Novel intermediate compounds useful in the production of diarylcycloalkyl derivatives

Abstract

The invention relates generally to intermediate compounds derived during the process for preparing diarylcycloalkyl derivatives which are activators for peroxisome proliferator-activated receptors (PPAR activators) and are therefore useful in the therapeutic treatment of a number of diseases and disorders of the central nervous system such as multiple sclerosis, Parkinson's Disease, psychiatric disorders and the like. The intermediate compounds of the present invention are defined structurally by the formulae (Ia): and formula (II): wherein the respective substituent groups are defined herein.

1 . A compound of formula (Ia)  
       
         
           
           
               
               
           
         
         wherein:  
         Ring A is C 3 -C 8 -cycloalkyl or C 3 -C 8 -cycloalkenyl, in which one or more carbon atoms in the cycloalkyl or cycloalkenyl rings may be replaced by oxygen atoms,  
         R1, R2, R4 and R5 are each independently selected from the group consisting of H, F, Cl, Br, OH, NO 2 , CF 3 , OCF 3 , C 1- C 6 -alkyl or —O—(C 1 -C 6 -alkyl),  
         R3 is selected from the group consisting of H, C 1 -C 6 -alkyl or benzyl, which may optionally be substituted by F, Cl, Br, OH, NO 2 , CF 3 , OCF 3 , C 1 -C 6 -alkyl or —O—(C 1 -C 6 -alkyl),  
         R6 is selected from the group consisting of C 1 -C 6 -alkyl, or benzyl, which may optionally be substituted by F, Cl, Br, OH, NO 2 , CF 3 , OCF 3 , C 1 -C 6 -alkyl or —O—(C 1 -C 6 -alkyl),  
         X is a C 1 -C 6 -alkyl, in which one or more carbon atoms in the alkyl group may be replaced by oxygen atoms, and;  
         Y is a C 1 -C 6 -alkyl, in which one or more carbon atoms in the alkyl group may be replaced by oxygen atoms  
       
     
     
         2 . The compound as recited in  claim 1  wherein: 
 Ring A is a cyclohexyl in which the X-containing and the Z3-containing substituents are in the cis-1,3-arrangement relative to the cyclohexyl fragment,    R1 is F, C 1 -C 3 -alkyl or —O—(C 1- C 3 -alkyl),    R2 is H,    R4 is H or C 1 -C 3 -alkyl,    X and Y are each independently C 1 -C 6 -alkyl,    R5 is a C 1 -C 6 -alkyl, and    R6 is a benzyl.    
     
     
         3 . A compound as defined by formula (II)  
       
         
           
           
               
               
           
         
         wherein:  
         Ring A is selected from the group consisting of C 3 -C 8 -cycloalkyl or C 3 -C 8 -cycloalkenyl, in which one or more carbon atoms in the cycloalkyl or cycloalkenyl rings may be replaced by oxygen atoms, and  
         Z3 is a base-stable and acid-labile protecting group.  
       
     
     
         4 . The compound as recited in  claim 3 , wherein: 
 Ring A is a cyclohexyl group in which the OH-containing and the Z3-containing substituents are in the cis-1,3-arrangement relative to the cyclohexyl fragment, and    Z3 is a tetrahydropyranyl group.