Method and intermediates for preparing 2-alkoxy and 2-aryloxy estrogen compounds

Abstract

The present invention relates to 2-alkoxy and 2-aryloxyestrogen compounds, and the intermediate compounds prepared during the preparation thereof, which intermediate compounds are useful intermediates in the preparation of certain physiologically active compounds.

1 . A compound of general formula (III) 
       
         
           
           
               
               
           
         
         wherein R a  is H, lower alkyl, alkenyl or alkynyl radical. 
       
     
     
         2 . A compound of general formula (IV) 
       
         
           
           
               
               
           
         
         wherein X is a member of the group consisting of O and 
       
       
         
           
           
               
               
           
         
         wherein R a  is H, lower alkyl, alkenyl or alkynyl radical; 
         and R is: 
         1) a linear, branched or cyclic alkyl radical containing from 1 to 8 carbon atoms, optionally substituted with 1-3 substituents selected from the group consisting of
 (a) halogen; 
 (b) OR b , wherein R b  is H, lower alky or aryl; 
 (c) (C1-C6) cycloalkyl, optionally substituted with 1-3 substituents selected from the group consisting of halogen, lower alkyl, aryl and OR b , wherein R b  is H, lower alkyl or aryl; 
 (d) (C6-C10) aryl, optionally substituted with 1-3 substituents selected from the group consisting of halogen, lower alkyl, aryl and OR b , wherein R b  is H, lower alkyl or aryl; 
 (e) (C6-C10) heteroaryl, optionally substituted with 1-3 substituents selected from the group consisting of halogen, lower alkyl, aryl and OR b , wherein R b  is H, lower alkyl or aryl; or 
 
         2) an aryl radical containing from 6 to 10 carbon atoms, optionally substituted with 1-3 substituents selected from the group consisting of
 (a) halogen; 
 (b) OR b , wherein R b  is H, lower alkyl or aryl; 
 (c) (C1-C6) linear, branched or cyclic alkyl, optionally substituted with 1-3 substituents selected from the group consisting of halogen, lower alkyl, aryl and OR b , wherein R b  is H, lower alkyl or aryl; 
 
         with the proviso that when X represents O, R is different from an alkyl radical containing from 1 to 6 carbon atoms. 
       
     
     
         3 . A compound of general formula (IVb) 
       
         
           
           
               
               
           
         
         wherein X is a member of the group consisting of O and 
       
       
         
           
           
               
               
           
         
         wherein R a  is H, lower alkyl, alkenyl or alkynyl radical; 
         and R is: 
         1) a linear, branched or cyclic alkyl radical containing from 1 to 8 carbon atoms, optionally substituted with 1-3 substituents selected from the group consisting of
 (a) halogen; 
 (b) OR b , wherein R b  is H, lower alkyl or aryl; 
 (c) (C1-C6) cycloalkyl, optionally substituted with 1-3 substituents selected from the group consisting of halogen, lower alkyl, aryl and OR b , wherein R b  is H, lower alkyl or aryl; 
 (d) (C6-C10) aryl, optionally substituted with 1-3 substituents selected from the group consisting of halogen, lower alkyl, aryl and OR b , wherein R b  is H, lower alkyl or aryl; 
 (e) (C6-C10) heteroaryl, optionally substituted with 1-3 substituents selected from the group consisting of halogen, lower alkyl, aryl and OR b , wherein R b  is H, lower alkyl or aryl; or 
 
         2) an aryl radical containing from 6 to 10 carbon atoms, optionally substituted with 1:3 substituents selected from the group consisting of 
         2) an aryl radical containing from 6 to 10 carbon atoms, optionally substituted with 1-3 substituents selected from the group consisting of
 (a) halogen; 
 (b) OR b , wherein R b  is H, lower alkyl or aryl; 
 (c) (C1-C6) linear, branched or cyclic alkyl, optionally substituted with 1-3 substituents selected from the group consisting of halogen, lower alkyl, aryl and ORb, wherein Rb is H, lower alkyl or aryl. 
 
       
     
     
         4 . A compound of general formula (I) 
       
         
           
           
               
               
           
         
         wherein X is a member of the group consisting of O and 
       
       
         
           
           
               
               
           
         
         wherein R a  is H, lower alkyl, alkenyl or alkynyl radical; 
         and R is: 
         an aryl radical containing from 6 to 10 carbon atoms, optionally substituted with 1-3 substituents selected from the group consisting of
 (a) halogen, 
 (b) OR b , wherein R b  is H, lower alkyl or aryl, 
 (c) (C1-C6) linear, branched or cyclic alkyl, optionally substituted with 1-3 substituents selected from the group consisting of halogen, lower alkyl, aryl and OR b .