Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...
Patent
1995-03-28
1999-02-09
Bernhardt, Emily
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Phosphorus containing other than solely as part of an...
544244, A61K 31675, C07F 96512
Patent
active
058694676
ABSTRACT:
This invention relates to new nucleotide analogues and solves the technical problem of their use as biologically active compounds. The subject of this invention are N-(2-phosphonylmethoxyethyl) and N-(3-hydroxy-2-phosphonylmethoxypropyl) derivatives of pyrimidine and purine bases, easily accessible from heterocyolic bases and their N-(2-hydroxyethyl) or N-(2,3-dihydroxypropyl) derivatives. Some of the compounds, according to this invention, exhibit a marked antiviral activity or can be converted into such active compounds by chemical transformations.
REFERENCES:
patent: 4287188 (1981-09-01), Schaeffer
patent: 4590269 (1986-05-01), Prisbe et al.
patent: 4659825 (1987-04-01), Holy et al.
patent: 4670424 (1987-06-01), MacCoss et al.
patent: 4724233 (1988-02-01), De Clercq et al.
patent: 4808716 (1989-02-01), Holy et al.
patent: 5047533 (1991-09-01), Reist et al.
patent: 5142051 (1992-08-01), Holy et al.
Organic Chemistry by Paul Karrer (2nd Ed.) pp. 92-102 (1946).
Andrei et al., "Susceptibilities of Several Drug-Resistant Herpes Simplex Virus Type 1 Strains to Alternative Antiviral Compounds," Antimicro AG & Chemo 39(7):1632-1635 (Jul. 1995).
Bronson et al., "Synthesis and Antiviral Activity of Phosphonylmethoxyethyl Derivatives of Purine and Pyrimidine Bases," Nucleotide Analogues 401:72-87 (1989).
Holy, A., "Synthetic Purine Nucleoside Analogues," Approaches to Antiviral Agents (Harnden, ed.) pp. 117-120 (1985).
Shepp et al., "Ineffectiveness of vidarabine in mucocutaneous herpes simplex virus infection," The Lancet p. 1344 (Jun. 2, 1990).
Skoldenberg et al., "Acyclovir versus vidarabine in herpes simplex encephalitis," The Lancet pp. 707-711 (Sep. 29, 1984).
Hakimelahi et al, "Design, Synthesis, and Structure--Activity Relationship of Novel Dinucleotide Analogs As Agents Against Herpes And Human Immunodeficiency Viruses, " J Med Chem 38:4648-4659 (1995).
Kim et al, "A new class of acyclic phosphonate nucleotide analogues: phosphonate isosteres of acyclovir and ganciclovir monophosphates as antiviral agents," J Med Chem 34(7):2286-2294 (1991).
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).
Barnard et al, "Selective inhibition of cytomegaloviruses by 9-(3'-ethylphosphono-1'-hydroxymethyl-1'-propyloxy-methyl)guanine," Antiviral Res 22:77-89 (1993).
Bimbaum et al, "Conformation features of acyclonucleosides: structure of acyclovir, and antiherpes agent," Can J Chem 62:2646-2652 (1984).
De Clercq, "Broad-Spectrum Anti-DNA Virus and Anti-Retrovirus Activity of Phosphonylmethoxyalkylpurines and -Pyrimidines," Biochem Pharm 42(5):963-972 (1991).
De Clercq et al, "A novel selective broad-spectrum anti-DNA virus agent," Nature 323:464-467 (1986).
De Clercq et al, "Broad-spectrum antiviral activity of adenosine analogues," Antiviral Res 4:119-133 (1984).
De Clercq et al, "Xylotubercidin against Herpes Simplex Virus Type 2 in Mice," Antimicro AG & Chemo 30(5):719-724 (1986).
Dvorakova et al, "Synthesis and Antiviral Activity of Acyclic Nucleoside and Nucleotide Derivatives of 8-Azaadenine," Collect Czech Chem Commun 58:253-255 (1993).
Dvorakova et al, "Synthesis and Biological Effects of N-(2-Phosphonomethoxyethyl) Derivatives of Deazapurine Bases," Collect Czech Chem Commun 58:1419-1429 (1993).
Franchetti et al, "8-Aza-1-Deazapurine Nucleosides As Antiviral Agents," Nucls & Nuclt 13(8):1739-1755 (1994).
Holy et al., "3'-0-Phosphonylmethyl-9-(S)-(2,3-dihydroxypropyl)adenine novel type of biologically active nucleotide analogue," Nuc Acids Res 14:277-278 (1984).
Holy et al., "Phosphonylmethyl Ethers of Nucleosides and Their Acyclic Analogues," J Am Chem Soc 4:51-71 (1989).
Keller et al, "Enzymatic Phosphorylation of Acyclic Nucleoside Analogs and Correlations with Antiherpetic Activities," Biochem Pharm 30(22):3071-3077 (1981).
Khare et al, "Inhibition of RNA Virus Replication in Vitro by 3-Deazacytidine and 3-Deazauridine (36571)," P.S.E.B.M. 140:880-884 (1972).
Kim et al., "Acyclic Purine Phosphonate Analogues as Antivral Agents. Synthesis and Structure--Activity Relationships," J Med Chem 33:1207-1213 (1990).
Kristyn et al, Izvestiya Akademiya Nauk SSSR, Sertya Khimichskaya, 8:1846-1850 (1975).
Pauwels et al, "Phosphonylmethoxyethyl Purine Derivatives, A New Class of Anti-Human Immunodeficiency Virus Agents," Antimicro AG & Chemo 32(7) 1025-1030 (1988).
Sidwell et al., "Effect of Phosphonic Acid Analogs of Acyclovir an Ganciclovir on In Vitro Cytomegalovirus Infections," Nucls & Nuclt 8:833-836 (1989).
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).
De Clercq Erik D. A.
Holy Antonin
Rosenberg Ivan
Bernhardt Emily
Hensley Max D.
Institute of Organic Chemistry and Biochemistry of the Academy o
Rega Stichting v.z.w.
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