JP7179014B2 - ニラパリブの製造方法 - Google Patents
ニラパリブの製造方法 Download PDFInfo
- Publication number
- JP7179014B2 JP7179014B2 JP2019557567A JP2019557567A JP7179014B2 JP 7179014 B2 JP7179014 B2 JP 7179014B2 JP 2019557567 A JP2019557567 A JP 2019557567A JP 2019557567 A JP2019557567 A JP 2019557567A JP 7179014 B2 JP7179014 B2 JP 7179014B2
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- Prior art keywords
- formula
- salt
- acid
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- monohydrate
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762489415P | 2017-04-24 | 2017-04-24 | |
| US201762489387P | 2017-04-24 | 2017-04-24 | |
| US62/489,387 | 2017-04-24 | ||
| US62/489,415 | 2017-04-24 | ||
| PCT/US2018/029131 WO2018200517A1 (en) | 2017-04-24 | 2018-04-24 | Methods of manufacturing of niraparib |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020517668A JP2020517668A (ja) | 2020-06-18 |
| JP2020517668A5 JP2020517668A5 (enExample) | 2021-06-17 |
| JP7179014B2 true JP7179014B2 (ja) | 2022-11-28 |
Family
ID=63919973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019557567A Active JP7179014B2 (ja) | 2017-04-24 | 2018-04-24 | ニラパリブの製造方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US11161834B2 (enExample) |
| EP (1) | EP3615513B1 (enExample) |
| JP (1) | JP7179014B2 (enExample) |
| KR (1) | KR102582624B1 (enExample) |
| CN (2) | CN110753684A (enExample) |
| AU (2) | AU2018258274C1 (enExample) |
| CA (1) | CA3060715C (enExample) |
| ES (1) | ES2926255T3 (enExample) |
| IL (1) | IL270068B (enExample) |
| MA (1) | MA48475A (enExample) |
| MX (1) | MX393879B (enExample) |
| SG (1) | SG11201909807TA (enExample) |
| TW (1) | TWI783993B (enExample) |
| WO (1) | WO2018200517A1 (enExample) |
| ZA (1) | ZA201906944B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11201811564QA (en) | 2016-06-29 | 2019-01-30 | Tesaro Inc | Methods of treating ovarian cancer |
| MX2019011496A (es) | 2017-03-27 | 2020-01-23 | Tesaro Inc | Composiciones de niraparib. |
| JP7179014B2 (ja) | 2017-04-24 | 2022-11-28 | テサロ, インコーポレイテッド | ニラパリブの製造方法 |
| KR20200018436A (ko) | 2017-05-09 | 2020-02-19 | 테사로, 인코포레이티드 | 암 치료를 위한 조합 요법 |
| CA3063715A1 (en) | 2017-05-18 | 2018-11-22 | Tesaro, Inc. | Combination therapies for treating cancer |
| EA202090573A1 (ru) | 2017-09-26 | 2020-09-07 | Тесаро, Инк. | Составы нирапариба |
| JP2020536066A (ja) | 2017-09-30 | 2020-12-10 | テサロ, インコーポレイテッド | 癌を治療するための併用療法 |
| CN111182923A (zh) | 2017-10-06 | 2020-05-19 | 特沙诺有限公司 | 组合疗法及其用途 |
| EP3860988A1 (en) | 2018-10-03 | 2021-08-11 | Tesaro, Inc. | Crystalline forms of niraparib freebase |
| CN112300074B (zh) * | 2019-08-02 | 2023-12-29 | 北京盈科瑞创新药物研究有限公司 | 一种吲唑甲酰胺类化合物及其制备方法和应用 |
| WO2023159066A1 (en) | 2022-02-15 | 2023-08-24 | Tesaro, Inc. | Use of niraparib for the treatment of brain cancer |
| WO2024142096A1 (en) * | 2022-12-29 | 2024-07-04 | Dr. Reddy’S Laboratories Limited | Process for preparation of niraparib tosylate and its intermediates |
| WO2025017711A1 (en) * | 2023-07-20 | 2025-01-23 | Natco Pharma Limited | An improved process for the preparation of niraparib tosylate monohydrate |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010515715A (ja) | 2007-01-10 | 2010-05-13 | イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・ピー・アー | ポリ(adp−リボース)ポリメラーゼ(parp)阻害剤としてのアミド置換インダゾール |
| JP2011509252A (ja) | 2008-01-08 | 2011-03-24 | メルク シャープ エンド ドーム リミテッド | 2−{4−[(3s)−ピペリジン−3−イル]フェニル}−2h−インダゾール−7−カルボキサミドの薬学的に許容される塩 |
| WO2014088983A1 (en) | 2012-12-07 | 2014-06-12 | Merck Sharp & Dohme Corp. | Regioselective n-2 arylation of indazoles |
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| US5837458A (en) | 1994-02-17 | 1998-11-17 | Maxygen, Inc. | Methods and compositions for cellular and metabolic engineering |
| US6335160B1 (en) | 1995-02-17 | 2002-01-01 | Maxygen, Inc. | Methods and compositions for polypeptide engineering |
| US5605793A (en) | 1994-02-17 | 1997-02-25 | Affymax Technologies N.V. | Methods for in vitro recombination |
| FI104465B (fi) | 1995-06-14 | 2000-02-15 | Valio Oy | Proteiinihydrolysaatteja allergioiden hoitamiseksi tai estämiseksi, niiden valmistus ja käyttö |
| JP4213771B2 (ja) | 1997-04-23 | 2009-01-21 | 株式会社カネカ | 光学活性アミノ化合物の製造方法 |
| WO1999029902A1 (en) | 1997-12-08 | 1999-06-17 | California Institute Of Technology | Method for creating polynucleotide and polypeptide sequences |
| JP4221100B2 (ja) | 1999-01-13 | 2009-02-12 | エルピーダメモリ株式会社 | 半導体装置 |
| GB0004297D0 (en) | 2000-02-23 | 2000-04-12 | Ucb Sa | 2-oxo-1 pyrrolidine derivatives process for preparing them and their uses |
| EP1272967A2 (en) | 2000-03-30 | 2003-01-08 | Maxygen, Inc. | In silico cross-over site selection |
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| JPWO2002100833A1 (ja) | 2001-06-12 | 2004-09-24 | 住友製薬株式会社 | Rhoキナーゼ阻害剤 |
| CN101048397A (zh) | 2004-09-29 | 2007-10-03 | 三菱制药株式会社 | 作为τ蛋白激酶1抑制剂的6-(吡啶基)-4-嘧啶酮衍生物 |
| JP4611441B2 (ja) | 2006-04-03 | 2011-01-12 | イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・ピー・アー | ポリ(adp−リボース)ポリメラーゼ(parp)阻害剤としてのアミド置換インダゾール及びベンゾトリアゾール誘導体 |
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| WO2008132142A2 (en) | 2007-04-27 | 2008-11-06 | Ucb Pharma S.A. | New heterocyclic derivatives useful for the treatment of cns disorders |
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| KR20140001965A (ko) | 2010-11-30 | 2014-01-07 | 다케다 야쿠힌 고교 가부시키가이샤 | 바이시클릭 화합물 |
| KR101585840B1 (ko) | 2011-02-08 | 2016-01-15 | 화이자 인코포레이티드 | 글루카곤 수용체 조절자 |
| US8802673B2 (en) | 2011-03-24 | 2014-08-12 | Hoffmann-La Roche Inc | Heterocyclic amine derivatives |
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| PT2928865T (pt) | 2012-12-07 | 2018-06-11 | Merck Sharp & Dohme | Processo de transaminação biocatalítica |
| US20160160294A1 (en) | 2014-12-08 | 2016-06-09 | Tesaro | Methods and materials for predicting response to niraparib |
| SG11201811564QA (en) | 2016-06-29 | 2019-01-30 | Tesaro Inc | Methods of treating ovarian cancer |
| CN106496187A (zh) * | 2016-09-14 | 2017-03-15 | 陕西科技大学 | 一种制备PARP抑制剂Niraparib的合成方法 |
| CN106432056A (zh) * | 2016-09-17 | 2017-02-22 | 青岛辰达生物科技有限公司 | 一种尼拉帕布中间体(3s)‑3‑(4‑氨基苯基)哌啶‑1‑甲酸叔丁酯的制备方法 |
| CN106432055A (zh) | 2016-09-17 | 2017-02-22 | 青岛辰达生物科技有限公司 | 一种尼拉帕布中间体4‑(哌啶‑3‑基)苯胺的制备方法 |
| CN106432057A (zh) * | 2016-09-17 | 2017-02-22 | 青岛云天生物技术有限公司 | 一种制备(3s)‑3‑(4‑氨基苯基)哌啶‑1‑甲酸叔丁酯的方法 |
| MX2019011496A (es) | 2017-03-27 | 2020-01-23 | Tesaro Inc | Composiciones de niraparib. |
| BR112019020191A2 (pt) | 2017-03-27 | 2020-04-22 | Tesaro Inc | formulações de niraparib |
| JP7179014B2 (ja) | 2017-04-24 | 2022-11-28 | テサロ, インコーポレイテッド | ニラパリブの製造方法 |
| KR20200018436A (ko) | 2017-05-09 | 2020-02-19 | 테사로, 인코포레이티드 | 암 치료를 위한 조합 요법 |
| CA3063715A1 (en) | 2017-05-18 | 2018-11-22 | Tesaro, Inc. | Combination therapies for treating cancer |
| EA202090573A1 (ru) | 2017-09-26 | 2020-09-07 | Тесаро, Инк. | Составы нирапариба |
| JP2020536066A (ja) | 2017-09-30 | 2020-12-10 | テサロ, インコーポレイテッド | 癌を治療するための併用療法 |
| CN111182923A (zh) | 2017-10-06 | 2020-05-19 | 特沙诺有限公司 | 组合疗法及其用途 |
| JP7337805B2 (ja) | 2017-12-27 | 2023-09-04 | テサロ, インコーポレイテッド | がんを処置する方法 |
| MX2020008258A (es) | 2018-02-05 | 2020-11-13 | Tesaro Inc | Formulaciones pediátricas de niraparib y métodos de tratamiento pediátricos. |
-
2018
- 2018-04-24 JP JP2019557567A patent/JP7179014B2/ja active Active
- 2018-04-24 US US16/608,059 patent/US11161834B2/en active Active
- 2018-04-24 WO PCT/US2018/029131 patent/WO2018200517A1/en not_active Ceased
- 2018-04-24 AU AU2018258274A patent/AU2018258274C1/en active Active
- 2018-04-24 CA CA3060715A patent/CA3060715C/en active Active
- 2018-04-24 MX MX2019012658A patent/MX393879B/es unknown
- 2018-04-24 MA MA048475A patent/MA48475A/fr unknown
- 2018-04-24 KR KR1020197034673A patent/KR102582624B1/ko active Active
- 2018-04-24 CN CN201880040321.0A patent/CN110753684A/zh active Pending
- 2018-04-24 EP EP18790167.3A patent/EP3615513B1/en active Active
- 2018-04-24 ES ES18790167T patent/ES2926255T3/es active Active
- 2018-04-24 IL IL270068A patent/IL270068B/en unknown
- 2018-04-24 CN CN202410234039.3A patent/CN118271233A/zh active Pending
- 2018-04-24 TW TW107113922A patent/TWI783993B/zh active
- 2018-04-24 SG SG11201909807T patent/SG11201909807TA/en unknown
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2019
- 2019-10-22 ZA ZA2019/06944A patent/ZA201906944B/en unknown
-
2021
- 2021-08-09 AU AU2021215116A patent/AU2021215116B2/en active Active
- 2021-10-29 US US17/452,928 patent/US11629137B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010515715A (ja) | 2007-01-10 | 2010-05-13 | イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・ピー・アー | ポリ(adp−リボース)ポリメラーゼ(parp)阻害剤としてのアミド置換インダゾール |
| JP2011509252A (ja) | 2008-01-08 | 2011-03-24 | メルク シャープ エンド ドーム リミテッド | 2−{4−[(3s)−ピペリジン−3−イル]フェニル}−2h−インダゾール−7−カルボキサミドの薬学的に許容される塩 |
| WO2014088983A1 (en) | 2012-12-07 | 2014-06-12 | Merck Sharp & Dohme Corp. | Regioselective n-2 arylation of indazoles |
Non-Patent Citations (2)
| Title |
|---|
| Chung, Cheol K.,Process Development of C-N Cross-Coupling and Enantioselective Biocatalytic Reactions for the Asymmetric Synthesis of Niraparib,Organic Process Research & Development ,2014年,18(1),,215-227 |
| Wallace, Debra J.,Development of a Fit-for-Purpose Large-Scale Synthesis of an Oral PARP Inhibitor,Organic Process Research & Development,2011年,15(4),,831-840 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2020517668A (ja) | 2020-06-18 |
| AU2021215116B2 (en) | 2022-12-01 |
| MA48475A (fr) | 2020-03-04 |
| US20220041575A1 (en) | 2022-02-10 |
| IL270068B (en) | 2022-06-01 |
| ES2926255T3 (es) | 2022-10-24 |
| CN118271233A (zh) | 2024-07-02 |
| NZ758948A (en) | 2024-04-26 |
| AU2018258274C1 (en) | 2021-12-02 |
| SG11201909807TA (en) | 2019-11-28 |
| CN110753684A (zh) | 2020-02-04 |
| TWI783993B (zh) | 2022-11-21 |
| ZA201906944B (en) | 2023-03-29 |
| AU2021215116A1 (en) | 2021-08-26 |
| WO2018200517A1 (en) | 2018-11-01 |
| CA3060715C (en) | 2024-10-01 |
| EP3615513B1 (en) | 2022-07-20 |
| AU2018258274B2 (en) | 2021-05-13 |
| US20200055837A1 (en) | 2020-02-20 |
| US11161834B2 (en) | 2021-11-02 |
| KR102582624B1 (ko) | 2023-09-22 |
| TW201841889A (zh) | 2018-12-01 |
| EP3615513A1 (en) | 2020-03-04 |
| US11629137B2 (en) | 2023-04-18 |
| EP3615513A4 (en) | 2020-12-09 |
| MX393879B (es) | 2025-03-24 |
| AU2018258274A1 (en) | 2019-11-14 |
| BR112019022320A2 (pt) | 2020-05-26 |
| CA3060715A1 (en) | 2018-11-01 |
| KR20200021456A (ko) | 2020-02-28 |
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