Epoxycarboxamide compound, azide compound, and amino alcohol compound, and process for preparing alpha-keto amide compound using them

Abstract

The present invention is to provide manufacturing intermediates which can be led to useful α-ketoamide compounds having protease-inhibiting activity extremely economically and stereoselectively, and to provide epoxycarboxamide compounds, azide compounds and amino alcohol compounds represented by the following formulae: wherein R 1 and R 2 each represents alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group; R 3 represents alkyl group, alkenyl group, aromatic hydrocarbon group, heterocyclic group, R 6 —O— or R 7 —N(R 8 )—; where R 6 represents alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group; R 7 and R 8 each represents hydrogen atom, alkyl group, alkenyl group, aromatic hydrocarbon group or heterocyclic group, and, R 4 and R 5 represent the same groups as R 7 and R 8 , respectively, and R 4 and R 5 optionally form a ring together; and X represents —O— or —N(R 9 )—, where R 9 represents hydrogen atom or alkyl group, and X optionally forms a ring together with R 4 or R 5 , and processes for preparing α-keto amide compound using the same.

1 . An epoxycarboxamide compound represented by the formula (I):  
       
         
           
           
               
               
           
         
         wherein R 1  represents a substituted or unsubstituted, straight, branched or cyclic alkyl group, a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group, where the substituent for the alkyl group, aromatic hydrocarbon group or heterocyclic group is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group or a substituted or unsubstituted arylthio group; and R 2  represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group, where the substituent for the aromatic hydrocarbon group or heterocyclic group is a hydroxy group, an oxo group, a halogen atom, a substituted or unsubstituted, straight, branched or cyclic alkenyl group having 2 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group, a nitro group, a substituted or unsubstituted amino group, a substituted or unsubstituted sulfonyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, an acyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted carbamoyl group, a substituted sulfonamide group, a substituted amide group, a mercapto group, a cyano group or a methylenedioxy group.  
       
     
     
         2 . The epoxycarboxamide compound according to  claim 1 , wherein the compound represented by the formula (I) is a compound represented by the following formula:  
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  have the same meanings as defined above.  
       
     
     
         3 . The epoxycarboxamide compound according to  claim 1 , wherein the compound represented by the formula (I) is a compound represented by the following formula:  
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  have the same meanings as defined above.  
       
     
     
         4 . The epoxycarboxamide compound according to  claim 1 , wherein the compound represented by the formula (I) is a compound represented by the following formula:  
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  have the same meanings as defined above.  
       
     
     
         5 . The epoxycarboxamide compound according to  claim 1 , wherein the compound represented by the formula (I) is a compound represented by the following formula:  
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  have the same meanings as defined above.  
       
     
     
         6 . The epoxycarboxamide compound according to  claim 1 , wherein R 1  is an unsubstituted alkyl group.  
     
     
         7 . The epoxycarboxamide compound according to  claim 6 , wherein R 1  is an n-butyl group.  
     
     
         8 . The epoxycarboxamide compound according to  claim 1 , wherein R 2  is a methylenedioxyphenyl group.