WO1999048499A1 - Paroxetine compositions - Google Patents
Paroxetine compositions Download PDFInfo
- Publication number
- WO1999048499A1 WO1999048499A1 PCT/GB1999/000922 GB9900922W WO9948499A1 WO 1999048499 A1 WO1999048499 A1 WO 1999048499A1 GB 9900922 W GB9900922 W GB 9900922W WO 9948499 A1 WO9948499 A1 WO 9948499A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- paroxetine
- solvent
- pharmaceutically acceptable
- adsorbed
- acceptable derivative
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2009—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
Definitions
- PAROXETINE COMPOSITIONS The present invention relates to new formulations of a pharmaceutically active compound, and in particular to a novel formulation of paroxetine.
- this compound is usually isolated as an acid salt, especially the hydrochloride.
- Paroxetine is approved for human use as the hydrochloride salt, and has been proposed for the treatment and prophylaxis of inter alia depression, obsessive compulsive disorder (OCD) and panic.
- Paroxetine hydrochloride has been described in the literature as a crystalline hemihydrate (see EP-A-0223403 of Beecham Group) and as various crystalline anhydrate forms (see WO96/24595 of SmithKline Beecham).
- Paroxetine free base has hitherto been disclosed in the literature as an oil, and so the free base has not itself been considered for therapeutic use, preference being given to crystalline forms which can be more easily purified and processes into dosage forms.
- paroxetine for example paroxetine free base
- paroxetine free base is advantageously formulated into pharmaceutical compositions when adsorbed on or absorbed by a solid carrier.
- the present invention provides a composition comprising paroxetine or a pharmaceutically acceptable derivative thereof adsorbed on or absorbed by a pharmaceutically acceptable solid carrier, and the use of the composition as a therapeutic agent or for the manufacture of a medicament.
- paroxetine may be obtained as a free-flowing powder that can be used directly (for example by direct compression into tablet form) or with further compounding ingredients in therapy.
- paroxetine used in carrying out this invention is preferably paroxetine free base, but may alternatively be a pharmaceutically acceptable derivative such as a salt, more especially the hydrochloride.
- composition of this invention is simply obtained by combining a solution of paroxetine with a suitable adsorbent or absorbent material and evaporating the solvent, for example by spray drying.
- the solvent is suitably toluene, ethanol, acetone, propan-2-ol, or ethyl acetate, or any other suitable solvent or mixture of solvents, in a paroxetine concentration of between 1 and 20%, more preferably between 1 and 4%.
- an oil obtained by removal of solvent from a solution may be blended with a solid adsorbent or absorbent material.
- the material selected as carrier for the paroxetine is an excipient suitable for tablet formation or as a fill material for gelatine capsules, such as cyclodextrin (beta and /or gamma), porous silicates, starch, lactose or calcium phosphate, silica, sorbitol, maltodextrin, microcrystalline or powdered cellulose, sodium or calcium carboxymethylcellulose, calcium carbonate, kaolin, magnesium aluminium silicate. Additionally, soluble excipients such as magnesium stearate may form part of the solution phase.
- the carrier is one that also has a taste-masking effect, for example ion- exchange resins.
- a solution of paroxetine free base may be prepared by addition of a base such as triethylamine to a solution of a crystalline paroxetine salt especially the hydrochloride or acetate.
- the solution may be prepared by basifying a solution of an amorphous paroxetine hydrochloride or a crystalline anhydrate or hydrated form of paroxetine hydrochloride.
- paroxetine free base may be prepared as a solution or oil by adding a base such as potassium hydroxide to a solution of a N-protected paroxetine compound such as N-phenoxycarbonyl paroxetine.
- composition of this invention comprising paroxetine adsorbed on or absorbed by a solid carrier may be formulated with or without conventional excipients for tablet formation or used as a powder fill for capsules.
- the amount of paroxetine used is adjusted such that in a single unit dose there is a therapeutically effective amount of paroxetine.
- the unit dose contains from 10 to 100 mg paroxetine (as measured in terms of the free base). More preferable the amount of paroxetine in a unit dose is lOmg, 20mg, 30mg, 40mg or 50mg. The most preferred amount of paroxetine in a unit dose is 20mg.
- paroxetine product of this invention includes treatment of: alcoholism, anxiety, depression, obsessive compulsive disorder, panic disorder, chronic pain, obesity, senile dementia, migraine, bulimia, anorexia, social phobia, pre-menstrual syndrome (PMS), adolescent depression, trichotillomania, dysthymia, and substance abuse, referred to below as "the disorders”.
