NO320854B1 - Heterocykliske, subsitituerte adenosinderivater, farmasoytiske preparater omfattende slike og anvendelse av derivatene for fremstilling av farmasoytiske preparater - Google Patents
Heterocykliske, subsitituerte adenosinderivater, farmasoytiske preparater omfattende slike og anvendelse av derivatene for fremstilling av farmasoytiske preparater Download PDFInfo
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- NO320854B1 NO320854B1 NO20015662A NO20015662A NO320854B1 NO 320854 B1 NO320854 B1 NO 320854B1 NO 20015662 A NO20015662 A NO 20015662A NO 20015662 A NO20015662 A NO 20015662A NO 320854 B1 NO320854 B1 NO 320854B1
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- Prior art keywords
- compound
- alkyl
- amino
- group
- methyl
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- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000003835 adenosine derivatives Chemical class 0.000 title description 5
- 125000000623 heterocyclic group Chemical group 0.000 title description 5
- 239000008194 pharmaceutical composition Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 80
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- -1 1-amino-3-methylpropyl Chemical group 0.000 claims description 19
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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- 229940044551 receptor antagonist Drugs 0.000 claims description 6
- 239000002464 receptor antagonist Substances 0.000 claims description 6
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- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 101150007969 ADORA1 gene Proteins 0.000 claims description 4
- 208000001871 Tachycardia Diseases 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 230000006794 tachycardia Effects 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000005475 oxolanyl group Chemical group 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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- 238000005481 NMR spectroscopy Methods 0.000 description 22
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- 101100284355 Rattus norvegicus Hr gene Proteins 0.000 description 5
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- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical group CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 5
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- QNEIZSSWCVSZOS-UHFFFAOYSA-N methyl 2-phenylmethoxyacetate Chemical compound COC(=O)COCC1=CC=CC=C1 QNEIZSSWCVSZOS-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- DIRLDPKYOATBIA-UHFFFAOYSA-N oxolan-3-yl acetate Chemical compound CC(=O)OC1CCOC1 DIRLDPKYOATBIA-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical group OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 230000006461 physiological response Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000036279 refractory period Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/167—Purine radicals with ribosyl as the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- 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
-
- 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
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/10—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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/317,523 US6576619B2 (en) | 1999-05-24 | 1999-05-24 | Orally active A1 adenosine receptor agonists |
| PCT/US2000/014036 WO2000071558A1 (en) | 1999-05-24 | 2000-05-19 | Orally active a1 adenosine receptor agonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20015662D0 NO20015662D0 (no) | 2001-11-20 |
| NO20015662L NO20015662L (no) | 2002-01-23 |
| NO320854B1 true NO320854B1 (no) | 2006-02-06 |
Family
ID=23234062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20015662A NO320854B1 (no) | 1999-05-24 | 2001-11-20 | Heterocykliske, subsitituerte adenosinderivater, farmasoytiske preparater omfattende slike og anvendelse av derivatene for fremstilling av farmasoytiske preparater |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6576619B2 (xx) |
| EP (1) | EP1181302B1 (xx) |
| JP (2) | JP2003520776A (xx) |
| KR (1) | KR100537032B1 (xx) |
| CN (1) | CN1183153C (xx) |
| AR (1) | AR035909A1 (xx) |
| AT (1) | ATE250621T1 (xx) |
| AU (1) | AU760658B2 (xx) |
| BR (1) | BR0010882A (xx) |
| CA (1) | CA2375040C (xx) |
| DE (1) | DE60005507T2 (xx) |
| ES (1) | ES2206238T3 (xx) |
| IL (2) | IL146471A0 (xx) |
| MX (1) | MXPA01012038A (xx) |
| NO (1) | NO320854B1 (xx) |
| NZ (1) | NZ515580A (xx) |
| TW (1) | TW593330B (xx) |
| WO (1) | WO2000071558A1 (xx) |
| ZA (1) | ZA200109626B (xx) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL127947A0 (en) | 1999-01-07 | 1999-11-30 | Can Fite Technologies Ltd | Pharmaceutical use of adenosine agonists |
| US6790839B2 (en) | 1999-01-07 | 2004-09-14 | Can-Fite Biopharma Ltd. | Pharmaceutical administration of adenosine agonists |
| PL372145A1 (en) * | 2002-02-19 | 2005-07-11 | Cv Therapeutics, Inc. | Partial and full agonists of a sb 1 /sb adenosine receptors |
| ATE425744T1 (de) * | 2002-04-29 | 2009-04-15 | Supernus Pharmaceuticals Inc | Pharmazeutische formulierungen mit verbesserter bioverfugbarkeit |
| EP1680100A4 (en) | 2003-11-04 | 2012-08-08 | Supernus Pharmaceuticals Inc | QUATERNARY AMMONIUM COMPOUNDS CONTAINING BIOAVAILABILITY ACTIVATORS |
| DE602004030931D1 (xx) * | 2003-11-04 | 2011-02-17 | Supernus Pharmaceuticals Inc | |
| JP2009541437A (ja) | 2006-06-27 | 2009-11-26 | ビオヴィトルム・アクチボラゲット（プブリクト） | 治療用化合物 |
| US7731604B2 (en) * | 2006-10-31 | 2010-06-08 | Taylor Made Golf Company, Inc. | Golf club iron head |
| CN101712709A (zh) * | 2008-10-06 | 2010-05-26 | 中国医学科学院药物研究所 | 三乙酰基-3-羟基苯基腺苷及其调血脂的用途 |
| DE102011005232A1 (de) | 2011-03-08 | 2012-09-13 | AristoCon GmbH & Co. KG | Adenosin und seine Derivate zur Verwendung in der Schmerztherapie |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2460929A1 (de) | 1974-12-21 | 1976-06-24 | Boehringer Sohn Ingelheim | Neue xanthinderivate, verfahren zu ihrer herstellung und ihre anwendung |
| US4364922A (en) | 1980-10-14 | 1982-12-21 | University Of Virginia Alumni Patents Foundation | Adenosine antagonists in the treatment and diagnosis of A-V node conduction disturbances |
| JPS57171998A (en) * | 1981-04-15 | 1982-10-22 | Fujisawa Pharmaceut Co Ltd | Adenosine derivative and its salt, preparation thereof and medicinal composition containing the same |
| DE3138397A1 (de) | 1981-09-26 | 1983-04-07 | Hoechst Ag, 6230 Frankfurt | "arzneimittel, darin enthaltene vicinale dihydroxyalkylxanthine und herstellungsverfahren fuer diese xanthinverbindungen" |
| US4593019A (en) | 1984-10-26 | 1986-06-03 | Warner-Lambert Company | N6 -tricyclic adenosines |
| AU577743B2 (en) | 1984-10-26 | 1988-09-29 | Warner-Lambert Company | N6-benzopyrano and benzothiopyrano adenosines |
| AU8274187A (en) | 1986-10-31 | 1988-05-25 | Warner-Lambert Company | Heteroaromatic derivatives of adenosine |
| US4954504A (en) | 1986-11-14 | 1990-09-04 | Ciba-Geigy Corporation | N9 -cyclopentyl-substituted adenine derivatives having adenosine-2 receptor stimulating activity |
| EP0355131B1 (en) * | 1987-10-28 | 1996-09-04 | Pro-Neuron, Inc. | Acyl deoxyribonucleoside derivatives and uses thereof |
| US4980379A (en) | 1988-06-30 | 1990-12-25 | The University Of Virginia | Use of adenosine antagonists in the treatment of bradyarrhythmias and hemodynamic depression associated with cardiopulmonary resucitation and/or cardiovascular collapse |
| DE8817122U1 (de) | 1988-12-22 | 1993-02-04 | Boehringer Ingelheim Kg, 55218 Ingelheim | Neue Xanthinderivate mit Adenosinantogenistischer Wirkung |
| WO1990009178A1 (en) | 1989-01-31 | 1990-08-23 | Whitby Research, Inc. | N6-substituted 9-methyladenines: a new class of adenosine receptor antagonists |
| US5017578A (en) | 1989-06-09 | 1991-05-21 | Hoechst-Roussel Pharmaceuticals Inc. | N-heteroaryl-purin-6-amines useful as analgesic and anticonvulsant agents |
| JPH06102662B2 (ja) | 1989-09-01 | 1994-12-14 | 協和醗酵工業株式会社 | キサンチン誘導体 |
