# US 2013/0158017 A1 · Methods for treating or preventing cancer and neurodegenerative diseases

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- Number: US 2013/0158017 A1
- Document ID: US20130158017A1
- Status: Published application
- Kind: A1
- Application number: 13/140,741
- Filed: 2009-12-21
- Published: 2013-06-20
- Earliest claimed: 2008-12-22
- Assignees: Sloan-Kettering Institute for Cancer Research
- Inventors: Lei Zhu; Yueming Li
- Web page: https://patentgrep.com/patent/US20130158017A1

## CPC

- A61K 31/5513: 1,4-Benzodiazepines, e.g. diazepam {or clozapine}
- A61K 31/381: having five-membered rings
- A61P 21/00: Drugs for disorders of the muscular or neuromuscular system
- 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
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 333/34: Sulfur atoms
- C07D 409/12: 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

Provided are methods of treating or preventing a neurodegenerative disease comprising administering to a subject having a neurodegenerative disease an effective amount of a compound of Formula I: where X, R1, R2, subscript m, subscript n and subscript v are as defined herein.

## Claims

### Claim 1

A method for treating or preventing cancer, comprising administering to a subject in need of treatment or prevention of the cancer an effective amount of a compound of Formula I, having any one of the following structures:
or a pharmaceutically acceptable salt thereof.

### Claim at position 2

2-18. (canceled)

### Claim 19

A method for treating or preventing cancer, comprising administering to a subject in need of treatment or prevention of the cancer an effective amount of a compound of Formula IIaa having the structure:
or a pharmaceutically acceptable salt thereof.

### Claim 20

A method for treating or preventing a neurodegenerative disease, comprising administering to a subject in need of treatment or prevention of the neurodegenerative disease an effective amount of a compound of Formula I
or a pharmaceutically acceptable salt thereof, wherein:
X is H, halo, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or cyano;
each R1 is independently H, halo, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or cyano;
R2 is
each R3 is independently H, halo, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or cyano;
Z1 is NH, O, or CH2;
Z2 is —(C1-C6 alkylene)-, —(C2-C6 alkenylene)-, or —(O—(C2-C6 alkylene))-;
m is 3;
n is 1;
p is an integer from 1 to 5;
q is 0; and
v is an integer from 1 to 3.

### Claim 21

(canceled)

### Claim 22 (depends on 20)

The method of claim 20, wherein the compound of Formula I has the following Formula Iaa
wherein:
X is halo;
each R1 is independently H, halo, C1-C6 alkyl, or C1-C6 haloalkyl; and
each R3 is independently H, halo, C1-C6 alkyl, or C1-C6 haloalkyl;
Z2 is —(C1-C6 alkylene)-, —(C2-C6 alkenylene)-, or —(O—(C2-C6 alkylene))-;
m is 3;
p is an integer from 1 to 5;
q is 0; and
v is an integer from 1 to 3.

### Claim 23 (depends on 20)

The method of claim 20, wherein each R1 is H.

### Claim 24

(canceled)

### Claim 25 (depends on 20)

The method of claim 20, wherein v is 1 and X is in the 5-position of the thiopheno group.

### Claim 26 (depends on 20)

The method of claim 20, wherein p is 1 and R3 is in the 4-position of the phenyl group.

### Claim 27 (depends on 22)

The method of claim 22, wherein the compound of Formula Iaa has the structure:
or a pharmaceutically acceptable salt thereof.

### Claim at position 12

28-30. (canceled)

### Claim 31

A method for treating or preventing a neurodegenerative disease, comprising administering to a subject in need of treatment or prevention of the neurodegenerative disease an effective amount of a compound of Formula II
or a pharmaceutically acceptable salt thereof, wherein:
X is H, halo, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or cyano;
each R1 is independently H, halo, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or cyano;
each R3 is independently H, halo, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or cyano;
R4 is
R5 is H, C1-C6 alkyl, or C1-C6 haloalkyl;
Z1 is NH, O, or CH2;
Z2 is —(C1-C6 alkylene)- or —(C2-C6 alkenylene)-;
m is 3;
n is 1;
p is 5;
t is 4;
q is 0 or 1; and
v is an integer from 1 to 3.

### Claim 32 (depends on 31)

The method of claim 31, wherein the compound of Formula II has the following Formula IIa
wherein:
X is H, halo, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or cyano;
each R1 is independently H, halo, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or cyano;
each R3 is independently H, halo, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, or cyano;
R5 is H, C1-C6 alkyl, or C1-C6 haloalkyl;
Z1 is NH, O or CH2;
Z2 is —(C1-C6 alkylene)- or —(C2-C6 alkenylene)-;
m is 3;
p is 5;
t is 4;
q is 0 or 1; and
v is an integer from 1 to 3.

### Claim 33 (depends on 32)

The method of claim 32, wherein the compound of Formula IIa has the following Formula IIaa
wherein:
X is halo;
each R1 is independently H, halo, C1-C6 alkyl, or C1-C6 haloalkyl;
each R3 is independently H, halo, C1-C6 alkyl, or C1-C6 haloalkyl;
Z2 is —(C1-C6 alkylene)- or —(C2-C6 alkenylene)-;
m is 3;
p is 5;
t is 4;
q is 0 or 1; and
v is an integer from 1 to 3.

### Claim 34 (depends on 31)

The method of claim 31, wherein each R1 is H.

### Claim 35 (depends on 31)

The method of claim 31, wherein R5 is H or methyl.

### Claim 36 (depends on 31)

The method of claim 31, wherein R5 is methyl.

### Claim 37 (depends on 31)

The method of claim 31, wherein q is 0.

### Claim 38 (depends on 31)

The method of claim 31, wherein v is 1 and X is in the 5-position of the thiopheno group.

### Claim 39 (depends on 33)

The method of claim 33, wherein the compound of Formula IIaa has the structure:
or a pharmaceutically acceptable salt thereof.

### Claim 40 (depends on 33)

The method of claim 33, wherein the compound of Formula IIaa has the structure:
or a pharmaceutically acceptable salt thereof.

### Claim 41 (depends on 31)

The method of claim 31, wherein the neurodegenerative disease is Alzheimer's disease, Parkinson's disease, ALS, or MS.

### Claim 42 (depends on 31)

The method of claim 31, wherein the neurodegenerative disease is Alzheimer's disease.