AP540A - Paroxetine tablets and process to prepare them. - Google Patents
Paroxetine tablets and process to prepare them. Download PDFInfo
- Publication number
- AP540A AP540A APAP/P/1994/000704A AP9400704A AP540A AP 540 A AP540 A AP 540A AP 9400704 A AP9400704 A AP 9400704A AP 540 A AP540 A AP 540A
- Authority
- AP
- ARIPO
- Prior art keywords
- paroxetine
- formulation
- tablet
- compressed
- tablets
- 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 claims abstract description 39
- 229960002296 paroxetine Drugs 0.000 title claims abstract description 39
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 238000009472 formulation Methods 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000007907 direct compression Methods 0.000 claims abstract description 5
- 238000007908 dry granulation Methods 0.000 claims abstract description 5
- 238000007906 compression Methods 0.000 claims abstract description 4
- 230000006835 compression Effects 0.000 claims abstract description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 14
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 7
- 235000019359 magnesium stearate Nutrition 0.000 claims description 7
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 7
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 7
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 7
- 229940080313 sodium starch Drugs 0.000 claims description 7
- 239000001506 calcium phosphate Substances 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 4
- 229910000389 calcium phosphate Inorganic materials 0.000 claims description 3
- 229960001714 calcium phosphate Drugs 0.000 claims description 3
- 235000011010 calcium phosphates Nutrition 0.000 claims description 3
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 claims description 3
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims description 3
- 241000237858 Gastropoda Species 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 235000010980 cellulose Nutrition 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- RBLGLDWTCZMLRW-UHFFFAOYSA-K dicalcium;phosphate;dihydrate Chemical compound O.O.[Ca+2].[Ca+2].[O-]P([O-])([O-])=O RBLGLDWTCZMLRW-UHFFFAOYSA-K 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 3
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 3
- 229940038472 dicalcium phosphate Drugs 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- PYHRZPFZZDCOPH-QXGOIDDHSA-N (S)-amphetamine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C[C@H](N)CC1=CC=CC=C1.C[C@H](N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-QXGOIDDHSA-N 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 229920003084 Avicel® PH-102 Polymers 0.000 description 1
- 208000032841 Bulimia Diseases 0.000 description 1
- 206010006550 Bulimia nervosa Diseases 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 206010036618 Premenstrual syndrome Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 206010041250 Social phobia Diseases 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 201000000484 premenstrual tension Diseases 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000005550 wet granulation Methods 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
- 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
- A61K9/2095—Tabletting processes; Dosage units made by direct compression of powders or specially processed granules, by eliminating solvents, by melt-extrusion, by injection molding, by 3D printing
-
- 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
- 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)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Proxetine formulated into tablets by using a formulation process in which water is absent.The process consists, preferably, of a dry direct compression of paroxetine into tablets or a dry granulation of paroxetine followed by compression into tablets.
Description
NOVEL FORMULATION
The present invention relates to novel formulations and to the use of the formulation in the treatment and/or prevention of certain disorders.
US Patent 4,007,196 describes certain compounds which possess antidepressant activity. One specific compound mentioned in this patent is known as paroxetine and which has the following formula:
This compound has been approved for human use and is being sold in many countries around the world as an anti-depressant agent.
It has been noticed that tablets of paroxetine often develop a pink hue which is highly undesirable.
To date, all tablets which have been sold have been formulated using an aqueous granulation process. It has surprisingly been found that formulation of paroxetine into tablets can be carried out reliably and on a commercial scale using a formulation process in which water is absent, such as by direct compression or by dry granulation.
It has also been surprisingly found that paroxetine formulated into a tablet using a process in which water is absent, is much less likely to develop a pink hue.
Accordingly, the present invention provides paroxetine which is formulated into tablets using a formulation process in which water is absent.
Examples of such a formulation process are dry direct compression of paroxetine or dry granulation of paroxetine followed by compression into tablets.
