AU2004303515A1 - Aminopyridine-derivatives as inductible no-synthase inhibitors - Google Patents
Aminopyridine-derivatives as inductible no-synthase inhibitors Download PDFInfo
- Publication number
- AU2004303515A1 AU2004303515A1 AU2004303515A AU2004303515A AU2004303515A1 AU 2004303515 A1 AU2004303515 A1 AU 2004303515A1 AU 2004303515 A AU2004303515 A AU 2004303515A AU 2004303515 A AU2004303515 A AU 2004303515A AU 2004303515 A1 AU2004303515 A1 AU 2004303515A1
- Authority
- AU
- Australia
- Prior art keywords
- phenyl
- imidazo
- pyridin
- methyl
- compounds
- 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.)
- Abandoned
Links
- 239000003112 inhibitor Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 359
- -1 nitro, amino Chemical group 0.000 claims description 163
- 239000001257 hydrogen Substances 0.000 claims description 86
- 229910052739 hydrogen Inorganic materials 0.000 claims description 86
- 150000003839 salts Chemical class 0.000 claims description 71
- 238000000034 method Methods 0.000 claims description 52
- 150000001204 N-oxides Chemical class 0.000 claims description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical group 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 15
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- QSUYHIGQOBHJJY-UHFFFAOYSA-N 6-[2-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)ethyl]-4-methylpyridin-2-amine Chemical compound CC1=CC(N)=NC(CCC=2NC3=NC=C(Br)C=C3N=2)=C1 QSUYHIGQOBHJJY-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 8
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims description 7
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical group C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 7
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- QRBGBBUDERZGMQ-UHFFFAOYSA-N 4-methyl-6-[2-(6-phenyl-1h-imidazo[4,5-b]pyridin-2-yl)ethyl]pyridin-2-amine Chemical compound CC1=CC(N)=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC=CC=2)=C1 QRBGBBUDERZGMQ-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 208000037976 chronic inflammation Diseases 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- FBAZEUBENLHZFK-UHFFFAOYSA-N 6-[2-[6-[4-(dimethylamino)phenyl]-1h-imidazo[4,5-b]pyridin-2-yl]ethyl]-4-methylpyridin-2-amine Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=C(NC(CCC=2N=C(N)C=C(C)C=2)=N2)C2=C1 FBAZEUBENLHZFK-UHFFFAOYSA-N 0.000 claims description 4
- LFMFPKKYRXFHHZ-UHFFFAOYSA-N R24 Chemical compound C1=C(Cl)C(C)=CC=C1NC1=NC(N)=C(C=CC=C2)C2=N1 LFMFPKKYRXFHHZ-UHFFFAOYSA-N 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 210000000056 organ Anatomy 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- FJGOWXFGCTUIPW-UHFFFAOYSA-N 6-[2-(1h-imidazo[4,5-b]pyridin-2-yl)ethyl]-4-methylpyridin-2-amine Chemical compound CC1=CC(N)=NC(CCC=2NC3=NC=CC=C3N=2)=C1 FJGOWXFGCTUIPW-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 230000002093 peripheral effect Effects 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- UIRDCXIQKFAZPW-UHFFFAOYSA-N 6-[2-[6-(4-chlorophenyl)-1h-imidazo[4,5-b]pyridin-2-yl]ethyl]-4-methylpyridin-2-amine Chemical compound CC1=CC(N)=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(Cl)=CC=2)=C1 UIRDCXIQKFAZPW-UHFFFAOYSA-N 0.000 claims description 2
- SXCSZNOYDRSCSH-UHFFFAOYSA-N 3-[2-[2-(6-amino-4-methylpyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]phenol Chemical compound CC1=CC(N)=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=C(O)C=CC=2)=C1 SXCSZNOYDRSCSH-UHFFFAOYSA-N 0.000 claims 1
- RTAGWYKEPBWWKZ-UHFFFAOYSA-N 4-[2-[2-(6-amino-4-methylpyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]benzonitrile Chemical compound CC1=CC(N)=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)C#N)=C1 RTAGWYKEPBWWKZ-UHFFFAOYSA-N 0.000 claims 1
- GGQOGDVJQSYHSF-UHFFFAOYSA-N 4-methyl-6-[2-[6-(4-methylphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]ethyl]pyridin-2-amine Chemical compound C1=CC(C)=CC=C1C1=CN=C(NC(CCC=2N=C(N)C=C(C)C=2)=N2)C2=C1 GGQOGDVJQSYHSF-UHFFFAOYSA-N 0.000 claims 1
- JGAITFGEWWNTQU-UHFFFAOYSA-N 4-methyl-6-[2-[6-(4-phenylmethoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]ethyl]pyridin-2-amine Chemical compound CC1=CC(N)=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=C1 JGAITFGEWWNTQU-UHFFFAOYSA-N 0.000 claims 1
- ZLRUSDPQJLCKBV-UHFFFAOYSA-N 4-methyl-6-[2-[6-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-1h-imidazo[4,5-b]pyridin-2-yl]ethyl]pyridin-2-amine Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C=C3N=C(CCC=4N=C(N)C=C(C)C=4)NC3=NC=2)C=C1 ZLRUSDPQJLCKBV-UHFFFAOYSA-N 0.000 claims 1
- SBQONCKGWDGHHJ-UHFFFAOYSA-N 6-[2-(1h-imidazo[4,5-b]pyridin-2-yl)ethyl]-4-methoxypyridin-2-amine Chemical compound COC1=CC(N)=NC(CCC=2NC3=NC=CC=C3N=2)=C1 SBQONCKGWDGHHJ-UHFFFAOYSA-N 0.000 claims 1
- PLLSKVHKFJDJPB-UHFFFAOYSA-N 6-[2-[6-(3,5-dichlorophenyl)-1h-imidazo[4,5-b]pyridin-2-yl]ethyl]-4-methylpyridin-2-amine Chemical compound CC1=CC(N)=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=C(Cl)C=C(Cl)C=2)=C1 PLLSKVHKFJDJPB-UHFFFAOYSA-N 0.000 claims 1
- YZAIJWXSDGBDES-UHFFFAOYSA-N 6-[2-[6-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridin-2-yl]ethyl]-4-methylpyridin-2-amine Chemical compound CC1=CC(N)=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(F)=CC=2)=C1 YZAIJWXSDGBDES-UHFFFAOYSA-N 0.000 claims 1
- LAUBQFHJZXIZLD-UHFFFAOYSA-N 6-[2-[6-(4-iodophenyl)-1h-imidazo[4,5-b]pyridin-2-yl]ethyl]-4-methylpyridin-2-amine Chemical compound CC1=CC(N)=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(I)=CC=2)=C1 LAUBQFHJZXIZLD-UHFFFAOYSA-N 0.000 claims 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 340
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 309
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Landscapes
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- Engineering & Computer Science (AREA)
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- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
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- Hospice & Palliative Care (AREA)
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- Communicable Diseases (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
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- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03022040.4 | 2003-10-01 | ||
| EP03022040 | 2003-10-01 | ||
| PCT/EP2004/052373 WO2005061496A1 (en) | 2003-10-01 | 2004-09-30 | Aminopyridine-derivatives as inductible no-synthase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2004303515A1 true AU2004303515A1 (en) | 2005-07-07 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004303515A Abandoned AU2004303515A1 (en) | 2003-10-01 | 2004-09-30 | Aminopyridine-derivatives as inductible no-synthase inhibitors |
Country Status (16)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007507463A (ja) | 2003-10-01 | 2007-03-29 | アルタナ ファルマ アクチエンゲゼルシャフト | 誘導性ＮＯシンターゼ阻害剤としてのイミダゾ［４，５−ｂ］ピリジン誘導体 |
| NZ546437A (en) | 2003-10-01 | 2009-09-25 | Altana Pharma Ag | Imidazopyridine-derivatives as inducible NO-synthase inhibitors |
| ATE399168T1 (de) | 2003-10-01 | 2008-07-15 | Nycomed Gmbh | Imidazopyridin-derivate und ihre verwendung als induzierbare no-synthase inhibitoren |
| US7453002B2 (en) | 2004-06-15 | 2008-11-18 | Bristol-Myers Squibb Company | Five-membered heterocycles useful as serine protease inhibitors |
| EP1866306B1 (en) | 2005-03-31 | 2009-06-17 | Nycomed GmbH | Imidazopyridine derivatives useful as inos inhibitors |
| JP2010531358A (ja) * | 2007-06-27 | 2010-09-24 | メルク・シャープ・エンド・ドーム・コーポレイション | ヒストン脱アセチル化酵素阻害剤としてのピリジル及びピリミジニル誘導体 |
| US20100278751A1 (en) * | 2009-04-30 | 2010-11-04 | Washington University | Radiolabeled 2-amino-4-alkyl-6-(haloalkyl)pyridine compounds and their use in diagnostic imaging |
| WO2011150156A2 (en) * | 2010-05-26 | 2011-12-01 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
