CA2734720C - Hydroxybutyrate ester and medical use thereof - Google Patents

Hydroxybutyrate ester and medical use thereof Download PDF

Info

Publication number
CA2734720C
CA2734720C CA2734720A CA2734720A CA2734720C CA 2734720 C CA2734720 C CA 2734720C CA 2734720 A CA2734720 A CA 2734720A CA 2734720 A CA2734720 A CA 2734720A CA 2734720 C CA2734720 C CA 2734720C
Authority
CA
Canada
Prior art keywords
compound
treating
hydroxybutyrate
subject
condition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CA2734720A
Other languages
English (en)
French (fr)
Other versions
CA2734720A1 (en
Inventor
Kieran Clarke
Richard Lewis Veech
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Oxford University Innovation Ltd
US Department of Health and Human Services
Original Assignee
Oxford University Innovation Ltd
US Department of Health and Human Services
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Oxford University Innovation Ltd, US Department of Health and Human Services filed Critical Oxford University Innovation Ltd
Publication of CA2734720A1 publication Critical patent/CA2734720A1/en
Application granted granted Critical
Publication of CA2734720C publication Critical patent/CA2734720C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
    • A61P5/16—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4 for decreasing, blocking or antagonising the activity of the thyroid hormones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Neurology (AREA)
  • Diabetes (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Pain & Pain Management (AREA)
  • Emergency Medicine (AREA)
  • Epidemiology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Nutrition Science (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Toxicology (AREA)
  • Food Science & Technology (AREA)
  • Biochemistry (AREA)
  • Hospice & Palliative Care (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Mycology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Polymers & Plastics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2734720A 2008-08-21 2009-04-16 Hydroxybutyrate ester and medical use thereof Active CA2734720C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US9075108P 2008-08-21 2008-08-21
US61/090,751 2008-08-21
PCT/US2009/040766 WO2010021766A1 (en) 2008-08-21 2009-04-16 Hydroxybutyrate ester and medical use thereof

Publications (2)

Publication Number Publication Date
CA2734720A1 CA2734720A1 (en) 2010-02-25
CA2734720C true CA2734720C (en) 2017-07-18

Family

ID=40885956

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2734720A Active CA2734720C (en) 2008-08-21 2009-04-16 Hydroxybutyrate ester and medical use thereof

Country Status (10)

Country Link
EP (3) EP2328858B1 (cg-RX-API-DMAC7.html)
JP (2) JP5773870B2 (cg-RX-API-DMAC7.html)
CN (1) CN102164884B (cg-RX-API-DMAC7.html)
AU (1) AU2009283171B2 (cg-RX-API-DMAC7.html)
CA (1) CA2734720C (cg-RX-API-DMAC7.html)
DK (2) DK3296284T3 (cg-RX-API-DMAC7.html)
ES (2) ES2907630T3 (cg-RX-API-DMAC7.html)
NO (1) NO2328858T3 (cg-RX-API-DMAC7.html)
PL (2) PL2328858T3 (cg-RX-API-DMAC7.html)
WO (1) WO2010021766A1 (cg-RX-API-DMAC7.html)

