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Anti-viral compound

A compound, alkyl technology, applied in antiviral compounds and in the fields of pharmacy and medicinal chemistry, can solve the problem of no therapeutic agent

Inactive Publication Date: 2001-04-25
ELI LILLY & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Thus, despite the recognized therapeutic potential associated with rhinovirus inhibitors and the research attempts undertaken to date, no effective therapeutic agent has emerged

Method used

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Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0115] 2-Chloro-5-benzoylpyridine

[0116] Aluminum chloride (100 g, 0.730 mol) was suspended in 200 ml of benzene under a nitrogen atmosphere. A solution of 6-chloronicotinoyl chloride (53 g, 0.30 mol) in 100 ml of benzene was added to the rapidly stirred suspension, which was then refluxed overnight. The reaction solution was cooled to room temperature, 1L of ethyl acetate was added, and the pH was adjusted to 8.5 with 5N sodium hydroxide. The aluminum salt precipitate that formed was filtered off. The filtrate was washed with water, dried over sodium sulfate, and concentrated in vacuo. The resulting tan solid was recrystallized from 3:2 ether:hexanes to give 54.6 g (83%) of the product as tan crystals. EA, MS (FD).

preparation example 2

[0118] 2-Chloro-5-(4-fluorobenzoyl)pyridine

[0119] Fluorobenzene (150ml, 1.60mmol) and 6-chloronicotinoyl chloride (17.7g, 100mmol) were converted into products in a substantially similar manner to Preparation 1 to obtain 15.2g of the product. (66.1%). EA, MS (FD), NMR.

preparation example 3

[0121] 2-Amino-5-benzoylpyridine

[0122] 2-Chloro-5-benzoylpyridine (100 g, 0.460 mol) was dissolved in 500 ml of 3A ethanol and 400 ml of anhydrous ammonia, placed in a high-pressure gas tank, and then heated at 145°C for 16 hours. The solvent was removed in vacuo and the remaining tan solid was recrystallized from ethanol / water to give 77.4 g (85%) of the product as a tan solid. EA, MS (FD).

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PUM

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Abstract

The present invention relates to compounds of Formula (I), which inhibit the growth of picornaviruses, Hepatitus viruses, enteroviruses, cardioviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus. In said Formula, A is phenyl, pyridyl, substituted phenyl, substituted pyridyl, or benzyl; R is hydrogen, COR4 or COCF; X is N-OH, O or CHR1 R1 is hydrogen, halo, CN, C -C alkyl -C≡ CH, CO(C -C alkyl), CO (C -C alkyl), or CONR2R3 R2 and R3 are independently hydrogen or C -C alkyl; A' is hydrogen, halo, C -C alkyl, benzyl, naphthyl, thienyl, furyl, pyridyl, pyrollyl, COR4 S(O)nR4 or a group of formula (II); R4 is C -C alkyl, phenyl, or substituted phenyl; n is 0,1, or 2; R5 is independently at each occurance hydrogen or halo; m is 1,2,3, or 4; and R6 is hydrogen, halo, CF, OH, CO H, NH, NO, CONHOCH, C -C alkyl, or CO (C -C alkyl), C -C alkoxy; or pharmaceutically acceptable salts thereof.

Description

field of invention [0001] The present invention relates to antiviral compounds and their applications in the fields of pharmacy and medicinal chemistry. Background of the invention [0002] The incidence of viral upper respiratory diseases, ie colds, is very high. It is estimated that there are nearly 1 billion cases each year in the United States alone. The main cause of common colds in humans is rhinovirus, a member of the picornaviridae family. More than 110 rhinovirus strains have been identified, making it impractical to develop a comprehensive rhinovirus vaccine. Therefore, chemotherapy seems to be a more ideal method. Another member of the picornavirus family is the enterovirus, which includes about 80 human pathogens. Many enteroviruses can cause cold-like symptoms, while others can cause more serious illnesses such as polio, conjunctivitis, aseptic meningitis and myocarditis. [0003] Illness associated with rhinovirus infection can manife...

Claims

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Application Information

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IPC IPC(8): A61KA61K31/437A61K31/44A61K31/444A61K31/50A61P1/16A61P31/12C07D471/04
CPCC07D471/04A61P1/16A61P31/12A61K31/437A61K31/444
Inventor J·埃兹奎拉-卡雷拉J·M·格鲁贝尔C·H·哈姆多赤R·E·霍尔梅斯W·A·斯皮策尔
Owner ELI LILLY & CO
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