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  Novel nucleosides and related processes, pharmaceutical compositions and methodsUSPTO Application #: 20050239726Title: Novel nucleosides and related processes, pharmaceutical compositions and methods Abstract: The invention provides novel nucleosides and related processes, pharmaceutical compositions, and methods. The novel nucleosides are useful in a wide variety of antiviral, antineoplastic, and antibacterial applications. Preferred embodiments of the instant invention include novel 2 halogen-substituted, 3 halogen-substituted, and 2′,3′dihalogen-substituted analogues of 3-deazaadenosine, and novel 3 halogen-substituted analogues of 3-deazaguanosine. Compounds of the instant invention, including 4-Amino-6-fluoro-1-(β-D-ribofuranosyl)imidazo[4,5-c]pyridine and 6-Amino-7-bromo-1,5-dihydro-1-β-D-ribofuranosylimidazo[4,5-c]pyridin-4-one, have exhibited potent antiviral and anticancer activity in vitro. The compounds are also useful in the concomitant treatment of bacterial infections associated with viral infections such as AIDS. (end of abstract) Agent: Coleman Sudol Sapone, P.C. - Bridge Port, CT, US Inventors: Alan C. Sartorelli, Yung-Chi Cheng, Mao-Chin Liu USPTO Applicaton #: 20050239726 - Class: 514043000 (USPTO) Related Patent Categories: Drug, Bio-affecting And Body Treating Compositions, Designated Organic Active Ingredient Containing (doai), O-glycoside, , Nitrogen Containing Hetero Ring The Patent Description & Claims data below is from USPTO Patent Application 20050239726. Brief Patent Description - Full Patent Description - Patent Application Claims
FIELD OF THE INVENTION [0001] The invention provides novel nucleosides and related processes, pharmaceutical compositions, and methods. The novel nucleosides are useful in a wide variety of antiviral, antineoplastic, and antibacterial applications. Preferred embodiments of the instant invention include novel 2 halogen-substituted, 3 halogen-substituted, and 2', 3'dihalogen-substituted analogues of 3-deazaadenosine, and novel 3 halogen-substituted analogues of 3-deazaguanosine. Compounds of the instant invention, including 4-Amino-6-fluoro-1-(.beta.-D-ribofuranosyl)i- midazo[4,5-c]pyridine and 6-Amino-7-bromo-1,5-dihydro-1-.beta.-D-ribofuran- osylimidazo[4,5-c]pyridin-4-one, have exhibited potent antiviral and anticancer activity in vitro. The compounds are also useful in the concomitant treatment of bacterial infections associated with viral infections such as AIDS. BACKGROUND OF THE INVENTION [0002] Considerable progress has been made in developing nucleosides with anticancer and/or antiviral activity by modifying the base portion of a nucleoside. For example, 3-deazaadenosine, a potent inhibitor of adenosylhomocysteine hydrolase, has been shown to have significant activity against herpes simplex virus type-1, human immunodeficiency virus and oncogenic DNA viruses. Bodner, A. J.; Cantoni, G. L.; Chiang, P. K. Biochem. Biophys. Res. Commun. 1981 98,476-481. Flexner, C. W.; Hildreth, J. E.; Kuncl, R. W.; Drachman, D. B. Lancet 1992 339, 438. Bader, J. P.; Brown, N. R.; Chiang, P. K.; Cantoni, G. L. Virology 1978 89, 494-505. Chiang, P. K.; Cantoni, G. L.; Bader, J. P.; Shannon, W. M.; Thomas, H. J.; Montgomery, J. A. Biochem. Biophys. Res. Commun. 1978 82 417-423. 3-Deazaguanosine has been reported to possess broad spectrum antiviral activity against a variety of DNA and RNA viruses, as well as antitumor activity against the L1210 leukemia and several mammary adenocarcinomas in mice. Allen, L. B.; Huffman, J. H.; Cook, P. D.; Meyer, R. B., Jr.; Robins, R. K.; Sidwell, R. W. Antimicrob. Agents Chemother. 1977 12, 114-119. Saunders, P. P.; Chao, L. Y.; Loo, T. L.; Robins, R. K. Biochem. Pharmacol. 