JP2005527602A5 - - Google Patents
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- Publication number
- JP2005527602A5 JP2005527602A5 JP2004501406A JP2004501406A JP2005527602A5 JP 2005527602 A5 JP2005527602 A5 JP 2005527602A5 JP 2004501406 A JP2004501406 A JP 2004501406A JP 2004501406 A JP2004501406 A JP 2004501406A JP 2005527602 A5 JP2005527602 A5 JP 2005527602A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- diazabicyclo
- propyl
- ene
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 racemates Chemical class 0.000 claims 79
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 37
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 239000000203 mixture Substances 0.000 claims 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 15
- 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 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 10
- GCJYLAWVUWEHLW-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]cyclopropanamine Chemical compound ClC1=CC=CC=C1CNC1CC1 GCJYLAWVUWEHLW-UHFFFAOYSA-N 0.000 claims 10
- IVEWTCACRDEAOB-UHFFFAOYSA-N 2-(2-methoxyphenyl)acetic acid Chemical compound COC1=CC=CC=C1CC(O)=O IVEWTCACRDEAOB-UHFFFAOYSA-N 0.000 claims 9
- 230000000877 morphologic effect Effects 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 239000002904 solvent Chemical class 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 claims 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 5
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 4
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 230000036454 renin-angiotensin system Effects 0.000 claims 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- SASNBVQSOZSTPD-UHFFFAOYSA-N n-methylphenethylamine Chemical compound CNCCC1=CC=CC=C1 SASNBVQSOZSTPD-UHFFFAOYSA-N 0.000 claims 2
- 235000019260 propionic acid Nutrition 0.000 claims 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 2
- LFGLSENCOIFTLS-MYQURODFSA-N (1r,5s)-n-[(2-chlorophenyl)methyl]-n-cyclopropyl-9-[(3s)-3-hydroxybutanoyl]-7-[4-[2-(2,3,6-trifluorophenoxy)propyl]phenyl]-3,9-diazabicyclo[3.3.1]non-6-ene-6-carboxamide Chemical compound C=1([C@@]2([H])CNC[C@](N2C(=O)C[C@H](C)O)(CC=1C=1C=CC(CC(C)OC=2C(=C(F)C=CC=2F)F)=CC=1)[H])C(=O)N(C1CC1)CC1=CC=CC=C1Cl LFGLSENCOIFTLS-MYQURODFSA-N 0.000 claims 1
- HKXOGUWLPNRQOJ-UBLOXDIOSA-N (1s,5r)-n-[(2-chlorophenyl)methyl]-n-cyclopropyl-3-[(3r)-3-hydroxybutanoyl]-7-[4-[3-(2,3,6-trifluorophenoxy)propyl]phenyl]-3,9-diazabicyclo[3.3.1]non-6-ene-6-carboxamide Chemical compound C=1([C@]2([H])CN(C[C@@](N2)(CC=1C=1C=CC(CCCOC=2C(=C(F)C=CC=2F)F)=CC=1)[H])C(=O)C[C@@H](C)O)C(=O)N(C1CC1)CC1=CC=CC=C1Cl HKXOGUWLPNRQOJ-UBLOXDIOSA-N 0.000 claims 1
- 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000002249 Diabetes Complications Diseases 0.000 claims 1
- 206010012655 Diabetic complications Diseases 0.000 claims 1
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- CDDQBIWIOSSSDK-ORLCUPCUSA-N N[C@@H](CO)C(N1C[C@H](C(C(O)=O)=C(C2)C3=CC=C(CCCOC(C(F)=CC=C4F)=C4F)C=C3)N[C@H]2C1)=O.ClC1=C(CNC2CC2)C=CC=C1 Chemical compound N[C@@H](CO)C(N1C[C@H](C(C(O)=O)=C(C2)C3=CC=C(CCCOC(C(F)=CC=C4F)=C4F)C=C3)N[C@H]2C1)=O.ClC1=C(CNC2CC2)C=CC=C1 CDDQBIWIOSSSDK-ORLCUPCUSA-N 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000001647 Renal Insufficiency Diseases 0.000 claims 1
