CN111094260A - 化合物及其在合成布瓦西坦(Brivaracetam)中间体及原料药中的用途 - Google Patents

化合物及其在合成布瓦西坦(Brivaracetam)中间体及原料药中的用途 Download PDF

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CN111094260A
CN111094260A CN201980004099.3A CN201980004099A CN111094260A CN 111094260 A CN111094260 A CN 111094260A CN 201980004099 A CN201980004099 A CN 201980004099A CN 111094260 A CN111094260 A CN 111094260A
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compound
acid
formula
sodium
reducing agent
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CN201980004099.3A
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CN111094260B (zh
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冯岩
王如勇
叶一章
张风森
龚轩
王中红
康心汕
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Fujian Haixi New Pharmaceutical Co ltd
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Fujian Haixi Pharmaceuticals Co Ltd
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    • 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
    • C07D307/30—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 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
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • 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
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • 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
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

本申请提供一种式III化合物，还提供其用于合成布瓦西坦(Brivaracetam)中间体及原料药中的用途以及合成方法。本申请所述方法涉及的原料廉价易得，可制备出高光学纯度的(R)‑4‑丙基‑二氢呋喃‑2‑酮，避免了繁琐的分离提纯步骤，降低了成本，更加适合于工业生产。

Description

PCT国内申请，说明书已公开。

Claims (40)

  1. PCT国内申请，权利要求书已公开。
CN201980004099.3A 2018-06-22 2019-06-20 化合物及其在合成布瓦西坦(Brivaracetam)中间体及原料药中的用途 Active CN111094260B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN2018106515599 2018-06-22
CN201810651559 2018-06-22
PCT/CN2019/092105 WO2019242692A1 (zh) 2018-06-22 2019-06-20 化合物及其在合成布瓦西坦(Brivaracetam)中间体及原料药中的用途

Publications (2)

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CN111094260A true CN111094260A (zh) 2020-05-01
CN111094260B CN111094260B (zh) 2021-05-11

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US (1) US11247977B2 (zh)
EP (1) EP3798211A4 (zh)
JP (1) JP7117796B2 (zh)
KR (1) KR102544330B1 (zh)
CN (1) CN111094260B (zh)
AU (1) AU2019291703B2 (zh)
CA (1) CA3103332C (zh)
SG (1) SG11202012596YA (zh)
WO (1) WO2019242692A1 (zh)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105646319A (zh) * 2015-12-30 2016-06-08 佛山市隆信医药科技有限公司 一种布瓦西坦的制备方法
CN106279074A (zh) * 2015-05-25 2017-01-04 苏州鹏旭医药科技有限公司 一种化合物及其制备方法和在合成布瓦西坦中的用途
CN106432030A (zh) * 2015-10-10 2017-02-22 苏州鹏旭医药科技有限公司 布瓦西坦的一种制备方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL3302441T3 (pl) 2015-05-25 2024-05-20 Suzhou Pengxu Pharmatech Co. Ltd Sposoby produkcji briwaracetamu
CN105837535A (zh) 2016-04-06 2016-08-10 成都拿盛科技有限公司 一种取代的手性γ-丁内酯的合成方法
CN105801530A (zh) 2016-04-13 2016-07-27 成都拿盛科技有限公司 一种4位取代的手性γ-丁内酯的合成方法
CN106008411A (zh) 2016-05-26 2016-10-12 上海华默西医药科技有限公司 手性4-取代基二氢呋喃-2(3h)-酮的制备方法
CN107652254A (zh) * 2017-11-14 2018-02-02 安徽华胜医药科技有限公司 一种制备丁内酯衍生物的方法
CN109134406A (zh) 2018-08-02 2019-01-04 丽珠集团新北江制药股份有限公司 一种布瓦西坦中间体及布瓦西坦的合成方法
WO2020143674A1 (en) 2019-01-09 2020-07-16 Fujian Haixi Pharmaceuticals Co., Ltd Compounds and their use in the synthesis of brivaracetam apis

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106279074A (zh) * 2015-05-25 2017-01-04 苏州鹏旭医药科技有限公司 一种化合物及其制备方法和在合成布瓦西坦中的用途
CN106432030A (zh) * 2015-10-10 2017-02-22 苏州鹏旭医药科技有限公司 布瓦西坦的一种制备方法
CN105646319A (zh) * 2015-12-30 2016-06-08 佛山市隆信医药科技有限公司 一种布瓦西坦的制备方法

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CARMEN M. RODRÍGUEZ 等: "Stereoselective Synthesis of Highly Substituted γ-Lactones and Butenolides by Intramolecular Michael Addition of Enantiomerically Enriched γ-[(Phenylthio)acyl]oxy α，β-Unsaturated Esters", 《J. ORG. CHEM.》 *
ROBIN，SYLVIE 等: "Microbiological Reduction of Keto-Sulfones. Application in a Three-Step Synthesis of (S)-(+)-β-Angelica Lactone", 《TETRAHEDRON: ASYMMETRY》 *
YUJI KAZUTA 等: "Development of Versatile cis- and trans-Dicarbon-Substituted Chiral Cyclopropane Units: Synthesis of (1S，2R)- and (1R，2R)-2-Aminomethyl-1-(1H-imidazol-4-yl)cyclopropanes and Their Enantiomers as Conformationally Restricted Analogues of Histamine", 《J. ORG. CHEM.》 *

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Publication number Publication date
WO2019242692A1 (zh) 2019-12-26
US20210261515A1 (en) 2021-08-26
EP3798211A4 (en) 2021-09-15
JP7117796B2 (ja) 2022-08-15
KR20210018454A (ko) 2021-02-17
SG11202012596YA (en) 2021-02-25
CA3103332C (en) 2023-03-07
US11247977B2 (en) 2022-02-15
CN111094260B (zh) 2021-05-11
AU2019291703A1 (en) 2021-01-21
KR102544330B1 (ko) 2023-06-20
JP2021528440A (ja) 2021-10-21
CA3103332A1 (en) 2019-12-26
AU2019291703B2 (en) 2021-09-23
EP3798211A1 (en) 2021-03-31

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Address after: 350002 Building 1, No. 20, Jinzhou North Road, Jinshan Industrial Zone, Cangshan District, Fuzhou City, Fujian Province

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Address before: 350002 No. 20 Jinzhou North Road, Jinshan Industrial Zone, Cangshan District, Fujian, Fuzhou

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Patentee before: Kang Xinshan

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Address after: The third and fourth floors of Block B, No. 177 Jinda Road, Jianxin Town, Cangshan District, Fuzhou City, Fujian Province, 350000

Patentee after: Fujian Haixi New Pharmaceutical Co.,Ltd.

Address before: 350002 Building 1, No. 20, Jinzhou North Road, Jinshan Industrial Zone, Cangshan District, Fuzhou City, Fujian Province

Patentee before: FUJIAN HAIXI PHARMACEUTICALS Co.,Ltd.

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