WO2001014369A3 - Process for the preparation of paroxetin.hcl - Google Patents
Process for the preparation of paroxetin.hcl Download PDFInfo
- Publication number
- WO2001014369A3 WO2001014369A3 PCT/EP2000/008176 EP0008176W WO0114369A3 WO 2001014369 A3 WO2001014369 A3 WO 2001014369A3 EP 0008176 W EP0008176 W EP 0008176W WO 0114369 A3 WO0114369 A3 WO 0114369A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- solvent
- propan
- acetic acid
- paroxetin
- hcl
- Prior art date
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 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- AHOUBRCZNHFOSL-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine Chemical compound C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000006184 cosolvent Substances 0.000 abstract 2
- 229960005183 paroxetine hydrochloride Drugs 0.000 abstract 2
- WZWBEBSJAMEOMN-TUYUPMGOSA-N (3s,4r)-3-(1,3-benzodioxol-5-yloxymethyl)-1-benzyl-4-(4-fluorophenyl)piperidine;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CN(CC=2C=CC=CC=2)CC1 WZWBEBSJAMEOMN-TUYUPMGOSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910000510 noble metal Inorganic materials 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Paroxetine hydrochloride is prepared by subjecting (-)-trans-1-benzyl-4-(4-fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl) piperidine hydrochloride to catalytic hydrogenation in the presence of a noble metal catalyst in a solvent system consisting of either a mixture of propan-2-o1 and a co-solvent, such as acetic acid, or a solvent other than propan-2-o1, preferably ethanol or methanol, optionally with a co-solvent such as water or acetic acid. Use of this solvent system reduces the amount of residual starting material in the paroxetine hydrochloride product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU75101/00A AU7510100A (en) | 1999-08-25 | 2000-08-18 | Novel process |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9920146.9A GB9920146D0 (en) | 1999-08-25 | 1999-08-25 | Novel process |
| GB9920146.9 | 1999-08-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2001014369A2 WO2001014369A2 (en) | 2001-03-01 |
| WO2001014369A3 true WO2001014369A3 (en) | 2001-09-20 |
Family
ID=10859797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2000/008176 WO2001014369A2 (en) | 1999-08-25 | 2000-08-18 | Process for the preparation of paroxetin.hcl |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU7510100A (en) |
| GB (1) | GB9920146D0 (en) |
| WO (1) | WO2001014369A2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2005000810A1 (en) * | 2003-06-27 | 2006-10-19 | 東レ・ファインケミカル株式会社 | Method for producing nitrogen-containing heterocyclic compound |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998001424A1 (en) * | 1996-07-08 | 1998-01-15 | Richter Gedeon Vegyészeti Gyár Rt. | N-benzylpiperidine and tetrahydropyridine derivatives |
-
1999
- 1999-08-25 GB GBGB9920146.9A patent/GB9920146D0/en not_active Ceased
-
2000
- 2000-08-18 AU AU75101/00A patent/AU7510100A/en not_active Abandoned
- 2000-08-18 WO PCT/EP2000/008176 patent/WO2001014369A2/en active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998001424A1 (en) * | 1996-07-08 | 1998-01-15 | Richter Gedeon Vegyészeti Gyár Rt. | N-benzylpiperidine and tetrahydropyridine derivatives |
Non-Patent Citations (1)
| Title |
|---|
| S.BUDAVARI: "THE MERCK INDEX", 1996, MERCK & CO., NJ, XP002162714, 12 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001014369A2 (en) | 2001-03-01 |
| GB9920146D0 (en) | 1999-10-27 |
| AU7510100A (en) | 2001-03-19 |
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