Compounds as chloride channel blocking agent

Patent metadata

Field	Value
Publication number	US-9834537-B2
Application number	US-201314092151-A
Country	US
Kind code	B2
Filing date	Nov 27, 2013
Priority date	Nov 27, 2013
Publication date	Dec 5, 2017
Grant date	Dec 5, 2017

Abstract

Disclosed is a novel compound to function as a calcium-dependent chloride channel blocking agent.

First claim

What is claimed is:

1. A chloride channel blocking agent, comprising a compound represented by formula 1b or a pharmaceutically acceptable salt compound thereof, wherein [Formula 1b] is:

wherein Y is —R 2 or —(CH 2 ) n R 2 (wherein n is an integer from 0 to 6);
R 1 denotes nitro; and
R 2 is a substituted or non-substituted naphthyl group.

2. The chloride channel blocking agent of claim 1 , wherein R 2 denotes 1-naphthyl, 2-naphthyl, 4-halo- 1-naphthyl, 2-trifluoromethylnaphthyl, 4-trifluoromethylnaphthyl, 2,4-di(trifluoromethyl)naphthyl, 2,4-difluoronaphthyl, 2,6-difluoronaphthyl, 3,4-dichloronaphthyl, 4-nitronaphthyl, 4-methylnaphthyl, 4-methoxynaphthyl, 5-methoxynaphthyl, 4-nitro-2-naphthyl, 4-methyl-2-naphthyl, 1-methoxy-2-naphthyl, 4-methoxy-2-naphthyl or 5-methoxy-2-naphthyl group.

3. The chloride channel blocking agent of claim 1 , wherein the compound is selected from:
compound No. 28: N-naphthyl-3-nitroanthranilic acid,
compound No. 29: N-((4-chloro)naphthyl)-3-nitroanthranilic acid,
compound No. 30: N-(2-naphthyl)-3-nitroanthranilic acid,
compound No. 31: N-naphthyl-4-nitroanthranilic acid,
compound No. 32: N-((4-fluoro)naphthyl)-4-nitroanthranilic acid,
compound No. 33: N-((4-chloro)naphthyl)-4-nitroanthranilic acid,
compound No. 34: N-((4-bromo)naphthyl)-4-nitroanthranilic acid,
compound No. 35: N-((4-nitro)naphthyl)-4-nitroanthranilic acid,
compound No. 36: N-((4-methoxy)naphthyl)-4-nitroanthranilic acid,
compound No. 37: N-(2-naphthyl)-4-nitroanthranilic acid,
compound No. 38: N-((1-methoxy)-2-naphthyl)-4-nitroanthranilic acid,
compound No. 39: N-((4-methoxy)-2-naphthyl)-4-nitroanthranilic acid,
compound No. 40: N-naphthyl-5-nitroanthranilic acid,
compound No. 41: N-((4-fluoro)naphthyl)-5-nitroanthranilic acid,
compound No. 42: N-((4-chloro)naphthyl)-5-nitroanthranilic acid,
compound No. 43: N-((4-bromo)naphthyl)-5-nitroanthranilic acid,
compound No. 44: N-((4-iodo)naphthyl)-5-nitroanthranilic acid,
compound No. 45: N-((2-methoxy)naphthyl)-5-nitroanthraniic acid,
compound No. 46: N-((3-methoxy)naphthyl)-5-nitroanthranilic acid,
compound No. 47: N-((4-methoxy)naphthyl)-5-nitroanthranilic acid,
compound No. 48: N-((5-methoxy)naphthyl)-5-nitroanthranilic acid,
compound No. 49: N-((6-methoxy)naphthyl)-5-nitroanthranilic acid,
compound No. 50: N-((7-methoxy)naphthyl)-5-nitroanthranilic acid,
compound No. 51: N-((8-methoxy)naphthyl)-5-nitroanthranilic acid,
compound No. 52: N-(2-naphthyl)-5-nitroanthranilic acid,
compound No. 53: N-((1-methoxy)-2-naphthyl)-5-nitroanthranilic acid,
compound No. 54: N-((3-methoxy)-2-naphthyl)-5-nitroanthranilic acid,
compound No. 55: N-((4-methoxy)-2-naphthyl)-5-nitroanthranilic acid,
compound No. 56: N-((5-methoxy)-2-naphthyl)-5-nitroanthranilic acid,
compound No. 57: N-((6-methoxy)-2-naphthyl)-5-nitroanthranilic acid,
compound No. 58: N-((7-methoxy)-2-naphthyl)-5-nitroanthranilic acid,
compound No. 59: N-((8-methoxy)-2-naphthyl)-5-nitroanthranilic acid,
compound No. 60: N-((7-bromo)-2-naphthyl)-5-nitroanthranilic acid,
compound No. 61: N-((7-iodo)-2-naphthyl)-5-nitroanthranilic acid,
compound No. 62: N-((4-bromo)-2-naphthyl)-5-nitroanthranilic acid,
compound No. 63: N-((4-iodo)-2-naphthyl)-5-nitroanthranilic acid,
compound No. 64: N-((8-bromo)-2-naphthyl)-5-nitroanthranilic acid,
compound No. 70: N-((4-bromo)naphthyl)-6-nitroanthranilic acid,
compound No. 73: 2-(2-naphthylmethylamino)-5-nitroanthranilic acid,
compound No. 74: 2-(2-naphthylethylamino)-5-nitroanthranilic acid,
compound No. 75: 2-(phenylethylamino)-5-nitroanthranilic acid,
or pharmaceutically acceptable salts thereof.

4. A pharmaceutical composition comprising the chloride channel blocking agent or pharmaceutically acceptable salts thereof according claim 1 , as an active ingredient.

5. A pharmaceutical composition comprising the chloride channel blocking agent or pharmaceutically acceptable salts thereof according claim 2 , as an active ingredient.

6. A pharmaceutical composition comprising the chloride channel blocking agent or pharmaceutically acceptable salts thereof according claim 3 , as an active ingredient.

7. A pharmaceutical composition comprising a compound represented by formula 1b or a pharmaceutically acceptable salt compound thereof in an amount effective for blocking a chloride channel, wherein
[Formula 1b] is:

wherein Y is —R 2 or —(CH 2 ) n R 2 (wherein n is an integer from 0 to 6);
R 1 denotes nitro; and
R 2 is a substituted or non-substituted naphthyl group.

Assignees

• Korea Inst Sci & Tech

Inventors

• Roh Eun Joo
• Lee Changjoon Justin
• Oh Soo Jin
• Hwang Seok Jin
• Jung Jong Hoon

Classifications

• C07C229/58

  having the nitrogen atom of at least one of the amino groups further bound to a carbon atom of a six-membered aromatic ring, e.g. N-phenyl-anthranilic acids · CPC title

• C07C229/56

  with amino and carboxyl groups bound in ortho-position · CPC title

• C07D333/40 Primary

  Thiophene-2-carboxylic acid · CPC title