# US 10,246,455 B2 · Histone deacetylase inhibitors

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- Number: US 10,246,455 B2
- Document ID: US10246455B2
- Status: Granted
- Kind: B2
- Application number: 15/302,739
- Filed: 2015-04-09
- Published: 2017-03-02
- Granted: 2019-04-02
- Earliest claimed: 2014-04-11
- Assignees: Taipei Medical University; National Health Research Institutes
- Applicants: Taipei Medical University; National Health Research Institutes
- Inventors: Jing-Ping Liou; Jang-Yang Chang; Jia-Yi Wang; Yun Yen
- Web page: https://patentgrep.com/patent/US10246455B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61K 31/437: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 209/08: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C07D 231/56: Benzopyrazoles; Hydrogenated benzopyrazoles
- C07D 487/04: Ortho-condensed systems
- 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

Fused bicycle indol, indoline, azoindole, or azoindoline compounds of Formula (I) set forth herein. Also disclosed are pharmaceutically acceptable salts of these compounds and pharmaceutical compositions containing the same. Further disclosed is a method for treating cancer, e.g., glioma, prostate cancer, and colorectal cancer, with these compounds.

## Claims

### Claim 1

A compound of formula (I):
wherein
R1 is SO2Ra, in which Ra is phenyl substituted with
R2 is H;
R3 is H;
X is C;
A is unsubstituted pyridine; and
is a double bond,
or a pharmaceutically acceptable salt or solvate thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the compound is selected from the group consisting of the following compounds:

### Claim 3 (depends on 2)

The compound of claim 2, wherein the compound is

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

A method of alleviating, relieving, altering, ameliorating, improving, or affecting cancer comprising administering to a subject in need thereof an effective amount of a compound of claim 1.

### Claim 6 (depends on 5)

The method of claim 5, wherein the cancer is glioma, prostate cancer, colorectal cancer, breast cancer, non-small-cell lung cancer, gastric cancer, oral cancer, nasopharyngeal cancer, T cell lymphoma, or B cell lymphoma.

### Claim 7 (depends on 6)

The method of claim 6, wherein the cancer is glioma, prostate cancer, or colorectal cancer.

### Claim 8 (depends on 5)

The method of claim 5, wherein the compound is orally administered to a subject in need thereof.

### Claim 9 (depends on 8)

The method of claim 8, wherein the compound is administered once a day.