MX390072B - Reaccion de prins e intermediarios utiles en la sintesis de macrolidos de halicondrina y analogos de los mismos. - Google Patents
Reaccion de prins e intermediarios utiles en la sintesis de macrolidos de halicondrina y analogos de los mismos.Info
- Publication number
- MX390072B MX390072B MX2018016329A MX2018016329A MX390072B MX 390072 B MX390072 B MX 390072B MX 2018016329 A MX2018016329 A MX 2018016329A MX 2018016329 A MX2018016329 A MX 2018016329A MX 390072 B MX390072 B MX 390072B
- Authority
- MX
- Mexico
- Prior art keywords
- synthesis
- prins
- reaction
- analogues
- intermediates useful
- Prior art date
Links
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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
- C07D307/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/28—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings 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
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed 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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662357031P | 2016-06-30 | 2016-06-30 | |
| PCT/US2017/040401 WO2018006031A1 (en) | 2016-06-30 | 2017-06-30 | Prins reaction and intermediates useful in the synthesis of halichondrin macrolides and analogs thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MX2018016329A MX2018016329A (es) | 2019-09-18 |
| MX390072B true MX390072B (es) | 2025-03-20 |
Family
ID=60786711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2018016329A MX390072B (es) | 2016-06-30 | 2017-06-30 | Reaccion de prins e intermediarios utiles en la sintesis de macrolidos de halicondrina y analogos de los mismos. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US11136335B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3478691A4 (cg-RX-API-DMAC7.html) |
| JP (3) | JP7068204B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102404629B1 (cg-RX-API-DMAC7.html) |
| CN (2) | CN109641917B (cg-RX-API-DMAC7.html) |
| IL (2) | IL263845B (cg-RX-API-DMAC7.html) |
| MX (1) | MX390072B (cg-RX-API-DMAC7.html) |
| SG (1) | SG11201811671XA (cg-RX-API-DMAC7.html) |
| WO (1) | WO2018006031A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2522663T3 (pl) | 2004-06-03 | 2015-08-31 | Eisai R&D Man Co Ltd | Produkty pośrednie do otrzymywania halichondryny B |
| JP5735277B2 (ja) | 2007-10-03 | 2015-06-17 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ハリコンドリンｂ類似体の合成のための中間体および方法 |
| SG182612A1 (en) | 2010-01-26 | 2012-08-30 | Eisai R&D Man Co Ltd | Furo [3, 2 -b] pyrane derivatives useful in the synthesis of halichondrin b analogs |
| JP6625533B2 (ja) | 2013-11-04 | 2019-12-25 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ハリコンドリンｂの類縁体の合成において有用な大環化反応および中間体 |
| MX376869B (es) | 2013-12-06 | 2025-03-07 | Eisai R&D Man Co Ltd | Metodos utiles en la sintesis de analogos de halicondrina b. |
| US10308661B2 (en) | 2015-05-07 | 2019-06-04 | Eisai R&D Management Co., Ltd. | Macrocyclization reactions and intermediates and other fragments useful in the synthesis of halichondrin macrolides |
| MX377663B (es) | 2016-02-12 | 2025-03-11 | Eisai R&D Man Co Ltd | Intermediarios en la sintesis de eribulina y metodos de sintesis relacionados. |
| CN118894868A (zh) | 2018-01-03 | 2024-11-05 | 卫材R&D管理有限公司 | 可用于合成软海绵素大环内酯及其类似物的普林斯反应和化合物 |
