RU2004120284A - Способы получения o-дезметилвенлафаксина - Google Patents
Способы получения o-дезметилвенлафаксина Download PDFInfo
- Publication number
- RU2004120284A RU2004120284A RU2004120284/04A RU2004120284A RU2004120284A RU 2004120284 A RU2004120284 A RU 2004120284A RU 2004120284/04 A RU2004120284/04 A RU 2004120284/04A RU 2004120284 A RU2004120284 A RU 2004120284A RU 2004120284 A RU2004120284 A RU 2004120284A
- Authority
- RU
- Russia
- Prior art keywords
- thiolate
- anion
- carried out
- alcohol
- reaction
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- 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
- A61P25/06—Antimigraine agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (21)
1. Способ получения O-дезметилвенлафаксина, который включает деметилирование венлафаксина анионом тиолата высокомолекулярного алкана, арилалкила или арена в спиртовом или простом эфирном растворителе или их смеси.
2. Способ по п.1, который проводят в спирте, этиленгликоле, простом эфире этиленгликоля или их смеси.
3. Способ по п.1, где растворителем является моноэтиловый эфир этиленгликоля, диметиловый эфир триэтиленгликоля или полиэтиленгликоль.
4. Способ по п.1, где растворителем является полиэтиленгликоль 400.
5. Способ по любому из пп.1-4, где реакцию проводят при от около 150°С до около 220°С.
6. Способ по любому из пп.1-4, где реакцию проводят при от около 170°С до около 220°С.
7. Способ по любому из пп.1-4, где реакцию проводят при от около 180°С до около 200°С.
8. Способ по любому из пп.1-4, где реакцию проводят от около 2 до около 5 ч.
9. Способ по любому из пп.1-4, где анион тиолата является анионом тиолата линейного или разветвленного алкана, содержащего от 8 до 20 атомов углерода.
10. Способ по п.9, где анион тиолата алкана является додекантиолатом.
11. Способ по любому из пп.1-4, где тиолом является анион тиолата арена, содержащего от 6 до 10 атомов углерода.
12. Способ по п.11, где анионом тиолата арена является тиолат бензола.
13. Способ по любому из пп.1-4 или 12, где анион тиолата получают в присутствии алкоксида.
14. Способ по п.13, где алкоксидом является метоксид.
15. Способ по любому из пп.1-4, 12 или 14, который проводят при стехиометрическом избытке тиолат:венлафаксин вплоть до около 3,0:1.
16. Способ по любому из пп.1-4, 12 или 14, где молярное отношение тиолат:венлафаксин составляет от около 1,15:1 до около 2,5:1.
17. Способ по любому из пп.1-4, 12 или 14, дополнительно предусматривающий нейтрализацию продукта до изоэлектрической точки в присутствии спирта, содержащего алкильную группу с прямой или разветвленной цепью, с от 1 до 6 атомами углерода.
18. Способ по п.17, где спиртом является изопропанол.
19. Способ по п.18, где реакционную смесь охлаждают до температуры от около 65°С до около 75°С перед прибавлением спирта.
20. Способ по п.18, где изоэлектрическая точка лежит в интервале рН от около 9,5 до около 10.
21. Способ получения 0-дезметилвенлафаксина, который включает стадии деметилирования венлафаксина додецилтиолатом и полиэтиленгликолем 400 в присутствии метилата натрия в метаноле при от около 180°С до около 200°С в течение от около 2 до около 5 ч; и нейтрализации продукта до около рН 9,5 в присутствии изопропанола.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33495301P | 2001-12-04 | 2001-12-04 | |
| US60/334,953 | 2001-12-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2004120284A true RU2004120284A (ru) | 2005-04-10 |
| RU2317286C2 RU2317286C2 (ru) | 2008-02-20 |
Family
ID=23309595
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004120284/04A RU2317286C2 (ru) | 2001-12-04 | 2002-12-03 | Способы получения o-дезметилвенлафаксина |
Country Status (29)
| Country | Link |
|---|---|
| US (4) | US6689912B2 (ru) |
| EP (1) | EP1451143B9 (ru) |
| JP (1) | JP4342312B2 (ru) |
| KR (1) | KR100939650B1 (ru) |
| CN (1) | CN1319934C (ru) |
| AR (1) | AR037622A1 (ru) |
| AT (1) | ATE403641T1 (ru) |
| AU (1) | AU2002357049B2 (ru) |
| BR (1) | BR0214701A (ru) |
| CA (1) | CA2466779C (ru) |
| CO (1) | CO5580816A2 (ru) |
| DE (1) | DE60228118D1 (ru) |
| DK (1) | DK1451143T3 (ru) |
| EC (1) | ECSP045135A (ru) |
| ES (1) | ES2311647T4 (ru) |
| HK (1) | HK1065778A1 (ru) |
| HU (1) | HUP0402269A3 (ru) |
| IL (3) | IL162253A0 (ru) |
| MX (1) | MXPA04005309A (ru) |
| NO (1) | NO20042680L (ru) |
| NZ (1) | NZ533316A (ru) |
| PL (1) | PL369299A1 (ru) |
| PT (1) | PT1451143E (ru) |
| RU (1) | RU2317286C2 (ru) |
| SI (1) | SI1451143T1 (ru) |
| TW (1) | TWI260982B (ru) |
| UA (1) | UA80543C2 (ru) |
| WO (1) | WO2003048104A1 (ru) |
| ZA (1) | ZA200405250B (ru) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6342533B1 (en) * | 1998-12-01 | 2002-01-29 | Sepracor, Inc. | Derivatives of (−)-venlafaxine and methods of preparing and using the same |
| CZ20013607A3 (cs) * | 1999-04-06 | 2002-06-12 | Sepracor Inc. | Farmaceutický prostředek |
| JP4220243B2 (ja) * | 2001-02-12 | 2009-02-04 | ワイス | Ｏ−デスメチル−ベンラファキシンの新規コハク酸塩 |
| UA80543C2 (en) * | 2001-12-04 | 2007-10-10 | Wyeth Corp | Method for the preparation of o-desmethylvenlafaxine |
| JP2009500420A (ja) * | 2005-07-06 | 2009-01-08 | セプラコア インコーポレーテッド | エスゾピクロン及びｏ−デスメチルベンラファキシンの組み合わせ、並びに閉経期並びに気分、不安、及び認知障害の治療方法 |
| AU2006322057A1 (en) * | 2005-12-05 | 2007-06-14 | Wyeth | Process for selective synthesis of enantiomers of substituted 1-(2-amino-1-phenyl-ethyl)-cyclohexanols |
| WO2007071404A1 (en) * | 2005-12-20 | 2007-06-28 | Synthon B.V. | Process for making desvenlafaxine |
| CA2646368A1 (en) * | 2006-04-17 | 2007-10-25 | Teva Pharmaceutical Industries Ltd. | Substantially pure o-desmethylvenlafaxine and processes for preparing it |
| MX2007016179A (es) * | 2006-04-17 | 2008-03-11 | Teva Pharma | Formas cristalinas de o-desmetilvenlafaxina. |
| WO2008035369A2 (en) * | 2006-06-30 | 2008-03-27 | Alembic Limited | Novel form of o-desmethyl venlafaxine |
| JP4763788B2 (ja) * | 2006-07-26 | 2011-08-31 | テバ ファーマシューティカル インダストリーズ リミティド | Ｏ−デスメチルベンラファキシンの合成方法 |
| US20090069601A1 (en) * | 2006-07-26 | 2009-03-12 | Valerie Niddam-Hildesheim | Processes for the synthesis of O-desmethylvenlafaxine |
| US20090137846A1 (en) * | 2006-07-26 | 2009-05-28 | Valerie Niddam-Hildesheim | Processes for the synthesis of O-Desmethylvenlafaxine |
| US20080221356A1 (en) * | 2006-07-26 | 2008-09-11 | Valerie Niddam-Hildesheim | Processes for the synthesis of O-desmethylvenlafaxine |
| US20090062572A1 (en) * | 2006-07-26 | 2009-03-05 | Valerie Niddam-Hildesheim | Processes for the synthesis of O-desmethylvenlafaxine |
| WO2008013994A2 (en) | 2006-07-26 | 2008-01-31 | Teva Pharmaceutical Industries Ltd. | Processes for the synthesis of o-desmethylvenlafaxine |
| WO2008013995A2 (en) * | 2006-07-26 | 2008-01-31 | Teva Pharmaceutical Industries Ltd. | Tridesmethylvenlafaxine and processes for the synthesis of o-desmethylvenlafaxine |
| US20100121108A1 (en) * | 2006-08-04 | 2010-05-13 | Medichem, S.A. | Process for synthesizing desvenlafaxine free base and salts or solvates thereof |
| EP2114862A1 (en) * | 2007-01-31 | 2009-11-11 | Merck Generics (UK) Limited | Process for the preparation of o-desmethyl venlafaxine |
| WO2008112313A2 (en) * | 2007-03-14 | 2008-09-18 | Teva Pharmaceutical Industries Ltd. | Processes for preparing solid states of o-desmethylvenlafaxine succinate |
