1 H -[1, 2, 3] triazole substituted amino acids and uses thereof

• US 8,722,014 B2
• Filed: 05/03/2010
• Issued: 05/13/2014
• Est. Priority Date: 05/01/2009
• Status: Expired due to Fees

• Current Assignee: Washington University In St Louis
• Original Assignee: Washington University In St Louis
• Inventors: Mach, Robert H., McConathy, Jonathan
• Primary Examiner(s): Hartley, Michael G
• Assistant Examiner(s): Donohue, Sean R
• Application Number:
  US12/772,760
• Publication Number:
  US 20100278732A1
• Time in Patent Office: 1,471 Days
• Field of Search: None
• US Class Current: 424/9.1
• CPC Class Codes: A61K 51/0453 having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
• CPC Class Codes: C07B 59/002 Heterocyclic compounds
• CPC Class Codes: C07D 249/04 1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles

Abstract

Tracers for cationic amino acid transport systems and methods of synthesis are disclosed, including compounds comprising a 1H-[1,2,3]triazole moiety. Further disclosed are uses of the analogues, including in vivo imaging of tumors by Positron emission tomography (PET) or Single Photon Emission Computed Tomography (SPECT).

Claims

1. A 1H-[1,2,3]triazole substituted amino acid of structure

2. A 1H-[1,2,3]triazole substituted amino acid in accordance with claim 1, wherein R₁ is CH₂, n is from 1 to 3, m is 0, p is 1, and F is an ¹⁸F.

3. A 1H-[1,2,3]triazole substituted amino acid in accordance with claim 1, wherein R₁ is CH₂, n is l, m is 0, p is 1, and F is an ¹⁸F.

4. A 1H-[1,2,3]triazole substituted amino acid in accordance with claim 1, wherein R₁ is CH₂, n is 2, m is 0, p is 1, and F is an ¹⁸F.

5. A 1H-[1,2,3]triazole substituted amino acid in accordance with claim 1, wherein R₁ is CH₂, n is 3, m is 0, p is 1, and F is an ¹⁸F.

6. A 1H-[1,2,3]triazole substituted amino acid or salt thereof in accordance with claim 1, wherein the acid is selected from the group consisting of

13. A method of imaging a tumor in a mammal, the method comprising:

administering to the mammal a 1H-[1,2,3]triazole substituted amino acid of claim 1; and

subjecting the mammal to PET scanning.

14. A method of imaging a tumor in a mammal in accordance with claim 13, wherein the 1H-[1,2,3]triazole substituted amino acid is selected from the group consisting of

15. A method of imaging a tumor in a mammal in accordance with claim 13, wherein the 1H-[1,2,3]triazole substituted amino acid is selected from the group consisting of

7. A 1H-[1,2,3]triazole substituted amino acid of structure

8. A 1H-[1,2,3]triazole substituted amino acid in accordance with claim 7, wherein R₂ is O, z is 1 to 3, y is 1, x is 2, and the F is an ¹⁸F.

9. A 1H-[1,2,3]triazole substituted amino acid in accordance with claim 7, wherein R₂ is O, z is 1, y is 1, x is 2, and the F is an ¹⁸F.

10. A 1H-[1,2,3]triazole substituted amino acid in accordance with claim 7, wherein R₂ is O, z is 2, y is 1, x is 2, and the F is an ¹⁸F.

11. A 1H-[1,2,3]triazole substituted amino acid in accordance with claim 7, wherein R₂ is O, z is 3, y is 1, x is 2, and the F is an ¹⁸F.

12. A 1H-[1,2,3]triazole substituted amino acid in accordance with claim 7, wherein the acid is selected from the group consisting of