Method of treating inflammatory bowel disease comprising administering a pharmaceutical composition comprising a 6-aminopyridin-3-ol compound or a pharmaceutically acceptable salt thereof as an active ingredient to a subject

Patent metadata

Field	Value
Publication number	US-2016354352-A1
Application number	US-201615237642-A
Country	US
Kind code	A1
Filing date	Aug 16, 2016
Priority date	Dec 21, 2011
Publication date	Dec 8, 2016
Grant date	—

Abstract

Provided is a method of treating inflammatory bowel disease comprising administering a pharmaceutical composition comprising a 6-aminopyridin-3-ol compound or a pharmaceutically acceptable salt thereof as an active ingredient to a subject, which inhibits colitis in a model of inflammatory bowel disease, and accordingly, they may be suitable for use as a drug for the prevention or treatment of inflammatory bowel disease.

First claim

What is claimed is:

1 . A method of treating inflammatory bowel disease, comprising:
administering a pharmaceutical composition comprising a 6-aminopyridin-3-ol compound of Formula 1 below or a pharmaceutically acceptable salt thereof as an active ingredient to a subject:

wherein
R 1 is a hydrogen, a C1 to C4 alkyl, or a phenyl, R 2 is a hydrogen, a C1 to C16 alkyl, a C1 to C16 hydroxyalkyl, a C2 to C4 (5-hydroxy-trimethylpyridin-2-yloxy)alkyl, a C3 to C7 cycloalkyl, a benzyl, a phenyl, a C1 to C4 alkylphenyl, a nitrophenyl, a halophenyl, a benzo[d][1,3]-dioxol-5-yl, or a pyridine-2-yl; or R 1 and R 2 are linked to each other to form a 5-membered ring or a 6-membered ring, thereby forming a heterocyclic compound, and are any one selected from pyrrolidine-1-yl, 4-methylpiperazine-1-yl, 6-morpholino, and 1H-pyrrol-1-yl, and each of R 3 to R 5 is a methyl.

2 . The method according to claim 1 , wherein R 1 is a hydrogen, a C1 to C4 alkyl, or a phenyl, R 2 is a hydrogen, a C6 to C16 alkyl, a C1 to C6 hydroxyalkyl, (5-hydroxy-3,4,6-trimethylpyridin-2-yloxy)propyl, a C5 to C6 cycloalkyl, a benzyl, a phenyl, a C1 to C4 alkylphenyl, a nitrophenyl, a halophenyl, or a benzo[d][1,3]-dioxol-5-yl or pyridine-2-yl; or R 1 and R 2 are linked to each other to form a 5-membered ring to a 6-membered ring, thereby forming a heterocyclic compound, and are each pyrrolidine-1-yl, 4-methylpiperazine-1-yl, 6-morpholino, or 1H-pyrrol-1-yl, and each of R 3 to R 5 is a methyl.

