# US 11,111,232 B2 · Substituted cyclobutylpyridine and cyclobutylpyrimidine compounds as indoleamine 2,3-dioxygenase (IDO) inhibitors

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- Number: US 11,111,232 B2
- Document ID: US11111232B2
- Status: Granted
- Kind: B2
- Application number: 16/753,050
- Filed: 2018-10-04
- Published: 2020-09-17
- Granted: 2021-09-07
- Earliest claimed: 2017-10-09
- Assignees: Merck Sharp & Dohme Corp.
- Applicants: Merck Sharp & Dohme Corp.
- Inventors: Catherine M. White; Abdelghani Achab; Indu T. Bharathan; Xavier Fradera; Yongxin Han; Derun Li; Jongwon Lim; Kun Liu; Meredeth Ann McGowan; Nunzio Sciammetta; Wensheng Yu; Hongjun Zhang; Hua Zhou
- Web page: https://patentgrep.com/patent/US11111232B2

## CPC

- C07D 213/75: Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- C07D 401/14: containing three or more hetero rings
- A61K 31/166: having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
- A61K 31/4418: having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
- A61P 35/00: Antineoplastic agents
- C07D 213/74: Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- C07D 213/81: Amides; Imides
- C07D 213/82: in position 3
- C07D 213/85: in position 3
- C07D 239/42: One nitrogen atom (nitro radicals C07D239/30)
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 413/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

## Abstract

Disclosed herein is a compound of formula (I), or a pharmaceutically acceptable salt thereof: Also disclosed herein are uses of a compound disclosed herein in the potential treatment or prevention of an IDO-associated disease or disorder. Also disclosed herein are compositions comprising a compound disclosed herein. Further disclosed herein are uses of a composition in the potential treatment or prevention of an IDO-associated disease or disorder.

## Claims

### Claim 1

A compound of formula (I), or a pharmaceutically acceptable salt thereof:
wherein:
each occurrence of A is independently selected from —CH═ and N═; provided that at least one A group is —N═ and at least one A group is —CH═;
L is selected from —NHC(O)— and —C(O)NH—;
W is selected from —C(O)NH— and —NHC(O)—;
R1 is selected from:
(1) C1-6 alkyl,
(2) —O—C1-6 alkyl,
(3) C3-6 cycloalkyl,
(4) aryl, and
(5) heterocyclyl;
wherein each of the C1-6 alkyl of (1) and (2) is optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) C3-6 cycloalkyl; and
wherein each of the C3-6 cycloalkyl of (3), aryl of (4), and heterocyclyl of (5) is optionally substituted with 1-3 substituents independently selected from (a) halogen, (b) —CN, (c) —O—C1-6 alkyl, and (d) C1-6 alkyl optionally substituted with 1-3 halogens;
R2 is selected from:
(1) C1-6 alkyl,
(2) C3-6 cycloalkyl,
(3) aryl, and
(4) heterocyclyl;
wherein the C1-6 alkyl of (1) is optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) C3-6 cycloalkyl; and
wherein each of the C3-6 cycloalkyl of (2), aryl of (3), and heterocyclyl of (4) is optionally substituted with 1-3 substituents independently selected from (a) halogen, (b) —CN, and (c) C1-6 alkyl optionally substituted with 1-3 halogens;
R3 is selected from H, halogen, —OH, and C1-6 alkyl optionally substituted with —OH; and each of R4 and R5 is independently selected from H, halogen, and C1-6 alkyl.

### Claim 2 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof,
wherein:
one A is —N═ and the three other A groups are each —CH═;
R3 is selected from (1) H, (2) —OH, and —CH3, optionally substituted with —OH; and
each of R4 and R5 is H.

### Claim 3 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein:
two A groups are each —N═ and the two other A groups are each —CH═;
R3 is H; and
each of R4 and R5 is H.

