STILBENE DERIVATIVES AND THEIR USE FOR BINDING AND IMAGING AMYLOID PLAQUES

• US 20100266500A1
• Filed: 04/22/2010
• Published: 10/21/2010
• Est. Priority Date: 12/17/2004
• Status: Active Grant

• Current Assignee: Trustees Of The University Of Pennsylvania (University of Pennsylvania)
• Original Assignee: Trustees Of The University Of Pennsylvania (University of Pennsylvania)
• Inventors: Kung, Mei-Ping, Kung, Hank F., Zhuang, Zhi-Ping
• Granted Patent: US 8,465,726 B2
• Time in Patent Office: Days
• US Class Current: 424/1.890
• CPC Class Codes: A61K 51/04 Organic compounds
• CPC Class Codes: A61P 25/28 for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
• CPC Class Codes: C07B 59/001 Acyclic or carbocyclic compounds
• CPC Class Codes: C07C 217/80 having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings

Abstract

This invention relates to a method of imaging amyloid deposits and to labeled compounds, and methods of making labeled compounds useful in imaging amyloid deposits. This invention also relates to compounds, and methods of making compounds for inhibiting the aggregation of amyloid proteins to form amyloid deposits, and a method of delivering a therapeutic agent to amyloid deposits.

Claims

1. A compound selected from the group consisting of:

methanesulfonic acid 2-[2-(4-{2-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-vinyl}-phenoxy)-ethoxyl-ethyl ester (10a);

methanesulfonic acid 2-{2-[2-(4-{2-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-vinyl}-phenoxy)-ethoxy}-ethyl ester (10b);

methanesulfonic acid 2-(2-{2-[2-(4-{2-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-vinyl}-phenoxy)-ethoxyl]-ethoxy}-ethoxy)-ethyl ester (10c); and

methanesulfonic acid 2-[2-(2-{2-[2-(4-{2-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-vinyl}-phenoxy)-ethoxy]-ethoxy}-ethoxy]-ethoxy)-ethyl ester (10d).

2. A process of making a compound of Formula [¹⁸F]12:

3. A kit for forming the imaging agents comprising a vial, wherein the vial contains a physiologically suitable solution of an intermediate of Formula I, in a concentration and at a pH suitable for optimal complexing conditions.

4. A compound selected from the group consisting of:

[4-(2-{4-[2-(2-Hydroxy-ethoxy)-ethoxy]-phenyl}-vinyl)-phenyl]-methyl-carbamic acid tert-butyl ester (9a);

{4-[2-(4-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethoxy)-phenyl)-vinyl]-phenyl}-methylcarbamic acid tert-butyl ester (9b);

(4-{2-[4-(2-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-phenyl]-vinyl}-phenyl)-methyl-carbamic acid tert-butyl ester (9c); and

[4-(2-{4-[2-(2-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-phenyl)-vinyl)-phenyl]-methyl-carbamic acid tert-butyl ester (9d).