# US 2016/0002213 A1 · Hepatitis c inhibitors and uses thereof

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- Number: US 2016/0002213 A1
- Document ID: US20160002213A1
- Status: Published application
- Kind: A1
- Application number: 14/852,984
- Filed: 2015-09-14
- Published: 2016-01-07
- Earliest claimed: 2010-12-22
- Assignees: AbbVie Inc.; Abbott Products GmbH
- Applicants: AbbVie Inc.; Abbott Products GmbH
- Inventors: Clarence J. Maring; John K. Pratt; William A. Carroll; Dachun LIU; David A. Betebenner; Douglas K. Hutchinson; Michael D. Tufano; Todd W. Rockway; Uwe Schoen; Axel Pahl; Adreas Witte
- Web page: https://patentgrep.com/patent/US20160002213A1

## CPC

- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- A61K 31/4178: not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
- A61K 31/422: not condensed and containing further heterocyclic rings
- A61K 31/4245: Oxadiazoles
- A61K 31/427: not condensed and containing further heterocyclic rings
- A61K 31/437: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A61K 31/506: not condensed and containing further heterocyclic rings
- A61K 31/513: having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61K 31/5395: having two or more nitrogen atoms in the same ring, e.g. oxadiazines
- A61K 31/541: Non-condensed thiazines containing further heterocyclic rings
- A61K 31/675: having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
- A61K 31/695: Silicon compounds
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 31/12: Antivirals
- A61P 31/14: for RNA viruses
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- B65D 88/703: {Air blowing devices, i.e. devices for the sudden introduction of compressed air into the container}
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/14: containing three or more hetero rings
- C07D 409/14: containing three or more hetero rings
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D 413/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C07D 471/04: Ortho-condensed systems
- C07F 9/65586: {at least one of the hetero rings does not contain nitrogen as ring hetero atom}
- F16K 31/363: the fluid acting on a piston (F16K31/38 takes precedence)
- Y10T 137/86405: Repeating cycle
- Y10T 137/86421: Variable
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- B65D: CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- F16K: VALVES; TAPS; COCKS; ACTUATING-FLOATS; DEVICES FOR VENTING OR AERATING {(devices for emptying and evacuating the excess liquid in valves or conduits F16L55/07)}
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

This disclosure relates to: (a) compounds and salts thereof that, inter alia, inhibit HCV; (b) intermediates useful for the preparation of such compounds and salts; (c) compositions comprising such compounds and salts; (d) methods for preparing such intermediates, compounds, salts, and compositions; (e) methods of use of such compounds, salts, and compositions; and (f) kits comprising such compounds, salts, and compositions.

## Claims

### Claim at position 1

1-26. (canceled)

