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 |
| CN201510648574.4 | 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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2018523633A JP2018523633A (ja) | 2018-08-23 |
| JP2018523633A5 true JP2018523633A5 (https=) | 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 (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=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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 |
| JP4334344B2 (ja) * | 2001-08-10 | 2009-09-30 | ユセベ ファルマ ソシエテ アノニム | オキソピロリジン化合物、当該化合物の調製、並びにレベチラセタム及び類似体の製造におけるその化合物の使用 |
| 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 |
| WO2007031263A1 (en) * | 2005-09-15 | 2007-03-22 | Ucb Pharma, S.A. | 4-substituted pyrr0lidin-2-0nes and their use |
| JP2009518335A (ja) | 2005-12-07 | 2009-05-07 | ユセベ ファルマ ソシエテ アノニム | ３−カルボキシ−２−オキソ−１−ピロリジン誘導体及びそれらの使用 |
| 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 |
| EP2571352A4 (en) | 2010-05-21 | 2014-09-17 | Sloan Kettering Inst Cancer | SELECTIVE HDAC HEMMER |
| CN103561732A (zh) | 2011-04-11 | 2014-02-05 | 阿克西里亚药品公司 | 治疗化合物 |
| 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 |
| WO2016191435A1 (en) * | 2015-05-25 | 2016-12-01 | Peng Wang | Processes to produce brivaracetam |
| ES2893301T3 (es) | 2015-11-03 | 2022-02-08 | Ucb Biopharma Sprl | Proceso para preparar 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 WO PCT/US2016/033965 patent/WO2016191435A1/en not_active Ceased
- 2016-05-24 EP EP16800643.5A patent/EP3302441B1/en active Active
- 2016-05-24 KR KR1020177037062A patent/KR102630456B1/ko active Active
- 2016-05-24 ES ES16800643T patent/ES2965746T3/es active Active
- 2016-05-24 US US15/575,373 patent/US10221134B2/en active Active
- 2016-05-24 HU HUE16800643A patent/HUE064612T2/hu unknown
- 2016-05-24 JP JP2017561732A patent/JP6872500B2/ja active Active
- 2016-05-24 BR BR112017025266A patent/BR112017025266A2/pt not_active Application Discontinuation
- 2016-05-24 HR HRP20240027TT patent/HRP20240027T1/hr unknown
- 2016-05-24 MX MX2017015133A patent/MX380263B/es unknown
- 2016-05-24 PL PL16800643.5T patent/PL3302441T3/pl unknown
-
2017
- 2017-11-23 IL IL255880A patent/IL255880B/en active IP Right Grant
-
2019
- 2019-01-24 US US16/256,596 patent/US11673862B2/en active Active
- 2019-01-24 US US16/256,522 patent/US12221413B2/en active Active
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