Haloisoquinoline carboxamide

• US 5,998,624 A
• Filed: 05/07/1998
• Issued: 12/07/1999
• Est. Priority Date: 05/07/1997
• Status: Expired due to Fees

• Current Assignee: Emory University
• Original Assignee: Emory University
• Inventors: Goodman, Mark M., Chappell, David, Alexander, R. W., Patterson, Randolph E.
• Primary Examiner(s): NORTHINGTON DAVIS, ZINNA
• Application Number:
  US09/074,056
• Time in Patent Office: 579 Days
• Field of Search: 546/146
• US Class Current: 546/146
• CPC Class Codes: C07D 217/26 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Abstract

Compounds of the invention have the general structure ##STR1## X, Y or Z are, respectively independently, H, F or an isotope thereof, Br or an isotope thereof, I or an isotope thereof, At or an isotope thereof, (R₁)W or (R₂)V and R is --(R₁)W, when W is H or F or an isotope thereof, R₁ is linear or branched alkyl of 1-4 carbon atoms, R₂ is vinyl, V is I or an isotope thereof and at least one of X, Y or Z is not H. The compounds of the invention bind to PK receptors.

Claims

1. A compound of the formula:

##STR4## Wherein X, Y and Z, independently of one another, are selected from the group consisting of H, F, ¹⁸ F, I, ¹²³ I, ¹²⁴ I, ¹²⁵ I, ¹³¹ I, Br, ⁷⁵ Br, ⁷⁶ Br, ⁷⁷ Br, ⁸² Br, ²¹⁰ At, ²¹¹ (R₁)W or (R₂)V;

R is --(R₁)W, wherein W is selected from the group consisting of F, and ¹⁸ F, and wherein R₁ is a linear or branched alkyl comprising from 1 to about 4 carbon atoms, R₂ is vinyl, wherein V is I, ¹²³ I, ¹²⁴ I, ¹²⁵ I or ¹³¹ I; and

at least one of X, Y or Z is not H.

2. The compound of claim 1 wherein R₁ is --(CH₂)₃ --.

3. The compound of claim 2 wherein W is F.

4. The compound of claim 2 wherein W is ¹⁸ F.

5. The compound of claim 1 wherein R₁ is --(CH₂)₂ --.

6. The compound of claim 5 wherein W is F.

7. The compound of claim 5 wherein W is ¹⁸ F.

8. The compound of claim 4 wherein X is selected from the group consisting of I, ¹²³ I, ¹²⁴ I, ¹²⁵ I, ¹³¹ I, and wherein Y and Z are each H.

9. The compound of claim 4 wherein Y is selected from the group consisting of I, ¹²³ I, ¹²⁴ I, ¹²⁵ I, ¹³¹ I, and wherein X and Z are each H.

10. The compound of claim 4 wherein Z is selected from the group consisting of I, ¹²³ I, ¹²⁴ I, ¹²⁵ I, ¹³¹ I, and wherein Y and X are each H.

11. The compound of claim 1 wherein R is sec-butyl.

12. The compound of claim 11 wherein X is selected from the group consisting of I, ²³¹ I, ¹²⁴ I, ¹²⁵ I, ¹³¹ I, and wherein Y and Z are each H.

13. The compound of claim 11 wherein Y is selected from the group consisting of I, ¹²³ I, ¹²⁴ I, ¹²⁵ I, ¹³¹ I, and wherein X and Z are each H.

14. The compound of claim 11 wherein Z is selected from the group consisting of I, ¹²³ I, ¹²⁴ I, ¹²⁵ I, ¹³¹ I, and wherein Y and X are each H.

15. The compound of claim 7 wherein X is selected from the group consisting of I, ¹²³ I, ¹²⁴ I, ¹²⁵ I, ¹³¹ I, and wherein Y and Z are each H.

16. The compound of claim 3 wherein X is selected from the group consisting of I, ¹²³ I, ¹²⁴ I, ¹²⁵ I, ¹³¹ I, and wherein Y and Z are each H.

17. The compound of claim 3 wherein Y is selected from the group consisting of I, ¹²³ I, ¹²⁴ I, ¹²⁵ I, ¹³¹ I, and wherein X and Z are each H.

18. The compound of claim 3 wherein Z is selected from the group consisting of I, ¹²³ I, ¹²⁴ I, ¹²⁵ I, ¹³¹ I, and wherein Y and X are each H.