The present invention therefore provides a formulation comprising direct compressed paroxetine admixed with dry excipients in the form of a tablet and a formulation comprising dry granulated and compressed paroxetine admixed with dry excipients in the form of a tablet.
It should be appreciated that the term dry means substantially dry as opposed to the wholesale addition of water which was previously employed in the wet granulation process.
’ 1 ’ BAD ORIGINAL $
0 L 0 0 / V6 /d/dV
P30835
Direct compression techniques are generally known in the art of pharmaceutical science. For example, paroxetine is conventionally admixed with dry excipients and compressed into tablets.
Dry granulation techniques are generally also known in the art of 5 pharmaceutical science. For example, paroxetine is conventionally admixed with dry excipients and compressed into large slugs or roller compacted into ribbon-like strands. The compacted material is then suitably milled to produce a free flowing powder which is then compressed into tablets.
Additional excipients may then be added and mixed with the free flowing 10 powder before being compressed into tablets.
Examples of excipients include calcium phosphate, microcrystalline cellulose, sodium starch glycollate and magnesium stearate which may be admixed in appropriate ratios.
It should be appreciated that particularly good results are obtained when 15 microcrystalline cellulose is absent from the formulation, this is surprising as tablets formulated in the absence of microcystalline cellulose are often prone to breaking up during manufacture or storage.
The paroxetine/excipient mixture may be compressed into an appropriate tablet shape. Preferred shapes include a pentagonal circumcircle, oval, round bi20 convex or a tilt-tablet such as those described in US Patent 4,493,822.
Paroxetine when incorporated into the above-mentioned tablets is suitably, present as the hydrochloride hemi-hydrate form which may be prepared according to the procedures outlined in US Patent 4,721,723.
The amount of paroxetine present in the above-mentioned tablets is in the 25 range of 10 to 100 mg of paroxetine as measured in terms of the free base.
Particularly preferred amounts include 10 mg, 20 mg, 30 mg, 40 mg and 50 mg of paroxetine as measured in terms of the free base. Particularly preferred amounts include 20 mg, 30 mg and 40 mg of paroxetine as measured in terms of the free base.
Suitable procedures for preparing paroxetine include those mentioned in US
Patents 4,009,196,4,902,801,4,861,893 and 5,039,803 and PCT/GB 93/00721.
It has been mentioned that paroxetine has particular utility in the treatment of depression, paroxetine may also be used in the treatment of mixed anxiety and depression, obsessive compulsive disorders, panic, pain, obesity, senile dementia, migraine, bulimia, anorexia, social phobia and the depression arising from premenstrual tension and adolescence.
The present invention therefore also provides a method of treating or preventing any of the above disorders which comprises administering an effective or
c.
t
-2BAD ORIGINAL
P30835
AP.0 0 5 4 0 prophylatic amount to a sufferer in need thereof of paroxetine which is formulated into a tablet using a process in which water is absent
The present invention further provides a pharmaceutical composition comprising paroxetine which is formulated into a tablet using a process in which water is absent for use in treating or preventing of the above disorders.
The present invention further provides the use of paroxetine which is formulated into a tablet using a process in which water is absent in the manufacture of a medicament for treating or preventing the above disorders.
The following examples illustrate the present invention:
Example 1
| INGREDIENTS | 20 mg Tablet | 30mg Tablet |
| Paroxetine hydrochloride hemihydrate | 22.67 mg | 34.0 mg |
| Dicalcium Phosphate (DCP) | 83.34 mg | 125.0 mg |
| Microcrystalline Cellulose | 50.67 mg | 76.0 mg |
| Sodium Starch Glycollate | 8.34 mg | 12.5 mg |
| Magnesium Stearate | 1.67 mg | 1 2.5 mg |
| Tablet Weight | 166.7 mg | 250.0 mg |
AP/P/ 94/00704
Commercial source of the ingredients
Dicalcium Phosphate Dihydrate - Emcompress or Ditab*
Microcrystalline Cellulose - Avicel PH 102*
Sodium Starch Glycollate - Explotab.* ♦ Tradenames
-3BAD ORIGINAL d
P30835
Method
1. Pass DCP through a screen and weigh it into a Planetary mixer.
2. Add 30 mesh Paroxetine to the bowl.
3. Add 20 mesh Avicel and Explotab and mix all the powders for 10 minutes.
4. Add magnesium Stearate and mix for 5 minutes.
Tablet into Pentagonal Tablets using the following punches:
mg Tablet 9.5 mm Circumcircle
20 mg Tablet 8.25 mm Circumcircle
The tablets are made satisfactorily on a single punch or a Rotary press.
-4BAD ORIGINAL Q
P30835
Example 2
| INGREDIENTS | 10 mg Tablet | 20 mg Tablet | 30mg Tablet |
| Paroxetine hydrochloride hemihydrate | 11.40 mg | 22.80 mg | 34.20 mg |
| Sodium Starch Glycollate | 2.98 mg | 5.95 mg | 8.93 mg |
| Granular Dicalcium Phosphate (DITAB) or Dicafos | 158.88 mg | 317.75 mg | 476.63 mg |
| Magnesium Stearate | 1.75 mg | 3.50 mg | 5.25 mg |
| Tablet Weight | 175.00 mg | 350.00 mg | 525.00 mg |
Method
AP/P/ 9 4 / 0 0 7 0 4
1. Paroxetine, Sodium Starch Glycollate and Dicalcium Phosphate Dihydrate are screened and mixed together in a suitable mixer.
(Planetary, Cuble or High Energy Shear mixer.)
2. Add Magnesium Stearate and compress it into a tablet using a single punch or Rotary Tablet machine.
Claims (15)
- Claims1. Paroxetine which is formulated into tablets using a formulation process in which water is absent.
- 2. A formulation process according to claim 1 which is a dry direct compression of paroxetine followed by compression into tablets or a dry granulation of paroxetine followed by compression into tablets.10
- 3. A formulation process according to claim 1 or 2 in which paroxetine is admixed with dry excipients.
- 4. A formulation process according to claim 3 in which the paroxetine admixed with dry excipients is compressed into large slugs or roller compacted into ribbon-like15 strands.
- 5. A formulation process according to claim 4 in which the compressed or compacted material is milled to produce a free flowing powder and compressed into tablets.
- 6. A formulation process according to claim 3, 4 or 5 in which the excipients are selected from calcium phosphate, microcrystalline cellulose, sodium starch glycollate and magnesium stearate which may be admixed in appropriate ratios.25
- 7. A formulation process according to claim 3,4, or 5 in which microcrystalline cellulose is absent from the formulation.
- 8. A formulation process according to claim 5 in which the tablet is compressed into a pentagonal circumcircle, oval, round bi-convex, or tilt-tablet shape.
- 9. A formulation process according to any one of claims 1 to 8 in which paroxetine is in the form of the hydrochloride hemi-hydrate.
- 10. A formulation comprising direct compressed paroxetine admixed with any 35 excipients in the form of a tablet.
- 11. A formulation comprising dry granulated and compressed paroxetine admixed with excipients in the form of a tablet.40
- 12. A formulation according to claim 10 or 11 in which the excipients are selected from calcium phosphate, microcrystalline cellulose, sodium starch glycollate and magnesium stearate which may be admixed in appropriate ratios.-6BAD o«g’nMP30835AP . Ο Ο 5 4 Ο
- 13. A formulation according to claim 10 or 11 in which the microcrystaliine cellulose is absent.
- 14. A formulation according to any one of claims 10 to 13 in which the tablet is5 compressed into a pentagonal circumcircle, oral, round bi-convex or tilt-tablet shape.
