# US 8,465,726 B2 · Stilbene derivatives and their use for binding and imaging amyloid plaques

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- Number: US 8,465,726 B2
- Document ID: US8465726B2
- Status: Granted
- Kind: B2
- Application number: 12/765,397
- Filed: 2010-04-22
- Published: 2010-10-21
- Granted: 2013-06-18
- Earliest claimed: 2004-12-17
- Assignees: The Trustees of the University of Pennsylvania
- Applicants: Hank F. Kung; Mei-Ping Kung; Zhi-Ping Zhuang
- Inventors: Hank F. Kung; Mei-Ping Kung; Zhi-Ping Zhuang
- Web page: https://patentgrep.com/patent/US8465726B2

## CPC

- A61K 51/04: Organic compounds
- 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
- C07B 59/001: {Acyclic or carbocyclic compounds}
- C07C 217/80: having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## 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

### Claim 1

A compound selected from the group consisting of:
methanesulfonic acid 2-[2-(4-{2-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-vinyl}-phenoxy)-ethoxy]-ethyl ester (10a);
methanesulfonic acid 2-{2-[2-(4-{2-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-vinyl}-phenoxy)-ethoxy]-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).

### Claim 2

A process of making a compound of Formula [18F] 12:
wherein n=2, 3, 4, or 5, comprising reacting a compound of Formula 10:
with [18F]F−/Krptofix 222 (“K222”) and K2CO3, in DMSO and treating the resulting mixture with aqueous HCl.

### Claim 3

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).

### Claim 4

A kit for forming imaging agents comprising a vial, wherein the vial contains a solution of a compound that is
methanesulfonic acid 2-[2-(4-{2-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-vinyl}-phenoxy)-ethoxy]-ethyl ester (10a);
methanesulfonic acid 2-{2-[2-(4-{2-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-vinyl}-phenoxy)-ethoxy]-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); or
methanesulfonic acid 2-[2-(2-{2-[2-(4-{2-[4-(tert-butoxycarbonyl-methyl-amino)-phenyl]-vinyl}-phenoxy)-ethoxy]-ethoxy}-ethoxy]-ethoxy)-ethyl ester (10d).