NO329605B1 - (Imidazol-1-yl-metyl)pyridazinforbindelser, fremgangsmate for fremstilling av slike, medikament inneholdende slike forbindelser, slike forbindelser for anvendelse som medikament samt slike forbindelser for behandling av sykdommer - Google Patents
(Imidazol-1-yl-metyl)pyridazinforbindelser, fremgangsmate for fremstilling av slike, medikament inneholdende slike forbindelser, slike forbindelser for anvendelse som medikament samt slike forbindelser for behandling av sykdommer Download PDFInfo
- Publication number
- NO329605B1 NO329605B1 NO20044666A NO20044666A NO329605B1 NO 329605 B1 NO329605 B1 NO 329605B1 NO 20044666 A NO20044666 A NO 20044666A NO 20044666 A NO20044666 A NO 20044666A NO 329605 B1 NO329605 B1 NO 329605B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- pyridazine
- methylimidazol
- prepared
- compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 272
- 238000000034 method Methods 0.000 title claims description 25
- 239000003814 drug Substances 0.000 title claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 5
- 201000010099 disease Diseases 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 7
- GFSWLEBKUPUQNQ-UHFFFAOYSA-N 3-(imidazol-1-ylmethyl)pyridazine Chemical class C1=CN=CN1CC1=CC=CN=N1 GFSWLEBKUPUQNQ-UHFFFAOYSA-N 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 208000002193 Pain Diseases 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 8
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- 208000030886 Traumatic Brain injury Diseases 0.000 claims abstract description 4
- 208000005298 acute pain Diseases 0.000 claims abstract description 4
- 125000005750 substituted cyclic group Chemical group 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 8
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 6
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 6
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- LRTWVDJKDKWTPA-UHFFFAOYSA-N 5-(3-cyclopropyl-4-fluorophenyl)-3-[(2-methylimidazol-1-yl)methyl]pyridazine Chemical compound CC1=NC=CN1CC1=CC(C=2C=C(C(F)=CC=2)C2CC2)=CN=N1 LRTWVDJKDKWTPA-UHFFFAOYSA-N 0.000 claims description 3
- CPMSTLZWOACPCE-UHFFFAOYSA-N 5-[3-(1,1-difluoroethyl)-4-fluorophenyl]-3-[(2-methylimidazol-1-yl)methyl]pyridazine Chemical compound CC1=NC=CN1CC1=CC(C=2C=C(C(F)=CC=2)C(C)(F)F)=CN=N1 CPMSTLZWOACPCE-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- IYKYZCLSQGHBCJ-UHFFFAOYSA-N 3-[(2-methylimidazol-1-yl)methyl]-5-[3-(trifluoromethyl)phenyl]pyridazine Chemical compound CC1=NC=CN1CC1=CC(C=2C=C(C=CC=2)C(F)(F)F)=CN=N1 IYKYZCLSQGHBCJ-UHFFFAOYSA-N 0.000 claims description 2
- ITXNRQKPXQBCQT-UHFFFAOYSA-N 5-(1-benzothiophen-5-yl)-3-[(2-methylimidazol-1-yl)methyl]pyridazine Chemical compound CC1=NC=CN1CC1=CC(C=2C=C3C=CSC3=CC=2)=CN=N1 ITXNRQKPXQBCQT-UHFFFAOYSA-N 0.000 claims description 2
- ULGGCXZAFZNRQJ-UHFFFAOYSA-N 5-(3,4-dihydronaphthalen-2-yl)-3-[(2-methylimidazol-1-yl)methyl]pyridazine;hydrochloride Chemical compound Cl.CC1=NC=CN1CC1=CC(C=2CCC3=CC=CC=C3C=2)=CN=N1 ULGGCXZAFZNRQJ-UHFFFAOYSA-N 0.000 claims description 2
- PNLLKCJWGKWZMA-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-3-[(2-methylimidazol-1-yl)methyl]pyridazine Chemical compound CC1=NC=CN1CC1=CC(C=2C=C(Cl)C(F)=CC=2)=CN=N1 PNLLKCJWGKWZMA-UHFFFAOYSA-N 0.000 claims description 2
- DZCQOJNPJQODAU-UHFFFAOYSA-N 5-(4-chloro-3-methylphenyl)-3-[(2-methylimidazol-1-yl)methyl]pyridazine Chemical compound CC1=NC=CN1CC1=CC(C=2C=C(C)C(Cl)=CC=2)=CN=N1 DZCQOJNPJQODAU-UHFFFAOYSA-N 0.000 claims description 2
- BJTKDJHHZFOIKH-UHFFFAOYSA-N 5-(4-fluoro-3-methylphenyl)-3-[(2-methylimidazol-1-yl)methyl]pyridazine Chemical compound CC1=NC=CN1CC1=CC(C=2C=C(C)C(F)=CC=2)=CN=N1 BJTKDJHHZFOIKH-UHFFFAOYSA-N 0.000 claims description 2
- WUQUOHYPXJCRTA-UHFFFAOYSA-N 5-[3-(1,1-difluoroethyl)-5-fluorophenyl]-3-[(2-methylimidazol-1-yl)methyl]pyridazine Chemical compound CC1=NC=CN1CC1=CC(C=2C=C(C=C(F)C=2)C(C)(F)F)=CN=N1 WUQUOHYPXJCRTA-UHFFFAOYSA-N 0.000 claims description 2
- DMTHXEXNJLRHOS-UHFFFAOYSA-N 5-[3-(1,1-difluoroethyl)phenyl]-3-[(2-methylimidazol-1-yl)methyl]pyridazine Chemical compound CC1=NC=CN1CC1=CC(C=2C=C(C=CC=2)C(C)(F)F)=CN=N1 DMTHXEXNJLRHOS-UHFFFAOYSA-N 0.000 claims description 2
- BOVUHBFXPNLTKF-UHFFFAOYSA-N 5-[3-(difluoromethyl)-4-fluorophenyl]-3-[(2-methylimidazol-1-yl)methyl]pyridazine Chemical compound CC1=NC=CN1CC1=CC(C=2C=C(C(F)=CC=2)C(F)F)=CN=N1 BOVUHBFXPNLTKF-UHFFFAOYSA-N 0.000 claims description 2
- MNPGTJZEDYCIFU-UHFFFAOYSA-N 5-[3-(difluoromethyl)-4-fluorophenyl]-3-[2-(2-ethylimidazol-1-yl)ethyl]pyridazine Chemical compound CCC1=NC=CN1CCC1=CC(C=2C=C(C(F)=CC=2)C(F)F)=CN=N1 MNPGTJZEDYCIFU-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 abstract description 7
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- QLLODBOKCIDPQU-UHFFFAOYSA-N 5-chloro-3-[(2-methylimidazol-1-yl)methyl]pyridazine Chemical compound CC1=NC=CN1CC1=CC(Cl)=CN=N1 QLLODBOKCIDPQU-UHFFFAOYSA-N 0.000 description 71
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- 239000011734 sodium Substances 0.000 description 16
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 14
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- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 9
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- XYIKKXJOYQGEJH-UHFFFAOYSA-N (5-methoxypyridazin-3-yl)methanol Chemical compound COC1=CN=NC(CO)=C1 XYIKKXJOYQGEJH-UHFFFAOYSA-N 0.000 description 7
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
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Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02010217 | 2002-05-16 | ||
| PCT/EP2003/005151 WO2003097637A1 (en) | 2002-05-16 | 2003-05-16 | (imidazol-1-yl-methyl)-pyridazine as nmda receptor blocker |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20044666L NO20044666L (no) | 2004-12-15 |
| NO329605B1 true NO329605B1 (no) | 2010-11-22 |
Family