- 206010063897 Renal ischaemia Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000007675 cardiac surgery Methods 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 230000008482 dysregulation Effects 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000028993 immune response Effects 0.000 claims 1
- 201000001881 impotence Diseases 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 201000006370 kidney failure Diseases 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- ILHIZUJWNGLALK-UHFFFAOYSA-N n-(2-phenylethyl)cyclopropanamine Chemical compound C1CC1NCCC1=CC=CC=C1 ILHIZUJWNGLALK-UHFFFAOYSA-N 0.000 claims 1
- KJYVKUQRRKDPAX-UHFFFAOYSA-N n-[(2,3-dichlorophenyl)methyl]cyclopropanamine Chemical compound ClC1=CC=CC(CNC2CC2)=C1Cl KJYVKUQRRKDPAX-UHFFFAOYSA-N 0.000 claims 1
- QWMNTOVGKJAROU-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]ethanamine Chemical compound CCNCC1=CC=CC=C1Cl QWMNTOVGKJAROU-UHFFFAOYSA-N 0.000 claims 1
- UZYPFBRRGVZJNV-UHFFFAOYSA-N n-[(2-fluorophenyl)methyl]cyclopropanamine Chemical compound FC1=CC=CC=C1CNC1CC1 UZYPFBRRGVZJNV-UHFFFAOYSA-N 0.000 claims 1
- WYQUCNZBUBLJHN-UHFFFAOYSA-N n-[(2-methylphenyl)methyl]cyclopropanamine Chemical compound CC1=CC=CC=C1CNC1CC1 WYQUCNZBUBLJHN-UHFFFAOYSA-N 0.000 claims 1
- BTBDLUOYLCXSMK-UHFFFAOYSA-N n-[(3,5-dimethoxyphenyl)methyl]cyclopropanamine Chemical compound COC1=CC(OC)=CC(CNC2CC2)=C1 BTBDLUOYLCXSMK-UHFFFAOYSA-N 0.000 claims 1
- NJHZDGHFBLATGX-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]cyclopropanamine Chemical compound ClC1=CC=CC=C1CCNC1CC1 NJHZDGHFBLATGX-UHFFFAOYSA-N 0.000 claims 1
- AOMAZSZEDRDSIF-UHFFFAOYSA-N n-[[3-(trifluoromethyl)phenyl]methyl]cyclopropanamine Chemical compound FC(F)(F)C1=CC=CC(CNC2CC2)=C1 AOMAZSZEDRDSIF-UHFFFAOYSA-N 0.000 claims 1
- USBAUXJPPHVCTF-UHFFFAOYSA-N n-benzylcyclopropanamine Chemical compound C=1C=CC=CC=1CNC1CC1 USBAUXJPPHVCTF-UHFFFAOYSA-N 0.000 claims 1
- 230000002988 nephrogenic effect Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 238000007631 vascular surgery Methods 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP0204705 | 2002-04-29 | ||
| PCT/EP2003/003721 WO2003093267A1 (en) | 2002-04-29 | 2003-04-08 | 7-aryl-3,9-diazabicyclo(3.3.1)non-6-ene derivatives and their use as renin inhibitors in the treatment of hypertension, cardiovascular or renal diseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005527602A JP2005527602A (ja) | 2005-09-15 |
| JP2005527602A5 true JP2005527602A5 (https=) | 2006-06-01 |
| JP4041123B2 JP4041123B2 (ja) | 2008-01-30 |
Family
ID=29286070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004501406A Expired - Fee Related JP4041123B2 (ja) | 2002-04-29 | 2003-04-08 | 新規なジアザビシクロノネン |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US7427613B2 (https=) |
| EP (1) | EP1501830B1 (https=) |
| JP (1) | JP4041123B2 (https=) |
| KR (1) | KR100783863B1 (https=) |
| CN (1) | CN1649870A (https=) |
| AT (1) | ATE527261T1 (https=) |
| AU (1) | AU2003233963B2 (https=) |
| BR (1) | BR0309498A (https=) |
| CA (1) | CA2483241C (https=) |
| CL (1) | CL2003002042A1 (https=) |
| CO (1) | CO5631443A2 (https=) |
| EC (1) | ECSP045378A (https=) |
| ES (1) | ES2372931T3 (https=) |
| HR (1) | HRP20041132A2 (https=) |
| IL (1) | IL164767A0 (https=) |
| IS (1) | IS7545A (https=) |
| MA (1) | MA27305A1 (https=) |
| MX (1) | MXPA04010608A (https=) |
| NO (1) | NO20045042L (https=) |
| NZ (1) | NZ536750A (https=) |
| PL (1) | PL372141A1 (https=) |
| RU (1) | RU2343153C2 (https=) |
| TW (1) | TW200514786A (https=) |
| UA (1) | UA80821C2 (https=) |
