AU2012289429B2 - Polymorphic forms of compounds as prolyl hydroxylase inhibitor, and uses thereof - Google Patents
Polymorphic forms of compounds as prolyl hydroxylase inhibitor, and uses thereof Download PDFInfo
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- AU2012289429B2 AU2012289429B2 AU2012289429A AU2012289429A AU2012289429B2 AU 2012289429 B2 AU2012289429 B2 AU 2012289429B2 AU 2012289429 A AU2012289429 A AU 2012289429A AU 2012289429 A AU2012289429 A AU 2012289429A AU 2012289429 B2 AU2012289429 B2 AU 2012289429B2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110207175.6 | 2011-07-22 | ||
| CN201110207175 | 2011-07-22 | ||
| CN201110209657.5 | 2011-07-25 | ||
| CN201110209657 | 2011-07-25 | ||
| CN201110211297 | 2011-07-26 | ||
| CN201110211297.2 | 2011-07-26 | ||
| PCT/CN2012/079058 WO2013013609A1 (en) | 2011-07-22 | 2012-07-23 | Polymorphic forms of compounds as prolyl hydroxylase inhibitor, and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| AU2012289429A1 AU2012289429A1 (en) | 2014-03-20 |
| AU2012289429A8 AU2012289429A8 (en) | 2014-05-22 |
| AU2012289429B2 true AU2012289429B2 (en) | 2016-07-28 |
Family
ID=47600518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2012289429A Active AU2012289429B2 (en) | 2011-07-22 | 2012-07-23 | Polymorphic forms of compounds as prolyl hydroxylase inhibitor, and uses thereof |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US9206134B2 (https=) |
| EP (1) | EP2734504B1 (https=) |
| JP (1) | JP6099644B2 (https=) |
| KR (1) | KR102029951B1 (https=) |
| CN (1) | CN104024227B8 (https=) |
| AU (1) | AU2012289429B2 (https=) |
| CA (1) | CA2842730C (https=) |
| ES (1) | ES2606631T3 (https=) |
| IL (1) | IL230580B (https=) |
| WO (1) | WO2013013609A1 (https=) |
| ZA (1) | ZA201401310B (https=) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2528232C (en) | 2003-06-06 | 2010-05-25 | Fibrogen, Inc. | Novel nitrogen-containing heteroaryl compounds and their use in increasing endogenous erythropoietin |
| NO2686520T3 (https=) | 2011-06-06 | 2018-03-17 | ||
| EP2872487B1 (en) * | 2012-07-16 | 2017-04-26 | Fibrogen, Inc. | Process for making isoquinoline compounds |
| KR20210130849A (ko) * | 2012-07-16 | 2021-11-01 | 피브로겐, 인크. | 프롤릴 하이드록실라제 억제제 [(4-하이드록시-1-메틸-7-페녹시-아이소퀴놀린-3-카보닐)-아미노]-아세트산의 결정형 |
| US8883823B2 (en) | 2012-07-16 | 2014-11-11 | Fibrogen, Inc. | Crystalline forms of a prolyl hydroxylase inhibitor |
| KR20210104173A (ko) | 2013-06-06 | 2021-08-24 | 피브로겐, 인크. | Hif 하이드록실라제 억제자의 약학적 제형 |
| SG10201910773VA (en) | 2013-06-13 | 2020-01-30 | Akebia Therapeutics Inc | Compositions and methods for treating anemia |
| AR099354A1 (es) * | 2013-11-15 | 2016-07-20 | Akebia Therapeutics Inc | Formas sólidas de ácido {[5-(3-clorofenil)-3-hidroxipiridin-2-carbonil]amino}acético, composiciones, y sus usos |
