LT5550B - Escitalopramo kristalinė bazė ir burnoje suyrančios tabletės, apimančios escitalopramo bazę - Google Patents
Escitalopramo kristalinė bazė ir burnoje suyrančios tabletės, apimančios escitalopramo bazę Download PDFInfo
- Publication number
- LT5550B LT5550B LT2008005A LT2008005A LT5550B LT 5550 B LT5550 B LT 5550B LT 2008005 A LT2008005 A LT 2008005A LT 2008005 A LT2008005 A LT 2008005A LT 5550 B LT5550 B LT 5550B
- Authority
- LT
- Lithuania
- Prior art keywords
- escitalopram
- base
- free base
- salt
- crystalline
- Prior art date
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- WSEQXVZVJXJVFP-FQEVSTJZSA-N escitalopram Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-FQEVSTJZSA-N 0.000 title description 145
- 229960004341 escitalopram Drugs 0.000 title description 140
- 239000003826 tablet Substances 0.000 description 154
- 239000000203 mixture Substances 0.000 description 90
- 239000002585 base Substances 0.000 description 89
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 66
- 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 61
- 238000000034 method Methods 0.000 description 61
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- WIHMBLDNRMIGDW-BDQAORGHSA-N escitalopram hydrobromide Chemical compound Br.C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WIHMBLDNRMIGDW-BDQAORGHSA-N 0.000 description 17
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
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- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 3
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- 229910052799 carbon Inorganic materials 0.000 description 1
- OFZCIYFFPZCNJE-UHFFFAOYSA-N carisoprodol Chemical compound NC(=O)OCC(C)(CCC)COC(=O)NC(C)C OFZCIYFFPZCNJE-UHFFFAOYSA-N 0.000 description 1
- 229960004587 carisoprodol Drugs 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
- 229960004630 chlorambucil Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000019700 dicalcium phosphate Nutrition 0.000 description 1
- 229940095079 dicalcium phosphate anhydrous Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 229960002563 disulfiram Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HAPOVYFOVVWLRS-UHFFFAOYSA-N ethosuximide Chemical compound CCC1(C)CC(=O)NC1=O HAPOVYFOVVWLRS-UHFFFAOYSA-N 0.000 description 1
- 229960002767 ethosuximide Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229960001031 glucose Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 229960002146 guaifenesin Drugs 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- PKMNZOFQIRXQDO-UHFFFAOYSA-N heptane;hexane Chemical compound CCCCCC.CCCCCCC PKMNZOFQIRXQDO-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960002247 lomustine Drugs 0.000 description 1
- 238000007909 melt granulation Methods 0.000 description 1
- CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical compound COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229960000762 perphenazine Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000011257 shell material Substances 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000008137 solubility enhancer Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IRYJRGCIQBGHIV-UHFFFAOYSA-N trimethadione Chemical compound CN1C(=O)OC(C)(C)C1=O IRYJRGCIQBGHIV-UHFFFAOYSA-N 0.000 description 1
