Granted Patent B2

US 12,264,156 · App. 17/252,146 · Granted Apr 1, 2025

Inventors: David Amantini (Romainville, FR); Reginald Christophe Xavier Brys (Mechelen, BE); Denis Bucher (Rheinfelden, CH); Steve Irma Joel De Vos (Mechelen, BE); Nicolas Desroy (Romainville, FR); Agnès Marie Joncour (Romainville, FR); Christophe Peixoto (Romainville, FR); Taoues Temal-Laïb (Romainville, FR); Amynata Tirera (Romainville, FR)

Assignee: GALAPAGOS NV

C07D471/04A61P1/00A61P17/06A61P19/02

Abstract

Claims (535)

1. A compound according to Formula I:

wherein,

X is N or CH;

Y is N or CR 2 b;

Z is

—NHR 3a ,

N-linked 4-7 membered heterocycloalkyl further having zero, one, or two additional heteroatoms independently selected from N, O, and S, optionally substituted with one or more independently selected R 15 groups, or

—NR 3b —, wherein the N atom and R 2a together with the atoms onto which they are attached form a fused 5-6 membered heterocycloalkenyl comprising one or two double bonds;

R 1 is

C 1-8 alkyl optionally substituted with one or more independently selected R 4 groups,

phenyl,

C 3-8 monocyclic or bridged polycyclic cycloalkyl optionally substituted with one or more independently selected R 5 groups,

4-8 membered monocyclic, spirocyclic, or bridged polycyclic heterocycloalkyl having one, two, or three heteroatoms independently selected from N, O, and S, which heterocycloalkyl is optionally substituted with one or more independently selected C 1-4 alkyl optionally substituted with one or more independently selected —CN or C(═O)—C 1-4 alkoxy, or

5-6 membered monocyclic heteroaryl having one, two, or three heteroatoms independently selected from N, O, and S;

R 2a and R 2b are independently selected from

halo,

C 1-4 alkyl,

C 1-4 alkoxy optionally substituted with one or more independently selected halo or C 1-4 alkoxy, and

NR 6a R 6b ;

R 3a is

C 1-6 alkyl optionally substituted with one or more independently selected halo or —CN, or

C 3-7 cycloalkyl optionally substituted with one or more independently selected halo or —OH;

R 3b is selected from H, C 3-7 cycloalkyl and C 1-6 alkyl optionally substituted with one or more independently selected halo or —CN;

each R 4 is independently selected from

halo,

—OH,

—CN,

phenyl,

—C(═O)OH,

—O—C(═O)—C 1-4 alkyl,

—O—S(═O) 2 —C 1-4 alkyl,

C 1-4 alkoxy optionally substituted with one or more independently selected

—OH

C 1-4 alkoxy,

4-8 membered monocyclic heterocycloalkyl having one, two, or three heteroatoms independently selected from N, O, and S, which heterocycloalkyl is optionally substituted with one or more independently selected C 1-4 alkyl, or

NR 7a R 7b , wherein each R 7a and R 7b is independently selected from H and C 1-4 alkyl,

C 3-7 cycloalkyl optionally substituted with one or more independently selected halo, —C(═O)—C 1-4 alkoxy, —NR 8a R 8b , or C 1-4 alkyl optionally substituted with one or more independently selected —NR 9a R 9b ,

5-6 membered monocyclic heterocycloalkyl comprising one or two N atoms fused to a 5-6 membered monocyclic heteroaryl having one, two, or three heteroatoms independently selected from N, O, and S, which heteroaryl is optionally substituted with one or more independently selected C 1-4 alkyl,

5-6 membered monocyclic heteroaryl having one, two, or three heteroatoms independently selected from N, O, and S, which heteroaryl is optionally substituted with one or more independently selected C 1-4 alkyl or C 3-7 cycloalkyl,

4-1l membered monocyclic, spirocyclic, or bridged polycyclic heterocycloalkyl having one, two, or three heteroatoms independently selected from N, O, and S, which heterocycloalkyl is optionally substituted with one or more independently selected R 10 ,

—NR 11a R 11b ,

—C(═O)—C 1-4 alkoxy, and

—C(═O)—NR 12a R 12b ;

each R is selected from

halo,

—CN, and

—N 13a R 13b ;

each R 6a and R 5b is independently selected from H and C 1-4 alkyl;

each R 10 is selected from

—OH,

phenyl,

═NH,

halo,

oxo,

—CN,

—C(═O)H,

C(═O)NH 2 ,

—C(═O)OH,

NR 14a R 14b ,

C 1-4 alkyl optionally substituted with one or more independently selected halo, —CN, —OH, —C(═O)—C 1-4 alkoxy, or C 1-4 alkoxy,

C 3-7 cycloalkyl,

4-6 membered monocyclic heterocycloalkyl having one, two, or three heteroatoms independently selected from N, O, and S,

—C(═O)—C 1-4 alkyl,

—S(═O) 2 —C 1-4 alkyl, and

—C(═O)—C 1-6 alkoxy;

each R 11a , R 11b is independently selected from

—H,

phenyl,

C 1-4 alkyl optionally substituted with one or more independently selected halo, —OH, —CN, or C 1-4 alkoxy,

C 3-7 cycloalkyl,

—C(═O)—C 1-4 alkoxy,

—C(═O)—C 1-4 alkyl optionally substituted with one or more independently selected halo, and

5-6 membered monocyclic heteroaryl having one, two, or three heteroatoms independently selected from N, O, and S;

each R 8a , R 8b , R 9a , R 9b , R 12a , R 12b R 13a , and R 13b is independently selected from H and C 1-4 alkyl;

each R 14a and R 14b is independently selected from 1, C 1-4 alkyl, and —S(═O) 2 —C 1-4 alkyl; and

each R 15 is independently selected from —OH, —CN, and C 1-4 alkyl optionally substituted with one or more independently selected halo or —CN.

2. A compound or pharmaceutically acceptable salt thereof, according to claim 1 , wherein

Z is

—NHR 3a , or

—NR 3b —, wherein the N atom and R 2a together with the atoms onto which they are attached form a fused 5-6 membered heterocycloalkenyl comprising one or two double bonds;

R 1 is

C 1-8 alkyl optionally substituted with one or more independently selected R 4 groups,

phenyl,

C 3-8 monocyclic or bridged polycyclic cycloalkyl optionally substituted with one or more independently selected R 5 groups,

4-8 membered monocyclic or spirocyclic heterocycloalkyl having one, two, or three heteroatoms independently selected from N, O, and S, which heterocycloalkyl is optionally substituted with one or more independently selected C 1-4 alkyl, or

5-6 membered monocyclic heteroaryl having one, two, or three heteroatoms independently selected from N, O, and S;

R 3a is

C 1-6 alkyl optionally substituted with one or more independently selected halo or —CN, or

C 3-7 cycloalkyl;

each R 4 is independently selected from

halo,

—OH,

—CN,

phenyl,

C 1-4 alkoxy optionally substituted with one or more independently selected —OH, C 1-4 alkoxy, or —NR 7a R 7b , wherein each R 7a and R 7b is independently selected from H and C 1-4 alkyl,

C 3-7 cycloalkyl optionally substituted with one or more independently selected halo, —C(═O)—C 1-4 alkoxy, —NR 8a R 8b , or C 1-4 alkyl optionally substituted with one or more independently selected —NR 9a R 9b ,

5-6 membered monocyclic heteroaryl having one, two, or three heteroatoms independently selected from N, O, and S, which heteroaryl is optionally substituted with one or more independently selected C 1-4 alkyl or C 3-7 cycloalkyl,

4-8 membered monocyclic or bridged polycyclic heterocycloalkyl having one, two, or three heteroatoms independently selected from N, O, and S, which heterocycloalkyl is optionally substituted with one or more independently selected R 10 ,

—NR 11a R 11b , and

—C(═O)—NR 12a R 12b ;

each R 10 is selected from

halo,

oxo,

—CN,

—C(═O)H,

—NR 14a R 14b ,

C 1-4 alkyl optionally substituted with one or more independently selected halo or C 1-4 alkoxy,

C 3-7 cycloalkyl,

—C(═O)—(C 1-4 alkyl,

—S(═O)—C 1-4 alkyl, and

—C(═O)—C 1-6 alkoxy;

each R 11a , R 11b is independently selected from

H,

phenyl,

C 1-4 alkyl optionally substituted with one or more independently selected halo, —OH, —CN, or C 1-4 alkoxy,

C 3-7 cycloalkyl,

—C(═O)— C 1-4 alkyl, and

5-6 membered monocyclic heteroaryl having one, two, or three heteroatoms independently selected from N, O, and S; and

each R 14a , and R 14b is independently selected from H and C 1-4 alkyl.

3. A compound or pharmaceutically acceptable salt thereof, according to claim 1 , wherein X is CH.

4. A compound or pharmaceutically acceptable salt thereof, according to claim 1 , wherein Y is CR 2b and R 2b is C 1-4 alkoxy.

5. A compound or pharmaceutically acceptable salt thereof, according to claim 1 , wherein R 2a is —O—CH 3 , substituted with one, two, or three independently selected halo.

6. A compound or pharmaceutically acceptable salt thereof, according to claim 1 , wherein Z is —NR 3b —, wherein the N atom and R 2a together with the atoms onto which they are attached form a fused 1,2,3,6-tetrahydropyridine.

