RU2007113811A - Способ получения оптически активных производных амина - Google Patents
Способ получения оптически активных производных амина Download PDFInfo
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- 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
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- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
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- 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
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
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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
- C07D307/77—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
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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Claims (17)
1. Способ получения (S)-2-(1,6,7,8-тетрагидро-2H-индено[5,4-b]фуран-8-ил)этиламина или его соли, который включает стадию (i): стадию асимметрического восстановления (E)-2-(1,6,7,8-тетрагидро-2H-индено[5,4-b]фуран-8-илиден)этиламина или его соли на катализаторе, и стадию (ii): стадию каталитического восстановления реакционного продукта, полученного на стадии (i), при температуре реакции от 40°C до 100°C и pH от 3 до 9 на катализаторе.
2. Способ по п.1, в котором температура реакции на стадии (ii) составляет от 50°C до 70°C.
3. Способ по п.1, в котором pH на стадии (ii) составляет от 5 до 7.
4. Способ по п.1, в котором катализатором на стадии (i) является Ru-BINAF катализатор.
5. Способ по п.1, в котором катализатором на стадии (ii) является Pd-C катализатор.
6. Способ получения кристаллов (S)-N-[2-(1,6,7,8-тетрагидро-2H-индено[5,4-b]фуран-8-ил)этил]пропионамида, включающий стадию (a): стадию пропионилирования аминогруппы (S)-2-(1,6,7,8-тетрагидро-2H-индено[5,4-b]фуран-8-ил)этиламина или его соли, полученного способом по п.1, и стадию (b): стадию кристаллизации путем добавления водного растворителя к реакционному раствору, полученному на стадии (a).
7. Кристаллы (S)-N-[2-(1,6,7,8-тетрагидро-2H-индено[5,4-b]фуран-8-ил)этил]пропионамида, в которых содержание каждого из соединений, представленных следующими формулами (I), (II), (III) и (IV), составляет 0,15% по массе или менее, и суммарное содержание соединений, представленных следующими формулами (I) -(IV), составляет 0,2% по массе или менее.
8. Кристаллы (S)-N-[2-(1,6,7,8-тетрагидро-2H-индено[5,4-b]фуран-8-ил)этил]пропионамида, в которых содержание каждого из соединений, представленных следующими формулами (I), (II), (III) и (IV), составляет 0,15% по массе или менее, и содержание соединения, представленного следующей формулой (II), составляет от 0,02 до 0,15% по массе, и, кроме того, суммарное содержание соединений, представленных следующими формулами (I)-(IV), составляет 0,2% по массе или менее.
М
9. Кристаллы по пп. 7 и 8, в которых содержание соединения, представленного формулой (I), составляет 0,10% по массе или менее.
10. Композиция, включающая (S)-N-[2-(1,6,7,8-тетрагидро-2H-индено[5,4-b]фуран-8-ил)этил]пропионамид и соединения, представленные следующими формулами (I), (II), (III) и (IV), в которой относительно 100 частей по массе (S)-N-[2-(i,6,7,8-тетрагидро-2H-индено[5,4-b]фуран-8-ил)этил]пропионамида, содержание каждого из соединений, представленных следующими формулами (I), (II), (III) и (IV), составляет от 0 до 0,15 частей по массе, и суммарное содержание соединений, представленных следующими формулами (I)-(IV), составляет от 0 до 0,2 частей по массе.
11. Композиция, включающая (S)-N-[2-(1,6,7,8-тетрагидро-2H-индено[5,4-b]фуран-8-ил)этил]пропионамид и соединения, представленные следующими формулами (I), (II), (III) и (IV), в которой относительно 100 частей по массе (S)-N-[2-(1,6,7,8-тетрагидро-2H-индено[5,4-b]фуран-8-ил)этил]пропионамида, содержание каждого из соединений, представленных следующими формулами (I), (III) и (IV), составляет от 0 до 0,15 частей по массе, и содержание соединения, представленного следующей формулой (II), составляет от 0,02 до 0,15 частей по массе, и дополнительно суммарное содержание соединений, представленных следующими формулами (I)-(IV), составляет от 0 до 0,2 частей по массе.
12. Композиция по пп.10 и 11, в которой содержание соединения, представленного формулой (I), составляет от 0 до 0,10 частей по массе относительно 100 частей по массе (S)-N-[2-(1,6,7,8-тетрагидро-2H-индено[5,4-b]фуран-8-ил) этил]пропионамида.
13. Кристаллы по п.7 или композиция по п.10, которую получают в промышленном масштабе.
14. Способ получения 1,2,6,7-тетрагидро-8H-индена[5,4-b]фуран-8-она, включающий стадию восстановления 4,5-дибром-1,2,6,7-тетрагидро-8H-индено[5,4-b]фуран-8-она на Pd-C катализаторе при условии:
давление водорода (МПа)>-0,02·суммарный объемный коэффициент массопередачи газ-жидкость (1/ч)+0,43.
15. Применение кристаллов по п.7 для получения профилактического или терапевтического средства при нарушении сна.
16. Композиция по п.10, которая является профилактическим или терапевтическим средством при нарушении сна.
17. Способ предотвращения или лечения нарушения сна, включающий введение кристаллов по п.8 или композиции по п.10.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004265307 | 2004-09-13 | ||
| JP2004-265307 | 2004-09-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2007113811A true RU2007113811A (ru) | 2008-10-20 |
| RU2385318C2 RU2385318C2 (ru) | 2010-03-27 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007113811/04A RU2385318C2 (ru) | 2004-09-13 | 2005-09-12 | Способ получения оптически активных производных амина |
Country Status (31)
| Country | Link |
|---|---|
| US (4) | US8097737B2 (ru) |
| EP (2) | EP2537842A1 (ru) |
| JP (2) | JP5127228B2 (ru) |
| KR (1) | KR101298335B1 (ru) |
| CN (2) | CN102516211A (ru) |
| AR (1) | AR050737A1 (ru) |
| AU (1) | AU2005283521B2 (ru) |
| BR (1) | BRPI0515170A (ru) |
| CA (2) | CA2579121C (ru) |
| CR (2) | CR8975A (ru) |
| EC (1) | ECSP077317A (ru) |
| ES (1) | ES2485890T3 (ru) |
| GE (1) | GEP20094725B (ru) |
| GT (2) | GT200500257AA (ru) |
| HN (1) | HN2005000548A (ru) |
| IL (2) | IL181462A (ru) |
| MA (1) | MA28855B1 (ru) |
| MX (1) | MX2007002822A (ru) |
| MY (2) | MY147822A (ru) |
| NO (1) | NO20071866L (ru) |
| NZ (1) | NZ553562A (ru) |
| PA (1) | PA8645701A1 (ru) |
| PE (3) | PE20060662A1 (ru) |
| RU (1) | RU2385318C2 (ru) |
| SA (1) | SA05260347A (ru) |
| SG (1) | SG151330A1 (ru) |
| TW (1) | TWI400220B (ru) |
| UA (1) | UA95598C2 (ru) |
| UY (1) | UY29118A1 (ru) |
| WO (1) | WO2006030739A1 (ru) |
| ZA (1) | ZA200701724B (ru) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5450056B2 (ja) * | 2007-03-19 | 2014-03-26 | 武田薬品工業株式会社 | アリルアミン不斉水素化法 |
| WO2008150953A1 (en) * | 2007-05-30 | 2008-12-11 | Dr. Reddy's Laboratories Ltd. | Process of making ramelteon and related substances |
| WO2008151170A2 (en) * | 2007-05-31 | 2008-12-11 | Teva Pharmaceutical Industries Ltd. | Process for the synthesis of ramelteon and its intermediates |
| WO2009060318A2 (en) * | 2007-07-12 | 2009-05-14 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of ramelteon and processes for preparation thereof |
| CN101531647B (zh) * | 2008-03-13 | 2012-10-31 | 常州亚邦制药有限公司 | (±)-2-(1,6,7,8-四氢-2H-茚并[5,4-b]呋喃-8-基)乙胺的拆分方法 |
| JP2011528012A (ja) * | 2008-07-14 | 2011-11-10 | レツク・フアーマシユーテイカルズ・デー・デー | ラメルテオンの調製における中間体としての６，７−ジヒドロ−１ｈ−インデノ［５，４−ｂ］フラン−８（２ｈ）−オンの合成 |
| US20100152468A1 (en) * | 2008-10-16 | 2010-06-17 | Teva Pharmaceutical Industries Ltd. | Process for the synthesis of ramelteon and its intermediates |
| EP2396309A1 (en) | 2009-02-12 | 2011-12-21 | LEK Pharmaceuticals d.d. | Synthesis of (s)-n-ý2-(1,6,7,8-tetrahydro-2h-indeno-ý5,4-b¨furan-8-yl)ethyl¨propionamide |
| CN101824012B (zh) * | 2009-03-02 | 2011-12-07 | 四川大学 | 2-(1,6,7,8-四氢-2H-茚并-[5,4-b]呋喃-8-基)乙腈及其制备方法和用途 |
| WO2010103553A1 (en) | 2009-03-10 | 2010-09-16 | Industriale Chimica S.R.L. | Process for the preparation of ramelteon |