- 229960004453 trimethadione Drugs 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 238000010792 warming 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Emergency Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200500912 | 2005-06-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LT2008005A LT2008005A (en) | 2008-10-27 |
| LT5550B true LT5550B (lt) | 2009-03-25 |
Family
ID=37546630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LT2008005A LT5550B (lt) | 2005-06-22 | 2008-01-21 | Escitalopramo kristalinė bazė ir burnoje suyrančios tabletės, apimančios escitalopramo bazę |
Country Status (39)
| Country | Link |
|---|---|
| EP (3) | EP2385044A1 (de) |
| JP (5) | JP4906852B2 (de) |
| KR (5) | KR20080018191A (de) |
| CN (2) | CN101928269A (de) |
| AR (2) | AR055062A1 (de) |
| AT (3) | AT10983U1 (de) |
| AU (2) | AU2006261452B2 (de) |
| BG (1) | BG66086B1 (de) |
| BR (1) | BRPI0612295A2 (de) |
| CA (2) | CA2646780A1 (de) |
| CY (1) | CY1112392T1 (de) |
| CZ (3) | CZ301286B6 (de) |
| DE (2) | DE602006019961D1 (de) |
| DK (3) | DK1896439T4 (de) |
| EA (2) | EA201001108A1 (de) |
| EE (1) | EE00773U1 (de) |
| ES (2) | ES2319073B1 (de) |
| FI (2) | FI20080548L (de) |
| GB (2) | GB2442160B (de) |
| HR (1) | HRP20110093T4 (de) |
| HU (1) | HUP0800135A3 (de) |
| IL (1) | IL187454A0 (de) |
| IS (1) | IS8705A (de) |
| LT (1) | LT5550B (de) |
| LV (1) | LV13677B (de) |
| MX (1) | MX2007015328A (de) |
| MY (2) | MY143239A (de) |
| NO (2) | NO20080359L (de) |
| PL (2) | PL384185A1 (de) |
| PT (1) | PT1896439E (de) |
| RS (1) | RS51575B2 (de) |
| SG (1) | SG169358A1 (de) |
| SI (1) | SI1896439T2 (de) |
| SK (1) | SK500402007A3 (de) |
| TR (2) | TR200708792T1 (de) |
| TW (2) | TWI347942B (de) |
| UA (1) | UA86536C2 (de) |
| WO (1) | WO2006136169A2 (de) |
| ZA (2) | ZA200711066B (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0123400D0 (en) | 2001-09-28 | 2001-11-21 | Novartis Ag | Organic compounds |
| WO2008059514A2 (en) * | 2006-07-31 | 2008-05-22 | Cadila Healthcare Limited | Process for preparing escitalopram |
| EP2134325A2 (de) * | 2007-03-01 | 2009-12-23 | Aurobindo Pharma Limited | Stabile solide dosierformen eines antidepressivums |
| DK2595979T3 (en) | 2010-07-23 | 2016-05-17 | Lundbeck & Co As H | A process for the purification of pharmaceutically acceptable salts of escitalopram |
| CN103360353A (zh) * | 2013-08-07 | 2013-10-23 | 中国药科大学 | 草酸艾司西酞普兰杂质的制备方法 |
| JP2018016569A (ja) * | 2016-07-26 | 2018-02-01 | 株式会社トクヤマ | （１ｓ）−１−［３−（ジメチルアミノ）プロピル］−１−（４−フルオロフェニル）−１，３−ジヒドロイソベンゾフラン−５−カルボニトリル蓚酸塩の製造方法 |
| WO2018190294A1 (ja) * | 2017-04-10 | 2018-10-18 | 東和薬品株式会社 | エスシタロプラム医薬組成物 |
| CN110711198B (zh) * | 2018-07-12 | 2022-03-15 | 山东大学 | D-甘露糖在制备抗抑郁药物中的应用 |
| KR102331187B1 (ko) | 2019-04-09 | 2021-11-26 | 주식회사 라이트팜텍 | 에스시탈로프람을 함유하는 안정성이 우수한 경구용 액제 조성물 및 그의 제조방법 |
| WO2022153262A1 (en) * | 2021-01-18 | 2022-07-21 | Anton Frenkel | Pharmaceutical dosage form |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4943590A (en) | 1988-06-14 | 1990-07-24 | H. Lundbeck A/S | Pharmaceutically useful (+)-1-(3-dimethylaminopropyl)-1-(4'-fluorophenyl)-1,3-dihydrosobenzofuran-5-carbonitrile and non-toxic acid addition salts thereof |
| WO2004056791A1 (en) | 2002-12-23 | 2004-07-08 | H. Lundbeck A/S | Escitalopram hydrobromide and a method for the preparation thereof |
| WO2005018617A1 (en) | 2003-08-19 | 2005-03-03 | Wyeth | Fast dissolving tablet |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1526331A (en) | 1976-01-14 | 1978-09-27 | Kefalas As | Phthalanes |
| JPH05222041A (ja) * | 1992-02-13 | 1993-08-31 | Mitsubishi Gas Chem Co Inc | アデニン誘導体の精製法 |
| FI962989A0 (fi) * | 1994-01-27 | 1996-07-26 | Univ Oklahoma | Nopeasti liukeneva oraalinen annosmuoto |
| US5607697A (en) * | 1995-06-07 | 1997-03-04 | Cima Labs, Incorporated | Taste masking microparticles for oral dosage forms |
| EP0993524B1 (de) | 1997-06-30 | 2002-11-20 | Beloit Technologies, Inc. | Verfahren und vorrichtung zum auftragen einer beschichtung auf eine bei hoher geschwindigkeit laufende papierbahn |
| TR200000066T2 (tr) | 1997-07-08 | 2000-11-21 | H. Lundbeck A/S | Sitalopram hazırlanması için yöntem. |
| ES2149734T3 (es) | 1997-11-11 | 2003-02-16 | Lundbeck & Co As H | Metodo para la preparacion de citalopram. |
| FR2785538B1 (fr) * | 1998-11-06 | 2004-04-09 | Prographarm Laboratoires | Comprime a delitement rapide perfectionne |
| US20020071864A1 (en) * | 1999-03-25 | 2002-06-13 | Yuhan Corporation | Rapidly disintegrable tablet for oral administration |
| ITMI991579A1 (it) | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| ITMI991581A1 (it) | 1999-06-25 | 2001-01-15 | Lundbeck & Co As H | Metodo per la preparazione di citalopram |
| JP2001226372A (ja) * | 1999-12-06 | 2001-08-21 | Sumika Fine Chemicals Co Ltd | ロサルタンの結晶性または結晶化された酸付加塩およびロサルタンの精製方法 |
| GB2357762B (en) * | 2000-03-13 | 2002-01-30 | Lundbeck & Co As H | Crystalline base of citalopram |
| US7510728B2 (en) * | 2000-10-06 | 2009-03-31 | Takeda Pharmaceutical Company Limited | Solid preparations |
| CN1469737A (zh) * | 2000-10-16 | 2004-01-21 | ��һ��������ҩ��ʽ���� | 口腔内快速崩解的药用组合物及其制备方法 |
| JP3798982B2 (ja) * | 2000-12-22 | 2006-07-19 | ハー・ルンドベック・アクチエゼルスカベット | 純粋なシタロプラムの製造方法 |
| CA2359810C (en) * | 2000-12-28 | 2002-11-05 | H. Lundbeck A/S | Process for the preparation of pure citalopram |
| EA200301195A1 (ru) * | 2001-05-01 | 2004-04-29 | Х. Лундбекк А/С | Применение энантиомерно чистого эсциталопрама |
| US6872405B2 (en) * | 2001-05-10 | 2005-03-29 | Yamanouchi Pharmaceutical Co., Ltd. | Quick-disintegrating tablet in buccal cavity and manufacturing method thereof |
| GB0113842D0 (en) * | 2001-06-07 | 2001-08-01 | Boots Co Plc | Therapeutic agents |
| AR034612A1 (es) * | 2001-06-25 | 2004-03-03 | Lundbeck & Co As H | Proceso para la preparacion del citalopram racemico y/o del s- o r-citalopram mediante la separacion de una mezcla de r- y s-citalopram |
| AR034759A1 (es) | 2001-07-13 | 2004-03-17 | Lundbeck & Co As H | Metodo para la preparacion de escitalopram |
| HRP20031073A2 (en) * | 2001-07-31 | 2004-04-30 | Lundbeck & Co As H | Crystalline composition containing escitalopram |
| IS7239A (is) | 2001-12-14 | 2004-04-29 | H. Lundbeck A/S | Aðferð til framleiðslu á essítalóprami |
| WO2003057132A2 (en) * | 2002-01-07 | 2003-07-17 | Sun Pharmaceutical Industries Limited | Process for the preparation of 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)- 1,3-dihydro-5-isobenzofuran carbonitrile |
| FR2834889B1 (fr) * | 2002-01-18 | 2004-04-02 | Roquette Freres | Forme pharmaceutique solide orodispersible |
| GB0204607D0 (en) * | 2002-02-27 | 2002-04-10 | Matrix Lab Ltd | Process |
| EP1517676A1 (de) * | 2002-05-03 | 2005-03-30 | Skyepharma Canada Inc. | Orale darreichungsformen mit fenofibrat |
| CN1510024A (zh) * | 2002-12-24 | 2004-07-07 | 北京德众万全药物技术开发有限公司 | 可用于制备西酞普兰(s)-对映异构体的新的化合物及其制备方法 |
| DE10305984A1 (de) * | 2003-02-13 | 2004-09-02 | Helm Ag | Salze organischer Säuren mit Clopidogrel und deren Verwendung zur Herstellung phamazeutischer Formulierungen |
| CN1819819B (zh) * | 2003-05-07 | 2011-03-09 | 株式会社三养社 | 用于制备速熔片的高度可塑性颗粒 |
| KR101159617B1 (ko) * | 2003-10-15 | 2012-06-27 | 후지카가쿠고교가부시키가이샤 | 구강내 속붕해성 정제 |
| AU2003282383A1 (en) * | 2003-11-20 | 2005-06-08 | Natco Pharma Limited | A process for the preparation of high purity escitalopram |
| HU227491B1 (en) * | 2003-11-25 | 2011-07-28 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | Tablet containing citalopram hydrogen bromide |
| BRPI0508266A (pt) * | 2004-03-05 | 2007-07-31 | Lundbeck & Co As H | partìculas cristalinas de oxalato de escitalopram, forma de dosagem única sólida, e, métodos para a fabricação de partìculas cristalinas de oxalato de escitalopram e para reduzir a quantidade de hidroxila que contém impurezas no citalopram, escitalopram ou uma mistura não racêmica de r- e s-citalopram |
| EP1877394A1 (de) * | 2005-04-04 | 2008-01-16 | Jubilant Organosys Limited | Verfahren zur herstellung von escitalopram oder seinen säureadditionssalzen |
-
2006
- 2006-06-15 TW TW095121358A patent/TWI347942B/zh not_active IP Right Cessation
- 2006-06-15 TW TW100102601A patent/TWI358407B/zh not_active IP Right Cessation
- 2006-06-21 MY MYPI2010000618A patent/MY143239A/en unknown
- 2006-06-21 MY MYPI20062933A patent/MY143252A/en unknown
- 2006-06-21 AR ARP060102654A patent/AR055062A1/es not_active Application Discontinuation
- 2006-06-22 HU HU0800135A patent/HUP0800135A3/hu unknown
- 2006-06-22 WO PCT/DK2006/000366 patent/WO2006136169A2/en not_active Ceased
- 2006-06-22 DK DK06742481.2T patent/DK1896439T4/en active
- 2006-06-22 TR TR2007/08792T patent/TR200708792T1/xx unknown
- 2006-06-22 CN CN201010286088XA patent/CN101928269A/zh active Pending
- 2006-06-22 PL PL384185A patent/PL384185A1/pl unknown
- 2006-06-22 KR KR1020077028918A patent/KR20080018191A/ko not_active Ceased
- 2006-06-22 CA CA002646780A patent/CA2646780A1/en not_active Abandoned
- 2006-06-22 BR BRPI0612295-7A patent/BRPI0612295A2/pt not_active IP Right Cessation
- 2006-06-22 EP EP10179318A patent/EP2385044A1/de not_active Withdrawn
- 2006-06-22 CA CA2612827A patent/CA2612827C/en not_active Expired - Fee Related
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4943590A (en) | 1988-06-14 | 1990-07-24 | H. Lundbeck A/S | Pharmaceutically useful (+)-1-(3-dimethylaminopropyl)-1-(4'-fluorophenyl)-1,3-dihydrosobenzofuran-5-carbonitrile and non-toxic acid addition salts thereof |
| WO2004056791A1 (en) | 2002-12-23 | 2004-07-08 | H. Lundbeck A/S | Escitalopram hydrobromide and a method for the preparation thereof |
| WO2005018617A1 (en) | 2003-08-19 | 2005-03-03 | Wyeth | Fast dissolving tablet |
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