IP Library Granted Patent US 9,951,065
Granted Patent B2
US 9,951,065 · App. 15/153,527 · Granted Apr 24, 2018

Benzimidazole and imadazopyridine carboximidamide compounds

Inventors: Mark J. Bartlett (Castro Valley, CA); Julian Andrew Codelli (Seattle, WA); Britton Kenneth Corkey (Redwood City, CA); Jennifer Leigh Cosman (Foster City, CA); Kristyna Elbel (South San Francisco, CA); Jennifer Alissa Loyer-Drew (Seattle, WA); David Sperandio (Palo Alto, CA); Joshua Van Veldhuizen (Seattle, WA); Hai Yang (San Mateo, CA); Suet Chung Yeung (Redmond, WA)
Assignee: Gilead Sciences, Inc.
C07D471/04A61K31/4184A61K31/437A61K31/438A61K31/439A61K31/444A61K31/4439A61K31/454A61K31/4545A61K31/4725A61K31/496A61K31/497A61K31/506A61K31/538A61K31/5377A61K31/5386A61K31/541A61K31/55A61K31/553A61K45/06C07D235/06C07D235/08C07D235/12C07D235/14C07D235/16C07D235/24C07D235/28C07D235/30C07D295/125C07D401/04C07D401/12C07D403/12C07D405/12C07D405/14C07D409/12C07D413/12C07D471/08C07D487/04
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Quick Facts
Patent No.
US 9,951,065
App. No.
15/153,527
Granted
Apr 24, 2018
Kind
B2
Abstract

The present disclosure provides indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors of Formula I: or pharmaceutically acceptable salts thereof, in which X, L, n, m, R 1 , R 2a , R 2b , R n , R m , and R t are as defined herein, as well as pharmaceutical compositions that include a compound of Formula I, or pharmaceutically acceptable salts thereof, and methods of using the same to treat conditions mediated by IDO1.

Claims (567)

1. A compound of Formula I:

wherein

R 1 is mono or bicyclic aryl or heteroaryl, wherein each mono or bicyclic aryl or heteroaryl is optionally substituted with one, two, or three substituents independently selected from hydroxyl, halo, —CN, C 1-6 haloalkyl, C 1-6 haloalkoxy, C 1-6 alkoxy, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, and C 3-6 cycloalkyl, wherein two of the optional substituents can join to form an additional partially saturated heterocyclic ring; and

wherein each C 1-6 alkoxy, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, and C 3-6 cycloalkyl is optionally substituted with one, two, or three substituents independently selected from hydroxyl, halo, —CN, —N(R 20 )(R 22 ) and C 3-6 cycloalkyl;

X is N or CR 2c ;

R 2a , R 2b , and R 2c are independently hydrogen, hydroxyl, halo, CN, C 1-6 haloalkyl, C 1-6 haloalkoxy, C 1-6 alkoxy, or C 1-6 alkyl;

R 2d and R 2e are independently hydrogen, C 1-6 haloalkyl, C 1-6 haloalkoxy, or C 1-6 alkyl;

n and m are independently 0, 1, 2, or 3;

each R n and R m are independently hydrogen, hydroxyl, halo, C 1-6 alkoxy, C 1-6 alkyl, C 3-6 cycloalkyl, aryl, heterocyclyl, or heteroaryl; or two R n or R m join to form a C 3-6 cycloalkyl; and

wherein each C 1-6 alkoxy, C 1-6 alkyl, C 3-6 cycloalkyl aryl, heterocyclyl, or heteroaryl is optionally substituted with one, two, or three substituents independently selected from hydroxyl, halo, —CN, —N(R 20 )(R 22 ), C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 haloalkoxy, C 1-6 alkoxy, C 1-6 alkyl, and C 3-6 cycloalkyl;

L is a bond, —NR 3 —, —C(O)—NR 3 —, —NR 3 —C(O)—, —NR 3 SO 2 —, —NR 3 SO 2 —NR 3 —, —SO 2 NR 3 —, —O—, —S—, or S(O) t —, where t is 0, 1 or 2;

each R 3 is independently hydrogen, C 1-6 alkyl, C 3-6 cycloalkyl, aryl, heterocyclyl, or heteroaryl; and

R t is hydrogen, C 1-6 alkyl, C 1-6 alkoxy, —C(O)R 20 , —C(O)OR 20 , —NC(O)OR 20 , —N(R 20 )(R 22 ), —C(O)N(R 20 )(R 22 ), —SO 2 R 20 , —N(R 20 )SO 2 (R 21 ), —N(R 20 )SO 2 —N(R 21 )(R 22 ), —SO 2 N(R 20 )(R 22 ), C 3-15 cycloalkyl, aryl, heteroaryl, or heterocyclyl, provided that when R t is C 1-6 alkoxy, —NC(O)OR 20 , —N(R 20 )(R 22 ), —N(R 20 )SO 2 (R 21 ), —N(R 20 )SO 2 —N(R 21 )(R 22 ), or —SO 2 N(R 20 )(R 22 ), and m is 0, then L is a bond;

