JP2020504134A5 - - Google Patents
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- Publication number
- JP2020504134A5 JP2020504134A5 JP2019536598A JP2019536598A JP2020504134A5 JP 2020504134 A5 JP2020504134 A5 JP 2020504134A5 JP 2019536598 A JP2019536598 A JP 2019536598A JP 2019536598 A JP2019536598 A JP 2019536598A JP 2020504134 A5 JP2020504134 A5 JP 2020504134A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxybutyrate
- glyceryl
- tbi
- ester
- administration
- 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
- WHBMMWSBFZVSSR-UHFFFAOYSA-N R3HBA Natural products CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims description 56
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 45
- 230000009529 traumatic brain injury Effects 0.000 claims description 45
- -1 glyceryl (3-hydroxybutyrate) ester Chemical class 0.000 claims description 41
- WHBMMWSBFZVSSR-UHFFFAOYSA-M 3-hydroxybutyrate Chemical compound CC(O)CC([O-])=O WHBMMWSBFZVSSR-UHFFFAOYSA-M 0.000 claims description 36
- 150000002148 esters Chemical class 0.000 claims description 25
- 150000002576 ketones Chemical class 0.000 claims description 24
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 12
- 230000000149 penetrating effect Effects 0.000 claims description 10
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 8
- 239000008103 glucose Substances 0.000 claims description 8
- 208000024891 symptom Diseases 0.000 claims description 8
- 230000037396 body weight Effects 0.000 claims description 7
- 230000006378 damage Effects 0.000 claims description 7
- 235000005911 diet Nutrition 0.000 claims description 7
- 230000037213 diet Effects 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 201000001421 hyperglycemia Diseases 0.000 claims description 6
- 235000021590 normal diet Nutrition 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical group CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 2
- 230000036470 plasma concentration Effects 0.000 claims 14
- 230000000694 effects Effects 0.000 claims 9
- CBTHKODKAPVTNY-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-hydroxybutanoate Chemical compound CC(O)CC(=O)OCC(O)CO CBTHKODKAPVTNY-UHFFFAOYSA-N 0.000 claims 8
- 238000011477 surgical intervention Methods 0.000 claims 7
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 230000007062 hydrolysis Effects 0.000 claims 4
- 238000006460 hydrolysis reaction Methods 0.000 claims 4
- 210000004958 brain cell Anatomy 0.000 claims 3
- 150000001720 carbohydrates Chemical class 0.000 claims 3
- 235000014633 carbohydrates Nutrition 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 230000000926 neurological effect Effects 0.000 claims 3
- 230000002085 persistent effect Effects 0.000 claims 3
- 102000004169 proteins and genes Human genes 0.000 claims 3
- 108090000623 proteins and genes Proteins 0.000 claims 3
- 241000282412 Homo Species 0.000 claims 2
- 238000007726 management method Methods 0.000 claims 2
- 230000000414 obstructive effect Effects 0.000 claims 2
- 230000001052 transient effect Effects 0.000 claims 2
- WHBMMWSBFZVSSR-GSVOUGTGSA-M (R)-3-hydroxybutyrate Chemical compound C[C@@H](O)CC([O-])=O WHBMMWSBFZVSSR-GSVOUGTGSA-M 0.000 claims 1
- AFENDNXGAFYKQO-UHFFFAOYSA-N 2-hydroxybutyric acid Chemical group CCC(O)C(O)=O AFENDNXGAFYKQO-UHFFFAOYSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- 230000002411 adverse Effects 0.000 claims 1
- 239000013590 bulk material Substances 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- 244000144972 livestock Species 0.000 claims 1
- 238000012423 maintenance Methods 0.000 claims 1
- 235000012054 meals Nutrition 0.000 claims 1
- 239000008280 blood Substances 0.000 description 15
- 210000004369 blood Anatomy 0.000 description 15
- 239000005862 Whey Substances 0.000 description 14
- 102000007544 Whey Proteins Human genes 0.000 description 14
- 108010046377 Whey Proteins Proteins 0.000 description 14
