KR102460385B1 - 비시클릭 헤테로아릴 치환된 화합물 - Google Patents
비시클릭 헤테로아릴 치환된 화합물 Download PDFInfo
- Publication number
- KR102460385B1 KR102460385B1 KR1020197004315A KR20197004315A KR102460385B1 KR 102460385 B1 KR102460385 B1 KR 102460385B1 KR 1020197004315 A KR1020197004315 A KR 1020197004315A KR 20197004315 A KR20197004315 A KR 20197004315A KR 102460385 B1 KR102460385 B1 KR 102460385B1
- Authority
- KR
- South Korea
- Prior art keywords
- methylquinoxalin
- methoxy
- thiazol
- oxy
- fluoro
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/498—Pyrazines or piperazines ortho- and peri-condensed with carbocyclic ring systems, e.g. quinoxaline, phenazine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662362113P | 2016-07-14 | 2016-07-14 | |
| US62/362,113 | 2016-07-14 | ||
| PCT/US2017/041878 WO2018013774A1 (en) | 2016-07-14 | 2017-07-13 | Bicyclic heteroaryl substituted compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20190027385A KR20190027385A (ko) | 2019-03-14 |
| KR102460385B1 true KR102460385B1 (ko) | 2022-10-27 |
Family
ID=59384258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020197004315A Active KR102460385B1 (ko) | 2016-07-14 | 2017-07-13 | 비시클릭 헤테로아릴 치환된 화합물 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US20190292176A1 (OSRAM) |
| EP (1) | EP3484878B1 (OSRAM) |
| JP (1) | JP7058256B2 (OSRAM) |
| KR (1) | KR102460385B1 (OSRAM) |
| CN (1) | CN109689647B (OSRAM) |
| ES (1) | ES2823180T3 (OSRAM) |
| WO (1) | WO2018013774A1 (OSRAM) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109689664B (zh) * | 2016-07-14 | 2022-04-15 | 百时美施贵宝公司 | 作为par4抑制剂的三环杂芳基取代的喹啉和氮杂喹啉化合物 |
| CN109689642B (zh) | 2016-07-14 | 2022-04-12 | 百时美施贵宝公司 | 经单环杂芳基取代的化合物 |
| JP6990228B2 (ja) | 2016-07-14 | 2022-01-13 | ブリストル－マイヤーズ スクイブ カンパニー | 二環式ヘテロアリール置換の化合物 |
| CN109836360B (zh) * | 2019-03-19 | 2021-08-13 | 南京恩泰医药科技有限公司 | 一种甲苯磺酸依度沙班中间体的制备方法及中间体化合物 |
| CN113024475B (zh) * | 2019-12-25 | 2022-08-09 | 宁夏大学 | 一种喹喔啉酮类化合物的合成方法 |
| CN111440146B (zh) * | 2020-05-15 | 2022-10-21 | 中国药科大学 | 一种具有par4拮抗活性的苯并三嗪类化合物及其应用 |
| JP7753950B2 (ja) * | 2022-03-30 | 2025-10-15 | 三菱ケミカル株式会社 | 環状亜硫酸エステルの製造方法 |
| JP2025525006A (ja) | 2022-07-28 | 2025-08-01 | バイエル、アクチエンゲゼルシャフト | ２－クロロ－３－フルオロ－４－アルコキシ－アニリンおよび２－フルオロ－３－クロロフェノールの調製のためのプロセス |
| CN118239941A (zh) * | 2022-12-22 | 2024-06-25 | 人福医药集团股份公司 | 制备p2x3抑制剂的方法 |
| CN115925588A (zh) * | 2022-12-26 | 2023-04-07 | 诚达药业股份有限公司 | 一种脂肪族亚磺酸钠盐的制备方法 |
| AR131541A1 (es) | 2023-01-07 | 2025-04-09 | Syngenta Crop Protection Ag | Compuestos de carboxamida novedosos |
| WO2025032129A1 (en) | 2023-08-08 | 2025-02-13 | Syngenta Crop Protection Ag | Novel aminoindane and aminotetraline compounds |
| US11976055B1 (en) | 2023-08-24 | 2024-05-07 | King Faisal University | 2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-3-ol as an antitumor and antimicrobial compound |
| US11986461B1 (en) | 2023-08-24 | 2024-05-21 | King Faisal University | 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-ol as an antitumor and antimicrobial compound |
| US11964959B1 (en) | 2023-09-05 | 2024-04-23 | King Faisal University | 3-(4,5-Diphenyl-2-(pyridin-3-yl)-1H-imidazol-1-yl)-N,N-dimethylpopan-1-amine as an antimicrobial compound |
| WO2025109114A1 (en) | 2023-11-24 | 2025-05-30 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
| US11952361B1 (en) | 2023-12-26 | 2024-04-09 | King Faisal University | 2-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl) pyridin-3-ol as an antitumor and antimicrobial compound |
| WO2025149629A1 (en) | 2024-01-12 | 2025-07-17 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
| WO2025149637A1 (en) | 2024-01-12 | 2025-07-17 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998020007A1 (en) * | 1996-11-06 | 1998-05-14 | Darwin Discovery Limited | Quinolines and their therapeutic use |
| US20110178041A1 (en) * | 2008-09-25 | 2011-07-21 | Yasushi Kohno | Heterocyclic biaryl derivative and pde inhibitor comprising same as active ingredient |
Family Cites Families (33)
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| CA1164459A (en) * | 1980-11-11 | 1984-03-27 | Yung-Hsiung Yang | Process for preparing (imidazo¬1,2-a|pyridine- 2-yl)-carbostyril or -3,4-dihydrocarbostyryl derivatives |
| YU136287A (en) * | 1986-07-25 | 1990-06-30 | Boehringer Kg | Process for preparing new 1,4 benzodiazepines |
| TW279162B (OSRAM) * | 1991-09-26 | 1996-06-21 | Mitsubishi Chem Corp | |
| JP2928079B2 (ja) | 1994-02-14 | 1999-07-28 | 永信薬品工業股▲ふん▼有限公司 | １−（置換ベンジル）−３−（置換アリール）縮合ピラゾール類、その製造法及びその用途 |
| US6166041A (en) | 1995-10-11 | 2000-12-26 | Euro-Celtique, S.A. | 2-heteroaryl and 2-heterocyclic benzoxazoles as PDE IV inhibitors for the treatment of asthma |
| US6313126B1 (en) * | 1999-01-07 | 2001-11-06 | American Home Products Corp | Arylpiperazinyl-cyclohexyl indole derivatives for the treatment of depression |
| US6387942B2 (en) | 2000-06-19 | 2002-05-14 | Yung Shin Pharmaceutical Ind. Co. Ltd | Method of treating disorders related to protease-activated receptors-induced cell activation |
| EP1348701A1 (en) | 2002-03-28 | 2003-10-01 | Warner-Lambert Company LLC | (2,4-disubstituted-thiazol-5-yl) amine compounds as PDE7 inhibitors |
| TW200517381A (en) | 2003-08-01 | 2005-06-01 | Genelabs Tech Inc | Bicyclic heteroaryl derivatives |
| US20050272784A1 (en) | 2004-05-07 | 2005-12-08 | Xiaobing Li | Inhibitors of bacterial Type III protein secretion systems |
| WO2006015259A2 (en) | 2004-07-28 | 2006-02-09 | Irm Llc | Compounds and compositions as modulators of steroid hormone nuclear receptors |
| RU2007130896A (ru) | 2005-01-14 | 2009-02-20 | Дженелэбс Текнолоджиз, Инк. (Us) | Индольные производные для лечения вирусных инфекций |
| US20080015193A1 (en) | 2006-06-20 | 2008-01-17 | Mendoza Jose S | Certain azoles exhibiting ATP-utilizing enzyme inhibitory activity, compositions, and uses thereof |
| MX2008015923A (es) | 2006-06-29 | 2009-01-13 | Hoffmann La Roche | Derivados de bencimidazol, metodo para su produccion, su uso como agonistas fxr y preparaciones farmaceuticas que los contienen. |
| WO2008073451A2 (en) | 2006-12-11 | 2008-06-19 | Sirtris Pharmaceuticals, Inc. | Benzoimidazole derivatives as sirtuin (sir) modulating compounds |
| EP2227770A4 (en) | 2007-11-30 | 2011-11-09 | Glaxosmithkline Llc | PROLYLHYDROXYLASEINHIBITOREN |
| CA2723135A1 (en) | 2008-05-01 | 2009-11-05 | Sirtris Pharmaceuticals, Inc. | Quenolines and related analogs as sirtuin modulators |
| BRPI0913031A2 (pt) | 2008-05-23 | 2019-11-26 | Novartis Ag | derivados de quinolina e quinoxalinas como inibidores de proteína tirosina quinase, seus usos e processo de fabricação, bem como composições farmacêuticas e combinação que os compreende |
