MX2018016329A - 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
- MX2018016329A MX2018016329A MX2018016329A MX2018016329A MX2018016329A MX 2018016329 A MX2018016329 A MX 2018016329A MX 2018016329 A MX2018016329 A MX 2018016329A MX 2018016329 A MX2018016329 A MX 2018016329A MX 2018016329 A MX2018016329 A MX 2018016329A
- Authority
- MX
- Mexico
- Prior art keywords
- macrolides
- analogs
- synthesis
- prins
- reaction
- Prior art date
Links
Classifications
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- 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
- 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
-
- 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
-
- 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
- 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
- C07D407/06—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
- 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
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- 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)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (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)
Abstract
La invención proporciona métodos para la síntesis de macrólidos de halicondrina o análogos de los mismos a través de una estrategia de reacción de delación. La estrategia de la presente invención implica someter un intermediario a condiciones de reacción de Prins para proporcionar un macrólido. La invención también proporciona compuestos útiles como compuestos intermediarios en la síntesis de macrólidos de halicondrina o análogos de los mismos y métodos para prepararlos.
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 true MX2018016329A (es) | 2019-09-18 |
| MX390072B 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 (es) |
| EP (1) | EP3478691A4 (es) |
| JP (3) | JP7068204B2 (es) |
| KR (1) | KR102404629B1 (es) |
| CN (2) | CN114805322B (es) |
| IL (2) | IL263845B (es) |
| MX (1) | MX390072B (es) |
| SG (1) | SG11201811671XA (es) |
| WO (1) | WO2018006031A1 (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2522663B1 (en) | 2004-06-03 | 2015-04-01 | Eisai R&D Management Co., Ltd. | Intermediates for the preparation of halichondrin 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 |
| CN102803254B (zh) | 2010-01-26 | 2016-09-14 | 卫材R&D管理有限公司 | 用于软海绵素b类似物合成的呋喃并[3,2-b]吡喃衍生物 |
| ES2787603T3 (es) | 2013-11-04 | 2020-10-16 | Eisai R&D Man Co Ltd | Reacciones de macrociclación y productos intermedios útiles en la síntesis de análogos de halicondrina B |
| HUE043088T2 (hu) | 2013-12-06 | 2019-08-28 | Eisai R&D Man Co Ltd | Halikondrin B analógok szintézisében alkalmazható eljárások |
| CN107849057B (zh) | 2015-05-07 | 2020-11-10 | 卫材R&D管理有限公司 | 用于合成软海绵素大环内酯的大环化反应及中间体和其他片段 |
| JP6786610B2 (ja) | 2016-02-12 | 2020-11-18 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | エリブリンの合成における中間体および関連する合成方法 |
| US11542269B2 (en) | 2018-01-03 | 2023-01-03 | Eisai R&D Management Co., Ltd. | Prins reaction and compounds useful in the synthesis of halichondrin macrolides and analogs thereof |
| CN110218213B (zh) * | 2018-03-02 | 2020-09-04 | 北京天一绿甫医药科技有限公司 | 吡喃稠环类化合物、其制备方法和用途 |
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 (es) | 1992-09-09 | 1995-09-01 | Hoechst Ag | |
| AU4255697A (en) | 1996-09-06 | 1998-03-26 | 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 |
| US6653341B1 (en) | 1998-06-17 | 2003-11-25 | Eisai Co., Ltd. | Methods and compositions for use in treating cancer |
| US8097648B2 (en) | 1998-06-17 | 2012-01-17 | Eisai R&D Management Co., Ltd. | Methods and compositions for use in treating cancer |
| AU762998B2 (en) | 1998-06-17 | 2003-07-10 | Eisai R&D Management Co., Ltd. | Macrocyclic analogs and methods of their use and preparation |
| DE10106647A1 (de) | 2001-02-12 | 2002-08-22 | Univ Hannover | Ratjadon-Derivate zum Hemmen des Zellwachstums |
