NO316946B1 - Syklopeptider, fremgangsmate for fremstilling derav, farmasoytiske preparater som inneholder syklopeptidene, fremgangsmate for fremstilling derav, samt anvendelse av syklopeptidene til fremstilling av legemidler - Google Patents
Syklopeptider, fremgangsmate for fremstilling derav, farmasoytiske preparater som inneholder syklopeptidene, fremgangsmate for fremstilling derav, samt anvendelse av syklopeptidene til fremstilling av legemidler Download PDFInfo
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- NO316946B1 NO316946B1 NO19963853A NO963853A NO316946B1 NO 316946 B1 NO316946 B1 NO 316946B1 NO 19963853 A NO19963853 A NO 19963853A NO 963853 A NO963853 A NO 963853A NO 316946 B1 NO316946 B1 NO 316946B1
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Classifications
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- C07K7/64—Cyclic peptides containing only normal peptide links
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Oncology (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Communicable Diseases (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Toxicology (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19534177A DE19534177A1 (de) | 1995-09-15 | 1995-09-15 | Cyclische Adhäsionsinhibitoren |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO963853D0 NO963853D0 (no) | 1996-09-13 |
| NO963853L NO963853L (no) | 1997-03-17 |
| NO316946B1 true NO316946B1 (no) | 2004-07-05 |
Family
ID=7772215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19963853A NO316946B1 (no) | 1995-09-15 | 1996-09-13 | Syklopeptider, fremgangsmate for fremstilling derav, farmasoytiske preparater som inneholder syklopeptidene, fremgangsmate for fremstilling derav, samt anvendelse av syklopeptidene til fremstilling av legemidler |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6001961A (fr) |
| EP (1) | EP0770622B1 (fr) |
| JP (3) | JP4115550B2 (fr) |
| KR (1) | KR100438244B1 (fr) |
| CN (1) | CN1203090C (fr) |
| AR (1) | AR003574A1 (fr) |
| AT (1) | ATE189461T1 (fr) |
| AU (1) | AU717574B2 (fr) |
| BR (1) | BR9603751A (fr) |
| CA (1) | CA2185489C (fr) |
| CO (1) | CO4750841A1 (fr) |
| CZ (1) | CZ286713B6 (fr) |
| DE (2) | DE19534177A1 (fr) |
| DK (1) | DK0770622T3 (fr) |
| ES (1) | ES2144179T3 (fr) |
| GR (1) | GR3033293T3 (fr) |
| HU (1) | HU224614B1 (fr) |
| ID (1) | ID18770A (fr) |
| MX (1) | MX9604100A (fr) |
| NO (1) | NO316946B1 (fr) |
| PL (1) | PL185125B1 (fr) |
| PT (1) | PT770622E (fr) |
| RU (1) | RU2157379C2 (fr) |
| SI (1) | SI0770622T1 (fr) |
| SK (1) | SK282391B6 (fr) |
| TR (1) | TR199600716A2 (fr) |
| TW (1) | TW517064B (fr) |
| UA (1) | UA49799C2 (fr) |
| ZA (1) | ZA967768B (fr) |
Families Citing this family (84)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5753230A (en) | 1994-03-18 | 1998-05-19 | The Scripps Research Institute | Methods and compositions useful for inhibition of angiogenesis |
| US7053041B1 (en) | 1996-05-31 | 2006-05-30 | The Scripps Research Institute | Methods and compositions useful for inhibition of αvβ5mediated angiogenesis |
| DE19613933A1 (de) * | 1996-04-06 | 1997-10-09 | Merck Patent Gmbh | Cyclische Adhäsionsinhibitoren |
| AU733303C (en) | 1996-05-31 | 2002-08-08 | Scripps Research Institute, The | Methods and compositions useful for inhibition of angiogenesis |
| PL330240A1 (en) * | 1996-05-31 | 1999-05-10 | Scripps Research Inst | Methods and compositions useful in inhibiting angiogenesis in which alphavbeta5 acts as intermediary |
