DE69000240T2 - Nifedipine enthaltende zusammensetzungen und verfahren zu ihrer herstellung. - Google Patents
Nifedipine enthaltende zusammensetzungen und verfahren zu ihrer herstellung.Info
- Publication number
- DE69000240T2 DE69000240T2 DE9090301005T DE69000240T DE69000240T2 DE 69000240 T2 DE69000240 T2 DE 69000240T2 DE 9090301005 T DE9090301005 T DE 9090301005T DE 69000240 T DE69000240 T DE 69000240T DE 69000240 T2 DE69000240 T2 DE 69000240T2
- Authority
- DE
- Germany
- Prior art keywords
- nifedipine
- polyvinylpyrrolidone
- particles
- weight
- pharmaceutical preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 title claims abstract description 63
- 229960001597 nifedipine Drugs 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims description 23
- 239000000203 mixture Substances 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000002245 particle Substances 0.000 claims abstract description 44
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 35
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract description 35
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 33
- 239000003085 diluting agent Substances 0.000 claims abstract description 21
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 14
- GUBGYTABKSRVRQ-QKKXKWKRSA-N lactose group Chemical group OC1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](O2)CO)[C@H](O1)CO GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000008101 lactose Substances 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 3
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 2
- 238000004090 dissolution Methods 0.000 abstract description 11
- 239000007909 solid dosage form Substances 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- 238000010348 incorporation Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000009472 formulation Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000013081 microcrystal Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 206010002383 Angina Pectoris Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000013268 sustained release Methods 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- 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
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- -1 aliphatic alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 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
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/167—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface
- A61K9/1676—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface having a drug-free core with discrete complete coating layer containing drug
-
- 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
- A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
- A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898903328A GB8903328D0 (en) | 1989-02-14 | 1989-02-14 | Nifedipine-containing pharmaceutical compositions and process for the preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69000240D1 DE69000240D1 (de) | 1992-09-10 |
| DE69000240T2 true DE69000240T2 (de) | 1993-02-11 |
Family
ID=10651674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE9090301005T Expired - Fee Related DE69000240T2 (de) | 1989-02-14 | 1990-01-31 | Nifedipine enthaltende zusammensetzungen und verfahren zu ihrer herstellung. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5145683A (enExample) |
| EP (1) | EP0385582B1 (enExample) |
| JP (1) | JPH07112974B2 (enExample) |
| AT (1) | ATE79032T1 (enExample) |
| AU (1) | AU626130B2 (enExample) |
| CA (1) | CA2008972C (enExample) |
| DE (1) | DE69000240T2 (enExample) |
| DK (1) | DK0385582T3 (enExample) |
| ES (1) | ES2052168T3 (enExample) |
| FI (1) | FI95347C (enExample) |
| GB (1) | GB8903328D0 (enExample) |
| GR (1) | GR3005477T3 (enExample) |
| IE (1) | IE64682B1 (enExample) |
| NO (1) | NO175925C (enExample) |
| NZ (1) | NZ232287A (enExample) |
| PH (1) | PH26850A (enExample) |