ID=29433072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20044666A NO329605B1 (no) | 2002-05-16 | 2004-10-28 | (Imidazol-1-yl-metyl)pyridazinforbindelser, fremgangsmate for fremstilling av slike, medikament inneholdende slike forbindelser, slike forbindelser for anvendelse som medikament samt slike forbindelser for behandling av sykdommer |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US7005432B2 (es) |
| EP (1) | EP1506190B1 (es) |
| JP (1) | JP4267569B2 (es) |
| KR (1) | KR100632868B1 (es) |
| CN (1) | CN1312151C (es) |
| AR (1) | AR040010A1 (es) |
| AT (1) | ATE329912T1 (es) |
| AU (1) | AU2003242542B2 (es) |
| BR (1) | BR0311177A (es) |
| CA (1) | CA2485926C (es) |
| CL (1) | CL2004001251A1 (es) |
| CY (1) | CY1105159T1 (es) |
| DE (1) | DE60306152T2 (es) |
| DK (1) | DK1506190T3 (es) |
| ES (1) | ES2265581T3 (es) |
| HK (1) | HK1080845A1 (es) |
| HR (1) | HRP20041060B1 (es) |
| IL (1) | IL164922A (es) |
| MA (1) | MA27117A1 (es) |
| ME (1) | MEP76708A (es) |
| MX (1) | MXPA04011253A (es) |
| NO (1) | NO329605B1 (es) |
| NZ (1) | NZ536310A (es) |
| PL (1) | PL211340B1 (es) |
| PT (1) | PT1506190E (es) |
| RS (1) | RS51200B (es) |
| RU (1) | RU2317294C2 (es) |
| SI (1) | SI1506190T1 (es) |
| TN (1) | TNSN04224A1 (es) |
| WO (1) | WO2003097637A1 (es) |
| ZA (1) | ZA200408789B (es) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7005432B2 (en) * | 2002-05-16 | 2006-02-28 | Hoffman-La Roche Inc. | Substituted imidazol-pyridazine derivatives |
| GB0218876D0 (en) * | 2002-08-13 | 2002-09-25 | Merck Sharp & Dohme | Therapeutic agents |
| CN100579579C (zh) * | 2002-10-01 | 2010-01-13 | 诺华疫苗和诊断公司 | 抗癌及抗感染性疾病组合物及其使用方法 |
| CN103204996B (zh) | 2005-05-03 | 2015-12-09 | 默克专利有限公司 | 有机电致发光器件 |
| US20090054392A1 (en) * | 2007-08-20 | 2009-02-26 | Wyeth | Naphthylpyrimidine, naphthylpyrazine and naphthylpyridazine analogs and their use as agonists of the wnt-beta-catenin cellular messaging system |
| JP5315710B2 (ja) * | 2008-02-07 | 2013-10-16 | セントラル硝子株式会社 | １−ブロモ−３−フルオロ−５−ジフルオロメチルベンゼンの製造方法 |
| DE102008015033A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte (Pyrazolyl-carbonyl)imidazolidinone und ihre Verwendung |
| KR20100135847A (ko) * | 2008-03-27 | 2010-12-27 | 에보텍 뉴로사이언시즈 게엠베하 | Ｎｍｄａ ｎｒ２ｂ―서브타입 선택적 길항제를 사용한 질병 치료 방법 |
| ME02337B (me) | 2009-02-05 | 2016-06-20 | Takeda Pharmaceuticals Co | Jedinjenja piridazinona |
| WO2012018058A1 (ja) * | 2010-08-04 | 2012-02-09 | 武田薬品工業株式会社 | 縮合複素環化合物 |
| WO2012019106A2 (en) * | 2010-08-06 | 2012-02-09 | Board Of Regents Of The University Of Nebraska | Positive and negative modulators of nmda receptors |
| WO2013160728A1 (en) | 2012-04-26 | 2013-10-31 | Alma Mater Studiorum - Universita' Di Bologna | Dual targeting compounds for the treatment of alzheimer's disease |
| WO2016025917A1 (en) * | 2014-08-15 | 2016-02-18 | Janssen Pharmaceuticals, Inc. | Triazoles as nr2b receptor inhibitors |
| US10071988B2 (en) | 2016-02-10 | 2018-09-11 | Janssen Pharmaceutica Nv | Substituted 1,2,3-triazoles as NR2B-selective NMDA modulators |
| JP6850300B2 (ja) | 2016-02-18 | 2021-03-31 | シンジェンタ パーティシペーションズ アーゲー | 殺有害生物活性ピラゾール誘導体 |
| WO2017158151A1 (en) | 2016-03-18 | 2017-09-21 | Savira Pharmaceuticals Gmbh | Pyrimidone derivatives and their use in the treatment, amelioration or prevention of a viral disease |
