# US 2014/0155493 A1 · Bis-aromatic anticancer agents

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- Number: US 2014/0155493 A1
- Document ID: US20140155493A1
- Status: Published application
- Kind: A1
- Application number: 14/176,809
- Filed: 2014-02-10
- Published: 2014-06-05
- Earliest claimed: 2008-04-10
- Assignees: The UAB Research Foundation
- Applicants: The Uab Research Foundation
- Inventors: Ahmad Safavy
- Web page: https://patentgrep.com/patent/US20140155493A1

## CPC

- C07C 323/16: the carbon skeleton containing six-membered aromatic rings
- A61K 31/047: having two or more hydroxy groups, e.g. sorbitol
- A61K 31/09: having two or more such linkages
- A61K 31/095: Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K 31/10: Sulfides; Sulfoxides; Sulfones
- A61P 35/00: Antineoplastic agents
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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

Treatment of cancer includes administering a compound of formula (I) to a subject. In particular, treatment of colorectal cancer is described.

## Claims

### Claim at position 1

1-24. (canceled)

### Claim 25

A method of treating cancer in a subject, the method comprising administering to the subject an effective amount of a compound according to formula (II):
wherein:
X is selected from: S; S═O; and SO2;
each Z is independently selected from H; C1-10 alkyl; OR1; halo; ═O; NR1R2; NO2; CN; SR1; SO2; COOR1; C5-12 cycloalkyl; C5-12 heterocycloalkyl; C5-12 aryl; and C5-12 heteroaryl; wherein the alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl may be substituted or unsubstituted;
each W is independently selected from: C1-10 alkyl; OR1; halo; NR1R2; NO2; CN; SR1; SO2; COOR1; C5-12 cycloalkyl; C5-12 heterocycloalkyl; C5-12 aryl; and C5-12 heteroaryl; wherein the alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl may be substituted or unsubstituted;
each R1 and R2 is independently H or C1-10 substituted or unsubstituted alkyl;
m is independently an integer from 0 to 10;
n is independently an integer from 0 to 10; and
each p is independently an integer from 0 to 5; or
a pharmaceutically acceptable salt form thereof.

### Claim 26 (depends on 25)

The method of claim 25, wherein the compound according to formula (II) is selected from:
a pharmaceutically acceptable salt form thereof.

### Claim 27 (depends on 25)

The method of claim 25, wherein the compound according to formula (II) is:
or a pharmaceutically acceptable salt form thereof.

### Claim 28 (depends on 25)

The method of claim 25, wherein the subject is a human.

### Claim 29 (depends on 25)

The method of claim 25, wherein the cancer is selected from: bladder cancer, brain cancer, breast cancer, colorectal cancer, cervical cancer, gastrointestinal cancer, genitourinary cancer, head and neck cancer, lung cancer, ovarian cancer, pancreatic cancer, prostate cancer, renal cancer, skin cancer, and testicular cancer.

### Claim 30 (depends on 29)

The method of claim 29, wherein the cancer is colorectal cancer.

### Claim 31 (depends on 29)

The method of claim 29, wherein the cancer is pancreatic cancer.

### Claim 32 (depends on 29)

The method of claim 29, wherein the cancer is prostate cancer.

### Claim 33

A method of promoting cell death in a cell, the method comprising contacting the cell with a therapeutically effective amount of a compound of formula (II):
wherein:
X is selected from: S; S═O; and SO2;
each Z is independently selected from H; C1-10 alkyl; OR1; halo; ═O; NR1R2; NO2; CN; SR1; SO2; COOR1; C5-12 cycloalkyl; C5-12 heterocycloalkyl; C5-12 aryl; and C5-12 heteroaryl; wherein the alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl may be substituted or unsubstituted;
each W is independently selected from: C1-10 alkyl; OR1; halo; NR1R2; NO2; CN; SR1; SO2; COOR1; C5-12 cycloalkyl; C5-12 heterocycloalkyl; C5-12 aryl; and C5-12 heteroaryl; wherein the alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl may be substituted or unsubstituted;
each R1 and R2 is independently H or C1-10 substituted or unsubstituted alkyl;
m is independently an integer from 0 to 10;
n is independently an integer from 0 to 10; and
each p is independently an integer from 0 to 5; or
a pharmaceutically acceptable salt form thereof.

### Claim 34

A pharmaceutical composition comprising one or more of a pharmaceutically acceptable carrier, excipient, diluent, or adjuvant; and a compound according to formula (II):
wherein:
X is selected from: S; S═O; and SO2;
each Z is independently selected from H; C1-10 alkyl; OR1; halo; ═O; NR1R2; NO2; CN; SR1; SO2; COOR1; C5-12 cycloalkyl; C5-12 heterocycloalkyl; C5-12 aryl; and C5-12 heteroaryl; wherein the alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl may be substituted or unsubstituted;
each W is independently selected from: C1-10 alkyl; OR1; halo; NR1R2; NO2; CN; SR1; SO2; COOR1; C5-12 cycloalkyl; C5-12 heterocycloalkyl; C5-12 aryl; and C5-12 heteroaryl; wherein the alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl may be substituted or unsubstituted;
each R1 and R2 is independently H or C1-10 substituted or unsubstituted alkyl;
m is independently an integer from 0 to 10;
n is independently an integer from 0 to 10; and
each p is independently an integer from 0 to 5; or
a pharmaceutically acceptable salt form thereof.

### Claim 35 (depends on 34)

The composition of claim 34, wherein the carrier, excipient, or diluent is a physiologically acceptable saline solution.

### Claim 36 (depends on 34)

The composition of claim 34, wherein the composition further comprises a pain relief agent, an antinausea agent, or an additional anticancer agent.