CA2905225C - Process for producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate - Google Patents

Process for producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate Download PDF

Info

Publication number
CA2905225C
CA2905225C CA2905225A CA2905225A CA2905225C CA 2905225 C CA2905225 C CA 2905225C CA 2905225 A CA2905225 A CA 2905225A CA 2905225 A CA2905225 A CA 2905225A CA 2905225 C CA2905225 C CA 2905225C
Authority
CA
Canada
Prior art keywords
hydroxybutyrate
alcohol
poly
process according
hydroxybutyl
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
CA2905225A
Other languages
English (en)
French (fr)
Other versions
CA2905225A1 (en
Inventor
Kieran Clarke
Richard Veech
Todd King
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 CA2905225A1 publication Critical patent/CA2905225A1/en
Application granted granted Critical
Publication of CA2905225C publication Critical patent/CA2905225C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/18Polyhydroxylic acyclic alcohols
    • C07C31/20Dihydroxylic alcohols
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/18Polyhydroxylic acyclic alcohols
    • C07C31/20Dihydroxylic alcohols
    • C07C31/2071,4-Butanediol; 1,3-Butanediol; 1,2-Butanediol; 2,3-Butanediol
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/02Preparation of carboxylic acid esters by interreacting ester groups, i.e. transesterification
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/03Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66Esters 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
    • C07C69/67Esters 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
    • C07C69/675Esters 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
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00Preparation of oxygen-containing organic compounds
    • C12P7/62Carboxylic acid esters
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07Optical isomers
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00Technologies for the production of fuel of non-fossil origin
    • Y02E50/10Biofuels, e.g. bio-diesel

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA2905225A 2013-03-14 2014-03-14 Process for producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate Active CA2905225C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361783167P 2013-03-14 2013-03-14
US61/783,167 2013-03-14
PCT/EP2014/055156 WO2014140308A1 (en) 2013-03-14 2014-03-14 Process for producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate

Publications (2)

Publication Number Publication Date
CA2905225A1 CA2905225A1 (en) 2014-09-18
CA2905225C true CA2905225C (en) 2021-05-04

Family

ID=50336299

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2905225A Active CA2905225C (en) 2013-03-14 2014-03-14 Process for producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate

Country Status (13)

