Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1993-05-21
1997-01-07
Woodward, Michael P.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514457, 514460, 549277, A61K 31365, A61K 3137, C07D49322
Patent
active
055917704
ABSTRACT:
The present invention provides novel antiviral compounds, refered to as calanolides, related compounds, and their derivatives, which may be isolated from plants, or derived from compounds from plants, of the genus Calophyllum in accordance with the present inventive method. The compounds and their derivatives may be used alone or in combination with other antiviral agents in compositions, such as pharmaceutical compositions, to inhibit the growth or replication of a virus, such as a retrovirus, in particular a human immunodeficiency virus, specifically HIV-1 or HIV-2.
REFERENCES:
Saunders, "Non-nucleoside inhibitors of HIV reverse transcriptase". . . , Drug Design & Discovery 8:255-263 (1993).
Ranjith et al., Phytochemistry, 24 (7), 1553-1556 (1985).
Bandara et al., "Two Chemically Distinct Groups of Calophyllum species From Sri Lanka," Phytochemistry, 25(2), 425-428 (1986).
Boyd, "Strategies for the Identification of New Agents for the Treatment of AIDS: A National Program to Facilitate the Discovery and Preclinical Development of New Drug Candidates for Clinical Evaluation," (Chapter 18) In AIDS: Etiology, Diagnosis, Treatment and Prevention, 2d edition, (DeVita, Jr. et al., eds., J. B. Lippincott Co., Philadelphia, 1988).
Boyer et al., "Analysis of Nonnucleoside Drug-Resistant Variants of Human Immunodeficiency Virus Type 1 Reverse Transcriptase," J. Virology, 67(4), 2412-2420 (1993).
Cragg et al., "Conservation of Biodiversity and the Potential for Development of Pharmaceutical Crops: Drug Discovery and Development at the United States National Cancer Institute," In Proceedings of the Symposium on The Industrial Utilization of Tropical Plants and the Conservation of Biodiversity, Enugu, Nigeria, Feb. 14-19, 1993 (in press).
Craig et al., "Antiviral properties of Ro 31-8959, An Inhibitor of Human Immunodeficiency Virus (HIV) Proteinase," Antiviral Research, 16, 295-305 (1991).
Dahanayake et al., "Chemical Investigation of Ceylonese Plants. Part VII. Extractives of Calophyllum thwaitesii Planch and Triana and Calophyllum walkeri Wight (Guttiferae)," J. C. S. Perkin I 2510-2514 (1974).
Dharmaratne et al., "Triterpenoids and Coumarins from the Leaves of Calophyllum Cordato-Oblongum," Phytochemistry, 24(7), 1553-1556 (1985).
Dharmaratne et al., "Xanthones from Roots of Three Calophyllum Series", Phytochemistry, 25(8), 1957-1959 (1986).
Gautier et al., "Structure of Calophynic Acid, A Novel Constituent of Calophyllum Inophyllum," Tetrahedron Letters, 27, 2715-2718 (1972).
Gulakowski et al, "A Semiautomated Multiparameter Approach for Anti-HIV Drug Screening," Journal of Virological Methods, 33, 87-100 (1991).
Gunasekera et al., "Chemical Investigation of Ceylonese Plants. Part 27. Extractives of Calophyllum cuneifolium Thw. and Calophyllum soulattri Burm. f. (Guttiferae)," J. C. S. Perkin I, 1505-1511 (1977).
Gunasekera et al., "Chemical Investigation of Ceylonese Plants. Part XVI. Extractives of Calophyllum cordato-oblongum Thw. (Guttiferae)," J.C.S. Perkin I, 2215-2220 (1975).
Gunatilaka et al., "Terpenoid and Biflavonoid Constituents of Calophyllum Calaba and Garcinia Spicata From Sri Lanka," Phytochemistry, 23(1), 323-328 (1984).
Gustafson et al., "A Nonpromoting Phorbol from the Samoan Medicinal Plant Homalanthus nutans Inhibits Cell Killing by HIV-1," J. Med. Chem., 35, 1978-1986 (1992).
Gustafson, et al., "AIDS-Antiviral Natural Products Research at the U.S. National Cancer Institute," in Natural Products as Antiviral Agents (Chu et al., eds., Plenum Press, New York 1992).
Hertzberg et al., "Kenetic Studies of HIV-1 Reverse Transcriptase Inhibition by Inophyllums, A Novel Class of Non-Nucleoside Inhibitors, Using a Scintillation Proximity Assay," Program and Abstracts of the Third International Conference on the Biotechnology of Microbial Products: Novel Pharmacological and Agrobiological Activities, P-42, 27 (Apr. 1993).
Hertzberg et al., "Novel Methods for Antiviral Drug Discovery," Programs and Abstracts of the Third International Conference on the Biotechnology of Microbial Products: Novel Pharmacological and Agrobiological Activities, S-9, 17 (Apr. 1993).