### Claim 4 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R1 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 substituents independently selected from (a) fluoro and (b) C3-6 cycloalkyl,
(2) —O—C1-6 alkyl,
(3) C3-6 cycloalkyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN,
(4) phenyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN, and
(5) a heterocyclyl selected from (a) a saturated 4-7 membered monocyclic heterocyclyl and (b) an aromatic 4-7 membered monocyclic heterocyclyl, wherein each heterocyclyl of (a) and (b) is optionally substituted with 1-3 substituents independently selected from (a) halogen, (b) —CN, and (c) C1-4 alkyl, optionally substituted with 1-3 halogens.

### Claim 5 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R1 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 substituents independently selected from (a) fluoro and (b) cyclopropyl,
(2) —O—C1-4 alkyl,
(3) cyclohexyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN,
(4) phenyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN, and
(5) a heterocyclyl selected from pyridinyl, pyrimidinyl, pyrrolidinyl, tetrahydropyranyl, and thiazolyl, wherein the heterocyclyl is optionally substituted with 1-3 substituents independently selected from (a) halogen, (b) —CN, and (c) C1-4 alkyl, optionally substituted with 1-3 halogens.

### Claim 6 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R2 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 halogens,
(2) C3-6 cycloalkyl, optionally substituted with 1-3 halogens,
(3) phenyl, optionally substituted with 1-3 halogens, and
(4) a heterocyclyl selected from (a) an aromatic 4-7 membered monocyclic heterocyclyl and (b) a 6-9 membered fused bicyclic ring containing one or more heteroatoms selected from N, O and S in either of the rings, wherein the heterocyclyl is optionally substituted with 1-3 halogens.

### Claim 7 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein R2 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 halogens,
(2) C3-6 cycloalkyl, optionally substituted with a halogen,
(3) phenyl, optionally substituted with 1-2 halogens, and
(4) a heterocyclyl selected from (a) pyridinyl and (b) benzo[d]thiazolyl, wherein the heterocyclyl is optionally substituted with 1-2 halogens.

### Claim 8 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein:
one A group is —N═ and the three other A groups are each —CH═;
R1 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 substituents independently selected from (a) fluoro and (b) C3-6 cycloalkyl,
(2) —O—C1-6 alkyl,
(3) C3-6 cycloalkyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN,
(4) phenyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN, and
(5) a heterocyclyl selected from (a) a saturated 4-7 membered monocyclic heterocyclyl and (b) an aromatic 4-7 membered monocyclic heterocyclyl, wherein each heterocyclyl of (a) and (b) is optionally substituted with 1-3 substituents independently selected from (a) halogen, (b) —CN, and (c) C1-4 alkyl, optionally substituted with 1-3 halogens;
R2 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 halogens,
(2) C3-6 cycloalkyl, optionally substituted with 1-3 halogens,
(3) phenyl, optionally substituted with 1-3 halogens, and
(4) a heterocyclyl selected from (a) an aromatic 4-7 membered monocyclic heterocyclyl and (b) a 6-9 membered fused bicyclic ring containing one or more heteroatoms selected from N, O and S in either of the rings, wherein the heterocyclyl is optionally substituted with 1-3 halogens;
R3 is selected from (1) H, (2) —OH, and (3) —CH3, optionally substituted with —OH; and each of R4 and R5 is H.

### Claim 9 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein:
one A group is —N═ and the three other A groups are each —CH═;
R1 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 substituents independently selected from (a) fluoro and (b) cyclopropyl,
(2) —O—C1-4 alkyl,
(3) cyclohexyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN,
(4) phenyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN, and
(5) a heterocyclyl selected from pyridinyl, pyrimidinyl, pyrrolidinyl, tetrahydropyranyl, and thiazolyl, wherein the heterocyclyl is optionally substituted with 1-3 substituents independently selected from (a) halogen, (b) —CN, and (c) C1-4 alkyl, optionally substituted with 1-3 halogens;
R2 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 halogens,
(2) C3-6 cycloalkyl, optionally substituted with a halogen,
(3) phenyl, optionally substituted with 1-2 halogens, and
(4) a heterocyclyl selected from (a) pyridinyl and (b) benzo[d]thiazolyl, wherein the heterocyclyl is optionally substituted with 1-2 halogens;
R3 is selected from (1) H, (2) —OH, and (3) —CH2—OH; and each of R4 and R5 is H.

