NO330766B1 - Viral Inhibitors - Google Patents
Viral Inhibitors Download PDFInfo
- Publication number
- NO330766B1 NO330766B1 NO20045731A NO20045731A NO330766B1 NO 330766 B1 NO330766 B1 NO 330766B1 NO 20045731 A NO20045731 A NO 20045731A NO 20045731 A NO20045731 A NO 20045731A NO 330766 B1 NO330766 B1 NO 330766B1
- Authority
- NO
- Norway
- Prior art keywords
- imidazo
- methyl
- pyridine
- phenyl
- bromophenyl
- Prior art date
Links
- 239000003443 antiviral agent Substances 0.000 title description 6
- 208000036142 Viral infection Diseases 0.000 claims abstract description 39
- 241000700605 Viruses Species 0.000 claims abstract description 39
- 230000009385 viral infection Effects 0.000 claims abstract description 38
- UBOOKRVGOBKDMM-UHFFFAOYSA-N 3h-imidazo[4,5-c]pyridine Chemical class C1=NC=C2NC=NC2=C1 UBOOKRVGOBKDMM-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000011282 treatment Methods 0.000 claims abstract description 26
- 241000710781 Flaviviridae Species 0.000 claims abstract description 11
- 241000709664 Picornaviridae Species 0.000 claims abstract description 10
- 230000002265 prevention Effects 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 141
- 238000002360 preparation method Methods 0.000 claims description 114
- -1 -CH2-NR<7>R<8> Chemical group 0.000 claims description 110
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 67
- 150000003839 salts Chemical class 0.000 claims description 35
- 239000003814 drug Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 31
- 241000711549 Hepacivirus C Species 0.000 claims description 29
- 208000015181 infectious disease Diseases 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 229940079593 drug Drugs 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 230000000840 anti-viral effect Effects 0.000 claims description 20
- 241001144416 Picornavirales Species 0.000 claims description 19
- 125000001624 naphthyl group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 16
- 238000002560 therapeutic procedure Methods 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 238000011321 prophylaxis Methods 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 230000002195 synergetic effect Effects 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
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- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 3
- VCMFXCQTFOCKOE-UHFFFAOYSA-N 2-(2-fluorophenyl)-5-[(4-iodophenyl)methyl]imidazo[4,5-c]pyridine Chemical compound FC1=CC=CC=C1C1=NC2=CN(CC=3C=CC(I)=CC=3)C=CC2=N1 VCMFXCQTFOCKOE-UHFFFAOYSA-N 0.000 claims description 3
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- HLFJMXLDHKSAOD-UHFFFAOYSA-N 5-[(4-bromophenyl)methyl]-2-(2-fluorophenyl)imidazo[4,5-c]pyridine Chemical compound FC1=CC=CC=C1C1=NC2=CN(CC=3C=CC(Br)=CC=3)C=CC2=N1 HLFJMXLDHKSAOD-UHFFFAOYSA-N 0.000 claims description 3
- MTWGESHKSOCJSY-UHFFFAOYSA-N 5-[(4-bromophenyl)methyl]-2-(phenylsulfanylmethyl)imidazo[4,5-c]pyridine Chemical compound C1=CC(Br)=CC=C1CN1C=C2N=C(CSC=3C=CC=CC=3)N=C2C=C1 MTWGESHKSOCJSY-UHFFFAOYSA-N 0.000 claims description 3
- JEZQKDRQFVEXFY-UHFFFAOYSA-N 5-[(4-bromophenyl)methyl]-2-naphthalen-1-ylimidazo[4,5-c]pyridine Chemical compound C1=CC(Br)=CC=C1CN1C=C2N=C(C=3C4=CC=CC=C4C=CC=3)N=C2C=C1 JEZQKDRQFVEXFY-UHFFFAOYSA-N 0.000 claims description 3
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- 239000002562 thickening agent Substances 0.000 description 1
- 125000005032 thiofuranyl group Chemical group S1C(=CC=C1)* 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
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- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
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- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
-
- 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
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- 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
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Virology (AREA)
- General Health & Medical 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)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0215293.2A GB0215293D0 (en) | 2002-07-03 | 2002-07-03 | Viral inhibitors |
| GB0313251A GB0313251D0 (en) | 2003-06-10 | 2003-06-10 | Viral inhibitors |
| PCT/BE2003/000117 WO2004005286A2 (en) | 2002-07-03 | 2003-07-03 | Viral inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20045731L NO20045731L (no) | 2005-03-17 |
| NO330766B1 true NO330766B1 (no) | 2011-07-11 |
Family
ID=30117086
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20045731A NO330766B1 (no) | 2002-07-03 | 2004-12-30 | Viral Inhibitors |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US7737162B2 (ko) |
| EP (2) | EP1521754B1 (ko) |
| JP (2) | JP4907082B2 (ko) |
| KR (2) | KR101184032B1 (ko) |
| CN (1) | CN1328279C (ko) |
| AT (1) | ATE522528T1 (ko) |
| AU (2) | AU2003243846B9 (ko) |
| BR (2) | BR122018077110B1 (ko) |
| CA (1) | CA2491243C (ko) |
| CY (1) | CY1112042T1 (ko) |
| DK (1) | DK1521754T3 (ko) |
| EA (1) | EA013562B1 (ko) |
| ES (2) | ES2525483T3 (ko) |
| GB (1) | GB0215293D0 (ko) |
| HK (2) | HK1082734A1 (ko) |
| IL (1) | IL166055A (ko) |
| MX (1) | MXPA04012965A (ko) |
| NO (1) | NO330766B1 (ko) |
| NZ (1) | NZ537473A (ko) |
| PT (2) | PT1521754E (ko) |
| SI (1) | SI1521754T1 (ko) |
| WO (1) | WO2004005286A2 (ko) |
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