AU2014230120B2 - Process for producing (R)-3hydroxybutyl (R)-3hydroxybutyrate - Google Patents

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

Info

Publication number
AU2014230120B2
AU2014230120B2 AU2014230120A AU2014230120A AU2014230120B2 AU 2014230120 B2 AU2014230120 B2 AU 2014230120B2 AU 2014230120 A AU2014230120 A AU 2014230120A AU 2014230120 A AU2014230120 A AU 2014230120A AU 2014230120 B2 AU2014230120 B2 AU 2014230120B2
Authority
AU
Australia
Prior art keywords
hydroxybutyrate
process according
alcohol
poly
ester
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.)
Ceased
Application number
AU2014230120A
Other languages
English (en)
Other versions
AU2014230120A1 (en
Inventor
Kieran Clarke
Todd King
Richard 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
United States Department of Health and Human Services
Original Assignee
Oxford University Innovation Ltd
GOVERNMENT OF USA AS REPRESENTED BY SECRETARY
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, GOVERNMENT OF USA AS REPRESENTED BY SECRETARY filed Critical Oxford University Innovation Ltd
Publication of AU2014230120A1 publication Critical patent/AU2014230120A1/en
Assigned to OXFORD UNIVERSITY INNOVATION LIMITED, GOVERNMENT OF THE USA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES reassignment OXFORD UNIVERSITY INNOVATION LIMITED Alteration of Name(s) of Applicant(s) under S113 Assignors: GOVERNMENT OF THE USA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES, ISIS INNOVATION LTD
Application granted granted Critical
Publication of AU2014230120B2 publication Critical patent/AU2014230120B2/en
Ceased legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/62—Carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation 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
    • C07C29/136—Preparation 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
    • C07C29/147—Preparation 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/18—Polyhydroxylic acyclic alcohols
    • C07C31/20—Dihydroxylic alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/18—Polyhydroxylic acyclic alcohols
    • C07C31/20—Dihydroxylic alcohols
    • C07C31/207—1,4-Butanediol; 1,3-Butanediol; 1,2-Butanediol; 2,3-Butanediol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/02—Preparation of carboxylic acid esters by interreacting ester groups, i.e. transesterification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, 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)
AU2014230120A 2013-03-14 2014-03-14 Process for producing (R)-3hydroxybutyl (R)-3hydroxybutyrate Ceased AU2014230120B2 (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
AU2014230120A1 AU2014230120A1 (en) 2015-10-08
AU2014230120B2 true AU2014230120B2 (en) 2018-06-21

Family

ID=50336299

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2014230120A Ceased AU2014230120B2 (en) 2013-03-14 2014-03-14 Process for producing (R)-3hydroxybutyl (R)-3hydroxybutyrate

Country Status (13)

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

Families Citing this family (30)

* 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
WO2009089144A1 (en) 2008-01-04 2009-07-16 Isis 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
WO2014071389A1 (en) 2012-11-05 2014-05-08 Veech Richard L 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
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
US9255059B2 (en) 2013-08-02 2016-02-09 Eastman Chemical Company Method for producing an alkyl 3-hydroxybutyrate
US9388114B2 (en) 2013-08-02 2016-07-12 Eastman Chemical Company Compositions including an alkyl 3-hydroxybutyrate
US9163202B2 (en) 2013-08-02 2015-10-20 Eastman Chemical Company Aqueous cleaning compositions including an alkyl 3-hydroxybutyrate
DK3400100T3 (da) * 2016-01-06 2020-10-26 Archer Daniels Midland Co Fremgangsmåde til fremstilling af 1,3-butandiol og til eventuelt yderligere fremstilling af (r)-3-hydroxybutyl (r)-3-hydroxybutyrat
RU2761829C2 (ru) 2016-06-07 2021-12-13 Зе Дж. Дэвид Глэдстоун Инститьютс Образуемые среднецепочечными жирными кислотами сложные эфиры бета-гидроксибутирата и бутандиола и композиции и способы на их основе
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
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
GB201710229D0 (en) 2017-06-27 2017-08-09 Tdeltas Ltd Compounds for new use
BR112020001285A2 (pt) 2017-07-21 2020-07-28 Buck Institute For Research On Aging s-enantiômeros de beta-hidroxibutirato e butanodiol e métodos para sua utilização
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
US12037317B2 (en) 2018-01-25 2024-07-16 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
WO2020147979A1 (de) * 2019-01-17 2020-07-23 Ioi Oleo Gmbh Verfahren zur herstellung von polyolbasierten estern von hydroxycarbonsäuren
GB201918657D0 (en) 2019-12-17 2020-01-29 Tdeltas Ltd Compounds for new use
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
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
US20240368644A1 (en) 2021-06-28 2024-11-07 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
US20260098281A1 (en) * 2024-10-04 2026-04-09 Romeo Tango, LLC Methods for producing highly purified (r)-3’-hydroxybutyl (r)-3’-hydroxybutyrate and use for enhancing bodily function and treating disease states

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010021766A1 (en) * 2008-08-21 2010-02-25 Isis Innovation Limited Hydroxybutyrate ester and medical use thereof

Family Cites Families (88)

* 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
AU6777487A (en) 1985-12-18 1987-07-15 Veech, R.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
EP0696605B1 (de) 1994-08-10 2000-09-20 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
EP0816316A4 (en) * 1995-03-10 1999-06-02 Nitto Chemical Industry Co Ltd Process for producing 1,2-ethanediol derivatives
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
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
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
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
WO1998051302A1 (en) 1997-05-15 1998-11-19 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
CA2338090C (en) 1998-07-22 2009-07-14 Metabolix, Inc. Nutritional and therapeutic compositions of 3-hydroxyacids for increasing blood ketone bodies
CA2339941A1 (en) 1998-09-15 2000-03-23 Btg International Limited Use of cyclic esters of r-3-hydroxybutyrate for treatment of metabolic and neural degenerative disorders
JP2003504070A (ja) * 1999-07-09 2003-02-04 フォルシュングスツェントルム ユーリッヒ ゲゼルシャフト ミット ベシュレンクテル ハフツング ケトカルボン酸及びそのエステルの還元のための方法
ES2752800T3 (es) 2000-05-01 2020-04-06 Cerecin Inc Uso de triglicéridos de cadena media para el tratamiento y la prevención de la enfermedad del Parkinson resultante de un metabolismo neuronal reducido
US8124589B2 (en) 2000-05-01 2012-02-28 Accera, Inc. Use of ketogenic compounds for treatment of age-associated memory impairment
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
US6897338B2 (en) 2001-12-18 2005-05-24 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
ES2574918T3 (es) 2003-06-02 2016-06-23 Isis Innovation Limited Tratamiento de la fatiga muscular
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
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
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
JP2009534317A (ja) 2006-04-12 2009-09-24 ユニリーバー・ナームローゼ・ベンノートシヤープ 皮膚に対する抗老化効果を有する経口組成物
WO2008005818A1 (en) 2006-06-30 2008-01-10 Stepan Co 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
WO2008074473A2 (en) 2006-12-19 2008-06-26 Basf Se Uses and methods for preventing and/or treating caries caused by mutants streptococci
US20080253997A1 (en) 2007-03-27 2008-10-16 Perscitus Biosciences, Llc Compositions and methods for 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
US20110003767A1 (en) 2007-05-14 2011-01-06 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
WO2009089144A1 (en) 2008-01-04 2009-07-16 Isis 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
CN102449157B (zh) * 2009-04-16 2015-06-03 伊希斯创新有限公司 使用短乳杆菌醇脱氢酶通过酶促对映选择性还原来制备(3r)-羟丁基(3r)-羟基丁酸酯的方法
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
RU2013142256A (ru) 2011-02-17 2015-03-27 СиЭйчДи БАЙОСАЙЕНС, ИНК. КОМПОЗИЦИИ, СОДЕРЖАЩИЕ ПЕРОКСИ-α-КЕТОКАРБОНОВУЮ КИСЛОТУ, И СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ИСПОЛЬЗОВАНИЯ
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
WO2014017046A1 (ja) 2012-07-23 2014-01-30 国立大学法人東京大学 放射線障害の予防及び／又は治療剤
WO2014071389A1 (en) 2012-11-05 2014-05-08 Veech Richard L 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
GB2515603B (en) 2013-03-14 2015-10-14 Isis Innovation Process for producing (R)-3-Hydroxybutyl (R)-3-Hydroxybutyrate
BR112015024186B1 (pt) 2013-03-19 2023-05-09 University Of South Florida Composições e métodos para produção de cetose de elevação e manutenção
GB201314127D0 (en) 2013-08-07 2013-09-18 Tdeltas Ltd Ketone body and ketone body ester for reducing muscle breakdown

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010021766A1 (en) * 2008-08-21 2010-02-25 Isis Innovation Limited Hydroxybutyrate ester and medical use thereof

Also Published As

Publication number Publication date
KR20160005687A (ko) 2016-01-15
DK2984066T3 (en) 2017-05-08
GB2515603A (en) 2014-12-31
AU2014230120A1 (en) 2015-10-08
WO2014140308A1 (en) 2014-09-18
SG11201507685UA (en) 2015-10-29
BR112015023334A2 (pt) 2017-07-18
US20140308719A1 (en) 2014-10-16
ES2623368T3 (es) 2017-07-11
CN105246870A (zh) 2016-01-13
BR112015023334B1 (pt) 2021-05-18
US11566268B2 (en) 2023-01-31
GB2515603B (en) 2015-10-14
CA2905225C (en) 2021-05-04
EP2984066B1 (en) 2017-02-01
JP2016511278A (ja) 2016-04-14
US20230295672A1 (en) 2023-09-21
GB201404577D0 (en) 2014-04-30
CA2905225A1 (en) 2014-09-18
EP2984066A1 (en) 2016-02-17
KR102265842B1 (ko) 2021-06-15
JP6110959B2 (ja) 2017-04-05
HK1205100A1 (zh) 2015-12-11

Similar Documents

Publication Publication Date Title
CA2905225C (en) Process for producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate
US9221741B2 (en) Ketocarboxylic acids, ketocarboxylic esters, methods of manufacture and uses thereof
CN114008014B (zh) 用于生产酰基封端的3-羟基羧酸的多元醇基酯的方法
CN113329990B (zh) 羟基羧酸甘油酯的生产方法
CN101735085A (zh) 动力学拆分制备d-丝氨酸的方法
CN102459621A (zh) 制备2-酮羧酸的方法
JP2008529475A (ja) カプシノイドの脱水縮合による製造方法、カプシノイドの安定化法、並びにカプシノイド組成物
CN113329992B (zh) 基于多元醇的羟基羧酸酯的生产方法
CN102442927A (zh) 一种阿伐他汀中间体(r)-(-)-4-氰基-3-羟基丁酸乙酯的制备方法
JP2025504449A5 (enExample)
CN116514648A (zh) 一种顺式神经酸的合成方法
US20130274505A1 (en) Process for producing a lactic ester from a fermentation liquor containing ammonium lactate
US20140212957A1 (en) Production of optically pure propane-1,2-diol
CN114106036A (zh) 一种L-α-甘油磷脂酰胆碱的分离提取方法
CN1394944A (zh) 一种由胡麻油经酯交换制取α－亚麻酸乙酯的方法
US11807600B2 (en) Synthesis of novel ketone body analogs for use as a nutritional supplement
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
JP5780651B2 (ja) エクオールの不斉合成法
JP2012236798A (ja) （３Ｒ）−３−ヒドロキシブタン酸−ｌ−メンチルの製造方法
CN101092358A (zh) 丁二酸二异丙酯的间歇制备方法
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
JP5618126B2 (ja) エステル化合物の製造方法
Peng et al. A new highly-enantioselective synthetic process for producing (S)-2-hydroxybutyric acid methyl ester
EP2998286A1 (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

Legal Events

Date Code Title Description
FGA Letters patent sealed or granted (standard patent)
MK14 Patent ceased section 143(a) (annual fees not paid) or expired