Phenylcarbamate compound and muscle relaxant containing the same

Abstract

A novel phenylcarbamate compound and a pharmaceutical composition containing the same are provided. More specifically, a novel phenylcarbamate compound, a composition for muscle relaxation containing the phenylcarbamate compound as an active ingredient, and a method of muscle relaxation comprising administering a therapeutically effective amount of the phenylcarbamate compound, are provided.

1 .- 17 . (canceled) 
     
     
         18 . A compound represented by the following Chemical Formula 1 or a pharmaceutically acceptable salt thereof: 
       
         
           
           
               
               
           
         
         wherein 
         X is chlorine, fluorine or iodine; 
         n is an integer from 1 to 5; 
         R 1  is a C 1 -C 4  linear or branched alkyl group; 
         A is hydrogen or a carbamoyl represented by 
       
       
         
           
           
               
               
           
         
         B is hydrogen or a carbamoyl represented by 
       
       
         
           
           
               
               
           
         
       
       and
 R 2  and R 3  are the same as or different from each other, and independently selected from the group consisting of hydrogen, a C 1 -C 4  linear or branched alkyl group, a C 3 -C 8  cycloalkyl group, 
 and benzyl group, and 
 with the proviso that: 
 A is H and B is a carbamoyl moiety; or A is a carbamoyl moiety and B is H, 
 if X is chlorine and n is 1, R 1  is methyl, isopropyl or butyl, and 
 if A is the carbamoyl represented by 
 
       
         
           
           
               
               
           
         
       
       B is hydrogen, R 1  is ethyl, and n is 2 at the same time, two X are located at the 2 and 3 positions of the aromatic ring. 
     
     
         19 . The compound or the pharmaceutically acceptable salt thereof according to  claim 18 , wherein the compound is in the form of racemate, enantiomer, diastereomer, a mixture of enantiomer, or a mixture of diastereomer. 
     
     
         20 . The compound or the pharmaceutically acceptable salt thereof according to  claim 18 , wherein
 X is chlorine, fluorine or iodine;   n is 1 or 2;   R 1  is methyl group, ethyl group, isopropyl group, or butyl group;   A is hydrogen or a carbamoyl represented by   
       
         
           
           
               
               
           
         
         B is hydrogen or a carbamoyl represented by 
       
       
         
           
           
               
               
           
         
         R 2  and R 3  are the same as or different from each other, and independently selected from the group consisting of hydrogen, methyl group, propyl group, isopropyl group, cyclopropyl group, cyclohexyl group, bicycloheptane group, and benzyl group, and 
         with the proviso that: 
         A is H and B is a carbamoyl moiety; or A is a carbamoyl moiety and B is H, 
         if X is chlorine and n is 1, R 1  is methyl, isopropyl or butyl, and 
         if A is the carbamoyl represented by 
       
       
         
           
           
               
               
           
         
       
       B is hydrogen, R 1  is ethyl, and n is 2 at the same time, two X are located at the 2 and 3 positions of the aromatic ring. 
     
     
         21 . A pharmaceutical composition containing a compound represented by the following Chemical Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient: 
       
         
           
           
               
               
           
         
         wherein 
         X is chlorine, fluorine or iodine; 
         n is an integer from 1 to 5; 
         R 1  is a C 1 -C 4  linear or branched alkyl group; 
         A is hydrogen or a carbamoyl represented by 
       
       
         
           
           
               
               
           
         
         B is hydrogen or a carbamoyl represented by 
       
       
         
           
           
               
               
           
         
         R 2  and R 3  are the same as or different from each other, and independently selected from the group consisting of hydrogen, a C 1 -C 4  linear or branched alkyl group, a C 3 -C 8  cycloalkyl group, and benzyl group; and 
         with the proviso that: 
         A is H and B is a carbamoyl moiety; or A is a carbamoyl moiety and B is H, 
         if X is chlorine and n is 1, R 1  is methyl, isopropyl or butyl, and 
         if A is the carbamoyl represented by 
       
       
         
           
           
               
               
           
         
       
       B is hydrogen, R 1  is ethyl, and n is 2 at the same time, two X are located at the 2 and 3 positions of the aromatic ring. 
     
     
         22 . The pharmaceutical composition according to  claim 21 , wherein
 X is chlorine, fluorine or iodine;   n is 1 or 2;   R 1  is methyl group, ethyl group, isopropyl group, or butyl group;   A is hydrogen or a carbamoyl represented by   
       
         
           
           
               
               
           
         
         B is hydrogen or a carbamoyl represented by 
       
       
         
           
           
               
               
           
         
         R 2  and R 3  are the same as or different from each other, and independently selected from the group consisting of hydrogen, methyl group, propyl group, isopropyl group, cyclopropyl group, cyclohexyl group, bicycloheptane group, and benzyl group, and with the proviso that: 
         A is H and B is a carbamoyl moiety; or A is a carbamoyl moiety and B is H, 
         if X is chlorine and n is 1, R 1  is methyl, isopropyl or butyl, and 
         if A is the carbamoyl represented by 
       
       
         
           
           
               
               
           
         
       
       B is hydrogen, R 1  is ethyl, and n is 2 at the same time, two X are located at the 2 and 3 positions of the aromatic ring. 
     
     
         23 . The pharmaceutical composition according to  claim 21 , wherein the compound is in the form of racemate, enantiomer, diastereomer, a mixture of enantiomer, or a mixture of diastereomer. 
     
     
         24 . A method of muscle relaxation comprising administering a therapeutically effective amount of a compound represented by the following Chemical Formula 1 or a pharmaceutically acceptable salt thereof to a subject in need of muscle relaxation:
 [Chemical Formula 1]   
       
         
           
           
               
               
           
         
         wherein 
         X is chlorine, fluorine or iodine; 
         n is an integer from 1 to 5; 
         R 1  is a C 1 -C 4  linear or branched alkyl group; 
         A is hydrogen or a carbamoyl represented by 
       
       
         
           
           
               
               
           
         
         B is hydrogen or a carbamoyl represented by 
       
       
         
           
           
               
               
           
         
         R 2  and R 3  are the same as or different from each other, and independently selected from the group consisting of hydrogen, a C 1 -C 4  linear or branched alkyl group, a C 3 -C 8  cycloalkyl group, and benzyl group; and 
         with the proviso that: 
         A is H and B is a carbamoyl moiety; or A is a carbamoyl moiety and B is H, 
         if X is chlorine and n is 1, R 1  is methyl, isopropyl or butyl, and 
         if A is the carbamoyl represented by 
       
       
         
           
           
               
               
           
         
         B is hydrogen, R 1  is ethyl, and n is 2 at the same time, two X are located at the 2 and 3 positions of the aromatic ring. 
       
     
     
         25 . The method according to  claim 24 , wherein
 X is chlorine, fluorine or iodine;   n is 1 or 2;   R 1  is methyl group, ethyl group, isopropyl group, or butyl group;   A is hydrogen or a carbamoyl represented by   
       
         
           
           
               
               
           
         
         B is hydrogen or a carbamoyl represented by 
       
       
         
           
           
               
               
           
         
         R 2  and R 3  are the same as or different from each other, and independently selected from the group consisting of hydrogen, methyl group, propyl group, isopropyl group, cyclopropyl group, cyclohexyl group, bicycloheptane group, and benzyl group, and 
         with the proviso that: 
         A is H and B is a carbamoyl moiety; or A is a carbamoyl moiety and B is H, 
         if X is chlorine and n is 1, R 1  is methyl, isopropyl or butyl, and 
         if A is the carbamoyl represented by 
       
       
         
           
           
               
               
           
         
       
       B is hydrogen, R 1  is ethyl, and n is 2 at the same time, two X are located at the 2 and 3 positions of the aromatic ring. 
     
     
         26 . The method according to  claim 24 , wherein the compound is in the form of racemate, enantiomer, diastereomer, a mixture of enantiomer, or a mixture of diastereomer. 
     
     
         27 . A method of treating a disease associated with muscle spasm comprising administering a therapeutically effective amount of a compound represented by the following Chemical Formula 1 or a pharmaceutically acceptable salt thereof to a subject in need of the treatment of a disease associated with muscle spasm selected from the group consisting of herniation of intervertebral disk, vascular disorders of the spinal cord, spastic spinal paralysis, cervical spondylosis, cerebral palsy, sequelae of injuries, and spinocerebellar degeneration:
 [Chemical Formula 1]   
       
         
           
           
               
               
           
         
         wherein 
         X is chlorine, fluorine or iodine; 
         n is an integer from 1 to 5; 
         R 1  is a C 1 -C 4  linear or branched alkyl group; 
         A is hydrogen or a carbamoyl represented by 
       
       
         
           
           
               
               
           
         
         B is hydrogen or a carbamoyl represented by 
       
       
         
           
           
               
               
           
         
         R 2  and R 3  are the same as or different from each other, and independently selected from the group consisting of hydrogen, a C 1 -C 4  linear or branched alkyl group, a C 3 -C 8  cycloalkyl group, and benzyl group; and 
         with the proviso that: 
         A is H and B is a carbamoyl moiety; or A is a carbamoyl moiety and B is H, 
         if X is chlorine and n is 1, R 1  is methyl, isopropyl or butyl, and 
         if A is the carbamoyl represented by 
       
       
         
           
           
               
               
           
         
       
       B is hydrogen, R 1  is ethyl, and n is 2 at the same time, two X are located at the 2 and 3 positions of the aromatic ring. 
     
     
         28 . The method according to  claim 27 , wherein
 X is chlorine, fluorine or iodine;   n is 1 or 2;   R 1  is methyl group, ethyl group, isopropyl group, or butyl group;   A is hydrogen or a carbamoyl represented by   
       
         
           
           
               
               
           
         
         B is hydrogen or a carbamoyl represented by 
       
       
         
           
           
               
               
           
         
         R 2  and R 3  are the same as or different from each other, and independently selected from the group consisting of hydrogen, methyl group, propyl group, isopropyl group, cyclopropyl group, cyclohexyl group, bicycloheptane group, and benzyl group, and 
         with the proviso that: 
         A is H and B is a carbamoyl moiety; or A is a carbamoyl moiety and B is H, 
         if X is chlorine and n is 1, R 1  is methyl, isopropyl or butyl, and 
         if A is the carbamoyl represented by 
       
       
         
           
           
               
               
           
         
       
       B is hydrogen, R 1  is ethyl, and n is 2 at the same time, two X are located at the 2 and 3 positions of the aromatic ring. 
     
     
         29 . The method according to  claim 27 , wherein the compound is in the form of racemate, enantiomer, diastereomer, a mixture of enantiomer, or a mixture of diastereomer.