SK1972001A3 - PROCESS FOR THE PREPARATION OF A NON-CRYSTALLINE ANHYDRATE FORMì (54) OF PAROXETINE HYDROCHLORIDE - Google Patents
PROCESS FOR THE PREPARATION OF A NON-CRYSTALLINE ANHYDRATE FORMì (54) OF PAROXETINE HYDROCHLORIDE Download PDFInfo
- Publication number
- SK1972001A3 SK1972001A3 SK197-2001A SK1972001A SK1972001A3 SK 1972001 A3 SK1972001 A3 SK 1972001A3 SK 1972001 A SK1972001 A SK 1972001A SK 1972001 A3 SK1972001 A3 SK 1972001A3
- Authority
- SK
- Slovakia
- Prior art keywords
- solvate
- paroxetine hydrochloride
- solvent
- heating
- propan
- 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 98
- 229960005183 paroxetine hydrochloride Drugs 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims description 41
- 238000002360 preparation method Methods 0.000 title description 4
- 239000012453 solvate Substances 0.000 claims abstract description 46
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000010438 heat treatment Methods 0.000 claims abstract description 17
- 230000001965 increasing effect Effects 0.000 claims abstract description 6
- 230000007423 decrease Effects 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 38
- 238000001035 drying Methods 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000004807 desolvation Methods 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 239000012065 filter cake Substances 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 208000007848 Alcoholism Diseases 0.000 claims description 3
- 208000032841 Bulimia Diseases 0.000 claims description 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 3
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
- 206010012289 Dementia Diseases 0.000 claims description 3
- 208000019695 Migraine disease Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 208000002193 Pain Diseases 0.000 claims description 3
- 206010041250 Social phobia Diseases 0.000 claims description 3
- 230000032683 aging Effects 0.000 claims description 3
- 239000003570 air Substances 0.000 claims description 3
- 201000007930 alcohol dependence Diseases 0.000 claims description 3
- 208000022531 anorexia Diseases 0.000 claims description 3
- 206010061428 decreased appetite Diseases 0.000 claims description 3
- 206010013663 drug dependence Diseases 0.000 claims description 3
- 208000024732 dysthymic disease Diseases 0.000 claims description 3
- 206010027599 migraine Diseases 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 239000013557 residual solvent Substances 0.000 claims description 3
- 208000011117 substance-related disease Diseases 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 206010036618 Premenstrual syndrome Diseases 0.000 claims 4
- 239000000047 product Substances 0.000 description 20
- 239000000523 sample Substances 0.000 description 15
- 238000006243 chemical reaction Methods 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 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 229960000656 paroxetine hydrochloride anhydrous Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 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
- 208000020401 Depressive disease Diseases 0.000 description 1
- 238000004971 IR microspectroscopy Methods 0.000 description 1
- 238000001530 Raman microscopy Methods 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000006101 laboratory sample Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4525—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9817196.0A GB9817196D0 (en) | 1998-08-07 | 1998-08-07 | Novel process |
| GBGB9828777.4A GB9828777D0 (en) | 1998-12-29 | 1998-12-29 | Novel compounds |
| PCT/GB1999/002592 WO2000008017A1 (fr) | 1998-08-07 | 1999-08-06 | Procede de preparation d'une forme anhydre non cristalline d'hydrochlorure de paroxetine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK1972001A3 true SK1972001A3 (en) | 2001-08-06 |
Family
ID=26314179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK197-2001A SK1972001A3 (en) | 1998-08-07 | 1999-08-06 | PROCESS FOR THE PREPARATION OF A NON-CRYSTALLINE ANHYDRATE FORMì (54) OF PAROXETINE HYDROCHLORIDE |
Country Status (23)
| Country | Link |
|---|---|
| EP (2) | EP1100796B1 (fr) |
| JP (1) | JP2002522434A (fr) |
| KR (1) | KR20010072323A (fr) |
| CN (1) | CN1321155A (fr) |
| AP (2) | AP0102072A0 (fr) |
| AT (1) | ATE239016T1 (fr) |
| AU (1) | AU5428999A (fr) |
| BG (1) | BG105310A (fr) |
| BR (1) | BR9912858A (fr) |
| CA (1) | CA2339857A1 (fr) |
| DE (1) | DE69907467T2 (fr) |
| DK (1) | DK1100796T3 (fr) |