| WO (1) | WO2003093267A1 (https=) |
| ZA (1) | ZA200408283B (https=) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004096804A1 (en) * | 2003-04-28 | 2004-11-11 | Actelion Pharmaceuticals Ltd | Diazabicyclononene and tetrahydropyridine derivatives as renin inhibitors |
| AU2004233575A1 (en) * | 2003-04-30 | 2004-11-11 | Actelion Pharmaceuticals Ltd | 9-azabicyclo'3.3.1!non-6-ee derivatives with a heteroatom at the 3-position as renin inhibitors |
| JP2006524657A (ja) * | 2003-04-30 | 2006-11-02 | アクテリオン ファマシューティカルズ リミテッド | 新規トロパン誘導体 |
| US20060235044A1 (en) * | 2003-04-30 | 2006-10-19 | Olivier Bezencon | Azabicyclononene derivatives |
| JP2006525259A (ja) * | 2003-05-02 | 2006-11-09 | アクテリオン ファマシューティカルズ リミテッド | 新規ジアザビシクロノネン誘導体 |
| WO2004105762A1 (en) * | 2003-05-30 | 2004-12-09 | Actelion Pharmaceuticals Ltd | Medical use of diazabicyclononene derivatives as inhibitors of parasite aspartic proteases |
| CN1863773A (zh) * | 2003-10-09 | 2006-11-15 | 埃科特莱茵药品有限公司 | 四氢吡啶衍生物 |
| EP1678176A1 (en) * | 2003-10-13 | 2006-07-12 | Actelion Pharmaceuticals Ltd. | Diazabicyclononene derivatives and their use as renin inhibitors |
| CN1930170A (zh) * | 2003-10-23 | 2007-03-14 | 埃科特莱茵药品有限公司 | 二氮杂二环壬烯及四氢吡啶衍生物用作肾素抑制剂 |
| WO2005054243A1 (en) * | 2003-12-05 | 2005-06-16 | Actelion Pharmaceuticals Ltd | Diazabicyclononene derivatives and their use as renin inhibitors |
| US20070135406A1 (en) * | 2003-12-05 | 2007-06-14 | Olivier Bezencon | Diazabicyclononene and tetrahydropyridine derivatives with a new side-chain |
| EP1786814B1 (en) * | 2004-08-25 | 2010-03-31 | Actelion Pharmaceuticals Ltd. | Bicyclononene derivatives as renin inhibitors |
| WO2006021403A1 (en) * | 2004-08-25 | 2006-03-02 | Actelion Pharmaceuticals Ltd | Bicyclononene derivatives |
| WO2006021401A2 (en) * | 2004-08-25 | 2006-03-02 | Actelion Pharmaceuticals Ltd | Bicylononene derivatives |
| WO2006021399A2 (en) * | 2004-08-25 | 2006-03-02 | Actelion Pharmaceuticals Ltd | Azabicyclononene derivatives as renin inhibitors |
| AR052263A1 (es) * | 2004-12-08 | 2007-03-07 | Actelion Pharmaceuticals Ltd | Derivado de diazabiciclononeno |
| WO2006063610A1 (en) * | 2004-12-17 | 2006-06-22 | Actelion Pharmaceuticals Ltd | Heteroaryl substituted diazabicyclononene derivatives |
| GB0428526D0 (en) | 2004-12-30 | 2005-02-09 | Novartis Ag | Organic compounds |
| CA2595986A1 (en) * | 2005-01-28 | 2006-08-03 | Actelion Pharmaceuticals Ltd | 7-{4-[2-(2,6-dichlor0-4-methylphenoxy)-ethoxy]phenyl}-3,9-diazabicyclo[3.3.1]non-6-ene-6-carboxylic acid cyclopropyl-(2,3-dimethylbenzyl)amides as inhibitors of renin for the treatment of hypertension |
| EP1893578A2 (en) * | 2005-05-27 | 2008-03-05 | Actelion Pharmaceuticals Ltd. | Novel piperidine carboxylic acid amide derivatives |
| GB0514203D0 (en) | 2005-07-11 | 2005-08-17 | Novartis Ag | Organic compounds |
| JP5306821B2 (ja) | 2005-12-30 | 2013-10-02 | ノバルティス アーゲー | レニン阻害剤としての３，５−置換ピペリジン化合物 |
| NZ570828A (en) | 2006-02-02 | 2011-07-29 | Actelion Pharmaceuticals Ltd | Secondary amines as renin inhibitors |
| AU2007224368A1 (en) * | 2006-03-08 | 2007-09-13 | Actelion Pharmaceuticals Ltd | New amines |
| JP2010527942A (ja) | 2007-05-24 | 2010-08-19 | メルク フロスト カナダ リミテツド | 新規類のレニン阻害剤 |
| NZ582098A (en) | 2007-06-25 | 2012-03-30 | Novartis Ag | N5-(2-ethoxyethyl)-n3-(2-pyridinyl)-3,5-piperidinedicarboxamide derivatives for use as renin inhibitors |
