IP Library › Granted Patent US 10,047,051

Granted Patent B2

US 10,047,051 · App. 15/164,317 · Granted Aug 14, 2018

Substituted pyridines and method of use

Inventors: Robert J. Altenbach (Chicago, IL); Marlon D. Cowart (Round Lake Beach, IL); Tom Roger Lisette De Munck (Mechelen, BE); Sébastien Jean Jacques Cédric Dropsit Montovert (Aulnay sous bois, FR); Gregory A. Gfesser (Lindenhurst, IL); Hans Kelgtermans (Mechelen, BE); Sébastien Laurent Xavier Martina (Mechelen, BE); Steven Emiel Van der Plas (Mechelen, BE); Xueqing Wang (Northbrook, IL)

Assignees: AbbVie S.á.r.l.; Galapagos NV

C07D213/81 A61K31/44 A61K31/443 A61K31/4427 A61K31/4439 A61K31/4545 A61K31/506 A61K31/513 A61K31/5377 A61K45/06 C07D401/06 C07D401/12 C07D401/14 C07D405/12 C07D491/107

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Quick Facts

Patent No.: US 10,047,051
App. No.: 15/164,317
Granted: Aug 14, 2018
Kind: B2

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Abstract

The invention discloses compounds of Formula I wherein X, R 1 , R 2 , and R 3 are as defined herein. The present invention relates to compounds and their use in the treatment of cystic fibrosis, methods for their production, pharmaceutical compositions comprising the same, and methods of treating cystic fibrosis by administering a compound of the invention.

Claims (578)

1. A compound of Formula I or a pharmaceutically acceptable salt thereof

wherein

X is

halo;

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

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

—OH;

C 1-4 alkoxy; or

—NR 11A R 11B ;

—NR 12A R 12B ;

cyclopropyl optionally substituted with one or more independently selected R 5 groups;

phenoxy optionally substituted with one or more independently selected R 5 groups; or

phenyl optionally substituted with one or more independently selected R 5 groups;

R 1 is

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

—OH;

C 1-4 alkoxy; or

4-6 membered monocyclic heterocycle comprising 1 or 2 heteroatoms independently selected from the group consisting of O, S, and N;

phenyl optionally substituted with one or more independently selected R 4 groups;

N-linked 4-6 membered monocyclic heterocycle comprising 1, 2, or 3 heteroatoms independently selected from the group consisting of N, O, and S, wherein the monocyclic heterocycle is optionally substituted with one or more independently selected R 5 groups;

N-linked 4-6 membered monocyclic heterocycle comprising 1, 2, or 3 heteroatoms independently selected from the group consisting of N, O, and S, fused to a phenyl, wherein the monocyclic heterocycle and the phenyl are optionally substituted with one or more independently selected R 5 groups;

C 3-7 cycloalkyl optionally substituted with one or more independently selected R 5 groups; or

—NR 6 R 7 ;

R 2 is

C 1-6 alkyl optionally substituted with one or more independently selected

—OH;

halo;

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

halo;

C 1-4 alkoxy;

C 3-7 cycloalkyl optionally substituted with one or more independently selected R 5 groups; or

4-6 membered monocyclic heterocycle comprising 1 or 2 heteroatoms independently selected from the group consisting of N, O, and S, wherein the monocyclic heterocycle is optionally substituted with one or more independently selected R 5 groups;

—C(═O)NR 8a R 8b ;

C 3-7 cycloalkyl optionally substituted with one or more independently selected

—OH;

halo;

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

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

—OH;

halo;

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

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

5-6 membered monocyclic heteroaryl comprising 1, 2, or 3 heteroatoms independently selected from the group consisting of O, S, and N, wherein the monocyclic heteroaryl is optionally substituted with one or more independently selected R 5 groups; or

phenyl optionally substituted with one or more independently selected R 5 groups;

C 3-7 cycloalkyl optionally substituted with one or more

—OH;

halo;

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

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

4-6 membered monocyclic heterocycle comprising 1 or 2 heteroatoms independently selected from the group consisting of O, S, and N, wherein the monocyclic heterocycle is optionally substituted with one or more

—OH;

halo;

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

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

4-6 membered monocyclic heterocycle comprising 1 or 2 heteroatoms independently selected from the group consisting of O, S, and N, fused to a phenyl ring, wherein the monocyclic heterocycle and the phenyl are optionally substituted with one or more independently selected R 5 groups;

5-11 membered spirocyclic heterocycle comprising 1 or 2 heteroatoms independently selected from the group consisting of O, S, and N, wherein the spirocyclic heterocycle is optionally substituted with one or more independently selected R 5 groups;

—NHC(═O)R 13 ;

and R 3 is H; or

R 2 and R 3 , together with the nitrogen atom to which they are attached form

an azetidine or a pyrrolidine ring, wherein the azetidine and the pyrrolidine are optionally substituted with one or more independently selected R 9 groups; or

a 7-11 membered spirocyclic heterocycle comprising one or more heteroatoms independently selected from the group consisting of N, O, and S; wherein the spirocyclic heterocycle is optionally substituted with one or more independently selected R 5 groups;

each R 4 is independently selected from the group consisting of:

halo;

C 1-4 alkyl optionally substituted with one or more independently selected halo; and

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

each R 5 is independently selected from the group consisting of:

—OH;

halo;

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

C 1-4 alkoxy;

halo; or

—OH; and

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

R 6 is H, C 1-4 alkyl, or C 3-7 cycloalkyl wherein the C 3-7 cycloalkyl is optionally substituted with one or more independently selected R 5 groups;

R 7 is

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

halo;

phenyl optionally substituted with one or more independently selected

halo;

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

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

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

4-6 membered monocyclic heterocycle comprising 1 or 2 heteroatoms independently selected from the group consisting of O, S, and N; wherein the monocyclic heterocycle is optionally substituted with one or more independently selected R 5 groups;

each R 8a and R 8b is independently selected from the group consisting of

C 1-4 alkyl optionally substituted with one or more independently selected halo; and

C 3-7 cycloalkyl optionally substituted with one or more independently selected R 5 groups;

each R 9 is independently selected from the group consisting of:

—OH;

halo;

—CN;

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

—OH;

halo; or

C 1-4 alkoxy;

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

C 3-7 cycloalkyl optionally substituted with one or more independently selected R 5 groups;

—C(═O)NR 10a R 10b ; and

each R 10a and R 10b is independently selected from the group consisting of H and C 1-4 alkyl;

each R 11a and R 11b is independently selected from the group consisting of

H; and

C 1-4 alkyl;

R 12a and R 12b are independently selected from the group consisting of

C 1-4 alkyl; and

C 3-7 cycloalkyl; and

R 13 is independently C 1-4 alkyl optionally substituted with one or more independently selected

—OH;

halo; or

C 1-4 alkoxy.

2. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 1 is phenyl optionally substituted with one, two, or three independently selected R 4 groups.

3. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 1 is N-linked 4-6 membered monocyclic heterocycle comprising 1, 2, or 3 heteroatoms independently selected from the group consisting of N, O, and S, wherein the monocyclic heterocycle is optionally substituted with 1, 2, or 3 independently selected R 5 groups.

4. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 1 is —NR 6 R 7 .

5. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein X is H, halo, or unsubstituted cyclopropyl.

6. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 2 is C 1-6 alkyl optionally substituted with 1, 2, or 3 independently selected

—OH;

fluoro;

C 1-4 alkoxy optionally substituted with 1, 2, or 3 independently selected

fluoro;

C 1-4 alkoxy;

C 3-7 cycloalkyl optionally substituted with 1, 2, or 3 independently selected R 5 groups; or

—OH;

fluoro;

C 1-4 alkoxy optionally substituted with 1, 2, or 3 fluoro, or

C 1-4 alkyl optionally substituted with 1, 2, or 3 fluoro;

phenyl optionally substituted with 1, 2, or 3 independently selected R 5 groups.

7. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 2 is C 3-6 alkyl substituted with one or two —OH, and optionally further substituted with 1, 2, or 3 fluoro; or optionally further substituted with one C 1-4 alkoxy which is optionally substituted with

1, 2, or 3 fluoro;

one C 1-4 alkoxy; or

one C 3-7 cycloalkyl optionally substituted with 1, 2, or 3 independently selected R 5 groups.

8. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 2 is C 1-6 alkyl substituted with one substituent wherein the substituent is

—C(═O)NR 8a R 8b ;

C 3-7 cycloalkyl optionally substituted with 1, 2, or 3 independently selected

—OH;

fluoro;

C 1-4 alkoxy optionally substituted with 1, 2, or 3 fluoro; or

C 1-4 alkyl optionally substituted with 1, 2, or 3 independently selected —OH, fluoro, or C 1-4 alkoxy;

—OH;

fluoro;

C 1-4 alkoxy optionally substituted with 1, 2, or 3 fluoro, or

C 1-4 alkyl optionally substituted with 1, 2, or 3 fluoro;

9. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 2 is C 3-6 cycloalkyl optionally substituted with 1, 2, or 3 independently selected —OH; fluoro; C 1-4 alkyl optionally substituted with 1, 2, or 3 fluoro; or C 1-4 alkoxy optionally substituted with 1, 2, or 3 fluoro.

10. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 2 is 4-6 membered monocyclic heterocycle comprising 1 or 2 heteroatoms independently selected from the group consisting of O, S, and N, wherein the monocyclic heterocycle is optionally substituted with 1, 2, or 3 independently selected —OH; fluoro; C 1-4 alkyl optionally substituted with 1, 2, or 3 fluoro; or C 1-4 alkoxy optionally substituted with 1, 2, or 3 fluoro.

11. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 2 and R 3 , together with the nitrogen atom to which they are attached form an azetidine or a pyrrolidine ring, wherein the azetidine and the pyrrolidine are optionally substituted with 1, 2, or 3 independently selected R 9 groups.

12. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 2 and R 3 , together with the nitrogen atom to which they are attached form an azetidine ring which is optionally substituted with 1, 2, or 3 independently selected R 9 groups.

13. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 1 is phenyl optionally substituted with one, two, or three independently selected R 4 groups; and

R 2 is C 1-6 alkyl optionally substituted with 1, 2, or 3 independently selected

—OH;

fluoro;

C 1-4 alkoxy optionally substituted with 1, 2, or 3 independently selected

fluoro;

C 1-4 alkoxy;

C 3-7 cycloalkyl optionally substituted with 1, 2, or 3 independently selected R 5 groups; or

—OH;

fluoro;

C 1-4 alkoxy optionally substituted with 1, 2, or 3 fluoro, or

C 1-4 alkyl optionally substituted with 1, 2, or 3 fluoro;

phenyl optionally substituted with 1, 2, or 3 independently selected R 5 groups.

14. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 1 is phenyl optionally substituted with one, two, or three independently selected R 4 groups; and

1, 2, or 3 fluoro;

one C 1-4 alkoxy; or

one C 3-7 cycloalkyl optionally substituted with 1, 2, or 3 independently selected

R 5 groups.

15. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 1 is phenyl optionally substituted with one, two, or three independently selected R 4 groups; and

R 2 is C 1-6 alkyl substituted with one substituent wherein the substituent is

—C(═O)NR 8a R 8b ;

C 3-7 cycloalkyl optionally substituted with 1, 2, or 3 independently selected

—OH;

fluoro;

C 1-4 alkoxy optionally substituted with 1, 2, or 3 fluoro; or

C 1-4 alkyl optionally substituted with 1, 2, or 3 independently selected —OH, fluoro, or C 1-4 alkoxy;

—OH;

fluoro;

C 1-4 alkoxy optionally substituted with 1, 2, or 3 fluoro, or

C 1-4 alkyl optionally substituted with 1, 2, or 3 fluoro;

16. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 1 is phenyl optionally substituted with one, two, or three independently selected R 4 groups; and

17. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 1 is phenyl optionally substituted with one, two, or three independently selected R 4 groups; and

18. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 1 is phenyl optionally substituted with one, two, or three independently selected R 4 groups; and

19. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 2 is C 3-6 alkyl substituted with one —OH and optionally further substituted with 1, 2, or 3 fluoro; or optionally further substituted with one C 1-4 alkoxy wherein the C 1-4 alkoxy is optionally substituted with 1, 2, or 3 fluoro.

20. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein

R 1 is —NR 6 R 7 ; and

21. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein

R 2 and R 3 are H.

22. The compound of claim 1 of Formula I-a, or a pharmaceutically acceptable salt thereof

wherein

n is 0, 1, or 2;

R 4A is H, F, CH 3 , —CH(CH 3 ) 2 , t-Bu, CF 3 , —OCH 3 , —O—CH(CH 3 ) 2 , or —OCF 3 ;

each R 4B is independently F or —OCF 3 ; and

X, R 2 , and R 3 , are as set forth in claim 1 .

23. The compound of claim 22 or a pharmaceutically acceptable salt thereof, wherein X is H.

24. The compound of claim 22 or a pharmaceutically acceptable salt thereof wherein

n is 0 or 1;

R 4A is F, CF 3 , or —OCF 3 ; and

R 4B is F.

25. The compound of claim 22 or a pharmaceutically acceptable salt thereof wherein

1, 2, or 3 fluoro;

one C 1-4 alkoxy; or

one C 3-7 cycloalkyl optionally substituted with 1, 2, or 3 independently selected R 5 groups.

26. The compound of claim 22 or a pharmaceutically acceptable salt thereof wherein

R 2 is C 3-6 alkyl substituted with one —OH, and optionally further substituted with 1, 2, or 3 fluoro or optionally further substituted with one C 1-4 alkoxy wherein the C 1-4 alkoxy is optionally substituted with one cyclopropyl or 1, 2, or 3 fluoro.

27. The compound of claim 22 or a pharmaceutically acceptable salt thereof wherein

R 2 is C 1-6 alkyl substituted with one —C(═O)NR 8a R 8b wherein R 8a and R 8b are independently selected from the group consisting of H; C 1-4 alkyl optionally substituted with 1, 2, or 3 fluoro; and cyclopropyl optionally substituted with 1, 2, or 3 independently selected R 5 groups.

28. The compound of claim 22 or a pharmaceutically acceptable salt thereof wherein

R 2 is C 3-6 cycloalkyl optionally substituted with 1 or 2 independently selected fluoro, CH 3 , CF 3 , —OH, or —OCH 3 .

29. The compound of claim 22 or a pharmaceutically acceptable salt thereof wherein

R 2 is oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, azetidinyl, pyrrolidinyl, or piperidinyl; each of which is optionally substituted with 1 or 2 independently selected fluoro, CH 3 , CF 3 , —OH, or —OCH 3 .

30. The compound of claim 22 or a pharmaceutically acceptable salt thereof wherein

R 2 and R 3 , together with the nitrogen atom to which they are attached form an azetidine ring which is optionally substituted with 1, 2, or 3 independently selected R 9 groups.

