KR102384266B1 - 연질 겔 캡슐에서 베타-하이드록시이소발레르산 제형의 안정화 - Google Patents
연질 겔 캡슐에서 베타-하이드록시이소발레르산 제형의 안정화 Download PDFInfo
- Publication number
- KR102384266B1 KR102384266B1 KR1020187037387A KR20187037387A KR102384266B1 KR 102384266 B1 KR102384266 B1 KR 102384266B1 KR 1020187037387 A KR1020187037387 A KR 1020187037387A KR 20187037387 A KR20187037387 A KR 20187037387A KR 102384266 B1 KR102384266 B1 KR 102384266B1
- Authority
- KR
- South Korea
- Prior art keywords
- soft gel
- capsule
- gel capsule
- liquid formulation
- excipient
- 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.)
- Active
Links
- 239000002775 capsule Substances 0.000 title claims abstract description 109
- AXFYFNCPONWUHW-UHFFFAOYSA-N beta-hydroxy-beta-methyl butyric acid Natural products CC(C)(O)CC(O)=O AXFYFNCPONWUHW-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- RWBRUCCWZPSBFC-UHFFFAOYSA-N 17-(1-hydroxyethyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(O)C)C1(C)CC2 RWBRUCCWZPSBFC-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000009472 formulation Methods 0.000 title description 9
- 230000006641 stabilisation Effects 0.000 title description 2
- 238000011105 stabilization Methods 0.000 title description 2
- 239000012669 liquid formulation Substances 0.000 claims abstract description 54
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 41
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims abstract description 19
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims abstract description 11
- ZKHQWZAMYRWXGA-KQYNXXCUSA-N Adenosine triphosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-N 0.000 claims abstract description 10
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229960001456 adenosine triphosphate Drugs 0.000 claims abstract description 10
- 229960004203 carnitine Drugs 0.000 claims abstract description 10
- 229960004956 glycerylphosphorylcholine Drugs 0.000 claims abstract description 10
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims abstract description 10
- 239000004381 Choline salt Substances 0.000 claims abstract description 8
- 235000019417 choline salt Nutrition 0.000 claims abstract description 8
- 150000003248 quinolines Chemical class 0.000 claims abstract description 8
- 229960003237 betaine Drugs 0.000 claims abstract description 7
- 239000011257 shell material Substances 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000002156 mixing Methods 0.000 claims description 13
- 229940023579 anhydrous betaine Drugs 0.000 claims description 11
- 239000004373 Pullulan Substances 0.000 claims description 8
- 229920001218 Pullulan Polymers 0.000 claims description 8
- 239000000679 carrageenan Substances 0.000 claims description 8
- 235000010418 carrageenan Nutrition 0.000 claims description 8
- 229920001525 carrageenan Polymers 0.000 claims description 8
- 229940113118 carrageenan Drugs 0.000 claims description 8
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 8
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 8
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 8
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 8
- 235000019423 pullulan Nutrition 0.000 claims description 8
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 claims description 8
- 229950010582 betaine anhydrous Drugs 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 22
- 239000000499 gel Substances 0.000 description 43
- 238000013112 stability test Methods 0.000 description 8
- 238000012430 stability testing Methods 0.000 description 8
- 150000004676 glycans Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920001282 polysaccharide Polymers 0.000 description 5
- 239000005017 polysaccharide Substances 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 210000003205 muscle Anatomy 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 208000014674 injury Diseases 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 102000015779 HDL Lipoproteins Human genes 0.000 description 2
- 108010010234 HDL Lipoproteins Proteins 0.000 description 2
- 102000007330 LDL Lipoproteins Human genes 0.000 description 2
- 108010007622 LDL Lipoproteins Proteins 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 235000015872 dietary supplement Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- AXFYFNCPONWUHW-UHFFFAOYSA-M 3-hydroxyisovalerate Chemical compound CC(C)(O)CC([O-])=O AXFYFNCPONWUHW-UHFFFAOYSA-M 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 208000029549 Muscle injury Diseases 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- -1 but not limited to Substances 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000020832 chronic kidney disease Diseases 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 229940126534 drug product Drugs 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002996 emotional effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000004220 muscle function Effects 0.000 description 1
- 230000037257 muscle growth Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 208000001076 sarcopenia Diseases 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4816—Wall or shell material
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
Landscapes
- Health & Medical Sciences (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)
- Public Health (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Neurology (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662341464P | 2016-05-25 | 2016-05-25 | |
| US62/341,464 | 2016-05-25 | ||
| PCT/US2017/034551 WO2017205673A1 (en) | 2016-05-25 | 2017-05-25 | Stabilization of beta-hydroxyisovaleric acid formulations in soft gel capsules |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20190021259A KR20190021259A (ko) | 2019-03-05 |
| KR102384266B1 true KR102384266B1 (ko) | 2022-04-06 |
Family
ID=60411620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020187037387A Active KR102384266B1 (ko) | 2016-05-25 | 2017-05-25 | 연질 겔 캡슐에서 베타-하이드록시이소발레르산 제형의 안정화 |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US10959957B2 (enExample) |
| EP (1) | EP3463327B1 (enExample) |
| JP (1) | JP6929939B2 (enExample) |
| KR (1) | KR102384266B1 (enExample) |
| CN (2) | CN121177244A (enExample) |
| AU (1) | AU2017270219B2 (enExample) |
| CA (1) | CA3024584A1 (enExample) |
| CO (1) | CO2018014085A2 (enExample) |
| MX (1) | MX2018014407A (enExample) |
| MY (1) | MY199597A (enExample) |
| RU (1) | RU2018145520A (enExample) |
| WO (1) | WO2017205673A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111888325A (zh) * | 2020-08-04 | 2020-11-06 | 瑞希(重庆)生物科技有限公司 | 一种卡拉胶凝胶、药物赋形剂和皮肤外用制剂 |
| JP7750505B2 (ja) * | 2021-10-14 | 2025-10-07 | 中日本カプセル 株式会社 | カプセル及びカプセルの製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015094925A1 (en) * | 2013-12-18 | 2015-06-25 | Capsugel Belgium Nv | Stable liquid filled hard capsule comprising beta-hydroxy-beta-methylbutyric acid |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2870062A (en) * | 1956-04-27 | 1959-01-20 | Scherer Corp R P | Gelatin composition for capsules |
| US5200191A (en) | 1991-09-11 | 1993-04-06 | Banner Gelatin Products Corp. | Softgel manufacturing process |
| US5569466A (en) | 1995-05-17 | 1996-10-29 | R. P. Scherer Corporation | Fill compositions for soft elastic gel capsules |
| US6340473B1 (en) * | 1999-07-07 | 2002-01-22 | R.P. Scherer Technologies, Inc. | Film forming compositions comprising modified starches and iota-carrageenan and methods for manufacturing soft capsules using same |
| DE10064312C2 (de) | 2000-12-22 | 2003-05-22 | Degussa | Cholinpyruvat-Hydrat, Verfahren zu dessen Herstellung, Cholinpyruvat-Hydrat enthaltende Formulierung sowie deren Verwendung |
| US7740878B2 (en) * | 2001-10-22 | 2010-06-22 | Danisco A/S | Use of betaine to enhance exercise performance |
| ES2294197T3 (es) | 2001-12-21 | 2008-04-01 | Supernus Pharmaceuticals, Inc. | Formulacion de capsula oral con estabilidad fisica aumentada. |
| DE10208568A1 (de) | 2002-02-27 | 2003-09-18 | Degussa Bioactives Deutschland | Verbindung, enthaltend Kreatin, eine Säure-Komponente und/oder einen Komplex-Bildner |
| DE10217557A1 (de) | 2002-04-19 | 2003-11-06 | Degussa Bioactives Gmbh | Funktionsnahrungsmittel enthaltend eine Phospholipid-haltige stabile Matrix |
| US20050215640A1 (en) | 2004-03-26 | 2005-09-29 | Baxter Jeffrey H | HMB compositions and uses thereof |
| US8231896B2 (en) * | 2004-11-08 | 2012-07-31 | R.P. Scherer Technologies, Llc | Non-gelatin soft capsule system |
| DE102004060914A1 (de) | 2004-12-17 | 2006-07-06 | Bioghurt Biogarde Gmbh & Co. Kg | Verwendung von Liponsäure-haltigen Cyclodextrin-Komplexen |
| EP2242489A1 (en) * | 2005-02-15 | 2010-10-27 | Jallal Messadek | Combination therapeutic compositions and method of use |
| DE102005061765A1 (de) | 2005-05-19 | 2006-11-23 | Degussa FreshTech Beverages LLC, Milwaukee | Füllmaterial für einen Getränkebehälter |
| CN101574146B (zh) * | 2008-05-07 | 2012-06-13 | 北京康比特体育科技股份有限公司 | 一种含有hmb的运动营养补剂 |
| JP2009153529A (ja) | 2009-04-17 | 2009-07-16 | Tsujido Chemical Corp | 食品組成物 |
| ES2608483T3 (es) * | 2009-12-18 | 2017-04-11 | Metabolic Technologies, Inc. | Método mejorado de administración de beta-hidroxi-beta-metilbutirato (HMB) |
| MX2013007347A (es) | 2010-12-22 | 2013-08-01 | Abbott Lab | Productos nutricionales que comprenden beta-hidroxi-beta metilbutirato de calcio y acido linoleico conjugado. |
| RU2631597C2 (ru) * | 2011-07-15 | 2017-09-25 | Нусерт Сайенсиз, Инк. | Композиции и способы модулирования метаболических путей |
| EP3733171B1 (en) * | 2012-09-10 | 2023-10-25 | Metabolic Technologies, LLC | Compositions comprising hmb and atp as well as their use |
| AU2013344753B2 (en) | 2012-11-13 | 2018-09-27 | Nusirt Sciences, Inc. | Compositions and methods for increasing energy metabolism |
| US20140272000A1 (en) | 2013-03-14 | 2014-09-18 | Metabolic Technologies, Inc. | Liquids and Foodstuffs Containing beta-hydroxy-beta-methylbutyrate (HMB) in the Free Acid Form and Methods of Manufacturing or Producing the Same |
| WO2014152098A1 (en) * | 2013-03-15 | 2014-09-25 | Banner Pharmacaps Inc. | Non-gelatin enteric soft capsules |
| JP2016520050A (ja) | 2013-05-01 | 2016-07-11 | アボット・ラボラトリーズＡｂｂｏｔｔ Ｌａｂｏｒａｔｏｒｉｅｓ | 老化筋肉再生の増強方法 |
| US20150366813A1 (en) * | 2014-06-20 | 2015-12-24 | Banner Life Sciences Llc | Liquid-filled immediate release soft gelatin capsules |
| JP2018090504A (ja) * | 2016-11-30 | 2018-06-14 | 株式会社東洋新薬 | 筋肉増強用組成物 |
-
2017
- 2017-05-25 MX MX2018014407A patent/MX2018014407A/es unknown
- 2017-05-25 MY MYPI2018002008A patent/MY199597A/en unknown
- 2017-05-25 CN CN202511046150.0A patent/CN121177244A/zh active Pending
- 2017-05-25 EP EP17803618.2A patent/EP3463327B1/en active Active
- 2017-05-25 JP JP2019514190A patent/JP6929939B2/ja active Active
- 2017-05-25 AU AU2017270219A patent/AU2017270219B2/en active Active
- 2017-05-25 CN CN201780031975.2A patent/CN109562087A/zh active Pending
- 2017-05-25 CA CA3024584A patent/CA3024584A1/en active Pending
- 2017-05-25 RU RU2018145520A patent/RU2018145520A/ru not_active Application Discontinuation
- 2017-05-25 WO PCT/US2017/034551 patent/WO2017205673A1/en not_active Ceased
- 2017-05-25 KR KR1020187037387A patent/KR102384266B1/ko active Active
- 2017-05-25 US US15/605,664 patent/US10959957B2/en active Active
-
2018
- 2018-12-24 CO CONC2018/0014085A patent/CO2018014085A2/es unknown
-
2021
- 2021-03-30 US US17/217,913 patent/US12133920B2/en active Active
-
2024
- 2024-11-04 US US18/936,798 patent/US20250057773A1/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015094925A1 (en) * | 2013-12-18 | 2015-06-25 | Capsugel Belgium Nv | Stable liquid filled hard capsule comprising beta-hydroxy-beta-methylbutyric acid |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3463327A4 (en) | 2020-01-22 |
| US20250057773A1 (en) | 2025-02-20 |
| KR20190021259A (ko) | 2019-03-05 |
| RU2018145520A3 (enExample) | 2020-08-26 |
| MX2018014407A (es) | 2019-02-21 |
| EP3463327A1 (en) | 2019-04-10 |
| EP3463327C0 (en) | 2024-04-17 |
| RU2018145520A (ru) | 2020-06-25 |
| US12133920B2 (en) | 2024-11-05 |
| AU2017270219B2 (en) | 2023-03-16 |
| WO2017205673A1 (en) | 2017-11-30 |
| JP2019517576A (ja) | 2019-06-24 |
| CN121177244A (zh) | 2025-12-23 |
| CO2018014085A2 (es) | 2019-03-18 |
| US10959957B2 (en) | 2021-03-30 |
| CA3024584A1 (en) | 2017-11-30 |
| JP6929939B2 (ja) | 2021-09-01 |
| US20170340572A1 (en) | 2017-11-30 |
| BR112018073949A2 (pt) | 2019-02-26 |
| US20210212953A1 (en) | 2021-07-15 |
| AU2017270219A1 (en) | 2018-11-29 |
| MY199597A (en) | 2023-11-08 |
| BR112018073949A8 (pt) | 2023-03-21 |
| EP3463327B1 (en) | 2024-04-17 |
| CN109562087A (zh) | 2019-04-02 |
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