| AU2008288648A1 (en) | 2007-08-20 | 2009-02-26 | Merck Frosst Canada Ltd. | Renin inhibitors |
| CN102015682B (zh) | 2008-05-05 | 2014-07-16 | 埃科特莱茵药品有限公司 | 作为肾素抑制剂的3,4-取代的哌啶衍生物 |
| CN109721613B (zh) * | 2017-10-27 | 2021-07-30 | 四川科伦博泰生物医药股份有限公司 | 含季铵离子的大环酰胺化合物及其药物组合物和用途 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3509161A (en) | 1967-07-10 | 1970-04-28 | Boehringer & Soehne Gmbh | 3-phenyl-granatene-(2)-derivatives |
| GB9020927D0 (en) | 1990-09-26 | 1990-11-07 | Beecham Group Plc | Pharmaceuticals |
| US5268361A (en) * | 1991-06-07 | 1993-12-07 | Sri International | Hydroxyazido derivatives and related compounds as renin inhibitors |
| US5374719A (en) * | 1993-06-04 | 1994-12-20 | Eli Lilly And Company | Process for converting loracarbef dihydrate to loracarbef monohydrate |
| RU2167865C2 (ru) * | 1995-09-07 | 2001-05-27 | Ф. Хоффманн-Ля Рош Аг | Производные пиперидина, способ их получения, фармацевтическая композиция на их основе и промежуточные вещества |
| EP0966464B1 (en) | 1997-03-03 | 2003-05-28 | Basilea Pharmaceutica AG | Substituted 2,4-diaminopyrimidines |
| US20060223795A1 (en) * | 2003-05-02 | 2006-10-05 | Oliver Bezencon | Novel diazabicyclononene derivatives |
| WO2005054243A1 (en) * | 2003-12-05 | 2005-06-16 | Actelion Pharmaceuticals Ltd | Diazabicyclononene derivatives and their use as renin inhibitors |
-
2003
- 2003-04-08 HR HR20041132A patent/HRP20041132A2/xx not_active Application Discontinuation
- 2003-04-08 NZ NZ536750A patent/NZ536750A/xx unknown
- 2003-04-08 WO PCT/EP2003/003721 patent/WO2003093267A1/en not_active Ceased
- 2003-04-08 AU AU2003233963A patent/AU2003233963B2/en not_active Ceased
- 2003-04-08 EP EP03727287A patent/EP1501830B1/en not_active Expired - Lifetime
- 2003-04-08 RU RU2004134320/04A patent/RU2343153C2/ru not_active IP Right Cessation
- 2003-04-08 MX MXPA04010608A patent/MXPA04010608A/es not_active Application Discontinuation
- 2003-04-08 US US10/513,103 patent/US7427613B2/en not_active Expired - Fee Related
- 2003-04-08 CA CA2483241A patent/CA2483241C/en not_active Expired - Fee Related
- 2003-04-08 KR KR1020047016845A patent/KR100783863B1/ko not_active Expired - Fee Related
- 2003-04-08 PL PL03372141A patent/PL372141A1/xx not_active Application Discontinuation
- 2003-04-08 JP JP2004501406A patent/JP4041123B2/ja not_active Expired - Fee Related
- 2003-04-08 BR BR0309498-7A patent/BR0309498A/pt not_active IP Right Cessation
- 2003-04-08 CN CNA038097664A patent/CN1649870A/zh active Pending
- 2003-04-08 IL IL16476703A patent/IL164767A0/xx unknown
- 2003-04-08 AT AT03727287T patent/ATE527261T1/de not_active IP Right Cessation
- 2003-04-08 ES ES03727287T patent/ES2372931T3/es not_active Expired - Lifetime
- 2003-08-04 UA UA20041109469A patent/UA80821C2/uk unknown
- 2003-10-10 CL CL200302042A patent/CL2003002042A1/es unknown
- 2003-10-23 TW TW092129421A patent/TW200514786A/zh unknown
-
2004
- 2004-10-13 ZA ZA200408283A patent/ZA200408283B/xx unknown
- 2004-10-22 EC EC2004005378A patent/ECSP045378A/es unknown
- 2004-10-22 MA MA27914A patent/MA27305A1/fr unknown
- 2004-10-22 CO CO04106347A patent/CO5631443A2/es not_active Application Discontinuation
- 2004-11-19 NO NO20045042A patent/NO20045042L/no not_active Application Discontinuation
- 2004-11-22 IS IS7545A patent/IS7545A/is unknown
-
2008
- 2008-07-07 US US12/168,666 patent/US20080312242A1/en not_active Abandoned
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