Lipid derivatives of phosphonacids for liposomal incorporation a

Details Lipid derivatives of phosphonacids for liposomal incorporation a Lipid derivatives of phosphonacids for liposomal incorporation a

1992-12-18

1995-10-31

Dees, Jose G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

554 78, 554 79, 554 80, C07C23300

Patent

active

054630924

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: 4052439 (1977-10-01), Herrin et al.
patent: 4215113 (1980-07-01), Eriksson et al.
patent: 4591583 (1986-05-01), Helgstrand et al.
patent: 4771041 (1988-09-01), Eriksson et al.
patent: 5072032 (1991-12-01), McKenna
patent: 5177064 (1993-01-01), Bodor
patent: 5194654 (1993-03-01), Hostetler et al.
Iyer, R. P. et al. (1989) Synthesis of acyloxyalkyl acylphosphonates as potential prodrugs of the antiviral, trisodium phosphonoformate (foscarnet sodium). Tetrahedron Letters. 30(51):7141-7144, 1989.
Agranoff, B. W., et al. (1963) "Cytindine diphosphate-DL-dipalmitin" Biological Preparations 10:46-51.
Alving, C. R., et al. (1978) "Therapy of Leishmaniasis: Superior efficacies of liposome-encapsulated drugs" Proc. Natl. Acad. Sci. USA 75:2959-2963.
Bangham, A. D., et al. (1965) "Diffusion of univalent ions across the lamellae of swollen phospholipids" J. Mol. Biol. 23:238-252.
Black, C. D. V., et al. (1977) "The use of pentostam liposomes in the chemotherapy of experimental leishmaniasis" Trans. Roy. Soc. Trop. Med. Hyg. 71:550-552.
Bligh, E. G., et al. (1959) "A rapid method of total lipid extraction and purification" Can. J. Biochem. 37:911.
Fischl, M. S., et al. (1987) "The efficacy of azidothymidine (AZT) in the treatment of patients with AIDS and AIDS-related complex" New Eng. J. Med. 317: 185-191.
Helgestrand, E., et al. (1978) "Trisodium phosphonoformate, a new antiviral compound" Science (Washington, D.C.) 201:819.
Herman, E. H., et al. (1983) "Prevention of chronic doxorubicin cardiotoxicity in beagles by liposomal encapsulation" Cancer Res. 43: 5427-5432.
Ho, D. W. H., et al. (1977) "Pharmacology of 5'-esters of 1-.beta.-D-arabinofuranosylcytosine.sup.1 " Cancer Res. 37:1640-1643.
Kim, S., et al. (1983) "Preparation of multivesicular liposomes" Biochim. Biophys. Acta 728:339-348.
Koenig, S. et al. (1986) "Detection of AIDS virus in macrophages in brain tissue from AIDS patients with encephalopathy" Science 233:1089-1093.
Lambert, R., et al. (1989) "Synthesis and antiviral activity of phosphonoacetic 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. (1989) "HIV with reduced sensitivity to zidovudine (AZT) isolated during prolonged therapy" Science 243:1731-1734.
Leserman, L. D., et al. (1990) "Targeting to cells of fluorescent liposomes covalently coupled with monoclonal antibody or protein A" Nature 288:602-604.
Lopez-Berestein, G. (1986) "Liposomal amphotericin B in the treatment of fungal infections" Ann. Int. Med. 103:694-699.
Matsushita, T., et al. (1981) "Phospholipid derivatives of nucleoside analogs as prodrugs with enhanced catabolic stability" Cancer Res. 41: 2707-2713.
Mayer, L. D., et al. (1986) "Vesicles of variable sizes produced by a rapid extrusion procedure" Biochim. Biophys. Acta 858:161-168.
Mayhew, E., et al. (1984) "Characterization of liposomes prepared using a microemulsifier" Biochim. et Biophys. Acta 775:169-175.
Oberg, B. (1983) "Antiviral effects of phosphonoformate (PFA, foscarnet sodium)" Pharmacol. Ther. 19:387-415.
Olson, F., et al. (1979) "Preparation of liposomes of defined size distribution by extrusion through polycarbonate membranes" Biochim. Biophys. Acta 557: 9-23.
Ostro, M. (1987) "Liposomes" Sci. Amer. 256:103-111.
Poste, G., et al. (1984) "The challenge of liposome targeting in vivo" Liposome Technology, vol. III, G. Gregoriadis, Ed., CRC Press, Boca Raton, pp. 1-28.
Richman, D. D., et al. (1987) "The toxicity of azidothymidine (AZT) in the treatment of patients with AIDS and AIDS-related complex" New Eng. J. Med. 317:192-197.
Richman, D. D., et al. (1987) "Failure of dideoxynucleosides to inhibit human immunodeficiency virus replication in cultured human macrophages" J. Exp. Med. 166: 1144-1149.
Rosenthal, A. F., et al. (1960) "A synthetic inhibitor of venom lecithinase A*" J. Biol. Chem. 235(8):2202-2206.
Salahuddin, S. Z., et al. (1985) "Human T lymphotropic virus type III infection of human alveolar macrophages" Blood 68:281-284.
Scherphof, G., (1986) "Chapter 5: Liposomes in biology and medicine (a biased review)," Lipids and Biomembrances, Past, Present and Future. Op den Kamp, J., Roelofsen, B. and Wirtz, K. W. A., Eds., Elsevier North Holland, Amsterdam, pp. 113-136.
Szoka, F., et al. (1978) "Procedure for preparation of liposomes with large internal aqueous space and high capture by reverse-phase evaporation" Proc. Natl. Acad. Sci. USA 75:4194-4198.
Szoka, F., et al. (1988) "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.
Tetrahedron Letters, vol. 30, No. 51, issued 1989, R. P. Lyer et al, "Synthesis of acyloxyalkyl acylphosphonates as potential prodrugs of the antiviral, trisodium phosphonoformate (foscarnet sodium)," pp. 7141-7144.

Affiliated with

Also associated with

Rating

Lipid derivatives of phosphonacids for liposomal incorporation a does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Lipid derivatives of phosphonacids for liposomal incorporation a, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Lipid derivatives of phosphonacids for liposomal incorporation a will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1773551