7. A compound or pharmaceutically acceptable salt thereof, according to claim 1 , wherein the compound is according to any one of Formulae IIIa-IIIc:

8. A compound or pharmaceutically acceptable salt thereof, according to claim 1 , wherein R 1 is —CH 3 or —CH 2 CH 3 , each of which is substituted with one R 4 group.

9. A compound or pharmaceutically acceptable salt thereof, according to claim 1 , wherein the compound is according to any one of Formulae IVa-IVf:

10. A compound or pharmaceutically acceptable salt thereof, according to claim 1 , wherein R 4 is —NH—CH 3 , —N(CH 3 ) 2 , —NH—CH 2 CH 3 , —N(CH 2 CH 3 ) 2 , —N(CH(CH 3 ) 2 ) 2 , or —N(CH 3 )—CH 2 CHF 2 .

11. A compound or pharmaceutically acceptable salt thereof, according to claim 1 , wherein R 4 is azetidinyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl, piperidinyl, tetrahydropyranyl, morpholinyl, dioxanyl, 2-oxa-5-azabicyclo[2.2.1]heptanyl, 3-oxa-8-azabicyclo[3.2.1]octanyl, or 8-oxa-3-azabicyclo[3.2.1]octanyl.

12. A compound or pharmaceutically acceptable salt thereof, according to claim 1 , wherein R 4 is morpholinyl.

13. A compound or pharmaceutically acceptable salt thereof, according to claim 1 , wherein R 4 is dioxanyl.

14. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a pharmaceutically effective amount of a compound or pharmaceutically acceptable salt thereof according to claim 1 .

15. A method for treatment of inflammatory diseases, fibrotic diseases, diseases involving impairment of cartilage turnover, diseases involving impairment of bone turnover, systemic lupus erythematosus, cancer, psoriasis, and/or inflammatory bowel diseases, comprising administering an effective amount of the compound or pharmaceutically acceptable salt thereof, according to claim 1 .

16. A method for treatment of inflammatory diseases, fibrotic diseases, diseases involving impairment of cartilage turnover, diseases involving impairment of bone turnover, systemic lupus erythematosus, cancer, psoriasis, and/or inflammatory bowel diseases, comprising administering a pharmaceutical composition according to claim 14 .

17. The compound of claim 1 , wherein the compound is

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-(7-tetrahydropyran-4-yloxyimidazo[1,2-a]pyridin-3-yl)benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(1-methyl-3-piperidyl)oxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(2-methoxy-2-methyl-propoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

2,6-dimethoxy-4-(7-tetrahydropyran-4-yloxyimidazo[1,2-a]pyridin-3-yl)-N-(2,2,2-trifluoroethyl)benzamide,

2,6-dimethoxy-4-[7-[(1-methyl-3-piperidyl)oxy]imidazo[1,2-a]pyridin-3-yl]-N-(2,2,2-trifluoroethyl)benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(1-methyl-4-piperidyl)oxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(4-methylpiperazin-1-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(1-piperidyl)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(2-methyl-2-morpholino-propoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(1-methyl-2-morpholino-ethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(dimethylamino)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(1-methylazetidin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(1-methylpyrrolidin-3-yl)oxyimidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(1-methylpyrrolidin-2-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

6-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-8-methoxy-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(3-methylimidazol-4-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(2-pyrrolidin-1-ylethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(3-morpholinopropoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(1,1-dioxo-1,4-thiazinan-4-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(1-methyl-2-piperidyl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(1-methyl-2-piperidyl)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(1-methyl-4-piperidyl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(1-methyl-5-oxo-pyrrolidin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

4-[7-(2-acetamidoethoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(1-methylpyrrolidin-2-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(1-methylazetidin-3-yl)oxyimidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-(2-hydroxyethoxy)imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

4-[7-(2-cyanoethoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(oxazol-2-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(oxazol-5-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

4-[7-(2-cyano-2-methyl-propoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(oxetan-2-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-(2-fluoroethoxy)imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(ethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(2-methoxyethoxy)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

8-methoxy-6-[7-[(1-methylazetidin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

8-methoxy-6-[7-[2-(1-piperidyl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

6-[7-[2-(1,1-dioxo-1,4-thiazinan-4-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-8-methoxy-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

N-cyclopropyl-4-[7-[(2,2-difluorocyclopropyl)methoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(3-pyridylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(2-methylpyrazol-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(2,2,2-trifluoro-1-methyl-ethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(thiazol-4-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(thiazol-2-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(tetrahydropyran-2-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(tetrahydropyran-4-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[[(2R)-1,4-dioxan-2-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-4-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-fluoro-6-methoxy-benzamide,

N-cyclopropyl-4-[7-[(3,3-difluorocyclobutyl)methoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

6-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-ethyl-8-methoxy-3,4-dihydroisoquinolin-1-one,

2-(2,2-difluoroethyl)-6-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-8-methoxy-3,4-dihydroisoquinolin-1-one,

8-methoxy-6-[7-(3-morpholinopropoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

N-cyclopropyl-4-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2-ethoxyethoxy)-6-methoxy-benzamide,

methyl 1-[[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxymethyl]cyclopropanecarboxylate,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-(7-norbornan-2-yloxyimidazo[1,2-a]pyridin-3-yl)benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(tetrahydropyran-3-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(oxazol-4-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

4-[7-(cyclopentylmethoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-4-[7-(3,3-difluorocyclopentoxy)imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(2-oxopyrrolidin-1-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(2-tetrahydropyran-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-[2-(dimethylamino)ethoxy]ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-(2,2-dimethylpropoxy)imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

2-[6-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-8-methoxy-1-oxo-3,4-dihydroisoquinolin-2-yl]acetonitrile,

4-(7-benzyloxyimidazo[1,2-a]pyridin-3-yl)-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-(cyclohexylmethoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

4-[7-(cyclobutylmethoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-(2-ethoxyethoxy)imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(2-hydroxyethoxy)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-(3-hydroxy-2,2-dimethyl-propoxy)imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-4-[7-[(3,3-difluorocyclopentyl)methoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-4-[7-[2-(3,3-difluorocyclobutyl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-4-[7-(4,4-difluorocyclohexoxy)imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(diisopropylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-4-[7-[[(2R)-1-(2,2-difluoroethyl)pyrrolidin-2-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[[(2R)-1-methylpyrrolidin-2-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(4-methylmorpholin-2-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[(1-ethyl-2-piperidyl)methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

8-methoxy-6-[7-[(2-methylpyrazol-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

8-methoxy-6-[7-[(3-methylimidazol-4-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

6-[7-[[(2R)-1,4-dioxan-2-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-8-methoxy-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

tert-butyl 2-[[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxymethyl]azetidine-1-carboxylate,

8-methoxy-6-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(3-methyloxetan-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-4-[7-(2,2-difluoroethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(2,2,2-trifluoroethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(tetrahydrofuran-3-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(tetrahydrofuran-2-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(pyrimidin-2-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(thiazol-5-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-4-[7-(cyclopropylmethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(1-methylcyclopropyl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-(1,4-dioxan-2-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(5-oxopyrrolidin-2-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(dimethylamino)-2-oxo-ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(1-methylimidazol-4-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(5-oxopyrrolidin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(4-pyridylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

4-[7-(2-amino-2-methyl-propoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(2-pyridylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(dimethylamino)-2-methyl-propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-4-[7-[2-(diethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-[(3-aminocyclobutyl)methoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-(azetidin-2-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(1-methylimidazol-2-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[[(2R)-1-methyl-2-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

4-[7-[2-(azetidin-1-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(morpholin-3-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(2-hydroxyethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

4-[7-(3-aminopropoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-[[1-(aminomethyl)cyclobutyl]methoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(methylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

4-[7-(2-aminoethoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(2-piperidylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[[(2S)-1,4-dioxan-2-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

4-[7-(2-amino-3-methyl-butoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

8-methoxy-6-[7-[2-(1-methylpyrrolidin-2-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

8-methoxy-6-[7-(2-pyrrolidin-1-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

8-methoxy-6-[7-[[(2R)-1-methylpyrrolidin-2-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

8-methoxy-6-[7-(oxetan-2-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

8-methoxy-6-[7-(oxazol-5-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

8-methoxy-6-[7-[(4-methylmorpholin-2-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

6-[7-[2-(diethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-8-methoxy-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(1-methylsulfonyl-2-piperidyl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

methyl 2-[[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxymethyl]piperidine-1-carboxylate,

4-[7-(2-aminobutoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-[(2S)-2-amino-4-methyl-pentoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-[(2S)-2-amino-2-cyclohexyl-ethoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-(2-amino-2-tetrahydrofuran-3-yl-ethoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-(2-amino-2-tetrahydropyran-4-yl-ethoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-(2-amino-2-tetrahydrofuran-2-yl-ethoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-(2-amino-2-cyclopropyl-ethoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-(2-aminopropoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[[(2S)-1-methyl-2-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

6-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-8-ethoxy-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

4-[7-[(1-acetyl-2-piperidyl)methoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[(1-formyl-3-piperidyl)methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(3-piperidylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(1-methylpyrrolidin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(2-pyridyloxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-fluoro-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-(methylamino)benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[(1-isopropyl-2-piperidyl)methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-4-[7-[[1-(2,2-difluoroethyl)-2-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

