Antiviral composition

Abstract

Chemical compounds, being the alkyl sulfate of sulfated saccharides, particularly, dextrin, dextran, and cyclodextrin, and pharmaceutical compositions containing these compounds. The compounds of the invention provide antiviral activity, particularly in the treatment and prevention of sexually-transmitted diseases. Methods of treating viral infection and preventing viral transmission include administration include administration of the compounds of the invention orally, topically, subcutaneously, by muscular injection, by intraperitoneal injection and by intravenous injection.

1 . A polysaccharide derivative containing at least one sulfate group and at least one alkylsulfate group.  
     
     
         2 . The compound of  claim 1 , wherein the polysaccharide is selected from the group consisting of dextrin, dextran, and cyclodextrin.  
     
     
         3 . The compound of  claim 1 , wherein the at least one alkylsulfate group is selected from the group consisting of methylsulfate, ethylsulfate and propylsulfate.  
     
     
         4 . A pharmaceutical composition unit dosage form comprising an active agent, present in an amount sufficient to provide antiviral activity, said active agent selected from the group consisting of alkylsulfate derivative of sulfated dextrin and alkylsulfate derivative of sulfated dextran, and at least one excipient.  
     
     
         5 . The pharmaceutical composition unit dosage form of  claim 4 , wherein the active agent is an ethyl sulfate derivative.  
     
     
         6 . The pharmaceutical composition unit dosage form of  claim 4 , wherein the active agent is an ethyl sulfate derivative.  
     
     
         7 . The pharmaceutical composition unit dosage form of  claim 4 , wherein the active agent is a propyl sulfate derivative.  
     
     
         8 . The pharmaceutical composition of  claim 4 , wherein the antiviral activity is provided against a virus selected from the group consisting of HIV, herpes viruses such as cytomegalovirus and herpes simplex, hepatitis agents, and the papilloma virus.  
     
     
         9 . A method of treating a viral infection comprising administering to a patient in need thereof a therapeutically effective amount of an active agent comprising an alkylsulfate derivative of a sulfated dextrin starting material having a molecular weight of at least 3,000, wherein the sulfated dextrin starting material is sulfonated to form the alklysulfate derivative of sulfated dextrin, wherein the range of sulfonation of the alkylsulfate derivative of sulfated dextrin is between 12 to 21%, wherein the sulfonation occurs in clusters of alkylsulfate groups and sulfate groups present on the branch point structures of the sulfated dextrin, and further wherein the ratio of alkylsulfate groups to sulfate groups is about 1 to 2.  
     
     
         10 . The method of  claim 9 , wherein the active agent is an methyl sulfate derivative.  
     
     
         11 . The method of  claim 9 , wherein the active agent is an ethyl sulfate derivative.  
     
     
         12 . The method of  claim 9 , wherein the active agent is an propyl sulfate derivative.  
     
     
         13 . The method of  claim 9 , wherein the antiviral activity is provided against a virus selected from the group consisting of HIV, herpes viruses such as cytomegalovirus and herpes simplex, hepatitis agents, and the papilloma virus.  
     
     
         14 . The method of  claim 9 , wherein the administering is selected from the group consisting of oral administering, topical administering, subcutaneous administering, administering by muscular injection, administering by intraperitoneal injection and administering by intravenous injection.  
     
     
         15 . The method of  claim 9 , wherein the administering occurs in combination with administering of another agent.  
     
     
         16 . A method of preventing viral transmission, comprising applying to a patient a therapeutically effective amount of an active agent comprising an alkylsulfate derivative of sulfated dextrin and alkylsulfate derivative of sulfated dextran as a topical formulation, wherein the alkylsulfate derivative of sulfate dextrin is prepared using a dextrin starting material having a molecular weight of at least 3,000.  
     
     
         17 . The method of  claim 16 , wherein the active agent is a methyl sulfate derivative.  
     
     
         18 . The method of  claim 16 , wherein the active agent is an ethyl sulfate derivative.  
     
     
         19 . The method of  claim 16 , wherein the active agent is a propyl sulfate derivative.  
     
     
         20 . The method of  claim 16 , wherein the viral transmission prevented is the transmission of a virus selected from the group consisting of HIV, herpes viruses, hepatitis agents, and the papilloma virus.  
     
     
         21 . A method of eliminating virus from entities selected from the group consisting of blood, blood products, organs and whole body preparations, comprising combining the entities with an effective amount of an active agent selected from the group consisting of alkylsulfate derivative of sulfated dextrin and alkylsulfate derivative of sulfated dextran as a topical formulation.  
     
     
         22 . The method of  claim 21 , wherein the active agent is a methyl sulfate dertivative.  
     
     
         23 . The method of  claim 21 , wherein the active agent is an ethyl sulfate derivative.  
     
     
         24 . The method of  claim 21 , wherein the active agent is a propyl sulfate derivative.  
     
     
         25 . The method of  claim 21 , wherein the virus eliminated is selected from the group consisting of HIV, herpes viruses, hepatitis agents, and the papilloma virus.  
     
     
         26 . The method of  claim 9 , wherein the sulfated dextrin staring material is sulfonated using compounds selected from the group consisting of a pyridine sulfurtrioxide complex, chlorosulfonic acid and methanesulfonyl chloride.  
     
     
         27 . The method of  claim 16 , wherein the alkylsulfate derivative of sulfate dextrin is prepared from the dextrin starting material using compounds selected from the group consisting of a pyridine sulfurtrioxide complex, chlorosulfonic acid and methanesulfonyl chloride.