PT90760B - Processo para a preparacao de complexos beta-ciclodextrina e de sais de ibuprofen e composicoes farmaceuticas que os contem - Google Patents
Processo para a preparacao de complexos beta-ciclodextrina e de sais de ibuprofen e composicoes farmaceuticas que os contem Download PDFInfo
- Publication number
- PT90760B PT90760B PT90760A PT9076089A PT90760B PT 90760 B PT90760 B PT 90760B PT 90760 A PT90760 A PT 90760A PT 9076089 A PT9076089 A PT 9076089A PT 90760 B PT90760 B PT 90760B
- Authority
- PT
- Portugal
- Prior art keywords
- ibuprofen
- beta
- cyclodextrin
- water
- solution
- Prior art date
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- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical class CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 title claims abstract description 76
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical class OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims description 20
- 229960001680 ibuprofen Drugs 0.000 claims abstract description 61
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 43
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims abstract description 40
- 239000001116 FEMA 4028 Substances 0.000 claims abstract description 39
- 229960004853 betadex Drugs 0.000 claims abstract description 39
- 159000000000 sodium salts Chemical class 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 28
- 239000000243 solution Substances 0.000 claims description 21
- 238000001694 spray drying Methods 0.000 claims description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 239000007921 spray Substances 0.000 claims description 6
- 239000004475 Arginine Substances 0.000 claims description 5
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 5
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 5
- 159000000003 magnesium salts Chemical class 0.000 claims description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 4
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 4
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- 239000007864 aqueous solution Substances 0.000 claims description 4
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- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims description 4
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- 235000019341 magnesium sulphate Nutrition 0.000 claims description 2
- 229940091250 magnesium supplement Drugs 0.000 claims description 2
- IAKLPCRFBAZVRW-XRDLMGPZSA-L magnesium;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoate;hydrate Chemical compound O.[Mg+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O IAKLPCRFBAZVRW-XRDLMGPZSA-L 0.000 claims description 2
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
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- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005303 weighing 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Nanotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Medical Informatics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB888813682A GB8813682D0 (en) | 1988-06-09 | 1988-06-09 | Pharmaceutical compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT90760A PT90760A (pt) | 1989-12-29 |
| PT90760B true PT90760B (pt) | 1994-10-31 |
Family
ID=10638367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT90760A PT90760B (pt) | 1988-06-09 | 1989-06-06 | Processo para a preparacao de complexos beta-ciclodextrina e de sais de ibuprofen e composicoes farmaceuticas que os contem |