Country Link
US (2) US11566268B2 (https=)
EP (1) EP2984066B1 (https=)
JP (1) JP6110959B2 (https=)
KR (1) KR102265842B1 (https=)
CN (1) CN105246870A (https=)
AU (1) AU2014230120B2 (https=)
BR (1) BR112015023334B1 (https=)
CA (1) CA2905225C (https=)
DK (1) DK2984066T3 (https=)
ES (1) ES2623368T3 (https=)
GB (1) GB2515603B (https=)
SG (1) SG11201507685UA (https=)
WO (1) WO2014140308A1 (https=)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1648952B1 (en) 2003-06-03 2018-03-07 THE UNITED STATES GOVERNMENT as represented by THE DEPARTMENT OF HEALTH AND HUMAN SERVICES Nutritional supplements and therapeutic compositions comprising (r)-3-hydroxybutyrate derivatives
EP2240017B1 (en) 2008-01-04 2019-03-13 Oxford University Innovation Limited Ketone bodies and ketone body esters as blood lipid lowering agents
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
DK2914251T3 (da) 2012-11-05 2019-11-04 Us Health Ketonlegemer til beskyttelse af væv mod beskadigelse som følge af ioniseringsstråling
GB201304467D0 (en) 2013-03-12 2013-04-24 Tdeltas Ltd Compound for use in protecting skin
GB2515603B (en) 2013-03-14 2015-10-14 Isis Innovation Process for producing (R)-3-Hydroxybutyl (R)-3-Hydroxybutyrate
US9249378B2 (en) 2013-08-02 2016-02-02 Eastman Chemical Company Aqueous cleaning compositions having enhanced properties
US9388114B2 (en) 2013-08-02 2016-07-12 Eastman Chemical Company Compositions including an alkyl 3-hydroxybutyrate
US9255059B2 (en) 2013-08-02 2016-02-09 Eastman Chemical Company Method for producing an alkyl 3-hydroxybutyrate
US9163202B2 (en) 2013-08-02 2015-10-20 Eastman Chemical Company Aqueous cleaning compositions including an alkyl 3-hydroxybutyrate
EP3400100B1 (en) * 2016-01-06 2020-09-23 Archer Daniels Midland Company Process for producing 1,3-butanediol and for optionally further producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate
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
GB201710229D0 (en) 2017-06-27 2017-08-09 Tdeltas Ltd Compounds for new use
WO2019018683A1 (en) 2017-07-21 2019-01-24 Buck Institute For Research On Aging BETA-HYDROXYBUTYRATE AND BUTANEDIOL ENANTIOMERS AND METHODS OF USE THEREOF
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
JP7039940B2 (ja) * 2017-11-09 2022-03-23 トヨタ自動車株式会社 車両制御装置
WO2019147503A1 (en) * 2018-01-25 2019-08-01 Buck Institute For Research On Aging Synthesis of 3-hydroxybutyryl 3-hydroxybutyrate and related compounds
GB2575623B (en) 2018-06-04 2022-10-26 Tdeltas Ltd 3-hydroxybutyrate esters for treating cancer cachexia
GB2577723A (en) 2018-10-04 2020-04-08 Tdeltas Ltd Compounds for new use
EP3880649B1 (de) * 2019-01-17 2023-03-15 KetoLipix Therapeutics GmbH Verfahren zur herstellung von polyolbasierten estern von hydroxycarbonsäuren
GB201918657D0 (en) 2019-12-17 2020-01-29 Tdeltas Ltd Compounds for new use
US12396974B2 (en) 2020-03-27 2025-08-26 KetoneAid Ketone ester as a therapeutic treatment of Covid-19 and related viral infections
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
EP4363599A1 (en) 2021-06-28 2024-05-08 PHB Industrial S.A. Methods to produce therapeutic formulations comprising hydroxybutirate and hydroxyvalerate, therapeutic formulations and uses thereof
WO2025143117A1 (ja) * 2023-12-28 2025-07-03 株式会社カネカ バイオマス由来ヒドロキシアルカン酸エステルの製造方法
CN119019245A (zh) * 2024-08-16 2024-11-26 上海康鑫化工有限公司 医药级3-羟基丁酸钠的制备方法