| CN103694172A (zh) * | 2013-12-26 | 2014-04-02 | 辽宁亿灵科创生物医药科技有限公司 | 含氮杂芳基化合物的衍生物 |
| AU2016209126A1 (en) | 2015-01-23 | 2017-08-10 | Akebia Therapeutics, Inc. | Solid forms of 2-(5-(3-fluorophenyl)-3-hydroxypicolinamido)acetic acid, compositions, and uses thereof |
| CN106146490B (zh) * | 2015-03-27 | 2018-10-23 | 沈阳三生制药有限责任公司 | 被芳氧基或杂芳氧基取代的5-羟基-1,7-萘啶化合物、其制备方法及其制药用途 |
| US11324734B2 (en) | 2015-04-01 | 2022-05-10 | Akebia Therapeutics, Inc. | Compositions and methods for treating anemia |
| CN104910113B (zh) * | 2015-05-21 | 2017-05-10 | 中国科学院宁波材料技术与工程研究所 | 一种羟基苯酐的制备方法 |
| CN104892509B (zh) * | 2015-06-04 | 2018-03-09 | 苏州明锐医药科技有限公司 | 诺得司他的制备方法 |
| US10450569B2 (en) | 2015-08-13 | 2019-10-22 | Somagenics, Inc. | Methods and compositions of short small hairpin RNAS and microRNAS for wound healing |
| CN105130888A (zh) | 2015-10-09 | 2015-12-09 | 中国药科大学 | 炔基吡啶类脯氨酰羟化酶抑制剂、其制备方法和医药用途 |
| CN106916105A (zh) * | 2015-12-28 | 2017-07-04 | 徐州万邦金桥制药有限公司 | 一种纯化可博美的方法 |
| CN106187888A (zh) * | 2016-07-18 | 2016-12-07 | 江苏德源药业股份有限公司 | Fg‑4592单晶及其制备方法 |
| CZ2016627A3 (cs) | 2016-10-07 | 2018-04-18 | Zentiva, K.S. | Způsob přípravy (7-fenoxy-4-hydroxy-1-methylisochinolin-3-karbonyl)glycinu (roxadustatu) a jeho intermediátů založený na souběžném otevírání oxazolového kruhu, štěpení etheru a tvorbě iminu |
| CN107954931B (zh) * | 2016-10-17 | 2021-06-22 | 上海医药集团青岛国风药业股份有限公司 | 一种诺得司他的制备方法 |
| CN108017583B (zh) * | 2016-11-01 | 2021-04-06 | 徐州万邦金桥制药有限公司 | 一种可博美的制备方法 |
| WO2019030711A1 (en) * | 2017-08-11 | 2019-02-14 | Dr. Reddy’S Laboratories Limited | POLYMORPHS AND CO-CRYSTALS OF ROXADUSTAT |
| US11192860B2 (en) * | 2017-09-04 | 2021-12-07 | Sandoz Ag | Co-crystal of an orally available HIF prolyl hydroxylase inhibitor |
| CA3083672A1 (en) * | 2017-12-01 | 2019-06-06 | Dr. Reddy's Laboratories Limited | Process for the preparation of roxadustat and its intermediates |
| CN109956870A (zh) * | 2017-12-14 | 2019-07-02 | 南京卡文迪许生物工程技术有限公司 | 一种罗沙司他的合成方法及其中间体化合物 |
| CN108059679B (zh) * | 2017-12-27 | 2020-03-24 | 吉林大学 | 一种人源单链抗体及其应用 |
| CN110218184B (zh) * | 2018-03-01 | 2022-09-27 | 广东东阳光药业有限公司 | 诺德司他共晶及其制备方法 |
| CN115246789B (zh) * | 2018-03-16 | 2023-10-17 | 上海医药集团青岛国风药业股份有限公司 | 一种诺得司他的制备方法 |
| CN108424388B (zh) * | 2018-04-19 | 2020-08-21 | 杭州科巢生物科技有限公司 | 一种慢性贫血药物的制备方法 |
| EP3790863A1 (en) | 2018-05-09 | 2021-03-17 | Akebia Therapeutics Inc. | Process for preparing 2-[[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino]acetic acid |
| CN110903242B (zh) * | 2018-09-14 | 2023-05-12 | 四川科伦药物研究院有限公司 | 罗沙司他中间体的制备方法 |
| CN109369525A (zh) * | 2018-12-29 | 2019-02-22 | 安礼特(上海)医药科技有限公司 | 罗沙司它的新晶型及其制备方法 |
| WO2020178847A1 (en) | 2019-03-01 | 2020-09-10 | Mylan Laboratories Limited | Cocrystal of roxadustat and d-proline |
| CN109776415B (zh) * | 2019-03-07 | 2020-11-17 | 福建南方制药股份有限公司 | 一种Roxadustat中间体的制备方法 |
| IL287258B2 (en) | 2019-04-18 | 2026-01-01 | Nikang Therapeutics Inc | Inhibitors as tetrahydro-1h-cyclopenta[cd] indene derivatives as hypoxia inducible factor -2alpha |
| CN109956901B (zh) * | 2019-04-25 | 2022-09-06 | 南京正大天晴制药有限公司 | 异喹啉酮类化合物的制备方法 |
| US20220340532A1 (en) | 2019-08-07 | 2022-10-27 | Teva Pharmaceuticals International Gmbh | Processes for the preparation of roxadustat and intermediates thereof |
| CN112679428A (zh) * | 2019-10-17 | 2021-04-20 | 罗欣药业(上海)有限公司 | 罗沙司他新晶型及其制备方法 |
| CN112679430B (zh) * | 2019-10-18 | 2023-05-05 | 上海迪赛诺化学制药有限公司 | 一种制备异喹啉酮类化合物的方法 |
| CN112679431B (zh) * | 2019-10-18 | 2023-05-05 | 上海迪赛诺化学制药有限公司 | 一种制备异喹啉酮类化合物的方法 |
| CN112679429B (zh) * | 2019-10-18 | 2023-05-05 | 上海迪赛诺化学制药有限公司 | 一种制备异喹啉酮类化合物的方法 |
| WO2021073623A1 (zh) * | 2019-10-18 | 2021-04-22 | 上海迪赛诺化学制药有限公司 | 一种制备异喹啉酮类化合物的方法 |
| JP2022553706A (ja) | 2019-10-22 | 2022-12-26 | ▲蘇▼州科睿思制▲葯▼有限公司 | 低酸素誘導因子-プロリルヒドロキシラーゼ阻害剤の結晶形 |
| US11524939B2 (en) | 2019-11-13 | 2022-12-13 | Akebia Therapeutics, Inc. | Solid forms of {[5-(3-chlorophenyl)-3-hydroxypyridine-2-carbonyl]amino} acetic acid |
| CN111205224B (zh) * | 2020-04-22 | 2020-08-25 | 南京佰麦生物技术有限公司 | 一种罗沙司他水合物的晶型及其制备方法和应用 |
| CN113801060B (zh) * | 2020-06-13 | 2025-06-27 | 苏州鹏旭医药科技有限公司 | 一种多取代异喹啉化合物的制备方法 |
| EP4169906B1 (en) | 2020-06-19 | 2024-09-04 | Jumpcan (Shanghai) Medical Technology Co., Ltd | Method for synthesis of roxadustat and intermediate thereof, and intermediate thereof |
| CN112500344B (zh) * | 2020-11-18 | 2022-07-01 | 江苏豪森药业集团有限公司 | 罗沙司他晶型及其制备方法 |
| CN112194624A (zh) * | 2020-11-18 | 2021-01-08 | 江苏豪森药业集团有限公司 | 一种异喹啉类化合物的晶型及其制备方法 |
| CN115144480B (zh) * | 2021-03-31 | 2023-11-28 | 成都倍特药业股份有限公司 | 一种从罗沙司他中间体中检测吗啉和/或四甲基甲烷二胺的方法 |
| CN115724796A (zh) * | 2021-08-26 | 2023-03-03 | 成都苑东生物制药股份有限公司 | 一种罗沙司他新晶型及其制备方法 |
| WO2023095162A1 (en) | 2021-11-26 | 2023-06-01 | Mylan Laboratories Limited | Cocrystal of roxadustat and nicotinamide |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004108681A1 (en) * | 2003-06-06 | 2004-12-16 | Fibrogen, Inc. | Nitrogen-containing heteroaryl compounds and their use in increasing endogenous erythropoietin |
| CN101394843A (zh) * | 2005-06-06 | 2009-03-25 | 菲布罗根公司 | 使用HIFα稳定剂的改进的贫血治疗 |
| CN101500569A (zh) * | 2006-06-15 | 2009-08-05 | 菲布罗根公司 | 用于治疗癌症贫血的hif羟化酶抑制剂 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5470285A (en) * | 1977-11-14 | 1979-06-05 | Tanabe Seiyaku Co Ltd | Production of 4-hydroxyisocarbostyryl-3-carboxylic analog |
| DE19746287A1 (de) * | 1997-10-20 | 1999-04-22 | Hoechst Marion Roussel De Gmbh | Substituierte Isochinolin-2-Carbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
