IP Library › Granted Patent US 10,087,185
Granted Patent B2
US 10,087,185 · App. 15/790,849 · Granted Oct 2, 2018

Fused bicylic pyridine compounds and their use as AMPA receptor modulators

Inventors: Michael K. Ameriks (San Diego, CA); Márió Gyuris (Budapest, HU); Brian Ngo Laforteza (San Diego, CA); Terry Patrick Lebold (San Diego, CA); Stephen Todd Meyer (San Diego, CA); Suchitra Ravula (San Diego, CA); Brad M. Savall (San Diego, CA); Brock T. Shireman (Poway, CA); Warren Stanfield Wade (San Diego, CA); János Gerencsér (Budapest, HU)
Assignee: Janssen Pharmaceutica NV
C07D471/04C07D401/14C07D417/14C07D487/04
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,087,185
App. No.
15/790,849
Granted
Oct 2, 2018
Kind
B2
Abstract

Provided herein are compounds of Formula (I), and pharmaceutically acceptable salts, N-oxides, or solvates thereof, Also provided herein are pharmaceutical compositions comprising compounds of Formula (I) and methods of using compounds of Formula (I).

Claims (185)

1. A compound of Formula (I):

wherein

Y is N or CH;

R 1 is selected from the group consisting of: H, halo, and C 1-6 alkyl;

R 2 is selected from the group consisting of: C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, and C 3-8 cycloalkyl;

R 3 is selected from the group consisting of: H, halo, C 1-6 alkyl, C 1-6 alkoxy, CN, and CF 3 ;

R 4 is selected from the group consisting of: C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, phenyl substituted with F, and pyridyl; and

is selected from the group consisting of: —CH═N—, —CH 2 —C(═O)—, and —S—C(═O)—; and

pharmaceutically acceptable salts, N-oxides, or solvates thereof.

2. The compound of claim 1 , wherein Y is N.

3. The compound of claim 1 , wherein Y is CH.

4. The compound of claim 1 , wherein R 1 is H.

5. The compound of claim 1 , wherein R 1 is Cl or F.

6. The compound of claim 1 , wherein R 1 is CH 3 or CH 2 CH 3 .

7. The compound of claim 1 , wherein R 2 is CF 3 , CHF 2 , or CF 2 (CH 3 ).

8. The compound of claim 1 , wherein R 2 is CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , or CH(CH 3 ) 2 .

9. The compound of claim 1 , wherein R 2 is cyclopropyl.

10. The compound of claim 1 , wherein R 2 is OCH 3 or OCH 2 CH 3 .

11. The compound of claim 1 , wherein R 3 is H, Cl, CH 3 , or CH 2 CH 3 .

12. The compound of claim 1 , wherein R 3 is OCH 3 or CN.

13. The compound of claim 1 , wherein R 3 is CF 3 .

14. The compound of claim 1 , wherein R 4 is CF 3 , CF 2 (CH 3 ), or CHF 2 .

15. The compound of claim 1 , wherein R 4 is OCH 3 .

16. The compound of claim 1 , wherein R 4 is CH 2 CH 3 .

17. The compound of claim 1 , wherein R 4 is 4-fluorophenyl, pyridin-3-yl, or pyridin-4-yl.

18. The compound of claim 1 , wherein

is —CH═N—.

19. The compound of claim 1 , wherein

is —CH 2 —C(═O)—.

20. The compound of claim 1 , wherein

is —S—C(═O)—.

