CA2971729C - Creatine prodrugs, compositions and methods of use thereof - Google Patents
Creatine prodrugs, compositions and methods of use thereof Download PDFInfo
- Publication number
- CA2971729C CA2971729C CA2971729A CA2971729A CA2971729C CA 2971729 C CA2971729 C CA 2971729C CA 2971729 A CA2971729 A CA 2971729A CA 2971729 A CA2971729 A CA 2971729A CA 2971729 C CA2971729 C CA 2971729C
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- compound
- alkyl
- creatine
- formula
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/06—Seven-membered rings
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Toxicology (AREA)
- Biochemistry (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462095295P | 2014-12-22 | 2014-12-22 | |
| US62/095,295 | 2014-12-22 | ||
| PCT/US2015/067283 WO2016106284A2 (en) | 2014-12-22 | 2015-12-22 | Creatine prodrugs, compositions and methods of use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2971729A1 CA2971729A1 (en) | 2016-06-30 |
| CA2971729C true CA2971729C (en) | 2024-02-20 |
Family
ID=56128653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2971729A Active CA2971729C (en) | 2014-12-22 | 2015-12-22 | Creatine prodrugs, compositions and methods of use thereof |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US9617230B2 (https=) |
| EP (2) | EP3771709B1 (https=) |
| JP (5) | JP6692372B2 (https=) |
| AR (2) | AR103254A1 (https=) |
| CA (1) | CA2971729C (https=) |
| ES (1) | ES2832333T3 (https=) |
| TW (3) | TWI700270B (https=) |
| WO (1) | WO2016106284A2 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9617230B2 (en) | 2014-12-22 | 2017-04-11 | Farmington Pharma Development | Creatine prodrugs, compositions and methods of use thereof |
| US11021501B2 (en) | 2015-03-30 | 2021-06-01 | Farmington Pharma Development | Creatine phosphate analog prodrugs, compositions and methods of use thereof |
| KR102678696B1 (ko) * | 2017-12-01 | 2024-06-27 | 울트라제닉스 파마수티컬 인코포레이티드 | 크레아틴 전구약물, 조성물과 이의 사용 방법 |
| CN110746325A (zh) * | 2018-07-24 | 2020-02-04 | 上海和辉光电有限公司 | 一种基于胍骨架的n型掺杂化合物及其应用 |
| CN114419050B (zh) * | 2022-03-31 | 2022-06-21 | 武汉大学 | 胃黏膜可视化程度量化方法、装置、终端及可读存储介质 |
Family Cites Families (59)
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| US4767627A (en) | 1985-05-29 | 1988-08-30 | Merck & Co., Inc. | Drug delivery device which can be retained in the stomach for a controlled period of time |
| US4915952A (en) | 1987-02-27 | 1990-04-10 | Alza Corporation | Composition comprising drug, HPC, HPMC and PEO |
| US4786503A (en) | 1987-04-06 | 1988-11-22 | Alza Corporation | Dosage form comprising parallel lamine |
| US5002772A (en) | 1988-05-31 | 1991-03-26 | Pfizer Inc. | Gastric retention system for controlled drug release |
| CA1340821C (en) | 1988-10-06 | 1999-11-16 | Nobuyuki Fukazawa | Heterocyclic compounds and anticancer-drug reinforcing agents containing them as effective components |
| US5007790A (en) | 1989-04-11 | 1991-04-16 | Depomed Systems, Inc. | Sustained-release oral drug dosage form |
| EP0595894B1 (en) | 1991-07-19 | 1995-12-20 | UNIROYAL CHEMICAL COMPANY, Inc. | Seed film compositions |
| US6235313B1 (en) | 1992-04-24 | 2001-05-22 | Brown University Research Foundation | Bioadhesive microspheres and their use as drug delivery and imaging systems |
| US5643909A (en) | 1993-04-19 | 1997-07-01 | Syntex (U.S.A.) Inc. | 10,11-Methanodibenzosuberane derivatives |
| US5451409A (en) | 1993-11-22 | 1995-09-19 | Rencher; William F. | Sustained release matrix system using hydroxyethyl cellulose and hydroxypropyl cellulose polymer blends |
| AU4151996A (en) | 1994-11-08 | 1996-05-31 | Avicena Group, Inc. | Use of creatine or creatine analogs for the treatment of diseases of the nervous system |
| US5945125A (en) | 1995-02-28 | 1999-08-31 | Temple University | Controlled release tablet |
| MY113429A (en) | 1995-02-28 | 2002-02-28 | Univ Temple | Controlled release tablet containing swellable polyethylene oxide |
| US5824638A (en) | 1995-05-22 | 1998-10-20 | Shire Laboratories, Inc. | Oral insulin delivery |
| AU721190B2 (en) | 1995-10-11 | 2000-06-29 | Avicena Group, Inc. | Use of creatine analogues for the treatment of disorders of glucose metabolism |
| US5783212A (en) | 1996-02-02 | 1998-07-21 | Temple University--of the Commonwealth System of Higher Education | Controlled release drug delivery system |
| IT1282650B1 (it) | 1996-02-19 | 1998-03-31 | Jagotec Ag | Compressa farmaceutica,caratterizzata da elevato aumento di volume a contatto con liquidi biologici |
| US6008252A (en) * | 1996-07-26 | 1999-12-28 | Beale; Paxton K. | Method for increasing muscle mass in a mammal |
| US6210710B1 (en) | 1997-04-28 | 2001-04-03 | Hercules Incorporated | Sustained release polymer blend for pharmaceutical applications |
| GB9710699D0 (en) | 1997-05-24 | 1997-07-16 | Danbiosyst Uk | Gastro-retentive controlled release system |
| US6635280B2 (en) | 1997-06-06 | 2003-10-21 | Depomed, Inc. | Extending the duration of drug release within the stomach during the fed mode |
| PT1003476E (pt) | 1997-08-11 | 2005-05-31 | Alza Corp | Forma de dosagem de agente activo de libertacao prolongada adaptada para retencao gastrica |
| US6090411A (en) | 1998-03-09 | 2000-07-18 | Temple University | Monolithic tablet for controlled drug release |
| US6797283B1 (en) | 1998-12-23 | 2004-09-28 | Alza Corporation | Gastric retention dosage form having multiple layers |
| US6476006B2 (en) | 2000-06-23 | 2002-11-05 | Teva Pharmaceutical Industries, Ltd. | Composition and dosage form for delayed gastric release of alendronate and/or other bis-phosphonates |
| US20030008007A1 (en) | 2001-04-23 | 2003-01-09 | Jose Gutierrez-Rocca | Release pharmaceutical construct for gastric retention |
| US20030013767A1 (en) | 2001-07-13 | 2003-01-16 | Samuel Bessman | Method of treating weight loss using creatine |
| US20040219186A1 (en) | 2001-08-16 | 2004-11-04 | Ayres James W. | Expandable gastric retention device |
| US6723340B2 (en) | 2001-10-25 | 2004-04-20 | Depomed, Inc. | Optimal polymer mixtures for gastric retentive tablets |
| AU2002363998A1 (en) | 2001-12-15 | 2003-06-30 | Spherics, Inc. | Bioadhesive drug delivery system with enhanced gastric retention |
| EP1478345A4 (en) | 2002-01-03 | 2010-11-17 | Glaxosmithkline Llc | NOVEL PHARMACEUTICAL DOSAGE FORMS AND PROCESS FOR PRODUCTION OF SAID DOSAGE FORMS |
| DE10221344A1 (de) | 2002-05-14 | 2003-12-04 | Hannover Med Hochschule | Transgene Ratte und ihre Verwendung im Tiermodell für die humane Chorea Huntington Erkrankung sowie Nukleinsäurekonstrukte, Vektoren und Zellen zu ihrer Erzeugung |
| BR0310100A (pt) | 2002-05-17 | 2007-04-27 | Esperion Therapeutics Inc | métodos para tratar, prevenir ou reduzir a lesão de reperfusão isquêmica em um tecido ou órgão, e para prevenir ou tratar de uma condição associada com a privação de oxigênio, seguida por suprimento de oxigênio aumentado a um tecido ou órgão em necessidade disto |
| US20040102525A1 (en) | 2002-05-22 | 2004-05-27 | Kozachuk Walter E. | Compositions and methods of treating neurological disease and providing neuroprotection |
| GB0214013D0 (en) | 2002-06-18 | 2002-07-31 | Euro Celtique Sa | Pharmaceutical product |
| WO2004002445A2 (en) | 2002-06-26 | 2004-01-08 | Cadila Healthcare Limited | Novel floating dosage form |
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| JPWO2005108370A1 (ja) * | 2004-04-16 | 2008-03-21 | 味の素株式会社 | ベンゼン化合物 |
| US20060046962A1 (en) | 2004-08-25 | 2006-03-02 | Aegis Therapeutics Llc | Absorption enhancers for drug administration |
| US20060045865A1 (en) | 2004-08-27 | 2006-03-02 | Spherics, Inc. | Controlled regional oral delivery |
| US20070012105A1 (en) | 2005-07-13 | 2007-01-18 | Barnes-Jewish Hospital | Method and apparatus for resistive characteristic assessment |
| US20070032750A1 (en) | 2005-07-15 | 2007-02-08 | Jeffrey Oster | Muscle strength assessment system |
| US7683043B2 (en) | 2006-06-06 | 2010-03-23 | Xenoport, Inc. | Creatine phosphate analog prodrugs, compositions and uses thereof |
| WO2007146085A2 (en) | 2006-06-06 | 2007-12-21 | Xenoport, Inc. | Creatine phosphate prodrugs, compositions and uses thereof |
| US20070281995A1 (en) * | 2006-06-06 | 2007-12-06 | Xenoport, Inc. | Creatine analog prodrugs, compositions and uses thereof |
| WO2008101310A1 (en) * | 2007-02-20 | 2008-08-28 | Multi Formulations Ltd. | Creatine-fatty acids |
| US7319157B1 (en) | 2007-02-20 | 2008-01-15 | Multi Formulations Ltd. | Creatine-fatty acids |
| US8426395B2 (en) | 2008-05-30 | 2013-04-23 | Northern Northern Innovations Holding Corp | Preparations containing creatine and imino sugars |
| WO2010005692A2 (en) | 2008-06-16 | 2010-01-14 | E. I. Du Pont De Nemours And Company | Insecticidal cyclic carbonyl amidines |
| HK1200459A1 (en) * | 2011-09-19 | 2015-08-07 | Gencia Corporation | Modified creatine compounds |
| US9233099B2 (en) | 2012-01-11 | 2016-01-12 | University Of Cincinnati | Methods of treating cognitive dysfunction by modulating brain energy metabolism |
| AR091857A1 (es) | 2012-07-25 | 2015-03-04 | Sova Pharmaceuticals Inc | INHIBIDORES DE CISTATIONIN-g-LIASA (CSE) |
| EP2692719B1 (en) * | 2012-07-30 | 2016-06-08 | Commissariat à l'Énergie Atomique et aux Énergies Alternatives | Method for preparing creatine fatty esters, creatine fatty esters thus prepared and uses thereof |
| ITTO20121098A1 (it) * | 2012-12-18 | 2014-06-19 | Univ Degli Studi Genova | Procedimento per sintetizzare derivati della creatina |
