Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...
Patent
1995-02-17
1997-11-18
Berch, Mark L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Phosphorus containing other than solely as part of an...
544267, 544276, 544277, 544313, 544314, 544317, 544243, 544244, A61K 31675, C07F 96561, C07F 96512, C07D47318
Patent
active
056887787
ABSTRACT:
Provided are compounds of the following formulae:
A phosphonomethoxymethyoxymethyl purine/pyrimidine derivative of the formula ##STR1## wherein X and X' are the same or different and are hydrogen or alkyl. R and R' are the same or different and are hydrogen, alkyl, hydroxyalkyl or alkanoyl;
B is a purine or pyrimidine base.
optionally R is taken together with X' to complete a cyclic phosphonate having the formula ##STR2## A 4'-phosphonomethoxytetrahydrofuranyl-1'-purine-pyrimidine of the formula ##STR3## wherein X and X' are the same or different and are hydrogen or alkyl, the dashed line is an optional bond,
Y and Z are the same or different and are hydrogen, hydroxyl or alkyl or Y+Z are taken together to form an epoxide or cyclopropyl, and
B is a purine or pyrimidine base.
REFERENCES:
patent: 3457255 (1969-07-01), Jones et al.
patent: 4724233 (1988-02-01), De Clercq et al.
patent: 4808716 (1989-02-01), Holy et al.
patent: 4977144 (1990-12-01), Fujimoto
patent: 5066654 (1991-11-01), Taylor, Jr.
patent: 5142051 (1992-08-01), Holy et al.
patent: 5223499 (1993-06-01), Greenlee
patent: 5470857 (1995-11-01), Borcherding
Holy, Nuclesides & Nucleotides 7, 667-670 (1988).
Yakota, Antiviral Agent. & Chemo. 5(2), 57-63 (1994).
Dvorakova, Coll. Czech. Chem. Comm 58, 1403, 1419 (1993).
Chu, T Het Chem 23, 289 (1986).
Borthwick, Tet. Letters 31, 767 (1990).
Townsend, Ed. "Chemistry of Nucleosides & Nucleotides" (Plenum, 1988), vol. 1 pp. 241, 242, 279, and 159.
Townsend Ed, "Chemistry of Nucleosides & Nucleotides" (Plenum, 1994) vol. 3, pp. 318, 319, 416.
Spector, Biochem. Pharmacol. 32, 2505 (1983).
Rosenberg, Coll. Czech. Chem Comm 53, 2753 (1988).
R.A. Foguet et al., "Process for the Preparation of 9-(2-Hydroxyethoxymethyl) guanine, used as an Antiviral Agent", Chemical Abstracts, vol. 107 (1987), No. 236377g, p. 757, col. 1.
Y. Kaneko, "Light Fading Inhibitor for Color Photographic Material", Chemical Abstracts, vol. 111 (1989), No. 205325s, p. 716, col. 1.
H-T. Ho et al., "Cellular Metabolism and Enzymatic Phosphorylation of An Anti-HIV Agent", Antiviral Research, vol. 17 (1) (1992), p. 66.
A. Holy et al., "Phosphonylmethyl Ethers of Nucleosides and Their Acyclic Analogues", American Chemical Society, Symposium Series, vol. 401 (1989), pp. 51-71.
C. U. Kim et al., "Synthesis and HIV Activity of Phosphonate Isosteres of D4T Monophosphate", Bioorganic & Medicinal Chemistry Letters, vol.2, No. 5, (1992) pp. 367-370.
C. U. Kim et al., "Synthesis and Anti-HIV Activity of Bioorganic & Medicinal Chemistry Letters, vol.2, No. 4, (1992), pp. 307-310.
C. Sergheraert et al., "Synthesis and Anti-HIV Evaluation of D4T and D4T 5'-Monophosphate Prodrugs", Journal of Medicinal Chemistry, vol. 36, No. 7, (1993), pp. 826-830.
Chow et al., "Stereospecific Vorbruggen-like Reactions of 1,2-Anhydro Sugars. An Alternative Route to the Synthesis of Nucleosides", J. Org. Chem., vol. 55, (1990), pp. 4211-4214.
Robins et al., "Synthesis, Transformation Chemistry, and Biological Activity of Guanine Nucleosides and Analogues", Nucleosides & Nucleotides, vol. 8 (5&6), (1989), pp. 725-741.
Zemlicka et al, "Nucleosides. XV. Decarboxylative Elimination of 2'-Deoxynucleoside Uronic Acids", Journal of the American Chemical Society, vol. 94, No. 9, (May 3, 1972), pp. 3213-3218.
Prisbe, et al. J. Med. Chem. 29 671 (1986).
Holy, et al. Nucl. Acid. Res., Symp. Ser. 14 277 (1984).
DeClercq, et al., Nature 323 464 (1986).
Kim, et al., Tet Lett. 31 3257 (1990).
Kim, et al., J. Org. Chem. 56 2642 (1991).
Kim, et al., Heterocycles 31 1571 (1990).
Kim, et al., J. Med. Chem. 34 2286 (1991).
"Ungesattigte Halogenzucker-Nucleoside Des Thymins (1)," Tet Lett 22:1737-1740 (structures only) (1971).
Bronson et al., "Synthesis and Antiviral Activity of Phosphonylmethoxyethyl Derivatives of Purine and Pyrimidine Bases," Nucleotide Analogs 72-87 (1989).
Kim Choung Un
Luh Bing Uh
Martin John C.
Misco Peter F.
Berch Mark L.
Hensley Max D.
Institute of Organic Chemistry and Biochemistry of the Academy o
Rega Stichting v.z.w.
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