JP2015057427A5 - - Google Patents
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- Publication number
- JP2015057427A5 JP2015057427A5 JP2014241939A JP2014241939A JP2015057427A5 JP 2015057427 A5 JP2015057427 A5 JP 2015057427A5 JP 2014241939 A JP2014241939 A JP 2014241939A JP 2014241939 A JP2014241939 A JP 2014241939A JP 2015057427 A5 JP2015057427 A5 JP 2015057427A5
- Authority
- JP
- Japan
- Prior art keywords
- compound according
- hydroxybutyl
- composition
- human body
- therapy
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 9
- 238000002560 therapeutic procedure Methods 0.000 claims 5
- AOWPVIWVMWUSBD-UHFFFAOYSA-N 3-hydroxybutyl 3-hydroxybutanoate Chemical group CC(O)CCOC(=O)CC(C)O AOWPVIWVMWUSBD-UHFFFAOYSA-N 0.000 claims 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- 108090001060 lipase Proteins 0.000 claims 2
- 102000004882 lipase Human genes 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
- 108010031797 Candida antarctica lipase B Proteins 0.000 claims 1
- 206010012601 Diabetes mellitus Diseases 0.000 claims 1
- 230000002058 anti-hyperglycaemic Effects 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 claims 1
- 150000001720 carbohydrates Chemical class 0.000 claims 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N diguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drugs Drugs 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 230000000580 secretagogue Effects 0.000 claims 1
- 231100000489 sensitizer Toxicity 0.000 claims 1
- 238000005809 transesterification reaction Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Claims (13)
-
- (3R)-ヒドロキシ酪酸(3R)-ヒドロキシブチルについて鏡像異性的に少なくとも90%に濃縮された、請求項１に記載の化合物。
- 下記式(I)：
- 請求項１〜３のいずれか１項に記載の化合物を含む、療法によるヒトの体の治療に使用するための組成物であって、前記ヒトの体は健康である、組成物。
- 請求項１〜３のいずれか１項に記載の化合物を含む、療法によるヒトの体の治療に使用するための組成物であって、個体は18.5〜24.9の肥満度指数を有する、組成物。
- 請求項１〜３のいずれか１項に記載の化合物を含む、療法によるヒトの体の治療に使用するための組成物であって、個体は25〜29.9の肥満度指数を有する、組成物。
- 請求項１〜３のいずれか１項に記載の化合物を含む、療法によるヒトの体の治療に使用するための組成物であって、個体は30〜39.9の肥満度指数を有する、組成物。
- 請求項１〜３のいずれか１項に記載の化合物を含む、療法によるヒトの体の治療に使用するための組成物であって、個体は40以上の肥満度指数を有する、組成物。
- 下記式(I)：
- リパーゼ酵素がカンジダ・アンタークティカ リパーゼBを含む、請求項９に記載の方法。
- 水、糖炭水化物、及び請求項１〜３のいずれか１項に記載の化合物を含む、再水和用組成物。
- 請求項１〜３のいずれか１項に記載の化合物と、インスリン増感剤、インスリン分泌促進剤、ビグアナイド系抗高血糖薬、及びそれらの組合せから選択される抗糖尿病薬とを含む、組合せ医薬。
- 成分が個別に糖尿病患者に投与される、請求項１２に記載の組合せ医薬。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9075108P | 2008-08-21 | 2008-08-21 | |
| US61/090,751 | 2008-08-21 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011523833A Division JP5773870B2 (ja) | 2008-08-21 | 2009-04-16 | ヒドロキシ酪酸エステル及びその医学的使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015057427A JP2015057427A (ja) | 2015-03-26 |
| JP2015057427A5 true JP2015057427A5 (ja) | 2015-06-18 |
| JP6092836B2 JP6092836B2 (ja) | 2017-03-08 |
Family
ID=40885956
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011523833A Active JP5773870B2 (ja) | 2008-08-21 | 2009-04-16 | ヒドロキシ酪酸エステル及びその医学的使用 |
| JP2014241939A Active JP6092836B2 (ja) | 2008-08-21 | 2014-11-28 | ヒドロキシ酪酸エステル及びその医学的使用 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011523833A Active JP5773870B2 (ja) | 2008-08-21 | 2009-04-16 | ヒドロキシ酪酸エステル及びその医学的使用 |
Country Status (11)
| Country | Link |
|---|---|
| EP (3) | EP2328858B1 (ja) |
| JP (2) | JP5773870B2 (ja) |
| CN (1) | CN102164884B (ja) |
| AU (1) | AU2009283171B2 (ja) |
| CA (1) | CA2734720C (ja) |
| DK (2) | DK2328858T3 (ja) |
| ES (2) | ES2907630T3 (ja) |
| HK (1) | HK1159604A1 (ja) |
| NO (1) | NO2328858T3 (ja) |
| PL (2) | PL2328858T3 (ja) |
| WO (1) | WO2010021766A1 (ja) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2670413T3 (es) | 2003-06-03 | 2018-05-30 | The United States Government As Represented By The Department Of Health And Human Services | Suplementos nutricionales y composiciones terapéuticas que comprenden derivados de (R)-3-hidroxibutirato |
| CN101969769A (zh) | 2008-01-04 | 2011-02-09 | 伊希斯创新有限公司 | 用作降低血脂药剂的酮体和酮体酯 |
| 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 |
| US8329938B2 (en) * | 2011-02-21 | 2012-12-11 | Eastman Chemical Company | Hydroxyalkanoic acid and hydroxyalkanoice acid oligomer esters of retinol |
| GB201206192D0 (en) * | 2012-04-05 | 2012-05-23 | Tdeltas Ltd | Ketone bodies and ketone body esters and for maintaining or improving muscle power output |
| JP6883384B2 (ja) * | 2012-11-05 | 2021-06-09 | ザ ユナイテッド ステイツ オブ アメリカ， アズ リプレゼンテッド バイ ザ セクレタリー， デパートメント オブ ヘルス アンド ヒューマン サービシーズ | 電離放射線による傷害から組織を防護するためのケトン体 |
| 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 |
| GB201314127D0 (en) * | 2013-08-07 | 2013-09-18 | Tdeltas Ltd | Ketone body and ketone body ester for reducing muscle breakdown |
| EP3094321B1 (en) * | 2014-01-13 | 2019-05-01 | University Of South Florida | Methods of sustaining dietary ketosis and its effects on lipid profile |
| CN103860533A (zh) * | 2014-02-12 | 2014-06-18 | 新乡医学院 | β羟基丁酸在治疗帕金森病中的应用 |
| CN106456686A (zh) * | 2014-03-19 | 2017-02-22 | 斯坦陵布什大学 | 用于治疗或增强肌肉组织的方法 |
| US11241403B2 (en) | 2016-03-11 | 2022-02-08 | Axcess Global Sciences, Llc | Beta-hydroxybutyrate mixed salt compositions and methods of use |
| US11103470B2 (en) | 2017-11-22 | 2021-08-31 | Axcess Global Sciences, Llc | Non-racemic beta-hydroxybutyrate compounds and compositions enriched with the R-enantiomer and methods of use |
| US10245242B1 (en) * | 2017-11-22 | 2019-04-02 | Axcess Global Sciences, Llc | Non-racemic beta-hydroxybutyrate compounds and compositions enriched with the R-enantiomer and methods of use |
| AU2017253109B2 (en) * | 2016-04-19 | 2023-03-23 | Axcess Global Sciences, Llc | Administration of butyrate, beta-hydroxybutyrate, and related compounds in humans |
| US12109182B2 (en) | 2016-04-19 | 2024-10-08 | Axcess Global Sciences, Llc | Administration of R-beta-hydroxybutyrate and related compounds in humans |
| US11026929B2 (en) | 2016-04-19 | 2021-06-08 | Keto Patent Group, Inc. | Administration of berberine metabolites |
| CN114292190A (zh) | 2016-06-07 | 2022-04-08 | J大卫格莱斯顿研究机构 | 丁二醇的中链脂肪酸酯，其组合物、口服制剂及其应用方法 |
| 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 |
