Pyrazolo[1,5-A]pyrimidines for antiviral treatment

Patent metadata

Field	Value
Publication number	US-9957275-B2
Application number	US-201715639970-A
Country	US
Kind code	B2
Filing date	Jun 30, 2017
Priority date	Jun 24, 2010
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

The invention provides compounds of Formula I or Formula II:

or a pharmaceutically acceptable salt or ester, thereof, as described herein. The compounds and compositions thereof are useful for treating Pneumovirinae virus infections. The compounds, compositions, and methods provided are particularly useful for the treatment of Human respiratory syncytial virus infections.

First claim

What is claimed is:

1. A compound of formula:

or a pharmaceutically acceptable salt thereof.

2. A process of making the compound of claim 1 or a pharmaceutically acceptable salt thereof, comprising reacting a compound of formula:

with a compound of formula:

to form the compound of claim 1 or a pharmaceutically acceptable salt thereof.

3. The process of claim 2 , wherein the reacting step is performed in a solvent comprising triethylamine and methanol.

4. The process of claim 2 , comprising heating the reaction to about 75° C.

5. The process of claim 2 , wherein the pharmaceutically acceptable salt is trifluoroacetic acid salt.

6. A process of making a compound of formula:

or a pharmaceutically acceptable salt thereof, comprising contacting the compound of claim 1 with an acid to form the compound of formula:

or a pharmaceutically acceptable salt thereof.

7. The process of claim 6 wherein the pharmaceutically acceptable salt is trifluoroacetic acid salt.

8. The process of claim 6 wherein the contacting step is performed in a solvent comprising trifluoroacetic acid and dichloromethane.

9. The process of claim 6 wherein the contacting step comprises stirring overnight.

10. A compound of formula:

or a pharmaceutically acceptable salt thereof.

11. A process of making the compound of claim 10 or a pharmaceutically acceptable salt thereof, comprising contacting a compound of formula:

with an acid of formula:

to form the compound of claim 10 or a pharmaceutically acceptable salt thereof.

12. The process of claim 11 wherein the contacting step is performed in a solution, the solution comprising a solvent and a reagent.

13. The process of claim 11 wherein the contacting step is performed in a solution, the solution comprising dimethylformamide and a reagent of formula:

14. The process of claim 11 wherein the contacting step further comprises contacting the compound of formula:

with an acid of formula:

and with triethylamine.

15. A compound of formula:

16. A process of making the compound of claim 15 comprising reacting a compound of formula:

with phosphorus oxychloride to form the compound of claim 15 .

17. The process of claim 16 wherein the reacting step is heated to 100° C.

Assignees

• Gilead Sciences Inc

Inventors

• Babaoglu Kerim
• Boojamra Constantine G
• Eisenberg Eugene J
• Hui Hon Chung
• Mackman Richard L
• Parrish Jay P
• Sangi Michael
• Saunders Oliver L
• Siegel Dustin
• Sperandio David
• Yang Hai

Classifications

• A61P31/14

  for RNA viruses · CPC title

• A61P31/12

  Antivirals · CPC title

• A61P31/16

  for influenza or rhinoviruses · CPC title

• A61P11/00

  Drugs for disorders of the respiratory system · CPC title

• A61K31/675

  having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate · CPC title