NO317884B1 - Nye polycykliske azaindolforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem - Google Patents
Nye polycykliske azaindolforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem Download PDFInfo
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- NO317884B1 NO317884B1 NO20005200A NO20005200A NO317884B1 NO 317884 B1 NO317884 B1 NO 317884B1 NO 20005200 A NO20005200 A NO 20005200A NO 20005200 A NO20005200 A NO 20005200A NO 317884 B1 NO317884 B1 NO 317884B1
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- ethyl
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- 238000002360 preparation method Methods 0.000 title claims abstract description 31
- -1 Polycyclic Azaindole Compounds Chemical class 0.000 title claims abstract description 14
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 11
- 239000002253 acid Substances 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 239000000543 intermediate Substances 0.000 claims abstract description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000002541 furyl group Chemical group 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 192
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 230000009471 action Effects 0.000 claims description 19
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 13
- 230000001193 melatoninergic effect Effects 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
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- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
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- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 2
- PDCUMQNKFDHOSG-UHFFFAOYSA-N N-[2-(15-methoxy-11,16-diazatetracyclo[9.7.0.02,7.012,17]octadeca-1(18),2,4,6,12(17),13,15-heptaen-18-yl)ethyl]acetamide Chemical compound C1CCC2=CC=CC=C2C2=C(CCNC(C)=O)C3=NC(OC)=CC=C3N21 PDCUMQNKFDHOSG-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004429 atom Chemical group 0.000 claims description 2
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- 229940079593 drug Drugs 0.000 claims description 2
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- 150000002366 halogen compounds Chemical class 0.000 claims description 2
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- ZBEIISOXYLXLTJ-UHFFFAOYSA-N n-[2-(3-methoxy-6,7,8,9-tetrahydropyrido[3,2-b]indolizin-5-yl)ethyl]acetamide Chemical compound C1CCCC2=C(CCNC(C)=O)C3=CC(OC)=CN=C3N21 ZBEIISOXYLXLTJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
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- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- RJZCHJDWURHAMY-UHFFFAOYSA-N n-[2-(2-methoxy-6,7,8,9-tetrahydropyrido[2,3-b]indolizin-10-yl)ethyl]furan-2-carboxamide Chemical compound C12=NC(OC)=CC=C2N2CCCCC2=C1CCNC(=O)C1=CC=CO1 RJZCHJDWURHAMY-UHFFFAOYSA-N 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 abstract description 2
- 125000005842 heteroatom Chemical group 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 125000006684 polyhaloalkyl group Polymers 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
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- 125000003118 aryl group Chemical group 0.000 abstract 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
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- 125000001041 indolyl group Chemical group 0.000 abstract 1
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- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 abstract 1
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- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
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- C—CHEMISTRY; METALLURGY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Reproductive Health (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Emergency Medicine (AREA)
- Psychology (AREA)
- Child & Adolescent Psychology (AREA)
