KR102630456B1 - 브리바라세탐의 제조 방법 - Google Patents

브리바라세탐의 제조 방법 Download PDF

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KR102630456B1
KR102630456B1 KR1020177037062A KR20177037062A KR102630456B1 KR 102630456 B1 KR102630456 B1 KR 102630456B1 KR 1020177037062 A KR1020177037062 A KR 1020177037062A KR 20177037062 A KR20177037062 A KR 20177037062A KR 102630456 B1 KR102630456 B1 KR 102630456B1
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compound
formula
xii
brivaracetam
alkyl
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KR20180012788A (ko
Inventor
펑 왕
피슈 리
치앙 웨이
위안화 리우
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쑤저우 펭슈 파마테크 씨오., 엘티디.
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Priority claimed from CN201510271449.6A external-priority patent/CN106279074B/zh
Priority claimed from CN201510430387.9A external-priority patent/CN106365986B/zh
Priority claimed from CN201510648574.4A external-priority patent/CN106432030B/zh
Application filed by 쑤저우 펭슈 파마테크 씨오., 엘티디. filed Critical 쑤저우 펭슈 파마테크 씨오., 엘티디.
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    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
    • C07C53/19—Acids containing three or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/38—Acyl halides
    • C07C53/46—Acyl halides containing halogen outside the carbonyl halide group
    • C07C53/50—Acyl halides containing halogen outside the carbonyl halide group of acids containing three or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/63—Halogen-containing esters of saturated acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C71/00—Esters of oxyacids of halogens

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrrole Compounds (AREA)
KR1020177037062A 2015-05-25 2016-05-24 브리바라세탐의 제조 방법 Active KR102630456B1 (ko)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
CN201510271449.6 2015-05-25
CN201510271449.6A CN106279074B (zh) 2015-05-25 2015-05-25 一种化合物及其制备方法和在合成布瓦西坦中的用途
CN201510430387.9 2015-07-21
CN201510430387.9A CN106365986B (zh) 2015-07-21 2015-07-21 化合物及其制备方法和在合成布瓦西坦中的用途
CN201510648574.4 2015-10-10
CN201510648574.4A CN106432030B (zh) 2015-10-10 2015-10-10 布瓦西坦的一种制备方法
CN201610099672.1 2016-02-24
CN201610099672 2016-02-24
PCT/US2016/033965 WO2016191435A1 (en) 2015-05-25 2016-05-24 Processes to produce brivaracetam

Publications (2)

Publication Number Publication Date
KR20180012788A KR20180012788A (ko) 2018-02-06
KR102630456B1 true KR102630456B1 (ko) 2024-01-29

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Country Status (12)

Country Link
US (3) US10221134B2 (https=)
EP (1) EP3302441B1 (https=)
JP (1) JP6872500B2 (https=)
KR (1) KR102630456B1 (https=)
BR (1) BR112017025266A2 (https=)
ES (1) ES2965746T3 (https=)
HR (1) HRP20240027T1 (https=)
HU (1) HUE064612T2 (https=)
IL (1) IL255880B (https=)
MX (1) MX380263B (https=)
PL (1) PL3302441T3 (https=)
WO (1) WO2016191435A1 (https=)

