Optically active pyranochromenyl phenol derivative and pharmaceutical composition comprising same

Abstract

The present invention relates to pyranochromenylphenol derivatives having different efficacies depending on the direction of optical activity and a pharmaceutical composition including the same, and in the pyranochromenylphenol derivatives, an R-enantiomer has excellent anti-diabetic efficacy by suppressing a rise in blood sugar and an S-enantiomer has excellent anti-obesity efficacy by suppressing an increase in body weight.

1 . An optically active pyranochromenylphenol compound of the following Chemical Formula (I), a pharmaceutically acceptable salt, or a solvate thereof: 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is a straight or branched C 2  to C 6  alkyl group unsubstituted or substituted by a straight or branched C 1  to C 5  alkyl group, a halogen atom, or a C 1  to C 5  thioalkyl group; 
         R 2  is a hydrogen atom, methyl, ethyl, methoxy, or ethoxy; and 
         R 3  and R 4  are each independently a hydrogen atom or a C 1  to C 2  alkyl group. 
       
     
     
         2 . The optically active pyranochromenylphenol compound, the pharmaceutically acceptable salt, or the solvate thereof of  claim 1 ,
 wherein R 1  is ethyl, n-propyl, isopropyl, n-butyl, 2-methylpropyl, n-pentyl, 2-methylbutyl, 3-methylbutyl, 2-ethylpropyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, or 2-ethylbutyl;   R 2  is a hydrogen atom; and   R 3  and R 4  are each methyl.   
     
     
         3 . The optically active pyranochromenylphenol compound, the pharmaceutically acceptable salt, or the solvate thereof of  claim 1 ,
 wherein R 1  is ethyl, n-propyl, isopropyl, n-butyl, 2-methylpropyl, n-pentyl, 2-methylbutyl, 3-methylbutyl, 2-ethylpropyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, or 2-ethylbutyl;   R 2  is methyl or methoxy; and   R 3  and R 4  are each methyl.   
     
     
         4 . The optically active pyranochromenylphenol compound, the pharmaceutically acceptable salt, or the solvate thereof of  claim 1 ,
 wherein the compound of Chemical Formula (I) is any one of the following compounds:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         5 . An optically active pyranochromenylphenol compound of the following Chemical Formula (II), a pharmaceutically acceptable salt, or a solvate thereof: 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is a straight or branched C 2  to C 6  alkyl group unsubstituted or substituted by a straight or branched C 1  to C 5  alkyl group, a halogen atom, or a C 1  to C 5  thioalkyl group; 
         R 2  is a hydrogen atom, methyl, ethyl, methoxy, or ethoxy; and 
         R 3  and R 4  are each independently a hydrogen atom or a C 1  to C 2  alkyl group. 
       
     
     
         6 . The optically active pyranochromenylphenol compound, the pharmaceutically acceptable salt, or the solvate thereof of  claim 5 ,
 wherein R 1  is ethyl, n-propyl, isopropyl, n-butyl, 2-methylpropyl, n-pentyl, 2-methylbutyl, 3-methylbutyl, 2-ethylpropyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, and 2-ethylbutyl;   R 2  is a hydrogen atom; and   R 3  and R 4  are each methyl.   
     
     
         7 . The optically active pyranochromenylphenol compound, the pharmaceutically acceptable salt, or the solvate thereof of  claim 5 ,
 wherein R 1  is ethyl, n-propyl, isopropyl, n-butyl, 2-methylpropyl, n-pentyl, 2-methylbutyl, 3-methylbutyl, 2-ethylpropyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, or 2-ethylbutyl;   R 2  is methyl or methoxy; and   R 3  and R 4  are each methyl.   
     
     
         8 . The optically active pyranochromenylphenol compound, the pharmaceutically acceptable salt, or the solvate thereof of  claim 5 ,
 wherein the compound of Chemical Formula (II) is any one of the following compounds:   
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         9 . A pharmaceutical composition for preventing or treating diabetes, comprising an optically active pyranochromenylphenol compound of the following Chemical Formula (I′), a pharmaceutically acceptable salt, or a solvate thereof: 
       
         
           
           
               
               
           
         
         wherein 
         R′ 1  is a straight or branched C 1  to C 6  alkyl group unsubstituted or substituted by a straight or branched C 1  to C 5  alkyl group, a halogen atom, or a C 1  to C 5  thioalkyl group; 
         R′ 2  is a hydrogen atom, methyl, ethyl, methoxy, or ethoxy; and 
         R′ 3  and R′ 4  are each independently a hydrogen atom or a C 1  to C 2  alkyl group. 
       
     
     
         10 . The pharmaceutical composition of  claim 9 , wherein the optically active pyranochromenylphenol compound of Chemical Formula (I′) is any one of the following compounds: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         11 . A pharmaceutical composition for preventing or treating obesity, comprising an optically active pyranochromenylphenol compound of the following Chemical Formula (II′), a pharmaceutically acceptable salt, or a solvate thereof: 
       
         
           
           
               
               
           
         
         wherein 
         R′ 1  is a substituted or unsubstituted straight or branched C 1  to C 6  alkyl group unsubstituted or substituted by a straight or branched C 1  to C 5  alkyl group, a halogen atom, or a C 1  to C 5  thioalkyl group; 
         R′ 2  is a hydrogen atom, methyl, ethyl, methoxy, or ethoxy; and 
         R′ 3  and R′ 4  are each independently a hydrogen atom or a C 1  to C 2  alkyl group. 
       
     
     
         12 . The pharmaceutical composition of  claim 10 , wherein the optically active pyranochromenylphenol compound of Chemical Formula (II′) is any one of the following compounds: