IP Library Granted Patent US 9,035,057
Granted Patent B2
US 9,035,057 · App. 13/516,783 · Granted May 19, 2015

Dihydroethidine analogues and uses thereof

Inventors: Robert H. Mach (Eureka, MO); Mark Mintun (Villanova, PA); Wenhua Chu (Saint Louis, MO); Laura Dugan (San Diego, CA)
Assignee: Washington University
C07D221/12C07D401/12
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Quick Facts
Patent No.
US 9,035,057
App. No.
13/516,783
Granted
May 19, 2015
Kind
B2
Abstract

Tracers for imaging distribution of reactive oxygen species (ROS) are disclosed. The tracers include radiolabeled dihydroethidine (DHE) analogues. Further disclosed are uses of the compounds, including methods of imaging tissue distribution of ROS in vivo by positron emission tomography (PET). Methods of synthesizing the compounds are also disclosed.

Claims (22)

1. A radiolabeled compound or salt thereof of structure

wherein R 1 is H or O—R 3 , R 3 is (CH 2 ) q CH 3 ,

q is an integer from 0 to 10; n is an integer from 0 to 3, m is an integer from 0 to 3, p is an integer from 0 to 3, R 2 is methyl or

a is an integer from 0 to 10, wherein at least one atom is a radioisotope and is a bond.

2. A radiolabeled compound or salt thereof in accordance with claim 1 , wherein the radioisotope is a positron-emitting radioisotope.

3. A radiolabeled compound or salt thereof in accordance with claim 1 wherein R 1 is H.

4. A radiolabeled compound or salt thereof in accordance with claim 1 , wherein the compound or salt thereof comprises an 11 CH 3 .

5. A radiolabeled compound or salt thereof in accordance with claim 1 , wherein R 3 is (CH 2 ) q —CH 3 and q is 0.

6. A radiolabeled compound or salt thereof in accordance with claim 5 , wherein R 3 is 11 CH 3 .

7. A radiolabeled compound or salt thereof in accordance with claim 1 , wherein R 3 is

n is an integer from 0 to 3, m is an integer from 0 to 3 and is a bond.

8. A radiolabeled compound or salt thereof in accordance with claim 1 , wherein R 1 is O—R 3 , R 3 is CH 3 .

9. A radiolabeled compound or salt thereof in accordance with claim 8 , wherein R 1 is O—R 3 , wherein R 3 is 11 CH 3 .

10. A radiolabeled compound or salt thereof in accordance with claim 1 , wherein R 1 is O—R 3 , R 3 is

n is an integer from 0 to 3, m is an integer from 0 to 3, F is 18 F and is a bond.

11. A radiolabeled compound or salt thereof in accordance with claim 10 , wherein n is 1.

12. A radiolabeled compound or salt thereof in accordance with claim 10 , wherein m is 2.

13. A radiolabeled compound or salt thereof in accordance with claim 10 , wherein n is 1 and m is 2.

14. A radiolabeled compound or salt thereof in accordance with claim 1 , wherein R 3 is,

p is an integer from 0 to 3, F is 18 F and is a bond.

15. A radiolabeled compound or salt thereof in accordance with claim 13 , wherein p is 2.

16. A radiolabeled compound or salt thereof in accordance with claim 1 , wherein the compound is selected from the group consisting of

Assignments (2)
CONFIRMATORY LICENSE Recorded Mar 31, 2017
From: WASHINGTON UNIVERSITY
To: NATIONAL INSTITUTES OF HEALTH (NIH), U.S. DEPT. OF HEALTH AND HUMAN SERVICES (DHHS), U.S. GOVERNMENT
Reel/Frame 042125/0990 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 7, 2015
From: MACH, ROBERT H; CHU, WENHUA; MINTUN, MARK A; DUGAN, LAURA
To: WASHINGTON UNIVERSITY
Reel/Frame 035345/0698 →
Continuity (2)
Provisional Application 61287115 · Dec 16, 2009
Related Publication 20130079522A1 · Mar 28, 2013