Granted Patent B2

US 12,410,167 · App. 18/480,164 · Granted Sep 9, 2025

Inventors: Stéphane Dorich (Pointe-Claire, CA); Jason Burch (Pointe-Claire, CA); Miguel St-Onge (Saint-Lazare, CA); Amandine Chefson (Montreal, CA); Alexandre Côté (Laval, CA); Ramsay Beveridge (Pointe-Claire, CA); Stéphane Ciblat (Montreal, CA)

Assignee: Ventus Therapeutics U.S., Inc.

C07D471/04A61K31/501A61K31/502A61K31/5025A61K31/5377C07D405/12C07D491/048C07D495/04C07D519/00

Abstract

Claims (28)

1. A compound of Formula (II):

or a pharmaceutically acceptable salt, solvate, clathrate, hydrate, stereoisomer, or tautomer thereof;

wherein:

Y is phenyl independently substituted with one, two, or three substituents selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl, halo, cyano, and —R 4 OR 5 , wherein at least one substitution is substituted at the para-position of the phenyl ring;

R 1 is C 1 -C 6 alkyl independently substituted with one or more halo and —R 4 OR 5 ;

R 2 and R 3 , together with the atoms to which they are attached, form a 5- to 9-membered heteroaryl optionally substituted with one or more R 2a ;

R 2a is hydrogen, C 1 -C 6 alkyl, halo or C 1 -C 6 haloalkyl;

R 4 is absent, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, or C 2 -C 6 alkynyl; and

R 5 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 8 cycloalkyl, 3- to 8-membered heterocycloalkyl, C 5 -C 10 aryl, or 5- to 9-membered heteroaryl.

2. The compound according to claim 1 , wherein Y is phenyl independently substituted with one, two, or three substituents selected from the group consisting of C 1 -C 6 haloalkyl, halo, and —R 4 OR 5 , wherein at least one substitution is substituted at the para-position of the phenyl ring.

3. The compound according to claim 2 , wherein R 1 is:

4. The compound according to claim 2 , wherein R 2 and R 3 , together with the atoms to which they are attached, form:

5. The compound according to claim 4 , wherein R 4 is absent and R 5 is hydrogen.

6. The compound according to claim 5 , wherein the compound is of Formula (II-i):

or a pharmaceutically acceptable salt, solvate, clathrate, hydrate, stereoisomer, or tautomer thereof, wherein R 2a is hydrogen.

7. The compound according to claim 5 , wherein the compound is of Formula (II-h):

or a pharmaceutically acceptable salt, solvate, clathrate, hydrate, stereoisomer, or tautomer thereof, wherein R 2a is hydrogen.

8. The compound according to claim 7 , wherein R 1 is C 1 -C 6 alkyl independently substituted with one or more —R 4 OR 5 .

9. The compound according to claim 7 , wherein R 1 is:

10. The compound according to claim 9 , wherein R 1 is

11. The compound according to claim 10 , wherein Y is phenyl independently substituted with one, two, or three substituents selected from the group consisting of C 1 -C 6 haloalkyl, halo, and —R 4 OR 5 , provided the phenyl is substituted at the para-position with halo.

12. The compound according to claim 11 , wherein the halo is chloro.

13. The compound according to claim 10 , wherein Y is phenyl independently substituted with two substituents selected from the group consisting of halo and —R 4 OR 5 , provided the phenyl is substituted at the para-position with halo.

14. The compound according to claim 13 , wherein one of the two substituents is halo at the para position and the other substituent is —R 4 OR 5 .

15. The compound according to claim 14 , wherein the halo is chloro.

16. The compound according to claim 1 , wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

17. A pharmaceutical composition comprising a compound according to claim 1 , or a pharmaceutically acceptable salt, solvate, clathrate, hydrate, stereoisomer, or tautomer thereof.

Continuity (3)

References Cited (400)