### Claim 10 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein:
two A groups are each —N═ and the two other A groups are each —CH═;
R1 is phenyl, optionally substituted with 1-2 halogens;
R2 is phenyl, optionally substituted with 1-2 halogens;
R3 is H; and
each of R4 and R5 is H.

### Claim 11 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, of formula (Ia):
wherein:
each occurrence of A is independently selected from —CH═ and —N═; provided that at least one A group is —N═ and at least one A group is —CH═;
R1 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 substituents independently selected from (a) fluoro and (b) C3-6 cycloalkyl,
(2) —O—C1-6 alkyl,
(3) C3-6 cycloalkyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN,
(4) phenyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN, and
(5) a heterocyclyl selected from (a) a saturated 4-7 membered monocyclic heterocyclyl and (b) an aromatic 4-7 membered monocyclic heterocyclyl, wherein each heterocyclyl of (a) and (b) is optionally substituted with 1-3 substituents independently selected from (a) halogen, (b) —CN, and (c) C1-4 alkyl, optionally substituted with 1-3 halogens;
R2 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 halogens,
(2) C3-6 cycloalkyl, optionally substituted with 1-3 halogens,
(3) phenyl, optionally substituted with 1-3 halogens, and
(4) a heterocyclyl selected from (a) an aromatic 4-7 membered monocyclic heterocyclyl and (b) a 6-9 membered fused bicyclic ring containing one or more heteroatoms selected from N, O and S in either of the rings, wherein the heterocyclyl is optionally substituted with 1-3 halogens;
R3 is selected from (1) H, (2) —OH, and (3) —CH3, optionally substituted with —OH; and each of R4 and R5 is H.

### Claim 12 (depends on 11)

The compound of claim 11, or a pharmaceutically acceptable salt thereof, wherein:
one A group is —N═ and the three other A groups are each —CH ═;
R1 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 substituents independently selected from (a) fluoro and (b) cyclopropyl,
(2) —O—C1-4 alkyl,
(3) cyclohexyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN,
(4) phenyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN, and
(5) a heterocyclyl selected from pyridinyl, pyrimidinyl, pyrrolidinyl, tetrahydropyranyl, and thiazolyl, wherein the heterocyclyl is optionally substituted with 1-3 substituents independently selected from (a) halogen, (b) —CN, and (c) C1-4 alkyl, optionally substituted with 1-3 halogens;
R2 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 halogens,
(2) C3-6 cycloalkyl, optionally substituted with a halogen,
(3) phenyl, optionally substituted with 1-2 halogens, and
(4) a heterocyclyl selected from (a) pyridinyl and (b) benzo[d]thiazolyl, wherein the heterocyclyl is optionally substituted with 1-2 halogens;
R3 is selected from (1) H, (2) —OH, and (3) —CH2—OH; and each of R4 and R5 is H.

### Claim 13 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, of formula (1b):
wherein:
each occurrence of A is independently selected from —CH ═ and —N═; provided that at least one A group is —N═ and at least one A group is —CH═;
R1 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 substituents independently selected from (a) fluoro and (b) C3-6 cycloalkyl,
(2) —O—C1-6 alkyl,
(3) C3-6 cycloalkyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN,
(4) phenyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN, and
(5) a heterocyclyl selected from (a) a saturated 4-7 membered monocyclic heterocyclyl and (b) an aromatic 4-7 membered monocyclic heterocyclyl, wherein each heterocyclyl of (a) and (b) is optionally substituted with 1-3 substituents independently selected from (a) halogen, (b) —CN, and (c) C1-4 alkyl, optionally substituted with 1-3 halogens;
R2 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 halogens,
(2) C3-6 cycloalkyl, optionally substituted with 1-3 halogens,
(3) phenyl, optionally substituted with 1-3 halogens, and
(4) a heterocyclyl selected from (a) an aromatic 4-7 membered monocyclic heterocyclyl and (b) a 6-9 membered fused bicyclic ring containing one or more heteroatoms selected from N, O and S in either of the rings, wherein the heterocyclyl is optionally substituted with 1-3 halogens;
R3 is selected from (1) H, (2) —OH, and (3) —CH3, optionally substituted with —OH; and each of R4 and R5 is H.