| WO2017158147A1 (en) | 2016-03-18 | 2017-09-21 | Savira Pharmaceuticals Gmbh | Pyrimidone derivatives and their use in the treatment, amelioration or prevention of a viral disease |
| TW201819376A (zh) | 2016-10-06 | 2018-06-01 | 比利時商健生藥品公司 | 經取代之１Ｈ－咪唑並［４，５－ｂ］吡啶－２（３Ｈ）－酮及其作為ＧＬＵＮ２Ｂ受體調節劑之用途 |
| EP3558318B1 (en) | 2016-12-22 | 2023-12-20 | Novartis AG | Nmda receptor modulators and uses thereof |
| JP7346441B2 (ja) | 2018-04-04 | 2023-09-19 | ヤンセン ファーマシューティカ エヌ．ベー． | 置換ピリジン及びピリミジン並びにｇｌｕｎ２ｂ受容体調節物質としてのそれらの使用 |
| RS64359B1 (sr) | 2018-08-03 | 2023-08-31 | Novartis Ag | Heteroaromatični modulatori nmda receptora i njihove upotrebe |
| MX2021015510A (es) | 2019-06-14 | 2022-04-11 | Janssen Pharmaceutica Nv | Pirazolo[4,3-b]piridinas sustituidas y su uso como moduladores del receptor glun2b. |
| EP3983072A1 (en) | 2019-06-14 | 2022-04-20 | Janssen Pharmaceutica NV | Pyrazine carbamates and their use as glun2b receptor modulators |
| BR112021024856A2 (pt) | 2019-06-14 | 2022-01-18 | Janssen Pharmaceutica Nv | Amidas pirazolo-piridina substituídas e seu uso como moduladores do receptor de glun2b |
| KR20220024403A (ko) | 2019-06-14 | 2022-03-03 | 얀센 파마슈티카 엔.브이. | 치환된 피라졸로-피라진 및 이들의 glun2b 수용체 조절제로서의 용도 |
| EP3982958A1 (en) | 2019-06-14 | 2022-04-20 | Janssen Pharmaceutica NV | Substituted heteroaromatic pyrazolo-pyridines and their use as glun2b receptor modulators |
| BR112021025132A2 (pt) | 2019-06-14 | 2022-01-25 | Janssen Pharmaceutica Nv | Carbamatos de piridina e seu uso como moduladores do receptor glun2b |
| CN114478210A (zh) * | 2022-02-26 | 2022-05-13 | 江苏壹药新材料有限公司 | 一种7-氯萘-2-甲醛的合成方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9708171A (pt) * | 1996-03-08 | 1999-07-27 | Hoffmann La Roche | Uso de derivados de 4-fenil-3,6-di-hidro-2h-piridila como bloqueadores de subtipo de receptor nmda |
| CA2220649C (en) * | 1996-12-03 | 2007-02-13 | F. Hoffmann-La Roche Ag | 4-hydroxy-piperidine derivatives |
| US6015824A (en) | 1998-02-10 | 2000-01-18 | Hoffmann-La Roche Ag | Pyrrolidine and piperidine derivatives and treatment of neurodegenerative disorders |
| TWI254043B (en) * | 1999-06-08 | 2006-05-01 | Hoffmann La Roche | Ethanesulfonyl-piperidine derivatives having good affinity to N-methyl-D-aspartate (NMDA) receptor |
| ATE257827T1 (de) * | 1999-07-21 | 2004-01-15 | Hoffmann La Roche | Triazolderivate |
| US6339093B1 (en) * | 1999-10-08 | 2002-01-15 | Hoffmann-La Roche Inc. | Isoquinoline derivatives |
| PT1278728E (pt) * | 2000-04-20 | 2004-10-29 | Hoffmann La Roche | Derivados de pirrolidina e de piperidina e sua utilizacao no tratamento de disturbios neurodegenerativos |
| US6432985B2 (en) * | 2000-04-25 | 2002-08-13 | Hoffmann-La Roche Inc. | Neuroprotective substituted piperidine compounds with activity as NMDA NR2B subtype selective antagonists |
| WO2002028814A2 (en) | 2000-10-06 | 2002-04-11 | Regents Of The University Of California | Nmda receptor channel blocker with neuroprotective activity |
