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 US9925164B1 (en) | 2017-01-12 | 2017-01-12 | Glyceryl 3-hydroxybutyrates for traumatic brain injury |
| US15/404,396 | 2017-01-12 | ||
| 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 (cg-RX-API-DMAC7.html) | 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 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3568129A4 (cg-RX-API-DMAC7.html) |
| JP (1) | JP7278593B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102443942B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN110114067A (cg-RX-API-DMAC7.html) |
| BR (1) | BR112019014128A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA3046355C (cg-RX-API-DMAC7.html) |
| IL (1) | IL267934B2 (cg-RX-API-DMAC7.html) |
| MX (1) | MX391851B (cg-RX-API-DMAC7.html) |
| MY (1) | MY207193A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2018132189A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| 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 |
| US12496283B2 (en) | 2016-04-19 | 2025-12-16 | Axcess Global Sciences, Llc | Administration of R-beta-hydroxybutyrate and related compounds in humans |
| US11806324B2 (en) | 2018-04-18 | 2023-11-07 | Axcess Global Sciences, Llc | Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies |
| SG11201809211QA (en) * | 2016-04-19 | 2018-11-29 | Keto Patent Group Inc | Administration of butyrate, beta-hydroxybutyrate, and related compounds in humans |
| 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 |
| CN113329990B (zh) * | 2019-01-17 | 2024-06-07 | 凯托利皮克斯治疗有限责任公司 | 羟基羧酸甘油酯的生产方法 |
| EP3880650B1 (de) * | 2019-01-17 | 2023-09-06 | KetoLipix Therapeutics GmbH | Verfahren zur herstellung von struktureinheiten auf basis von glyceriden von hydroxycarbonsäuren enthaltenden lipiden |
| US12472200B2 (en) | 2019-05-15 | 2025-11-18 | Axcess Global Sciences, Llc | Autobiotic compositions and method for promoting healthy gut microbiome |
| WO2020242478A1 (en) * | 2019-05-30 | 2020-12-03 | Neuroenergy Ventures, Inc. | Glyceryl tris (beta-hydroxybutyrate) and neuronal transient ischemic attacks |
| CN114008015B (zh) * | 2019-06-12 | 2024-02-20 | 凯托利皮克斯治疗有限责任公司 | 羟基羧酸多元醇酯、特别是聚甘油酯的制备方法 |
| US20220380289A1 (en) * | 2019-06-12 | 2022-12-01 | Ioi Oleo Gmbh | Method for producing polyol-based esters of ketocarboxylic acids |
| 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 |
| US12167993B2 (en) | 2019-06-21 | 2024-12-17 | Axcess Global Sciences, Llc | Non-vasoconstricting energy-promoting compositions containing ketone bodies |
| WO2022012767A1 (de) * | 2020-07-13 | 2022-01-20 | Ioi Oleo 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 |
| US20240342121A1 (en) * | 2021-07-09 | 2024-10-17 | Georgia State University Research Foundation, Inc. | The use of beta-hydroxybutyrates for the treatment or prevention of aneurysms and dissections |
| AU2022387742A1 (en) | 2021-11-12 | 2024-06-27 | Arxada Ag | Polyol-derived compounds |
| 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 |
| WO2023167989A2 (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 |
| AU749638B2 (en) | 1997-03-17 | 2002-06-27 | Btg International Limited | Therapeutic compositions |
| US6323237B1 (en) | 1997-03-17 | 2001-11-27 | Btg International Limited | Therapeutic compositions |
| GB0420856D0 (en) * | 2004-09-20 | 2004-10-20 | Ketocytonyx Inc | Cns modulators |
| JP5707024B2 (ja) * | 2005-05-26 | 2015-04-22 | ザ リージェンツ オブ ザ ユニバーシティ オブ コロラド，ア ボディー コーポレイトＴＨＥ ＲＥＧＥＮＴＳ ＯＦ ＴＨＥ ＵＮＩＶＥＲＳＩＴＹ ＯＦ ＣＯＬＯＲＡＤＯ，ａ ｂｏｄｙ ｃｏｒｐｏｒａｔｅ | 外傷性脳損傷、脊髄損傷および関連状態を治療するために補体副経路を阻害する作用剤 |
| HUE035852T2 (en) | 2006-04-03 | 2018-05-28 | Accera Inc | Use of ketogen compounds to treat memory decline |
| WO2008005818A1 (en) * | 2006-06-30 | 2008-01-10 | Stepan Co | Glyceride esters for the treatment of diseases associated with reduced neuronal metabolism of glucose |
| WO2008128095A1 (en) | 2007-04-12 | 2008-10-23 | Regents Of The University Of Minnesota | Ischemia/reperfusion protection compositions and methods of using |
| 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 |
| BRPI1005372A2 (pt) | 2009-01-24 | 2018-03-06 | Phytopharm Plc | metodo de indução da homeostase- regulada de fatores neurotroficos agente; composição; e; uso de um ou mais agentes selecionados de saponinas esteroidais de a/b-cis furostano, furosteno espirostano e espirosteno, e as suas formas de eter, cetona e glicosiladas |
| 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 |
| ES2752030T3 (es) | 2012-11-05 | 2020-04-02 | Us Health | Cuerpos cetónicos para proteger los tejidos del daño por radiación ionizante |
| EP2925308B1 (en) | 2012-11-28 | 2019-12-25 | University Of South Florida | Targeting cancer with metabolic therapy and hyperbaric oxygen |
| WO2014153416A1 (en) | 2013-03-19 | 2014-09-25 | University Of South Florida | Compositions and methods for producing elevated and sustained ketosis |
| 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 |
| EP3549928B1 (en) | 2014-01-13 | 2021-09-22 | University of South Florida | Methods of sustaining dietary ketosis and its effects on muscle fatigue |
| 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 |
| WO2017011294A1 (en) | 2015-07-10 | 2017-01-19 | Cognate Nutritionals, Inc. | Prophylaxis and mitigation of migraine headaches using 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 |
| US20190091189A1 (en) | 2016-03-21 | 2019-03-28 | 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 |
| SG11201809211QA (en) | 2016-04-19 | 2018-11-29 | 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 |
| AU2017322708A1 (en) | 2016-09-12 | 2019-03-21 | University Of South Florida | Neuroregeneration improved by ketone |
-
2017
- 2017-01-12 US US15/404,396 patent/US9925164B1/en active Active
- 2017-11-30 MY MYPI2019003665A patent/MY207193A/en unknown
- 2017-11-30 IL IL267934A patent/IL267934B2/en unknown
- 2017-11-30 EP EP17891194.7A patent/EP3568129A4/en active Pending
- 2017-11-30 KR KR1020197020924A patent/KR102443942B1/ko active Active
- 2017-11-30 CN CN201780080457.XA patent/CN110114067A/zh active Pending
- 2017-11-30 MX MX2019008269A patent/MX391851B/es unknown
- 2017-11-30 BR BR112019014128-6A patent/BR112019014128A2/pt not_active Application Discontinuation
- 2017-11-30 WO PCT/US2017/063853 patent/WO2018132189A1/en not_active Ceased
- 2017-11-30 JP JP2019536598A patent/JP7278593B2/ja active Active
- 2017-11-30 CA CA3046355A patent/CA3046355C/en active Active
-
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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