# US 2014/0155445 A1 · Compounds and Methods for Treating Cancer and Diseases of the Central Nervous System

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- Number: US 2014/0155445 A1
- Document ID: US20140155445A1
- Status: Published application
- Kind: A1
- Application number: 14/030,702
- Filed: 2013-09-18
- Published: 2014-06-05
- Earliest claimed: 2007-06-14
- Assignees: Queen's University at Kingston; Osta Biotechnologies; The Sir Mortimer B. Davis - Jewish General Hospital
- Applicants: Osta Biotechnologies Inc.
- Inventors: Ajay Gupta; Hyman M. Schipper; Moulay Alaoui-Jamali; Walter A. Szarek; Kanji Nakatsu; Jason Z. Vlahakis
- Web page: https://patentgrep.com/patent/US20140155445A1

## CPC

- C07D 233/56: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- A61K 31/4164: 1,3-Diazoles
- A61K 31/4174: Arylalkylimidazoles, e.g. oxymetazolin, naphazoline, miconazole
- A61K 31/4178: not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/16: Anti-Parkinson drugs
- 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: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

## Abstract

Disclosed are compounds of the general formula (I): compositions comprising an effective amount of said compounds either alone or in combination with other chemotherapeutic agents, and methods useful for treating or preventing cancer and for inhibiting tumour tissue growth. These compounds attenuate the oxidative damage associated with increased heme-oxygenase activity and can reduce cell proliferation in transformed cells. In addition, the described compounds and compositions are useful as neuroprotectants and for treating or preventing neurodegenerative disorders and other diseases of the central nervous system.

## Claims

### Claim at position 1

1-32. (canceled)

### Claim 33

A method of treating or preventing Alzheimer's disease or Parkinson's disease, comprising administering to an individual in need thereof a compound of Formula (I):
where
T is phenyl optionally substituted with alkyl, perfluoroalkyl, alkyloxy, alkenyl, alkynyl, cycloalkyl, aryl, aryloxy, arylalkyl, mercaptoalkyl, or a moiety selected from the group consisting of F, Cl, Br, I, OH, SH, CN, NR8R9, NO2, CO2R10 and CHO, wherein R8, R9 and R10 are unsubstituted and are independently hydrogen, alkyl, perfluoroalkyl, alkyloxy, alkenyl, alkynyl, cycloalkyl, aryl, aryloxy, arylalkyl, or mercaptoalkyl;
n is 3 to 6:
C represents carbon, each C of (C)n being unsubstituted; and
D is imidazolyl;
or a pharmaceutically acceptable salt or ester thereof.

### Claim at position 3

34-36. (canceled)

### Claim 37 (depends on 33)

The method of claim 33, wherein D is 1,3-imidazolyl.

### Claim 38 (depends on 33)

The method of claim 33, wherein n is 3 to 4.

### Claim 39 (depends on 33)

The method of claim 33, wherein n is 4.

### Claim 40 (depends on 33)

The method of claim 33, wherein T is substituted with perfluoroalkyl.

### Claim 41 (depends on 33)

The method of claim 33, wherein T is selected from the group consisting of: 4-chlorophenyl, 3-methoxyphenyl, 2-amino-4-chlorophenyl, 4-methoxyphenyl, phenyl, 4 fluorophenyl, 4-bromophenyl, 4-iodophenyl, 2-hydroxyphenyl, 4-nitrophenyl, biphenyl-4-yl, 3,4-dichlorophenyl, 4-isopropylphenyl, 4-tert-butylphenyl, 4-hydroxyphenyl, 4-(trifluoromethyl)phenyl), and 4-benzoylphenyl.

### Claim 42

(canceled)

### Claim 43 (depends on 33)

The method of claim 33, wherein said compound is selected from the group consisting of: 4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)butane hydrochloride (QC-105); 1-(3-Phenyl-propyl)-1H-imidazole hydrochloride (QC-172); 1-[4-(4-Bromo-phenyl)-butyl]1H-imidazole hydrochloride (QC-199); 1-[4-(4-(Trifluoromethyl)phenyl)butyl]-1H-imidazole hydrochloride (QC-234); and pharmaceutically acceptable salts thereof.

### Claim 44 (depends on 33)

The method of claim 33, wherein said compound is 1-[4-(4 Bromo-phenyl)-butyl]-1H-imidazole hydrochloride (QC-199); or pharmaceutically acceptable salts thereof.

### Claim 45 (depends on 33)

The method according to claim 33, wherein the disease is Alzheimer's disease.

### Claim at position 13

46-89. (canceled)

### Claim 90 (depends on 33)

The method according to claim 33, wherein the disease is Parkinson's disease.

### Claim 91 (depends on 40)

The method of claim 40, wherein T is substituted with Br.

### Claim 92 (depends on 40)

The method of claim 40, wherein T is substituted with Cl.