Compounds, compositions, and methods for control of hepatitis c viral infections

A compound of the formula (I):

• or a pharmaceutically acceptable salt thereof, wherein:
• R1 is selected from the group consisting of substituted aryl, unsubstituted aryl substituted heteroaryl, unsubstituted heteroaryl, polyhaloalkyl, substituted alkyl, unsubstituted alkyl, substituted cycloalkyl, unsubstituted cycloalkyl, substituted arylalkyl, unsubstituted arylalkyl, substituted heteroarylalkyl, and unsubstituted heteroarylalkyl groups;
• R2 is selected from the group consisting of polyhaloalkyl, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted arylalkyl, unsubstituted arylalkyl, substituted heteroarylalkyl, and unsubstituted heteroarylalkyl groups;
• R3 is selected from the group consisting of substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted alkyl, unsubstituted alkyl, cycloalkyl, substituted arylalkyl, unsubstituted arylalkyl, heteroalkyl, alkoxy, alkyl thio, aryloxy, hydrogen, amino, —COOH, —CO—NH2, —CO—O—R″3, —CO—S—R″3, and —CO—NR′3-R″3 groups, wherein R′3 is a hydrogen, alkyl, substituted aryl, unsubstituted aryl, substituted heteroaryl or unsubstituted heteroaryl group, and wherein R″3 is substituted aryl, unsubstituted aryl, substituted alkyl, unsubstituted alkyl, substituted cycloalkyl, unsubstituted cycloalkyl, or —(X)—R, wherein X is a —(CH2)n— or —CO— linker group, wherein n is 1, 2, or 3, and wherein R is a substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted alkyl, unsubstituted alkyl, substituted cycloalkyl, unsubstituted cycloalkyl, unsubstituted arylalkyl, substituted arylalkyl, or heteroalkyl group;
• R4 is selected from the group consisting of hydrogen, alkyl, cyano (CN), hydroxyl, nitro, chloro, bromo, fluoro, iodo, —COOH, —CO—NH2, —CO—O—R″4, —CO—S—R″4, and —CO—NR′4-R″4 groups, wherein R′4 is a hydrogen, substituted alkyl, unsubstituted alkyl, substituted aryl, unsubstituted aryl, substituted heteroaryl or unsubstituted heteroaryl group, and wherein R″4 is —(X)—R, wherein X is a —(CH2)n— or —CO— linker group, wherein n is 1, 2, or 3, and wherein R is a substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, adamantyl, alkyl, cycloalkyl, unsubstituted arylalkyl, substituted arylalkyl, or heteroalkyl group;
• and wherein said compound or salt thereof is an enantiomer with R1 and R2 in a syn configuration that inhibits hepatitis C viral replication, said enantiomer being substantially free of other enantiomeric forms.

An enantiomer being substantially free of other enantiomeric forms, of the formula:

• or a pharmaceutically acceptable salt thereof, wherein:
• R1 is unsubstituted thienyl-2, substituted thienyl-2, unsubstituted furyl-2, or substituted furyl-2;
• R2 is a polyhaloalkyl selected from the group consisting of —CCl3, —CBr3, —CF3, —CF2Cl, —CF2Br, —CF2I, —CCl2F, and —CBr2F;
• R3 is —CO—NH2 or R3 is —CO—NHR′3-R″3, wherein R′3 is hydrogen and R″3 is -phenyl-m-(CHOH)—CH3, furan-2-yl-methyl, substituted furan-2-yl-methyl, thiophene-2-yl-methyl, or substituted thiophene-2-yl-methyl;
• and R4 is hydrogen, chlorine, or bromine.

A pharmaceutical composition comprising (a) a compound of the formula (I):

• or a pharmaceutically acceptable salt thereof, wherein:
• R1 is selected from the group consisting of substituted aryl, unsubstituted aryl-substituted heteroaryl, unsubstituted heteroaryl, polyhaloalkyl, substituted alkyl, unsubstituted alkyl, substituted cycloalkyl, unsubstituted cycloalkyl, substituted arylalkyl, unsubstituted arylalkyl, substituted heteroarylalkyl, and unsubstituted heteroarylalkyl groups;
• R2 is selected from the group consisting of polyhaloalkyl, substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted arylalkyl, unsubstituted arylalkyl, substituted heteroarylalkyl, and unsubstituted heteroarylalkyl groups;
• R3 is selected from the group consisting of substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted alkyl, unsubstituted alkyl, cycloalkyl, substituted arylalkyl, unsubstituted arylalkyl, heteroalkyl, alkoxy, alkyl thio, aryloxy, hydrogen, amino, —COOH, —CO—NH2, —CO—O—R″3, —CO—S—R″3, and —CO—NR′3-R″3 groups, wherein R′3 is a hydrogen, alkyl, substituted aryl, unsubstituted aryl, substituted heteroaryl or unsubstituted heteroaryl group, and wherein R″3 is substituted aryl, unsubstituted aryl, substituted alkyl, unsubstituted alkyl, substituted cycloalkyl, unsubstituted cycloalkyl, or —(X)—R, wherein X is a —(CH2)n— or —CO— linker group, wherein n is 1, 2, or 3, and wherein R is a substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, substituted alkyl, unsubstituted alkyl, substituted cycloalkyl, unsubstituted cycloalkyl, unsubstituted arylalkyl, substituted arylalkyl, or heteroalkyl group;
• R4 is selected from the group consisting of hydrogen, alkyl, cyano (CN), hydroxyl, nitro, chloro, bromo, fluoro, iodo, —COOH, —CO—NH2, —CO—O—R″4, —CO—S—R″4, and —CO—NR′4-R″4 groups, wherein R′4 is a hydrogen, substituted alkyl, unsubstituted alkyl, substituted aryl, unsubstituted aryl, substituted heteroaryl or unsubstituted heteroaryl group, and wherein R″4 is —(X)—R, wherein X is a —(CH2)n— or —CO— linker group, wherein n is 1, 2, or 3, and wherein R is a substituted aryl, unsubstituted aryl, substituted heteroaryl, unsubstituted heteroaryl, adamantyl, alkyl, cycloalkyl, unsubstituted arylalkyl, substituted arylalkyl, or heteroalkyl group;
• and wherein said compound or salt thereof is an enantiomer with R1 and R2 in a syn configuration that inhibits hepatitis C viral replication, said enantiomer being substantially free of other enantiomeric forms;
• and
• (b) one or more pharmaceutically acceptable carriers.