| WO1998037914A1 (fr) * | 1997-02-26 | 1998-09-03 | Toray Industries, Inc. | Remedes contre l'hepatite |
| DE19842415A1 (de) * | 1998-09-16 | 2000-03-23 | Merck Patent Gmbh | Pharmazeutische Zubereitung |
| WO2000038715A2 (fr) | 1998-12-23 | 2000-07-06 | G.D. Searle & Co. | Procede d'utilisation d'un antagoniste de l'integrine et radiotherapie en tant que polytherapie dans le traitement des neoplasies |
| US6521593B1 (en) * | 1999-02-01 | 2003-02-18 | Childrens Hospital Los Angeles | Methods for inhibiting brain tumor growth |
| RU2236251C2 (ru) * | 1999-02-12 | 2004-09-20 | Дзе Скриппс Рисерч Инститьют | Способы лечения опухолей и метастазов с использованием комбинации антиангиогенной терапии и иммунотерапии |
| UA71608C2 (en) * | 1999-03-11 | 2004-12-15 | Merck Patent Gmbh | A method for producing the cyclic pentapeptide |
| NZ515686A (en) | 1999-06-01 | 2005-01-28 | Biogen Inc | A blocking monoclonal antibody to integrin VLA-1 and its use for the treatment of inflammatory disorders such as arthritis |
| US6518244B2 (en) | 2000-03-09 | 2003-02-11 | Intimax Corporation | Combinations of heparin cofactor II agonist and platelet IIb/IIIa antagonist, and uses thereof |
| KR20030061390A (ko) * | 2000-11-01 | 2003-07-18 | 메르크 파텐트 게엠베하 | 안구 질환 치료용 조성물 및 방법 |
| UA75898C2 (en) * | 2000-11-14 | 2006-06-15 | Merck Patent Gmbh | Method for prophylaxis and treatment of eye diseases using antagonist of integrin receptors |
| WO2002055106A2 (fr) * | 2001-01-09 | 2002-07-18 | Merck Patent Gmbh | Polytherapie faisant appel a des inhibiteurs de recepteurs tyrosine kinase et a des inhibiteurs d'angiogenese |
| KR100927670B1 (ko) | 2001-04-13 | 2009-11-20 | 바이오겐 아이덱 엠에이 인코포레이티드 | Ｖｌａ-1에 대한 항체들 |
| AU2002316855B2 (en) | 2001-04-24 | 2008-03-13 | Merck Patent Gmbh | Combination therapy using anti-angiogenic agents and TNFalpha |
| CN1658894A (zh) * | 2002-02-14 | 2005-08-24 | 默克专利股份有限公司 | 用于治疗眼病的方法和组合物 |
| DE10228049A1 (de) * | 2002-06-24 | 2004-01-15 | Merck Patent Gmbh | Flüssige Zubereitung enthaltend Oligopeptide |
| TWI476206B (zh) | 2003-07-18 | 2015-03-11 | Amgen Inc | 對肝細胞生長因子具專一性之結合劑 |
| DE10337863A1 (de) * | 2003-08-18 | 2005-03-17 | Merck Patent Gmbh | Verwendung von Chromen-4-on-Derivaten |
| RU2463308C2 (ru) | 2005-12-22 | 2012-10-10 | НоваБиотикс Лимитед | Циклические противомикробные пептиды |
| US9181303B2 (en) | 2005-12-22 | 2015-11-10 | Novabiotics Limited | Treatment of bacterial infections with cyclic antimicrobial peptides |
| US20080108664A1 (en) * | 2005-12-23 | 2008-05-08 | Liu Belle B | Solid-state form of AMG 706 and pharmaceutical compositions thereof |
| ES2425396T3 (es) | 2006-01-18 | 2013-10-15 | Merck Patent Gmbh | Terapia específica usando ligandos de integrinas para el tratamiento del cáncer |
| EP1987023B1 (fr) * | 2006-02-10 | 2010-11-24 | Amgen, Inc | Formes hydrate d'amg706 |
| JP5496658B2 (ja) * | 2006-05-25 | 2014-05-21 | バイオジェン・アイデック・エムエイ・インコーポレイテッド | 脳卒中を処置する方法 |
| PE20121506A1 (es) | 2006-07-14 | 2012-11-26 | Amgen Inc | Compuestos triazolopiridinas como inhibidores de c-met |
| DK2101805T3 (da) | 2007-01-18 | 2013-01-21 | Merck Patent Gmbh | Integrinligander til anvendelse i behandling af cancer |
| US20080241270A1 (en) * | 2007-03-30 | 2008-10-02 | Neal Robert A | Fluid composition for inhibiting surgical adhesion formation and related method of production |
