Novel isonitramine compound and composition containing same for preventing or treating metabolic diseases

Abstract

Provided are a pharmaceutical composition for preventing or treating metabolic diseases and a health food for alleviating metabolic diseases, each of which the pharmaceutical composition and the health food includes, a stereoisomer of isonitramine or a derivative thereof, or a racemic mixture of the stereoisomers, wherein such a compound exhibits effects of inhibiting fat content or differentiation of an adipocyte, inhibiting activity of a carbohydrate metabolism enzyme, protecting pancreas, inhibiting blood sugar, and promoting insulin secretion, and thus can be favorably utilized in the treatment of metabolic diseases, such as obesity, diabetes, and hyperlipidemia.

1 . A pharmaceutical composition for preventing or treating a metabolic disease, the pharmaceutical composition comprising, as an active ingredient, a stereoisomer represented by Formula 1 or a racemic mixture thereof: 
       
         
           
           
               
               
           
         
         wherein, in Formula 1, 
         X is selected from the group consisting of a hydrogen atom, a C 1 -C 10  alkyl group, an acyl group, an allyl group, and a benzyl group, wherein, when X is an allyl group, one or more halogen may be substituted for the unsaturated carbon, or when X is 
       
       
         
           
           
               
               
           
         
       
       R 1  to R 5  are each independently a hydrogen atom, a nitro group, a halogen atom, a cyano group, a hydroxyl group, a dimethylamino group, a methylsulfonylamide group, a trifluoromethyl group, a C 1 -C 3  alkyl group, a C 1 -C 3  alkoxy group, a vinyl group, an aryl group, a phenoxy group, or a benzoxy group;
 Y is selected from the group consisting of a hydrogen atom, a C 1 -C 10  alkyl group, an acyl group, an allyl group, and a benzyl group, wherein, when Y is an allyl group, one or more halogen may be substituted for the unsaturated carbon, or when Y is 
 
       
         
           
           
               
               
           
         
       
       R 1  to R 5  are each independently a hydrogen atom, a nitro group, a halogen atom, a cyano group, a hydroxyl group, a dimethylamino group, a methylsulfonylamide group, a trifluoromethyl group, a C 1 -C 3  alkyl group, a C 1 -C 3  alkoxy group, a vinyl group, an aryl group, a phenoxy group, or a benzoxy group; and
 carbon atoms at the 6 th  position and the 7 th  position are each a chiral center. 
 
     
     
         2 . The pharmaceutical composition of  claim 1 , wherein the metabolic disease is selected from the group consisting of obesity, diabetes, hyperlipidemia, hypertriglyceridemia, liver disease, arteriosclerosis, stroke, myocardial infarction, cardiovascular disease, hyperglycemia, insulin resistance, and hyperinsulinemia. 
     
     
         3 . A health food for preventing or treating a metabolic disease, the health food comprising, as an active ingredient, a stereoisomer represented by Formula 1 or a racemic mixture thereof: 
       
         
           
           
               
               
           
         
         wherein, in Formula 1, 
         X is selected from the group consisting of a hydrogen atom, a C 1 -C 10  alkyl group, an acyl group, an allyl group, and a benzyl group, wherein, when X is an allyl group, one or more halogen may be substituted for the unsaturated carbon, or when X is 
       
       
         
           
           
               
               
           
         
       
       R 1  to R 5  are each independently a hydrogen atom, a nitro group, a halogen atom, a cyano group, a hydroxyl group, a dimethylamino group, a methylsulfonylamide group, a trifluoromethyl group, a C 1 -C 3  alkyl group, a C 1 -C 3  alkoxy group, a vinyl group, an aryl group, a phenoxy group, or a benzoxy group;
 Y is selected from the group consisting of a hydrogen atom, a C 1 -C 10  alkyl group, an acyl group, an allyl group, and a benzyl group, wherein, when Y is an allyl group, one or more halogen may be substituted for the unsaturated carbon, or when Y is 
 
       
         
           
           
               
               
           
         
       
       R 1  to R 5  are each independently a hydrogen atom, a nitro group, a halogen atom, a cyano group, a hydroxyl group, a dimethylamino group, a methylsulfonylamide group, a trifluoromethyl group, a C 1 -C 3  alkyl group, a C 1 -C 3  alkoxy group, a vinyl group, an aryl group, a phenoxy group, or a benzoxy group; and
 carbon atoms at the 6 th  position and the 7 th  position are each a chiral center. 
 
     
     
         4 - 9 . (canceled)