| MX2019007597A (es) * | 2016-12-23 | 2019-12-19 | Univ Leuven Kath | 3-hidroxibutirato solo o en combinacion para su uso en el tratamiento de cuidados intensivos. |
| 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 |
| 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 |
| US12090129B2 (en) | 2017-11-22 | 2024-09-17 | Axcess Global Sciences, Llc | Non-racemic beta-hydroxybutyrate compounds and compositions enriched with the R-enantiomer and methods of use |
| US11202769B2 (en) | 2017-11-22 | 2021-12-21 | Axcess Global Sciences, Llc | Ketone body esters of s-beta-hydroxybutyrate and/or s-1,3-butanediol for modifying metabolic function |
| US10925843B2 (en) | 2018-04-18 | 2021-02-23 | Axcess Global Sciences, Llc | Compositions and methods for keto stacking with beta-hydroxybutyrate and acetoacetate |
| US11944598B2 (en) | 2017-12-19 | 2024-04-02 | Axcess Global Sciences, Llc | Compositions containing s-beta-hydroxybutyrate or non-racemic mixtures enriched with the s-enatiomer |
| WO2019147503A1 (en) | 2018-01-25 | 2019-08-01 | Buck Institute For Research On Aging | Synthesis of 3-hydroxybutyryl 3-hydroxybutyrate and related compounds |
| GB2572185A (en) * | 2018-03-21 | 2019-09-25 | Chain Biotechnology Ltd | Pharmaceutical compositions |
| US11806324B2 (en) | 2018-04-18 | 2023-11-07 | Axcess Global Sciences, Llc | Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies |
| GB2575623B (en) * | 2018-06-04 | 2022-10-26 | Tdeltas Ltd | 3-hydroxybutyrate esters for treating cancer cachexia |
| CA3022995C (en) * | 2018-06-12 | 2019-10-15 | Ketofibe (9211-3133 Quebec Inc.) | Novel ketogenic compounds, compositions, methods and use thereof |
| JP7515407B2 (ja) * | 2018-06-21 | 2024-07-12 | ソシエテ・デ・プロデュイ・ネスレ・エス・アー | ニコチンアミドアデニンジヌクレオチド（ｎａｄ＋）前駆体及び少なくとも１種のケトン又はケトン前駆体を使用する組成物及び方法 |
| GB2577723A (en) * | 2018-10-04 | 2020-04-08 | Tdeltas Ltd | Compounds for new use |
| FI3880649T3 (fi) | 2019-01-17 | 2023-05-30 | Ketolipix Therapeutics Gmbh | Menetelmä hydroksikarboksyylihappojen polyolipohjaisten estereiden tuottamiseksi |
| CN109700021A (zh) * | 2019-03-04 | 2019-05-03 | 清华大学 | 3-羟基丁酸及其衍生物在制备预防和治疗肥胖及肥胖相关疾病的产品中的应用 |
| US20220257546A1 (en) | 2019-05-10 | 2022-08-18 | Ketoswiss Ag | Ketone bodies enclosed in microbeads |
| AU2020278825A1 (en) * | 2019-05-21 | 2021-10-21 | Société des Produits Nestlé S.A. Entre-deux-Villes 1800 Vevey Switzerland | Dietary butyrate |
| WO2020249198A1 (de) * | 2019-06-12 | 2020-12-17 | Ioi Oleo Gmbh | Verfahren zur herstellung von polyolbasierten estern von acylverkappten 3-hydroxycarbonsäuren |
| EP3956286B1 (de) * | 2019-06-12 | 2023-12-13 | KetoLipix Therapeutics GmbH | Verfahren zur herstellung von polyolbasierten estern, insbesondere polyglycerinestern, von hydroxycarbonsäuren |
| US11950616B2 (en) | 2019-06-21 | 2024-04-09 | Axcess Global Sciences, Llc | Non-vasoconstricting energy-promoting compositions containing ketone bodies |
| 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 |
| US20230174454A1 (en) * | 2020-05-12 | 2023-06-08 | Genomatica, Inc. | Process of synthesizing and purifying (3r)-hydroxybutyl (3r)-hydroxybutanoate |
| US20230257337A1 (en) * | 2020-07-13 | 2023-08-17 | Ioi Oleo Gmbh | Method for producing polygylcerol esters of polycarboxylic acids esterified with oxobutanol |
| 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 |
| EP4366720A1 (en) * | 2021-07-09 | 2024-05-15 | Georgia State University Research Foundation, Inc. | The use of beta-hydroxybutyrates for the treatment or prevention of aneurysms and dissections |
| CN117677383A (zh) | 2021-07-17 | 2024-03-08 | 瑞士凯托股份公司 | 酮体或生酮化合物与镇痛剂或抗氧化剂的组合 |
| IT202100020441A1 (it) | 2021-07-30 | 2023-01-30 | Unichem Estense S R L | Miscela di un mono-estere e un di-estere, in cui detti mono-estere e di-estere sono esteri dell’acido (R)-3-idrossibutanoico con un polialcol, processo per la preparazione della miscela e relativi usi medici |
| US11969430B1 (en) | 2023-03-10 | 2024-04-30 | Axcess Global Sciences, Llc | Compositions containing paraxanthine and beta-hydroxybutyrate or precursor for increasing neurological and physiological performance |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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. |
| 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 |
| EP1641444B1 (en) | 2003-06-02 | 2016-03-23 | Isis Innovation Limited | Treatment of muscle fatigue |
| ES2670413T3 (es) * | 2003-06-03 | 2018-05-30 | The United States Government As Represented By The Department Of Health And Human Services | Suplementos nutricionales y composiciones terapéuticas que comprenden derivados de (R)-3-hidroxibutirato |
| 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 |
| US8452351B2 (en) * | 2008-06-02 | 2013-05-28 | Qualcomm Incorporated | Methods and apparatus for saving battery power in mobile stations |
-
2009
- 2009-04-16 EP EP09789596.5A patent/EP2328858B1/en active Active
- 2009-04-16 PL PL09789596T patent/PL2328858T3/pl unknown
- 2009-04-16 CA CA2734720A patent/CA2734720C/en active Active
- 2009-04-16 JP JP2011523833A patent/JP5773870B2/ja active Active
- 2009-04-16 ES ES17176132T patent/ES2907630T3/es active Active
- 2009-04-16 DK DK09789596.5T patent/DK2328858T3/en active
- 2009-04-16 AU AU2009283171A patent/AU2009283171B2/en active Active
- 2009-04-16 EP EP21211530.7A patent/EP4011374A1/en active Pending
- 2009-04-16 DK DK17176132.3T patent/DK3296284T3/da active
- 2009-04-16 ES ES09789596.5T patent/ES2655367T3/es active Active
- 2009-04-16 CN CN200980136723.1A patent/CN102164884B/zh active Active
- 2009-04-16 PL PL17176132T patent/PL3296284T3/pl unknown
- 2009-04-16 WO PCT/US2009/040766 patent/WO2010021766A1/en active Application Filing
- 2009-04-16 NO NO09789596A patent/NO2328858T3/no unknown
- 2009-04-16 EP EP17176132.3A patent/EP3296284B1/en active Active
-
2012
- 2012-01-05 HK HK12100075.4A patent/HK1159604A1/xx unknown
-
2014
- 2014-11-28 JP JP2014241939A patent/JP6092836B2/ja active Active
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