New aziridine derivatives and their preparation methods

Abstract

The present invention relates to new aziridine derivative that is represented by following general chemical formulae (la) or (lb), and to their preparation method. In the above mentioned chemical formulae, R 2 and R 3 can be same or different, and they are hydrogen, low-quality alkyl or cycloalkyl respectively; R 4 can be selected among hydrogen, alkyl, aril, or amino protective group, and amino protective group is, for example, (PH) 3 C, FMOC (9-fluorenylmethyl oxycarbonyl), alkoxycarbonyl, ariloxycarbonyl, aralkyloxycarbonyl and R 5 CO, R 5 SO 2 where R 5 is alkyl or aril or aralkyl.

1 . Aziridine derivatives of the following formula (Ia) or (Ib)  
     
       
         
         
             
             
         
       
     
     where R 2  and R 3  may be the same or different and, respectively represent hydrogen, low alkyl or cycloalkyl, and R 4  is selected from the group comprising hydrogen, alkyl, aryl, aralkyl and amino protecting group.  
   
   
       2 . The compound of  claim 1 , wherein said amino protecting group is selected from the group comprising a t-butoxycarbonyl, benzyloxycarbonyl, CH 3 —Ph—SO  2 —; (Ph) 3 C, and FMOC(9-fluorenylmethyloxycarbonyl).  
   
   
       3 . The compound of  claim 1 , wherein said R4 represents a t-butoxycarbonyl.  
   
   
       4 . A method for preparing aziridine derivatives of the following formula (Ia) or (Ib)  
     
       
         
         
             
             
         
       
     
     where R 2  and R 3  may be the same or different and respectively represent hydrogen, low alkyl or cycloalkyl, and R4 is selected from the group comprising hydrogen, alkyl, aryl, aralkyl and amino protecting group, 
 which is comprised of steps  
 (a) step of reacting the epoxy compound of formula (la) or (lb) in which R 2  and R 3  may be same or different and respectively represent hydrogen or low alkyl group, with NaN 3  to prepare 1-azido-2-hydroxy-3,4-isopropylidenebutane-2,3,4-triol derivatives of formula (2a) or (2b) in which R 2  and R 3  are same as defined above; and  
                     
 (b) step of forming amino ring structure of said compound of formula (2a) or (2b) and protecting by the amino protecting group to prepare said compound of formula (Ia) or (Ib).  
 
   
   
       5 . The method of  claim 4 , wherein said amino protecting group is selected from the group comprising a t-butoxycarbonyl, benzyloxycarbonyl, CH  3 —Ph—SO 2 —; (Ph) 3 C, and FMOC(9-fluorenylmethyloxycarbonyl).  
   
   
       6 . A method for preparing aziridine derivatives of the following formula (II)  
     
       
         
         
             
             
         
       
     
     where R 1  represents phenyl or phenyl substituted with halogen, alkyl, alkoxy, ROCOCH 2 O— in which R represents alkyl, or benzyloxy group; phenylthio or alkylthio; heteroaryl with more than one nitrogen, oxygen or sulfur atom; cycloalkyl or cycloalkyl substituted with alkyl group; alkyl or alkenyl with C 1 -C 4  carbon atoms; alkenyl substituted with a phenyl or OC 4 H 6 N—(CH 2 ) 2 —Ph—; heterocycle including a nitrogen and/or oxygen; and heterocycle including a nitrogen and/or oxygen with an alkyl group and R4 is selected from the group comprising hydrogen, alkyl, aryl, aralkyl and amino protecting group, 
 which is comprised of steps  
 (a) adding said R 1  to the compound of the following formula (I)  
                     
 where R 2  and R 3  may be the same or different and respectively represent hydrogen, low alkyl or cycloalkyl, and R4 is selected from the group comprising hydrogen, alkyl, aryl, aralkyl and amino protecting group, to prepare the compound of the following formula (6)  
                     
 where R 1 , R 2 , R 3  and R4 are same as defined above, removing hydroxyl protecting group of said compound of formula (6) to prepare the compound of the following formula (7)  
                     
 where R 1  and R4 are the same as defined above, and  
 (b) epoxidation of said compound of formula (7) to prepare the said compound of formula (II).  
 
   
   
       7 . The method of  claim 6 , wherein said R 1  represents a phenyl or phenylthio group.  
   
   
       8 . The method of  claim 6 , wherein said compound of the formula (I) is prepared by the method which is comprised of steps 
 (a) step of reacting the epoxy compound of formula (la) or (lb) in which R 2  and R 3  may be the same or different and respectively represent hydrogen or low alkyl group, with NaN 3  to prepare 1-azido-2-hydroxy-3,4-isopropylidenebutane-2,3,4-triol derivatives of formula (2a) or (2b) in which R 2  and R 3  are the same as defined above; and                          (b) step of forming amino ring structure of said compound of said compound of formula (2a) or (2b) and protecting group to prepare said compound of formula (I).    
   
   
       9 . The compound of  claim 2 , wherein said R4 represents a t-butoxycarbonyl.