JP7270630B2 - 抗癌剤として有用なテトラヒドロキナゾリン誘導体 - Google Patents
抗癌剤として有用なテトラヒドロキナゾリン誘導体 Download PDFInfo
- Publication number
- JP7270630B2 JP7270630B2 JP2020542790A JP2020542790A JP7270630B2 JP 7270630 B2 JP7270630 B2 JP 7270630B2 JP 2020542790 A JP2020542790 A JP 2020542790A JP 2020542790 A JP2020542790 A JP 2020542790A JP 7270630 B2 JP7270630 B2 JP 7270630B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- group
- indazol
- compound
- 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
- 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
- C07D403/14—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 three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- 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
- 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
- C07D487/10—Spiro-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862628350P | 2018-02-09 | 2018-02-09 | |
| US62/628,350 | 2018-02-09 | ||
| US201862651796P | 2018-04-03 | 2018-04-03 | |
| US62/651,796 | 2018-04-03 | ||
| US201862782408P | 2018-12-20 | 2018-12-20 | |
| US62/782,408 | 2018-12-20 | ||
| PCT/IB2019/050993 WO2019155399A1 (en) | 2018-02-09 | 2019-02-07 | Tetrahydroquinazoline derivatives useful as anticancer agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021513534A JP2021513534A (ja) | 2021-05-27 |
| JP2021513534A5 JP2021513534A5 (https=) | 2022-02-10 |
| JP7270630B2 true JP7270630B2 (ja) | 2023-05-10 |
Family
ID=65724485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020542790A Active JP7270630B2 (ja) | 2018-02-09 | 2019-02-07 | 抗癌剤として有用なテトラヒドロキナゾリン誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10590115B2 (https=) |
| EP (1) | EP3749665A1 (https=) |
| JP (1) | JP7270630B2 (https=) |
| CA (1) | CA3090482C (https=) |
| PY (1) | PY1909256A (https=) |
| TW (1) | TW201942116A (https=) |
| UY (1) | UY38076A (https=) |
| WO (1) | WO2019155399A1 (https=) |
Families Citing this family (84)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102444509B1 (ko) | 2016-05-18 | 2022-09-19 | 미라티 테라퓨틱스, 인크. | Kras g12c 억제제 |
| US10647715B2 (en) | 2017-11-15 | 2020-05-12 | Mirati Therapeutics, Inc. | KRas G12C inhibitors |
| LT3710439T (lt) | 2017-11-15 | 2023-05-10 | Mirati Therapeutics, Inc. | Kras g12c inhibitoriai |
| TW202012415A (zh) | 2018-05-08 | 2020-04-01 | 瑞典商阿斯特捷利康公司 | 化學化合物 |
| AU2019320945C1 (en) * | 2018-08-16 | 2021-09-30 | F. Hoffmann-La Roche Ag | Fused ring compounds |
| WO2020085504A1 (ja) | 2018-10-26 | 2020-04-30 | 大鵬薬品工業株式会社 | 光照射ザンドマイヤー反応を用いたクロロアゾールカルボキシレート誘導体の製造方法 |
| US20220152026A1 (en) | 2019-02-12 | 2022-05-19 | Novartis Ag | Pharmaceutical combination comprising tno155 and a krasg12c inhibitor |
| KR102934231B1 (ko) | 2019-03-05 | 2026-03-06 | 아스트라제네카 아베 | 항암제로 유용한 융합 삼환식 화합물 |
| JP7502337B2 (ja) * | 2019-05-20 | 2024-06-18 | カリフォルニア インスティチュート オブ テクノロジー | Ｋｒａｓ ｇ１２ｃインヒビター及びその使用 |
| CN114269735B (zh) * | 2019-08-26 | 2024-02-23 | 南京创济生物医药有限公司 | 二氢或四氢喹唑啉类化合物及其中间体、制备方法和应用 |
| WO2021058018A1 (en) * | 2019-09-29 | 2021-04-01 | Beigene, Ltd. | Inhibitors of kras g12c |
| UA129778C2 (uk) | 2019-10-28 | 2025-07-30 | Мерк Шарп Енд Доум Елелсі | Низькомолекулярні інгібітори g12c-мутантного kras |
| TW202132316A (zh) | 2019-11-04 | 2021-09-01 | 美商銳新醫藥公司 | Ｒａｓ抑制劑 |
| IL322454A (en) | 2019-11-04 | 2025-09-01 | Revolution Medicines Inc | ras inhibitors |
| AU2020377925A1 (en) | 2019-11-04 | 2022-05-05 | Revolution Medicines, Inc. | Ras inhibitors |
| CN114630832A (zh) * | 2019-11-15 | 2022-06-14 | 四川海思科制药有限公司 | 一种嘧啶并环衍生物及其在医药上的应用 |
| EP4065231A1 (en) | 2019-11-27 | 2022-10-05 | Revolution Medicines, Inc. | Covalent ras inhibitors and uses thereof |
| EP4067343A4 (en) | 2019-11-29 | 2024-01-03 | Taiho Pharmaceutical Co., Ltd. | NEW PHENOLIC COMPOUND OR SALT THEREOF |
| WO2021109737A1 (zh) * | 2019-12-02 | 2021-06-10 | 上海璎黎药业有限公司 | 一种含氧杂环化合物、其制备方法及应用 |
| CN112979664B (zh) * | 2019-12-02 | 2024-03-01 | 上海璎黎药业有限公司 | 一种含氧杂环化合物、其制备方法及应用 |
| CN112094269B (zh) * | 2020-01-01 | 2021-12-07 | 上海凌达生物医药有限公司 | 一类饱和六元环并杂环类化合物、制备方法和用途 |
| WO2021139748A1 (en) * | 2020-01-08 | 2021-07-15 | Ascentage Pharma (Suzhou) Co., Ltd. | Spirocyclic tetrahydroquinazolines |
| GB202001344D0 (en) | 2020-01-31 | 2020-03-18 | Redx Pharma Plc | Ras Inhibitors |
| WO2023205701A1 (en) | 2022-04-20 | 2023-10-26 | Kumquat Biosciences Inc. | Macrocyclic heterocycles and uses thereof |
| AU2021233058B2 (en) | 2020-03-12 | 2024-05-16 | D3 Bio(Wuxi) Co., Ltd | Pyrimidoheterocyclic compounds and application thereof |
| TWI811656B (zh) * | 2020-04-22 | 2023-08-11 | 大陸商德昇濟醫藥（無錫）有限公司 | 嘧啶并雜環類化合物及其應用 |
| WO2021216770A1 (en) * | 2020-04-22 | 2021-10-28 | Accutar Biotechnology Inc. | Substituted tetrahydroquinazoline compounds as kras inhibitors |
| WO2021244603A1 (en) * | 2020-06-04 | 2021-12-09 | Shanghai Antengene Corporation Limited | Inhibitors of kras g12c protein and uses thereof |
| US20230026856A1 (en) * | 2020-06-05 | 2023-01-26 | Sparcbio Llc | Heterocyclic compounds and methods of use thereof |
| WO2021248082A1 (en) * | 2020-06-05 | 2021-12-09 | Sparcbio Llc | Heterocyclic compounds and methods of use thereof |
| US20230023009A1 (en) * | 2020-06-05 | 2023-01-26 | Sparcbio Llc | Heterocyclic compounds and methods of use thereof |
| IL299131A (en) | 2020-06-18 | 2023-02-01 | Revolution Medicines Inc | Methods for delaying, preventing and treating acquired resistance to RAS inhibitors |
| US20250195521A1 (en) | 2020-09-03 | 2025-06-19 | Revolution Medicines, Inc. | Use of sos1 inhibitors to treat malignancies with shp2 mutations |
| CA3194067A1 (en) | 2020-09-15 | 2022-03-24 | Revolution Medicines, Inc. | Ras inhibitors |
| JP2023544450A (ja) | 2020-09-23 | 2023-10-23 | エラスカ・インコーポレイテッド | 三環式ピリドン及びピリミドン |
| EP4247807A4 (en) * | 2020-11-23 | 2024-10-16 | Merck Sharp & Dohme LLC | 6,7-DIHYDRO-PYRANO[2,3-D PYRIMIDINE AS INHIBITORS OF THE KRAS G12C MUTANT |
| EP4262803A4 (en) | 2020-12-16 | 2025-03-12 | Mirati Therapeutics, Inc. | Tetrahydropyridopyrimidine pan-kras inhibitors |
| WO2022133345A1 (en) | 2020-12-18 | 2022-06-23 | Erasca, Inc. | Tricyclic pyridones and pyrimidones |
| US20240100172A1 (en) | 2020-12-21 | 2024-03-28 | Hangzhou Jijing Pharmaceutical Technology Limited | Methods and compounds for targeted autophagy |
| CN114685502A (zh) * | 2020-12-25 | 2022-07-01 | 由理生物医药（上海）有限公司 | 作为kras-g12c抑制剂的螺环类化合物 |
| WO2022171013A1 (zh) * | 2021-02-09 | 2022-08-18 | 南京明德新药研发有限公司 | 四氢喹唑啉类化合物 |
| KR20240017811A (ko) | 2021-05-05 | 2024-02-08 | 레볼루션 메디슨즈, 인크. | 암의 치료를 위한 ras 억제제 |
| TW202309052A (zh) | 2021-05-05 | 2023-03-01 | 美商銳新醫藥公司 | Ｒａｓ抑制劑 |
| CN115385937A (zh) * | 2021-05-25 | 2022-11-25 | 江苏恒瑞医药股份有限公司 | 嘧啶并环烷基类化合物、其制备方法及其在医药上的应用 |
| TW202317100A (zh) | 2021-06-23 | 2023-05-01 | 瑞士商諾華公司 | 包含ｋｒａｓ ｇ１２ｃ抑制劑的藥物組合及其用於治療癌症之用途 |
| KR20240055778A (ko) | 2021-09-01 | 2024-04-29 | 노파르티스 아게 | Tead 억제제를 포함하는 제약 조합물 및 암의 치료를 위한 이의 용도 |
| EP4389751A1 (en) | 2021-09-03 | 2024-06-26 | Kumquat Biosciences Inc. | Heterocyclic compounds and uses thereof |
| AR127308A1 (es) | 2021-10-08 | 2024-01-10 | Revolution Medicines Inc | Inhibidores ras |
| CN119212994A (zh) | 2021-12-17 | 2024-12-27 | 建新公司 | 作为shp2抑制剂的吡唑并吡嗪化合物 |
| EP4227307A1 (en) | 2022-02-11 | 2023-08-16 | Genzyme Corporation | Pyrazolopyrazine compounds as shp2 inhibitors |
| JP2025510572A (ja) | 2022-03-08 | 2025-04-15 | レボリューション メディシンズ インコーポレイテッド | 免疫不応性肺癌を治療するための方法 |
| WO2023199180A1 (en) | 2022-04-11 | 2023-10-19 | Novartis Ag | Therapeutic uses of a krasg12c inhibitor |
| WO2023240263A1 (en) | 2022-06-10 | 2023-12-14 | Revolution Medicines, Inc. | Macrocyclic ras inhibitors |
| GB202212641D0 (en) | 2022-08-31 | 2022-10-12 | Jazz Pharmaceuticals Ireland Ltd | Novel compounds |
| CN120659773A (zh) | 2022-11-09 | 2025-09-16 | 锐新医药公司 | 化合物、复合物以及其制备方法和用途 |
| AU2024241633A1 (en) | 2023-03-30 | 2025-11-06 | Revolution Medicines, Inc. | Compositions for inducing ras gtp hydrolysis and uses thereof |
| CR20250420A (es) | 2023-04-07 | 2025-11-20 | Revolution Medicines Inc | Inhibidores macrocíclicos de ras |
| AR132338A1 (es) | 2023-04-07 | 2025-06-18 | Revolution Medicines Inc | Inhibidores de ras |
| CN121464140A (zh) | 2023-04-14 | 2026-02-03 | 锐新医药公司 | Ras抑制剂的结晶形式、含有其的组合物及其使用方法 |
| CN121100123A (zh) | 2023-04-14 | 2025-12-09 | 锐新医药公司 | Ras抑制剂的结晶形式 |
| TW202508595A (zh) | 2023-05-04 | 2025-03-01 | 美商銳新醫藥公司 | 用於ｒａｓ相關疾病或病症之組合療法 |
| PE20252789A1 (es) | 2023-05-24 | 2025-12-22 | Kumquat Biosciences Inc | Compuestos heterociclicos y usos de estos |
