	US 7,541,352 B2
	Compounds for the treatment of hepatitis C
Kap-Sun Yeung, Madison, Conn. (US); John F. Kadow, Wallingford, Conn. (US); and Katharine A. Grant-Young, Madison, Conn. (US)
Assigned to Bristol-Myers Squibb Company, Princeton, N.J. (US)
Filed on Jan. 30, 2008, as Appl. No. 12/22,541.
Claims priority of provisional application 60/887846, filed on Feb. 02, 2007.
Claims priority of provisional application 60/894881, filed on Mar. 14, 2007.
Prior Publication US 2008/0188458 A1, Aug. 07, 2008
This patent is subject to a terminal disclaimer.
Int. Cl. A61P 31/00 (2006.01); A61K 31/55 (2006.01); C07D 223/14 (2006.01)

U.S. Cl. 514—214.01 [540/576]

16 Claims

1. A compound of formula I

where:

R¹is CO₂R⁶or CONR⁷R⁸;

R²is COR¹², COCOR¹³, SO₂N(R¹⁴)(R¹⁵), or SO₂R¹⁶;

R³is hydrogen or alkyl;

R⁴is hydrogen, halo, alkyl, alkenyl, hydroxy, benzyloxy, or alkoxy;

R⁵is cycloalkyl;

R⁶is hydrogen or alkyl;

R⁷is hydrogen, alkyl, alkylSO₂, cycloalkylSO₂, haloalkylSO₂, (R⁹)₂NSO₂, or (R¹⁰)SO₂;

R⁸is hydrogen or alkyl;

R⁹is hydrogen or alkyl;

R¹⁰is azetidinyl, pyrrolidinyl, piperidinyl, N—(R¹¹)piperazinyl, morpholinyl, thiomorpholinyl, homopiperidinyl, N—(R¹¹)homopiperazinyl, or homomorpholinyl;

R¹¹is hydrogen or alkyl; and

R¹²is amino, alkylamino, or dialkylamino;

or R¹²is 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 R¹²is

R¹³is hydroxy, alkoxy, amino, alkylamino, or dialkylamino;

or R¹³is 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 R¹³is

R¹⁴is hydrogen, or alkyl;

R¹⁵is hydrogen or alkyl;

R¹⁶is alkyl, cycloalkyl, or haloalkyl;

or R¹⁶is 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 R¹⁶is phenyl substituted with 0-3 substituents selected from cyano, halo, alkyl, haloalkyl, alkoxy, and haloalkoxy;

R¹⁷is 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.