Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Reexamination Certificate
2005-11-01
2005-11-01
Wilson, James O. (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
C514S045000, C514S256000, C514S269000, C514S274000, C514S300000, C536S025300, C536S028100, C536S028200, C536S028400, C536S028500, C536S022100, C536S024300, C536S024500, C536S026230, C536S026260, C536S026700, C536S026800, C536S027140, C536S028540, C544S314000
Reexamination Certificate
active
06960568
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.
REFERENCES:
patent: 4381344 (1983-04-01), Rideout et al.
patent: 6211158 (2001-04-01), Seela et al.
patent: 6455506 (2002-09-01), Townsend et al.
Minakawa et al. J. Org.Chem. 64, 7158-7172, 1999.
Rousseau, Robert J. et al.; The Synthesis of 4-Amino-β-D-ribofuranosylimidazo (4,5-c) pyridine (3-Deazaadenosine) and Related Nucleotides; Biochemistry; pp 756-760, 1966.
Montgomery, John A. et. al; 3-Deaza-6-methylthiopurine Ribonucleoside1;vol. 9; pp 105-107, 1966.
Rousseau, Robert J., et al; The Synthesis of 3-Deaze-6-thioguanine and Certain Related Derivatives; Apr. 1974; vol. 11; pp. 233-235.
May, Jesse A, et. al; A General Synthesis of 4-Substituted 1-(β-o-Ribofuranosyl) imidazo-(4,5-c) pyridines +; 1975, J.C.S. Perkin; pp 125-129.
Cook, P. Dan, et. al; A New Class of Potent Guanine Antimetabolites. Synthesis of 3-Deazaguanine, 3-Deazaguanosine, and 3-Deazaguanylic Acid by a Novel Ring Closure or Imidazole Precursors; May 14, 1975; Journal of American Chemical Society; pp 2916, 2917.
May, Jesse A. et al.; Synthesis of 6-Amino-1-(β-D-Ribofuranosyl) Imidazo [4,5-c]-Pyridin-4-Thione (3-Deaza-6-Thioguanosine) and Certain Related Derivatives1; 1975; pp 371-394.
Cook, P. Dan et al; Synthesis of 3-Deazaguanine, 3-Deazaguanosine, and 3-Deazaguanylic Acid by a Novel Ring Closure of Imidazole Precursors; Mar. 17, 1976; Journal of the American Chemical Society; pp 1492-1498.
Montgomery, John A. et al.; A Comparison of Two Methods for the Preparation of 3-Deazapurine Ribonucelosides; Apr., 1977; vol. 14; pp 195-197.
Chiang, Peter K. et al.; S-Adenosyl-τ—honocysteine Hydrolase: Analogues of S-Adensoyl-τ—homocysteine as Potential Inhibitors; May 19, 1977; Molecular Pharmacology; pp 393-947.
May, Jesse A. et al.; Synthesis of 6-Amino-1-(β-D-Ribofuranosyl) Imidazo [4,5-c]-Pyridin-4-Thione (3-Deaza-6-Thioguanosine) and Certain Related Derivatives1; 1975; pp 371-394.
Cook, P. Dan et al.; Synthesis of 3-Deazaguanine, 3-Deazaguanosine, and 3-Deazaguanylic Acid by a Novel Ring Closure of Imidazole Precursors; Mar. 17, 1976; Journal of the American Chemical Society; pp 1492-1498.
Montgomery, John A. et al.; A Comparison of Two Methods for the Preparation of 3-Deazapurine Ribonucelosides; Apr., 1977; vol. 14; pp 195-197.
Chiang, Peter K. et al.; S-Adenosyl-τ—honocysteine Hydrolase: Analogues of S-Adenosyl-τ—homocysteine as Potential Inhibitors; May 19, 1977; Molecular Pharmacology; pp 939-947.
Allen, Louis B. et al.; Antiviral Activity of 3-Deazaguanine, 3-Deazaguanosine, & 3-Deazaguanylic Acid; Antimicrobial Agents and Chemothreapy; Jul., 1977; vol. 12, No. 1; pp 114-119.
Cook, Dan P. et al.; Synthesis of 7-and 9-β-D- Ribofuranosides of 3-Deaza-6-thioguanine and 3-Deaza-2,6-diaminopurine by a Novel Ring Closure of 4(5)-Cyano-5(4)-cynnomethylimidazole β-D- Ribofuranosides; 1978; J. Org. Chem.; vol. 43, No. 2; pp 289-293.
Chiang, Peter K. et al.; Adenosylhomocysteine inhibitors: Synthesis of 5′-deoxy—5′—(isobutylthio)-3-deazaadenosine and its effect onRous sarcomavirus and Gross murine leukemia virus; May 30, 1978; Biochemical and Biophysical Research Communications; vol. No. 82, No. 2; pp 417-423.
Bader, John P. et al.; 3-Deazaadenosine, an Inhibitor of Adenosylhomocysteine Hydrolase Inhibits Reproduction ofRous sarcomavirus and Transformation of Chick Embryo Cells; 1978; Virology; pp 494, 360-365, 1063.
