Lipid derivatives of phosphonoacids for liposomal incorporation

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...

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514547, 514723, 514885, 554 78, 554 80, 568 8, 568 9, 568672, A01N 5718

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057444617

ABSTRACT:
Lipid-containing prodrugs are provided for treating viral infections due to herpes, influenza, hepatitis B, Epstein-Barr, and varicella zoster viruses, as well as cytomegalovirus and derivatives of antiviral agents. The compounds comprise phosphonoacids having antiviral activity which are linked, either through the phosphate group or carboxyl group of the phosphonoacid, to one of a selected group of lipids. Phosphonoacetic acid and phosphonoformic acid are thus linked to phospholipids, glycerolipids, sphingolipids, glycolipids, or fatty acids. The compounds persist, after intracellular hydrolysis, as the antiviral phosphonoacids. The lipid prodrugs are effective in improving the efficacy of antiviral phosphonoacids by prolonging their antiviral activity following administration.

REFERENCES:
patent: 300687 (1884-07-01), Cantin et al.
patent: 4052439 (1977-10-01), Herrin et al.
patent: 4150125 (1979-04-01), Herrin et al.
patent: 4215113 (1980-07-01), Eriksson et al.
patent: 4291024 (1981-09-01), Turcotte et al.
patent: 4591583 (1986-05-01), Helgstrand et al.
patent: 4771041 (1988-09-01), Eriksson et al.
patent: 4810697 (1989-03-01), Speiser et al.
patent: 5072032 (1991-12-01), McKenna
patent: 5177064 (1993-01-01), Bodor
patent: 5194654 (1993-03-01), Hostetler et al.
patent: 5223263 (1993-06-01), Hostetler et al.
Hostetler et al. (1990) J. Biol. Chem. 265:6112-17.
Lopez-Bernstein, G. (1986) Ann. Int. Med. 105:130-131.
Agranoff, B.W., et al. "Cytindine diphosphate-DL-dipalmitin" Biochemical Preparations 10:47-51 (1963).
Alving, C.R., et al., "Therapy of leishmaniasis: superior efficacies of liposome-encapsulated drugs" Proc. Natl. Acad. Sci. 72:2959-2963 (1978).
Bangham, A.D., et al. "Diffusion of univalent ions across the lamellae of swollen phospholipids" J. Mol. Biol. 13:238-252 (1965).
Black C.D.V., et al. "The Use of pentostam liposomes in the chemotherapy of experimental leishmaniasis" Trans. Roy. Soc. Trop. Med. Hyg. 71:550-552 (1977).
Bligh E.G., et al. "A rapid method of total lipid extraction and purification" Can. J. Biochem. & Physiol. 37:911-917 (1959).
Fischl M.S., et al., "The efficacy of azidothymidine (AZT) in the treatment of patients with AIDS and AIDS-related complex" New Eng. J. Med. 317:185-191 (1987).
Helgstrand, E., et al., "Trisodium phosphonoformate, a new antiviral compound" Science 201:819 (1978).
Herman, E.H., et al. "Prevention of chronic doxorubicin cardiotoxicity in beagles by liposomal encapsulation" Cancer Res. 43:5427-5431 (1983).
Ho, D.W.H. et al. "Pharmacology of 5' esters of 1-.beta.-D-arabinofuranosylcytosine.sup.1 " Cancer Res. 37:1640-1643 (1977).
Iyer, R.P. et al. "Synthesis of acyloxyalkyl acylphosphonates as potential prodrugs of antiviral, trisodium phosphonoformate" Tetrahedron Letters 30(51):7141-7144 (1989).
Kim, S., et al. "Preparation of multivesicular liposomes" Biochim. Biophys. Acta. 728:339-348 (1983).
Koenig, S., et al. "Detection of AIDS virus in macrophages in brain tissue from AIDS patients with encephalopathy" Science 233:1089-1093 (1986).
Lambert, R., et al. "Synthesis and antiviral activity of phosphonacetic and phosphonoformic acid esters of 5'-bromo-2'-deoxyuridine and relate pyrimidine nucleosides and acyclonucleosides" J. Med. Chem. 32:367-374.
Larder, B.A., et al. "HIV with reduced sensitivity to zidovudine (AZT) isolated during prolonged therapy" Science 243:1731-1734 (1989).
Leserman, L.D., et al. "Targeting to cells of fluorescent liposomes covalently coupled with monoclonal antibody or protein A" Nature 288:602-604 (1980).
Lopez-Berestein, G., "Liposomal amphotericin B in the treatment of fungal infections" Ann. Int. Med. 103:694-699 (1986).
Matsushita, T., et al. "Phospholipid derivatives of nucleoside analogs as prodrugs with enhanced carabolic stability" Cancer Res. 421:2707-2713 (1981).
Mayhew, E., et al. "Characterization of liposomes prepared using a microemulsifier" Biochim. Biophys. Acta. 775:169-174 (1984).
Mayer, L.D., et al. "Vesicles of variable sized produced by a rapid extrusion procedure" Biochim. Biophys. Acta. 858:161-168 (1986).
Oberg, B. "Antiviral effects of phosphonoformate (PFA, foscarnet sodium)" Pharmacol. Ther. 19:387-415 (1983).
Ostro, M. "Liposomes" Sci. Am. 256:103-111 (1987).
Olson, F. et al. "Preparation of liposomes of defined size distribution by extrusion through polycarbonate membranes" Biochim. Biophys. Acta. 557:9-23 (1979).
Poste, G., et al. "The challenge of liposome targeting in vivo" Liposome Technology, vol. III, G. Gregoriadis, Ed., CRC Press, Boca Raton, pp. 1-28 (1984).
Richman, D.D., et al. "The toxicity of azidothymidine (AZT) in the treatment of patients with AIDS and AIDS-related complex" New Eng. J. Med. 317:192-197 (1987).
Richman, D.D., et al. "Failure of dideoxynucleosides to inhibit human immunodeficiency virus replication in cultured human macrophages" J. Exp. Med. 166:1144-1149 (1987).
Rosenthal, A.F., et al. "A synthetic inhibitor of venom licithinase A" Biol. Chem. 235(8):2202-2206 (1960).
Salahuddin, S.Z., et al. "Human T lymphotropic virus type III infection of human alveolar macrophages" Blood 68:281-284 (1986).
Scherphof, G., "Chapter 5: Liposomes in biology and medicine (a biased review)" Lipids and Biomembranes, Past PResent and Furture, J.A.F. Op den Kamp et al,. Eds., Elsevier North Holland, Amsterdam, pp. 113-136 (1986).
Szoka, F., et al. "Increased efficacy of phosphonoformate and phosphonoacetate inhibition of herpes simples virus type 2 replication by encapsulation in liposomes" Antimicrobial Agents and Chemotherapy 32(6):858-864 (1988).
Szoka, F., et al. "Procedure for preparation of liposomes with large internal aqueous space and high capture by reverse-phase evaporation" Proc. Nat. Acad. Sci. 75:4194-4198 (1978).

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