DE60137577D1 - Verfahren zur racemisierung von 1-benzyl-4-(4-fluorophenyl)-3-hydroxymethyl-1,2,3,6-tetrahydropyridin und dessen verwendung in der synthese von paroxetin - Google Patents
Verfahren zur racemisierung von 1-benzyl-4-(4-fluorophenyl)-3-hydroxymethyl-1,2,3,6-tetrahydropyridin und dessen verwendung in der synthese von paroxetinInfo
- Publication number
- DE60137577D1 DE60137577D1 DE60137577T DE60137577T DE60137577D1 DE 60137577 D1 DE60137577 D1 DE 60137577D1 DE 60137577 T DE60137577 T DE 60137577T DE 60137577 T DE60137577 T DE 60137577T DE 60137577 D1 DE60137577 D1 DE 60137577D1
- Authority
- DE
- Germany
- Prior art keywords
- tetrahydropyridine
- hydroxymethyl
- benzyl
- paroxetin
- racemizing
- 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.)
- Expired - Lifetime
Links
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 title abstract 2
- STCJUTRPNGTJGE-UHFFFAOYSA-N [1-benzyl-4-(4-fluorophenyl)-3,6-dihydro-2h-pyridin-3-yl]methanol Chemical compound C1C=C(C=2C=CC(F)=CC=2)C(CO)CN1CC1=CC=CC=C1 STCJUTRPNGTJGE-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229960002296 paroxetine Drugs 0.000 abstract 1
- 230000006340 racemization Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- 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
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0021147.4A GB0021147D0 (en) | 2000-08-30 | 2000-08-30 | Chemical process |
| PCT/EP2001/009998 WO2002018338A1 (en) | 2000-08-30 | 2001-08-30 | Process for the racemisation of 1-benzyl-4-(4-fluorophenyl)-3-hydroxymethyl-1,2,3,6-tetrahydropyridine to be used as intermediate in the synthesis of paroxetine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE60137577D1 true DE60137577D1 (de) | 2009-03-19 |
Family
ID=9898420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60137577T Expired - Lifetime DE60137577D1 (de) | 2000-08-30 | 2001-08-30 | Verfahren zur racemisierung von 1-benzyl-4-(4-fluorophenyl)-3-hydroxymethyl-1,2,3,6-tetrahydropyridin und dessen verwendung in der synthese von paroxetin |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6949650B2 (https=) |
| EP (1) | EP1315701B1 (https=) |
| JP (1) | JP2004518620A (https=) |
| AT (1) | ATE421953T1 (https=) |
| AU (1) | AU2002213865A1 (https=) |
| CA (1) | CA2420579C (https=) |
| CZ (1) | CZ2003503A3 (https=) |
| DE (1) | DE60137577D1 (https=) |
| ES (1) | ES2320631T3 (https=) |
| GB (1) | GB0021147D0 (https=) |
| HR (1) | HRP20030227A2 (https=) |
| HU (1) | HUP0302910A3 (https=) |
| IL (2) | IL154302A0 (https=) |
| NO (1) | NO324944B1 (https=) |
| SK (1) | SK2342003A3 (https=) |
| WO (1) | WO2002018338A1 (https=) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2748140A (en) * | 1954-10-07 | 1956-05-29 | Rohm & Haas | 3-hydroxymethyl-4-phenyltetrahydro-pyridines and their esters |
| GB1422263A (en) | 1973-01-30 | 1976-01-21 | Ferrosan As | 4-phenyl-piperidine compounds |
| CN1068597C (zh) * | 1995-05-17 | 2001-07-18 | 诺沃挪第克公司 | 制备4－芳基－哌啶衍生物的方法 |
| GB9526645D0 (en) * | 1995-12-28 | 1996-02-28 | Chiroscience Ltd | Stereoselective synthesis |
| HU221921B1 (hu) * | 1996-07-08 | 2003-02-28 | Richter Gedeon Vegyészeti Gyár Rt. | N-benzil-piperidin- és tetrahidropiridinszármazékok és eljárás azok előállítására |
| GB9710004D0 (en) | 1997-05-17 | 1997-07-09 | Knoll Ag | Chemical process |
| DE19900576A1 (de) * | 1999-01-09 | 2000-07-13 | Merck Patent Gmbh | Benzolderivate |
-
2000
- 2000-08-30 GB GBGB0021147.4A patent/GB0021147D0/en not_active Ceased
-
2001
- 2001-08-30 ES ES01982224T patent/ES2320631T3/es not_active Expired - Lifetime
- 2001-08-30 EP EP01982224A patent/EP1315701B1/en not_active Expired - Lifetime
- 2001-08-30 IL IL15430201A patent/IL154302A0/xx unknown
- 2001-08-30 WO PCT/EP2001/009998 patent/WO2002018338A1/en not_active Ceased
- 2001-08-30 SK SK234-2003A patent/SK2342003A3/sk unknown
- 2001-08-30 DE DE60137577T patent/DE60137577D1/de not_active Expired - Lifetime
- 2001-08-30 AU AU2002213865A patent/AU2002213865A1/en not_active Abandoned
- 2001-08-30 HR HR20030227A patent/HRP20030227A2/xx not_active Application Discontinuation
- 2001-08-30 AT AT01982224T patent/ATE421953T1/de not_active IP Right Cessation
- 2001-08-30 US US10/362,531 patent/US6949650B2/en not_active Expired - Fee Related
- 2001-08-30 HU HU0302910A patent/HUP0302910A3/hu unknown
- 2001-08-30 CA CA002420579A patent/CA2420579C/en not_active Expired - Fee Related
- 2001-08-30 CZ CZ2003503A patent/CZ2003503A3/cs unknown
- 2001-08-30 JP JP2002523456A patent/JP2004518620A/ja not_active Ceased
-
2003
- 2003-02-05 IL IL154302A patent/IL154302A/en not_active IP Right Cessation
- 2003-02-25 NO NO20030876A patent/NO324944B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0302910A3 (en) | 2008-02-28 |
| EP1315701A1 (en) | 2003-06-04 |
| IL154302A (en) | 2008-11-03 |
| GB0021147D0 (en) | 2000-10-11 |
| HRP20030227A2 (en) | 2005-02-28 |
| CA2420579A1 (en) | 2002-03-07 |
| NO324944B1 (no) | 2008-01-07 |
| WO2002018338A1 (en) | 2002-03-07 |
| EP1315701B1 (en) | 2009-01-28 |
| ES2320631T3 (es) | 2009-05-27 |
| AU2002213865A1 (en) | 2002-03-13 |
| IL154302A0 (en) | 2003-09-17 |
| US20040014786A1 (en) | 2004-01-22 |
| US6949650B2 (en) | 2005-09-27 |
| JP2004518620A (ja) | 2004-06-24 |
| CZ2003503A3 (cs) | 2003-08-13 |
| HUP0302910A2 (hu) | 2004-01-28 |
| NO20030876L (no) | 2003-02-25 |
| SK2342003A3 (en) | 2003-09-11 |
| ATE421953T1 (de) | 2009-02-15 |
| NO20030876D0 (no) | 2003-02-25 |
| CA2420579C (en) | 2009-11-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |