Method for treating pain

Abstract

The present invention provides pharmaceutical compositions useful in a method for treating neuropathic pain, said method comprising administration of a pain-ameliorating effective amount of the compound according to formula I wherein R is an alk(en)yl group, R1 is an alkylen(yl) group, n is 0 or 1 and Ar is a carbocyclic aryl group.

1 . A pharmaceutical composition comprising, as the active compound, a pain-ameliorating effective amount of a N-alk(en)yl carbocyclic aryl alk(yl)enyl-carbo-serotonin adduct.  
   
   
       2 . The composition of  claim 1  wherein said compound is represented by formula I  
     
       
         
         
             
             
         
       
     
     wherein R is an alk(en)yl group, R 1  is an alkylen(yl) group, n is 0 or 1 and Ar is a carbocyclic aryl group.  
   
   
       3 . The composition of  claim 2  wherein R is an alkyl or alkenyl group comprising from 1 to 7 carbon atoms and R 1  is an alkylene comprising from 3 to 6 carbon atoms and Ar is selected from the group consisting of phenyl, naphthyl and biphenyl and lower alkyl substituted derivatives thereof.  
   
   
       4 . The composition of  claim 3  wherein R is selected from the group consisting of CH 3 CH 2 , CH 3 CH 2 CH 2 , CH 3 CH 2 CH 2 CH 2 , CH 3 CHCH and CH 3 CHCHCH 2 CHCHCH 2  and R 1  is selected from the group consisting of CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2  and CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 .  
   
   
       5 . The composition of  claim 3  wherein the compound of formula I is selected from the group consisting of  
     
       
         
         
             
             
         
       
     
   
   
       6 . A method for treating neuropathic pain, said method comprising administration of a pain-ameliorating effective amount of N-alk(en)yl carbocyclic aryl alk(yl)enyl-carbo-serotonin adduct.  
   
   
       7 . The method of  claim 6  wherein said compound is represented by formula I  
     
       
         
         
             
             
         
       
     
     wherein R is an alk(en)yl group, R 1  is an alkylen(yl) group, n is 0 or 1 and Ar is a carbocyclic aryl group.  
   
   
       8 . The method of  claim 7  wherein R is an alkyl or alkenyl group comprising from 1 to 7 carbon atoms and R 1  is an alkylene comprising from 3 to 6 carbon atoms and Ar is selected from the group consisting of phenyl, naphthyl and biphenyl and lower alkyl substituted derivatives thereof.  
   
   
       9 . The method of  claim 7  wherein R is selected from the group consisting of CH 3 CH 2 , CH 3 CH 2 CH 2 , CH 3 CH 2 CH 2 CH 2 , CH 3 CHCH and CH 3 CHCHCH 2 CHCHCH 2  and R 1  is selected from the group consisting of CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2  and CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 .  
   
   
       10 . The method of  claim 7  wherein the compound of formula I may be selected from the group consisting of  
     
       
         
         
             
             
         
       
     
   
   
       11 . A method comprising binding a N-alk(en)yl carbocyclic aryl alk(yl)enyl-carbo-serotonin adduct to the TRPV1 channel of a warm-blooded animal, such as a human being, so as to beneficially inhibit the activity of said channel to thereby ameliorate pain.  
   
   
       12 . The method of  claim 11  wherein said compound is represented by formula I  
     
       
         
         
             
             
         
       
     
     wherein R is an alk(en)yl group, R 1  is an alkylen(yl) group, n is 0 or 1 and Ar is a carbocyclic aryl group.  
   
   
       13 . The method of  claim 12  wherein R is an alkyl or alkenyl group comprising from 1 to 7 carbon atoms and R 1  is an alkylene comprising from 3 to 6 carbon atoms and Ar is selected from the group consisting of phenyl, naphthyl and biphenyl and lower alkyl substituted derivatives thereof.  
   
   
       14 . The method of  claim 13  wherein R is selected from the group consisting of CH 3 CH 2 , CH 3 CH 2 CH 2 , CH 3 CH 2 CH 2 CH 2 , CH 3 CHCH and CH 3 CHCHCH 2 CHCHCH 2 and R 1  is selected from the group consisting of CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2  and CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 .  
   
   
       15 . The method of  claim 13  wherein the compound of formula I may be selected from the group consisting of  
     
       
         
         
             
             
         
       
     
   
   
       16 . A method comprising binding a N-alk(en)yl carbocyclic aryl alk(yl)enyl-carbo-serotonin adduct to the fatty acid amide hydrolase of a warm-blooded animal, such as a human being, so as to activate said receptor to enhance endocannabinoid levels in said animal to thereby ameliorate pain.  
   
   
       17 . The method of  claim 1  wherein said compound is represented by formula I  
     
       
         
         
             
             
         
       
     
     wherein R is an alk(en)yl group, R 1  is an alkylen(yl) group, n is 0 or 1 and Ar is a carbocyclic aryl group.  
   
   
       18 . The method of  claim 17  wherein R is an alkyl or alkenyl group comprising from 1 to 7 carbon atoms and R 1  is an alkylene comprising from 3 to 6 carbon atoms and Ar is selected from the group consisting of phenyl, naphthyl and biphenyl and lower alkyl substituted derivatives thereof.  
   
   
       19 . The method of  claim 18  wherein R is selected from the group consisting of CH 3 CH 2 , CH 3 CH 2 CH 2 , CH 3 CH 2 CH 2 CH 2 , CH 3 CHCH and CH 3 CHCHCH 2 CHCHCH 2  R 1  is selected from the group consisting of CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2  and CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 .  
   
   
       20 . The method of  claim 18  wherein the compound of formula I is selected from the group consisting of  
     
       
         
         
             
             
         
       
     
   
   
       21 . A compound according to formula I  
     
       
         
         
             
             
         
       
     
     wherein R is an alk(en)yl group, R 1  is an alkylen(yl) group, n is 0 or 1 and Ar is a carbocyclic aryl group.  
   
   
       22 . The compound of  claim 21  wherein R is an alkyl or alkenyl group comprising from 1 to 7 carbon atoms, R is an methyl alkylene or methyl alkenyl group selected from the group consisting of R 1  is an alkylene group consisting from 3 to 6 carbon atoms and Ar is selected from the group consisting of phenyl, naphthyl and biphenyl and C 1  to C 4  alkyl substituted derivatives thereof.  
   
   
       23 . The compound of  claim 22  wherein R is selected from the group consisting of CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 , and R 1  is selected from the group consisting of R is an methyl alkylene and methyl alkenyl group such as CH 3 CH 2 , CH 3 CH 2 CH 2 , CH 3 CH 2 CH 2 CH 2 , CH 3 CHCH and CH 3 CHCHCH 2 CHCHCH 2 .  
   
   
       24 . The compound of  claim 22  wherein said compound is selected from the group consisting of  
     
       
         
         
             
             
         
       
     
     to the TRPV1 channel of a warm-blooded animal so as to beneficially inhibit the activity of said channel to activation to thereby ameliorate pain.  
   
   
       25 . A method of treating neuropathic pain, said method comprising administration of a pain-ameliorating amount of the composition of  claim 1  to a warm-blooded animal to thereby bind the N-alk(en)yl carbocyclic aryl alk(yl)enyl-carbo-serotonin adduct to the TRPV1 channel so as to beneficially inhibit the activity of said channel and activate the cannabinoid receptor to enhance endocannabinoid levels in said animal to thereby ameliorate pain.