### Claim 14 (depends on 13)

The compound of claim 13, or a pharmaceutically acceptable salt thereof, wherein:
one A group is —N═ and the three other A groups are each —CH ═;
R1 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 substituents independently selected from (a) fluoro and (b) cyclopropyl,
(2) —O—C1-4 alkyl,
(3) cyclohexyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN,
(4) phenyl, optionally substituted with 1-3 substituents independently selected from (a) halogen and (b) —CN, and
(5) a heterocyclyl selected from pyridinyl, pyrimidinyl, pyrrolidinyl, tetrahydropyranyl, and thiazolyl, wherein the heterocyclyl is optionally substituted with 1-3 substituents independently selected from (a) halogen, (b) —CN, and (c) C1-4 alkyl, optionally substituted with 1-3 halogens;
R2 is selected from:
(1) C1-6 alkyl, optionally substituted with 1-3 halogens,
(2) C3-6 cycloalkyl, optionally substituted with a halogen,
(3) phenyl, optionally substituted with 1-2 halogens, and
(4) a heterocyclyl selected from (a) pyridinyl and (b) benzo[d]thiazolyl, wherein the heterocyclyl is optionally substituted with 1-2 halogens;
R3 is selected from (1) H, (2) —OH, and (3) —CH2—OH; and each of R4 and R5 is H.