Country Status (18)
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3827974A1 (de) * | 1988-08-18 | 1990-02-22 | Boehringer Mannheim Gmbh | Kombinationspraeparate von proteinkinase-c-inhibitoren mit lipiden, lipid-analoga, cytostatica oder inhibitoren von phospholipasen |
| MY106598A (en) * | 1988-08-31 | 1995-06-30 | Australian Commercial Res & Development Ltd | Compositions and methods for drug delivery and chromatography. |
| DE3922441A1 (de) * | 1989-07-07 | 1991-01-17 | Pharmatrans Sanaq Ag | Ibuprofen- und s-(+)-ibuprofen-zubereitungen und verfahren zu ihrer herstellung |
| US5262179A (en) * | 1989-09-13 | 1993-11-16 | Nicholas Kiwi Pty Ltd. | Non-effervescent ibuprofen compositions |
| FR2660195B1 (fr) * | 1990-03-28 | 1994-10-07 | Crinex Sa Laboratoires | Composition pharmaceutique a macher, antiinflammatoire et/ou analgesique. |
| EP0505180B1 (en) * | 1991-03-22 | 1996-10-09 | Merck & Co. Inc. | High-content ibuprofen lysinate pharmaceutical formulation |
| ATE196426T1 (de) * | 1991-06-21 | 2000-10-15 | Takeda Chemical Industries Ltd | Zyklodextrin-zusammensetzung enthaltend fumagillol-derivate |
| US5321014A (en) * | 1991-06-28 | 1994-06-14 | The United States Of America As Represented By The Department Of Health And Human Services | Molecular encapsulation and delivery of alkenes alkynes and long chain alkanes, to living mammalian cells |
| IT1255007B (it) * | 1991-07-01 | 1995-10-11 | Altergon Sa | Sale solubile dell'ibuprofen c0n n-(2-idrossietil) pirrolidina e composizioni farmaceutiche che li contengono. |
| GB9207990D0 (en) * | 1992-04-10 | 1992-05-27 | Smithkline Beecham Plc | Pharmaceutical composition |
| IT1272149B (it) * | 1993-03-26 | 1997-06-11 | Zambon Spa | Composizione farmeceutiche ad attivita' analgesica |
| HU210922B (en) * | 1993-05-24 | 1995-09-28 | Europharmaceuticals Sa | Nimesulide alkali salt cyclodextrin inclusion complexes their preparation and pharmaceutical compositions containing them |
| CN1088600C (zh) * | 1993-07-31 | 2002-08-07 | 史密丝克莱恩比彻姆有限公司 | 布洛芬－β－环糊精配合物的用途 |
| US5582351A (en) * | 1993-08-09 | 1996-12-10 | Tsau; Josef | Convenient to use aspartame and method of making |
| GB9316580D0 (en) * | 1993-08-10 | 1993-09-29 | Smithkline Beecham Plc | Pharmaceutical composition |
| US5866162A (en) * | 1993-08-10 | 1999-02-02 | Smithkline Beecham P.L.C. | Pharmaceutical composition containing a drug/β-cyclodextrin complex in combination with an acid-base couple |
| ZA949715B (en) * | 1993-12-14 | 1996-06-06 | Lilly Co Eli | Aqueous solution inclusion complexes of benzothiophene compounds with water soluble cyclodextrins and pharmaceutical formulations and methods thereof |
| US5646131A (en) * | 1994-02-22 | 1997-07-08 | The Arab Company For Drug Industries And Medical Applicances (Acdima) | Method for solubilizing drugs using cyclodextrins and carboxylic acids |
| WO1995032737A1 (en) * | 1994-05-27 | 1995-12-07 | Farmarc Nederland Bv | Pharmaceutical composition |
| BE1008307A3 (fr) * | 1994-06-16 | 1996-04-02 | Europharmaceuticals Sa | Sel de nimesulide hydrosoluble, solution aqueuse le contenant, sa preparation et son utilisation. |
| ZA959469B (en) * | 1994-11-15 | 1996-05-15 | South African Druggists Ltd | Pharmaceutical composition |
| US5942501A (en) * | 1996-08-16 | 1999-08-24 | Collaborative Laboratories, Inc. | Cyclodextrin derivative complex |
| IT1301966B1 (it) | 1998-07-30 | 2000-07-20 | Zambon Spa | Composizioni farmaceutiche ad attivita' analgesica |
