# US 9,040,727 B2 · Histone deacetylase inhibitor of benzamides and use thereof

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- Number: US 9,040,727 B2
- Document ID: US9040727B2
- Status: Granted
- Kind: B2
- Application number: 14/129,407
- Filed: 2012-06-26
- Published: 2014-08-07
- Granted: 2015-05-26
- Earliest claimed: 2011-06-27
- Assignees: Shanghai Institute of Pharmaceutical Industry; Sinopharm A-think Pharmaceutical Co., Ltd; Sinopharm A-Think Medical and Pharmaceutical Research & Development (Beijing) Co., Ltd.
- Applicants: Jianqi Li; Qingwei Zhang; Zhidan Jia; Jiajing Wang
- Inventors: Jianqi Li; Qingwei Zhang; Zhidan Jia; Jiajing Wang
- Web page: https://patentgrep.com/patent/US9040727B2

## CPC

- C07C 237/48: having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system of the same carbon skeleton
- A61P 5/00: Drugs for disorders of the endocrine system
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 35/00: Antineoplastic agents
- A61P 37/00: Drugs for immunological or allergic disorders
- A61P 37/02: Immunomodulators
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 237/42: having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
- C07D 209/42: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 213/75: Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- C07D 235/24: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D 307/85: attached in position 2
- C07D 307/87: Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D 307/88: with one oxygen atom directly attached in position 1 or 3
- C07D 333/70: attached in position 2
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Disclosed in the present invention is a novel histone deacetylase inhibitor of benzamides and use thereof. The inhibitor has good efficacy in treating diseases caused by abnormal gene expression, such as tumors, endocrine disorders, immune system diseases, genetic diseases and nerve system diseases. The histone deacetylase inhibitor of benzamides is a compound of the following general chemical structural formula (I) or a salt thereof.

## Claims

### Claim 1

A compound selected from the group consisting of:
V-1 N-(4-(2-aminophenylaminocarbonyl)phenyl)-2-naphthamide,
V-2 N-(4-(2-amino-5-fluorophenylaminocarbonyl)phenyl)-2-naphthamide,
V-2′ N-(4-(2-amino-5-fluorophenylaminocarbonyl)phenyl)-2-naphthamide hydrochloride,
V-3 N-(4-(2-aminophenylaminocarbonyl)phenyl)-6-methoxy-2-naphthamide,
V-4 N-(4-(2-amino-5-fluorophenylaminocarbonyl)phenyl)-6-methoxy-2-naphthamide,
V-5 N-(4-(2-aminophenylaminocarbonyl)phenyl)-1H-indole-2-carboxamide,
V-5′ N-(4-(2-aminophenylaminocarbonyl)phenyl)-1H-indole-2-carboxamide hydrobromide,
V-6 N-(4-(3-aminopyridine-4-carbamoyl)phenyl)-1H-indole-2-carboxamide,
V-6′ N-(4-(3-aminopyridine-4-carbamoyl)phenyl)-1H-indole-2-carboxamide sulfate,
V-7 N-(4-(2-amino-5-fluorophenylaminocarbonyl)phenyl)-1H-indole-2-carboxamide,
V-8 N-(4-(2-aminophenylaminocarbonyl)phenyl)benzofuran-2-carboxamide,
V-8′ N-(4-(2-aminophenylaminocarbonyl)phenyl)benzofuran-2-carboxamide mesylate,
V-9 N-(4-(2-amino-5-fluorophenylaminocarbonyl)phenyl)benzofuran-2-carboxamide,
V-10 N-(4-(2-amino-5-thienylphenylaminocarbonyl)phenyl)benzofuran-2-carboxamide,
V-11 N-(4-(2-amino-5-phenylphenylaminocarbonyl)phenyl)benzofuran-2-carboxamide,
V-12 N-(4-(2-aminophenylaminocarbonyl)phenyl)-1H-benzimidazol-2-carboxamide,
V-13 N-(4-(2-amino-5-fluorophenylaminocarbonyl)phenyl)-1H-benzimidazol-2-carboxamide,
V-13′ N-(4-(2-amino-5-fluorophenylaminocarbonyl)phenyl)-1H-benzimidazol-2-carboxamide trifluoroacetate,
V-14 N-(4-(2-amino-5-furylphenylaminocarbonyl)phenyl)-1H-benzimidazol-2-carboxamide,
V-15 N-(4-(2-aminophenylaminocarbonyl)phenyl)-1-naphthamide,
V-16 N-(4-(3-aminopyridine-4-carbamoyl)phenyl)-1-naphthamide,
V-17 N-(4-(2-amino-5-fluorophenylaminocarbonyl)phenyl)-1-naphthamide,
V-18 N-(4-(2-aminophenylaminocarbonyl)phenyl)-5-fluoro-1H-indole-2-carboxamide,
V-18′ N-(4-(2-aminophenylaminocarbonyl)phenyl)-5-fluoro-1H-indole-2-carboxamide malate,
V-19 N-(4-(2-aminophenylaminocarbonyl)phenyl)-5-methyl-1H-indole-2-carboxamide,
V-20 N-(4-(2-aminophenylaminocarbonyl)phenyl)-5-trifluoromethyl-1H-indole-2-carboxamide,
V-20′ N-(4-(2-aminophenylaminocarbonyl)phenyl)-5-trifluoromethyl-1H-indole-2-carboxamide maleate,
V-21 N-(4-(2-aminophenylaminocarbonyl)phenyl)-3-methoxybenzofuran-2-carboxamide,
V-22 N-(4-(2-aminophenylaminocarbonyl)phenyl)-5-methylamino-1H-indole-2-carboxamide,
V-23 N-(4-(2-aminophenylaminocarbonyl)phenyl)-5-amino-1H-indole-2-carboxamide,
V-24 N-(4-(2-aminophenylaminocarbonyl)phenyl)benzothiophene-2-carboxamide,
V-25 5-acetamido-N-(4-(2-aminophenylaminocarbonyl)phenyl)-1H-indole-2-carboxamide,
V-26 5-acetyl-N-(4-(2-aminophenylaminocarbonyl)phenyl)-1H-indole-2-carboxamide,
V-27 N-(4-(2-amino-5-fluorophenylaminocarbonyl)phenyl)benzothiophene-2-carboxamide, and
V-28 N-(4-(3-aminopyridine-4-carbamoyl)phenyl)benzothiophene-2-carboxamide; and salts thereof.

### Claim 2 (depends on 1)

A pharmaceutical composition comprising a therapeutically effective amount of the compound or a salt thereof according to claim 1, and a pharmaceutically acceptable carrier.

### Claim 3 (depends on 1)

A method for treating a tumor, comprising administering a therapeutically effective amount of the compound or a salt thereof according to claim 1 to a patient in need thereof.