Method for treating liver disease by administering pharmaceutical composition comprising catechol derivative

Abstract

The present invention relates to a compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt thereof. The compound according to the present invention can be usefully used for the prevention or treatment of autophagy-related diseases.

1 . A method of treating liver diseases in a subject in need thereof, the method comprising administering to the subject a therapeutically effective amount of a pharmaceutical composition comprising a compound represented by Chemical Formula 1 below, or a pharmaceutically acceptable salt thereof: 
       
         
           
           
               
               
           
         
         wherein, in Chemical Formula 1, 
         R 1  and R 2  are each independently C 1-4  alkyl, or R 1  and R 2  are connected together to form C 1-4  alkylene, 
         R 3  is C 1-4  alkyl, C 1-4  alkyl substituted with C 5-10  heteroaryl, C 5-10  aryl, or C 5-10  heteroaryl, 
         X is CH, or N, and 
         Y is NH, or O. 
       
     
     
         2 . The method according to  claim 1 , wherein R 1  and R 2  are methyl, or R 1  and R 2  are connected together to form methylene or ethylene. 
     
     
         3 . The method according to  claim 1 , wherein R 3  is methyl, ethyl, isopropyl, isobutyl, pyridinylmethyl, phenyl, or pyridine. 
     
     
         4 . The method according to  claim 1 , wherein
 R 1  and R 2  are each independently C 1-4  alkyl, or R 1  and R 2  are connected together to form C 1-4  alkylene,   R 3  is C 1-4  alkyl, C 1-4  alkyl substituted with C 5-10  heteroaryl, C 5-10  aryl, or C 5-10  heteroaryl,   X is CH, and   Y is NH.   
     
     
         5 . The method according to  claim 1 , wherein
 R 1  and R 2  are connected together to form C 1-4  alkylene,   R 3  is C 1-4  alkyl, or C 6-10  aryl,   X is N, and   Y is NH.   
     
     
         6 . The method according to  claim 1 , wherein
 R 1  and R 2  are methyl, or R 1  and R 2  are connected together to form methylene,   R 3  is isopropyl, isobutyl, or phenyl,   X is CH, and   Y is NH.   
     
     
         7 . The method according to  claim 1 , wherein the compound is any one selected from the group consisting of:
 1) 5-(3,4-dimethoxyphenyl)-N-isopropylthiophene-2-carboxamide,   2) 5-(benzo[d][1,3]dioxol-5-yl)-N-isopropylthiophene-2-carboxamide,   3) 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-isopropylthiophene-2-carboxamide,   4) 5-(3,4-dimethoxyphenyl)-N-isobutylthiophene-2-carboxamide,   5) 5-(benzo[d][1,3]dioxol-5-yl)-N-isobutylthiophene-2-carboxamide,   6) 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-isobutylthiophene-2-carboxamide,   7) 5-(3,4-dimethoxyphenyl)-N-phenylthiophene-2-carboxamide,   8) 5-(benzo[d][1,3]dioxol-5-yl)-N-phenylthiophene-2-carboxamide,   9) 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-phenylthiophene-2-carboxamide,   10) 5-(benzo[d][1,3]dioxol-5-yl)-N-(pyridin-2-yl)thiophene-2-carboxamide,   11) 5-(benzo[d][1,3]dioxol-5-yl)-N-(pyridin-2-ylmethyl)thiophene-2-carboxamide,   12) 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-(pyridin-2-ylmethyl)thiophene-2-carboxamide,   13) 2-(benzo[d][1,3]dioxol-5-yl)-N-isopropylthiazole-5-carboxamide,   14) 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-isopropylthiazole-5-carboxamide,   15) 2-(benzo[d][1,3]dioxol-5-yl)-N-isobutylthiazole-5-carboxamide,   16) 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-isobutylthiazole-5-carboxamide,   17) 2-(benzo[d][1,3]dioxol-5-yl)-N-phenylthiazole-5-carboxamide,   18) 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N-phenylthiazole-5-carboxamide,   19) methyl 5-(benzo[d][1,3]dioxol-5-yl)thiophene-2-carboxylate, and   20) ethyl 2-(benzo[d][1,3]dioxol-5-yl)thiazole-5-carboxylate.   
     
     
         8 . The method according to  claim 1 , wherein the liver diseases are liver fibrosis, liver cirrhosis, hepatitis, alcoholic liver disease, fatty liver, or non-alcoholic steatohepatitis.