| WO2008143933A1 (fr) * | 2007-05-15 | 2008-11-27 | Cvpath Institute, Inc. | Revêtements d'endoprothèse vasculaire avec peptides sélectifs d'intégrine ou mimétiques |
| JP5341889B2 (ja) | 2007-07-17 | 2013-11-13 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 操作された抗αＶインテグリンハイブリッド抗体 |
| GB0718957D0 (en) * | 2007-09-28 | 2007-11-07 | Ge Healthcare Ltd | Optical imaging agents |
| CL2008002444A1 (es) | 2007-08-21 | 2009-09-04 | Amgen Inc | Anticuerpo o fragmento del mismo que se une a la proteina c-fms humana; molecula de acido nucleico que la codifica; vector y celula huesped; metodo de elaboracion; composicion farmaceutica que la comprende; y su uso para tratar o prevenir una condicion asociada con c-fms en un paciente. |
| US20110027209A1 (en) * | 2008-04-08 | 2011-02-03 | Merck Patent Gesellschaft | Compositions Containing Cyclic Peptides And Methods Of Use |
| CA2747937C (fr) | 2008-12-23 | 2019-02-26 | Merck Patent Gmbh | Biomarqueurs pour inhibiteurs ayant une activite antiangiogenique |
| CA2762652C (fr) | 2009-05-20 | 2018-10-02 | Merck Patent Gmbh | Nouvelles substances solides a base d'acide [2s,5r,8s,11s)-5-benzyl-11-(3-guanidino-propyl)-8-isopropyl-7-methyl-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentaaza-cyclopentadec-2-yl] acet ique et procedes de production associes |
| JP2012528079A (ja) | 2009-05-25 | 2012-11-12 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 癌を治療するためのインテグリンリガンドの連続投与 |
| NZ601109A (en) * | 2009-12-10 | 2014-06-27 | Merck Patent Gmbh | Pharmaceutical composition comprising oligopeptides, preferably cilengitide |
| EP2407478A1 (fr) | 2010-07-14 | 2012-01-18 | GENETADI Biotech, S.L. | Nouveaux cyclotetrapeptides ayant des propriétés pro-angiogenèse |
| CN103153328A (zh) | 2010-07-16 | 2013-06-12 | 默克专利股份有限公司 | 肽在乳腺癌和/或骨转移灶的治疗中的用途 |
| US20130202652A1 (en) * | 2010-07-30 | 2013-08-08 | Alnylam Pharmaceuticals, Inc. | Methods and compositions for delivery of active agents |
| WO2012069149A1 (fr) | 2010-11-23 | 2012-05-31 | Merck Patent Gmbh | Solution contenant des oligopeptides cycliques |
| PL2672994T3 (pl) | 2011-02-11 | 2018-11-30 | Merck Patent Gmbh | Przeciwciało przeciwko integrynie alfa-v do leczenia raka prostaty |
| WO2012110200A1 (fr) | 2011-02-18 | 2012-08-23 | Merck Patent Gmbh | Peptide cyclique, cyclo-(l‑arginyl-glycyl-l‑aspartyl-d‑phénylalanyl- n‑méthyl-l‑valyle), compositions associées et utilisation dans des méthodes de traitement de la maladie du greffon contre l'hôte |
| WO2012146729A1 (fr) * | 2011-04-29 | 2012-11-01 | Philipps-Universität Marburg | Peptides lasso utilisés en tant qu'échafaudages pour la greffe de peptides |
| WO2012167870A1 (fr) | 2011-06-09 | 2012-12-13 | Merck Patent Gmbh | Traitement de cancers et de métastases à l'aide de suspensions de cilengitide dans un véhicule |
| WO2013025939A2 (fr) | 2011-08-16 | 2013-02-21 | Indiana University Research And Technology Corporation | Composés et méthodes de traitement du cancer par l'inhibition du récepteur de l'urokinase |
| ES2732243T3 (es) | 2012-02-16 | 2019-11-21 | Santarus Inc | Composiciones farmacéuticas de anticuerpos ANTI-VLA1 (CD49A) |
| AR090263A1 (es) | 2012-03-08 | 2014-10-29 | Hoffmann La Roche | Terapia combinada de anticuerpos contra el csf-1r humano y las utilizaciones de la misma |
| WO2014036022A1 (fr) | 2012-08-29 | 2014-03-06 | Amgen Inc. | Composés quinazolinones et leurs dérivés |
