# US 2008/0188458 A1 · Compounds for the Treatment of Hepatitis C

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- Number: US 2008/0188458 A1
- Document ID: US20080188458A1
- Status: Published application
- Kind: A1
- Application number: 12/022,541
- Filed: 2008-01-30
- Published: 2008-08-07
- Earliest claimed: 2007-02-02
- Assignees: Bristol-Myers Squibb Company
- Inventors: Kap-Sun Yeung; John F. Kadow; Katharine A. Grant-Young
- Web page: https://patentgrep.com/patent/US20080188458A1

## CPC

- C07D 487/04: Ortho-condensed systems
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 31/12: Antivirals
- A61P 31/16: for influenza or rhinoviruses
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention encompasses compounds of formula I as well as compositions and methods of using the compounds. The compounds have activity against hepatitis C virus (HCV) and are useful in treating those infected with HCV.

## Claims

### Claim 1

A compound of formula I
where:
R1 is CO2R6 or CONR7R8;
R2 is COR2, COCOR, SO2N(R14)(R15), or SO2R16;
R3 is hydrogen or alkyl;
R4 is hydrogen, halo, alkyl, alkenyl, hydroxy, benzyloxy, or alkoxy;
R5 is cycloalkyl;
R6 is hydrogen or alkyl;
R7 is hydrogen, alkyl, alkylSO2, cycloalkylSO2, haloalkylSO2, (R9)2NSO2, or (R10)SO2;
R8 is hydrogen or alkyl;
R9 is hydrogen or alkyl;
R10 is azetidinyl, pyrrolidinyl, piperidinyl, N—(R11)piperazinyl, morpholinyl, thiomorpholinyl, homopiperidinyl, N—(R11)homopiperazinyl, or homomorpholinyl;
R11 is hydrogen or alkyl; and
R12 is amino, alkylamino, or dialkylamino;
or R12 is azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, homopiperidinyl, homopiperazinyl, or homomorpholinyl, and is substituted with 0-3 substituents selected from alkyl, alkoxy, and phenyl wherein phenyl is substituted with 0-3 substituents selected from cyano, halo, alkyl, and alkoxy;
or R12 is
R13 is hydroxy, alkoxy, amino, alkylamino, or dialkylamino;
or R13 is azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, homopiperidinyl, homopiperazinyl, or homomorpholinyl, and is substituted with 0-3 substituents selected from alkyl, alkoxy, and phenyl wherein phenyl is substituted with 0-3 substituents selected from cyano, halo, alkyl, and alkoxy;
or R13 is
R14 is hydrogen, or alkyl;
R15 is hydrogen or alkyl;
R16 is alkyl, cycloalkyl, or haloalkyl;
or R16 is azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, homopiperidinyl, homopiperazinyl, or homomorpholinyl, and is substituted with 0-3 substituents selected from alkyl, alkylcarbonyl, alkoxycarbonyl, benzyl, and benzyloxycarbonyl;
or R16 is phenyl substituted with 0-3 substituents selected from cyano, halo, alkyl, haloalkyl, alkoxy, and haloalkoxy;
R17 is hydrogen, alkyl, cycloalkyl, (cycloalkyl)alkyl, benzyl, alkylcarbonyl, alkoxycarbonyl, benzyloxycarbonyl, alkylSO2, or pyridinyl; and
X is absent, a bond, or methylene;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

A compound of claim 1 where R1 is CONR7R8; R7 is alkylSO2, cycloalkylSO2, haloalkylSO2, (R9)2NSO2, or (R10)SO2; and R8 is hydrogen.

### Claim 3 (depends on 1)

A compound of claim 1 where R2 is COR12.

### Claim 4 (depends on 1)

A compound of claim 1 where R2 is COCOR13.

### Claim 5 (depends on 1)

A compound of claim 1 where R2 is SO2N(R14)(R15) or SO2R16.

### Claim 6 (depends on 1)

A compound of claim 1 where R3 is hydrogen.

### Claim 7 (depends on 1)

A compound of claim 1 where R4 is hydrogen.

### Claim 8 (depends on 1)

A compound of claim 1 where R4 is methoxy.

### Claim 9 (depends on 1)

A compound of claim 1 where R5 is cyclohexyl.

### Claim 10 (depends on 1)

A compound of claim 1 where R12 or R13 is dimethylamino, pyrrolidinyl, morpholinyl, dimethylmorpholinyl, piperazinyl, trimethylpiperazinyl, or
where R17 is alkyl.

### Claim 11 (depends on 1)

A compound of claim 1 where X is absent.

### Claim 12 (depends on 1)

A compound of claim 1 where X is a bond.

### Claim 13 (depends on 1)

A compound of claim 1 where X is methylene.

### Claim 14 (depends on 1)

A compound of claim 1 selected from the group consisting of
or a pharmaceutically acceptable salt thereof.

### Claim 15 (depends on 1)

A composition comprising a compound of claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

### Claim 16 (depends on 15)

The composition of claim 15 further comprising at least one additional compound having therapeutic benefits for HCV wherein the compound is selected from the group consisting of interferons, cyclosporins, interleukins, HCV metalloprotease inhibitors, HCV serine protease inhibitors, HCV polymerase inhibitors, HCV helicase inhibitors, HCV NS4B protein inhibitors, HCV entry inhibitors, HCV assembly inhibitors, HCV egress inhibitors, HCV NS5A protein inhibitors, HCV NS5B protein inhibitors, and HCV replicon inhibitors.

### Claim 17 (depends on 1)

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

### Claim 18 (depends on 17)

The method of claim 17 further comprising administering at least one additional compound having therapeutic benefits for HCV wherein the compound is selected from the group consisting of interferons, cyclosporins, interleukins, HCV metalloprotease inhibitors, HCV serine protease inhibitors, HCV polymerase inhibitors, HCV helicase inhibitors, HCV NS4B protein inhibitors, HCV entry inhibitors, HCV assembly inhibitors, HCV egress inhibitors, HCV NS5A protein inhibitors, HCV NS5B protein inhibitors, and HCV replicon inhibitors.