Families Citing this family (59)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK1648952T3 (en) 2003-06-03 2018-05-28 The Us Gov As Represented By The Department Of Health And Human Services Dietary supplements and therapeutic compositions comprising (R) -3-hydroxybutyrate derivatives
DK2240017T3 (da) 2008-01-04 2019-06-17 Univ Oxford Innovation Ltd Ketonlegemer og ketonlegemsestere som blodlipid-sænkende midler
US8642654B2 (en) 2009-04-16 2014-02-04 Isis Innovation Limited Hydroxybutyrate ester and medical use thereof
GB201002983D0 (en) 2010-02-22 2010-04-07 Tdeltas Ltd Nutritinal composition
US8329938B2 (en) * 2011-02-21 2012-12-11 Eastman Chemical Company Hydroxyalkanoic acid and hydroxyalkanoice acid oligomer esters of retinol
GB201206192D0 (en) * 2012-04-05 2012-05-23 Tdeltas Ltd Ketone bodies and ketone body esters and for maintaining or improving muscle power output
ES2752030T3 (es) * 2012-11-05 2020-04-02 Us Health Cuerpos cetónicos para proteger los tejidos del daño por radiación ionizante
GB201304467D0 (en) * 2013-03-12 2013-04-24 Tdeltas Ltd Compound for use in protecting skin
CA2905225C (en) 2013-03-14 2021-05-04 Isis Innovation Limited Process for producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate
GB201314127D0 (en) * 2013-08-07 2013-09-18 Tdeltas Ltd Ketone body and ketone body ester for reducing muscle breakdown
EP3549928B1 (en) * 2014-01-13 2021-09-22 University of South Florida Methods of sustaining dietary ketosis and its effects on muscle fatigue
CN103860533A (zh) * 2014-02-12 2014-06-18 新乡医学院 β羟基丁酸在治疗帕金森病中的应用
CN106456686A (zh) * 2014-03-19 2017-02-22 斯坦陵布什大学 用于治疗或增强肌肉组织的方法
US10245242B1 (en) * 2017-11-22 2019-04-02 Axcess Global Sciences, Llc Non-racemic beta-hydroxybutyrate compounds and compositions enriched with the R-enantiomer and methods of use
US11241403B2 (en) 2016-03-11 2022-02-08 Axcess Global Sciences, Llc Beta-hydroxybutyrate mixed salt compositions and methods of use
US11103470B2 (en) 2017-11-22 2021-08-31 Axcess Global Sciences, Llc Non-racemic beta-hydroxybutyrate compounds and compositions enriched with the R-enantiomer and methods of use
US12109182B2 (en) 2016-04-19 2024-10-08 Axcess Global Sciences, Llc Administration of R-beta-hydroxybutyrate and related compounds in humans
US11944598B2 (en) 2017-12-19 2024-04-02 Axcess Global Sciences, Llc Compositions containing s-beta-hydroxybutyrate or non-racemic mixtures enriched with the s-enatiomer
US12496283B2 (en) 2016-04-19 2025-12-16 Axcess Global Sciences, Llc Administration of R-beta-hydroxybutyrate and related compounds in humans
SG11201809211QA (en) * 2016-04-19 2018-11-29 Keto Patent Group Inc Administration of butyrate, beta-hydroxybutyrate, and related compounds in humans
US11806324B2 (en) 2018-04-18 2023-11-07 Axcess Global Sciences, Llc Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies
US10925843B2 (en) 2018-04-18 2021-02-23 Axcess Global Sciences, Llc Compositions and methods for keto stacking with beta-hydroxybutyrate and acetoacetate
US12329734B2 (en) 2017-12-19 2025-06-17 Axcess Global Sciences, Llc Use of S-beta-hydroxybutyrate compounds for induction and maintenance of flow
US11026929B2 (en) 2016-04-19 2021-06-08 Keto Patent Group, Inc. Administration of berberine metabolites
US11202769B2 (en) 2017-11-22 2021-12-21 Axcess Global Sciences, Llc Ketone body esters of s-beta-hydroxybutyrate and/or s-1,3-butanediol for modifying metabolic function
MX385367B (es) 2016-06-07 2025-03-18 The J David Gladstone Inst Esteres de acidos grasos de cadena media de beta-hidroxibutirato y butanodiol y composiciones y metodos para usar los mismos.
US20180057846A1 (en) 2016-08-30 2018-03-01 KetoneAid Inc. Partially buffered free acid and/or ketone blend for rapid onset ketosis and metabolic therapy
MX390420B (es) * 2016-12-23 2025-03-20 Univ Leuven Kath 3-hidroxibutirato solo o en combinación para su uso en el tratamiento de cuidados intensivos.
US12171735B2 (en) 2017-04-19 2024-12-24 Axcess Global Sciences, Llc Administration of butyrate, beta-hydroxybutyrate, cannabidiol, and related compounds in humans
GB201710229D0 (en) * 2017-06-27 2017-08-09 Tdeltas Ltd Compounds for new use
EP3654963A4 (en) * 2017-07-21 2021-04-14 Buck Institute for Research on Aging BETA-HYDROXYBUTYRATE AND BUTANEDIOL S ENANTIOMERS AND THEIR METHODS OF USE
US11760963B2 (en) 2017-08-23 2023-09-19 KetoneAid Inc. Ketogenic beer and alcoholic beverage mixture containing non-racemic ethyl 3-hydroxybutyrate and/or 1,3 butanediol
GB201715654D0 (en) 2017-09-27 2017-11-08 Tdeltas Ltd Method of treatment
US12090129B2 (en) 2017-11-22 2024-09-17 Axcess Global Sciences, Llc Non-racemic beta-hydroxybutyrate compounds and compositions enriched with the R-enantiomer and methods of use
US12037317B2 (en) 2018-01-25 2024-07-16 Buck Institute For Research On Aging Synthesis of 3-hydroxybutyryl 3-hydroxybutyrate and related compounds
GB2572185A (en) * 2018-03-21 2019-09-25 Chain Biotechnology Ltd Pharmaceutical compositions
GB2575623B (en) * 2018-06-04 2022-10-26 Tdeltas Ltd 3-hydroxybutyrate esters for treating cancer cachexia
CA3022995C (en) * 2018-06-12 2019-10-15 Ketofibe (9211-3133 Quebec Inc.) Novel ketogenic compounds, compositions, methods and use thereof
US20210267251A1 (en) * 2018-06-21 2021-09-02 Societe Des Produits Nestle S.A. Compositions and methods using a nicotinamide adenine dinucleotide (nad+) precursor and at least one ketone or ketone precursor
GB2577723A (en) * 2018-10-04 2020-04-08 Tdeltas Ltd Compounds for new use
CN113329992B (zh) * 2019-01-17 2024-04-30 凯托利皮克斯治疗有限责任公司 基于多元醇的羟基羧酸酯的生产方法
CN109700021A (zh) * 2019-03-04 2019-05-03 清华大学 3-羟基丁酸及其衍生物在制备预防和治疗肥胖及肥胖相关疾病的产品中的应用
BR112021021557A2 (pt) 2019-05-10 2021-12-28 Ketoswiss Ag Corpos de cetona confinados em microesferas
US12472200B2 (en) 2019-05-15 2025-11-18 Axcess Global Sciences, Llc Autobiotic compositions and method for promoting healthy gut microbiome
WO2020234348A1 (en) * 2019-05-21 2020-11-26 Société des Produits Nestlé S.A. Dietary butyrate
CN114008015B (zh) * 2019-06-12 2024-02-20 凯托利皮克斯治疗有限责任公司 羟基羧酸多元醇酯、特别是聚甘油酯的制备方法
US20250197566A1 (en) * 2019-06-12 2025-06-19 Ioi Oleo Gmbh Process for preparing polyol-based esters of acyl-capped hydroxy carboxylic acids
US11950616B2 (en) 2019-06-21 2024-04-09 Axcess Global Sciences, Llc Non-vasoconstricting energy-promoting compositions containing ketone bodies
US11969430B1 (en) 2023-03-10 2024-04-30 Axcess Global Sciences, Llc Compositions containing paraxanthine and beta-hydroxybutyrate or precursor for increasing neurological and physiological performance
US12167993B2 (en) 2019-06-21 2024-12-17 Axcess Global Sciences, Llc Non-vasoconstricting energy-promoting compositions containing ketone bodies
WO2021195477A1 (en) * 2020-03-27 2021-09-30 Ketoneaid, Inc. Ketone ester as a therapeutic treatment of covid-19, long covid, and related viral infections
US20230174454A1 (en) * 2020-05-12 2023-06-08 Genomatica, Inc. Process of synthesizing and purifying (3r)-hydroxybutyl (3r)-hydroxybutanoate
WO2022012767A1 (de) * 2020-07-13 2022-01-20 Ioi Oleo Gmbh Verfahren zur herstellung von polyglycerinestern von mit oxobutanol veresterten polycarbonsäuren
US20240228422A1 (en) * 2020-07-13 2024-07-11 Ioi Oleo Gmbh Process for preparing oxobutanol esters of polymeric carboxylic acids
US12186297B2 (en) 2020-08-26 2025-01-07 Axcess Global Sciences, Llc Compositions and methods for increasing lean-to-fat mass ratio
CN113045416B (zh) * 2021-03-23 2023-08-18 南京纽邦生物科技有限公司 一种(r)-3-羟基丁酰-(r)-3-羟基丁酯的制备方法
US20240342121A1 (en) * 2021-07-09 2024-10-17 Georgia State University Research Foundation, Inc. The use of beta-hydroxybutyrates for the treatment or prevention of aneurysms and dissections
CA3219283A1 (en) 2021-07-17 2023-01-26 Elena GROSS Combination of a ketone body or ketogenic compound with an analgesic or antioxidant
IT202100020441A1 (it) 2021-07-30 2023-01-30 Unichem Estense S R L Miscela di un mono-estere e un di-estere, in cui detti mono-estere e di-estere sono esteri dell’acido (R)-3-idrossibutanoico con un polialcol, processo per la preparazione della miscela e relativi usi medici