Poonian, Mohibdar S, et al; Synthesis of Arabinofuranosyl Derivatives of 3-Deazaguanine; 1979; Journal of Medical Chemistry; vol. 22, No. 8; pp 958-962.
Streeter, David G., et al.; 7-Ribosyl-3-Deazaguanine-Mechanism of Antibacterial Action; 1980; Biomedical Pharmacology; vol. 29; pp 1791-1797.
Guranowski, Andrzej, et al; Adenosine Analogues as Substrates and Inhibitors of S-Adenosylhomocusteine Hydrolase; 1981; American Chemical Society; pp 110-115.
Actions of 3-deazaguanine and 3-deazaguanosine on variant lines of Chinese hamster ovary cells; 1981; Biochemical Pharmacology; vol. 30, No. 16; pp 2374-2376.
Bodner, Ann J., et al; Anti-Viral Activity of 3-Deazaadenosine and 5′-Deoxy-5′-Isobutylthio-3-Deazaadenosine (3-deaza-SIBA); Jan. 30, 1981; Biochemical and Biophysical Research Communications; vol. 98, No. 2; pp 476-481.
Khwaja, Tasneem A.; 3-Deazaguanine, a Candidate Drug for the Chemotherapy of Breast Carcinomas?; Oct., 1982; Cancer Treatment Reports; vol. 66, No. 10; pp 1853-1858.
Montgomery, J.A., et al; 1-β-D-Arabinofuranosyl-1-H-inidazo [4,5-,] pyridine (ara-3-Deazaadenine); 1981; American Chemical Society; pp 96-98.
Mian, A. Mohsin, et al; Synthesis and Antitumor Activity of 2-Deoxyribofuranosides of 3-Deazaguanine; 1983; American Chemical Society; pp 286-291.
Revankar, Ganapathi, R., et al; Synthesis and Antiviral/Antitumor Activities of Certain 3-Deazaguanine Nucleosides and Nucleotides; 1984; American Chemical Society; pp 1389-1396.
Gupta, Pranab K., et al; A new synthesis of certain 7-(β-D-ribofuranosyl) and 7-(2-deoxy-β-D-ribofuranosyl)and 7-(2-deoxy-β-D-ribofuranosyl) derivatives of 3-deazaguanine via the sodium salt glycosylation procedure; 1985; Nucleic Acids Research; vol. 13, No. 14; pp 5341-5352.
Berry, David A. et al; Synthesis of 8-Amino-3-deazaguanine via Imidazole Precursors. Antitumor Activity and Inhibition of Purine Nucleoside Phosphorylase; 1986; J. Med. Chem.; pp 2034-2037.
Krenitsky, Thomas K. et al; Imidazo [4,5-c] pyridines (3-Deazapurines) and Their Nucleosides as Immunosuppressive and Antiiflammatory Agents; 1986; J. Med. Chem.; pp 138-143.
Mian, A. Mohsin, et al; Antitumor Activity and Mechanism of Action of 6-Thio-3-deazaguanine; Apr. 1, 1987; Cancer Research 47; pp 1863-1866.
Bennett, L. Lee, et al; Alterations in Nucleotide Pools Induced by 3-Deazaadenosine and Related Compounds; 1988; Biochemical Pharmology; vol. 37, No. 7; pp 1233-1244.
McGee, Danny P.C., et al; Synthesis and Antiviral Activity of the 3-Deaza Analogue of 9-((1,3-Dihydroxy-2-Propoxy)Methyl) Guanine; 1990; Nucleosides & Nucleotides; pp 815-826.
Serafinowski, Pawel; Synthesis of 2′,3′-Dideoxy-3-deazaadenosine and Some of its Analogues; Sep., 1990; pp 757-760.
Seels, Frank, et al; 173.3-Deazaguanine N7-and N9-(2′-Deoxy-β-D-ribofuranosides): Building Blocks for Solid-Phase Synthesis and Incorporation into Oligodeoxyribonucelotides; 1991; Helvetica Chmica Acta; vol. 74; pp1790-1800.
Minakawa, Noriaki et al; Nucleosides and Nucleotides. 114. A Convenient Method for the Synthesis of 3-Deazapurine Nucleosides from AICA-Ribsode1; 1994; Tetrahedron Letters, vol. 34, No. 4; pp 661-664.
Acevedo, Oscar, L., et al; Synthesis of Several 2′-Deoxy-3-Alkyl(Aryl)-3-Deazaguanosines: Mild Alkylation of a Cyanomethyl Imidazole with Electrophiles; 1993; Nucleosides and Nucleotides; pp 403-416.
Siddiqi, Suhaib, M. et al; 3-Deaza-5′-noraristeromycin and Their Antiviral Properties; 1995; Journal of Medical Chemistry; vol. 38, No. 6; pp 1035-1038.
Cheng Yung-Chi
Liu Mao-Chin
Sartorelli Alan C.
Coleman Henry D.
Khare Devesh
Sapone William J.
Sudol R. Nell
Wilson James O.
LandOfFree
Nucleosides and related processes, pharmaceutical... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Nucleosides and related processes, pharmaceutical..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Nucleosides and related processes, pharmaceutical... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3457782