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)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
  • Diabetes (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Endocrinology (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Nutrition Science (AREA)
  • Psychology (AREA)
  • Psychiatry (AREA)
  • Toxicology (AREA)
  • Food Science & Technology (AREA)
  • Biochemistry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Child & Adolescent Psychology (AREA)
  • Cardiology (AREA)
  • Mycology (AREA)
  • Hospice & Palliative Care (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) EP4011374A1 (enExample)
JP (2) JP5773870B2 (enExample)
CN (1) CN102164884B (enExample)
AU (1) AU2009283171B2 (enExample)
CA (1) CA2734720C (enExample)
DK (2) DK3296284T3 (enExample)
ES (2) ES2655367T3 (enExample)
NO (1) NO2328858T3 (enExample)
PL (2) PL3296284T3 (enExample)
WO (1) WO2010021766A1 (enExample)

Families Citing this family (62)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2004245567B2 (en) 2003-06-03 2011-06-23 Oxford University Innovation Limited Nutritional supplements and therapeutic compositions comprising (R)-3-hydroxybutyrate derivatives
ES2730879T3 (es) 2008-01-04 2019-11-13 Univ Oxford Innovation Ltd Cuerpos de cetona y ésteres de cuerpos de cetona como agentes reductores de lípidos de la sangre
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
AU2013337308B2 (en) 2012-11-05 2018-06-21 Tdeltas Ketone bodies to protect tissues from damage by ionizing radiation
GB201304467D0 (en) 2013-03-12 2013-04-24 Tdeltas Ltd Compound for use in protecting skin
CN105246870A (zh) * 2013-03-14 2016-01-13 伊希斯创新有限公司 (r)-3-羟基丁酸(r)-3-羟基丁酯的制备方法
GB201314127D0 (en) * 2013-08-07 2013-09-18 Tdeltas Ltd Ketone body and ketone body ester for reducing muscle breakdown
WO2015156865A1 (en) 2014-01-13 2015-10-15 University Of South Florida Methods of sustaining dietary ketosis and its effects on lipid profile
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
EP3125912B1 (en) * 2014-03-19 2019-05-29 Stellenbosch University Method for treating or enhancing muscle tissue
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
US11241403B2 (en) 2016-03-11 2022-02-08 Axcess Global Sciences, Llc Beta-hydroxybutyrate mixed salt compositions and methods of use
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
US11806324B2 (en) 2018-04-18 2023-11-07 Axcess Global Sciences, Llc Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies
US12496283B2 (en) 2016-04-19 2025-12-16 Axcess Global Sciences, Llc Administration of R-beta-hydroxybutyrate and related compounds in humans
US12521378B2 (en) 2016-04-19 2026-01-13 Axcess Global Sciences, Llc Administration of R-beta-hydroxybutyrate salt blend and related compounds in humans
US12533346B2 (en) 2016-04-19 2026-01-27 Axcess Global Sciences, Llc 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
US12329734B2 (en) 2017-12-19 2025-06-17 Axcess Global Sciences, Llc Use of S-beta-hydroxybutyrate compounds for induction and maintenance of flow
US10925843B2 (en) 2018-04-18 2021-02-23 Axcess Global Sciences, Llc Compositions and methods for keto stacking with beta-hydroxybutyrate and acetoacetate
US20230346721A1 (en) 2018-04-18 2023-11-02 Axcess Global Sciences, Llc Beta-hydroxybutyric acid compositions and methods for delivery of ketone bodies
SG11201809211QA (en) * 2016-04-19 2018-11-29 Keto Patent Group Inc Administration of butyrate, beta-hydroxybutyrate, and related compounds in humans
US11026929B2 (en) 2016-04-19 2021-06-08 Keto Patent Group, Inc. Administration of berberine metabolites
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
US12109182B2 (en) 2016-04-19 2024-10-08 Axcess Global Sciences, Llc Administration of R-beta-hydroxybutyrate and related compounds in humans
WO2017213999A1 (en) 2016-06-07 2017-12-14 The J. David Gladstone Institutes Medium chain fatty acid esters of beta-hydroxybutyrate and butanediol and compositions and methods for using same
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
IL272173B2 (en) * 2017-07-21 2025-06-01 Buck Inst Res Aging S-enantiomers of beta-hydroxybutyrate and butanediol and methods for using same
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
WO2019147503A1 (en) 2018-01-25 2019-08-01 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
US12403152B2 (en) * 2018-06-21 2025-09-02 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
WO2020147979A1 (de) * 2019-01-17 2020-07-23 Ioi Oleo Gmbh Verfahren zur herstellung von polyolbasierten estern von hydroxycarbonsäuren
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
JP2022532709A (ja) 2019-05-10 2022-07-19 ケトスイス アーゲー マイクロビーズに封入されたケトン体
US12472200B2 (en) 2019-05-15 2025-11-18 Axcess Global Sciences, Llc Autobiotic compositions and method for promoting healthy gut microbiome
US20220218647A1 (en) * 2019-05-21 2022-07-14 Societe Des Produits Nestle S.A. Dietary butyrate
US20230020342A1 (en) * 2019-06-12 2023-01-19 Ioi Oleo Gmbh Method for producing polyol-based esters, in particular polyglycerol esters, from hydroxy carboxylic acids
CN114008014B (zh) * 2019-06-12 2024-03-22 凯托利皮克斯治疗有限责任公司 用于生产酰基封端的3-羟基羧酸的多元醇基酯的方法
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
US11950616B2 (en) 2019-06-21 2024-04-09 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
EP4146337B1 (de) * 2020-07-13 2024-04-17 KetoLipix Therapeutics GmbH Verfahren zur herstellung von polyglycerinestern von mit oxobutanol veresterten polycarbonsäuren
WO2022012766A1 (de) * 2020-07-13 2022-01-20 Ioi Oleo Gmbh Verfahren zur herstellung von oxobutanol-estern von polymeren carbonsäuren
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
WO2023283654A1 (en) * 2021-07-09 2023-01-12 Georgia State University Research Foundation, Inc. The use of beta-hydroxybutyrates for the treatment or prevention of aneurysms and dissections
JP2024525851A (ja) 2021-07-17 2024-07-12 ケトスイス アーゲー ケトン体またはケト原性化合物と鎮痛剤または抗酸化剤との組み合わせ
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
DK1641444T3 (en) 2003-06-02 2016-06-27 Isis Innovation Treatment of muscle fatigue
AU2004245567B2 (en) * 2003-06-03 2011-06-23 Oxford University Innovation Limited Nutritional supplements and therapeutic compositions comprising (R)-3-hydroxybutyrate derivatives
JP5145240B2 (ja) * 2005-11-29 2013-02-13 ビーエーエスエフ ソシエタス・ヨーロピア ポリマー中の側鎖をエステル交換またはエステル化する方法
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
AU2009283171B2 (en) 2014-08-14
EP4011374A1 (en) 2022-06-15
NO2328858T3 (enExample) 2018-03-10
PL3296284T3 (pl) 2022-06-13
DK3296284T3 (da) 2022-02-28
DK2328858T3 (en) 2018-01-15
ES2655367T3 (es) 2018-02-19
EP3296284B1 (en) 2021-12-01
EP3296284A1 (en) 2018-03-21
HK1159604A1 (en) 2012-08-03
CA2734720A1 (en) 2010-02-25
AU2009283171A1 (en) 2010-02-25
CN102164884B (zh) 2015-03-11
JP6092836B2 (ja) 2017-03-08
PL2328858T3 (pl) 2018-06-29
JP5773870B2 (ja) 2015-09-02
WO2010021766A1 (en) 2010-02-25
ES2907630T3 (es) 2022-04-25
EP2328858B1 (en) 2017-10-11
JP2015057427A (ja) 2015-03-26
CN102164884A (zh) 2011-08-24
EP2328858A1 (en) 2011-06-08
JP2012500264A (ja) 2012-01-05

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

MPN Maintenance fee for patent paid

Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 16TH ANNIV.) - STANDARD

Year of fee payment: 16

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20250407

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20250407