### Claim 27

A compound having formula (I), or a pharmaceutically acceptable salt thereof,
wherein:
R1 is formula (ii) or (v);
R1a, at each occurrence, is each independently hydrogen, halogen, C1-C3alkyl, or C1-C3haloalkyl;
R1b, at each occurrence, is each independently hydrogen, halogen, C1-C3alkyl, or C1-C3haloalkyl, wherein, optionally, two geminal R1b taken together are oxo;
R2 is C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10haloalkenyl, C2-C10haloalkynyl, or L2A-G2a;
L2A is a bond, C2alkenylene, or C2alkynylene;
G2a is C6-C10aryl or 5- to 10-membered heteroaryl, wherein the aryl or heteroaryl is optionally substituted with 1, 2, or 3 substituents selected from the group consisting of R20, L2B-R21, G2b and L2B-G2b;
L2B and L2C, at each occurrence, are each independently C1-C6alkylene, C2-C6alkenylene, or C2-C6alkynylene;
R20 is hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10haloalkenyl, C2-C10haloalkynyl, halogen, —N(R2a)C(O)R2b, —C(O)N(R2a)(R2b), —O—R2b, —C(O)R2b, —OC(O)R2b, —CO2H, —CO2R2b, —N(R2a)C(O)N(R2a)(R2b), —S—R2b, —S(O)2R2b, —S(O)R2b, —SO2N(R2a)(R2b), —N(R2a)(R2b), —N(R2a)S(O)2R2b, N(R2a)C(O)O(R2b), or —C(═CH2)R2b;
R21 is —N(R2a)C(O)R2b, —C(O)N(R2a)(R2b), —O—R2b, —C(O)R2b, —OC(O)R2b, —CO2H, —CO2R2b, —N(R2a)C(O)N(R2a)(R2b), —S—R2b, —S(O)2R2b, —S(O)R2b, —SO2N(R2a)(R2b), —N(R2a)(R2b), —N(R2a)S(O)2R2b, N(R2a)C(O)O(R2b), or —C(═CH2)R2b;
R2a, at each occurrence, is each independently hydrogen, C1-C6alkyl, C1-C6haloalkyl, or C3-C8cycloalkyl, wherein the C3-C8cycloalkyl is optionally substituted with 1, 2, 3, or 4 substituents selected from the group consisting of halogen, oxo, C1-C3alkyl, and C1-C3haloalkyl;
R2b, at each occurrence, is each independently hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10haloalkenyl, C2-C10haloalkynyl, -L2C-R2c, G2b or -L2C-G2b;
R2c is —N(R2d)C(O)R2d, —C(O)N(R2d)(R2d), —O—R2d, —C(O)R2d, —OC(O)R2d, —CO2H, —CO2R2d, —N(R2d)C(O)N(R2d)(R2d), —S—R2d, —S(O)2R2d, —S(O)R2d, —SO2N(R2d)(R2d), —N(R2d)(R2d), —N(R2d)S(O)2R2d, or N(R2d)C(O)O(R2d);
R2d, at each occurrence, is each independently hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkylene-OH, or C3-C8cycloalkyl, wherein the C3-C8cycloalkyl is optionally substituted with 1, 2, 3, or 4 substituents selected from the group consisting of halogen, oxo, C1-C3alkyl, and C1-C3haloalkyl;
G2b is C3-C10cycloalkyl, C5-C10cycloalkenyl, C6-C10aryl, 3- to 10-membered heterocyclyl, or 5- to 10-membered heteroaryl, wherein G2b is optionally substituted with 1, 2, 3, 4, or 5 substituents selected from the group consisting of C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10haloalkenyl, C2-C10haloalkynyl, halogen, oxo, cyano, hydroxy, —O—C1-C6alkyl, —O—C1-C6haloalkyl, —C1-C3alkylene-O—H, —C1-C3alkylene-O—C1-C6alkyl, C(O)H, —C1-C3alkylene-NH2, —NH2, —NO2, —C(O)C1-C6alkyl, —C(O)OC1-C6alkyl, and G2c;
G2c is C6-C10aryl or 5- to 10-membered heteroaryl, wherein G2c is optionally substituted with 1, 2, 3, 4, or 5 substituents selected from the group consisting of C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10haloalkenyl, C2-C10haloalkynyl, halogen, oxo, cyano, hydroxy, —O—C1-C6alkyl, —O—C1-C6haloalkyl, —C1-C3alkylene-O—H, —C1-C3alkylene-O—C1-C6alkyl, C(O)H, —C1-C3alkylene-NH2, —NH2, —NO2, —C(O)C1-C6alkyl, and —C(O)OC1-C6alkyl;