| DE4019892A1 (de) | 1990-06-22 | 1992-01-02 | Boehringer Ingelheim Kg | Neue xanthinderivate |
| US5561134A (en) * | 1990-09-25 | 1996-10-01 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties |
| US5432164A (en) | 1991-10-24 | 1995-07-11 | Novo Nordisk A/S | C2,N6 -disubstituted adenosine derivatives |
| DE4205306B4 (de) | 1992-02-21 | 2005-11-24 | Glüsenkamp, Karl-Heinz, Dr. | Säureamide, Arzneimittel mit denselben und Verfahren zur Herstellung von Säureamiden |
| US5288721A (en) | 1992-09-22 | 1994-02-22 | Cell Therapeutics, Inc. | Substituted epoxyalkyl xanthines |
| WO1994016702A1 (en) | 1993-01-26 | 1994-08-04 | Kyowa Hakko Kogyo Co., Ltd. | Remedy for irregular bowel movement |
| EP0708781B1 (en) | 1993-07-13 | 2001-10-04 | THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, Department of Health and Human Services | A 3 adenosine receptor agonists |
| US5446046A (en) | 1993-10-28 | 1995-08-29 | University Of Florida Research Foundation | A1 adenosine receptor agonists and antagonists as diuretics |
| US5789416B1 (en) * | 1996-08-27 | 1999-10-05 | Cv Therapeutics Inc | N6 mono heterocyclic substituted adenosine derivatives |
| GB9723590D0 (en) * | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| GB9723566D0 (en) * | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
-
1999
- 1999-05-24 US US09/317,523 patent/US6576619B2/en not_active Expired - Lifetime
-
2000
- 2000-05-19 EP EP00932688A patent/EP1181302B1/en not_active Expired - Lifetime
- 2000-05-19 CA CA002375040A patent/CA2375040C/en not_active Expired - Fee Related
- 2000-05-19 ES ES00932688T patent/ES2206238T3/es not_active Expired - Lifetime
- 2000-05-19 WO PCT/US2000/014036 patent/WO2000071558A1/en active IP Right Grant
- 2000-05-19 DE DE60005507T patent/DE60005507T2/de not_active Expired - Lifetime
- 2000-05-19 JP JP2001511301A patent/JP2003520776A/ja active Pending
- 2000-05-19 CN CNB008080658A patent/CN1183153C/zh not_active Expired - Fee Related
- 2000-05-19 AT AT00932688T patent/ATE250621T1/de not_active IP Right Cessation
- 2000-05-19 MX MXPA01012038A patent/MXPA01012038A/es active IP Right Grant
- 2000-05-19 KR KR10-2001-7015044A patent/KR100537032B1/ko not_active IP Right Cessation
- 2000-05-19 AU AU50376/00A patent/AU760658B2/en not_active Ceased
- 2000-05-19 IL IL14647100A patent/IL146471A0/xx active IP Right Grant
- 2000-05-19 NZ NZ515580A patent/NZ515580A/en not_active IP Right Cessation
- 2000-05-19 BR BR0010882-0A patent/BR0010882A/pt not_active Application Discontinuation
- 2000-05-24 AR ARP000102555A patent/AR035909A1/es active IP Right Grant
- 2000-07-14 TW TW089110048A patent/TW593330B/zh not_active IP Right Cessation
-
2001
- 2001-11-13 IL IL146471A patent/IL146471A/en not_active IP Right Cessation
- 2001-11-20 NO NO20015662A patent/NO320854B1/no not_active IP Right Cessation
- 2001-11-22 ZA ZA200109626A patent/ZA200109626B/en unknown
-
2006
- 2006-07-31 JP JP2006207713A patent/JP2006348040A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000071558A1 (en) | 2000-11-30 |
| AU5037600A (en) | 2000-12-12 |
| JP2006348040A (ja) | 2006-12-28 |
| CA2375040C (en) | 2006-02-07 |
| KR100537032B1 (ko) | 2005-12-16 |
| CA2375040A1 (en) | 2000-11-30 |
| TW593330B (en) | 2004-06-21 |
| IL146471A0 (en) | 2002-07-25 |
| NO20015662L (no) | 2002-01-23 |
| CN1183153C (zh) | 2005-01-05 |
| US6576619B2 (en) | 2003-06-10 |
| ES2206238T3 (es) | 2004-05-16 |
| US20020091099A1 (en) | 2002-07-11 |
| JP2003520776A (ja) | 2003-07-08 |
| CN1390228A (zh) | 2003-01-08 |
| DE60005507T2 (de) | 2004-06-24 |
| AU760658B2 (en) | 2003-05-22 |
| NZ515580A (en) | 2004-06-25 |
| BR0010882A (pt) | 2002-06-11 |
| MXPA01012038A (es) | 2002-05-06 |
| AR035909A1 (es) | 2004-07-28 |
| DE60005507D1 (de) | 2003-10-30 |
| EP1181302A1 (en) | 2002-02-27 |
| NO20015662D0 (no) | 2001-11-20 |
| EP1181302B1 (en) | 2003-09-24 |
| IL146471A (en) | 2007-06-03 |
| ATE250621T1 (de) | 2003-10-15 |
| ZA200109626B (en) | 2004-03-10 |
| KR20020092777A (ko) | 2002-12-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |