Hydroxybutyrate ester and medical use thereof

Abstract

A compound which is 3-hydroxybutyl 3-hydroxybutyrate enantiomerically enriched with respect to (3R)-hydroxybutyl (3R)-hydroxybutyrate of formula (I) is an effective and palatable precursor to the ketone body (3R)-hydroxybutyrate and may therefore be used to treat a condition which is caused by, exacerbated by or associated with elevated plasma levels of free fatty acids in a human or animal subject, for instance a condition where weight loss or weight gain is implicated, or to promote alertness or improve cognitive function, or to treat, prevent or reduce the effects of neurodegeneration, free radical toxicity, hypoxic conditions or hyperglycaemia.

1 . A compound which is (3R)-hydroxybutyl (3R)-hydroxybutyrate of formula (I): 
       
         
           
           
               
               
           
         
       
     
     
         2 . An ingestible composition which comprises a compound as defined in  claim 1  and a dietetically or pharmaceutically acceptable carrier. 
     
     
         3 . A composition according to  claim 2  which is a food product, a beverage, a drink, a food supplement, a dietary supplement, a functional food, a nutraceutical or a medicament. 
     
     
         4 . (canceled) 
     
     
         5 . A method of treating a condition which is caused by, exacerbated by or associated with elevated plasma levels of free fatty acids in a human or animal subject, which method comprises administering to the subject a compound as defined in  claim 1 . 
     
     
         6 . A method of treating a condition where weight loss or weight gain is implicated, which method comprises administering to a subject in need thereof a compound as defined in  claim 1 . 
     
     
         7 . A method of suppressing appetite, treating obesity, promoting weight loss, maintaining a healthy weight or decreasing the ratio of fat to lean muscle, which method comprises administering to a subject in need thereof a compound as defined in  claim 1 . 
     
     
         8 . A method of preventing or treating a condition selected from cognitive dysfunction, a neurodegenerative disease or disorder, muscle impairment, fatigue and muscle fatigue, which method comprises administering to a subject in need thereof a compound as defined in  claim 1 . 
     
     
         9 . A method of treating a patient suffering from a condition selected from diabetes, hyperthyroidism, metabolic syndrome X, or for treating a geriatric patient, which method comprises administering thereto a compound as defined in  claim 1 . 
     
     
         10 . A method of treating, preventing, or reducing the effects of, neuro degeneration, free radical toxicity, hypoxic conditions or hyperglycaemia which method comprises administering to a subject in need thereof a compound as defined in  claim 1 . 
     
     
         11 . A method according to  claim 10 , wherein the neurodegeneration is caused by aging, trauma, anoxia or a neurodegenerative disease or disorder. 
     
     
         12 . A method of preventing or treating a neurodegenerative disease or disorder selected from Alzheimer's disease, Parkinson's disease, amyotrophic lateral sclerosis, epilepsy, astrocytoma, glioblastoma and Huntington's chorea, which method comprises administering to a subject in need thereof a compound as defined in  claim 1 . 
     
     
         13 . A method of promoting alertness or improving cognitive function in a subject, which method comprises administering to said subject a compound as defined in  claim 1 . 
     
     
         14 . The compound of  claim 1 , wherein the compound is enantiomerically enriched to at least 90%. 
     
     
         15 . The compound of  claim 1 , wherein the compound is enantiomerically enriched to at least 95%. 
     
     
         16 . The compound of  claim 1 , wherein the compound is enantiomerically enriched to at least 97%. 
     
     
         17 . The compound of  claim 1 , wherein the compound is enantiomerically enriched to at least 98%. 
     
     
         18 . The compound of  claim 1 , wherein the compound is enantiomerically enriched to at least 99%. 
     
     
         19 . A method of preventing or treating muscle impairment or muscle fatigue in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the compound of  claim 1 .