| EP2328896B1 (en) | 2008-07-23 | 2013-10-23 | Vertex Pharmaceuticals Incorporated | Tri-cyclic pyrazolopyridine kinase inhibitors |
| US20130072473A1 (en) | 2011-05-09 | 2013-03-21 | Proteostasis Therapeutics, Inc. | Compounds for treating protein folding disorders |
| TW201348226A (zh) | 2012-02-28 | 2013-12-01 | Amgen Inc | 作為ｐｉｍ抑制劑之醯胺 |
| SG11201406759YA (en) | 2012-04-26 | 2014-11-27 | Bristol Myers Squibb Co | Imidazothiadiazole derivatives as protease activated receptor 4 (par4) inhibitors for treating platelet aggregation |
| BR112014026643B1 (pt) | 2012-04-26 | 2023-03-07 | Universite De Montreal | Derivados de imidazotiadiazol e imidazopirazina como inibidores de receptor 4 ativado por protease (par4) para o tratamento de agregação de plaqueta, seus usos e composição farmacêutica |
| MX2014012741A (es) | 2012-04-26 | 2015-04-13 | Bristol Myers Squibb Co | Derivados de imidazotiadiazol e imidazopirazina como inhibidores del receptor 4 activado de proteasa (par4) para tratamiento de agregacion plaquetaria. |
| US9617279B1 (en) | 2014-06-24 | 2017-04-11 | Bristol-Myers Squibb Company | Imidazooxadiazole compounds |
| US9598419B1 (en) | 2014-06-24 | 2017-03-21 | Universite De Montreal | Imidazotriazine and imidazodiazine compounds |
| US10238638B2 (en) | 2015-02-26 | 2019-03-26 | Universite De Montreal | Benzothiazole and benzothiophene compounds |
| ES2929208T3 (es) | 2015-02-26 | 2022-11-25 | Univ Montreal | Compuestos de imidazotiadiazol como inhibidores de PAR4 |
| WO2016180536A1 (en) * | 2015-05-13 | 2016-11-17 | Selvita S.A. | Substituted quinoxaline derivatives |
| WO2017019828A1 (en) | 2015-07-30 | 2017-02-02 | Bristol-Myers Squibb Company | Aryl substituted bicyclic heteroaryl compounds |
| JP6990228B2 (ja) | 2016-07-14 | 2022-01-13 | ブリストル－マイヤーズ スクイブ カンパニー | 二環式ヘテロアリール置換の化合物 |
| CN109689642B (zh) | 2016-07-14 | 2022-04-12 | 百时美施贵宝公司 | 经单环杂芳基取代的化合物 |
| CN109689664B (zh) | 2016-07-14 | 2022-04-15 | 百时美施贵宝公司 | 作为par4抑制剂的三环杂芳基取代的喹啉和氮杂喹啉化合物 |
-
2017
- 2017-07-13 WO PCT/US2017/041878 patent/WO2018013774A1/en not_active Ceased
- 2017-07-13 ES ES17742925T patent/ES2823180T3/es active Active
- 2017-07-13 EP EP17742925.5A patent/EP3484878B1/en active Active
- 2017-07-13 KR KR1020197004315A patent/KR102460385B1/ko active Active
- 2017-07-13 US US16/317,248 patent/US20190292176A1/en not_active Abandoned
- 2017-07-13 CN CN201780056202.XA patent/CN109689647B/zh active Active
- 2017-07-13 JP JP2019501619A patent/JP7058256B2/ja active Active
-
2020
- 2020-12-16 US US17/123,265 patent/US12060347B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998020007A1 (en) * | 1996-11-06 | 1998-05-14 | Darwin Discovery Limited | Quinolines and their therapeutic use |
| US20110178041A1 (en) * | 2008-09-25 | 2011-07-21 | Yasushi Kohno | Heterocyclic biaryl derivative and pde inhibitor comprising same as active ingredient |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20190027385A (ko) | 2019-03-14 |
| US20210163465A1 (en) | 2021-06-03 |
| CN109689647B (zh) | 2023-01-20 |
| JP7058256B2 (ja) | 2022-04-21 |
| CN109689647A (zh) | 2019-04-26 |
| EP3484878B1 (en) | 2020-08-19 |
| US12060347B2 (en) | 2024-08-13 |
| WO2018013774A1 (en) | 2018-01-18 |
| ES2823180T3 (es) | 2021-05-06 |
| EP3484878A1 (en) | 2019-05-22 |
| JP2019528247A (ja) | 2019-10-10 |
| US20190292176A1 (en) | 2019-09-26 |
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