A and B together are a bicyclic heteroaryl, wherein A is formula (vi) or formula (vii):
wherein,
V1 and V2 are each C, or one of V1 and V2 is N and the other is C, wherein, when V3 is N, O or S or when A is (vii), V2 is C;
when A is (vi), V3 is CR7, NR7, N, O, or S; or, when A is (vii), V3 is N;
R7 is hydrogen, C1-C3alkyl, C1-C3haloalkyl, or C3-C6cycloalkyl;
is a single or double bond;
W1 is N or CR6, W2 is N or CR5, W3 is N or CR4, and W4 is N or CR3, wherein none, one or two of W1, W2, W3 and W4 is N;
W5 is N or CR6, and W6 is N or CR5, wherein none or one of W5 and W6 is N;
W7 is N, O, or S;
R3 and R6 are each independently hydrogen, C1-C3alkyl, C1-C3haloalkyl, halogen, —OC1-C3alkyl, or —OC1-C3haloalkyl;
R4 is hydrogen, halogen, C1-C6alkyl, C1-C6haloalkyl, —O—C1-C6alkyl, —O—C1-C6haloalkyl, cyano, —NH2, L4A-OH, 5-membered heteroaryl optionally substituted with 1 or 2 alkyl or halogen, 5-membered heterocycle or —N(R40)(SO2R4a);
R40 is hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, C2-C10haloalkenyl, C2-C10haloalkynyl, C3-C8cycloalkyl, 3- to 8-membered heterocyclyl, -L4A-G4a, -L4A-C(O)-L4B-G4a, -L4A-O-L4B-G4a, -L4A-S(O)2-L4B-G4a, -L4A-N(R4b)(L4B-G4a), -L4A-N(R4b)C(O)-L4B-G4a, -L4A-N(R4b)S(O)2-L4B-G4a, or -L4A-R4c, wherein the C1-C10alkyl, C2-C10alkenyl, and C2-C10alkynyl are each optionally substituted with 2, 3, or 4 hydroxy substituents; and wherein the C3-C8cycloalkyl or 3- to 8-membered heterocyclyl is each optionally substituted with L4B-G4b and optionally substituted with 1, 2, 3, or 4 substituents selected from the group consisting of halogen, oxo, C1-C3alkyl, C1-C3haloalkyl, —O—C1-C3alkyl, and —O—C1-C3haloalkyl;
L4A is C1-C10alkylene, C2-C10alkenylene, or C2-C10alkynylene, wherein L4A is optionally substituted with 1, 2, 3, 4, or 5 substituents selected from the group consisting of halogen, C1-C6alkyl, and C1-C6haloalkyl;
G4a is C3-C12cycloalkyl, C6-C12aryl, 3- to 12-membered heterocyclyl, or 5- to 12-membered heteroaryl, wherein G4a is optionally substituted with L4C-G4b and optionally substituted with 1, 2, 3, 4, or 5 substituents selected from the group consisting of halogen, oxo, C1-C3alkyl, C1-C3haloalkyl, —OH, —O—C1-C3alkyl, —O—C1-C3haloalkyl, thioxo, —NH2, —NH(C1-C3alkyl), and —N(C1-C3alkyl)2;
L4B and L4C, at each occurrence, are each independently a bond, C1-C6alkylene, C2-C6alkenylene, or C2-C6alkynylene, wherein L4B and L4C are each optionally substituted with 1, 2, 3, 4, or 5 substituents selected from the group consisting of halogen, C1-C6alkyl, and C1-C6haloalkyl;
G4b is C3-C12cycloalkyl, 3- to 12-membered heterocyclyl, C6-C12aryl, or 5- to 12-membered heteroaryl, wherein G4b is optionally substituted with 1, 2, 3, 4, or 5 substituents selected from the group consisting of halogen, oxo, C1-C6alkyl, C1-C6haloalkyl, hydroxy, —O—C1-C6alkyl, —O—C1-C6haloalkyl, —S(O)—C1-C6alkyl, —S(O)2—C1-C6alkyl, —C(O)—C1-C6alkyl, C1-C3alkylene-OH, C1-C3alkylene-O—C1-C3alkyl, C1-C3alkylene-N(C1-C3alkyl)2, and C1-C3alkylene-(N-heterocyclyl);