| HRP20211836T1 (hr) | 2013-09-24 | 2022-03-04 | Fujifilm Corporation | Novi spoj koji sadrži dušik ili njegova sol, ili njegov metalni kompleks |
| SG10201902609TA (en) | 2015-03-25 | 2019-04-29 | Fujifilm Corp | Method for producing novel nitrogen-containing compound or salt thereof, and production intermediate of same |
| AU2016340763B2 (en) * | 2015-10-23 | 2021-04-22 | Jai Prakash | Integrin binding peptides and uses thereof |
| JP7034914B2 (ja) | 2015-11-23 | 2022-03-14 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 線維症および／または線維性疾患の治療のための抗α－ｖインテグリン抗体 |
| EP3207937A1 (fr) | 2016-02-17 | 2017-08-23 | Royal College of Surgeons in Ireland | Procédé de traitement ou de prévention d'une sepsie |
| MX2019007643A (es) | 2016-12-22 | 2019-09-09 | Amgen Inc | Benzoisotiazol, isotiazolo[3,4-b]piridina, quinazolina, ftalazina, pirido[2,3-d]piridazina y derivados de pirido[2,3-d]pirimidina como inhibirores de kras g12c para tratar el cancer de pulmon, pancreatico o colorrectal. |
| JOP20190272A1 (ar) | 2017-05-22 | 2019-11-21 | Amgen Inc | مثبطات kras g12c وطرق لاستخدامها |
| EP4403175A3 (fr) | 2017-09-08 | 2024-10-02 | Amgen Inc. | Inhibiteurs de kras g12c et leurs procédés d'utilisation |
| WO2019213516A1 (fr) | 2018-05-04 | 2019-11-07 | Amgen Inc. | Inhibiteurs de kras g12c et leurs procédés d'utilisation |
| AU2019262599B2 (en) | 2018-05-04 | 2023-10-12 | Amgen Inc. | KRAS G12C inhibitors and methods of using the same |
| EP3790886B1 (fr) | 2018-05-10 | 2024-06-26 | Amgen Inc. | Inhibiteurs du kras g12c pour le traitement du cancer |
| AU2019278998B2 (en) | 2018-06-01 | 2023-11-09 | Amgen Inc. | KRAS G12C inhibitors and methods of using the same |
| CA3099799A1 (fr) | 2018-06-11 | 2019-12-19 | Amgen Inc. | Inhibiteurs de kras g12c pour le traitement du cancer |
| US11285156B2 (en) | 2018-06-12 | 2022-03-29 | Amgen Inc. | Substituted piperazines as KRAS G12C inhibitors |
| JP7516029B2 (ja) | 2018-11-16 | 2024-07-16 | アムジエン・インコーポレーテツド | Ｋｒａｓ ｇ１２ｃ阻害剤化合物の重要な中間体の改良合成法 |
| US11053226B2 (en) | 2018-11-19 | 2021-07-06 | Amgen Inc. | KRAS G12C inhibitors and methods of using the same |
| JP7377679B2 (ja) | 2018-11-19 | 2023-11-10 | アムジエン・インコーポレーテツド | がん治療のためのｋｒａｓｇ１２ｃ阻害剤及び１種以上の薬学的に活性な追加の薬剤を含む併用療法 |
| MX2021007157A (es) | 2018-12-20 | 2021-08-16 | Amgen Inc | Heteroarilamidas utiles como inhibidores de kif18a. |
| MA54543A (fr) | 2018-12-20 | 2022-03-30 | Amgen Inc | Inhibiteurs de kif18a |
| WO2020132651A1 (fr) | 2018-12-20 | 2020-06-25 | Amgen Inc. | Inhibiteurs de kif18a |
| AU2020232616A1 (en) | 2019-03-01 | 2021-09-09 | Revolution Medicines, Inc. | Bicyclic heterocyclyl compounds and uses thereof |
| EP3738593A1 (fr) | 2019-05-14 | 2020-11-18 | Amgen, Inc | Dosage d'inhibiteur de kras pour le traitement de cancers |
| KR20220011670A (ko) | 2019-05-21 | 2022-01-28 | 암젠 인크 | 고체 상태 형태 |
| US20220372018A1 (en) | 2019-08-02 | 2022-11-24 | Amgen Inc. | Kif18a inhibitors |
| US20220281843A1 (en) | 2019-08-02 | 2022-09-08 | Amgen Inc. | Kif18a inhibitors |
| US20230192681A1 (en) | 2019-11-14 | 2023-06-22 | Amgen Inc. | Improved synthesis of kras g12c inhibitor compound |
| JP2023509701A (ja) | 2020-01-07 | 2023-03-09 | レヴォリューション・メディスンズ，インコーポレイテッド | Ｓｈｐ２阻害剤投薬およびがんを処置する方法 |
| WO2021224234A1 (fr) | 2020-05-04 | 2021-11-11 | Helmholtz-Zentrum für Infektionsforschung GmbH | Utilisation antivirale de cilengitide |
