WO1994022435A1 - A new composition containing selegiline - Google Patents
A new composition containing selegiline Download PDFInfo
- Publication number
- WO1994022435A1 WO1994022435A1 PCT/FI1994/000128 FI9400128W WO9422435A1 WO 1994022435 A1 WO1994022435 A1 WO 1994022435A1 FI 9400128 W FI9400128 W FI 9400128W WO 9422435 A1 WO9422435 A1 WO 9422435A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- selegiline
- acid
- lubricant
- composition according
- composition
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 40
- 229960003946 selegiline Drugs 0.000 title claims abstract description 16
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 title claims abstract description 16
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 25
- 239000000314 lubricant Substances 0.000 claims abstract description 19
- 235000019359 magnesium stearate Nutrition 0.000 claims abstract description 16
- -1 fatty acid esters Chemical class 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 11
- 239000000194 fatty acid Substances 0.000 claims abstract description 11
- 229930195729 fatty acid Natural products 0.000 claims abstract description 11
- 235000015112 vegetable and seed oil Nutrition 0.000 claims abstract description 10
- 239000008158 vegetable oil Substances 0.000 claims abstract description 9
- 239000008247 solid mixture Substances 0.000 claims abstract description 6
- IYETZZCWLLUHIJ-UHFFFAOYSA-N methyl-(1-phenylpropan-2-yl)-prop-2-ynylazanium;chloride Chemical compound Cl.C#CCN(C)C(C)CC1=CC=CC=C1 IYETZZCWLLUHIJ-UHFFFAOYSA-N 0.000 claims description 24
- 229960003678 selegiline hydrochloride Drugs 0.000 claims description 24
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
- 239000002385 cottonseed oil Substances 0.000 claims description 4
- 235000012343 cottonseed oil Nutrition 0.000 claims description 4
- 235000002906 tartaric acid Nutrition 0.000 claims description 4
- 239000011975 tartaric acid Substances 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 3
- DMBUODUULYCPAK-UHFFFAOYSA-N 1,3-bis(docosanoyloxy)propan-2-yl docosanoate Chemical group CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCCCCCC DMBUODUULYCPAK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004135 Bone phosphate Substances 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 230000000368 destabilizing effect Effects 0.000 abstract description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000008187 granular material Substances 0.000 description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 235000015165 citric acid Nutrition 0.000 description 5
- 229960004106 citric acid Drugs 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000000843 powder Substances 0.000 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 description 4
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 229940016286 microcrystalline cellulose Drugs 0.000 description 4
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 4
- 239000008108 microcrystalline cellulose Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 229920002261 Corn starch 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
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 235000019759 Maize starch Nutrition 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 229920003081 Povidone K 30 Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 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 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 1
- 241001440269 Cutina Species 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 102000010909 Monoamine Oxidase Human genes 0.000 description 1
- 108010062431 Monoamine oxidase Proteins 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229960003805 amantadine Drugs 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229960002303 citric acid monohydrate Drugs 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000007907 direct compression Methods 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
Definitions
- the invention relates to a new stable composition suitable for oral administration comprising a pharmaceutically acceptable acid addition salt of selegiline e.g. the hydrochloride.
- Selegiline ((-) N-(1-phenyl isopropyl)-N-methyl-N-propionyl amine) is a
- the invention relates to a new stable solid composition suitable for oral administration comprising a pharmaceutically acceptable acid addition salt of selegiline e.g. selegiline hydrochloride. It was observed during long term o stability studies of different formulations of selegiline hydrochloride that tablets containing magnesium stearate are not stable. Under stressed conditions i.e. heat (60 °C) combined with humidity (relative humidity of 75 %), the instability increases i.e. the content of selegiline hydrochloride decreases.
- the present invention overcomes the destabilizing effect of stearic acid salts by decreasing the amount of magnesium stearate below a certain level, e.g. by replacing all or a substantial part of the magnesium stearate with another lubricant such as a fatty acid ester, polyethylene glycol, colloidal silicon dioxide or vegetable oil.
- Tables 2, 3 and 4 show different compositions of selegiline hydrochloride according to the invention: In table 2 magnesium strearate is replaced with glyceryl tribehenate (Compritol) and in table 3 with cotton seed oil (Sterotex). In table 4 a pharmaceutically acceptable acid (citric acid) is added keeping the amount of magnesium stearate at the same level as that of the conventional oral compositions.
