IP Library › Granted Patent US 12,448,369

Granted Patent B2

US 12,448,369 · App. 18/882,644 · Granted Oct 21, 2025

Quinolinone amide compounds and uses thereof

Inventors: Natalie Anne Hawryluk (Nederland, CO); Stephen Thomas Schlachter (Boulder, CO); Kevin Koch (Niwot, CO); Michael Joseph Luzzio (Groton, CT); Alan James Russell (Boulder, CO); Marc Justin Evanchik (Boulder, CO); Carlos Luis Del Rio (San Mateo, CA); Kevin Hunt (Boulder, CO)

Assignee: Edgewise Therapeutics, Inc.

C07D405/12 A61K31/4353 A61K31/506 C07D221/04 C07D401/12

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Quick Facts

Patent No.: US 12,448,369
App. No.: 18/882,644
Granted: Oct 21, 2025
Kind: B2

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Abstract

The present disclosure generally relates to substituted quinolinone amide compounds or salts of Formula (I), (II-A), (IV), or (III) and pharmaceutical compositions thereof. The substituted quinolinone amide compounds or salts of Formula (I), (II-A), (IV), or (III) disclosed herein may be used to treat or prevent cardiac disease in an individual in need thereof.

Claims (152)

1. A compound represented by Formula (II-A):

or a salt thereof, wherein:

X 11 is selected from C(R 17a ) and N;

X 12 is selected from C(R 17b ) and N;

X 13 is selected from C(R 17c ) and N;

Y 11 is selected from C(R 17d ) and N;

Y 12 is selected from C(R 17e ) and N;

R 11a , R 11b , R 11c and R 11d are each independently selected from:

hydrogen, halogen, —NO 2 , —CN, —N 3 , —OR 19a , —SR 19a , —N(R 19a ) 2 , —C(O)R 19a , —C(O)N(R 19a ) 2 , —N(R 19a )C(O)R 19a , —N(R 19a )C(O)N(R 19a ) 2 , —OC(O)N(R 19a ) 2 , —N(R 19a )C(O)OR 19a , —C(O)OR 19a , —OC(O)R 19a , —S(O)R 19a , and —S(O) 2 R 19a ;

C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl, each of which is optionally substituted with one or more substituents independently selected from halogen, —OR 19a , —SR 19a , —N(R 19a ) 2 , —C(O)R 19a , —C(O)N(R 19a ) 2 , —N(R 19a )C(O)R 19a , —C(O)OR 19a , —OC(O)R 19a , —N(R 19a )C(O)N(R 19a ) 2 , —OC(O)N(R 19a ) 2 , —N(R 19a )C(O)OR 19a , —S(O)R 19a , —S(O) 2 R 19a , —NO 2 , ═O, ═S, ═N(R 19a ), —CN, C 3-10 carbocycle and 3- to 10-membered heterocycle, wherein the C 3-10 carbocycle and 3- to 10-membered heterocycle are each optionally substituted with one or more substituents independently selected from R 18a ; and

C 3-10 carbocycle and 3- to 10-membered heterocycle, each of which is optionally substituted with one or more substituents independently selected from halogen, —OR 19a , —SR 19a , —N(R 19a ) 2 , —C(O)R 19a , —C(O)N(R 19a ) 2 , —N(R 19a )C(O)R 19a , —N(R 19a )C(O)N(R 19a ) 2 , —OC(O)N(R 19a ) 2 , —N(R 19a )C(O)OR 19a , —C(O)OR 19a , —OC(O)R 19a , —S(O)R 19a , —S(O) 2 R 19a , —NO 2 , ═O, ═S, ═N(R 19a ), —CN, C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl, wherein the C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted with one or more substituents independently selected from R 18a ;

wherein when R 11a , R 11b , and R 11c are each hydrogen; then R 11d is not hydrogen;

wherein when R 11b is —OCH 3 , then R 11c is not —OMe;

R 12 is selected from:

hydrogen, halogen, —NO 2 , —CN, —OR 19b , —SR 19b , —N(R 19b ) 2 , —C(O)R 19b , —C(O)N(R 19b ) 2 , —N(R 19b )C(O)R 19b , —N(R 19b )C(O)N(R 19b ) 2 , —OC(O)N(R 19b ) 2 , —N(R 19b )C(O)OR 19b , —C(O)OR 19b , —OC(O)R 19b , —S(O)R 19b , and —S(O) 2 R 19b ;

C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl, each of which is optionally substituted with one or more substituents independently selected from halogen, —OR 19b , —SR 19b , —N(R 19b ) 2 , —C(O)R 19b , —C(O)N(R 19b ) 2 , —N(R 19b )C(O)R 19b , —C(O)OR 19b , —OC(O)R 19b , —N(R 19b )C(O)N(R 19b ) 2 , —OC(O)N(R 19b ) 2 , —N(R 19b )C(O)OR 19b , —S(O)R 19b , —S(O) 2 R 19b , —NO 2 , ═O, ═S, ═N(R 19b ), —CN, C 3-10 carbocycle, and 3- to 10-membered heterocycle, wherein the C 3-10 carbocycle and 3- to 10-membered heterocycle are each optionally substituted with one or more substituents independently selected from R 18b ; and

C 3-10 carbocycle and 3- to 10-membered heterocycle, each of which is optionally substituted with one or more substituents independently selected from halogen, —OR 19b , —SR 19b , —N(R 19b ) 2 , —C(O)R 19b , —C(O)N(R 19b ) 2 , —N(R 19b )C(O)R 19b , —N(R 19b )C(O)N(R 19b ) 2 , —OC(O)N(R 19b ) 2 , —N(R 19b )C(O)OR 19b , —C(O)OR 19b , —OC(O)R 19b , —S(O)R 19b , —S(O) 2 R 19b , —NO 2 , ═O, ═S, ═N(R 19b ), —CN, C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl, wherein the C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl are each optionally substituted with one or more substituents independently selected from R 18b ;

R 13 is selected from:

hydrogen, halogen, —OR 19c , —SR 19c , —N(R 19c ) 2 , —NO 2 , and —CN;

C 1-6 alkyl optionally substituted with one or more substituents independently selected from halogen, —OR 19c , —SR 19c , —N(R 19c ) 2 , —NO 2 , and —CN; and

C 3-10 carbocycle and 3- to 10-membered heterocycle, each of which is optionally substituted with one or more substituents independently selected from —OR 19c , —SR 19c , —N(R 19c ) 2 , —C(O)R 19c , —C(O)N(R 19c ) 2 , —N(R 19c )C(O)R 19c , —N(R 19c )C(O)N(R 19c ) 2 , —OC(O)N(R 19c ) 2 , —N(R 19c )C(O)OR 19c , —C(O)OR 19c , —OC(O)R 19c , —S(O)R 19c , —S(O) 2 R 19c , —NO 2 , and —CN;

R 14 is selected from:

hydrogen, halogen, —OR 19d , —SR 19d , —N(R 19d ) 2 , —NO 2 , and —CN;

C 1-6 alkyl which is optionally substituted with one or more substituents independently selected from halogen, —OR 19d , —SR 19d , —N(R 19d ) 2 , —NO 2 , and —CN; and

C 3-10 carbocycle and 3- to 10-membered heterocycle, each of which is optionally substituted with one or more substituents independently selected from halogen, —OR 19d , —SR 19d , —N(R 19d ) 2 , —C(O)R 19d , —C(O)N(R 19d ) 2 , —N(R 19d )C(O)R 19d , —N(R 19d )C(O)N(R 19d ) 2 , —OC(O)N(R 19d ) 2 , —N(R 19d )C(O)OR 19d , —C(O)OR 19d , —OC(O)R 19d , —S(O)R 19d , —S(O) 2 R 19d , —NO 2 , ═O, ═S, ═N(R 19d ), and —CN;