| US6287603B1 (en) * | 1999-09-16 | 2001-09-11 | Nestec S.A. | Cyclodextrin flavor delivery systems |
| ES2171110B1 (es) * | 2000-03-03 | 2003-06-16 | Aplicaciones Farmacodinamicas | Composicion farmaceutica a base de ibuprofeno y procedimiento para su preparacion. |
| US7141555B2 (en) * | 2000-12-19 | 2006-11-28 | Cephalon, Inc. | Modafinil compound and cyclodextrin mixtures |
| US7704975B2 (en) * | 2000-12-19 | 2010-04-27 | Cephalon, Inc. | Modafinil compound and cyclodextrin mixtures |
| US6727286B2 (en) | 2001-11-02 | 2004-04-27 | Cumberland Pharmaceuticals Inc. | Pharmaceutical composition of 2-(4-isobutylphenyl) propionic acid |
| KR100451485B1 (ko) * | 2002-03-28 | 2004-10-06 | 주식회사종근당 | 푸마질롤 유도체 또는 그 염의 포접 화합물, 및 이를포함하는 약제학적 조성물 |
| US20060233873A1 (en) * | 2003-01-24 | 2006-10-19 | Julien Meissonnier | Dispersion of taste masked crystals or granules of active substances, chewable soft capsules filled with said dispersion, and process for preparing same |
| FR2850275B1 (fr) * | 2003-01-24 | 2005-04-08 | Scherer Technologies Inc R P | Capsules molles a macher contenant une substance active a gout masque |
| US20050137262A1 (en) * | 2003-12-22 | 2005-06-23 | Hu Patrick C. | Highly concentrated pourable aqueous solutions of potassium ibuprofen, their preparation and their uses |
| PL381799A1 (pl) * | 2004-06-07 | 2007-07-09 | Strides Arcolab Limited | Kompozycja farmaceutyczna zawierająca trwały i klarowny roztwór leku przeciwzapalnego w miękkiej kapsułce żelatynowej i sposób jej wytwarzania |
| GB2423710A (en) * | 2005-03-01 | 2006-09-06 | Boots Healthcare Int Ltd | Lozenge production process |
| KR100730393B1 (ko) * | 2005-06-10 | 2007-06-20 | 한국콜마 주식회사 | 이부프로펜 및 아르기닌을 함유하는 약학 조성물의제조방법 |
| EP1942877A4 (en) * | 2005-11-02 | 2011-09-14 | Teikoku Pharma Usa Inc | ORGANOLEPTICALLY ACCEPTABLE IBUPROFEN ORAL DOSAGE FORMULATIONS, METHODS OF PREPARATION AND USE THEREOF |
| WO2007109057A2 (en) * | 2006-03-16 | 2007-09-27 | Novartis Ag | Solid dosage form containing a taste masked active agent |
| FR2914187B1 (fr) * | 2007-03-28 | 2011-01-21 | Pf Medicament | Complexes d'ibuprofene, de cyclodextrines et d'agents ternaires, et leurs utilisations en pharmaceutique. |
| WO2011001228A1 (en) * | 2008-08-14 | 2011-01-06 | Shasun Chemicals And Drugs Limited | Aryl alkyl carboxylic acid salts, process for preparation and dosage forms |
| EP2238973A1 (en) | 2009-04-07 | 2010-10-13 | Cephalon France | Lyophilized preparations of proteasome inhibitors |
| EP2253329B1 (en) * | 2009-04-27 | 2016-09-21 | Laboratorio de Aplicaciones Farmacodinamicas, S.A. | Ibuprofen lysinate oral suspension |
| ES2347754B8 (es) * | 2009-04-27 | 2012-06-04 | Laboratorio De Aplicaciones Farmacodinamicas, S.A | Suspension oral de lisinato de ibuprofeno |
| TW201038296A (en) * | 2009-04-27 | 2010-11-01 | Aplicaciones Farmacodinamicas S A Lab De | Ibuprofen lysinate oral suspension |
| TWI542344B (zh) * | 2009-06-22 | 2016-07-21 | 惠氏有限責任公司 | 異丁苯丙酸鈉錠及製備包含異丁苯丙酸鈉之醫藥組合物之方法 |
| CN101978955A (zh) * | 2010-11-05 | 2011-02-23 | 航天中心医院 | 右旋布洛芬氨基酸盐片剂及其制备方法 |
| US10098964B2 (en) | 2015-03-12 | 2018-10-16 | The Board Of Trustees Of The University Of Illinois | Inclusion complexes and methods for making the same |
| CN114588107B (zh) * | 2022-04-06 | 2023-04-18 | 河北一品生物医药有限公司 | 一种布洛芬赖氨酸盐注射液及其制备方法 |
| GR1010732B (el) * | 2023-06-02 | 2024-07-25 | Ιουλια Κλεωνος Τσετη | Φαρμακευτικη συνθεση ιβουπροφαινης και παρακεταμολης για απο του στοματος χορηγηση |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5646837A (en) * | 1979-09-27 | 1981-04-28 | Kowa Yakuhin Kogyo Kk | Preparation of ibuprofen clathrate compound |