| TR200909798T1 (tr) * | 2007-07-12 | 2010-05-21 | Dr. Reddy's Laboratories Ltd. | O-desmetilvenlafaksin. |
| IN2007CH01519A (ru) * | 2007-07-16 | 2009-09-11 | Matrix Lab Ltd | |
| WO2009034434A2 (en) * | 2007-09-10 | 2009-03-19 | Cadila Pharmaceuticals Limited | An improved process for the preparation of o-desmethylvenlafaxine |
| US20110118357A1 (en) * | 2007-10-26 | 2011-05-19 | Generics Limited | Process for preparing o-desmethylvenlafaxine |
| US8063250B2 (en) * | 2007-11-26 | 2011-11-22 | Teva Pharmaceutical Industries, Ltd. | Crystal forms of O-desmethylvenlafaxine fumarate |
| WO2009084038A2 (en) * | 2007-12-28 | 2009-07-09 | Ind-Swift Laboratories Limited | Improved process for the preparation of 0-desmethyl-venlafaxine |
| WO2009151494A1 (en) * | 2008-03-06 | 2009-12-17 | Teva Pharmaceutical Industries Ltd. | Processes for the preparation of o-desmethylvenlafaxine, free from its dimer impurities |
| EP2119696A1 (en) | 2008-05-16 | 2009-11-18 | Krka | Preparation of O-desmethylvenlafaxine salts |
| EP2119695A1 (en) | 2008-05-16 | 2009-11-18 | Krka | Preparation of O-desmethylvenlafaxine salts |
| US20110112200A1 (en) * | 2008-06-16 | 2011-05-12 | Valerie Niddam-Hildesheim | Solid states of o-desmethylvenlafaxine salts |
| US20100016638A1 (en) * | 2008-07-21 | 2010-01-21 | Zdenko Hamersak | Method for preparation of o-desmethylvenlafaxine using polythiolates |
| AU2009275667A1 (en) * | 2008-07-30 | 2010-02-04 | Generics [Uk] Limited | Process for the preparation of O-desmethylvenlafaxine |
| CZ2008756A3 (cs) | 2008-11-27 | 2010-03-24 | Zentiva, A. S. | Zpusob prípravy desvenlafaxinu a jeho solí |
| CZ200969A3 (cs) | 2009-02-06 | 2010-06-30 | Zentiva, K.S. | Nové soli desvenlafaxinu a zpusob jejich prípravy |
| CZ302145B6 (cs) | 2009-07-15 | 2010-11-10 | Zentiva, K. S. | Zpusob prípravy desvenlafaxinu a jeho solí |
| WO2011007136A2 (en) | 2009-07-16 | 2011-01-20 | Cipla Limited | Process for the preparation of o-desmethyl venlafaxine and intermediate for use therein |
| US20110098506A1 (en) * | 2009-10-26 | 2011-04-28 | Intas Pharmaceuticals Limited | Method of preparing o-desmethylvenlafaxine |
| US20110184067A1 (en) * | 2010-01-25 | 2011-07-28 | Intas Pharmaceuticals Ltd. | O-desmethylvenlafaxine succinate polymorph & process for preparing thereof |
| CA2795023A1 (en) | 2010-03-29 | 2011-10-06 | Pliva Hrvatska D.O.O. | Crystal forms of o-desmethylvenlafaxine fumarate |
| CZ303249B6 (cs) | 2010-04-06 | 2012-06-20 | Zentiva, K.S. | Zpusob výroby 4-(2-(substituovaných)-1-(1-hydroxycyklohexyl)ethyl)fenolu O-demethylací jejich methyletheru pomocí nepáchnoucích aromatických thiolu |
| EP2394976A1 (en) | 2010-06-11 | 2011-12-14 | LEK Pharmaceuticals d.d. | Process for demethylating aromatic methyl ethers using 3-mercaptopropionic acid |
| EP3580198B1 (en) | 2017-02-09 | 2023-08-09 | R L Finechem Private Limited | A process for preparation of1-[2-(dimethylamino)-1-(4-hydroxyphenyl) ethyl]-cyclohexanol and salts thereof |
| CN109232189B (zh) * | 2018-09-25 | 2021-10-08 | 杭州盛弗泰新材料科技有限公司 | 一种高纯度1-羟基芘的制备方法 |
| CN109665966A (zh) * | 2018-11-01 | 2019-04-23 | 山东蒲济医药科技有限公司 | 一种琥珀酸去甲文拉法辛化合物的制备方法 |
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|---|---|---|---|---|
| DE2741009A1 (de) * | 1976-09-22 | 1978-03-23 | Sandoz Ag | 4-styryl-4-indolinol-derivate, ihre verwendung und herstellung |
| US4535186A (en) | 1983-04-19 | 1985-08-13 | American Home Products Corporation | 2-Phenyl-2-(1-hydroxycycloalkyl or 1-hydroxycycloalk-2-enyl)ethylamine derivatives |
| CA1227304A (en) | 1984-08-01 | 1987-09-29 | Raymond C. Francis | Delignification of pulp |
| GB8902209D0 (en) | 1989-02-01 | 1989-03-22 | Wyeth John And Brother Limited | Preparation of cyclohexanol derivatives and novel thioamide intermediates |
| US6197828B1 (en) * | 1998-12-01 | 2001-03-06 | Sepracor, Inc. | Derivatives of (+)-venlafaxine and methods of preparing and using the same |
| US6342533B1 (en) * | 1998-12-01 | 2002-01-29 | Sepracor, Inc. | Derivatives of (−)-venlafaxine and methods of preparing and using the same |
| CZ20013607A3 (cs) | 1999-04-06 | 2002-06-12 | Sepracor Inc. | Farmaceutický prostředek |
| AU5738700A (en) | 1999-06-15 | 2001-01-02 | American Home Products Corporation | Enantiomers of o-desmethyl venlafaxine |
| JP2004504026A (ja) | 2000-07-18 | 2004-02-12 | バイエル アクチェンゲゼルシャフト | ヒトｄｅｓｃ１様セリンプロテアーゼの調節 |
| JP4220243B2 (ja) * | 2001-02-12 | 2009-02-04 | ワイス | Ｏ−デスメチル−ベンラファキシンの新規コハク酸塩 |
| UA80543C2 (en) * | 2001-12-04 | 2007-10-10 | Wyeth Corp | Method for the preparation of o-desmethylvenlafaxine |
-
2002
- 2002-03-12 UA UA20040705306A patent/UA80543C2/uk unknown
- 2002-11-26 US US10/304,871 patent/US6689912B2/en not_active Expired - Fee Related
- 2002-11-27 TW TW091134427A patent/TWI260982B/zh not_active IP Right Cessation
- 2002-12-03 HU HU0402269A patent/HUP0402269A3/hu active IP Right Revival
- 2002-12-03 ES ES02804479T patent/ES2311647T4/es not_active Expired - Lifetime
- 2002-12-03 JP JP2003549297A patent/JP4342312B2/ja not_active Expired - Fee Related
- 2002-12-03 WO PCT/US2002/038403 patent/WO2003048104A1/en active Application Filing
- 2002-12-03 CA CA2466779A patent/CA2466779C/en not_active Expired - Lifetime
- 2002-12-03 SI SI200230743T patent/SI1451143T1/sl unknown
- 2002-12-03 IL IL16225302A patent/IL162253A0/xx active IP Right Grant
- 2002-12-03 DE DE60228118T patent/DE60228118D1/de not_active Expired - Lifetime
- 2002-12-03 CN CNB028242386A patent/CN1319934C/zh not_active Expired - Fee Related
- 2002-12-03 PT PT02804479T patent/PT1451143E/pt unknown
- 2002-12-03 RU RU2004120284/04A patent/RU2317286C2/ru not_active IP Right Cessation
- 2002-12-03 NZ NZ533316A patent/NZ533316A/en unknown
- 2002-12-03 AU AU2002357049A patent/AU2002357049B2/en not_active Ceased
- 2002-12-03 PL PL02369299A patent/PL369299A1/xx unknown
- 2002-12-03 BR BR0214701-7A patent/BR0214701A/pt not_active Application Discontinuation
- 2002-12-03 AR ARP020104669A patent/AR037622A1/es unknown
- 2002-12-03 KR KR1020047008512A patent/KR100939650B1/ko not_active IP Right Cessation
- 2002-12-03 MX MXPA04005309A patent/MXPA04005309A/es active IP Right Grant
- 2002-12-03 DK DK02804479T patent/DK1451143T3/da active
- 2002-12-03 EP EP02804479A patent/EP1451143B9/en not_active Expired - Lifetime
- 2002-12-03 AT AT02804479T patent/ATE403641T1/de not_active IP Right Cessation
-
2003
- 2003-12-31 US US10/750,196 patent/US20040158101A1/en not_active Abandoned
-
2004
- 2004-05-31 IL IL162253A patent/IL162253A/en not_active IP Right Cessation
- 2004-06-01 CO CO04050957A patent/CO5580816A2/es active IP Right Grant
- 2004-06-04 EC EC2004005135A patent/ECSP045135A/es unknown
- 2004-06-25 NO NO20042680A patent/NO20042680L/no not_active Application Discontinuation
- 2004-07-01 ZA ZA2004/05250A patent/ZA200405250B/en unknown
- 2004-11-01 HK HK04108589A patent/HK1065778A1/xx not_active IP Right Cessation
-
2007
- 2007-06-01 US US11/756,772 patent/US7435854B2/en not_active Expired - Fee Related
-
2008
- 2008-09-11 IL IL194034A patent/IL194034A/en not_active IP Right Cessation
- 2008-09-11 US US12/208,990 patent/US20090018365A1/en not_active Abandoned
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