Family Cites Families (89)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1141293B (de) * 1958-08-22 1962-12-20 Iromedica A G Verfahren zur Herstellung von o-[Bis-(4, 4'-oxyphenyl)-methyl]-benzyl-alkohol (Phenolphthalol)
US3984566A (en) 1974-02-25 1976-10-05 Scott Eugene J Van Method of alleviating the symptoms of dandruff
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
US4380549A (en) 1975-07-23 1983-04-19 Scott Eugene J Van Topical treatment of dry skin
JPS54138126A (en) 1978-04-17 1979-10-26 Ajinomoto Co Inc Remedy for diabetes
EP0250559A1 (en) 1985-12-18 1988-01-07 VEECH, Richard L. Parenteral nutrition therapy with amino acids
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
US4916074A (en) 1986-10-30 1990-04-10 Chisso Corporation Process for producing optically active compounds
JP2579779B2 (ja) 1987-10-08 1997-02-12 日本車輌製造株式会社 飼料の製造法
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.
JPH0383950A (ja) 1989-08-28 1991-04-09 Kanegafuchi Chem Ind Co Ltd グリセリド誘導体およびその製造法
JP2873497B2 (ja) 1990-09-03 1999-03-24 理化学研究所 脂質代謝調節剤
EP0537113A1 (en) 1991-10-10 1993-04-14 SANDOZ NUTRITION Ltd. Energy supplementary food
JP2884123B2 (ja) 1992-01-17 1999-04-19 高砂香料工業株式会社 生分解性光学活性ポリマー、その中間体オリゴマー、およびそれらの製造方法
US5654266A (en) 1992-02-10 1997-08-05 Chen; Chung-Ho Composition for tissues to sustain viability and biological functions in surgery and storage
US5281691A (en) 1992-06-19 1994-01-25 Eastman Kodak Company Poly(3-hydroxyalkanoates)
US5468507A (en) 1993-07-13 1995-11-21 Czap; Al F. Composition containing a desired flavoring agent and medium chain triglycerides
JP3193542B2 (ja) 1993-09-08 2001-07-30 カネボウ株式会社 皮膚老化防止化粧料
WO1995009144A1 (en) 1993-09-30 1995-04-06 Eastman Chemical Company Nutritive water soluble glycerol esters of hydroxy butyric acid
DE4427492A1 (de) 1994-08-03 1996-02-08 Boehringer Mannheim Gmbh Verfahren zur Analyse einer medizinischen Probe unter Vermeidung von Störbeiträgen aufgrund von Hämolyse
ATE196486T1 (de) 1994-08-10 2000-10-15 Peter Neuenschwander Biokompatibles blockcopolymer
JPH08191664A (ja) 1995-01-12 1996-07-30 Yoshihide Hagiwara 新規コーヒー抽出物の製造法
WO1996028405A1 (fr) * 1995-03-10 1996-09-19 Nitto Chemical Industry Co., Ltd. Procede de production de derives de 1,2-ethanediol
US6306828B1 (en) 1995-04-06 2001-10-23 Baxter International, Inc. Enantiomerically-enhanced nutritional energy substrates
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
US6126953A (en) 1996-08-19 2000-10-03 The Procter & Gamble Company Fragrance delivery systems for personal care articles
JPH10175855A (ja) 1996-10-16 1998-06-30 Taisho Pharmaceut Co Ltd 肉体疲労改善剤
US6316038B1 (en) 1997-03-17 2001-11-13 Btg International Limited Therapeutic compositions
CN1315473C (zh) 1997-03-17 2007-05-16 英国技术集团国际有限公司 治疗组合物
US20090253781A1 (en) 2002-05-24 2009-10-08 Btg International Limited Therapeutic compositions
US6323237B1 (en) 1997-03-17 2001-11-27 Btg International Limited Therapeutic compositions
JPH10265378A (ja) 1997-03-25 1998-10-06 Ofutekusu:Kk 角膜上皮損傷治療剤
US6232346B1 (en) 1997-03-27 2001-05-15 Michael J. Sole Composition for improvement of cellular nutrition and mitochondrial energetics
JP3869071B2 (ja) 1997-05-14 2007-01-17 三栄源エフ・エフ・アイ株式会社 甘味食品
AU7580098A (en) 1997-05-15 1998-12-08 University Of Washington Composition and methods for treating alzheimer's disease and other amyloidoses
