NO324706B1 - Benzodiazepinderivater, fremstilling av disse, medikament inneholdende slike forbindelser samt anvendelse av disse for fremstilling av medikament for behandling av sykdommer - Google Patents
Benzodiazepinderivater, fremstilling av disse, medikament inneholdende slike forbindelser samt anvendelse av disse for fremstilling av medikament for behandling av sykdommer Download PDFInfo
- Publication number
- NO324706B1 NO324706B1 NO20032208A NO20032208A NO324706B1 NO 324706 B1 NO324706 B1 NO 324706B1 NO 20032208 A NO20032208 A NO 20032208A NO 20032208 A NO20032208 A NO 20032208A NO 324706 B1 NO324706 B1 NO 324706B1
- Authority
- NO
- Norway
- Prior art keywords
- benzodiazepine
- triazolo
- imidazo
- ethyl
- carboxylate
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 96
- 239000003814 drug Substances 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 8
- 229940079593 drug Drugs 0.000 title claims description 6
- 201000010099 disease Diseases 0.000 title claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 6
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 title 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 title 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 65
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims description 41
- 239000000460 chlorine Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 35
- NZTCFMPWFGWRBN-UHFFFAOYSA-N 3H-[1,2,4]triazolo[4,3-d][1,4]benzodiazepine-10-carboxylic acid Chemical compound N1=NCN2C=CN=C3C(=C21)C=C(C=C3)C(=O)O NZTCFMPWFGWRBN-UHFFFAOYSA-N 0.000 claims description 24
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
- NKWDDGCMDWGDLU-UHFFFAOYSA-N 3H-[1,2,4]triazolo[4,3-d][1,4]benzodiazepine Chemical compound N1=NCN2C=CN=C3C(=C21)C=CC=C3 NKWDDGCMDWGDLU-UHFFFAOYSA-N 0.000 claims description 16
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- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- -1 methoxy, methyl Chemical group 0.000 claims description 9
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- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 8
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- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 3
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- 239000004744 fabric Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229940125425 inverse agonist Drugs 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 210000005171 mammalian brain Anatomy 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- KIHLTOMYTLZHOE-UHFFFAOYSA-N n,n-diethyl-2-hydrazinyl-2-oxoacetamide Chemical compound CCN(CC)C(=O)C(=O)NN KIHLTOMYTLZHOE-UHFFFAOYSA-N 0.000 description 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 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
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 230000031836 visual learning Effects 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00124332 | 2000-11-16 | ||
| PCT/EP2001/012887 WO2002040487A2 (en) | 2000-11-16 | 2001-11-08 | Benzodiazepine derivatives as gaba a receptor modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20032208L NO20032208L (no) | 2003-05-15 |
| NO20032208D0 NO20032208D0 (no) | 2003-05-15 |
| NO324706B1 true NO324706B1 (no) | 2007-12-03 |
Family
ID=8170315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20032208A NO324706B1 (no) | 2000-11-16 | 2003-05-15 | Benzodiazepinderivater, fremstilling av disse, medikament inneholdende slike forbindelser samt anvendelse av disse for fremstilling av medikament for behandling av sykdommer |
Country Status (41)
| Country | Link |
|---|---|
| US (1) | US6743789B2 (ru) |
| EP (1) | EP1337535B1 (ru) |
| JP (1) | JP4088151B2 (ru) |
| KR (1) | KR100504300B1 (ru) |
| CN (1) | CN1191255C (ru) |
| AR (1) | AR031345A1 (ru) |
| AT (1) | ATE268776T1 (ru) |
| AU (2) | AU2002217007B2 (ru) |
| BG (1) | BG107817A (ru) |
| BR (1) | BR0115393A (ru) |
| CA (1) | CA2427576C (ru) |
| CZ (1) | CZ295256B6 (ru) |
| DE (1) | DE60103776T2 (ru) |
| DK (1) | DK1337535T3 (ru) |
| EC (1) | ECSP034607A (ru) |
| ES (1) | ES2220831T3 (ru) |
| GC (1) | GC0000375A (ru) |
| GT (1) | GT200100230A (ru) |
| HK (1) | HK1062442A1 (ru) |
| HR (1) | HRP20030360A2 (ru) |
| HU (1) | HUP0303281A3 (ru) |
| IL (1) | IL155813A0 (ru) |
| JO (1) | JO2359B1 (ru) |
| MA (1) | MA26962A1 (ru) |
| MX (1) | MXPA03004251A (ru) |
| MY (1) | MY141675A (ru) |
| NO (1) | NO324706B1 (ru) |
| NZ (1) | NZ525413A (ru) |
| PA (1) | PA8532401A1 (ru) |
| PE (1) | PE20020583A1 (ru) |
| PL (1) | PL362925A1 (ru) |
| PT (1) | PT1337535E (ru) |
| RU (1) | RU2278865C2 (ru) |
| SI (1) | SI1337535T1 (ru) |
| SK (1) | SK7232003A3 (ru) |
| TR (1) | TR200402073T4 (ru) |
| TW (1) | TWI239333B (ru) |
| UY (1) | UY27026A1 (ru) |
| WO (1) | WO2002040487A2 (ru) |
| YU (1) | YU35603A (ru) |
| ZA (1) | ZA200303435B (ru) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6686352B2 (en) * | 2001-05-18 | 2004-02-03 | Hoffmann-La Roche Inc. | Substituted imidazo [1,5-a] pyrimido [5,4-d] [1] benzazepine derivatives |
| WO2004113321A1 (ja) * | 2003-06-19 | 2004-12-29 | Daiichi Pharmaceutical Co., Ltd. | 選択的なアミノ置換基導入法 |
| PL1691811T3 (pl) | 2003-12-11 | 2014-12-31 | Sunovion Pharmaceuticals Inc | Skojarzenie leku uspokajającego i modulatora neuroprzekaźnikowego oraz sposoby poprawy jakości snu i leczenia depresji |
| CA2577060A1 (en) | 2004-08-13 | 2006-02-23 | Amgen Inc. | Substituted benzofused heterocycles |
| CN101039678B (zh) | 2004-10-12 | 2011-06-15 | 弗·哈夫曼-拉罗切有限公司 | 用于治疗认知障碍的咪唑并[1,5-a]三唑并[1,5-d]苯并二氮杂䓬衍生物 |
| CN101084220B (zh) * | 2004-10-20 | 2010-12-15 | 弗·哈夫曼-拉罗切有限公司 | 卤素取代的苯并二氮杂*衍生物 |
| RU2007112940A (ru) | 2004-10-20 | 2008-11-27 | Ф.Хоффманн-Ля Рош Аг (Ch) | Производные имидазобензодиазепина |
| ES2307230T3 (es) | 2004-12-14 | 2008-11-16 | F. Hoffmann-La Roche Ag | Imidazo-benzodiacepinas tetraciclicas como moduladores de los receptores gaba. |
| US8510055B2 (en) | 2005-08-03 | 2013-08-13 | The Johns Hopkins University | Methods for characterizing and treating cognitive impairment in aging and disease |
| WO2007019312A2 (en) * | 2005-08-03 | 2007-02-15 | The Johns Hopkins University | Methods for characterizing and treating cognitive impairment in aging and disease |
| ATE477255T1 (de) * | 2005-10-11 | 2010-08-15 | Hoffmann La Roche | Imidazobenzdiazepinderivate |
| CA2625210A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| WO2009139916A1 (en) * | 2008-05-16 | 2009-11-19 | Synta Pharmaceuticals Corp. | Tricyclic triazole compounds that modulate hsp90 activity |
| AU2009317386B2 (en) * | 2008-11-18 | 2013-07-25 | F. Hoffmann-La Roche Ag | Alkylcyclohexylethers of dihydrotetraazabenzoazulenes |
| ES2431279T3 (es) * | 2008-11-28 | 2013-11-25 | F. Hoffmann-La Roche Ag | Arilciclohexiléteres de dihidro-tetraazabenzoazulenos para uso como antagonistas del receptor V1A de la vasopresina |
| CU20090172A6 (es) | 2009-10-09 | 2011-10-05 | Facultad De Quimica Universidad De La Habana | Sistemas tricíclicos y tetracíclicos con actividad sobre el sistema nervioso central y vascular |
| AU2011328993B2 (en) | 2010-11-15 | 2017-03-02 | Agenebio, Inc. | Pyridazine derivatives, compositions and methods for treating cognitive impairment |
| US20150374705A1 (en) | 2012-02-14 | 2015-12-31 | Shanghai Institues for Biological Sciences | Substances for treatment or relief of pain |
| WO2014047413A1 (en) * | 2012-09-21 | 2014-03-27 | Uwm Research Foundation, Inc. | Novel gabaa agonists and methods of using to control airway hyperresponsiveness and inflammation in asthma |
| JP6883988B2 (ja) * | 2013-12-20 | 2021-06-09 | エージンバイオ， インコーポレイテッド | ベンゾジアゼピン誘導体、組成物、および認知障害を処置するための方法 |
| EA036844B1 (ru) | 2015-06-19 | 2020-12-28 | Эйджинбайо, Инк. | Производные бензодиазепина, композиции и способы для лечения когнитивного нарушения |
| US10059718B2 (en) | 2016-01-04 | 2018-08-28 | Tabomedex Biosciences, LLC | Fused quadracyclic compounds, compositions and uses thereof |
| US10973479B2 (en) | 2016-05-16 | 2021-04-13 | Canon Medical Systems Corporation | X-ray diagnosis apparatus, X-ray diagnosis apparatus controlling method, and X-ray diagnosis system |
| BR112019012821A2 (pt) | 2016-12-19 | 2019-11-26 | Agenebio Inc | derivados de benzodiazepina, composições e métodos para o tratamento do comprometimento cognitivo |
| US20180170941A1 (en) * | 2016-12-19 | 2018-06-21 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| KR102512548B1 (ko) | 2017-12-22 | 2023-03-22 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 함질소 화합물 |
| JP7514534B2 (ja) * | 2018-06-19 | 2024-07-11 | エージンバイオ， インコーポレイテッド | 認知障害を処置するためのベンゾジアゼピン誘導体、組成物および方法 |
| KR102151969B1 (ko) * | 2019-12-11 | 2020-09-04 | 주식회사 지투비 | 투과도 가변창의 제조방법 및 그에 의해 제조된 투과도 가변창 |
| CN112979658B (zh) * | 2021-02-22 | 2022-05-31 | 南湖实验室 | 一种氟马西尼的制备方法 |
| US20240132513A1 (en) | 2022-08-19 | 2024-04-25 | Agenebio, Inc. | Benzazepine derivatives, compositions, and methods for treating cognitive impairment |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK174086D0 (da) | 1986-04-16 | 1986-04-16 | Ferrosan As | Nye benzodiazepinderivater samt fremgangsmaade til fremstilling af samme |
| TW201311B (ru) | 1991-06-17 | 1993-03-01 | Hoffmann La Roche |
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2001
- 2001-11-07 TW TW090127658A patent/TWI239333B/zh not_active IP Right Cessation
- 2001-11-08 DK DK01996541T patent/DK1337535T3/da active
- 2001-11-08 YU YU35603A patent/YU35603A/sh unknown
- 2001-11-08 SI SI200130125T patent/SI1337535T1/xx unknown
- 2001-11-08 BR BR0115393-5A patent/BR0115393A/pt not_active IP Right Cessation
- 2001-11-08 AU AU2002217007A patent/AU2002217007B2/en not_active Ceased
- 2001-11-08 EP EP01996541A patent/EP1337535B1/en not_active Expired - Lifetime
- 2001-11-08 PT PT01996541T patent/PT1337535E/pt unknown
- 2001-11-08 MX MXPA03004251A patent/MXPA03004251A/es active IP Right Grant
- 2001-11-08 TR TR2004/02073T patent/TR200402073T4/xx unknown
- 2001-11-08 DE DE60103776T patent/DE60103776T2/de not_active Expired - Lifetime
- 2001-11-08 US US10/007,883 patent/US6743789B2/en not_active Expired - Fee Related
- 2001-11-08 SK SK723-2003A patent/SK7232003A3/sk unknown
- 2001-11-08 JP JP2002543495A patent/JP4088151B2/ja not_active Expired - Fee Related
- 2001-11-08 AU AU1700702A patent/AU1700702A/xx active Pending
- 2001-11-08 NZ NZ525413A patent/NZ525413A/en unknown
- 2001-11-08 HU HU0303281A patent/HUP0303281A3/hu unknown
- 2001-11-08 AT AT01996541T patent/ATE268776T1/de not_active IP Right Cessation
- 2001-11-08 PL PL01362925A patent/PL362925A1/xx not_active Application Discontinuation
- 2001-11-08 RU RU2003116895/04A patent/RU2278865C2/ru not_active IP Right Cessation
- 2001-11-08 CA CA002427576A patent/CA2427576C/en not_active Expired - Fee Related
- 2001-11-08 ES ES01996541T patent/ES2220831T3/es not_active Expired - Lifetime
- 2001-11-08 IL IL15581301A patent/IL155813A0/xx unknown
- 2001-11-08 KR KR10-2003-7006609A patent/KR100504300B1/ko not_active IP Right Cessation
- 2001-11-08 CN CNB018189415A patent/CN1191255C/zh not_active Expired - Fee Related
- 2001-11-08 WO PCT/EP2001/012887 patent/WO2002040487A2/en active IP Right Grant
- 2001-11-08 CZ CZ20031597A patent/CZ295256B6/cs not_active IP Right Cessation
- 2001-11-12 JO JO2001183A patent/JO2359B1/en active
- 2001-11-13 GC GCP20011724 patent/GC0000375A/en active
- 2001-11-14 PE PE2001001135A patent/PE20020583A1/es not_active Application Discontinuation
- 2001-11-15 UY UY27026A patent/UY27026A1/es not_active Application Discontinuation
- 2001-11-15 GT GT200100230A patent/GT200100230A/es unknown
- 2001-11-15 MY MYPI20015253A patent/MY141675A/en unknown
- 2001-11-15 PA PA20018532401A patent/PA8532401A1/es unknown
- 2001-11-15 AR ARP010105323A patent/AR031345A1/es not_active Application Discontinuation
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2003
- 2003-05-05 ZA ZA200303435A patent/ZA200303435B/en unknown
- 2003-05-07 HR HR20030360A patent/HRP20030360A2/hr not_active Application Discontinuation
- 2003-05-15 NO NO20032208A patent/NO324706B1/no unknown
- 2003-05-15 EC EC2003004607A patent/ECSP034607A/es unknown
- 2003-05-16 BG BG107817A patent/BG107817A/bg unknown
- 2003-05-16 MA MA27163A patent/MA26962A1/fr unknown
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2004
- 2004-07-21 HK HK04105348A patent/HK1062442A1/xx not_active IP Right Cessation
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