IP Library Granted Patent US 9,522,908
Granted Patent B2
US 9,522,908 · App. 14/047,362 · Granted Dec 20, 2016

Ezrin inhibitors and methods of making and using

Inventors: Milton L. Brown (Brookeville, MD); Mikell Paige (Fairfax, VA); Jeffrey A. Torestsky (Silver Spring, MD); Aykut Uren (Rockville, MD); George Kosturko (Alexandria, VA); Gullay Bulut (Washington, DC)
Assignee: Gerogetown University
C07D413/12C07D209/48C07D215/24C07D215/38C07D217/24C07D237/30C07D401/06C07D401/12C07D471/04
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Quick Facts
Patent No.
US 9,522,908
App. No.
14/047,362
Granted
Dec 20, 2016
Kind
B2
Abstract

The invention encompasses compound and pharmaceutical composition comprising the compound of the following Formula (I): or pharmaceutically acceptable salts or prodrugs thereof, that are useful for inhibiting ezrin protein in a cell or for inhibiting the growth of a cancer cell.

Claims (28)

1. A compound of

or pharmaceutically acceptable salts thereof,

wherein

E, F and G are present;

 is

wherein

D is H, OH, NO 2 , CN, carboxy, SH, CF 3 , C 1 to C 10 alkoxy, NH 2 , or NR 13 R 14 ; wherein R 13 and

R 14 are each independently H, C 1 to C 15 linear chain or branched chain alkyl;

E is —(CH 2 ) 2 —;

F is a bond, O, S,

 and

G is

wherein

R 1 and R 5 are each indepdently H, halogen, NO 2 , CN, carboxy, SH, CF 3 , C 1 to C 5 alkoxy, C 1 to C 5 alkyl group, NHCONH 2 , NH—SO 2 CH 3 , NH—NH—NH 2 , NH 2 , or NR 13 R 14 , and R 3 , R 6 -R 12 and X 1 -X 5 are each independently selected from H, halogen, OH, NO 2 , CN, carboxy, SH, CF 3 , C 1 to C 5 alkoxy, C 1 to C 5 alkyl group, NHCONH 2 , NH—SO 2 CH 3 , NH—NH—NH 2 , NH 2 , or NR 13 R 14 , and R 2 and R 4 are each independently selected from H, halogen, OH, NO 2 , CN, carboxy, SH, CF 3 , C 1 to C 5 alkyl group, NHCONH 2 , NH—SO 2 CH 3 , NH—NH—NH 2 , NH 2 , or NR 13 R 14 ;

with the proviso that when R 3 is OH and

 is

R 2 and R 4 are not both H, OH, or the same halogen.

2. The compound of claim 1 , wherein D is hydrogen.

3. The compound of claim 1 , wherein D is NH 2 or NR 13 R 14 .

4. The compound of claim 1 , wherein

D is H, F is a bond; and

G is

5. The compound of claim 1 , wherein R 3 is hydroxy or methoxy.

6. A method of inhibiting ezrin protein in a cell comprising administering to the cell the compound of claim 1 , or a pharmaceutically acceptable salt thereof.

7. A method of inhibiting the growth of a cancer cell comprising administering to the cell an amount of at least one compound of claim 1 wherein the cancer cell is an osteosarcoma cell or a lung cancer cell.

8. The method of claim 7 wherein the cancer cell is an osteosarcoma cell.

9. The method of claim 8 , wherein the osteosarcoma cell is in a subject.

10. The compound of claim 1 , wherein the compound is selected from the group consisting of

Assignments (2)
CONFIRMATORY LICENSE Recorded Dec 14, 2015
From: GEORGETOWN UNIVERSITY
To: US ARMY, SECRETARY OF THE ARMY
Reel/Frame 037279/0280 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 11, 2015
From: BROWN, MILTON L.; PAIGE, MIKELL; TORESTSKY, JEFFREY A.; UREN, AYKUT; BULUT, GULAY
To: GEORGETOWN UNIVERSITY
Reel/Frame 036298/0237 →
Continuity (3)
Continuation 13818223
Provisional Application 61375823 · Aug 21, 2010
Related Publication 20140135325A1 · May 15, 2014