| AU2021345111A1 (en) | 2020-09-15 | 2023-04-06 | Revolution Medicines, Inc. | Indole derivatives as Ras inhibitors in the treatment of cancer |
| US20240082347A1 (en) | 2021-01-22 | 2024-03-14 | Royal College Of Surgeons In Ireland | Treatment of coronavirus |
| AR127308A1 (es) | 2021-10-08 | 2024-01-10 | Revolution Medicines Inc | Inhibidores ras |
| WO2023172940A1 (fr) | 2022-03-08 | 2023-09-14 | Revolution Medicines, Inc. | Méthodes de traitement du cancer du poumon réfractaire immunitaire |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4792525A (en) * | 1982-08-04 | 1988-12-20 | La Jolla Cancer Research Foundation | Tetrapeptide |
| US4578079A (en) * | 1982-08-04 | 1986-03-25 | La Jolla Cancer Research Foundation | Tetrapeptide |
| US4517686A (en) * | 1982-08-04 | 1985-05-21 | La Jolla Cancer Research Foundation | Polypeptide |
| US4589881A (en) * | 1982-08-04 | 1986-05-20 | La Jolla Cancer Research Foundation | Polypeptide |
| US4508921A (en) * | 1984-06-28 | 1985-04-02 | Merck & Co., Inc. | Process for preparation of alpha-alkyl amino acids |
| JP2945680B2 (ja) * | 1988-09-09 | 1999-09-06 | 旭硝子株式会社 | ペプチド誘導体およびその用途 |
| DE4310643A1 (de) * | 1993-04-01 | 1994-10-06 | Merck Patent Gmbh | Cyclische Adhäsionsinhibitoren |
-
1995
- 1995-09-15 DE DE19534177A patent/DE19534177A1/de not_active Withdrawn
-
1996
- 1996-08-31 EP EP96113972A patent/EP0770622B1/fr not_active Expired - Lifetime
- 1996-08-31 DE DE59604363T patent/DE59604363D1/de not_active Expired - Lifetime
- 1996-08-31 SI SI9630172T patent/SI0770622T1/xx unknown
- 1996-08-31 PT PT96113972T patent/PT770622E/pt unknown
- 1996-08-31 ES ES96113972T patent/ES2144179T3/es not_active Expired - Lifetime
- 1996-08-31 DK DK96113972T patent/DK0770622T3/da active
- 1996-08-31 AT AT96113972T patent/ATE189461T1/de active
- 1996-09-10 CZ CZ19962643A patent/CZ286713B6/cs not_active IP Right Cessation
- 1996-09-10 AU AU65580/96A patent/AU717574B2/en not_active Ceased
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- 1996-09-12 SK SK1167-96A patent/SK282391B6/sk not_active IP Right Cessation
- 1996-09-12 TR TR96/00716A patent/TR199600716A2/xx unknown
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- 1996-09-13 AR ARP960104340A patent/AR003574A1/es active IP Right Grant
- 1996-09-13 PL PL96316071A patent/PL185125B1/pl not_active IP Right Cessation
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- 1996-09-13 CA CA002185489A patent/CA2185489C/fr not_active Expired - Fee Related
- 1996-09-13 HU HU9602507A patent/HU224614B1/hu not_active IP Right Cessation
- 1996-09-13 UA UA96093558A patent/UA49799C2/uk unknown
- 1996-09-13 ZA ZA967768A patent/ZA967768B/xx unknown
- 1996-09-13 RU RU96118225/14A patent/RU2157379C2/ru not_active IP Right Cessation
- 1996-09-13 NO NO19963853A patent/NO316946B1/no not_active IP Right Cessation
- 1996-09-13 JP JP26372596A patent/JP4115550B2/ja not_active Expired - Fee Related
- 1996-09-14 KR KR1019960039979A patent/KR100438244B1/ko not_active IP Right Cessation
- 1996-09-16 TW TW085111375A patent/TW517064B/zh not_active IP Right Cessation
- 1996-09-16 US US08/694,387 patent/US6001961A/en not_active Expired - Lifetime
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2000
- 2000-04-21 GR GR20000400975T patent/GR3033293T3/el unknown
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2006
- 2006-08-30 JP JP2006234221A patent/JP2007016042A/ja not_active Withdrawn
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