Antiviral compounds of three linked aryl moieties to treat diseases such as hepatitis c

A compound having the formula:

• or a pharmaceutically acceptable salt thereof, wherein:
• A is 5-membered monocyclic heteroaryl or bicyclic heteroaryl, wherein said 5-membered monocyclic heteroaryl group or said bicyclic heteroaryl group can be optionally and independently substituted on one or more ring carbon atoms by C1-C6 alkyl, —O—(C1-C6 alkyl) or halo;
• B is arylene or heteroarylene, wherein said arylene group can be substituted with R12;
• and wherein said heteroarylene group can be optionally and independently substituted on one or more ring nitrogen atoms with R10 and on one or more ring carbon atoms with R12;
• such that when B is a multicyclic ring system, then A and D are each bonded to the same ring of B;
• D is 5-membered monocyclic heteroaryl or bicyclic heteroaryl, wherein said 5-membered monocyclic heteroaryl group or said bicyclic heteroaryl group can be optionally and independently substituted on one or more ring carbon atoms by C1-C6 alkyl, —O—(C1-C6 alkyl) or halo;
• L1 is a bond, —[C(R13)2]q—, —[C(R13)2]m—C(R—)═C(R13)—[C(R13)2]m—, —[C(R13)2]m—(C≡C)q—[C(R13)2]m—, —[C(R13)2]m—N(R14)—[C(R13)2]m—, -alkylene-C(O)—, —C(O)— or —CF2—;
• L2 is a bond, —[C(R13)2]q—, —[C(R13)2]m—C(R13)═C(R13)—[C(R13)2]m—, —[C(R13)2]m—(C≡C)q—[C(R13)2]m—, —[C(R13)2]m—N(R14)—[C(R13)2]m—, —C(O)-alkylene-, —C(O)— or —CF2—, such that at least one of L1 and L2 is other than a bond;
• R1 is selected from:
• wherein an R1 group can be optionally and independently substituted with:
• (a) one to three groups, which can be the same or different, and are selected from halo, —OH, —C1-C3 alkyl, —O—(C1-C3 alkyl) and —C1-C3 haloalkyl, or
• (b) one to seven 2H groups;
• or an R1 group can be optionally fused to a C3-C5 cycloalkyl group at two of the R1 group's adjacent ring carbon atoms, or an R1 group can form a spirocycle with a cyclopentyl, cyclobutyl, cyclopropyl or cyclohexyl group at one of the R1 group's ring carbon atoms;
• R2 is selected from:
• wherein an R2 group can be optionally and independently substituted with:
• (a) one to three groups, which can be the same or different, and are selected from halo, —OH, —C1-C3 alkyl, —O—(C1-C3 alkyl) and —C1-C3 haloalkyl, or
• (b) one to seven 2H groups;
• or an R2 group can be optionally fused to a C3-C5 cycloalkyl group at two of the R2 group's adjacent ring carbon atoms, or an R2 group can form a spirocycle with a cyclopentyl, cyclobutyl, cyclopropyl or cyclohexyl group at one of the R2 group's ring carbon atoms:
• each occurrence of R5 is independently selected from:
• (a) —C(O)—(C1-C6 alkyl), optionally substituted by one to eight R3 groups, wherein each occurrence of R3 is independently selected from:
• (i) —O—(C1-C3 alkyl),
• (ii) phenyl, which can be optionally and independently substituted with one to four groups, selected from halo, C1-C3 alkyl and —O—(C1-C3 alkyl),
• (iii) —NH2,
• (iv) —NH(C1-C3 alkyl),
• (v) —N(C1-C3 alkyl)2,
• (vi) —NHC(O)—O—(C1-C6 alkyl),
• (vii) —N(C1-C3 alkyl)-C(O)—O—(C1-C6 alkyl),
• (viii) C1-C3 fluoroalkyl,
• (ix) C2-C6 alkynyl,
• (x) C3-C7 cycloalkyl,
• (xi) pyrrolidinyl,
• (xii) piperidinyl,
• (xiii) pyranyl,
• (xiv) —NHSO2-alkyl, and
• (xv) 2H;
• (b)
• wherein x is 1 or 2, and each occurrence of R4 is independently selected from the group consisting of H, C1-C3 alkyl, —O—(C1-C3 alkyl) and F;
• and
• (c) H;
• each occurrence of R10 is independently H, —C1-C6 alkyl, —[C(R12)2]p-(3 to 7-membered cycloalkyl), —[C(R12)2]p-(4 to 7-membered heterocycloalkyl), —[C(R12)2]p-aryl, —[C(R12)2]p-heteroaryl, —C1-C6 haloalkyl or —C1-C6 hydroxyalkyl, wherein said 3 to 7-membered cycloalkyl group, said 4 to 7-membered heterocycloalkyl group, said aryl group or said heteroaryl group can be optionally and independently substituted with up to two R13 groups, and wherein two R10 groups that are attached to a common nitrogen atom, together with the nitrogen atom to which they are attached, can optionally join to form a 4 to 7-membered heterocycloalkyl group;
• each occurrence of R12 is independently H, halo, —C1-C6 haloalkyl, —CN,
• —C1-C6 alkyl, —C1-C6 alkylene-OR16, —C1-C6 alkylene-N(R15)2, —C(O)—(C1-C6 alkyl), —OR16, —NHC(O)—(C1-C6alkyl), 3 to 7-membered cycloalkyl, 3 to 7-membered heterocycloalkyl, aryl or heteroaryl, wherein said 3 to 7-membered cycloalkyl group, said 3 to 7-membered heterocycloalkyl group, said aryl group or said heteroaryl group can be optionally and independently substituted with up to 3 substituents, which can be the same or different, and are selected from C1-C6 alkyl, halo, —C1-C6 haloalkyl, —C1-C6 hydroxyalkyl, —OH, —C(O)NH—(C1-C6 alkyl), —C(O)N(C1-C6 alkyl)2, —O—(C1-C6 alkyl), —NH2, —NH(C1-C6 alkyl), —N(C1-C6 alkyl)2 and —NHC(O)—(C1-C6 alkyl),
• each occurrence of R13 is independently H, —C1-C6 haloalkyl, —C1-C6 alkyl, —(C1-C6 alkylene)-O—(C1-C6 alkyl), —C(O)—(C1-C6 alkyl), —C(O)O(C1-C6 alkyl);
• each occurrence of R14 is independently H, —C1-C6 alkyl, 3 to 6-membered cycloalkyl or 4 to 6-membered heterocycloalkyl;
• each occurrence of R15 is independently H, —C1-C6 alkyl, —C1-C6 haloalkyl, 3 to 7-membered cycloalkyl, 4 to 7-membered heterocycloalkyl, aryl or heteroaryl, such that two R15 groups that are attached to a common nitrogen atom, together with the nitrogen atom to which they are attached, can optionally join to form a 4 to 7-membered heterocycloalkyl group;
• each occurrence of R16 is independently H, —C1-C6 alkyl, —C1-C6 haloalkyl, 3 to 7-membered cycloalkyl, 4 to 7-membered heterocycloalkyl, aryl or heteroaryl;
• each occurrence of m is independently 0 or 1;
• each occurrence of p is independently an integer ranging from to 3;
• and
• each occurrence of q is independently an integer ranging from 1 to 3.