JP2020502250A5 - - Google Patents
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- Publication number
- JP2020502250A5 JP2020502250A5 JP2019534701A JP2019534701A JP2020502250A5 JP 2020502250 A5 JP2020502250 A5 JP 2020502250A5 JP 2019534701 A JP2019534701 A JP 2019534701A JP 2019534701 A JP2019534701 A JP 2019534701A JP 2020502250 A5 JP2020502250 A5 JP 2020502250A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxybutyrate
- ester
- glyceryltris
- administration
- compound
- 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 3-hydroxybutyric acid Chemical group CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims description 39
- WHBMMWSBFZVSSR-UHFFFAOYSA-M 3-hydroxybutyrate Chemical compound CC(O)CC([O-])=O WHBMMWSBFZVSSR-UHFFFAOYSA-M 0.000 claims description 32
- -1 glyceryl (3-hydroxybutyrate) ester Chemical class 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 18
- 230000036470 plasma concentration Effects 0.000 claims description 18
- 208000019695 Migraine disease Diseases 0.000 claims description 16
- 206010027599 migraine Diseases 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000002576 ketones Chemical class 0.000 claims description 13
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 8
- 230000037396 body weight Effects 0.000 claims description 6
- 208000024891 symptom Diseases 0.000 claims 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 13
- 239000000203 mixture Substances 0.000 claims 8
- CBTHKODKAPVTNY-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-hydroxybutanoate Chemical compound CC(O)CC(=O)OCC(O)CO CBTHKODKAPVTNY-UHFFFAOYSA-N 0.000 claims 3
- 230000007062 hydrolysis Effects 0.000 claims 3
- 238000006460 hydrolysis reaction Methods 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical group CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- 230000001684 chronic 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
- 206010019233 Headaches Diseases 0.000 claims 1
- 239000005862 Whey Substances 0.000 claims 1
- 102000007544 Whey Proteins Human genes 0.000 claims 1
- 108010046377 Whey Proteins Proteins 0.000 claims 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 229940125961 compound 24 Drugs 0.000 claims 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 230000003252 repetitive effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 230000001052 transient effect Effects 0.000 claims 1
- 235000003642 hunger Nutrition 0.000 description 3
- 230000037351 starvation Effects 0.000 description 3
- 230000036765 blood level Effects 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 235000020887 ketogenic diet Nutrition 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 208000010444 Acidosis Diseases 0.000 description 1
- 208000007976 Ketosis Diseases 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 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 1
- 230000007950 acidosis Effects 0.000 description 1
- 208000026545 acidosis disease Diseases 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000035861 hyperketonemia Effects 0.000 description 1
- 230000004140 ketosis Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15/389,828 US20180177753A1 (en) | 2016-12-23 | 2016-12-23 | Glyceryl 3-hydroxybutyrates for migraine symptom management |
| US15/389,828 | 2016-12-23 | ||
| PCT/US2017/063832 WO2018118369A1 (en) | 2016-12-23 | 2017-11-30 | Glyceryl 3-hydroxybutyrates for migraine symptom management |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020502250A JP2020502250A (ja) | 2020-01-23 |
| JP2020502250A5 true JP2020502250A5 (https=) | 2021-01-14 |
| JP7108320B2 JP7108320B2 (ja) | 2022-07-28 |
Family
ID=62624821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019534701A Active JP7108320B2 (ja) | 2016-12-23 | 2017-11-30 | 片頭痛の症状を管理するためのグリセリル３－ヒドロキシブチラート |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US20180177753A1 (https=) |
| EP (1) | EP3558458B1 (https=) |
| JP (1) | JP7108320B2 (https=) |
| KR (1) | KR102390608B1 (https=) |
| CN (1) | CN110167637B (https=) |
| BR (1) | BR112019012431A2 (https=) |
| CA (1) | CA3046350C (https=) |
| ES (1) | ES2962879T3 (https=) |
| IL (1) | IL267540B (https=) |
| MX (1) | MX389468B (https=) |
| MY (1) | MY190308A (https=) |
| PT (1) | PT3558458T (https=) |
| WO (1) | WO2018118369A1 (https=) |
Families Citing this family (37)
| 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 |
| US12533346B2 (en) | 2016-04-19 | 2026-01-27 | Axcess Global Sciences, Llc | Administration of berberine metabolites |
| US12521378B2 (en) | 2016-04-19 | 2026-01-13 | Axcess Global Sciences, Llc | Administration of R-beta-hydroxybutyrate salt blend and related compounds in humans |