wherein said C 1-6 alkyl, C 1-6 alkoxy, C 3-15 cycloalkyl, aryl, heterocyclyl, or heteroaryl is optionally substituted with one, two, or three substituents independently selected from hydroxyl, halo, —NO 2 , C 1-6 haloalkyl, C 1-6 haloalkoxy, —C(O)R 20 , —N(R 20 )(R 22 ), SO 2 R 20 , —N(R 20 )SO 2 (R 21 ), —N(R 20 )SO 2 —N(R 21 )(R 22 ), SO 2 N(R 20 )(R 22 ), C 3-6 cycloalkyl, —CN, C 1-6 alkoxy, C 1-6 alkyl, and heterocyclyl; and wherein said heterocyclyl is optionally substituted with one or two oxo;

wherein said C 3-6 cycloalkyl, C 1-6 alkyl or C 1-6 alkoxy is optionally substituted with one, two, or three substituents independently selected from hydroxyl, halo, —NO 2 , C 1-6 haloalkyl, C 1-6 haloalkoxy, C 1-6 alkoxy, —N(R 20 )(R 22 ), —SO 2 R 20 , —N(R 20 )SO 2 (R 22 ), —N(R 20 )SO 2 —N(R 21 )(R 22 )—, and —SO 2 N(R 20 )(R 22 ); and said C 1-6 alkyl is optionally substituted with aryl;

R 20 , R 21 , and R 22 are independently selected from hydrogen, C 1-6 alkyl, C 1-6 haloalkyl, C 3-6 cycloalkyl, aryl, heterocyclyl, and heteroaryl;

wherein said aryl, heterocyclyl, or heteroaryl is optionally substituted with one, two, or three halogen;

or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

2. The compound of claim 1 , wherein the compound is represented by Formula IV:

or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

3. The compound of claim 1 wherein R 1 is bicyclic aryl or heteroaryl optionally substituted with one, two, or three substituents independently selected from hydroxyl, halo, —CN, C 1-6 haloalkyl, C 1-6 haloalkoxy, C 1-6 alkoxy, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, and C 3-6 cycloalkyl; or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

4. The compound of claim 1 wherein R 1 is phenyl optionally substituted with one, two, or three substituents independently selected from hydroxyl, halo, —CN, C 1-6 haloalkyl, C 1-6 haloalkoxy, C 1-6 alkoxy, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, and C 3-6 cycloalkyl, and wherein two of the optional substituents can join to form an additional partially saturated heterocyclic ring;

or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

5. The compound of claim 1 wherein R 1 is selected from the group consisting of

or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

6. The compound of claim 1 wherein X is N; or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

7. The compound of claim 1 wherein X is CR 2c ; or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

8. The compound of claim 1 wherein L is a bond; or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

9. The compound of claim 1 wherein L is —NR 3 ; or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

10. The compound of claim 1 wherein R t is hydrogen; or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

11. The compound of claim 1 wherein R t is C 1-6 alkyl optionally substituted with one, two, or three substituents independently selected from hydroxyl, halo, —NO 2 , C 1-6 haloalkyl, C 1-6 haloalkoxy, C 3-6 cycloalkyl, —CN, and C 1-6 alkoxy; or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

12. The compound of claim 1 wherein R t is C 3-15 cycloalkyl, aryl, heteroaryl, or heterocyclyl, wherein said cycloalkyl, aryl, heterocyclyl, or heteroaryl is optionally substituted with one, two, or three substituents independently selected from hydroxyl, halo, —NO 2 , C 1-6 haloalkyl, C 1-6 haloalkoxy, C 3-6 cycloalkyl, —CN, C 1-6 alkoxy and C 1-6 alkyl; or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

13. The compound of claim 1 wherein L is —NR 3 and R t is C 3-15 cycloalkyl, aryl, heteroaryl, or heterocyclyl, wherein said cycloalkyl, aryl, heterocyclyl, or heteroaryl is optionally substituted with one, two, or three substituents independently selected from hydroxyl, halo, —NO 2 , C 1-6 haloalkyl, C 1-6 haloalkoxy, C 3-6 cycloalkyl, —CN, and C 1-6 alkoxy; or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

14. The compound of claim 1 wherein the group

is selected from the group consisting of:

or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

15. A compound selected from the group consisting of:

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-4-methyl-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-4-(trifluoromethoxy)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-6-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-5-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-4-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

4-Chloro-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-4-(trifluoromethyl)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-6-fluoro-N′-hydroxy-7-methyl-3H-benzimidazole-4-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

6-Chloro-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-benzo[d]imidazole-4-carboximidamide,

4-Bromo-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-Amino-N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-Amino-N-(3-bromo-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-Amino-N-(3-bromophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-Amino-N-(3-chlorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-Amino-4,5-difluoro-N-(4-fluoro-3-(trifluoromethyl)phenyl)-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-Amino-N-(3-bromophenyl)-4-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-Amino-N-(3-bromo-4-fluorophenyl)-4-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-Amino-N-(3-chlorophenyl)-4-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-Amino-4-fluoro-N-(4-fluoro-3-(trifluoromethyl)phenyl)-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-Amino-N-(3-chloro-4-fluorophenyl)-4-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-Amino-N-(3-chloro-4-fluorophenyl)-4-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-morpholinoethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chlorophenyl)-4,5-difluoro-N′-hydroxy-2-(((3-methoxypropyl)amino)methyl)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chlorophenyl)-2-(((cyclopropylmethyl)amino)methyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chlorophenyl)-2-((dimethylamino)methyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide

N-(3-Chlorophenyl)-4,5-difluoro-N′-hydroxy-2-((isopropylamino)methyl)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chlorophenyl)-2-((ethylamino)methyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chlorophenyl)-4,5-difluoro-N′-hydroxy-2-(hydroxymethyl)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chlorophenyl)-4,5-difluoro-N′-hydroxy-2-((methylamino)methyl)-1H-benzo[d]imidazole-7-carboximidamide,

2-(Aminomethyl)-N-(3-chlorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-morpholino-1H-benzo-[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-4-fluoro-N′-hydroxy-2-((2-(methylsulfonyl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-4-fluoro-N′-hydroxy-2-((2-morpholinoethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(methylsulfonyl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-((2-(4,4-difluoropiperidin-1-yl)ethyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((1-morpholinopropan-2-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(methylamino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-((3-(dimethylamino)propyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-methoxyethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(pyrrolidin-1-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-((2-(diethylamino)ethyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-((2-(dimethylamino)ethyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chlorophenyl)-4,5-difluoro-N′-hydroxy-2-(1-methylpiperidin-3-yl)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-6,7-difluoro-N′-hydroxy-2-(((3-methoxypropyl)amino)methyl)-1H-benzo[d]imidazole-4-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(hydroxymethyl)-1H-benzo[d]imidazole-7-carboximidamide,

2-(Aminomethyl)-N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((methylamino)methyl)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(((cyclopropylmethyl)amino)methyl)-4,5-difluoro-N-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-((ethylamino)methyl)-6,7-difluoro-N′-hydroxy-1H-benzo[d]imidazole-4-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-6,7-difluoro-N′-hydroxy-2-((isopropylamino)methyl)-1H-benzo[d]imidazole-4-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-((dimethylamino)methyl)-6,7-difluoro-N′-hydroxy-1H-benzo[d]imidazole-4-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(2-(dimethylamino)ethyl)-6,7-difluoro-N′-hydroxy-1H-benzo[d]imidazole-4-carboximidamide,

N-(3-Bromo-4-fluorophenyl)-2-(2-(dimethylamino)ethyl)-6,7-difluoro-N′-hydroxy-1H-benzo[d]imidazole-4-carboximidamide,

N-(3-Bromophenyl)-2-(2-(dimethylamino)ethyl)-6,7-difluoro-N′-hydroxy-1H-benzo[d]imidazole-4-carboximidamide,

N-(3-Chlorophenyl)-2-(2-(dimethylamino)ethyl)-6,7-difluoro-N′-hydroxy-1H-benzo[d]imidazole-4-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-6,7-difluoro-N′-hydroxy-2-(2-(methylamino)ethyl)-1H-benzo[d]imidazole-4-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(2-(diethylamino)ethyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(5-Chloro-2-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(5-Bromo-2,4-difluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(5-Chloro-2,4-difluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3,5-Dichloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-2,4-difluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Cyclopropyl-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N′-Hydroxy-N-(4-(trifluoromethoxy)phenyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(Benzofuran-4-yl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(Benzofuran-6-yl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(Benzofuran-7-yl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(benzofuran-5-yl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(5-Bromo-2-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Bromo-5-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N′-Hydroxy-N-(3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Fluoro-5-(trifluoromethyl)phenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(2,5-Dichlorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(6-Fluoro-[1,1′-biphenyl]-3-yl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-(But-1-yn-1-yl)-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-(Cyclopropylethynyl)-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Bromophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Bromo-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chlorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(4-Fluoro-3-(trifluoromethyl)phenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(4-Fluoro-3-(prop-1-yn-1-yl)phenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Bromo-4-chlorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3,4-Dichlorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(4-Chlorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(4-Bromophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(4-Fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Cyano-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N′-Hydroxy-N-(4-(trifluoromethyl)phenyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N′-Hydroxy-N-(3-methoxyphenyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(4-Fluoro-3-isopropylphenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N′-Hydroxy-N-(p-tolyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Ethynylphenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Ethylphenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Ethynyl-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-(Difluoromethyl)phenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-Hydroxy-N-(3-(trifluoromethoxy)phenyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-Hydroxy-N-phenyl-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(4-Fluoro-3-(trifluoromethoxy)phenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-Hydroxy-N-(naphthalen-2-yl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloronaphthalen-2-yl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N′-hydroxy-N-(naphthalen-1-yl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(4-Chloronaphthalen-1-yl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(4-Fluoro-3-methoxyphenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-methyl-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-ethyl-N-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-cyclopropyl-N-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(methoxymethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

4-(3-Chloro-4-fluorophenyl)-3-(2-(hydroxymethyl)-1H-imidazo[4,5-b]pyridin-7-yl)-1,2,4-oxadiazol-5(4H)-one,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(morpholinomethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-((dimethylamino)methyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-((ethyl amino)methyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-((Benzyl amino)methyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-((isopropylamino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(((cyclopropylmethyl)amino)methyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((2,2,2-trifluoroethyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-((cyclopropylamino)methyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((3-methoxypropyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((pyridin-2-ylmethyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((3-methoxypropyl)(methyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((2-methoxybenzyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((2-methoxyethyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((2-(pyridin-2-yl)ethyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((pyridin-3-ylmethyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2((((tetrahydro-2H-pyran-2-yl)methyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-((phenylamino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-((((tetrahydro-2H-pyran-3-yl)methyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((pyrimidin-2-ylmethyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((3-morpholinopropyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((tetrahydro-2H-pyran-4-yl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((pyridin-4-ylmethyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((pyrazin-2-ylmethyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-((((tetrahydrofuran-3-yl)methyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(((2-(dimethylamino)ethyl)amino)methyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((2-(pyrimidin-2-yl)ethyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((3-hydroxypropyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(pyrrolidin-1-ylmethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(piperidin-1-ylmethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-((neopentylamino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(((2,2-difluoroethyl)amino)methyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((3-hydroxy-2,2-dimethylpropyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(((thiazol-2-ylmethyl)amino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-((7-(N-(3-Chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-1H-imidazo[4,5-b]pyridin-2-yl)methyl)acetamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(thiophen-2-yl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(pyridin-3-yl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(1H-pyrrol-2-yl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(1H-imidazol-2-yl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(1H-pyrazol-5-yl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(4-methyl-1H-imidazol-2-yl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(pyrrolidin-2-yl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-Amino-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(cyclopropylamino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(phenylamino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(phenethylamino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-((2,2,2-trifluoroethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(methylamino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

Isopropyl (7-(N-(3-chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-1H-imidazo[4,5-b]pyridin-2-yl)carbamate,

Ethyl (7-(N-(3-chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-1H-imidazo[4,5-b]pyridin-2-yl)carbamate,

N-(3-Chloro-4-fluorophenyl)-2-((cyclopropylmethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-((3,3-difluorocyclobutyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(ethylamino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(cyclobutylamino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(isopropylamino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chlorophenyl)-N′-hydroxy-2-(methylamino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-((2-(diethylamino)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-((2-morpholinoethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(dimethylamino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-(Chloromethyl)-N-(4-fluoro-3-(trifluoromethyl)phenyl)-N′-hydroxy-3H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(4-Fluoro-3-(trifluoromethyl)phenyl)-N′-hydroxy-2-(hydroxymethyl)-3H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(1-hydroxyethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(hydroxy(phenyl)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(cyclopropyl(hydroxy)methyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(2-hydroxypropan-2-yl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(2,2,2-trifluoro-1-hydroxyethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(hydroxymethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-((methylamino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-(Aminomethyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(phenylsulfonamidomethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(methylsulfonamidomethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-((pyrimidin-2-ylamino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(2-hydroxyethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(2-(dimethylamino)ethyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(2-(diethylamino)ethyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(2-((cyclopropylmethyl)(methyl)amino)ethyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(2-((2,2-difluoroethyl)(methyl)amino)ethyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(2-(methylamino)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-(2-Aminoethyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(2-((2-methoxyethyl)amino)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(2-morpholinoethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(2-(piperidin-1-yl)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-(2-((2-methoxyethyl)(methyl)amino)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-(2-(dimethylamino)-1-hydroxyethyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-((isobutylamino)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-3-methyl-3H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-[2-(2-methoxyethylamino)ethyl]-3H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-[3-(dimethylamino)propyl]-6,7-difluoro-N′-hydroxy-3H-benzimidazole-4-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-7-fluoro-N′-hydroxy-2-(3-morpholin-4-ylpropylamino)-3H-benzimidazole-4-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-2-((2-(dimethylamino)ethylamino]-7-fluoro-N′-hydroxy-3H-benzimidazole-4-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-[(1-methylpiperidin-2-yl)methylamino]-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-Chloro-4-fluorophenyl)-N′-hydroxy-2-[(1-methylpyrrolidin-3-yl)amino]-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(2-(ethylamino)ethyl)-N′-hydroxy-3H-imidazo[4, 5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(2-(isopropylamino)ethyl)-3H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(2-(isobutylamino)ethyl)-3H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(2-(cyclopropylamino)ethyl)-N′-hydroxy-3H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(2-((cyclopropylmethyl)amino)ethyl)-N′-hydroxy-3H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-(2-(2-amino-4,5-dihydro-1H-imidazol-1-yl)ethyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(2-(methylsulfonamido)ethyl)-1H-benzo[d]imidazole-7-carboximidamide,

2-(2-aminoethyl)-N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-methoxyethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

tert-butyl (2-(7-(N-(3-chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-4,5-difluoro-1H-benzo[d]imidazol-2-yl)ethyl)carbamate,

N-(3-chloro-4-fluorophenyl)-2-((2-(4,4-difluoropiperidin-1-yl)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(dimethylamino)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(methylamino)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((1-methylazepan-3-yl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(2-methoxyethyl)(methyl)amino)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(2,2-difluoroethyl)(methyl)amino)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((3-morpholinopropyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(piperidin-1-yl)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-cyclohexylethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(tetrahydro-2H-pyran-4-yl)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2,2-difluoroethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(oxetan-3-ylamino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((tetrahydrofuran-3-yl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((tetrahydro-2H-pyran-4-yl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

3-((7-(N-(3-chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-4,5-difluoro-1H-benzo[d]imidazol-2-yl)amino)propanamide),

N-(3-chloro-4-fluorophenyl)-2-((2-((2,2-difluoroethyl)amino)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(cyclopropyl(methyl)amino)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(cyclopropyl(2-methoxyethyl)amino)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-((2-(azetidin-1-yl)ethyl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((3-methoxypropyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(2-oxopyrrolidin-1-yl)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(morpholinosulfonyl)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(3-fluoropiperidin-1-yl)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-bromo-4-fluorophenyl)-N′-hydroxy-2-((2-morpholinoethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(methyl(tetrahydro-2H-pyran-4-yl)amino)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(isopropyl(methyl)amino)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-(((1-aminocyclopropyl)methyl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-((2-(1-aminocyclopropyl)ethyl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-((2-(2-oxa-5-azabicyclo[4.1.0]heptan-5-yl)ethyl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-((2-(7-oxa-4-azaspiro[2.5]octan-4-yl)ethyl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

(R)-(3-chloro-4-fluorophenyl)-2-((2-(3-fluoropyrrolidin-1-yl)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

(S)-(3-chloro-4-fluorophenyl)-2-((2-(3-fluoropyrrolidin-1-yl)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-((2-(2-azabicyclo[4.1.0]heptan-2-yl)ethyl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-((2-(4-azaspiro[2.5]octan-4-yl)ethyl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(3-fluoroazetidin-1-yl)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(3,3-difluoroazetidin-1-yl)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-((2-(4-azaspiro[2.4]heptan-4-yl)ethyl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((3-(3-fluoropiperidin-1-yl)propyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(phenylamino)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(methyl(phenyl)amino)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(((1,1-dioxidotetrahydro-2H-thiopyran-3-yl)methyl)amino)-N-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-ethoxycyclopropyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-bromo-4-fluorophenyl)-N′-hydroxy-2-(methylamino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-(2-(azepan-1-yl)ethyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-(2-(azetidin-1-yl)ethyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

(R)—N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(2-(3-hydroxypyrrolidin-1-yl)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

(S)—N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(2-(3-hydroxypyrrolidin-1-yl)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(2-(4-hydroxypiperidin-1-yl)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-bromo-4-fluorophenyl)-2-(2-(dimethylamino)ethyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chlorophenyl)-2-(2-(dimethylamino)ethyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-bromophenyl)-2-(2-(dimethylamino)ethyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(2-(methylsulfonamido)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(2-(sulfamoylamino)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chlorophenyl)-N′-hydroxy-2-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-bromophenyl)-N′-hydroxy-2-(2-(pyrrolidin-1-yl)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(2-(7-(N-(3-chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-1H-imidazo[4,5-b]pyridin-2-yl)ethyl)acetamide,

N-(3-chlorophenyl)-N′-hydroxy-2-(2-(piperidin-1-yl)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-bromophenyl)-N′-hydroxy-2-(2-(piperidin-1-yl)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

Methyl (2-(7-(N-(3-chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-1H-imidazo[4,5-b]pyridin-2-yl)ethyl)carbamate,

N-(3-chloro-4-fluorophenyl)-2-(2-((2,4-dimethoxybenzyl)amino)ethyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-(2-(4-benzylpiperidin-1-yl)ethyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-(2-(3-azabicyclo[3.3.1]nonan-3-yl)ethyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-(2-(3-azabicyclo[3.2.1]octan-3-yl)ethyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((1-methylpiperidin-3-yl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

(S)—N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(3-hydroxypyrrolidin-1-yl)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

(S)—N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(3-hydroxypyrrolidin-1-yl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((1-(2-methoxyethyl)pyrrolidin-3-yl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(((4-methylmorpholin-3-yl)methyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(pyrrolidin-1-yl)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(((4-((methylsulfonyl)methyl)tetrahydro-2H-pyran-4-yl)methyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(methylsulfonyl)benzyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-((1-acetylpiperidin-3-yl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((ethylamino)methyl)-4-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((dimethylamino)methyl)-4-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4-fluoro-N′-hydroxy-2-((isopropylamino)methyl)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4-fluoro-N′-hydroxy-2-((methylamino)methyl)-1H-benzo[d]imidazole-7-carboximidamide,

2-(aminomethyl)-N-(3-chloro-4-fluorophenyl)-4-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-hydroxy-2-methylpropyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-hydroxypropyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

2-((7-(N-(3-chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-4,5-difluoro-1H-benzo[d]imidazol-2-yl)amino)acetamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-hydroxyethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((3-hydroxycyclobutyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((3-(pyridin-2-yl amino)propyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-sulfamoylethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(((1-methyl-1H-pyrazol-5-yl)methyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

2-((2-(1H-pyrazol-1-yl)ethyl)amino)-N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-((7-(N-(3-chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-4,5-difluoro-1H-benzo[d]imidazol-2-yl)amino)-N,N-dimethylacetamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(2-hydroxy-2-methylpropyl)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((4-(dimethylamino)butyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((piperidin-3-ylmethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((1-methylpiperidin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-bromophenyl)-N′-hydroxy-2-((2-morpholinoethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-5-fluoro-N′-hydroxy-4-methoxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((pyridin-2-ylmethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-((2-(1H-pyrazol-1-yl)ethyl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(((1-methyl-1H-pyrazol-3-yl)methyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((4,4,4-trifluorobutyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((3,3,3-trifluoropropyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(2-methoxyethoxy)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((3-(cyclopropyl(methyl)amino)propyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((3-(cyclopropylamino)propyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((3-(cyclopropyl(ethyl)amino)propyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(4-fluoropiperidin-l-yl)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(2,2,2-trifluoroethoxy)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((3-(2,2,2-trifluoroethoxy)propyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(3-methoxypiperidin-1-yl)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((3-(difluoromethoxy)propyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

(R)—N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(((tetrahydrofuran-2-yl)methyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

(S)—N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(((tetrahydrofuran-2-yl)methyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(tetrahydrofuran-2-yl)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(piperidin-2-ylmethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(1-(dimethylamino)propan-2-yl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(2-(methylamino)propyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(2-(dimethylamino)propyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(pyrrolidin-2-ylmethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chlorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(pyrrolidin-1-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-bromophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(pyrrolidin-1-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-bromo-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(pyrrolidin-1-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