| CA2381630A1 (en) | 2001-04-23 | 2002-10-23 | Leonard Theodore Meltzer | Method for preventing dyskinesias |
| DE10120159A1 (de) | 2001-04-25 | 2002-10-31 | Merck Patent Gmbh | NMDA-Antagonisten und NMDA-Agonisten zur Behandlung von Suchterkrankungen |
| US7005432B2 (en) * | 2002-05-16 | 2006-02-28 | Hoffman-La Roche Inc. | Substituted imidazol-pyridazine derivatives |
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2003
- 2003-05-09 US US10/434,955 patent/US7005432B2/en not_active Expired - Fee Related
- 2003-05-15 AR ARP030101685A patent/AR040010A1/es active IP Right Grant
- 2003-05-16 ES ES03752750T patent/ES2265581T3/es not_active Expired - Lifetime
- 2003-05-16 RU RU2004136979/04A patent/RU2317294C2/ru not_active IP Right Cessation
- 2003-05-16 AT AT03752750T patent/ATE329912T1/de active
- 2003-05-16 NZ NZ536310A patent/NZ536310A/en not_active IP Right Cessation
- 2003-05-16 MX MXPA04011253A patent/MXPA04011253A/es active IP Right Grant
- 2003-05-16 KR KR1020047018485A patent/KR100632868B1/ko not_active IP Right Cessation
- 2003-05-16 PL PL374224A patent/PL211340B1/pl unknown
- 2003-05-16 ME MEP-767/08A patent/MEP76708A/xx unknown
- 2003-05-16 CN CNB038111926A patent/CN1312151C/zh not_active Expired - Fee Related
- 2003-05-16 BR BR0311177-6A patent/BR0311177A/pt not_active IP Right Cessation
- 2003-05-16 CA CA002485926A patent/CA2485926C/en not_active Expired - Fee Related
- 2003-05-16 DK DK03752750T patent/DK1506190T3/da active
- 2003-05-16 RS YUP-985/04A patent/RS51200B/sr unknown
- 2003-05-16 SI SI200330332T patent/SI1506190T1/sl unknown
- 2003-05-16 JP JP2004505370A patent/JP4267569B2/ja not_active Expired - Fee Related
- 2003-05-16 DE DE60306152T patent/DE60306152T2/de not_active Expired - Lifetime
- 2003-05-16 AU AU2003242542A patent/AU2003242542B2/en not_active Ceased
- 2003-05-16 PT PT03752750T patent/PT1506190E/pt unknown
- 2003-05-16 EP EP03752750A patent/EP1506190B1/en not_active Expired - Lifetime
- 2003-05-16 WO PCT/EP2003/005151 patent/WO2003097637A1/en active IP Right Grant
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- 2004-05-24 CL CL200401251A patent/CL2004001251A1/es unknown
- 2004-10-28 IL IL164922A patent/IL164922A/en not_active IP Right Cessation
- 2004-10-28 NO NO20044666A patent/NO329605B1/no not_active IP Right Cessation
- 2004-10-29 ZA ZA2004/08789A patent/ZA200408789B/en unknown
- 2004-11-11 TN TNP2004000224A patent/TNSN04224A1/fr unknown
- 2004-11-12 HR HR20041060 patent/HRP20041060B1/xx not_active IP Right Cessation
- 2004-11-12 MA MA27943A patent/MA27117A1/fr unknown
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2006
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- 2006-08-22 CY CY20061101161T patent/CY1105159T1/el unknown
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| CHAD | Change of the owner's name or address (par. 44 patent law, par. patentforskriften) |
Owner name: EVOTEC INTERNATIONAL GMBH, DE |
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| MM1K | Lapsed by not paying the annual fees |