JP2015514104A5 - - Google Patents
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- Publication number
- JP2015514104A5 JP2015514104A5 JP2015503897A JP2015503897A JP2015514104A5 JP 2015514104 A5 JP2015514104 A5 JP 2015514104A5 JP 2015503897 A JP2015503897 A JP 2015503897A JP 2015503897 A JP2015503897 A JP 2015503897A JP 2015514104 A5 JP2015514104 A5 JP 2015514104A5
- Authority
- JP
- Japan
- Prior art keywords
- composition
- composition according
- ketone body
- power output
- 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.)
- Granted
Links
- 150000002576 ketones Chemical class 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 16
- WHBMMWSBFZVSSR-GSVOUGTGSA-N (R)-3-hydroxybutyric acid Chemical compound C[C@@H](O)CC(O)=O WHBMMWSBFZVSSR-GSVOUGTGSA-N 0.000 claims description 6
- WHBMMWSBFZVSSR-UHFFFAOYSA-N R3HBA Natural products CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims description 6
- HIWZHLUXGVVBPK-NZSKALFASA-N (3r)-butane-1,3-diol;(3r)-3-hydroxybutanoic acid Chemical compound C[C@@H](O)CCO.C[C@@H](O)CC(O)=O HIWZHLUXGVVBPK-NZSKALFASA-N 0.000 claims description 5
- 239000008280 blood Substances 0.000 claims description 5
- 210000004369 blood Anatomy 0.000 claims description 5
- -1 butanediol ester Chemical class 0.000 claims description 4
- 210000003205 muscle Anatomy 0.000 claims description 4
- 229940068196 placebo Drugs 0.000 claims description 4
- 239000000902 placebo Substances 0.000 claims description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001720 carbohydrates Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 239000003925 fat Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 235000011194 food seasoning agent Nutrition 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 210000002027 skeletal muscle Anatomy 0.000 claims description 2
- 229940088594 vitamin Drugs 0.000 claims description 2
- 229930003231 vitamin Natural products 0.000 claims description 2
- 235000013343 vitamin Nutrition 0.000 claims description 2
- 239000011782 vitamin Substances 0.000 claims description 2
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 2
- SJZRECIVHVDYJC-UHFFFAOYSA-M 4-hydroxybutyrate Chemical compound OCCCC([O-])=O SJZRECIVHVDYJC-UHFFFAOYSA-M 0.000 claims 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims 1
- 229940057917 medium chain triglycerides Drugs 0.000 claims 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- PUPZLCDOIYMWBV-SCSAIBSYSA-N (R)-butane-1,3-diol Chemical compound C[C@@H](O)CCO PUPZLCDOIYMWBV-SCSAIBSYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1206192.5A GB201206192D0 (en) | 2012-04-05 | 2012-04-05 | Ketone bodies and ketone body esters and for maintaining or improving muscle power output |
| GB1206192.5 | 2012-04-05 | ||
| PCT/EP2013/057250 WO2013150153A1 (en) | 2012-04-05 | 2013-04-05 | Ketone bodies and ketone body esters for maintaining or improving muscle power output |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015514104A JP2015514104A (ja) | 2015-05-18 |
| JP2015514104A5 true JP2015514104A5 (https=) | 2016-06-02 |
| JP6241956B2 JP6241956B2 (ja) | 2017-12-06 |
Family
ID=46176983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015503897A Active JP6241956B2 (ja) | 2012-04-05 | 2013-04-05 | 筋パワー出力を維持又は改善するためのケトン体及びケトン体エステル |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20150164855A1 (https=) |
| EP (1) | EP2833882B1 (https=) |
| JP (1) | JP6241956B2 (https=) |
| AU (1) | AU2013244931B2 (https=) |
| CA (1) | CA2873092C (https=) |
| ES (1) | ES2748050T3 (https=) |
| GB (1) | GB201206192D0 (https=) |
| SG (1) | SG11201406343PA (https=) |
| WO (1) | WO2013150153A1 (https=) |
Families Citing this family (70)
| 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 |
| 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 |
| JP2015141458A (ja) * | 2014-01-27 | 2015-08-03 | 株式会社タニタ | ダイエット支援装置、方法、及びプログラム |
| JP6721583B2 (ja) * | 2014-07-21 | 2020-07-15 | オウルン イリオピストＯｕｌｕｎ Ｙｌｉｏｐｉｓｔｏ | ３−ヒドロキシブチラートのオリゴマー体 |
| US10245243B1 (en) * | 2017-12-19 | 2019-04-02 | Axcess Global Sciences, Llc | Non-racemic beta-hydroxybutyrate compounds and compositions enriched with the S-enantiomer and methods of use |
| US11241403B2 (en) | 2016-03-11 | 2022-02-08 | Axcess Global Sciences, Llc | Beta-hydroxybutyrate mixed salt compositions and methods of use |