### Claim 15 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt thereof, selected from the group consisting of:
3-chloro-N-(5-(1-(4-chlorobenzamido)cyclobutyl)pyridin-2-yl)benzamide,
3-chloro-N-(5-(1(4-fluorophenyl)carbamoyl)cyclobutyl)pyridin-2-yl)benzamide,
3-chloro-N-(5-{1-[(3 ,3,3-trifluoropropyl)carbamoyl]cyclobutyl) pyridin-2-yl)benzamide, 3-chloro-N- {5-(propylcarbamoyl)cyclobutyl]pyridin-2-yl}benzamide, N-(4-fluorophenyl)-1-(6-(4,4,4-trifluorobutanamido)pyridin-3-yl)cyclobutane-1-carboxamide, 6-chloro-N-(5-{1-[(6-fluoropyridin-3-yl)carbamoyl] cyclobutyl}pyridin-2-yl)pyridine-2-carboxamide, N-(5-{1-[(6-fluoropyridin-3-yl)carbamoyl]cyclobutyl}pyridin-2-yl)cyclohexanecarboxamide, N-(5-{1-[(6-fluoropyridin-3-yl)carbamoyl]cyclobutyl}pyridin-2-yl)-6-methylpyridine-2-carboxamide, 4,4-difluoro-N-(5-{1-[(4-fluorophenyl)carbamoyl] cyclobutyl}pyridin-2-yl)cyclohexane-1-carboxamide, (1 S,3R)-3-cyano-N-(5-{1-[(4-fluorophenyl)carbamoyl]cyclobutyl}pyridin-2-yl)cyclohexane-1-carboxamide, 1-{6-[(4,4-dimethylpentanoyl)amino]pyridin-3-yl}-N-(4-fluorophenyl)cyclobutane-1-carboxamide, 1-{6-[(3-cyclopropylpropanoyl)amino]pyridin-3-yl}-N-(6-fluoropyridin-3-yl)cyclobutane-1-carboxamide, (1R,3R)-3-cyano-N-(5-{1-[(4-fluorophenyl)carbamoyl] cyclobutyl}pyridin-2-yl)cyclohexane-1-carboxamide, 3-chloro-2-fluoro-N-(5-{1-[(4-fluorophenyl)carbamoyl] cyclobutyl}pyridin-2-yl)benzamide, N-(5-{1-[(4-fluorophenyl)carbamoyl]cyclobutyl}pyridin-2-yl)cyclohexanecarboxamide, 5-chloro-2-fluoro-N-(5-{1-[(4-fluorophenyl)carbamoyl] cyclobutyl}pyridin-2-yl)benzamide, 3,3-difluoro-N-(5-{1-[(4-fluorophenyl)carbamoyl] cyclobutyl}pyridin-2-yl)cyclohexane-1-carboxamide, 1-{6-[(3-cyclopropylpropanoyl)amino]pyridin-3-yl}-N-(4-fluorophenyl)cyclobutane-1-carboxamide, tert-butyl (5-{1-[(4-fluorophenyl)carbamoyl] cyclobutyl}pyridin-2-yl)carbamate, N-(5-{1-[(4-fluorophenyl)carbamoyl]cyclobutyl}pyridin-2-yl)oxane-4-carboxamide, 3-chloro-2,6-difluoro-N-(5-{1-[(4-fluorophenyl)carbamoyl]cyclobutyl}pyridin-2-yl)benzamide, N-(5-{1-[(4-fluorophenyl)carbamoyl]cyclobutyl}pyridin-2-yl)oxane-3-carboxamide, 3-fluoro-N-(5-(1-((4-fluorophenyl)carbamoyl)cyclobutyl)pyridin-2-yl)benzamide, 3-cyano-N-(5-{1-[(4-fluorophenyl)carbamoyl]cyclobutyl}pyridin-2-yl)benzamide, 5-chloro-N-(5-{1-[(4-fluorophenyl)carbamoyl] cyclobutyl}pyridin-2-yl)pyridine-3-carboxamide, 4-chloro-N-(5-{1-[(4-fluorophenyl)carbamoyl] cyclobutyl}pyridin-2-yl)pyridine-2-carboxamide, N-(4-fluorophenyl)-1- {64(3-methylbutanoyl)amino]pyridin-3-yl} cyclobutane- 1-carboxamide, 5-fluoro-N-(5-{1-[(4-fluorophenyl)carbamoyl]cyclobutyl}pyridin-2-yl)pyridine-3-carboxamide, N-(5-{1-[(4-fluorophenyl)carbamoyl]cyclobutyl}pyridin-2-yl)-2-(trifluoromethyl)pyridine-4-carboxamide, 1- {6-[(cyclopropylacetyl)amino]pyridin-3-yl}-N-(4-fluorophenyl)cyclobutane-1-carboxamide, N-(5-{1-[(4-fluorophenyl)carbamoyl]cyclobutyl}pyridin-2-yl)pyrrolidine-1-carboxamide, 5-cyano-N-(5-{1-[(4-fluorophenyl)carbamoyl]cyclobutyl}pyridin-2-yl)pyridine-3-carboxamide, 5-chloro-N-(5-(1-((4,4-difluorocyclohexyl)carbamoyl)cyclobutyl)pyridin-2-yl)nicotinamide, 