Compounds for producing substituted sulfoxides, process for producing the same and use thereof

Abstract

Disclosed herein are novel compounds which are useful as intermediates for producing substituted sulfoxide compounds and a process for producing the same. Further disclosed is a process for producing the substituted sulfoxide compounds used as pharmacologically active agents, employing the novel intermediates of the present invention.

1 . A compound of formula 9 
       
         
           
           
               
               
           
         
       
       wherein
 R represents hydrogen atom or alkyl group such as methyl; 
 R″ represents an alkyl or alkoxy group such as methyl and methoxy; 
 R″″ represents a group selected from methyl, chloromethyl, hydroxymethyl or a compound of formula 10 or 11, wherein when R″″ is methyl, N is present as N-Oxide 
 
       
         
           
           
               
               
           
         
         R′″ represents a hydrogen atom or an alkoxy group optionally interrupted by one or more heteroatoms, or a heterocyclic group, the alkoxy group selected from methoxy and difluoromethoxy and the heterocyclic group selected from pyrrole. 
       
     
     
         2 . A compound of formula-7a or its enantiomer, 
       
         
           
           
               
               
           
         
       
       wherein,
 R represents hydrogen atom or alkyl group such as methyl; 
 R″ represents a group selected from an alkyl or alkoxy such as methyl and methoxy; and 
 R′″ represents a hydrogen atom or an alkoxy group optionally interrupted by one or more heteroatoms, or a heterocyclic group, the alkoxy group selected from methoxy and difluoromethoxy and the heterocyclic group selected from pyrrole. 
 
     
     
         3 . A compound of formula-6, 
       
         
           
           
               
               
           
         
       
       wherein
 R represents a hydrogen atom or an alkyl group such as methyl; 
 R″ represents an alkyl or alkoxy group such as methyl and methoxy; and 
 R′″ represents a hydrogen atom or an alkoxy group optionally interrupted by one or more heteroatoms, or a heterocyclic group, the alkoxy group selected from methoxy and difluoromethoxy and the heterocyclic group selected from pyrrole. 
 
     
     
         4 . A compound of formula-4 
       
         
           
           
               
               
           
         
       
       wherein,
 R represents a hydrogen atom or alkyl group such as methyl; and 
 R″ represents an alkyl or alkoxy group such as methyl and methoxy. 
 
     
     
         5 . A compound of formula-5 
       
         
           
           
               
               
           
         
       
       wherein,
 R represents a hydrogen atom or alkyl group such as methyl; and 
 R″ represents an alkyl or alkoxy group such as methyl and methoxy. 
 
     
     
         6 . A compound of formula-3 
       
         
           
           
               
               
           
         
       
       wherein,
 R represents an a hydrogen atom or alkyl group such as methyl; and 
 R″ represents an alkyl or alkoxy group such as methyl and methoxy. 
 
     
     
         7 . A process for producing substituted sulfoxide compound of formula-I or formula-Ia, 
       
         
           
           
               
               
           
         
       
       in which
 R represents hydrogen atom or lower alkyl group such as methyl, ethyl; 
 R′ represents an alkyl group containing 1-6 carbon atoms, optionally interrupted by one or more oxygen atom(s) or haloalkyl,
 the alkyl group is selected from methyl, ethyl, n-propyl, isopropyl, butyl and the optionally interrupted alkyl group is selected from 3-methoxypropyl group and the haloalkyl group is selected from trifluoroethyl, difluoromethyl; 
 
 R″ represents an alkyl group selected from methyl, ethyl or propyl or an alkoxy group such as methoxy, ethoxy; 
 R′″ represents a hydrogen atom or an alkoxy group optionally interrupted by one or more heteroatoms; or a heterocyclic group, 
 the alkoxy group selected from methoxy and difluoromethoxy and the heterocyclic group selected from pyrrole; 
 
       wherein the process comprising reacting benzimidazole sulfoxide of Formula-7a or 7b 
       
         
           
           
               
               
           
         
       
       with an alcohol of formula HOR′ to obtain substituted sulfoxide compound of formula-I or formula-Ib in the presence of a suitable base. 
     
     
         8 . The process according to  claim 7 , wherein the alcohol of the formula HOR′ is selected from trifluoroethanol, 3-methoxypropanol or methanol. 
     
     
         9 . The process according to  claim 7 , wherein the base used is selected from sodium hydroxide, potassium hydroxide, sodium hydride, calcium hydroxide, barium hydroxide, magnesium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium methoxide, sodium tertiary butoxide or potassium tertiary butoxide. 
     
     
         10 . The process according to  claim 7 , wherein the solvent used is selected from dimethylsulfoxide, dimethylformamide, dimethyl acetate, N-methylpyrrolidone, methanol, ethanol, dioxane, toluene, xylene, tetrahydrofuran, dichloromethane acetonitrile, sulpholane or mixtures thereof.