| US12496283B2 (en) | 2016-04-19 | 2025-12-16 | Axcess Global Sciences, Llc | Administration of R-beta-hydroxybutyrate and related compounds in humans |
| 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 |
| US12109182B2 (en) | 2016-04-19 | 2024-10-08 | Axcess Global Sciences, Llc | Administration of R-beta-hydroxybutyrate and related compounds in humans |
| 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 |
| US12329734B2 (en) | 2017-12-19 | 2025-06-17 | Axcess Global Sciences, Llc | Use of S-beta-hydroxybutyrate compounds for induction and maintenance of flow |
| US11806324B2 (en) | 2018-04-18 | 2023-11-07 | Axcess Global Sciences, Llc | Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies |
| 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 |
| US20230346721A1 (en) | 2018-04-18 | 2023-11-02 | Axcess Global Sciences, Llc | Beta-hydroxybutyric acid compositions and methods for delivery of ketone bodies |
| FI3558280T3 (fi) | 2016-12-21 | 2023-07-13 | Univ Kinderspital Beider Basel | Migreenin ennaltaehkäisy ja hoito |
| US10376528B2 (en) | 2017-03-10 | 2019-08-13 | Tecton Group, Llc | Composition comprising ketone body and nicotinamide adenine dinucleotide modulator and methyl donor |
| 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 |
| ES2941943T3 (es) | 2019-01-17 | 2023-05-26 | Ketolipix Therapeutics Gmbh | Método para la producción de glicéridos de ácidos hidroxicarboxílicos |
| 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 |
| KR20220016145A (ko) * | 2019-05-30 | 2022-02-08 | 뉴로에너지 벤처스 인코포레이티드 | 글리세릴 트리스(베타-하이드록시부티레이트) 및 신경 일과성 허혈 발작 |
| 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 |
| 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 |
| IT201900018491A1 (it) * | 2019-10-10 | 2021-04-10 | Dr Schaer S P A | Procedimento di purificazione del tris-(3-idrossibutirrato)-gliceril estere |
| IT201900018488A1 (it) * | 2019-10-10 | 2021-04-10 | Dr Schaer S P A | Procedimento di preparazione del tris-(3-idrossibutirrato)-gliceril estere |
| US12186297B2 (en) | 2020-08-26 | 2025-01-07 | Axcess Global Sciences, Llc | Compositions and methods for increasing lean-to-fat mass ratio |
| CN118591523A (zh) * | 2021-11-12 | 2024-09-03 | 阿萨达股份公司 | 多元醇衍生的化合物 |
| US20250002446A1 (en) * | 2021-11-26 | 2025-01-02 | Arxada Ag | Acetoacetate Based Ketals |
| US20240299548A1 (en) * | 2022-01-18 | 2024-09-12 | Today, Inc. | Molecules, formulations, and methods for nutritional support of athletes, patients, and others |
| US12023382B2 (en) | 2022-01-18 | 2024-07-02 | Today Inc. | Molecules, formulations, and methods for nutritional support of athletes, patients, and others |
| 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 (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007115282A2 (en) | 2006-04-03 | 2007-10-11 | 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 |
| 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 |
| US20120034193A1 (en) * | 2009-01-24 | 2012-02-09 | Daryl Rees | Treatment of neurotrophic factor mediated disorders |
| WO2012154837A2 (en) | 2011-05-09 | 2012-11-15 | 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 |
| DK2914251T3 (da) | 2012-11-05 | 2019-11-04 | Us Health | Ketonlegemer til beskyttelse af væv mod beskadigelse som følge af ioniseringsstråling |
| WO2014085652A1 (en) | 2012-11-28 | 2014-06-05 | University Of South Florida | Targeting cancer with metabolic therapy and hyperbaric oxygen |
| 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 |
| 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 |
| 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 |
| JP2019526607A (ja) | 2016-09-12 | 2019-09-19 | ユニバーシティ・オブ・サウス・フロリダ | ケトンにより改善された神経再生 |
| FI3558280T3 (fi) | 2016-12-21 | 2023-07-13 | Univ Kinderspital Beider Basel | Migreenin ennaltaehkäisy ja hoito |
-
2016
- 2016-12-23 US US15/389,828 patent/US20180177753A1/en not_active Abandoned
-
2017
- 2017-11-30 WO PCT/US2017/063832 patent/WO2018118369A1/en not_active Ceased
- 2017-11-30 CA CA3046350A patent/CA3046350C/en active Active
- 2017-11-30 IL IL267540A patent/IL267540B/en unknown
- 2017-11-30 KR KR1020197020923A patent/KR102390608B1/ko active Active
- 2017-11-30 ES ES17884757T patent/ES2962879T3/es active Active
- 2017-11-30 MX MX2019006844A patent/MX389468B/es unknown
- 2017-11-30 MY MYPI2019003609A patent/MY190308A/en unknown
- 2017-11-30 EP EP17884757.0A patent/EP3558458B1/en active Active
- 2017-11-30 BR BR112019012431A patent/BR112019012431A2/pt not_active Application Discontinuation
- 2017-11-30 CN CN201780078046.7A patent/CN110167637B/zh active Active
- 2017-11-30 PT PT178847570T patent/PT3558458T/pt unknown
- 2017-11-30 JP JP2019534701A patent/JP7108320B2/ja active Active
-
2018
- 2018-12-14 US US16/220,365 patent/US10792269B2/en active Active
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