IP Library Granted Patent US 7,019,144
Granted Patent B2
US 7,019,144 · App. 10/608,709 · Granted Mar 28, 2006

1,2,4-Triazole derivative, method for preparing the same, and pharmaceutical composition containing the same

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Quick Facts
Patent No.
US 7,019,144
App. No.
10/608,709
Granted
Mar 28, 2006
Kind
B2
Abstract

A 1,2,4-Triazole derivative of formula 1 or a non-toxic salt thereof, a preparation method thereof, and a pharmaceutical composition containing the derivative or the salt as an active ingredient are provided.

Claims (62)

1. A 1,2,4-triazole derivative represented by formula 1:

wherein:

R 1 is a C 3 –C 6 cycloalkyl group; a C 3 –C 6 cycloalkenyl group; a phenyl group; a phenyl group substituted with one or more selected from the group consisting of a C 1 –C 6 alkyl group, a C 1 –C 6 haloalkyl group, a C 1 –C 6 alkoxy group, a C 1 –C 6 haloalkoxy group, a halogen group, an amino group, a monoalkylamino group, a dialkylamino group, a nitro group, and a cyano group; a styrenyl group; a C 1 –C 6 alkoxy styrenyl group; or a pyridyl group;

R 2 is a methyl group; and

A, B, C, or D is independently carbon;

or a non-toxic salt thereof.

2. The 1,2,4-triazole derivative according to claim 1 , which is selected from the group consisting of:

1-(4-methanesulfonylphenyl)-5-phenyl-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(4-bromophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3-bromophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(4-fluorophenyl )-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3,5-dichloro-4-methoxyphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(4-chlorophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3,4-dichlorophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3,4-dimethoxyphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3,4-difluorophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

1-(4-methanesulfonylphenyl)-5-(4-methoxyphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3,4-dimethoxyphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

1-(4-methanesulfonylphenyl)-5-p-tolyl-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3,4-dimethylphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3-chloro-4-methylphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(4-chloro-3-methylphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3-chloro-4-methoxyphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(4-chloro-3-methoxyphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3-fluoro-4-methylphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(4-fluoro-3-methylphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3-fluoro-4-methoxyphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

1-(4-methanesulfonylphenyl)-3-trifluoromethyl-5-(4-trifluoromethylphenyl)-1H-[1,2,4]triazole;

5-(4-ethoxyphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

1-(4-methanesulfonylphenyl)-5-(4-trifluoromethoxyphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(4-t-butylphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(4-cyanophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-[4-(N-methylamino)phenyl]-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-[4-(N,N-dimethylamino)phenyl]-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(4-aminophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3-trifluoromethylphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3-methoxyphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

1-(4-methanesulfonylphenyl)-5-m-tolyl-3-trifluoromethyl-1H-[1,2,4]triazole;

1-(4-methanesulfonylphenyl)-5-o-tolyl-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(2-bromophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(2-methoxyphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(2,4-difluorophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(2,5-difluorophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(2,4,5-trifluorophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(2,3-dichlorophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(2,4-dichlorophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3,5-difluorophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3,5-dimethoxyphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(2,4-dimethoxyphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3,4,5-trimethoxyphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(2-fluoro-4-trifluoromethylphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(2-chloro-4-nitrophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(2,4-dichloro-5-fluorophenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-(3-fluoro-4-methylphenyl)-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-benzo[1,3]dioxol-5-yl-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

3-[2-(4-methanesulfonylphenyl)-5-trifluoromethyl-2H-[1,2,4]triazol-3-yl]pyridine;

4-[2-(4-methanesulfonylphenyl)-5-trifluoromethyl-2H-[1,2,4]triazol-3-yl]pyridine;

5-cyclohexyl-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-cyclohexen-1-yl-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

5-styryl-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole; and

5-[2-(4-methoxyphenyl)-vinyl]-1-(4-methanesulfonylphenyl)-3-trifluoromethyl-1H-[1,2,4]triazole;

or a non toxic salt thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 2, 2008
From: CJ CORPORATION
To: CJ CHEILJEDANG CORPORATION
Reel/Frame 020891/0901 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 27, 2003
From: CHO, IL HWAN; PARK, HYUN JUNG; NOH, JI YOUNG; RYU, HYUNG CHUL; PARK, SANG WOOK; JUNG, SUNG HAK; LEE, SUNG HAK; KIM, JONG HOON; LIM, JEE WOONG; LYU, CHUN SEON; KIM, DAL HYUN; KIM, YOUNG HOON; YEON, KYU JEONG; CHAE, MYEONG YUN; MIN, IN KI; JIN, HAE TAK; KANG, KYOUNG RAE
To: CJ CORP.
Reel/Frame 014266/0455 →