31. The compound of claim 22 or a pharmaceutically acceptable salt thereof wherein

R 2 is

wherein

R A is H or CH 3 ; and

R B , R C , and R D are H; or

R B , R C , and R D are fluoro; or

R B and R C are H, and R D is C 1-4 alkoxy, —OCH 2 -cyclopropyl, or —OCH 2 CF 3 .

32. The compound of claim 31 or a pharmaceutically acceptable salt thereof wherein

n is 0 or 1;

R 4A is F, CF 3 , or —OCF 3 ,

R A is H; and

R B , R C , and R D are fluoro; or

R B and R C are H, and R D is —OCH 3 , —OCH 2 CH 3 , —OCH(CH 3 ) 2 , —OC(CH 3 ) 3 , —OCH 2 -cyclopropyl, or —OCH 2 CF 3 .

33. The compound of claim 31 or a pharmaceutically acceptable salt thereof wherein

X is H;

n is 0; and

R 4A is F.

34. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of:

3-amino-N-(2-hydroxy-2-methylpropyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(3,3,3-trifluoro-2-hydroxy-2-methylpropyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(2-hydroxy-3-methoxypropyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3-hydroxypyrrolidin-1-yl)methanone;

3-amino-N-[(4-hydroxy-1-methylpiperidin-4-yl)methyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(3,3,3-trifluoro-2-hydroxypropyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(tetrahydrofuran-2-ylmethyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(1,4-dioxan-2-ylmethyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[2-(morpholin-4-yl)ethyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-[(4-fluorophenyl)sulfonyl]-N-(2-hydroxy-2-methylpropyl)pyridine-2-carboxamide;

3-amino-N-(2-hydroxy-2-methylpropyl)-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(1-hydroxybutan-2-yl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(1-hydroxy-3-methylbutan-2-yl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(2-hydroxyethyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(1-hydroxycyclopropyl)methyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(2-hydroxy-3,3-dimethylbutyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

rac-3-amino-N-[(1R,2R)-2-hydroxycyclohexyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(3-hydroxy-2,2-dimethylpropyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-[(4-fluorophenyl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxy-2-methylpropyl)pyridine-2-carboxamide;

3-amino-N-[(2R)-2-hydroxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2S)-2-hydroxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-{[1-(hydroxymethyl)cyclopropyl]methyl}-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-{[1-(hydroxymethyl)cyclobutyl]methyl}-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(3-hydroxy-2-methylpropyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-[(4-fluorophenyl)sulfonyl]-N-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-N-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-[(4-fluorophenyl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-N-[(3-hydroxytetrahydrofuran-3-yl)methyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-[(4-fluorophenyl)sulfonyl]-N-[(1-hydroxycyclopropyl)methyl]pyridine-2-carboxamide;

3-amino-N-[3-(cyclopropylmethoxy)-2-hydroxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3-hydroxyazetidin-1-yl)methanone;

rac-3-amino-N-[(3R,4S)-4-hydroxytetrahydro-2H-pyran-3-yl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(4-hydroxy-2,2-dimethylbutyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[2-hydroxy-2-(tetrahydro-2H-pyran-4-yl)ethyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-[(4-fluorophenyl)sulfonyl]-N-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-N-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[3-(2-ethoxyethoxy)-2-hydroxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-[(3-fluorophenyl)sulfonyl]-N-(2-hydroxy-2-methylpropyl)pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3,3-difluoroazetidin-1-yl)methanone;

3-amino-N-[2-hydroxy-1-(4-methylphenyl)ethyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3-methoxyazetidin-1-yl)methanone;

3-amino-N-[1-(ethylamino)-1-oxopropan-2-yl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(1,3-dihydroxypropan-2-yl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(4-hydroxybutyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2R)-1-hydroxy-4-methylpentan-2-yl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[2-(ethylamino)-2-oxoethyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2S)-1-amino-3-methyl-1-oxobutan-2-yl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2R)-2,3-dihydroxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(3-hydroxy-3-methylbutyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(4,4,4-trifluoro-3-hydroxybutyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(3S)-3-hydroxybutyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(3-hydroxy-4-methoxybutyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(4-amino-4-oxobutan-2-yl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

N 2 -[(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)carbonyl]-L-leucinamide;

3-amino-N-[2-oxo-2-(propan-2-ylamino)ethyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[2-(cyclopropylamino)-2-oxoethyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3,3-dimethylazetidin-1-yl)methanone;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)[3-(morpholin-4-yl)azetidin-1-yl]methanone;

1-[(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)carbonyl]azetidine-3-carbonitrile;

1-[(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)carbonyl]-N,N-dimethylazetidine-3-carboxamide;

3-amino-N-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(azetidin-1-yl)methanone;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)[3-(hydroxymethyl)azetidin-1-yl]methanone;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3-fluoroazetidin-1-yl)methanone;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(2-oxa-6-azaspiro[3.3]hept-6-yl)methanone;

3-amino-N-[(2R)-2-hydroxy-3-methoxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2R)-2-hydroxy-3-methoxypropyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-{[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonyl}-N-(2-hydroxy-3-methoxypropyl)pyridine-2-carboxamide;

3-amino-5-[(4-fluorophenyl)sulfonyl]-N-(4,4,4-trifluoro-3-hydroxybutyl)pyridine-2-carboxamide;

3-amino-N-[2-hydroxy-2-(tetrahydrofuran-3-yl)ethyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

rac-3-amino-N-[(3R,4S)-4-hydroxytetrahydrofuran-3-yl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(2-hydroxyethyl)-5-{[2-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[2-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3-hydroxyazetidin-1-yl)methanone;

(3-amino-5-{[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3-hydroxyazetidin-1-yl)methanone;

(3-amino-5-{[2-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3,3-difluoroazetidin-1-yl)methanone;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone;

3-amino-N-(2-hydroxy-3-methoxypropyl)-5-{[2-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]-5-{[2-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2S)-2-hydroxypropyl]-5-{[2-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

rac-3-amino-N-[(3R,4S)-4-hydroxytetrahydro-2H-pyran-3-yl]-5-{[2-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-[(4,4-difluoropiperidin-1-yl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

(3-amino-5-{[2-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3-cyclopropyl-3-hydroxyazetidin-1-yl)methanone;

3-amino-N-(2-hydroxy-4-methylpentyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(3-ethoxy-2-hydroxypropyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3-hydroxy-3-methylazetidin-1-yl)methanone;

3-amino-N-[2-hydroxy-3-(propan-2-yloxy)propyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)(3-hydroxy-3-methylazetidin-1-yl)methanone;

3-amino-N-[2-hydroxy-3-(propan-2-yloxy)propyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2S)-1-amino-1-oxobutan-2-yl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-[cyclopropyl(methyl)sulfamoyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-N-(3,3,3-trifluoro-2-hydroxypropyl)-5-{[4-(trifluoromethyl)piperidin-1-yl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-[(3,3-difluoroazetidin-1-yl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}-N-[(2R)-2-hydroxy-3-methoxypropyl]pyridine-2-carboxamide;

3-amino-N-[(2S)-2-hydroxypropyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(3R)-tetrahydrofuran-3-ylmethyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(3S)-tetrahydrofuran-3-ylmethyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)(3,3-difluoroazetidin-1-yl)methanone;

3-amino-N-[2-oxo-2-(propan-2-ylamino)ethyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone;

3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}-N-[(3R)-tetrahydrofuran-3-ylmethyl]pyridine-2-carboxamide;

3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}-N-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-5-[cyclopropyl(2-methoxyethyl)sulfamoyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-(2,3-dihydro-4H-1,4-benzoxazin-4-yl sulfonyl)-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)(3,3-dimethylazetidin-1-yl)methanone;

(3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)(3,3-dimethylazetidin-1-yl)methanone;

(3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone;

3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}-N-[2-oxo-2-(propan-2-ylamino)ethyl]pyridine-2-carboxamide;

3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}-N-[(3S)-tetrahydrofuran-3-ylmethyl]pyridine-2-carboxamide;

3-amino-5-{[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonyl}-N-[(3R)-tetrahydrofuran-3-ylmethyl]pyridine-2-carboxamide;

3-amino-5-{[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonyl}-N-[(3S)-tetrahydrofuran-3-ylmethyl]pyridine-2-carboxamide;

3-amino-5-{[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonyl}-N-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-N-{[1-(ethoxymethyl)cyclobutyl]methyl}-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)[3-(2,2-difluoroethoxy)azetidin-1-yl]methanone;

3-amino-N-(trans-3-methoxycyclobutyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(6-oxa-2-azaspiro[3.5]non-2-yl)methanone;

3-amino-N-(3,3-difluorocyclobutyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(3-methoxypropyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[2-(1-methylcyclopropyl)ethyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(6-oxa-2-azaspiro[3.4]oct-2-yl)methanone;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3-methylazetidin-1-yl)methanone;

3-amino-N-(tetrahydrofuran-3-yl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(3R)-tetrahydrofuran-3-yl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(tetrahydro-2H-pyran-4-ylmethyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3-ethyl-3-fluoroazetidin-1-yl)methanone;

3-amino-N-[3-(cyclopropylmethoxy)-2-hydroxypropyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[3-(cyclopropylmethoxy)-2-hydroxypropyl]-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}-N-[2-hydroxy-3-(propan-2-yloxy)propyl]pyridine-2-carboxamide;

(3-amino-5-{[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3,3-dimethylazetidin-1-yl)methanone;

3-amino-5-{[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonyl}-N-[2-oxo-2-(propan-2-ylamino)ethyl]pyridine-2-carboxamide;

3-amino-5-[(3,4-difluorobenzyl)(methyl)sulfamoyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-[(2,4-difluorobenzyl)(methyl)sulfamoyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-[(4-methoxybenzyl)(methyl)sulfamoyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-(morpholin-4-yl sulfonyl)-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-N-[(3R)-tetrahydro-2H-pyran-3-yl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[2-(furan-2-yl)ethyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2S)-1-hydroxybutan-2-yl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(tetrahydro-2H-pyran-3-ylmethyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(3S)-tetrahydrofuran-3-yl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(4R)-3,4-dihydro-2H-chromen-4-yl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(tetrahydro-2H-pyran-4-yl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[2-(1,3-dioxolan-2-yl)ethyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2S)-1-hydroxy-3-methylbutan-2-yl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(1-oxaspiro[4.5]dec-3-yl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(1-oxaspiro[4.4]non-3-yl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(oxetan-3-yl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(2-cyclopropylethyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(3,3-difluorocyclobutyl)methyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)[3-(methoxymethyl)-3-methylazetidin-1-yl]methanone;