| DE3346123A1 (de) * | 1983-12-21 | 1985-06-27 | Janssen Pharmaceutica, N.V., Beerse | Pharmazeutische praeparate von in wasser schwerloeslichen oder instabilen arzneistoffen und verfahren zu ihrer herstellung |
| US4795698A (en) * | 1985-10-04 | 1989-01-03 | Immunicon Corporation | Magnetic-polymer particles |
| GB8613688D0 (en) * | 1986-06-05 | 1986-07-09 | Euro Celtique Sa | Pharmaceutical composition |
| CA1298290C (en) * | 1987-01-09 | 1992-03-31 | Herand M. Markarian | Solution ibuprofen complexes, compositions and processes for preparing the same |
-
1988
- 1988-06-09 GB GB888813682A patent/GB8813682D0/en active Pending
-
1989
- 1989-05-18 AU AU34927/89A patent/AU609988B2/en not_active Ceased
- 1989-05-19 NZ NZ229204A patent/NZ229204A/en unknown
- 1989-05-24 GB GB8911938A patent/GB2219585B/en not_active Expired - Lifetime
- 1989-05-24 ZA ZA893913A patent/ZA893913B/xx unknown
- 1989-05-25 US US07/356,691 patent/US5019563A/en not_active Expired - Lifetime
- 1989-05-29 CA CA000600940A patent/CA1320192C/en not_active Expired - Fee Related
- 1989-06-01 AT AT89305535T patent/ATE83924T1/de not_active IP Right Cessation
- 1989-06-01 EP EP89305535A patent/EP0346006B1/en not_active Expired - Lifetime
- 1989-06-01 ES ES89305535T patent/ES2052914T3/es not_active Expired - Lifetime
- 1989-06-01 DE DE8989305535T patent/DE68904121T2/de not_active Expired - Fee Related
- 1989-06-06 PT PT90760A patent/PT90760B/pt not_active IP Right Cessation
- 1989-06-06 JP JP1143961A patent/JPH02243649A/ja active Pending
- 1989-06-07 FI FI892780A patent/FI93692C/fi not_active IP Right Cessation
- 1989-06-07 NO NO892340A patent/NO175039B/no unknown
- 1989-06-08 DK DK280789A patent/DK280789A/da not_active Application Discontinuation
- 1989-06-08 KR KR1019890007835A patent/KR910000138A/ko not_active Ceased
- 1989-06-12 IE IE175789A patent/IE61616B1/en not_active IP Right Cessation
-
1992
- 1992-12-31 GR GR920403100T patent/GR3006729T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ229204A (en) | 1992-03-26 |
| FI93692B (fi) | 1995-02-15 |
| NO892340L (no) | 1989-12-11 |
| GB2219585B (en) | 1991-11-06 |
| NO175039C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1994-08-24 |
| IE891757L (en) | 1989-12-09 |
| DE68904121D1 (de) | 1993-02-11 |
| DK280789A (da) | 1989-12-12 |
| GB8911938D0 (en) | 1989-07-12 |
| ZA893913B (en) | 1990-02-28 |
| DE68904121T2 (de) | 1993-05-06 |
| GB2219585A (en) | 1989-12-13 |
| ES2052914T3 (es) | 1994-07-16 |
| IE61616B1 (en) | 1994-11-16 |
| EP0346006A1 (en) | 1989-12-13 |
| FI892780L (fi) | 1989-12-10 |
| NO175039B (no) | 1994-05-16 |
| AU609988B2 (en) | 1991-05-09 |
| ATE83924T1 (de) | 1993-01-15 |
| FI93692C (fi) | 1995-05-26 |
| KR910000138A (ko) | 1991-01-29 |
| GR3006729T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-06-30 |
| AU3492789A (en) | 1989-12-14 |
| GB8813682D0 (en) | 1988-07-13 |
| DK280789D0 (da) | 1989-06-08 |
| FI892780A0 (fi) | 1989-06-07 |
| US5019563A (en) | 1991-05-28 |
| JPH02243649A (ja) | 1990-09-27 |
| PT90760A (pt) | 1989-12-29 |
| CA1320192C (en) | 1993-07-13 |
| NO892340D0 (no) | 1989-06-07 |
| EP0346006B1 (en) | 1992-12-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG3A | Patent granted, date of granting |
Effective date: 19940419 |
|
| MM3A | Annulment or lapse |
Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 19961031 |