WO1999058113A2 - Nouvelle formulation contenant de la paroxetine - Google Patents
Nouvelle formulation contenant de la paroxetine Download PDFInfo
- Publication number
- WO1999058113A2 WO1999058113A2 PCT/GB1999/001520 GB9901520W WO9958113A2 WO 1999058113 A2 WO1999058113 A2 WO 1999058113A2 GB 9901520 W GB9901520 W GB 9901520W WO 9958113 A2 WO9958113 A2 WO 9958113A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- paroxetine
- anhydrous
- tablets
- hemihydrate
- paroxetine hydrochloride
- Prior art date
Links
- 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 78
- 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 description 25
- 229960002296 paroxetine Drugs 0.000 title claims description 24
- 239000000203 mixture Substances 0.000 title description 9
- 238000009472 formulation Methods 0.000 title description 7
- 229960005183 paroxetine hydrochloride Drugs 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 claims description 13
- 238000007907 direct compression Methods 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 235000000346 sugar Nutrition 0.000 claims description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 4
- 238000007906 compression Methods 0.000 claims description 4
- 230000006835 compression Effects 0.000 claims description 4
- 239000008101 lactose Substances 0.000 claims description 4
- -1 monosaccharide sugars Chemical class 0.000 claims description 4
- 239000002274 desiccant Substances 0.000 claims description 3
- 238000007908 dry granulation Methods 0.000 claims description 3
- 239000007888 film coating Substances 0.000 claims description 3
- 238000009501 film coating Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229920000881 Modified starch Polymers 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920003124 powdered cellulose Polymers 0.000 claims description 2
- 235000019814 powdered cellulose Nutrition 0.000 claims description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 38
- 235000019359 magnesium stearate Nutrition 0.000 description 19
- 229920003109 sodium starch glycolate Polymers 0.000 description 16
- 229940079832 sodium starch glycolate Drugs 0.000 description 16
- 239000008109 sodium starch glycolate Substances 0.000 description 16
- GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 11
- DMBUODUULYCPAK-UHFFFAOYSA-N 1,3-bis(docosanoyloxy)propan-2-yl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCCCCCC DMBUODUULYCPAK-UHFFFAOYSA-N 0.000 description 5
- OKMWKBLSFKFYGZ-UHFFFAOYSA-N 1-behenoylglycerol Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)CO OKMWKBLSFKFYGZ-UHFFFAOYSA-N 0.000 description 4
- 229940049654 glyceryl behenate Drugs 0.000 description 4
- VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000832 lactitol Substances 0.000 description 3
- 235000010448 lactitol Nutrition 0.000 description 3
- 229960003451 lactitol Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229920002785 Croscarmellose sodium Polymers 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 2
- 229960001681 croscarmellose sodium Drugs 0.000 description 2
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 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
- 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
- 208000020401 Depressive disease Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- 230000002411 adverse Effects 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000007757 hot melt coating Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 201000000484 premenstrual tension Diseases 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
Definitions
- the present invention relates to novel formulations and to the use of the formulations in the treatment and/or prevention of certain disorders
- This compound has been approved for human use and is marketed, in the form of its hydrochloride salt, m many count ⁇ es around the world as an anti-depressant agent
- WO 95/16448 discloses that paroxetine is likely to develop a pink colour unless it is formulated into tablets using a formulation process in which water is absent, such as dry direct compression of paroxetine or dry granulation of paroxetine followed by compression into tablets
- dry was used to denote substantially dry as opposed to the wholesale addition of water which had been previously employed in the wet granulation process
- paroxetine hydrochlo ⁇ de anhydrate has a tendency to convert at least partially to the hemihydrate dunng the tabletting process Although not dangerous, this creates difficulties in establishing and maintaining a reference standard for regulatory and quality control purposes Accordingly, the present invention provides paroxetine hydrochloride. in a form other than the hemihydrate, which is formulated into tablets under conditions such there is no detectable conversion to hemihydrate during the tabletting process.
- the paroxetine hydrochloride may, for example be amorphous or in the form of a crystalline anhydrate.
- excipients which are essentially anhydrous. That is to say, they contain less than 2%, more especially less than 1.5%. preferably less than 1 % water.
- dibasic calcium phosphate anhydrous can be used to form oral swallow tablets with paroxetine hydrochloride anhydrate without undesired conversion to hemihydrate during the tabletting process.
- the tabletting process may for example comprise dry direct compression of paroxetine or dry granulation of paroxetine followed by compression into tablets.
- the tablets are then packaged with a desiccant in order to prevent conversion of anhydrate to hemihydrate on storage.
- the present invention also provides a process for the preparation of paroxetine hydrochloride anhydrate tablets free of detectable hemihydrate which is characterised by the use of conditions such there is no detectable conversion of the anhydrate to hemihydrate during the tabletting process.
- Such conditions can be achieved by the use of essentially anhydrous excipients.
- tabletting can also be carried out under conditions of low relative humiditv
- excipients with the necessary low moisture content suitable for direct compression include materials such as dibasic calcium phosphate anhydrous.
- anhydrous direct compression lactose monosaccharide sugars eg mannitol. disaccharide sugars eg lactitol. powdered cellulose, pregelatinised starch and similar materials.
- Dibasic calcium phosphate anhydrous is commercially available in a pharmaceutically acceptable grade, eg A-TAB (Rhone Poulenc).
- Anhydrous direct compression lactose is commercially available in a pharmaceutically acceptable grade. eg anhydrous direct tabletting (Quest International Inc).
- Direct compression lactilol is commercially available in a pharmaceutically acceptable grade, eg Finlac DC (Xyrofin).
- paroxetine hydrochloride anhydrate is mixed with dibasic calcium phosphate anhydrous, and/or anhydrous direct compression grade lactose(s), and/or microcrystalline cellulose (in particular A-TAB. lactose anhydrous direct tabletting, and Avicel PHI 12 dried to a moisture content of 0.8- 1.5%) in a suitable blender.
- Other pharmaceutically acceptable excipients may also be added such as disintegrants eg sodium starch glycolate, croscarmellose sodium, and colloidal silicon dioxide (in particular Explotab (dried to a moisture content of ⁇ 2%).
- Ac-Di-Sol. and Syloid 244. respectively lubricants such as magnesium stearate; and glidants such as colloidal silicon dioxide, and talc.
- the composition is then mixed and compressed using standard pharmaceutical procedures.
- the tablets can be film coated.
- Standard aqueous film coating is not appropiate for such a moisture sensitive product; however, the tablets can be coated with hydrophobic coating materials, such as glyceryl behenate. using a hot melt coating technique.
- tablet cores are coated with a 2% w/w of glyceryl behenate (in particular Compritol 888). 2% levels of glyceryl behenate do not adversely affect the dissolution of the dosage form in the gastric environment.
- Glyceryl behenate is commercially available in a pharmaceutically acceptable grade, eg Compritol 888 (Gattefosse).
- a modified aqueous film coating procedure using Opadry AMB (Aqueous Moisture Barrier) can also be utilised.
- tablet cores are coated with a 2% w/w of Opadry AMB.
- Opadry AMB is commercially available in a pharmaceutically acceptable grade, eg Opadry OY-B-31006 (Colorcon).
- Coated tablets are then packaged in standard pharmaceutical container/closure presentations, optionally with a desiccant.
- compositional ranges of key excipients on a w/w basis are provided :
- the amounts of lubricants are in the range 0.5 to 2.0%. most preferably 0.5 to 1.0%.
- the disintegrants are controlled in the range 0.5 to 8.0%. most preferably 2.0 to 4.0%.
- the amounts of anhydrous diluents are controlled in the range 50.0 to 95.0%. Mixtures of the principal diluents can be used to assist in flow and compression properties of the formulation.
- the amounts of film coat are controlled in the range 1.0 to 3.0%. most preferably 2.0%.
- 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 used in the formulation is in the form of the hydrochloride anhydrate which may be prepared according to the procedures outlined in WO 96/24595.
- 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.
- 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 prophylactic amount of an oral swallow tablet prepared in accordance with the present invention.
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)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
L'invention concerne un chlorhydrate de paroxétine, sous une forme autre qu'un semi-hydrate, que l'on formule en comprimés dans des conditions telles qu'aucune conversion de la paroxétine en son semi-hydrate n'est détectable au cours du processus de fabrication des comprimés.
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SK1714-2000A SK17142000A3 (sk) | 1998-05-13 | 1999-05-13 | Hydrochlorid paroxetínu vo forme inej než hemihydrát formulovaný do tabliet, spôsob výroby tabliet hydrochloridu paroxetínu a súprava zahrnujúca takéto tablety |
| KR1020007012706A KR20010043574A (ko) | 1998-05-13 | 1999-05-13 | 파록세틴을 함유하는 신규 제형 |
| BR9910401-6A BR9910401A (pt) | 1998-05-13 | 1999-05-13 | Nova formulação contendo paroxetina |
| PL99344573A PL344573A1 (en) | 1998-05-13 | 1999-05-13 | Novel formulation containing paroxetine |
| EA200001174A EA200001174A1 (ru) | 1998-05-13 | 1999-05-13 | Новая готовая препаративная форма, содержащая пароксетин |
| APAP/P/2000/002019A AP2000002019A0 (en) | 1998-05-13 | 1999-05-13 | Novel formulation containing paroxetine. |
| CA002331871A CA2331871A1 (fr) | 1998-05-13 | 1999-05-13 | Nouvelle formulation contenant de la paroxetine |
| AU39409/99A AU3940999A (en) | 1998-05-13 | 1999-05-13 | Novel formulation containing paroxetine |
| IL13959499A IL139594A0 (en) | 1998-05-13 | 1999-05-13 | Novel formulation containing paroxetine |
| EP99922302A EP1077682A2 (fr) | 1998-05-13 | 1999-05-13 | Nouvelle formulation contenant de la paroxetine |
| JP2000547965A JP2002514591A (ja) | 1998-05-13 | 1999-05-13 | 新規なパロキセチンを含む処方 |
| NO20005683A NO20005683L (no) | 1998-05-13 | 2000-11-10 | Ny formulering inneholdende paroxetin |
| BG105010A BG105010A (en) | 1998-05-13 | 2000-11-30 | Medicamentous form containing paroxetine |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9810181.9A GB9810181D0 (en) | 1998-05-13 | 1998-05-13 | Novel formulations |
| GB9810181.9 | 1998-05-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1999058113A2 true WO1999058113A2 (fr) | 1999-11-18 |
| WO1999058113A3 WO1999058113A3 (fr) | 2000-02-17 |
Family
ID=10831927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GB1999/001520 WO1999058113A2 (fr) | 1998-05-13 | 1999-05-13 | Nouvelle formulation contenant de la paroxetine |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1077682A2 (fr) |
| JP (1) | JP2002514591A (fr) |
| KR (1) | KR20010043574A (fr) |
| CN (1) | CN1308521A (fr) |
| AP (1) | AP2000002019A0 (fr) |
| AU (1) | AU3940999A (fr) |
| BG (1) | BG105010A (fr) |
| BR (1) | BR9910401A (fr) |
| CA (1) | CA2331871A1 (fr) |
| EA (1) | EA200001174A1 (fr) |
| GB (1) | GB9810181D0 (fr) |
| HU (1) | HUP0102064A2 (fr) |
| ID (1) | ID28019A (fr) |
| IL (1) | IL139594A0 (fr) |
| NO (1) | NO20005683L (fr) |
| PL (1) | PL344573A1 (fr) |
| SK (1) | SK17142000A3 (fr) |
| TR (1) | TR200003350T2 (fr) |
| WO (1) | WO1999058113A2 (fr) |
| ZA (1) | ZA200006562B (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001058449A1 (fr) * | 2000-02-11 | 2001-08-16 | Smithkline Beecham Plc | Formulation de paroxetine dispersible dans l'eau |
| US6703408B2 (en) * | 2001-10-22 | 2004-03-09 | Synthon Bct Technologies, Llc | N-formyl derivatives of paroxetine |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2359812C (fr) | 2000-11-20 | 2004-02-10 | The Procter & Gamble Company | Formes posologiques pharmaceutiques a couches multiples permettant de reduire l'impact des revetement fractures |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995016448A1 (fr) * | 1993-12-15 | 1995-06-22 | Smithkline Beecham Plc | Comprimes de paroxetine et leur procede de preparation |
| WO1998009963A1 (fr) * | 1996-09-09 | 1998-03-12 | Pentech Pharmaceuticals, Inc. | Composition de paroxetine amorphe |
