IP Library › Granted Patent US 12,202,811
Granted Patent B2
US 12,202,811 · App. 17/095,653 · Granted Jan 21, 2025

Compounds for treating prostate cancer

Inventors: Peter Wipf (Pittsburgh, PA); Erin M. Skoda (Columbia, MD); Zhou Wang (Pittsburgh, PA)
Assignee: University of Pittsburgh—Of the Commonwealth System of Higher Education
C07D295/192A61K31/4525A61K31/495A61K31/496A61K31/551A61K31/58A61K45/06C07D213/70C07D261/08C07D295/26C07D317/54C07D333/16C07D413/12
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Quick Facts
Patent No.
US 12,202,811
App. No.
17/095,653
Granted
Jan 21, 2025
Kind
B2
Abstract

A compound, or a pharmaceutically acceptable salt or ester thereof, having a formula I of: R 20 —(Z) b —(Y) c —(R 21 ) a —X—R 22 —R 23 wherein R 20 is an aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl, substituted heterocycloalkyl, alkoxy, aryloxy, a silyl-containing group, a boryl-containing group, a phosphine-containing group, amino, a thio-containing group, a seleno-containing group, halide, or a nitro-containing group; Z is alkanediyl, substituted alkanediyl, cycloalkanediyl, or substituted cycloalkanediyl; Y is S, O, or NR 10 , wherein R 10 is H or alkyl; R 21 is alkanediyl, substituted alkanediyl, cycloalkanediyl, substituted cycloalkanediyl, alkadienyl, substituted alkadienyl, alkatrienyl, substituted alkatrienyl; X is —C(═O)— or —S(═O)(═O)—; R 22 is a moiety that includes at least one divalent amino radical; R 23 is an aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl, substituted heterocycloalkyl, alkoxy, aryloxy, a silyl-containing group, a boryl-containing group, a phosphine-containing group, amino, a thio-containing group, a seleno-containing group, halide, or a nitro-containing group; a is 0 or 1; b is 0 or 1; and c is 0 or 1; provided that if X is —C(═O)— then Y is not S.

Claims (37)

1. A method for treating prostate cancer in a subject, comprising administering to the subject a therapeutically effective amount of a compound, or a pharmaceutically acceptable salt or ester thereof, of formula I:

R 20 —(Z) b —(Y) c —(R 21 ) a —X—R 22 —R 23   I

wherein R 20 is an aryl, substituted aryl, heteroaryl, or substituted heteroaryl;

Z is alkanediyl or substituted alkanediyl;

Y is S, O, or NR 10 , wherein R 10 is H or alkyl;

R 21 is cycloalkanediyl or substituted cycloalkanediyl;

X is —C(═O)—;

R 22 is

R 23 is a substituted phenyl having a structure of:

wherein each of R 1 -R 5 is individually H, alkyl, halogen, cyano, or substituted alkynyl, provided that at least one of R 1 -R 5 is not H;

a is 1;

b is 0; and

c is 0;

provided that if X is —C(═O)— then Y is not S.

2. The method of claim 1 , wherein the prostate cancer is castration-resistant prostate cancer.

3. The method of claim 1 , wherein the compound is orally administered.

4. The method of claim 1 , wherein the compound is used in combination with androgen deprivation therapy.

5. The method of claim 1 , wherein the compound is co-administered with abiratrone.

6. The method of claim 1 , wherein the method further comprises identifying a subject that is in need of treatment with the compound.

7. The method of claim 1 , wherein R 21 is cyclopropanediyl.

8. The method of claim 1 , wherein R 21 is:

9. The method of claim 1 , wherein R 1 is alkyl, halogen or cyano.

10. The method of claim 1 , wherein the compound is selected from:

or a pharmaceutically acceptable salt thereof.

11. The method of claim 2 , wherein R 21 is cyclopropanediyl.

12. The method of claim 4 , wherein R 21 is cyclopropanediyl.

13. The method of claim 1 , wherein R 1 is alkyl and R 4 is halogen.

14. The method of claim 13 , wherein R 21 is cyclopropanediyl.

15. The method of claim 1 , wherein R 20 is substituted phenyl.

16. The method of claim 15 , wherein R 21 is cyclopropanediyl.

17. The method of claim 1 , wherein R 21 is cyclopropanediyl; and R 1 is alkyl, halogen or cyano.

18. The method of claim 2 , wherein R 21 is cyclopropanediyl; and R 1 is alkyl, halogen or cyano.

19. The method of claim 4 , wherein R 21 is cyclopropanediyl; and R 1 is alkyl, halogen or cyano.

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

or a pharmaceutically acceptable salt thereof.

21. The method of claim 2 , wherein the compound is selected from:

or a pharmaceutically acceptable salt thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 12, 2020
From: WIPF, PETER; SKODA, ERIN M.; WANG, ZHOU
To: UNIVERSITY OF PITTSBURGH - OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION
Reel/Frame 054354/0328 →
Continuity (3)
Division 15023349
Provisional Application 61880747 · Sep 20, 2013
Related Publication 20210061779A1 · Mar 4, 2021
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