CA2330142A1 - An improved synthesis and purification of (r*,r*)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol hydrochloride - Google Patents
An improved synthesis and purification of (r*,r*)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol hydrochloride Download PDFInfo
- Publication number
- CA2330142A1 CA2330142A1 CA002330142A CA2330142A CA2330142A1 CA 2330142 A1 CA2330142 A1 CA 2330142A1 CA 002330142 A CA002330142 A CA 002330142A CA 2330142 A CA2330142 A CA 2330142A CA 2330142 A1 CA2330142 A1 CA 2330142A1
- Authority
- CA
- Canada
- Prior art keywords
- tramadol
- trans
- cis
- additive
- grignard reaction
- 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.)
- Abandoned
Links
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B49/00—Grignard reactions
-
- 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
- C07C213/02—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 involving the formation of amino groups from compounds containing 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8649898P | 1998-05-22 | 1998-05-22 | |
| US60/086,498 | 1998-05-22 | ||
| PCT/US1999/011336 WO1999061405A1 (en) | 1998-05-22 | 1999-05-20 | An improved synthesis and purification of (r*,r*)-2-[ (dimethylamino) methyl]-1-( 3-methoxyphenyl) cyclohexanol hydrochloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2330142A1 true CA2330142A1 (en) | 1999-12-02 |
Family
ID=22198976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002330142A Abandoned CA2330142A1 (en) | 1998-05-22 | 1999-05-20 | An improved synthesis and purification of (r*,r*)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol hydrochloride |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6399829B1 (https=) |
| EP (1) | EP1077923B1 (https=) |
| JP (1) | JP2002516302A (https=) |
| AT (1) | ATE257147T1 (https=) |
| CA (1) | CA2330142A1 (https=) |
| DE (1) | DE69913955T2 (https=) |
| DK (1) | DK1077923T3 (https=) |
| ES (1) | ES2212849T3 (https=) |
| WO (1) | WO1999061405A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001510180A (ja) * | 1997-07-15 | 2001-07-31 | ラシンスキィ・リミテッド | トラマドール、その塩酸塩、及びそれらの製造方法 |
| KR100342919B1 (ko) * | 1999-10-21 | 2002-07-04 | 박노중 | 트랜스체 염산 트라마돌의 분리 제조방법 |
| RU2165922C1 (ru) * | 2000-07-19 | 2001-04-27 | Государственный научно-исследовательский институт органической химии и технологии | Способ получения трамадола |
| DE10049483A1 (de) * | 2000-09-29 | 2002-05-02 | Gruenenthal Gmbh | Substituierte 1-Aminobutan-3-ol-Derivate |
| DE10049481A1 (de) | 2000-09-29 | 2002-05-02 | Gruenenthal Gmbh | Substituierte C-Cyclohexylmethylamin-Derivate |
| DE10108308A1 (de) | 2001-02-21 | 2002-08-29 | Gruenenthal Gmbh | Verfahren zur Isolierung und Reinigung von (1RS,2RS)-2[(Dimethylamino)methyl]-1-(3-methoxyphenyl)-cyclohexanol |
| US6649783B2 (en) | 2001-10-03 | 2003-11-18 | Euro-Celtique, S.A. | Synthesis of (+/-)-2-((dimethylamino)methyl)-1-(aryl)cyclohexanols |
| DE10236510A1 (de) * | 2002-08-09 | 2004-02-19 | Grünenthal GmbH | Verfahren zur Herstellung von 2-[(Dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol |
| JP2004115510A (ja) * | 2002-09-05 | 2004-04-15 | Toray Fine Chemicals Co Ltd | ピペラジン誘導体の製造方法 |
| EP1785412A1 (en) * | 2005-11-14 | 2007-05-16 | IPCA Laboratories Limited | Tramadol recovery process |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3652589A (en) * | 1967-07-27 | 1972-03-28 | Gruenenthal Chemie | 1-(m-substituted phenyl)-2-aminomethyl cyclohexanols |
| IL103096A (en) * | 1992-09-08 | 1996-12-05 | Chemagis Ltd | Process for purification 2 -]) Dimethylamino (methyl-1-) 3-methoxycinyl (cyclohexanol and its salts. |
| IL116281A (en) * | 1995-12-07 | 1999-06-20 | Chemagis Ltd | Process for the purification of (rr,ss)-2-dimethylaminomethyl-1-(3-methoxyphenyl) cyclohexanol and its salts |
-
1999
- 1999-05-20 EP EP99930115A patent/EP1077923B1/en not_active Expired - Lifetime
- 1999-05-20 WO PCT/US1999/011336 patent/WO1999061405A1/en not_active Ceased
- 1999-05-20 US US09/700,889 patent/US6399829B1/en not_active Expired - Fee Related
- 1999-05-20 DK DK99930115T patent/DK1077923T3/da active
- 1999-05-20 CA CA002330142A patent/CA2330142A1/en not_active Abandoned
- 1999-05-20 ES ES99930115T patent/ES2212849T3/es not_active Expired - Lifetime
- 1999-05-20 DE DE69913955T patent/DE69913955T2/de not_active Expired - Fee Related
- 1999-05-20 AT AT99930115T patent/ATE257147T1/de not_active IP Right Cessation
- 1999-05-20 JP JP2000550815A patent/JP2002516302A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1077923A1 (en) | 2001-02-28 |
| WO1999061405A1 (en) | 1999-12-02 |
| JP2002516302A (ja) | 2002-06-04 |
| EP1077923B1 (en) | 2004-01-02 |
| US6399829B1 (en) | 2002-06-04 |
| DE69913955D1 (de) | 2004-02-05 |
| ES2212849T3 (es) | 2004-08-01 |
| DE69913955T2 (de) | 2004-12-16 |
| ATE257147T1 (de) | 2004-01-15 |
| DK1077923T3 (da) | 2004-04-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20100927 |