3-alkyl pyridinium compound from red sea sponge with potent antiviral activity

Abstract

Method for treating a viral infection in a patient, comprising administering to the patient a therapeutically effective amount of a compound, or a pharmaceutically acceptable salt thereof, comprising a moiety represented by figure (I), wherein R1 is a saturated or unsaturated bivalent hydrocarbon group. Viruses subject to treatment can include HIV and flaviviruses such as west nile, dengue, or hepatitis C virus. Compositions and methods of isolation and purification are also described including from the Red Sea sponge.

What is claimed is: 
     
         1 . A method for treating a viral infection in a patient, comprising administering to the patient a therapeutically effective amount of a compound, or a pharmaceutically acceptable salt thereof, comprising at least one moiety represented by Formula (1): 
       
         
           
           
               
               
           
         
         wherein R 1  is a saturated or unsaturated bivalent hydrocarbon group. 
       
     
     
         2 . The method of  claim 1 , wherein the moiety is represented by Formula (2): 
       
         
           
           
               
               
           
         
         wherein y is 5-15. 
       
     
     
         3 . The method of any one of  claims 1 - 2 , wherein the compound is represented by Formula (3): 
       
         
           
           
               
               
           
         
       
       wherein x and y, independently of each other, are each 5-15. 
     
     
         4 . The method of any one of  claims 1 - 3 , wherein the compound is represented by Formula (4): 
       
         
           
           
               
               
           
         
       
     
     
         5 . The method of  claim 1 , wherein the compound comprises at least two moieties represented by Formula (1). 
     
     
         6 . The method of  claim 2 , wherein the compound comprises at least two moieties represented by Formula (2). 
     
     
         7 . The method of any one of  claims 1 - 6 , wherein the compound is not a salt. 
     
     
         8 . The method of any one of  claims 1 - 6 , wherein the compound is a pharmaceutically acceptable salt. 
     
     
         9 . The method of any one of  claims 1 - 8 , wherein the patient is infected with a retrovirus. 
     
     
         10 . The method of any one of  claims 1 - 9 , wherein the patient is infected with a lentivirus. 
     
     
         11 . The method of any one of  claims 1 - 10 , wherein the patient is infected with an HIV virus. 
     
     
         12 . The method of any one of  claims 1 - 11 , wherein the patient is infected with an HIV-1 virus. 
     
     
         13 . The method of any one of  claims 1 - 12 , wherein the patient is infected with a flavivirus virus. 
     
     
         14 . The method of any one  claims 1 - 13 , wherein the patient is infected with a dengue virus. 
     
     
         15 . The method of any one of  claims 1 - 14 , wherein the patient is infected with a West Nile virus. 
     
     
         16 . The method of any one of  claims 1 - 15 , wherein the patient is infected with a hepatitis C virus. 
     
     
         17 . The method of any one of  claims 1 - 16 , wherein the patient is infected with a yellow fever virus. 
     
     
         18 . The method of any one of  claims 1 - 17 , wherein the therapeutically effective amount is provided in the form of a solid having an amount of active ingredient of at least 1 wt. %. 
     
     
         19 . The method of any one of  claims 1 - 18 , wherein the therapeutically effective amount is provided in the form of a solid having an amount of active ingredient of at least 5 wt. %. 
     
     
         20 . A composition comprising: a compound, or a pharmaceutically acceptable salt thereof, comprising a moiety represented by Formula (1): 
       
         
           
           
               
               
           
         
       
       wherein R 1  is a saturated or unsaturated bivalent hydrocarbon group. 
     
     
         21 . The composition of  claim 20 , wherein the moiety is represented by Formula (2): 
       
         
           
           
               
               
           
         
         wherein y is 5-15. 
       
     
     
         22 . The composition of  claim 20 , wherein the compound is represented by Formula (3): 
       
         
           
           
               
               
           
         
         wherein x and y, independently of each other, are each 5-15. 
       
     
     
         23 . The composition of  claim 20 , wherein the compound is represented by Formula (4): 
       
         
           
           
               
               
           
         
       
     
     
         24 . The composition of any one of  claims 20 - 23 , wherein the compound is not a salt. 
     
     
         25 . The composition of any one of  claims 20 - 23 , wherein the compound is a pharmaceutically acceptable salt. 
     
     
         26 . The composition of any one of  claims 20 - 25 , the composition consisting essentially of an isolated and purified form of the compound, or a pharmaceutically acceptable salt thereof. 
     
     
         27 . The composition of  claim 21 , the composition consisting essentially of an isolated and purified form of the compound, or a pharmaceutically acceptable salt thereof. 
     
     
         28 . The composition of  claim 22 , the composition consisting essentially of an isolated and purified form of the compound, or a pharmaceutically acceptable salt thereof. 
     
     
         29 . The composition of  claim 23 , the composition consisting essentially of an isolated and purified form of the compound, or a pharmaceutically acceptable salt thereof. 
     
     
         30 . The composition of  claim 24 , the composition consisting essentially of an isolated and purified form of the compound. 
     
     
         31 . The composition of  claim 25 , the composition consisting essentially of an isolated and purified form of the compound in the form of a pharmaceutically acceptable salt thereof. 
     
     
         32 . A method of isolation and purification comprising: isolating and purifying the composition of any one of  claims 20 - 31  from a natural source. 
     
     
         33 . The method of  claim 32 , wherein the natural source is from the Red Sea. 
     
     
         34 . The method of  claim 32 , wherein the natural source is from a Red Sea sponge. 
     
     
         35 . The method of  claim 32 , wherein the natural source is from a Red Sea sponge  Amphimedon chloros.    
     
     
         36 . A method for treating a viral infection in a patient, comprising administering to the patient a therapeutically effective amount of a compound, or a pharmaceutically acceptable salt thereof, which inhibits NS3 protease. 
     
     
         37 . A method for treating a viral infection in a patient, comprising administering to the patient a therapeutically effective amount of a compound, or a pharmaceutically acceptable salt thereof, comprising at least one alkyl pyridinium compound. 
     
     
         38 . The method of  claim 37 , wherein the alkyl pyridinium compound, or pharmaceutically acceptable salt, is a 3-alkyl pyridinium compound. 
     
     
         39 . The method of any one of  claims 37 - 38 , wherein the alkyl pyridinium compound, or pharmaceutically acceptable salt, is a polymer alkyl pyridinium compound. 
     
     
         40 . The method of any one of  claims 37 - 39 , wherein the alkyl pyridinium compound, or pharmaceutically acceptable salt, has a number average molecular weight of 30,000 daltons to 50,000 daltons.