| US10973792B2 (en) | 2019-02-13 | 2021-04-13 | Axcess Global Sciences, Llc | Racemic beta-hydroxybutyrate mixed salt-acid compositions and methods of use |
| US11185518B2 (en) | 2017-12-19 | 2021-11-30 | Axcess Global Sciences, Llc | S-beta-hydroxybutyrate compounds and compositions enriched with S-enantiomer |
| US10973786B2 (en) | 2016-03-11 | 2021-04-13 | Axcess Global Sciences, Llc | R-beta-hydroxybutyrate, S-beta-hydroxybutyrate, and RS-beta-hydroxybutyrate mixed salt compositions |
| US10736861B2 (en) | 2016-03-11 | 2020-08-11 | Axcess Global Sciences, Llc | Mixed salt compositions for producing elevated and sustained ketosis |
| 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 |
| 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 |
| US20190091189A1 (en) * | 2016-03-21 | 2019-03-28 | Csilla Ari D'Agostino | Administration of exogenous ketone to lower blood glucose |
| US12496283B2 (en) | 2016-04-19 | 2025-12-16 | Axcess Global Sciences, Llc | Administration of R-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 |
| US20230346721A1 (en) | 2018-04-18 | 2023-11-02 | Axcess Global Sciences, Llc | Beta-hydroxybutyric acid compositions and methods for delivery of ketone bodies |
| US12533346B2 (en) | 2016-04-19 | 2026-01-27 | Axcess Global Sciences, Llc | Administration of berberine metabolites |
| 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 |
| 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 |
| US12599579B2 (en) | 2016-04-19 | 2026-04-14 | Axcess Global Sciences, Llc | Compositions and compounds containing ketone bodies and/or ketone body precursors and one or more amino acids |
| US12521378B2 (en) | 2016-04-19 | 2026-01-13 | Axcess Global Sciences, Llc | Administration of R-beta-hydroxybutyrate salt blend and related compounds in humans |
| US12329734B2 (en) | 2017-12-19 | 2025-06-17 | Axcess Global Sciences, Llc | Use of S-beta-hydroxybutyrate compounds for induction and maintenance of flow |
| US10925843B2 (en) | 2018-04-18 | 2021-02-23 | Axcess Global Sciences, Llc | Compositions and methods for keto stacking with beta-hydroxybutyrate and acetoacetate |
| US11806324B2 (en) | 2018-04-18 | 2023-11-07 | Axcess Global Sciences, Llc | Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies |
| 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 |
| FI3558280T3 (fi) * | 2016-12-21 | 2023-07-13 | Univ Kinderspital Beider Basel | Migreenin ennaltaehkäisy ja hoito |
| AU2017381059B2 (en) * | 2016-12-23 | 2023-11-30 | Katholieke Universiteit Leuven | 3-hydroxybutyrate alone or in combination for use in the treatment of critical care treatment |
| CN110691847A (zh) | 2017-03-31 | 2020-01-14 | 基因组股份公司 | 3-羟基丁酰基-CoA脱氢酶变体以及使用方法 |
| US20210101855A1 (en) | 2017-03-31 | 2021-04-08 | Genomatica, Inc. | Process and systems for obtaining 1,3-butanediol from fermentation broths |
| CA3058219A1 (en) | 2017-03-31 | 2018-10-04 | Genomatica, Inc. | Aldehyde dehydrogenase variants and methods of use |
| US20190231742A1 (en) * | 2017-04-20 | 2019-08-01 | Theodore B. VANITALLIE | Nutritional agents used to prevent and treat hypersensitivity and other allergic-type disorders |
| GB201710229D0 (en) | 2017-06-27 | 2017-08-09 | Tdeltas Ltd | Compounds for new 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 |
| 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 |
| JP2021519276A (ja) * | 2018-03-23 | 2021-08-10 | コンサート ファーマシューティカルズ インコーポレイテッド | Ｄ−β−ヒドロキシ酪酸の重水素化類似体およびその使用 |
| US11129802B2 (en) | 2018-08-27 | 2021-09-28 | Axcess Global Sciences, Llc | Compositions and methods for delivering cannabidiol and ketone bodies |
| US11241401B2 (en) | 2020-02-06 | 2022-02-08 | Axcess Global Sciences, Llc | Enantiomerically pure r-beta-hydroxybutyrate mixed salt-acid compositions |
| US10980772B2 (en) | 2018-08-27 | 2021-04-20 | Axcess Global Sciences, Llc | Compositions and methods for delivering tetrahydrocannabinol and ketone bodies |
| US11419836B2 (en) | 2019-02-13 | 2022-08-23 | Axcess Global Sciences, Llc | Racemic and near racemic beta-hydroxybutyrate mixed salt-acid compositions |
| GB2575623B (en) * | 2018-06-04 | 2022-10-26 | Tdeltas Ltd | 3-hydroxybutyrate esters for treating cancer cachexia |
