weak base functional groups is greater than about 10 to about 1. 
     
     
         25 . The hydrogel of  claim 17 , wherein the BHB is D-BHB. 
     
     
         26 . A method for increasing ketone levels comprising administering to a subject in need thereof a therapeutically effective amount of a compound as claimed in  claim 1 , wherein BHB has an intolerable taste and the compound or hydrogel is substantially free of the intolerable-taste. 
     
     
         27 . The method according to  claim 20 , for promoting ketosis, for promoting weight loss or suppressing appetite, for preventing or treating neurodegenerative conditions, for preventing or treating traumatic brain injuries, for treating a condition caused by muscle impairment or muscle fatigue, for the prevention or the improvement of treatment for cancer, for treating diabetes, or for regulating or lowering blood glucose levels.