ATE257147T1 - Ein verbessertes synthese- und reinigungsverfahren für (r*,r*)-2- ((dimethylamino)methyl)-1-(3-methoxyphenyl) cyclohexanol hydrochlorid - Google Patents
Ein verbessertes synthese- und reinigungsverfahren für (r*,r*)-2- ((dimethylamino)methyl)-1-(3-methoxyphenyl) cyclohexanol hydrochloridInfo
- Publication number
- ATE257147T1 ATE257147T1 AT99930115T AT99930115T ATE257147T1 AT E257147 T1 ATE257147 T1 AT E257147T1 AT 99930115 T AT99930115 T AT 99930115T AT 99930115 T AT99930115 T AT 99930115T AT E257147 T1 ATE257147 T1 AT E257147T1
- Authority
- AT
- Austria
- Prior art keywords
- dimethylamino
- methyl
- trans
- methoxyphenyl
- hydrochloride
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000000746 purification Methods 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000000654 additive Substances 0.000 abstract 3
- 230000000996 additive effect Effects 0.000 abstract 3
- 229960004380 tramadol Drugs 0.000 abstract 3
- TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 238000003747 Grignard reaction Methods 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- PLDWAJLZAAHOGG-UHFFFAOYSA-N 1-bromo-3-methoxybenzene Chemical compound COC1=CC=CC(Br)=C1 PLDWAJLZAAHOGG-UHFFFAOYSA-N 0.000 abstract 1
- HFNCOTSLOKKPHU-UHFFFAOYSA-N cyclohexanol;hydrochloride Chemical compound Cl.OC1CCCCC1 HFNCOTSLOKKPHU-UHFFFAOYSA-N 0.000 abstract 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 239000002904 solvent Substances 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
-
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8649898P | 1998-05-22 | 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 |
|---|---|
| ATE257147T1 true ATE257147T1 (de) | 2004-01-15 |
Family
ID=22198976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT99930115T ATE257147T1 (de) | 1998-05-22 | 1999-05-20 | Ein verbessertes synthese- und reinigungsverfahren für (r*,r*)-2- ((dimethylamino)methyl)-1-(3-methoxyphenyl) cyclohexanol hydrochlorid |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6399829B1 (de) |
| EP (1) | EP1077923B1 (de) |
| JP (1) | JP2002516302A (de) |
| AT (1) | ATE257147T1 (de) |
| CA (1) | CA2330142A1 (de) |
| DE (1) | DE69913955T2 (de) |
| DK (1) | DK1077923T3 (de) |
| ES (1) | ES2212849T3 (de) |
| WO (1) | WO1999061405A1 (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999003820A1 (en) * | 1997-07-15 | 1999-01-28 | Russinsky Limited | Tramadol, salts thereof and process for their preparation |
| 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 (de) | 2005-11-14 | 2007-05-16 | IPCA Laboratories Limited | Verfahren zur Rückgewinnung von Tramadol |
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 CA CA002330142A patent/CA2330142A1/en not_active Abandoned
- 1999-05-20 US US09/700,889 patent/US6399829B1/en 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
- 1999-05-20 ES ES99930115T patent/ES2212849T3/es not_active Expired - Lifetime
- 1999-05-20 DK DK99930115T patent/DK1077923T3/da active
- 1999-05-20 WO PCT/US1999/011336 patent/WO1999061405A1/en not_active Ceased
- 1999-05-20 DE DE69913955T patent/DE69913955T2/de not_active Expired - Fee Related
- 1999-05-20 EP EP99930115A patent/EP1077923B1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69913955T2 (de) | 2004-12-16 |
| CA2330142A1 (en) | 1999-12-02 |
| DE69913955D1 (de) | 2004-02-05 |
| WO1999061405A1 (en) | 1999-12-02 |
| US6399829B1 (en) | 2002-06-04 |
| EP1077923B1 (de) | 2004-01-02 |
| DK1077923T3 (da) | 2004-04-13 |
| JP2002516302A (ja) | 2002-06-04 |
| EP1077923A1 (de) | 2001-02-28 |
| ES2212849T3 (es) | 2004-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| UEP | Publication of translation of european patent specification |
Ref document number: 1077923 Country of ref document: EP |
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| REN | Ceased due to non-payment of the annual fee |