Phosphorous organic compounds and their use

Abstract

The invention relates to phosphorous organic compounds of general formula (I), wherein B is an ether group of formula (II) or a keto group of formula (III) or a pentagonal or hexagonal cyclic compound. The invention also relates to the use of these compounds for producing drugs for treatment or prevention of human or animal infections due to viruses, bacteria, fungi or parasites, as well as their use as fungicide, bactericide and herbicide in plants.

1 - 26 . (canceled)  
     
     
         27 . Phosphorous organic compounds having a formula (I)  
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are independently selected from a group consisting of hydrogen, substituted or unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted aralkyl, halogen, OX 1  and OX 2 , and further wherein at least one of R 1  and R 2  is OH;  
         wherein X 1  and X 2  are independently selected from a group consisting of hydrogen, substituted or unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted cycloalkyl and substituted and unsubstituted aralkyl, and further wherein at least one of X 1  and X 2  is hydrogen;  
         wherein Z is a keto group represented by the formula III  
         
           
             
             
                 
                 
             
           
         
         A 3  is selected from a group consisting of alkylene radicals, alkenylene radicals and hydroxyalkylene radicals;  
         A 4  includes at least two carbons and is selected from a group consisting of alkylene radicals, alkenylene radicals and hydroxyalkylene radicals; and  
         R 3  and R 4  are independently selected from a group consisting of hydrogen and halogen.  
       
     
     
         28 . Phosphorous organic compounds according to  claim 27 , wherein: 
 R 2  is selected from a group consisting of acetyl and formyl;    A 3  is selected from a group consisting of methylene, ethylene, ethenylene, 2-hydroxypropylene, hydroxymethylene, and hydroxyethylene;    A 4  is methylene;    R 3  is selected from a group consisting of hydrogen, methyl, ethyl, hexadecyl, octadecyl and OX 3 ; and    X 3  and X 4  are independently selected from a group consisting hydrogen, sodium, potassium, methyl, ethyl, hexadecyl and octadecyl.    
     
     
         29 . Phosphorous organic compounds according to  claim 28 , wherein the compounds include one or more compounds selected from a group consisting of ((N-formyl-N-hydroxyamino)-methoxy)-methyl phosphonic acid disodium salt, ((N-acetyl-N-hydroxyamino)-methoxy)-methyl phosphonic acid disodium salt, (2-(N-formyl-N-hydroxy amino)-ethenoxy)-methyl phosphonic acid disodium salt, (2-(N-acetyl-N-hydroxyamino)-ethenoxy)-methyl phosphonic acid disodium salt, (3-(N-formyl-N-hydroxyamino)-2-hydroxy propoxy)-methyl phosphonic acid disodium salt, and (3-(N-acetyl-N-hydroxyamino)-2-hydroxypropoxy)-methyl phosphonic acid disodium salt.  
     
     
         30 . Phosphorous organic compounds having a formula (I)  
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are independently selected from a group consisting of hydrogen, substituted or unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted aralkyl, halogen, OX, and OX 2 , and further wherein at least one of R 1  and R 2  is OH;  
         wherein X 1  and X 2  are independently selected from a group consisting of hydrogen, substituted or unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkynyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted cycloalkyl and substituted and unsubstituted aralkyl, and further wherein at least one of X 1  and X 2  is hydrogen;  
         wherein Z is a keto group represented by the formula III  
         
           
             
             
                 
                 
             
           
         
         A 3  is selected from a group consisting of alkylene radicals, alkenylene radicals and hydroxyalkylene radicals;  
         A 4  includes at least two carbons and is selected from a group consisting of alkylene radicals, alkenylene radicals and hydroxyalkylene radicals;  
         R 3  and R4 are independently selected from a group consisting of hydrogen and halogen; and  
         pharmaceutically acceptable salts, esters, amides of the esters and salts of the esters thereof.  
       
     
     
         31 . A composition comprising: 
 a compound according to  claim 30;  and    a pharmaceutically acceptable excipient.    
     
     
         32 . A composition comprising: 
 a first pharmaceutically active ingredient, the first pharmaceutically active ingredient being a compound according to  claim 30;  and    a second pharmaceutically active ingredient.    
     
     
         33 . The composition according to  claim 32  wherein the second pharmaceutically active ingredient is selected from the group consisting of sulfonamide, sulfadoxin, artemisinin, atovaquon, chinin, chloroquine, hydroxychloroquin, mefloquin, halofantrin, pyrimethamine, armesin, tetracycline, doxycyclin, proquanil, metronidazol, praziquantil, niclosamide, mebendazol, pyrantel, tiabendazole, diethylcarbazin, piperazin, pyrivinum, metrifonate, oxamniquin, bithionol and suramin.  
     
     
         34 . A composition according to  claim 32  wherein the second pharmaceutically active ingredient is selected from the group consisting of penicillins, cephalosporins, β-lactam antibiotics other than penicillins and cephalosporins, tetracyclines, aminoglycosides, monobactams, β-lactamase inhibitors; chloramphenicols, quinolones, macrolides, nitroimidazoles, antiviral agents, interferons, tibol derivatives, protemase inhibitors, antifungal agents, azoles, glycopeptides, sulfonamides, lincosamides, streptogramins, clindamycin, fusidic acid, fosfomycin, folic acid, betulinic acid, semianthrachinones, xanthones, naphtoquinones, aryammoalcohols, quinine, quinidines, diaminopyrimidines, artemisinin, dihydroartemisinin, arte-mether, arte-ether, arte-sunate, atovaquon, suramin, diethylcarbamazine, invermectin, bithionol, oxamiquine, metrifonate, piperazine and embonate.  
     
     
         35 . A composition for treating an infection comprising 
 an effective amount of a compound according to  claim 30;  and    a pharmaceutically acceptable excipient.    
     
     
         36 . A composition according to  claim 35  wherein: 
 the infection is caused by bacteria.    
     
     
         37 . A composition according to  claim 35  wherein: 
 the infection is caused by a virus.    
     
     
         38 . A composition according to  claim 35  wherein: 
 the infection is caused by a parasite.