Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...
Patent
1995-06-07
1998-08-11
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Phosphorus containing other than solely as part of an...
544243, C07F 902, A61K 31675
Patent
active
057927561
ABSTRACT:
There are disclosed novel oral prodrugs of phosphonate nucleotide analogs which are hydrolyzable under physiological conditions to yield compounds which are useful as antiviral agents, especially as agents effective against RNA and DNA viruses. They may also find use as antitumor agents.
REFERENCES:
patent: 3929840 (1975-12-01), Christensen
patent: 4816447 (1989-03-01), Ashton
patent: 4816570 (1989-03-01), Farquhar
patent: 4968788 (1990-11-01), Farquhar
patent: 5032680 (1991-07-01), Kawai
patent: 5476938 (1995-12-01), Vemishetti et al.
Bacon, T.H., "Comparative Activity of Penciclovir Acyclovir Against epstein-Barr Virus, " Antiviral Res 23:99 (1994).
Balzarini et al. "Differential Antiherpesvirus and Antiretrovirus Effects of the (S) and (R) Enantiomers of Acyclic Nucleoside Phosphonates," Antimicro AG & Chemo 37(2):332-338 (1993).
Barditch-Crovo et al., "A Randomized, Double-Blind, Placebo-Controlled Phase I/II Evaluation of Orally Bioavailable Prodrug of the Anti-HIV Nucleotide, PMEA," 8th International Conference on Antiviral Research, Santa Fe, NM Abstract #9;A229 (Apr. 23-28, 1995).
Barditch-Crovo et al., "Copy of Slides of the Abstract #9 Presentation," 8th International Conference on Antiviral Research, Santa Fe, NM 14 pages (Apr. 23-28, 1995).
Beres, "Synthesis and Antitumor and Antiviral Properties of 5-Halo- and 5-(Trifluoromethyl)-2'-deoxyuridine 3',5'-Cyclic Monophosphates and Neutral Triesters," J Med Chem 29:1243-1249 (1986).
Bronson et al., "Synthesis and Antiviral Activity of Phosphonylmethoxyethyl Derivatives of Purine and Pyrimidine Bases," J Am Chem Soc 401:72-87 (1989).
De Clercq,"Broad-Spectrum Anti-DNA Virus and Anti-Retrovirus Activity of Phosphonylmethoxalkylpurines and -Pyrimidines," Biochem Pharm 42(5):963-972 (1991).
Eto, "Specific Effects of 4-Morpholine-N,N'-dicyclohexylcarboxamidine as a Catalyst for the Alkylation and Phosphrorylation of Ribonucleosides by a Two-step Phosphorylating Agent, Mtbo: Its Application to the Synthesis of Cytokinin-like Nucleotides," Biol Chem 55(8):1999 (1991).
Farquhar et al, "Biologically Reversible Phosphate-Protective Groups," J Pharm Sci 72:324-325 (1983).
Farrow et al, "Synthesis and Biological Properties of Novel Phosphotriesters: A New Approach to the Introduction of Biologically Active Nucleotides into Cells," J Med Chem 33:1400-1406 (1990).
Germershausan, "Comparison of the Modes of Antiviral Action of 2'-Nor-deoxyguanosine and its Cyclic Phosphate, 2'-Nor-cyclic GMP," Antimicro AG & Chemo 29:1025 (1986).
Hartmann et al., "In vitro activity of acyclic nucleoside phosphonate derivatives against feline immunodeficiency virus in Crandell feline kidney cells and feline peripheral blood lymphocytes," Antiviral Chem & Chemo 5(1):13-19 (1994).
Holy et al., "Phosphonylmethyl Ethers of Nucleosides and Their Acyclic Anlogues," Nucleotide Analogues 51-71 (1989).
Hoover et al., "Early therapy of feline leukemia virus infection (FeLV-Faids) with 9-(2-phosphonymethoxyethyl)adenine (PMEA)," Antiviral Res 16:77-92 (1991).
Iyer et al., "Synthesis of Acyloxyalkyl Acylphosphonates as Potential Prodrugs of the Antiviral, Trisodium Phosphonoformate (Foscarnet Sodium)," Tet Lett 30(51):7141:7144 (1989).
Kumar et al., "Synthesis and Biological Evaluation of Some Cyclic Phosphoramidate Nucleoside Derivatives," J Med Chem 33:2368-2375 (1990).