2-(2,2-difluoroethyl)-8-(difluoromethoxy)-6-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-3,4-dihydroisoquinolin-1-one,

4-[7-(cyclobutoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(oxetan-3-yloxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-methyl-2-(methylamino)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(pyrrolidin-2-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

2-(difluoromethoxy)-4-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-fluoro-N-(2,2,2-trifluoroethyl)benzamide,

N-cyclopropyl-2,6-bis(difluoromethoxy)-4-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-(7-phenoxyimidazo[1,2-a]pyridin-3-yl)benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-[2-(methoxymethyl)morpholin-4-yl]ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

4-(7-benzyloxyimidazo[1,2-c]pyrimidin-3-yl)-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-[(3S)-3-fluoropyrrolidin-1-yl]ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(methylamino)cyclobutoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(2-oxaspiro[3.3]heptan-6-yloxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-(7-tetrahydrofuran-3-yloxyimidazo[1,2-a]pyridin-3-yl)benzamide,

4-[7-(3-cyanocyclobutoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

2-(difluoromethoxy)-4-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-(methylamino)-N-(2,2,2-trifluoroethyl)benzamide,

2-(difluoromethoxy)-4-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-N-(2,2,2-trifluoroethyl)benzamide,

6-[7-[2-(dimethylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-8-(methylamino)-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(2-methylpyrrolidin-2-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

4-[7-[(1-aminocyclohexyl)methoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-[(3-aminooxetan-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-[(1-aminocyclopropyl)methoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(2-methyl-2-piperidyl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[(1-ethylimidazol-2-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

4-[7-[(1-aminocyclobutyl)methoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[(1-isopropylimidazol-2-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

4-[7-[(3-aminotetrahydrofuran-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(2,6-dimethylmorpholin-4-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

4-[7-[2-(3-cyanomorpholin-4-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-[2-(trifluoromethyl)morpholin-4-yl]ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(3,3-difluoropyrrolidin-1-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(4,4-difluoro-1-piperidyl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[[1-(2,2,2-trifluoroethyl)-2-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-[methyl(2-pyridyl)amino]ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(N-methylanilino)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

8-methoxy-6-[7-[2-(methylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

N-cyclopropyl-4-[7-[2-(3,3-difluoroazetidin-1-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

tert-butyl 3-[[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxymethyl]-3-fluoro-azetidine-1-carboxylate,

tert-butyl 3-[[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxymethyl]-3-methyl-azetidine-1-carboxylate,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[[(2S)-4,4-difluoro-1-methyl-pyrrolidin-2-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

8-methoxy-6-[7-[[(2R)-4-methylmorpholin-2-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

8-methoxy-6-[7-[[(2S)-4-methylmorpholin-2-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(3,3-dimethylmorpholin-4-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(2,2-dimethylmorpholin-4-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-4-[7-[2-(2-cyclopropylmorpholin-4-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

2-cyclopropyl-8-methoxy-6-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]-3,4-dihydroisoquinolin-1-one,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[(2,5-dimethylpyrazol-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(1-methylpyrazol-4-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(1-methylpyrazol-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(4-methylmorpholin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(dimethylamino)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(dimethylamino)butoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(1-methylpyrazol-4-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-4-[7-[(5-cyclopropyl-1,3,4-oxadiazol-2-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[(3-fluoroazetidin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(3-methylazetidin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-(2-hydroxy-1,1-dimethyl-ethoxy)imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

8-methoxy-6-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]-2H-isoquinolin-1-one,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(3,3-difluoro-1-piperidyl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(3-fluoro-1-piperidyl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

4-[7-[2-(2-cyanomorpholin-4-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(2-methylmorpholin-4-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

4-[7-[2-[cyanomethyl(methyl)amino]ethoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-[2-(3-cyano-1-piperidyl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

8-methoxy-6-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]-3,4-dihydro-2H-isoquinolin-1-one,

2-(2,2-difluoroethyl)-8-methoxy-6-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]-3,4-dihydroisoquinolin-1-one,

2-(2,2-difluoroethyl)-6-[7-[[(2R)-1,4-dioxan-2-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-8-methoxy-3,4-dihydroisoquinolin-1-one,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[(1,3-dimethylazetidin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

8-methoxy-6-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)isoquinolin-1-one,

N-cyclopropyl-2-methoxy-6-methyl-4-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-[methyl(4-pyridyl)amino]ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

2-cyclopropyl-8-(difluoromethoxy)-6-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]-3,4-dihydroisoquinolin-1-one,