| EA (1) | EA200100221A1 (fr) |
| ES (1) | ES2198940T3 (fr) |
| HU (1) | HUP0105466A3 (fr) |
| ID (1) | ID27914A (fr) |
| IL (1) | IL141286A0 (fr) |
| NO (1) | NO20010629L (fr) |
| PL (1) | PL345885A1 (fr) |
| PT (1) | PT1100796E (fr) |
| SK (1) | SK1972001A3 (fr) |
| TR (1) | TR200100444T2 (fr) |
| WO (1) | WO2000008017A1 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1394160A1 (fr) | 1996-06-13 | 2004-03-03 | SUMIKA FINE CHEMICALS Co., Ltd. | Procédé pour la préparation de hydrochlorure cristallin de paroxetine |
| JP3796351B2 (ja) * | 1998-04-13 | 2006-07-12 | 住友化学株式会社 | パロキセチン塩酸塩無水和物の乾燥方法 |
| GB9923446D0 (en) * | 1999-10-04 | 1999-12-08 | Smithkline Beecham Plc | Novel process |
| EP1345955B1 (fr) * | 2000-11-17 | 2008-08-20 | Eli Lilly And Company | Dipeptide de lactame utile pour inhiber la liberation du peptide beta-amyloide |
| WO2004035052A1 (fr) | 2002-10-16 | 2004-04-29 | Takeda Pharmaceutical Company Limited | Preparations solides stables |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1422263A (en) * | 1973-01-30 | 1976-01-21 | Ferrosan As | 4-phenyl-piperidine compounds |
| EP0223403B1 (fr) * | 1985-10-25 | 1993-08-04 | Beecham Group Plc | Dérivé de pipéridine, sa préparation et son utilisation comme médicament |
| AR001982A1 (es) * | 1995-02-06 | 1998-01-07 | Smithkline Beecham Plc | Clorhidrato de paroxetina anhidratado, y procedimiento para su preparacion |
| EP0952831A1 (fr) * | 1997-01-15 | 1999-11-03 | Smithkline Beecham Plc | Compositions a base de paroxetine |
| JP3796351B2 (ja) * | 1998-04-13 | 2006-07-12 | 住友化学株式会社 | パロキセチン塩酸塩無水和物の乾燥方法 |
-
1999
- 1999-08-06 CA CA002339857A patent/CA2339857A1/fr not_active Abandoned
- 1999-08-06 DE DE69907467T patent/DE69907467T2/de not_active Expired - Fee Related
- 1999-08-06 PL PL99345885A patent/PL345885A1/xx not_active Application Discontinuation
- 1999-08-06 AU AU54289/99A patent/AU5428999A/en not_active Abandoned
- 1999-08-06 AP APAP/P/2001/002072A patent/AP0102072A0/en unknown
- 1999-08-06 AP AP2001002072A patent/AP2001002072A0/xx unknown
- 1999-08-06 EP EP99940290A patent/EP1100796B1/fr not_active Expired - Lifetime
- 1999-08-06 KR KR1020017001635A patent/KR20010072323A/ko not_active Withdrawn
- 1999-08-06 EP EP02080022A patent/EP1321465A3/fr not_active Withdrawn
- 1999-08-06 IL IL14128699A patent/IL141286A0/xx unknown
- 1999-08-06 WO PCT/GB1999/002592 patent/WO2000008017A1/fr not_active Ceased
- 1999-08-06 JP JP2000563650A patent/JP2002522434A/ja active Pending
- 1999-08-06 CN CN99811643A patent/CN1321155A/zh active Pending
- 1999-08-06 SK SK197-2001A patent/SK1972001A3/sk unknown
- 1999-08-06 AT AT99940290T patent/ATE239016T1/de not_active IP Right Cessation
- 1999-08-06 PT PT99940290T patent/PT1100796E/pt unknown
- 1999-08-06 TR TR2001/00444T patent/TR200100444T2/xx unknown
- 1999-08-06 BR BR9912858-6A patent/BR9912858A/pt not_active Application Discontinuation
- 1999-08-06 ES ES99940290T patent/ES2198940T3/es not_active Expired - Lifetime
- 1999-08-06 ID IDW20010296A patent/ID27914A/id unknown
- 1999-08-06 HU HU0105466A patent/HUP0105466A3/hu unknown
- 1999-08-06 EA EA200100221A patent/EA200100221A1/ru unknown
- 1999-08-06 DK DK99940290T patent/DK1100796T3/da active
-
2001
- 2001-02-06 NO NO20010629A patent/NO20010629L/no not_active Application Discontinuation
- 2001-03-06 BG BG105310A patent/BG105310A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK1038230A1 (en) | 2002-03-08 |
| ATE239016T1 (de) | 2003-05-15 |
| EA200100221A1 (ru) | 2001-08-27 |
| BR9912858A (pt) | 2001-11-20 |
| BG105310A (en) | 2001-12-29 |
| ES2198940T3 (es) | 2004-02-01 |
| WO2000008017A1 (fr) | 2000-02-17 |
| DE69907467T2 (de) | 2004-03-11 |
| EP1321465A2 (fr) | 2003-06-25 |
| AP2001002072A0 (en) | 2001-03-31 |
| EP1100796A1 (fr) | 2001-05-23 |
| HUP0105466A3 (en) | 2002-11-28 |
| TR200100444T2 (tr) | 2001-07-23 |
| AU5428999A (en) | 2000-02-28 |
| HUP0105466A2 (hu) | 2002-05-29 |
| EP1321465A3 (fr) | 2003-09-03 |
| EP1100796B1 (fr) | 2003-05-02 |
| CN1321155A (zh) | 2001-11-07 |
| DE69907467D1 (de) | 2003-06-05 |
| NO20010629D0 (no) | 2001-02-06 |
| AP0102072A0 (en) | 2001-02-06 |
| PT1100796E (pt) | 2003-09-30 |
| KR20010072323A (ko) | 2001-07-31 |
| IL141286A0 (en) | 2002-03-10 |
| ID27914A (id) | 2001-05-03 |
| JP2002522434A (ja) | 2002-07-23 |
| NO20010629L (no) | 2001-03-20 |
| PL345885A1 (en) | 2002-01-14 |
| CA2339857A1 (fr) | 2000-02-17 |
| DK1100796T3 (da) | 2003-08-25 |
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