3 . The method according to claim 1 , wherein the compound or pharmaceutically acceptable salt thereof is selected from 6-amino-2,4,5-trimethylpyridin-3-ol; 6-(hexylamino)-2,4,5-trimethylpyridin-3-ol; 6-(hexadecylamino)-2,4,5-trimethylpyridin-3-ol; 6-(benzylamino)-2,4,5-trimethylpyridin-3-ol; 6-((3-hydroxypropyl)amino)-2,4,5-trimethylpyridin-3-ol; 6-(3-((5-hydroxy-3,4,6-trimethylpyridin-2-yl)amino)propoxy)-2,4,5-trimethylpyridin-3-ol; 6-(cyclopentylamino)-2,4,5-trimethylpyridin-3-ol; 6-(cyclohexylamino)-2,4,5-trimethylpyridin-3-ol; 2,4,5-trimethyl-6-(phenylamino)pyridin-3-ol; 2,4,5-trimethyl-6-(m-tolylamino)pyridin-3-ol; 2,4,5-trimethyl-6-(p-tolylamino)pyridin-3-ol; 2,4,5-trimethyl-6-((4-propylphenyl)amino)pyridin-3-ol; 6-((2-isopropylphenyl)amino)-2,4,5-trimethylpyridin-3-ol; 6-((4-(tert-butyl)phenyl)amino)-2,4,5-trimethylpyridin-3-ol; 6-((4-methoxyphenyl)amino)-2,4,5-trimethylpyridin-3-ol; 6-((3-isopropoxyphenyl)amino)-2,4,5-trimethylpyridin-3-ol; 6-(benzo[d][1,3]dioxol-5-ylamino)-2,4,5-trimethylpyridin-3-ol; 6-((3-fluorophenyl)amino)-2,4,5-trimethylpyridin-3-ol; 6-((4-fluorophenyl)amino)-2,4,5-trimethylpyridin-3-ol; 6-((3-chlorophenyl)amino)-2,4,5-trimethylpyridin-3-ol; 6-((4-chlorophenyl)amino)-2,4,5-trimethylpyridin-3-ol; 6-((3-bromophenyl)amino)-2,4,5-trimethylpyridin-3-ol; 6-((4-bromophenyl)amino)-2,4,5-trimethylpyridin-3-ol; 2,4,5-trimethyl-6-((3-nitrophenyl)amino)pyridin-3-ol; 2,4,5-trimethyl-6-((4-nitrophenyl)amino)pyridin-3-ol; 2,4,5-trimethyl-6-(pyridin-2-ylamino)pyridin-3-ol; 2,4,5-trimethyl-6-(pyrrolidin-1-yl)pyridin-3-ol; 2,4,5-trimethyl-6-(piperidin-1-yl)pyridin-3-ol; 2,4,5-trimethyl-6-(4-methylpiperazin-1-yl)pyridin-3-ol; 2,4,5-trimethyl-6-morpholinopyridin-3-ol; 2,4,5-trimethyl-6-(methyl(phenyl)amino)pyridin-3-ol; 2,4,5-trimethyl-6-(methyl(m-tolyl)amino)pyridin-3-ol; 2,4,5-trimethyl-6-(methyl(p-tolyl)amino)pyridin-3-ol; 6-((4-fluorophenyl)(methyl)amino)-2,4,5-trimethylpyridin-3-ol; 6-((4-chlorophenyl)(methyl)amino)-2,4,5-trimethylpyridin-3-ol; 6-(diphenylamino)-2,4,5-trimethylpyridin-3-ol; 2,4,5-trimethyl-6-(methyl(pyridin-2-yl)amino)pyridin-3-ol and 2,4,5-trimethyl-6-(1H-pyrrol-1-yl)pyridin-3-ol.

4 . The method according to claim 1 , wherein the pharmaceutically acceptable salt is an acid-added salt from an organic acid selected from the group consisting of an oxalic acid, a maleic acid, a fumaric acid, a malic acid, a tartaric acid, a citric acid, a benzoic acid, methanesulfonic acid and camphorsulfonic acid.

5 . The method according to claim 1 , wherein the pharmaceutically acceptable salt is an acid-added salt from an inorganic acid selected from the group consisting of a hydrochloric acid, a sulfuric acid, a phosphoric acid, and a hydrobromic acid.

Assignees

• Univ Yeungnam Res Cooperation Foundation

Inventors

• Jeong Byeong Seon
• Kim Jung Ae
• Kim Dong Guk
• Kang You Ra
• Nam Tae Gyu

Classifications

• A61K31/4412

  having oxo groups directly attached to the heterocyclic ring · CPC title

• A61K31/5377 Primary

  not condensed and containing further heterocyclic rings, e.g. timolol · CPC title

• A61K31/496

  Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin · CPC title

• A61K31/443

  containing a five-membered ring with oxygen as a ring hetero atom · CPC title

• A61K31/4439

  containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465) · CPC title