R4a and R4b, at each occurrence, are each independently hydrogen, C1-C6alkyl, C1-C6haloalkyl, or C3-C8cycloalkyl, wherein the C3-C8cycloalkyl is optionally substituted with 1, 2, 3, or 4 substituents selected from the group consisting of halogen, oxo, C1-C3alkyl, and C1-C3haloalkyl;
R4c is —O—R4b, —OC(O)R4b, —O—Si(C1-C6alkyl)3, —CN, —C(O)R4b, —CO2R4b, —C(O)N(R4b)2, —C(O)N(R4b)S(O)2R4b, —S—R4b, —S(O)2R4b, —S(O)R4b, —SO2N(R4b)2, —N(R4b)2, —N(R4b)C(O)R4b, —N(R4b)S(O)2R4b, —C(NOH)N(R4b)2, —C(O)C(OH)(R4b)2, or —P(O)(OR4b)2;
R5 is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, —O—C1-C6alkyl, —O—C1-C6haloalkyl, —O—C3-C6cycloalkyl, or G5a, wherein the C3-C6cycloalkyl groups are optionally substituted with 1, 2, 3, or 4 substituents selected from the group consisting of halogen, C1-C3alkyl, C1-C3haloalkyl, and oxo;
G5a is phenyl, wherein G5a is substituted with —C(O)N(R5a)-L5B-G5b, —C(O)-G5f, or —C(O)N(R5a)(R5e), and optionally substituted with 1, 2, or 3 substituents selected from the group consisting of C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, halogen, —O—R5b, CN, —N(R5b)C(O)R5b, —C(O)N(R5a)(R5b), —C(O)R5b, —OC(O)R5b, —CO2H, —CO2R5b, —N(R5b)C(O)N(R5a)(R5b), —S—R5b, —S(O)2R5b, —S(O)R5b, —SO2N(R5a)(R5b), —N(R5a)(R5b), —N(R5b)S(O)2R5b, N(R5b)C(O)O(R5b), -L5A-O—R5b, -L5A-CN, -L5A-N(R5b)C(O)R5b, -L5A-C(O)N(R5a)(R5b), -L5A-C(O)R5b, -L5A-OC(O)R5b, -L5A-CO2H, -L5A-CO2R5b, -L5A-N(R5b)C(O)N(R5a)(R5b), -L5A-S—R5b, -L5A-S(O)2R5b, -L5A-S(O)R5b, -L5A-SO2N(R5a)(R5b), -L5A-N(R5a)(R5b), -L5A-N(R5b)S(O)2R5b, -L5A-N(R5b)C(O)O(R5b), -G5d, and -L5A-G5d;
G5b is C3-C12cycloalkyl, C6-C12aryl, 3- to 12-membered heterocyclyl, or 5- to 12-membered heteroaryl, wherein each G5b is optionally substituted with 1, 2, 3, 4, or 5 substituents selected from the group consisting of oxo, halogen, C1-C6alkyl, C1-C6haloalkyl, —O—R5d, —CN, —N(R5d)C(O)R5d, —CON(R5a)(R5d), —C(O)R5d, —OC(O)R5d, —CO2H, —CO2R5d, —N(R5d)C(O)N(R5d)2, —S—R5d, —S(O)2R5d, —S(O)R5d, —SO2N(R5a)(R5d), —N(R5a)(R5d), —N(R5d)S(O)2R5d, N(R5d)C(O)O(R5d), -L5C-O—R5d, -L5C-CN, -L5C-N(R5d)C(O)R5d, -L5C-CON(R5a)(R5d), -L5C-C(O)R5d, -L5C-OC(O)R5d, -L5C-CO2H, -L5C-CO2R5d, -L5C-N(R5d)C(O)N(R5d)2, -L5C-S—R5d, -L5C-S(O)2R5d, -L5C-S(O)R5d, -L5C-SO2N(R5a)(R5d), -L5C-N(R5a)(R5d), -L5C-N(R5d)S(O)2R5d, -L5C-N(R5d)C(O)O(R5d), G5c, and -L5C-G5c;
G5c, at each occurrence, is each independently C3-C8cycloalkyl, C6-C10aryl, 4- to 10-membered heterocyclyl, or 5- to 10-membered heteroaryl, wherein G5c is optionally substituted with 1, 2, 3, 4, or 5 substituents selected from the group consisting of halogen, oxo, C1-C6alkyl, C1-C6haloalkyl, —O—C1-C6alkyl, and —O—C1-C6haloalkyl;
G5d, is at each occurrence, is each independently C3-C8cycloalkyl, C6-C10aryl, 4- to 10-membered heterocyclyl, or 5- to 10-membered heteroaryl, wherein G5d is optionally substituted with 1, 2, 3, 4, or 5 substituents selected from the group consisting of oxo, halogen, C1-C6alkyl, C1-C6haloalkyl, —O—R5d, —CN, —N(R5d)C(O)R5d, —CON(R5a)(R5d), —C(O)R5d, —OC(O)R5d, —CO2H, —CO2R5d, —N(R5d)C(O)N(R5d)2, —S—R5d, —S(O)2R5d, —S(O)R5d, —SO2N(R5a)(R5d), —N(R5a)(R5d), —N(R5d)S(O)2R5d, N(R5d)C(O)O(R5d), -L5C-O—R5d, -L5C-CN, -L5C-N(R5d)C(O)R5d, -L5C-CON(R5a)(R5d), -L5C-C(O)R5d, -L5C-OC(O)R5d, -L5C-CO2H, -L5C-CO2R5d, -L5C-N(R5d)C(O)N(R5d)2, -L5C-S—R5d, -L5C-S(O)2R5d, -L5C-S(O)R5d, -L5C-SO2N(R5a)(R5d), -L5C-N(R5a)(R5d), -L5C-N(R5d)S(O)2R5d, -L5C-N(R5d)C(O)O(R5d), G5c, and -L5C-G5c;
