JP7206188B2 - Iii型受容体チロシンキナーゼ阻害剤としてのキノキサリン化合物 - Google Patents
Iii型受容体チロシンキナーゼ阻害剤としてのキノキサリン化合物 Download PDFInfo
- Publication number
- JP7206188B2 JP7206188B2 JP2019519329A JP2019519329A JP7206188B2 JP 7206188 B2 JP7206188 B2 JP 7206188B2 JP 2019519329 A JP2019519329 A JP 2019519329A JP 2019519329 A JP2019519329 A JP 2019519329A JP 7206188 B2 JP7206188 B2 JP 7206188B2
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- carbonitrile
- amino
- quinoxaline
- phenyl
- 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.)
- Active
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Classifications
-
- 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
- A61K31/498—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
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—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
- C07D401/04—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
- C07D401/14—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
- C07D403/12—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
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
- C07D413/02—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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662406328P | 2016-10-10 | 2016-10-10 | |
| US62/406,328 | 2016-10-10 | ||
| PCT/US2017/055809 WO2018071348A1 (en) | 2016-10-10 | 2017-10-09 | Quinoxaline compounds as type iii receptor tyrosine kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019530708A JP2019530708A (ja) | 2019-10-24 |
| JP2019530708A5 JP2019530708A5 (https=) | 2020-11-12 |
| JP7206188B2 true JP7206188B2 (ja) | 2023-01-17 |
Family
ID=61905910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019519329A Active JP7206188B2 (ja) | 2016-10-10 | 2017-10-09 | Iii型受容体チロシンキナーゼ阻害剤としてのキノキサリン化合物 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US10689362B2 (https=) |
| EP (1) | EP3523285A4 (https=) |
| JP (1) | JP7206188B2 (https=) |
| KR (1) | KR102609813B1 (https=) |
| CN (1) | CN110325515B (https=) |
| AU (1) | AU2017342928B2 (https=) |
| BR (1) | BR112019007271A2 (https=) |
| CA (1) | CA3039919A1 (https=) |
| IL (1) | IL265829B (https=) |
| RU (1) | RU2019113764A (https=) |
| SG (1) | SG11201903091VA (https=) |
| TW (1) | TWI648266B (https=) |
| WO (1) | WO2018071348A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2023542041A (ja) * | 2020-09-21 | 2023-10-04 | ハチソン メディファルマ リミテッド | ヘテロ芳香族化合物及びその使用 |
| JP2024515976A (ja) * | 2021-04-26 | 2024-04-11 | ザ ボード オブ トラスティーズ オブ ザ レランド スタンフォード ジュニア ユニバーシティー | 骨格再生のための機能不全骨格幹細胞の生化学的活性化 |
| WO2023082145A1 (en) * | 2021-11-11 | 2023-05-19 | 4B Technologies (Suzhou) Limited | Intermediate compound of quinoxaline and preparation process thereof |
| CN114605391B (zh) * | 2022-02-21 | 2024-01-26 | 广州六顺生物科技股份有限公司 | 喹喔啉类衍生物及其制备方法和应用 |
| CN115141177B (zh) * | 2022-08-30 | 2022-12-09 | 福贝生物科技(苏州)有限公司 | 喹喔啉类化合物马来酸盐的新晶型及其制备方法 |
| CN121793964A (zh) * | 2023-07-18 | 2026-04-03 | 安立玺荣生医股份有限公司 | 增强喹喔啉iii型受体酪氨酸激酶抑制剂的吸收的方法 |
| WO2025067450A1 (zh) * | 2023-09-28 | 2025-04-03 | 福贝生物医药科技(北京)有限公司 | 一种固体分散体、药物组合物、其制备方法及其用途 |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009534410A (ja) | 2006-04-19 | 2009-09-24 | ノバルティス アクチエンゲゼルシャフト | 6−o−置換ベンゾオキサゾールおよびベンゾチアゾール化合物ならびにcsf−1rシグナル伝達を阻害する方法 |
| JP2010510321A (ja) | 2006-11-22 | 2010-04-02 | プレキシコン,インコーポレーテッド | C−fmsおよび/またはc−kit活性を調節する化合物およびその用途 |
| JP2013503824A (ja) | 2009-09-04 | 2013-02-04 | バイエル・ファルマ・アクチェンゲゼルシャフト | チロシンスレオニンキナーゼ阻害剤としての置換アミノキノキサリン |
| JP2013528580A (ja) | 2010-04-30 | 2013-07-11 | アステックス、セラピューティックス、リミテッド | ピラゾリルキナゾリンキナーゼ阻害剤 |
| WO2013112950A2 (en) | 2012-01-25 | 2013-08-01 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
| WO2013157540A1 (ja) | 2012-04-17 | 2013-10-24 | 富士フイルム株式会社 | 含窒素複素環化合物またはその塩 |
| JP2013543883A (ja) | 2010-11-29 | 2013-12-09 | アステックス、セラピューティックス、リミテッド | 癌疾患の治療のためのfgfrキナーゼ阻害剤としての置換ベンゾピラジン誘導体 |
| JP2014534212A (ja) | 2011-10-28 | 2014-12-18 | アステックス、セラピューティックス、リミテッドAstex Therapeutics Limited | Fgfrキナーゼ阻害を介した抗癌ベンゾピラジン |
| WO2016077632A2 (en) | 2014-11-13 | 2016-05-19 | Buck Institute For Research On Aging | Inhibition of proline catabolism for the treatment of cancer and other therapeutic applications |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6143764A (en) * | 1995-11-07 | 2000-11-07 | Kirin Beer Kabushiki Kaisha | Quinoline and quinazoline derivatives inhibiting platelet-derived growth factor receptor autophosphorylation and pharmaceutical compositions containing the same |
| WO2000023444A1 (en) * | 1998-10-21 | 2000-04-27 | Abbott Laboratories | 5,7-disubstituted-4-aminopyrido[2,3-d]pyrimidine compounds |
| US7304092B1 (en) * | 2002-11-12 | 2007-12-04 | Yale University | Compounds and methods for treating tumors, cancer and hyperproliferative diseases |
| FR2856686A1 (fr) * | 2003-06-25 | 2004-12-31 | Sod Conseils Rech Applic | Benzothiazole-4,7-diones et benzooxazole-4,7-diones substituees en position 5 ou 6 et leurs procedes de preparation |
| GB0509227D0 (en) * | 2005-05-05 | 2005-06-15 | Chroma Therapeutics Ltd | Intracellular enzyme inhibitors |
| CN101432281B (zh) * | 2006-04-19 | 2013-08-28 | 诺瓦提斯公司 | 6-0-取代的苯并*唑和苯并噻唑化合物以及抑制csf-1r信号传导的方法 |
| GEP20125502B (en) * | 2008-05-23 | 2012-04-25 | Novartis Ag | Derivatives of quinolines and quinoxalines as protein tyrosine kinase inhibitors |
| US9725421B2 (en) | 2012-11-12 | 2017-08-08 | Neupharma, Inc. | Substituted quinoxalines as B-raf kinase inhibitors |
-
2017
- 2017-10-09 US US16/340,685 patent/US10689362B2/en active Active
- 2017-10-09 JP JP2019519329A patent/JP7206188B2/ja active Active
- 2017-10-09 SG SG11201903091VA patent/SG11201903091VA/en unknown
- 2017-10-09 AU AU2017342928A patent/AU2017342928B2/en active Active
- 2017-10-09 KR KR1020197012725A patent/KR102609813B1/ko active Active
- 2017-10-09 CA CA3039919A patent/CA3039919A1/en active Pending
- 2017-10-09 WO PCT/US2017/055809 patent/WO2018071348A1/en not_active Ceased
- 2017-10-09 CN CN201780075303.1A patent/CN110325515B/zh active Active
- 2017-10-09 EP EP17859434.7A patent/EP3523285A4/en active Pending
- 2017-10-09 RU RU2019113764A patent/RU2019113764A/ru not_active Application Discontinuation
- 2017-10-09 BR BR112019007271A patent/BR112019007271A2/pt not_active Application Discontinuation
- 2017-10-11 TW TW106134711A patent/TWI648266B/zh active
-
2019
- 2019-04-04 IL IL265829A patent/IL265829B/en unknown
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009534410A (ja) | 2006-04-19 | 2009-09-24 | ノバルティス アクチエンゲゼルシャフト | 6−o−置換ベンゾオキサゾールおよびベンゾチアゾール化合物ならびにcsf−1rシグナル伝達を阻害する方法 |
| JP2010510321A (ja) | 2006-11-22 | 2010-04-02 | プレキシコン,インコーポレーテッド | C−fmsおよび/またはc−kit活性を調節する化合物およびその用途 |
| JP2013503824A (ja) | 2009-09-04 | 2013-02-04 | バイエル・ファルマ・アクチェンゲゼルシャフト | チロシンスレオニンキナーゼ阻害剤としての置換アミノキノキサリン |
| JP2013528580A (ja) | 2010-04-30 | 2013-07-11 | アステックス、セラピューティックス、リミテッド | ピラゾリルキナゾリンキナーゼ阻害剤 |
| JP2013543883A (ja) | 2010-11-29 | 2013-12-09 | アステックス、セラピューティックス、リミテッド | 癌疾患の治療のためのfgfrキナーゼ阻害剤としての置換ベンゾピラジン誘導体 |
| JP2014534212A (ja) | 2011-10-28 | 2014-12-18 | アステックス、セラピューティックス、リミテッドAstex Therapeutics Limited | Fgfrキナーゼ阻害を介した抗癌ベンゾピラジン |
| WO2013112950A2 (en) | 2012-01-25 | 2013-08-01 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
| WO2013157540A1 (ja) | 2012-04-17 | 2013-10-24 | 富士フイルム株式会社 | 含窒素複素環化合物またはその塩 |
| WO2016077632A2 (en) | 2014-11-13 | 2016-05-19 | Buck Institute For Research On Aging | Inhibition of proline catabolism for the treatment of cancer and other therapeutic applications |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3523285A1 (en) | 2019-08-14 |
| AU2017342928B2 (en) | 2021-09-09 |
| CN110325515B (zh) | 2023-06-20 |
| WO2018071348A1 (en) | 2018-04-19 |
| CA3039919A1 (en) | 2018-04-19 |
| KR102609813B1 (ko) | 2023-12-07 |
| AU2017342928A1 (en) | 2019-05-23 |
| JP2019530708A (ja) | 2019-10-24 |
| EP3523285A4 (en) | 2020-04-22 |
| RU2019113764A3 (https=) | 2021-01-29 |
| RU2019113764A (ru) | 2020-11-13 |
| IL265829B (en) | 2022-06-01 |
| TWI648266B (zh) | 2019-01-21 |
| IL265829A (en) | 2019-06-30 |
| CN110325515A (zh) | 2019-10-11 |
| TW201817720A (zh) | 2018-05-16 |
| BR112019007271A2 (pt) | 2019-09-17 |
| US10689362B2 (en) | 2020-06-23 |
| KR20190059959A (ko) | 2019-05-31 |
| SG11201903091VA (en) | 2019-05-30 |
| US20190308949A1 (en) | 2019-10-10 |
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