MacCoss, "The Synthesis, Characterization, and Preliminary Biological Evaluation of 1-Beta-D-Arabinofuranosylcytosine-5'-Diphosphate-L-1,2-Dipalmitin," Biochem Biophys Res Comm 85:714 (1978).
Midoux, "Drug Targeting: Anti-HSV-1 Activity of Mannosylated polymer-Bound 9-(2-Phosphonylmethoxyethyl Adenine," Biochem Biophys Res Comm 167(3):1044-1049 (1990).
Naesens, "Pharmacokinetics in Mic of Bis(POM)-PMEA, the Bis(pivaloyloxymethyl) Ester Prodrug of 9-(2-Phosphonylmethoxyethyl)adenine," 8th International Conference on Antiviral Research, Santa Fe, NM Abstract#98:A277 (Apr. 23-28, 1995).
Naesens et al., "Antiviral Efficacy in Mice of Oral Bis(POM)-PMEA, the Bis(pivaloyloxymethyl) Ester of Prodrug of 9-(2-Phosphonylmethoxyethyl)adenine," 8th International Conference on Antiviral Research, Santa Fe, NM Abstract#96:A229 (Apr. 23-28, 1995).
Naesens et al., "Efficacy of Oral 9-(2-phosphonylmethoxyethyl)-2,6-diaminopurine (PMEDAP) in the Treatment of Retrovirus and Cytomegalovirus Infections in Mice," Journal of Medical Virology 39:167-172 (1993).
Naesens et al., "Single-dose administration of 9-(2-phosphonylmethoxyethy)adenine (PMEA) and 9-(2-phosphonylmethoxyethyl)-2,6diaminopurine (PMEDAP) in the prophylaxis of retrovirus infection in vivo," Antiviral Res 16:53-64 (1991).
Rosenberg et al. "Phosphonylmethoxyalkyl and Phosphonylalkyl Derivatives of Adenine," Collect Czech Chem Commun 53:2753-2777 (1988).
Rosenberg et al, "Synthesis of Potential Prodrugs and Matebolites of 9-(S)-(3-Hydroxy-2-Phosphonylmethoxypropyl)Adenines," Collect Czech Chem Commun 52:2792-2800 (1987).
Snoeck et al, "Antiviral activity of anti-cytomegalovirus agents (HPMPC, HPMPA) assessed by a flow cytometric method and DNA hybridization technique," Antiviral Res 16:1-9 (1991).
Snoeck et al, "New Acyclic nucleoside phosphonate derivatives as inhibitors of human cytomegalovirus," 29th Interscience Conference on Antimicrobial Agents and Chemotherapy p. 327, Abstract No. 1334 (Sep. 17-20, 1989).
Spadari, "Antivirals based on Inhibition of Herpesvirus Thymidine Kinases," Drug News and Perspective 2:333 (1989).
Srivastva et al. "Bioreversible Phosphate Protective Groups: Synthesis and Stability of Model Acyloxymethyl Phosphates," Bioorg chem 12:118-129 (1984).
Starrett et al, "Synthesis and in vitro evaluation of a phosphonate prodrug: bis(pivaloyloxymethyl) 9-(2-phosphonylmethoxyethyl)adenine," Antiviral Res 19:267-273 (1992).
Starrett et al., "Synthesis, Oral Bioavailability Determination, and in Vitro Evaluation of Prodrugs of the Antiviral Agent (1994).
Vahlenkamp et al., "(R)-9-(2-Phosphonylmethoxypropyl)-2,6-Diaminopurine Is a Potent Inhibitor of Feline Immunodeficiency Virus Infection," Antimicro AG & Chemo 39(3):746-749 (1955).
Yokota et al, "Inhibitory effects of acyclic nucleoside phosphonate analogues on hepatitis B virus DNA synthesis in HB611 cells," Antiviral Chem & Chemo 5(2):57-63 (1994).
Yokota et al., Antiviral Chemistry and Chemotherapy 5(2): 57-63, Mar. 1994.
Bronson Joanne J.
Mansuri Muzammil M.
Martin John C.
Starrett, Jr. John E.
Tortolani David R.
Coleman Brenda
Hensley Max D.
Institute of Organic Chemistry and Biochemistry of the Academy o
Rega Stichting v.z.w.
Shah Mukund J.
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