R5a, at each occurrence, is each independently hydrogen, C1-C6alkyl, C1-C6haloalkyl, or C3-C8cycloalkyl, wherein the C3-C8cycloalkyl is optionally substituted with 1, 2, 3, or 4 substituents selected from the group consisting of halogen, oxo, C1-C3alkyl, and C1-C3haloalkyl;
R5b, at each occurrence, is each independently hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C10alkynyl, C1-C10haloalkyl, -L5D-G5e, or -L5G-R5C;
R5c, at each occurrence, is each independently —CON(R5a)(R5g), —O—R5g, —OC(O)R5g, —CN, —C(O)R5g, —CO2H, —CO2R5g, —N(R5g)C(O)N(R5g)2, —S—R5g, —S(O)2R5g, —S(O)R5g, —SO2N(R5a)(R5g), —N(R5a)(R5g), —N(R5g)C(O)R5g, or —N(R5g)S(O)2R5g;
R5d, at each occurrence, is each independently hydrogen, C1-C6alkyl, C1-C6haloalkyl, or -L5F-G5c;
R5e, at each occurrence, is each independently hydrogen, C1-C10alkyl, C2-C10alkenyl, C2-C1 alkynyl, C1-C10haloalkyl, or -L5E-R5f;
R5f is —CON(R5a)(R5d), —O—R5d, —OC(O)R5d, —CN, —C(O)R5d, —CO2H, —CO2R5d, —N(R5d)C(O)N(R5d)2, —S—R5d, —S(O)2R5d, —S(O)R5d, —SO2N(R5a)(R5d), —N(R5a)(R5d), —N(R5d)C(O)R5d, or —N(R5d)S(O)2R5d;
R5g is hydrogen, C1-C6alkyl, C1-C6haloalkyl, or -L5H-G5e;
G5e, at each occurrence, is each independently C3-C8cycloalkyl, C6-C10aryl, 4- to 10-membered heterocyclyl, or 5- to 10-membered heteroaryl, wherein G5e is optionally substituted with 1, 2, 3, or 4 substituents selected from the group consisting of halogen, oxo, C1-C6alkyl, C1-C6haloalkyl, —OH, —O—C1-C6alkyl, and —O—C1-C6haloalkyl;
G5f is 4- to 10-membered heterocyclyl, wherein G5f is optionally substituted with 1, 2, 3, or 4 substituents selected from the group consisting of halogen, oxo, C1-C6alkyl, C1-C6haloalkyl, —O—C1-C6alkyl, and —O—C1-C6haloalkyl;
L5A, at each occurrence, is each independently C1-C6alkylene or C3-C8cycloalkyl, wherein L5A is each optionally substituted with 1, 2, 3, or 4 halogen;
L5B is a bond, C1-C6alkylene, or C3-C8cycloalkyl, wherein L5B is optionally substituted with 1, 2, 3, or 4 halogen and 1 or 2 hydroxy;
L5C, at each occurrence, is each independently C1-C6alkylene or C3-C8cycloalkyl, wherein L5C is each optionally substituted with 1, 2, 3, or 4 halogen and 1 or 2 hydroxy;
L5D, at each occurrence, is each independently a bond, C1-C6alkylene, or C3-C8cycloalkyl, wherein L5D is each optionally substituted with 1, 2, 3, or 4 halogen and 1 or 2 hydroxy;
L5E, at each occurrence, is each independently C1-C6alkylene, wherein L5E is optionally substituted with 1, 2, 3, or 4 halogen and 1 or 2 hydroxy;
L5F, at each occurrence, is each independently bond or C1-C6alkylene, wherein L5F is optionally substituted with 1, 2, 3, or 4 halogen and 1 or 2 hydroxy;
L5G, at each occurrence, is each independently C1-C6alkylene, wherein L5G is optionally substituted with 1, 2, 3, or 4 halogen and 1 or 2 hydroxy; and
L5H, at each occurrence, is each independently a bond, C1-C6alkylene, or C3-C8cycloalkyl, wherein L5H is each optionally substituted with 1, 2, 3, or 4 halogen and 1 or 2 hydroxy.