- Anesthesiology (AREA)
- Nutrition Science (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9912900A FR2799757B1 (fr) | 1999-10-15 | 1999-10-15 | Nouveaux derives polycycliques azaindoliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20005200D0 NO20005200D0 (no) | 2000-10-16 |
| NO20005200L NO20005200L (no) | 2001-04-17 |
| NO317884B1 true NO317884B1 (no) | 2004-12-27 |
Family
ID=9550991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20005200A NO317884B1 (no) | 1999-10-15 | 2000-10-16 | Nye polycykliske azaindolforbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US6495543B1 (de) |
| EP (1) | EP1092717B1 (de) |
| JP (1) | JP3519357B2 (de) |
| KR (1) | KR100460783B1 (de) |
| CN (1) | CN1151152C (de) |
| AT (1) | ATE230745T1 (de) |
| AU (1) | AU772126B2 (de) |
| BR (1) | BR0004823A (de) |
| CA (1) | CA2323720C (de) |
| DE (1) | DE60001138T2 (de) |
| DK (1) | DK1092717T3 (de) |
| EA (1) | EA003666B1 (de) |
| ES (1) | ES2189730T3 (de) |
| FR (1) | FR2799757B1 (de) |
| HK (1) | HK1036061A1 (de) |
| HU (1) | HUP0004007A3 (de) |
| MX (1) | MXPA00009729A (de) |
| NO (1) | NO317884B1 (de) |
| NZ (1) | NZ507525A (de) |
| PL (1) | PL343187A1 (de) |
| PT (1) | PT1092717E (de) |
| SI (1) | SI1092717T1 (de) |
| ZA (1) | ZA200005667B (de) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6269533B2 (en) * | 1999-02-23 | 2001-08-07 | Advanced Research Corporation | Method of making a patterned magnetic recording head |
| FR2799757B1 (fr) * | 1999-10-15 | 2001-12-14 | Adir | Nouveaux derives polycycliques azaindoliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP1132389A1 (de) * | 2000-03-06 | 2001-09-12 | Vernalis Research Limited | Neue Azaindolyl-Derivate für die Behandlung von Fettleibigheit |
| DE10143079A1 (de) * | 2001-09-03 | 2003-05-15 | Zentaris Ag | Cyclische Indol- und Heteroindolderivate, deren Herstellung und Verwendung als Arzneimittel |
| US20050267303A1 (en) * | 2001-09-04 | 2005-12-01 | Zentaris Ag | Cyclic indole and heteroindole derivatives and methods for making and using as pharmaceuticals |
| GB0202015D0 (en) * | 2002-01-29 | 2002-03-13 | Hoffmann La Roche | Piperazine Derivatives |
| US7595311B2 (en) * | 2002-05-24 | 2009-09-29 | Exelixis, Inc. | Azepinoindole derivatives as pharmaceutical agents |
| TWI329111B (en) * | 2002-05-24 | 2010-08-21 | X Ceptor Therapeutics Inc | Azepinoindole and pyridoindole derivatives as pharmaceutical agents |
| ES2425143T3 (es) | 2002-11-28 | 2013-10-11 | Suven Life Sciences Limited | N-Arilsulfonil-3-aminoalcoxiindoles |
| EA009367B1 (ru) * | 2002-12-18 | 2007-12-28 | Сувен Лайф Сайенсиз Лимитед | ПРОИЗВОДНЫЕ 5-ТИА-5-ДИОКСО-4b-АЗАИНДЕНО[2,1-a]ИНДЕНА, ОБЛАДАЮЩИЕ АФФИННОСТЬЮ К РЕЦЕПТОРУ СЕРОТОНИНА |
| DE202007014474U1 (de) * | 2007-10-16 | 2009-03-05 | Schwan-Stabilo Cosmetics Gmbh & Co. Kg | Aufgespritzte Applikatoren |
| MX2011001062A (es) * | 2008-07-30 | 2011-03-24 | Ferrer Int | Compuestos de 1,6-dihidro-2h-3-oxa-6-aza-as-indaceno. |
| WO2010031184A1 (en) * | 2008-09-22 | 2010-03-25 | Merck Frosst Canada Ltd. | Azaindole derivatives as crth2 receptor antagonists |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3910901A (en) * | 1972-02-14 | 1975-10-07 | Ayerst Mckenna & Harrison | Oxazinoindole- and thiazinoindole derivatives |
| US3912729A (en) * | 1972-02-14 | 1975-10-14 | Ayerst Mckenna & Harrison | Oxazinoindole- and thiazinoindole derivatives |
| US3962236A (en) * | 1972-02-14 | 1976-06-08 | Ayerst Mckenna And Harrison Ltd. | Oxazinoindole- and thiazinoindole derivatives |
| US3910903A (en) * | 1974-02-14 | 1975-10-07 | Ayerst Mckenna & Harrison | Oxazinoindole- and thiazinoindole derivatives |
| US4012511A (en) * | 1974-05-28 | 1977-03-15 | Ayerst Mckenna & Harrison Ltd. | Oxazinoindole derivatives useful as antidepressants |
| US4066763A (en) * | 1975-07-07 | 1978-01-03 | Ayerst Mckenna And Harrison Ltd. | Thiazinoindoles useful as antidepressants |
| EP0183993A3 (de) * | 1984-11-16 | 1987-12-09 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | 2H-Imidazo[1',2':1,2]pyrrolo[3,4-b]pyridine und deren Verwendung als Unkrautbekämpfungsmittel |
| DE3674028D1 (de) * | 1985-03-12 | 1990-10-18 | Ciba Geigy Ag | Heterocyclisch kondensierte pyridin-verbindungen als herbizide. |
| DK155524C (da) * | 1987-03-18 | 1989-09-11 | Ferrosan As | Kondenserede imidazolderivater og farmaceutiske praeparater indeholdende disse |
| EP0572863A1 (de) * | 1992-06-05 | 1993-12-08 | F. Hoffmann-La Roche Ag | ZNS Pyrazinoindole |
| MX9305947A (es) * | 1992-09-29 | 1994-06-30 | Smithkline Beecham Plc | Compuestos antagonistas del receptor 5-ht4, procedimiento para su preparacion y composiciones farmaceuticas que las contienen. |
| FR2732969B1 (fr) * | 1995-04-14 | 1997-05-16 | Adir | Nouveaux composes pyridiniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2762598A1 (fr) * | 1997-04-25 | 1998-10-30 | Adir | Nouveaux composes heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennnent |
| FR2763335B1 (fr) * | 1997-05-16 | 2000-11-24 | Adir | Nouveaux composes heterocycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2766824B1 (fr) * | 1997-07-30 | 1999-09-10 | Adir | Nouveaux composes heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| GB9902047D0 (en) * | 1999-01-29 | 1999-03-17 | Cerebrus Ltd | Chemical compounds XI |
| FR2799757B1 (fr) * | 1999-10-15 | 2001-12-14 | Adir | Nouveaux derives polycycliques azaindoliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| GB0019117D0 (en) * | 2000-08-03 | 2000-09-27 | Univ Barcelona | Derivatives of variolin B |
| CN101448012B (zh) * | 2002-11-12 | 2013-04-24 | 雷特泽遥距管理有限责任公司 | 具有ip能力分区的数据存储设备 |
-
1999
- 1999-10-15 FR FR9912900A patent/FR2799757B1/fr not_active Expired - Fee Related
-
2000
- 2000-10-04 MX MXPA00009729A patent/MXPA00009729A/es active IP Right Grant
- 2000-10-12 US US09/689,578 patent/US6495543B1/en not_active Expired - Fee Related
- 2000-10-13 DE DE60001138T patent/DE60001138T2/de not_active Expired - Fee Related
- 2000-10-13 HU HU0004007A patent/HUP0004007A3/hu unknown
- 2000-10-13 ZA ZA200005667A patent/ZA200005667B/xx unknown
- 2000-10-13 ES ES00402832T patent/ES2189730T3/es not_active Expired - Lifetime
- 2000-10-13 NZ NZ507525A patent/NZ507525A/en unknown
- 2000-10-13 SI SI200030043T patent/SI1092717T1/xx unknown
- 2000-10-13 AU AU66502/00A patent/AU772126B2/en not_active Ceased
- 2000-10-13 DK DK00402832T patent/DK1092717T3/da active
- 2000-10-13 EA EA200000948A patent/EA003666B1/ru not_active IP Right Cessation
- 2000-10-13 PL PL00343187A patent/PL343187A1/xx not_active Application Discontinuation
- 2000-10-13 PT PT00402832T patent/PT1092717E/pt unknown
- 2000-10-13 JP JP2000314109A patent/JP3519357B2/ja not_active Expired - Fee Related
- 2000-10-13 CN CNB001304739A patent/CN1151152C/zh not_active Expired - Fee Related
- 2000-10-13 AT AT00402832T patent/ATE230745T1/de not_active IP Right Cessation
- 2000-10-13 BR BR0004823-2A patent/BR0004823A/pt not_active Application Discontinuation
- 2000-10-13 EP EP00402832A patent/EP1092717B1/de not_active Expired - Lifetime
- 2000-10-13 CA CA002323720A patent/CA2323720C/fr not_active Expired - Fee Related
- 2000-10-16 KR KR10-2000-0060725A patent/KR100460783B1/ko not_active IP Right Cessation
- 2000-10-16 NO NO20005200A patent/NO317884B1/no not_active IP Right Cessation
-
2001
- 2001-09-25 HK HK01106736A patent/HK1036061A1/xx not_active IP Right Cessation
-
2002
- 2002-10-09 US US10/267,238 patent/US6667304B2/en not_active Expired - Fee Related
- 2002-10-09 US US10/267,303 patent/US7235550B2/en not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
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| MM1K | Lapsed by not paying the annual fees |