KR20210029165A - 비아릴에테르형 퀴나졸린 유도체 - Google Patents
비아릴에테르형 퀴나졸린 유도체 Download PDFInfo
- Publication number
- KR20210029165A KR20210029165A KR1020207038066A KR20207038066A KR20210029165A KR 20210029165 A KR20210029165 A KR 20210029165A KR 1020207038066 A KR1020207038066 A KR 1020207038066A KR 20207038066 A KR20207038066 A KR 20207038066A KR 20210029165 A KR20210029165 A KR 20210029165A
- Authority
- KR
- South Korea
- Prior art keywords
- oxy
- fluoro
- mmol
- group
- piperidin
- 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.)
- Withdrawn
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- 0 CN*C1=N*(Oc(cc2)cc(F)c2Nc2c(cc(c(OC)c3)OC(CC4)CCN4C(C=C)=O)c3ncn2)S=C1 Chemical compound CN*C1=N*(Oc(cc2)cc(F)c2Nc2c(cc(c(OC)c3)OC(CC4)CCN4C(C=C)=O)c3ncn2)S=C1 0.000 description 2
- VWABZYXGESOZAK-UHFFFAOYSA-N COc(c(OC(CC1)CCN1C(C=C)=O)c1)cc2c1c(Nc(ccc(Oc1n[nH]cc1)c1)c1F)ncn2 Chemical compound COc(c(OC(CC1)CCN1C(C=C)=O)c1)cc2c1c(Nc(ccc(Oc1n[nH]cc1)c1)c1F)ncn2 VWABZYXGESOZAK-UHFFFAOYSA-N 0.000 description 2
- RMJADSDVHNPREX-AATRIKPKSA-N CC(C)(C)CCC(C[n](cc1F)nc1Oc(cc1)cc(Cl)c1Nc1c(cc(c(OC)c2)NC(/C=C/CN(CC3)CC3F)=O)c2ncn1)=O Chemical compound CC(C)(C)CCC(C[n](cc1F)nc1Oc(cc1)cc(Cl)c1Nc1c(cc(c(OC)c2)NC(/C=C/CN(CC3)CC3F)=O)c2ncn1)=O RMJADSDVHNPREX-AATRIKPKSA-N 0.000 description 1
- YTCJHXKTPYOOOO-UHFFFAOYSA-N CC(C)(C)OC(Nc(ccc(Oc1n[nH]cc1)c1)c1F)=O Chemical compound CC(C)(C)OC(Nc(ccc(Oc1n[nH]cc1)c1)c1F)=O YTCJHXKTPYOOOO-UHFFFAOYSA-N 0.000 description 1
- VBBOZJFSLMRWDL-UHFFFAOYSA-N CC(C)(C)OC([n](cc1)nc1Oc(cc1)cc(F)c1N)=O Chemical compound CC(C)(C)OC([n](cc1)nc1Oc(cc1)cc(F)c1N)=O VBBOZJFSLMRWDL-UHFFFAOYSA-N 0.000 description 1
- UCPOTYREPYUEJM-UHFFFAOYSA-N CC(C)c1nnc(-c2c[s]c(Oc(cc3)cc(F)c3Nc3c(cc(c(OC)c4)OC(CC5)CCN5C(C=C)=O)c4ncn3)n2)[o]1 Chemical compound CC(C)c1nnc(-c2c[s]c(Oc(cc3)cc(F)c3Nc3c(cc(c(OC)c4)OC(CC5)CCN5C(C=C)=O)c4ncn3)n2)[o]1 UCPOTYREPYUEJM-UHFFFAOYSA-N 0.000 description 1
- AQOLDUFMOSQKFA-UHFFFAOYSA-N COC(Cc1cc(Oc(cc2)cc(F)c2N)ccc1)=O Chemical compound COC(Cc1cc(Oc(cc2)cc(F)c2N)ccc1)=O AQOLDUFMOSQKFA-UHFFFAOYSA-N 0.000 description 1
- ZUGAWBOAFUZIFQ-UHFFFAOYSA-N COC(Cc1cccc(Oc(cc2)cc(F)c2Nc(c2c3)ncnc2cc(OC)c3[N+]([O-])=O)c1)=O Chemical compound COC(Cc1cccc(Oc(cc2)cc(F)c2Nc(c2c3)ncnc2cc(OC)c3[N+]([O-])=O)c1)=O ZUGAWBOAFUZIFQ-UHFFFAOYSA-N 0.000 description 1
- UUNGLILFVFCJBI-UHFFFAOYSA-N COc(cc(c1c2)ncnc1Nc(ccc(Oc(cc1)n[n]1-c1cc(Cl)ncc1)c1)c1F)c2OC(CC1)CCN1C(C=C)=O Chemical compound COc(cc(c1c2)ncnc1Nc(ccc(Oc(cc1)n[n]1-c1cc(Cl)ncc1)c1)c1F)c2OC(CC1)CCN1C(C=C)=O UUNGLILFVFCJBI-UHFFFAOYSA-N 0.000 description 1
- MJFJWOAETHEGGW-UHFFFAOYSA-N COc1cc2ncnc(Cl)c2cc1[N+]([O-])=O Chemical compound COc1cc2ncnc(Cl)c2cc1[N+]([O-])=O MJFJWOAETHEGGW-UHFFFAOYSA-N 0.000 description 1
- AZYFQNMMWYRZSI-UHFFFAOYSA-N COc1cc2ncnc(Nc(ccc(Oc(cc3)n[n]3-c3cc(F)ncc3)c3)c3F)c2cc1OC(CC1)CCN1C(C=C)=O Chemical compound COc1cc2ncnc(Nc(ccc(Oc(cc3)n[n]3-c3cc(F)ncc3)c3)c3F)c2cc1OC(CC1)CCN1C(C=C)=O AZYFQNMMWYRZSI-UHFFFAOYSA-N 0.000 description 1
- KBXJZVJSKPOONS-RMKNXTFCSA-N Cc1nnc(-c2cc(Oc(cc3)cc(F)c3Nc3c(cc(c(OC)c4)NC(/C=C/CN(C)C)=O)c4ncn3)ccc2)[o]1 Chemical compound Cc1nnc(-c2cc(Oc(cc3)cc(F)c3Nc3c(cc(c(OC)c4)NC(/C=C/CN(C)C)=O)c4ncn3)ccc2)[o]1 KBXJZVJSKPOONS-RMKNXTFCSA-N 0.000 description 1
- BTIWRYYXDMPWIY-UHFFFAOYSA-N Cc1nnc(-c2cccc(Oc(cc3)cc(F)c3Nc3c(cc(c(OC)c4)N)c4ncn3)c2)[o]1 Chemical compound Cc1nnc(-c2cccc(Oc(cc3)cc(F)c3Nc3c(cc(c(OC)c4)N)c4ncn3)c2)[o]1 BTIWRYYXDMPWIY-UHFFFAOYSA-N 0.000 description 1
- FGSAQRJRWCZLOB-UHFFFAOYSA-N Fc1cc(Cl)ncc1 Chemical compound Fc1cc(Cl)ncc1 FGSAQRJRWCZLOB-UHFFFAOYSA-N 0.000 description 1
- WLAKUAILRGATSL-UHFFFAOYSA-N Fc1cc(F)ncc1 Chemical compound Fc1cc(F)ncc1 WLAKUAILRGATSL-UHFFFAOYSA-N 0.000 description 1
Images
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
- C07D417/14—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
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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
- C07D417/02—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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JPJP-P-2018-127829 | 2018-07-04 | ||
| JP2018127829 | 2018-07-04 | ||
| PCT/JP2019/026483 WO2020009156A1 (ja) | 2018-07-04 | 2019-07-03 | ビアリールエーテル型キナゾリン誘導体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20210029165A true KR20210029165A (ko) | 2021-03-15 |
Family
ID=69059535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020207038066A Withdrawn KR20210029165A (ko) | 2018-07-04 | 2019-07-03 | 비아릴에테르형 퀴나졸린 유도체 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20230025510A1 (https=) |
| EP (1) | EP3822263A4 (https=) |
| JP (1) | JP7288904B2 (https=) |
| KR (1) | KR20210029165A (https=) |
| CN (1) | CN112334460A (https=) |
| AU (1) | AU2019297889A1 (https=) |
| BR (1) | BR112020027064A2 (https=) |
| CA (1) | CA3105602A1 (https=) |
| CO (1) | CO2021000800A2 (https=) |
| IL (1) | IL279858A (https=) |
| MX (1) | MX2021000014A (https=) |
| PH (1) | PH12021550003A1 (https=) |
| SG (1) | SG11202013218QA (https=) |
