CA2540239A1 - Imidazo(4,5-b)pyridine-derivatives as inducible no-synthase inhibitors - Google Patents
Imidazo(4,5-b)pyridine-derivatives as inducible no-synthase inhibitors Download PDFInfo
- Publication number
- CA2540239A1 CA2540239A1 CA002540239A CA2540239A CA2540239A1 CA 2540239 A1 CA2540239 A1 CA 2540239A1 CA 002540239 A CA002540239 A CA 002540239A CA 2540239 A CA2540239 A CA 2540239A CA 2540239 A1 CA2540239 A1 CA 2540239A1
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- CA
- Canada
- Prior art keywords
- compounds
- alkyl
- hydrogen
- formula
- alkoxy
- 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
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- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 title abstract description 31
- 101710089543 Nitric oxide synthase, inducible Proteins 0.000 title abstract description 30
- 239000003112 inhibitor Substances 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 142
- -1 nitro, amino Chemical group 0.000 claims description 125
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 37
- 150000002431 hydrogen Chemical group 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
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- 150000002367 halogens Chemical group 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
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- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 230000014759 maintenance of location Effects 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
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- 230000006386 memory function Effects 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- HWAPHAUYWJRCDS-UHFFFAOYSA-N methyl 3-(4-methoxypyridin-2-yl)-2,2-dimethylpropanoate Chemical compound COC(=O)C(C)(C)CC1=CC(OC)=CC=N1 HWAPHAUYWJRCDS-UHFFFAOYSA-N 0.000 description 1
- CNFIVUKCSNCIOZ-UHFFFAOYSA-N methyl 3-hydroxy-3-(4-methoxypyridin-2-yl)-2,2-dimethylpropanoate Chemical compound COC(=O)C(C)(C)C(O)C1=CC(OC)=CC=N1 CNFIVUKCSNCIOZ-UHFFFAOYSA-N 0.000 description 1
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
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- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000002858 neurotransmitter agent Substances 0.000 description 1
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- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012740 non-selective inhibitor Substances 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 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
- 239000003883 ointment base Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical group [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 208000027753 pain disease Diseases 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
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- 239000006072 paste Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000064 phosphane Inorganic materials 0.000 description 1
- 150000003002 phosphanes Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000007180 physiological regulation Effects 0.000 description 1
- 201000006292 polyarteritis nodosa Diseases 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 230000029279 positive regulation of transcription, DNA-dependent Effects 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000036515 potency Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000007363 regulatory process Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000010410 reperfusion Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229960004617 sapropterin Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 206010040400 serum sickness Diseases 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000009121 systemic therapy Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000009529 traumatic brain injury Effects 0.000 description 1
- YOQSDQBWPAFIFE-UHFFFAOYSA-M tributyl-[1-(1h-imidazo[4,5-b]pyridin-2-yl)propyl]phosphanium;chloride Chemical compound [Cl-].C1=CN=C2NC(C(CC)[P+](CCCC)(CCCC)CCCC)=NC2=C1 YOQSDQBWPAFIFE-UHFFFAOYSA-M 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000005500 uronium group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
- C07D471/04—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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03022042 | 2003-10-01 | ||
| EP03022042.0 | 2003-10-01 | ||
| PCT/EP2004/052370 WO2005030768A1 (en) | 2003-10-01 | 2004-09-30 | Imidazo(4,5-b)pyridine-derivatives as inducible no-synthase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2540239A1 true CA2540239A1 (en) | 2005-04-07 |
Family
ID=34384569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002540239A Abandoned CA2540239A1 (en) | 2003-10-01 | 2004-09-30 | Imidazo(4,5-b)pyridine-derivatives as inducible no-synthase inhibitors |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US7329677B2 (enExample) |
