AU2013244931B2 - Ketone bodies and ketone body esters for maintaining or improving muscle power output - Google Patents
Ketone bodies and ketone body esters for maintaining or improving muscle power output Download PDFInfo
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- AU2013244931B2 AU2013244931B2 AU2013244931A AU2013244931A AU2013244931B2 AU 2013244931 B2 AU2013244931 B2 AU 2013244931B2 AU 2013244931 A AU2013244931 A AU 2013244931A AU 2013244931 A AU2013244931 A AU 2013244931A AU 2013244931 B2 AU2013244931 B2 AU 2013244931B2
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- Prior art keywords
- ketone
- power output
- hydroxybutyrate
- blood
- monoester
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/225—Polycarboxylic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/06—Anabolic agents
Landscapes
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Endocrinology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
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| 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 |
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| AU2013244931A1 AU2013244931A1 (en) | 2014-11-20 |
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| AU2013244931A Active AU2013244931B2 (en) | 2012-04-05 | 2013-04-05 | Ketone bodies and ketone body esters for maintaining or improving muscle power output |
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| US (1) | US20150164855A1 (https=) |
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| GB (1) | GB201206192D0 (https=) |
| SG (1) | SG11201406343PA (https=) |
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Families Citing this family (70)
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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 |
| 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 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5693850A (en) * | 1993-09-30 | 1997-12-02 | Eastman Chemical Company | Nutritive water soluble glycerol esters of hydroxy butyric acid |
| 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 |
| WO2006010137A1 (en) * | 2004-07-09 | 2006-01-26 | Owens-Brockway Glass Container Inc. | Servo mechanism test stand |
| WO2010021766A1 (en) * | 2008-08-21 | 2010-02-25 | Isis Innovation Limited | Hydroxybutyrate ester and medical use thereof |
| WO2011101171A1 (en) * | 2010-02-22 | 2011-08-25 | Tdeltas Limited | Nutritional composition |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2006020137A2 (en) * | 2004-07-16 | 2006-02-23 | Ketocytonyx Inc. | Oligomeric compounds |
| US8642654B2 (en) * | 2009-04-16 | 2014-02-04 | Isis Innovation Limited | Hydroxybutyrate ester and medical use thereof |
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- 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
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5693850A (en) * | 1993-09-30 | 1997-12-02 | Eastman Chemical Company | Nutritive water soluble glycerol esters of hydroxy butyric acid |
| 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 |
| WO2006010137A1 (en) * | 2004-07-09 | 2006-01-26 | Owens-Brockway Glass Container Inc. | Servo mechanism test stand |
| WO2010021766A1 (en) * | 2008-08-21 | 2010-02-25 | Isis Innovation Limited | Hydroxybutyrate ester and medical use thereof |
| WO2011101171A1 (en) * | 2010-02-22 | 2011-08-25 | Tdeltas Limited | Nutritional composition |
Non-Patent Citations (3)
| Title |
|---|
| BOIARINOV GA ET AL: "Effect of sodium oxybutyrate on macroergic phosphates, function and ultrastructure of the myocardium in blood loss.", BIULLETEN' EKSPERIMENTAL'NOI BIOLOGll I MEDITSINY. MAR 1984, vol. 97, no. 3, pages 309-312. * |
| CLARK BM ET AL: "Dilated cardiomyopathy and acute liver injury associated with combined use of ephedra, [gamma]-hydroxybutyrate, and anabolic steroids", PHARMACOTHERAPY vol. 25, no. 5, May 2005, pages 756-761. * |
| OSTROVSKAYA RU ET AL: "Effect of prolonged administration of sodium hydroxybutyrate on the working capacity and muscle tissue in rats", FARMAKOLOGIYA I TOKSIKOLOGIYA 1981 SU, vol. 44, no. 5, pages 534-539. * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB201206192D0 (en) | 2012-05-23 |
| CA2873092A1 (en) | 2013-10-10 |
| JP2015514104A (ja) | 2015-05-18 |
| WO2013150153A1 (en) | 2013-10-10 |
| EP2833882A1 (en) | 2015-02-11 |
| ES2748050T3 (es) | 2020-03-12 |
| US20150164855A1 (en) | 2015-06-18 |
| SG11201406343PA (en) | 2014-11-27 |
| JP6241956B2 (ja) | 2017-12-06 |
| CA2873092C (en) | 2020-08-04 |
| EP2833882B1 (en) | 2019-07-24 |
| AU2013244931A1 (en) | 2014-11-20 |
| HK1206999A1 (en) | 2016-01-22 |
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