Antiviral compounds of three linked aryl moieties to treat diseases such as hepatitis C

Patent metadata

Field	Value
Publication number	US-8980920-B2
Application number	US-201013375094-A
Country	US
Kind code	B2
Filing date	May 28, 2010
Priority date	May 29, 2009
Publication date	Mar 17, 2015
Grant date	Mar 17, 2015

Abstract

The present invention relates to novel Linked Tricyclic Aryl Compounds, compositions comprising at least one Linked Tricyclic Compound, and methods of using Linked Tricyclic Aryl Compounds for treating or preventing HCV infection in a patient. in one aspect, the present invention provides Compounds of Formula (I): and pharmaceutically acceptable salts thereof, wherein: Non-limiting examples of the Compounds of Formula (II) include compound 56.

First claim

What is claimed is:

1. A compound having the formula:

or a pharmaceutically acceptable salt thereof,
wherein:
A is

B is selected from:

wherein either one of the two available bonds of each depicted group can be connected to either of the two groups flanking B;
D is:

L 1 is a bond, —CH 2 —, —CH 2 —CH 2 —, —CH 2 —C(O)—, —NHCH 2 —, —NH, —C(O)—, —N(CH 3 )—, —CH═CH— or —C≡C—;
L 2 is a bond, —CH 2 —, —CH 2 —CH 2 —, —C≡C—, —NH, —C(O)— or —N(CH 3 )—, such that at least one of L 1 and L 2 is other than a bond;
R 1 is:

R 2 is:

each occurrence of R 5 is independently —C(O)—C(R 21 )—NHC(O)O-alkyl, —C(O)—C(alkyl)-NHC(O)N(R 20 ) 2 , —C(O)—C(R 20 )—N(R 20 ) 2 , —C(O)-alkyl, —C(O)O-alkyl or —C(O)—C(alkyl)-NHS(O) 2 -alkyl;
each occurrence of R 20 is independently H or —C 1 -C 4 alkyl; and
each occurrence of R 21 is independently phenyl or —C 1 -C 4 alkyl.

2. The compound of claim 1 , wherein A-R 1 and D-R 2 are each independently selected from

3. The compound of claim 2 , wherein B is:

wherein either one of the two available bonds of each depicted group can be connected to either of the two groups flanking B.

4. The compound of claim 2 , wherein each occurrence of R 5 is independently selected from:

5. The compound of claim 4 , wherein B is:

wherein either one of the two available bonds of each depicted group can be connected to either of the two groups flanking B.

6. The compound of claim 4 , wherein each occurrence of R 5 is

7. A compound having the structure:

or a pharmaceutically acceptable salt thereof.

8. A pharmaceutical composition comprising at least one compound of claim 1 or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable carrier.

Assignees

• Zeng Qingbei
• Chen Kevin X
• Nair Anilkumar Gopinadhan
• Rosenblum Stuart B
• Kozlowski Joseph A
• Njoroge F George
• Merck Sharp & Dohme

Inventors

• Zeng Qingbei
• Chen Kevin X
• Nair Anilkumar Gopinadhan
• Rosenblum Stuart B
• Kozlowski Joseph A
• Njoroge F George

Classifications

• A61P31/16

  for influenza or rhinoviruses · CPC title

• A61P31/14

  for RNA viruses · CPC title

• C07D403/14 Primary

  containing three or more hetero rings · CPC title

• A61P31/12

  Antivirals · CPC title