Fatty acid derivative labeled with positron-emitting radionuclide

Patent metadata

Field	Value
Publication number	US-12029797-B2
Application number	US-201917261328-A
Country	US
Kind code	B2
Filing date	Jul 19, 2019
Priority date	Jul 20, 2018
Publication date	Jul 9, 2024
Grant date	Jul 9, 2024

Abstract

Provided is a labeled fatty acid derivative for diagnostic imaging that enables quantification of fatty acid metabolic activity in the heart muscle.
[Means for Solution]
The present inventors have conducted intensive investigations on a method that enables quantification of fatty acid metabolic activity and thus have found that a labeled fatty acid derivative typified by 3-{[(5Z)-3-[ 18 F]fluorotetradeca-5-en-1-yl]sulfanyl}propanoic acid or a salt thereof has excellent accumulation to the heart muscle and thus enables imaging of fatty acid metabolic activity by positron emission tomography (PET). Therefore, the labeled fatty acid derivative of the present invention can be used as a radiolabeled tracer for rapid and non-invasive quantification of fatty acid metabolic activity in the heart muscle, diagnostic imaging of heart disease typified by an ischemic heart disease, diagnostic imaging of the therapeutic effect of a therapeutic drug for heart disease, and the like.

First claim

The invention claimed is:

1. A labeled fatty acid derivative represented by formula (I) or a salt thereof,

(in the formula, any one of R 1 to R 3 is 18 F, the other two are H, and Me is a methyl group).

2. The labeled fatty acid derivative or a salt thereof according to claim 1 , wherein R 1 is H.

3. The labeled fatty acid derivative or a salt thereof according to claim 1 , wherein the labeled fatty acid derivative is 3-{[(5Z)-3-[ 18 F]fluorotetradeca-5-en-1-yl]sulfanyl}propanoic acid.

4. The labeled fatty acid derivative or a salt thereof according to claim 1 , wherein the labeled fatty acid derivative is 3-{[(5Z)-2-[ 18 F]fluorotetradeca-5-en-1-yl]sulfanyl}propanoic acid.

5. A composition for diagnostic imaging comprising:
the labeled fatty acid derivative or a salt thereof according to claim 1 ; and
a pharmaceutically acceptable carrier.

6. A method for diagnostic imaging of heart disease comprising: administering a detectable amount of the labeled fatty acid derivative or a salt thereof according to claim 1 to a subject.

7. The method for diagnostic imaging according to claim 6 , wherein the heart disease is an ischemic heart disease.

8. A method for producing the labeled fatty acid derivative or a salt thereof according to claim 1 , comprising:
allowing a [ 18 F]fluoride ion to react with the compound represented by formula (1i) or a salt thereof:

(in the formula, any one of R 11 to R 31 is a leaving group, the other two are H, and R′ is an H or a lower alkyl group which may be substituted, and Me is a methyl group.

9. The composition for diagnostic imaging according to claim 5 , wherein the labeled fatty acid derivative is 3-{[(5Z)-3- 18 F fluorotetradeca-5-en-1-yl]sulfanyl}propanoic acid.

10. The composition for diagnostic imaging according to claim 5 , wherein the labeled fatty acid derivative is 3-{[(5Z)-2- 18 F fluorotetradeca-5-en-1-yl]sulfanyl}propanoic acid.

11. The method for diagnostic imaging according to claim 6 , wherein the labeled fatty acid derivative is 3-{[(5Z)-3- 18 F fluorotetradeca-5-en-1-yl]sulfanyl}propanoic acid.

12. The method for diagnostic imaging according to claim 6 , wherein the labeled fatty acid derivative is 3-{[(5Z)-2- 18 F fluorotetradeca-5-en-1-yl]sulfanyl}propanoic acid.

13. The method for diagnostic imaging according to claim 6 , wherein further comprising the step of imaging the labeled fatty acid derivative or a salt thereof in the heart of the subject.

14. The method for diagnostic imaging according to claim 13 , where the imaging is by positron emission tomography (PET).

Assignees

• Astellas Pharma Inc

Inventors

• Murakami Yoshihiro
• Fushiki Hiroshi
• Fujita Yuji

Classifications

• C07B2200/05

  Isotopically modified compounds, e.g. labelled · CPC title

• C07B59/001 Primary

  Acyclic or carbocyclic compounds · CPC title

• A61K2123/00

  Preparations for testing in vivo · CPC title

• A61K51/0402 Primary

  carboxylic acid carriers, fatty acids (amino acids A61K51/0406) · CPC title

• G01T1/161

  Applications in the field of nuclear medicine, e.g. in vivo counting {(apparatus for radiation diagnosis A61B6/00)} · CPC title