| EP3608323B1 (en) * | 2018-03-02 | 2021-11-03 | Beijing Tienyi Lufu Pharmatech Co. Ltd. | Pyran fused ring compound, preparation method therefor and use thereof |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU652180A1 (ru) | 1975-12-16 | 1979-03-15 | Краснодарский политехнический институт | 1(Фурил-2,)-2-(2-,, формилфурил-5,, ) этилен или его метильное производное как промежуточный продукт дл синтеза фуран-2,5-дикарбоновой кислоты и способ его получени |
| US5338865A (en) | 1992-03-12 | 1994-08-16 | President And Fellows Of Harvard College | Synthesis of halichondrin B and norhalichondrin B |
| US5436238A (en) | 1992-03-12 | 1995-07-25 | President And Fellows Of Harvard College | Halichondrins and related compounds |
| GB9206244D0 (en) | 1992-03-23 | 1992-05-06 | Pharma Mar Sa | Cytotoxic compound from a marine sponge |
| TW255880B (cg-RX-API-DMAC7.html) | 1992-09-09 | 1995-09-01 | Hoechst Ag | |
| CA2264298A1 (en) | 1996-09-06 | 1998-03-12 | Eli Lilly And Company | Catalytic selective sulfonylation process |
| US6870058B2 (en) | 1996-12-03 | 2005-03-22 | The Trustees Of The University Of Pennsylvania | Compounds which mimic the chemical and biological properties of discodermolide |
| EP2272839B1 (en) | 1998-06-17 | 2012-08-22 | Eisai R&D Management Co., Ltd. | Intermediate compounds for the preparation of halichondrin analogs |
| US8097648B2 (en) | 1998-06-17 | 2012-01-17 | Eisai R&D Management Co., Ltd. | Methods and compositions for use in treating cancer |
| US6653341B1 (en) | 1998-06-17 | 2003-11-25 | Eisai Co., Ltd. | Methods and compositions for use in treating cancer |
| DE10106647A1 (de) | 2001-02-12 | 2002-08-22 | Univ Hannover | Ratjadon-Derivate zum Hemmen des Zellwachstums |
| PL2522663T3 (pl) | 2004-06-03 | 2015-08-31 | Eisai R&D Man Co Ltd | Produkty pośrednie do otrzymywania halichondryny B |
| US20060045846A1 (en) | 2004-08-30 | 2006-03-02 | Horstmann Thomas E | Reagents and methods for labeling terminal olefins |
| WO2006076100A2 (en) | 2004-12-09 | 2006-07-20 | Eisai Co. Ltd. | Tubulin isotype screening in cancer therapy using halichondrin b analogs |
| JP2009510005A (ja) | 2005-09-26 | 2009-03-12 | シムライズ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング・ウント・コンパニー・コマンジツト・ゲゼルシヤフト | 分子内プリンス反応および該反応に適する触媒 |
| WO2008010776A1 (en) | 2006-07-21 | 2008-01-24 | Agency For Science, Technology And Research | Aigialomycin d and derivatives thereof and their use in treating cancer or malaria or a microbial infection |
| JPWO2009014105A1 (ja) | 2007-07-20 | 2010-10-07 | 株式会社山田養蜂場本社 | 新規カルボン酸およびそれを有効成分とする抗うつ用組成物 |
| JP5735277B2 (ja) | 2007-10-03 | 2015-06-17 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ハリコンドリンｂ類似体の合成のための中間体および方法 |
| CN101910180A (zh) | 2007-11-16 | 2010-12-08 | 卫材R&D管理有限公司 | 用于软海绵素b类似物合成的新颖中间体和用于该中间体的新颖脱磺酰化反应 |
| US8598373B2 (en) | 2008-04-04 | 2013-12-03 | Eisai R&D Management Co., Ltd. | Halichondrin B analogs |
| JP5371091B2 (ja) | 2009-01-23 | 2013-12-18 | 三菱レイヨン株式会社 | モノスルホン酸エステルの製造方法 |
| SG182612A1 (en) | 2010-01-26 | 2012-08-30 | Eisai R&D Man Co Ltd | Furo [3, 2 -b] pyrane derivatives useful in the synthesis of halichondrin b analogs |
| WO2012147900A1 (en) | 2011-04-28 | 2012-11-01 | Eisai R&D Management Co., Ltd. | Microreactor process for halichondrin b analog synthesis |
