Ethylene glycol esters as photoactive agents

Abstract

New compounds useful in photodynamic therapy are of the formula and their 1,4-diene isomers and the metallated and/or labeled and/or conjugated forms thereof wherein each R 1 is independently alkyl(1-6C); each n is independently an integer of 0-6; and R 2 is vinyl or a derivative form thereof.

1 . A compound of the formula  
     
       
         
         
             
             
         
       
       and their 1,4-diene isomers  
       and the metallated and/or labeled and/or conjugated forms thereof 
 wherein each R 1  is independently alkyl (1-6C);  
 
       each n is independently an integer of 0-6; and  
       R 2  is vinyl or a derivative form thereof.  
     
   
   
       2 . The compound of  claim 1  wherein R 2  is vinyl, —CHOR′, —CHO, —COOR′, —CH(OR′)CH 3 , —CH(OR′)CH 2 OR′, —CH(SR′)CH 3 , —CH(NR′) 2 CH 3 , —CH(CN)CH 3 , —CH(COOR′)CH 3 , —CH(OOCR′)CH 3 , —CH(NR′COR′)CH 3 , —CH(CONR 12 )CH 3 , —CH(halo)CH 3 , or —CH(halo)CH 2 (halo) wherein R′ is H, or a hydrocarbon radical (1-6C) optionally substituted with a heteroatom substitutent.  
   
   
       3 . The compound of  claim 1  wherein R 2  is an organic group of less than 12C resulting from direct or indirect derivatization of a vinyl substitutent.  
   
   
       4 . The compound of  claim 1  wherein R 2  is a group containing 1-3 tetrapyrrole-type nuclei.  
   
   
       5 . The compound of  claim 1  which is in a metallated form.  
   
   
       6 . The compound of  claim 1  which is in conjugated form.  
   
   
       7 . The compound of  claim 1  which is labeled.  
   
   
       8 . The compound of  claim 1  which does not contain a metal ion.  
   
   
       9 . The compound of  claim 1  wherein R 2  is vinyl.  
   
   
       10 . The compound of  claim 1  wherein each R 1  is methyl.  
   
   
       11 . The compound of  claim 1  wherein both n are 2.  
   
   
       12 . The compound of  claim 11  wherein R 2  is vinyl and both R 1  are methyl.= 
   
   
       13 . The compound of  claim 1  which is of formulas 1-4.  
   
   
       14 . The compound of  claim 13  wherein R 2  is vinyl, —CHOR′, —CHO, —COOR′, —CH(OR′)CH 3 , —CH(OR′)CH 2 OR′, —CH(SR′)CH 3 , —CH(NR′) 2 CH 3 , —CH(CN)CH 3 , —CH(COOR′)CH 3 , —CH(OOCR′)CH 3 , —CH(NR′COR′)CH 3 , —CH(CONR′ 2 )CH 3 , —CH(halo)CH 3 , or —CH(halo)CH 2 (halo) wherein R′ is H, or a hydrocarbon radical (1-6C) optionally substituted with a heteroatom substitutent.  
   
   
       15 . The compound of  claim 13  wherein R 2  is an organic group of less than 12C resulting from direct or indirect derivatization of a vinyl substitutent.  
   
   
       16 . The compound of  claim 13  wherein R 2  is vinyl.  
   
   
       17 . The compound of  claim 13  wherein each R 1  is methyl.  
   
   
       18 . The compound of  claim 13  wherein both n are 2.  
   
   
       19 . The compound of  claim 18  wherein R 2  is vinyl and both R 1  are methyl.  
   
   
       20 . The compound of  claim 12  which is of the formula  
     
       
         
         
             
             
         
       
       and the metallated and/or labeled and/or conjugated forms thereof.  
     
   
   
       21 . The compound of  claim 20  which is in a metallated form.  
   
   
       22 . The compound of  claim 20  which is in conjugated form.  
   
   
       23 . The compound of  claim 20  which is labeled.  
   
   
       24 . The compound of  claim 20  which does not contain a metal ion.  
   
   
       25 . A pharmaceutical composition which comprises the compound of  claim 1  in admixture with at least one pharmaceutically acceptable excipient.  
   
   
       26 . A pharmaceutical composition which comprises the compound of  claim 20  in admixture with at least one pharmaceutically acceptable excipient.  
   
   
       27 . An improved method to conduct photodynamic therapy or diagnosis wherein said method comprises administering a photoactive compound to a subject in need of said therapy or diagnosis wherein the improvement comprises use of the compound of  claim 1  as the photoactive agent.  
   
   
       28 . An improved method to conduct photodynamic therapy or diagnosis wherein said method comprises administering a photoactive compound to a subject in need of said therapy or diagnosis wherein the improvement comprises use of the compound of  claim 20  as the photoactive agent.  
   
   
       29 . An improved method to conduct photodynamic therapy or diagnosis wherein said method comprises administering a photoactive compound to a subject in need of said therapy or diagnosis wherein the improvement comprises use of the compound of  claim 21  as the photoactive agent.  
   
   
       30 . An improved method to conduct photodynamic therapy or diagnosis wherein said method comprises administering a photoactive compound to a subject in need of said therapy or diagnosis wherein the improvement comprises use of the compound of  claim 22  as the photoactive agent.  
   
   
       31 . An improved method to conduct photodynamic therapy or diagnosis wherein said method comprises administering a photoactive compound to a subject in need of said therapy or diagnosis wherein the improvement comprises use of the compound of  claim 23  as the photoactive agent.  
   
   
       32 . An improved method to conduct photodynamic therapy or diagnosis wherein said method comprises administering a photoactive compound to a subject in need of said therapy or diagnosis wherein the improvement comprises use of the compound of  claim 24  as the photoactive agent.