- the disorders include treatment of: alcoholism, anxiety, depression, obsessive compulsive disorder, panic disorder, chronic pain, obesity, senile dementia, migraine, bulimia, anorexia, social phobia, pre-menstrual syndrome (PMS), adolescent depression, trichotillomania, dysthymia, and substance abuse, referred to below as "the disorders”.
- the present invention also provides:
- a pharmaceutical composition for treatment or prophylaxis of the disorders comprising paroxetine or a pharmaceutically acceptable derivative thereof adsorbed on or absorbed by a solid carrier and, optionally, at least one further pharmaceutically acceptable excipient; the use of paroxetine or a pharmaceutically acceptable derivative thereof adsorbed on or absorbed by a solid carrier to manufacture a medicament for the treatment or prophylaxis of the disorders; and
- a method of treating the disorders which comprises administering an effective or prophylactic amount of paroxetine or a pharmaceutically acceptable derivative thereof adsorbed on or absorbed by a solid carrier to a person suffering from one or more of the disorders.
- Example 1 Preparation of tablet pre-mix containing paroxetine free base.
- a mixture of dibasic calcium phosphate dihydrate (408 g), hydroxypropylmethyl cellulose (25 g) and sodium starch glycollate (25 g) was blended in a key granulator for 3 minutes at a stir rate of 240 r.p.m. and an impeller rate of 3000 r.p.m.
- Purified water (57 ml) was added at a rate of approximately 4 ml/minute for 13.5 minutes while the key granulator was set at a stir rate of 240 r.p.m. and the impeller rate was set at 1500 r.p.m.
- the mixture was stirred for a further 1 minute, and the resulting granules dried in an air oven at 50°C for 3 hours.
- This product is suitable for direct compression into tablets containing 10, 20, or 30 mg paroxetine.
- N-phenoxycarbonyl paroxetine 50.0g
- potassium hydroxide 45.0g
- toluene 750ml
- distilled water 500ml
- the organic layer was separated, dried over magnesium sulfate and concentrated to a total volume of 85ml.
- Toluene (100ml) was added to an aliquot of the solution of paroxetine free amine in toluene ( 0.43g/ml) ( 2.4 ml) and to this solution was added Celite ( 25. Og ) and the mixture stirred for 5 minutes. Solvent was removed under reduced pressure (water bath 55°C) to afford the Celite supported paroxetine free amine as a free moving powdery solid (26. Og).
- This product may be mixed with additional excipients and compressed into tablets or added directly to capsule shells to make a product containing a therapeutic dose of paroxetine.
- Example 3 Spray drying of paroxetine hydrochloride solution onto a suspended carrier material.
- Anhydrous paroxetine hydrochloride 60 g was dissolved in anhydrous ethanol (725 ml) and the clear solution slurried with maltodextrin DE4-6 (506 g).
- the uniform suspension was spray-dried in a Niro Mobile Minor (TM) closed cycle spray dryer using nitrogen as the process gas, a rotary atomiser wheel spinning at 27,000 r.p.m. (alternatively a co- current or fountain two-fluid nozzle could be used), an inlet temperature of 96-104 C and outlet temperature of 44-50 C at a feed rate of 4.1 kg per hour.
- a white free-flowing product was recovered (490 g) which was found to have a mean particle size of 84 microns.
- a mixture of dibasic calcium phosphate dihydrate (408 g), hydroxypropylmethyl cellulose (25 g) and sodium starch glycollate (25 g) was blended in a key granulator for 3 minutes at a stir rate of 240 r.p.m. and an impeller rate of 3000 r.p.m.
- Purified water (57 ml) was added at a rate of approximately 4ml/minute for 13.5 minutes while the key granulator was set at a stir rate of 240 r.p.m. and the impeller rate was set at 1500 r.p.m.
- the mixture was stirred for a further 1 minute, and the resulting granules dried in an air oven at 50°C for 3 hours.
- N-phenoxycarbonyl paroxetine 50.0 g
- potassium hydroxide 45.0 g
- toluene 750 ml
- distilled water 500 ml
- Tablet granules ( 25. Og ), prepared as in Example 4, were added and the mixture stirred at 60°C for 5 minutes. Solvent was removed under reduced pressure at 60°C for 5 minutes.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Inorganic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
Claims
Priority Applications (14)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PL99343095A PL343095A1 (en) | 1998-03-24 | 1999-03-24 | Paroxetine compositions |
JP2000537547A JP2002507569A (en) | 1998-03-24 | 1999-03-24 | Paroxetine composition |
CA002324612A CA2324612A1 (en) | 1998-03-24 | 1999-03-24 | Paroxetine compositions |
NZ506893A NZ506893A (en) | 1998-03-24 | 1999-03-24 | Paroxetine compositions adsorbed or absorbed by a solid carrier |
KR1020007010550A KR20010042145A (en) | 1998-03-24 | 1999-03-24 | Paroxetine Compositions |
IL13847899A IL138478A0 (en) | 1998-03-24 | 1999-03-24 | Paroxetine compositions |
APAP/P/2000/001914A AP2000001914A0 (en) | 1998-03-24 | 1999-03-24 | Paroxetine compositions. |
EA200000977A EA003393B1 (en) | 1998-03-24 | 1999-03-24 | Paroxetine compositions |
BR9908991-2A BR9908991A (en) | 1998-03-24 | 1999-03-24 | Compositions of paroxetine |
AU30451/99A AU754765B2 (en) | 1998-03-24 | 1999-03-24 | Paroxetine compositions |
EP99911940A EP1063993A1 (en) | 1998-03-24 | 1999-03-24 | Paroxetine compositions |
SK1410-2000A SK14102000A3 (en) | 1998-03-24 | 1999-03-24 | Paroxetine compositions |
NO20004740A NO313404B1 (en) | 1998-03-24 | 2000-09-22 | A pharmaceutical composition comprising paroxetine, a process for the preparation of the composition, and its use |
BG104865A BG104865A (en) | 1998-03-24 | 2000-10-16 | Paroxetinne-containing compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9806312.6 | 1998-03-24 | ||
GBGB9806312.6A GB9806312D0 (en) | 1998-03-24 | 1998-03-24 | Novel formulations |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09646622 A-371-Of-International | 2000-11-28 | ||
US10/134,917 Continuation US6699882B2 (en) | 1998-03-24 | 2002-04-29 | Paroxetine compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999048499A1 true WO1999048499A1 (en) | 1999-09-30 |
Family
ID=10829181
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1999/000922 WO1999048499A1 (en) | 1998-03-24 | 1999-03-24 | Paroxetine compositions |
Country Status (20)
Country | Link |
---|---|
EP (1) | EP1063993A1 (en) |
JP (1) | JP2002507569A (en) |
CN (1) | CN1125639C (en) |
AP (1) | AP2000001914A0 (en) |
AU (1) | AU754765B2 (en) |
BG (1) | BG104865A (en) |
BR (1) | BR9908991A (en) |
CA (1) | CA2324612A1 (en) |
EA (1) | EA003393B1 (en) |
GB (1) | GB9806312D0 (en) |
HU (1) | HUP0101326A3 (en) |
ID (1) | ID26485A (en) |
IL (1) | IL138478A0 (en) |
NO (1) | NO313404B1 (en) |
NZ (1) | NZ506893A (en) |
PL (1) | PL343095A1 (en) |
SK (1) | SK14102000A3 (en) |
TR (1) | TR200002750T2 (en) |
WO (1) | WO1999048499A1 (en) |
ZA (1) | ZA200005697B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000078288A2 (en) * | 1999-06-22 | 2000-12-28 | Smithkline Beecham P.L.C. | Novel process for paroxetine compositions |
DK200100341A (en) * | 2001-03-02 | 2002-09-03 | Gea Farmaceutisk Fabrik As | Process for the preparation of pharmaceutical tablets containing paroxetine hydrochloride anhydrate |
US8062664B2 (en) | 2003-11-12 | 2011-11-22 | Abbott Laboratories | Process for preparing formulations of lipid-regulating drugs |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2531097C (en) * | 2003-07-02 | 2012-10-09 | Abbott Laboratories | Process for preparing formulations of lipid-regulating drugs |
HU1000278D0 (en) * | 2010-05-28 | 2010-07-28 | Egis Gyogyszergyar Nyilvanosan | Novel pharmaceutical use uf silicic acid |
CN103961333B (en) * | 2014-05-07 | 2020-02-21 | 浙江华海药业股份有限公司 | Paroxetine mesylate capsule and preparation method thereof |
