Novel Pharmaceutical Intermediates and Methods for Preparing the Same

Abstract

A pharmaceutical intermediate including a first indole moiety which is associated with an optionally carboxylated hexahydroazepino moiety, an optionally carboxylated azonane moiety, or a second, optionally carboxylated indole moiety, having an alkyl, allyl, phenylallyl, cinnamyl, alkenyl, and/or alkyl-alkenyl substituent pendant from a nitrogen atom of the same.

1 . A pharmaceutical intermediate comprising the structure of formula I: 
       
         
           
           
               
               
           
         
         wherein:
 R 1 -R 4 , R 6 -R 8 , and R 10 -R 14  are each independently selected from the group consisting of H; OH; and an alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, aryl, alkaryl, aralkyl, alkoxy, alkanoyl, aroyl, alkenyl, and/or alkyl-alkenyl group containing approximately 1 to approximately 25 carbon atom(s); 
 R 5  is selected from the group consisting of an alkyl, allyl, phenylallyl, cinnamyl, alkenyl, and/or alkyl-alkenyl group containing approximately 1 to approximately 25 carbon atom(s); 
 R 9  is selected from the group consisting of H; OH; and an alcohol, ether, ester, amide, hydrazide, cyanide, and/or ketone group containing approximately 1 to approximately 25 carbon atom(s); and 
 X 1 -X 2  are each independently selected from the group consisting of N, O, and S. 
 
       
     
     
         2 . The pharmaceutical intermediate according to  claim 1 , comprising the structure of formula II: 
       
         
           
           
               
               
           
         
         wherein:
 R 1  is selected from the group consisting of an alkyl, allyl, phenylallyl, cinnamyl, alkenyl, and/or alkyl-alkenyl group containing approximately 1 to approximately 25 carbon atom(s); 
 R 2  is selected from the group consisting of H; OH; and an alcohol, ether, ester, amide, hydrazide, cyanide, and/or ketone group containing approximately 1 to approximately 25 carbon atom(s); and 
 R 3  is selected from the group consisting of H; OH; and an alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, aryl, alkaryl, aralkyl, alkoxy, alkanoyl, aroyl, alkenyl, and/or alkyl-alkenyl group containing approximately 1 to approximately 25 carbon atom(s). 
 
       
     
     
         3 . The pharmaceutical intermediate according to  claim 1 , comprising the structure of formula III: 
       
         
           
           
               
               
           
         
         wherein:
 wherein R 1  is selected from the group consisting of an alkyl, allyl, phenylallyl, cinnamyl, alkenyl, and/or alkyl-alkenyl group containing approximately 1 to approximately 25 carbon atom(s). 
 
       
     
     
         4 . The pharmaceutical intermediate according to  claim 1 , comprising the structure of formula IV: 
       
         
           
           
               
               
           
         
         wherein:
 R 1 -R 3  are each independently selected from the group consisting of H, CH 3 , and C 6 H 5 . 
 
       
     
     
         5 - 18 . (canceled)