NZ546394A - Aminopyridine derivatives as inductible NO-synthase inhibitors - Google Patents
Aminopyridine derivatives as inductible NO-synthase inhibitorsInfo
- Publication number
- NZ546394A NZ546394A NZ546394A NZ54639404A NZ546394A NZ 546394 A NZ546394 A NZ 546394A NZ 546394 A NZ546394 A NZ 546394A NZ 54639404 A NZ54639404 A NZ 54639404A NZ 546394 A NZ546394 A NZ 546394A
- Authority
- NZ
- New Zealand
- Prior art keywords
- phenyl
- pyridin
- imidazo
- methyl
- alkyl
- Prior art date
Links
- 108010021487 Nitric Oxide Synthase Proteins 0.000 title description 16
- 102000008299 Nitric Oxide Synthase Human genes 0.000 title description 15
- 239000003112 inhibitor Substances 0.000 title description 7
- 150000003927 aminopyridines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 356
- 150000003839 salts Chemical class 0.000 claims abstract description 73
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 52
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 36
- 208000037976 chronic inflammation Diseases 0.000 claims abstract description 5
- 230000001154 acute effect Effects 0.000 claims abstract description 4
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims abstract description 4
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 4
- 210000000056 organ Anatomy 0.000 claims abstract description 4
- 230000002093 peripheral effect Effects 0.000 claims abstract description 3
- -1 nitro, amino Chemical group 0.000 claims description 166
- 239000001257 hydrogen Substances 0.000 claims description 86
- 229910052739 hydrogen Inorganic materials 0.000 claims description 86
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical group 0.000 claims description 39
- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 claims description 28
- 101710089543 Nitric oxide synthase, inducible Proteins 0.000 claims description 27
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)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 15
- 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 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 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 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 8
- 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
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 230000002401 inhibitory effect Effects 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
- 230000005764 inhibitory process Effects 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 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
- 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 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 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
- QHRNEEVPKPLWSF-UHFFFAOYSA-N 4-methyl-6-[2-[6-(3-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=C(OCC=3C=CC=CC=3)C=CC=2)=C1 QHRNEEVPKPLWSF-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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
- 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
- YWZLURUJNGVPPI-UHFFFAOYSA-N 4-methyl-6-[2-[6-(4-piperidin-1-ylsulfonylphenyl)-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)S(=O)(=O)N2CCCCC2)=C1 YWZLURUJNGVPPI-UHFFFAOYSA-N 0.000 claims 1
- LVBRCVUIFGCBOO-UHFFFAOYSA-N 4-methyl-6-[2-[6-(4-pyrrolidin-1-ylsulfonylphenyl)-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)S(=O)(=O)N2CCCC2)=C1 LVBRCVUIFGCBOO-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
- HGPHOYJZAWYPBA-UHFFFAOYSA-N 4-methyl-6-[2-[6-[4-(trifluoromethyl)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)C(F)(F)F)=C1 HGPHOYJZAWYPBA-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
- MMFAYEYGPWKRKF-UHFFFAOYSA-N 6-[2-[6-[4-(azetidin-1-ylsulfonyl)phenyl]-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(=CC=2)S(=O)(=O)N2CCC2)=C1 MMFAYEYGPWKRKF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 6
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- 239000000243 solution Substances 0.000 description 81
- 238000004809 thin layer chromatography Methods 0.000 description 73
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- 238000000034 method Methods 0.000 description 50
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Endocrinology (AREA)
- Psychology (AREA)
- Obesity (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
|---|---|
| NZ546394A true NZ546394A (en) | 2009-08-28 |
Family
