# US 9,040,021 B2 · Heterocyclic compounds as imaging probes of tau pathology

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- Number: US 9,040,021 B2
- Document ID: US9040021B2
- Status: Granted
- Kind: B2
- Application number: 13/885,466
- Filed: 2011-11-07
- Published: 2013-09-12
- Granted: 2015-05-26
- Earliest claimed: 2010-11-16
- Assignees: Ge Healthcare Limited
- Applicants: Clare Jones; Amanda Ewan; Duncan Wynn; Alessandra Gaeta; James Nairne
- Inventors: Clare Jones; Amanda Ewan; Duncan Wynn; Alessandra Gaeta; James Nairne
- Web page: https://patentgrep.com/patent/US9040021B2

## CPC

- A61K 51/0455: {having six-membered rings with one nitrogen as the only ring hetero atom}
- A61P 25/00: Drugs for disorders of the nervous system
- 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
- C07D 215/12: with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D 215/14: Radicals substituted by oxygen atoms
- C07D 215/18: Halogen atoms or nitro radicals
- C07D 215/36: Sulfur atoms (C07D215/24 takes precedence)
- C07D 295/067: with the ring nitrogen atoms and the substituents attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Heterocyclic compounds of formula (I) useful as imaging probes of Tau pathology in Alzheimer's disease are described. Compositions and methods of making such compounds are also described.

## Claims

### Claim 1

A compound of Formula (IV):
wherein R1 is independently H, halogen, OH, COOH, SO3H, NH2, NO2, CONHNH2, alkyl, or alkoxy;
R2 is independently H, halogen, OH, COOH, SO3H, NH2, NO2, CONHNH2, alkyl, or alkoxy;
n is an integer from 0-4; and
m is an integer from 0-2;
wherein at least one of R1 and R2 is optionally a radionuclide or optionally substituted with a radionuclide; and
wherein F is optionally 18F.

### Claim 2 (depends on 1)

A pharmaceutical composition comprising a compound according claim 1 and a pharmaceutically acceptable carrier or excipient.

### Claim 3 (depends on 1)

A method of imaging comprising administering a compound of claim 1 wherein said R1 or R2 is a radionuclide or substituted with a radionuclide or the F of the compound of Formula (IV) is 18F or a pharmaceutical composition thereof.

### Claim 4 (depends on 1)

A method of detecting tau aggregates and/or in vivo comprising the steps of:
i) administering to a subject a radiolabeled compound of claim 1, or a pharmaceutical composition thereof;
ii) allowing said radiolabeled compound to bind to NFTs in said subject;
iii) detecting signals emitted by said radiolabeled compound;
iv) generating an image representative of the location and/or amount of said signals; and,
determining the distribution and extent of said tau aggregates in said subject.