2-((2-aminoethyl)amino)-N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(2-((7-(N-(3-chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-4,5-difluoro-1H-benzo[d]imidazol-2-yl)amino)ethyl)acetamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(methylsulfonamido)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(cyclopropanesulfonamido)ethyl)amino)-4,5-difluoro-N-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

Methyl (2-((7-(N-(3-chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-4,5-difluoro-1H-benzo[d]imidazol-2-yl)amino)ethyl)carbamate,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(sulfamoylamino)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(phenylsulfonamido)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-cyanoethyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(3-ethylureido)ethyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((pyridin-2-ylmethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((pyridin-3-ylmethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((pyridin-3-ylmethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

2-(((1H-imidazol-2-yl)methyl)amino)-N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-chloro-N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-((2-aminobenzyl)amino)-N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(dimethylamino)benzyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(((1-methyl-1H-imidazol-2-yl)methyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((pyrimidin-2-ylmethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((3-(dimethylamino)-2,2-dimethylpropyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((3-(dimethylamino)-2-methylpropyl)amino)-4,5-difluoro-N-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((3-(dimethylamino)butyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(1-methylpyrrolidin-2-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(1-methylpiperidin-2-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(((4-methylmorpholin-2-yl)methyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(((4-methylmorpholin-2-yl)methyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(((1-methyl-1H-pyrazol-5-yl)methyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-((7-(N-(3-chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-1H-imidazo[4,5-b]pyridin-2-yl)amino)-N,N-dimethylacetamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(3-(hydroxymethyl)azetidin-1-yl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((oxetan-3-ylmethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(1-methyl-1H-imidazol-2-yl)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((3-(pyridin-2-ylamino)propyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(neopentylamino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(isobutylamino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(((tetrahydro-2H-pyran-2-yl)methyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(((tetrahydrofuran-3-yl)methyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4-fluoro-N′-hydroxy-2-((2-morpholinoethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-N-methyl-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-amino-N-(3-chloro-4-fluorophenyl)-5-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-amino-N-(3-chlorophenyl)-5-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-amino-N-(3-bromophenyl)-5-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-amino-N-(3-bromo-4-fluorophenyl)-5-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-4,5-difluoro-N-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(diethylamino)ethyl)amino)-4-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4-fluoro-N′-hydroxy-2-((2-(pyrrolidin-1-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-morpholinopropyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((1-(dimethylamino)propan-2-yl)amino)-4,5-difluoro-N-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(dimethylamino)ethyl)amino)-5-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-5-fluoro-N′-hydroxy-2-((2-(pyrrolidin-1-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((3-(dimethylamino)-2,2-dimethylpropyl)amino)-4-fluoro-N-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-bromo-4-fluorophenyl)-2-((2-(dimethylamino)ethyl)amino)-4-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-bromophenyl)-2-((2-(dimethylamino)ethyl)amino)-4-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chlorophenyl)-2-((2-(dimethylamino)ethyl)amino)-4-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chlorophenyl)-2-((3-(dimethylamino)propyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-bromophenyl)-2-((3-(dimethylamino)propyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-bromo-4-fluorophenyl)-2-((3-(dimethylamino)propyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((3-(dimethylamino)propyl)amino)-4-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((3-(dimethylamino)propyl)amino)-5-fluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-((2-(benzyl(methyl)amino)ethyl)amino)-N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(2-((cyclohexylmethyl)(methyl)amino)ethyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(2-(methyl(neopentyl)amino)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(2-(cyclohexyl(methyl)amino)ethyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(methyl((tetrahydro-2H-pyran-4-yl)methyl)amino)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(methylamino)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

2-(2-(benzyl(methyl)amino)ethyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(2-ethylbutyl)(methyl)amino)ethyl)amino)-4,5-difluoro-N-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-((cyclopropylmethyl)(methyl)amino)ethyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(2-(methyl((tetrahydro-2H-pyran-4-yl)methyl)amino)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-(2-(((1,4-dioxan-2-yl)methyl)(methyl)amino)ethyl)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(2-(methyl(2-(tetrahydro-2H-pyran-4-yl)ethyl)amino)ethyl)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(cyclopropylamino)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(cyclopropyl(ethyl)amino)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(2-((7-(N-(3-chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-1H-imidazo[4,5-b]pyridin-2-yl)amino)ethyl)acetamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(methylsulfonamido)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(cyclopropyl(isopropyl)amino)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(cyclopropyl(2-hydroxyethyl)amino)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-((2-aminoethyl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(((5-oxopyrrolidin-3-yl)methyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-(((1H-pyrazol-5-yl)methyl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-((7-(N-(3-chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-1H-imidazo[4,5-b]pyridin-2-yl)amino)propyl)acetamide,

2-((3-aminopropyl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(sulfamoylamino)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(phenylsulfonamido)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

Methyl (2-((7-(N-(3-chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-1H-imidazo[4,5-b]pyridin-2-yl)amino)ethyl)carbamate,

N-(3-chloro-4-fluorophenyl)-2-((2-(cyclopropanesulfonamido)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-((trifluoromethyl)sulfonamido)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-(((1H-imidazol-2-yl)methyl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-(((1H-imidazol-5-yl)methyl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(((3-methyl-1,2,4-oxadiazol-5-yl)methyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-bromophenyl)-N′-hydroxy-2-(methylamino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

