Compounds with hydroxycarbonyl-halogenoalkyl side chains

Abstract

The present invention provides a compound consisting of a moiety and a group chemically bonded to said moiety, wherein said moiety contains a compound having low activity following oral administration or its parent scaffold and said group has the following general formula (1): in which R 1 represents a hydrogen atom, etc., R 2 represents a C 1 -C 7 halogenoalkyl group, etc., m represents an integer of 2 to 14, and n represents an integer of 2 to 7, or enantiomers of the compound, or hydrates or pharmaceutically acceptable salts of the compound or enantiomers thereof. The above compound is advantageous in pharmaceutical use because the group of general formula (1) allows compounds such as anti-estrogenic ones to show a significantly increased activity following oral administration when attached to the parent scaffolds of the compounds.

1 . A compound consisting of a moiety and a group chemically bonded to said moiety, wherein said moiety contains a compound having low activity following oral administration or its parent scaffold and said group has the following formula (1):  
       
         
           
           
               
               
           
         
       
       In which 
 R 1  represents a hydrogen atom or a slat-forming metal;  
 R 2  represents a linear or branched C 1 -C 7  halogenoalkyl group,  
 M represents an integer of 2 to 14; and  
 N represents an integer of 2 to 7,  
 or enantiomers of the first-mentioned compound, or hydrates or pharmaceutically acceptable salts of the first-mentioned compound or enantiomers thereof.  
 
     
     
         2 . A process for preparing a compound according to  claim 1  comprising the steps of: 
 i) subjecting to olefin metathesis a compound of formula:                          wherein R 11  and R 12  are protecting groups, with a compound of formula:                          wherein R 13  is a protecting group, m 1  represents an integer of m-2, R 2  represents a linear or branched C 1 -C 7  halogenoalkyl group, m represents an integer of 2 to 14, and n represents an integer of 2 to 7.    ii) hydrogenation of the double bond;    iii) deprotection of the —OR 11  group;    iv) hydrolysis of the —CO 2 R 13  group; and    v) decarboxylation of one carboxyl group,    with the proviso that when the compound of formula (II) is used in step i), step v) is excluded from the process.    
     
     
         3 . A process for preparing a compound  
       
         
           
           
               
               
           
         
         wherein R 13  is a protecting group; m 1 , R 2 , m and n are as defined in  claim 1.