6-[7-[[(2S)-1,4-dioxan-2-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-8-methoxy-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(pyridazin-3-ylmethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(4-methyl-1,2,4-triazol-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(3-methyl-2-oxo-oxazolidin-5-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(3-methyl-1,2,4-oxadiazol-5-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

2-(difluoromethoxy)-6-methoxy-4-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]-N-(2,2,2-trifluoroethyl)benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[(5-methyl-1,2,4-oxadiazol-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(3-methylmorpholin-4-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-[(3S)-3-methylmorpholin-4-yl]ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-[(3R)-3-methylmorpholin-4-yl]ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-4-[7-[2-[cyclopropyl(2,2-difluoroethyl)amino]ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-4-[7-[2-[2,2-difluoroethyl(methyl)amino]ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-4-[7-[2-[2,2-difluoroethyl(2-methoxyethyl)amino]ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-[methyl(pyrimidin-2-yl)amino]ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-[methyl(pyrimidin-4-yl)amino]ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-[methyl(pyridazin-4-yl)amino]ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methyl-4-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

6-[7-[[(2R)-1,4-dioxan-2-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-8-methoxy-3,4-dihydro-2H-isoquinolin-1-one,

2-(difluoromethoxy)-6-methyl-4-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]-N-(2,2,2-trifluoroethyl)benzamide,

6-[7-[2-(3,3-difluoroazetidin-1-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-8-methoxy-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

8-methoxy-6-[7-[2-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

8-methoxy-6-[7-[2-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

2-(2,2-difluoroethyl)-8-(difluoromethoxy)-6-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]-3,4-dihydroisoquinolin-1-one,

tert-butyl 3-fluoro-3-[[3-[8-methoxy-1-oxo-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-6-yl]imidazo[1,2-a]pyridin-7-yl]oxymethyl]azetidine-1-carboxylate,

tert-butyl 3-[[3-[8-methoxy-1-oxo-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-6-yl]imidazo[1,2-a]pyridin-7-yl]oxymethyl]-3-methyl-azetidine-1-carboxylate,

6-[7-[(3-fluoroazetidin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-8-methoxy-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

8-methoxy-6-[7-[(3-methylazetidin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

6-[7-[(3-fluoro-1-methyl-azetidin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-8-methoxy-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

6-[7-[(1,3-dimethylazetidin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-8-methoxy-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

N-cyclopropyl-3-methoxy-5-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]pyridine-2-carboxamide,

4-[7-(1-cyanocyclopentoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

8-methoxy-6-(7-methoxyimidazo[1,2-a]pyridin-3-yl)-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

8-methoxy-6-[7-[2-[(3S)-3-methylmorpholin-4-yl]ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

6-[7-(2-hydroxyethoxy)imidazo[1,2-a]pyridin-3-yl]-8-methoxy-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

8-methoxy-6-[7-[2-[(3R)-3-methylmorpholin-4-yl]ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(2-methoxy-1,1-dimethyl-ethoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

3-methoxy-5-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]-N-(2,2,2-trifluoroethyl)pyridine-2-carboxamide,

3-methoxy-5-[7-[(2-methylpyrazol-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-N-(2,2,2-trifluoroethyl)pyridine-2-carboxamide,

4-[7-(1-cyano-1-methyl-ethoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

6-(7-ethoxyimidazo[1,2-a]pyridin-3-yl)-8-methoxy-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one,

5-[7-[[(2R)-1,4-dioxan-2-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-3-methoxy-N-(2,2,2-trifluoroethyl)pyridine-2-carboxamide,

3-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]-6-(2,2,2-trifluoroethyl)-5H-pyrrolo[3,4-b]pyridin-7-one,

N-cyclopropyl-3-(difluoromethoxy)-5-[7-(2-morpholinoethoxy)imidazo[1,2-a]pyridin-3-yl]pyridine-2-carboxamide,

ethyl 2-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxyacetate,

4-[7-[[1-(cyanomethyl)-2-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-[[(1R,5S)-8-azabicyclo[3.2.1]octan-3-yl]oxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-[[(1S,5R)-8-(2-cyanoethyl)-8-azabicyclo[3.2.1]octan-3-yl]oxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

ethyl 2-[(1R,5S)-3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxy-8-azabicyclo[3.2.1]octan-8-yl]acetate,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(2-oxa-6-azaspiro[3.3]heptan-6-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

4-[7-[3-(azetidin-1-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(3-pyrrolidin-1-ylpropoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(4-isopropylpiperazin-1-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(4-hydroxy-1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-(3-piperazin-1-ylpropoxy)imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(4-isopropylpiperazin-1-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[(1-isopropyl-3-piperidyl)methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(8-oxa-5-azaspiro[3.5]nonan-5-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxypropyl acetate,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[(4-isopropylmorpholin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(2-oxa-7-azaspiro[3.4]octan-7-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(3-hydroxyazetidin-1-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[(1-isopropylpyrrolidin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[[1-(oxetan-3-yl)pyrrolidin-3-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[[1-(oxetan-3-yl)pyrrolidin-2-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(2,6-dimethyl-1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

4-[7-[3-(2-azaspiro[3.3]heptan-2-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(2,6-dimethyl-1-piperidyl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[(1-isopropylpyrrolidin-2-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(2,8-dioxa-5-azaspiro[3.5]nonan-5-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(6-hydroxy-2-azaspiro[3.3]heptan-2-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-[2-(4-isopropylpiperazin-1-yl)ethoxy]ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-[1-(oxetan-3-yl)pyrrolidin-2-yl]ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(6-oxa-1-azaspiro[3.3]heptan-1-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-(1-isopropylpyrrolidin-2-yl)ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

4-[7-[3-(1-azaspiro[3.3]heptan-1-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(2-oxa-8-azaspiro[3.5]nonan-8-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-[2-(1-piperidyl)ethoxy]ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(2-morpholinoethoxy)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-4-[7-[2-[2-(diethylamino)ethoxy]ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(1-methyl-6,7-dihydro-4H-imidazo[4,5-c]pyridin-5-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(3,4-dihydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(7,8-dihydro-5H-1,6-naphthyridin-6-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(6,8-dihydro-5H-imidazo[1,2-a]pyrazin-7-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(6,8-dihydro-5H-[1,2,4]triazolo[1,5-a]pyrazin-7-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[[(3S)-pyrrolidin-3-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[[(3S)-3-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[[(3S)-1-isopropylpyrrolidin-3-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[[(3S)-1-(oxetan-3-yl)pyrrolidin-3-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[[(3S)-1-(oxetan-3-yl)-3-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(3-hydroxypyrrolidin-1-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(2-methyl-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-hydroxy-3-(1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

4-[7-[[1-(cyanomethyl)azetidin-3-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-[[1-(2-cyanoethyl)azetidin-3-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(2-oxo-1-oxa-3, 8-diazaspiro[4.5]decan-8-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(3-methyl-2-oxo-1-oxa-3,8-diazaspiro[4.5]decan-8-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-[4-[methyl(methylsulfonyl)amino]-1-piperidyl]propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(1-imino-1-oxo-1,4-thiazinan-4-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(3-hydroxy-1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[[(3S)-1-isopropyl-3-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-(2-hydroxy-3-morpholino-propoxy)imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(1,1-dioxo-1,4-thiazinan-4-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(1,1-dioxo-1»{circumflex over ( )}{6}-thia-6-azaspiro[3.3]heptan-6-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxypropyl methanesulfonate,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[[(3R)-pyrrolidin-3-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[[(3R)-3-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[[(3R)-1-(oxetan-3-yl)pyrrolidin-3-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[[(3R)-1-isopropylpyrrolidin-3-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[[(3R)-1-isopropyl-3-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[[(3R)-1-(oxetan-3-yl)-3-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[[(3S)-1-(2-hydroxyethyl)-3-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[[(3S)-1-(2-hydroxyethyl)pyrrolidin-3-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[[1-(2-hydroxy-2-methyl-propyl)azetidin-3-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[[1-(2-hydroxyethyl)azetidin-3-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-4-[7-[3-(4,4-difluoro-3-hydroxy-1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-4-[7-[3-(3,3-difluoro-4-hydroxy-pyrrolidin-1-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-[3-(3-cyano-1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(4-methylsulfonyl-1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[[(3R)-1-(2-hydroxyethyl)pyrrolidin-3-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

4-[7-[[(3S)-1-(2-cyanoethyl)pyrrolidin-3-yl]methoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

4-[7-[[(3S)-1-(2-cyanoethyl)-3-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-[(2R,6S)-2,6-dimethyl-1-piperidyl]propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

2-(difluoromethoxy)-N-[(1S,2R)-2-hydroxycyclobutyl]-6-methoxy-4-[7-[3-(1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

2-(difluoromethoxy)-N-[(1R,2S)-2-hydroxycyclobutyl]-6-methoxy-4-[7-[3-(1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

[2-(difluoromethoxy)-6-methoxy-4-[7-[3-(1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]phenyl]-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone,

2-[1-[2-(difluoromethoxy)-6-methoxy-4-[7-[3-(1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzoyl]-3-hydroxy-azetidin-3-yl]acetonitrile,

N-(cyanomethyl)-2-(difluoromethoxy)-6-methoxy-4-[7-[3-(1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

1-[2-(difluoromethoxy)-6-methoxy-4-[7-[3-(1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzoyl]azetidine-3-carbonitrile,