### Claim 28 (depends on 27)

The compound or salt of claim 27, wherein:
R2 is L2A-G2a, wherein L2A is a bond;
W2 is CR5;
W3 is CR4;
R4 is hydrogen, —N(R40)(SO2R4a), or a 5-membered heteroaryl optionally substituted with 1 or 2 halogen or alkyl; and
R5 is hydrogen, C3-C6cycloalkyl, —O—C1-C6alkyl, or G5a, wherein the C3-C6cycloalkyl is optionally substituted with 1, 2, 3, or 4 substituents selected from the group consisting of halogen, C1-C3alkyl, C1-C3haloalkyl, and oxo.

### Claim 29 (depends on 27)

The compound or salt of claim 27, wherein:
R1 is formula (ii);
R2 is L2A-G2a, wherein L2A is a bond;
R4 is hydrogen, —N(R40)(SO2R4a), or a 5-membered heteroaryl optionally substituted with 1 or 2 halogen or alkyl; and
R5 is hydrogen, C3-C6cycloalkyl, —O—C1-C6alkyl, or G5a, wherein the C3-C6cycloalkyl is optionally substituted with 1, 2, 3, or 4 substituents selected from the group consisting of halogen, C1-C3alkyl, C1-C3haloalkyl, and oxo.

### Claim 30 (depends on 29)

The compound or salt of claim 29, wherein:
V1 and V2 are each C, or one of V1 and V2 is N and the other is C; wherein, when V3 is O or S or when A is formula (vii), V2 is C;
when A is formula (vi), V3 is CR7, NR7, N, O, or S;
when A is formula (vii), V3 is N, O, or S;
W1 is N or CR6, W2 is N or CR5, W3 is N or CR4, W4 is N or CR3, wherein none, one, or two of W1, W2, W3 and W4 is N;
W5 is N or CR6, W6 is N or CR5, wherein none or one of W5 and W6 is N; and
W7 is N, O, or S.

### Claim 31 (depends on 27)

The compound or salt of claim 27, wherein:
R1 is formula (v);
R2 is L2A-G2a, wherein L2A is a bond;
R4 is hydrogen, —N(R40)(SO2R4a), or a 5-membered heteroaryl optionally substituted with 1 or 2 halogen or alkyl; and
R5 is hydrogen, C3-C6cycloalkyl, —O—C1-C6alkyl, or G5a, wherein the C3-C6cycloalkyl is optionally substituted with 1, 2, 3, or 4 substituents selected from the group consisting of halogen, C1-C3alkyl, C1-C3haloalkyl, and oxo.

### Claim 32 (depends on 31)

The compound or salt of claim 31, wherein:
V1 and V2 are each C, or one of V1 and V2 is N and the other is C; wherein, when V3 is O or S or when A is formula (vii), V2 is C;
when A is formula (vi), V3 is CR7, NR7, N, O, or S;
when A is formula (vii), V3 is N, O, or S;
W1 is N or CR6, W2 is N or CR5, W3 is N or CR4, W4 is N or CR3, wherein none, one, or two of W1, W2, W3 and W4 is N;
W5 is N or CR6, W6 is N or CR5, wherein none or one of W5 and W6 is N; and
W7 is N, O, or S.

### Claim 33 (depends on 27)

The compound or salt of claim 27, wherein:
R2 is L2A-G2a, wherein L2A is a bond;
R4 is hydrogen, —N(R40)(SO2R4a), or a 5-membered heteroaryl optionally substituted with 1 or 2 halogen or alkyl;
R5 is hydrogen, C3-C6cycloalkyl, —O—C1-C6alkyl, or G5a, wherein the C3-C6cycloalkyl groups are optionally substituted with 1, 2, 3, or 4 substituents selected from the group consisting of halogen, C1-C3alkyl, C1-C3haloalkyl, and oxo:
V1 and V2 are each C, or one of V1 and V2 is N and the other is C; wherein V2 is C when V3 is O;
V3 is N or O, when A is formula (vi);
W1 is CR6;
W2 is CR5;
W3 is CR4; and
W4 is CR3.

### Claim 34 (depends on 33)

The compound or salt of claim 33, wherein:
R1 is formula (ii);
R2 is L2A-G2a, wherein L2A is a bond;
G2a is phenyl, wherein the phenyl is optionally substituted with 1, 2, or 3 substituents selected from the group consisting of, R20, L2B-R21, G2b, and L2B-G2b;
R4 is —N(R40)(SO2R4a);
V1 and V2 are each C;
V3 is O;
W1 is CR6;
W2 is CR5;
W3 is CR4; and
W4 is CR3.

### Claim 35 (depends on 33)

The compound or salt of claim 33, wherein:
R1 is formula (v);
R2 is L2A-G2a, wherein L2A is a bond;
G2a is phenyl, wherein the phenyl is optionally substituted with 1, 2, or 3 substituents selected from the group consisting of, R20, L2B-R21, G2b, and L2B-G2b;
R4 is —N(R40)(SO2R4a);
R5 is cyclopropyl;
V1 and V2 are each C;
V3 is O;
W1 is CR6;
W2 is CR5;
W3 is CR4; and
W4 is CR3.

### Claim 36 (depends on 27)

The compound of claim 27, wherein the compound is selected from the group consisting of:
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(4-hydroxybutyl)methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[2-(methylsulfonyl)ethyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(3-methylbutyl)methanesulfonamide;
3-[3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-5-yl]-4-methyl-N-(1-phenylcyclopropyl)benzamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[3-(1,1-dioxidothiomorpholin-4-yl)propyl]methanesulfonamide;
N-(5-cyano-5-methylhexyl)-N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]methanesulfonamide;
diethyl (3-{[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino}propyl)phosphonate;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(4,4,4-trifluorobutyl)methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(3,3,3-trifluoropropyl)methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[3-(1H-pyrrol-1-yl)propyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(5,6,6-trifluorohex-5-en-1-yl)methanesulfonamide;
ethyl 4-{[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino}butanoate;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[4-(methylsulfonyl)butyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[2-(1,1-dioxidotetrahydrothiophen-3-yl)ethyl]methanesulfonamide;
3-{[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino}propane-1-sulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(3-hydroxy-3-methylbutyl)methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[3-(morpholin-4-yl)propyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[3-(dimethylamino)propyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[2-(pyrrolidin-1-yl)ethyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[2-(diethylamino)ethyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[3-(piperidin-1-yl)propyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[3-(diethylamino)propyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[3-(pyrrolidin-1-yl)propyl]methanesulfonamide;
N-(3-cyanopropyl)-N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(5-hydroxypentyl)methanesulfonamide;
4-{[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino}butanoic acid;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(2-hydroxyethyl)methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-(3-hydroxypropyl)methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[2-(methylsulfinyl)ethyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[3-(methylsulfinyl)propyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[3-(methylsulfonyl)propyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[2-(ethylsulfinyl)ethyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[2-(ethylsulfonyl)ethyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[3-(ethylsulfonyl)propyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[3-(ethylsulfinyl)propyl]methanesulfonamide;
N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(5-oxo-5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-1-benzofuran-6-yl]-N-(4-methoxybenzyl)methanesulfonamide;
N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(6-oxo-1,6-dihydropyrimidin-2-yl)-1-benzofuran-6-yl]-N-(3-methylbutyl)methanesulfonamide;
N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(5-oxo-5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-1-benzofuran-6-yl]-N-(3-methylbutyl)methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[3-(1H-tetrazol-5-yl)propyl]methanesulfonamide;
(1 Z)-4-{[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl](methylsulfonyl)amino}-N-hydroxybutanimidamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[3-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)propyl]methanesulfonamide;
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[3-(5-thioxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)propyl]methanesulfonamide; and
N-[5-cyclopropyl-3-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)-2-(4-fluorophenyl)-1-benzofuran-6-yl]-N-[3-(5-oxo-4,5-dihydro-1,2,4-thiadiazol-3-yl)propyl]methanesulfonamide.

### Claim 37 (depends on 27)

A pharmaceutical composition comprising one or more compounds of claim 27 or pharmaceutically acceptable salts thereof; one or more excipients; and optionally one or more additional therapeutic agents.

### Claim 38 (depends on 27)

A method of treating HCV infection, comprising administering a therapeutically effective amount of one or more compounds of claim 27 or pharmaceutically acceptable salts thereof, optionally in combination with one or more additional therapeutic agents.

### Claim 39 (depends on 38)

The method of claim 38, wherein the HCV infection is from an HCV virus of genotype 1a, 1b, 2a, 3a or 4a.

### Claim 40 (depends on 38)

The method of claim 38, wherein the HCV infection is from a mutant of an HCV virus.

### Claim 41 (depends on 27)

A method for inhibiting replication of an HCV virus, comprising exposing the virus to one or more compounds of claim 27 or pharmaceutically acceptable salts thereof, optionally in combination with one or more additional therapeutic agents.