HUP9700140A2 - Eljárás O-demetil-tramadol enantiomerek előállítására - Google Patents
Eljárás O-demetil-tramadol enantiomerek előállításáraInfo
- Publication number
- HUP9700140A2 HUP9700140A2 HU9700140A HUP9700140A HUP9700140A2 HU P9700140 A2 HUP9700140 A2 HU P9700140A2 HU 9700140 A HU9700140 A HU 9700140A HU P9700140 A HUP9700140 A HU P9700140A HU P9700140 A2 HUP9700140 A2 HU P9700140A2
- Authority
- HU
- Hungary
- Prior art keywords
- tramadol
- base
- enantiomer
- demethyl
- enantiomeres
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 abstract 3
- TVYLLZQTGLZFBW-GOEBONIOSA-N (S,S)-tramadol Chemical class COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 abstract 3
- UWJUQVWARXYRCG-UHFFFAOYSA-N o-desmethyltramadol Chemical compound CN(C)CC1CCCCC1(O)C1=CC=CC(O)=C1 UWJUQVWARXYRCG-UHFFFAOYSA-N 0.000 abstract 3
- 229960004380 tramadol Drugs 0.000 abstract 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- 239000001263 FEMA 3042 Substances 0.000 abstract 1
- 238000003916 acid precipitation Methods 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003518 caustics Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 239000012452 mother liquor Substances 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229940033123 tannic acid Drugs 0.000 abstract 1
- 229920002258 tannic acid Polymers 0.000 abstract 1
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
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- 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)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
A találmány az O-demetil-tramadől enantiőmerjeinek előállításieljárására és fájdalőmcsillapító hatóanyagként történő felhasználásáravőnatkőzik.Az eljárást az jellemzi, hőgy valamely racém tramadőlsót bázissáalakítanak, a (-)-tramadől enantiőmert L-(+)-bőrkősavval végzettkicsapás útján elválasztják és a tramadőlbázis felszabadítása űtándiizőbűtil-alűmíniűm-hidriddel az O-demetil-tramadől (-)-enantiőmerjévé alakítják, és a bőrkősavas kicsapás anyalúgjából az O-demetil-tramadől (+)-enantiőmerjét a tramadőlbázis felszabadításávalés dizőbű- til-alűmíniűm-hidriddel történő reagáltatással előállítják.ŕ
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19601744A DE19601744C2 (de) | 1996-01-19 | 1996-01-19 | Verfahren zur Herstellung der Enantiomeren von O-Demethyltramadol |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| HU9700140D0 HU9700140D0 (en) | 1997-03-28 |
| HUP9700140A2 true HUP9700140A2 (hu) | 1998-01-28 |
| HUP9700140A3 HUP9700140A3 (en) | 2000-03-28 |
| HU223661B1 HU223661B1 (hu) | 2004-11-29 |
Family
ID=7783111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9700140A HU223661B1 (hu) | 1996-01-19 | 1997-01-16 | Eljárás O-demetil-tramadol enantiomerek előállítására |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US5728885A (hu) |
| EP (1) | EP0786450B1 (hu) |
| JP (1) | JPH09216857A (hu) |
| KR (1) | KR100507396B1 (hu) |
| CN (1) | CN1073085C (hu) |
| AR (1) | AR005390A1 (hu) |
| AT (1) | ATE191454T1 (hu) |
| AU (1) | AU705195B2 (hu) |
| BR (1) | BR9700079A (hu) |
| CA (1) | CA2195372C (hu) |
| CO (1) | CO4520186A1 (hu) |
| CZ (1) | CZ292427B6 (hu) |
| DE (2) | DE19601744C2 (hu) |
| DK (1) | DK0786450T3 (hu) |
| ES (1) | ES2147341T3 (hu) |
| GR (1) | GR3033390T3 (hu) |
