Iodo-nonoxynol-9-derivatives and methods for their use

Abstract

Mono- and di-iodinated nonoxynol-9-derivatives and methods for their use are disclosed.

What is claimed is:  
     
         1 . A compound of the formula:  
       wherein R is a carbon atom containing moiety having at least 6 carbon atoms, Q is H or I, and n=1-25.  
     
     
         2 . The compound according to    claim 1   , wherein n=8.  
     
     
         3 . The compound according to    claim 1   , wherein n=9.  
     
     
         4 . The compound according to    claim 2   , wherein Q is H.  
     
     
         5 . The compound according to    claim 1   , wherein Q is I.  
     
     
         6 . The compound according to    claim 1   , wherein n is from 4 to 15.  
     
     
         7 . The compound according to    claim 6   , wherein n is 6-8.  
     
     
         8 . The compound according to    claim 7   , wherein n=6.  
     
     
         9 . The compound according to    claim 7   , wherein n=7.  
     
     
         10 . The compound according to    claim 7   , wherein n=8.  
     
     
         11 . The compound according to    claim 1   , wh ich is water-soluble.  
     
     
         12 . The compound according to    claim 1   , which is water insoluble.  
     
     
         13 . The compound according to    claim 1   , wherein one or both iodine atoms are radioisotopes, and the iodine radioisotopes are selected from the group consisting of 123-iodine, 125-iodine and 131-iodine.  
     
     
         14 . The compound according to    claim 1   , wherein R is nonyl or octyl.  
     
     
         15 . A pharmaceutical composition comprising a compound of the formula:  
       
         
           
           
               
               
           
         
       
       wherein R is a carbon atom containing moiety having at least 6 carbon atoms, Q is H or I, and n=1-25, and a pharmaceutically acceptable carrier.  
     
     
         16 . The composition according to    claim 15   , in a form suitable for oral administration selected from the group consisting of tablets, lozenges, granules, dragees, capsules, and pills.  
     
     
         17 . The composition according to    claim 15   , further comprising polyvinylpyrrolidone (PVP).  
     
     
         18 . The composition according to    claim 15   , in a form suitable for vaginal application.  
     
     
         19 . The composition according to    claim 18   , in a form selected from the group consisting of a sponge, cream liquid douche, gel, jelly, aerosol foam, impregnated tampon, a controlled delivery device, and a lubricant on a condom or a cap diaphragm.  
     
     
         20 . A method for preventing conception, the method comprising the step of: 
 administering an effective amount of a compound of the formula:                          wherein R is a carbon atom containing moiety having at least 6 carbon atoms, Q is H or I, and n=1-25.    
     
     
         21 . The method of    claim 20   , comprising: 
 topically administering the compound to a vaginal cavity.    
     
     
         22 . The method of    claim 20   , comprising: 
 orally administering the compound.    
     
     
         23 . The method of    claim 20   , comprising administering the compound at a concentration between about 0.04 to about 100 mg/kg.  
     
     
         24 . The method of claims  20 , comprising administering the compound at a concentration between about 0.01 to about 1 mg/kg.  
     
     
         25 . A method for reducing or preventing transmission of a sexually transmitted disease, the method comprising the step of: 
 administering an effective amount of a compound of the formula:                          wherein R is a carbon atom containing moiety having at least 6 carbon atoms, Q is H or I, and n=1-25, and a pharmaceutically acceptable carrier.    
     
     
         26 . The method of    claim 25   , comprising: 
 topically administering the compound to a vaginal cavity.    
     
     
         27 . The method of    claim 25   , comprising: 
 orally administering the compound.    
     
     
         28 . The method of    claim 25   , comprising administering the compound at a concentration between about 0.04 to about 100 mg/kg.  
     
     
         29 . The method of    claim 25   , comprising administering the compound at a concentration between about 0.01 to about 1 mg/kg.  
     
     
         30 . A process for preparing a compound of formula:  
       
         
           
           
               
               
           
         
       
       wherein R is a carbon atom containing moiety having at least 6 carbon atoms, Q is H or I, and n=1-25, comprising the steps of: 
 reacting thallium trifluoroacetate with a compound of formula:  
                     
 wherein Q and n are as defined above to form an electrophilic thallium intermediate, and  
 iodinating the intermediate.  
 
     
     
         31 . The process of    claim 30   , further comprising: 
 isolating at least one iodinated oligomer.