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US 8,133,884 B2Granted
Compounds for the treatment of hepatitis C
AssigneeBristol-Myers Squibb Company
InventorsScott W. Martin, Carl P. Bergstrom, Min Ding, Xiaofan Zheng, Robert G. Gentles
Life of this patent
Estimating the term…
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.
Claims13
A compound of formula I
- where:
- R1 is CO2R5 or CONR6R7;
- R2 is furanyl, pyrrolyl, thienyl, pyrazolyl, isoxazolyl, isothiazolyl, imidazolyl, oxazolyl, thiazolyl, oxadiazolyl, triazolyl, or tetrazolyl;
- and R2 is substituted with 1 substituent selected from the group consisting of cycloalkyl, tetrahydrofuranyl, tetrahydropyranyl, phenyl, pyrimidinyl, pyrazinyl, pyridinonyl, benzimidazolyl, piperidinyl substituted with 0-1 alkyl substituents, and pyridinyl substituted with 0-1 alkyl substituents;
- and R2 is substituted with 1 substituent selected from CO2R5, CON(R12)2, and COR13;
- and R2 is substituted with 0-1 substituents selected from oxo, amino, alkyl, and haloalkyl;
- R3 is hydrogen, halo, alkyl, alkenyl, hydroxy, benzyloxy, or alkoxy;
- R4 is cycloalkyl;
- R5 is hydrogen or alkyl;
- R6 is hydrogen, alkyl, alkylSO2, cycloalkylSO2, haloalkylSO2, (R9)(R10)NSO2, or (R11)SO2;
- R7 is hydrogen or alkyl;
- R8 is hydrogen, alkyl, cycloalkyl, (cycloalkyl)alkyl, alkylcarbonyl, cycloalkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkylSO2, cycloalkylSO2, haloalkylSO2, aminocarbonyl, (alkylamino)carbonyl, (dialkylamino)carbonyl, benzyl, benzyloxycarbonyl, or pyridinyl;
- R9 is hydrogen or alkyl;
- R10 is hydrogen or alkyl;
- R11 is azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, homopiperidinyl, homopiperazinyl, or homomorpholinyl, and is substituted with 0-1 alkyl substituents;
- R12 is hydrogen, alkyl, alkoxyalkyl, aminoalkyl, (alkylamino)alkyl, (dialkylamino)alkyl, or (R11)alkyl;
- R13 is azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, homopiperidinyl, homopiperazinyl, or homomorpholinyl, and is substituted with 0-3 substituents selected from halo, alkyl, cycloalkyl, alkoxyalkyl, amino, alkylamino, dialkylamino, R11, aminoalkyl, (alkylamino)alkyl, (dialkylamino)alkyl, (R11)alkyl, or CO2R5;
- or R13 is a [4.3.0] or [3.3.0] bicyclic diamine attached to the carbonyl through one nitrogen, and is substituted with 0-2 R8 substituents;
- R14 is hydrogen, alkyl, cycloalkyl, (cycloalkyl)alkyl, aminoalkyl, (alkylamino)alkyl, (dialkylamino)alkyl, or benzyl;
- R15 is hydrogen, alkyl, cycloalkyl, (cycloalkyl)alkyl, aminoalkyl, (alkylamino)alkyl, (dialkylamino)alkyl, or benzyl;
- or NR14R15 taken together is azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, N-(alkyl)piperazinyl, morpholinyl, thiomorpholinyl, homopiperidinyl, or homomorpholinyl;
- R16 is hydrogen or alkyl;
- R17 is hydrogen, alkyl, or cycloalkyl;
- and
- X is methylene, a bond, or absent;
- or a pharmaceutically acceptable salt thereof.
23 more elements
Dependencies are inferred from the claim text.