IP Library Granted Patent US 7,834,031
Granted Patent B2
US 7,834,031 · App. 11/991,727 · Granted Nov 16, 2010

Radiolabeled glycine transporter inhibitors

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Quick Facts
Patent No.
US 7,834,031
App. No.
11/991,727
Granted
Nov 16, 2010
Kind
B2
Abstract

The present invention is directed to radiolabeled glycine transporter inhibitors which are useful for the labeling and diagnostic imaging of glycine transporters in mammals.

Claims (38)

1. A compound of the formula:

wherein:

A is selected from N and CH;

R 2a and R 2b are independently selected from the group consisting of:

(1) hydrogen,

(2) fluoro,

(3) chloro, and

(4) bromo;

R 3 is C 1-6 alkyl, which is unsubstituted or substituted with fluoro;

R 4 is selected from the group consisting of:

(1) hydrogen, and

(2) C 1-3 alkyl;

one of X and Y is selected from the group consisting of:

(1) 18 F,

(2) —O( 11 CH 3 ), and

(3) —O(CD 2 18 F),

and the other of X and Y is hydrogen;

or a pharmaceutically acceptable salt thereof or an individual enantiomer or diastereomer thereof.

2. The compound of claim 1 of the formula Ia:

wherein R 4 is C 1-3 alkyl;

or a pharmaceutically acceptable salt thereof.

3. The compound of claim 1 of the formula Ib:

or a pharmaceutically acceptable salt thereof.

4. The compound of claim 1 wherein R 2a and R 2b are independently selected from the group consisting of:

(1) hydrogen,

(2) fluoro, and

(3) chloro.

5. The compound of claim 4 wherein R 2a is chloro and R 2b is chloro.

6. The compound of claim 4 wherein R 2a is chloro and R 2b is hydrogen.

7. The compound of claim 4 wherein R 2a is fluoro and R 2b is hydrogen.

8. The compound of claim 1 wherein R 3 is —CH 2 CH 3 .

9. The compound of claim 1 wherein X is 18 F and Y is hydrogen.

10. The compound of claim 1 wherein X is hydrogen and Y is 18 F.

11. The compound of claim 1 wherein X is —O( 11 CH 3 ) and Y is hydrogen.

12. The compound of claim 1 wherein X is hydrogen and Y is —O(CD 2 18 F).

13. A compound which is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

14. A radiopharmaceutical composition which comprises the compound of claim 1 and a pharmaceutically acceptable carrier or excipient.

Assignments (5)
MERGER Recorded Aug 8, 2022
From: MERCK SHARP & DOHME CORP.
To: MERCK SHARP & DOHME LLC
Reel/Frame 061102/0145 →
CHANGE OF NAME Recorded Aug 29, 2012
From: SCHERING CORPORATION
To: MERCK SHARP & DOHME CORP.
Reel/Frame 028866/0511 →
MERGER Recorded Aug 27, 2012
From: MERCK SHARP & DOHME CORP.
To: SCHERING CORPORATION
Reel/Frame 028850/0515 →
CHANGE OF NAME Recorded Jan 26, 2010
From: MERCK & CO., INC.
To: MERCK SHARP & DOHME CORP.
Reel/Frame 023906/0803 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 29, 2008
From: BURNS, H. DONALD; HAMILL, TERENCE G.; LINDSLEY, CRAIG W.
To: MERCK & CO., INC.
Reel/Frame 022037/0708 →