IP Library Granted Patent US 10,526,345
Granted Patent B2
US 10,526,345 · App. 15/478,883 · Granted Jan 7, 2020

Compounds as GPR119 agonists

Inventors: Rakesh Ishwar Patil (IMT Manesar, IN); Jeevan Verma (IMT Manesar, IN); Dharmesh Shah (IMT Manesar, IN); Sazid Ali (IMT Manesar, IN); Srinivasa Reddy Bapuram (IMT Manesar, IN); Santosh Kumar Rai (IMT Manesar, IN); Anil Kumar (IMT Manesar, IN)
Assignee: MANKIND PHARMA LTD.
C07D513/04A61P3/04A61P3/10
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Quick Facts
Patent No.
US 10,526,345
App. No.
15/478,883
Granted
Jan 7, 2020
Kind
B2
Abstract

The present invention relates to novel compounds of formula (I) as GPR119 agonist, composition compositions containing such compounds and method of preparation thereof.

Claims (540)

1. A compound of formula (II):

wherein,

Y is selected from H, OH, halogen, C 1-6 alkyl, C 1-6 alkoxy, amino, —NH(Alkyl), —N(Alkyl) 2 , —NH-aralkyl, —CONH 2 , —OCH(CH 3 ) 2 ;

R 1 is selected from:

R 2 is selected from

R 3 is selected from H, OH, halogen, C 1-6 alkyl, C 1-6 alkoxy, amino, —NH(Alkyl), —N(Alkyl) 2 , —NH-aralkyl, —CF 3 , —CH 2 OCH 3 , OR

and pharmaceutically acceptable salts, hydrates and stereoisomers thereof.

2. The compound of claim 1 , having active GLP-1 secretion greater than ˜1 fold with respect to vehicle.

3. The compound of claim 1 , having significant dose dependent glucose reduction at both 3 mpk and 10 mpk in oral glucose tolerance test in rat model.

4. The compound of claim 1 , having significant dose dependent glucose reduction at both 3 mpk and 10 mpk in oral glucose tolerance test in mice model.

5. The compound of claim 1 , showing increase in insulin secretion at an EC50 of less than 1 μM in an in-vitro model of pancreatic beta cells.

6. The compound of claim 1 , wherein R1 is

7. The compound of claim 1 , wherein R1 is

8. The compound of claim 1 , wherein R1 is

9. The compound of claim 1 , wherein Y is hydrogen.

10. A compound of claim 1 having the structure:

1001

3-isopropyl-5-(1-(5-(4-(methyl- sulfonyl)phenoxy)thiazolo [5,4-b]pyridin-2- yl)piperidin-4-yl)-1,2,4- oxadiazole

1002

3-isopropyl-5-(4-(((5-(4- (methylsulfonyl)phenoxy)thiazolo [5,4-b]pyridin-2- yl)oxy)methyl)piperidin-1- yl)-1,2,4-oxadiazole

1003

3-isopropyl-5-(1-(2-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-5- yl)piperidin-4-yl)-1,2,4- oxadiazole

1004

3-isopropyl-5-(1-(5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)piperidin-4-yl)-1,2,4- oxadiazole

1005

3-isopropyl-5-(4-((5-(4- (methylsulfonyl)phenoxy) thiazolo[5,4-b]pyridin-2- yl)oxy)piperidin-1-yl)- 1,2,4-oxadiazole

1006

3-isopropyl-5-(4-(((5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy)methyl)piperidin-1- yl)-1,2,4-oxadiazole

1007

3-isopropyl-5-(4-((5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy)piperidin-1-yl)- 1,2,4-oxadiazole

1008

2-(4-(5-ethylpyrimidin-2- yl)piperazin-1-yl)-5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridine

1009

5-((1-benzylpiperidin-4- yl)methoxy)-2-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridine

1010

2-(4-(5-ethylpyrimidin-2- yl)piperazin-1-yl)-5-(4- (methylsulfonyl)phenoxy) thiazolo[5,4-b]pyridine

1011

isopropyl 4-(5-(4-(methyl- sulfonyl)phenyl)thiazolo [5,4-b]pyridin-2-yl)-5,6- dihydropyridine-1(2H)- carboxylate

1012

isopropyl 4-(5-(4-(methyl- sulfonyl)phenyl)thiazolo [5,4-b]pyridin-2-yl) piperazine-1-carboxylate

1013

isopropyl 4-(5-(4-(methyl- sulfonyl)phenyl)thiazolo [5,4-b]pyridin-2-yl) piperidine-1-carboxylate

1014

1-(5-ethylpyrimidin-2-yl)-N- (5-(4-(methylsulfonyl) phenyl)thiazolo[5,4-b] pyridin-2-yl)piperidine- 4-carboxamide

1015

2-(4-(5-(4-(methylsulfonyl) phenyl)thiazolo[5,4- b]pyridin-2-yl)-5,6- dihydropyridin-1(2H)- yl)ethanol

1016

isopropyl 4-(methyl(5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)amino)piperidine-1- carboxylate

1017

N-(1-(5-ethylpyrimidin-2- yl)piperidin-4-yl)-N- methyl-5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- amine

1018

isopropyl 4-((5-(4-(dimethyl carbamoyl)phenyl)thiazolo [5,4-b]pyridin-2- yl)(methyl)amino) piperidine-1-carboxylate

1019

isopropyl (5-(4-(methyl- sulfonyl)phenyl)thiazolo [5,4-b]pyridin-2-yl)carbonate

11. The compound of claim 1 having the structure:

1020

3-isopropyl-5-(4-(1-((5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy)ethyl)piperidin-1- yl)-1,2,4-oxadiazole

1021

3-isopropyl-5-(1-(5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)pyrrolidin-3-yl)-1,2,4- oxadiazole

1022

4-(2-(4-(3-isopropyl-1,2,4- oxadiazol-5-yl)piperidin-1- yl)thiazolo[5,4-b]pyridin- 5-yl)-N,N- dimethylbenzamide

1023

N-(1-(3-isopropyl-1,2,4- oxadiazol-5-yl)piperidin-4- yl)-N-methyl-5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- amine

1024

4-(2-(4-(3-isopropyl-1,2,4- oxadiazol-5-yl)piperidin-1- yl)thiazolo[5,4-b]pyridin- 5-yl)-N-(2- methoxyethyl)benzamide

1025

N-(3-fluoro-4- (methylsulfonyl)phenyl)-2- (4-(3-isopropyl-1,2,4- oxadiazol-5-yl)piperidin-1- yl)thiazolo[5,4-b]pyridin- 5-amine