Methyl (3-((7-(N-(3-chloro-4-fluorophenyl)-N′-hydroxycarbamimidoyl)-1H-imidazo[4,5-b]pyridin-2-yl)amino)propyl)carbamate,

N-(3-bromophenyl)-N′-hydroxy-2-methoxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-bromophenyl)-N′-hydroxy-2-(((2-(methylsulfonyl)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-bromophenyl)-N′-hydroxy-2-(((2-(methylsulfonamido)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-bromophenyl)-N′-hydroxy-2-(((2-sulfamoylethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(((5-methyl-1,3,4-oxadiazol-2-yl)methyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(((1-methylpiperidin-2-yl)methyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(((4-methylmorpholin-3-yl)methyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-bromophenyl)-2-((2-(dimethylamino)ethyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chlorophenyl)-2-((2-(dimethylamino)ethyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-bromo-4-fluorophenyl)-2-((2-(dimethylamino)ethyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-2-((3-morpholinopropyl)amino)-1H-benzo[d]imidazole-7-carboxamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((3-(pyrrolidin-1-yl)propyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

2-(((3R)-4-amino-1-methylpyrrolidin-3-yl)amino)-N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(dimethylamino)-2-phenylethyl)amino)-4,5-difluoro-N-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(((1R,2R)-2-(dimethylamino)cyclohexyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(((1-(dimethylamino)cyclopentyl)methyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(((1S,3S)-3-(dimethylamino)cyclohexyl)amino)-4,5-difluoro-N-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(((1S,3R)-3-(dimethylamino)cyclohexyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(((1-(dimethylamino)cyclobutyl)methyl)amino)-4,5-difluoro-N-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((1-methylpiperidin-4-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((1-methylpiperidin-3-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(((1S,2S)-2-(dimethylamino)cyclohexyl)amino)-4,5-difluoro-N-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

(S)—N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(piperidin-3-ylamino)-1H-benzo[d]imidazole-7-carboximidamide,

(R)—N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(piperidin-3-ylamino)-1H-benzo[d]imidazole-7-carboximidamide,

(S)—N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(((1-methylpyrrolidin-3-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((3-(dimethylamino)-2-hydroxypropyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(4-methyl-3-oxopiperazin-l-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(((1-(dimethylamino)cyclohexyl)methyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((1-methylazepan-3-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

(S)—N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(((2-(3-hydroxypyrrolidin-l-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((1-(2-methoxyethyl)piperidin-3-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((1-(2-methoxyethyl)pyrrolidin-3-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((1-isopropylpiperidin-3-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(3-methoxyazetidin-l-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

(R)—N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((1-methylpyrrolidin-3-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(((3R,4R)-4-methoxy-1-methylpyrrolidin-3-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

(S)—N-(3-chlorophenyl)-4,5-difluoro-N′-hydroxy-2-((1-methylpiperidin-3-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

(R)—N-(3-chlorophenyl)-4,5-difluoro-N′-hydroxy-2-((1-methylpiperidin-3-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(dimethylamino)cyclopentyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

(S)-2-(azepan-3-ylamino)-N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

(R)-2-(azepan-3-ylamino)-N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(pyrrolidin-3-ylamino)-1H-benzo[d]imidazole-7-carboximidamide,

(R)—N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((1-(oxetan-3-yl)piperidin-3-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(((1,4-dimethylpiperidin-2-yl)methyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((morpholin-3-ylmethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(((3R,4S)-4-hydroxypyrrolidin-3-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(((1R,5R)-8-methyl-8-azabicyclo[3.2.1]octan-2-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

(S)—N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-(((2-(2-(trifluoromethyl)pyrrolidin-1-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-2-(((hexahydro-1H-pyrrolizin-7a-yl)methyl)amino)-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(((3,3-dimethylazetidin-2-yl)methyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((4-(pyrrolidin-1-yl)tetrahydro-2H-pyran-3-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

2-(((1S,2R)-2-aminocyclohexyl)amino)-N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(((3S,4S)-4-(diethylamino)tetrahydrofuran-3-yl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

2-((1,4-oxazepan-6-yl)amino)-N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-((2S,6R)-2,6-dimethylmorpholino)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(((3R,4R)-4-methoxy-1-methylpyrrolidin-3-yl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(((3R,4R)-4-(diethylamino)tetrahydrofuran-3-yl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

(S)—N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(((2-(2-(trifluoromethyl)pyrrolidin-1-yl)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

(R)—N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-(((4-methylmorpholin-3-yl)methyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(2,6-dimethylmorpholino)propyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(2,6-dimethylmorpholino)-2-methylpropyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(2,5-dimethylmorpholino)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(((1R,2R)-2-(dimethylamino)cyclopentyl)amino)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(dimethylamino)ethyl)thio)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(dimethylamino)ethyl)thio)-4,5-difluoro-N′-hydroxy-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(2-(hydroxymethyl)piperidin-l-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(2-(hydroxymethyl)pyrrolidin-l-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(3,3-difluoropyrrolidin-l-yl)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-sulfamoylethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(methylsulfonyl)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((pyrimidin-2-ylmethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

(R)—N-(3-chlorophenyl)-4,5-difluoro-N′-hydroxy-2-((1-(2-methoxyethyl)pyrrolidin-3-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

