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Heterocyclic compounds as rsv inhibitors

Inactive Publication Date: 2017-08-10
ENANTA PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides compounds that can be used to treat or prevent viral infections, particularly HRSV. These compounds can be selected from a group of specific formulas and can have various substituents. The invention also provides pharmaceutical compositions containing these compounds and methods of using them to treat or prevent viral infections.

Problems solved by technology

However, in infants and toddlers the virus can cause lower respiratory tract infections including bronchiolitis or pneumonia with many of them requiring hospitalization.
Currently, there is no vaccine available to prevent HRSV infection.
The high cost of palivizumab treatment limits its use for general purposes.
Ribavirin has also been used to treat HRSV infections but its effectiveness is limited.

Method used

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  • Heterocyclic compounds as rsv inhibitors
  • Heterocyclic compounds as rsv inhibitors
  • Heterocyclic compounds as rsv inhibitors

Examples

Experimental program
Comparison scheme
Effect test

example 1

Step f

[0208]

[0209]To a solution of 4-(4-morpholinyl)benzoic acid (100 mg, 0.46 mmol) in DCM (5 mL) was added thionoyl chloride (1 mL), and then the resulting mixture was refluxed for 4 hrs. After removed most solvent thionoyl chloride, the residual thionoyl chloride was further removed by azeotropic drying with toluene (20 mL×2). The residue was dissolved in DCM (4 mL), and then diisopropylethylamine (0.5 mL) and compound from Example 1 step e (122 mg, 0.46 mmol) were added. The mixture was stirred at rt for 12 hrs, then diluted with DCM (20 mL) and water (5 mL). The organic layer was washed with aq. NaHCO3 (2N, 10 mL), brine (20 mL), dried over Na2SO4, filtered and evaporated. The residue was purified by silica gel column chromatography to give the title compound (70 mg, 31%) as a white solid. ESI MS m / z=488.43 [M+H]+.

example 2

[0210]

[0211]Example 2 was prepared using a procedure similar to that used to prepare Example 1 where 3-(4-morpholinylmethyl)benzoic acid was used in place of 4-(4-morpholinylmethyl)benzoic acid in step f. ESI MS m / z=488.43 [M+H]+.

example 3

[0212]

[0213]Example 3 was prepared using a procedure similar to that used to prepare Example 1 where 4-(4-morpholinyl)benzoic acid was used in place of 4-(4-morpholinylmethyl)benzoic acid in step f ESI MS m / z=474.18 [M+H]+.

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Abstract

The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof:which inhibit Respiratory Syncytial Virus (RSV). The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from RSV infection. The invention also relates to methods of treating an RSV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

Description

RELATED APPLICATION[0001]This application claims the benefit of U.S. Provisional Application No. 62 / 279,320, filed on Jan. 15, 2016. The entire teachings of the above application are incorporated herein by reference.TECHNICAL FIELD[0002]The present invention relates generally to compounds and pharmaceutical compositions useful as Respiratory Syncytial Virus (RSV) inhibitors.BACKGROUND OF THE INVENTION[0003]Human respiratory syncytial virus (HRSV) is a negative-sense, single stranded, RNA paramyxovirus (KM. Empey, et al., Rev. Anti-Infective Agents, 2010, 50(1 May), 1258-1267). RSV is the leading cause of acute lower respiratory tract infections (ALRI) and affects patients of all ages. The symptoms in adults are usually not severe and are typically analogous to a mild cold. However, in infants and toddlers the virus can cause lower respiratory tract infections including bronchiolitis or pneumonia with many of them requiring hospitalization. Nearly all children have been infected by a...

Claims

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Application Information

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IPC IPC(8): C07D519/00A61K31/55A61K31/554A61K31/553A61K31/551C07D491/048C07D495/04A61K45/06
CPCC07D519/00C07D495/04A61K31/55A61K45/06A61K31/553A61K31/551C07D491/048A61K31/554C07D401/14C07D401/06C07D487/04C07D498/04C07D513/04
Inventor YU, JIANMINGSHOOK, BRIAN C.BLAISDELL, THOMAS P.KIM, IN JONGPANARESE, JOSEPHMCGRATH, KEVINNEGRETTI-EMMANUELLI, SOLYMAROR, YAT SUN
Owner ENANTA PHARM INC
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