| AU2012344697A1 (en) | 2011-11-30 | 2014-07-10 | Alphora Research Inc. | Process for preparation of (3R)-2,4-di-leaving group-3-methylbut-1-ene |
| AU2013239290B2 (en) | 2012-03-30 | 2017-08-03 | Sandoz Ag | Synthetic process for preparation of macrocyclic C1-keto analogs of Halichondrin B and intermediates useful therein |
| CN105431438A (zh) | 2013-07-03 | 2016-03-23 | 阿方拉研究股份有限公司 | 用于制备软海绵素b 的大环c1-酮基类似物的合成方法和可用于其中的中间体、包括含有-so2-(对甲苯基)基团的中间体 |
| JP6625533B2 (ja) | 2013-11-04 | 2019-12-25 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ハリコンドリンｂの類縁体の合成において有用な大環化反応および中間体 |
| MX376869B (es) | 2013-12-06 | 2025-03-07 | Eisai R&D Man Co Ltd | Metodos utiles en la sintesis de analogos de halicondrina b. |
| US10208058B2 (en) | 2014-09-09 | 2019-02-19 | Cipla Limited | Process for the preparation of macrocyclic ketone analogs of halichondrin B or pharmaceutically acceptable salts and intermediates thereof |
| US10308661B2 (en) | 2015-05-07 | 2019-06-04 | Eisai R&D Management Co., Ltd. | Macrocyclization reactions and intermediates and other fragments useful in the synthesis of halichondrin macrolides |
| MX377663B (es) | 2016-02-12 | 2025-03-11 | Eisai R&D Man Co Ltd | Intermediarios en la sintesis de eribulina y metodos de sintesis relacionados. |
| WO2018217894A1 (en) | 2017-05-24 | 2018-11-29 | Eisai R&D Management Co., Ltd. | Fluorine-labelled halichondrin derivatives and related methods of synthesis |
| CN118894868A (zh) | 2018-01-03 | 2024-11-05 | 卫材R&D管理有限公司 | 可用于合成软海绵素大环内酯及其类似物的普林斯反应和化合物 |
-
2017
- 2017-06-30 CN CN201780052964.2A patent/CN109641917B/zh active Active
- 2017-06-30 WO PCT/US2017/040401 patent/WO2018006031A1/en not_active Ceased
- 2017-06-30 CN CN202210653392.6A patent/CN114805322B/zh active Active
- 2017-06-30 EP EP17821400.3A patent/EP3478691A4/en not_active Withdrawn
- 2017-06-30 MX MX2018016329A patent/MX390072B/es unknown
- 2017-06-30 US US16/313,196 patent/US11136335B2/en active Active
- 2017-06-30 SG SG11201811671XA patent/SG11201811671XA/en unknown
- 2017-06-30 KR KR1020197002930A patent/KR102404629B1/ko active Active
- 2017-06-30 JP JP2018568296A patent/JP7068204B2/ja active Active
-
2018
- 2018-12-19 IL IL263845A patent/IL263845B/en unknown
-
2021
- 2021-11-28 IL IL288460A patent/IL288460B2/en unknown
-
2022
- 2022-04-28 JP JP2022073976A patent/JP7440563B2/ja active Active
-
2024
- 2024-02-15 JP JP2024020885A patent/JP2024056892A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP7068204B2 (ja) | 2022-05-16 |
| US11136335B2 (en) | 2021-10-05 |
| RU2019102375A (ru) | 2020-07-30 |
| JP2019524674A (ja) | 2019-09-05 |
| JP7440563B2 (ja) | 2024-02-28 |
| SG11201811671XA (en) | 2019-01-30 |
| IL288460A (en) | 2022-01-01 |
| KR102404629B1 (ko) | 2022-06-02 |
| CN114805322B (zh) | 2025-05-30 |
| RU2019102375A3 (cg-RX-API-DMAC7.html) | 2021-07-05 |
| MX2018016329A (es) | 2019-09-18 |
| IL288460B1 (en) | 2023-04-01 |
| IL263845B (en) | 2022-01-01 |
| CN114805322A (zh) | 2022-07-29 |
| CN109641917A (zh) | 2019-04-16 |
| IL263845A (en) | 2019-01-31 |
| WO2018006031A1 (en) | 2018-01-04 |
| JP2024056892A (ja) | 2024-04-23 |
| IL288460B2 (en) | 2023-08-01 |
| JP2022105115A (ja) | 2022-07-12 |
| EP3478691A1 (en) | 2019-05-08 |
| EP3478691A4 (en) | 2020-07-22 |
| CN109641917B (zh) | 2022-06-14 |
| US20190161495A1 (en) | 2019-05-30 |
| KR20190039103A (ko) | 2019-04-10 |
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