Substituted 2-phenyl (AZA)benzofuran compounds for the treatment of hepatitis C

Patent metadata

Field	Value
Publication number	US-10214534-B2
Application number	US-201515317541-A
Country	US
Kind code	B2
Filing date	Jun 10, 2015
Priority date	Jun 11, 2014
Publication date	Feb 26, 2019
Grant date	Feb 26, 2019

Abstract

Compounds of Formula I, including their salts, as well as compositions and methods of using the compounds are set forth. The compounds have activity against hepatitis C virus (HCV) and may be useful in treating those infected with HCV:

First claim

We claim:

1. A compound of Formula I, or a pharmaceutically acceptable salt thereof:

wherein
X is N or C—R 10 ;
R 1 is methyl;
R 2 is OAr 1 ;
Ar 1 is phenyl or pyridinyl and is substituted with 0-3 substituents selected from the group of cyano, halo, alkyl, cycloalkyl, haloalkyl, hydroxy, alkoxy, and haloalkoxy;
R 3 is hydrogen, halo, or alkyl;
R 4 , R 5 , R 6 , R 7 , R 8 are each independently selected from the group of hydrogen, halo, alkyl, cycloalkyl, haloalkyl, halocycloalkyl, hydroxyalkyl, hydroxycycloalkyl, alkoxyalkyl, alkoxycycloalkyl, alkoxy, hydroxyalkyloxy, alkoxyalkyloxy, and CON(R 202 )(R 203 );
R 202 and R 203 are each independently selected from the group of hydrogen, alkyl, and cycloalkyl;
R 9 is selected from the group of haloalkyl and NR 301 R 302 ;
R 301 is selected from the group of hydrogen, alkyl, cycloalkyl, (cycloalkyl)alkyl, benzyl, alkylcarbonyl, haloalkylcarbonyl, alkyl sulfonyl, phenyl sulfonyl, (alkoxyphenyl)sulfonyl and (haloalkoxyphenyl)sulfonyl;
R 302 is hydrogen, alkyl, hydroxyalkyl, or alkoxyalkyl; and
R 10 is hydrogen.

2. The compound of claim 1 , wherein R 5 is CON(R 202 )(R 203 ), or a pharmaceutically acceptable salt thereof.

3. The compound of claim 2 , wherein R 202 and R 203 are each hydrogen or alkyl, or a pharmaceutically acceptable salt thereof.

4. The compound of claim 1 , wherein R 9 is NR 301 R 302 , or a pharmaceutically acceptable salt thereof.

5. The compound of claim 4 , wherein R 301 is hydrogen, alkyl or alkylsulfonyl, or a pharmaceutically acceptable salt thereof.

6. The compound of claim 5 , wherein R 302 is alkyl, or a pharmaceutically acceptable salt thereof.

7. A composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, excipient and/or diluent.

8. A method of treating hepatitis C infection comprising administering a therapeutically effective amount of a compound of claim 1 to a patient.

Assignees

• Bristol Myers Squibb Co

Inventors

• Wang Tao
• Zhang Zhongxing
• Parcella Kyle E
• Eastman Kyle J
• Kadow John F

Classifications

• C07D491/04

  Ortho-condensed systems · CPC title

• C07D307/84

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title

• A61P31/00

  Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics · CPC title

• C07D491/048 Primary

  the oxygen-containing ring being five-membered · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title