JP2018523633A5 - - Google Patents
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- JP2018523633A5 JP2018523633A5 JP2017561732A JP2017561732A JP2018523633A5 JP 2018523633 A5 JP2018523633 A5 JP 2018523633A5 JP 2017561732 A JP2017561732 A JP 2017561732A JP 2017561732 A JP2017561732 A JP 2017561732A JP 2018523633 A5 JP2018523633 A5 JP 2018523633A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- xii
- alkyl
- brivaracetam
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 78
- 238000002360 preparation method Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 14
- -1 alkyl (S) -2-aminobutanoate Chemical compound 0.000 claims description 9
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims description 3
- 238000010640 amide synthesis reaction Methods 0.000 claims description 3
- 238000007098 aminolysis reaction Methods 0.000 claims description 3
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 17
- MSYKRHVOOPPJKU-BDAKNGLRSA-N brivaracetam Chemical compound CCC[C@H]1CN([C@@H](CC)C(N)=O)C(=O)C1 MSYKRHVOOPPJKU-BDAKNGLRSA-N 0.000 claims 9
- 229960002161 brivaracetam Drugs 0.000 claims 9
- 229920006395 saturated elastomer Polymers 0.000 claims 8
- HNNJFUDLLWOVKZ-VKHMYHEASA-N (2s)-2-aminobutanamide Chemical compound CC[C@H](N)C(N)=O HNNJFUDLLWOVKZ-VKHMYHEASA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000003107 substituted aryl group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000011968 lewis acid catalyst Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Substances C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 claims 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 15
- NVTUTJMZAZZKAZ-ZCFIWIBFSA-N (4r)-4-propyloxolan-2-one Chemical compound CCC[C@H]1COC(=O)C1 NVTUTJMZAZZKAZ-ZCFIWIBFSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- UQDYDAFRKKAVQO-ZOCYIJKUSA-N (2R)-3-[[[(2S)-1-amino-1-oxobutan-2-yl]amino]methyl]-2-ethylhexanoic acid Chemical compound CCCC([C@@H](CC)C(O)=O)CN[C@@H](CC)C(N)=O UQDYDAFRKKAVQO-ZOCYIJKUSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- IIRSUSYXTYJBDQ-BRFYHDHCSA-N (2R)-3-(bromomethyl)-2-ethylhexanoic acid Chemical compound CCCC(CBr)[C@@H](CC)C(=O)O IIRSUSYXTYJBDQ-BRFYHDHCSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- HZVJPBPAJMKQEC-JAMMHHFISA-N ethyl (4R)-2-oxo-4-propyloxolane-3-carboxylate Chemical compound C(CC)[C@@H]1C(C(OC1)=O)C(=O)OCC HZVJPBPAJMKQEC-JAMMHHFISA-N 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- HDBMIDJFXOYCGK-DFWYDOINSA-N (2s)-2-aminobutanamide;hydrochloride Chemical compound Cl.CC[C@H](N)C(N)=O HDBMIDJFXOYCGK-DFWYDOINSA-N 0.000 description 1
- NYIXDCWAFHWQTI-ZCFIWIBFSA-N (3R)-3-(chloromethyl)hexanoyl chloride Chemical compound ClC[C@@H](CC(=O)Cl)CCC NYIXDCWAFHWQTI-ZCFIWIBFSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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 |
| CN201510648574.4A CN106432030B (zh) | 2015-10-10 | 2015-10-10 | 布瓦西坦的一种制备方法 |
| CN201510648574.4 | 2015-10-10 | ||
| 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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2018523633A JP2018523633A (ja) | 2018-08-23 |
| JP2018523633A5 true JP2018523633A5 (enExample) | 2019-06-27 |
| JP6872500B2 JP6872500B2 (ja) | 2021-05-19 |
Family
ID=57394289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017561732A Active JP6872500B2 (ja) | 2015-05-25 | 2016-05-24 | ブリバラセタムを製造する方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US10221134B2 (enExample) |
| EP (1) | EP3302441B1 (enExample) |
| JP (1) | JP6872500B2 (enExample) |
| KR (1) | KR102630456B1 (enExample) |
| BR (1) | BR112017025266A2 (enExample) |
| ES (1) | ES2965746T3 (enExample) |
| HR (1) | HRP20240027T1 (enExample) |
| HU (1) | HUE064612T2 (enExample) |
| IL (1) | IL255880B (enExample) |
| MX (1) | MX380263B (enExample) |
| PL (1) | PL3302441T3 (enExample) |
| WO (1) | WO2016191435A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20240027T1 (hr) * | 2015-05-25 | 2024-04-26 | Suzhou Pengxu Pharmatech Co., Ltd. | Postupci za proizvodnju brivaracetama |
