18F labeled amino acids, derivatives thereof and method of making same

Patent metadata

Field	Value
Publication number	US-11534114-B2
Application number	US-201716327638-A
Country	US
Kind code	B2
Filing date	Aug 23, 2017
Priority date	Aug 23, 2016
Publication date	Dec 27, 2022
Grant date	Dec 27, 2022

Abstract

The present invention provides 18F-labeled amino acids or derivatives thereof having formula (I) and methods of making same, which can be suitable for PET imaging:

First claim

The invention claimed is:

1. A compound having a formula (I):

or a salt thereof or a stereoisomer thereof, wherein:

n 1 is 2, 3, 4 or 5;
n 2 and n 3 are 0;
R 1 is alkyl;
R 2 is alkyl;
R 3 is H;
R 4 is H or COR 10 , wherein R 10 is an amino acid residue or peptide;
R 5 is H or COR 10 , wherein R 10 is an amino acid residue or peptide;
R 6 is —OH; and
R 7 is H.

2. The compound according to claim 1 , wherein n 1 is 2.

3. The compound according to claim 1 , wherein n 1 is 3.

4. The compound according to claim 1 , wherein R 1 and R 2 are methyl.

5. The compound according to claim 1 , wherein R 4 and R 5 are both H.

6. The compound according to claim 1 , wherein one of R 4 and R 5 is H, and the other is COR 10 .

7. The compound according to claim 1 , wherein the amino acid residue is an amino acid selected from the group consisting of lysine (K), aspargine (N), glycine (G), alanine (A), glutamic acid (E), phenylalanine (F), histidine (H), and aspartic acid (D).

8. The compound according to claim 1 , wherein the peptide comprises two or more amino acids selected from the group consisting of lysine (K), aspargine (N), glycine (G), alanine (A), glutamic acid (E), phenylalanine (F), histidine (H), and aspartic acid (D).

9. The compound according to claim 1 , wherein the amino acid residue is glutamic acid (E).

10. A compound of claim 1 , which is:

11. A 18 F-labeled compound, which is:

12. A method of PET imaging comprising administering a compound of claim 1 to a subject.

13. A method of diagnosis of a proliferative disease comprising administering a compound of claim 1 to a subject.

14. A compound of claim 1 , which is:

15. A method of PET imaging comprising administering a compound of claim 10 to a subject.

16. A method of diagnosis of a proliferative disease comprising administering a compound of claim 10 to a subject.

17. A method of PET imaging comprising administering a compound of claim 11 to a subject.

18. A method of diagnosis of a proliferative disease comprising administering a compound of claim 11 to a subject.

19. A method of PET imaging comprising administering a compound of claim 14 to a subject.

20. A method of diagnosis of a proliferative disease comprising administering a compound of claim 14 to a subject.

Assignees

• Univ Fraser Simon

Inventors

• Schaffer Paul
• Yang Hua
• Britton Robert
• Nodwell Matthew
• Yuan Zheliang

Classifications

• C07C229/36

  with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton · CPC title

• C07C229/20

  the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups · CPC title

• C07K1/13

  Labelling of peptides · CPC title

• C07K5/06191

  containing heteroatoms different from O, S, or N · CPC title

• C07C275/16

  being further substituted by carboxyl groups · CPC title