- 208000027418 Wounds and injury Diseases 0.000 description 4
- 208000014674 injury Diseases 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 206010000410 Acetonaemia Diseases 0.000 description 2
- 208000007976 Ketosis Diseases 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 235000020887 ketogenic diet Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 208000008348 Post-Concussion Syndrome Diseases 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 235000019577 caloric intake Nutrition 0.000 description 1
- 235000020827 calorie restriction Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 230000003345 hyperglycaemic effect Effects 0.000 description 1
- 230000035861 hyperketonemia Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15/404,396 | 2017-01-12 | ||
| US15/404,396 US9925164B1 (en) | 2017-01-12 | 2017-01-12 | Glyceryl 3-hydroxybutyrates for traumatic brain injury |
| PCT/US2017/063853 WO2018132189A1 (en) | 2017-01-12 | 2017-11-30 | Glyceryl 3-hydroxybutyrates for traumatic brain injury |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020504134A JP2020504134A (ja) | 2020-02-06 |
| JP2020504134A5 true JP2020504134A5 (https=) | 2021-01-14 |
| JP7278593B2 JP7278593B2 (ja) | 2023-05-22 |
Family
ID=61633011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019536598A Active JP7278593B2 (ja) | 2017-01-12 | 2017-11-30 | 外傷性脳損傷のためのグリセリル３－ヒドロキシブチラート |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US9925164B1 (https=) |
| EP (1) | EP3568129A4 (https=) |
| JP (1) | JP7278593B2 (https=) |
| KR (1) | KR102443942B1 (https=) |
| CN (1) | CN110114067A (https=) |
| BR (1) | BR112019014128A2 (https=) |
| CA (1) | CA3046355C (https=) |
| IL (1) | IL267934B2 (https=) |
| MX (1) | MX391851B (https=) |
| MY (1) | MY207193A (https=) |
| WO (1) | WO2018132189A1 (https=) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US11241403B2 (en) | 2016-03-11 | 2022-02-08 | Axcess Global Sciences, Llc | Beta-hydroxybutyrate mixed salt compositions and methods of use |
| US12496283B2 (en) | 2016-04-19 | 2025-12-16 | Axcess Global Sciences, Llc | Administration of R-beta-hydroxybutyrate and related compounds in humans |
| US12521378B2 (en) | 2016-04-19 | 2026-01-13 | Axcess Global Sciences, Llc | Administration of R-beta-hydroxybutyrate salt blend 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 |
| 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 |
| US11806324B2 (en) | 2018-04-18 | 2023-11-07 | Axcess Global Sciences, Llc | Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies |
| US11026929B2 (en) | 2016-04-19 | 2021-06-08 | Keto Patent Group, Inc. | 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 |
| CA3021784A1 (en) * | 2016-04-19 | 2017-10-26 | Keto Patent Group, Inc. | Administration of butyrate, beta-hydroxybutyrate, and related compounds in humans |
| US10925843B2 (en) | 2018-04-18 | 2021-02-23 | Axcess Global Sciences, Llc | Compositions and methods for keto stacking with beta-hydroxybutyrate and acetoacetate |
| US12109182B2 (en) | 2016-04-19 | 2024-10-08 | Axcess Global Sciences, Llc | Administration of R-beta-hydroxybutyrate 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 |
| 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 |
| US12533346B2 (en) | 2016-04-19 | 2026-01-27 | Axcess Global Sciences, Llc | Administration of berberine metabolites |
| US10376528B2 (en) | 2017-03-10 | 2019-08-13 | Tecton Group, Llc | Composition comprising ketone body and nicotinamide adenine dinucleotide modulator and methyl donor |
| US12171735B2 (en) | 2017-04-19 | 2024-12-24 | Axcess Global Sciences, Llc | Administration of butyrate, beta-hydroxybutyrate, cannabidiol, and related compounds in humans |
| 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 |
| BR112021014012A2 (pt) * | 2019-01-17 | 2021-09-21 | Ioi Oleo Gmbh | Processo para a produção de lipídeos que contêm unidades estruturais com base em glicerídeos de ácidos hidroxicarboxílicos |
| ES2941943T3 (es) * | 2019-01-17 | 2023-05-26 | Ketolipix Therapeutics Gmbh | Método para la producción de glicéridos de ácidos hidroxicarboxílicos |
| US12472200B2 (en) | 2019-05-15 | 2025-11-18 | Axcess Global Sciences, Llc | Autobiotic compositions and method for promoting healthy gut microbiome |
| PL3976021T3 (pl) * | 2019-05-30 | 2025-07-21 | Neuroenergy Ventures, Inc. | Tri(beta-hydroksymaślan) glicerolu do zastosowania w leczeniu i zapobieganiu przemijającym atakom niedokrwiennym neuronów |
| US20230020342A1 (en) * | 2019-06-12 | 2023-01-19 | Ioi Oleo Gmbh | Method for producing polyol-based esters, in particular polyglycerol esters, from hydroxy carboxylic acids |
| JP7546828B2 (ja) * | 2019-06-12 | 2024-09-09 | ケトリピックス セラポーティクス ゲーエムベーハー | ケトカルボン酸のポリオールベースのエステルの製造方法 |
| US12167993B2 (en) | 2019-06-21 | 2024-12-17 | Axcess Global Sciences, Llc | Non-vasoconstricting energy-promoting compositions containing ketone bodies |
| 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 |
| US11950616B2 (en) | 2019-06-21 | 2024-04-09 | Axcess Global Sciences, Llc | Non-vasoconstricting energy-promoting compositions containing ketone bodies |
| EP4146337B1 (de) * | 2020-07-13 | 2024-04-17 | KetoLipix Therapeutics GmbH | Verfahren zur herstellung von polyglycerinestern von mit oxobutanol veresterten polycarbonsäuren |
| US12186297B2 (en) | 2020-08-26 | 2025-01-07 | Axcess Global Sciences, Llc | Compositions and methods for increasing lean-to-fat mass ratio |
| EP4366720A4 (en) * | 2021-07-09 | 2025-05-07 | Georgia State University Research Foundation, Inc. | The use of beta-hydroxybutyrates for the treatment or prevention of aneurysms and dissections |
| MX2024005533A (es) | 2021-11-12 | 2024-07-29 | Arxada Ag | Compuestos derivados de polioles. |
| US20250002446A1 (en) | 2021-11-26 | 2025-01-02 | Arxada Ag | Acetoacetate Based Ketals |
| US12023382B2 (en) | 2022-01-18 | 2024-07-02 | Today Inc. | Molecules, formulations, and methods for nutritional support of athletes, patients, and others |
| WO2023139357A1 (en) * | 2022-01-18 | 2023-07-27 | Today Inc. | Molecules, nutritional formulations, and methods of providing nutritional support |
| US20230277484A1 (en) * | 2022-03-04 | 2023-09-07 | Guardian Biosciences, LLC | Compositions and methods to promote brain health |
| WO2024083889A1 (en) | 2022-10-18 | 2024-04-25 | Arxada Ag | Polyol-derived compounds |
| WO2025074001A2 (en) | 2023-10-05 | 2025-04-10 | Arxada Ag | Enzymatic reduction of acetoacetate |
| WO2025196156A1 (en) | 2024-03-20 | 2025-09-25 | Arxada Ag | Continuous hydrogenation process of acetoacetate esters |
| WO2025224319A1 (en) | 2024-04-25 | 2025-10-30 | Arxada Ag | Reduction of acetoacetate esters in the presence of amines |
Family Cites Families (32)
| 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 |
| US6323237B1 (en) | 1997-03-17 | 2001-11-27 | Btg International Limited | Therapeutic compositions |
| CA2283642C (en) * | 1997-03-17 | 2012-05-15 | Btg International Limited | Therapeutic compositions |
| US8124589B2 (en) | 2000-05-01 | 2012-02-28 | Accera, Inc. | Use of ketogenic compounds for treatment of age-associated memory impairment |
| GB0420856D0 (en) * | 2004-09-20 | 2004-10-20 | Ketocytonyx Inc | Cns modulators |
| WO2006128006A1 (en) | 2005-05-26 | 2006-11-30 | The Regents Of The University Of Colorado | Inhibition of the alternative complement pathway for treatment of traumatic brain injury, spinal cord injury and related conditions |
| 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 |
| BRPI0811052A2 (pt) | 2007-04-12 | 2015-01-27 | Univ Minnesota | Composições de proteção de isquemia/reperfusão e métodos de uso. |
| JP2009173766A (ja) | 2008-01-24 | 2009-08-06 | Ono Kogei Kk | 炭素繊維含有コーティング組成物およびその調製方法 |
| US8642654B2 (en) | 2009-04-16 | 2014-02-04 | Isis Innovation Limited | Hydroxybutyrate ester and medical use thereof |
| WO2010084356A1 (en) | 2009-01-24 | 2010-07-29 | Phytopharm Plc | Treatment of neurotrophic factor mediated disorders |
| GB201002983D0 (en) * | 2010-02-22 | 2010-04-07 | Tdeltas Ltd | Nutritinal composition |
| CA2873057C (en) | 2011-05-09 | 2020-02-25 | University Of South Florida | The use of ketone esters for prevention of cns oxygen toxicity |
| US20140072654A1 (en) | 2011-12-23 | 2014-03-13 | Savind, Inc. | Cancer with metabolic therapy and hyperbaric oxygen |
| FR2997302B1 (fr) | 2012-10-29 | 2015-02-06 | Assist Publ Hopitaux De Paris | Prevention et traitement des deficits en pyruvate deshydrogenase |
| EP2914251B1 (en) | 2012-11-05 | 2019-08-21 | The United States of America, as represented by The Secretary, Department of Health and Human Services | Ketone bodies to protect tissues from damage by ionizing radiation |
| WO2014085652A1 (en) | 2012-11-28 | 2014-06-05 | University Of South Florida | Targeting cancer with metabolic therapy and hyperbaric oxygen |
| KR102499654B1 (ko) | 2013-03-19 | 2023-02-13 | 유니버시티 오브 사우스 플로리다 | 상승되고 지속되는 케톤증을 생성하기 위한 조성물 및 방법 |
| WO2015034812A2 (en) * | 2013-09-04 | 2015-03-12 | Beth Israel Deaconess Medical Center | A new ketogenic diet and its use in treating the critically ill |
| WO2015156865A1 (en) | 2014-01-13 | 2015-10-15 | University Of South Florida | Methods of sustaining dietary ketosis and its effects on lipid profile |
| US20160078782A1 (en) | 2014-09-17 | 2016-03-17 | The Trustees Of Boston College | Glucose Ketone Index for MetabolicTherapy |
| US9364456B1 (en) | 2015-06-30 | 2016-06-14 | University Of South Florida | Ketone esters for treatment of angelman syndrome |
| US20180200220A1 (en) | 2015-07-10 | 2018-07-19 | Cognate Nutritionals, Inc. | Prophylaxis and mitigation of migraine headaches using ketogenic medium chain triglycerides, ketone esters, and other ketogenic sources |
| US10292952B2 (en) | 2016-03-11 | 2019-05-21 | Axcess Global Sciences, Llc | Mixed salt compositions for maintaining or restoring electrolyte balance while producing elevated and sustained ketosis |
| WO2017165445A1 (en) | 2016-03-21 | 2017-09-28 | Csilla Ari D'agostino | Administration of exogenous ketone to lower blood glucose |
| US10376482B2 (en) | 2016-04-03 | 2019-08-13 | Franco Cavaleri | Butyrate and beta-hydroxybutyrate compositions |
| CA3021784A1 (en) | 2016-04-19 | 2017-10-26 | Keto Patent Group, Inc. | Administration of butyrate, beta-hydroxybutyrate, and related compounds in humans |
| WO2018009208A1 (en) | 2016-07-08 | 2018-01-11 | Cognate Nutritionals, Inc. | Nutritional mitiggation of the cns effects of traumatic brain injury |
| US10588877B2 (en) | 2016-07-21 | 2020-03-17 | Savind, Inc. | Compositions comprising β-hydroxybutyric acid and salt, and methods of using the same |
| 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 |
| US20180055797A1 (en) | 2016-08-31 | 2018-03-01 | KetoneAid Inc. | Non-racemic ketone salts for rapid-onset nutritional ketosis and metabolic therapy |
| CN109890381A (zh) | 2016-09-12 | 2019-06-14 | 南佛罗里达大学 | 酮改善神经再生 |
-
2017
- 2017-01-12 US US15/404,396 patent/US9925164B1/en active Active
- 2017-11-30 IL IL267934A patent/IL267934B2/en unknown
- 2017-11-30 JP JP2019536598A patent/JP7278593B2/ja active Active
- 2017-11-30 BR BR112019014128-6A patent/BR112019014128A2/pt not_active Application Discontinuation
- 2017-11-30 CA CA3046355A patent/CA3046355C/en active Active
- 2017-11-30 EP EP17891194.7A patent/EP3568129A4/en active Pending
- 2017-11-30 WO PCT/US2017/063853 patent/WO2018132189A1/en not_active Ceased
- 2017-11-30 KR KR1020197020924A patent/KR102443942B1/ko active Active
- 2017-11-30 CN CN201780080457.XA patent/CN110114067A/zh active Pending
- 2017-11-30 MY MYPI2019003665A patent/MY207193A/en unknown
- 2017-11-30 MX MX2019008269A patent/MX391851B/es unknown
-
2018
- 2018-03-01 US US15/909,240 patent/US10736867B2/en active Active
-
2020
- 2020-06-10 US US16/897,349 patent/US11638702B2/en active Active
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