21. The compound of claim 1 , and pharmaceutically acceptable salts, solvates, or N-oxides thereof, having the structure of Formula (1A):

wherein

R 1 is selected from the group consisting of: H, halo, CH 3 , and CH 2 CH 3 ;

R 2 is selected from the group consisting of: C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, and C 3-8 cycloalkyl;

R 4 is selected from the group consisting of: C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, phenyl substituted with F, and pyridyl; and

R 5 is selected from the group consisting of:

22. The compound of claim 1 , and pharmaceutically acceptable salts, solvates, or N-oxides thereof, having the structure of Formula (1B):

wherein

R 1 is H, or C 1-6 alkyl;

R 2 is selected from the group consisting of: C 1-6 alkyl, C 1-6 haloalkyl, and C 3-8 cycloalkyl;

R 4 is CF 2 H or CF 3 ; and

R 5 is selected from the group consisting of:

23. A compound selected from the group consisting of:

5-(7-Chloro-1H-indazol-5-yl)-2,6-bis(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Methyl-1H-indazol-5-yl)-2,6-bis(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(2,6-Bis(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-7-chloroindolin-2-one;

5-(2,6-Bis(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-7-methylindolin-2-one;

8-Chloro-5-(7-chloro-1H-indazol-5-yl)-2,6-bis(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-8-methyl-2,6-bis(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-2-(difluoromethyl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Methyl-1H-indazol-5-yl)-2-(difluoromethyl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

7-Chloro-5-(2-(difluoromethyl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

7-Methyl-5-(2-(difluoromethyl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

2-(Difluoromethyl)-6-(trifluoromethyl)-5-(7-(trifluoromethyl)-1H-indazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(2-(Difluoromethyl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-7-methoxyindolin-2-one;

5-(7-Chloro-1H-indazol-5-yl)-2-(difluoromethyl)-6-methoxy-[1,2,4]triazolo[1,5-a]pyridine;

2-(Difluoromethyl)-6-methoxy-5-(7-methyl-1H-indazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine;

2-(Difluoromethyl)-6-methoxy-5-(7-(trifluoromethyl)-1H-indazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-6-(difluoromethyl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

6-(Difluoromethyl)-5-(7-methyl-1H-indazol-5-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

7-Chloro-5-(6-(difluoromethyl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

5-[6-(Difluoromethyl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-7-methyl-indolin-2-one;

5-[6-(Difluoromethyl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]-7-methoxy-indolin-2-one;

5-(7-Chloro-1H-indazol-5-yl)-2-methyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

2-Methyl-5-(7-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

7-Chloro-5-(2-methyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

7-Methyl-5-(2-methyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

5-(7-Chloro-1H-indazol-5-yl)-2-ethyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

2-Ethyl-5-(7-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

7-Chloro-5-(2-ethyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

5-(2-Ethyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-7-methylindolin-2-one;

8-Chloro-5-(7-chloro-1H-indazol-5-yl)-2-ethyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

8-Chloro-2-ethyl-5-(7-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-2-ethyl-8-fluoro-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

7-Chloro-5-[2-ethyl-8-fluoro-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl]indolin-2-one;

2-Cyclopropyl-8-fluoro-5-(7-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-8-fluoro-2-isopropyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-2-ethyl-8-methyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-2-isopropyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

2-Isopropyl-5-(7-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-2-cyclopropyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

2-Cyclopropyl-5-(7-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

7-Chloro-5-(2-cyclopropyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

5-(2-Cyclopropyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-7-methylindolin-2-one;

5-(7-Chloro-1H-indazol-5-yl)-2-(1,1-difluoroethyl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-2-methoxy-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-6-(difluoromethyl)-2-ethyl-[1,2,4]triazolo[1,5-a]pyridine;

6-(Difluoromethyl)-2-ethyl-5-(7-methyl-1H-indazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine;

7-Chloro-5-(6-(difluoromethyl)-2-ethyl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

5-(6-(Difluoromethyl)-2-ethyl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-7-methylindolin-2-one;

5-(7-Chloro-1H-indazol-5-yl)-2-cyclopropyl-6-(difluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

2-Cyclopropyl-6-(difluoromethyl)-5-(7-methyl-1H-indazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-6-methoxy-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

6-Methoxy-5-(7-methyl-1H-indazol-5-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

6-Ethyl-5-(7-methyl-1H-indazol-5-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-6-(1,1-difluoroethyl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

6-(2-(Difluoromethyl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)benzo[d]thiazol-2(3H)-one;

6-(4-Fluorophenyl)-5-(7-methyl-1H-indazol-5-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