US6727258B2 (en) 1997-10-29 2004-04-27 King Pharmaceutical Research & Development, Inc. Allosteric adenosine receptor modulators
GB9723590D0 (en) 1997-11-08 1998-01-07 Glaxo Group Ltd Chemical compounds
DE69922206T2 (de) 1998-07-22 2005-11-24 Metabolix, Inc., Cambridge Nahrungs- und therapeutische verwendung von hydroxyalkanoat oligomere
DK1123094T3 (da) 1998-09-15 2007-08-20 Btg Int Ltd Terapeutiske præparater (II)
EP1194582A1 (de) * 1999-07-09 2002-04-10 Forschungszentrum Jülich Gmbh Verfahren zur reduktion von keto-carbonsäuren und deren estern
WO2007115282A2 (en) 2006-04-03 2007-10-11 Accera, Inc. Use of ketogenic compounds for treatment of age-associated memory impairment
AU2001257451A1 (en) 2000-05-01 2001-11-12 Accera, Inc. Use of medium chain triglycerides for the treatment and prevention of alzheimer's disease and other diseases resulting from reduced neuronal metabolism
US20070179197A1 (en) 2000-05-01 2007-08-02 Accera, Inc. Compositions and methods for improving or preserving brain function
EP2275468A1 (en) 2000-07-14 2011-01-19 Metabolix, Inc. Polyurethanes obtained from hydroxyalkanoates and isocyanates
US6970737B1 (en) 2000-09-13 2005-11-29 Ge Medical Systems Information Technologies, Inc. Portable ECG device with wireless communication interface to remotely monitor patients and method of use
AUPR177300A0 (en) 2000-11-29 2000-12-21 Centre For Molecular Biology And Medicine Therapeutic methods
US20050129783A1 (en) 2001-04-19 2005-06-16 Mccleary Edward L. Composition and method for treatment of neurophysiological conditions and maintenance of neurophysiological health
GB0118931D0 (en) 2001-08-02 2001-09-26 Oxford Biosensors Ltd Voltammetric ion-selective biosensor
WO2003051813A1 (en) 2001-12-18 2003-06-26 Metabolix, Inc. Methods of making intermediates from polyhydroxyalkanoates
GB0130684D0 (en) 2001-12-21 2002-02-06 Oxford Biosensors Ltd Micro-band electrode
DE20205184U1 (de) 2002-03-27 2002-12-19 Bartz, Volker, 35440 Linden Blutfettsenker zur oralen Einnahme
GB0211449D0 (en) 2002-05-17 2002-06-26 Oxford Biosensors Ltd Analyte measurement
US8996090B2 (en) 2002-06-03 2015-03-31 Exostat Medical, Inc. Noninvasive detection of a physiologic parameter within a body tissue of a patient
CN1483355A (zh) 2002-09-16 2004-03-24 岚 高 抗疲劳饮料配方
WO2004105742A1 (en) 2003-06-02 2004-12-09 Isis Innovation Limited Treatment of muscle fatigue
EP1648952B1 (en) 2003-06-03 2018-03-07 THE UNITED STATES GOVERNMENT as represented by THE DEPARTMENT OF HEALTH AND HUMAN SERVICES Nutritional supplements and therapeutic compositions comprising (r)-3-hydroxybutyrate derivatives
JP2005247821A (ja) 2004-02-06 2005-09-15 Ophtecs Corp 炎症性サイトカインの産生を抑制するための眼科用組成物
DE102004007029A1 (de) 2004-02-12 2005-09-08 Consortium für elektrochemische Industrie GmbH Verfahren zur enantioselektiven Reduktion von Ketoverbindungen durch Enzyme
US20050181275A1 (en) 2004-02-18 2005-08-18 Jang Bor Z. Open electrochemical cell, battery and functional device
WO2006020137A2 (en) 2004-07-16 2006-02-23 Ketocytonyx Inc. Oligomeric compounds
US20060057691A1 (en) 2004-09-15 2006-03-16 Karunakaran Narasimhan Process for the extraction of polyhydroxyalkanoates from biomass
US8124063B2 (en) 2004-10-25 2012-02-28 Conopco, Inc. Method for moisturizing human skin using dihydroxypropyltri(C1-C3 alkyl) ammonium salts
