JP2018517768A5 - - Google Patents
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- Publication number
- JP2018517768A5 JP2018517768A5 JP2018513721A JP2018513721A JP2018517768A5 JP 2018517768 A5 JP2018517768 A5 JP 2018517768A5 JP 2018513721 A JP2018513721 A JP 2018513721A JP 2018513721 A JP2018513721 A JP 2018513721A JP 2018517768 A5 JP2018517768 A5 JP 2018517768A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- mixture
- production method
- optically active
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 20
- 238000004519 manufacturing process Methods 0.000 claims 14
- 238000000034 method Methods 0.000 claims 11
- 239000000203 mixture Substances 0.000 claims 10
- -1 heterocyclic aldehyde compound Chemical class 0.000 claims 9
- 150000001412 amines Chemical class 0.000 claims 8
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical group CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 4
- 230000009466 transformation Effects 0.000 claims 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims 2
- OXOBKZZXZVFOBB-MRXNPFEDSA-N (2r)-2-benzhydrylpyrrolidine Chemical compound C1CCN[C@H]1C(C=1C=CC=CC=1)C1=CC=CC=C1 OXOBKZZXZVFOBB-MRXNPFEDSA-N 0.000 claims 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims 1
- CQZXDIHVSPZIGF-UHFFFAOYSA-N 1-methylimidazole-4-carbaldehyde Chemical compound CN1C=NC(C=O)=C1 CQZXDIHVSPZIGF-UHFFFAOYSA-N 0.000 claims 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims 1
- BNYKZFOZWZMEJD-UHFFFAOYSA-N 3-methylimidazole-4-carbaldehyde Chemical compound CN1C=NC=C1C=O BNYKZFOZWZMEJD-UHFFFAOYSA-N 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 1
- 229910000160 potassium phosphate Inorganic materials 0.000 claims 1
- 235000011009 potassium phosphates Nutrition 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 claims 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562167232P | 2015-05-27 | 2015-05-27 | |
| US62/167,232 | 2015-05-27 | ||
| PCT/EP2016/052176 WO2016146299A1 (en) | 2015-05-27 | 2016-02-02 | Separation of enantiomers of 3-ethylbicyclo[3.2.0]hept-3-en-6-one |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018517768A JP2018517768A (ja) | 2018-07-05 |
| JP2018517768A5 true JP2018517768A5 (https=) | 2019-03-14 |
| JP6775009B2 JP6775009B2 (ja) | 2020-10-28 |
Family
ID=55404679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018513721A Active JP6775009B2 (ja) | 2015-05-27 | 2016-02-02 | ３−ビシクロ［３．２．０］ヘプ−３−エン−６オンエンの鏡像異性体の分離 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10150723B2 (https=) |
| EP (1) | EP3303308B1 (https=) |
| JP (1) | JP6775009B2 (https=) |
| KR (1) | KR102598202B1 (https=) |
| CN (1) | CN107667097B (https=) |
| AU (1) | AU2016232606A1 (https=) |
| BR (1) | BR112017025135B1 (https=) |
| CA (1) | CA2986954C (https=) |
| RU (1) | RU2734475C2 (https=) |
| WO (1) | WO2016146299A1 (https=) |
| ZA (1) | ZA201708769B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114264751B (zh) * | 2021-12-28 | 2024-02-27 | 江苏威凯尔医药科技有限公司 | 一种高效液相色谱法分离米洛巴林中间体及其对映异构体的方法 |
| CN115745764B (zh) * | 2022-12-08 | 2024-03-12 | 重庆华森制药股份有限公司 | 一种米洛巴林中间体的制备方法 |
| WO2024134671A1 (en) * | 2022-12-21 | 2024-06-27 | Bhisaj Pharmaceuticals Pvt Ltd | Preparation of 3-ethylbicyclo[3.2.0]hept-3-en-6-one |
| CN116903468B (zh) * | 2023-07-14 | 2024-01-26 | 山东新时代药业有限公司 | 一种米洛巴林中间体的制备方法 |
| CN117886708A (zh) * | 2023-12-05 | 2024-04-16 | 浙江天宇药业股份有限公司 | 一种苯磺酸米洛巴林的合成方法 |
| CN117924061B (zh) * | 2024-01-17 | 2026-03-20 | 北京海步医药科技有限公司 | 一种3-烷基双环[3.2.0]庚-3-烯-6-酮的拆分方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU147182A1 (ru) * | 1961-07-18 | 1961-11-30 | Е.С. Жданович | Способ расщеплени синтетического рацемического альфа-окси-бета1-бета-диметил-гамма-бутиролактона |
| EP0074856A3 (en) * | 1981-09-16 | 1984-02-01 | Glaxo Group Limited | Resolution of racemic bicycloheptenones |
| WO2010084798A1 (ja) * | 2009-01-21 | 2010-07-29 | 第一三共株式会社 | ３環性化合物 |
| JP5557292B2 (ja) | 2009-03-26 | 2014-07-23 | 第一三共株式会社 | 二環性γ−アミノ酸誘導体の製造方法 |
| HUE035366T2 (en) | 2011-06-08 | 2018-05-02 | Daiichi Sankyo Co Ltd | A method for the preparation of a bicyclic compound by Claisen rearrangement |
| ES2659162T3 (es) * | 2011-06-08 | 2018-03-14 | Daiichi Sankyo Company, Limited | Procedimiento de producción de compuesto bicíclico a través de una sal de iminio |
| KR101944575B1 (ko) * | 2011-12-15 | 2019-04-17 | 다이이찌 산쿄 가부시키가이샤 | 부제 촉매를 사용하는 2고리형 화합물의 광학 분할 방법 |
| WO2013089189A1 (ja) * | 2011-12-16 | 2013-06-20 | 第一三共株式会社 | ヒドロキシスルホン酸を経由する二環性化合物の光学分割方法 |
| EP2837689B1 (en) * | 2012-04-10 | 2017-02-15 | Daiichi Sankyo Company, Limited | Optical resolution method for bicyclic compound using enzyme |
| JP2013245215A (ja) * | 2012-05-29 | 2013-12-09 | Daiichi Sankyo Co Ltd | 不斉環化反応による光学活性二環性化合物の製造方法 |
| JP6491213B2 (ja) * | 2013-12-18 | 2019-03-27 | ノヴァッセイ エスエー | 疼痛および他の障害の治療のためのガンマ−アミノ酪酸（ｇａｂａ）類似体 |
-
2016
- 2016-02-02 CN CN201680030795.8A patent/CN107667097B/zh not_active Expired - Fee Related
- 2016-02-02 US US15/576,720 patent/US10150723B2/en not_active Expired - Fee Related
- 2016-02-02 WO PCT/EP2016/052176 patent/WO2016146299A1/en not_active Ceased
- 2016-02-02 EP EP16705440.2A patent/EP3303308B1/en active Active
- 2016-02-02 RU RU2017143338A patent/RU2734475C2/ru active
- 2016-02-02 JP JP2018513721A patent/JP6775009B2/ja active Active
- 2016-02-02 AU AU2016232606A patent/AU2016232606A1/en not_active Abandoned
- 2016-02-02 KR KR1020177037104A patent/KR102598202B1/ko active Active
- 2016-02-02 CA CA2986954A patent/CA2986954C/en active Active
- 2016-02-02 BR BR112017025135-3A patent/BR112017025135B1/pt not_active IP Right Cessation
-
2017
- 2017-12-21 ZA ZA2017/08769A patent/ZA201708769B/en unknown
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