# US 9,433,609 B2 · Benzimidazole-imidazole derivatives

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- Number: US 9,433,609 B2
- Document ID: US9433609B2
- Status: Granted
- Kind: B2
- Application number: 13/836,816
- Filed: 2013-03-15
- Published: 2014-04-17
- Granted: 2016-09-06
- Earliest claimed: 2009-11-04
- Assignees: Janssen Sciences Ireland UC
- Applicants: Janssen Sciences Ireland UC
- Inventors: Koen Vandyck; Stefaan Julien Last; Ioannis Nicolaos Houpis; Pierre Jean-Marie Bernard Raboisson
- Web page: https://patentgrep.com/patent/US9433609B2

## CPC

- C07D 403/14: containing three or more hetero rings
- A61K 31/40: having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K 31/41: having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K 31/4164: 1,3-Diazoles
- A61K 31/4184: condensed with carbocyclic rings, e.g. benzimidazoles
- A61K 31/55: having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 31/12: Antivirals
- A61P 31/14: for RNA viruses
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 405/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Inhibitors of HCV replication of formula I including stereochemically isomeric forms, and salts, solvates thereof, wherein R and R′ are, each independently, —CR1R2R3, aryl, heteroaryl or heteroC4-6cycloalkyl, 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

### Claim 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 C1-3alkyl;
R and R′ are, each independently, —CR1R2R3, aryl, heteroaryl, or heteroC4-6cycloalkyl, whereby aryl and heteroaryl may optionally be substituted with 1 or 2 substituents selected from halo and methyl; and wherein
R1 is hydrogen;
C1-4alkyl optionally substituted with methoxy or dimethylamino;
phenyl optionally substituted with 1, 2 or 3 substituents independently selected from halo, C1-4alkoxy, and trifluoromethoxy;
1,3-benzodioxolanyl;
benzyl optionally substituted with 1, 2 or 3 substituents independently selected from halo and methoxy;
C3-6cycloalkyl;
heteroaryl;
heteroC4-6cycloalkyl; or
heteroarylmethyl;
R2 is hydrogen, hydroxyl, amino, mono- or di-C1-4alkylamino, C1-4alkylcarbonylamino, C1-4alkyloxycarbonylamino, C1-4alkylaminocarbonylamino, piperidin-1-yl or imidazol-1-yl;
R3 is hydrogen,
or R1 and R3 together form a cyclopropyl group;
or R2 and R3 form oxo;
or a pharmaceutically acceptable salt or a solvate thereof;
wherein the compound is not

### Claim 2 (depends on 1)

The method of claim 1 wherein A is 2,6-naphthylene optionally substituted with 1, 2, or 3 substituents selected from halo and C1-3alkyl.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

The method of claim 1 wherein R1 is different from unsubstituted 2-propyl and when R1 in R is 1-methoxyethyl, then R1 in R′ is different from 1-methoxyethyl.

### Claim 5 (depends on 1)

The method of claim 1 wherein
R1 is other than 2 propyl when R2 is methoxycarbonylamino; and
R1 in R′ is other than 1-methoxyethyl when R2 in R′ is methoxycarbonylamino.

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 1)

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

### Claim 8 (depends on 1)

The method of claim 1 wherein R and R′ each independently are —CR1R2R3.

### Claim 9 (depends on 1)

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.

### Claim 10 (depends on 1)

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.