JP2016511278A5 - - Google Patents
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- JP2016511278A5 JP2016511278A5 JP2015562212A JP2015562212A JP2016511278A5 JP 2016511278 A5 JP2016511278 A5 JP 2016511278A5 JP 2015562212 A JP2015562212 A JP 2015562212A JP 2015562212 A JP2015562212 A JP 2015562212A JP 2016511278 A5 JP2016511278 A5 JP 2016511278A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxybutyrate
- process according
- poly
- alcohol
- 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.)
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- 238000000034 method Methods 0.000 claims 8
- WHBMMWSBFZVSSR-GSVOUGTGSA-M (R)-3-hydroxybutyrate Chemical compound C[C@@H](O)CC([O-])=O WHBMMWSBFZVSSR-GSVOUGTGSA-M 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- 238000005809 transesterification reaction Methods 0.000 claims 4
- -1 (R) -3-hydroxybutyrate ester Chemical class 0.000 claims 2
- ALDKXMLLZDHWRZ-UHFFFAOYSA-N bis(2-methoxyethoxy)alumanylium;hydride;sodium Chemical compound [H-].[Na].COCCO[Al+]OCCOC ALDKXMLLZDHWRZ-UHFFFAOYSA-N 0.000 claims 2
- 238000004821 distillation Methods 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- PUPZLCDOIYMWBV-SCSAIBSYSA-N (R)-butane-1,3-diol Chemical compound C[C@@H](O)CCO PUPZLCDOIYMWBV-SCSAIBSYSA-N 0.000 claims 1
- 229920002261 Corn starch Polymers 0.000 claims 1
- 240000000111 Saccharum officinarum Species 0.000 claims 1
- 235000007201 Saccharum officinarum Nutrition 0.000 claims 1
- AOWPVIWVMWUSBD-RNFRBKRXSA-N [(3R)-3-hydroxybutyl] (3R)-3-hydroxybutanoate Chemical compound C[C@@H](O)CCOC(=O)C[C@@H](C)O AOWPVIWVMWUSBD-RNFRBKRXSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000002378 acidificating Effects 0.000 claims 1
- CROBTXVXNQNKKO-UHFFFAOYSA-N borohydride Chemical compound [BH4-] CROBTXVXNQNKKO-UHFFFAOYSA-N 0.000 claims 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000008120 corn starch Substances 0.000 claims 1
- 238000007871 hydride transfer reaction Methods 0.000 claims 1
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 claims 1
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical group [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 239000003638 reducing agent Substances 0.000 claims 1
- YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Substances [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- ODGROJYWQXFQOZ-UHFFFAOYSA-N sodium;boron(1-) Chemical compound [B-].[Na+] ODGROJYWQXFQOZ-UHFFFAOYSA-N 0.000 claims 1
Claims (9)
- (i) ポリ-(R)-3-ヒドロキシブチレートをエステル交換条件下で、ポリ-(R)-3-ヒドロキシブチレートをエステル交換することができるC 1-6 の1価、2価又は3価のアルコールと接触させて、ポリ-(R)-3-ヒドロキシブチレートをエステル交換して(R)-3-ヒドロキシブチレートと前記アルコールのエステルを生成し、
(ii) 工程i)の生成物を第一の部分及び第二の部分に分離し、(R)-3-ヒドロキシブチレートエステルの第一の部分を還元して(R)-1,3-ブタンジオールを生成し、
(iii) エステル交換条件下で工程ii) からの(R)-1,3-ブタンジオールをエステル交換されたエステルの第二の部分と接触させて(R)-3-ヒドロキシブチル-(R)-3-ヒドロキシブチレートを生成することを特徴とする(R)-3-ヒドロキシブチル(R)-3-ヒドロキシブチレートの製造方法。 - ポリ-(R)-3-ヒドロキシブチレートをトウモロコシ澱粉又はサトウキビから得る、請求項1記載の方法。
- ポリ-(R)-3-ヒドロキシブチレートを工程i)でエタノールを使用してエステル交換する、請求項1又は2記載の方法。
- アルコール対ポリ-(R)-3-ヒドロキシブチレートの質量比が1:1 から10:1までである、請求項1から3のいずれか1項記載の方法。
- 工程i)を酸性条件で行なう、請求項1から4のいずれか1項記載の方法。
- 工程i)の生成物を処理して酸を中和し、アルコールを蒸留により除去する、請求項1から5のいずれか1項記載の方法。
- 蒸留を110 ℃〜150 ℃の温度で行なう、請求項6記載の方法。
- 工程ii) における還元が、ヒドリド移動試薬を使用して(R)-3-ヒドロキシブチレートエステルを還元することを含む、請求項1から7のいずれか1項記載の方法。
- 還元剤が水素化リチウムアルミニウム、水素化ナトリウムビス(2-メトキシエトキシ)アルミニウム、ホウ水素化ナトリウム、ホウ水素化ニッケルから選ばれる、請求項8記載の方法。
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 (3)
Publication Number | Publication Date |
---|---|
JP2016511278A JP2016511278A (ja) | 2016-04-14 |
JP2016511278A5 true JP2016511278A5 (ja) | 2016-07-14 |
JP6110959B2 JP6110959B2 (ja) | 2017-04-05 |
Family
ID=50336299
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015562212A Active JP6110959B2 (ja) | 2013-03-14 | 2014-03-14 | (r)−3−ヒドロキシブチル(r)−3−ヒドロキシブチレートの製造方法 |
Country Status (14)
Country | Link |
---|---|
US (2) | US11566268B2 (ja) |
EP (1) | EP2984066B1 (ja) |
JP (1) | JP6110959B2 (ja) |
KR (1) | KR102265842B1 (ja) |
CN (1) | CN105246870A (ja) |
AU (1) | AU2014230120B2 (ja) |
BR (1) | BR112015023334B1 (ja) |
CA (1) | CA2905225C (ja) |
DK (1) | DK2984066T3 (ja) |
ES (1) | ES2623368T3 (ja) |
GB (1) | GB2515603B (ja) |
HK (1) | HK1205100A1 (ja) |
SG (1) | SG11201507685UA (ja) |
WO (1) | WO2014140308A1 (ja) |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004108740A2 (en) | 2003-06-03 | 2004-12-16 | The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Nutritional supplements and therapeutic compositions comprising (r)-3-hydroxybutyrate derivatives |
TR201908522T4 (tr) | 2008-01-04 | 2019-07-22 | The Government Of The U S A As Represented By The Secretary Dept Of Health And Human Services | Kan lipidi düşürücü maddeler olarak keton gövdeleri ve keton gövde esterleri. |
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 |
CA2922223C (en) | 2012-11-05 | 2021-11-09 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services And Human Services | 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 |
JP6110959B2 (ja) | 2013-03-14 | 2017-04-05 | オックスフォード ユニヴァーシティ イノヴェーション リミテッド | (r)−3−ヒドロキシブチル(r)−3−ヒドロキシブチレートの製造方法 |
US9249378B2 (en) | 2013-08-02 | 2016-02-02 | Eastman Chemical Company | Aqueous cleaning compositions having enhanced properties |
US9163202B2 (en) | 2013-08-02 | 2015-10-20 | Eastman Chemical Company | Aqueous cleaning compositions including an alkyl 3-hydroxybutyrate |
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 |
US20190023632A1 (en) * | 2016-01-06 | 2019-01-24 | Archer Daniels Midland Company | Process for producing 1,3-butanediol and for optionally further producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate |
CN109477993B (zh) | 2016-06-07 | 2023-03-28 | J大卫格莱斯顿研究机构 | β-羟基丁酸酯和丁二醇的中链脂肪酸酯和组合物及其使用方法 |
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 |
EP3654963A4 (en) | 2017-07-21 | 2021-04-14 | Buck Institute for Research on Aging | BETA-HYDROXYBUTYRATE AND BUTANEDIOL S ENANTIOMERS AND THEIR METHODS OF USE |
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 |
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 |
DK3880649T3 (da) * | 2019-01-17 | 2023-05-30 | Ketolipix Therapeutics Gmbh | Fremgangsmåde til fremstilling af polyolbaserede estere af hydroxycarboxylsyrer |
GB201918657D0 (en) | 2019-12-17 | 2020-01-29 | Tdeltas Ltd | Compounds for new use |
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 |
Family Cites Families (90)
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) |
SU507322A1 (ru) | 1973-07-26 | 1976-03-25 | Московский Научно-Исследовательский Институт Косметологии | Регул тор гормонального обмена кожи |
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 |
WO1987003806A1 (en) | 1985-12-18 | 1987-07-02 | 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 |
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 |
JP4740426B2 (ja) | 1997-03-17 | 2011-08-03 | ビーティージー・インターナショナル・リミテッド | 治療用組成物 |
US6316038B1 (en) | 1997-03-17 | 2001-11-13 | Btg International Limited | Therapeutic compositions |
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 |
ES2285772T3 (es) | 1997-05-15 | 2007-11-16 | University Of Washington | Composicion y metodos para tratar la enfermedad de alzheimer y otras amiloidosis. |
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 |
WO2000015216A1 (en) | 1998-09-15 | 2000-03-23 | Btg International Limited | Therapeutic compositions (ii) |
EP1194582A1 (de) * | 1999-07-09 | 2002-04-10 | Forschungszentrum Jülich Gmbh | Verfahren zur reduktion von keto-carbonsäuren und deren estern |
US20070179197A1 (en) | 2000-05-01 | 2007-08-02 | Accera, Inc. | Compositions and methods for improving or preserving brain function |
ES2323940T3 (es) | 2000-05-01 | 2009-07-28 | Accera, Inc. | Uso de trigliceridos de cadena media para el tratamiento y prevencion de la enfermedad de alzheimer. |
JP5327825B2 (ja) | 2000-07-14 | 2013-10-30 | メタボリックス,インコーポレイテッド | ヒドロキシアルカノエート及びイソシアネ―トから得られるポリウレタン |
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 |
WO2004108740A2 (en) | 2003-06-03 | 2004-12-16 | The Government Of The United States Of America As Represented By The Secretary Of 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 |
US7947736B2 (en) | 2004-07-16 | 2011-05-24 | Btg International Limited | 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 |
US20070135376A1 (en) | 2005-06-20 | 2007-06-14 | Accera, Inc. | Method to reduce oxidative damage and improve mitochondrial efficiency |
ATE455807T1 (de) | 2005-11-29 | 2010-02-15 | Basf Se | Verfahren zur um- oder veresterung von seitenketten in polymeren |
KR20090003148A (ko) | 2006-04-03 | 2009-01-09 | 액세라인크 | 나이와 관련된 기억 손상의 치료를 위한 케톤 생성조성물의 용도 |
ES2393212T3 (es) | 2006-04-12 | 2012-12-19 | Unilever N.V. | Composición oral con un efecto antienvejecimiento sobre la piel |
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 |
RU2446208C9 (ru) | 2006-12-19 | 2012-11-10 | Басф Се | Применение и способ профилактики или лечения кариеса, вызванного mutans streptococci, отличных от streptococcus mutans |
WO2008119032A1 (en) | 2007-03-27 | 2008-10-02 | 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 |
JP2010527360A (ja) | 2007-05-14 | 2010-08-12 | ニューエラ・ファーマシューティカルズ・インコーポレーテッド | 神経細胞の代謝低下の処置のためのアセチル−coaカルボキシラーゼの阻害剤 |
WO2009023357A2 (en) | 2007-05-25 | 2009-02-19 | University Of Rochester | Curcumin derivatives and their use as radioprotectors |
TR201908522T4 (tr) | 2008-01-04 | 2019-07-22 | The Government Of The U S A As Represented By The Secretary Dept Of Health And Human Services | Kan lipidi düşürücü maddeler olarak keton gövdeleri ve keton gövde esterleri. |
US8642654B2 (en) | 2009-04-16 | 2014-02-04 | Isis Innovation Limited | Hydroxybutyrate ester and medical use thereof |
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 |
AU2009344282B2 (en) | 2009-04-16 | 2014-12-11 | Government Of The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | 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 |
WO2012112951A1 (en) | 2011-02-17 | 2012-08-23 | Chd Bioscience, Inc. | COMPOSITIONS COMPRISING PEROXY α-KETOCARBOXYLIC ACID AND METHODS FOR PRODUCING AND USING THE SAME |
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 |
CA2922223C (en) | 2012-11-05 | 2021-11-09 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services And Human Services | 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 |
JP6110959B2 (ja) | 2013-03-14 | 2017-04-05 | オックスフォード ユニヴァーシティ イノヴェーション リミテッド | (r)−3−ヒドロキシブチル(r)−3−ヒドロキシブチレートの製造方法 |
MY180761A (en) | 2013-03-19 | 2020-12-08 | Univ 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 |
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2014
- 2014-03-14 JP JP2015562212A patent/JP6110959B2/ja active Active
- 2014-03-14 AU AU2014230120A patent/AU2014230120B2/en active Active
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- 2014-03-14 WO PCT/EP2014/055156 patent/WO2014140308A1/en active Application Filing
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- 2014-03-14 CN CN201480022083.2A patent/CN105246870A/zh active Pending
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