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WO2016191435A1 (en) 2015-05-25 2016-12-01 Peng Wang Processes to produce brivaracetam
CN107056643A (zh) * 2017-03-01 2017-08-18 苏州鹏旭医药科技有限公司 一种化合物的晶型a及其制备纯化方法
WO2018141276A1 (zh) * 2017-02-05 2018-08-09 苏州鹏旭医药科技有限公司 布瓦西坦中间体的晶型a及其制备方法和布瓦西坦的晶型c及其制备方法
CN108503609B (zh) * 2017-02-24 2019-12-24 北京艾百诺医药股份有限公司 一种制备光学纯的(r)-4-正丙基-二氢呋喃-2(3h)-酮的方法
CN108503573B (zh) * 2017-02-24 2019-11-22 北京艾百诺医药股份有限公司 一种布瓦西坦的新的制备方法
CN108689903B (zh) * 2017-04-06 2019-12-24 北京艾百诺医药股份有限公司 一种布瓦西坦的新的制备方法
US20210163410A1 (en) * 2017-05-29 2021-06-03 Msn Laboratories Private Limited, R&D Center An improved process for the preparation of (2s)-2-[(4r)-2-oxo-4-propyltetrahydro-1h-pyrrol-1-yl] butanamide and its intermediates thereof
WO2019087172A1 (en) * 2017-12-19 2019-05-09 Glenmark Pharmaceuticals Limited Process for preparation of brivaracetam
CN108409557A (zh) * 2018-05-17 2018-08-17 丽珠集团新北江制药股份有限公司 布瓦西坦新中间体及其合成方法和应用
IT201800006320A1 (it) * 2018-06-14 2019-12-14 Processo per la sintesi asimmetrica di (r)-4-propildiidrofuran-2(3h)-one
CN110615744B (zh) 2018-06-20 2023-01-06 上海朴颐化学科技有限公司 一种布瓦西坦中间体及其制备方法
US11247977B2 (en) 2018-06-22 2022-02-15 Fujian Haixi Pharmaceuticals Co., Ltd. Compound and use thereof in synthesis of brivaracetam intermediate and crude drug
US20220064111A1 (en) * 2019-01-17 2022-03-03 Clininvent Research Pvt. Ltd. Enantioselective synthesis of brivaracetam and intermediates thereof
CN112110843A (zh) * 2019-06-20 2020-12-22 北京万全德众医药生物技术有限公司 一种布瓦西坦的新制备方法
WO2021260721A1 (en) * 2020-06-23 2021-12-30 Clininvent Research Pvt. Ltd. A new cost effective and scalable process for synthesizing pure brivaracetam
EP4077278B1 (en) 2020-12-14 2025-03-12 Alivus Life Sciences Limited Process for the preparation of brivaracetam
US11400074B1 (en) * 2021-02-01 2022-08-02 Divi's Laboratories Ltd. Enzymatic process for the preparation of (2S)-2-[(4R)-2-oxo-4-propyl-pyrrolidin-1-yl]butyric acid and its conversion into brivaracetam
US20240343689A1 (en) * 2021-08-16 2024-10-17 Optimus Drugs Private Limited Synthesis of brivaracetam
CN114634437B (zh) * 2022-03-29 2023-05-30 武汉氟本氘合新材料科技有限公司 一种布瓦西坦的简易制备方法
US11884623B2 (en) * 2022-05-23 2024-01-30 Divi's Laboratories Ltd. Process for the preparation of (R)-4-propyl pyrrolidine-2-one, a key intermediate for synthesis of brivaracetam
CN114989061A (zh) * 2022-08-03 2022-09-02 江苏同禾药业有限公司 一种布瓦西坦的制备方法
CN115466233B (zh) * 2022-09-28 2024-08-23 合肥立方制药股份有限公司 一种布瓦西坦中间体（r）-4-丙基-二氢呋喃-2-酮的合成方法

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Publication number Publication date
JP2018523633A (ja) 2018-08-23
CA2984832A1 (en) 2016-12-01
WO2016191435A1 (en) 2016-12-01
EP3302441B1 (en) 2023-12-13
IL255880B (en) 2021-02-28
EP3302441C0 (en) 2023-12-13
MX2017015133A (es) 2018-08-01
IL255880A (en) 2018-01-31
JP6872500B2 (ja) 2021-05-19
US20190152908A1 (en) 2019-05-23
BR112017025266A2 (pt) 2018-08-07
US10221134B2 (en) 2019-03-05
US12221413B2 (en) 2025-02-11
EP3302441A1 (en) 2018-04-11
US20180155284A1 (en) 2018-06-07
PL3302441T3 (pl) 2024-05-20
US20190152909A1 (en) 2019-05-23
KR20180012788A (ko) 2018-02-06
MX380263B (es) 2025-03-12
HRP20240027T1 (hr) 2024-04-26
ES2965746T3 (es) 2024-04-16
US20240199541A9 (en) 2024-06-20
HUE064612T2 (hu) 2024-04-28
US11673862B2 (en) 2023-06-13
EP3302441A4 (en) 2019-01-09

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