| TW (1) | TW202012391A (https=) |
| WO (1) | WO2020009156A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020262998A1 (ko) * | 2019-06-26 | 2020-12-30 | 한미약품 주식회사 | 항 종양 활성을 갖는 신규 퀴나졸린 유도체 및 이를 포함하는 약학 조성물 |
| US20230271936A1 (en) * | 2020-08-10 | 2023-08-31 | Abbisko Therapeutics Co., Ltd | Efgr inhibitor, preparation method therefor and application thereof |
| WO2022105908A1 (zh) * | 2020-11-23 | 2022-05-27 | 上海和誉生物医药科技有限公司 | Egfr抑制剂及其制备方法与在药学上的应用 |
| CN113264888A (zh) * | 2021-03-04 | 2021-08-17 | 江苏康可得生物技术股份有限公司 | 酪氨酸激酶抑制剂及其药物应用 |
| KR20230156767A (ko) * | 2021-03-19 | 2023-11-14 | 베이징 사이텍-엠큐 파마슈티컬즈 리미티드 | 퀴나졸린계 화합물, 조성물 및 퀴나졸린계 화합물의 적용 |
| EP4323356A1 (en) | 2021-04-13 | 2024-02-21 | Nuvalent, Inc. | Amino-substituted heterocycles for treating cancers with egfr mutations |
| US20250136595A1 (en) * | 2022-02-09 | 2025-05-01 | Enliven Inc. | Acylated heterocyclic quinazoline derivatives as inhibitors of erbb2 |
| TW202404590A (zh) * | 2022-04-05 | 2024-02-01 | 美商纜圖藥品公司 | Egfr抑制劑 |
| CN117384162A (zh) * | 2022-05-17 | 2024-01-12 | 浙江文达医药科技有限公司 | 选择性her2抑制剂 |
| WO2025167927A1 (zh) * | 2024-02-05 | 2025-08-14 | 苏州韬略生物科技股份有限公司 | 三取代喹唑啉衍生物及其酸加成盐及其药物组合物和用途 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008150118A2 (en) | 2007-06-05 | 2008-12-11 | Hanmi Pharm. Co., Ltd. | Novel amide derivative for inhibiting the growth of cancer cells |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU228446B1 (en) * | 1996-04-12 | 2013-03-28 | Warner Lambert Co | Kinazoline derivatives as irreversible inhibitors of protein-kinase, pharmaceutical compositions containing these compounds and use thereof |
| CA2527017A1 (en) * | 2003-05-27 | 2004-12-09 | Pfizer Products Inc. | Quinazolines and pyrido [3,4-d] pyrimidines as receptor tyrosine kinase inhibitors |
| WO2013173254A1 (en) * | 2012-05-14 | 2013-11-21 | Dawei Zhang | Bicyclic compounds as kinases inhibitors |
| CN103965120B (zh) * | 2013-01-25 | 2016-08-17 | 上海医药集团股份有限公司 | 喹啉及喹唑啉衍生物、制备方法、中间体、组合物及应用 |
| MA46852A (fr) | 2016-11-17 | 2019-09-25 | Univ Texas | Composés à activité antitumorale contre des cellules cancéreuses porteuses de mutations egfr ou her2 exon 20 |
| WO2020262998A1 (ko) * | 2019-06-26 | 2020-12-30 | 한미약품 주식회사 | 항 종양 활성을 갖는 신규 퀴나졸린 유도체 및 이를 포함하는 약학 조성물 |
-
2019
- 2019-07-02 TW TW108123293A patent/TW202012391A/zh unknown
- 2019-07-03 WO PCT/JP2019/026483 patent/WO2020009156A1/ja not_active Ceased
- 2019-07-03 CA CA3105602A patent/CA3105602A1/en active Pending
- 2019-07-03 JP JP2020529034A patent/JP7288904B2/ja active Active
- 2019-07-03 BR BR112020027064-4A patent/BR112020027064A2/pt not_active Application Discontinuation
- 2019-07-03 AU AU2019297889A patent/AU2019297889A1/en not_active Abandoned
- 2019-07-03 KR KR1020207038066A patent/KR20210029165A/ko not_active Withdrawn
- 2019-07-03 MX MX2021000014A patent/MX2021000014A/es unknown
- 2019-07-03 EP EP19830650.8A patent/EP3822263A4/en not_active Withdrawn
- 2019-07-03 CN CN201980044514.8A patent/CN112334460A/zh active Pending
- 2019-07-03 SG SG11202013218QA patent/SG11202013218QA/en unknown
- 2019-07-03 US US17/257,238 patent/US20230025510A1/en not_active Abandoned
-
2020
- 2020-12-30 IL IL279858A patent/IL279858A/en unknown
-
2021
- 2021-01-03 PH PH12021550003A patent/PH12021550003A1/en unknown
- 2021-01-25 CO CONC2021/0000800A patent/CO2021000800A2/es unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008150118A2 (en) | 2007-06-05 | 2008-12-11 | Hanmi Pharm. Co., Ltd. | Novel amide derivative for inhibiting the growth of cancer cells |
Non-Patent Citations (16)
| Title |
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| Coussens L, et al.,Science. 1985 ; 230 (4730) : 1132 - 1139. |
| Das, M. et al., Proc. Natl Acad. Sci. USA, 74, 2790 - 2794 (1977). |
| Fukushige S et al., Mol Cell Biol 6 : 955 - 958, 1986. |
| Gravalos C, et al., Ann Oncol 19 : 1523 - 1529, 2008. |
| Hardwick R, et al., Eur. J Surg Oncol. 1997 (23) : 30 - 35. |
| Hyman D. M., et al., Nature. 2018 Feb 8 ; 554 (7691) : 189 - 194 |
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| Maria E. A. et al., Clin Cancer Res ; 18 (18) September 15, 2012 |
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| Yoshihisa K. et al., Cancer Sci, September 2016, 107 (9), 1179 - 1186 |
Also Published As
| Publication number | Publication date |
|---|---|
| PH12021550003A1 (en) | 2021-09-20 |
| IL279858A (en) | 2021-03-01 |
| AU2019297889A1 (en) | 2021-02-18 |
| EP3822263A1 (en) | 2021-05-19 |
| CA3105602A1 (en) | 2020-01-09 |
| JPWO2020009156A1 (ja) | 2021-07-15 |
| MX2021000014A (es) | 2021-03-09 |
| CO2021000800A2 (es) | 2021-02-08 |
| WO2020009156A1 (ja) | 2020-01-09 |
| EP3822263A4 (en) | 2022-03-16 |
| SG11202013218QA (en) | 2021-02-25 |
| CN112334460A (zh) | 2021-02-05 |
| TW202012391A (zh) | 2020-04-01 |
| US20230025510A1 (en) | 2023-01-26 |
| JP7288904B2 (ja) | 2023-06-08 |
| BR112020027064A2 (pt) | 2021-05-25 |
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