CN104027306A (en) * | 2014-06-25 | 2014-09-10 | 万特制药(海南)有限公司 | Paroxetine oral suspension and preparation method thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0223403A2 (en) * | 1985-10-25 | 1987-05-27 | Beecham Group Plc | Piperidine derivative, its preparation, and its use as medicament |
DE19603797A1 (en) * | 1995-02-06 | 1996-08-14 | Smithkline Beecham Plc | New forms of paroxetine hydrochloride |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1422263A (en) * | 1973-01-30 | 1976-01-21 | Ferrosan As | 4-phenyl-piperidine compounds |
CA2206592A1 (en) * | 1996-05-30 | 1997-11-30 | Shu-Zhong Wang | Method of producing amorphous paroxetine hydrochloride |
-
1998
- 1998-03-24 GB GBGB9806312.6A patent/GB9806312D0/en not_active Ceased
-
1999
- 1999-03-24 TR TR2000/02750T patent/TR200002750T2/en unknown
- 1999-03-24 BR BR9908991-2A patent/BR9908991A/en not_active IP Right Cessation
- 1999-03-24 NZ NZ506893A patent/NZ506893A/en unknown
- 1999-03-24 CA CA002324612A patent/CA2324612A1/en not_active Abandoned
- 1999-03-24 HU HU0101326A patent/HUP0101326A3/en unknown
- 1999-03-24 EA EA200000977A patent/EA003393B1/en not_active IP Right Cessation
- 1999-03-24 AP APAP/P/2000/001914A patent/AP2000001914A0/en unknown
- 1999-03-24 ID IDW20001883A patent/ID26485A/en unknown
- 1999-03-24 EP EP99911940A patent/EP1063993A1/en not_active Withdrawn
- 1999-03-24 CN CN99804347A patent/CN1125639C/en not_active Expired - Fee Related
- 1999-03-24 IL IL13847899A patent/IL138478A0/en unknown
- 1999-03-24 SK SK1410-2000A patent/SK14102000A3/en unknown
- 1999-03-24 WO PCT/GB1999/000922 patent/WO1999048499A1/en not_active Application Discontinuation
- 1999-03-24 PL PL99343095A patent/PL343095A1/en unknown
- 1999-03-24 JP JP2000537547A patent/JP2002507569A/en active Pending
- 1999-03-24 AU AU30451/99A patent/AU754765B2/en not_active Withdrawn - After Issue
-
2000
- 2000-09-22 NO NO20004740A patent/NO313404B1/en unknown
- 2000-10-16 BG BG104865A patent/BG104865A/en unknown
- 2000-10-16 ZA ZA200005697A patent/ZA200005697B/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0223403A2 (en) * | 1985-10-25 | 1987-05-27 | Beecham Group Plc | Piperidine derivative, its preparation, and its use as medicament |
DE19603797A1 (en) * | 1995-02-06 | 1996-08-14 | Smithkline Beecham Plc | New forms of paroxetine hydrochloride |
WO1996024595A1 (en) * | 1995-02-06 | 1996-08-15 | Smithkline Beecham Plc | New forms of paroxetin hydrochloride |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000078288A2 (en) * | 1999-06-22 | 2000-12-28 | Smithkline Beecham P.L.C. | Novel process for paroxetine compositions |
WO2000078288A3 (en) * | 1999-06-22 | 2001-02-15 | Smithkline Beecham Plc | Novel process for paroxetine compositions |
DK200100341A (en) * | 2001-03-02 | 2002-09-03 | Gea Farmaceutisk Fabrik As | Process for the preparation of pharmaceutical tablets containing paroxetine hydrochloride anhydrate |
WO2002069969A1 (en) * | 2001-03-02 | 2002-09-12 | A/S Gea Farmaceutisk Fabrik | A process for the manufacture of pharmaceutical tablets containing paroxetine hydrochloride anhydrate |
US8062664B2 (en) | 2003-11-12 | 2011-11-22 | Abbott Laboratories | Process for preparing formulations of lipid-regulating drugs |
Also Published As
Publication number | Publication date |
---|---|
EA200000977A1 (en) | 2001-02-26 |
CA2324612A1 (en) | 1999-09-30 |
SK14102000A3 (en) | 2001-03-12 |
NO20004740D0 (en) | 2000-09-22 |
NO20004740L (en) | 2000-10-03 |
JP2002507569A (en) | 2002-03-12 |
EA003393B1 (en) | 2003-04-24 |
CN1294512A (en) | 2001-05-09 |
CN1125639C (en) | 2003-10-29 |
PL343095A1 (en) | 2001-07-30 |
ID26485A (en) | 2001-01-11 |
BG104865A (en) | 2001-05-31 |
NZ506893A (en) | 2003-06-30 |
TR200002750T2 (en) | 2000-12-21 |
GB9806312D0 (en) | 1998-05-20 |
AU754765B2 (en) | 2002-11-21 |
HUP0101326A3 (en) | 2002-06-28 |
BR9908991A (en) | 2000-12-12 |
AP2000001914A0 (en) | 2000-09-30 |
IL138478A0 (en) | 2001-10-31 |
EP1063993A1 (en) | 2001-01-03 |
ZA200005697B (en) | 2001-10-02 |
HUP0101326A2 (en) | 2002-05-29 |
AU3045199A (en) | 1999-10-18 |
NO313404B1 (en) | 2002-09-30 |
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