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1051853B (it) * 1975-01-07 1981-05-20 Basf Ag Butandiol 1.3 3 mono 3 idros sibutirrati butandiol 1.3 1mono 3 idrossibutirrati e processi per la loro preparazione
JPH0755158B2 (ja) * 1986-10-30 1995-06-14 チッソ株式会社 光学活性エステルの製造法
BE1001209A3 (fr) * 1987-11-19 1989-08-22 Solvay Compositions pharmaceutiques contenant un derive de l'acide 3-hydroxybutanoique choisi parmi les oligomeres de cet acide et les esters de cet acide ou de ces oligomeres avec du 1,3-butanediol.
JP4598203B2 (ja) * 1995-12-01 2010-12-15 ビーティージー・インターナショナル・リミテッド 脳機能改善剤
WO2004105742A1 (en) 2003-06-02 2004-12-09 Isis Innovation Limited Treatment of muscle fatigue
DK1648952T3 (en) 2003-06-03 2018-05-28 The Us Gov As Represented By The Department Of Health And Human Services Dietary supplements and therapeutic compositions comprising (R) -3-hydroxybutyrate derivatives
WO2007063037A2 (de) * 2005-11-29 2007-06-07 Basf Se Verfahren zur um- oder veresterung von seitenketten in polymeren
US8452351B2 (en) * 2008-06-02 2013-05-28 Qualcomm Incorporated Methods and apparatus for saving battery power in mobile stations

Also Published As

Publication number Publication date
EP4011374A1 (en) 2022-06-15
CN102164884B (zh) 2015-03-11
CA2734720A1 (en) 2010-02-25
EP2328858A1 (en) 2011-06-08
PL3296284T3 (pl) 2022-06-13
PL2328858T3 (pl) 2018-06-29
JP6092836B2 (ja) 2017-03-08
JP2015057427A (ja) 2015-03-26
EP2328858B1 (en) 2017-10-11
EP3296284A1 (en) 2018-03-21
AU2009283171B2 (en) 2014-08-14
ES2655367T3 (es) 2018-02-19
HK1159604A1 (en) 2012-08-03
AU2009283171A1 (en) 2010-02-25
DK3296284T3 (da) 2022-02-28
EP3296284B1 (en) 2021-12-01
JP5773870B2 (ja) 2015-09-02
DK2328858T3 (en) 2018-01-15
NO2328858T3 (cg-RX-API-DMAC7.html) 2018-03-10
CN102164884A (zh) 2011-08-24
JP2012500264A (ja) 2012-01-05
ES2907630T3 (es) 2022-04-25
WO2010021766A1 (en) 2010-02-25

Similar Documents

Publication Publication Date Title
CA2734720C (en) Hydroxybutyrate ester and medical use thereof
US8642654B2 (en) Hydroxybutyrate ester and medical use thereof
TWI811222B (zh) 用於減少肝臟脂肪的3-羥基丁酸酯化合物
JP4820299B2 (ja) 肥満、心臓血管疾患及び冠状動脈疾患の予防及び治療のための組成物
JP5587780B2 (ja) フコキサンチン又はこれを含有する海藻類抽出物を含有する脂質代謝性疾患の予防又は治療用組成物
JP6193229B2 (ja) 血管内皮機能低下の予防または改善剤
US20200385331A1 (en) Alternative ketone esters and production processes thereof
JP2021501119A (ja) 丹参抽出物を含む内臓脂肪型肥満予防、改善又は治療組成物
EP2990048A1 (en) Nitric oxide concentration elevating agent
US20190119705A1 (en) Substantially non-racemic ketone ester of beta hydroxybutyrate and production process thereof
EP3801490A1 (en) Compounds for use in cancer cachexia
WO2002100393A1 (fr) Compositions destinees a ameliorer les troubles de manque d'attention/d'hyperactivite
KR20150110821A (ko) 케톤체 축적 억제제
US20080161413A1 (en) Agent for increasing adiponectin in blood
HK1159604B (en) Hydroxybutyrate ester and medical use thereof
JP2004292355A (ja) 抗ストレス剤
JP2023173641A (ja) 内臓脂肪低減剤およびその用途
CN112450436A (zh) 一种具有改善心血管功能的组合物及应用
WO2007049628A1 (ja) 血液流動性改善剤
JP2007246488A (ja) 消化性潰瘍改善組成物

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20140409