R 14′ is selected from:

hydrogen, halogen, —OR 19d , —SR 19d , —N(R 19d ) 2 , —NO 2 , and —CN; and

C 1-6 alkyl which is optionally substituted with one or more substituents independently selected from halogen, —OR 19d , —SR 19d , —N(R 19d ) 2 , —NO 2 , and —CN; and

R 14 together with R 14′ form a C 3-10 carbocycle, or 3- to 10-membered heterocycle, wherein the C 3-10 carbocycle or 3- to 10-membered heterocycle is optionally substituted with one or more substituents independently selected from R 18c ;

R 15 is selected from:

hydrogen, halogen, —OR 19e , —SR 19e , —N(R 19e ) 2 —NO 2 , and —CN; and

C 1-6 alkyl optionally substituted with one or more substituents independently selected from R 18d ; or

R 15 together with R 17a form a 3- to 10-membered heterocycle, wherein the 3- to 10-membered heterocycle is optionally substituted with one or more substituents independently selected from R 18f ; or

R 15 together with R 17b form a 3- to 10-membered heterocycle, wherein the 3- to 10-membered heterocycle is optionally substituted with one or more substituents independently selected from R 18f ; or

R 15 , R 16 , and R 17b together form a bridged heterocycle, wherein the bridged heterocycle is optionally substituted with one or more substituents independently selected from R 18f ;

R 16 is selected from:

hydrogen, halogen, —OR 19f , —SR 19f , —N(R 19f ) 2 , —NO 2 , and —CN; and

C 1-6 alkyl optionally substituted with one or more substituents independently selected from R 18e ; or

R 16 together with R 17a form a 3- to 10-membered heterocycle, wherein the 3- to 10-membered heterocycle is optionally substituted with one or more substituents independently selected from R 18f ; or

R 16 together with R 17b form a 3- to 10-membered heterocycle, wherein the 3- to 10-membered heterocycle is optionally substituted with one or more substituents independently selected from R 18f ; or

R 15 , R 16 , and R 17b together form a bridged heterocycle, wherein the bridged heterocycle is optionally substituted with one or more substituents independently selected from R 18f ;

R 17a , R 17b , R 17c , R 17d , and R 17e are each independently selected from:

hydrogen, halogen, —OR 19g , —SR 19g , —N(R 19g ) 2 , —NO 2 , —CN, and —N 3 ; and

C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl, each of which is optionally substituted with one or more substituents independently selected from R 18f ; or

R 15 together with R 17a form a 3- to 10-membered heterocycle, wherein the 3- to 10-membered heterocycle is optionally substituted with one or more substituents independently selected from R 18f ; or

R 15 together with R 17b form a 3- to 10-membered heterocycle, wherein the 3- to 10-membered heterocycle is optionally substituted with one or more substituents independently selected from R 18f ; or

R 16 together with R 17a form a 3- to 10-membered heterocycle, wherein the 3- to 10-membered heterocycle is optionally substituted with one or more substituents independently selected from R 18f ; or

R 16 together with R 17b form a 3- to 10-membered heterocycle, wherein the 3- to 10-membered heterocycle is optionally substituted with one or more substituents independently selected from R 18f ; or

R 15 , R 16 , and R 17b together form a bridged heterocycle, wherein the bridged heterocycle is optionally substituted with one or more substituents independently selected from R 18f ;

each R 18a , R 18b , R 18c , R 18d , R 18e , and R 18f is independently selected from:

halogen, —OR 19h , —SR 19h , —N(R 19h ) 2 , —C(O)R 19h , —C(O)N(R 19h ) 2 , —N(R 19h )C(O)R 19h , —N(R 19h )C(O)N(R 19h ) 2 , OC(O)N(R 19h ) 2 , —N(R 19h )C(O)OR 19h , —C(O)OR 19h , —OC(O)R 19h , —S(O)R 19h , —S(O) 2 R 19h , —NO 2 , ═O, ═S, ═N(R 19h ), and —CN; and

C 1-3 alkyl, C 2-3 alkenyl, and C 2-3 alkynyl, each of which is optionally substituted with one or more substituents independently selected from halogen, —OR 19h , —SR 19h , —N(R 19h ) 2 , —C(O)R 19h , —C(O)N(R 19h ) 2 , —N(R 19h )C(O)R 19h , —N(R 19h )C(O)N(R 19h ) 2 , —OC(O)N(R 19h ) 2 , —N(R 19h )C(O)OR 19h , —C(O)OR 19h , —OC(O)R 19h , —S(O)R 19h , —S(O) 2 R 19h , —NO 2 , ═O, ═S, ═N(R 19h ), and —CN; and

each R 19a , R 19b , R 19c , R 19d , R 19e , R 19f , R 19g , and R 19h is independently selected from:

hydrogen;

C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl, each of which is optionally substituted with one or more substituents independently selected from halogen, —CN, —OH, —SH, —NO 2 , —NH 2 , ═O, ═S, —O—C 1-6 alkyl, —S—C 1-6 alkyl, —N(C 1-6 alkyl) 2 , —NH(C 1-6 alkyl), C 3-10 carbocycle, and 3- to 10-membered heterocycle; and

C 3-10 carbocycle and 3- to 10-membered heterocycle, each of which is optionally substituted with one or more substituents independently selected from halogen, —CN, —OH, —SH, —NO 2 , —NH 2 , ═O, ═S, —O—C 1-6 alkyl, —S—C 1-6 alkyl, —N(C 1-6 alkyl) 2 , —NH(C 1-6 alkyl), C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-10 carbocycle, 3- to 10-membered heterocycle, and C 1-6 haloalkyl.

2. The compound or salt of claim 1 , wherein R 11a , R 11b , R 11c , and R 11d are each independently selected from hydrogen, halogen, —CN, C 1-6 alkyl, and C 3-10 carbocycle;

wherein when R 11a , R 11b , and R 11c are each hydrogen; then R 11d is selected from: halogen, —CN, C 1-6 alkyl, and C 3-10 carbocycle.

3. The compound or salt of claim 1 , wherein R 11b is —F; and R 11a R 11c , and R 11d are each independently selected from hydrogen, —F, —CN, and methyl.

4. The compound or salt of claim 1 , wherein R 11a is —F, R 11b is —H, and R 11d is —H.

5. The compound or salt of claim 1 , wherein R 12 is hydrogen, and R 15 is hydrogen.

6. The compound or salt of claim 1 , wherein R 12 is hydrogen, and R 15 is hydrogen, and R 16 is —CH 3 .

7. The compound or salt of claim 1 , wherein R 13 is selected from hydrogen, methyl, ethyl, —OH, —OMe, —CF 3 , —C(H)F 2 , —N(H)Me, and cyclopropyl.

8. The compound or salt of claim 1 , wherein R 13 is selected from hydrogen.

9. The compound or salt of claim 1 , wherein either: (i) R 14 is fluoro, and R 14′ is fluoro; or (ii) R 14 and R 14′ together form a cyclopropane ring that is optionally substituted; or (iii) R 14 is hydrogen, and R 14′ is hydrogen.

10. The compound or salt of claim 1 , wherein each R 17a , R 17b , R 17c , R 17d , and R 17e is independently selected from: hydrogen, halogen, —OR 19g , and —CN; and C 1-6 alkyl and C 2-6 alkynyl, each of which is optionally substituted with one or more substituents independently selected from R 18f .

11. The compound or salt of claim 1 , wherein R 17a , R 17b , R 17c , R 17d , and R 17e are each independently selected from hydrogen, methyl, —F, and —CN.

12. The compound or salt of claim 1 , wherein R 17a , R 17b , R 17c , R 17d , and R 17 are each independently selected from hydrogen and —CN.

13. The compound or salt of claim 1 , wherein one of X 11 and X 12 is N, or both X 11 and X 12 are N.

14. The compound or salt of claim 1 , wherein Y 12 is C(CN).

15. The compound or salt of claim 1 , wherein Y 11 is C(H), and X 13 is C(H).

16. The compound or salt of claim 1 , wherein R 16 and R 17a are taken together to form a 3- to 10-membered heterocycle which is optionally substituted with one or more substituents independently selected from halogen and—CN.

17. The compound of claim 1 , wherein the compound is

or a salt thereof.

18. The compound of claim 1 , wherein the compound is

or a salt thereof.

19. The compound of claim 1 , wherein the compound is

or a salt thereof.

20. The compound of claim 1 , wherein the compound is

or a salt thereof.

21. The compound of claim 1 , wherein the compound is

or a salt thereof.

22. The compound of claim 1 , wherein the compound is

or a salt thereof.

23. The compound of claim 1 , wherein the compound is

or a salt thereof.

24. The compound of claim 1 , wherein the compound is

or a salt thereof.

25. The compound of claim 1 , wherein the compound is

or a salt thereof.

26. The compound of claim 1 , wherein the compound is

or a salt thereof.

27. A pharmaceutical composition comprising a compound or salt of claim 1 and a pharmaceutically acceptable excipient.

28. The compound of claim 1 , wherein the compound is

or a salt thereof.

29. The compound of claim 1 , wherein the compound is

or a salt thereof.

30. The compound of claim 1 , wherein the compound is

or a salt thereof.

31. The compound of claim 1 , wherein the compound is

or a salt thereof.

32. The compound of claim 1 , wherein the compound is

or a salt thereof.

33. The compound of claim 1 , wherein the compound is

or a salt thereof.

34. The compound of claim 1 , wherein the compound is

or a salt thereof.

35. The compound of claim 1 , wherein the compound is

or a salt thereof.

36. The compound of claim 1 , wherein the compound is

or a salt thereof.

37. The compound of claim 1 , wherein the compound is

or a salt thereof.

38. The compound of claim 1 , wherein the compound is

or a salt thereof.

39. The compound of claim 1 , wherein the compound is

or a salt thereof.

40. The compound of claim 1 , wherein the compound is

or a salt thereof.

41. The compound of claim 1 , wherein the compound is

or a salt thereof.

42. The compound of claim 1 , wherein the compound is

or a salt thereof.

43. The compound of claim 1 , wherein the compound is

or a salt thereof.

44. The compound of claim 1 , wherein the compound is

or a salt thereof.

45. The compound of claim 1 , wherein the compound is

or a salt thereof.

46. The compound of claim 1 , wherein the compound is

or a salt thereof.

47. The compound of claim 1 , wherein the compound is

or a salt thereof.

48. The compound of claim 1 , wherein the compound is

or a salt thereof.

49. The compound of claim 1 , wherein the compound is

or a salt thereof.

50. The compound of claim 1 , wherein the compound is

or a salt thereof.

51. The compound of claim 1 , wherein the compound is

or a salt thereof.

52. The compound of claim 1 , wherein the compound is

or a salt thereof.

53. The compound of claim 1 , wherein the compound is

or a salt thereof.

54. The compound of claim 1 , wherein the compound is

or a salt thereof.

55. The compound of claim 1 , wherein the compound is

or a salt thereof.

56. The compound of claim 1 , wherein the compound is

or a salt thereof.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2025

From: HUNT, KEVIN

To: EDGEWISE THERAPEUTICS, INC.

Reel/Frame 070718/0244 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 6, 2025

From: HAWRYLUK, NATALIE ANNE; SCHLACHTER, STEPHEN THOMAS; KOCH, KEVEN; LUZZIO, MICHAEL JOSEPH; RUSSELL, ALAN JAMES; EVANCHIK, MARC JUSTIN; DEL RIO, CARLOS LUIS

To: EDGEWISE THERAPEUTICS, INC.

Reel/Frame 070431/0648 →

Continuity (3)

Continuation PCTUS2024021528 · Mar 26, 2024

Provisional Application 63492441 · Mar 27, 2023

Related Publication 20250026740A1 · Jan 23, 2025

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