BR112019012431A2 - uso de um éster de (3-hidroxibutirato) de glicerila e de um éster de tris(dl-3-hidroxibutirato) de glicerila - Google Patents
uso de um éster de (3-hidroxibutirato) de glicerila e de um éster de tris(dl-3-hidroxibutirato) de glicerila Download PDFInfo
- Publication number
- BR112019012431A2 BR112019012431A2 BR112019012431A BR112019012431A BR112019012431A2 BR 112019012431 A2 BR112019012431 A2 BR 112019012431A2 BR 112019012431 A BR112019012431 A BR 112019012431A BR 112019012431 A BR112019012431 A BR 112019012431A BR 112019012431 A2 BR112019012431 A2 BR 112019012431A2
- Authority
- BR
- Brazil
- Prior art keywords
- hydroxybutyrate
- glyceryl
- migraine
- ester
- acyl
- Prior art date
Links
- -1 glyceryl (3-hydroxybutyrate) ester Chemical class 0.000 title claims description 38
- WHBMMWSBFZVSSR-UHFFFAOYSA-M 3-hydroxybutyrate Chemical compound CC(O)CC([O-])=O WHBMMWSBFZVSSR-UHFFFAOYSA-M 0.000 title claims description 36
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 title claims description 32
- 239000007983 Tris buffer Substances 0.000 title claims description 25
- 150000002148 esters Chemical class 0.000 title claims description 18
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 98
- 206010027599 migraine Diseases 0.000 claims abstract description 83
- 208000024891 symptom Diseases 0.000 claims abstract description 38
- WHBMMWSBFZVSSR-UHFFFAOYSA-N R3HBA Natural products CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 30
- 230000003252 repetitive effect Effects 0.000 claims description 18
- 150000002576 ketones Chemical class 0.000 claims description 17
- 206010019233 Headaches Diseases 0.000 claims description 16
- 231100000869 headache Toxicity 0.000 claims description 16
- 239000008280 blood Substances 0.000 claims description 15
- 210000004369 blood Anatomy 0.000 claims description 15
- 230000001684 chronic effect Effects 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 230000001667 episodic effect Effects 0.000 claims description 10
- 208000037048 Prodromal Symptoms Diseases 0.000 claims description 8
- 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 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- CBTHKODKAPVTNY-UHFFFAOYSA-N 2,3-dihydroxypropyl 3-hydroxybutanoate Chemical compound CC(O)CC(=O)OCC(O)CO CBTHKODKAPVTNY-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000004519 grease Substances 0.000 claims 10
- 125000002252 acyl group Chemical group 0.000 claims 7
- WHBMMWSBFZVSSR-GSVOUGTGSA-M (R)-3-hydroxybutyrate Chemical compound C[C@@H](O)CC([O-])=O WHBMMWSBFZVSSR-GSVOUGTGSA-M 0.000 claims 2
- WTKMPKREPYCDPG-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-hydroxybutanoate Chemical compound CCC(O)C(=O)OCC(O)CO WTKMPKREPYCDPG-UHFFFAOYSA-N 0.000 claims 1
- AFENDNXGAFYKQO-UHFFFAOYSA-N 2-hydroxybutyric acid Chemical group CCC(O)C(O)=O AFENDNXGAFYKQO-UHFFFAOYSA-N 0.000 claims 1
- YPTDKZCIRCQPNH-UHFFFAOYSA-N CCC(CC(CO)O)(C(=O)O)O Chemical compound CCC(CC(CO)O)(C(=O)O)O YPTDKZCIRCQPNH-UHFFFAOYSA-N 0.000 claims 1
- ZZVQIOPAEDURET-UHFFFAOYSA-N [3-hydroxy-2-(3-hydroxybutanoyloxy)propyl] 3-hydroxybutanoate Chemical compound CC(O)CC(=O)OCC(CO)OC(=O)CC(C)O ZZVQIOPAEDURET-UHFFFAOYSA-N 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 235000020887 ketogenic diet Nutrition 0.000 description 22
- 238000011282 treatment Methods 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- 229960003133 ergot alkaloid Drugs 0.000 description 6
- 150000004667 medium chain fatty acids Chemical class 0.000 description 6
- 230000002265 prevention Effects 0.000 description 6
- 235000005911 diet Nutrition 0.000 description 5
- 230000037213 diet Effects 0.000 description 5
- 238000002651 drug therapy Methods 0.000 description 5
- 239000013589 supplement Substances 0.000 description 5
- 206010015037 epilepsy Diseases 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- 230000000007 visual effect Effects 0.000 description 4
- 206010022489 Insulin Resistance Diseases 0.000 description 3
- 230000036765 blood level Effects 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000003642 hunger Nutrition 0.000 description 3
- 229940057917 medium chain triglycerides Drugs 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 208000018522 Gastrointestinal disease Diseases 0.000 description 2
- 208000007976 Ketosis Diseases 0.000 description 2
- 206010034960 Photophobia Diseases 0.000 description 2
- 206010047571 Visual impairment Diseases 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 230000001054 cortical effect Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 230000000763 evoking effect Effects 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 230000035861 hyperketonemia Effects 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical group CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 2
- 229940012843 omega-3 fatty acid Drugs 0.000 description 2
- 239000006014 omega-3 oil Substances 0.000 description 2
- 235000021085 polyunsaturated fats Nutrition 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- 230000037351 starvation Effects 0.000 description 2
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 description 1
- 206010000410 Acetonaemia Diseases 0.000 description 1
- 208000010444 Acidosis Diseases 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 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 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 238000008214 LDL Cholesterol Methods 0.000 description 1
- 208000000060 Migraine with aura Diseases 0.000 description 1
- 206010029148 Nephrolithiasis Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 206010047513 Vision blurred Diseases 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
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 230000004397 blinking Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000037149 energy metabolism Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013350 formula milk Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 125000005908 glyceryl ester group Chemical group 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 230000004140 ketosis Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 235000021084 monounsaturated fats Nutrition 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000007996 neuronal plasticity Effects 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 235000020665 omega-6 fatty acid Nutrition 0.000 description 1
- 229940033080 omega-6 fatty acid Drugs 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 238000011422 pharmacological therapy Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
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Classifications
-
- 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
-
- 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
- A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
- A61K31/231—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms having one or two double bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| 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 |
| PCT/US2017/063832 WO2018118369A1 (en) | 2016-12-23 | 2017-11-30 | Glyceryl 3-hydroxybutyrates for migraine symptom management |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BR112019012431A2 true BR112019012431A2 (pt) | 2020-04-14 |
Family
ID=62624821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112019012431A BR112019012431A2 (pt) | 2016-12-23 | 2017-11-30 | uso de um éster de (3-hidroxibutirato) de glicerila e de um éster de tris(dl-3-hidroxibutirato) de glicerila |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US20180177753A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3558458B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP7108320B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102390608B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN110167637B (cg-RX-API-DMAC7.html) |
| BR (1) | BR112019012431A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA3046350C (cg-RX-API-DMAC7.html) |
| ES (1) | ES2962879T3 (cg-RX-API-DMAC7.html) |
| IL (1) | IL267540B (cg-RX-API-DMAC7.html) |
| MX (1) | MX389468B (cg-RX-API-DMAC7.html) |
| MY (1) | MY190308A (cg-RX-API-DMAC7.html) |
| PT (1) | PT3558458T (cg-RX-API-DMAC7.html) |
| WO (1) | WO2018118369A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (33)
| 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 |
| US11806324B2 (en) | 2018-04-18 | 2023-11-07 | Axcess Global Sciences, Llc | Beta-hydroxybutyric acid compositions and methods for oral delivery of ketone bodies |
| 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 |
| US12109182B2 (en) | 2016-04-19 | 2024-10-08 | Axcess Global Sciences, Llc | Administration of R-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 |
| 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 |
| US12329734B2 (en) | 2017-12-19 | 2025-06-17 | Axcess Global Sciences, Llc | Use of S-beta-hydroxybutyrate compounds for induction and maintenance of flow |
| US12496283B2 (en) | 2016-04-19 | 2025-12-16 | Axcess Global Sciences, Llc | Administration of R-beta-hydroxybutyrate and related compounds in humans |
| DK3558280T3 (da) | 2016-12-21 | 2023-08-21 | Univ Kinderspital Beider Basel | Forebyggelse og behandling af migræne |
| 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 |
| EP3880650B1 (de) * | 2019-01-17 | 2023-09-06 | KetoLipix Therapeutics GmbH | Verfahren zur herstellung von struktureinheiten auf basis von glyceriden von hydroxycarbonsäuren enthaltenden lipiden |
| 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 |
| BR112021017954A2 (pt) | 2019-03-14 | 2021-11-16 | Neuroenergy Ventures Inc | Formulação de mascaramento de sabor para compostos de corpo cetônico |
| 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 |
| US20250197566A1 (en) * | 2019-06-12 | 2025-06-19 | Ioi Oleo Gmbh | Process for preparing polyol-based esters of acyl-capped hydroxy carboxylic 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 |
| 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 |
| 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 |
| 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 |
|---|---|---|---|---|
| GB0420856D0 (en) * | 2004-09-20 | 2004-10-20 | Ketocytonyx Inc | Cns modulators |
| 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 |
| 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 |
| 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 |
| GB201314127D0 (en) * | 2013-08-07 | 2013-09-18 | Tdeltas Ltd | Ketone body and ketone body ester for reducing muscle breakdown |
| 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 |
| 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 |
| AU2017322708A1 (en) | 2016-09-12 | 2019-03-21 | University Of South Florida | Neuroregeneration improved by ketone |
| DK3558280T3 (da) | 2016-12-21 | 2023-08-21 | Univ Kinderspital Beider Basel | Forebyggelse og behandling af migræne |
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2016
- 2016-12-23 US US15/389,828 patent/US20180177753A1/en not_active Abandoned
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2017
- 2017-11-30 CN CN201780078046.7A patent/CN110167637B/zh active Active
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- 2017-11-30 PT PT178847570T patent/PT3558458T/pt unknown
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- 2017-11-30 CA CA3046350A patent/CA3046350C/en active Active
- 2017-11-30 BR BR112019012431A patent/BR112019012431A2/pt not_active Application Discontinuation
- 2017-11-30 JP JP2019534701A patent/JP7108320B2/ja active Active
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- 2017-11-30 MY MYPI2019003609A patent/MY190308A/en unknown
- 2017-11-30 EP EP17884757.0A patent/EP3558458B1/en active Active
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2018
- 2018-12-14 US US16/220,365 patent/US10792269B2/en active Active
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| CA3046350A1 (en) | 2018-06-28 |
| JP7108320B2 (ja) | 2022-07-28 |
| EP3558458B1 (en) | 2023-10-18 |
| US10792269B2 (en) | 2020-10-06 |
| MX2019006844A (es) | 2019-08-16 |
| US20180177753A1 (en) | 2018-06-28 |
| PT3558458T (pt) | 2023-11-27 |
| MY190308A (en) | 2022-04-13 |
| IL267540B (en) | 2022-07-01 |
| EP3558458A1 (en) | 2019-10-30 |
| WO2018118369A1 (en) | 2018-06-28 |
| CN110167637A (zh) | 2019-08-23 |
| KR102390608B1 (ko) | 2022-04-25 |
| CA3046350C (en) | 2022-08-16 |
| CN110167637B (zh) | 2023-03-14 |
| KR20190099465A (ko) | 2019-08-27 |
| EP3558458A4 (en) | 2020-08-12 |
| IL267540A (en) | 2019-08-29 |
| JP2020502250A (ja) | 2020-01-23 |
| ES2962879T3 (es) | 2024-03-21 |
| MX389468B (es) | 2025-03-20 |
| US20190117612A1 (en) | 2019-04-25 |
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