# US 2016/0354352 A1 · 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

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- Number: US 2016/0354352 A1
- Document ID: US20160354352A1
- Status: Published application
- Kind: A1
- Application number: 15/237,642
- Filed: 2016-08-16
- Published: 2016-12-08
- Earliest claimed: 2011-12-21
- Assignees: Research Cooperation Foundation of Yeungnam University
- Applicants: Research Cooperation Foundation of Yeungnam University
- Inventors: Byeong Seon JEONG; Jung Ae KIM; Dong Guk KIM; You Ra KANG; Tae Gyu NAM
- Web page: https://patentgrep.com/patent/US20160354352A1

## CPC

- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61K 31/4412: having oxo groups directly attached to the heterocyclic ring
- A61K 31/496: Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- 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)

## 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.

## Claims

### Claim 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
R1 is a hydrogen, a C1 to C4 alkyl, or a phenyl, R2 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 R1 and R2 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 R3 to R5 is a methyl.

### Claim 2 (depends on 1)

The method according to claim 1, wherein R1 is a hydrogen, a C1 to C4 alkyl, or a phenyl, R2 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 R1 and R2 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 R3 to R5 is a methyl.

### Claim 3 (depends on 1)

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.

### Claim 4 (depends on 1)

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.

### Claim 5 (depends on 1)

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.