- 15. A formulation according to any one of claims 10 to 14 in which the paroxetine is in the form of the hydrochloride hemi-hydrate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939325644A GB9325644D0 (en) | 1993-12-15 | 1993-12-15 | Novel formulation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9400704A0 AP9400704A0 (en) | 1995-01-31 |
| AP540A true AP540A (en) | 1996-09-20 |
Family
ID=10746644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1994/000704A AP540A (en) | 1993-12-15 | 1994-12-13 | Paroxetine tablets and process to prepare them. |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US6113944A (en) |
| EP (1) | EP0734260B2 (en) |
| JP (1) | JP3037757B2 (en) |
| KR (1) | KR100367796B1 (en) |
| CN (1) | CN1071116C (en) |
| AP (1) | AP540A (en) |
| AT (1) | ATE180973T1 (en) |
| AU (1) | AU697982B2 (en) |
| BG (1) | BG62755B1 (en) |
| BR (1) | BR9408219A (en) |
| CA (4) | CA2274387A1 (en) |
| CZ (1) | CZ287891B6 (en) |
| DE (1) | DE69419033T2 (en) |
| DK (1) | DK0734260T4 (en) |
| DZ (1) | DZ1835A1 (en) |
| ES (1) | ES2132610T5 (en) |
| FI (1) | FI962445A0 (en) |
| GB (1) | GB9325644D0 (en) |
| GR (1) | GR3031047T3 (en) |
| HU (1) | HUT75880A (en) |
| IL (1) | IL111978A (en) |
| MA (1) | MA23395A1 (en) |
| MY (1) | MY112123A (en) |
| NO (1) | NO307366B1 (en) |
| NZ (1) | NZ277790A (en) |
| OA (1) | OA10297A (en) |
| PL (1) | PL314980A1 (en) |
| RO (1) | RO115413B1 (en) |
| RU (1) | RU2146141C1 (en) |
| SA (1) | SA94150373B1 (en) |
| SI (1) | SI0734260T2 (en) |
| SK (1) | SK282620B6 (en) |
| UA (1) | UA42745C2 (en) |
| WO (1) | WO1995016448A1 (en) |
| ZA (1) | ZA949900B (en) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020086053A1 (en) * | 1993-12-15 | 2002-07-04 | Smithkline Beecham Plc | Formulations, tablets of paroxetine and process to prepare them |
| SK283608B6 (en) * | 1995-02-06 | 2003-10-07 | Smithkline Beecham Plc | Anhydrous paroxetine hydrochloride, process for its preparation and use |
| US6548084B2 (en) | 1995-07-20 | 2003-04-15 | Smithkline Beecham Plc | Controlled release compositions |
| GB9605828D0 (en) * | 1996-03-20 | 1996-05-22 | Smithkline Beecham Plc | Treatment method |
| US6638948B1 (en) * | 1996-09-09 | 2003-10-28 | Pentech Pharmaceuticals, Inc. | Amorphous paroxetine composition |
| WO1998056787A1 (en) | 1997-06-10 | 1998-12-17 | Synthon B.V. | 4-Phenylpiperidine compounds |
| US5955475A (en) * | 1997-06-30 | 1999-09-21 | Endo Pharmaceuticals Inc. | Process for manufacturing paroxetine solid dispersions |
| US6699882B2 (en) | 1998-03-24 | 2004-03-02 | Smithkline Beecham P.L.C. | Paroxetine compositions |
| US6168805B1 (en) | 1998-05-07 | 2001-01-02 | Endo Pharmaceuticals, Inc. | Aqueous process for manufacturing paroxetine solid dispersions |
| GB9810181D0 (en) * | 1998-05-13 | 1998-07-08 | Smithkline Beecham Plc | Novel formulations |
| DE19821625C1 (en) * | 1998-05-15 | 2000-01-05 | Merck Patent Gmbh | Pharmaceutical preparation |
| CH689805A8 (en) * | 1998-07-02 | 2000-02-29 | Smithkline Beecham Plc | Paroxetine methanesulfonate, process for its preparation and pharmaceutical compositions containing it. |
| WO2000078290A2 (en) * | 1999-06-22 | 2000-12-28 | Smithkline Beecham P.L.C. | Pharmaceutical composition comprising a salt of paroxetine |
| GB0003232D0 (en) * | 2000-02-11 | 2000-04-05 | Smithkline Beecham Plc | Novel composition |
| WO2002017921A2 (en) * | 2000-08-28 | 2002-03-07 | Synthon B.V. | Paroxetine compositions and processes for making the same |
| DE20100529U1 (en) * | 2001-01-11 | 2001-05-10 | Synthon Bv | Pharmaceutical tablet comprising paroxetine mesylate |
| DK1522539T3 (en) | 2001-07-31 | 2007-05-07 | Lundbeck & Co As H | Crystalline composition containing excitalopram |
| PT1440067E (en) * | 2001-10-22 | 2005-02-28 | Synthon Bv | N-FORMYL PAROXETINE DERIVATIVES |
| AU2002359857B8 (en) * | 2001-12-28 | 2009-01-08 | Teva Pharmaceutical Industries Ltd. | A stable pharmaceutical formulation of paroxetine hydrochloride anhydrous and a process for preparation thereof |
| US20040220153A1 (en) * | 2002-09-24 | 2004-11-04 | Jost-Price Edward Roydon | Methods and reagents for the treatment of diseases and disorders associated with increased levels of proinflammatory cytokines |
| US20050266082A1 (en) * | 2004-05-26 | 2005-12-01 | Patel Satishkumar A | Preparation of stable paroxetine HC1 ER tablets using a melt granulation process |
| JP2008504263A (en) * | 2004-06-23 | 2008-02-14 | メルク エンド カムパニー インコーポレーテッド | Estrogen receptor modulator |
| WO2006018318A1 (en) * | 2004-08-18 | 2006-02-23 | Synthon B.V. | Liquid paroxetine compositions |
| US20060039975A1 (en) * | 2004-08-20 | 2006-02-23 | Zalman Vilkov | Paroxetine formulations |
| US20060216345A1 (en) * | 2005-03-24 | 2006-09-28 | Sun Pharmaceutical Industries Limited | Oral pharmaceutical composition including paroxetine |
| US20070112031A1 (en) * | 2005-11-14 | 2007-05-17 | Gant Thomas G | Substituted phenylpiperidines with serotoninergic activity and enhanced therapeutic properties |
| US20080033050A1 (en) * | 2006-08-04 | 2008-02-07 | Richards Patricia Allison Tewe | Method of treating thermoregulatory disfunction with paroxetine |
| US9138430B2 (en) * | 2007-12-27 | 2015-09-22 | Mylan Specialty L.P. | Formulation and method for the release of paroxetine in the large intestine |
| CA2937365C (en) | 2016-03-29 | 2018-09-18 | F. Hoffmann-La Roche Ag | Granulate formulation of 5-methyl-1-phenyl-2-(1h)-pyridone and method of making the same |
| CN109771381B (en) * | 2017-11-13 | 2021-02-19 | 北京福元医药股份有限公司 | Paroxetine medicinal preparation |
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 |
| EP0269303A2 (en) * | 1986-11-11 | 1988-06-01 | Novo Nordisk A/S | Piperidine derivative for treating pain |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50116401A (en) * | 1974-03-04 | 1975-09-11 | ||
| ZA813205B (en) † | 1980-12-05 | 1983-03-30 | Smith Kline French Lab | Dosage units |
| GB8430581D0 (en) * | 1984-12-04 | 1985-01-09 | Ferrosan As | Treatment |
| GB8520154D0 (en) * | 1985-08-10 | 1985-09-18 | Beecham Group Plc | Chemical process |
| EP0223334B1 (en) * | 1985-08-10 | 1991-07-10 | Beecham Group Plc | Process for the preparation of aryl-piperidine carbinols |
| GB8714707D0 (en) * | 1987-06-23 | 1987-07-29 | Beecham Group Plc | Chemical process |
| EP0558679A1 (en) * | 1990-11-24 | 1993-09-08 | BEECHAM GROUP plc | Use of paroxetine for the treatment of senile dementia, bulimia, migraine or anorexia |
