Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus acids or salts thereof
Patent
1989-06-21
1991-12-10
Evans, J. E.
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus acids or salts thereof
558 88, 558179, C07F 938, A61K 31095
Patent
active
050720325
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 mammals infected with HIV.
REFERENCES:
patent: 2629731 (1953-02-01), Harman
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A. P. Cava and MK. I. Levinson Thionation Reactions of Laweson's Reagents, Tetrahedron Report Number 192, vol. 4, No. 22 (1983), pp. 5063-5072.
N. G. Zabirov, R. A. Cherkasov, I. S. Khalikov, and A. N. Pudovik, Reactions with Trialkyl Phosphites and Triphenylphosphine, Zhurnal Obshchei Khimii, 56 No. 12 (1986) pp. 2673-2677.
N. G. Zabirov, R. A. Cherkasov, A. N. Pudovik, Method for the Preparation of Acid Phosphorothioites and Phosphonothioates, Zhurnal Obshchie Khimii, 56 No. 5 (1986) pp. 1189-1190.
B. Borecka, J. Chojnowski, M. Cyprvk, J. Michalski and J. Zielinska, Synthetic and Mechanistic Aspects of the Reaction of Trialkysilylhalides With Thio and Seleno Esters of Phosphorus, Journal of Organometallic Chemistry 171 (1979) pp. 17-34.
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