| EP (1) | EP1675853B1 (enExample) |
| JP (1) | JP2007507463A (enExample) |
| KR (1) | KR20060092221A (enExample) |
| CN (1) | CN1856492A (enExample) |
| AT (1) | ATE398617T1 (enExample) |
| AU (1) | AU2004276012A1 (enExample) |
| BR (1) | BRPI0415038A (enExample) |
| CA (1) | CA2540239A1 (enExample) |
| DE (1) | DE602004014523D1 (enExample) |
| IL (1) | IL173629A0 (enExample) |
| MX (1) | MXPA06003347A (enExample) |
| NO (1) | NO20061343L (enExample) |
| RS (1) | RS20060205A (enExample) |
| WO (1) | WO2005030768A1 (enExample) |
| ZA (1) | ZA200601139B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004303515A1 (en) | 2003-10-01 | 2005-07-07 | Altana Pharma Ag | Aminopyridine-derivatives as inductible no-synthase inhibitors |
| WO2005030771A1 (en) | 2003-10-01 | 2005-04-07 | Altana Pharma Ag | Imidazopyridine-derivatives as inductible no-synthase inhibitors |
| ATE399168T1 (de) | 2003-10-01 | 2008-07-15 | Nycomed Gmbh | Imidazopyridin-derivate und ihre verwendung als induzierbare no-synthase inhibitoren |
| KR100863692B1 (ko) * | 2006-12-08 | 2008-10-15 | 울산대학교 산학협력단 | 퇴행성질환 및 염증질환에 대한 예방치료 효과를 갖는7-하이드록시-6-메톡시-1,2,3,4-테트라하이드로이소퀴놀린유도체 |
| WO2009029625A1 (en) * | 2007-08-27 | 2009-03-05 | Kalypsys, Inc. | 4- [heterocyclyl-methyl] -8-fluoro-quinolin-2-ones useful as nitric oxide synthase inhibitors |
| GB201512635D0 (en) | 2015-07-17 | 2015-08-26 | Ucl Business Plc | Uses of therapeutic compounds |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| AU2003226706A1 (en) | 2002-03-27 | 2003-10-08 | Altana Pharma Ag | Novel alkoxypyridine-derivatives |
| AU2004303515A1 (en) | 2003-10-01 | 2005-07-07 | Altana Pharma Ag | Aminopyridine-derivatives as inductible no-synthase inhibitors |
| WO2005030771A1 (en) | 2003-10-01 | 2005-04-07 | Altana Pharma Ag | Imidazopyridine-derivatives as inductible no-synthase inhibitors |
| ATE399168T1 (de) | 2003-10-01 | 2008-07-15 | Nycomed Gmbh | Imidazopyridin-derivate und ihre verwendung als induzierbare no-synthase inhibitoren |
| EP1673371B1 (en) | 2003-10-01 | 2008-08-06 | Nycomed GmbH | Imidazopyridine-derivatives as inducible no-synthase inhibitors |
-
2004
- 2004-09-30 AT AT04787257T patent/ATE398617T1/de not_active IP Right Cessation
- 2004-09-30 RS YUP-2006/0205A patent/RS20060205A/sr unknown
- 2004-09-30 DE DE602004014523T patent/DE602004014523D1/de not_active Expired - Fee Related
- 2004-09-30 JP JP2006530260A patent/JP2007507463A/ja not_active Withdrawn
- 2004-09-30 EP EP04787257A patent/EP1675853B1/en not_active Expired - Lifetime
- 2004-09-30 US US10/573,203 patent/US7329677B2/en not_active Expired - Fee Related
- 2004-09-30 BR BRPI0415038-4A patent/BRPI0415038A/pt not_active IP Right Cessation
- 2004-09-30 AU AU2004276012A patent/AU2004276012A1/en not_active Abandoned
- 2004-09-30 CN CNA2004800277964A patent/CN1856492A/zh active Pending
- 2004-09-30 CA CA002540239A patent/CA2540239A1/en not_active Abandoned
- 2004-09-30 MX MXPA06003347A patent/MXPA06003347A/es not_active Application Discontinuation
- 2004-09-30 KR KR1020067005877A patent/KR20060092221A/ko not_active Withdrawn
- 2004-09-30 WO PCT/EP2004/052370 patent/WO2005030768A1/en not_active Ceased
-
2006
- 2006-02-08 ZA ZA200601139A patent/ZA200601139B/en unknown
- 2006-02-09 IL IL173629A patent/IL173629A0/en unknown
- 2006-03-24 NO NO20061343A patent/NO20061343L/no not_active Application Discontinuation
-
2007
- 2007-12-17 US US12/000,709 patent/US20080108652A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA06003347A (es) | 2006-06-08 |
| US20080108652A1 (en) | 2008-05-08 |
| US20070010549A1 (en) | 2007-01-11 |
| AU2004276012A1 (en) | 2005-04-07 |
| KR20060092221A (ko) | 2006-08-22 |
| WO2005030768A1 (en) | 2005-04-07 |
| RS20060205A (sr) | 2008-08-07 |
| DE602004014523D1 (de) | 2008-07-31 |
| NO20061343L (no) | 2006-03-24 |
| ATE398617T1 (de) | 2008-07-15 |
| IL173629A0 (en) | 2006-07-05 |
| EP1675853B1 (en) | 2008-06-18 |
| US7329677B2 (en) | 2008-02-12 |
| EP1675853A1 (en) | 2006-07-05 |
| CN1856492A (zh) | 2006-11-01 |
| BRPI0415038A (pt) | 2006-12-12 |
| ZA200601139B (en) | 2007-05-30 |
| JP2007507463A (ja) | 2007-03-29 |
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| EP1490366B1 (en) | alkoxypyridine-derivatives | |
| US20080108652A1 (en) | Imidazo (4,5-B) pyridine-derivatives as inducible no-synthase inhibitors | |
| EP1675854B1 (en) | Imidazopyridine-derivatives as inductible no-synthase inhibitors | |
| EP1673371B1 (en) | Imidazopyridine-derivatives as inducible no-synthase inhibitors | |
| EP1599473B1 (en) | Imidazo 4,5-b quinoline-derivatives and their use as no-synthase inhibitors | |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |