3-β-D-ribofuranosylthiazolo[4-5-d]pyrimidine...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

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C514S046000

Reexamination Certificate

active

07943759

ABSTRACT:
The invention is directed to 3-β-D-ribofuranosylthiazolo[4,5-d]pyrimidine nucleosides and pharmaceutical compositions containing such compounds that have immunomodulatory activity. The invention is also directed to the therapeutic or prophylactic use of such compounds and compositions, and to methods of treating diseases and disorders described herein, by administering effective amounts of such compounds.

REFERENCES:
patent: 4539205 (1985-09-01), Goodman et al.
patent: 4643992 (1987-02-01), Goodman et al.
patent: 5011828 (1991-04-01), Goodman et al.
patent: 5041542 (1991-08-01), Robins et al.
patent: 5166141 (1992-11-01), Goodman et al.
patent: 5395937 (1995-03-01), Nikolaides et al.
patent: 5821236 (1998-10-01), Krenitsky et al.
patent: 6028076 (2000-02-01), Hirota et al.
patent: 6329381 (2001-12-01), Kurimoto et al.
patent: 6376501 (2002-04-01), Isobe et al.
patent: 6924271 (2005-08-01), Averett et al.
patent: 7321033 (2008-01-01), Averett et al.
patent: 7745415 (2010-06-01), Averett et al.
patent: 2002/0173655 (2002-11-01), Dellaria et al.
patent: 2003/0065005 (2003-04-01), Charles et al.
patent: 2003/0100764 (2003-05-01), Bonk et al.
patent: 2003/0162806 (2003-08-01), Dellaria et al.
patent: 2003/0176458 (2003-09-01), Dellaria et al.
patent: 2003/0186949 (2003-10-01), Dellaria et al.
patent: 2003/0195209 (2003-10-01), Dellaria et al.
patent: 2004/0063658 (2004-04-01), Roberts et al.
patent: 2005/0054590 (2005-03-01), Averett
patent: 2005/0070556 (2005-03-01), Averett et al.
patent: 2005/0182001 (2005-08-01), Averett et al.
patent: 2006/0160830 (2006-07-01), Webber et al.
patent: 2008/0020989 (2008-01-01), Haley et al.
patent: 2008/0032999 (2008-02-01), Haley et al.
patent: 0882727 (1998-12-01), None
patent: 1035123 (2000-09-01), None
patent: 1043021 (2000-10-01), None
patent: 1386923 (2004-02-01), None
patent: WO-94/07904 (1994-04-01), None
patent: WO-94/17043 (1994-08-01), None
patent: WO-98/17279 (1998-04-01), None
patent: WO-03/045968 (2003-06-01), None
Krogsgaard-Larsen, Textbook of Drug Design and Discovery, Third Edition, CRC, Jul. 2002, Sections 14.3 and 14.3.1.
U.S. Appl. No. 11/873,202, Kucera.
U.S. Appl. No. 11/601,719, Wang et al.
Akira, “Mammalian Toll-like receptors”,Current Opinion, 2003, 15: 5-11.
Akira, “Toll-Like Receptor Signalling”,Immunology, 2004, 4:499-511.
Alexander et al., “(Acyloxy)alkyl Carbamates as Novel Bioreversible Prodrugs for Amines: Increased Permeation through Biological Membranes”, J. Med. Chem., 1988, 31:318-322.
Applequist et al., “Variable expression of Toll-like receptor in murine innate and adaptive immune cell lines”,Int. Immunol., 2002, 14(9):1065-74.
Barrio et al., “Regioselective Fluorination of Substituted Guanines with Dilute F2: A Facile Entry to 8-Fluoroguanine Derivatives”,J. Org. Chem., 1996, 61:6084-6085.
Bottcher et al., “Differential regulation of Toll-like receptor mRNAs in experimental murine central nervous system infections”,Neurosci. Lett., 2003, 344(1):17-20.
