Preparation and use of thiophosphonates and thio-analogues of phosphonoformic acid
OwnerCharles E. McKennainventor
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Abstract
Methods for converting phosphonates into thiophosphonates and specific thiophosphonate compounds so produced are disclosed and claimed. The methods start with a reaction mixture formed of a phosphonate compound, including one or more strong electron-withdrawing groups located adjacent to the phosphorus in the compound, a slight excess of Lawesson's reagent, and a polar aprotic solvent. The reaction mixture is heated until reaction is complete and may be followed with separation or hydrolyzation steps to produce thiophosphonic acids and their addition salts. One of these thio-analogues, thiophosphonoformic acid (TPFA) is particularly effective at inhibiting HIV replication and in treating HIV infection.
Claims7
A method for the conversion of trimethyl phosphonoformate into trimethyl thionophosphonoformate, said method comprising the steps of:
- forming a reaction mixture of trimethyl phosphonoformate, an effective amount of Lawesson's reagent and polar, aprotic solvent;
- and
- heating said reaction mixture until conversion is substantially complete.
A method of treating a human infected with the human immunodeficiency virus (HIV) to inhibit HIV activity comprising the administration of a pharmaceutically effective amount of thiophosphonoformic acid (TPFA) or a pharmaceutically acceptable salt thereof.
A method of treating a human infected with the human immunodeficiency virus (HIV) to inhibit HIV activity comprising the administration of a pharmaceutical composition comprising an effective amount of thiophosphonoformic acid (TPFA) or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
Dependencies are inferred from the claim text.