Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Reexamination Certificate
2005-07-05
2005-07-05
Wilson, James O. (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
C514S081000, C514S085000, C514S089000, C536S029200, C544S124000, C544S242000, C544S243000, C544S278000
Reexamination Certificate
active
06914052
ABSTRACT:
The present invention relates to dideoxynucleoside analog compounds containing a dideoxy ribofuranosyl moiety that exhibit selective anti-viral activity coupled with substantially low toxicity toward the host cells. In particular, the compounds according to the present invention show potent inhibition of the replication of the human immunodeficiency virus (HIV), while remaining substantially inert toward host cell DNA. Compounds according to the present invention exhibit primary utility as agents for inhibiting the growth or replication of retroviruses, particularly HIV. The compounds of the invention comprise a (2,3′-dideoxy-β-ribofuranosyl) ring coupled to a heterocyclic nucleobase that lacks an “O2 carbonyl”, that enables them to selectively react with and inhibit viral reverse transcriptase, while remaining substantially unreactive toward human DNA polymerases.
REFERENCES:
patent: 4092472 (1978-05-01), Townsend et al.
patent: 5627160 (1997-05-01), Lin et al.
patent: 6117849 (2000-09-01), Zimmermann et al.
patent: 6159951 (2000-12-01), Karpeisky et al.
patent: 6232300 (2001-05-01), Schinazi et al.
patent: 6248878 (2001-06-01), Matulic-Adamic et al.
patent: 6312892 (2001-11-01), Barany et al.
patent: 6447998 (2002-09-01), Froehler et al.
patent: 6495672 (2002-12-01), Froehler et al.
patent: 6576453 (2003-06-01), Barany et al.
patent: 2003/0082545 (2003-05-01), Barany et al.
patent: 0 038 569 (1981-10-01), None
patent: 0 043 722 (1982-01-01), None
patent: 0 236 935 (1987-09-01), None
patent: 0 544 010 (1993-06-01), None
patent: 01-066197 (1989-03-01), None
patent: WO 90/11081 (1990-10-01), None
patent: WO 94/01117 (1994-01-01), None
patent: WO 94/18971 (1994-09-01), None
patent: W O 97/41140 (1997-11-01), None
Searls et al., “Nucleoside Analogue Substitutions in the Trinucleotide DNA Template Recognition Sequence 3'-(CTG)-5' and Their Effects on the Activity of Bacteriophage T7 Primase,”Biochemistry, 39(15), 4375-4382 (Apr. 18, 2000).
Hildbrand et al. (I), “5-Substituted 2-Aminopyridine C-Nucleosides as Protonated Cytidine Equivalents: Increasing Efficiency and Specificity in DNA Triple-Helix Formation,”J. American Chemical Society, 119(24), 5499-5511 (Jun. 18, 1997).
Bates et al., “Efficient Triple Helix Formation by Oligonucleotides Containing α- or β-2-amino-5-(2-deoxy-D-ribofuranosyl)pyridine Residues,”Nucleic Acids Research, 24(21), 4176-4184 (Nov. 1, 1996).
Hildbrand et al. (II), Enhancing DNA Triple Helix Stability at Neutral pH by the Use of Oligonucleotides Containing a More Basic Deoxycyidine Analog,Angewandte Chemie, Intl. Ed., 35(17), 1968-1970 (1996); see alsoChemical Abstracts, 126(1), p. 943, Abstr. No. 8456u (Jan. 6, 1997).
Hsieh et al., “Synthesis of Two Pyridine C-Nucleosides as ‘Deletion-Modified’ Analogues of dT and dC,”Journal of Organic Chemistry, 60(16), 5356-5359 (Aug. 11, 1995).
Chen et al., “Use of pKaDifferences to Enhance the Formation of Base Triplets Involving C-G and G-C Base Pairs,”Journal of Organic Chemistry, 65(22), 7468-7474 (Nov. 3, 2000).
Minakawa et al., “Nucleosides and Nucleotides. 184. Synthesis and Conformational Investigation of Anti-Fixed 3-Deaza-3-halopurine Ribonucleosides,”Journal of Organic Chemistry, 64(19), 7158-7172 (Sep. 17, 1999).
Aoyagi et al. (I), “Nucleosides and Nucleotides. 115. Synthesis of 3-Alkyl-3-deazainosines v ia Palladium-Catalyzed Intramolecular Cyclization: A New Conformational Lock with the Alkyl Group at the 3-Position of 2-Deazainosine in Anti-Conformation,”Tetrahedron Letters, 34(1), 103-106 (Jan. 1, 1993).
Aoyagi et al. (II), “Synthesis of Imidazo[4,5-e][1,4]diazepine and 3-Substituted 3-Deazapurine Nucleosides from 1-Substituted Inosines,”18th Symposium on Nucleic Acids Chemistry, Nucleic Acids Symposium Series, 25, 57-58 (Oct. 29-31, 1991); see alsoChemical Abstracts, 117(25), Abstr. No. 251690d(Dec. 21, 1992).
Yamagata et al., “Conformation of 3-Substituted Purine Nucleosides Studied by X-Ray Crystallography and Theoretical Calculations,”Nucleosides&Nucleotides, 13(6&7), 1327-1335 (1994); see alsoChemical Abstracts, 121(13), p. 1073, Abstr. No. 158083f (Sep. 26, 1994);.
Orr et al., “DNA Chain Termination Activity and Inhibition of Human Immunodeficiency Virus Reverse Transcriptase by Carbocyclic 2',3'-Didehydro-2'.3'-dideoxyguanosine Triphosphate,”Journal of Biological Chemistry, 267(6), 4177-4182 (Feb. 25, 1992).
Serafinowski, et al.; “Synthesis and Antiviral Activity of Some New S-Adenosyl-L-Homocysteine Derivatives”;J. Med. Chem.; (1992); 35: 4576-4583.
Aoyagi, et al.; “Nucleosides and Nucleotides. 115. Synthesis of 3-Alkyl-3-Deazainosines via Palladium-Catalyzed Intramolecular Cyclization: A New Conformational Lock with the Alkyl Group at the 3-Position of the 3-Deazainosine in Anti-Conformation”;Tetrahedron Letters; (1993); 34: 1, 103-106.
Hildbrand, et al.; “Synthesis of Carbocyclic C-Nucleosides Containing Nonnatural Pyrimidine Bases”;Helvetica Chimica Acta; (1996); 79: 3, 702-709.
Chen, et al.; “Use of PKaDifferences To Enhance the Formation of Base Triplets Involving C-G amd G-C Base Pairs”;J. Org. Chem.; (2000); 65: 7468-7474.: ACS web publ. on Sep. 15, 2000.
Copy of International Search Report; International Application No.: PCT/US02/07447; mailed Oct. 2, 2002.
Stolze, et al.; “Synthesis of 3'-Sugar- and Base-Modified Nucleotides and Their Application as Potent Chain Terminators in DNA Sequencing”; (1999);Helvetica Chimica. ACTA; vol. 82, pp. 1311-1323.
Guo, et al.; “Inhibition of DNA polymerase reactions by pyrimidine nucleotide analogues lacking the 2-keto group”; (1998);Nucleic Acids Research; vol. 26, No. 8, pp. 1863-1869.
Chen DongLi
Fraley Andrew W.
Lan Tao
McLaughlin Larry W.
Crane, Esq. L. E.
Palmer & Dodge LLP
The Trustees of Boston College
Wilson James O.
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