ID=34707254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ546394A NZ546394A (en) | 2003-10-01 | 2004-09-30 | Aminopyridine derivatives as inductible NO-synthase inhibitors |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US7317021B2 (enExample) |
| EP (1) | EP1670798A1 (enExample) |
| JP (1) | JP2007507464A (enExample) |
| KR (1) | KR20060092219A (enExample) |
| CN (1) | CN100415746C (enExample) |
| AU (1) | AU2004303515A1 (enExample) |
| BR (1) | BRPI0415034A (enExample) |
| CA (1) | CA2540230A1 (enExample) |
| EA (1) | EA200600601A1 (enExample) |
| IL (1) | IL173628A0 (enExample) |
| MX (1) | MXPA06003345A (enExample) |
| NO (1) | NO20061789L (enExample) |
| NZ (1) | NZ546394A (enExample) |
| RS (1) | RS20060206A (enExample) |
| WO (1) | WO2005061496A1 (enExample) |
| ZA (1) | ZA200601140B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA06003351A (es) | 2003-10-01 | 2006-06-08 | Altana Pharma Ag | Derivados de imidazopiridina como inhibidores de no-sintasa inducible. |
| KR20060092220A (ko) | 2003-10-01 | 2006-08-22 | 알타나 파마 아게 | 유도성 ｎｏ-신타아제 저해제로서의 이미다조피리딘 유도체 |
| KR20060092221A (ko) | 2003-10-01 | 2006-08-22 | 알타나 파마 아게 | 유도성 ｎｏ-신타제 억제제로서의이미다조（4,5-ｂ）피리딘 유도체 |
| US7453002B2 (en) | 2004-06-15 | 2008-11-18 | Bristol-Myers Squibb Company | Five-membered heterocycles useful as serine protease inhibitors |
| WO2006103255A1 (en) | 2005-03-31 | 2006-10-05 | Nycomed Gmbh | Imidazopyridine derivatives useful as inos inhibitors |
| AU2008271170A1 (en) * | 2007-06-27 | 2009-01-08 | Merck Sharp & Dohme Corp. | Pyridyl and pyrimidinyl derivatives as histone deacetylase inhibitors |
| 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 |
| CA2800618C (en) | 2010-05-26 | 2018-08-28 | 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4045564A (en) * | 1974-02-18 | 1977-08-30 | Ab Hassle | Benzimidazole derivatives useful as gastric acid secretion inhibitors |
| SE418966B (sv) | 1974-02-18 | 1981-07-06 | Haessle Ab | Analogiforfarande for framstellning av foreningar med magsyrasekretionsinhiberande verkan |
| 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 |
| ATE384722T1 (de) * | 2002-03-27 | 2008-02-15 | Nycomed Gmbh | Alkoxypyridinderivate |
| MXPA06003351A (es) | 2003-10-01 | 2006-06-08 | Altana Pharma Ag | Derivados de imidazopiridina como inhibidores de no-sintasa inducible. |
| KR20060092220A (ko) | 2003-10-01 | 2006-08-22 | 알타나 파마 아게 | 유도성 ｎｏ-신타아제 저해제로서의 이미다조피리딘 유도체 |
| KR20060092221A (ko) | 2003-10-01 | 2006-08-22 | 알타나 파마 아게 | 유도성 ｎｏ-신타제 억제제로서의이미다조（4,5-ｂ）피리딘 유도체 |
| BRPI0414873A (pt) | 2003-10-01 | 2006-12-12 | Altana Pharma Ag | derivados de imidazopiridina como inibidores de no-sintase induzìveis |
-
2004
- 2004-09-30 EP EP04820599A patent/EP1670798A1/en not_active Withdrawn
- 2004-09-30 US US10/573,204 patent/US7317021B2/en not_active Expired - Fee Related
- 2004-09-30 AU AU2004303515A patent/AU2004303515A1/en not_active Abandoned
- 2004-09-30 EA EA200600601A patent/EA200600601A1/ru unknown
- 2004-09-30 JP JP2006530261A patent/JP2007507464A/ja not_active Withdrawn
- 2004-09-30 RS YUP-2006/0206A patent/RS20060206A/sr unknown
- 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 CA CA002540230A patent/CA2540230A1/en not_active Abandoned
- 2004-09-30 MX MXPA06003345A patent/MXPA06003345A/es not_active Application Discontinuation
- 2004-09-30 WO PCT/EP2004/052373 patent/WO2005061496A1/en not_active Ceased
- 2004-09-30 CN CNB2004800278079A patent/CN100415746C/zh not_active Expired - Fee Related
- 2004-09-30 KR KR1020067005860A patent/KR20060092219A/ko not_active Withdrawn
-
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 |
|---|---|
| MXPA06003345A (es) | 2006-06-08 |
| US20100280002A1 (en) | 2010-11-04 |
| JP2007507464A (ja) | 2007-03-29 |
| US20070043072A1 (en) | 2007-02-22 |
| AU2004303515A1 (en) | 2005-07-07 |
| ZA200601140B (en) | 2007-05-30 |
| HK1096968A1 (zh) | 2007-06-15 |
| US7781453B2 (en) | 2010-08-24 |
| US20080176894A1 (en) | 2008-07-24 |
| IL173628A0 (en) | 2006-07-05 |
| CN100415746C (zh) | 2008-09-03 |
| US7317021B2 (en) | 2008-01-08 |
| WO2005061496A8 (en) | 2006-02-16 |
| WO2005061496A1 (en) | 2005-07-07 |
| CN1856493A (zh) | 2006-11-01 |
| EA200600601A1 (ru) | 2006-10-27 |
| CA2540230A1 (en) | 2005-07-07 |
| NO20061789L (no) | 2006-04-24 |
| RS20060206A (sr) | 2008-08-07 |
| EP1670798A1 (en) | 2006-06-21 |
| BRPI0415034A (pt) | 2006-12-12 |
| KR20060092219A (ko) | 2006-08-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) |