KR102265842B1 - (ｒ)­３­하이드록시부틸 (ｒ)­３­하이드록시부티레이트를 생산하는 방법 - Google Patents

(ｒ)­３­하이드록시부틸 (ｒ)­３­하이드록시부티레이트를 생산하는 방법 Download PDF

Info

Publication number
KR102265842B1
KR102265842B1 KR1020157029333A KR20157029333A KR102265842B1 KR 102265842 B1 KR102265842 B1 KR 102265842B1 KR 1020157029333 A KR1020157029333 A KR 1020157029333A KR 20157029333 A KR20157029333 A KR 20157029333A KR 102265842 B1 KR102265842 B1 KR 102265842B1
Authority
KR
South Korea
Prior art keywords
hydroxybutyrate
alcohol
poly
hydroxybutyl
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.)
Expired - Fee Related
Application number
KR1020157029333A
Other languages
English (en)
Korean (ko)
Other versions
KR20160005687A (ko
Inventor
키어런 클라크
리차드 비치
토드 킹
Original Assignee
옥스포드 유니버시티 이노베이션 리미티드
더 유나이티드 스테이츠 오브 어메리카, 애즈 리프리젠티드 바이 더 세크러테리, 디파트먼트 오브 헬쓰 앤드 휴먼 서비씨즈
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 옥스포드 유니버시티 이노베이션 리미티드, 더 유나이티드 스테이츠 오브 어메리카, 애즈 리프리젠티드 바이 더 세크러테리, 디파트먼트 오브 헬쓰 앤드 휴먼 서비씨즈 filed Critical 옥스포드 유니버시티 이노베이션 리미티드
Publication of KR20160005687A publication Critical patent/KR20160005687A/ko
Application granted granted Critical
Publication of KR102265842B1 publication Critical patent/KR102265842B1/ko
Expired - Fee Related 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)
KR1020157029333A 2013-03-14 2014-03-14 (ｒ)­３­하이드록시부틸 (ｒ)­３­하이드록시부티레이트를 생산하는 방법 Expired - Fee Related KR102265842B1 (ko)

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
KR20160005687A KR20160005687A (ko) 2016-01-15
KR102265842B1 true KR102265842B1 (ko) 2021-06-15

Family

ID=50336299

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020157029333A Expired - Fee Related KR102265842B1 (ko) 2013-03-14 2014-03-14 (ｒ)­３­하이드록시부틸 (ｒ)­３­하이드록시부티레이트를 생산하는 방법

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

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050182235A1 (en) 2001-12-18 2005-08-18 Metabolix Inc., A Delaware Corporation Methods of making intermediates from polyhydroxyalkanoates
JP2008513017A (ja) * 2004-09-15 2008-05-01 ザ プロクター アンド ギャンブル カンパニー バイオマスからポリヒドロキシアルカノエート類を抽出する方法
WO2010021766A1 (en) 2008-08-21 2010-02-25 Isis Innovation Limited Hydroxybutyrate ester and medical use thereof

Family Cites Families (86)

* 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
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
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
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

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050182235A1 (en) 2001-12-18 2005-08-18 Metabolix Inc., A Delaware Corporation Methods of making intermediates from polyhydroxyalkanoates
JP2008513017A (ja) * 2004-09-15 2008-05-01 ザ プロクター アンド ギャンブル カンパニー バイオマスからポリヒドロキシアルカノエート類を抽出する方法
WO2010021766A1 (en) 2008-08-21 2010-02-25 Isis Innovation Limited Hydroxybutyrate ester and medical use thereof
JP2012500264A (ja) * 2008-08-21 2012-01-05 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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
John A. O’Neill et al, ‘A Simple Enantioselective Synthesis of γ-Valerolactone’, Tetrahedron: Asymmetry, 1994, Vol.5, No.1, pp.117-118*

Also Published As

Publication number Publication date
ES2623368T3 (es) 2017-07-11
JP6110959B2 (ja) 2017-04-05
CA2905225C (en) 2021-05-04
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
GB2515603A (en) 2014-12-31
KR20160005687A (ko) 2016-01-15

Similar Documents

Publication Publication Date Title
KR102265842B1 (ko) (ｒ)­３­하이드록시부틸 (ｒ)­３­하이드록시부티레이트를 생산하는 방법
US9034613B2 (en) Process for the preparation of (3R)-hydroxybutyl (3R)-hydroxybutyrate by enzymatic enantioselective reduction employing Lactobacillus brevis alcohol dehydrogenase
CN104086523A (zh) 一种制备坎格列净中间体2-(4-氟苯基)-5-[(5-卤代-2-甲基苯基)甲基]噻吩的方法
CA2614408C (en) Asymmetric reduction of 1,1,1-trifluoroacetone
US20140212957A1 (en) Production of optically pure propane-1,2-diol
CN116514648A (zh) 一种顺式神经酸的合成方法
EP2737074B1 (en) Process for producing L-carnitine from beta-lactones employing lipases
CN114106036A (zh) 一种L-α-甘油磷脂酰胆碱的分离提取方法
US10815504B2 (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
CN116287036B (zh) 一种生产1，3-二油酰2-棕榈酰甘油的方法
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
JP2012236798A (ja) （３Ｒ）−３−ヒドロキシブタン酸−ｌ−メンチルの製造方法
JP4789889B2 (ja) （ｒ）−２−アルキルシクロペンタノンの製造方法
Ida et al. INVESTIGATION OF Pd (II)-CATALYZED CYCLIZATION OF CHIRAL
CN121554356A (zh) 一种高品质生物基1,9-壬二醇的制备方法
JPWO2023138854A5 (https=)
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

Legal Events

Date Code Title Description
PA0105 International application

St.27 status event code: A-0-1-A10-A15-nap-PA0105

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PG1501 Laying open of application

St.27 status event code: A-1-1-Q10-Q12-nap-PG1501

R18-X000 Changes to party contact information recorded

St.27 status event code: A-3-3-R10-R18-oth-X000

P22-X000 Classification modified

St.27 status event code: A-2-2-P10-P22-nap-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

R15-X000 Change to inventor requested

St.27 status event code: A-3-3-R10-R15-oth-X000

R16-X000 Change to inventor recorded

St.27 status event code: A-3-3-R10-R16-oth-X000

A201 Request for examination
P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PA0201 Request for examination

St.27 status event code: A-1-2-D10-D11-exm-PA0201

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

St.27 status event code: A-1-2-D10-D21-exm-PE0902

R18-X000 Changes to party contact information recorded

St.27 status event code: A-3-3-R10-R18-oth-X000

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

R18-X000 Changes to party contact information recorded

St.27 status event code: A-3-3-R10-R18-oth-X000

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

St.27 status event code: A-1-2-D10-D22-exm-PE0701

GRNT Written decision to grant
PR0701 Registration of establishment

St.27 status event code: A-2-4-F10-F11-exm-PR0701

PR1002 Payment of registration fee

St.27 status event code: A-2-2-U10-U12-oth-PR1002

Fee payment year number: 1

PG1601 Publication of registration

St.27 status event code: A-4-4-Q10-Q13-nap-PG1601

R18-X000 Changes to party contact information recorded

St.27 status event code: A-5-5-R10-R18-oth-X000

R18-X000 Changes to party contact information recorded

St.27 status event code: A-5-5-R10-R18-oth-X000

R18-X000 Changes to party contact information recorded

St.27 status event code: A-5-5-R10-R18-oth-X000

PC1903 Unpaid annual fee

St.27 status event code: A-4-4-U10-U13-oth-PC1903

Not in force date: 20240611

Payment event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

R18-X000 Changes to party contact information recorded

St.27 status event code: A-5-5-R10-R18-oth-X000

PC1903 Unpaid annual fee

St.27 status event code: N-4-6-H10-H13-oth-PC1903

Ip right cessation event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

Not in force date: 20240611