Benzimidazole derivatives

1. A compound represented by Formula (I):

or a pharmaceutically acceptable salt thereof, wherein:

D is an optionally substituted linear alkyl, linear alkenyl or linear alkynyl group comprising one to eight carbon atoms, A is a cyclic group, wherein said cyclic group is independently selected from the group consisting of aryl, heteroaryl, heterocyclic, C 3 -C 8 cycloalkyl, and C 3 -C 8 cycloalkenyl, each optionally substituted, T is absent, E is absent and Z is absent; or, alternatively, D is absent, A is absent, T is an optionally substituted linear alkyl, linear alkenyl or linear alkynyl group comprising one to eight carbon atoms, E is a cyclic group, wherein said cyclic group is independently selected from the group consisting of aryl, heteroaryl, heterocyclic, C 3 -C 8 cycloalkyl, and C 3 -C 8 cycloalkenyl, each optionally substituted, and Z is absent;

Ring B is an optionally substituted imidazolyl;

R 1 at each occurrence is independently selected from the group consisting of hydrogen, halogen, cyano, optionally substituted C 1 -C 4 alkyl, —O—R 11 , —NR a R b , —C(O)R 11 , —CO 2 R 11 , and —C(O)NR a R b ;

R 11 at each occurrence is independently hydrogen or optionally substituted C 1 -C 8 alkyl;

R a and R b at each occurrence are each independently selected from the group consisting of hydrogen, optionally substituted C 1 -C 8 alkyl, and optionally substituted C 2 -C 8 alkenyl; or R a and R b can be taken together with the nitrogen atom to which they are attached to form an optionally substituted heterocyclic or optionally substituted heteroaryl group;

u is independently 1, 2, or 3;

Q and J are each independently selected from:

R 3 and R 4 at each occurrence are each independently selected from the group consisting of hydrogen, optionally substituted C 1 -C 8 alkyl, optionally substituted C 2 -C 8 alkenyl, and optionally substituted C 3 -C 8 cycloalkyl; or alternatively, R 3 and R 4 can be taken together with the carbon atom to which they are attached to form optionally substituted C 3 -C 8 cycloalkyl or optionally substituted heterocyclic;

R 5 at each occurrence is independently hydrogen, optionally substituted C 1 -C 8 alkyl, or optionally substituted C 3 -C 8 cycloalkyl;

R 6 is selected from the group consisting of —C(O)—R 12 , —C(O)—C(O)—R 12 , —S(O) 2 —R 12 , and —C(S)—R u ;

R 12 at each occurrence is independently selected from the group consisting of —O—R 11 , —NR a R b , —R 13 , and —NR c R d ; wherein

R 13 at each occurrence is independently selected from the group consisting of: hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, heterocyclic, aryl, and heteroaryl, each optionally substituted; and

R c and R d at each occurrence are each independently selected from the group consisting of hydrogen, —R 13 , —C(O)—R 13 , —C(O)—OR 13 , —S(O) 2 —R 13 , —C(O)N(R 13 ) 2 , and —S(O) 2 N(R 13 ) 2 ;

m is 0, 1, or 2;

n is 1, 2, 3, or 4;

X at each occurrence is independently selected from O, S, S(O), SO 2 , and C(R 7 ) 2 ; provided that when m is 0, X is C(R 7 ) 2 , and further provided that at least one X is C(R 7 ) 2 wherein the two geminal R 7 groups of X are taken together with the carbon atom to which they are attached to form a spiro, optionally substituted C 3 -C 8 cycloalkyl or optionally substituted heterocyclic ring; and

R 7 at each occurrence is independently selected from the group consisting of: hydrogen, halogen, cyano, —O—R 11 , —NR a R b , optionally substituted aryl, optionally substituted heteroaryl, and optionally substituted —C 1 -C 4 alkyl; or two vicinal R 7 groups are taken together with the two adjacent atoms to which they are attached to form a fused, optionally substituted C 3 -C 8 cycloalkyl or optionally substituted heterocyclic ring; or alternatively two geminal R 7 groups are taken together with the carbon atom to which they are attached to form a spiro, optionally substituted C 3 -C 8 cycloalkyl or optionally substituted heterocyclic ring.

2. The compound of claim 1 , wherein one of Q and J is selected from:

wherein X is CH 2 , CF 2 , CHF, or CH(OH); or a pharmaceutically acceptable salt thereof.

3. The compound of claim 1 , wherein each of D, A, and Z are absent and each of T and E are present; or a pharmaceutically acceptable salt thereof.

4. A compound of claim 1 , represented by Formula (II), or a pharmaceutically acceptable salt thereof:

wherein m is 1; n is 1 or 2; u is 1 or 2; E is phenyl, monocyclic heteroaryl, bicyclic aryl, or bicyclic heteroaryl, each optionally substituted; T is optionally substituted C 2 -C 4 alkenyl or optionally substituted C 2 -C 4 alkenyl; R 1 at each occurrence is independently hydrogen or halogen; R 7 at each occurrence is independently hydrogen or methyl; alternatively, the two geminal R 7 groups are taken together with the carbon to which they are attached to form a spiro, optionally substituted C 3 -C 8 cycloalkyl; or yet alternatively, two vicinal R 7 groups are taken together with the two adjacent atoms to which they are attached to form a fused, optionally substituted C 3 -C 8 cycloalkyl; X at each occurrence is independently selected from O, S, S(O), SO 2 , and C(R 7 ) 2 ; provided that when m is 0, X is C(R 7 ) 2 , and further provided that at least one X is C(R 7 ) 2 wherein the two geminal R 7 groups of X are taken together with the carbon atom to which they are attached to form a spiro, optionally substituted C 3 -C 8 cycloalkyl; and R 12 at each occurrence is independently optionally substituted C 1 -C 8 alkyl.

5. A compound represented by Formula (III-a) or (III-b):

wherein n is 1 or 2; X at each occurrence is independently CH 2 , CHF, CH(OH), CHMe, CF 2 , or C(R 7 ) 2 ; wherein R 7 at each occurrence is independently hydrogen or methyl; alternatively, two geminal R 7 groups are taken together with the carbon to which they are attached to form a spiro cyclopropyl; or yet alternatively, two vicinal R 7 groups are taken together with the two adjacent atoms to which they are attached to form a fused cyclopropyl; provided that at least one X is C(R 7 ) 2 wherein the two geminal R 7 groups of X are taken together with the carbon atom to which they are attached to form a spiro cyclopropyl; and R 12 at each occurrence is independently C 1 -C 8 alkyl optionally substituted with amino, hydroxy, protected amino, or O(C 1 -C 4 alkyl); or a pharmaceutically acceptable salt thereof.

6. A compound selected from the group of compounds 520 to 525 shown below, or a pharmaceutically acceptable salt thereof:

520

521

522

523

524

525

7. A pharmaceutical composition comprising a compound or a combination of compounds according to claim 1 or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable carrier or excipient.

8. A method of treating hepatitis C virus infection comprising administering to a patient in need of such treatment a therapeutically effective amount of a compound or combination of compounds of claim 1 , or a pharmaceutically acceptable salt thereof.

9. The pharmaceutical composition of claim 7 , further comprising an agent selected from ribavirin and amantadine.

10. The composition of claim 7 , further comprising ritonavir.

11. The compound of claim 1 , wherein the two geminal R 7 groups of X are taken together with the carbon atom to which they are attached to form a spiro, optionally substituted C 3 -C 8 cycloalkyl.

12. The compound of claim 4 , wherein T is an optionally substituted C 2 -C 4 alkynyl.