PE20120617A1 - Procesos para preparar cobicistat y sus productos intermedios - Google Patents
Procesos para preparar cobicistat y sus productos intermediosInfo
- Publication number
- PE20120617A1 PE20120617A1 PE2011001737A PE2011001737A PE20120617A1 PE 20120617 A1 PE20120617 A1 PE 20120617A1 PE 2011001737 A PE2011001737 A PE 2011001737A PE 2011001737 A PE2011001737 A PE 2011001737A PE 20120617 A1 PE20120617 A1 PE 20120617A1
- Authority
- PE
- Peru
- Prior art keywords
- compound
- formula
- prepare
- cobicistat
- processes
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/70—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by reduction of unsaturated amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/34—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/02—Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C307/04—Diamides of sulfuric acids
- C07C307/06—Diamides of sulfuric acids having nitrogen atoms of the sulfamide groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- 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
- 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
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16649809P | 2009-04-03 | 2009-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20120617A1 true PE20120617A1 (es) | 2012-05-26 |
Family
ID=42634770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2011001737A PE20120617A1 (es) | 2009-04-03 | 2010-04-01 | Procesos para preparar cobicistat y sus productos intermedios |
Country Status (27)
| Country | Link |
|---|---|
| US (4) | US8497396B2 (enExample) |
| EP (2) | EP2414325B1 (enExample) |
| JP (8) | JP5612662B2 (enExample) |
| KR (3) | KR20180077324A (enExample) |
| CN (4) | CN104876888B (enExample) |
| AP (1) | AP2887A (enExample) |
| AR (1) | AR076027A1 (enExample) |
| AU (1) | AU2010232559B2 (enExample) |
| BR (1) | BRPI1012638B8 (enExample) |
| CA (4) | CA2925137C (enExample) |
| CL (1) | CL2011002370A1 (enExample) |
| CO (1) | CO6400216A2 (enExample) |
| EA (2) | EA201590979A1 (enExample) |
| EC (1) | ECSP11011391A (enExample) |
| ES (1) | ES2548252T3 (enExample) |
| HK (1) | HK1223912A1 (enExample) |
| IL (4) | IL215399A (enExample) |
| MX (2) | MX2011010397A (enExample) |
| NZ (4) | NZ617773A (enExample) |
| PE (1) | PE20120617A1 (enExample) |
| PT (1) | PT2414325E (enExample) |
| SG (2) | SG174585A1 (enExample) |
| TW (2) | TW201518283A (enExample) |
| UA (1) | UA108738C2 (enExample) |
| UY (1) | UY32535A (enExample) |
| WO (1) | WO2010115000A2 (enExample) |
| ZA (1) | ZA201107430B (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA108738C2 (uk) | 2009-04-03 | 2015-06-10 | Спосіб одержання інгібітора цитохром р450 монооксигенази та залучені проміжні сполуки | |
| JP2012140390A (ja) * | 2011-01-06 | 2012-07-26 | Sumitomo Chemical Co Ltd | α−アミノ−γ−ブチロラクトンの製造方法 |
| ES2543923T3 (es) * | 2011-05-02 | 2015-08-25 | Gilead Sciences, Inc. | Sales sólidas amorfas de Cobicistat (GS-9350) |
| MX2014009344A (es) * | 2012-02-03 | 2015-05-11 | Gilead Sciences Inc | Metodos e intermediarios para preparar agentes farmaceuticos. |
| WO2014047849A1 (zh) * | 2012-09-27 | 2014-04-03 | 上海迪赛诺化学制药有限公司 | 细胞色素p450单加氧酶抑制剂中间体及其制法和用途 |
| CN103694196A (zh) * | 2012-09-27 | 2014-04-02 | 上海迪赛诺化学制药有限公司 | 细胞色素p450单加氧酶抑制剂中间体及其制法和用途 |
| WO2014057498A2 (en) | 2012-10-08 | 2014-04-17 | Mylan Laboratories Ltd. | Process for the preparation of cobicistat intermediates |
| WO2014105777A1 (en) * | 2012-12-26 | 2014-07-03 | Assia Chemical Industries Ltd. | Cobicostat dichlohydrate salt |
| CN104370777A (zh) * | 2013-08-13 | 2015-02-25 | 上海迪赛诺化学制药有限公司 | 合成(2r,5r)-1,6-二苯基己烷-2,5-二胺及其盐的中间体及所述中间体的制备方法和应用 |
| JP2016538312A (ja) * | 2013-11-29 | 2016-12-08 | マイラン ラボラトリーズ リミテッドＭｙｌａｎ Ｌａｂｏｒａｔｏｒｉｅｓ Ｌｉｍｉｔｅｄ | 非晶質のコビシスタットの固体分散体 |
| EP3077373B1 (en) | 2013-12-03 | 2018-09-12 | Mylan Laboratories Ltd. | Preparation of cobicistat intermediates |
| CN104193643B (zh) * | 2014-09-12 | 2016-02-10 | 宁波九胜创新医药科技有限公司 | 用于合成抗艾滋病药物增强剂cobicistat的中间体 |
| CN104447472A (zh) * | 2014-11-06 | 2015-03-25 | 江苏森萱医药化工股份有限公司 | D)-2-苄基-n,n-二甲基氮杂环丙烷基-1-磺酰胺合成方法 |
| CN104557565B (zh) * | 2015-01-08 | 2016-07-06 | 浙江工业大学 | 抗艾滋病药物增强剂Cobicistat关键中间体盐酸盐的制备方法 |
| US10454867B2 (en) * | 2015-02-09 | 2019-10-22 | Airwatch Llc | Enhanced e-mail delivery to mobile devices |
| US10351556B2 (en) * | 2015-02-18 | 2019-07-16 | Msn Laboratories Private Limited | Process for the preparation of 1,3-thiazol-5-ylmethyl [(2R,5R)-5-{[(2s)-2-[(methyl{[2-(propan-2-yl)-1,3-thiazol-4YL] methyl} carbamoyl) amino]-4-(morpholin-4-yl)butanoyl]amino)-1,6-diphenylhexan-2-yl]carbamate |
| CN107674039A (zh) * | 2016-08-01 | 2018-02-09 | 上海朴颐化学科技有限公司 | 一种可比西他中间体的制备方法 |
| US20180085387A1 (en) | 2016-09-27 | 2018-03-29 | Gilead Sciences, Inc. | Therapeutic compositions for treatment of human immunodeficiency virus |
| CN109912530A (zh) * | 2017-12-13 | 2019-06-21 | 上海奥博生物医药技术有限公司 | 一种可比司他原料杂质的制备方法 |
| CN109232301B (zh) * | 2018-10-15 | 2021-01-01 | 天津希恩思生化科技有限公司 | 一种四异丙基肼的制备方法 |
| CN110642721B (zh) * | 2018-12-21 | 2022-09-30 | 安徽贝克生物制药有限公司 | 盐酸司来吉兰的制备方法 |
| CN110878071A (zh) * | 2019-11-21 | 2020-03-13 | 华南农业大学 | 一种α-氨基-γ-丁内酯及其盐的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1183026E (pt) * | 1999-06-04 | 2006-11-30 | Abbott Lab | Formulações farmacêuticas melhoradas incluindo ritonavir |
| US20030153771A1 (en) | 2001-09-27 | 2003-08-14 | Kolb Hartmuth C. | Large scale synthesis of optically pure aziridines |
| WO2003106445A1 (en) * | 2002-06-12 | 2003-12-24 | Qsi Pharma A/S | Compounds and methods for controlling bacterial virulence |
| EP1771536A1 (en) * | 2004-07-23 | 2007-04-11 | The Procter and Gamble Company | Liquid detergent composition for improved low temperature grease cleaning and starch soil cleaning |
| US7786153B2 (en) * | 2005-03-02 | 2010-08-31 | Abbott Laboratories Inc. | Compounds that are useful for improving pharmacokinetics |
| KR101477822B1 (ko) * | 2006-07-07 | 2015-01-02 | 길리애드 사이언시즈, 인코포레이티드 | 치료제의 약동학 특성의 모듈레이터 |
| PT3150586T (pt) * | 2007-02-23 | 2020-03-31 | Gilead Sciences Inc | Moduladores de propriedades farmacocinéticas de agentes terapêuticos |
| KR20100040896A (ko) * | 2007-07-06 | 2010-04-21 | 길리애드 사이언시즈, 인코포레이티드 | 치료제의 약동학적 특성의 조절제 |
| PT2231628E (pt) * | 2008-01-04 | 2015-12-29 | Gilead Sciences Inc | Inibidores de citocromo p450 |
| EA201591353A1 (ru) | 2008-05-02 | 2016-01-29 | Джилид Сайэнс, Инк. | Применение частиц твердого носителя для улучшения технологических характеристик фармацевтического агента |
| UA108738C2 (uk) | 2009-04-03 | 2015-06-10 | Спосіб одержання інгібітора цитохром р450 монооксигенази та залучені проміжні сполуки |
-
2010
- 2010-01-04 UA UAA201111540A patent/UA108738C2/ru unknown
- 2010-03-31 TW TW103133537A patent/TW201518283A/zh unknown
- 2010-03-31 TW TW99109929A patent/TWI464165B/zh active
- 2010-03-31 AR ARP100101077 patent/AR076027A1/es unknown
- 2010-04-01 PT PT107130759T patent/PT2414325E/pt unknown
- 2010-04-01 NZ NZ617773A patent/NZ617773A/en unknown
- 2010-04-01 ES ES10713075.9T patent/ES2548252T3/es active Active
- 2010-04-01 NZ NZ726536A patent/NZ726536A/en unknown
- 2010-04-01 KR KR1020187018487A patent/KR20180077324A/ko not_active Ceased
- 2010-04-01 EP EP10713075.9A patent/EP2414325B1/en active Active
- 2010-04-01 MX MX2011010397A patent/MX2011010397A/es active IP Right Grant
- 2010-04-01 KR KR1020177009970A patent/KR101874557B1/ko active Active
- 2010-04-01 CN CN201510160505.9A patent/CN104876888B/zh active Active
- 2010-04-01 WO PCT/US2010/029633 patent/WO2010115000A2/en not_active Ceased
- 2010-04-01 CA CA2925137A patent/CA2925137C/en active Active
- 2010-04-01 EP EP15171216.3A patent/EP3009434A1/en not_active Withdrawn
- 2010-04-01 EA EA201590979A patent/EA201590979A1/ru unknown
- 2010-04-01 BR BRPI1012638A patent/BRPI1012638B8/pt active IP Right Grant
- 2010-04-01 JP JP2012503704A patent/JP5612662B2/ja active Active
- 2010-04-01 SG SG2011069937A patent/SG174585A1/en unknown
- 2010-04-01 NZ NZ708978A patent/NZ708978A/en unknown
- 2010-04-01 CN CN202010112624.8A patent/CN111217808A/zh active Pending
- 2010-04-01 MX MX2013003678A patent/MX338731B/es unknown
- 2010-04-01 CN CN201710518109.8A patent/CN107382997B/zh active Active
- 2010-04-01 KR KR1020117026120A patent/KR101728375B1/ko active Active
- 2010-04-01 CA CA2754698A patent/CA2754698C/en active Active
- 2010-04-01 AP AP2011005864A patent/AP2887A/xx active
- 2010-04-01 CA CA3008903A patent/CA3008903C/en active Active
- 2010-04-01 SG SG10201404926UA patent/SG10201404926UA/en unknown
- 2010-04-01 PE PE2011001737A patent/PE20120617A1/es active IP Right Grant
- 2010-04-01 AU AU2010232559A patent/AU2010232559B2/en active Active
- 2010-04-01 US US12/752,639 patent/US8497396B2/en active Active
- 2010-04-01 CA CA3083433A patent/CA3083433C/en active Active
- 2010-04-01 CN CN201080014307.7A patent/CN102438982B/zh active Active
- 2010-04-01 NZ NZ59486410A patent/NZ594864A/en unknown
- 2010-04-01 EA EA201190179A patent/EA022739B1/ru unknown
- 2010-04-05 UY UY32535A patent/UY32535A/es not_active Application Discontinuation
-
2011
- 2011-09-06 CO CO11114749A patent/CO6400216A2/es not_active Application Discontinuation
- 2011-09-26 CL CL2011002370A patent/CL2011002370A1/es unknown
- 2011-09-27 IL IL215399A patent/IL215399A/en active IP Right Grant
- 2011-10-11 ZA ZA2011/07430A patent/ZA201107430B/en unknown
- 2011-10-12 EC ECSP11011391 patent/ECSP11011391A/es unknown
-
2013
- 2013-06-24 US US13/925,302 patent/US8853210B2/en active Active
-
2014
- 2014-05-20 JP JP2014104007A patent/JP5986599B2/ja active Active
- 2014-09-03 US US14/476,622 patent/US9115100B2/en active Active
-
2015
- 2015-03-10 IL IL237642A patent/IL237642A/en active IP Right Grant
- 2015-03-10 IL IL237643A patent/IL237643A/en active IP Right Grant
- 2015-07-14 US US14/799,090 patent/US9428473B2/en active Active
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2016
- 2016-01-28 JP JP2016014135A patent/JP6180561B2/ja active Active
- 2016-09-09 HK HK16110713.7A patent/HK1223912A1/en unknown
-
2017
- 2017-01-11 IL IL250068A patent/IL250068A0/en unknown
- 2017-02-27 JP JP2017034914A patent/JP6336161B2/ja active Active
- 2017-07-28 JP JP2017146329A patent/JP6491706B2/ja active Active
-
2018
- 2018-06-18 JP JP2018115527A patent/JP2018162274A/ja not_active Withdrawn
-
2020
- 2020-08-07 JP JP2020134426A patent/JP2020189861A/ja not_active Withdrawn
-
2022
- 2022-10-19 JP JP2022167506A patent/JP2023002679A/ja not_active Withdrawn
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