IP Library › Granted Patent US 12,509,431
Granted Patent B2
US 12,509,431 · App. 18/882,649 · Granted Dec 30, 2025

1,4-dihydroquinazolinone compounds and uses thereof

Inventors: Natalie Anne Hawryluk (Nederland, CO); Stephen Thomas Schlachter (Boulder, CO); Marc Justin Evanchik (Boulder, CO); Carlos Luis Del Rio (San Mateo, CA); Alan James Russell (Boulder, CO); Kevin Koch (Niwot, CO); Michael Mark DuVall (Vancouver, WA); Michael Joseph Luzzio (Groton, CT); Kevin Hunt (Boulder, CO)
Assignee: EDGEWISE THERAPEUTICS, INC.
C07D239/80A61K31/517A61K31/519A61K31/527A61K31/5383A61P9/00C07D401/12C07D401/14C07D403/12C07D405/12C07D405/14C07D409/12C07D413/12C07D413/14C07D417/12C07D471/04C07D471/18C07D487/04C07D487/10C07D491/048C07D491/052C07D491/056C07D491/20C07D498/04
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Quick Facts
Patent No.
US 12,509,431
App. No.
18/882,649
Filed
Sep 11, 2024
Granted
Dec 30, 2025
Kind
B2
Art Unit
1624
USPC
514/210.18
Abstract

Provided dihydroquinazolinone and azadihydroquinazolinone compounds for treating cardiac indications such as hypertrophic cardiomyopathy and diastolic dysfunction.

Claims (96)

1. A compound represented by Formula (II):

or a salt thereof, wherein:

n is 0, 1, 2, 3, or 4;

each R 1 is independently selected from:

halogen, —NO 2 , —CN, —OR 10a , —SR 10a , —N(R 10a ) 2 , —C(O)R 10a , —C(O)N(R 10a ) 2 , —N(R 10a )C(O)R 10a , —N(R 10a )C(O)N(R 10a ) 2 , —OC(O)N(R 10a ) 2 , —N(R 10a )C(O)OR 10a , —C(O)OR 10a , —OC(O)R 10a , —S(O)R 10a , and —S(O) 2 R 10a ;

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 10a , —SR 10a , —N(R 10a ) 2 , —C(O)R 10a , —C(O)N(R 10a ) 2 , —N(R 10a )C(O)R 10a , —C(O)OR 10d , —OC(O)R 10a , —N(R 10a )C(O)N(R 10a ) 2 , —OC(O)N(R 10a ) 2 , —N(R 10a )C(O)OR 10a , —S(O)R 10a , —S(O) 2 R 10a , —NO 2 , ═O, ═S, ═N(R 10a ), —CN, C 3-10 carbocycle and 3- to 10-membered heterocycle, wherein each C 3-10 carbocycle and 3- to 10-membered heterocycle is optionally substituted with one or more substituents independently selected from R 9a ; 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 10a , —SR 10a , —N(R 10a ) 2 , —C(O)R 10a , —C(O)N(R 10a ) 2 , —N(R 10a )C(O)R 10a , —N(R 10a )C(O)N(R 10a ) 2 , —OC(O)N(R 10a ) 2 , —N(R 10a )C(O)OR 10a , —C(O)OR 10a , —OC(O)R 10a , —S(O)R 10a , —S(O) 2 R 10a , —NO 2 , ═O, ═S, ═N(R 10a ), —CN, C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl, wherein each C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl is optionally substituted with one or more substituents independently selected from R 9a ;

R 2 is selected from:

halogen, —NO 2 , —CN, —OR 10b , —SR 10b , —N(R 10b ) 2 , —C(O)R 10b , —C(O)N(R 10b ) 2 , —N(R 10b )C(O)R 10b , —N(R 10b )C(O)N(R 10b ) 2 , —OC(O)N(R 10b ) 2 , —N(R 10b )C(O)OR 10b , —C(O)OR 10b , —OC(O)R 10b , —S(O)R 10b , and —S(O) 2 R 10b ;

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 10b , —SR 10b , —N(R 10b ) 2 , —C(O)R 10b , —C(O)N(R 10b ) 2 , —N(R 10b )C(O)R 10b , —C(O)OR 10b , —OC(O)R 10b , —N(R 10b )C(O)N(R 10b ) 2 , —OC(O)N(R 10b ) 2 , —N(R 10b )C(O)OR 10b , —S(O)R 10b , —S(O) 2 R 10b , —NO 2 , ═O, ═S, ═N(R 10b ), —CN, C 3-10 carbocycle, and 3- to 10-membered heterocycle, wherein each C 3-10 carbocycle and 3- to 10-membered heterocycle is optionally substituted with one or more substituents independently selected from R 9b ; 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 10b , —SR 10b , —N(R 10b ) 2 , —C(O)R 10b , —C(O)N(R 10b ) 2 , —N(R 10b )C(O)R 10b , —N(R 10b )C(O)N(R 10b ) 2 , —OC(O)N(R 10b ) 2 , —N(R 10b )C(O)OR 10b , —C(O)OR 10b , —OC(O)R 10b , —S(O)R 10b , —S(O) 2 R 10b , —NO 2 , ═O, ═S, ═N(R 10b ), —CN, C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl, wherein each C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl is optionally substituted with one or more substituents independently selected from R 9b ; or

R 2 together with R 11 form a 3- to 10-membered heterocycle or C 3-10 carbocycle, wherein the 3- to 10-membered heterocycle or C 3-10 carbocycle is optionally substituted with one or more substituents independently selected from R 9b ′;

R 3 and R 4 are each independently selected from:

hydrogen, halogen, —OR 10c , —SR 10c , —N(R 10c ) 2 , —NO 2 , and —CN; and

C 1-6 alkyl optionally substituted with one or more substituents independently selected from halogen, —OR 10c , —SR 10c , —N(R 10c ) 2 , —NO 2 , and —CN; or

R 3 together with R 4 form a 3- to 10-membered heterocycle or C 3-10 carbocycle, wherein the 3- to 10-membered heterocycle or C 3-10 carbocycle is optionally substituted with one or more substituents independently selected from R 9c ;

R 5 and R 6 are each independently selected from:

hydrogen, halogen, —OR 10d , —SR 10d , —N(R 10d ) 2 , —NO 2 , and —CN; and

C 1-6 alkyl optionally substituted with one or more substituents independently selected from halogen, —OR 10d , —SR 10d , —N(R 10d ) 2 , —NO 2 , and —CN; or

R 5 together with R 6 form a 3- to 10-membered heterocycle or C 3-10 carbocycle, wherein the 3- to 10-membered heterocycle or C 3-10 carbocycle is optionally substituted with one or more substituents independently selected from R 9d ;

R 7 is selected from:

hydrogen and C 1-6 alkyl optionally substituted with one or more substituents independently selected from halogen, —OR 10e , —SR 10e , —N(R 10e ) 2 , —NO 2 , and —CN;

R 8 is selected from:

hydrogen and C 1-6 alkyl optionally substituted with one or more substituents independently selected from halogen, —OR 10f , —SR 10f , —N(R 10f ) 2 , —NO 2 , and —CN;

R 11 is selected from:

halogen, —NO 2 , —CN, —OR 10g , —SR 10g , —N(R 10g ) 2 , —C(O)R 10g , —C(O)N(R 10g ) 2 , —N(R 10g )C(O)R 10g , —N(R 10g )C(O)N(R 10g ) 2 , —OC(O)N(R 10g ) 2 , —N(R 10g )C(O)OR 10g , —C(O)OR 10g , —OC(O)R 10g , —S(O)R 10g , and —S(O) 2 R 10g ; 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 halogen, —OR 10g , —SR 10g , —N(R 10g ) 2 , —C(O)R 10g , —C(O)N(R 10g ) 2 , —N(R 10g )C(O)R 10g , —C(O)OR 10g , —OC(O)R 10g , —N(R 10g )C(O)N(R 10g ) 2 , —OC(O)N(R 10g ) 2 , —N(R 10g )C(O)OR 10g , —S(O)R 10g , —S(O) 2 R 10g , —NO 2 , ═S, ═N(R 10g ), —CN, C 3-10 carbocycle and 3- to 10-membered heterocycle, wherein each C 3-10 carbocycle and 3- to 10-membered heterocycle is optionally substituted with one or more substituents independently selected from R 9g ;

R 12 is selected from:

hydrogen;

C 1-6 alkyl optionally substituted with one or more substituents independently selected from the group consisting of halogen, —CN, —OH, —OR 10h —N(R 10h ) 2 , —NO 2 , —C(O)R 10h , —SR 10h , and —S(O)R 10h ; and

C 3-6 carbocycle and 3- to 10-membered heterocycle, each of which is optionally substituted with one or more substituents independently selected from the group consisting of halogen, —CN, —OH, —OR 10h , —N(R 10h ) 2 , —NO 2 , —C(O)R 10h , —SR 10h , and —S(O)R 10h ; or