5-chloro-N-(5-{1-[(5-fluoropyridin-2-yl)carbamoyl] cyclobutyl}pyridin-2-yl)pyridine-3-carboxamide, N-cyclohexyl-5-(1-((4-fluorophenyl)carbamoyl)cyclobutyl)picolinamide, 3-chloro-N-(6-((4(4-fluorophenyl)carbamoyl)cyclobutyl)pyridin-3-yl)benzamide, 3-chloro-N-(6-{1-[(5-fluoropyridin-2-yl)carbamoyl] cyclobutyl}pyridin-3-yl)benzamide, 3-chloro-N-(2-((4-fluorophenyl)carbamoyl)cyclobutyl)pyrimidin-5-yl)benzamide, N-(6-(1-(6-chloronicotinamido)cyclobutyl)pyridin-3-yl)oxazole-2-carboxamide, 6-chloro-N-(1-{5-[(1,3-thiazole-2-carbonyl)amino]pyridin-2-yl} cyclobutyl)pyridine-3-carboxamide, 6-chloro-N-(1-{5-[(3 , 5-difluorobenzene-1-carbonyl)amino]pyridin-2-yl}cyclobutyl)pyridine-3-carboxamide, 6-chloro-N-(1-{5-[(3-chlorobenzene-1-carbonyl)amino]pyridin-2-yl}cyclobutyl)pyridine-3-carboxamide, 6-chloro-N-(1-{5-[(2-chloropyridine-4-carbonyl)amino]pyridin-2-yl}cyclobutyl)pyridine-3-carboxamide, 5-chloro-N-(6-{1-[(6-chloropyridine-3-carbonyl)amino]cyclobutyl}pyridin-3-yl)pyridine-3-carboxamide, 6-chloro-N-[1-(5-{[2-(trifluoromethyl)pyridine-4-carbonyl]amino}pyridin-2-yl)cyclobutyl]pyridine-3-carboxamide, 6-chloro-N-(1-{5-[(2-methylpyridine-4-carbonyl)amino]pyridin-2-yl}cyclobutyl)pyridine-3-carboxamide, 6-chloro-N-(1-{5-[(4-cyanobenzene-1-carbonyl)amino]pyridin-2-yl}cyclobutyl)pyridine-3-carboxamide, 6-chloro-N-(1-{5-[(3-cyanobenzene-1-carbonyl)amino]pyridin-2-yl}cyclobutyl)pyridine-3-carboxamide, N-(6- {1-[(6-chloropyridine-3-carbonyl)amino]cyclobutyl}pyridin-3-yl)-5-cyanopyridine-3-carboxamide, N-(6- {1-[(6-chloropyridine-3-carbonyl)amino]cyclobutyl}pyridin-3-yl)pyrimidine-2-carboxamide, 6-chloro-N-(1-{5-[(3-fluorobenzene-1-carbonyl)amino]pyridin-2-yl}cyclobutyl)pyridine-3-carboxamide, bromo-N-(1-(5-(3-chlorobenzamido)pyridin-2-yl)cyclobutyl)benzo[d]thiazole-2-carboxamide, 3-chloro-N-(6-(1-(propylcarbamoyl)cyclobutyl)pyridin-3-yl)benzamide, 3-cyano-N-(6-(14(4-fluorophenyl)carbamoyl)cyclobutyl)-2-hydroxypyridin-3-yl)benzamide, and 3-chloro-N-(6-(14(4-fluorophenyl)carbamoyl)cyclobutyl)-2-(hydroxymethyl)pyridin-3-yl)benzamide.

### Claim 16 (depends on 1)

A composition which comprises an inert carrier and a compound of claim 1 or a pharmaceutically acceptable salt thereof.

### Claim 17 (depends on 1)

A method for treating an IDO-associated disease or disorder in a mammalian subject which comprises administering to the subject an effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof.

### Claim 18 (depends on 1)

A method for treating an IDO-associated disease or disorder in a mammalian subject which comprises administering to the subject an effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof in combination with another anti-cancer agent.

### Claim 19 (depends on 1)

The method of claim 1, wherein the IDO-associated disease or disorder is a cancer, viral infection, HCV infection, depression, neurodegenerative disorders, trauma, age-related cataracts, organ transplantation, and autoimmune diseases.

### Claim 20 (depends on 19)

The method of claim 19, wherein the cancer is a cancer of the colon, pancreas, breast, prostate, lung, brain, ovary, cervix, testes, renal, head and neck, lymphoma, leukemia, and melanoma.