| 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 |
| WO2019242692A1 (zh) | 2018-06-22 | 2019-12-26 | 福建海西新药创制有限公司 | 化合物及其在合成布瓦西坦(Brivaracetam)中间体及原料药中的用途 |
| WO2020148787A1 (en) * | 2019-01-17 | 2020-07-23 | 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 |
| ES3032398T3 (en) * | 2020-12-14 | 2025-07-18 | Alivus Life Sciences Ltd | 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 |
| WO2023021363A1 (en) * | 2021-08-16 | 2023-02-23 | 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 |
| 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 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0004297D0 (en) | 2000-02-23 | 2000-04-12 | Ucb Sa | 2-oxo-1 pyrrolidine derivatives process for preparing them and their uses |
| WO2003014080A2 (en) * | 2001-08-10 | 2003-02-20 | Ucb, S.A. | Oxopyrrolidine compounds, preparation of said compounds and their use in the manufacturing of levetiracetam and analogues |
| KR101124098B1 (ko) | 2003-09-24 | 2012-03-21 | 유씨비 파마, 에스.에이. | 2-옥소-1-피롤리딘 유도체를 제조하는 방법 |
| TW200724139A (en) * | 2005-05-05 | 2007-07-01 | Warner Lambert Co | Androgen modulators |
| BRPI0615830A2 (pt) | 2005-09-15 | 2012-12-18 | Ucb Pharma Sa | composto, processos para a preparação de derivados de 2-oxo-pirrolidin-1-ila, para preparação dos compostos de modo substancial diastereoisomericamente puros, para a preparação de brivaracetam e para a preparação de seletracetam, e, uso de 4-substituìdo-pirrolidin-2-onas |
| CA2632453A1 (en) | 2005-12-07 | 2007-06-14 | Ucb Pharma, S.A. | 3-carboxy- 2-oxo-1 -pyrrolidine derivatives and their uses |
| US8338621B2 (en) * | 2005-12-21 | 2012-12-25 | Ucb S.A. | Process for the preparation of 2-oxo-1-pyrrolidine derivatives |
| KR20070081959A (ko) | 2006-02-14 | 2007-08-20 | (주)지앤테크 | 은이 포함된 정수기용 필터 |
| KR100846419B1 (ko) | 2007-08-10 | 2008-07-15 | 한국과학기술원 | 프레가발린의 신규한 제조 방법 |
| KR100915671B1 (ko) * | 2007-08-14 | 2009-09-04 | 한국과학기술원 | 치환된 γ-부티로락톤의 광학선택적 제조방법 |
| US20120021469A1 (en) * | 2009-03-27 | 2012-01-26 | Codexis, Inc. | Amidases and methods of their use |
| AU2011255281A1 (en) | 2010-05-21 | 2013-01-10 | Sloan-Kettering Institute For Cancer Research | Selective HDAC inhibitors |
| RU2013150118A (ru) * | 2011-04-11 | 2015-05-20 | Ахтелиа Фармасьютикалз | Терапевтические соединения |
| US20140228579A1 (en) * | 2013-02-14 | 2014-08-14 | Brock Unviersity | Method for the catalytic reduction of acid chlorides and imidoyl chlorides |
| CN103819389A (zh) * | 2014-02-17 | 2014-05-28 | 北京博泽德润医药科技开发有限公司 | 一种左乙拉西坦制备方法 |
| HRP20240027T1 (hr) | 2015-05-25 | 2024-04-26 | Suzhou Pengxu Pharmatech Co., Ltd. | Postupci za proizvodnju brivaracetama |
| DK3371150T3 (en) | 2015-11-03 | 2021-11-15 | UCB Biopharma SRL | Fremgangsmåde til at fremstille brivaracetam |
| 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 |
| WO2020148731A1 (en) | 2019-01-19 | 2020-07-23 | Stereokem Pvt. Ltd. | Process for preparation of brivaracetam intermediates and use thereof |
-
2016
- 2016-05-24 HR HRP20240027TT patent/HRP20240027T1/hr unknown
- 2016-05-24 ES ES16800643T patent/ES2965746T3/es active Active
- 2016-05-24 KR KR1020177037062A patent/KR102630456B1/ko active Active
- 2016-05-24 EP EP16800643.5A patent/EP3302441B1/en active Active
- 2016-05-24 WO PCT/US2016/033965 patent/WO2016191435A1/en not_active Ceased
- 2016-05-24 JP JP2017561732A patent/JP6872500B2/ja active Active
- 2016-05-24 PL PL16800643.5T patent/PL3302441T3/pl unknown
- 2016-05-24 HU HUE16800643A patent/HUE064612T2/hu unknown
- 2016-05-24 MX MX2017015133A patent/MX380263B/es unknown
- 2016-05-24 US US15/575,373 patent/US10221134B2/en active Active
- 2016-05-24 BR BR112017025266A patent/BR112017025266A2/pt not_active Application Discontinuation
-
2017
- 2017-11-23 IL IL255880A patent/IL255880B/en active IP Right Grant
-
2019
- 2019-01-24 US US16/256,522 patent/US12221413B2/en active Active
- 2019-01-24 US US16/256,596 patent/US11673862B2/en active Active
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