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Imidazo[4,5-c]pyridine compounds and methods of antiviral treatment

a technology of pyridine compounds and pyridines, applied in the field of pyridine compounds of imidazo4, can solve the problems of chronic carriers at risk of developing cirrhosis and/or liver cancer, significant economic losses world-wide, and acute fatal diseases

Inactive Publication Date: 2005-10-06
PUERSTINGER GERHARD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Pestiviruses such as the Classical Swine Fever Virus (CSFV), the Bovine Viral Diarrhea Virus (BVDV) and the Border Disease Virus (BDV) cause infections of domestic livestock (respectively pigs, cattle and sheep) and are responsible for significant economic losses world-wide.
BVDV, the prototypic representative of the pestivirus genus is ubiquitous and causes a range of clinical manifestations, including abortion, teratogenesis, respiratory problems, chronic wasting disease, immune system dysfunction, and predisposition to secondary viral and bacterial infections and may also cause acute fatal disease.
These chronic carriers are at risk of developing cirrhosis and / or liver cancer.
However, sustained response is only observed in about 40% of the patients and treatment is associated with serious adverse effects.
Furthermore, the study of specific inhibitors of HCV replication has been hampered by the fact that it is not possible to propagate HCV (efficiently) in cell culture.
Currently, there is no treatment strategy available for controlling infections caused by pestiviruses.
Clinical response with pleconaril has been observed in some studies, but the compound has not been approved by the Food and Drug Administration (hearing of Mar. 18, 2002).

Method used

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  • Imidazo[4,5-c]pyridine compounds and methods of antiviral treatment
  • Imidazo[4,5-c]pyridine compounds and methods of antiviral treatment
  • Imidazo[4,5-c]pyridine compounds and methods of antiviral treatment

Examples

Experimental program
Comparison scheme
Effect test

example 1

2-(2,3-difluorophenyl)-3H-imidazo[4,5-c]pyridine

[0266]

[0267] Phosphorous pentoxide (24.56 g) was dissolved in methanesulfonic acid (165.8 mL) at 50° C. with stirring. To the solution, 3,4-diaminopyridine (12.3 g, 0.1 mmoles) and 2,3-difluorobenzoic acid (19.4 g, 0.12 moles) were added. The reaction mixture was heated to 190° C. for 3 hours. The reaction was done three times. The reaction mixtures was cooled to 50° C. and poured into ice with stirring. At this stage, all three batches were combined. The reaction mixture was neutralized by the addition of NaOH with stirring until the pH is 8. Solid material precipitated out of solution, was collected by filtration and air-dried. The final product was re-crystallized from ethanol / water twice to yield 36 g of 2-(2,3-difluorophenyl)-3H-imidazo[4,5-c]pyridine. 1H 300 Mhz (CD3OD) sigma 7.3-7.42 (m, 1p); 7.43-7.58 (m, 1p); 7.70 (d, 1p); 8.0 (m, 1p); 8.34 (d, 1p); and 8.95 (s, 1p). LC / MS data M / z=232.

[0268] Following the above taught proce...

example 2

5-((3-(4-chlorophenyl)isoxazol-5-yl)methyl)-2-(2-fluorophenyl) 20-5H-imidazo[4,5-c]pyridine

[0269]

[0270] To a suspension of 2-(2-fluorophenyl)-3H-imidazo[4,5-c]pyridine (11.0 g, 50.0 mmoles) in DMF was added a 10% (w / v) solution of aqueous NaOH. To this solution, 5-(chloromethyl)-3-(4-chlorophenyl)isoxazole (13.68 g, 60.0 mmoles) dissolved in DMF was added. The reaction mixture was stirred at room temperature and monitored every half hour by LCMS. The reaction was stopped at 4 hours, after LCMS showed no progress between at 2 hour and 4 hour monitor points. The reaction product was triturated with first with water and then with EtoAc (3×). The material was crystallized by dissolving the material in MeOH with heat, followed by precipitation with water. This crystallization process was then repeated yielding 5((3-(4-chlorophenyl)isoxazol-5-yl)methyl)-2-(2-fluorophenyl)-5H-imidazo[4,5-c]pyridine (15.385 g, 38 mmole) as white crystal at a yield of 74%. 1H 300 Mhz (d6-DMSO) sigma 6.02 (s...

example 3a

5-(4-(trifluoromethoxy)benzyl)-2-(2,3-difluorophenyl)-5H-imidazo[4,5-c]pyridine

[0271]

[0272] First, 2-(2,3-difluorophenyl)-3H-imidazo[4,5-c]pyridine (20 g, 86.6 mmole) was added to 430 mL of DMF; Some of the solid material did not dissolve. To this solution was added 43 mL of a 10% NaOH (w / v) solution. With vigorous stirring, the un-dissolved material went into solution. The resulting solution was divided into 30 equal portions of 16.3 mL, 3 mmole of 2-(2,3-difluorophenyl)-3H-imidazo[4,5-c]pyridine so as to fit into a microwave reaction vessel. To each reaction vessel was added of 11-(chloromethyl)-4-(trifluoromethoxy)benzene (693 mg, 3 mmole). Each reaction mixture was microwaved for 1 minute at 110° C. Following the completion of all the microwave reactions, all of the reaction vessels were combined (one was lost due to breakage of the vessel) into three batches for workup. For each batch, DMF was removed by vacuum, and the resulting material was washed three times with deionized ...

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Abstract

The present invention relates to pharmaceutical compositions for the treatment or prevention of viral infections comprising as an active principle at least one imidazo[4,5-c]pyridine prodrug having the general formula (A): wherein the substituents are described in the specification. The invention also relates to processes for the preparation and screening of compounds according to the invention having above mentioned general formula and their use in the treatment or prophylaxis of viral infections.

Description

FIELD OF THE INVENTION [0001] The present invention relates to a series of novel imidazo[4,5-c]pyridine compounds, processes for their preparation, their use to treat or prevent viral infections and their use to manufacture a medicine to treat or prevent viral infections, particularly infections with viruses belonging to the family of the Flaviviridae and Picornaviridae and more preferably infections with hepatitis-C-virus (HCV). BACKGROUND OF THE INVENTION [0002] The family of the Flaviviridae consists of 3 genera, the pestiviruses, the flaviviruses and the hepaciviruses and also contains the hepatitis G virus (HGV / GBV-C) that has not yet been assigned to a genus. Pestiviruses such as the Classical Swine Fever Virus (CSFV), the Bovine Viral Diarrhea Virus (BVDV) and the Border Disease Virus (BDV) cause infections of domestic livestock (respectively pigs, cattle and sheep) and are responsible for significant economic losses world-wide. BVDV, the prototypic representative of the pest...

Claims

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Application Information

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IPC IPC(8): A61K31/437A61K31/4745C07D471/02C07D471/04C07D519/00
CPCC07D471/04A61P3/12A61P31/12A61P31/14A61P43/00A61K31/4353A61K31/437
Inventor BONDY, STEVENDOWDY, ERICKIM, CHOUNGNEYTS, JOHANOARE, DAVIDPUERSTINGER, GERHARDZIA, VAHID
Owner PUERSTINGER GERHARD
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