JP6526066B2 - リポ酸コリンエステル組成物及び使用方法 - Google Patents
リポ酸コリンエステル組成物及び使用方法 Download PDFInfo
- Publication number
- JP6526066B2 JP6526066B2 JP2016573672A JP2016573672A JP6526066B2 JP 6526066 B2 JP6526066 B2 JP 6526066B2 JP 2016573672 A JP2016573672 A JP 2016573672A JP 2016573672 A JP2016573672 A JP 2016573672A JP 6526066 B2 JP6526066 B2 JP 6526066B2
- Authority
- JP
- Japan
- Prior art keywords
- mass
- aqueous
- lipoic acid
- pharmaceutical composition
- choline ester
- 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.)
- Expired - Fee Related
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- -1 Lipoic acid choline ester Chemical class 0.000 title claims description 138
- 239000000203 mixture Substances 0.000 title claims description 136
- 235000019136 lipoic acid Nutrition 0.000 title claims description 112
- 229960002663 thioctic acid Drugs 0.000 title claims description 111
- 229960001231 choline Drugs 0.000 title claims description 98
- 238000000034 method Methods 0.000 title claims description 38
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 109
- 239000008194 pharmaceutical composition Substances 0.000 claims description 82
- 239000007864 aqueous solution Substances 0.000 claims description 59
- 238000002360 preparation method Methods 0.000 claims description 48
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 45
- 238000003860 storage Methods 0.000 claims description 42
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 30
- 239000003814 drug Substances 0.000 claims description 25
- 239000003755 preservative agent Substances 0.000 claims description 25
- 229960000686 benzalkonium chloride Drugs 0.000 claims description 23
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical group [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 23
- 229940079593 drug Drugs 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 235000004279 alanine Nutrition 0.000 claims description 20
- 239000000872 buffer Substances 0.000 claims description 20
- 239000012535 impurity Substances 0.000 claims description 20
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- 150000001413 amino acids Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims description 4
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- 125000003158 alcohol group Chemical group 0.000 claims description 3
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- AGBQKNBQESQNJD-UHFFFAOYSA-M lipoate Chemical compound [O-]C(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-M 0.000 claims 2
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- 235000011187 glycerol Nutrition 0.000 description 38
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- QMADNKDMPGZUKN-UTONKHPSSA-M 2-[5-[(3R)-dithiolan-3-yl]pentanoyloxy]ethyl-trimethylazanium chloride Chemical compound [Cl-].C[N+](C)(C)CCOC(=O)CCCC[C@@H]1CCSS1 QMADNKDMPGZUKN-UTONKHPSSA-M 0.000 description 22
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- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 13
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- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 4
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- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- A61K9/00—Medicinal preparations characterised by special physical form
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- A61K31/33—Heterocyclic compounds
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- A61K31/385—Heterocyclic compounds having sulfur as a ring hetero atom having two or more sulfur atoms in the same ring
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/186—Quaternary ammonium compounds, e.g. benzalkonium chloride or cetrimide
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- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0048—Eye, e.g. artificial tears
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/10—Ophthalmic agents for accommodation disorders, e.g. myopia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461947378P | 2014-03-03 | 2014-03-03 | |
| US61/947,378 | 2014-03-03 | ||
| PCT/US2015/018505 WO2015134510A1 (en) | 2014-03-03 | 2015-03-03 | Lipoic acid choline ester compositions and methods of use |
Publications (3)
| Publication Number | Publication Date |
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| JP2017511816A JP2017511816A (ja) | 2017-04-27 |
| JP2017511816A5 JP2017511816A5 (OSRAM) | 2018-04-12 |
| JP6526066B2 true JP6526066B2 (ja) | 2019-06-05 |
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| EP (1) | EP3113613A4 (OSRAM) |
| JP (1) | JP6526066B2 (OSRAM) |
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| CN (2) | CN106455563A (OSRAM) |
| AU (2) | AU2015227307A1 (OSRAM) |
| BR (1) | BR112016020181A8 (OSRAM) |
| CA (1) | CA2941518A1 (OSRAM) |
| IL (1) | IL247529B (OSRAM) |
| MX (1) | MX384877B (OSRAM) |
| RU (1) | RU2735790C2 (OSRAM) |
| WO (1) | WO2015134510A1 (OSRAM) |
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| WO2017053646A1 (en) * | 2015-09-24 | 2017-03-30 | Encore Vision, Inc. | Lipoic acid choline ester compositions and methods to generate biocompatible ophthalmic formulations |
| JOP20190057A1 (ar) * | 2016-09-23 | 2019-03-24 | Encore Vision Inc | تركيبات استر كولين حمض الليبويك وطرق تثبيتها إلى منتجات عقار ذات صلة دوائية |
| US10052343B1 (en) | 2017-02-03 | 2018-08-21 | Gene Signal International Sa | Sterile formulation comprising a stable phosphorothioate oligonucleotide |
| CN107089967A (zh) * | 2017-05-12 | 2017-08-25 | 苏州富士莱医药股份有限公司 | 一种r‑硫辛酸胆碱酯卤化物的制备方法 |
| CN106967044B (zh) * | 2017-05-12 | 2019-02-22 | 苏州富士莱医药股份有限公司 | 制备r-硫辛酸胆碱酯卤化物的方法 |
| CN109394745A (zh) * | 2017-08-17 | 2019-03-01 | 博瑞生物医药（苏州）股份有限公司 | 一种包含左旋肉碱和β-羟基丁酸化合物的组合物 |
| TW202103696A (zh) * | 2019-04-17 | 2021-02-01 | 日商參天製藥股份有限公司 | 硫辛酸前藥 |
| US20200383946A1 (en) * | 2019-05-07 | 2020-12-10 | Aciont Inc. | Lipoic acid formulations |
| CN113387923A (zh) * | 2020-03-13 | 2021-09-14 | 诺华股份有限公司 | 硫辛酸胆碱酯盐的药物组合物及使用其的治疗方法 |
| CN113717770B (zh) * | 2020-05-25 | 2022-06-03 | 中国石油天然气股份有限公司 | 一种金属加工油 |
| GB202305212D0 (en) | 2023-04-06 | 2023-05-24 | Elixa Mediscience Ltd | Compounds |
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-
2015
- 2015-03-03 BR BR112016020181A patent/BR112016020181A8/pt not_active IP Right Cessation
- 2015-03-03 CA CA2941518A patent/CA2941518A1/en not_active Abandoned
- 2015-03-03 KR KR1020167026593A patent/KR20160145558A/ko not_active Ceased
- 2015-03-03 RU RU2016137784A patent/RU2735790C2/ru active
- 2015-03-03 EP EP15758583.7A patent/EP3113613A4/en not_active Withdrawn
- 2015-03-03 AU AU2015227307A patent/AU2015227307A1/en not_active Abandoned
- 2015-03-03 CN CN201580012000.6A patent/CN106455563A/zh active Pending
- 2015-03-03 CN CN202011555416.1A patent/CN112641720A/zh active Pending
- 2015-03-03 MX MX2016011290A patent/MX384877B/es unknown
- 2015-03-03 WO PCT/US2015/018505 patent/WO2015134510A1/en not_active Ceased
- 2015-03-03 JP JP2016573672A patent/JP6526066B2/ja not_active Expired - Fee Related
- 2015-03-03 US US15/118,910 patent/US20160354340A1/en not_active Abandoned
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2016
- 2016-08-29 IL IL247529A patent/IL247529B/en active IP Right Grant
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2019
- 2019-09-22 US US16/578,368 patent/US11426381B2/en active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| CA2941518A1 (en) | 2015-09-11 |
| EP3113613A4 (en) | 2019-03-13 |
| JP2017511816A (ja) | 2017-04-27 |
| CN112641720A (zh) | 2021-04-13 |
| AU2019240641A1 (en) | 2019-10-24 |
| EP3113613A1 (en) | 2017-01-11 |
| AU2015227307A1 (en) | 2016-10-13 |
| WO2015134510A1 (en) | 2015-09-11 |
| CN106455563A (zh) | 2017-02-22 |
| US20200281891A1 (en) | 2020-09-10 |
| BR112016020181A8 (pt) | 2021-06-29 |
| BR112016020181A2 (pt) | 2017-08-15 |
| IL247529A0 (en) | 2016-11-30 |
| AU2019240641B2 (en) | 2020-10-29 |
| US11426381B2 (en) | 2022-08-30 |
| US20160354340A1 (en) | 2016-12-08 |
| MX2016011290A (es) | 2017-04-27 |
| KR20160145558A (ko) | 2016-12-20 |
| RU2735790C2 (ru) | 2020-11-09 |
| IL247529B (en) | 2020-10-29 |
| RU2016137784A3 (OSRAM) | 2018-10-18 |
| RU2016137784A (ru) | 2018-04-03 |
| MX384877B (es) | 2025-03-14 |
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