Ligands for imaging cardiac innervation

Patent metadata

Field	Value
Publication number	US-11241509-B2
Application number	US-201815986680-A
Country	US
Kind code	B2
Filing date	May 22, 2018
Priority date	Dec 26, 2006
Publication date	Feb 8, 2022
Grant date	Feb 8, 2022

Abstract

Novel compounds that find use as imaging agents within nuclear medicine applications (PET imaging) for imaging of cardiac innervation are disclosed. These PET based radiotracers may exhibit increased stability, decreased NE release thereby reducing side effects, improved quantitative data, and/or high affinity for VMAT over prior radiotracers. In some instances the compounds are developed by derivatizing certain compounds with 18F in a variety of positions: aryl, alkyl, a keto, benzylic, beta-alkylethers, gamma-propylalkylethers and beta-proplylalkylethers. Alternatively or additionally, a methyl group a is added to the amine, and/or the catechol functionality is either eliminated or masked as a way of making these compounds more stable.

First claim

What is claimed is:

1. A compound having Structure Chi as follows:

or a salt thereof;
wherein R selected from the group consisting of OR 3 , OCH 2 CH 2 F, and OCH 2 CH 2 Im;
R 1 is selected from the group consisting of H, OR 3 , F, Cl, Br, and I; and
R 2 is H;
R 3 is alkyl;

wherein said alkyl, of R 3 is substituted with one or more groups selected from halogen, Im, COOR 4 , CON(R 4 ) 2 ,SR 4 , OR 4 , and NHC(=O)NH 2 ;
R 4 is alkyl; and
wherein Im is an imaging agent selected from the group consisting of 18 F, 76 Br, 124 I, and 131 I.

2. The compound of claim 1 , wherein the alkyl group is substituted with a functional group selected from the group consisting of F, Cl, Br, I, Im, COOR 4 , CON(R 4 ) 2 , SR 4 , OR 4 and NHC(=O)NH2.

3. The compound of claim 1 , wherein Im is 18 F.

4. A compound of the formula:

or a pharmaceutically acceptable salt thereof.

Assignees

• Lantheus Medical Imaging Inc

Inventors

• Purohit Ajay
• Harris Thomas D
• Radeke Heike S
• Robinson Simon P
• Yu Ming
• Casebier David S
• Azure Michael T

Classifications

• C07B59/001

  Acyclic or carbocyclic compounds · CPC title

• A61K51/0459

  having six-membered rings with two nitrogen atoms as the only ring hetero atoms, e.g. piperazine · CPC title

• C07B2200/05

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

• C07C215/60

  the chain having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring · CPC title

• C07D233/54

  having two double bonds between ring members or between ring members and non-ring members · CPC title