| EP2522663B1 (en) | 2004-06-03 | 2015-04-01 | Eisai R&D Management Co., Ltd. | Intermediates for the preparation of halichondrin 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 |
| WO2007039342A1 (en) | 2005-09-26 | 2007-04-12 | Symrise Gmbh & Co. Kg | Intramolecular prins reaction and catalysts suitable therefor |
| 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 |
| WO2009014105A1 (ja) | 2007-07-20 | 2009-01-29 | Yamada Apiculture Center, Inc. | 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 |
| RU2010118063A (ru) | 2007-11-16 | 2011-12-27 | ЭЙСАЙ Ар энд Ди МЕНЕДЖМЕНТ КО., ЛТД. (JP) | Новое промежуточное соединение для синтеза аналога галихондрина в и новая реакция десульфонилирования, применяемая для получения промежуточного соединения |
| BRPI0911269A2 (pt) | 2008-04-04 | 2015-09-29 | Eisai R&D Man Co Ltd | análogos de halicondrina b |
| 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 |
| CN102803254B (zh) | 2010-01-26 | 2016-09-14 | 卫材R&D管理有限公司 | 用于软海绵素b类似物合成的呋喃并[3,2-b]吡喃衍生物 |
| WO2012147900A1 (en) | 2011-04-28 | 2012-11-01 | Eisai R&D Management Co., Ltd. | Microreactor process for halichondrin b analog synthesis |
| EP2785687B1 (en) | 2011-11-30 | 2019-02-20 | Sandoz AG | Process for preparation of (3r)-2,4-di-leaving group-3-methylbut-1-ene |
| US9278979B2 (en) | 2012-03-30 | 2016-03-08 | Alphora Research Inc. | Synthetic process for preparation of macrocyclic C1-keto analogs of halichondrin B and intermediates useful therein |
| WO2015000070A1 (en) | 2013-07-03 | 2015-01-08 | Alphora Research Inc. | Synthetic process for preparation of macrocyclic c1-keto analogs of halichondrin b and intermediates useful therein including intermediates containing -so2-(p-tolyl) groups |
| ES2787603T3 (es) | 2013-11-04 | 2020-10-16 | Eisai R&D Man Co Ltd | Reacciones de macrociclación y productos intermedios útiles en la síntesis de análogos de halicondrina B |
| HUE043088T2 (hu) | 2013-12-06 | 2019-08-28 | Eisai R&D Man Co Ltd | Halikondrin B analógok szintézisében alkalmazható eljárások |
| WO2016038624A1 (en) | 2014-09-09 | 2016-03-17 | Cipla Limited | "process for the preparation of macrocyclic ketone analogs of halichondrin b or pharmaceutically acceptable salts and intermediates thereof" |
| CN107849057B (zh) | 2015-05-07 | 2020-11-10 | 卫材R&D管理有限公司 | 用于合成软海绵素大环内酯的大环化反应及中间体和其他片段 |
| JP6786610B2 (ja) | 2016-02-12 | 2020-11-18 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | エリブリンの合成における中間体および関連する合成方法 |
| WO2018217894A1 (en) | 2017-05-24 | 2018-11-29 | Eisai R&D Management Co., Ltd. | Fluorine-labelled halichondrin derivatives and related methods of synthesis |
| US11542269B2 (en) | 2018-01-03 | 2023-01-03 | Eisai R&D Management Co., Ltd. | Prins reaction and compounds useful in the synthesis of halichondrin macrolides and analogs thereof |
-
2017
- 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 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
- 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 US US16/313,196 patent/US11136335B2/en 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 |
|---|---|
| RU2019102375A3 (es) | 2021-07-05 |
| CN109641917A (zh) | 2019-04-16 |
| JP7068204B2 (ja) | 2022-05-16 |
| IL288460B2 (en) | 2023-08-01 |
| WO2018006031A1 (en) | 2018-01-04 |
| JP7440563B2 (ja) | 2024-02-28 |
| EP3478691A4 (en) | 2020-07-22 |
| SG11201811671XA (en) | 2019-01-30 |
| CN114805322B (zh) | 2025-05-30 |
| JP2022105115A (ja) | 2022-07-12 |
| US11136335B2 (en) | 2021-10-05 |
| IL288460A (en) | 2022-01-01 |
| IL288460B1 (en) | 2023-04-01 |
| US20190161495A1 (en) | 2019-05-30 |
| JP2024056892A (ja) | 2024-04-23 |
| CN109641917B (zh) | 2022-06-14 |
| KR102404629B1 (ko) | 2022-06-02 |
| IL263845A (en) | 2019-01-31 |
| EP3478691A1 (en) | 2019-05-08 |
| JP2019524674A (ja) | 2019-09-05 |
| IL263845B (en) | 2022-01-01 |
| KR20190039103A (ko) | 2019-04-10 |
| RU2019102375A (ru) | 2020-07-30 |
| CN114805322A (zh) | 2022-07-29 |
| MX390072B (es) | 2025-03-20 |
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