| EP4721766A1 (en) | 2023-06-02 | 2026-04-08 | Daiichi Sankyo Company, Limited | Combination of (anti-her3 antibody)-drug conjugate and rasg12c inhibitor |
| CN121263417A (zh) | 2023-06-30 | 2026-01-02 | 金橘生物科技公司 | 取代的稠合三环胺化合物及其作为ras抑制剂的用途 |
| US20250049810A1 (en) | 2023-08-07 | 2025-02-13 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
| AU2024360465A1 (en) | 2023-10-12 | 2026-04-09 | Revolution Medicines, Inc. | Macrocyclic ras inhibitors |
| AU2024361909A1 (en) | 2023-10-20 | 2026-03-26 | Merck Sharp & Dohme Llc | Small molecule inhibitors of kras proteins |
| WO2025171055A1 (en) | 2024-02-06 | 2025-08-14 | Kumquat Biosciences Inc. | Heterocyclic conjugates and uses thereof |
| WO2025171296A1 (en) | 2024-02-09 | 2025-08-14 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2025230971A1 (en) | 2024-04-30 | 2025-11-06 | Kumquat Biosciences Inc. | Macrocyclic heterocycles as anticancer agents |
| TW202547461A (zh) | 2024-05-17 | 2025-12-16 | 美商銳新醫藥公司 | Ｒａｓ抑制劑 |
| WO2025255438A1 (en) | 2024-06-07 | 2025-12-11 | Revolution Medicines, Inc. | Methods of treating a ras protein-related disease or disorder |
| WO2025265060A1 (en) | 2024-06-21 | 2025-12-26 | Revolution Medicines, Inc. | Therapeutic compositions and methods for managing treatment-related effects |
| WO2026006747A1 (en) | 2024-06-28 | 2026-01-02 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026015801A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Methods of treating a ras related disease or disorder |
| WO2026015796A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Methods of treating a ras related disease or disorder |
| WO2026015825A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Use of ras inhibitor for treating pancreatic cancer |
| WO2026015790A1 (en) | 2024-07-12 | 2026-01-15 | Revolution Medicines, Inc. | Methods of treating a ras related disease or disorder |
| WO2026035947A1 (en) | 2024-08-07 | 2026-02-12 | Tesseract Medicines Us, Llc | Kras-targeting covalent-induced drug conjugates comprising a topoisomerase payload |
| WO2026035945A1 (en) | 2024-08-07 | 2026-02-12 | Tesseract Medicines Us, Llc | Covalent-induced drug conjugates targeting kras and comprising a topoisomerase payload |
| WO2026050446A1 (en) | 2024-08-29 | 2026-03-05 | Revolution Medicines, Inc. | Ras inhibitors |
| WO2026064527A1 (en) | 2024-09-19 | 2026-03-26 | Tesseract Medicines Us, Llc | Kras-targeting covalent-induced drug conjugates comprising a tubulin inhibitor payload |
| WO2026064520A1 (en) | 2024-09-19 | 2026-03-26 | Tesseract Medicines Us, Llc | Covalent-induced drug conjugates targeting kras and comprising a tubulin inhibitor payload |
| WO2026072904A2 (en) | 2024-09-26 | 2026-04-02 | Revolution Medicines, Inc. | Compositions and methods for treating lung cancer |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020025968A1 (en) | 1998-04-15 | 2002-02-28 | Rifat Pamukcu | Method for inhibiting neoplastic cells and related conditions by exposure to 4-aminoquinazoline derivatives |
| JP2015526420A (ja) | 2012-07-20 | 2015-09-10 | クリーブ バイオサイエンシズ インコーポレイテッド | ｐ９７複合体の阻害剤としての融合ピリミジン |
| WO2017087528A1 (en) | 2015-11-16 | 2017-05-26 | Araxes Pharma Llc | 2-substituted quinazoline compounds comprising a substituted heterocyclic group and methods of use thereof |
| WO2017201161A1 (en) | 2016-05-18 | 2017-11-23 | Mirati Therapeutics, Inc. | Kras g12c inhibitors |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| GB9518953D0 (en) | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| WO2000035296A1 (en) | 1996-11-27 | 2000-06-22 | Wm. Wrigley Jr. Company | Improved release of medicament active agents from a chewing gum coating |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| WO2013026900A1 (en) * | 2011-08-23 | 2013-02-28 | Syngenta Participations Ag | Pyridine derivatives as microbiocides |
| EP3444251B1 (en) | 2013-12-11 | 2023-06-07 | Biogen MA Inc. | Biaryl compounds useful for the treatment of human diseases in oncology, neurology and immunology |
-
2019
- 2019-01-31 TW TW108103754A patent/TW201942116A/zh unknown
- 2019-02-01 US US16/265,012 patent/US10590115B2/en active Active
- 2019-02-07 UY UY38076A patent/UY38076A/es not_active Application Discontinuation
- 2019-02-07 JP JP2020542790A patent/JP7270630B2/ja active Active
- 2019-02-07 EP EP19710144.7A patent/EP3749665A1/en not_active Withdrawn
- 2019-02-07 WO PCT/IB2019/050993 patent/WO2019155399A1/en not_active Ceased
- 2019-02-07 CA CA3090482A patent/CA3090482C/en active Active
- 2019-02-08 PY PY201901909256A patent/PY1909256A/es unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020025968A1 (en) | 1998-04-15 | 2002-02-28 | Rifat Pamukcu | Method for inhibiting neoplastic cells and related conditions by exposure to 4-aminoquinazoline derivatives |
| JP2015526420A (ja) | 2012-07-20 | 2015-09-10 | クリーブ バイオサイエンシズ インコーポレイテッド | ｐ９７複合体の阻害剤としての融合ピリミジン |
| WO2017087528A1 (en) | 2015-11-16 | 2017-05-26 | Araxes Pharma Llc | 2-substituted quinazoline compounds comprising a substituted heterocyclic group and methods of use thereof |
| WO2017201161A1 (en) | 2016-05-18 | 2017-11-23 | Mirati Therapeutics, Inc. | Kras g12c inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2019155399A1 (en) | 2019-08-15 |
| PY1909256A (es) | 2020-07-16 |
| UY38076A (es) | 2019-10-01 |
| CA3090482A1 (en) | 2019-08-15 |
| US10590115B2 (en) | 2020-03-17 |
| EP3749665A1 (en) | 2020-12-16 |
| TW201942116A (zh) | 2019-11-01 |
| JP2021513534A (ja) | 2021-05-27 |
| CA3090482C (en) | 2023-01-31 |
| US20190248767A1 (en) | 2019-08-15 |
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