IP Library Granted Patent US 10,882,834
Granted Patent B2
US 10,882,834 · App. 15/023,349 · Granted Jan 5, 2021

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 10,882,834
App. No.
15/023,349
Granted
Jan 5, 2021
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 R20 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(=0)- or —S(=0)(=0)-; 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(=0)- then Y is not S.

Claims (41)

1. 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 unsubstituted phenyl;

Z is alkanediyl or substituted alkanediyl;

Y is S;

R 21 is

X is —C(═O)— or —S(═O)(═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 R 1 is not H and R 4 is halogen;

a is 1;

b is 0 or 1; and

c is 0 or 1;

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

2. The compound of claim 1 , wherein R 4 is chloro.

3. The compound of claim 1 , wherein b and c are each 0, and X is —C(═O)—.

4. The compound of claim 1 , wherein X is —C(═O)—.

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

6. A pharmaceutical composition comprising at least one pharmaceutically acceptable additive and a compound of claim 1 .

7. The pharmaceutical composition of claim 6 , wherein the pharmaceutically acceptable additive is selected from physiological saline, balanced salt solution, aqueous dextrose, glycerol, mannitol, lactose, starch or magnesium stearate.

8. 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 unsubstituted phenyl;

Z is alkanediyl or substituted alkanediyl;

Y is S;

R 21 is

X is —C(═O)— or —S(═O)(=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 R 1 is alkyl, halogen or cyano and R 4 is halogen;

a is 1;

b is 0 or 1; and

c is 0 or 1;

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

9. The compound of claim 8 , wherein R 1 is methyl.

10. The compound of claim 8 , wherein b and c are each 0, and X is —C(═O)—.

11. The compound of claim 8 , wherein X is —C(═O)—.

12. A pharmaceutical composition comprising at least one pharmaceutically acceptable additive and a compound of claim 8 .

13. The pharmaceutical composition of claim 12 , wherein the pharmaceutically acceptable additive is selected from physiological saline, balanced salt solution, aqueous dextrose, glycerol, mannitol, lactose, starch or magnesium stearate.

14. A pharmaceutical composition comprising at least one pharmaceutically acceptable additive and a compound of claim 2 .

15. The pharmaceutical composition of claim 14 , wherein the pharmaceutically acceptable additive is selected from physiological saline, balanced salt solution, aqueous dextrose, glycerol, mannitol, lactose, starch or magnesium stearate.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 5, 2016
From: WIPF, PETER; SKODA, ERIN M.; WANG, ZHOU
To: UNIVERSITY OF PITTSBURGH - OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION
Reel/Frame 038190/0493 →
Continuity (2)
Provisional Application 61880747 · Sep 20, 2013
Related Publication 20160264540A1 · Sep 15, 2016