Boat tropanes
Radiopharmaceutical compounds are disclosed. A tropane compound is linked through the N atom at the 8-position to a chelating ligand capable of complexing technetium or rhenium to produce a neutral labeled complex that selectively binds to the dopamine transporter over the serotonin transporter with a ratio of 10 or more. These compounds can be prepared as separate diastereoisomers as well as a mixture of diastereoisomers. Also disclosed are radiopharmaceutical kits for preparing the labeled radiopharmaceutical compounds.
1. A compound having the following structural formula:
wherein
R 1 is α or β and COR a ;
R 2 is α and is selected from C 6 H 4 X, C 6 H 3 XY, C 10 H 7 X, and C 10 H 6 XY;
R a is C 1 –C 5 alkyl;
X and Y are independently selected from R a , H, Br, Cl, I, F, OH, and OCH 3 ;
wherein the compound is in the 1R or 1S configuration; and
Rb is either H or CH 3 .
2. The compound according to claim 1 , wherein R a is methyl.
3. The compound according to claim 1 , wherein R a is ethyl.
4. The compound according to claim 1 , wherein R a is propyl.
5. The compound according to claim 1 , wherein R a is isopropyl.
6. The compound according to claim 1 selected from the group consisting of:
a. 2β-(1-Propanoyl)-3β-(4-fluorophenyl)tropane;
b. 2β-(1-Propanoyl)-3β-(3,4-dichlorophenyl)tropane;
c. 2β-(1-Propanoyl)-3β-(4-fluorophenyl)nortropane; and
d. 2β-(1-Propanoyl)-3β-(3,4-dichlorophenyl)nortropane.
7. A compound having the following structural formula:
wherein R 1 is β and COR a ;
R 2 is α and is selected from C 6 H 4 X, C 6 H 3 XY, C 10 H 7 X, and C 10 H 6 XY;
R a is C 1 –C 5 alkyl;
X and Y are independently selected from R a , H, Br, Cl, I, F, OH, and OCH 3 ;
wherein the compound is in the 1R or 1S configuration; and
R b is either H or CH 3 .
8. The compound of claim 7 , wherein R a is ethyl.
9. The compound of claim 8 , wherein R 2 is C 6 H 4 X.
10. The compound of claim 9 , wherein X is F.
11. 2β-(1-Propanoyl)-3α-(4-fluorophenyl)-tropane.
12. (1R)-2β-( 1-Propanoyl)-3α-(4-fluorophenyl)-tropane.