1026

5-(4-(methylsulfonyl)phenyl)- 2-(1-tosyl-1,2,3,6- tetrahydropyridin-4- yl)thiazolo[5,4-b]pyridine

1027

N,N-dimethyl-4-(5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2-yl)- 5,6-dihydropyridine-1(2H)- carboxamide

1028

N,N-dimethyl-4-(5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)piperidine-1- carboxamide

1029

(4-(2-(4-(3-isopropyl-1,2,4- oxadiazol-5-yl)piperidin-1- yl)thiazolo[5,4-b]pyridin- 5-yl)phenyl)(morpholino) methanone

1030

N,N-diisopropyl-4-(5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2-yl)- 5,6-dihydropyridine-1(2H)- carboxamide

1031

(S)-3-isopropyl-5-(4-(1-((5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy)ethyl)piperidin-1- yl)-1,2,4-oxadiazole

1032

(R)-3-isopropyl-5-(4-(1-((5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy)ethyl)piperidin-1- yl)-1,2,4-oxadiazole

1033

3-cyclopropyl-5-(4-((5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy)piperidin-1-yl)- 1,2,4-oxadiazole

1034

isopropyl 4-(2-((5-(4-(methyl- sulfonyl)phenyl)thiazolo [5,4-b]pyridin-2- yl)oxy)ethyl)-5,6- dihydropyridine-1(2H)- carboxylate

1035

3-isopropyl-5-(4-(2-((5-(4- (methylsulfonyl)phenyl)thiazolo [5,4-b]pyridin-2- yl)oxy)ethyl)-5,6- dihydropyridin-1(2H)-yl)- 1,2,4-oxadiazole

1036

3-isopropyl-5-(4-(2-methoxy- 1-((5-(4-(methylsulfonyl) phenyl)thiazolo[5,4- b]pyridin-2- yl)oxy)ethyl)piperidin-1- yl)-1,2,4-oxadiazole

1037

3-isopropyl-5-(4-(1-((7- methyl-5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy)ethyl)piperidin-1- yl)-1,2,4-oxadiazole

1038

3-isopropyl-5-(4-(((7-methyl- 5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy)methyl)piperidin-1- yl)-1,2,4-oxadiazole

1039

3-isopropyl-5-(4-(1-((6- methyl-5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy)ethyl)piperidin-1- yl)-1,2,4-oxadiazole

12. The compound of claim 1 having the structure:

1040

5-(4-(cyclopropyl((5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy)methyl)piperidin-1- yl)-3-isopropyl-1,2,4- oxadiazole

1041

3-isopropyl-5-(4-(2-((5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy)ethylidene) piperidin-1-yl)-1,2,4- oxadiazole

1042

3-isopropyl-5-(4-(2-((5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy)ethyl)piperidin-1- yl)-1,2,4-oxadiazole

1043

3-isopropyl-5-(4-(2-((5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy)propyl)piperidin-1- yl)-1,2,4-oxadiazole

1044

3-isopropyl-5-(4-(2-((5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy) propylidene)piperidin-1- yl)-1,2,4-oxadiazole

1045

(S)-4-(2-(1-(1-(3-isopropyl- 1,2,4-oxadiazol-5- yl)piperidin-4- yl)ethoxy)thiazolo[5,4- b]pyridin-5-yl)-N,N- dimethylbenzamide

1046

3-fluoro-4-(2-(1-(1-(3- isopropyl-1,2,4-oxadiazol- 5-yl)piperidin-4- yl)ethoxy)thiazolo[5,4- b]pyridin-5-yl)-N,N- dimethylbenzamide

1047

2-fluoro-4-(2-(1-(1-(3- isopropyl-1,2,4-oxadiazol- 5-yl)piperidin-4- yl)ethoxy)thiazolo[5,4- b]pyridin-5-yl)-N,N- dimethylbenzamide

1048

3-cyclopropyl-5-(4-(1-((5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy)ethyl)piperidin-1- yl)-1,2,4-oxadiazole

1049

N-cyclopropyl-4-(2-(1-(1-(3- isopropyl-1,2,4-oxadiazol- 5-yl)piperidin-4- yl)ethoxy)thiazolo[5,4- b]pyridin-5-yl)benzamide

1050

4-(2-(1-(1-(3-isopropyl-1,2,4- oxadiazol-5-yl)piperidin-4- yl)ethoxy)thiazolo[5,4- b]pyridin-5-yl)-N-(2- methoxyethyl)benzamide

1051

(4-(2-(1-(1-(3-isopropyl-1,2,4- oxadiazol-5-yl)piperidin-4- yl)ethoxy)thiazolo[5,4- b]pyridin-5- yl)phenyl)(morpholino) methanone

1052

N-cyclopropyl-4-(2-(1-(1-(3- isopropyl-1,2,4-oxadiazol- 5-yl)piperidin-4- yl)ethoxy)thiazolo[5,4- b]pyridin-5-yl)-N-methyl benzamide

1053

5-(4-(methylsulfonyl)phenyl)- 2-(1-(1-(5- propylpyrimidin-2-yl) piperidine-4- yl)ethoxy)thiazolo[5,4-b] pyridine

1054

3-isopropyl-5-(4-(1-((5- (pyridin-3-yl)thiazolo[5,4- b]pyridin-2-yl)oxy) ethyl)piperidin-1-yl)-1,2,4- oxadiazole

1055

2-(1-(1-(5-ethylpyrimidin-2- yl)piperidin-4-yl)ethoxy)- 5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridine

1056

isopropyl 4-(1-((5-(4-(methyl- sulfonyl)phenyl)thiazolo [5,4-b]pyridin-2-yl)oxy)ethyl) piperidine-1-carboxylate

1057

3-isopropyl-5-(4-(1-((5-(4- ((methylsulfonyl)methyl) phenyl)thiazolo[5,4-b] pyridin-2- yl)oxy)ethyl)piperidin-1- yl)-1,2,4-oxadiazole

1058

5-isopropyl-3-(4-(1-((5-(4- (methylsulfonyl)phenyl)thiazolo [5,4-b]pyridin-2-yl)oxy)ethyl) piperidin-1-yl)-1,2,4- oxadiazole

1059

3-isopropyl-5-(4-(1-((5-(4- (methylsulfonyl)phenyl)thiazolo [5,4-b]pyridin-2- yl)oxy)ethyl)phenyl)-1,2,4- oxadiazole

13. The compound of claim 1 having the structure:

1060

5-(3-fluoro-4-((5-(4-(methyl sulfonyl)phenyl)thiazolo [5,4-b]pyridin-2- yl)oxy)piperidin-1-yl)-3- isopropyl-1,2,4-oxadiazole