6-(4-Fluorophenyl)-5-(1H-indazol-5-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(6-(4-Fluorophenyl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-7-methylindolin-2-one;

5-(7-Methyl-1H-indazol-5-yl)-6-(pyridin-3-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Methyl-1H-indazol-5-yl)-6-(pyridin-4-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

6-(4-Fluorophenyl)-2-methyl-5-(7-methyl-1H-indazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine;

2-Ethyl-6-(4-fluorophenyl)-5-(7-methyl-1H-indazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine;

2-Cyclopropyl-6-(4-fluorophenyl)-5-(7-methyl-1H-indazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(2,6-Bis(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl)-7-chloro-1H-indazole;

5-(2,6-Bis(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl)-7-methyl-1H-indazole;

5-(2,6-Bis(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl)-7-methylindolin-2-one;

5-(2,6-Bis(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl)-7-chloroindolin-2-one;

5-(2-Cyclopropyl-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl)-7-methylindolin-2-one;

5-(2-Cyclopropyl-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl)-7-chloroindolin-2-one;

5-(2-Cyclopropyl-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl)-7-methyl-1H-indazole;

7-Chloro-5-(2-cyclopropyl-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl)-1H-indazole;

5-(2-Isopropyl-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl)-7-methylindolin-2-one;

5-(2-Isopropyl-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl)-7-chloroindolin-2-one;

7-Chloro-5-(2-isopropyl-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl)-1H-indazole; and

5-(2-Isopropyl-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl)-7-methyl-1H-indazole; and

pharmaceutically acceptable salts, N-oxides or solvates thereof.

24. A compound selected from the group consisting of:

7-Chloro-5-(2-cyclopropyl-8-methyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

2-Cyclopropyl-8-methyl-5-(7-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-6-(difluoromethyl)-8-methyl-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-2-(difluoromethyl)-8-methyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

2-(Difluoromethyl)-8-methyl-5-(7-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

2-(Difluoromethyl)-8-methyl-5-(7-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-2-cyclopropyl-8-ethyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

2-Cyclopropyl-8-ethyl-5-(7-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(2-Cyclopropyl-8-ethyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-7-methylindolin-2-one;

5-(7-Chloro-1H-indazol-5-yl)-8-methyl-2-propyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

8-Methyl-5-(7-methyl-1H-indazol-5-yl)-2-propyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

7-Methyl-5-(8-methyl-2-propyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

2-(Difluoromethyl)-8-methyl-5-(7-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-2-(difluoromethyl)-8-ethyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

2-(Difluoromethyl)-8-ethyl-5-(7-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-2,8-diethyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

2,8-Diethyl-5-(7-methyl-1H-indazol-5-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-6-(difluoromethyl)-8-ethyl-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

6-(Difluoromethyl)-8-ethyl-5-(7-methyl-1H-indazol-5-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-2-cyclopropyl-6-(difluoromethyl)-8-ethyl-[1,2,4]triazolo[1,5-a]pyridine;

2-Cyclopropyl-6-(difluoromethyl)-8-ethyl-5-(7-methyl-1H-indazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine;

6-(Difluoromethyl)-8-methyl-5-(7-methyl-1H-indazol-5-yl)-2-propyl-[1,2,4]triazolo[1,5-a]pyridine;

8-Chloro-5-(7-chloro-1H-indazol-5-yl)-2-propyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

7-Chloro-5-(8-chloro-2-propyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

5-(8-Chloro-2-propyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-7-methylindolin-2-one;

5-(2-Cyclopropyl-8-methyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-7-methylindolin-2-one;

7-Chloro-5-(2-ethyl-8-methyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

2-Ethyl-8-methyl-6-(trifluoromethyl)-5-(7-(trifluoromethyl)-1H-indazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(2-Ethyl-8-methyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-7-(trifluoromethyl)indolin-2-one;

7-Chloro-5-(2-ethyl-8-methyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

7-Ethyl-5-(8-methyl-2,6-bis(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

7-Methyl-5-(8-methyl-2,6-bis(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

