CN109890790A - 一种奥司他韦及其异构体的制备方法 - Google Patents

一种奥司他韦及其异构体的制备方法 Download PDF

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Publication number
CN109890790A
CN109890790A CN201880003804.3A CN201880003804A CN109890790A CN 109890790 A CN109890790 A CN 109890790A CN 201880003804 A CN201880003804 A CN 201880003804A CN 109890790 A CN109890790 A CN 109890790A
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formula
compound
compound shown
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acid
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CN109890790B (zh
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陈红军
廖守主
王仲清
曾磊
刘壮丰
罗忠华
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Guangdong HEC Pharmaceutical
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Sunshine Lake Pharma Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/61—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon 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
    • C07D303/40—Compounds containing oxirane rings with hydrocarbon 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 by ester radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)

Abstract

本发明涉及一种制备奥司他韦及其异构体的中间体，本发明所述的中间体，是在mitsunobu反应条件下利用邻基参与作用在室温下制备获得。更进一步的，本发明还提供了一种以上述中间体或者上述制备方法为关键步骤的制备奥司他韦及其异构体的方法。本发明所述的方法具有高效、温和、低毒、经济环保等优点，非常适合工业化生产。

Description

PCT国内申请，说明书已公开。

Claims (13)

  1. PCT国内申请，权利要求书已公开。
CN201880003804.3A 2017-06-20 2018-06-15 一种奥司他韦及其异构体的制备方法 Active CN109890790B (zh)

Applications Claiming Priority (3)

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CN2017104695179 2017-06-20
CN201710469517 2017-06-20
PCT/CN2018/091465 WO2018233562A1 (zh) 2017-06-20 2018-06-15 一种奥司他韦及其异构体的制备方法

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CN109890790B CN109890790B (zh) 2020-04-21

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111153818A (zh) * 2020-03-13 2020-05-15 遂成药业股份有限公司 一种制备抗病毒药物达菲中间体叔丁胺衍生物i的方法
CN112812033A (zh) * 2021-02-01 2021-05-18 山东大学 一种奥司他韦的新合成方法
CN113024396A (zh) * 2019-12-25 2021-06-25 上海奥博生物医药技术有限公司 一种奥司他韦的制备方法及其中间体

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111763152B (zh) * 2019-04-01 2024-03-29 上海医药集团股份有限公司 一种乙酰氨基类物质的制备方法
CN110563600B (zh) * 2019-09-19 2020-06-16 北京新领先医药科技发展有限公司 一种磷酸奥司他韦的制备方法
CN114057595B (zh) * 2022-01-17 2022-06-10 深圳市海滨制药有限公司 一种磷酸奥司他韦的合成方法
CN115417783A (zh) * 2022-08-18 2022-12-02 苏州匠化生物科技有限公司 一种合成奥司他韦对映异构体的方法

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1113053C (zh) * 1996-08-23 2003-07-02 吉里德科学公司 环己烯羧酸衍生物的制备
CN1759093A (zh) * 2003-03-13 2006-04-12 弗·哈夫曼-拉罗切有限公司 用于制备1,2－二氨基化合物的不使用叠氮化物的方法
JP2009215239A (ja) * 2008-03-11 2009-09-24 Tadakatsu Bandai オセルタミビル及びその類縁化合物の製造方法
WO2009137916A1 (en) * 2008-05-12 2009-11-19 Brock University Processes and intermediates for the preparation of oseltamivir and analogs thereof
WO2011047466A1 (en) * 2009-10-23 2011-04-28 Brock University Process and compounds for the manufacture of oseltamivir and analogs thereof, and new antiviral agents
CN103402973A (zh) * 2011-03-08 2013-11-20 公益财团法人微生物化学研究会 化合物及其生产方法，以及用于生产磷酸奥司他韦的方法
WO2015049700A1 (en) * 2013-10-04 2015-04-09 Council Of Scientific And Industrial Research A process for the preparation of intermediate for the preparation of oseltamivir phosphate
CN106278928A (zh) * 2016-08-10 2017-01-04 宜昌东阳光长江药业股份有限公司 一种磷酸奥司他韦异构体杂质的合成方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1113053C (zh) * 1996-08-23 2003-07-02 吉里德科学公司 环己烯羧酸衍生物的制备
CN1759093A (zh) * 2003-03-13 2006-04-12 弗·哈夫曼-拉罗切有限公司 用于制备1,2－二氨基化合物的不使用叠氮化物的方法
JP2009215239A (ja) * 2008-03-11 2009-09-24 Tadakatsu Bandai オセルタミビル及びその類縁化合物の製造方法
WO2009137916A1 (en) * 2008-05-12 2009-11-19 Brock University Processes and intermediates for the preparation of oseltamivir and analogs thereof
WO2011047466A1 (en) * 2009-10-23 2011-04-28 Brock University Process and compounds for the manufacture of oseltamivir and analogs thereof, and new antiviral agents
CN103402973A (zh) * 2011-03-08 2013-11-20 公益财团法人微生物化学研究会 化合物及其生产方法，以及用于生产磷酸奥司他韦的方法
WO2015049700A1 (en) * 2013-10-04 2015-04-09 Council Of Scientific And Industrial Research A process for the preparation of intermediate for the preparation of oseltamivir phosphate
CN106278928A (zh) * 2016-08-10 2017-01-04 宜昌东阳光长江药业股份有限公司 一种磷酸奥司他韦异构体杂质的合成方法

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BARRY M. TROST 等: "A Concise Synthesis of (-)-Oseltamivir", 《ANGEW.CHEM.INT.ED.》 *
BARRY M. TROST 等: "Development of a Concise Synthesis of (-)-Oseltamivir (Tamiflu)", 《CHEM.EUR.J.》 *
王小龙 等: "Mitsunobu反应在构建化学键中的研究进展", 《有机化学》 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113024396A (zh) * 2019-12-25 2021-06-25 上海奥博生物医药技术有限公司 一种奥司他韦的制备方法及其中间体
CN113024396B (zh) * 2019-12-25 2024-01-30 上海奥博生物医药股份有限公司 一种奥司他韦的制备方法及其中间体
CN111153818A (zh) * 2020-03-13 2020-05-15 遂成药业股份有限公司 一种制备抗病毒药物达菲中间体叔丁胺衍生物i的方法
CN111153818B (zh) * 2020-03-13 2023-03-28 遂成药业股份有限公司 一种制备抗病毒药物达菲中间体叔丁胺衍生物i的方法
CN112812033A (zh) * 2021-02-01 2021-05-18 山东大学 一种奥司他韦的新合成方法
CN112812033B (zh) * 2021-02-01 2022-02-15 山东大学 一种奥司他韦的新合成方法

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Address after: 523808 No.1, Gongye North Road, Songshanhu Park, Dongguan City, Guangdong Province

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