Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Reexamination Certificate
2011-08-30
2011-08-30
McIntosh, III, Traviss C (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
C536S018700, C536S029200, C536S055000
Reexamination Certificate
active
08008264
ABSTRACT:
Provided are pyrrolo[1,2-f][1,2,4]triazinyl, imidazo[1,5-f][1,2,4]triazinyl, imidazo[1,2-f][1,2,4]triazinyl, and [1,2,4]triazolo[4,3-f][1,2,4]triazinyl nucleosides, nucleoside phosphates and prodrugs thereof, wherein the 1′ position of the nucleoside sugar is substituted. The compounds, compositions, and methods provided are useful for the treatment of Flaviviridae virus infections, particularly hepatitis C infections.
REFERENCES:
patent: 4816570 (1989-03-01), Farquhar
patent: 4968788 (1990-11-01), Farquhar
patent: 5663159 (1997-09-01), Starrett, Jr. et al.
patent: 5792756 (1998-08-01), Starrett, Jr. et al.
patent: 6312662 (2001-11-01), Erion et al.
patent: 7105493 (2006-09-01), Sommadossi et al.
patent: 7608597 (2009-10-01), Sommadossi et al.
patent: 2004/0006002 (2004-01-01), Sommadossi et al.
patent: 2010/0021425 (2010-01-01), Butler et al.
patent: 2010/0298257 (2010-11-01), Ross et al.
patent: WO-1991/019721 (1991-12-01), None
patent: WO-2000/056734 (2000-09-01), None
patent: WO-2000/56734 (2000-09-01), None
patent: WO-01/32153 (2001-05-01), None
patent: WO-01/60315 (2001-08-01), None
patent: WO-01/90121 (2001-11-01), None
patent: WO-02/18404 (2002-03-01), None
patent: WO-02/32920 (2002-04-01), None
patent: WO-2002/032920 (2002-04-01), None
patent: WO-02/057287 (2002-07-01), None
patent: WO-02/057425 (2002-07-01), None
patent: WO-2004/046331 (2004-06-01), None
patent: WO-05/123087 (2005-12-01), None
patent: WO-2006/031725 (2006-03-01), None
patent: WO-06/050161 (2006-05-01), None
patent: WO-2006/065335 (2006-06-01), None
patent: WO-2006/121820 (2006-11-01), None
patent: WO-2007/027248 (2007-03-01), None
patent: WO-2007/056170 (2007-05-01), None
patent: WO-2007/064883 (2007-06-01), None
patent: WO-2007/064931 (2007-06-01), None
patent: WO2008/005542 (2008-01-01), None
patent: WO-2008/005542 (2008-01-01), None
patent: WO-2008/41079 (2008-04-01), None
patent: WO-2008/79206 (2008-07-01), None
patent: WO-2008/082601 (2008-07-01), None
patent: WO-2008/085508 (2008-07-01), None
patent: WO-2008/089105 (2008-07-01), None
patent: WO-2008/116064 (2008-09-01), None
patent: WO2008/141079 (2008-11-01), None
patent: WO-2008/141079 (2008-11-01), None
patent: WO-2009/131926 (2009-10-01), None
patent: WO-2009/132123 (2009-10-01), None
patent: WO-2009/132135 (2009-10-01), None
patent: WO-2010/002877 (2010-01-01), None
patent: WO-2010/036407 (2010-04-01), None
Arimilli, MN et al. (1997) “Synthesis, in vitro biological evaluation and oral bioavailability of 9-[2-(phosphonomethoxy)propyl]adenine (PMPA) prodrugs”,Antiviral Chemistry & Chemotherapy, vol. 8(6), p. 557-564.
Benzaria, S. et al. (1996) Synthesis in Vitro Antiviral Evaluation, and Stability Studies of Bis(S-acyl-2-thioethyl) Ester Derivatives of 9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA) as Potential PMEA Prodrugs with Improved Oral Bioavailability,Jounral of Medicinal Chemistry, vol. 39, pp. 4958-4965.
Bio, M. et al. (2004) , “Practical Synthesis of a Potent Hepatitis C Virus RNA Replication Inhibitor”,Journal of Organic Chemistry, vol. 69, pp. 6257-6266.
Bobeck D.R. et al. (2010) “Advances in nucleoside monophosphate prodrugs as anti-HCV agents”, Antiviral Therapy, vol. 15, pp. 935-950.
Bojack G. et al. (2001), “Design and Synthesis of Inhibitors of Adenosine and AMP Deaminases”,Organic Letters, vol. 3(6), pp. 839-842.
Boyer, N. et al. (2000), “Pathogenesis, diagnosis and management of hepatitis C”,Journal of Hepatology, vol. 32, pp. 98-112.
Calisher, C. et al. (1989) “Antigenic Relationships between Flaviviruses as Determined by Cross-neutralization Tests with Polyclonal Antisera”,Journal of General Virology, vol. 70, pp. 37-43.
De Clercq, E. (2001) “Antiviral drugs: current state of the art”,Journal of Clinical Virology, vol. 22, pp. 73-89.
De Clercq, E. (2001) “Molecular Targets for Antiviral Agents”The Journal of Pharmacology and Experimental Therapeutics, vol. 297(1), pp. 1-10.