GB0427145D0 (en) 2004-12-10 2005-01-12 Ketocytonyx Inc Compositions for use in surgery
ITTO20040918A1 (it) 2004-12-29 2005-03-29 Luigi Ambrosio Idrogel polimerici superassorbenti biodegradabili e procedimento per la loro preparazione
WO2007001883A2 (en) 2005-06-20 2007-01-04 Accera, Inc. Method to reduce oxidative damage and improve mitochondrial efficiency
CA2631264A1 (en) 2005-11-29 2007-06-07 Basf Se Process for esterifying or transesterifying side chains in polymers
PL2004160T3 (pl) 2006-04-12 2013-02-28 Unilever Nv Doustna kompozycja o przeciwstarzeniowym działaniu na skórę
US7807718B2 (en) 2006-06-30 2010-10-05 Sami A. Hashim Glyceride esters for the treatment of diseases associated with reduced neuronal metabolism of glucose
JP5030553B2 (ja) 2006-11-24 2012-09-19 有限会社ノーベル医学研究所 ドライマウスおよび/または唾液分泌障害を処置するための医薬
EP2094830B1 (en) 2006-12-19 2013-04-10 Basf Se Uses and methods for preventing and/or treating caries caused by mutans streptococci
EP2141995B1 (en) 2007-03-27 2014-11-05 Perscitus Biosciences, LLC Compositions and their uses in protecting cells from toxic exposures
JP5065742B2 (ja) 2007-04-18 2012-11-07 三栄源エフ・エフ・アイ株式会社 香味の発現性及び持続性が改善された調味食品
CA2685380A1 (en) 2007-05-14 2008-11-20 Neuera Pharmaceuticals, Inc. Inhibitors of acetyl-coa carboxylase for treatment of neuronal hypometabolism
WO2009023357A2 (en) 2007-05-25 2009-02-19 University Of Rochester Curcumin derivatives and their use as radioprotectors
EP2240017B1 (en) 2008-01-04 2019-03-13 Oxford University Innovation Limited Ketone bodies and ketone body esters as blood lipid lowering agents
JP5773870B2 (ja) * 2008-08-21 2015-09-02 アイシス イノヴェイション リミテッド ヒドロキシ酪酸エステル及びその医学的使用
US8642654B2 (en) 2009-04-16 2014-02-04 Isis Innovation Limited Hydroxybutyrate ester and medical use thereof
US9034613B2 (en) 2009-04-16 2015-05-19 Isis Innovation Limited Process for the preparation of (3R)-hydroxybutyl (3R)-hydroxybutyrate by enzymatic enantioselective reduction employing Lactobacillus brevis alcohol dehydrogenase
GB201002983D0 (en) 2010-02-22 2010-04-07 Tdeltas Ltd Nutritinal composition
FR2958154B1 (fr) 2010-04-01 2012-06-08 Oreal Procede de soin et/ou de maquillage des rides
JP6291256B2 (ja) 2011-02-17 2018-03-14 シーエイチディー・バイオサイエンス,インコーポレーテッド ペルオキシα−ケトカルボン酸を含む組成物、および該組成物を産生し、そして用いるための方法
WO2012113415A1 (en) 2011-02-24 2012-08-30 N.V. Nutricia Ketogenic diet composition for the treatment of chemo therapy and/or radiation therapy patients
GB201206192D0 (en) 2012-04-05 2012-05-23 Tdeltas Ltd Ketone bodies and ketone body esters and for maintaining or improving muscle power output
US9895331B2 (en) 2012-07-23 2018-02-20 The University Of Tokyo Prophylactic and/or therapeutic agent for radiation damage
DK2914251T3 (da) 2012-11-05 2019-11-04 Us Health Ketonlegemer til beskyttelse af væv mod beskadigelse som følge af ioniseringsstråling
GB201304467D0 (en) * 2013-03-12 2013-04-24 Tdeltas Ltd Compound for use in protecting skin
GB2515603B (en) 2013-03-14 2015-10-14 Isis Innovation Process for producing (R)-3-Hydroxybutyl (R)-3-Hydroxybutyrate
CA2902603C (en) 2013-03-19 2021-03-02 University Of South Florida Compositions and methods for producing elevated and sustained ketosis
GB201314127D0 (en) 2013-08-07 2013-09-18 Tdeltas Ltd Ketone body and ketone body ester for reducing muscle breakdown

Also Published As

Publication number Publication date
ES2623368T3 (es) 2017-07-11
JP6110959B2 (ja) 2017-04-05
US20140308719A1 (en) 2014-10-16
HK1205100A1 (zh) 2015-12-11
US20230295672A1 (en) 2023-09-21
DK2984066T3 (en) 2017-05-08
GB201404577D0 (en) 2014-04-30
SG11201507685UA (en) 2015-10-29
BR112015023334A2 (pt) 2017-07-18
CA2905225A1 (en) 2014-09-18
EP2984066B1 (en) 2017-02-01
GB2515603B (en) 2015-10-14
BR112015023334B1 (pt) 2021-05-18
EP2984066A1 (en) 2016-02-17
CN105246870A (zh) 2016-01-13
AU2014230120A1 (en) 2015-10-08
JP2016511278A (ja) 2016-04-14
US11566268B2 (en) 2023-01-31
WO2014140308A1 (en) 2014-09-18
AU2014230120B2 (en) 2018-06-21
KR102265842B1 (ko) 2021-06-15
GB2515603A (en) 2014-12-31
KR20160005687A (ko) 2016-01-15

Similar Documents

Publication Publication Date Title
CA2905225C (en) Process for producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate
EP2419519B1 (en) Process for producing (3r)-hydroxybutyl (3r)-hydroxybutyrate by enzymatic enantioselective reduction employing alcohol dehydrogenases or keto reductases
US9221741B2 (en) Ketocarboxylic acids, ketocarboxylic esters, methods of manufacture and uses thereof
WO2012033845A2 (en) Catalytic dehydration of lactic acid and lactic acid esters
CN101735085A (zh) 动力学拆分制备d-丝氨酸的方法
US20140212957A1 (en) Production of optically pure propane-1,2-diol
EP1783108B1 (en) Method for producing halogen-substituted benzenedimethanol
CN114106036A (zh) 一种L-α-甘油磷脂酰胆碱的分离提取方法
CN104230880A (zh) 2-((4r, 6r)-6-氨乙基-2,2-二甲基-1,3-二氧六环-4-基)乙酸酯的简便制备方法
US10081820B2 (en) Method for producing (Z)-2-benzoyloxy-12-heptadecene and (2S,12Z)-2-hydroxy-12-heptadecene and method for producing (2S,12Z)-2-acetoxy-12-heptadecene
US11807600B2 (en) Synthesis of novel ketone body analogs for use as a nutritional supplement
JP2012236798A (ja) (3R)−3−ヒドロキシブタン酸−l−メンチルの製造方法
CN121554356A (zh) 一种高品质生物基1,9-壬二醇的制备方法
CN118206450A (zh) 合成3-羟基丁酸甘油酯的方法
JP4789889B2 (ja) (r)−2−アルキルシクロペンタノンの製造方法
CN101100424A (zh) 制备混合碳酸烷基酯的方法
JPH08113550A (ja) 光学活性3−ヒドロキシヘキサン酸類の製造方法
JP5618126B2 (ja) エステル化合物の製造方法
CN120505376A (zh) 一种脂肪酶催化制备维生素a中间体的方法
Peng et al. A new highly-enantioselective synthetic process for producing (S)-2-hydroxybutyric acid methyl ester
JPH11113589A (ja) (r)−2−ヒドロキシ−4−フェニルブタン酸エステルの製法
van Nispen et al. 4.2 Synthesis of the (R)-Butyrate Esters of Secondary Alcohols by Dynamic Kinetic Resolution Employing a Bis (tetrafluorosuccinato)-bridged Ru (II) Complex

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20190225

H11 Ip right ceased following rejected request for revival

Free format text: ST27 STATUS EVENT CODE: T-6-6-H10-H11-H101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: TIME LIMIT FOR REVERSAL EXPIRED

Effective date: 20250916

H13 Ip right lapsed

Free format text: ST27 STATUS EVENT CODE: N-4-6-H10-H13-H100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE AND LATE FEE NOT PAID BY DEADLINE OF NOTICE

Effective date: 20251106