IP Library Granted Patent US 9,433,609
Granted Patent B2
US 9,433,609 · App. 13/836,816 · Granted Sep 6, 2016

Benzimidazole-imidazole derivatives

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Quick Facts
Patent No.
US 9,433,609
App. No.
13/836,816
Granted
Sep 6, 2016
Kind
B2
Abstract

Inhibitors of HCV replication of formula I including stereochemically isomeric forms, and salts, solvates thereof, wherein R and R′ are, each independently, —CR 1 R 2 R 3 , aryl, heteroaryl or heteroC 4-6 cycloalkyl, whereby aryl and heteroaryl may optionally be substituted with 1 or 2 substituents selected from halo and methyl. The present invention also relates to processes for preparing said compounds, pharmaceutical compositions containing them and their use in HCV therapy.

Claims (30)

1. A method of treating HCV infection in a mammal comprising administer to said mammal a composition comprising a compound of Formula I:

or a stereoisomeric form thereof, wherein:

A is naphthylene, which is optionally substituted with 1, 2 or 3 substituents selected from halo and C 1-3 alkyl;

R and R′ are, each independently, —CR 1 R 2 R 3 , aryl, heteroaryl, or heteroC 4-6 cycloalkyl, whereby aryl and heteroaryl may optionally be substituted with 1 or 2 substituents selected from halo and methyl; and wherein

R 1 is hydrogen;

C 1-4 alkyl optionally substituted with methoxy or dimethylamino;

phenyl optionally substituted with 1, 2 or 3 substituents independently selected from halo, C 1-4 alkoxy, and trifluoromethoxy;

1,3-benzodioxolanyl;

benzyl optionally substituted with 1, 2 or 3 substituents independently selected from halo and methoxy;

C 3-6 cycloalkyl;

heteroaryl;

heteroC 4-6 cycloalkyl; or

heteroarylmethyl;

R 2 is hydrogen, hydroxyl, amino, mono- or di-C 1-4 alkylamino, C 1-4 alkylcarbonylamino, C 1-4 alkyloxycarbonylamino, C 1-4 alkylaminocarbonylamino, piperidin-1-yl or imidazol-1-yl;

R 3 is hydrogen,

or R 1 and R 3 together form a cyclopropyl group;

or R 2 and R 3 form oxo;

or a pharmaceutically acceptable salt or a solvate thereof;

wherein the compound is not

2. The method of claim 1 wherein A is 2,6-naphthylene optionally substituted with 1, 2, or 3 substituents selected from halo and C 1-3 alkyl.

3. The method of claim 1 wherein A is 2,6-napthylene.

4. The method of claim 1 wherein R 1 is different from unsubstituted 2-propyl and when R 1 in R is 1-methoxyethyl, then R 1 in R′ is different from 1-methoxyethyl.

5. The method of claim 1 wherein

R 1 is other than 2 propyl when R 2 is methoxycarbonylamino; and

R 1 in R′ is other than 1-methoxyethyl when R 2 in R′ is methoxycarbonylamino.

6. The method of claim 1 wherein R and R′ are different from one another.

7. The method of claim 1 wherein R and R′ are the same.

8. The method of claim 1 wherein R and R′ each independently are —CR 1 R 2 R 3 .

9. The method of claim 1 comprising administering to a mammal a composition comprising (a) a compound of Formula I as defined 1, and (b) another HCV inhibitor, as a combined preparation for simultaneous, separate or sequential use in the treatment of HCV infections.

10. The method of claim 1 comprising administering to a mammal a composition comprising (a) a compound of Formula I as defined by 1, and (b) an immunomodulatory agent, as a combined preparation for simultaneous, separate or sequential use in the treatment of HCV infections.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 24, 2015
From: JANSSEN R & D IRELAND
To: JANSSEN SCIENCES IRELAND UC
Reel/Frame 035496/0382 →