Radiolabelled fluorobenzamide analogues, their synthesis and use in diagnostic imaging

• US 8,193,360 B2
• Filed: 04/07/2011
• Issued: 06/05/2012
• Est. Priority Date: 07/31/2003
• Status: Expired due to Fees

• Current Assignee: Washington University In St Louis
• Original Assignee: Washington University In St Louis
• Inventors: Mach, Robert H., Tu, Zhude
• Primary Examiner(s): CHANDRAKUMAR, NIZAL S
• Application Number:
  US13/082,215
• Publication Number:
  US 20110230662A1
• Time in Patent Office: 425 Days
• Field of Search: 546/151
• US Class Current: 546/151
• CPC Class Codes: A61K 31/47 Quinolines; Isoquinolines
• CPC Class Codes: A61K 31/495 having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazinesA61K31/48 takes precedence ; with three nitrogen atoms A61K31/53
• CPC Class Codes: A61K 51/04 Organic compounds
• CPC Class Codes: A61K 51/0497 conjugates with a carrier being an organic compounds
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: C07C 323/41 Y being a hydrogen or an acyclic carbon atom
• CPC Class Codes: C07D 217/04 with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
• CPC Class Codes: C07D 257/02 not condensed with other rings
• CPC Class Codes: C07D 295/13 to an acyclic saturated chain

Abstract

Fluoroalkoxybenzamide compounds which selectively bind Sigma-2 receptors are disclosed. These compounds, when labelled with ¹⁸F, can be used as radiotracers for imaging of tumors by positron emission tomography (PET). In addition, these compounds, when labelled with ¹²³I, can be used as radiotracers for imaging of tumors by single photon emission computed tomography (SPECT). Methods for synthesis of these compounds are also disclosed.

Claims

1. A method for synthesizing a radiolabelled fluoroalkoxybenzamide compound of structure

2. A method for synthesizing a radiolabelled fluoroalkoxybenzamide compound in accordance with claim 1, wherein m=2, n=4, R₁ is selected from the group consisting of H and OCH₃, and R₂ is selected from the group consisting of CH₃, Br and I.

3. A method for synthesizing a radiolabelled fluoroalkoxybenzamide compound in accordance with claim 1, wherein m=2, n=4, R₁ is OCH₃, and R₂ is I.

4. A method for synthesizing a radiolabelled fluoroalkoxybenzamide compound in accordance with claim 1, wherein the organic solvent is dimethyl sulfoxide.

5. A method for synthesizing a radiolabelled fluoroalkoxybenzamide compound in accordance with claim 1, wherein the organic solvent is acetonitrile.