# US 2014/0194509 A1 · Hydroxybutyrate ester and medical use thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0194509 A1 - Document ID: US20140194509A1 - Status: Published application - Kind: A1 - Application number: 14/101,834 - Filed: 2013-12-10 - Published: 2014-07-10 - Earliest claimed: 2008-08-21 - Assignees: The Government of the USA, as represented by the Secretary, Department of Health and Human Services; Isis Innovation Limited - Applicants: Government of the USA, as Represented by the Secretary, Department of Health and Human Services; Isis Innovation Limited - Inventors: Kieran Clarke; Richard Lewis Veech - Web page: https://patentgrep.com/patent/US20140194509A1 ## CPC - A23L 2/52: Adding ingredients (adding preservatives A23B70/10) - A23L 33/10: using additives (addition of substantially indigestible substances A23L33/21) - A61K 31/22: of acyclic acids, e.g. pravastatin - A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00) - A61P 21/00: Drugs for disorders of the muscular or neuromuscular system - A61P 25/16: Anti-Parkinson drugs - A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia - C07C 69/675: of saturated hydroxy-carboxylic acids - A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs - C07B 2200/07: Optical isomers - A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B) - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION - C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F) ## 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. ## Claims ### Claim 1 An ingestible compound which is 3-hydroxybutyl 3-hydroxybutyrate enantiomerically enriched with respect to (3R)-hydroxybutyl (3R)-hydroxybutyrate of formula (I): ### Claim at position 2 2-4. (canceled) ### Claim 5 (depends on 1) 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, wherein the method comprises administering to the subject a compound as defined in claim 1. ### Claim 6 (depends on 1) A method of treating a condition where weight loss or weight gain is implicated, wherein the method comprises administering to a subject in need thereof a compound as defined in claim 1. ### Claim 7 (depends on 1) A method of suppressing appetite, treating obesity, promoting weight loss, maintaining a healthy weight or decreasing the ratio of fat to lean muscle, wherein the method comprises administering to a subject in need thereof a compound as defined in claim 1. ### Claim 8 (depends on 1) A method of treating a condition selected from cognitive dysfunction, a neurodegenerative disease or disorder, muscle impairment, fatigue and muscle fatigue, wherein the method comprises administering to a subject having condition or prior to the subject having said condition a compound as defined in claim 1. ### Claim 9 (depends on 1) 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 to the patient a compound as defined in claim 1. ### Claim 10 (depends on 1) A method of treating, preventing, or reducing the effects of, neuro degeneration, free radical toxicity, hypoxic conditions or hyperglycaemia, wherein the method comprises administering to a subject in need thereof a compound as defined in claim 1. ### Claim 11 (depends on 10) The method according to claim 10, wherein the neurodegeneration is caused by aging, trauma, anoxia or a neurodegenerative disease or disorder. ### Claim 12 (depends on 1) 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, wherein the method comprises administering to a subject in need thereof a compound as defined in claim 1. ### Claim 13 (depends on 1) A method of promoting alertness or improving cognitive function in a subject, wherein the method comprises administering to said subject a compound as defined in claim 1. ### Claim 14 (depends on 1) An ingestible compound according to claim 1, wherein the compound is enantiomerically enriched to at least 90%. ### Claim 15 (depends on 7) The method according to claim 7, wherein the subject is a healthy subject. ### Claim 16 (depends on 9) The method according to claim 9, wherein the patient has diabetes, and wherein the patient has a body mass index (BMI) of 25 or more. ### Claim 17 (depends on 1, 9) The method according to claim 9, wherein the patient has diabetes, and wherein the method comprises administering to the patient a compound as defined in claim 1 in combination with a conventional anti-diabetic agent. ### Claim 18 A process for preparing a compound which is (3R)-hydroxybutyl (3R)-hydroxybutyrate of formula (I): wherein the process comprises: a) reacting ethyl (3R)-hydroxybutyrate and (R)-1,3-butanediol under transesterification conditions in the presence of a lipase enzyme to produce a crude reaction product comprising 3-hydroxybutyl 3-hydroxybutyrate; and b) treating the crude reaction product to produce 3-hydroxybutyl 3-hydroxybutyrate enantiomerically enriched with respect to (3R)-hydroxybutyl (3R)-hydroxybutyrate. ### Claim 19 (depends on 18) The process according to claim 18, wherein the process comprises filtering the crude reaction product from step a of the process. ### Claim 20 (depends on 1) A composition for rehydration, wherein the composition comprises the compound according to claim 1, water, and a sugar carbohydrate.