Epothilone derivatives, a process for their production thereof and their use

Abstract

The present invention relates to epothilon derivatives, processes for their production and their use in the manufacture of medicaments and plant protection agents.

1 - 17 . (cancelled)  
     
     
         18 . A compound of formula:  
       
         
           
           
               
               
           
         
       
       wherein 
 R 1  is a H atom or a C 1 - to C 8 -alkyl group,  
 X-Y is a group of the formula —CH 2 CH(OP)— or —CH═CH—,  
 P is a protecting group, and  
 each R is independently a C 1 - to C 8 -alkyl group or a C 2 - to C 6 -alkenyl group.  
 
     
     
         19 . The compound of  claim 18  wherein at least one R is a C 1 - to C 6 -alkyl group.  
     
     
         20 . The compound of  claim 18  wherein at least one R is a C 1 - to C 4 -alkyl group.  
     
     
         21 . The compound of  claim 18  wherein at least one R is a C 2 - to C 6 -alkenyl group.  
     
     
         22 . The compound of  claim 18  wherein at least one R is a C 2 - to C 4 -alkenyl group.  
     
     
         23 . The compound of  claim 18  wherein R 1  is a H atom or a C 1 - to C 6 -alkyl group.  
     
     
         24 . The compound of  claim 18  wherein R 1  is a H atom or a methyl group.  
     
     
         25 . A process for preparing a compound of the formula  
       
         
           
           
               
               
           
         
         wherein 
 R 1  is a H atom or a C 1 - to C 8 -alkyl group,  
 X-Y is a group of the formula —CH 2 CH(OP)— or —CH═CH—,  
 P is a protecting group, and  
 each R is independently a C 1 - to C 8 -alkyl group or a C 2 - to C 6 -alkenyl group;  
 comprising: reacting a compound of the formula 2:  
                     
 with a compound of the formula HC[B(OR) 2 ] 3 .  
 
       
     
     
         26 . The process according to  claim 25  wherein the compound of the formula HC[B(OR) 2 ] 3  is tris(ethylenedioxyboryl)methane.  
     
     
         27 . The process according to  claim 25  wherein the compound of the formula 2 and the compound of the formula HC[B(OR) 2 ] 3  are reacted in the presence of a strong base.  
     
     
         28 . The process according to  claim 27  wherein the strong base is a C 1 -C 4 -alkyl lithium compound or a di-C 1 -C 4 -alkylamine lithium compound.  
     
     
         29 . The process according to  claim 28  wherein the strong base is butyllithium or dimethylamine lithium compound.  
     
     
         30 . The process according to  claim 25  wherein the compound of the formula II and the compound of the formula HC[B(OR) 2 ] 3  are reacted at a temperature of less than about −30° C.