IP Library › Granted Patent US 11,505,548
Granted Patent B2
US 11,505,548 · App. 16/858,410 · Granted Nov 22, 2022

Heterocyclic compounds and their use for treatment of helminthic infections and diseases

Inventors: Natalie Hawryluk (San Diego, CA); Stacie S. Canan (La Jolla, CA); Kevin R. Condroski (Lafayette, CO); Graham Kyne (Kalamazoo, MI); Matthew Bedore (Portage, MI); Sanjay Menon (Kalamazoo, MI)
Assignees: CELGENE CORPORATION; ZOETIS LLC
C07D417/14A61P33/10C07D413/14C07D471/04A61K31/165A61K31/732
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Quick Facts
Patent No.
US 11,505,548
App. No.
16/858,410
Granted
Nov 22, 2022
Kind
B2
Abstract

Provided herein are Heterocyclic compounds of formula I: and pharmaceutically acceptable salts, tautomers, isotopologues, or stereoisomers thereof, wherein W, X, Y, R 1 , R 2 , and R N are as defined herein, compositions comprising an effective amount of a Heterocyclic Compound, and methods for treating or preventing animal and human filarial worm infections and diseases.

Claims (390)

1. A compound of formula (II)

or pharmaceutically acceptable salts, tautomers, isotopologues, or stereoisomers thereof, wherein:

W is N, NR, or S;

X is N, NR, O, or S;

Y is N, NR, O, or S;

R 1 is 2-pyridyl, 3-pyridyl, pyrazinyl, or pyrimidyl, each unsubstituted or substituted with one or more substituents independently selected from halogen, CN, substituted or unsubstituted C 1-4 alkyl, substituted or unsubstituted C 3-7 cycloalkyl, substituted or unsubstituted 3-6 membered heterocyclyl, —NR 2 , —COOR, —OR 3 , —SO 2 NR 2 , —SO 2 (substituted or unsubstituted heterocyclyl), —N(R)CO(R 4 ), —CON(R 5 ) 2 , and substituted or unsubstituted C 6-10 aryl;

R 2 is

each unsubstituted or substituted with one or more substituents Z, wherein Z is independently selected from halogen, CN, substituted or unsubstituted C 1-4 alkyl, substituted or unsubstituted C 3-7 cycloalkyl, substituted or unsubstituted 3-6 membered heterocyclyl, —NR(substituted or unsubstituted C 3-7 cycloalkyl), —N(R)COR, —COOR, —SO 2 (C 1-3 alkyl), —SO 2 NR 2 , —SO 2 (substituted or unsubstituted heterocyclyl), —OR 6 , and —CON(R 7 ) 2 ; or two Z together with the carbons to which they are attached form a substituted or unsubstituted 5-6 membered heterocyclyl or substituted or unsubstituted C 5-6 heteroaryl;

Each R 3 is independently selected from substituted or unsubstituted C 1-5 alkyl, or substituted or unsubstituted 3-6 membered heterocyclyl;

Each R 4 is independently selected from substituted or unsubstituted C 1-5 alkyl, or substituted or unsubstituted C 3-6 cycloalkyl;

Each R 5 is independently selected from H, substituted or unsubstituted C 1-5 alkyl, substituted or unsubstituted C 3-6 cycloalkyl, and substituted or unsubstituted (C 1-3 alkyl)(C 3-6 cycloalkyl), or two R 5 and the nitrogen to which they are attached form a substituted or unsubstituted 3 to 6 membered heterocyclyl;

Each R 6 is independently selected from substituted or unsubstituted C 1-5 alkyl, substituted or unsubstituted C 3-6 cycloalkyl, —(C 1-3 alkyl)(substituted or unsubstituted C 3-6 cycloalkyl), or substituted or unsubstituted 3-8 membered heterocyclyl;

Each R 7 is independently selected from H, and substituted or unsubstituted C 1-5 alkyl, or two R 7 and the nitrogen to which they are attached form a substituted or unsubstituted 3 to 6 membered heterocyclyl;

R N is H, or substituted or unsubstituted C 1-5 alkyl; and

each R is independently selected from H and substituted or unsubstituted C 1-4 alkyl;

provided R 1 and R 2 are not both unsubstituted.

2. The compound of claim 1 , wherein the compound is a compound of formula (IIa)

or pharmaceutically acceptable salts, tautomers, isotopologues, or stereoisomers thereof.

3. The compound of claim 2 , wherein Y is N.

4. The compound of claim 1 , wherein R 1 is substituted with one or more substituents independently selected from halogen, CN, substituted or unsubstituted C 1-4 alkyl, substituted or unsubstituted C 3-7 cycloalkyl, substituted or unsubstituted 3-6 membered heterocyclyl, substituted or unsubstituted C 6-10 aryl, —NR 2 , —COOR, —OR 3 , —SO 2 NR 2 , —SO 2 (substituted or unsubstituted heterocyclyl), —N(R)CO(R 4 ), and —CON(R 5 ) 2 .

5. The compound of claim 1 , wherein R 1 is substituted with one or more substituents independently selected from Cl, F, Br, CN, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , —CH(CH 3 )CH 2 CH 3 , —CH 2 CH(CH 3 ) 2 , —C(CH 3 ) 3 , —CH 2 F, —CHF 2 , —CF 3 ; substituted or unsubstituted cycloalkyl selected from cyclopropyl, cyclobutyl, and cyclopentyl; substituted or unsubstituted heterocyclyl selected from pyrrolidyl, pyrrolidinonyl, piperidyl, piperazinyl, and morpholinyl; substituted or unsubstituted phenyl; —NH 2 , —NHCH 3 , —N(CH 3 ) 2 , —COOH, —COOCH 3 , —OR 3 , —SO 2 N(CH 3 ) 2 ; —S 02 (aziridinyl), —NHCO(R 4 ), —N(CH 3 )CO(R 4 ), —N(CH 2 CH 3 )CO(R 4 ), —N(CH 2 CH 2 CH 3 )CO(R 4 ), —N(CH 2 CH(CH 3 ) 2 )CO(R 4 ), and —CON(R 5 ) 2 .

6. The compound of claim 1 , wherein R 3 is —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , tetrahydrofuranyl, tetrahydropyranyl, piperidyl, or 1-(CH 3 )-piperidyl.

7. The compound of claim 1 , wherein R 4 is selected from —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 ; substituted or unsubstituted cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

8. The compound of claim 1 , wherein each R 5 is independently selected from H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 ; substituted or unsubstituted cycloalkyl selected from cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; substituted or unsubstituted (alkyl)-(cycloalkyl) selected from —CH 2 -cyclopropyl, —CH 2 -cyclobutyl, and —CH 2 -cyclopentyl; or two R 5 and the nitrogen to which they are attached form a pyrrolidyl.

9. The compound of claim 1 , wherein R 1 is 2-pyridyl, 3-pyridyl or pyrazinyl.

10. The compound of claim 1 , wherein R 2 is substituted with one or more substituents Z, wherein Z is independently selected from halogen, CN, substituted or unsubstituted C 1-4 alkyl, substituted or unsubstituted C 3-7 cycloalkyl, substituted or unsubstituted 3-6 membered heterocyclyl, —NR(substituted or unsubstituted C 3-7 cycloalkyl), —N(R)COR, —COOR, —SO 2 (C 1-3 alkyl), —SO 2 NR 2 , —SO 2 (substituted or unsubstituted heterocyclyl), —OR 6 , and —CON(R 7 ) 2 , or two Z together with the carbons to which they are attached form a substituted or unsubstituted 5-6 membered heterocyclyl or substituted or unsubstituted C 5-6 heteroaryl.

11. The compound of claim 1 , wherein R 2 is substituted with one or more substituents independently selected from Cl, F, Br, CN, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , —CH(CH 3 )CH 2 CH 3 , —C(CH 3 ) 3 , —CH 2 F, —CHF 2 , —CF 3 ; substituted or unsubstituted cycloalkyl selected from cyclopropyl, cyclobutyl, and cyclopentyl; substituted or unsubstituted heterocyclyl selected from piperidyl, piperazinyl, morpholinyl and thiomorpholinyl; —NH(bicyclo[1.1.1]pentyl), —N(CH 3 )(bicyclo[1.1.1]pentyl); —NHCO(CH 3 ), —N(CH 3 )CO(CH 3 ), —NHCO(CH 2 CH 3 ), —N(CH 3 )CO(CH 2 CH 3 ); —COOH, —COOCH 3 ; —SO 2 CH 3 , —SO 2 CH 2 CH 3 ; —SO 2 NHCH 3 , —SO 2 N(CH 3 ) 2 ; —SO 2 (aziridinyl), —SO 2 (piperidyl), —SO 2 (1-methyl-aziridinyl), —SO 2 (1-methyl-piperidyl), SO 2 (1-cyclopropyl-piperidyl), —OR 6 , and —CON(R 7 ) 2 .

12. The compound of claim 1 , wherein R 6 is selected from —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH(CH 3 )CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , —CH(CH 3 )CH 2 CH 3 , —C(CH 3 ) 3 , —CH 2 F, —CHF 2 , —CF 3 , —CH 2 CH 2 F, —CH 2 CHF 2 , —CH 2 CF 3 , cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, difluorocyclobutyl, difluorocyclopentyl, —CH 2 -cyclopropyl, —CH 2 -cyclobutyl, oxetanyl, piperidyl, fluoropiperidyl, -(1-methyl-piperidyl), -(1-isopropyl-piperidyl), -(1-isopropyl-fluoropiperidyl), -(1-isopropyl-difluoropiperidyl), -(1-cyclopropyl-piperidyl), -(1-cyclobutyl-piperidyl), -(1-cyclopentyl-piperidyl), -(1-cyclopropyl-fluoropiperidyl), -(1-cyclopropyl-difluoropiperidyl), -(1-CH 2 -cyclopropyl-piperidyl), -(1-acetyl-piperidyl), -(1-(COCH(CH 3 ) 2 )-piperidyl), tetrahydrofuranyl, tetrahydropyranyl, -(2-methyl-2-azaspiro[3.3]heptyl), -(2-cyclopropyl-2-azaspiro[3.3]heptyl), and -(6-methyl-6-azaspiro[3.4]octyl).

13. The compound of claim 1 , wherein each R 7 is independently selected from —H, —CH 3 , —CH 2 CH 3 , —CH 2 F, —CHF 2 , —CF 3 , —CH 2 CH 2 F, —CH 2 CHF 2 , and —CH 2 CF 3 , or two R 7 and the nitrogen to which they are attached form a heterocycle selected from unsubstituted or substituted pyrrolidyl, piperidyl, piperazinyl, or morpholinyl.

14. The compound of claim 1 , wherein R 2 is 2-pyridyl substituted with two substituents Z, wherein the two Z together with the carbons to which they are attached form a substituted or unsubstituted 5-membered heterocyclyl.

15. The compound of claim 14 , wherein the two Z together with the carbons to which they are attached form a substituted or unsubstituted dihydropyrrolyl or dihydrofuryl.

16. The compound of claim 15 , wherein R 2 is a substituted or unsubstituted 6,7-dihydro-5H-pyrrolo[3,4-b]pyridyl; 2,3-dihydro-1H-pyrrolo[2,3-c]pyridyl; 2,3-dihydro-1H-pyrrolo[3,4-c]pyridyl; 2-oxo-2,3-dihydro-1H-pyrrolo[2,3-c]pyridyl; or 2,3-dihydrofuro[2,3-c]pyridyl.

17. The compound of claim 1 , wherein the compound is selected from:

3-(pyridin-2-yl)-N-(5- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

N-(5-methoxypyridin-2-yl)- 3-(pyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(pyridin-2-yl)-N-(5- (trifluoromethyl)pyridin-3- yl)-1,2,4-thiadiazol-5-amine

N-(5-(piperazin-1-yl)pyridin- 2-yl)-3-(pyridin-2-yl)-1,2,4- thiadiazol-5-amine

N-(5-morpholinopyridin-2- yl)-3-(pyridin-2-yl)-1,2,4- thiadiazol-5-amine

N-(5-(piperidin-1-yl)pyridin- 2-yl)-3-(pyridin-2-yl)-1,2,4- thiadiazol-5-amine

N-(5-(4-methylpiperazin-1- yl)pyridin-2-yl)-3-(pyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(pyridin-2-yl)-N-(5- (pyrrolidin-1-yl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(pyridin-2-yl)-N-(5- (tetrahydro-2H-pyran-4- yloxy)pyridin-2-yl)-1,2,4- thiadiazol-5-amine

N-(5-(piperidin-4- yloxy)pyridin-2-yl)-3- (pyridin-2-yl)-1,2,4- thiadiazol-5-amine

N-(5-(1-methylpiperidin-4- yloxy)pyridin-2-yl)-3- (pyridin-2-yl)-1,2,4- thiadiazol-5-amine

N-(3-fluoropyridin-2-yl)-3- (4-methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

N-(4-methylpyridin-2-yl)-3- (3-(trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

N-(3-fluoropyridin-2-yl)-3- (4-methylpyridin-2-yl)-1,2,4- oxadiazol-5-amine

N-(3-methylpyridin-2-yl)-3- (5-(tetrahydro-2H-pyran-4- yloxy)pyridin-2-yl)-1,2,4- thiadiazol-5-amine

N-(3-methylpyridin-2-yl)-3- (5-(tetrahydro-2H-pyran-4- yloxy)pyridin-2-yl)-1,2,4- oxadiazol-5-amine

N,N-dimethyl-6-(5-(3- methylpyridin-2-ylamino)- 1,2,4-thiadiazol-3- yl)nicotinamide

3-(5-(1-methylpiperidin-4- yloxy)pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-isopropoxypyridin-2-yl)- N-(3-methylpyridin-2-yl)- 1,2,4-thiadiazol-5-amine

3-(5-isopropoxypyridin-2-yl)- N-(3-methylpyridin-2-yl)- 1,2,4-oxadiazol-5-amine

3-(5-(1-methylpiperidin-4- yloxy)pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,2,4- oxadiazol-5-amine

N,N-dimethyl-2-(5-(3- methylpyridin-2-ylamino)- 1,2,4-thiadiazol-3- yl)isonicotinamide

N3-methyl-N2-(3-(4- methylpyridin-2-yl)-1,2,4- thiadiazol-5-yl)pyridine-2,3- diamine

N-(3-methoxypyridin-2-yl)- 3-(4-methylpyridin-2-yl)- 1,2,4-thiadiazol-5-amine

N-(5-ethoxypyridin-2-yl)-3- (3-fluoropyridin-2-yl)-1,2,4- oxadiazol-5-amine

4-(6-(5-((3-methylpyridin-2- yl)amino)-1,2,4-thiadiazol-3- yl)pyridin-3- yl)thiomorpholine 1,1- dioxide

3-(3-fluoropyridin-2-yl)-N- (4-(trifluoromethyl)pyridin-2- yl)-1,2,4-oxadiazol-5-amine

3-(pyridin-2-yl)-N-(4- (trifluoromethyl)pyridin-2- yl)-1,2,4-oxadiazol-5-amine

N-(6-(5-(3-methylpyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)pyridin-3-yl)acetamide

N-(3-fluoropyridin-2-yl)-3- (5-(1-methylpiperidin-4- yloxy)pyridin-2-yl)-1,2,4- thiadiazol-5-amine

N,N-dimethyl-6-(5-(3- methylpyridin-2-ylamino)- 1,2,4-thiadiazol-3- yl)pyridine-3-sulfonamide

5-(3-methylpyridin-2-yl)-N- (pyridin-2-yl)-1,3,4- oxadiazol-2-amine

N,3-di(pyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-(1-methylpiperidin-4- yloxy)pyridin-2-yl)-N-(4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

N-(5-ethoxypyridin-2-yl)-3- (4-methoxypyridin-2-yl)- 1,2,4-oxadiazol-5-amine

3-(5-(1-methylpiperidin-4- yloxy)pyridin-2-yl)-N- (pyrimidin-2-yl)-1,2,4- thiadiazol-5-amine

3-(4-methylpyridin-2-yl)-N- (3-(trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(5-cyclopropoxypyridin-2- yl)-N-(3-methylpyridin-2-yl)- 1,2,4-thiadiazol-5-amine

3-(5-(1-methylpiperidin-4- yloxy)pyrimidin-2-yl)-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

2-(5-(3-methylpyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)isonicotinonitrile

N-(5-(3-methylpyridin-2-yl)- 4H-1,2,4-triazol-3-yl)pyridin- 2-amine

3-(3-methylpyridin-2-yl)-N- (5-(pyrrolidin-1-yl)pyridin-2- yl)-1,2,4-oxadiazol-5-amine

3-(5-methoxypyridin-2-yl)- N-(5-(tetrahydro-2H-pyran-4- yloxy)pyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(4-(1-methylpiperidin-4- yl)pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-(1-cyclopropylpiperidin- 4-yloxy)pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-methoxypyridin-2-yl)- N-(4-(tetrahydro-2H-pyran-4- yloxy)pyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-methoxypyridin-2-yl)- N-(4-(tetrahydro-2H-pyran-4- yloxy)pyridin-2-yl)-1,2,4- oxadiazol-5-amine

3-(5-(1-methylpiperidin-4- yl)pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

N-(5-(1-methylpiperidin-4- yl)pyridin-2-yl)-3-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-methoxypyridin-2-yl)- N-(5-(1-methylpiperidin-4- yl)pyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(3-methylpyridin-2-yl)-N- (5-(pyrrolidin-1-yl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

N-(3-methylpyridin-2-yl)-3- (5-(trifluoromethoxy)pyridin- 2-yl)-1,2,4-thiadiazol-5- amine

N3-methyl-N2-(3-(5-(1- methylpiperidin-4- yloxy)pyridin-2-yl)-1,2,4- thiadiazol-5-yl)pyridine-2,3- diamine

3-(5-isopropoxypyridin-2-yl)- N-(3- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(5-(1-methylpiperidin-4- yloxy)pyridin-2-yl)-N-(3- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

N2-(3-(5-isopropoxypyridin- 2-yl)-1,2,4-thiadiazol-5-yl)- N3,N3-dimethylpyridine-2,3- diamine

(4-methylpiperazin-1-yl)(6- (5-(3-methylpyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)pyridin-3-yl)methanone

(6-(5-(3-methylpyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)pyridin-3- yl)(morpholino)methanone

N3,N3-dimethyl-N2-(3-(5-(1- methylpiperidin-4- yloxy)pyridin-2-yl)-1,2,4- thiadiazol-5-yl)pyridine-2,3- diamine

6-(5-(3-methylpyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)-N-(2,2,2- trifluoroethyl)nicotinamide

(6-(5-(3-methylpyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)pyridin-3-yl)(pyrrolidin-1- yl)methanone

3-(4-(1-methylpiperidin-4- yloxy)pyridin-2-yl)-N-(3- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

5-(5-(1-methylpiperidin-4- yloxy)pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,3,4- thiadiazol-2-amine

5-(5-isopropoxypyridin-2-yl)- N-(3-methylpyridin-2-yl)- 1,3,4-thiadiazol-2-amine

3-(4-cyclopropoxypyridin-2- yl)-N-(3-methylpyridin-2-yl)- 1,2,4-thiadiazol-5-amine

N-(5-isopropyl-4- (trifluoromethyl)pyridin-2- yl)-3-(5-methoxypyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(4-isopropylpyridin-2-yl)- N-(3- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

N-(5-cyclopentylpyridin-2- yl)-3-(5-methoxypyridin-2- yl)-1,2,4-thiadiazol-5-amine

N-(3-(5-isopropoxypyridin-2- yl)-1H-1,2,4-triazol-5-yl)-3- methylpyridin-2-amine

N-(3-(5-isopropoxypyridin-2- yl)-1H-1,2,4-triazol-5-yl)-3- (trifluoromethyl)pyridin-2- amine

3-methyl-N-(3-(5-(1- methylpiperidin-4- yloxy)pyridin-2-yl)-1H-1,2,4- triazol-5-yl)pyridin-2-amine

3-(5-(1-cyclopentylpiperidin- 4-yloxy)pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5- (cyclopropylmethoxy)pyridin- 2-yl)-N-(3-methylpyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(5-cyclopropoxypyridin-2- yl)-N-(3-isopropylpyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(5-(1- (cyclopropylmethyl)piperidin- 4-yloxy)pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

N-(3-cyclopropylpyridin-2- yl)-3-(5-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(5-(6-methyl-6- azaspiro[3.4]octan-2- yloxy)pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

N2-(3-(5- cyclopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5-yl)-N3,N3- dimethylpyridine-2,3- diamine

N-(3-methylpyridin-2-yl)-3- (5-(methylsulfonyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(5-cyclopropoxypyridin-2- yl)-N-(3-methoxypyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(5-isopropoxypyridin-2-yl)- N-(3-methoxypyridin-2-yl)- 1,2,4-thiadiazol-5-amine

3-(5-(2-cyclopropyl-2- azaspiro[3.3]heptan-6- yloxy)pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-(1-cyclopropyl-3,3- difluoropiperidin-4- yloxy)pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(4-cyclopropylpyridin-2- yl)-N-(3- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(4-cyclopropylpyridin-2- yl)-N-(4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(4-isopropylpyridin-2-yl)- N-(4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(5-(1-cyclopropyl-3,3- difluoropiperidin-4- yloxy)pyridin-2-yl)-N-(3- isopropylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-(2-methyl-2- azaspiro[3.3]heptan-6- yloxy)pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-((3S,4R)-1-cyclopropyl- 3-fluoropiperidin-4- yloxy)pyridin-2-yl)-N-(3- isopropylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-((3R,4R)-1-cyclopropyl- 3-fluoropiperidin-4- yloxy)pyridin-2-yl)-N-(3- isopropylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-((3R,4R)-1-cyclopropyl- 3-fluoropiperidin-4- yloxy)pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-((3S)-1-cyclopropyl-3- fluoropiperidin-4- yloxy)pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-cyclopropoxy-3- (trifluoromethyl)pyridin-2- yl)-N-(3-methylpyridin-2-yl)- 1,2,4-thiadiazol-5-amine

3-(3-isopropoxypyridin-2-yl)- N-(4-(pyrrolidin-1- yl)pyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-cyclopropoxypyridin-2- yl)-N-(5-isopropyl-4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(4-cyclopropoxypyridin-2- yl)-N-(5-isopropyl-4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(3-cyclopropoxypyridin-2- yl)-N-(5-isopropyl-4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(5-isopropoxypyridin-2-yl)- N-methyl-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

N-(4-(pyrrolidin-1- yl)pyridin-2-yl)-3-(4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(5-(1-methylpiperidin-4- ylsulfonyl)pyridin-2-yl)-N- (3-methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

N3,N3-dimethyl-N2-(3-(5- (2,2,2- trifluoroethoxy)pyridin-2-yl)- 1,2,4-thiadiazol-5- yl)pyridine-2,3-diamine

3-(5-cyclopropoxy-4- (trifluoromethyl)pyridin-2- yl)-N-(3-methylpyridin-2-yl)- 1,2,4-thiadiazol-5-amine

N-(5-(5- cyclopropoxypyridin-2-yl)-1- methyl-1H-1,2,4-triazol-3- yl)-3-methylpyridin-2-amine

5-(4-isopropylpyridin-2-yl)- N-(3-methylpyridin-2-yl)- 1,3,4-oxadiazol-2-amine

N-(3-methoxypyridin-2-yl)- 3-(5-(2,2,2- trifluoroethoxy)pyridin-2-yl)- 1,2,4-thiadiazol-5-amine

6-(3-(5-cyclopropoxypyridin- 2-yl)-1,2,4-thiadiazol-5- ylamino)-N- (cyclopropylmethyl)nicotinamide

6-(3-(5-cyclopropoxypyridin- 2-yl)-1,2,4-thiadiazol-5- ylamino)-N-(3,3- difluorocyclobutyl)nicotinamide

N2-(3-(5-isopropoxypyridin- 2-yl)-1,2,4-thiadiazol-5-yl)- N3-methylpyridine-2,3- diamine

3-(5-cyclopropoxy-4- (trifluoromethyl)pyridin-2- yl)-N-(3-isopropylpyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(5-(cyclopropylmethoxy)- 4-(trifluoromethyl)pyridin-2- yl)-N-(3-methylpyridin-2-yl)- 1,2,4-thiadiazol-5-amine

N2-(3-(5-cyclopropoxy-4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-yl)- N3,N3-dimethylpyridine-2,3- diamine

1-(4-(6-(3-(5- cyclopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3- yl)piperazin-1-yl)ethanone

1-(4-(6-(3-(5- cyclopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3- yl)piperazin-1-yl)-3,3,3- trifluoropropan-1-one

3-(6-(cyclopropylmethyl)- 6,7-dihydro-5H-pyrrolo[3,4- b]pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-isopropoxypyridin-2-yl)- N-(3-isopropylpyridin-2-yl)- 1,2,4-thiadiazol-5-amine

3-(5-isopropoxypyridin-2-yl)- N-(3-(pyrrolidin-1- yl)pyridin-2-yl)-1,2,4- thiadiazol-5-amine

N2-(3-(3- cyclopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5-yl)-N3,N3- dimethylpyridine-2,3- diamine

N2-(3-(5- (cyclopropylmethoxy)pyridin- 2-yl)-1,2,4-thiadiazol-5-yl)- N3,N3-dimethylpyridine-2,3- diamine

3-(5-isopropoxypyridin-2-yl)- N-(5-isopropyl-4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

N2-(3-(5- (difluoromethoxy)pyridin-2- yl)-1,2,4-thiadiazol-5-yl)- N3,N3-dimethylpyridine-2,3- diamine

N2-(3-(5-fluoropyridin-2-yl)- 1,2,4-thiadiazol-5-yl)-N3,N3- dimethylpyridine-2,3- diamine

N2-(3-(5-(1-cyclopropyl-3,3- difluoropiperidin-4- yloxy)pyridin-2-yl)-1,2,4- thiadiazol-5-yl)-N3- methylpyridine-2,3-diamine

N2-(3-(5-(1-cyclopropyl-3,3- difluoropiperidin-4- yloxy)pyridin-2-yl)-1,2,4- thiadiazol-5-yl)-N3,N3- dimethylpyridine-2,3- diamine

3-(5-isopropoxypyrazin-2- yl)-N-(3-methylpyridin-2-yl)- 1,2,4-thiadiazol-5-amine

3-(5-methoxypyrazin-2-yl)- N-(3-methylpyridin-2-yl)- 1,2,4-thiadiazol-5-amine

N2-(3-(5-isopropoxypyrazin- 2-yl)-1,2,4-thiadiazol-5-yl)- N3,N3-dimethylpyridine-2,3- diamine

3-(5- (difluoromethoxy)pyridin-2- yl)-N-(3-isopropylpyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(5-fluoropyridin-2-yl)-N- (3-isopropylpyridin-2-yl)- 1,2,4-thiadiazol-5-amine

3-(5-(1-cyclopropyl-3,3- difluoropiperidin-4- yloxy)pyridin-2-yl)-N-(3- methoxypyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-isopropoxypyridin-2-yl)- N-(3-isopropylpyridin-2-yl)- N-methyl-1,2,4-thiadiazol-5- amine

N-ethyl-3-(5- isopropoxypyridin-2-yl)-N- (3-methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

N2-(5-(5-isopropoxypyridin- 2-yl)-1,3,4-oxadiazol-2-yl)- N3,N3-dimethylpyridine-2,3- diamine

N2-(3-(5-isopropoxypyridin- 2-yl)-1,2,4-oxadiazol-5-yl)- N3,N3-dimethylpyridine-2,3- diamine

3-(5-cyclopropoxy-4- (trifluoromethyl)pyridin-2- yl)-N-(3-methoxypyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(5-isopropoxypyridin-2-yl)- N-(3-methylpyrazin-2-yl)- 1,2,4-thiadiazol-5-amine

N2-(3-(5-(3,3- difluorocyclobutoxy)pyridin- 2-yl)-1,2,4-thiadiazol-5-yl)- N3,N3-dimethylpyridine-2,3- diamine

3-(5-(3,3- difluorocyclobutoxy)pyridin- 2-yl)-N-(3-methoxypyridin- 2-yl)-1,2,4-thiadiazol-5- amine-

3-(5-isopropoxypyridin-2-yl)- N-isopropyl-N-(3- methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

N2-(3-(5-isopropoxypyridin- 2-yl)-1,2,4-thiadiazol-5-yl)- N2,N3,N3-trimethylpyridine- 2,3-diamine

N2-(3-(5-isopropoxypyridin- 2-yl)-1H-1,2,4-triazol-5-yl)- N3,N3-dimethylpyridine-2,3- diamine

N3,N3-dimethyl-N2-(3-(5-(1- methylazetidin-3- ylsulfonyl)pyridin-2-yl)- 1,2,4-thiadiazol-5- yl)pyridine-2,3-diamine

N3,N3-dimethyl-N2-(3-(5-(1- methylpiperidin-4- ylsulfonyl)pyridin-2-yl)- 1,2,4-thiadiazol-5- yl)pyridine-2,3-diamine

5-isopropyl-N-(1-methyl-5- (pyridin-2-yl)-1H-1,2,4- triazol-3-yl)-4- (trifluoromethyl)pyridin-2- amine

N2-(3-(5-isopropoxypyridin- 2-yl)-1,2,4-thiadiazol-5-yl)- N3,N3-dimethylpyrazine-2,3- diamine

N2-(3-(5-(1- cyclopropylpiperidin-4- ylsulfonyl)pyridin-2-yl)- 1,2,4-thiadiazol-5-yl)-N3,N3- dimethylpyridine-2,3- diamine

N-(5-(4-isopropoxypyridin-2- yl)-1-methyl-1H-1,2,4- triazol-3-yl)-5-isopropyl-4- (trifluoromethyl)pyridin-2- amine

N2-(3-(4-isopropoxy-5- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-yl)- N3,N3-dimethylpyridine-2,3- diamine

N-(5-(3-isopropoxypyridin-2- yl)-1-methyl-1H-1,2,4- triazol-3-yl)-5-isopropyl-4- (trifluoromethyl)pyridin-2- amine

N2-(3-(5-isobutoxypyridin-2- yl)-1,2,4-thiadiazol-5-yl)- N3,N3-dimethylpyridine-2,3- diamine

N2-(3-(5-isobutoxypyrazin-2- yl)-1,2,4-thiadiazol-5-yl)- N3,N3-dimethylpyridine-2,3- diamine

3-(4-cyclopropoxy-5- (trifluoromethyl)pyridin-2- yl)-N-(3-methylpyridin-2-yl)- 1,2,4-thiadiazol-5-amine

3-(4-isopropoxy-5- (trifluoromethyl)pyridin-2- yl)-N-(3-methylpyridin-2-yl)- 1,2,4-thiadiazol-5-amine

N2-(3-(4-cyclopropoxy-5- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-yl)- N3,N3-dimethylpyridine-2,3- diamine

5-(5-isopropoxypyridin-2-yl)- N-(5-isopropyl-4- (trifluoromethyl)pyridin-2- yl)-1,3,4-oxadiazol-2-amine

N2-(3-(6- isopropoxypyridazin-3-yl)- 1,2,4-thiadiazol-5-yl)-N3,N3- dimethylpyridine-2,3- diamine

N2-(3-(5-isopropoxy-4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-yl)- N3,N3-dimethylpyridine-2,3- diamine

N-(2-(3-(5- isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylacetamide

N2-(5-(5-methoxypyrazin-2- yl)-1,3,4-oxadiazol-2-yl)- N3,N3-dimethylpyridine-2,3- diamine

N2-(3-(5-isopropoxypyridin- 2-yl)-1,2,4-thiadiazol-5-yl)- N2,N3-dimethylpyridine-2,3- diamine

N2-(5-(5-isopropoxy-4- (trifluoromethyl)pyridin-2- yl)-1,3,4-oxadiazol-2-yl)- N3,N3-dimethylpyridine-2,3- diamine

N-(2-(3-(5- isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3- yl)acetamide

N3,N3-dimethyl-N2-(3-(1- methyl-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5- yl)pyridine-2,3-diamine

N3,N3-dimethyl-N2-(3-(2- methyl-2,3-dihydro-1H- pyrrolo[3,4-c]pyridin-4-yl)- 1,2,4-thiadiazol-5- yl)pyridine-2,3-diamine

2-(3-(5-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)nicotinamide

3-(5-isopropoxypyridin-2-yl)- N-(5-isopropyl-3- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(5-isopropoxypyridin-2-yl)- N-(5-isopropyl-3- methoxypyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(5-isopropoxy-4- (trifluoromethyl)pyridin-2- yl)-N-(3-methoxypyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(5-isopropoxy-4- (trifluoromethyl)pyridin-2- yl)-N-(3-isopropylpyridin-2- yl)-1,2,4-thiadiazol-5-amine

N-(2-(3-(5- isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylisobutyramide

N-(2-(3-(5- isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylcyclopropanecarboxamide

N-(2-(3-(5- isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylcyclobutanecarboxamide

N-(2-(3-(5- isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylcyclopentanecarboxamide

5-(4-isopropoxypyridin-2-yl)- N-(3-methylpyridin-2-yl)- 1,3,4-thiadiazol-2-amine

5-(4-methoxypyridin-2-yl)- N-(5- (trifluoromethyl)pyridin-2- yl)-1,3,4-thiadiazol-2-amine

5-(4-isopropoxypyridin-2-yl)- N-(5-methoxypyridin-2-yl)- 1,3,4-thiadiazol-2-amine

3-(4-methoxypyridin-2-yl)- N-(5- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

N-(5-isopropylpyridin-2-yl)- 3-(4-methoxypyridin-2-yl)- 1,2,4-thiadiazol-5-amine

1-(2-(3-(5- isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3- yl)pyrrolidin-2-one

1-(2-(3-(5-isopropoxy-4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)pyridin-3- yl)pyrrolidin-2-one

5-(5-isopropoxypyridin-2-yl)- N-(5-methoxypyridin-2-yl)- 1,3,4-oxadiazol-2-amine

5-(5-isopropoxypyridin-2-yl)- N-(5-isopropylpyridin-2-yl)- 1,3,4-thiadiazol-2-amine

N-(5-isopropyl-4- (trifluoromethyl)pyridin-2- yl)-3-(4-methoxypyridin-2- yl)-1,2,4-thiadiazol-5-amine

3-(4-(cyclohexyloxy)pyridin- 2-yl)-N-(5-methoxypyridin- 2-yl)-1,2,4-thiadiazol-5- amine

N-(5-isopropoxypyridin-2- yl)-3-(4-methoxypyridin-2- yl)-1,2,4-thiadiazol-5-amine

N-(5-isopropylpyridin-2-yl)- 3-(5-methoxypyridin-2-yl)- 1,2,4-thiadiazol-5-amine

N-(2-(3-(5-isopropoxy-4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylcyclopropanecarboxamide

N-(2-(3-(5-isopropoxy-4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylacetamide

2-(3-(5-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)-N,N- dimethylnicotinamide

2-(3-(5-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)-N- methylnicotinamide

(2-(3-(5-isopropoxypyridin- 2-yl)-1,2,4-thiadiazol-5- ylamino)pyridin-3- yl)(pyrrolidin-1- yl)methanone

N-(3,3-difluorocyclobutyl)-2- (3-(5-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)-N- methylnicotinamide

5-isopropoxy-N,N-dimethyl- 2-(5-(3-methylpyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)isonicotinamide

5-isopropoxy-2-(5-(3- isopropylpyridin-2-ylamino)- 1,2,4-thiadiazol-3-yl)-N,N- dimethylisonicotinamide

5-isopropoxy-N,N-dimethyl- 2-(5-(3-(2-oxopyrrolidin-1- yl)pyridin-2-ylamino)-1,2,4- thiadiazol-3- yl)isonicotinamide

N-(3,3-difluorocyclobutyl)-6- (3-(5-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)-5- isopropylnicotinamide

methyl 5-isopropoxy-2-(5-(3- methylpyridin-2-ylamino)- 1,2,4-thiadiazol-3- yl)isonicotinate

methyl 5-isopropoxy-2-(5-(3- isopropylpyridin-2-ylamino)- 1,2,4-thiadiazol-3- yl)isonicotinate

5-isopropoxy-2-(5-(3- isopropylpyridin-2-ylamino)- 1,2,4-thiadiazol-3- yl)isonicotinamide

N-methyl-N-(2-(3-(5- (tetrahydro-2H-pyran-4- yloxy)pyridin-2-yl)-1,2,4- thiadiazol-5-ylamino)pyridin- 3-yl)acetamide

5-isopropoxy-2-(5-(3- methylpyridin-2-ylamino)- 1,2,4-thiadiazol-3- yl)isonicotinonitrile

5-isopropoxy-2-(5-(3- isopropylpyridin-2-ylamino)- 1,2,4-thiadiazol-3- yl)isonicotinonitrile

N-methyl-N-(2-(3-(1-methyl- 2,3-dihydro-1H-pyrrolo[2,3- c]pyridin-5-yl)-1,2,4- thiadiazol-5-ylamino)pyridin- 3-yl)acetamide

N-(2-(3-(5-(3,3-difluoro-1- isopropylpiperidin-4- yloxy)pyridin-2-yl)-1,2,4- thiadiazol-5-ylamino)pyridin- 3-yl)-N-methylacetamide

1-(2-(3-(5- (bicyclo[1.1.1]pentan-1- ylamino)pyridin-2-yl)-1,2,4- thiadiazol-5-ylamino)pyridin- 3-yl)pyrrolidin-2-one

N-(2-(3-(5- isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- isopropylacetamide

N-(2-(3-(1-isopropyl-2,3- dihydro-1H-pyrrolo[2,3- c]pyridin-5-yl)-1,2,4- thiadiazol-5-ylamino)pyridin- 3-yl)-N-methylacetamide

N-(2-(3-(5- (bicyclo[1.1.1]pentan-1- ylamino)pyridin-2-yl)-1,2,4- thiadiazol-5-ylamino)pyridin- 3-yl)-N-methylacetamide

N-methyl-N-(2-(3-(4- methylpyridin-2-yl)-1,2,4- thiadiazol-5-ylamino)pyridin- 3-yl)acetamide

3-(5-methoxypyridin-2-yl)- N-(5- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

N-(5-isopropyl-4- (trifluoromethyl)pyridin-2- yl)-3-(3-methoxypyridin-2- yl)-1,2,4-thiadiazol-5-amine

5-(4-isopropoxypyridin-2-yl)- N-(3-methylpyridin-2-yl)- 1,3,4-oxadiazol-2-amine

5-(4-isopropoxypyridin-2-yl)- N-(5-methoxypyridin-2-yl)- 1,3,4-oxadiazol-2-amine

3-(4-(cyclohexyloxy)pyridin- 2-yl)-N-(5- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5-amine

5-(4-(cyclohexyloxy)pyridin- 2-yl)-N-(5-methoxypyridin- 2-yl)-1,3,4-oxadiazol-2- amine

N-(5-isopropoxypyridin-2- yl)-3-(5-methoxypyridin-2- yl)-1,2,4-thiadiazol-5-amine

N-(2-(3-(4-isopropylpyridin- 2-yl)-1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylacetamide

N-(2-(3-(4-isopropylpyridin- 2-yl)-1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylcyclopropanecarboxamide

5-isopropoxy-N,N-dimethyl- 2-(5-(3- (trifluoromethyl)pyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)isonicotinamide

5-isopropoxy-2-(5-(5- isopropyl-3- (trifluoromethyl)pyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)-N,N- dimethylisonicotinamide

5-isopropoxy-2-(5-(3- (trifluoromethyl)pyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)isonicotinamide

5-isopropoxy-2-(5-(5- isopropyl-3- (trifluoromethyl)pyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)isonicotinamide

N-(2-(3-(5- isopropoxypyridin-2-yl)- 1,2,4-oxadiazol-5- ylamino)pyridin-3-yl)-N- methylacetamide

N-(2-(3-(4-isopropyl-5- methylpyridin-2-yl)-1,2,4- thiadiazol-5-ylamino)pyridin- 3-yl)-N-methylacetamide

N-(2-(3-(5- isopropoxypyridin-2-yl)- 1,2,4-oxadiazol-5- ylamino)pyridin-3-yl)-N- methylcyclopropanecarboxamide

2-(3-(5-isopropoxy-4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)-N,N- dimethylnicotinamide

N-(2-(3-(4-cyano-5- isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylacetamide

N-(2-(3-(4-cyano-5- isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylcyclopropanecarboxamide

N-(2-(3-(5-ethoxy-4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylacetamide

N,N-dimethyl-2-(3-(1- methyl-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5- ylamino)nicotinamide

4-isopropyl-N,N-dimethyl-6- (5-(3-methylpyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)nicotinamide

6-(3-(5-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)-5- methylnicotinonitrile

5-(4-isopropoxypyridin-2-yl)- N-(5-isopropylpyridin-2-yl)- 1,3,4-thiadiazol-2-amine

5-(4-(cyclohexyloxy)pyridin- 2-yl)-N-(5-methoxypyridin- 2-yl)-1,3,4-thiadiazol-2- amine

5-(4-(1-methylpiperidin-4- yloxy)pyridin-2-yl)-N-(3- methylpyridin-2-yl)-1,3,4- thiadiazol-2-amine

N-(4-phenylpyridin-2-yl)-5- (pyridin-2-yl)-1,3,4- oxadiazol-2-amine

5-(3-methylpyridin-2-yl)-N- (4-methylpyridin-2-yl)-1,3,4- oxadiazol-2-amine

N-(4-phenylpyridin-2-yl)-3- (pyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(3-methylpyridin-2-yl)-N- (4-methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

3-(3-methylpyridin-2-yl)-N- (4-methylpyridin-2-yl)-1,2,4- oxadiazol-5-amine

N-(4-phenylpyridin-2-yl)-5- (pyridin-2-yl)-1,3,4- thiadiazol-2-amine

4-phenyl-N-(5-(pyridin-2-yl)- 4H-1,2,4-triazol-3-yl)pyridin- 2-amine

4-methyl-N-(5-(3- methylpyridin-2-yl)-4H- 1,2,4-triazol-3-yl)pyridin-2- amine

N-(4-isopropoxypyridin-2- yl)-5-(5-methoxypyridin-2- yl)-1,3,4-thiadiazol-2-amine

5-(3-methylpyridin-2-yl)-N- (4-methylpyridin-2-yl)-1,3,4- thiadiazol-2-amine

N-(4-isopropoxypyridin-2- yl)-3-(5-methoxypyridin-2- yl)-1,2,4-thiadiazol-5-amine

N-(4-phenylpyridin-2-yl)-3- (pyridin-2-yl)-1,2,4- oxadiazol-5-amine

N-(2-(3-(5- isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5-ylamino)- 5-(trifluoromethyl)pyridin-3- yl)-N-methylacetamide

N-(2-(3-(5- isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5-ylamino)- 5-(trifluoromethyl)pyridin-3- yl)-N- methylcyclopropanecarboxamide

N-methyl-N-(2-(3-(1-methyl- 2,3-dihydro-1H-pyrrolo[2,3- c]pyridin-5-yl)-1,2,4- thiadiazol-5-ylamino)-5- (trifluoromethyl)pyridin-3- yl)acetamide

2-(3-(5-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)-N,N-dimethyl-5- (trifluoromethyl)nicotinamide

(2-(3-(5-isopropoxy-4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)pyridin-3- yl)(pyrrolidin-1- yl)methanone

5-isopropoxy-2-(5-(5-methyl- 3-(trifluoromethyl)pyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)isonicotinamide

5-isopropoxy-2-(5-(5- methoxy-3- (trifluoromethyl)pyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)isonicotinamide

5-isopropoxy-N,N-dimethyl- 2-(5-(5-methyl-3- (trifluoromethyl)pyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)isonicotinamide

N-(4-isopropoxypyridin-2- yl)-5-(5-methoxypyridin-2- yl)-1,3,4-oxadiazol-2-amine

N-(4-isopropoxypyridin-2- yl)-3-(5-methoxypyridin-2- yl)-1,2,4-oxadiazol-5-amine

4-isopropoxy-N-(5-(5- methoxypyridin-2-yl)-4H- 1,2,4-triazol-3-yl)pyridin-2- amine

3-methyl-N-(5-(5- (tetrahydro-2H-pyran-4- yloxy)pyridin-2-yl)-4H-1,2,4- triazol-3-yl)pyridin-2-amine

N-(3-methylpyridin-2-yl)-5- (5-(tetrahydro-2H-pyran-4- yloxy)pyridin-2-yl)-1,3,4- thiadiazol-2-amine

2-(3-(4-(difluoromethyl)-5- isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5-ylamino)- N,N-dimethylnicotinamide

N-(2-(3-(4-(difluoromethyl)- 5-isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylacetamide

N-cyclopropyl-2-(3-(5- isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5-ylamino)- N-methylnicotinamide

N-cyclopropyl-2-(3-(5- isopropoxy-4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)-N- methylnicotinamide

5-isopropoxy-2-(5-(5- methoxy-3- (trifluoromethyl)pyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)-N,N- dimethylisonicotinamide

2-methyl-1-(4-(6-(5-(3- methylpyridin-2-ylamino)- 1,2,4-thiadiazol-3-yl)pyridin- 3-yloxy)piperidin-1- yl)propan-1-one

1-(4-(6-(5-(3-methylpyridin- 2-ylamino)-1,2,4-thiadiazol- 3-yl)pyridin-3- yloxy)piperidin-1- yl)ethanone

1-(5-(5-(3- (trifluoromethyl)pyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-1- yl)ethanone

N-(2-(3-(5-isopropoxy-4- (trifluoromethyl)pyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)-5- (trifluoromethyl)pyridin-3- yl)-N-methylacetamide

N-methyl-N-(6-(5-(3- methylpyridin-2-ylamino)- 1,2,4-thiadiazol-3-yl)pyridin- 3-yl)acetamide

N-methyl-N-(4-methyl-6-(5- (3-methylpyridin-2-ylamino)- 1,2,4-thiadiazol-3-yl)pyridin- 3-yl)acetamide

N-(2-(3-(2,2-dimethyl-2,3- dihydrofuro[2,3-c]pyridin-5- yl)-1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylacetamide

N-(2-(3-(2,2-dimethyl-2,3- dihydrofuro[2,3-c]pyridin-5- yl)-1,2,4-thiadiazol-5- ylamino)-5- (trifluoromethyl)pyridin-3- yl)-N-methylacetamide

N-(2-(3-(1-isopropyl-2,3- dihydro-1H-pyrrolo[2,3- c]pyridin-5-yl)-1,2,4- thiadiazol-5-ylamino)-5- (trifluoromethyl)pyridin-3- yl)-N-methylacetamide

N-(5-(difluoromethyl)-2-(3- (5-isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylacetamide

N-(5-methyl-3- (trifluoromethyl)pyridin-2- yl)-3-(4-(oxetan-3- yloxy)pyridin-2-yl)-1,2,4- thiadiazol-5-amine

methyl 2-(3-(5- isopropoxypyridin-2-yl)- 1,2,4-thiadiazol-5- ylamino)nicotinate

N,N-dimethyl-6-(5-(3- methylpyridin-2-ylamino)- 1,2,4-oxadiazol-3- yl)nicotinamide

6-(5-(3-methylpyridin-2- ylamino)-1,2,4-thiadiazol-3- yl)nicotinonitrile

N-(6-(3-(3-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5-ylamino)- 5-(trifluoromethyl)pyridin-3-yl)- N-methylacetamide

N-(2-(3-(3,3-dimethyl-2-oxo- 2,3-dihydro-1H-pyrrolo[2,3- c]pyridin-5-yl)-1,2,4-thiadiazol- 5-ylamino)-5- (trifluoromethyl)pyridin-3-yl)- N-methylacetamide

2-(3-(3-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5-ylamino)- N,N-dimethyl-5- (trifluoromethyl)nicotinamide

N-methyl-N-(5- (trifluoromethyl)-2-(3-(1,3,3- trimethyl-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)acetamide

N-(2-(3-(2,2-dimethyl-2,3- dihydro-1H-pyrrolo[2,3- c]pyridin-5-yl)-1,2,4-thiadiazol- 5-ylamino)-5- (trifluoromethyl)pyridin-3-yl)- N-methylacetamide

N-(3-(azetidin-1- ylsulfonyl)pyridin-2-yl)-3-(4- (cyclohexyloxy)pyridin-2-yl)- 1,2,4-thiadiazol-5-amine

N-(6-(3-(4-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5-ylamino)- 5-(trifluoromethyl)pyridin-3-yl)- N-methylacetamide

2-(3-(5-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5-ylamino)- N,N-dimethyl-5- (trifluoromethyl)pyridine-3- sulfonamide

N-methyl-N-(5- (trifluoromethyl)-2-(3-(1,3,3- trimethyl-2-oxo-2,3-dihydro- 1H-pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)acetamide

N-(6-(3-(4-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5-ylamino)- 5-methylpyridin-3-yl)-N- methylacetamide

2-(3-(4-isopropylpyridin-2-yl)- 1,2,4-thiadiazol-5-ylamino)- N,N-dimethyl-5- (trifluoromethyl)nicotinamide

N,N-dimethyl-5- (trifluoromethyl)-2-(3-(1,3,3- trimethyl-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5- ylamino)nicotinamide

N-methyl-N-(5- (trifluoromethyl)-2-(3-(1,2,2- trimethyl-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)acetamide

N,N-dimethyl-5- (trifluoromethyl)-2-(3-(1,3,3- trimethyl-2-oxo-2,3-dihydro- 1H-pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5- ylamino)nicotinamide

N,N-dimethyl-5- (trifluoromethyl)-2-(3-(1,2,2- trimethyl-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5- ylamino)nicotinamide

N-(6-(5-(1-isopropyl-2,3- dihydro-1H-pyrrolo[2,3- c]pyridin-5-yl)-1H-1,2,4-triazol- 3-ylamino)-5- (trifluoromethyl)pyridin-3-yl)- N-methylacetamide

N-(2-(5-(1-isopropyl-2,3- dihydro-1H-pyrrolo[2,3- c]pyridin-5-yl)-1H-1,2,4-triazol- 3-ylamino)-5- (trifluoromethyl)pyridin-3-yl)- N-methylacetamide

3-(2,2-dimethyl-2,3- dihydrofuro[2,3-c]pyridin-5-yl)- N-(5-isopropyl-4- (trifluoromethyl)pyridin-2-yl)- 1,2,4-thiadiazol-5-amine

N-(6-(3-(5-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5-ylamino)- 5-methylpyridin-3-yl)-N- methylacetamide

N-(3-(azetidin-1- ylsulfonyl)pyridin-2-yl)-3-(5- isopropoxypyridin-2-yl)-1,2,4- thiadiazol-5-amine

N-(6-(3-(1-isopropyl-2,3- dihydro-1H-pyrrolo[2,3- c]pyridin-5-yl)-1,2,4-thiadiazol- 5-ylamino)-5- (trifluoromethyl)pyridin-3-yl)- N-methylacetamide

N-(6-(3-(5-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5-ylamino)- 5-(trifluoromethyl)pyridin-3-yl)- N-methylacetamide

N-(2-(3-(4-isopropylpyridin-2- yl)-1,2,4-thiadiazol-5-ylamino)- 5-(trifluoromethyl)pyridin-3-yl)- N-methylacetamide

N-(3-(3-(1-isopropyl-1H- pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5- ylamino)pyrazin-2-yl)-N- methylacetamide

N2-(3-(1-isopropyl-1H- pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5-yl)-N3- methylpyrazine-2,3-diamine

N-(2-(3-(1-isopropyl-2,3- dihydro-1H-pyrrolo[3,2- c]pyridin-6-yl)-1,2,4-thiadiazol- 5-ylamino)-5- (trifluoromethyl)pyridin-3-yl)- N-methylacetamide

5-(3-methylpyridin-2-yl)-N-(4- methylpyridin-2-yl)-1,2,4- thiadiazol-3-amine

N-methyl-N-(2-(3-(4- (tetrahydro-2H-pyran-4- yloxy)pyridin-2-yl)-1,2,4- thiadiazol-5-ylamino)-5- (trifluoromethyl)pyridin-3- yl)acetamide

N,N-dimethyl-2-(3-(1-methyl- 2,3-dihydro-1H-pyrrolo[2,3- c]pyridin-5-yl)-1,2,4-thiadiazol- 5-ylamino)pyridine-3- sulfonamide

2-(3-(4-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5-ylamino)- N,N-dimethylpyridine-3- sulfonamide

N-(3-(3-(1-isopropyl-2,3- dihydro-1H-pyrrolo[2,3- c]pyridin-5-yl)-1,2,4-thiadiazol- 5-ylamino)pyrazin-2-yl)-N- methylacetamide

N-(2-(3-(2-isopropyl-2,3- dihydro-1H-pyrrolo[3,4- c]pyridin-6-yl)-1,2,4-thiadiazol- 5-ylamino)pyridin-3-yl)-N- methylacetamide

N-(2-(3-(2-isopropyl-2,3- dihydro-1H-pyrrolo[3,4- c]pyridin-6-yl)-1,2,4-thiadiazol- 5-ylamino)-5- (trifluoromethyl)pyridin-3-yl)- N-methylacetamide

1-(2-(3-(5-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5-ylamino)- 5-(trifluoromethyl)pyridin-3- yl)pyrrolidin-2-one

N-(3-(3-(5-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5- ylamino)pyrazin-2-yl)-N- methylacetamide

N-(2-(3-(6- isopropoxypyridazin-3-yl)- 1,2,4-thiadiazol-5-ylamino)-5- (trifluoromethyl)pyridin-3-yl)- N-methylacetamide

3-(5-isopropoxypyrimidin-2-yl)- N-(3-methylpyridin-2-yl)-1,2,4- thiadiazol-5-amine

N-(2-(3-(5- isopropoxypyrimidin-2-yl)- 1,2,4-thiadiazol-5-ylamino)-5- (trifluoromethyl)pyridin-3-yl)- N-methylacetamide

N-(2-(3-(4-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5-ylamino)- 5-(trifluoromethyl)pyridin-3-yl)- N-methylacetamide

N-(2-(3-(4-methoxypyridin-2- yl)-1,2,4-thiadiazol-5-ylamino)- 5-(trifluoromethyl)pyridin-3-yl)- N-methylacetamide

N-(3-((5-(5-isopropoxypyridin- 2-yl)-1,3,4-oxadiazol-2- yl)(methyl)amino)-5- (trifluoromethyl)pyridin-2- yl)acetamide

2-(3-(5-isopropoxy-4- (trifluoromethyl)pyridin-2-yl)- 1,2,4-thiadiazol-5-ylamino)- N,N-dimethylpyridine-3- sulfonamide

2-(3-(5-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5-ylamino)- N,N-dimethylpyridine-3- sulfonamide

N-(5-isopropyl-4- (trifluoromethyl)pyridin-2-yl)-3- (1-methyl-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5-amine

N-(5-isopropyl-3- (trifluoromethyl)pyridin-2-yl)-3- (1-methyl-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5-amine

3-(1-methyl-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-5-yl)-N- (3-methyl-5- (trifluoromethyl)pyridin-2-yl)- 1,2,4-thiadiazol-5-amine

N-methyl-N-(2-(3-(pyridin-2- yl)-1,2,4-thiadiazol-5-ylamino)- 5-(trifluoromethyl)pyridin-3- yl)acetamide

N-methyl-N-(2-(3-(5-(oxetan-3- yloxy)pyridin-2-yl)-1,2,4- thiadiazol-5-ylamino)pyridin-3- yl)acetamide

isopropyl 2-(3-(5- isopropoxypyridin-2-yl)-1,2,4- thiadiazol-5-ylamino)nicotinate

(2-(3-(5-isopropoxypyridin-2- yl)-1,2,4-thiadiazol-5-ylamino)- 5-(trifluoromethyl)pyridin-3- yl)(pyrrolidin-1-yl)methanone

N-methyl-N-(2-(3-(5-(oxetan-3- yloxy)pyridin-2-yl)-1,2,4- thiadiazol-5-ylamino)-5- (trifluoromethyl)pyridin-3- yl)acetamide

N-(5-(difluoromethyl)-2-(3-(1- methyl-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5- ylamino)pyridin-3-yl)-N- methylacetamide

N-methyl-N-(5- (trifluoromethyl)-6-((3-(1,3,3- trimethyl-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5-yl)amino)- 1l2-piperidin-3-yl)acetamide

N-methyl-N-(5- (trifluoromethyl)-6-((3-(1,2,2- trimethyl-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5- yl)amino)pyridin-3- yl)acetamide

N-methyl-N-(5- (trifluoromethyl)-6-((3-(1,3,3- trimethyl-2-oxo-2,3-dihydro- 1H-pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5- yl)amino)pyridin-3- yl)acetamide

N-(6-((3-(2,2-dimethyl-2,3- dihydro-1H-pyrrolo[2,3- c]pyridin-5-yl)-1,2,4-thiadiazol- 5-yl)amino)-5- (trifluoromethyl)pyridin-3-yl)- N-methylacetamide

N3,N3-dimethyl-5- (trifluoromethyl)-N2-(3-(1,2,2- trimethyl-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-5-yl)-3H- 1,2l2,4-thiadiazol-5-yl)pyridine- 2,3-diamine

5-(5-((3-(dimethylamino)-5- (trifluoromethyl)pyridin-2- yl)amino)-1,2,4-thiadiazol-3- yl)-1,3,3-trimethyl-1,3-dihydro- 2H-pyrrolo[2,3-c]pyridin-2-one

N-(2-((3-(1-isopropyl-3,3- dimethyl-2,3,3a,6-tetrahydro- 1H-pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4l2-thiadiazol-5-yl)amino)- 5-(trifluoromethyl)pyridin-3-yl)- N-methylacetamide

N-(6-((3-(1-isopropyl-3,3- dimethyl-2,3,3a,6-tetrahydro- 1H-pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5-yl)amino)-5- (trifluoromethyl)pyridin-3-yl)- N-methylacetamide

5-(cyclohexyloxy)-N-(5-(5- methoxypyridin-2-yl)-1H-1,2,4- triazol-3-yl)pyridin-2-amine

5-(cyclohexyloxy)-N-(5-(5- methoxypyridin-2-yl)-1-methyl- 1H-1,2,4-triazol-3-yl)pyridin-2- amine

5-isopropoxy-N-(5-(5- methoxypyridin-2-yl)-1-methyl- 1H-1,2,4-triazol-3-yl)pyridin-2- amine

N-methyl-N-(5- (trifluoromethyl)-2-((3-(1,2,2- trimethyl-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-5- yl)amino)pyridin-3- yl)acetamide

N-(5-(cyclohexyloxy)pyridin-2- yl)-5-(5-methoxypyridin-2-yl)- 1,3,4-oxadiazol-2-amine

N-(5-(cyclohexyloxy)pyridin-2- yl)-5-(5-methoxypyridin-2-yl)- 1,3,4-thiadiazol-2-amine

N-(3-methylpyridin-2-yl)-5-(5- ((tetrahydro-2H-pyran-4- yl)oxy)pyridin-2-yl)-1,2,4- thiadiazol-3-amine

N-methyl-N-(5- (trifluoromethyl)-6-((5-(1,3,3- trimethyl-2,3,3a,6,7,7a- hexahydro-1H-pyrrolo[2,3- c]pyridin-5-yl)-1,2,4-thiadiazol- 3-yl)amino)pyridin-3- yl)acetamide

N-(2-((5-(3,3-dimethyl-2,3- dihydro-1H-pyrrolo[2,3- c]pyridin-5-yl)-1,2,4-thiadiazol- 3-yl)amino)-5- (trifluoromethyl)pyridin-3-yl)- N-methylacetamide

N-(2-((5-(2,2-dimethyl-2,3- dihydro-1H-pyrrolo[2,3- c]pyridin-5-yl)-1,2,4-thiadiazol- 3-yl)amino)-5- (trifluoromethyl)pyridin-3-yl)- N-methylacetamide

N-methyl-N-(5- (trifluoromethyl)-2-((5-(1,2,2- trimethyl-2,3-dihydro-1H- pyrrolo[2,3-c]pyridin-5-yl)- 1,2,4-thiadiazol-3- yl)amino)pyridin-3- yl)acetamide

N-methyl-N-(5- (trifluoromethyl)-6-((5-(1,2,2- trimethyl-2,3-dihydro-1H- pyrrolo[2,3-c1pyridin-5-yl)- 1,2,4-thiadiazol-3- yl)amino)pyridin-3- yl)acetamide

N-(2-((5-(5-(tert-butoxy)-1,6- dihydropyridin-2-yl)-1,2,4- thiadiazol-3-yl)amino)-5- (trifluoromethyl)-2,3- dihydropyridin-3-yl)-N- methylacetamide.

18. A pharmaceutical composition comprising an effective amount of a compound of claim 1 or a pharmaceutically acceptable salt, tautomer, isotopologue, or stereoisomer thereof, and a pharmaceutically acceptable carrier, excipient or vehicle.

19. A method of killing a filarial worm, comprising contacting the filarial worm with a compound of claim 1 , or a pharmaceutical composition of claim 18 , or a pharmaceutically acceptable salt, tautomer, isotopologue, or stereoisomer thereof, in an amount effective to kill the filarial worm.

20. A method of inhibiting growth or molt of a filarial worm, comprising contacting the filarial worm with a compound of claim 1 , or a pharmaceutical composition of claim 18 , or a pharmaceutically acceptable salt, tautomer, isotopologue, or stereoisomer thereof, in an amount effective to inhibit growth or molt of the filarial worm.

21. A method of inhibiting motility of a filarial worm, comprising contacting the filarial worm with a compound of claim 1 , or a pharmaceutical composition of claim 18 , or a pharmaceutically acceptable salt, tautomer, isotopologue, or stereoisomer thereof, in an amount effective to inhibit motility of the filarial worm.

22. A method for the treatment or prevention of helminthic infections and diseases, the methods comprising administering to a subject an effective amount of a compound of claim 1 , or a pharmaceutical composition of claim 18 , or a pharmaceutically acceptable salt, tautomer, isotopologue, or stereoisomer thereof.

23. A method for the treatment or prevention of helminthic infections and diseases, the methods comprising administering to a subject an effective amount of a compound of claim 1 , or a pharmaceutical composition of claim 18 , or a pharmaceutically acceptable salt, tautomer, isotopologue, or stereoisomer thereof in combination with another anti-parasitic agent.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 22, 2021
From: SIGNAL PHARMACEUTICALS, LLC
To: CELGENE CORPORATION
Reel/Frame 056646/0849 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 22, 2021
From: HAWRYLUK, NATALIE ANNE; CANAN, STACIE SARA
To: CELGENE CORPORATION
Reel/Frame 057491/0108 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2021
From: KYNE, GRAHAM; BEDORE, MATTHEW; MENON, SANJAY
To: ZOETIS LLC
Reel/Frame 055979/0495 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2021
From: CONDROSKI, KEVIN R.
To: SIGNAL PHARMACEUTICALS, LLC
Reel/Frame 055982/0373 →
Continuity (2)
Provisional Application 62839552 · Apr 26, 2019
Related Publication 20200339559A1 · Oct 29, 2020
Cited By (4)
US 12,304,903 US 12,338,235 US 12,544,336 US 12,655,138