1061

4-(2-(1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl) ethoxy) thiazolo[5,4-b]pyridin-5- yl)-N-methylbenzene- sulfonamide

1062

5-(4-(1-((5-(4-(ethylsulfonyl) phenyl)thiazolo[5,4-b] pyridin-2-yl)oxy)ethyl) piperidin-1-yl)-3-isopropyl- 1,2,4-oxadiazole

1063

5-(4-(1-((5-(4-(cyclopropyl sulfonyl)phenyl)thiazolo [5,4-b]pyridin-2-yl)oxy) ethyl)piperidin-1-yl)-3- isopropyl-1,2,4-oxadiazole

1064

5-(4-(1-((5-(4-(cyclopropyl sulfinyl)phenyl)thiazolo [5,4-b]pyridin-2-yl)oxy) ethyl)piperidin-1-yl)-3- isopropyl-1,2,4-oxadiazole

1065

4-(2-(1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl) ethoxy) thiazolo[5,4-b]pyridin-5- yl)benzonitrile

1066

4-(2-(1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy) thiazolo[5,4-b]pyridin- 5-yl)-N-(2-methoxyethyl) benzenesulfonamide

1067

3-isopropyl-5-(4-(1-((5-(4- ((2-methoxyethyl)sulfonyl) phenyl)thiazolo[5,4-b] pyridin-2-yl)oxy) ethyl) piperidin-1-yl)-1,2,4- oxadiazole

1068

3-isopropyl-5-(4-(1-((5- (4-((2-methoxyethyl) sulfinyl)phenyl)thiazolo [5,4-b]pyridin-2-yl)oxy) ethyl) piperidin-1-yl)- 1,2,4-oxadiazole

1069

3-isopropyl-5-(4-(1-((5-(6- (methylsulfonyl)pyridin-3- yl)thiazolo[5,4-b]pyridin- 2-yl)oxy)ethyl)piperidin-1- yl)-1,2,4-oxadiazole

1070

(R)-3-isopropyl-5-(4-(1- ((5-(pyridin-4-yl)thiazolo [5,4-b]pyridin-2-yl)oxy) ethyl)piperidin-1-yl)-1,2,4- oxadiazole

1071

(R)-4-(2-(1-(1-(3- isopropyl-1,2,4-oxadiazol- 5-yl)piperidin-4- yl)ethoxy)thiazolo[5,4-b] pyridin-5-yl)-1- methylpyridin-1-ium

1072

4-(2-(4-(3-isopropyl-1,2,4- oxadiazol-5-yl)piperidin-1- yl) thiazolo[5,4-b]pyridin- 5-yl)-N- methylbenzenesulfonamide

1073

4-(2-(4-(3-isopropyl-1,2,4- oxadiazol-5-yl)piperidin- 1-yl)thiazolo[5,4-b] pyridin-5-yl)-N-(2- methoxyethyl)benzene sulfonamide

1074

N-(4-(2-(1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy) thiazolo[5,4-b]pyridin-5- yl)phenyl)methane- sulfonamide

1075

2-(1-(1-(1-methyl-1H- tetrazol-5-yl)piperidin-4- yl)ethoxy)-5-(4-(methyl- sulfonyl)phenyl)thiazolo [5,4-b]pyridine

1076

(S)-5-(4-(1-((5-(3- fluoropyridin-4- yl)thiazolo[5,4-b]pyridin- 2-yl)oxy)ethyl)piperidin- 1-yl)-3-isopropyl-1,2,4- oxadiazole

1077

3-isopropyl-5-(1-(5- (pyridin-4-yl)thiazolo [5,4-b]pyridin-2-yl) piperidin-4-yl)-1,2,4- oxadiazole

1078

3-isopropyl-5-(1-(5-(4-((2- methoxyethyl)sulfonyl) phenyl)thiazolo[5,4-b] pyridin-2-yl)piperidin-4- yl)-1,2,4-oxadiazole

1079

5-(4-(1-((5-(4-(1H- tetrazol-1-yl)phenyl) thiazolo[5,4-b]pyridin-2- yl)oxy)ethyl)piperidin- 1-yl)-3-isopropyl-1,2,4- oxadiazole

14. The compound of claim 1 having the structure:

1080

3-isopropyl-5-(1-(5-(6- (methylsulfonyl)pyridin- 3-yl)thiazolo[5,4-b] pyridin-2-yl)piperidin- 4-yl)-1,2,4-oxadiazole

1081

5-(4-(1-((5-(2-fluoro- pyridin-4-yl)thiazolo [5,4-b]pyridin-2-yl) oxy)ethyl)piperidin-1- yl)-3-isopropyl-1,2,4- oxadiazole

1082

(S)-3-isopropyl-5-(4-(1- ((5-(6-(methylsulfonyl) pyridin-3-yl)thiazolo [5,4-b]pyridin-2-yl)oxy) ethyl)piperidin-1-yl)- 1,2,4-oxadiazole

1083

3-isopropyl-5-(4-(((5- (pyridin-4-yl)thiazolo [5,4-b]pyridin-2-yl) oxy)methyl)piperidin- 1-yl)-1,2,4-oxadiazole

1084

5-(4-(((5-(3-fluoro- pyridin-4-yl)thiazolo [5,4-b]pyridin-2-yl) oxy)methyl)piperidin- 1-yl)-3-isopropyl- 1,2,4-oxadiazole

1085

5-(4-(((5-(4-(1H- tetrazol-1-yl)phenyl) thiazolo[5,4-b] pyridin-2-yl)oxy) methyl)piperidin-1- yl)-3-isopropyl-1,2,4- oxadiazole

1086

5-(4-(((5-(2-fluoro- pyridin-4-yl)thiazolo [5,4-b]pyridin-2-yl) oxy)methyl)piperidin- 1-yl)-3-isopropyl- 1,2,4-oxadiazole

1087

2-(1-(1-(5-ethylpyridin- 2-yl)piperidine-4-yl) ethoxy)-5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridine

1088

5-(4-(methylsulfonyl) phenyl)-2-(1-(1-(5- vinylpyridin-2-yl) piperidin-4-yl)ethoxy) thiazolo[5,4-b]pyridine

1089

(S)-5-(4-(methyl- sulfonyl)phenyl)-2- (1-(1-(5-propyl- pyrimidin-2-yl) piperidin-4-yl)ethoxy) thiazolo [5,4-b]pyridine

1090

(R)-5-(4- (methylsulfonyl) phenyl)-2-(1-(1-(5- propylpyrimidin-2- yl)piperidin-4-yl) ethoxy)thiazolo [5,4-b]pyridine

1091

3-isopropyl-5-(4-(((5- (6-(methylsulfonyl) pyridin-3-yl)thiazolo [5,4-b]pyridin-2-yl) oxy)methyl)piperidin- 1-yl)-1,2,4-oxadiazole

1092

(S)-3-isopropyl-5-(4- (1-((5-(pyridin-4-yl) thiazolo[5,4-b]pyridin- 2-yl)oxy)ethyl) piperidin-1-yl)-1,2,4- oxadiazole

1093

(S)-5-(4-(1-((5-(2- fluoropyridin-4- yl)thiazolo[5,4-b] pyridin-2-yl)oxy)ethyl) piperidin-1-yl)-3- isopropyl-1,2,4- oxadiazole

1094

3-isopropyl-5-(4- (2,2,2-trifluoro-1- ((5-(4-(methylsulfonyl) phenyl)thiazolo[5,4-b] pyridin-2-yl)oxy) ethyl)piperidin-1-yl)- 1,2,4-oxadiazole

1095

(S)-5-(4-(1-((5-(4- (cyclopropylsulfonyl) phenyl)thiazolo [5,4-b] pyridin-2-yl) oxy)ethyl)piperidin-1- yl)-3-isopropyl-1,2,4- oxadiazole

1096

(S)-5-(4-(1-((5-(3- fluoropyridin-4- yl)thiazolo[5,4-b] pyridin-2-yl)oxy)ethyl) piperidin-1-yl)-3- isopropyl-1,2,4- oxadiazole

1097

2-isopropyl-5-(4-(1- ((5-(4-(methylsulfonyl) phenyl)thiazolo[5,4-b] pyridin-2-yl)oxy)ethyl) piperidin-1-yl)-1,3,4- oxadiazole

1098

4-(2-(1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl) ethoxy) thiazolo[5,4-b]pyridin- 5-yl)pyridine 1-oxide

1099

(S)-5-(6-(methyl- sulfonyl)pyridin-3-yl)- 2-(1-(1-(5-propyl- pyrimidin-2-yl) piperidin-4-yl)ethoxy) thiazolo [5,4-b] pyridine

15. The compound of claim 1 having the structure

1100

5-(4-(1-((5-(3-fluoro-4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin- 2-yl)oxy)ethyl) piperidin-1-yl)-3- isopropyl-1,2,4- oxadiazole

1101

(S)-5-(2-fluoropyridin- 4-yl)-2-(1-(1-(5-propyl- pyrimidin-2-yl) piperidin-4-yl)ethoxy) thiazolo [5,4-b] pyridine

1102

3-isopropyl-5-(4- (2,2,2-trifluoro-1-((5- (6-(methylsulfonyl) pyridin-3-yl)thiazolo [5,4-b]pyridin-2-yl) oxy) ethyl)piperidin- 1-yl)-1,2,4-oxadiazole

1103

3-isopropyl-5-(4- (2,2,2-trifluoro-1- ((5-(2-fluoropyridin- 4-yl)thiazolo[5,4-b] pyridin-2-yl)oxy) ethyl) piperidin-1- yl)-1,2,4-oxadiazole

1104

(S)-2-(1-(1-(5-ethyl- pyrimidin-2-yl) piperidin-4-yl)ethoxy)- 5-(2-fluoropyridin-4- yl)thiazolo[5,4-b] pyridine

1105

3-isopropyl-5-(4-(1- ((5-(4-(methyl sulfonyl)phenyl) thiazolo[5,4-b]pyridin- 2-yl)oxy)ethyl) cyclohexyl)-1,2,4- oxadiazole

1106

(S)-2-(1-(1-(5-ethyl- pyrimidin-2-yl) piperidin-4-yl)ethoxy)- 5-(6-(methylsulfonyl) pyridin-3-yl) thiazolo [5,4-b]pyridine

1107

2-(1-(1-(3-isopropyl- 1,2,4-thiadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(4-(methylsulfonyl) phenyl)thiazolo[5,4-b] pyridine

1108

3-isopropyl-5-(4-(1- ((6-(4-(methyl sulfonyl)phenyl)thiazolo [4,5-b] pyrazin-2-yl) oxy)ethyl)piperidin- 1-yl)-1,2,4-oxadiazole

1109

2-(1-(1-(cyclopropyl- sulfonyl)piperidin-4- yl)ethoxy)-5-(4- (methylsulfonyl) phenyl)thiazolo[5,4-b] pyridine

1110

6-(4-(methylsulfonyl) phenyl)-2-(1-(1-(5- propylpyrimidin-2-yl) piperidin-4-yl)ethoxy) thiazolo[4,5-b] pyrazine

1111

5-(4-(1-((5-(2-fluoro-4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin- 2-yl)oxy)ethyl) piperidin-1-yl)-3- isopropyl-1,2,4- oxadiazole

1112

5-(3-fluoro-4-(1-((5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin- 2-yl)oxy)ethyl) piperidin-1-yl)-3- isopropyl-1,2,4- oxadiazole

1113

2-(1-(1-(5-isopropyl- pyrimidin-2-yl)piperidin- 4-yl)ethoxy)-5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridine

1114

(S)-3-isopropyl-5-(4-(1- ((6-(6-(methylsulfonyl) pyridin-3-yl) thiazolo [4,5-b]pyrazin-2-yl)oxy) ethyl)piperidin-1-yl)- 1,2,4-oxadiazole

1115

5-(4-(methylsulfonyl) phenyl)-2-(1-(1- (propylsulfonyl) piperidin-4-yl)ethoxy) thiazolo[5,4-b]pyridine

1116

5-(4-(1-((5-(2- chloropyrimidin-5- yl)thiazolo[5,4-b] pyridin-2-yl) oxy) ethyl)piperidin-1-yl)- 3-isopropyl-1,2,4- oxadiazole

1117

1-methylcyclopropyl 4-(1-((5-(4-(methyl- sulfonyl)phenyl) thiazolo[5,4-b]pyridin- 2-yl)oxy)ethyl) piperidine-1- carboxylate

1118

5-(4-(methylsulfonyl) phenyl)-2-(1-(1-(5- (prop-1-en-2-yl) pyrimidin-2-yl) piperidin-4-yl)ethoxy) thiazolo [5,4-b] pyridine

1119

(S)-5-(4-(1-((5-(2- chloropyrimidin-5- yl)thiazolo[5,4-b] pyridin-2-yl)oxy) ethyl) piperidin-1-yl)- 3-isopropyl-1,2,4- oxadiazole

16. The compound of claim 1 having the structure:

1120

2-(1-(1-(5-chloro- pyrimidin-2-yl) piperidin-4-yl)ethoxy)- 5-(4-(methylsulfonyl) phenyl)thiazolo[5,4-b] pyridine

1121

3-isopropyl-5-(4-(1-((5- (thiazol-5-yl)thiazolo [5,4-b]pyridin-2-yl)oxy) ethyl)piperidin-1-yl)- 1,2,4-oxadiazole

1122

3-isopropyl-5-(4-(1-((5- (isoxazol-4-yl)thiazolo [5,4-b]pyridin-2-yl)oxy) ethyl)piperidin-1-yl)- 1,2,4-oxadiazole

1123

3-isopropyl-5-(4-(1-((5- (2-methylpyridin-4-yl) thiazolo[5,4-b]pyridin- 2-yl)oxy)ethyl) piperidin-1-yl)-1,2,4- oxadiazole

1124

3-isopropyl-5-(4-(1-((5- (isothiazol-4-yl)thiazolo [5,4-b]pyridin-2-yl)oxy) ethyl)piperidin-1-yl)- 1,2,4-oxadiazole

1125

3-isopropyl-5-(4-(1-((5- (3-methylisothiazol-4- yl)thiazolo[5,4-b]pyridin- 2-yl)oxy)ethyl) piperidin- 1-yl)-1,2,4-oxadiazole

1126

4-(2-(1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy) thiazolo[5,4-b]pyridin- 5-yl)pyridin-2(1H)- one

1127

4-(2-(1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy) thiazolo[5,4-b]pyridin- 5-yl)-1-methylpyridin- 2(1H)-one

1128

5-((3R,4S)-3-fluoro-4- (((5-(4-(methylsulfonyl) phenyl)thiazolo[5,4-b] pyridin-2-yl)oxy)methyl) piperidin-1-yl)-3- isopropyl-1,2,4- oxadiazole

1129

5-((3S,4S)-3-fluoro-4- (((5-(4-(methylsulfonyl) phenyl)thiazolo[5,4-b] pyridin-2-yl)oxy)methyl) piperidin-1-yl)-3- isopropyl-1,2,4- oxadiazole

1130

3-isopropyl-5-(4-(1-(5- (4-(methylsulfonyl) phenyl)thiazolo[5,4-b] pyridin-2-yl)ethoxy) piperidin-1-yl)-1,2,4- oxadiazole

1131

5-(4-(1-((5-(4-(methyl- sulfonyl)phenyl)thiazolo [5,4-b]pyridin-2-yl)oxy) ethyl)piperidin-1-yl)- 3-(trifluoromethyl)- 1,2,4-oxadiazole

1132

5-(4-(1-((5-(2-chloro- pyridin-4-yl)thiazolo [5,4-b]pyridin-2-yl)oxy) ethyl)piperidin-1-yl)-3- isopropyl-1,2,4- oxadiazole

1133

3-isopropyl-5-(4-(1- ((5-(2-(methylsulfonyl) pyrimidin-5-yl)thiazolo [5,4-b]pyridin-2-yl)oxy) ethyl)piperidin-1-yl)- 1,2,4-oxadiazole

1134

3-isopropyl-5-(4-(1- ((5-(pyridazin-4-yl) thiazolo[5,4-b]pyridin- 2-yl)oxy)ethyl) piperidin-1-yl)-1,2,4- oxadiazole

1135

2-((S)-1-(1-(5-ethyl- pyrimidin-2-yl) piperidin-4-yl)ethoxy)- 5-(2-chloropyrimidin- 5-yl)thiazolo[5,4-b] pyridine

1136

2-((S)-1-(1-(5-chloro- pyrimidin-2-yl) piperidin-4-yl)ethoxy)- 5-(6-(methylsulfonyl) pyridin-3-yl)thiazolo [5,4-b]pyridine

1137

2-(1-(1-(5-cyclopropyl- pyrimidin-2-yl)piperidin- 4-yl)ethoxy)-5-(6- (methylsulfonyl)pyridin- 3-yl)thiazolo[5,4-b] pyridine

1138

2-((S)-1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(2-(methylsulfinyl) pyrimidin-5-yl)thiazolo [5,4-b]pyridine

1139

N-(5-(2-(1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy) thiazolo[5,4-b]pyridin-5- yl)pyrimidin-2-yl)-N- methylacetamide

17. The compound of claim 1 having the structure:

1140

2-((R)-1-(1-(3- isopropyl-1,2,4- oxadiazol-5-yl) pyrrolidin-3-yl)ethoxy)- 5-(6-(methylsulfonyl) pyridin-3-yl)thiazolo [5,4-b]pyridine

1141

2-((S)-1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) pyrrolidin-3-yl)ethoxy)- 5-(6-(methylsulfonyl) pyridin-3-yl)thiazolo [5,4-b]pyridine

1142

2-(1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(6-chloropyridin-3- yl)thiazolo[5,4-b] pyridine

1143

2-((S)-1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(2-chloropyridin-4- yl)thiazolo[5,4-b] pyridine

1144

1-(5-(2-(1-(1-(3- isopropyl-1,2,4- oxadiazol-5-yl) piperidin-4-yl)ethoxy) thiazolo[5,4-b] pyridin-5-yl)pyridin- 2-yl)imidazolidin- 2-one

1145

2-((S)-1-(1-(3- (trifluoromethyl)-1,2,4- oxadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(6-(methylsulfonyl) pyridin-3-yl)thiazolo [5,4-b]pyridine

1146

1-(5-(2-(1-(1-(3- isopropyl-1,2,4- oxadiazol-5-yl) piperidin-4-yl)ethoxy) thiazolo[5,4-b]pyridin- 5-yl)pyridin-2-yl) pyrrolidin-2-one

1147

2-(1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(6-(trifluoromethyl) pyridin-3-yl)thiazolo [5,4-b]pyridine

1148

2-(1-(1-(5-chloro- pyrazin-2-yl)piperidin- 4-yl)ethoxy)-5-(4- (methylsulfonyl)phenyl) thiazolo[5,4-b]pyridine

1149

2-(1-(1-(5-ethyl- pyrimidin-2-yl) piperidin-4-yl)ethoxy)- 5-(pyridin-4-yl) thiazolo[5,4-b]pyridine

1150

2-(1-(1-(5-propyl- pyrimidin-2-yl) piperidin-4-yl)ethoxy)- 5-(pyridin-4-yl)thiazolo [5,4-b]pyridine

