IP Library › Granted Patent US 7,842,680

Granted Patent B2

US 7,842,680 · App. 12/406,033 · Granted Nov 30, 2010

Diene and triene compounds and formulations

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 7,842,680
App. No.: 12/406,033
Granted: Nov 30, 2010
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

The instant invention provides potent antiandrogen compounds, such as 3β-acetoxyandrost-1,5-diene-17-ethylene ketal and 3β-hydroxyandrost-1,5-diene-17-ethylene ketal, and methods for their use in the prevention and treatment of biological conditions mediated by androgen receptors. Thus, for example, compounds of the invention are useful in the prevention and treatment of prostrate cancer. Furthermore, it has been discovered that compounds of the invention are useful in the prevention and treatment of androgen-independent cancers such as androgen-independent prostrate cancer. Finally, inventive compounds may be used to treat antiandrogen induced withdrawal syndrome.

Claims (54)

1. A compound of the structure

or a pharmaceutically acceptable salt of the compound and wherein,

A is —C(O)— or —CR 9 R 10 —;

G is —C(O)— or —CR 3 R 4 —;

K is —CR 1 R 2 —;

R and R′ independently are —F, —Cl, —Br, —I, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkene, substituted or unsubstituted lower alkyne, —CN, —COOR 14 , —C(O)NR 14 R 15 , —NO 2 , —NR 14 R 15 , —NR 14 —C(O)—R 15 , —OH, substituted or unsubstituted lower alkoxy, and —S(O) 0-2 R 14 ;

R 1 is —OR 11 , —C(O)—R 12 , —C(O)—NR 12 R 13 , —C(O)—OR 12 , —C(S)—R 12 , —C(S)—OR 12 or —S(O) 0-2 —R 12 ;

R 2 and R 4 independently are —H, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkene or substituted or unsubstituted lower alkyne;

R 3 and R 5 independently are —H, —F, —Cl, —Br, —I, substituted and unsubstituted lower alkyl, substituted and unsubstituted lower alkene, substituted and unsubstituted lower alkyne, —CN, —COOR 14 , —C(O)NR 14 R 15 , —NO 2 , —NR 14 R 15 , —NR 14 —C(O)—R 15 , —OH, substituted and unsubstituted lower alkoxy or —S(O) 0-2 R 14 ;

R 6 is —H, —F, —Cl, —Br, —I, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkene, substituted or unsubstituted lower alkyne, —CN, —COOR 14 , —C(O)NR 14 R 15 , —NO 2 , —NR 14 R 15 , —NR 14 —C(O)—R 15 , —OH, substituted and unsubstituted lower alkoxy or and —S(O) 0-2 R 14 ;

R 7 and R 8 independently are —H or substituted or unsubstituted lower alkyl;

R 9 is —OH or substituted or unsubstituted lower alkoxy;

R 10 is substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkene, substituted or unsubstituted lower alkyne, substituted or unsubstituted —S(O) 0-2 (lower alkyl), or R 9 and R 10 , together with the carbon to which they are attached, form a 5-, 6-, or 7-member heterocyclyl or cycloalkyl group;

R 11 is —H, substituted or unsubstituted alkyl, substituted or unsubstituted alkene, substituted or unsubstituted alkyne, —C(O)—R 12 , —C(O)—NR 12 R 13 , —C(O)—OR 12 , —C(S)—R 12 , —NR 12 R 13 , —S(O) 2 —R 12 , —S(O) 2 —OR 12 , and —P(O)(OR 12 )(OR 13 ) 0-1 ;

R 12 and R 13 independently are —H, substituted or unsubstituted alkyl, substituted or unsubstituted alkene, substituted or unsubstituted alkyne, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclyl or substituted or unsubstituted heterocyclylalkyl;

R 14 and R 15 independently are —H, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkene, substituted or unsubstituted lower alkyne, substituted or unsubstituted C 6-10 aryl, or substituted or unsubstituted C 7-12 arylalkyl;

n is 0, 1, or 2; and

n′ is 0, 1 or 2.

2. The compound of claim 1 wherein R 1 is —OR 11 or —C(O)—R 12 .

3. The compound of claim 1 wherein R 5 is —OH.

4. The compound of claim 1 of the structure

5. The compound of claim 4 having the of the structure

wherein R 16 is —H, alkyl or fluoroalkyl.

6. The compound of claim 5 wherein R 16 is —H.

7. The compound of claim 4 of the structure

8. The compound of claim 1 of the structure

9. The compound of claim 8 of the structure

10. The compound of claim 1 of the structure

11. The compound of claim 10 of the structure

wherein R 16 is —H, alkyl or fluoroalkyl.

12. The compound of claim 10 of the structure

13. A pharmaceutical formulation comprising one or more excipients and a compound of the structure

or a pharmaceutically acceptable salt of the compound and wherein,

A is —C(O)— or —CR 9 R 10 —;

G is —C(O)— or —CR 3 R 4 —;

K is —CR 1 R 2 —;

R 1 is —OR 11 , —C(O)—R 12 , —C(O)—NR 12 R 13 , —C(O)—OR 12 , —C(S)—R 12 , —C(S)—OR 12 or —S(O) 0-2 —R 12 ;

R 2 and R 4 independently are —H, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkene or substituted or unsubstituted lower alkyne;

R 7 and R 8 independently are —H or substituted or unsubstituted lower alkyl;

R 9 is —OH or substituted or unsubstituted lower alkoxy;

n is 0, 1, or 2; and

n′ is 0, 1 or 2.

14. The pharmaceutical formulation of claim 13 wherein the compound has the structure

wherein R 16 is —H, alkyl or fluoroalkyl.

15. The compound of claim 14 wherein R 16 is —H.

16. The pharmaceutical formulation of claim 13 wherein the compound has the structure

17. The pharmaceutical formulation of claim 13 wherein the compound has the structure

Assignments (6)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 8, 2021

From: NEURMEDIX, INC.