Granted Patent B2

US 12,583,850 · App. 19/293,960 · Granted Mar 24, 2026

Inventors: Elliot J. Androphy (Indianapolis, IN); Samy Meroueh (Carmel, IN); Anne Rietz (Indianapolis, IN); Zhijan Lu (Indianapolis, IN)

Assignees: THE TRUSTEES OF INDIANA UNIVERSITY; KOVINA THERAPEUTICS INC.

C07D413/14A61K31/517A61K31/519A61K31/5377C07D403/04C07D403/14C07D471/04C07D487/08C07D487/10C07D495/04

Abstract

Claims (45)

1 . A compound of Formula III:

or a pharmaceutically acceptable salt thereof,

wherein:

Y is CH or N;

X 3 is CH or N;

W is —(CH 2 ) n or —CH═CH—;

R 31 is —CH═CH 2 , —CR 51 ═CH 2 , —CH═CHCH 2 N(CH 3 ) 2 , —CH═CHCH 3 , —CH 2 (halo), or —CH 3 , wherein R 51 is H or halo;

R 35 is H or halo;

R 36 is H, halo, —OCH 3 , —OCH 2 CH 3 , —OCH 2 CH 2 OCH 3 , —OCH 2 CH 2 —N-pyrrolidine, or —CONHCH 3 ;

R 40 is H, —OCH 3 , —OCH 2 CH 3 , or —OCH 2 CH 2 OCH 3 ;

R 41 is H or —C 1 -C 4 alkyl;

R 42 is H, —CN, or —C 1 -C 4 alkyl, or R 41 and R 42 together with the atoms to which they are attached form a 3- to 6-membered heterocycloalkyl ring; and

n is 2, 3, or 4.

2 . The compound of claim 1 , wherein W is

3 . The compound of claim 1 , wherein X 3 is CH.

4 . The compound of claim 1 , wherein Y is N.

5 . The compound of claim 1 , wherein R 31 is —CH═CH 2 , —CH═CHCH 2 N(CH 3 ) 2 , or —CH═CHCH 3 .

6 . The compound of claim 5 , wherein R 31 is —CH═CH 2 .

7 . The compound of claim 1 , wherein R 35 is H or F.

8 . The compound of claim 7 , wherein R 36 is —OCH 3 , —OCH 2 CH 3 , or —OCH 2 CH 2 OCH 3 .

9 . The compound of claim 1 , wherein R 40 is —OCH 3 or —OCH 2 CH 3 .

10 . The compound of claim 1 , wherein R 41 is H.

11 . The compound of claim 8 , wherein R 42 is —C 1 -C 4 alkyl.

12 . The compound of claim 1 , wherein R 41 and R 42 together with the atoms to which they are attached form a 4- to 6-membered heterocycloalkyl ring.

13 . The compound of claim 1 , wherein X 3 is CH, Y is CH, and W is

14 . The compound of claim 13 , wherein R 31 is —CH═CH 2 , —CH═CHCH 2 N(CH 3 ) 2 , or —CH═CHCH 3 .

15 . The compound of claim 14 , wherein R 35 is H or F.

16 . The compound of claim 15 , wherein R 36 is —OCH 3 , —OCH 2 CH 3 , or —OCH 2 CH 2 OCH 3 .

17 . The compound of claim 16 , wherein R 40 is —OCH 3 or —OCH 2 CH 3 .

18 . The compound of claim 17 , wherein R 41 is H.

19 . The compound of claim 18 , wherein R 42 is —C 1 -C 4 alkyl.

20 . The compound of claim 1 , wherein X 3 is CH, Y is N, and W is

21 . The compound of claim 20 , wherein R 31 is —CH═CH 2 , or —CH═CHCH 2 N(CH 3 ) 2 , —CH═CHCH 3 .

22 . The compound of claim 21 , wherein R 35 is H or F.

23 . The compound of claim 22 , wherein R 36 is —OCH 3 , —OCH 2 CH 3 , or —OCH 2 CH 2 OCH 3 .

24 . The compound of claim 23 , wherein R 40 is —OCH 3 or —OCH 2 CH 3 .

25 . The compound of claim 24 , wherein R 41 is H.

26 . The compound of claim 25 , wherein R 42 is —C 1 -C 4 alkyl.

27 . The compound of claim 1 , wherein the compound of Formula III has the structure:

or a pharmaceutically acceptable salt thereof.

28 . The compound of claim 27 , wherein the compound of Formula III has the structure:

or a pharmaceutically acceptable salt thereof.

29 . The compound of claim 27 , wherein the compound of Formula III has the structure:

or a pharmaceutically acceptable salt thereof.

30 . A method of treating an HPV-induced cancer in a subject, comprising administering to the subject a therapeutically effective amount of the compound of claim 1 .

Continuity (3)

References Cited (167)