1981 30, 2374-2376. Revankar, G. R.; Gupta, P. K.; Adams, A. D.; Dalley, N. K.; McKernan, P. A.; Cook, P. D.; Canonico, P. G.; Robins, R. K. J. Med. Chem., 1984 27, 1389-1396. [0003] Certain 2-halogen-substituted purine nucleosides have exhibited cytotoxicity in vitro and anticancer activity in vivo. Carson, D. A.; Wasson, D. B.; Kaye, J.; Ullman, B.; Martin, D. W., Jr.; Robins, R. K.; Montgomery, J. A. Proc. Natl. Acad. Sci. USA 1980 77, 6865-6869. Hutton, J. J.; Von Hoff, D. D.; Kuhn, J.; Phillips, J.; Hersh, M.; Clark, G. Cancer Res. 1984 44, 4183-4186. Secrist, J. A., III; Shortnacy, A. T.; Montgomery, J. A. J. Med. Chem. 1988 31, 405-410. Montgomery, J. A.; Shortnacy-Fowler, A. T.; Clayton, S. D.; Riordan, J. M.; Secrist, J. A., III. J. Med. Chem. 1992 35, 397-401. Among these analogues, Fludarabine phosphate (9-.beta.-D-arabinofuranosyl-2-fluoroadenine 5'-O-phosphate) and Cladribine (2-chloro-2'-deoxy-.beta.-D-adenosine) are currently used as anticancer agents. [0004] However, notwithstanding the progress that has been made in identifying nucleosides having anticancer and/or antiviral activity, the need exists for biologically-active nucleosides that exhibit a wide range of antiviral and/or anticancer properties and that may be employed in antiviral and anticancer pharmaceutical compositions. Such nucleosides must be safe and well-tolerated and be suitable for use in numerous pharmaceutical dosage forms and routes of administration. Preferably, such nucleosides would exhibit both antineoplastic and antiviral activity upon administration to a patient in need, and would also be useful in treating bacterial infections such as tuberculosis and associated viral infections such as AIDS. OBJECTS OF THE INVENTION [0005] It is an object of the instant invention to provide novel, biologically-active nucleosides useful in a wide range of antiviral, antineoplastic, and antibacterial applications. [0006] It is a further object of the instant invention to provide novel, biologically-active nucleosides that may be employed in antiviral and anticancer pharmaceutical compositions and which are also effective against bacterial infections and bacterial infections associated with viral infections such as AIDS. [0007] It is a further object of the instant invention to provide novel, biologically-active nucleosides that are safe and well-tolerated. [0008] It is a further object of the instant invention to provide methods of using novel, biologically-active nucleosides to treat viral, bacterial and neoplastic conditions. [0009] It is a further object of the instant invention to provide novel processes for making novel, biologically-active nucleosides. SUMMARY OF THE INVENTION [0010] In accordance with the above stated objects, the instant invention provides novel nucleosides of the formula (I): 1 [0011] and anomers, pharmaceutically acceptable salts, solvates, or polymorphs thereof where R.sup.1, R.sup.2 and R.sup.3 are selected from OH, SH, NRR' or a halogen group (F, Cl, Br or I); R.sup.4 and R.sup.5 are selected from H, OH, a halogen group or together form an unsaturated double bond between the 2' and 3' positions (i.e., the carbons to which R.sup.4 and R.sup.5 are attached); and R and R' are independently selected from H or a C.sub.1-C.sub.3 alkyl group. The invention also provides antiviral, bacterial and antineoplastic (including anticancer) pharmaceutical compositions comprising the novel nucleosides, methods of using these pharmaceutical compositions to treat a wide variety of viral, bacterial and neoplastic conditions, and processes for making the novel nucleosides. [0012] The beta-anomer of compounds of formula (1) is preferred, and that anomer is illustrated below in formula (II): 2 [0013] Preferred nucleosides of the instant invention include compounds of the following formulae (III) through (X): 3 [0014] where X is a halogen group (F, Cl, Br or I); 4 [0015] where X is a halogen group (F, Cl, Br or I) and A is an alkyl group; 5 [0016] where X is a halogen group (F, Cl, Br or I); 6 [0017] where X is a halogen group (F, Cl, Br or I); 7 [0018] where X is a halogen group (F, Cl, Br or I); 8 [0019] where X and Y are the same or different and are a halogen group (F, Cl, Br or I); 9 [0020] where X and Y are the same or different and are a halogen group (F, Cl, Br or I); and 10 Continue reading... 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