| EP2243775A1 (en) | 2009-04-07 | 2010-10-27 | LEK Pharmaceuticals d.d. | Synthesis of 1-(2,3-Dihydrobenzofuran-4-YL)ethanone as intermediate in the preparation of ramelteon |
| WO2011027323A1 (en) | 2009-09-03 | 2011-03-10 | Ranbaxy Laboratories Limited | Process for the preparation of ramelteon |
| WO2011027319A1 (en) | 2009-09-03 | 2011-03-10 | Ranbaxy Laboratories Limited | Process for the preparation of an intermediate for ramelteon |
| CN101665477B (zh) * | 2009-09-21 | 2012-05-09 | 四川大学 | (e)-3-(苯并呋喃-5-基)丙烯酸酯类化合物、其制备方法和用途 |
| CN101648931B (zh) * | 2009-09-21 | 2012-05-09 | 四川大学 | 一种3-(2,3-二氢苯并呋喃-5-基)-丙酸的制备方法 |
| EP2483258A1 (en) | 2009-09-29 | 2012-08-08 | Lonza Ltd. | Process for preparing 1,2,6,7-tetrahydro-8h-indeno[5,4-b]furan-8-one |
| WO2012035303A2 (en) | 2010-09-17 | 2012-03-22 | Cipla Limited Et Al | A novel process for synthesis of ramelteon, and key intermediates for the synthesis of ramelteon |
| CN103664849B (zh) * | 2012-08-31 | 2017-03-29 | 上海阳帆医药科技有限公司 | 制备2‑(1,6,7,8‑四氢‑2H‑茚并[5,4‑b]呋喃‑8‑亚基乙胺的方法 |
| CN102924410A (zh) * | 2012-10-29 | 2013-02-13 | 华润赛科药业有限责任公司 | 一种雷美替胺的制备方法及其中间体 |
| CN103396387A (zh) * | 2013-08-07 | 2013-11-20 | 安徽联创药物化学有限公司 | 雷美替胺中间体的制备方法 |
| CN105277628B (zh) * | 2014-07-07 | 2017-05-31 | 南京长澳医药科技有限公司 | 通过高效液相色谱法分离测定雷美替胺及其杂质的方法 |
| CN104402848B (zh) * | 2014-09-22 | 2017-02-08 | 珠海联邦制药股份有限公司 | 雷美替胺中的杂质化合物的制备方法及制备的标准品 |
| CN105622557B (zh) * | 2014-11-05 | 2018-12-04 | 上海医药工业研究院 | 雷美替胺中间体及其制备方法 |
| KR102359229B1 (ko) | 2020-04-16 | 2022-02-07 | 제이투에이치바이오텍 (주) | 라멜테온의 제조 방법 및 이러한 제조 방법에 이용되는 중간체 화합물 |
| CN115477628A (zh) * | 2022-10-17 | 2022-12-16 | 江苏海悦康医药科技有限公司 | 一种雷美替胺二聚体的合成方法 |
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| JPH0757758B2 (ja) | 1988-10-24 | 1995-06-21 | 高砂香料工業株式会社 | ルテニウム―ホスフィン錯体 |
| US6060503A (en) | 1991-12-02 | 2000-05-09 | Endorecherche, Inc. | Benzopyran-containing compounds and method for their use |
| PT812835E (pt) | 1995-03-02 | 2001-08-30 | Sankyo Co | Derivados opticamente activos de tiazolidinona |
| EP1199304A1 (en) * | 1997-03-05 | 2002-04-24 | Takeda Chemical Industries, Ltd. | Bicyclic compounds and pharmaceutical composition containing tricyclic compound for treating or preventing sleep disorders |
| US6034239A (en) * | 1996-03-08 | 2000-03-07 | Takeda Chemical Industries, Ltd. | Tricyclic compounds, their production and use |
| JP2884153B2 (ja) | 1996-03-08 | 1999-04-19 | 武田薬品工業株式会社 | 三環性化合物、その製造法および剤 |
| JP4242940B2 (ja) | 1997-02-13 | 2009-03-25 | 高砂香料工業株式会社 | 光学活性アミン誘導体の製造法 |
| JP4081161B2 (ja) * | 1997-09-05 | 2008-04-23 | 武田薬品工業株式会社 | 光学活性化合物の製造法 |
| JP3509637B2 (ja) * | 1998-06-09 | 2004-03-22 | 武田薬品工業株式会社 | 睡眠障害予防治療剤 |
| CA2332521C (en) * | 1998-06-09 | 2009-02-10 | Takeda Chemical Industries, Ltd. | Pharmaceutical composition for treating or preventing sleep disorders |
| CA2650698C (en) * | 2000-11-17 | 2013-05-28 | Takeda Pharmaceutical Company Limited | Copolyvidone-containing preparation |
| JP3633895B2 (ja) * | 2000-11-17 | 2005-03-30 | 武田薬品工業株式会社 | コポリビドン含有製剤 |
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