3-amino-N-(cyclopropylmethyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(4-methyltetrahydro-2H-pyran-3-yl)methyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)[3-(trifluoromethyl)azetidin-1-yl]methanone;

(3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)[3-(difluoromethoxy)azetidin-1-yl]methanone;

(3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)[3-hydroxy-3-(propan-2-yl)azetidin-1-yl]methanone;

(3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)[3-(trifluoromethyl)azetidin-1-yl]methanone;

(3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)[3-(difluoromethoxy)azetidin-1-yl]methanone;

(3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)[3-hydroxy-3-(propan-2-yl)azetidin-1-yl]methanone;

3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}-N-(2-hydroxy-4-methoxy-2-methylbutyl)pyridine-2-carboxamide;

(3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)(3,3-difluoroazetidin-1-yl)methanone;

(3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)[3-(2-hydroxypropan-2-yl)azetidin-1-yl]methanone;

3-amino-N-[2-hydroxy-3-(2-methylpropoxy)propyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(2-hydroxy-4-methoxy-2-methylbutyl)-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-{[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonyl}-N-[2-hydroxy-3-(propan-2-yloxy)propyl]pyridine-2-carboxamide;

3-amino-N-[3-(cyclopropylmethoxy)-2-hydroxypropyl]-5-{[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}-N-[2-hydroxy-3-(2-methylpropoxy)propyl]pyridine-2-carboxamide;

3-amino-5-{[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonyl}-N-[2-hydroxy-3-(2-methylpropoxy)propyl]pyridine-2-carboxamide;

(3-amino-5-{[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3,3-difluoroazetidin-1-yl)methanone;

(3-amino-5-{[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone;

(3-amino-5-{[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)[3-(2-hydroxypropan-2-yl)azetidin-1-yl]methanone;

(3-amino-5-{[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)[3-hydroxy-3-(propan-2-yl)azetidin-1-yl]methanone;

{3-amino-5-[(4-fluorophenyl)sulfonyl]pyridin-2-yl}[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone;

3-amino-N-[(2R)-2-hydroxy-3-methoxypropyl]-5-{[2-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)[3-(2-hydroxypropan-2-yl)azetidin-1-yl]methanone;

3-amino-5-{[(2R)-2-methylpyrrolidin-1-yl]sulfonyl}-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-{[(3S)-3-fluoropyrrolidin-1-yl]sulfonyl}-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-{[(2S)-2-methylpyrrolidin-1-yl]sulfonyl}-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-[(3-methylpiperidin-1-yl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-[(3,3-difluoropiperidin-1-yl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-[(4-methylpiperidin-1-yl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-[(3,5-dimethylpiperidin-1-yl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-[(3,3-difluoropyrrolidin-1-yl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-[(4-fluorobenzyl)(methyl)sulfamoyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-N-(3-methylbutan-2-yl)-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(2-methylpropyl)-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[2-(tetrahydrofuran-2-ylmethoxy)ethyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(2,2-dimethylpropyl)-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[2-(propan-2-yloxy)ethyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}-N-[4-(trifluoromethyl)tetrahydro-2H-pyran-4-yl]pyridine-2-carboxamide;

3-amino-5-[(3-fluoropiperidin-1-yl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-[(4-fluoropiperidin-1-yl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-[(4-methoxypiperidin-1-yl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-[(4-tert-butylpiperidin-1-yl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-N-(3,3,3-trifluoro-2-hydroxypropyl)-5-{[4-(trifluoromethoxy)piperidin-1-yl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-[(3,3-dimethylazetidin-1-yl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-{[(3R)-tetrahydrofuran-3-ylmethyl]sulfamoyl}-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-N-[2-hydroxy-3-(2,2,2-trifluoroethoxy)propyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(2-methoxyethyl)-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)(3,3-difluoropyrrolidin-1-yl)methanone;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl) [(3R)-3-fluoropyrrolidin-1-yl]methanone;

3-amino-N-[(1R,2S)-2-hydroxycyclopentyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridin-2-yl)[(3S)-3-fluoropyrrolidin-1-yl]methanone;

3-amino-N-[(3S)-1-methylpyrrolidin-3-yl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(3R)-1-methylpyrrolidin-3-yl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(2,2,2-trifluoroethyl)-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(1-methylazetidin-3-yl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-{methyl[4-(trifluoromethyl)benzyl]sulfamoyl}-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}-N-(3,3,3-trifluoropropyl)pyridine-2-carboxamide;

3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}-N-[2-hydroxy-3-(2,2,2-trifluoroethoxy)propyl]pyridine-2-carboxamide;

3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}-N-[3-(trifluoromethyl)oxetan-3-yl]pyridine-2-carboxamide;

