# US 10,865,196 B2 · Compounds for treatment of cancer

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- Number: US 10,865,196 B2
- Document ID: US10865196B2
- Status: Granted
- Kind: B2
- Application number: 15/872,199
- Filed: 2018-01-16
- Published: 2019-03-28
- Granted: 2020-12-15
- Earliest claimed: 2008-06-16
- Assignees: University of Tennessee Research Foundation; Oncternal Therapeutics, Inc.
- Applicants: University of Tennessee Research Foundation; Oncternal Therapeutics, Inc
- Inventors: Duane D. Miller; Jianjun Chen; James T. Dalton; Chien-Ming Li; Sunjoo Ahn; Wei Li
- Web page: https://patentgrep.com/patent/US10865196B2

## CPC

- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- A61K 31/4178: not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
- A61K 31/421: 1,3-Oxazoles, e.g. pemoline, trimethadione
- A61K 31/426: 1,3-Thiazoles
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- 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 233/02: having no double bonds between ring members or between ring members and non-ring members
- C07D 233/22: Radicals substituted by oxygen atoms
- C07D 233/54: having two double bonds between ring members or between ring members and non-ring members
- C07D 263/06: with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
- C07D 263/14: with radicals substituted by oxygen atoms
- C07D 263/32: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 277/04: having no double bonds between ring members or between ring members and non-ring members
- C07D 277/24: Radicals substituted by oxygen atoms
- C07D 277/28: Radicals substituted by nitrogen atoms
- C07D 277/56: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D 413/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/06: linked by a carbon chain containing only aliphatic carbon atoms
- 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

The present invention relates to a compound of formula XXII and a compound of formula 17ya, which are defined as anywhere in the specification, to a composition comprising the same, and to a method of using thereof in the treatment of various forms of cancer.

## Claims

### Claim 1

A compound selected from the following group:
(2-(1-H-indol-1-yl)imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone;
(2-(1-H-indol-2-yl)imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone;
(2-(1-H-indol-4-yl)imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone;
(2-(1-H-indol-5-yl)imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone;
(2-(1-H-indol-6-yl)imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone; and
(2-(1-H-indol-7-yl)imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone,
or a pharmaceutically acceptable salt thereof, a hydrate thereof, or a combination thereof.

### Claim 2 (depends on 1)

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

### Claim 3

A method of treating cancer by administering a therapeutically effective amount of a compound selected from the following group:
(2-(1-H-indol-1-yl)imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone;
(2-(1-H-indol-2-yl)imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone;
(2-(1-H-indol-4-yl)imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone;
(2-(1-H-indol-5-yl)imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone;
(2-(1-H-indol-6-yl)imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone; and
(2-(1-H-indol-7-yl)imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone,
or a pharmaceutically acceptable salt thereof, a hydrate thereof, or a combination thereof.

### Claim 4 (depends on 3)

The method according to claim 3, wherein the cancer is prostate cancer, breast cancer, ovarian cancer, skin cancer, lung cancer, colon cancer, leukemia, renal cancer or CNS cancer, or a combination thereof.

### Claim 5 (depends on 3)

The method according to claim 3, wherein the compound is administered systemically.

### Claim 6 (depends on 3)

The method according to claim 3, wherein the compound is administered orally, topically, transdermally, parenterally, subcutaneously, intravenously, intramuscularly, intraperitoneally, by intranasal instillation, by intracavitary or intravesical instillation, intraocularly, intraarterially, intralesionally, or by application to mucous membranes.

### Claim 7 (depends on 3)

The method according to claim 3, wherein the compound is administered directly to a site where cancer cells are present.

### Claim 8 (depends on 3)

The method according to claim 3, wherein the is administered in an amount of about 0.01 mg to about 100 mg per kg·body weight.

### Claim 9 (depends on 3)

The method according to claim 3, wherein the compound is administered periodically.

### Claim 10 (depends on 3)

The method according to claim 3, wherein the compound is administered in combination with another cancer therapy.