1151

2-(1-(1-(5-chloro- pyrazin-2-yl)piperidin- 4-yl)ethoxy)-5-(6- (methylsulfonyl) pyridin-3-yl)thiazolo [5,4-b]pyridine

1152

2-((S)-1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(6-(trifluoromethyl) pyridin-3-yl)thiazolo [5,4-b]pyridine

1153

2-((S)-1-(1-(5- propylpyrimidin-2- yl)piperidin-4-yl) ethoxy)-5-(pyridin- 4-yl)thiazolo [5,4-b]pyridine

1154

2-((S)-1-(1-(5-ethyl- pyrimidin-2-yl) piperidin-4-yl)ethoxy)- 5-(6-(trifluoromethyl) pyridin-3-yl)thiazolo [5,4-b]pyridine

1155

2-((S)-1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(3-fluoro-4-(methyl- sulfonyl)phenyl) thiazolo[5,4-b]pyridine

1156

2-(1-(1-(3-ethyl-1,2,4- oxadiazol-5-yl)piperidin- 4-yl)ethoxy)-5-(6- (methylsulfonyl)pyridin- 3-yl)thiazolo[5,4-b] pyridine

1157

2-(1-(1-(5-methyl- pyrimidin-2-yl) piperidin-4-yl)ethoxy)- 5-(6-(methylsulfonyl) pyridin-3-yl)thiazolo [5,4-b]pyridine

1158

2-(1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(5-(methylsulfonyl) pyrazin-2-yl)thiazolo [5,4-b]pyridine

1159

2-(1-(1-(5-(trifluoro- methyl)pyrimidin-2- yl)piperidin-4-yl) ethoxy)-5-(6- (methylsulfonyl) pyridin-3-yl)thiazolo [5,4-b]pyridine

1160

2-((S)-1-(1-(3-ethyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(6-(methylsulfonyl) pyridin-3-yl)thiazolo [5,4-b]pyridine

1161

2-(1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(5-(methylsulfonyl) pyridin-2-yl)thiazolo [5,4-b]pyridine

1162

2-(1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(6-(methylsulfonyl) pyridin-3-yl)thiazolo [5,4-d]pyrimidine

1163

2-(1-(1-(5-(methoxy- methyl)pyrimidin-2-yl) piperidin-4-yl)ethoxy)- 5-(6-(methylsulfonyl) pyridin-3-yl)thiazolo [5,4-b]pyridine

1164

2-((R)-1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(6-(cyclopropyl- sulfonyl)pyridin-3-yl) thiazolo[5,4-b]pyridine

1165

2-((R)-1-(1-(5- (methoxymethyl) pyrimidin-2-yl) piperidin-4-yl)ethoxy)- 5-(6-(methylsulfonyl) pyridin-3-yl)thiazolo [5,4-b]pyridine

1166

2-((S)-(1-(1-(5- (trifluoromethyl) pyrimidin-2-yl) piperidin-4-yl)ethoxy)- 5-(6-(methylsulfonyl) pyridin-3-yl)thiazolo [5,4-b]pyridine

1167

2-((S)-1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(2-fluoro-6-(methyl- sulfonyl)pyridin-3-yl) thiazolo[5,4-b]pyridine

1168

2-((R)-1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(2-methyl-6-(methyl- sulfonyl)pyridin-3-yl) thiazolo[5,4-b]pyridine

1169

2-((R)-1-(1-(3-isopropyl- 1,2,4-oxadiazol-5-yl) piperidin-4-yl)ethoxy)- 5-(2-methyl-4-(methyl- sulfonyl)phenyl) thiazolo[5,4-b]pyridine

18. The compound of claim 1 , which is

3-isopropyl-5-(1-(5-(4-(methylsulfonyl)phenoxy)thiazolo[5,4-b]pyridin-2-yl)piperidin-4-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(((5-(4-(methylsulfonyl)phenoxy)thiazolo[5,4-b]pyridin-2-yl)oxy)methyl)piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(1-(2-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-5-yl)piperidin-4-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(1-(5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)piperidin-4-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-((5-(4-(methylsulfonyl)phenoxy)thiazolo[5,4-b]pyridin-2-yl)oxy)piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)methyl)piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)piperidin-1-yl)-1,2,4-oxadiazole;

2-(4-(5-ethylpyrimidin-2-yl)piperazin-1-yl)-5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridine;

5-((1-benzylpiperidin-4-yl)methoxy)-2-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridine;

2-(4-(5-ethylpyrimidin-2-yl)piperazin-1-yl)-5-(4-(methylsulfonyl)phenoxy)thiazolo[5,4-b]pyridine;

isopropyl 4-(5-(4-(methyl sulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)-5,6-dihydropyridine-1 (2H)-carboxylate;

isopropyl4-(5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl) piperazine-1-carboxylate;

isopropyl-4-(5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl) piperidine-1-carboxylate;

1-(5-ethylpyrimidin-2-yl)-N-(5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)piperidine-4-carboxamide;

2-(4-(5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)-5,6-dihydropyridin-1(2H)-yl)ethanol;

isopropyl-4-(methyl(5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)amino)piperidine-1-carboxylate;

N-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-N-methyl-5-(4-(methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2-amine;

isopropyl 4-((5-(4-(dimethyl carbamoyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)(methyl)amino)piperidine-1-carboxylate;

isopropyl (5-(4-(methyl sulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl) carbonate;

3-isopropyl-5-(4-(1-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(1-(5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)pyrrolidin-3-yl)-1,2,4-oxadiazole;

4-(2-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)thiazolo[5,4-b]pyridin-5-yl)-N,N-dimethylbenzamide;

N-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)-N-methyl-5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-amine;

4-(2-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)thiazolo[5,4-b]pyridin-5-yl)-N-(2-methoxyethyl)benzamide; OR

N-(3-fluoro-4-(methylsulfonyl)phenyl)-2-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)thiazolo[5,4-b]pyridin-5-amine.

19. The compound of claim 1 , which is

5-(4-(methylsulfonyl)phenyl)-2-(1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)thiazolo[5,4-b]pyridine;

N,N-dimethyl-4-(5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)-5,6-dihydropyridine-1 (2H)-carboxamide;

N,N-dimethyl-4-(5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)piperidine-1-carboxamide;

(4-(2-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)thiazolo[5,4-b]pyridin-5-yl)phenyl)(morpholino)methanone;

N,N-diisopropyl-4-(5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)-5,6-dihydropyridine-1 (2H)-carboxamide;

(S)-3-isopropyl-5-(4-(1-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

(R)-3-isopropyl-5-(4-(1-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

3-cyclopropyl-5-(4-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)piperidin-1-yl)-1,2,4-oxadiazole;

isopropyl 4-(2-((5-(4-(methyl sulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)-5,6-dihydropyridine-1 (2H)-carboxylate;

3-isopropyl-5-(4-(2-((5-(4-(methyl sulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)-5,6-dihydropyridin-1 (2H)-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(2-methoxy-1-((5-(4-(methylsulfonyl); phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole 3-isopropyl-5-(4-(1-((7-methyl-5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(((7-methyl-5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)methyl)piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(1-((6-methyl-5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

5-(4-(cyclopropyl((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)methyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

3-isopropyl-5-(4-(2-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethylidene) piperidin-1-yl)-1,2,4-oxadiazole; OR

3-isopropyl-5-(4-(2-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole.

20. The compound of claim 1 , which is

3-isopropyl-5-(4-(2-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)propyl) piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(2-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)propylidene) piperidin-1-yl)-1,2,4-oxadiazole;

(S)-4-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridin-5-yl)-N,N-dimethylbenzamide;

3-fluoro-4-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridin-5-yl)-N,N-dimethylbenzamide;

2-fluoro-4-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridin-5-yl)-N,N-dimethylbenzamide;

3-cyclopropyl-5-(4-(1-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

N-cyclopropyl-4-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo [5,4-b]pyridin-5-yl)benzamide;

4-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridin-5-yl)-N-(2-methoxyethyl)benzamide;

(4-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl) ethoxy)thiazolo[5,4-b]pyridin-5-yl)phenyl)(morpholino)methanone;

N-cyclopropyl-4-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo [5,4-b]pyridin-5-yl)-N-methylbenzamide;

5-(4-(methylsulfonyl)phenyl)-2-(1-(1-(5-propylpyrimidin-2-yl) piperidine-4-yl)ethoxy)thiazolo [5,4-b]pyridine;

3-isopropyl-5-(4-(1-((5-(pyridin-3-yl)thiazolo[5,4-b]pyridin-2-yl)oxy) ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

2-(1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridine;

isopropyl-4-(1-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidine-1-carboxylate;

3-isopropyl-5-(4-(1-((5-(4-((methylsulfonyl)methyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

5-isopropyl-3-(4-(1-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(1-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)phenyl)-1,2,4-oxadiazole;

5-(3-fluoro-4-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

4-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridin-5-yl)-N-methylbenzenesulfonamide;

5-(4-(1-((5-(4-(ethylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

5-(4-(1-((5-(4-(cyclopropylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

5-(4-(1-((5-(4-(cyclopropylsulfinyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

4-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridin-5-yl)benzonitrile;

4-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridin-5-yl)-N-(2-methoxyethyl)benzene sulfonamide;

3-isopropyl-5-(4-(1-((5-(4-((2-methoxyethyl)sulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl) piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(1-((5-(4-((2-methoxyethyl)sulfinyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl) piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(1-((5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

(R)-3-isopropyl-5-(4-(1-((5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

(R)-4-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridin-5-yl)-1-methylpyridin-1-ium;

4-(2-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)thiazolo[5,4-b]pyridin-5-yl)-N-methylbenzenesulfonamide;

4-(2-(4-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)thiazolo[5,4-b]pyridin-5-yl)-N-(2-methoxyethyl) benzenesulfonamide;

N-(4-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridin-5-yl)phenyl)methanesulfonamide;

2-(1-(1-(1-methyl-1H-tetrazol-5-yl)piperidin-4-yl)ethoxy)-5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridine;

(S)-5-(4-(1-((5-(3-fluoropyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

3-isopropyl-5-(1-(5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)piperidin-4-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(1-(5-(4-((2-methoxyethyl)sulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)piperidin-4-yl)-1,2,4-oxadiazole;

5-(4-(1-((5-(4-(1H-tetrazol-1-yl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

3-isopropyl-5-(1-(5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridin-2-yl)piperidin-4-yl)-1,2,4-oxadiazole; OR

5-(4-(1-((5-(2-fluoropyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole.

21. The compound of claim 1 , which is

(S)-3-isopropyl-5-(4-(1-((5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(((5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)methyl)piperidin-1-yl)-1,2,4-oxadiazole;

5-(4-(((5-(3-fluoropyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)methyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

5-(4-(((5-(4-(1H-tetrazol-1-yl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)methyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

5-(4-(((5-(2-fluoropyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)methyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

2-(1-(1-(5-ethylpyridin-2-yl)piperidine-4-yl)ethoxy)-5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridine;

5-(4-(methylsulfonyl)phenyl)-2-(1-(1-(5-vinylpyridin-2-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridine;

(S)-5-(4-(methylsulfonyl)phenyl)-2-(1-(1-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)thiazolo [5,4-b]pyridine;

(R)-5-(4-(methylsulfonyl)phenyl)-2-(1-(1-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)thiazolo [5,4-b]pyridine;

3-isopropyl-5-(4-(((5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)methyl)piperidin-1-yl)-1,2,4-oxadiazole;

(S)-3-isopropyl-5-(4-(1-((5-(pyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

(S)-5-(4-(1-((5-(2-fluoropyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

3-isopropyl-5-(4-(2,2,2-trifluoro-1-((5-(4-(methylsulfonyl)phenyl) thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

(S)-5-(4-(1-((5-(4-(cyclopropylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

(S)-5-(4-(1-((5-(3-fluoropyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

2-isopropyl-5-(4-(1-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,3,4-oxadiazole;

4-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl) ethoxy)thiazolo[5,4-b]pyridin-5-yl)pyridine 1-oxide;

(S)-5-(6-(methylsulfonyl)pyridin-3-yl)-2-(1-(1-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)thiazolo [5,4-b]pyridine;

5-(4-(1-((5-(3-fluoro-4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

(S)-5-(2-fluoropyridin-4-yl)-2-(1-(1-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridine;

3-isopropyl-5-(4-(2,2,2-trifluoro-1-((5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridin-2-yl)oxy) ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(2,2,2-trifluoro-1-((5-(2-fluoropyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl) piperidin-1-yl)-1,2,4-oxadiazole;

(S)-2-(1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(2-fluoropyridin-4-yl)thiazolo[5,4-b]pyridine;

3-isopropyl-5-(4-(1-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl) cyclohexyl)-1,2,4-oxadiazole;

(S)-2-(1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(6-(methylsulfonyl)pyridin-3-yl) thiazolo[5,4-b]pyridine;

2-(1-(1-(3-isopropyl-1,2,4-thiadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(4-(methyl sulfonyl)phenyl)thiazolo[5,4-b]pyridine;

3-isopropyl-5-(4-(1-((6-(4-(methyl sulfonyl)phenyl)thiazolo[4,5-b] pyrazin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

2-(1-(1-(cyclopropylsulfonyl)piperidin-4-yl)ethoxy)-5-(4-(methyl sulfonyl)phenyl)thiazolo[5,4-b] pyridine;

6-(4-(methylsulfonyl)phenyl)-2-(1-(1-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)thiazolo[4,5-b]pyrazine;

5-(4-(1-((5-(2-fluoro-4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole; OR

5-(3-fluoro-4-(1-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole.

22. The compound of claim 1 , which is

2-(1-(1-(5-isopropylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridine;

(S)-3-isopropyl-5-(4-(1-((6-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[4,5-b]pyrazin-2-yl)oxy) ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

5-(4-(methylsulfonyl)phenyl)-2-(1-(1-(propylsulfonyl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridine;

5-(4-(1-((5-(2-chloropyrimidin-5-yl)thiazolo[5,4-b]pyridin-2-yl) oxy)ethyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

1-methylcyclopropyl4-(1-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl) piperidine-1-carboxylate;

5-(4-(methylsulfonyl)phenyl)-2-(1-(1-(5-(prop-1-en-2-yl)pyrimidin-2-yl)piperidin-4-yl)ethoxy)thiazolo [5,4-b]pyridine;

(S)-5-(4-(1-((5-(2-chloropyrimidin-5-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

2-(1-(1-(5-chloropyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridine;

3-isopropyl-5-(4-(1-((5-(thiazol-5-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(1-((5-(isoxazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(1-((5-(2-methylpyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(1-((5-(isothiazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(1-((5-(3-methylisothiazol-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

4-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridin-5-yl)pyridin-2(1H)-one;

4-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridin-5-yl)-1-methylpyridin-2(1H)-one;

5-((3R,4S)-3-fluoro-4-(((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)methyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

5-((3S,4S)-3-fluoro-4-(((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)methyl) piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

3-isopropyl-5-(4-(1-(5-(4-(methyl sulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)ethoxy)piperidin-1-yl)-1,2,4-oxadiazole;

5-(4-(1-((5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-3-(trifluoromethyl)-1,2,4-oxadiazole;

5-(4-(1-((5-(2-chloropyridin-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-3-isopropyl-1,2,4-oxadiazole;

3-isopropyl-5-(4-(1-((5-(2-(methylsulfonyl)pyrimidin-5-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(1-((5-(pyridazin-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

3-isopropyl-5-(4-(1-((5-(pyridazin-4-yl)thiazolo[5,4-b]pyridin-2-yl)oxy)ethyl)piperidin-1-yl)-1,2,4-oxadiazole;

2-((S)-1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(2-chloropyrimidin-5-yl)thiazolo[5,4-b]pyridine;

2-((S)-1-(1-(5-chloropyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-(1-(1-(5-cyclopropylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-((S)-1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(2-(methylsulfinyl)pyrimidin-5-yl)thiazolo[5,4-b]pyridine;

N-(5-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridin-5-yl)pyrimidin-2-yl)-N-methylacetamide;

2-((R)-1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)pyrrolidin-3-yl)ethoxy)-5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-((S)-1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)pyrrolidin-3-yl)ethoxy)-5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine; OR

2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(6-chloropyridin-3-yl)thiazolo[5,4-b]pyridine.

23. The compound of claim 1 , which is

2-((S)-1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(2-chloropyridin-4-yl)thiazolo[5,4-b]pyridine;

1-(5-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridin-5-yl)pyridin-2-yl)imidazolidin-2-one;

2-((S)-1-(1-(3-(trifluoromethyl)-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

1-(5-(2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)thiazolo[5,4-b]pyridin-5-yl)pyridin-2-yl)pyrrolidin-2-one;

2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(6-(trifluoromethyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-(1-(1-(5-chloropyrazin-2-yl)piperidin-4-yl)ethoxy)-5-(4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridine;

2-(1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridine;

2-(1-(1-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridine;

2-(1-(1-(5-chloropyrazin-2-yl)piperidin-4-yl)ethoxy)-5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-((S)-1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(6-(trifluoromethyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-((S)-1-(1-(5-propylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(pyridin-4-yl)thiazolo[5,4-b]pyridine;

2-((S)-1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(6-(trifluoromethyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-((S)-1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(3-fluoro-4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridine;

2-(1-(1-(3-ethyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-(1-(1-(5-methylpyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(5-(methylsulfonyl)pyrazin-2-yl)thiazolo[5,4-b]pyridine;

2-(1-(1-(5-(trifluoromethyl)pyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-((S)-1-(1-(3-ethyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(5-(methylsulfonyl)pyridin-2-yl)thiazolo[5,4-b]pyridine;

2-(1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-d]pyrimidine;

2-(1-(1-(5-(methoxymethyl)pyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-((R)-1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(6-(cyclopropylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-((R)-1-(1-(5-(methoxymethyl)pyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-((S)-1-(1-(5-(trifluoromethyl)pyrimidin-2-yl)piperidin-4-yl)ethoxy)-5-(6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-((S)-1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(2-fluoro-6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine;

2-((R)-1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(2-methyl-6-(methylsulfonyl)pyridin-3-yl)thiazolo[5,4-b]pyridine; OR

2-((R)-1-(1-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)ethoxy)-5-(2-methyl-4-(methylsulfonyl)phenyl)thiazolo[5,4-b]pyridine.

24. A method of treating diseases and conditions mediated through GPR119 comprising administering the compound of claim 1 to a patient in need thereof.

25. The method of claim 24 , wherein said disease is metabolic disorder.

26. The method of claim 2 , wherein said disease is diabetes.

27. The method of claim 2 , wherein said disease is Type II diabetes.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 28, 2017
From: PATIL, RAKESH ISHWAR; VERMA, JEEVAN; SHAH, DHARMESH; ALI, SAZID; BAPURAM, SRINIVASA REDDY; RAI, SANTOSH KUMAR; KUMAR, ANIL
To: MANKIND PHARMA LTD.
Reel/Frame 044501/0364 →
Priority Claims (1)
IN 201611012425 · Apr 8, 2016 · national
Continuity (1)
Related Publication 20170291910A1 · Oct 12, 2017