Compounds useful for treating hepatitis C virus

Abstract

A series of compounds of Formula I are disclosed which are useful in treating viral hepatitus C.

We claim:  
     
         1 . A compound of Formula I  
       
         
           
           
               
               
           
         
       
       wherein: 
 Q is CH or N;  
 R 1  is tetrazolyl, MeCONHSO 2 —, PhCONHSO 2 —, R 5 O 2 C(CH 2 ) 0-3 CONHSO 2 —,  
 R 2  is  
                     
  —CH 2 Ar 1 , —CHPh 2  , —CH 2 CO(4-FPh), —CH 2 CO(4-CF 3 Ph), or —CH 2 CONp where Np is naphthyl;  
 R 3  is C 5-7 cycloalkyl; 
 R 4  is hydrogen, Ar 2 , or Ar 3 ;  
 Ar 1  is selected from the following group: phenyl, halophenyl,  
                     
                     Ar 2  is phenyl, naphthyl, or biphenyl, optionally substituted with 1-3 substituents selected from the group comprising halogen, C 1-6  alkyl, hydroxyC 1-6 alkyl, C 1-6 alkoxy, C 1-6 sulfoxy, C 1-2 perfluoroalkyl, hydroxy, formyl, C 1-6 alkylcarbonyl, cyano, nitro, C 1-6 alkylamido, CO 2 R 5 , CONR 5 R 5 , C 1-6 alkylsulfonamido, and dioxolane;    Ar 3  is thienyl, furanyl, pyrrolyl, benzothiophenyl, benzofuranyl, indolyl, quinolinyl, or pyrimidinyl optionally substituted with 1-2 substituents selected from the group comprising C 1-6 alkyl, formyl, acetoxy, trifluoroacetoxy, and t-butoxycarbonyl;    
 R 5  is hydrogen or C 1-6 alkyl;  
 R 6  is halogen, methoxy, CO 2 R 5  or CONR 7 R 8 ; 
 R 7  and R 8  are independently hydrogen, C 1-6 alkyl, —CH(Me)CO 2 R 5 , —(CH 2 ) 1-3 CO 2 R 5 , —(CH 2 ) 1-3 CONR 5 R 5 , —(CH 2 ) 1-3 OH,  
                     
  or  
                     
  or R 7  and R 8  taken together with the nitrogen to which they are attached form pyrrolidine, morpholine, piperidine, 4-hydroxypiperidine, piperazine, or 4-methylpiperazine;  
 or a pharmaceutically acceptable salt, solvate, or prodrug thereof.  
 
 
 
     
     
         2 . A compound of  claim 1  wherein R 3  is cyclohexyl.  
     
     
         3 . A compound of  claim 1  wherein R 1  is tetrazolyl and R 2  is  
       
         
           
           
               
               
           
         
       
     
     
         4 . A compound of  claim 3  wherein R 4  is Ar 2 .  
     
     
         5 . A compound of  claim 4  wherein R 3  is cyclohexyl.  
     
     
         6 . A compound of  claim 3  wherein R 4  is Ar 3 .  
     
     
         7 . A compound of  claim 6  wherein R 3  is cyclohexyl.  
     
     
         8 . A compound of  claim 3  wherein R 4  is hydrogen.  
     
     
         9 . A compound of  claim 8  wherein R 3  is cyclohexyl.  
     
     
         10 . A compound of  claim 1  wherein R 2  is —CH 2 Ar 1 .  
     
     
         11 . A compound of  claim 10  wherein R 3  is cyclohexyl.  
     
     
         12 . A composition useful for treating hepatitus C comprising a therapeutic amount of a compound of  claim 1  and a pharmaceutically acceptable carrier.  
     
     
         13 . A method for treating hepatitus C comprising administering a therapeutically effective amount of a compound of  claim 1  to a patient.