7-Methoxy-5-(8-methyl-2,6-bis(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

8-Methyl-5-(7-methyl-1H-indazol-5-yl)-2,6-bis(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(8-Methyl-2,6-bis(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-2-oxoindoline-7-carbonitrile;

5-(7-Chloro-1H-indazol-5-yl)-6-(difluoromethyl)-8-methyl-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

7-Chloro-5-(6-(difluoromethyl)-8-methyl-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

6-(Difluoromethyl)-8-methyl-5-(7-methyl-1H-indazol-5-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-2-cyclopropyl-6-(difluoromethyl)-8-methyl-[1,2,4]triazolo[1,5-a]pyridine;

7-Chloro-5-(2-cyclopropyl-6-(difluoromethyl)-8-methyl-[1,2,4]triazolo[1,5-a]pyridin-5-yl)indolin-2-one;

2-Cyclopropyl-6-(difluoromethyl)-8-methyl-5-(7-methyl-1H-indazol-5-yl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-6-(difluoromethyl)-2-ethyl-8-methyl-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-2,8-dimethyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

5-(7-Chloro-1H-indazol-5-yl)-2-ethoxy-8-methyl-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine;

7-Chloro-5-(2-cyclopropyl-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl)-1H-indazole;

5-[6-(Difluoromethyl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl]-7-methyl-indolin-2-one;

7-(7-Chloro-1H-indazol-5-yl)-6-(difluoromethyl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine;

6-(Difluoromethyl)-7-(7-methyl-1H-indazol-5-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine;

5-[6-(Difluoromethyl)-4-methyl-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl]-7-methyl-indolin-2-one;

6-(Difluoromethyl)-4-methyl-7-(7-methyl-1H-indazol-5-yl)-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine;

7-Chloro-5-[6-(difluoromethyl)-4-methyl-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-7-yl]indolin-2-one; and

7-(7-Chloro-1H-indazol-5-yl)-6-(difluoromethyl)-4-methyl-2-(trifluoromethyl)pyrazolo[1,5-a]pyridine; and

pharmaceutically acceptable salts, N-oxides or solvates thereof.

25. A pharmaceutical composition comprising:

(A) an effective amount of at least one compound of Formula (I):

wherein

Y is N or CH;

R 1 is selected from the group consisting of: H, halo, C 1-6 alkyl;

R 2 is selected from the group consisting of: C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, and C 3-8 cycloalkyl;

R 3 is selected from the group consisting of: H, halo, C 1-6 alkyl, C 1-6 alkoxy, CN, and CF 3 ;

R 4 is selected from the group consisting of: C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy, phenyl substituted with F, and pyridyl; and

is selected from the group consisting of: —CH═N—, —CH 2 —C(═O)—, and —S—C(═O)—; and

pharmaceutically acceptable salts, N-oxides or solvates of compounds of Formula (I); and

(B) at least one pharmaceutically acceptable excipient.

26. A pharmaceutical composition comprising an effective amount of at least one compound of claim 22 and at least one pharmaceutically acceptable excipient.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 23, 2023
From: JANSSEN PHARMACEUTICA NV
To: RAPPORT THERAPEUTICS, INC.
Reel/Frame 063079/0430 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 18, 2023
From: JANSSEN PHARMACEUTICA NV
To: PRECISION NEUROSCIENCE NEWCO, INC.
Reel/Frame 062404/0771 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 23, 2018
From: AMERIKS, MICHAEL K.; GYURIS, MÁRIÓ; LAFORTEZA, BRIAN NGO; LEBOLD, TERRY PATRICK; MEYER, STEPHEN TODD; RAVULA, SUCHITRA; SAVALL, BRAD M.; SHIREMAN, BROCK T.; WADE, WARREN STANFIELD; GERENCSÉR, JÁNOS
To: JANSSEN PHARMACEUTICA NV
Reel/Frame 046674/0504 →
Continuity (2)
Provisional Application 62412868 · Oct 26, 2016
Related Publication 20180111933A1 · Apr 26, 2018
Cited By (1)
US 12,304,908