3-amino-N-[(1S,2S)-2-hydroxycyclopentyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

rac-3-amino-N-[(3R,4S)-4-hydroxytetrahydro-2H-pyran-3-yl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(2-hydroxyethyl)-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

rac-3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}-N-[(3R,4S)-4-hydroxytetrahydro-2H-pyran-3-yl]pyridine-2-carboxamide;

3-amino-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}-N-(2-hydroxyethyl)pyridine-2-carboxamide;

3-amino-5-[(4-methoxyphenyl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-N-[2-hydroxy-3-(2-methoxyethoxy)propyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(3-methoxypropyl)-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(cyclopropylmethyl)-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(3-tert-butoxy-2-hydroxypropyl)-5-{[2-fluoro-4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-[methyl(3,3,3-trifluoropropyl)sulfamoyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methanone;

3-amino-N-(1-hydroxy-2-methylpropan-2-yl)-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(1-hydroxycyclopropyl)methyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)[(3R,4R)-3,4-dihydroxypyrrolidin-1-yl]methanone;

3-amino-N-[(4-hydroxy-1-methylpiperidin-4-yl)methyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)[3-(2,2-difluoroethoxy)azetidin-1-yl]methanone;

(3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)[3-(methoxymethyl)-3-methylazetidin-1-yl]methanone;

(3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl) [(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]methanone;

3-amino-N-[(2S)-1-hydroxybutan-2-yl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(3R,4S)-4-hydroxytetrahydro-2H-pyran-3-yl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(3,3,3-trifluoro-2-hydroxypropyl)-5-{[3-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-{[4-(propan-2-yloxy)phenyl]sulfonyl}-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-[(tetrahydrofuran-2-ylmethyl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-N-(2-hydroxy-3-methoxypropyl)-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[2-(trifluoromethoxy)ethyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(2,2-difluoro-3-hydroxypropyl)-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2S)-3-(cyclopropylmethoxy)-2-hydroxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2S)-2-hydroxy-3-(propan-2-yloxy)propyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-(phenyl sulfonyl)-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-[(4-methylphenyl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-{[4-(propan-2-yl)phenyl]sulfonyl}-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-5-[(4-tert-butylphenyl)sulfonyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide;

3-amino-N-[(2R)-2-hydroxy-3-(2,2,2-trifluoroethoxy)propyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2S)-2-hydroxy-3-(2,2,2-trifluoroethoxy)propyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-6-bromo-5-[(4-fluorophenyl)sulfonyl]-N-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-N-[(2R)-3-(cyclopropylmethoxy)-2-hydroxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2R)-2-hydroxy-3-(propan-2-yloxy)propyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-(phenylsulfonyl)-N-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-5-[(3-fluorophenyl)sulfonyl]-N-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]pyridine-2-carboxamide;

[3-amino-5-(phenylsulfonyl)pyridin-2-yl][3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone;

{3-amino-5-[(3-fluorophenyl)sulfonyl]pyridin-2-yl}[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone;

3-amino-N-[(3S,4R)-4-hydroxytetrahydro-2H-pyran-3-yl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-6-cyclopropyl-N-(2-hydroxyethyl)-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-6-(4-fluorophenyl)-5-[(4-fluorophenyl)sulfonyl]-N-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-6-cyclopropyl-N-(2-hydroxyethyl)-5-(phenylsulfonyl)pyridine-2-carboxamide;

3-amino-5-(cyclopentylsulfonyl)-6-(4-fluorophenyl)-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-6-(4-fluorophenyl)-5-[(2-hydroxyethyl)sulfonyl]-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-5-(ethyl sulfonyl)-6-(4-fluorophenyl)-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-6-(4-fluorophenyl)-N-[(2S)-2-hydroxypropyl]-5-(propan-2-ylsulfonyl)pyridine-2-carboxamide;

3-amino-6-(4-fluorophenyl)-N-[(2S)-2-hydroxypropyl]-5-[(2-methoxyethyl)sulfonyl]pyridine-2-carboxamide;

3-amino-N-[(2S)-2-hydroxypropyl]-5-{[(2S)-2-methylpyrrolidin-1-yl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-[(4-fluorobenzyl)sulfamoyl]-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-5-{[2-(hydroxymethyl)pyrrolidin-1-yl]sulfonyl}-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-5-[(4-fluorobenzyl)(methyl)sulfamoyl]-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-5-{[(2S)-2-methylpyrrolidin-1-yl]sulfonyl}-N-[2-oxo-2-(propan-2-ylamino)ethyl]pyridine-2-carboxamide;

1-[(3-amino-5-{[(2S)-2-methylpyrrolidin-1-yl]sulfonyl}pyridin-2-yl)carbonyl]azetidine-3-carboxamide;

(3-amino-5-{[(2S)-2-methylpyrrolidin-1-yl]sulfonyl}pyridin-2-yl)(3-hydroxyazetidin-1-yl)methanone;

3-amino-N-(3-fluoro-2-hydroxypropyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-6-cyclopropyl-5-[(4-fluorophenyl)sulfonyl]-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-6-cyclopropyl-5-(ethylsulfonyl)-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-N-(2-hydroxy-3-methoxypropyl)-5-{[(2S)-2-methylpyrrolidin-1-yl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2S)-2-hydroxypropyl]-5-[(2-methoxyethyl)(methyl)sulfamoyl]pyridine-2-carboxamide;

3-amino-5-[cyclobutyl(methyl)sulfamoyl]-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide;

3-amino-N-(3,3-difluoro-2-hydroxypropyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(2S)-2-hydroxypropyl]-6-methoxy-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(4-methoxypyrimidin-2-yl)methyl]-5-{[(2S)-2-methylpyrrolidin-1-yl]sulfonyl}pyridine-2-carboxamide;

3-amino-5-{[(2S)-2-methylpyrrolidin-1-yl]sulfonyl}-N-[(6-oxo-1,6-dihydropyrimidin-2-yl)methyl]pyridine-2-carboxamide;

3-amino-6-(dimethylamino)-N-[(2S)-2-hydroxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-6-(3-fluorophenoxy)-N-[(2S)-2-hydroxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-6-(cyclopropylamino)-N-[(2S)-2-hydroxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(methoxyacetyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carbohydrazide;

3-amino-N-(hydroxyacetyl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carbohydrazide;

3-amino-N-[(2S)-2-hydroxypropyl]-6-(2-methoxyethoxy)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-6-[2-(dimethylamino)ethoxy]-N-[(2S)-2-hydroxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-6-cyclopropyl-N-[(2S)-2-hydroxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-(1H-pyrazol-3-yl)-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[1-(hydroxymethyl)cyclopropyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

3-amino-N-[(1S,2S)-2-methoxycyclopentyl]-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridine-2-carboxamide;

(3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)(3-fluoro-3-methylazetidin-1-yl)methanone;

(3-amino-5-{[4-(trifluoromethyl)phenyl]sulfonyl}pyridin-2-yl)(6-oxa-2-azaspiro[3.5]non-2-yl)methanone;

3-amino-N-[(2R)-2-hydroxy-3-methoxypropyl]-5-(phenylsulfonyl)pyridine-2-carboxamide;

3-amino-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide; and

3-amino-6-bromo-5-[(4-fluorophenyl)sulfonyl]pyridine-2-carboxamide.

35. A pharmaceutical composition comprising a therapeutically effective amount of a compound of Formula I according to claim 1 , or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable carrier.

36. A compound of claim 1 or a pharmaceutically acceptable salt thereof, or a pharmaceutical composition of claim 34 , for use in medicine.

37. A compound of claim 1 or a pharmaceutically acceptable salt thereof, or a pharmaceutical composition of claim 34 , for use in treatment of cystic fibrosis.

38. A method for treating cystic fibrosis in a subject comprising administering a therapeutically effective amount of a compound of Formula I according to claim 1 , or a pharmaceutically acceptable salt thereof, to a subject in need thereof.

39. A pharmaceutical composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt thereof, and one or more correctors.

40. A method for treating cystic fibrosis in a subject comprising administering a compound of claim 1 or a pharmaceutically acceptable salt thereof, and one or more correctors, to a subject in need thereof.

41. A pharmaceutical composition comprising a compound of claim 1 or a pharmaceutically acceptable salt thereof, and one or more additional therapeutic agents.

42. The pharmaceutical composition of claim 41 wherein the additional therapeutic agents are selected from the group consisting of CFTR modulators and CFTR amplifiers.

43. The pharmaceutical composition of claim 41 wherein the additional therapeutic agents are CFTR modulators.

44. A method for treating cystic fibrosis in a subject comprising administering a compound of claim 1 or a pharmaceutically acceptable salt thereof, and one or more additional therapeutic agents.

45. The method of claim 44 wherein the additional therapeutic agents are selected from the group consisting of CFTR modulators and CFTR amplifiers.

46. The method of claim 44 the wherein the additional therapeutic agents are CFTR modulators.

47. 3 -amino-N-[(2S)-2-hydroxypropyl]-5-{[4-(trifluoromethoxy)phenyl]sulfonyl}pyridine-2-carboxamide or a pharmaceutically acceptable salt thereof.

Assignments (3)

MERGER Recorded May 13, 2020

From: ABBVIE S.Á.R.L.

To: ABBVIE OVERSEAS S.Á.R.L.

Reel/Frame 052647/0794 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 14, 2016

From: VAN DER PLAS, STEVEN EMIEL; KELGTERMANS, HANS; MARTINA, SÉBASTIEN LAURENT XAVIER; DE MUNCK, TOM ROGER LISETTE; DROPSIT MONTOVERT, SÉBASTIEN JEAN JACQUES CÉDRIC

To: GALAPAGOS NV

Reel/Frame 040038/0985 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 13, 2016

From: ALTENBACH, ROBERT J.; COWART, MARLON D.; GFESSER, GREGORY A.; WANG, XUEQING

To: ABBVIE S.Á.R.L.

Reel/Frame 039148/0427 →

Continuity (2)

Provisional Application 62169881 · Jun 2, 2015

Related Publication 20160355480A1 · Dec 8, 2016