| GB9209687D0 (en) * | 1992-05-06 | 1992-06-17 | Smithkline Beecham Plc | Novel process |
| US5776969A (en) * | 1997-02-27 | 1998-07-07 | Eli Lilly And Company | Treatment of sleep disorders |
-
1993
- 1993-12-15 GB GB939325644A patent/GB9325644D0/en active Pending
-
1994
- 1994-12-13 MY MYPI94003326A patent/MY112123A/en unknown
- 1994-12-13 SA SA94150373A patent/SA94150373B1/en unknown
- 1994-12-13 ZA ZA949900A patent/ZA949900B/en unknown
- 1994-12-13 AP APAP/P/1994/000704A patent/AP540A/en active
- 1994-12-13 DZ DZ940132A patent/DZ1835A1/en active
- 1994-12-13 MA MA23723A patent/MA23395A1/en unknown
- 1994-12-14 CA CA002274387A patent/CA2274387A1/en not_active Abandoned
- 1994-12-14 ES ES95904476T patent/ES2132610T5/en not_active Expired - Lifetime
- 1994-12-14 BR BR9408219A patent/BR9408219A/en not_active Application Discontinuation
- 1994-12-14 RU RU96114954A patent/RU2146141C1/en not_active IP Right Cessation
- 1994-12-14 CA CA002274389A patent/CA2274389C/en not_active Expired - Fee Related
- 1994-12-14 HU HU9601665A patent/HUT75880A/en not_active Application Discontinuation
- 1994-12-14 DE DE69419033T patent/DE69419033T2/en not_active Expired - Lifetime
- 1994-12-14 NZ NZ277790A patent/NZ277790A/en not_active IP Right Cessation
- 1994-12-14 EP EP95904476A patent/EP0734260B2/en not_active Expired - Lifetime
- 1994-12-14 RO RO96-01196A patent/RO115413B1/en unknown
- 1994-12-14 WO PCT/EP1994/004164 patent/WO1995016448A1/en not_active Ceased
- 1994-12-14 UA UA96062355A patent/UA42745C2/en unknown
- 1994-12-14 DK DK95904476T patent/DK0734260T4/en active
- 1994-12-14 SK SK756-96A patent/SK282620B6/en not_active IP Right Cessation
- 1994-12-14 AU AU13145/95A patent/AU697982B2/en not_active Ceased
- 1994-12-14 AT AT95904476T patent/ATE180973T1/en not_active IP Right Cessation
- 1994-12-14 CN CN94194457A patent/CN1071116C/en not_active Expired - Fee Related
- 1994-12-14 CA CA002178637A patent/CA2178637C/en not_active Expired - Fee Related
- 1994-12-14 PL PL94314980A patent/PL314980A1/en unknown
- 1994-12-14 CA CA002214575A patent/CA2214575C/en not_active Expired - Fee Related
- 1994-12-14 SI SI9430251T patent/SI0734260T2/en not_active IP Right Cessation
- 1994-12-14 IL IL11197894A patent/IL111978A/en unknown
- 1994-12-14 CZ CZ19961763A patent/CZ287891B6/en not_active IP Right Cessation
- 1994-12-14 JP JP07516534A patent/JP3037757B2/en not_active Expired - Fee Related
- 1994-12-14 KR KR1019960703153A patent/KR100367796B1/en not_active Expired - Fee Related
-
1996
- 1996-06-06 BG BG100648A patent/BG62755B1/en unknown
- 1996-06-12 FI FI962445A patent/FI962445A0/en not_active Application Discontinuation
- 1996-06-14 NO NO962547A patent/NO307366B1/en not_active IP Right Cessation
- 1996-06-14 OA OA60845A patent/OA10297A/en unknown
-
1998
- 1998-06-30 US US09/108,138 patent/US6113944A/en not_active Expired - Fee Related
-
1999
- 1999-08-19 GR GR990402125T patent/GR3031047T3/en unknown
Patent 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 |
| EP0269303A2 (en) * | 1986-11-11 | 1988-06-01 | Novo Nordisk A/S | Piperidine derivative for treating pain |
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