(R)—N-(3-bromophenyl)-4,5-difluoro-N′-hydroxy-2-((1-(2-methoxyethyl)pyrrolidin-3-yl)amino)-1H-benzo[d]imidazole-7-carboximidamide,

(S)—N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((1-(oxetan-3-yl)piperidin-3-yl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((1-(2-methoxyethyl)piperidin-3-yl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((1-cyclopropylpyrrolidin-3-yl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

(R)—N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((1-(oxetan-3-yl)piperidin-3-yl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((2-(4-methyl-3-oxopiperazin-1-yl)ethyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((2-(3,3-difluoropiperidin-1-yl)ethyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

2-((1-acetylpyrrolidin-3-yl)amino)-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((1-(methylsulfonyl)pyrrolidin-3-yl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((3-(methylsulfonyl)propyl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-(((1,1-dioxidotetrahydrothiophen-3-yl)methyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide,

N-(3-chloro-4-fluorophenyl)-2-((3-((4-fluorophenyl)sulfonyl)propyl)amino)-N′-hydroxy-1H-imidazo[4,5-b]pyridine-7-carboximidamide, and

(R)—N-(3-chloro-4-fluorophenyl)-N′-hydroxy-2-((1-(oxetan-3-yl)pyrrolidin-3-yl)amino)-1H-imidazo[4,5-b]pyridine-7-carboximidamide;

or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

16. A pharmaceutical composition comprising a compound of claim 1 or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof, and at least one pharmaceutically acceptable vehicle.

17. The compound of claim 1 , selected from the group consisting of:

N-(3-chloro-4-fluorophenyl)-2-[2-(dimethylamino)ethylamino]-6,7-difluoro-N′-hydroxy-3H-benzimidazole-4-carboximidamide;

N-(3-bromophenyl)-N′-hydroxy-3H-imidazo[4,5-b]pyridine-7-carboximidamide;

N-(3-bromo-4-fluorophenyl)-N′-hydroxy-3H-imidazo[4,5-b]pyridine-7-carboximidamide;

N-(3-chlorophenyl)-N′-hydroxy-3H-imidazo[4,5-b]pyridine-7-carboximidamide; and

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(2-(hydroxymethyl)pyrrolidin-l-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide;

or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

18. A method of inhibiting an IDO1 protein in a patient having a disease, wherein the disease is responsive to IDO1 protein inhibition, comprising administering a compound of claim 1 , or a pharmaceutically acceptable salt thereof.

19. A method of inhibiting an IDO1 protein in a patient afflicted with a disease, wherein the disease is responsive to IDO1 protein inhibition, comprising administering a compound selected from the group consisting of:

N-(3-chloro-4-fluorophenyl)-2-[2-(dimethylamino)ethylamino]-6,7-difluoro-N′-hydroxy-3H-benzimidazole-4-carboximidamide;

N-(3-bromophenyl)-N′-hydroxy-3H-imidazo[4,5-b]pyridine-7-carboximidamide;

N-(3-bromo-4-fluorophenyl)-N′-hydroxy-3H-imidazo[4,5-b]pyridine-7-carboximidamide;

N-(3-chlorophenyl)-N′-hydroxy-3H-imidazo[4,5-b]pyridine-7-carboximidamide; and

N-(3-chloro-4-fluorophenyl)-4,5-difluoro-N′-hydroxy-2-((2-(2-(hydroxymethyl)pyrrolidin-l-yl)ethyl)amino)-1H-benzo[d]imidazole-7-carboximidamide;

or a pharmaceutically acceptable salt, tautomer, optical isomer, stereoisomer, or mixture thereof.

20. The method of claim 18 , wherein the disease is cancer.

21. The method of claim 19 , wherein the disease is cancer.

22. The method of claim 18 , further comprising administering to the subject at least one additional therapeutic agent selected from the group consisting of PD1 inhibitors and/or PD-L1 inhibitors.

23. The method of claim 19 , further comprising administering to the subject at least one additional therapeutic agent selected from the group consisting of PD1 inhibitors and/or PD-L1 inhibitors.

Assignments (2)
CORRECTIVE ASSIGNMENT TO CORRECT THE FIRST ASSIGNOR NAME PREVIOUSLY RECORDED AT REEL: 038749 FRAME: 0484. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT . Recorded Sep 7, 2016
From: BARTLETT, MARK J.; CODELLI, JULIAN ANDREW; CORKEY, BRITTON KENNETH; COSMAN, JENNIFER LEIGH; ELBEL, KRISTYNA; LOYER-DREW, JENNIFER ALISSA; SPERANDIO, DAVID; VELDHUIZEN, JOSHUA VAN; YANG, HAI; YEUNG, SUET CHUNG
To: GILEAD SCIENCES, INC.
Reel/Frame 039939/0834 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 31, 2016
From: BARLETT, MARK J.; CODELLI, JULIAN ANDREW; CORKEY, BRITTON KENNETH; COSMAN, JENNIFER LEIGH; ELBEL, KRISTYNA; LOYER-DREW, JENNIFER ALISSA; SPERANDIO, DAVID; VAN VELDHUIZEN, JOSHUA; YANG, HAI; YEUNG, SUET CHUNG
To: GILEAD SCIENCES, INC.
Reel/Frame 038749/0484 →
Continuity (2)
Provisional Application 62162531 · May 15, 2015
Related Publication 20160333009A1 · Nov 17, 2016