| ZA (1) | ZA90904B (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5624683A (en) * | 1986-08-06 | 1997-04-29 | Eisai Co., Ltd. | Sustained-release multi-granule tablet |
| GB9200607D0 (en) * | 1992-01-13 | 1992-03-11 | Ethical Pharma Ltd | Pharmaceutical compositions containing nifedipine and process for the preparation thereof |
| US6726930B1 (en) * | 1993-09-09 | 2004-04-27 | Penwest Pharmaceuticals Co. | Sustained release heterodisperse hydrogel systems for insoluble drugs |
| US5773025A (en) | 1993-09-09 | 1998-06-30 | Edward Mendell Co., Inc. | Sustained release heterodisperse hydrogel systems--amorphous drugs |
| US5455046A (en) * | 1993-09-09 | 1995-10-03 | Edward Mendell Co., Inc. | Sustained release heterodisperse hydrogel systems for insoluble drugs |
| US5662933A (en) * | 1993-09-09 | 1997-09-02 | Edward Mendell Co., Inc. | Controlled release formulation (albuterol) |
| DE59410044D1 (de) * | 1994-12-29 | 2002-03-21 | Shire Deutschland Gmbh & Co Kg | Pharmazeutische zubereitungen, enthaltend nifedipin und verfahren zu ihrer herstellung |
| US5871776A (en) * | 1995-01-31 | 1999-02-16 | Mehta; Atul M. | Controlled-release nifedipine |
| CN1049114C (zh) * | 1995-12-07 | 2000-02-09 | 上海华联制药公司 | 一种制备缓释药物制剂的方法 |
| JP3148256B2 (ja) | 1996-07-08 | 2001-03-19 | エドワード メンデル カンパニー．，インコーポレーテッド | 高用量難溶性薬物用持続放出マトリックス |
| EP0852141A1 (en) | 1996-08-16 | 1998-07-08 | J.B. Chemicals & Pharmaceuticals Ltd. | Nifedipine containing pharmaceutical extended release composition and a process for the preparation thereof |
| IT1284604B1 (it) * | 1996-09-27 | 1998-05-21 | Roberto Valducci | Composizioni farmaceutiche a rilascio controllato per somministrazione orale contenenti nifedipina come sostanza attiva |
| US5837379A (en) * | 1997-01-31 | 1998-11-17 | Andrx Pharmaceuticals, Inc. | Once daily pharmaceutical tablet having a unitary core |
| US5922352A (en) * | 1997-01-31 | 1999-07-13 | Andrx Pharmaceuticals, Inc. | Once daily calcium channel blocker tablet having a delayed release core |
| IN186245B (enExample) | 1997-09-19 | 2001-07-14 | Ranbaxy Lab Ltd | |
| US6056977A (en) | 1997-10-15 | 2000-05-02 | Edward Mendell Co., Inc. | Once-a-day controlled release sulfonylurea formulation |
| US6485748B1 (en) | 1997-12-12 | 2002-11-26 | Andrx Pharmaceuticals, Inc. | Once daily pharmaceutical tablet having a unitary core |
| US6168806B1 (en) | 1999-03-05 | 2001-01-02 | Fang-Yu Lee | Orally administrable nifedipine pellet and process for the preparation thereof |
| US20040115134A1 (en) * | 1999-06-22 | 2004-06-17 | Elan Pharma International Ltd. | Novel nifedipine compositions |
| JP4627825B2 (ja) * | 1999-09-27 | 2011-02-09 | 三生医薬株式会社 | 被包粒状物質及びその製造方法 |
| HK1042427A1 (zh) * | 1999-09-30 | 2002-08-16 | Penwest Pharmaceuticals Co. | 用於高溶度药物的持续释放基质方法 |
| RU2188635C2 (ru) * | 1999-10-12 | 2002-09-10 | Открытое акционерное общество "Щелковский витаминный завод" | Композиционный состав лекарственного средства - блокатора медленных кальциевых каналов |
| US7364752B1 (en) | 1999-11-12 | 2008-04-29 | Abbott Laboratories | Solid dispersion pharamaceutical formulations |
| EP1175205B1 (en) * | 1999-11-12 | 2006-06-14 | Abbott Laboratories | Solid dispersion comprising ritonavir, fenofibrate or griseofulvin |
| DE10026698A1 (de) * | 2000-05-30 | 2001-12-06 | Basf Ag | Selbstemulgierende Wirkstoffformulierung und Verwendung dieser Formulierung |
| KR20030034171A (ko) * | 2001-07-06 | 2003-05-01 | 엔도 파마슈티걸즈, 인크. | 옥시모르폰 제어 방출 제형 |
| US8377952B2 (en) | 2003-08-28 | 2013-02-19 | Abbott Laboratories | Solid pharmaceutical dosage formulation |
| US8025899B2 (en) | 2003-08-28 | 2011-09-27 | Abbott Laboratories | Solid pharmaceutical dosage form |
| WO2008067164A2 (en) * | 2006-11-15 | 2008-06-05 | Abbott Laboratories | Solid pharmaceutical dosage formulations |
| GB2460915B (en) * | 2008-06-16 | 2011-05-25 | Biovascular Inc | Controlled release compositions of agents that reduce circulating levels of platelets and methods therefor |
