SK9242000A3 - Process for the preparation of paroxetine hydrochloride - Google Patents
Process for the preparation of paroxetine hydrochloride Download PDFInfo
- Publication number
- SK9242000A3 SK9242000A3 SK924-2000A SK9242000A SK9242000A3 SK 9242000 A3 SK9242000 A3 SK 9242000A3 SK 9242000 A SK9242000 A SK 9242000A SK 9242000 A3 SK9242000 A3 SK 9242000A3
- Authority
- SK
- Slovakia
- Prior art keywords
- paroxetine hydrochloride
- propan
- solvate
- preparation
- paroxetine
- Prior art date
Links
- 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 title claims abstract description 77
- 229960005183 paroxetine hydrochloride Drugs 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000012453 solvate Substances 0.000 claims abstract description 19
- 239000006184 cosolvent Substances 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- 238000002425 crystallisation Methods 0.000 claims description 9
- 230000008025 crystallization Effects 0.000 claims description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229960000656 paroxetine hydrochloride anhydrous Drugs 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 8
- 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 description 6
- 229960002296 paroxetine Drugs 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 206010036618 Premenstrual syndrome Diseases 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 208000032841 Bulimia Diseases 0.000 description 1
- 206010006550 Bulimia nervosa Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 206010041250 Social phobia Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- GGZDLAOKPXEJCP-UHFFFAOYSA-N phenyl piperidine-1-carboxylate Chemical compound C1CCCCN1C(=O)OC1=CC=CC=C1 GGZDLAOKPXEJCP-UHFFFAOYSA-N 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9726907.0A GB9726907D0 (en) | 1997-12-19 | 1997-12-19 | Novel compounds |
| PCT/GB1998/003836 WO1999032484A1 (en) | 1997-12-19 | 1998-12-18 | Process for the preparation of paroxetine hydrochloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK9242000A3 true SK9242000A3 (en) | 2001-01-18 |
Family
ID=10823933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK924-2000A SK9242000A3 (en) | 1997-12-19 | 1998-12-18 | Process for the preparation of paroxetine hydrochloride |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1042318A1 (no) |
| JP (1) | JP2001526288A (no) |
| KR (1) | KR20010033317A (no) |
| CN (1) | CN1281448A (no) |
| AP (1) | AP2000001836A0 (no) |
| AU (1) | AU1769899A (no) |
| BG (1) | BG104604A (no) |
| BR (1) | BR9813638A (no) |
| CA (1) | CA2315066A1 (no) |
| EA (1) | EA200000689A1 (no) |
| GB (1) | GB9726907D0 (no) |
| HU (1) | HUP0004503A3 (no) |
| ID (1) | ID24733A (no) |
| IL (1) | IL136590A0 (no) |
| NO (1) | NO20003145D0 (no) |
| OA (1) | OA11635A (no) |
| PL (1) | PL341358A1 (no) |
| SK (1) | SK9242000A3 (no) |
| TR (1) | TR200001933T2 (no) |
| WO (1) | WO1999032484A1 (no) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9919001D0 (en) * | 1999-08-12 | 1999-10-13 | Smithkline Beecham Plc | Novel process |
| GB9923439D0 (en) * | 1999-10-04 | 1999-12-08 | Smithkline Beecham Plc | Novel process |
| NL1017421C2 (nl) | 2001-02-21 | 2002-01-15 | Synthon Bv | Werkwijze voor het vervaardigen van paroxetine. |
| IL163593A0 (en) * | 2002-02-22 | 2005-12-18 | Teva Pharma | Preparation of paroxetine involving novel intermediates |
| KR100672184B1 (ko) | 2004-09-21 | 2007-01-19 | 주식회사종근당 | 파록세틴의 콜린산 또는 콜린산 유도체 염 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0223403B1 (en) * | 1985-10-25 | 1993-08-04 | Beecham Group Plc | Piperidine derivative, its preparation, and its use as medicament |
| SK283608B6 (sk) * | 1995-02-06 | 2003-10-07 | Smithkline Beecham Plc | Bezvodý hydrochlorid paroxetínu, spôsob jeho výroby a použitie |
| CA2187128A1 (en) * | 1996-10-04 | 1997-06-26 | K. S. Keshava Murthy | New and useful polymorph of anhydrous paroxetine hydrochloride |
-
1997
- 1997-12-19 GB GBGB9726907.0A patent/GB9726907D0/en not_active Ceased
-
1998
- 1998-12-18 JP JP2000525421A patent/JP2001526288A/ja active Pending
- 1998-12-18 TR TR2000/01933T patent/TR200001933T2/xx unknown
- 1998-12-18 IL IL13659098A patent/IL136590A0/xx unknown
- 1998-12-18 HU HU0004503A patent/HUP0004503A3/hu unknown
- 1998-12-18 SK SK924-2000A patent/SK9242000A3/sk unknown
- 1998-12-18 CN CN98811920A patent/CN1281448A/zh active Pending
- 1998-12-18 AU AU17698/99A patent/AU1769899A/en not_active Abandoned
- 1998-12-18 CA CA002315066A patent/CA2315066A1/en not_active Abandoned
- 1998-12-18 OA OA1200000182A patent/OA11635A/en unknown
- 1998-12-18 PL PL98341358A patent/PL341358A1/xx unknown
- 1998-12-18 EA EA200000689A patent/EA200000689A1/ru unknown
- 1998-12-18 AP APAP/P/2000/001836A patent/AP2000001836A0/en unknown
- 1998-12-18 KR KR1020007006764A patent/KR20010033317A/ko not_active Withdrawn
- 1998-12-18 ID IDW20001158A patent/ID24733A/id unknown
- 1998-12-18 EP EP98962563A patent/EP1042318A1/en not_active Withdrawn
- 1998-12-18 BR BR9813638-0A patent/BR9813638A/pt not_active Application Discontinuation
- 1998-12-18 WO PCT/GB1998/003836 patent/WO1999032484A1/en not_active Ceased
-
2000
- 2000-06-16 NO NO20003145A patent/NO20003145D0/no not_active Application Discontinuation
- 2000-07-13 BG BG104604A patent/BG104604A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010033317A (ko) | 2001-04-25 |
| GB9726907D0 (en) | 1998-02-18 |
| TR200001933T2 (tr) | 2000-12-21 |
| AP2000001836A0 (en) | 2000-06-30 |
| IL136590A0 (en) | 2001-06-14 |
| JP2001526288A (ja) | 2001-12-18 |
| AU1769899A (en) | 1999-07-12 |
| HUP0004503A2 (hu) | 2002-03-28 |
| CA2315066A1 (en) | 1999-07-01 |
| BG104604A (en) | 2001-03-30 |
| WO1999032484A1 (en) | 1999-07-01 |
| EA200000689A1 (ru) | 2000-12-25 |
| OA11635A (en) | 2004-11-22 |
| BR9813638A (pt) | 2000-10-17 |
| PL341358A1 (en) | 2001-04-09 |
| ID24733A (id) | 2000-08-03 |
| HUP0004503A3 (en) | 2002-04-29 |
| CN1281448A (zh) | 2001-01-24 |
| EP1042318A1 (en) | 2000-10-11 |
| NO20003145L (no) | 2000-06-16 |
| NO20003145D0 (no) | 2000-06-16 |
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