| US20160289175A1 (en) * | 2013-11-05 | 2016-10-06 | Ultragenyx Pharmaceutical Inc. | Creatine analogs and the use thereof |
| ITTO20131070A1 (it) * | 2013-12-24 | 2015-06-25 | Univ Degli Studi Genova | Applicazione terapeutica di un derivato di creatina |
| US9617230B2 (en) | 2014-12-22 | 2017-04-11 | Farmington Pharma Development | Creatine prodrugs, compositions and methods of use thereof |
| WO2016110822A1 (en) * | 2015-01-09 | 2016-07-14 | Universita' Degli Studi Di Genova | Carboxylic biacyl creatine derivative, uses and method of synthesis thereof |
| US11021501B2 (en) | 2015-03-30 | 2021-06-01 | Farmington Pharma Development | Creatine phosphate analog prodrugs, compositions and methods of use thereof |
-
2015
- 2015-12-21 US US14/975,950 patent/US9617230B2/en active Active
- 2015-12-22 EP EP20184803.3A patent/EP3771709B1/en active Active
- 2015-12-22 EP EP15874283.3A patent/EP3237391B1/en active Active
- 2015-12-22 WO PCT/US2015/067283 patent/WO2016106284A2/en not_active Ceased
- 2015-12-22 CA CA2971729A patent/CA2971729C/en active Active
- 2015-12-22 TW TW104143162A patent/TWI700270B/zh active
- 2015-12-22 JP JP2017552008A patent/JP6692372B2/ja active Active
- 2015-12-22 TW TW111136599A patent/TWI832450B/zh active
- 2015-12-22 TW TW109123072A patent/TWI779312B/zh active
- 2015-12-22 ES ES15874283T patent/ES2832333T3/es active Active
- 2015-12-22 AR ARP150104265A patent/AR103254A1/es active IP Right Grant
-
2017
- 2017-04-07 US US15/481,568 patent/US10344007B2/en active Active
-
2019
- 2019-05-22 US US16/419,596 patent/US11407722B2/en active Active
-
2020
- 2020-04-14 JP JP2020072408A patent/JP7037597B2/ja active Active
-
2021
- 2021-05-14 AR ARP210101331A patent/AR122096A2/es unknown
-
2022
- 2022-03-04 JP JP2022033882A patent/JP7676338B2/ja active Active
-
2025
- 2025-04-30 JP JP2025075259A patent/JP2025118733A/ja active Pending
- 2025-12-16 JP JP2025252487A patent/JP2026048846A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP7037597B2 (ja) | 2022-03-16 |
| US20160176829A1 (en) | 2016-06-23 |
| TWI700270B (zh) | 2020-08-01 |
| JP7676338B2 (ja) | 2025-05-14 |
| JP2018502911A (ja) | 2018-02-01 |
| EP3771709C0 (en) | 2024-03-20 |
| EP3771709B1 (en) | 2024-03-20 |
| US20190337909A1 (en) | 2019-11-07 |
| EP3771709A1 (en) | 2021-02-03 |
| ES2832333T3 (es) | 2021-06-10 |
| US10344007B2 (en) | 2019-07-09 |
| JP2020128379A (ja) | 2020-08-27 |
| TW202304854A (zh) | 2023-02-01 |
| EP3237391A2 (en) | 2017-11-01 |
| US20170342039A1 (en) | 2017-11-30 |
| AR103254A1 (es) | 2017-04-26 |
| JP2026048846A (ja) | 2026-03-17 |
| JP6692372B2 (ja) | 2020-05-13 |
| EP3237391A4 (en) | 2018-10-03 |
| WO2016106284A2 (en) | 2016-06-30 |
| TWI779312B (zh) | 2022-10-01 |
| US11407722B2 (en) | 2022-08-09 |
| JP2022078213A (ja) | 2022-05-24 |
| TWI832450B (zh) | 2024-02-11 |
| US9617230B2 (en) | 2017-04-11 |
| AR122096A2 (es) | 2022-08-10 |
| TW202041504A (zh) | 2020-11-16 |
| WO2016106284A3 (en) | 2016-10-13 |
| JP2025118733A (ja) | 2025-08-13 |
| TW201629011A (zh) | 2016-08-16 |
| EP3237391B1 (en) | 2020-09-02 |
| CA2971729A1 (en) | 2016-06-30 |
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