| GB201512635D0 (en) | 2015-07-17 | 2015-08-26 | Ucl Business Plc | Uses of therapeutic compounds |
| CN117215117A (zh) | 2017-05-15 | 2023-12-12 | 索尼公司 | 照明单元和显示设备 |
| US12240815B2 (en) * | 2020-02-24 | 2025-03-04 | Northwestern University | Potent and selective human neuronal nitric oxide synthase inhibitors |
Family Cites Families (11)
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| SE418966B (sv) * | 1974-02-18 | 1981-07-06 | Haessle Ab | Analogiforfarande for framstellning av foreningar med magsyrasekretionsinhiberande verkan |
| US4045564A (en) | 1974-02-18 | 1977-08-30 | Ab Hassle | Benzimidazole derivatives useful as gastric acid secretion inhibitors |
| GB8307865D0 (en) * | 1983-03-22 | 1983-04-27 | Fujisawa Pharmaceutical Co | Benzimidazole derivatives |
| AU650953B2 (en) * | 1991-03-21 | 1994-07-07 | Novartis Ag | Inhaler |
| SE512835C2 (sv) * | 1996-01-08 | 2000-05-22 | Astrazeneca Ab | Doseringsform innehållande en mångfald enheter alla inneslutande syralabil H+K+ATPas-hämmare |
| AUPP873799A0 (en) * | 1999-02-17 | 1999-03-11 | Fujisawa Pharmaceutical Co., Ltd. | Pyridine compounds |
| BR0308785A (pt) | 2002-03-27 | 2005-01-11 | Altana Pharma Ag | Derivados de alcoxipiridina |
| EP1673371B1 (en) | 2003-10-01 | 2008-08-06 | Nycomed GmbH | Imidazopyridine-derivatives as inducible no-synthase inhibitors |
| JP2007507463A (ja) | 2003-10-01 | 2007-03-29 | アルタナ ファルマ アクチエンゲゼルシャフト | 誘導性ＮＯシンターゼ阻害剤としてのイミダゾ［４，５−ｂ］ピリジン誘導体 |
| NZ546437A (en) | 2003-10-01 | 2009-09-25 | Altana Pharma Ag | Imidazopyridine-derivatives as inducible NO-synthase inhibitors |
| ATE399168T1 (de) | 2003-10-01 | 2008-07-15 | Nycomed Gmbh | Imidazopyridin-derivate und ihre verwendung als induzierbare no-synthase inhibitoren |
-
2004
- 2004-09-30 EP EP04820599A patent/EP1670798A1/en not_active Withdrawn
- 2004-09-30 JP JP2006530261A patent/JP2007507464A/ja not_active Withdrawn
- 2004-09-30 CN CNB2004800278079A patent/CN100415746C/zh not_active Expired - Fee Related
- 2004-09-30 AU AU2004303515A patent/AU2004303515A1/en not_active Abandoned
- 2004-09-30 BR BRPI0415034-1A patent/BRPI0415034A/pt not_active IP Right Cessation
- 2004-09-30 NZ NZ546394A patent/NZ546394A/en unknown
- 2004-09-30 US US10/573,204 patent/US7317021B2/en not_active Expired - Fee Related
- 2004-09-30 WO PCT/EP2004/052373 patent/WO2005061496A1/en not_active Ceased
- 2004-09-30 KR KR1020067005860A patent/KR20060092219A/ko not_active Withdrawn
- 2004-09-30 EA EA200600601A patent/EA200600601A1/ru unknown
- 2004-09-30 MX MXPA06003345A patent/MXPA06003345A/es not_active Application Discontinuation
- 2004-09-30 CA CA002540230A patent/CA2540230A1/en not_active Abandoned
- 2004-09-30 RS YUP-2006/0206A patent/RS20060206A/sr unknown
-
2006
- 2006-02-08 ZA ZA200601140A patent/ZA200601140B/en unknown
- 2006-02-09 IL IL173628A patent/IL173628A0/en unknown
- 2006-04-24 NO NO20061789A patent/NO20061789L/no not_active Application Discontinuation
-
2007
- 2007-11-16 US US11/984,364 patent/US7781453B2/en not_active Expired - Fee Related
-
2010
- 2010-07-14 US US12/836,279 patent/US20100280002A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| NO20061789L (no) | 2006-04-24 |
| IL173628A0 (en) | 2006-07-05 |
| US7317021B2 (en) | 2008-01-08 |
| CN1856493A (zh) | 2006-11-01 |
| JP2007507464A (ja) | 2007-03-29 |
| US20080176894A1 (en) | 2008-07-24 |
| WO2005061496A8 (en) | 2006-02-16 |
| RS20060206A (sr) | 2008-08-07 |
| NZ546394A (en) | 2009-08-28 |
| BRPI0415034A (pt) | 2006-12-12 |
| US20070043072A1 (en) | 2007-02-22 |
| CA2540230A1 (en) | 2005-07-07 |
| WO2005061496A1 (en) | 2005-07-07 |
| HK1096968A1 (zh) | 2007-06-15 |
| MXPA06003345A (es) | 2006-06-08 |
| EP1670798A1 (en) | 2006-06-21 |
| US7781453B2 (en) | 2010-08-24 |
| EA200600601A1 (ru) | 2006-10-27 |
| ZA200601140B (en) | 2007-05-30 |
| CN100415746C (zh) | 2008-09-03 |
| KR20060092219A (ko) | 2006-08-22 |
| US20100280002A1 (en) | 2010-11-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |