IP Library Granted Patent US 9,555,039
Granted Patent B2
US 9,555,039 · App. 14/115,849 · Granted Jan 31, 2017

Piperidine derivatives and compositions for the inhibition of nicotinamide phosphoribosyltransferase (NAMPT)

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Quick Facts
Patent No.
US 9,555,039
App. No.
14/115,849
Granted
Jan 31, 2017
Kind
B2
Abstract

The present invention relates to compounds and compositions for the inhibition of NAMPT, their synthesis, applications and antidotes. An illustrative compound of the invention is shown below: Formula (I)

Claims (327)

1. A compound of Formula II:

wherein

W is —C(O)—, —S(O)—, or —S(O) 2 —;

R is an aryl or bicyclic heteroaryl;

wherein said heteroaryl contains 1, 2, or 3 heteroatoms independently selected from N, S, and O, with the proviso that no two adjacent ring heteroatoms are both S or both O; and

each of said aryl or heteroaryl is optionally substituted with one or more substituents which can be the same or different and are independently selected from the group consisting of deuterium, halo, cyano, amino, aminoalkyl, (amino)alkoxy, —CONH 2 , —C(O)NH(alkyl), —C(O)N(alkyl) 2 , —C(O)NH(aryl), —C(O)N(aryl) 2 , —CF 3 , —CHF 2 , —CH 2 F, -alkyl, alkoxy, hydroxyl, hydroxyalkyl, (alkoxyalkyl)amino, —N(R 3 )—C(O)-alkyl, —N(R 3 )—C(O)-aryl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl, with the proviso that no two adjacent ring heteroatoms in said heteroaryl are both S or both O;

G is aryl, heteroaryl, cycloalkyl, heterocycloalkyl or —NR 1 R 2 ;

wherein each of said aryl, heteroaryl, heterocycloalkyl, and cycloalkyl is either unsubstituted or substituted with 1, 2, 3, or 4 substituents which can be the same or different and are independently selected from the group consisting of deuterium, halo, cyano, amino, aminoalkyl, (amino)alkoxy-, —CONH 2 , —C(O)NH(alkyl), —C(O)N(alkyl) 2 , —C(O)NH(aryl), —C(O)N(aryl) 2 , —CF 3 , —CHF 2 , —CH 2 F, alkyl, alkenyl, alkynyl, alkoxy, hydroxyl, hydroxyalkyl, aryloxy, (alkoxyalkyl)amino, —N(R 3 )—C(O)-alkyl, —N(R 3 )—C(O)-aryl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl; and

R 1 and R 2 are the same or they are different, and are independently selected from H, C 1 to C 7 alkyl, C 1 to C 7 alkoxy, C 1 to C 4 hydroxyalkyl, aryl, heteroaryl, heterocycloalkyl, and cycloalkyl, and

wherein heteroatoms of said heteroaryl and heterocycloalkyl are independently selected from N, O, and S, with the proviso that no two adjacent ring heteroatoms are both S or both O; and

further wherein R 1 and R 2 are each unsubstituted or optionally substituted with one or more substituents which can be the same or different and are independently selected from the group consisting of deuterium, halo, cyano, amino, aminoalkyl, (amino)alkoxy, —CONH 2 , —C(O)NH(alkyl), —C(O)N(alkyl) 2 , —C(O)NH(aryl), —C(O)N(aryl) 2 , —CF 3 , —CHF 2 , —CH 2 F, alkyl, hydroxyalkyl, -alkoxy, hydroxyl, hydroxyalkyl, carboxy, (alkoxyalkyl)amino, -alkylamine, aminocarbonyl, —CHO, —N(R 3 )—C(O)-alkyl, —N(R 3 )—C(O)-aryl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl;

R 3 is H, alkyl or arylalkyl; and

n is 4, 5 or 6;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 , wherein W is —C(O)—.

3. The compound of claim 1 , wherein W is —S(O) 2 —.

4. The compound of claim 1 , wherein n is 4.

5. The compound of claim 1 , wherein R 3 is H.

6. The compound of claim 1 , wherein R is selected from the group consisting of thienopyridine, 1H-pyrrolopyidine, pyrrolopyidine, imidazopyridine, pyrazolopyridine, quinolone, and furopyridine, each optionally substituted.

7. The compound of claim 1 , wherein R is selected from the group consisting of thieno[2,3-c]pyridin-2-yl, 1H-pyrrolo[3,2-c]pyidin-2-yl, 1H-pyrrolo[3,2-c]pyidin-2-yl, imidazo[1,2-a]pyridin-6-yl, pyrazolo[3,4-b]pyridin-5-yl, quinolin-6-yl, and furo[2,3-c]pyridin-2-yl.

8. The compound of claim 1 , wherein G is selected from the group consisting of aryl, heteroaryl, cycloalkyl, and heterocycloalkyl, each optionally substituted.

9. The compound of claim 1 , wherein G is selected from the group consisting of phenyl, thiazole, pyridine, piperidine, imidazole, furan, oxazole, pyridine, cyclohexyl, indole, benzodioxolane, benzothiophene, benzothiazole, imidazopyridine, and aza-indole, each optionally substituted.

10. The compound of claim 1 , wherein G is selected from the group consisting of phenyl, thiazol-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, indol-2-yl, indol-6-yl, imidazol-2-yl, imidazol-4-yl, piperidin-4-yl, furan-3-yl, oxazol-4-yl, pyridin-2-yl, cyclohexyl, benzodioxolane, benzothiophene, benzothiazole, imidazol[1,2-a]pyridin-6-yl, and 1H-pyrrolo[3,2-c]pyidin-2-yl, each optionally substituted.

11. The compound of claim 1 , wherein G is substituted with 1-4 substituents selected from the group consisting of halo, amino, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, acyl, haloalkoxy, aryl, heteroaryl, alkoxyalkyl, and mercapto.

12. The compound of claim 1 , wherein G is substituted with 1-3 substituents selected from the group consisting of halo, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, aryl, and heteroaryl.

13. The compound of claim 1 , wherein G is selected from the group consisting of imidazo[1,2-a]pyridine-6-yl, 1H-pyrrolo[3,2-c]pyridine, thieno[2,3-c]pyridin-2-yl, and furo[2,3-c]pyridin-2-yl, each optionally substituted.

14. The compound of claim 1 , wherein G is thieno[2,3-c]pyridin-2-yl or imidazo[1,2-a]pyridine.

15. A compound selected from the group consisting of:

N-(4-{1-[(3,5-dichlorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(3-fluoro-4-methoxybenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[2-(trifluoromethoxy)benzene]sulfonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(trifluoromethyl)phenyl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[6-(morpholin-4-yl)pyridin-3-yl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(dimethyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-cyclohexanecarbonylpiperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(propan-2-yloxy)phenyl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2-fluorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(1H-indol-2-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(4-chloro-2-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2,4-difluorophenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-{4-[1-(propane-2-sulfonyl)piperidin-4-yl]butyl}-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[2-(2-methyl-1,3-thiazol-4-yl)acetyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(1-methyl-1H-imidazol-4-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(5-fluoropyridin-2-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(dimethyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2-fluoro-3-methylphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(3-ethoxyphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(4-chlorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(4-fluorophenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(pyridin-3-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(propan-2-yloxy)benzene]sulfonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2,5-dichlorophenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2,6-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(pyridin-4-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-fluorophenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(3-(1-benzoylpiperidin-4-yl)propyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-fluoro-2-methylphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(difluoromethoxy)phenyl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2,6-difluorophenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2,3-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(1-acetylpiperidin-4-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(4-chlorobenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2-fluoro-5-methylbenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[2-(trifluoromethoxy)phenyl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[5-(methoxymethyl)pyridin-2-yl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(1H-indol-2-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[4-(propan-2-yl oxy)phenyl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(1H-indol-2-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(3-chlorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2,6-difluorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(1H-indol-6-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2,3-difluorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-[4-(1-benzoylazetidin-3-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(furan-3-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2,3-difluorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(5-methylpyrazin-2-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2-ethoxyphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2,3-dichlorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-cyclohexanecarbonylpiperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(5-chloro-2-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2-ethoxypyridin-3-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-{4-[1-(benzenesulfonyl)piperidin-4-yl]butyl}-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3,5-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2, 3-c]pyridine-2-carboxamide

N-(4-{1-[(3,4-difluorobenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2,5-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(difluoromethoxy)phenyl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(4-fluoro-3-methylbenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(5-methylpyrazin-2-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2H-1,3-benzodioxol-5-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2-fluorophenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(5-chloro-2-methoxypyridin-3-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(4-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(3-chloro-4-fluorobenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(4-methoxy-3-methylbenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(trifluoromethyl)pyridin-3-yl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-fluoro-4-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2,4-dichlorophenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-cyclohexanecarbonylpiperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2,6-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-{[4-({4-[(pyrrolidin-1-yl)carbonyl]benzene}sulfonyl)phenyl]methyl}-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

N-[4-(1-{[5-(methoxymethyl)pyridin-2-yl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2,5-difluorobenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(trifluoromethoxy)phenyl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[6-(propan-2-yl)pyridin-3-yl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(3-fluorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2,5-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(3,4-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2, 3-c]pyridine-2-carboxamide

N-(4-{1-[(2-phenyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2-phenyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-[4-(1-{[2-(trifluoromethyl)-1,3-thiazol-4-yl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(5-fluoropyridin-2-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(5-fluoro-2-methylphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[6-(morpholin-4-yl)pyridin-3-yl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(dimethyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[2-(2-methyl-1,3-thiazol-4-yl)acetyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2,5-dimethoxybenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2,6-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2-ethoxyphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-fluoro-2-methylphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(5-fluoro-1H-indol-2-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[2-(1-methyl-1H-indol-3-yl)acetyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(4-fluoro-2-methylbenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2-fluorobenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3,4-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(trifluoromethyl)pyridin-3-yl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(3,5-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(5-fluoro-2-methoxybenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-fluoro-4-methylphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2,3-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2,5-difluorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(3-cyanobenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-methoxybenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2-chlorobenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-{4-[1-(pyridine-3-sulfonyl)piperidin-4-yl]butyl}-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(trifluoromethyl)benzene]sulfonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2-chlorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(3-fluoro-2-methylphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[4-(trifluoromethyl)phenyl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2-chlorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(trifluoromethoxy)benzene]sulfonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3,4-difluorophenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(5-fluoro-1H-indol-2-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(5-fluoropyridin-2-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[2-(trifluoromethoxy)phenyl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(1H-indol-5-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2,5-dichlorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2-ethoxyphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(4-methoxybenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[2-(methylsulfanyl)pyridin-3-yl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(difluoromethoxy)phenyl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(furan-3-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2-methoxy-5-methylbenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2H-1,3-benzodioxol-5-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2,3-difluorophenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-{4-[1-({1H-pyrrolo[3,2-c]pyridin-2-yl}carbonyl)piperidin-4-yl]butyl}-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(trifluoromethyl)pyridin-3-yl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(4-methyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[2-(trifluoromethyl)-1,3-thiazol-4-yl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2,4-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[2-(trifluoromethoxy)phenyl]carbonyl}piperidin-4-yl)butyl]thieno[2, 3-c]pyridine-2-carboxamide

N-[2-(1-benzoylpiperidin-4-yl)ethyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-{4-[1-({1H-pyrrolo[3,2-c]pyridin-2-yl}carbonyl)piperidin-4-yl]butyl}thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(3-fluoro-4-methylphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(3-fluoro-4-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[5-(trifluoromethyl)pyridin-2-yl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3,4-dimethoxybenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(4-methyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(5-fluoro-1H-indol-2-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-[4-(1-{[2-(trifluoromethyl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(4-chloro-2-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(5-chloro-2-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2,5-difluorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(6-methylpyridin-3-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(4-fluorobenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(1-benzothiophen-2-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-[4-(1-{[2-(methylsulfanyl)pyridin-3-yl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(pyridin-2-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[5-(trifluoromethyl)pyridin-2-yl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(1,3-benzothiazol-6-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(1-methyl-1H-imidazol-4-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(4-methyl-1,3-thiazol-5-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-{[4-({4-[(pyrrolidin-1-yl)carbonyl]benzene}sulfonyl)phenyl]methyl}furo[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(1,3-benzothiazol-6-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(3-fluorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[2-(4-phenylphenyl)ethyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-{4-[1-(5-methyl-1,2-oxazole-4-sulfonyl)piperidin-4-yl]butyl}-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3,4-difluorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2,5-dichlorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[5-(trifluoromethyl)pyridin-2-yl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(pyridin-3-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2,4-dichlorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-[4-(1-{[6-(propan-2-yl)pyridin-3-yl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(1H-indol-6-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2-methylpyridin-3-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2,4-dichlorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-benzoylpiperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(4-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2, 3-c]pyridine-2-carboxamide

N-(4-{1-[(2,5-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2, 3-c]pyridine-2-carboxamide

N-(4-{1-[(2-chlorophenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2-methylpyridin-3-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-fluorobenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2-fluorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-[4-(1-{[4-(propan-2-yl)-1,3-oxazol-5-yl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2-methyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2-fluoro-3-methylphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(3,5-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[6-(propan-2-yl)pyridin-3-yl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(1-methyl-1H-indol-2-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[5-(propan-2-yl)pyridin-2-yl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2,4-difluorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2,4-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-[4-(1-benzoylpiperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-chlorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[2-(pyridin-3-yl)-1,3-thiazol-4-yl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2-ethoxypyridin-3-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(3-ethoxyphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2,4-dimethoxybenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2,5-difluorophenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[2-(1-methyl-1H-indol-3-yl)acetyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(trifluoromethoxy)phenyl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-{4-[1-({1H-pyrrolo[3,2-c]pyridin-2-yl}carbonyl)piperidin-4-yl]butyl}imidazo[1,2-a]pyridine-6-carboxamide

N-[6-(4-chlorophenoxy)hexyl]quinoline-6-carboxamide

N-(4-{1-[(2-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(4-benzoylpiperazin-1-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(5-chloro-2-methoxypyridin-3-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{4-[(3-methoxyphenyl)carbonyl]piperazin-1-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-fluoro-4-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2, 3-c]pyridine-2-carboxamide

N-(4-{1-[(5-chloro-2-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2,6-difluorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-{4-[1-({imidazo[1,2-a]pyridin-6-yl}carbonyl)piperidin-4-yl]butyl}imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[5-(methoxymethyl)pyridin-2-yl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-[4-(1-{[3-(trifluoromethyl)benzene]sulfonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-chlorophenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(3,5-dichlorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(pyridin-2-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[2-(pyridin-3-yl)-1,3-thiazol-4-yl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(1-methyl-1H-indol-2-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2-methylbenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(1-methyl-1H-indol-2-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[4-(trifluoromethoxy)phenyl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[2-(trifluoromethyl)-1,3-thiazol-4-yl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(3-fluoro-4-methylphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2H-1,3-benzodioxol-5-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3,4-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(2,4-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-{[4-({4-[(pyrrolidin-1-yl)carbonyl]benzene}sulfonyl)phenyl]methyl}thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(pyridin-3-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(4-chloro-2-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3,4-dichlorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3,5-dichlorophenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-(benzyloxy)phenethyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(6-methylpyridin-3-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[5-(propan-2-yl)pyridin-2-yl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(3-ethoxyphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[2-(trifluoromethyl)benzene]sulfonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[2-(2-methyl-1,3-thiazol-4-yl)acetyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(3,4-dichlorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(1-acetylpiperidin-4-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(1-benzothiophen-2-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(1H-pyrazol-1-yl)phenyl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(3-chlorobenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2-methyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[5-(propan-2-yl)pyridin-2-yl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(4-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-{4-[1-({thieno[2,3-c]pyridin-2-yl}carbonyl)piperidin-4-yl]butyl}thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(3,5-difluorobenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-chloro-4-methoxybenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(2,3-dimethoxyphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(3,4-difluorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2,4-difluorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2-fluoro-3-methylphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(4-chlorophenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[4-(1H-pyrazol-1-yl)phenyl]carbonyl}piperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-{4-[1-(1-methyl-1H-pyrazole-3-sulfonyl)piperidin-4-yl]butyl}-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(6-methylpyridin-3-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2-ethoxypyridin-3-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-benzoylpiperidin-4-yl)butyl]imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(1H-indol-6-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2-methoxyphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2,3-dichlorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2-methyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-{2-[1-(benzenesulfonyl)piperidin-4-yl]ethyl}-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(propan-2-yl)-1,3-oxazol-5-yl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-{4-[1-({imidazo[1,2-a]pyridin-6-yl}carbonyl)piperidin-4-yl]butyl}-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-fluoro-4-methylbenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(4-methylbenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3-fluoro-2-methylbenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(3,4-dichlorophenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[4-(propan-2-yloxy)phenyl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-[4-(1-{[4-(1H-pyrazol-1-yl)phenyl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[2-(trifluoromethyl)pyrimidin-5-yl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(5-fluoro-2-methylphenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-[4-(1-{[2-(methylsulfanyl)pyridin-3-yl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(2-phenyl-1,3-thiazol-4-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[2-(pyridin-3-yl)-1,3-thiazol-4-yl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(5-methylpyrazin-2-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{1-[(1,3-benzothiazol-6-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-(4-{4-[(3-chlorophenyl)carbonyl]piperazin-1-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(1H-indol-5-yl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(1-benzothiophen-2-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[3-(trifluoromethoxy)benzene]sulfonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[2-(1-methyl-1H-indol-3-yl)acetyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(furan-3-yl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

N-[4-(1-{[6-(trifluoromethyl)pyridin-3-yl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(4-cyanobenzene)sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(1-methyl-1H-imidazol-2-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[6-(morpholin-4-yl)pyridin-3-yl]carbonyl}piperidin-4-yl)butyl]thieno[2,3-c]pyridine-2-carboxamide

N-[4-(1-{[4-(trifluoromethyl)phenyl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(1H-indol-5-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(4-fluorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[(4-chlorophenyl)carbonyl]piperidin-4-yl}butyl)thieno[2,3-c]pyridine-2-carboxamide

N-(4-{1-[6-(trifluoromethyl)pyridine-3-sulfonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(3-(1-benzoylpiperidin-4-yl)butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(4-fluorophenyl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-[4-(1-{[4-(propan-2-yl)-1,3-oxazol-5-yl]carbonyl}piperidin-4-yl)butyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxamide

N-(4-{1-[(5-chloro-2-methoxypyridin-3-yl)carbonyl]piperidin-4-yl}butyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxamide and

N-(4-{1-[(5-fluoro-2-methylphenyl)carbonyl]piperidin-4-yl}butyl)imidazo[1,2-a]pyridine-6-carboxamide

and pharmaceutically acceptable salts thereof.

16. A pharmaceutical composition comprising at least one compound of claim 1 , or a pharmaceutically acceptable salt thereof, and at least one pharmaceutically acceptable carrier.

17. A method of preventing or inhibiting a condition in a patient by administering a therapeutically effective amount of at least one compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein said condition is selected from the group consisting of cancer, ovarian cancer, breast cancer, uterine cancer, colon cancer, cervical cancer, lung cancer, prostate cancer, skin cancer, bladder cancer, pancreatic cancer, leukemia, lymphoma, Hodgkin's disease, non-small cell lung cancer, small cell lung cancer, multiple myeloma, squamous cell cancers, kidney cancer, urethral and bladder cancers, cancers of head and neck, and cancers of the brain and central nervous system.

18. The method of claim 17 , wherein said condition is a cancer.

19. The method of claim 18 , wherein said cancer is selected from the group consisting of leukemia, lymphoma, ovarian cancer, breast cancer, uterine cancer, colon cancer, cervical cancer, lung cancer, prostate cancer, skin cancer, CNS cancer, bladder cancer, pancreatic cancer, and Hodgkin's disease.

Assignments (10)
RELEASE OF SECURITY INTEREST Recorded Oct 17, 2023
From: FIRST-CITIZENS BANK & TRUST COMPANY, AS AGENT
To: VALO HEALTH, INC.; VALO HEALTH, LLC
Reel/Frame 065255/0660 →
SECURITY INTEREST Recorded Jul 6, 2023
From: VALO HEALTH, LLC; VALO HEALTH, INC.
To: FIRST-CITIZENS BANK & TRUST COMPANY, AS AGENT
Reel/Frame 064207/0957 →
MERGER Recorded Sep 8, 2021
From: VALO EARLY DISCOVERY, INC.
To: VALO HEALTH, INC.
Reel/Frame 057438/0025 →
CHANGE OF NAME Recorded Sep 16, 2020
From: INTEGRAL EARLY DISCOVERY, INC.
To: VALO EARLY DISCOVERY, INC.
Reel/Frame 053787/0138 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 5, 2020
From: FORMA THERAPEUTICS, INC.
To: INTEGRAL EARLY DISCOVERY, INC.
Reel/Frame 053402/0298 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 3, 2020
From: FORMA TM, LLC
To: FORMA THERAPEUTICS, INC.
Reel/Frame 053387/0440 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 22, 2019
From: BAIR, KENNETH W.; BAUMEISTER, TIMM R.; BUCKMELTER, ALEXANDRE J.; CLODFELTER, KARL H.; HAN, BINGSONG; KUNTZ, JUDITH D.; LIN, JIAN; REYNOLDS, DOMINIC J.; SMITH, CHASE C.; WANG, ZHONGGUO; ZHENG, XIAOZHANG
To: FORMA THERAPEUTICS, INC.
Reel/Frame 048671/0243 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 15, 2016
From: BAIR, KENNETH W; BAUMEISTER, TIMM R; BUCKMELTER, ALEX J; CLODFELTER, KARL H; LIN, JIAN; REYNOLDS, DOMINIC; SMITH, CHASE C; ZHENG, XIAOZHANG; WANG, ZHONGGUO; KUNTZ, JUDITH; HAN, BINGSONG
To: FORMA THERAPEUTICS, INC.
Reel/Frame 040740/0308 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 15, 2016
From: FORMA THERAPEUTICS, INC.
To: FORMA TM, LLC
Reel/Frame 040940/0704 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 15, 2016
From: BAIR, KENNETH W; BAUMEISTER, TIMM R; BUCKMELTER, ALEX J; CLODFELTER, KARL H; HAN, BINGSONG; KUNTZ, JUDITH; LIN, JIAN; REYNOLDS, DOMINIC J; SMITH, CHASE C; WANG, ZHONGGUO; ZHENG, XIAOZHANG
To: FORMA THERAPEUTICS, INC.
Reel/Frame 040993/0159 →