| RU2629843C1 (ru) * | 2016-05-24 | 2017-09-04 | федеральное государственное автономное образовательное учреждение высшего образования Первый Московский государственный медицинский университет имени И.М. Сеченова Министерства здравоохранения Российской Федерации (Сеченовский университет) | Способ получения мази нифедипина (варианты) |
| CN109172534B (zh) * | 2018-10-23 | 2020-08-07 | 迪沙药业集团有限公司 | 一种硝苯地平缓释片剂组合物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1579818A (en) * | 1977-06-07 | 1980-11-26 | Yamanouchi Pharma Co Ltd | Nifedipine-containing solid preparation composition |
| US4285665A (en) * | 1978-05-08 | 1981-08-25 | Johnson, Matthey & Co., Limited | Engines |
| DE3033919A1 (de) * | 1980-09-09 | 1982-04-22 | Bayer Ag, 5090 Leverkusen | Feste arzneizubereitungen enthaltend nifedipin und verfahren zu ihrer herstellung |
| JPS5846019A (ja) * | 1981-09-14 | 1983-03-17 | Kanebo Ltd | 持続性ニフエジピン製剤 |
| DE3318649A1 (de) * | 1983-05-21 | 1984-11-22 | Bayer Ag, 5090 Leverkusen | Zweiphasenformulierung |
| FR2556964A1 (fr) * | 1983-12-23 | 1985-06-28 | Ile De France | Nouvelles formes galeniques du sulpiride utilisables par voie orale |
| DE3424553A1 (de) * | 1984-07-04 | 1986-01-09 | Bayer Ag, 5090 Leverkusen | Feste arzneizubereitungen mit dihydropyridinen und verfahren zu ihrer herstellung |
| IT1178511B (it) * | 1984-09-14 | 1987-09-09 | Pharmatec Spa | Procedimento per la preparazione di una forma solida per uso orale a base di nifedipina con rilascio |
| IT1187751B (it) * | 1985-10-15 | 1987-12-23 | Eurand Spa | Procedimento per la preparazione di formulazioni solidi di nifedipina ad elevata biodisponibilita' e ad effetto prolungato e formulazioni cosi' ottenute |
| SE457326B (sv) * | 1986-02-14 | 1988-12-19 | Lejus Medical Ab | Foerfarande foer framstaellning av en snabbt soenderfallande kaerna innehaallande bl a mikrokristallin cellulosa |
-
1989
- 1989-02-14 GB GB898903328A patent/GB8903328D0/en active Pending
-
1990
- 1990-01-25 IE IE28690A patent/IE64682B1/en not_active IP Right Cessation
- 1990-01-26 NO NO900370A patent/NO175925C/no unknown
- 1990-01-30 US US07/472,659 patent/US5145683A/en not_active Expired - Lifetime
- 1990-01-30 NZ NZ232287A patent/NZ232287A/en unknown
- 1990-01-31 DE DE9090301005T patent/DE69000240T2/de not_active Expired - Fee Related
- 1990-01-31 AU AU48937/90A patent/AU626130B2/en not_active Ceased
- 1990-01-31 AT AT90301005T patent/ATE79032T1/de not_active IP Right Cessation
- 1990-01-31 ES ES90301005T patent/ES2052168T3/es not_active Expired - Lifetime
- 1990-01-31 DK DK90301005.6T patent/DK0385582T3/da active
- 1990-01-31 EP EP90301005A patent/EP0385582B1/en not_active Expired - Lifetime
- 1990-01-31 CA CA002008972A patent/CA2008972C/en not_active Expired - Fee Related
- 1990-02-07 ZA ZA90904A patent/ZA90904B/xx unknown
- 1990-02-08 FI FI900633A patent/FI95347C/fi not_active IP Right Cessation
- 1990-02-09 PH PH40039A patent/PH26850A/en unknown
- 1990-02-13 JP JP2032325A patent/JPH07112974B2/ja not_active Expired - Lifetime
-
1992
- 1992-08-20 GR GR920401816T patent/GR3005477T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2008972C (en) | 1996-09-03 |
| NO175925B (no) | 1994-09-26 |
| AU626130B2 (en) | 1992-07-23 |
| EP0385582A1 (en) | 1990-09-05 |
| DE69000240D1 (de) | 1992-09-10 |
| NZ232287A (en) | 1992-01-29 |
| GB8903328D0 (en) | 1989-04-05 |
| IE900286L (en) | 1990-08-14 |
| NO175925C (no) | 1995-01-04 |
| FI95347B (fi) | 1995-10-13 |
| FI95347C (fi) | 1996-01-25 |
| NO900370L (no) | 1990-08-15 |
| US5145683A (en) | 1992-09-08 |
| EP0385582B1 (en) | 1992-08-05 |
| ATE79032T1 (de) | 1992-08-15 |
| PH26850A (en) | 1992-11-05 |
| JPH07112974B2 (ja) | 1995-12-06 |
| DK0385582T3 (da) | 1992-09-14 |
| FI900633A0 (fi) | 1990-02-08 |
| NO900370D0 (no) | 1990-01-26 |
| GR3005477T3 (enExample) | 1993-05-24 |
| CA2008972A1 (en) | 1990-08-14 |
| IE64682B1 (en) | 1995-08-23 |
| JPH02235815A (ja) | 1990-09-18 |
| AU4893790A (en) | 1990-08-23 |
| ES2052168T3 (es) | 1994-07-01 |
| ZA90904B (en) | 1991-06-26 |
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