IP Library Granted Patent US 11,731,958
Granted Patent B2
US 11,731,958 · App. 17/015,797 · Granted Aug 22, 2023

Carboxamide compounds and uses thereof

Inventors: Oleg Vechorkin (Wilmington, DE); Jun Pan (Media, PA); Alexander Sokolsky (Philadelphia, PA); Evan Styduhar (Claymont, DE); Wenqing Yao (Chadds Ford, PA)
Assignee: Incyte Corporation
C07D403/14C07D239/26C07D401/12C07D401/14C07D403/12C07D413/12C07D413/14C07D487/04C07D487/08
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Quick Facts
Patent No.
US 11,731,958
App. No.
17/015,797
Granted
Aug 22, 2023
Kind
B2
Abstract

Disclosed are compounds of Formula (I′) methods of using the compounds for inhibiting HPK1 activity and pharmaceutical compositions comprising such compounds. The compounds are useful in treating, preventing or ameliorating diseases or disorders associated with HPK1 activity such as cancer.

Claims (30)

1. A method for treating a cancer in a patient, said method comprising: administering to the patient a therapeutically effective amount of a compound selected from:

N-(2-((2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-5-fluorophenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide;

N-(2-((1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl)-4-(4-cyanopyridin-3-yl)phenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide; and

N-(2-((2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-4-(4-cyanopyridin-3-yl)phenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide,

or a pharmaceutically acceptable salt of any of the aforementioned;

wherein the cancer is selected from breast cancer, colorectal cancer, lung cancer, ovarian cancer, pancreatic cancer, Burkitt's lymphoma, acute promonocytic leukemia, and hepatocellular carcinoma.

2. The method of claim 1 , wherein the cancer is selected from breast cancer, colorectal cancer, lung cancer, ovarian cancer, and pancreatic cancer.

3. The method of claim 1 , wherein the cancer is breast cancer.

4. The method of claim 1 , wherein the cancer is colorectal cancer.

5. The method of claim 1 , wherein the cancer is lung cancer.

6. The method of claim 1 , wherein the cancer is ovarian cancer.

7. The method of claim 1 , wherein the cancer is pancreatic cancer.

8. The method of claim 1 , wherein the cancer is Burkitt's lymphoma.

9. The method of claim 1 , wherein the cancer is acute promonocytic leukemia.

10. The method of claim 1 , wherein the compound is N-(2-((2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-5-fluorophenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide, or a pharmaceutically acceptable salt thereof.

11. The method of claim 1 , wherein the compound is N-(2-((2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-5-fluorophenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide.

12. The method of claim 2 , wherein the compound is N-(2-((2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-5-fluorophenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide, or a pharmaceutically acceptable salt thereof.

13. The method of claim 8 , wherein the compound is N-(2-((2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-5-fluorophenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide, or a pharmaceutically acceptable salt thereof.

14. The method of claim 9 , wherein the compound is N-(2-((2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-5-fluorophenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide, or a pharmaceutically acceptable salt thereof.

15. The method of claim 1 , wherein the compound is N-(2-((1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl)-4-(4-cyanopyridin-3-yl)phenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide, or a pharmaceutically acceptable salt thereof.

16. The method of claim 1 , wherein the compound is N-(2-((1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl)-4-(4-cyanopyridin-3-yl)phenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide.

17. The method of claim 2 , wherein the compound is N-(2-((1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl)-4-(4-cyanopyridin-3-yl)phenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide, or a pharmaceutically acceptable salt thereof.

18. The method of claim 8 , wherein the compound is N-(2-((1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl)-4-(4-cyanopyridin-3-yl)phenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide, or a pharmaceutically acceptable salt thereof.

19. The method of claim 9 , wherein the compound is N-(2-((1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl)-4-(4-cyanopyridin-3-yl)phenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide, or a pharmaceutically acceptable salt thereof.

20. The method of claim 1 , wherein the compound is N-(2-((2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-4-(4-cyanopyridin-3-yl)phenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide, or a pharmaceutically acceptable salt thereof.

21. The method of claim 1 , wherein the compound is N-(2-((2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-4-(4-cyanopyridin-3-yl)phenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide.

22. The method of claim 2 , wherein the compound is N-(2-((2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-4-(4-cyanopyridin-3-yl)phenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide, or a pharmaceutically acceptable salt thereof.

23. The method of claim 8 , wherein the compound is N-(2-((2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-4-(4-cyanopyridin-3-yl)phenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide, or a pharmaceutically acceptable salt thereof.

24. The method of claim 9 , wherein the compound is N-(2-((2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-yl)-4-(4-cyanopyridin-3-yl)phenyl)-2-(2-fluoro-6-methoxyphenyl)pyrimidine-4-carboxamide, or a pharmaceutically acceptable salt thereof.

25. The method of claim 1 , wherein the cancer is hepatocellular carcinoma.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 22, 2020
From: VECHORKIN, OLEG; PAN, JUN; SOKOLSKY, ALEXANDER; STYDUHAR, EVAN; YE, QINDA; YAO, WENQING
To: INCYTE CORPORATION
Reel/Frame 053845/0864 →
Continuity (5)
Division 16278865 · Feb 19, 2019
Provisional Application 62750371 · Oct 25, 2018
Provisional Application 62672772 · May 17, 2018
Provisional Application 62632702 · Feb 20, 2018
Related Publication 20210094934A1 · Apr 1, 2021
Cited By (3)
US 12,384,778 US 12,466,815 US 12,516,059