Process for production of glucopyranosyloxypyrazole derivative

Abstract

The present invention relates to a method for preparing the glucopyranosyloxypyrazole derivatives which are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, diabetic complications, obesity or the like. A glucopyranosyloxypyrazole derivative can be easily and efficiently prepared by allowing a benzylpyrazole derivative represented by the general formula: wherein R 1 , R 2 , R 3 , R 4 and R 5 may be the same or different, for example each of them is a hydrogen atom, a halogen atom or an alkyl, alkoxy, arylmethyloxy group or the like, R 6 is an alkyl group, for example R 7 is a hydrogen atom or an alkyl, alkoxy, arylmethyloxy group or the like, to react with a compound represented by the general formula: wherein as an example, PG 1 is a pivaloyl group or the like, as an example, X 1 is a bromine atom or the like, therefore the present invention is extremely useful as a method for preparing pharmaceutical compounds.

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         4 . A method for preparing a glucopyranosyloxypyrazole derivative represented by the general formula: 
       
         
           
           
               
               
           
         
         wherein Q 1  is a group represented by the general formula: 
       
       
         
           
           
               
               
           
         
         in which PG 1  is an acetyl group, an arylcarbonyl group, a pivaloyl group or an arylmethyl group, and R 1 , R 2 , R 3 , R 4  and R 5  may be the same or different, each of them is a hydrogen atom, a halogen atom, a C 1-6  alkyl group, a haloC 1-6  alkyl group, a C 3-6  cycloalkyl group, a C 3-6  cycloalkyloxy group, a C 3-6  cycloalkyl(C 1-6  alkoxy) group, a C 1-6  alkoxy group, a C 1-6  alkylthio group, a haloC 1-6  alkoxy group, an aryl group, an aryloxy group, a heteroaryl group, an aryl(C 1-6  alkyl) group, an aryl(C 1-6  alkoxy) group, a C 2-6  alkenyl group, a C 2-6  alkynyl group, a heteroC 3-6  cycloalkyl group, a heteroC 3-6  cycloalkyloxy group, a heteroC 3-6  cycloalkyl(C 1-6  alkyl) group, a C 1-6  alkoxy group substituted by an amino group which is mono-substituted by a C 1-6  alkyl group or a C 1-6  alkoxy group substituted by an amino group which is di-substituted by a C 1-6  alkyl group, R 6  is a C 1-6  alkyl group, a haloC 1-6  alkyl group or a C 3-6  cycloalkyl group, and R 7  is a hydrogen atom, a C 1-6  alkyl group, a C 1-6  alkoxy group or an arylmethyloxy group, which comprises allowing a benzylpyrazole derivative represented by the general formula: 
       
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6  and R 7  have the same meanings as defined above to react with a compound represented by the general formula: 
       
       
         
           
           
               
               
           
         
         in which PG 1  has the same meaning as defined above, and X 1  is a bromine atom or a chlorine atom in the presence of a base selected from the group consisting of potassium tert-butoxide, potassium carbonate, sodium carbonate and cesium carbonate. 
       
     
     
         5 . A method for preparing a glucopyranosyloxypyrazole derivative represented by the general formula: 
       
         
           
           
               
               
           
         
         wherein Q 11  is a group represented by the general formula: 
       
       
         
           
           
               
               
           
         
         in which PG 11  is an arylcarbonyl group, a pivaloyl group or an arylmethyl group, and R 1 , R 2 , R 3 , R 4  and R 5  may be the same or different, each of them is a hydrogen atom, a halogen atom, a C 1-6  alkyl group, a haloC 1-6  alkyl group, a C 3-6  cycloalkyl group, a C 3-6  cycloalkyloxy group, a C 3-6  cycloalkyl(C 1-6  alkoxy) group, a C 1-6  alkoxy group, a C 1-6  alkylthio group, a haloC 1-6  alkoxy group, an aryl group, an aryloxy group, a heteroaryl group, an aryl(C 1-6  alkyl) group, an aryl(C 1-6  alkoxy) group, a C 2-6  alkenyl group, a C 2-6  alkynyl group, a heteroC 3-6  cycloalkyl group, a heteroC 3-6  cycloalkyloxy group, a heteroC 3-6  cycloalkyl(C 1-6  alkyl) group, a C 1-6  alkoxy group substituted by an amino group which is mono-substituted by a C 1-6  alkyl group or a C 1-6  alkoxy group substituted by an amino group which is di-substituted by a C 1-6  alkyl group, R 6  is a C 1-6  alkyl group, a haloC 1-6  alkyl group or a C 3-6  cycloalkyl group, and R 7  is a hydrogen atom, a C 1-6  alkyl group, a C 1-6  alkoxy group or an arylmethyloxy group, which comprises allowing a benzylpyrazole derivative represented by the general formula: 
       
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6  and R 7  have the same meanings as defined above to react with a compound represented by the general formula: 
       
       
         
           
           
               
               
           
         
         in which PG 11  has the same meaning as defined above, and X 1  is a bromine atom or a chlorine atom in the presence of a base selected from the group consisting of potassium tert-butoxide, potassium carbonate, sodium carbonate and cesium carbonate.