CA2187128A1 - Polymorphe nouveau et efficace, a base de chlorhydrate de paroxetine anhydre - Google Patents

Polymorphe nouveau et efficace, a base de chlorhydrate de paroxetine anhydre

Info

Publication number: CA2187128A1
Authority: CA; Canada
Prior art keywords: paroxetine hydrochloride; form iii; anhydrous; paroxetine; schedule
Prior art date: 1996-10-04
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.): Abandoned

Application number

CA002187128A

Other languages

English (en)

Inventor

K. S. Keshava Murthy

Allan Rey

Gamini Weeratunga

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Apotex Pharmachem Inc

Original Assignee

Brantford Chemicals Inc

Priority date (The priority date 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 date listed.)

1996-10-04

Filing date

1996-10-04

Publication date

1997-06-26

1996-10-04 Application filed by Brantford Chemicals Inc filed Critical Brantford Chemicals Inc

1996-10-04 Priority to CA002187128A priority Critical patent/CA2187128A1/fr

1997-06-26 Publication of CA2187128A1 publication Critical patent/CA2187128A1/fr

Status Abandoned legal-status Critical Current

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 description 67
229960005183 paroxetine hydrochloride Drugs 0.000 title claims description 28
229960000656 paroxetine hydrochloride anhydrous Drugs 0.000 claims abstract description 16
238000002844 melting Methods 0.000 claims abstract description 8
230000008018 melting Effects 0.000 claims abstract description 8
238000002329 infrared spectrum Methods 0.000 claims abstract description 6
238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
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 11
229960002296 paroxetine Drugs 0.000 description 11
239000000463 material Substances 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 8
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 8
238000000034 method Methods 0.000 description 8
229940043265 methyl isobutyl ketone Drugs 0.000 description 8
239000000047 product Substances 0.000 description 6
-1 dichloromethane Chemical class 0.000 description 5
239000002552 dosage form Substances 0.000 description 4
239000012458 free base Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000007812 deficiency Effects 0.000 description 2
238000000113 differential scanning calorimetry Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000010961 commercial manufacture process Methods 0.000 description 1
238000001938 differential scanning calorimetry curve Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000007580 dry-mixing Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000013020 final formulation Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001757 thermogravimetry curve Methods 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA002187128A 1996-10-04 1996-10-04 Polymorphe nouveau et efficace, a base de chlorhydrate de paroxetine anhydre Abandoned CA2187128A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA002187128A CA2187128A1 (fr)	1996-10-04	1996-10-04	Polymorphe nouveau et efficace, a base de chlorhydrate de paroxetine anhydre

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA002187128A CA2187128A1 (fr)	1996-10-04	1996-10-04	Polymorphe nouveau et efficace, a base de chlorhydrate de paroxetine anhydre

Publications (1)

Publication Number	Publication Date
CA2187128A1 true CA2187128A1 (fr)	1997-06-26

Family

ID=4159025

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002187128A Abandoned CA2187128A1 (fr)	1996-10-04	1996-10-04	Polymorphe nouveau et efficace, a base de chlorhydrate de paroxetine anhydre

Country Status (1)

Country	Link
CA (1)	CA2187128A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5874447A (en) *	1997-06-10	1999-02-23	Synthon B. V.	4-Phenylpiperidine compounds for treating depression
WO1999032484A1 (fr) *	1997-12-19	1999-07-01	Smithkline Beecham Plc	Procede de preparation d'hydrochlorure de paroxetine
WO2000001693A1 (fr) *	1998-07-07	2000-01-13	Medichem, S.A.	Polymorphe de maleate de paroxetine et formulations pharmaceutiques le contenant
US6063927A (en) *	1998-07-02	2000-05-16	Smithkline Beecham Plc	Paroxetine derivatives
WO2000032592A1 (fr) *	1998-11-28	2000-06-08	Smithkline Beecham Plc	Procede de fabrication d'hydrochlorure de paroxetine
WO2001012623A1 (fr) *	1999-08-12	2001-02-22	Smithkline Beecham P.L.C.	Procede de preparation d'hydrochlorure de paroxetine anhydre
US6436956B1 (en)	1996-12-24	2002-08-20	Brantford Chemicals Inc.	Useful form of anhydrous paroxetine hydrochloride
WO2002102382A1 (fr) *	2001-06-14	2002-12-27	Teva Pharmaceutical Industries Ltd.	Procede de preparation de paroxetine hcl limitant la formation de composes colores en rose
WO2005019209A3 (fr) *	2003-06-12	2005-05-12	Cadila Healthcare Ltd	Nouvelle forme d'hydrochlorure de paroxetine anhydre et son procede de preparation

1996
- 1996-10-04 CA CA002187128A patent/CA2187128A1/fr not_active Abandoned

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6436956B1 (en)	1996-12-24	2002-08-20	Brantford Chemicals Inc.	Useful form of anhydrous paroxetine hydrochloride
US6900327B2 (en)	1997-06-10	2005-05-31	Synthon Bct Technologies, Llc	4-phenylpiperidine compounds
US5874447A (en) *	1997-06-10	1999-02-23	Synthon B. V.	4-Phenylpiperidine compounds for treating depression
US7598271B1 (en)	1997-06-10	2009-10-06	Noven Therapeutics, Llc	Crystalline paroxetine methane sulfonate
WO1999032484A1 (fr) *	1997-12-19	1999-07-01	Smithkline Beecham Plc	Procede de preparation d'hydrochlorure de paroxetine
US6063927A (en) *	1998-07-02	2000-05-16	Smithkline Beecham Plc	Paroxetine derivatives
WO2000001693A1 (fr) *	1998-07-07	2000-01-13	Medichem, S.A.	Polymorphe de maleate de paroxetine et formulations pharmaceutiques le contenant
ES2138937A1 (es) *	1998-07-07	2000-01-16	Medichem Sa	Polimorfo de maleato de paroxetina y formulaciones farmaceuticas que lo contienen.
US6440459B1 (en)	1998-07-07	2002-08-27	Medichem, S.A.	Paroxetine maleate polymorph and pharmaceutical compositions containing it
WO2000032592A1 (fr) *	1998-11-28	2000-06-08	Smithkline Beecham Plc	Procede de fabrication d'hydrochlorure de paroxetine
WO2001012623A1 (fr) *	1999-08-12	2001-02-22	Smithkline Beecham P.L.C.	Procede de preparation d'hydrochlorure de paroxetine anhydre
WO2002102382A1 (fr) *	2001-06-14	2002-12-27	Teva Pharmaceutical Industries Ltd.	Procede de preparation de paroxetine hcl limitant la formation de composes colores en rose
WO2005019209A3 (fr) *	2003-06-12	2005-05-12	Cadila Healthcare Ltd	Nouvelle forme d'hydrochlorure de paroxetine anhydre et son procede de preparation

Legal Events

Date	Code	Title	Description
1996-10-04	EEER	Examination request
1999-10-04	FZDE	Discontinued

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