β-2′- or 3′-halonucleosides

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai

Reexamination Certificate

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C514S042000, C514S043000, C514S046000, C514S047000, C514S048000

Reexamination Certificate

active

06949522

ABSTRACT:
The present invention includes compounds and compositions of β-halonucleosides, as well as methods to treat HIV, HBV or abnormal cellular proliferation comprising administering said compounds or compositions.

REFERENCES:
patent: 4211773 (1980-07-01), Lopez et al.
patent: 4625020 (1986-11-01), Brundidge et al.
patent: 4666892 (1987-05-01), Fox et al.
patent: 4681933 (1987-07-01), Chu et al.
patent: 4963662 (1990-10-01), Matthes et al.
patent: 5034518 (1991-07-01), Montgomery et al.
patent: 5128458 (1992-07-01), Montgomery et al.
patent: 5215970 (1993-06-01), Datema et al.
patent: 5246924 (1993-09-01), Fox et al.
patent: 5336764 (1994-08-01), Marquez et al.
patent: 5424416 (1995-06-01), Jones et al.
patent: 5426183 (1995-06-01), Kjell
patent: 5446029 (1995-08-01), Eriksson et al.
patent: 5565438 (1996-10-01), Chu et al.
patent: 5567688 (1996-10-01), Chu et al.
patent: 5574149 (1996-11-01), Van Tuttle et al.
patent: 5587362 (1996-12-01), Chu et al.
patent: 5637574 (1997-06-01), Burns et al.
patent: 5663154 (1997-09-01), Burns et al.
patent: 5703058 (1997-12-01), Schinazi et al.
patent: 5817799 (1998-10-01), Marquez et al.
patent: 6348587 (2002-02-01), Schinazi et al.
patent: 6355790 (2002-03-01), Rosenblatt et al.
patent: 0 292 023 (1988-11-01), None
patent: 0 316 017 (1989-05-01), None
patent: 0 352 248 (1990-01-01), None
patent: 0 357 571 (1990-03-01), None
patent: 0 409 227 (1991-01-01), None
patent: 0 463 470 (1992-01-01), None
patent: WO 88/09001 (1988-10-01), None
patent: WO 92/08727 (1992-05-01), None
patent: WO 94/14831 (1994-07-01), None
patent: WO 99/43691 (1999-09-01), None
patent: WO 01/90121 (2001-11-01), None
patent: WO 01/92282 (2001-12-01), None
Koshida et al. Antimicrobial Agents and Chemotherapy, 1989, pp. 2083-2088.
Pai Balakrishna, et al., Inhibition of Hepatitis B Virus by a Novel L-Nucleoside, 2′-Fluoro-5-Methyl-β-L-arabinofuranosyl Uracil,Antimicrobial Agents and Chemotherapy,Feb. 1996, 380-356.
Belen'kii, S. M.; Schinazi, R. S. Multiple drug effect analysis with confidence interval.Antiviral. Res.1994, 25, 1-11.
Bobek, M.; Bloch, A.; Parthasarathy, R.; Whistler, R. L. Synthesis and biological activity of 5-fluoro-4′-thiouridine and some related nucleosides.J. Med. Chem.1975, 18, 784-787), including 9-(4-thio-D-xylofuranosyl)adenine.
Choi, Y.; Choo, H.; Chong, Y.; Lee, S.; Olgen, S.; Schinazi, R. F.; Chu, C. K. Synthesis and potent anti-HIV activity of L-2′,3′-didehydro-2′,3′-dideoxy-2′-fluoro-4′-thiocytidine.Org. Lett.2002, 4, 305-307.
Chong, Y.; Gumina, G.; Chu, C. K.Tetrahedron Asymmetry.2000, 11, 4853-4875.
Chu, et al., Use of 2′-Fluoro-5-methyl-β-L-arabinofuranosyluracil as a Novel Antiviral Agent for Hepatitis B Virus and Epstein-Barr Virus;Antimicrobial Agents and Chemotherapy,Apr. 1995, 979-981.
Cooperwood et al.Nucleosides Nucleotides2000, 19 (1&2), 219.
Desgranges, C.; Razaka, G.; Rabaud, M.; Bricaud, H.; Balzarini, J.; De Clercq, E. Phosphorolysis of (E)-5-(2-bromovinyl)-2′-deoxyuridine (BVDU) and other 5-substituted-2′-deoxyuridines by purified human thymidine phosphorylase and intact blood-platelets.Biochem. Pharmacol.1983, 32, 3583-3590.
Dyson, M. R.; Coe, P. L.; Walker, R. T. The synthesis and antiviral properties of E-5-(2-bromovinyl)-4′-thio-2′-deoxyuridine.J. Chem. Soc., Chem. Commun.1991, 741-742.
Dyson, M. R.; Coe, P. L.; Walker, R. T. The synthesis and antiviral activity of some 4′-thio-2′-deoxy nucleoside analogs.J. Med. Chem.1991, 34, 2782-2786.
Ford, H. Jr.; Dai, F.; Mu, L.; Siddiqui, M. A.; Nicklaus, M. C.; Anderson, L.; Marquez, V. E.; Barchi, J. J. Jr. Adenosine deaminase prefers a distinct sugar ring conformation for binding and catalysis: Kinetic and structural studies.Biochemistry,2000, 39, 2581-2592.
Fu, Y.-L.; Bobek, M. InNucleic Acid Chemistry;Townsend, L.; Tipson, R. S., Eds.; John Wiley & Sons: New York, 1978; pp 317-323.
Hanessian, S.; Murray, P. J. Stereochemical control of nature's biosynthetic pathways: A general strategy for the synthesis of polypropionate-derived structural units from a single chiral progenitor.Tetrahedron1987, 43, 5055-5072.
Herdewijn, P. Structural requirements for activiral activity in nucleosides.Drug Discov. Today,1997, 2, 235-242.
Borthwick, et al., Synthesis and Enzymatic Resolution of Carbocyclic 2′-Ara-fluoro-Guanosine: A Potent New Anti-Herpetic Agent,J. Chem. Soc., Chem. Commun,1988.
Bouffard, Kinetic Studies of 2′,2′-difluorodeoxycytidine (Gemcitabine) with Purified Human Deoxycytidine Kinase and Cytidine Deaminase,BioChemical Pharmacology,vol. 45 (No. 9) pp. 4857-1861, 1993.
Lee et al.J. Med. Chem.2002, 45, 1313-1320.
Lee, K.; Choi, Y.; Gullen, E.; Schlueter-Wirtz, S.; Schinazi, R. F.; Cheng, Y.-C.; Chu, C. K. Synthesis and anti-HIV and anti-HBV activities of 2′-fluoro-2′,3′-unsaturated L-nucleosides.J. Med. Chem.1999, 42, 1320-1328.
Lee, K.; Chu, C. K. Molecular modeling approach to understanding the mode of action of L-nucleosides as antiviral agents.Antimicrob. Agents Chemother.2001, 45, 138-144.
Ma et al.,J. Med. Chem.1996, 39 (14), 2835.
Marquez, V. E.; Tseng, C. K.-H.; Mitsuya, H.; Aoki, S.; Kelley, J. A.; Ford, H. Jr.; Roth, J. S.; Broder, S.; Johns, D. G.; Driscoll, J. S. Acid-stable 2′-fluoro purine dideoxynucleosides as active agents against HIV.J. Med. Chem.1990, 33, 978-985.
Martin, et.al., Synthesis and Antiviral Activity of Monofluoro and Difluoro Analogues of Pyrimidine Deoxyribonucleosides against Human Immunodeficiency Virus (HIV-1),J. Med. Chem.1990, 33, 2137-2145.
Ototani, N.; Whistler, R. L. Preparation and antitumor activity of 4′-thio analogs of 2,2′-anhydro-1-β-D-arabinofuranosylcytosine.J. Med. Chem.1974, 17, 535-537.
Parks, R. E., Jr.; Stoeckler, J. D.; Cambor, C.; Savarese, T. M.; Crabtree, G. W.; Chu, S.-H. In Molecular Actions and Targets for Cancer Chemotherapeutic Agents; Sartorelli, A. C. Lazo, J. S., Bertino, J. R., Eds.; Academic Press: New York, 1981; pp 229-252.
Philpott, M.S., Ebner, J.P., Hoover, E.A., “Evaluation of 9-(2-phosphonylmethoxyethyl) adenine therapy for feline immunodeficiency virus using a quantitative polymerase chain reaction,”Vet. Immunol. Immunopathol.35:155166, 1992.
Reist, E. J.; Gueffroy, D. E.; Goodman, L. Synthesis of 4-thio-D-& L-ribofuranose and corresponding adenine nucleosides.J. Am. Chem. Soc.1964, 86, 5658-5663.
Reist, E. J.; Fisher, L. V.; Gueffroy, E.; Goodman, L. Neighboring-group participation. Preparation of dithiopentose sugars via a thioacylonium ion intermediate.J. Org. Chem.1968, 33, 189-192.
Secrist III, J. A.; Riggs, R. H.; Tiwari, K. N.; Montgomery, J. A. Synthesis and anti-HIV activity of 4′-thio-2′,3′-dideoxynucleosides.J. Med. Chem.1992, 35, 533-538.
Secrist III, J. A.; Tiwari, K. N.; Riordan, J. M.; Montgomery, J. A. Synthesis and biological activity of 2′-deoxy-4-′thio pyrimidine nucleosides,J. Med. Chem.1991, 34, 2361-2366.
Secrist, J. A.; Tiwari, K. N.; Shortnacy-Fowler, A. T.; Messini, L.; Riordan, J. M.; Montgomery, J. A. Synthesis and biological activity of certain 4′-thio-D-arabinofuranosylpurine nucleosides.J. Med. Chem.1998, 41, 3865-3871.
Sellon D.C., “Equine Infectious Anemia,”Vet. Clin. North Am. Equine Pract. United States,9: 321-336, 1993.
Sterzycki, et al., Synthesis and Anti-HIV Activity of Several 2′-Fluoro-Containing Pyrimidine Nucleosides,J. Med. Chem.1990.
Takagi, R.; Nakamura, M.; Hashizume, M.; Kojima, S.; Ohkata, K. Stereoselective cyclopropanation of 3-aryl-2-phosphonoacrylates induced by the (-)-8-phenylmenthyl group as a chiral auxiliary.Tetrahedron lett.2001, 42, 5891-5895.
Uenishi, J.; Motoyama, M.; Nishiyama, Y.; Wakabayashi, S. Stereocontrolled preparation of cyclic xanthate—A novel synthetic route to 4-thiofuranose and 4′-thionucleoside.J. Chem. Soc., Chem. Commun.1991, 1421-1422.
Wang, P.; Hong, J. H.; Cooperwood, J. S.; Chu, C. K. Recent advances in L-nucleosides: chemistry and biol

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