Mandelic acid condensation polymers

Abstract

Disclosed herein are compounds and compositions useful for reducing the risk of infection. In particular, disclosed herein are mandelic acid condensation polymers, compositions comprising such compounds, processes for producing such compounds, and methods of using such compounds.

1 . An isolated compound of formula (I) 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt, ester, amide, or prodrug form thereof, wherein 
         R 1 , R 2 , and R 3  are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycle, heteroaryl, aryl, and counterion; 
         R 4  is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycle, heteroaryl, and aryl; 
         R 5 , R 6 , and R 7  are each independently selected from the group consisting of alkyl, alkoxy, and halogen; 
         n is an integer greater than zero; and 
         x, y, and z are each an integer independently selected from the group consisting of 0, 1, 2, 3, and 4. 
       
     
     
         2 . The compound of  claim 1 , wherein
 R 1 , R 2 , R 3 , and R 4  are hydrogen; and   x, y, and z are 0.   
     
     
         3 . The compound of  claim 1 , wherein
 R 1 , R 2 , and R 3  are methyl or sodium cation;   R 4  is hydrogen; and   x, y, and z are 0.   
     
     
         4 . (canceled) 
     
     
         5 . The compound of  claim 1 , wherein n is an integer independently selected from 1 to 70. 
     
     
         6 . The compound of  claim 1 , wherein n is an integer independently selected from 10 to 22. 
     
     
         7 . The compound of  claim 1 , having formula (I-A) or (I-B), 
       
         
           
           
               
               
           
         
       
     
     
         8 .- 12  (canceled) 
     
     
         13 . The composition of  claim 1 , having a molecular weight range of about 600 to about 6,000. 
     
     
         14 .- 23 . (canceled) 
     
     
         24 . A compound according to  claim 1 , comprising repeating units of formula (II), 
       
         
           
           
               
               
           
         
         wherein R 2  is independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycle, heteroaryl, aryl, and counterion. 
       
     
     
         25 . The compound of  claim 24 , comprising about 1 to about 60 repeating units of formula (II). 
     
     
         26 . The compound of  claim 24 , wherein R 2  is selected from hydrogen, methyl, and sodium cation. 
     
     
         27 . The compound of  claim 24 , wherein R 2  is hydrogen. 
     
     
         28 .- 36 . (canceled) 
     
     
         37 . A composition comprising a compound according to  claim 1 , and a pharmaceutically acceptable carrier. 
     
     
         38 . A process for producing mandelic acid condensation polymers, comprising:
 cooling a strong acid to a temperature below 0° C.; and   adding mandelic acid or a mandelic acid derivative to the strong acid to provide a reaction mixture.   
     
     
         39 . The process of  claim 38 , wherein the mandelic acid or mandelic acid derivative is added over a period of about 30 minutes. 
     
     
         40 . The process of  claim 38 , wherein the reaction mixture is maintained at a temperature ranging from about −35° C. to about −30° C. for a period of about 1 hour. 
     
     
         41 . The process of  claim 38 , wherein the strong acid is concentrated sulfuric acid. 
     
     
         42 . The process of  claim 38 , wherein production of the polymer is conducted under neat reaction conditions. 
     
     
         43 .- 63 . (canceled) 
     
     
         64 . A method for protecting an individual from contracting a sexually transmitted disease through contact with a bodily fluid, said method comprising applying to the body or portion of the body of the individual an effective amount of a protective agent, wherein the protective agent comprises a compound according to  claim 1 . 
     
     
         65 . A method of reducing the risk of transmission of a sexually transmitted pathogen to a human subject, comprising contacting the pathogen or cells susceptible to infection by the pathogen with an effective amount of a compound according to  claim 1 , thereby reducing the risk of transmission of the pathogen. 
     
     
         66 . The method of  claim 64 , wherein the sexually transmitted disease is HIV/AIDS.