Substituted sulfoxide compounds, methods for preparing the same and use thereof

Abstract

Disclosed are an optically pure compound having formula I, its pharmaceutically acceptable salt and its pharmaceutically acceptable solvate, and a use thereof in manufacturing medicaments and pharmaceutical compositions. A process for preparing the compound defined therein is also provided.

1 . An optically pure compound of formula I,  
       
         
           
           
               
               
           
         
         its pharmaceutically acceptable salt and its pharmaceutically acceptable solvate.  
       
     
     
         2 . Use of an optically pure compound of formula I,  
       
         
           
           
               
               
           
         
         its pharmaceutically acceptable salt or its pharmaceutically acceptable solvate in manufacturing medicaments or pharmaceutical compositions.  
       
     
     
         3 . The use of  claim 2 , wherein the medicaments or pharmaceutical compositions are useful for treatment of a disease associated with excessive gastric acid.  
     
     
         4 . The use of  claim 3 , wherein the disease comprises gastric ulcer, duodenal ulcer, gastro-oesophageal reflux diseases or Zollinger-Ellison syndrome.  
     
     
         5 . A pharmaceutical composition, comprising a therapeutically effective amount of an optically pure compound of formula I,  
       
         
           
           
               
               
           
         
         its pharmaceutically acceptable salt, its pharmaceutically acceptable solvate or a mixture thereof, and a pharmaceutically acceptable carrier.  
       
     
     
         6 . The pharmaceutical composition of  claim 5  formulated in the form of a capsule, tablet, powder, solution, suspension, syrup, pill, granule, elixir, tincture, implant, emulsion or injection.  
     
     
         7 . A compound having formula III,  
       
         
           
           
               
               
           
         
       
     
     
         8 . A process for preparing a compound having formula III, comprising reacting a compound of formula V with a compound of formula VI,  
       
         
           
           
               
               
           
         
       
     
     
         9 . A process for preparing an optically pure compound of formula I, comprising oxidizing a pro-chiral sulphide of formula II in chloroform in the presence of an oxidant,  
       
         
           
           
               
               
           
         
       
     
     
         10 . A process of  claim 9 , further comprising adding a 4 Å molecule sieve.  
     
     
         11 . A process of  claim 10 , wherein the 4 Å molecule sieve has a particle size of 4-8 mesh.  
     
     
         12 . A process of  claim 9 , wherein the process is carried out at a temperature from room temperature to about 110° C.  
     
     
         13 . A process of  claim 12 , wherein the process is carried out at a temperature from about 30° C. to about 80° C.  
     
     
         14 . A process of  claim 13 , wherein the process is carried out at a temperature of about 31° C.  
     
     
         15 . A process of  claim 9 , wherein the oxidant is a hydroperoxide, and the process is carried out in the presence of a base and a chiral titanium complex.  
     
     
         16 . A method for treating a disease associated with excessive gastric acid in a subject, comprising administering to the subject a therapeutically effective amount of an optically pure compound of formula I,  
       
         
           
           
               
               
           
         
         its pharmaceutically acceptable salt, its pharmaceutically acceptable solvate or a mixture thereof.  
       
     
     
         17 . The method of  claim 16 , wherein the disease comprises gastric ulcer, duodenal ulcer, gastro-oesophageal reflux diseases or Zollinger-Ellison syndrome.