Granted Patent B2

US 12,655,128 · App. 18/422,258 · Granted Jun 16, 2026

Inventors: Jason D. Brubaker (Cambridge, MA); Joseph L. Kim (Wayland, MA); Kevin J. Wilson (Cambridge, MA); Douglas Wilson (Ayer, MA); Lucian V. DiPietro (Gloucester, MA)

Assignee: Rigel Pharmaceuticals, Inc.

C07D401/14C07D239/30C07D239/36C07D403/14

Abstract

Claims (23)

1 . A compound having the structural formula (IIb):

or a pharmaceutically acceptable salt thereof, wherein:

X 1 is selected from N, CH and C (halo);

X 2 is selected from N and CH;

X 3 is selected from N and CH;

R 12 is selected from hydrogen, hydroxyl, halo and O—C 1 -C 4 alkyl;

each of R 13a , R 13b , R 18a and R 18b is independently selected from hydrogen and C 1 -C 4 alkyl;

R 14 is selected from hydrogen, —C 1 -C 4 alkyl and —O—C 1 -C 4 alkyl;

R 15 is selected from hydrogen and —C 1 -C 4 alkyl;

R 16 is selected from hydrogen and —C 1 -C 4 alkyl;

R 17b is selected from hydrogen and halo; and

R 17a and R 17c are independently selected from hydrogen and —C 1 -C 4 alkyl.

2 . The compound of claim 1 , wherein X 1 is selected from N, CH and C(Cl).

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

4 . The compound of claim 2 , wherein X 3 is CH.

5 . The compound of claim 1 , wherein R 12 is selected from hydrogen, hydroxyl, fluoro and —O—CH 3 .

6 . The compound of claim 1 , wherein each of R 13a , R 13b , R 18a and R 18b is independently selected from hydrogen, methyl and ethyl; and wherein at least one pair of R 13a and R 13b or R 18a and R 18b is simultaneously hydrogen.

7 . The compound of claim 1 , wherein R 14 is selected from hydrogen, —CH 3 , —CH 2 CH 3 , —OCH 3 and —OCH 2 CH 3 .

8 . The compound of claim 1 , wherein R 15 is selected from hydrogen and —CH 3 .

9 . The compound of claim 1 , wherein R 16 is selected from hydrogen and —CH 3 .

10 . The compound of claim 1 , wherein R 17b is selected from hydrogen, chloro and fluoro.

11 . The compound of claim 1 , wherein R 17a and R 17c are simultaneously hydrogen or —CH 3 , wherein when R 17a and R 17c are simultaneously —CH 3 , R 17b is hydrogen.

12 . A pharmaceutical composition comprising a compound of claim 1 ; and a pharmaceutically acceptable carrier.

Assignments (5)

Continuity (7)

References Cited (301)