| WO1998031365A1 (fr) * | 1997-01-15 | 1998-07-23 | Smithkline Beecham Plc | Compositions a base de paroxetine |
| WO1999032092A1 (fr) * | 1997-12-19 | 1999-07-01 | Smithkline Beecham Corporation | Comprimes a dispersion rapide |
-
1998
- 1998-05-13 GB GBGB9810181.9A patent/GB9810181D0/en not_active Ceased
-
1999
- 1999-05-13 KR KR1020007012706A patent/KR20010043574A/ko not_active Withdrawn
- 1999-05-13 EP EP99922302A patent/EP1077682A2/fr not_active Withdrawn
- 1999-05-13 PL PL99344573A patent/PL344573A1/xx unknown
- 1999-05-13 CN CN99808325A patent/CN1308521A/zh active Pending
- 1999-05-13 ID IDW20002347A patent/ID28019A/id unknown
- 1999-05-13 HU HU0102064A patent/HUP0102064A2/hu unknown
- 1999-05-13 CA CA002331871A patent/CA2331871A1/fr not_active Abandoned
- 1999-05-13 JP JP2000547965A patent/JP2002514591A/ja active Pending
- 1999-05-13 EA EA200001174A patent/EA200001174A1/ru unknown
- 1999-05-13 IL IL13959499A patent/IL139594A0/xx unknown
- 1999-05-13 SK SK1714-2000A patent/SK17142000A3/sk unknown
- 1999-05-13 TR TR2000/03350T patent/TR200003350T2/xx unknown
- 1999-05-13 BR BR9910401-6A patent/BR9910401A/pt not_active Application Discontinuation
- 1999-05-13 AP APAP/P/2000/002019A patent/AP2000002019A0/en unknown
- 1999-05-13 AU AU39409/99A patent/AU3940999A/en not_active Abandoned
- 1999-05-13 WO PCT/GB1999/001520 patent/WO1999058113A2/fr not_active Application Discontinuation
-
2000
- 2000-11-10 NO NO20005683A patent/NO20005683L/no not_active Application Discontinuation
- 2000-11-13 ZA ZA200006562A patent/ZA200006562B/en unknown
- 2000-11-30 BG BG105010A patent/BG105010A/xx unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995016448A1 (fr) * | 1993-12-15 | 1995-06-22 | Smithkline Beecham Plc | Comprimes de paroxetine et leur procede de preparation |
| WO1998009963A1 (fr) * | 1996-09-09 | 1998-03-12 | Pentech Pharmaceuticals, Inc. | Composition de paroxetine amorphe |
| WO1998031365A1 (fr) * | 1997-01-15 | 1998-07-23 | Smithkline Beecham Plc | Compositions a base de paroxetine |
| WO1999032092A1 (fr) * | 1997-12-19 | 1999-07-01 | Smithkline Beecham Corporation | Comprimes a dispersion rapide |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001058449A1 (fr) * | 2000-02-11 | 2001-08-16 | Smithkline Beecham Plc | Formulation de paroxetine dispersible dans l'eau |
| AU2001232079B2 (en) * | 2000-02-11 | 2004-11-25 | Smithkline Beecham Plc | Water dispersible formulation of paroxetine |
| US6703408B2 (en) * | 2001-10-22 | 2004-03-09 | Synthon Bct Technologies, Llc | N-formyl derivatives of paroxetine |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1308521A (zh) | 2001-08-15 |
| KR20010043574A (ko) | 2001-05-25 |
| BR9910401A (pt) | 2001-01-09 |
| WO1999058113A3 (fr) | 2000-02-17 |
| HUP0102064A2 (hu) | 2002-05-29 |
| ZA200006562B (en) | 2002-02-13 |
| EP1077682A2 (fr) | 2001-02-28 |
| TR200003350T2 (tr) | 2001-03-21 |
| ID28019A (id) | 2001-05-03 |
| AU3940999A (en) | 1999-11-29 |
| EA200001174A1 (ru) | 2001-06-25 |
| SK17142000A3 (sk) | 2001-06-11 |
| GB9810181D0 (en) | 1998-07-08 |
| JP2002514591A (ja) | 2002-05-21 |
| NO20005683L (no) | 2000-12-05 |
| AP2000002019A0 (en) | 2000-12-31 |
| CA2331871A1 (fr) | 1999-11-18 |
| NO20005683D0 (no) | 2000-11-10 |
| IL139594A0 (en) | 2002-02-10 |
| BG105010A (en) | 2001-07-31 |
| PL344573A1 (en) | 2001-11-05 |
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