R 12 , R 11 , and R 2 come together to form a C 5 -C 10 bridged ring system;

each R 9a is independently selected from:

halogen, —OR 10a , —SR 10a , —N(R 10a ) 2 , —C(O)R 10a , —C(O)N(R 10a ) 2 , —N(R 10a )C(O)R 10a , —N(R 10a )C(O)N(R 10a ) 2 , —OC(O)N(R 10a ) 2 , —N(R 10a )C(O)OR 10a , —C(O)OR 10a , —OC(O)R 10a , —S(O)R 10a , —S(O) 2 R 10a , —NO 2 , ═O, ═S, ═N(R 10a ), 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 10a , —SR 10a , —N(R 10a ) 2 , —C(O)R 10a , —C(O)N(R 10a ) 2 , —N(R 10a )C(O)R 10a , —N(R 10a )C(O)N(R 10a ) 2 , —OC(O)N(R 10a ) 2 , —N(R 10a )C(O)OR 10a , —C(O)OR 10a , —OC(O)R 10a , —S(O)R 10a , —S(O) 2 R 10a , —NO 2 , ═O, ═S, ═N(R 10a ), and —CN;

each R 9b is independently selected from:

halogen, —OR 10b , —SR 10b , —N(R 10b ) 2 , —C(O)R 10b , —C(O)N(R 10b ) 2 , —N(R 10b )C(O)R 10b , —N(R 10b )C(O)N(R 10b ) 2 , —OC(O)N(R 10b ) 2 , —N(R 10b )C(O)OR 10b , —C(O)OR 10b , —OC(O)R 10b , —S(O)R 10b , —S(O) 2 R 10b , —NO 2 , ═O, ═S, ═N(R 10b ), 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 10b , —SR 10b , —N(R 10b ) 2 , —C(O)R 10b , —C(O)N(R 10b ) 2 , —N(R 10b )C(O)R 10b , —N(R 10b )C(O)N(R 10b ) 2 , —OC(O)N(R 10b ) 2 , —N(R 10b )C(O)OR 10b , —C(O)OR 10b , —OC(O)R 10b , —S(O)R 10b , —S(O) 2 R 10b , —NO 2 , ═O, ═S, ═N(R 10b ), and —CN;

each R 9b ′ is independently selected from:

halogen, —OR 10b , —SR 10b , —N(R 10b ) 2 , —C(O)R 10b , —C(O)N(R 10b ) 2 , —N(R 10b )C(O)R 10b , —N(R 10b )C(O)N(R 10b ) 2 , —OC(O)N(R 10b ) 2 , —N(R 10b )C(O)OR 10b , —C(O)OR 10b , —OC(O)R 10b , —S(O)R 10b , —S(O) 2 R 10b , —NO 2 , ═O, ═S, ═N(R 10b ), 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 10b , —SR 10b , —N(R 10b ) 2 , —C(O)R 10b , —C(O)N(R 10b ) 2 , —N(R 10b )C(O)R 10b , —N(R 10b )C(O)N(R 10b ) 2 , —OC(O)N(R 10b ) 2 , —N(R 10b )C(O)OR 10b , —C(O)OR 10b , —OC(O)R 10b , —S(O)R 10b , —S(O) 2 R 10b , —NO 2 , ═O, ═S, ═N(R 10b ), and —CN;

each R 9c is independently selected from:

halogen, —OR 10c , —SR 10c , —N(R 10c ) 2 , —C(O)R 10c , —C(O)N(R 10c ) 2 , —N(R 10c )C(O)R 10c , —N(R 10c )C(O)N(R 10c ) 2 , —OC(O)N(R 10c ) 2 , —N(R 10c )C(O)OR 10c , —C(O)OR 10c , —OC(O)R 10c , —S(O)R 10c , —S(O) 2 R 10c , —NO 2 , ═O, ═S, ═N(R 10c ), 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 10c , —SR 10c , —N(R 10c ) 2 , —C(O)R 10c , —C(O)N(R 10c ) 2 , —N(R 10c )C(O)R 10c , —N(R 10c )C(O)N(R 10c ) 2 , —OC(O)N(R 10c ) 2 , —N(R 10c )C(O)OR 10c , —C(O)OR 10c , —OC(O)R 10c , —S(O)R 10c , —S(O) 2 R 10c , —NO 2 , ═O, ═S, ═N(R 10c ), and —CN;

each R 9d is independently selected from:

halogen, —OR 10d , —SR 10d , —N(R 10d ) 2 , —C(O)R 10d , —C(O)N(R 10d ) 2 , —N(R 10d )C(O)R 10d , —N(R 10d )C(O)N(R 10d ) 2 , —OC(O)N(R 10d ) 2 , —N(R 10d )C(O)OR 10d , —C(O)OR 10d , —OC(O)R 10d , —S(O)R 10d , —S(O) 2 R 10d , —NO 2 , ═O, ═S, ═N(R 10d ), 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 10d , —SR 10d , —N(R 10d ) 2 , —C(O)R 10d , —C(O)N(R 10d ) 2 , —N(R 10d )C(O)R 10d , —N(R 10d )C(O)N(R 10d ) 2 , —OC(O)N(R 10d ) 2 , —N(R 10d )C(O)OR 10d , —C(O)OR 10d , —OC(O)R 10d , —S(O)R 10d , —S(O) 2 R 10d , —NO 2 , ═O, ═S, ═N(R 10d ), and —CN;

each R 9g is independently selected from:

halogen, —OR 10g , —SR 10g , —N(R 10g ) 2 , —C(O)R 10g , —C(O)N(R 10g ) 2 , —N(R 10g )C(O)R 10g , —N(R 10g )C(O)N(R 10g ) 2 , —OC(O)N(R 10g ) 2 , —N(R 10g )C(O)OR 10g , —C(O)OR 10g , —OC(O)R 10g , —S(O)R 10g , —S(O) 2 R 10g , —NO 2 , ═O, ═S, ═N(R 10g ), 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 10g , —SR 10g , —N(R 10g ) 2 , —C(O)R 10g , —C(O)N(R 10g ) 2 , —N(R 10g )C(O)R 10g , —N(R 10g )C(O)N(R 10g ) 2 , —OC(O)N(R 10g ) 2 , —N(R 10g )C(O)OR 10g , —C(O)OR 10g , —OC(O)R 10g , —S(O)R 10g , —S(O) 2 R 10g , —NO 2 , ═O, ═S, ═N(R 10g ), and —CN; and

each R 10a , R 10b , R 10c , R 10d , R 10e , R 10f , R 10g and R 10h 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 n is 1 or 2.

3. The compound or salt of claim 1 , wherein each R 1 is independently selected from: halogen, —CN, —OR 10a , —SR 10a , —N(R 10a ) 2 , and C 1-6 alkyl, wherein the C 1-6 alkyl is optionally substituted with one or more substituents independently selected from halogen, —OR 10a , —SR 10a , —N(R 10a ) 2 , ═O, and —CN, wherein each R 10a is independently selected from hydrogen and C 1-6 alkyl.

4. The compound or salt of claim 1 , wherein each R 1 is independently selected from: —F, —Br, —CN, —OH, and —CH 3 .

5. The compound or salt of claim 1 , wherein R 2 is selected from: optionally substituted C 5-10 carbocycle and optionally substituted 5- to 10-membered heterocycle.

6. The compound or salt of claim 5 , wherein R 2 is selected from: optionally substituted C 6-10 carbocycle and optionally substituted 5- to 10-membered heterocycle.

7. The compound or salt of claim 1 , wherein R 2 is selected from optionally substituted phenyl and optionally substituted 5- to 10-membered heteroaryl, each of which is optionally substituted with one or more substituents independently selected from halogen, —OR 10b , —CN, C 1-6 alkyl, C 2-6 alkenyl, and C 2-6 alkynyl, and wherein each R 10b is independently selected from hydrogen and C 1-6 alkyl.

8. The compound or salt of claim 7 , wherein R 2 is selected from phenyl, pyridinyl, pyrimidinyl, pyrazinyl, and pyridazinyl, any one of which is optionally substituted.

9. The compound or salt of claim 7 , wherein R 2 is selected from optionally substituted 5- to 10-membered heteroaryl.

10. The compound or salt of claim 1 , wherein R 2 together with R 11 form a 6- to 10-membered heterocycle or C 3-10 carbocycle, wherein the 3- to 10-membered heterocycle or C 3-10 carbocycle is optionally substituted with one or more substituents independently selected from R 9b ′.

11. The compound or salt of claim 1 , wherein R 3 and R 4 are each independently selected from: hydrogen, —OH, and C 1 alkyl.

12. The compound or salt of claim 1 , wherein R 5 and R 6 are each hydrogen.

13. The compound or salt of claim 1 , wherein each of R 7 and R 8 is independently selected from hydrogen and C 1-6 alkyl.

14. The compound or salt of claim 13 , wherein R 7 is hydrogen, and R 8 is hydrogen.

15. The compound or salt of claim 1 , wherein R 11 is selected from: C 1-3 alkyl optionally substituted with one or more —OH.

16. The compound or salt of claim 1 , wherein R 12 is hydrogen.

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. The compound of claim 1 , wherein the compound is

or a salt thereof.

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

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.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 6, 2025
From: HAWRYLUK, NATALIE ANNE; SCHLACHTER, STEPHEN THOMAS; EVANCHIK, MARC JUSTIN; DEL RIO, CARLOS LUIS; RUSSELL, ALAN JAMES; KOCH, KEVIN; DUVALL, MICHAEL MARK; LUZZIO, MICHAEL JOSEPH
To: EDGEWISE THERAPEUTICS, INC.
Reel/Frame 070430/0599 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 6, 2025
From: HUNT, KEVIN
To: EDGEWISE THERAPEUTICS, INC.
Reel/Frame 070430/0656 →
Continuity (3)
Continuation PCTUS2023075138 · Sep 26, 2023
Provisional Application 63377175 · Sep 26, 2022
Related Publication 20250154111A1 · May 15, 2025
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