[2-(difluoromethoxy)-6-methoxy-4-[7-[3-(1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]phenyl]-[3-(difluoromethyl)-3-hydroxy-azetidin-1-yl]methanone,

2-(difluoromethoxy)-N-[(1R,2R)-2-hydroxycyclobutyl]-6-methoxy-4-[7-[3-(1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

2-(difluoromethoxy)-N-[(1S,2S)-2-hydroxycyclobutyl]-6-methoxy-4-[7-[3-(1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-[4-fluoro-4-(hydroxymethyl)-1-piperidyl]propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

1-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxypropyl]-4-fluoro-piperidine-4-carboxamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(3-hydroxy-3-methyl-azetidin-1-yl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

ethyl 1-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxypropyl]-4-fluoro-piperidine-4-carboxylate,

4-[7-(3-amino-2,2-difluoro-propoxy)imidazo[1,2-a]pyridin-3-yl]-N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-benzamide,

methyl N-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxy-2,2-difluoro-propyl]carbamate,

1-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxypropyl]-4-fluoro-piperidine-4-carboxylic acid,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(2-pyridylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(pyrimidin-2-ylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-6-methoxy-4-[7-[2-(pyrimidin-4-ylamino)ethoxy]imidazo[1,2-a]pyridin-3-yl]benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[[(3R)-1-(2-hydroxyethyl)-3-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-4-[7-[2-[(2,2-difluoroacetyl)amino]ethoxy]imidazo[1,2-a]pyridin-3-yl]-2-(difluoromethoxy)-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[(3-hydroxy-1-isopropyl-pyrrolidin-3-yl)methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[[(3R,4S)-4-hydroxy-3-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[[(3S,4R)-4-hydroxy-3-piperidyl]methoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[3-(1,1-dioxo-1,4-thiazinan-4-yl)-2-hydroxy-propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-hydroxy-3-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-hydroxy-3-[(3R)-3-hydroxypyrrolidin-1-yl]propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

ethyl 1-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxypropyl]piperidine-4-carboxylate,

ethyl 1-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxypropyl]-4-phenyl-piperidine-4-carboxylate,

N-cyclopropyl-2-(difluoromethoxy)-4-[7-[2-hydroxy-3-(4-hydroxy-1-piperidyl)propoxy]imidazo[1,2-a]pyridin-3-yl]-6-methoxy-benzamide,

ethyl 1-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxypropyl]-4-methyl-piperidine-4-carboxylate,

ethyl 1-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxypropyl]-4-hydroxy-piperidine-4-carboxylate,

ethyl 1-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxy-2-hydroxy-propyl]-4-methyl-piperidine-4-carboxylate,

ethyl 1-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxy-2-hydroxy-propyl]-4-hydroxy-piperidine-4-carboxylate,

ethyl 1-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxy-2-hydroxy-propyl]-4-fluoro-piperidine-4-carboxylate,

ethyl 1-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxypropyl]-3-methyl-azetidine-3-carboxylate,

methyl (2S)-4-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxy-2-hydroxy-propyl]morpholine-2-carboxylate,

methyl (2S)-4-[2-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxyethyl]morpholine-2-carboxylate,

ethyl 1-[2-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxyethyl]-4-fluoro-piperidine-4-carboxylate,

tert-butyl 1-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxypropyl]azetidine-3-carboxylate,

ethyl 1-[2-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxyethyl]piperidine-3-carboxylate,

methyl 1-[2-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxyethyl]azetidine-3-carboxylate,

tert-butyl 1-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxy-2-hydroxy-propyl]azetidine-3-carboxylate,

ethyl 1-[3-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxypropyl]piperidine-3-carboxylate,

2-[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxyacetic acid, or

ethyl 2-[2-[[3-[4-(cyclopropylcarbamoyl)-3-(difluoromethoxy)-5-methoxy-phenyl]imidazo[1,2-a]pyridin-7-yl]oxymethyl]-1-piperidyl]acetate.

18. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a pharmaceutically effective amount of a compound or pharmaceutically acceptable salt thereof according to claim 17 .

19. A method for treatment of inflammatory diseases, fibrotic diseases, diseases involving impairment of cartilage turnover, diseases involving impairment of bone turnover, systemic lupus erythematosus, cancer, psoriasis, and/or inflammatory bowel diseases, comprising administering an effective amount of the compound or pharmaceutically acceptable salt thereof, according to claim 17 .

20. A method for treatment of inflammatory diseases, fibrotic diseases, diseases involving impairment of cartilage turnover, diseases involving impairment of bone turnover, systemic lupus erythematosus, cancer, psoriasis, and/or inflammatory bowel diseases, comprising administering a pharmaceutical composition according to claim 18 .

Assignments (6)

Priority Claims (2)

Continuity (1)

References Cited (60)