| US7893071B2 (en) * | 2001-04-23 | 2011-02-22 | University Of Virginia Patent Foundation | Synthesis and evaluation of novel phthalimide mimics as anti-angiogenic |
| US7189697B2 (en) | 2004-04-13 | 2007-03-13 | Trustees Of Tufts College | Compositions and uses of a galectin for treatment of dry eye syndrome |
| JP5202327B2 (ja) | 2005-12-09 | 2013-06-05 | アムジエン・インコーポレーテツド | プロリルヒドロキシラーゼ阻害活性を示すキノロンベースの化合物、およびこの組成物、およびこの使用 |
| EP2476669A1 (en) * | 2006-01-27 | 2012-07-18 | Fibrogen, Inc. | Cyanoisoquinoline compounds and methods of use thereof |
| JP4311416B2 (ja) | 2006-06-30 | 2009-08-12 | 株式会社日立製作所 | 渦電流探傷法による表面欠陥長さ評価方法 |
| AU2010273101B2 (en) | 2009-07-15 | 2016-02-25 | Beijing Betta Pharmaceuticals Co., Ltd. | Compounds as hypoxia mimetics, and compositions, and uses thereof |
-
2012
- 2012-07-23 US US14/233,902 patent/US9206134B2/en active Active
- 2012-07-23 CN CN201280036322.0A patent/CN104024227B8/zh active Active
- 2012-07-23 EP EP12817360.6A patent/EP2734504B1/en not_active Not-in-force
- 2012-07-23 JP JP2014520521A patent/JP6099644B2/ja not_active Expired - Fee Related
- 2012-07-23 AU AU2012289429A patent/AU2012289429B2/en active Active
- 2012-07-23 WO PCT/CN2012/079058 patent/WO2013013609A1/en not_active Ceased
- 2012-07-23 KR KR1020147004452A patent/KR102029951B1/ko not_active Expired - Fee Related
- 2012-07-23 ES ES12817360.6T patent/ES2606631T3/es active Active
- 2012-07-23 CA CA2842730A patent/CA2842730C/en active Active
-
2014
- 2014-01-22 IL IL230580A patent/IL230580B/en active IP Right Grant
- 2014-02-20 ZA ZA2014/01310A patent/ZA201401310B/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004108681A1 (en) * | 2003-06-06 | 2004-12-16 | Fibrogen, Inc. | Nitrogen-containing heteroaryl compounds and their use in increasing endogenous erythropoietin |
| CN101394843A (zh) * | 2005-06-06 | 2009-03-25 | 菲布罗根公司 | 使用HIFα稳定剂的改进的贫血治疗 |
| CN101500569A (zh) * | 2006-06-15 | 2009-08-05 | 菲布罗根公司 | 用于治疗癌症贫血的hif羟化酶抑制剂 |
Also Published As
| Publication number | Publication date |
|---|---|
| IL230580A0 (en) | 2014-03-31 |
| CN104024227A (zh) | 2014-09-03 |
| JP6099644B2 (ja) | 2017-03-22 |
| ES2606631T3 (es) | 2017-03-24 |
| AU2012289429A1 (en) | 2014-03-20 |
| KR20140049004A (ko) | 2014-04-24 |
| ZA201401310B (en) | 2015-04-29 |
| US9206134B2 (en) | 2015-12-08 |
| WO2013013609A1 (en) | 2013-01-31 |
| US20150031721A1 (en) | 2015-01-29 |
| EP2734504A4 (en) | 2014-12-31 |
| EP2734504A1 (en) | 2014-05-28 |
| IL230580B (en) | 2019-07-31 |
| CA2842730A1 (en) | 2013-01-31 |
| CN104024227B8 (zh) | 2025-07-29 |
| CN104024227B (zh) | 2015-12-02 |
| CA2842730C (en) | 2018-08-21 |
| JP2014524920A (ja) | 2014-09-25 |
| KR102029951B1 (ko) | 2019-11-08 |
| EP2734504B1 (en) | 2016-09-14 |
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