JP6906811B2 - アルキル置換複素環化合物、そのための調製方法およびその医学的用途 - Google Patents
アルキル置換複素環化合物、そのための調製方法およびその医学的用途 Download PDFInfo
- Publication number
- JP6906811B2 JP6906811B2 JP2019515464A JP2019515464A JP6906811B2 JP 6906811 B2 JP6906811 B2 JP 6906811B2 JP 2019515464 A JP2019515464 A JP 2019515464A JP 2019515464 A JP2019515464 A JP 2019515464A JP 6906811 B2 JP6906811 B2 JP 6906811B2
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- Japan
- Prior art keywords
- alkyl
- mmol
- cancer
- ethynyl
- dimethoxyphenyl
- 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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- 0 CC*C(C(C(C#Cc1cc(OC)cc(*C)c1)=[N+])=CNCC(CC1)CCC1C(C=C)=O)=O Chemical compound CC*C(C(C(C#Cc1cc(OC)cc(*C)c1)=[N+])=CNCC(CC1)CCC1C(C=C)=O)=O 0.000 description 9
- WLPAQAXAZQUXBG-UHFFFAOYSA-N C=CC(N1CCCC1)=O Chemical compound C=CC(N1CCCC1)=O WLPAQAXAZQUXBG-UHFFFAOYSA-N 0.000 description 2
- NSOLQPRPCPDXPO-UHFFFAOYSA-N B=CCN1CCCC1 Chemical compound B=CCN1CCCC1 NSOLQPRPCPDXPO-UHFFFAOYSA-N 0.000 description 1
- RELMYZLTNPSHKJ-UHFFFAOYSA-N C=CC(N1CCCC1)O Chemical compound C=CC(N1CCCC1)O RELMYZLTNPSHKJ-UHFFFAOYSA-N 0.000 description 1
- IJJJSNBMFDDFBC-UHFFFAOYSA-N CC(OCCC#N)=O Chemical compound CC(OCCC#N)=O IJJJSNBMFDDFBC-UHFFFAOYSA-N 0.000 description 1
- OVRKATYHWPCGPZ-UHFFFAOYSA-N CC1CCOCC1 Chemical compound CC1CCOCC1 OVRKATYHWPCGPZ-UHFFFAOYSA-N 0.000 description 1
- RIZBLVRXRWHLFA-UHFFFAOYSA-N Cc1cc(OC)cc(OC)c1 Chemical compound Cc1cc(OC)cc(OC)c1 RIZBLVRXRWHLFA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
-
- 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
-
- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and 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
- C07D401/02—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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D401/06—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 only aliphatic carbon 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
- C07D403/04—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
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon 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
- C07D403/14—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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610833890.3 | 2016-09-19 | ||
| CN201610833890.3A CN107840842A (zh) | 2016-09-19 | 2016-09-19 | 炔代杂环化合物、其制备方法及其在医药学上的应用 |
| PCT/CN2017/072570 WO2018049781A1 (zh) | 2016-09-19 | 2017-01-25 | 炔代杂环化合物、其制备方法及其在医药学上的应用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019529444A JP2019529444A (ja) | 2019-10-17 |
| JP2019529444A5 JP2019529444A5 (enExample) | 2020-03-05 |
| JP6906811B2 true JP6906811B2 (ja) | 2021-07-21 |
Family
ID=61618562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019515464A Active JP6906811B2 (ja) | 2016-09-19 | 2017-01-25 | アルキル置換複素環化合物、そのための調製方法およびその医学的用途 |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US10710981B2 (enExample) |
| EP (1) | EP3517535B1 (enExample) |
| JP (1) | JP6906811B2 (enExample) |
| KR (1) | KR102783517B1 (enExample) |
| CN (2) | CN107840842A (enExample) |
| AU (1) | AU2017327954B2 (enExample) |
| CA (1) | CA3036594C (enExample) |
| ES (1) | ES2925212T3 (enExample) |
| MX (1) | MX390747B (enExample) |
| RU (1) | RU2729069C1 (enExample) |
| SG (1) | SG10202102822RA (enExample) |
| WO (1) | WO2018049781A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN119350306A (zh) | 2018-12-13 | 2025-01-24 | 英特维特国际股份有限公司 | 1-[(3r,4s)-4-氰基四氢吡喃-3-基]-3-[(2-氟-6-甲氧基-4-吡啶基)氨基]吡唑-4-甲酰胺制备方法 |
| WO2020131674A1 (en) | 2018-12-19 | 2020-06-25 | Array Biopharma Inc. | 7-((3,5-dimethoxyphenyl)amino)quinoxaline derivatives as fgfr inhibitors for treating cancer |
| MX2021009863A (es) | 2019-03-21 | 2021-11-12 | Onxeo | Una molecula dbait en combinacion con inhibidor de quinasa para el tratamiento del cancer. |
| WO2021089791A1 (en) | 2019-11-08 | 2021-05-14 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for the treatment of cancers that have acquired resistance to kinase inhibitors |
| KR20220120638A (ko) * | 2019-12-26 | 2022-08-30 | 베이징 이노케어 파마 테크 씨오., 엘티디. | (s)-1-(1-아크릴로일피롤리딘-3-일)-3-((3,5-디메톡시페닐)에티닐)-5-(메틸아미노)-1h-피라졸-4-카르복사미드의 결정질 형태 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| BR112022024729A2 (pt) * | 2020-06-05 | 2023-02-28 | Kinnate Biopharma Inc | Inibidores de quinases do receptor do fator de crescimento de fibroblastos |
| JP2023528880A (ja) * | 2020-06-05 | 2023-07-06 | キネート バイオファーマ インク． | 線維芽細胞増殖因子受容体キナーゼの阻害剤 |
| WO2022042613A1 (zh) * | 2020-08-27 | 2022-03-03 | 上海和誉生物医药科技有限公司 | 一种1h-吡唑-4-酰胺衍生物，其制备方法和应用 |
| CA3204407A1 (en) * | 2021-01-12 | 2022-07-21 | Yucheng PANG | Process for preparing (s)-1-(1-acryloylpyrrolidin-3-yl)-3-((3,5-dimethoxyphenyl) ethynyl)-5-(methylamino)-1h-pyrazole-4-carboxamide |
| CN115433190B (zh) * | 2021-06-02 | 2024-09-20 | 药雅科技(上海)有限公司 | 不可逆杂环化合物fgfr抑制剂的制备方法和用途 |
| CN114853739B (zh) * | 2021-02-03 | 2023-09-22 | 药雅科技(上海)有限公司 | 一种炔代吡嗪类fgfr抑制剂及其制备方法和用途 |
| CN115043832B (zh) * | 2021-03-08 | 2023-08-22 | 药雅科技(上海)有限公司 | 一种fgfr抑制剂炔代杂环类化合物及其制备方法和用途 |
| CA3235435A1 (en) * | 2021-11-03 | 2023-05-11 | Xiangyang Chen | Amorphous solid dispersion comprising (s)-1-(1-acryloylpyrrolidin-3-yl)-3-((3,5-dimethoxyphenyl) ethynyl)-5-(methylamino)-1h-pyrazole-4-carboxamide |
| CN118354772A (zh) * | 2021-11-16 | 2024-07-16 | 北京诺诚健华医药科技有限公司 | 治疗头颈癌的方法 |
| KR20240115884A (ko) * | 2021-12-08 | 2024-07-26 | 킨네이트 바이오파마 인크. | Fgfr 키나제 억제제를 이용하는 암의 치료 |
| WO2023107870A1 (en) * | 2021-12-08 | 2023-06-15 | Kinnate Biopharma Inc. | Inhibitors of fibroblast growth factor receptor kinases |
| KR20240119095A (ko) * | 2021-12-08 | 2024-08-06 | 킨네이트 바이오파마 인크. | Fgfr 저해제의 고체 상태 형태 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2833948B1 (fr) * | 2001-12-21 | 2004-02-06 | Sod Conseils Rech Applic | Nouveaux derives de benzimidazole et leur utilisation en tant que medicament |
| RU2340605C2 (ru) | 2002-06-27 | 2008-12-10 | Ново Нордиск А/С | Арилкарбонильные производные в качестве терапевтических средств |
| CN1508130A (zh) | 2002-12-18 | 2004-06-30 | 中国科学院大连化学物理研究所 | N-苯基-n’-嘧啶基取代脲类衍生物的合成方法 |
| US7150894B2 (en) * | 2003-05-01 | 2006-12-19 | Kraft Foods Holdings, Inc. | Acid whey texture system |
| WO2006009741A1 (en) | 2004-06-23 | 2006-01-26 | Eli Lilly And Company | Kinase inhibitors |
| FR2889526B1 (fr) | 2005-08-04 | 2012-02-17 | Aventis Pharma Sa | 7-aza-indazoles substitues, compositions les contenant, procede de fabrication et utilisation |
| CA2630079A1 (en) | 2005-11-16 | 2007-05-24 | Sgx Pharmaceuticals, Inc. | Pyrazolothiazole protein kinase modulators |
| FR2908409B1 (fr) | 2006-11-10 | 2009-01-09 | Sanofi Aventis Sa | Pyrazoles substituees,compositions les contenant,procede de fabrication et utilisation |
| US7737149B2 (en) * | 2006-12-21 | 2010-06-15 | Astrazeneca Ab | N-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]-4-(3,5-dimethylpiperazin-1-yl)benzamide and salts thereof |
| CN101611014B (zh) * | 2006-12-21 | 2012-05-30 | 阿斯利康(瑞典)有限公司 | 用作fgfr抑制剂的酰氨基吡唑类化合物 |
| HUE034598T2 (en) | 2008-06-16 | 2018-02-28 | Univ Tennessee Res Found | Compound for cancer treatment |
| FR2947546B1 (fr) | 2009-07-03 | 2011-07-01 | Sanofi Aventis | Derives de pyrazoles, leur preparation et leur application en therapeutique |
| GB2474748B (en) * | 2009-10-01 | 2011-10-12 | Amira Pharmaceuticals Inc | Polycyclic compounds as lysophosphatidic acid receptor antagonists |
| WO2011109059A1 (en) * | 2010-03-01 | 2011-09-09 | Gtx, Inc. | Compounds for treatment of cancer |
| WO2013014039A1 (en) * | 2011-07-28 | 2013-01-31 | Nerviano Medical Sciences S.R.L. | Alkynyl substituted pyrimidinyl-pyrroles active as kinases inhibitors |
| WO2013024427A1 (en) | 2011-08-16 | 2013-02-21 | Glenmark Pharmaceuticals S.A. | Novel urea derivatives as tec kinase inhibitors and uses thereof |
| CN103848810A (zh) * | 2012-11-30 | 2014-06-11 | 北京赛林泰医药技术有限公司 | 鲁顿酪氨酸激酶抑制剂 |
| WO2015008844A1 (ja) * | 2013-07-18 | 2015-01-22 | 大鵬薬品工業株式会社 | Ｆｇｆｒ阻害剤耐性癌の治療薬 |
| DK3023100T3 (da) * | 2013-07-18 | 2019-05-27 | Taiho Pharmaceutical Co Ltd | Antitumorlægemiddel til intermitterende administration af fgfr-hæmmer |
| KR101862493B1 (ko) | 2013-10-25 | 2018-05-29 | 노파르티스 아게 | Fgfr4 억제제로서의 고리-융합된 비시클릭 피리딜 유도체 |
| EP3274344B1 (en) | 2015-03-25 | 2019-04-24 | Novartis Ag | Formylated n-heterocyclic derivatives as fgfr4 inhibitors |
-
2016
- 2016-09-19 CN CN201610833890.3A patent/CN107840842A/zh not_active Withdrawn
-
2017
- 2017-01-25 RU RU2019112046A patent/RU2729069C1/ru active
- 2017-01-25 WO PCT/CN2017/072570 patent/WO2018049781A1/zh not_active Ceased
- 2017-01-25 KR KR1020197011454A patent/KR102783517B1/ko active Active
- 2017-01-25 EP EP17849992.7A patent/EP3517535B1/en active Active
- 2017-01-25 CN CN201780057036.5A patent/CN109843873B/zh active Active
- 2017-01-25 SG SG10202102822RA patent/SG10202102822RA/en unknown
- 2017-01-25 MX MX2019003143A patent/MX390747B/es unknown
- 2017-01-25 JP JP2019515464A patent/JP6906811B2/ja active Active
- 2017-01-25 AU AU2017327954A patent/AU2017327954B2/en active Active
- 2017-01-25 ES ES17849992T patent/ES2925212T3/es active Active
- 2017-01-25 CA CA3036594A patent/CA3036594C/en active Active
-
2019
- 2019-03-14 US US16/353,806 patent/US10710981B2/en active Active
-
2020
- 2020-07-10 US US16/925,738 patent/US11059805B2/en active Active
-
2021
- 2021-07-07 US US17/369,850 patent/US11572353B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP3517535A1 (en) | 2019-07-31 |
| JP2019529444A (ja) | 2019-10-17 |
| MX2019003143A (es) | 2019-06-17 |
| AU2017327954B2 (en) | 2022-02-03 |
| KR20190052113A (ko) | 2019-05-15 |
| ES2925212T3 (es) | 2022-10-14 |
| RU2729069C1 (ru) | 2020-08-04 |
| CA3036594C (en) | 2024-02-13 |
| US10710981B2 (en) | 2020-07-14 |
| CN109843873B (zh) | 2022-06-17 |
| WO2018049781A1 (zh) | 2018-03-22 |
| US11059805B2 (en) | 2021-07-13 |
| AU2017327954A1 (en) | 2019-05-02 |
| US20210332027A1 (en) | 2021-10-28 |
| KR102783517B1 (ko) | 2025-03-19 |
| CA3036594A1 (en) | 2018-03-22 |
| MX390747B (es) | 2025-03-21 |
| SG10202102822RA (en) | 2021-05-28 |
| US20200339541A1 (en) | 2020-10-29 |
| US20190210997A1 (en) | 2019-07-11 |
| EP3517535B1 (en) | 2022-06-29 |
| CN109843873A (zh) | 2019-06-04 |
| US11572353B2 (en) | 2023-02-07 |
| CN107840842A (zh) | 2018-03-27 |
| EP3517535A4 (en) | 2020-02-26 |
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