Hizi et al., "Specific Inhibition of the Reverse Transcriptase of Human Immunodeficiency Virus Type 1 and the Chimeric Enzymes of Human Immunodeficiency Viruses Type 1 and Type 2 by Nonnucleoside Inhibitors," Antimicrob. Agents Chemother., 37, 1037-1042 (1993).
Kashman et al., "The Calanolides, a Novel HIV-Inhibitory Class of Courmarin Derivatives from the Tropical Rainforest Tree, Calophyllum lanigerum," J. Med. Chem., 35, 2735-2743 (1992).
Kumar et al., "Calocalabaxanthone, The Putative Isoprenyl Precursor of Calabaxanthone From Calophyllum Calaba," Phytochemistry, 21(3), 807-809 (1982).
Mabberlay, The Plant Book, (p. 92) (Cambridge University Press, 1987).
McCaffrey et al., "A Rapid Fluorometric DNA Assay for the Measurement of Cell Density and Proliferation In Vitro," In Vitro Cellular & Developmental Biology, 24(3, Part I), 247-252 (Mar., 1988).
Merigan, "Treatment of AIDS with Combinations of Antiretroviral Agents," Amer. J. of Medicine, 90(suppl. 4A), 8S-17S (Apr. 10, 1991).
Ohtani et al., "Absolute Configuration of Marine Diterpenes Possessing a Xenicane Skelton. An Application of an Advanced Mosher's Method," Tetrahedron Letters, 30(24), 3147-3150 (1989).
Ohtani et al., "A New Aspect of the High-Field NMR Application of Mosher's Method. The Absolute Configuration of Marine Triterpene Sipholenol-A," J. Org. Chem., 56, 1296-1298 (1991).
Patil et al., "The Inophyllums, Novel Inhibitors of HIV-1 Reverse Transcriptase," Programs and Abstracts of the Third International Conference on the Biotechnology of Microbial Products: Novel Pharmacological and Agrobiological Activities, P-31, 26 (Apr. 1993).
Pauwels et al., "Potent and selective inhibition HIV-1 Replication In Vitro by A Novel Series of TIBO Derivatives," Nature, 343, 470-474 (1990).
Rink et al., "Cytoplasmic pH and Free Mg.sup.2+ in Lymphocytes," J. of Cell Biology, 95, 189-196 (Oct., 1982).
Samaraweera et al., "Calozeylanic Acid, A New Bark Acid From Three Calophyllum Species," Tetrahedron Letters, 22(50), 5083-5086 (1981).
Shih et al., "Chimeric Human Immunodeficiency Virus Type 1/Type 2 Reverse Transcriptases Display Reversed Sensitivity to Nonnucleoside Analog Inhibitors," Proc. Natl. Acad. Sci. USA, 88, 9878-9882 (Nov. 1991).
Soejarto et al., "Challenges in Developing a New Drug from Tropical Rain Forest Plants," In Proceedings of the Symposium on the Industrial Utilization of Tropical Plants and the Conservation of Biodiversity, Enugu, Nigeria, Feb. 14-19, 1993 (in press).
Somanathan et al., "Chemical Investigation of Ceylonese Plants. Part VIII. Trapezifolixanthone, a New Di-isoprenylated Xanthone from the Bark of Calophyllum trapezifolium Thw. (Guttiferae)," J. C. S. Perkin I, 2515-2517 (1974).
Stout et al., "Calophyllum Products III. The Structures of Blancoic Acids," J. of Organic Chemistry, 33, 4185-4190 (1968).
Stout et al., "The Structure of Costatolide," J. of Organic Chemistry, 29, 3604-3609 (1964).
Swagler et al., "Pharmacokinetics of Anti-HIV Nucleosides in Microswine," J. Pharm. Pharmacol., 43, 823-826 (1991).
Vydac Reverse Phase HPLC Brochure, 26-27 (1992).
Weislow et al., "New Soluble-Formazan Assay for HIV-1 Cytopathic Effects: Application to High-Flux Screening of Synthetic and Natural Products for AIDS-Antiviral Activity," J. National Cancer Institute, 81(8), 577-586 (Apr. 19, 1989).
White et al., "A TIBO Derivative, R82913, Is A Potent Inhibitor of HIV-1 Reverse Transcriptase with Heteropolymer Templates," Antiviral Research, 16, 257-266 (1991).
Chaturvedi, et al., "Anticonvulsant and Antiinflammatory Activity of Natural Plant Coumarins and Triterpenoids", Research Communications In Chemical Pathology and Pharmacology, 9(1), 11-22 (Sep. 1974).
Kawazu et al., "Piscicidal Constituents of Capophyllum Inophyllum", Chemical Abstracts, 78(3), 207 (Jan. 22, 1973).
Boyd Michael R.
Cardellina, II John H.
Cragg Gordon M.
Fuller Richard W.
Gustafson Kirk R.
The Board of Trustees of the University of Illinois
The United States of America as represented by the Department of
Woodward Michael P.
LandOfFree
Calanolide and related antiretroviral compounds, compositions, 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 Calanolide and related antiretroviral compounds, compositions, a, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Calanolide and related antiretroviral compounds, compositions, a will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1764708