| EP3856896A1 (en) | 2018-09-26 | 2021-08-04 | Genomatica, Inc. | Aldehyde dehydrogenase variants and methods of using same |
| GB2577723A (en) * | 2018-10-04 | 2020-04-08 | Tdeltas Ltd | Compounds for new use |
| ES2941943T3 (es) | 2019-01-17 | 2023-05-26 | Ketolipix Therapeutics Gmbh | Método para la producción de glicéridos de ácidos hidroxicarboxílicos |
| ES3039676T3 (en) * | 2019-01-17 | 2025-10-23 | Ketolipix Therapeutics Gmbh | Method for producing polyol-based esters of optionally acylated hydroxy carboxylic acids |
| EP3880649B1 (de) * | 2019-01-17 | 2023-03-15 | KetoLipix Therapeutics GmbH | Verfahren zur herstellung von polyolbasierten estern von hydroxycarbonsäuren |
| WO2020147980A1 (de) * | 2019-01-17 | 2020-07-23 | Ioi Oleo Gmbh | Verfahren zur herstellung von struktureinheiten auf basis von glyceriden von hydroxycarbonsäuren enthaltenden lipiden |
| CA3097783C (en) * | 2019-03-14 | 2023-01-03 | Neuroenergy Ventures, Inc. | Taste-masking formulation for ketone body compounds |
| US12472200B2 (en) | 2019-05-15 | 2025-11-18 | Axcess Global Sciences, Llc | Autobiotic compositions and method for promoting healthy gut microbiome |
| CN114008014B (zh) * | 2019-06-12 | 2024-03-22 | 凯托利皮克斯治疗有限责任公司 | 用于生产酰基封端的3-羟基羧酸的多元醇基酯的方法 |
| ES2969217T3 (es) * | 2019-06-12 | 2024-05-17 | Ketolipix Therapeutics Gmbh | Procedimiento para la producción de ésteres a base de poliol, en particular ésteres de poliglicerol, de ácidos hidroxicarboxílicos |
| 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 |
| US12167993B2 (en) | 2019-06-21 | 2024-12-17 | Axcess Global Sciences, Llc | Non-vasoconstricting energy-promoting compositions containing ketone bodies |
| US11950616B2 (en) | 2019-06-21 | 2024-04-09 | Axcess Global Sciences, Llc | Non-vasoconstricting energy-promoting compositions containing ketone bodies |
| US11033553B2 (en) | 2019-06-21 | 2021-06-15 | Axcess Global Sciences, Llc | Non-vasoconstricting energy-promoting compositions containing ketone bodies |
| EP4114203A1 (en) | 2020-03-05 | 2023-01-11 | VitaNav, Inc. | COMPOSITION OF (D)-ß-HYDROXYBUTYRIC ACID, (D)-ß-HYDROXYVALERIC ACID, AND (D)-1,3 BUTANEDIOL AS A NUTRITIONAL SUPPLEMENT AND THERAPEUTIC AGENT |
| US12396974B2 (en) | 2020-03-27 | 2025-08-26 | KetoneAid | Ketone ester as a therapeutic treatment of Covid-19 and related viral infections |
| JP7737231B2 (ja) * | 2020-03-31 | 2025-09-10 | 大阪瓦斯株式会社 | ジオール化合物およびその重合体ならびにそれらの製造方法 |
| US12186297B2 (en) | 2020-08-26 | 2025-01-07 | Axcess Global Sciences, Llc | Compositions and methods for increasing lean-to-fat mass ratio |
| 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 |
| US11807600B2 (en) | 2021-11-12 | 2023-11-07 | Samuel J. Rozzoni | Synthesis of novel ketone body analogs for use as a nutritional supplement |
| CN118591523A (zh) * | 2021-11-12 | 2024-09-03 | 阿萨达股份公司 | 多元醇衍生的化合物 |
| GB202219317D0 (en) * | 2022-12-20 | 2023-02-01 | Amazentis Sa | Methods for improving mitophagy in subjects |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995009144A1 (en) * | 1993-09-30 | 1995-04-06 | Eastman Chemical Company | Nutritive water soluble glycerol esters of hydroxy butyric acid |
| 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 |
| 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 |
| US7117715B2 (en) * | 2004-07-09 | 2006-10-10 | Owens-Brockway Glass Container Inc. | Servo mechanism test stand |
| WO2006020137A2 (en) * | 2004-07-16 | 2006-02-23 | Ketocytonyx Inc. | Oligomeric compounds |
| 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 |
| 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 |
-
2012
- 2012-04-05 GB GBGB1206192.5A patent/GB201206192D0/en not_active Ceased
-
2013
- 2013-04-05 US US14/390,495 patent/US20150164855A1/en active Pending
- 2013-04-05 AU AU2013244931A patent/AU2013244931B2/en active Active
- 2013-04-05 ES ES13718524T patent/ES2748050T3/es active Active
- 2013-04-05 CA CA2873092A patent/CA2873092C/en active Active
- 2013-04-05 EP EP13718524.5A patent/EP2833882B1/en active Active
- 2013-04-05 SG SG11201406343PA patent/SG11201406343PA/en unknown
- 2013-04-05 WO PCT/EP2013/057250 patent/WO2013150153A1/en not_active Ceased
- 2013-04-05 JP JP2015503897A patent/JP6241956B2/ja active Active
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