De Francesco, R. et al. (2003) “Approaching a new era for hepatitis C virus therapy: inhibitors of the NS3-4A serine protease and the NS5B RNA-dependent RNA polymerase”,Antiviral Research, vol. 58, pp. 1-16.
De Lombaert, S. et al. (1994)N--Phosphonomethyl Dipeptides and Their Phosphonate Prodrugs, a New Generation of Neutral Endopeptidase (NEP, EC 3.4.24.11) Inhibitors1,Journal of Medicinal Chemistry, vol. 37, pp. 498-511.
Di Bisceglie, A. et al. (1999) “The Unmet Challenges of Hepatitis C”,Scientific American, Inc. Oct, pp. 80-85.
Dolzhenko, A.V. et al. (2008) “Pyrazolo[1,5-a][1,3,5]Triazines(5-AZA-9- Deazapurines):Synthesis and Biological Activity1” -Heterocycles, vol. 75, no. 7.
Dudfield, P. et al. (1999) “Synthesis of C- ribosyl imidazo[2,1-f][1,2,4]triazines as inhibitors of adenosine and AMP deaminases,” J. Chem.Soc, Perkin Trans I2929-2936.
Dudfield, P.J. et al. (1999) “Synthesis of C--ribosyl 1,2,4-triazolo[3,44}][1,2,4]triazines as inhibitors of adenosine and Amp deaminases”, J. Chem. Soc., Perkin Trans 1, pp. 2937-2942.
Dymock, B. et al. (2000) “Novel approaches to the treatment of hepatits C virus infection”,Antiviral Chemistry & Chemotherapy, vol. 11, pp. 79-96.
Farquhar, D. et al. (1983), “Biologically Reversible Phosphate-Protective Groups”,Journal of Pharmaceutical Sciences, vol. 72(3), pp. 324-325.
Gleeson, P.M. et al. (2003) “Prediction of the potency of inhibitors of adenosine deaminase by QM/MM calculations”Chem. Comm.pp. 2180-2181.
Gordon, C.P. et al. (2005) “Control of Hepatitis C: A Medicinal Chemistry Perspective”,Journal of Medicinal Chemistry, vol. 48(1), pp. 1-20.
Haraguchi, K. et al. (1995) “Stereoselective Synthesis of 1'-C-Branched Uracil Nucleosides From Uridine,”Nucleosides & Nucleotides14(3-5):417-420.
Hayashi, M. et al. (1992) “C-Nucleosides, a Synthesis of 2-Substituted 7-(-β-D-Ribofuranosyl)-Pyrrolo [2,14]-1,2,4-Triazines. A New Type of “Purine Like” C-Nucleoside,”Heterocycles34(3):569-574.
Hecker, S.J.et al. (2007), “Liver Targeted Prodrugs of 2'-C--Methyladenosine for Therapy of Hepatitis C Virus Infection”,Journal of Medicinal Chemistry, vol. 50, pp. 3891-3896.
International Search Report and Written Opinion for PCT/US2009/041432 mailed on Aug. 11, 2009.
International Search Report for PCT/US2009/041447, mailed on Aug. 7, 2009.
International Search Report for PCT/US2010/049471, mailed Nov. 18, 2010.
International Search Report for PCT/US2010/049508, filed Sep. 20, 2010, mail date Nov. 5, 2010.
Itoh, Y. et al. (1995) “Divergent and Stereocontrolled Approach to the Synthesis of Uracil Nucleosides Branched at the Anomeric Position,”J. Org. Chem,. 60:656-662.
Moradpour, D. et al. (2007) “Replication of hepatitis C virus”,Nature Reviews Microbiology, Jun., vol. 5, pp. 453-463.
Nishimura, N. (2001) “Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin,”Carbohydrate Research331:77-82.
Otter, B. et al. (1996) “Conformational Properties of Purine-LikeC-Nucleosides”,Nucleosides & Nucleotides, vol. 15(1-3), pp. 793-807.
Patil, S. et al. (1994) “4-Aza-7,9-Dideazaadenosine, a New Cytotoxic Synthetic C-Nucleoside Analogue of Adenosine,”Tetrahedron Letters35(30):5339-5342.
Patil, S.A. et al. (1994) “Synthesis of Pyrrolo[2,1-f][1,2,4]triazine Congeners of Nucleic Acid Purines via the N-Amination of 2-Substituted Pyrroles[1 ]”,Journal of Heterocyclic Chemistry, vol. 31, pp. 781-786.
Puech, F. et al. (1993) “Intracellular delivery of nucleoside monophosphates through a reductase-mediated activiation process”Antiviral Research, vol. 22, pp. 155-174.
Ramasamy, K. et al. (1986) “Synthesis and Antitumor Activity of Certain 3-(3-DRibofuranosy1-1,2,4-triazolo[3,44]-1,2,4-triazines Related to Formycin Prepared via Ring Closure of a 1,2,4-Triazine Precursor&
Butler Thomas
Cho Aesop
Kim Choung U.
Parrish Jay
Saunders Oliver L.
Gilead Sciences, Inc.
McIntosh, III Traviss C
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