- glyceryl tribehenate Compritol
- a pharmaceutically acceptable acid citric acid
- compositions were prepared as follows: Selegiline hydrochloride, lactose (or mannitol and maize starch, respectively) and polyvidone were sieved and mixed in a granulator. The powder blend was moistened and granulated with ethanol. The granules were dried and sieved. Microcrystalline cellulose, citric acid (when used) and the lubricant (Compritol, Sterotex and magnesium stearate, respectively) were sieved and mixed with the granules. The powder was tabletted using 6 mm (diameter) punches.
- Table 2 A composition containing Compritol.
- Table 4 A composition containing citric acid.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Emergency Medicine (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP94911961A EP0643578A1 (en) | 1993-04-02 | 1994-03-31 | A new composition containing selegiline |
| DE0643578T DE643578T1 (de) | 1993-04-02 | 1994-03-31 | Neue zusammensetzung, die selegilin enthält. |
| FI945716A FI945716A0 (fi) | 1993-04-02 | 1994-03-31 | Uusi selegiliiniä sisältävä valmiste |
| AU64300/94A AU663995C (en) | 1993-04-02 | 1994-03-31 | A new composition containing selegiline |
| NO944631A NO944631D0 (no) | 1993-04-02 | 1994-12-01 | Sammensetning inneholdende selegilin |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9301112-0 | 1993-04-02 | ||
| SE19939301112A SE9301112D0 (sv) | 1993-04-02 | 1993-04-02 | A new composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1994022435A1 true WO1994022435A1 (en) | 1994-10-13 |
Family
ID=20389464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/FI1994/000128 WO1994022435A1 (en) | 1993-04-02 | 1994-03-31 | A new composition containing selegiline |
Country Status (8)
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996018386A1 (en) * | 1994-12-14 | 1996-06-20 | Enbalt Trading Limited | Pharmaceutical tablet formulations for direct compression |
| WO1996040094A1 (en) * | 1995-06-07 | 1996-12-19 | Deprenyl Animal Health, Inc. | Use of selegiline to treat hearing loss in mammals |
| FR2753904A1 (fr) * | 1996-10-01 | 1998-04-03 | Gattefosse Ets Sa | Composition pharmaceutique a liberation modifiee de principe actif, comportant une matrice, et procede de fabrication |
| DE19743323A1 (de) * | 1997-09-30 | 1999-04-01 | Iip Inst Fuer Ind Pharmazie Fo | Feste Arzneimittelzusammensetzung auf der Grundlage von Selegilin |
| US5919482A (en) * | 1994-12-23 | 1999-07-06 | Orion-Yhtyma Oy | Gelatine capsule containing selegiline or derivative and paraffin as carrier |
| US6242002B1 (en) | 1998-03-31 | 2001-06-05 | Arzneimittelwerk Dresden Gmbh | Effervescent formulations |
| US6635278B1 (en) | 1998-12-15 | 2003-10-21 | Gilead Sciences, Inc. | Pharmaceutical formulations |
| WO2013107441A1 (de) * | 2012-01-18 | 2013-07-25 | Stada Arzneimittel Ag | Verfahren zur herstellung einer festen pharmazeutischen zusammensetzung, enthaltend den wirkstoff rasagilin |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2346069C (en) * | 1998-10-07 | 2008-09-09 | Kyowa Hakko Kogyo Co., Ltd. | Tablet and tablet production method |
| JP5258144B2 (ja) * | 2004-12-21 | 2013-08-07 | 株式会社分子生理化学研究所 | 吸収性の改善された固形状のコエンザイムｑ１０経口製剤の製造方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3137125A (en) * | 1962-02-26 | 1964-06-16 | Kyryluk William Frederick | Solar motor |
| US4018543A (en) * | 1975-09-19 | 1977-04-19 | The Raymond Lee Organization, Inc. | Whirlwind power system |
| US4224528A (en) * | 1979-05-14 | 1980-09-23 | Argo William H | Solar thermal and wind energy power source |
| US4935639A (en) * | 1988-08-23 | 1990-06-19 | Yeh Dong An | Revolving power tower |
| US5300817A (en) * | 1993-04-16 | 1994-04-05 | Baird William R | Solar venturi turbine |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU193662B (en) * | 1983-12-20 | 1987-11-30 | Chinoin Gyogyszer Es Vegyeszet | Process for producing synergetic pharmaceutical composition of antidepressive aktivity |
| DE3710966A1 (de) * | 1986-04-16 | 1987-12-03 | Degussa | Synergistische kombination von amantadin und selegilin |
| HU208484B (en) * | 1988-08-17 | 1993-11-29 | Chinoin Gyogyszer Es Vegyeszet | Process for producing pharmaceutical composition containing acid additional salt of selegilin as active component for treating schisofrenia |
| US5190763A (en) * | 1990-05-07 | 1993-03-02 | Alza Corporation | Dosage form indicated for the management of abnormal posture, tremor and involuntary movement |
| US5057321A (en) * | 1990-06-13 | 1991-10-15 | Alza Corporation | Dosage form comprising drug and maltodextrin |
-
1993
- 1993-04-02 SE SE19939301112A patent/SE9301112D0/xx unknown
-
1994
- 1994-03-31 EP EP96110727A patent/EP0739628A2/en not_active Withdrawn
- 1994-03-31 JP JP6521719A patent/JP2752792B2/ja not_active Expired - Fee Related
- 1994-03-31 CA CA002137164A patent/CA2137164C/en not_active Expired - Fee Related
- 1994-03-31 NZ NZ263568A patent/NZ263568A/en unknown
- 1994-03-31 ES ES94911961T patent/ES2083936T1/es active Pending
- 1994-03-31 DE DE0643578T patent/DE643578T1/de active Pending
- 1994-03-31 EP EP94911961A patent/EP0643578A1/en not_active Withdrawn
- 1994-03-31 WO PCT/FI1994/000128 patent/WO1994022435A1/en not_active Application Discontinuation
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3137125A (en) * | 1962-02-26 | 1964-06-16 | Kyryluk William Frederick | Solar motor |
| US4018543A (en) * | 1975-09-19 | 1977-04-19 | The Raymond Lee Organization, Inc. | Whirlwind power system |
| US4224528A (en) * | 1979-05-14 | 1980-09-23 | Argo William H | Solar thermal and wind energy power source |
| US4935639A (en) * | 1988-08-23 | 1990-06-19 | Yeh Dong An | Revolving power tower |
| US5300817A (en) * | 1993-04-16 | 1994-04-05 | Baird William R | Solar venturi turbine |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996018386A1 (en) * | 1994-12-14 | 1996-06-20 | Enbalt Trading Limited | Pharmaceutical tablet formulations for direct compression |
| EP1057479A1 (en) * | 1994-12-14 | 2000-12-06 | Enbalt Trading Limited | Pharmaceutical tablet formulations for direct compression |
| US5919482A (en) * | 1994-12-23 | 1999-07-06 | Orion-Yhtyma Oy | Gelatine capsule containing selegiline or derivative and paraffin as carrier |
| WO1996040094A1 (en) * | 1995-06-07 | 1996-12-19 | Deprenyl Animal Health, Inc. | Use of selegiline to treat hearing loss in mammals |
| FR2753904A1 (fr) * | 1996-10-01 | 1998-04-03 | Gattefosse Ets Sa | Composition pharmaceutique a liberation modifiee de principe actif, comportant une matrice, et procede de fabrication |
| DE19743323A1 (de) * | 1997-09-30 | 1999-04-01 | Iip Inst Fuer Ind Pharmazie Fo | Feste Arzneimittelzusammensetzung auf der Grundlage von Selegilin |
| DE19743323C2 (de) * | 1997-09-30 | 2000-05-25 | Iip Inst Fuer Ind Pharmazie Fo | Feste Arzneimittelzusammensetzung auf der Grundlage von Selegilin |
| US6242002B1 (en) | 1998-03-31 | 2001-06-05 | Arzneimittelwerk Dresden Gmbh | Effervescent formulations |
| US6635278B1 (en) | 1998-12-15 | 2003-10-21 | Gilead Sciences, Inc. | Pharmaceutical formulations |
| WO2013107441A1 (de) * | 2012-01-18 | 2013-07-25 | Stada Arzneimittel Ag | Verfahren zur herstellung einer festen pharmazeutischen zusammensetzung, enthaltend den wirkstoff rasagilin |
Also Published As
| Publication number | Publication date |
|---|---|
| SE9301112D0 (sv) | 1993-04-02 |
| DE643578T1 (de) | 1996-09-19 |
| CA2137164A1 (en) | 1994-10-13 |
| JP2752792B2 (ja) | 1998-05-18 |
| AU663995B2 (en) | 1995-10-26 |
| CA2137164C (en) | 1997-04-08 |
| JPH07506845A (ja) | 1995-07-27 |
| ES2083936T1 (es) | 1996-05-01 |
| AU6430094A (en) | 1994-10-24 |
| EP0643578A1 (en) | 1995-03-22 |
| NZ263568A (en) | 1996-01-26 |
| EP0739628A2 (en) | 1996-10-30 |
| EP0739628A3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1996-11-27 |
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