| HK (1) | HK1004810A1 (hu) |
| HU (1) | HU223661B1 (hu) |
| IL (1) | IL120029A (hu) |
| IN (1) | IN181540B (hu) |
| MY (1) | MY116593A (hu) |
| NO (1) | NO306943B1 (hu) |
| NZ (1) | NZ299998A (hu) |
| PE (1) | PE29998A1 (hu) |
| PL (1) | PL187373B1 (hu) |
| PT (1) | PT786450E (hu) |
| RU (1) | RU2185371C2 (hu) |
| SI (1) | SI0786450T1 (hu) |
| SK (1) | SK282629B6 (hu) |
| UA (1) | UA45342C2 (hu) |
| UY (1) | UY24438A1 (hu) |
| ZA (1) | ZA97367B (hu) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19712398A1 (de) * | 1997-03-25 | 1998-10-01 | Gruenenthal Gmbh | Orale Anwendung von (+)-0-Demethyltramadol als Schmerzmittel |
| PE20010623A1 (es) | 1999-10-05 | 2001-07-07 | Gruenenthal Chemie | Uso de (+)-tramadol y/o o-demetiltramadol para tratamiento de urgencia urinaria incrementada y/o incontinencia urinaria |
| WO2001034125A2 (en) * | 1999-11-09 | 2001-05-17 | Darwin Discovery Limited | Therapeutic use and formulation of (-)-tramadol |
| DE10049483A1 (de) * | 2000-09-29 | 2002-05-02 | Gruenenthal Gmbh | Substituierte 1-Aminobutan-3-ol-Derivate |
| DE10108122A1 (de) | 2001-02-21 | 2002-10-02 | Gruenenthal Gmbh | Arzneimittel auf Basis von Tramadol |
| DE10108123A1 (de) * | 2001-02-21 | 2002-10-02 | Gruenenthal Gmbh | Wirkstoffkombination |
| DE10109763A1 (de) * | 2001-02-28 | 2002-09-05 | Gruenenthal Gmbh | Pharmazeutische Salze |
| US20050176790A1 (en) | 2001-02-28 | 2005-08-11 | Johannes Bartholomaus | Pharmaceutical salts |
| CN1289071C (zh) | 2001-03-16 | 2006-12-13 | Dmi生物科学公司 | 曲马朵物质在制备用于延缓男性射精的药物中的用途 |
| US6649783B2 (en) * | 2001-10-03 | 2003-11-18 | Euro-Celtique, S.A. | Synthesis of (+/-)-2-((dimethylamino)methyl)-1-(aryl)cyclohexanols |
| US6780891B2 (en) | 2001-11-30 | 2004-08-24 | Sepracor Inc. | Tramadol analogs and uses thereof |
| US20040248979A1 (en) * | 2003-06-03 | 2004-12-09 | Dynogen Pharmaceuticals, Inc. | Method of treating lower urinary tract disorders |
| DE102005033732B4 (de) | 2005-05-27 | 2014-02-13 | Grünenthal GmbH | Trennung stereoisomerer N,N-Dialkylamino-2-alkyl-3-hydroxy-3-phenyl-alkane |
| EP1785412A1 (en) * | 2005-11-14 | 2007-05-16 | IPCA Laboratories Limited | Tramadol recovery process |
| KR20140054312A (ko) * | 2007-02-12 | 2014-05-08 | 디엠아이 바이오사이언시스 인코포레이티드 | 조루 및 발기부전을 동시에 치료하는 방법 |
| MX2009008511A (es) | 2007-02-12 | 2010-01-20 | Dmi Biosciences Inc | Reduccion de efectos secundarios de tramadol. |
| WO2011110595A1 (de) * | 2010-03-10 | 2011-09-15 | Grünenthal GmbH | Kristalline salze und/oder cokristalle von o-desmethyltramadol |
| EP2383255A1 (en) | 2010-04-28 | 2011-11-02 | Lacer, S.A. | New compounds, synthesis and use thereof in the treatment of pain |
| EP2530072A1 (en) | 2011-06-03 | 2012-12-05 | Lacer, S.A. | New compounds, synthesis and use thereof in the treatment of pain |
| US10702485B2 (en) | 2011-07-09 | 2020-07-07 | Syntrix Biosystems Inc. | Compositions and methods for overcoming resistance to tramadol |
| EP3684753A1 (en) | 2017-09-18 | 2020-07-29 | R L Fine Chem Private Limited | A process for preparation of o-desmethyltramadol and salts thereof |
| US11000488B2 (en) | 2019-03-22 | 2021-05-11 | Syntrix Biosystems Inc. | Treating pain using desmetramadol |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1518663A1 (de) * | 1965-08-02 | 1969-12-18 | Gruenenthal Chemie | Basisch substituierte Cycloalken-derivate und Verfahren zu ihrer Herstellung |
| US3652589A (en) * | 1967-07-27 | 1972-03-28 | Gruenenthal Chemie | 1-(m-substituted phenyl)-2-aminomethyl cyclohexanols |
| ZW14392A1 (en) * | 1991-09-06 | 1994-05-11 | Mcneilab Inc | "Compositions comprising a tramadol material and any of codeine, oxycodone or bydrocodone and their use" |
| ATE169498T1 (de) | 1991-09-06 | 1998-08-15 | Mcneilab Inc | Zusammensetzung, die eine tramadol-verbindung und acetaminophen enthält, und ihre verwendung |
| JPH06122686A (ja) * | 1992-10-12 | 1994-05-06 | Fujisawa Pharmaceut Co Ltd | ラセミ体の光学分割法 |
-
1996
- 1996-01-19 DE DE19601744A patent/DE19601744C2/de not_active Expired - Fee Related
- 1996-12-18 PE PE1996000931A patent/PE29998A1/es not_active Application Discontinuation
- 1996-12-21 ES ES96120727T patent/ES2147341T3/es not_active Expired - Lifetime
- 1996-12-21 AT AT96120727T patent/ATE191454T1/de active
- 1996-12-21 SI SI9630187T patent/SI0786450T1/xx unknown
- 1996-12-21 DK DK96120727T patent/DK0786450T3/da active
- 1996-12-21 PT PT96120727T patent/PT786450E/pt unknown
- 1996-12-21 DE DE59604885T patent/DE59604885D1/de not_active Expired - Lifetime
- 1996-12-21 EP EP96120727A patent/EP0786450B1/de not_active Expired - Lifetime
- 1996-12-23 NZ NZ299998A patent/NZ299998A/en not_active IP Right Cessation
- 1996-12-30 MY MYPI96005545A patent/MY116593A/en unknown
- 1996-12-30 CO CO96068522A patent/CO4520186A1/es unknown
-
1997
- 1997-01-07 AR ARP970100068A patent/AR005390A1/es active IP Right Grant
- 1997-01-09 IN IN46CA1997 patent/IN181540B/en unknown
- 1997-01-10 UY UY24438A patent/UY24438A1/es not_active IP Right Cessation
- 1997-01-10 BR BR9700079A patent/BR9700079A/pt not_active Application Discontinuation
- 1997-01-16 ZA ZA97367A patent/ZA97367B/xx unknown
- 1997-01-16 HU HU9700140A patent/HU223661B1/hu not_active IP Right Cessation
- 1997-01-17 UA UA97010174A patent/UA45342C2/uk unknown
- 1997-01-17 US US08/784,078 patent/US5728885A/en not_active Expired - Lifetime
- 1997-01-17 PL PL97318002A patent/PL187373B1/pl not_active IP Right Cessation
- 1997-01-17 CN CN97102072A patent/CN1073085C/zh not_active Expired - Fee Related
- 1997-01-17 IL IL12002997A patent/IL120029A/xx not_active IP Right Cessation
- 1997-01-17 CZ CZ1997157A patent/CZ292427B6/cs not_active IP Right Cessation
- 1997-01-17 CA CA002195372A patent/CA2195372C/en not_active Expired - Fee Related
- 1997-01-17 RU RU97100984/04A patent/RU2185371C2/ru not_active IP Right Cessation
- 1997-01-17 JP JP9006904A patent/JPH09216857A/ja not_active Ceased
- 1997-01-17 KR KR1019970001204A patent/KR100507396B1/ko not_active IP Right Cessation
- 1997-01-17 NO NO970212A patent/NO306943B1/no not_active IP Right Cessation
- 1997-01-17 SK SK67-97A patent/SK282629B6/sk not_active IP Right Cessation
- 1997-01-17 AU AU12216/97A patent/AU705195B2/en not_active Ceased
-
1998
- 1998-05-08 HK HK98103999A patent/HK1004810A1/xx not_active IP Right Cessation
-
2000
- 2000-05-09 GR GR20000401077T patent/GR3033390T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HFG4 | Patent granted, date of granting |
Effective date: 20041007 |
|
| MM4A | Lapse of definitive patent protection due to non-payment of fees |