CA2905225C - Process for producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate - Google Patents
Process for producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate Download PDFInfo
- 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.)
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Classifications
-
- 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
- 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
- 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)
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 (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)
| 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 |
Family Cites Families (89)
| 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 |
| ES2655367T3 (es) * | 2008-08-21 | 2018-02-19 | Oxford University Innovation Limited | Bebida que comprende éster de hidroxibutirato y uso médico de la misma |
| 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 |
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- 2014-03-14 WO PCT/EP2014/055156 patent/WO2014140308A1/en not_active Ceased
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- 2014-03-14 BR BR112015023334-1A patent/BR112015023334B1/pt not_active IP Right Cessation
- 2014-03-14 KR KR1020157029333A patent/KR102265842B1/ko not_active Expired - Fee Related
- 2014-03-14 EP EP14711210.6A patent/EP2984066B1/en active Active
- 2014-03-14 CN CN201480022083.2A patent/CN105246870A/zh active Pending
- 2014-03-14 DK DK14711210.6T patent/DK2984066T3/en active
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|---|---|
| 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 |
| 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 |
| AU2014230120B2 (en) | 2018-06-21 |
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