GB2515603B - Process for producing (R)-3-Hydroxybutyl (R)-3-Hydroxybutyrate - Google Patents

Process for producing (R)-3-Hydroxybutyl (R)-3-Hydroxybutyrate

Info

Publication number
GB2515603B
GB2515603B GB1404577.7A GB201404577A GB2515603B GB 2515603 B GB2515603 B GB 2515603B GB 201404577 A GB201404577 A GB 201404577A GB 2515603 B GB2515603 B GB 2515603B
Authority
GB
United Kingdom
Prior art keywords
hydroxybutyrate
hydroxybutyl
producing
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
GB1404577.7A
Other languages
English (en)
Other versions
GB201404577D0 (en
GB2515603A (en
Inventor
Kieran Clarke
Richard Lewis Veech
M 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 GB201404577D0 publication Critical patent/GB201404577D0/en
Publication of GB2515603A publication Critical patent/GB2515603A/en
Application granted granted Critical
Publication of GB2515603B publication Critical patent/GB2515603B/en
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)
GB1404577.7A 2013-03-14 2014-03-14 Process for producing (R)-3-Hydroxybutyl (R)-3-Hydroxybutyrate Expired - Fee Related GB2515603B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US201361783167P 2013-03-14 2013-03-14

Publications (3)

Publication Number Publication Date
GB201404577D0 GB201404577D0 (en) 2014-04-30
GB2515603A GB2515603A (en) 2014-12-31
GB2515603B true GB2515603B (en) 2015-10-14

Family

ID=50336299

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1404577.7A Expired - Fee Related GB2515603B (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=)

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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

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WO2010120300A1 (en) * 2009-04-16 2010-10-21 Isis Innovation Limited Process for the preparation of (3r)-hydr0xybutyl (3r) -hydroxybutyrate by enzymatic enantioselective reduction employing lactobacillus brevis alcohol dehydrogenase
GB2511941A (en) * 2013-03-12 2014-09-17 Tdeltas Ltd Compound for use in protecting skin

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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
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CA2905225A1 (en) 2014-09-18
EP2984066B1 (en) 2017-02-01
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CN105246870A (zh) 2016-01-13
AU2014230120A1 (en) 2015-10-08
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AU2014230120B2 (en) 2018-06-21
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GB2515603A (en) 2014-12-31
KR20160005687A (ko) 2016-01-15

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