Bruno et al., “Mouse pre-immunocytes as non-proliferating multipotent precursors of macrophages, interferon-producing cells, CD8α+and CD8α−dendritic cells”,Eur. J. Immunol., 2001, 31(11):3403-12.
Chuang et al., “Cloning and characterication of a sub-family of human Toll-like receptors: hTLR7, hTLR8 and hTLR9”,Eur. Cytokine Netw., Sep. 2000, 11(3):372-8.
Diebold et al, “Innate antiviral responses by means of TLR7-mediated recognition of single-stranded RNA”,Science, 2004, 303(5663):1481-2.
Doxsee et al, “The Immune Response Modifier and Toll-like Receptor 7 Agonist S-27609 Selectively Induces IL-12 and TNF-α Production in CD11c+CD11b+CD8−Dendritic Cells”,J. Immunol., 2003, 171(3):1156-63).
Du et al.,Eur. Cytokine Netw., 2000, 11(3), 362-71.
Edwards et al., “Toll-like receptor expression in murine DC subsets: lack of TLR7 expression by CD8α+DC correlates with unresponsiveness to imidazoquinolines”,Eur. J. Immunol., 2003, 33(4):827-33.
Fan et al., “Pyrimidines. 24. Analogues and Derivatives of 2-Amino-5-bromo-6-phenyl-4(3H)-pyrimidinone (ABPP)”, J.Heterocyclic Chem., Nov. 1993, 30:1273-1276.
Fried, et al., “5-Substituted 2-Amino-6-phenyl-4(3H)-pyrimidinones. Antiviral- and Interferon-Inducing Agents”,J. Med. Chem., 1980, 23:237-239.
Fujiwara et al., “Synthesis and Bioactivities of Novel Piperidylpyrimidine Derivatives: Inhibitors of Tumor Necrosis Factor-Alpha Production”,Bioorg. Med. Chem. Lett., 2000, 10(12):1317-1320.
Furneaux et al., “Improved Syntheses of 3H,5H-Pyrrolo[3,2-d]pyrimidines”,J. Org. Chem., 64(22), 8411-8412 (1999).
Gangwar et al., “Synthesis of a Novel Esterase-Sensitive Cyclic Prodrug of a Hexapeptide Using an (Acyloxy)alkoxy Promoiety)”, J. Org. Chem., 1997, 62:1356-1362.
Gibson et al., “Plasmacytoid dendritic cells produce cytokines and mature in response to the TLR7 agonists, imiquimod and resiquimod”,Cell Immunol., 2002, 218(1-2):74-86.
Girgis et al., “Direct C-Flycosylation of Guanine Analogues: The Synthesis and Antiviral Activity of Certain 7- and 9-DeazaguanineC-Nucleosides”, J.Med. Chem., 1990, 33:2750-2755.
Heil et al., “The Toll-like receptor 7 (TLR7)-specific stimulus loxoribine uncovers a strong relationship within the TLR7, 8 and 9 subfamily”,Eur. J. Immunol., 2003, 33(11):2987-97.
Hemmi et al., “Small anti-viral compounds activate immune cells via the TLR7 MyD88-dependent signaling pathway”,Nat. Immunol., 2002, 3(2):196-200.
Henry et al., “Synthesis and Broad-Spectrum Antiviral Activity of 7,8-Dihydro-7-methyl-8-thioxoguanosine”,J. Med. Chem., 1990, 33:2127-2130.
Hirota et al., “Discovery of 8-Hydroxyadenines as a Novel Type of Interferon Inducer”,J. Med. Chem., 2002, 45:5419-5422.
Horng et al., “The adaptor molecule TIRAP provides signaling specificity for Toll-like receptors”,Nature, 2002, 420(6913):329-333.
Hornung et al., “Quantitative Expression of Toll-Like Receptor 1-10 mRNA in Cellular Subsets of Human Peripheral Blood Mononuclear Cells and Sensitivity to CpG Oligodeoxynucleotides”,J. Immunol., 2002, 168(9):4531-4537.
International Search Report (PCT/US2004/028236) dated Mar. 14, 2005.
International Search Report (PCT/US02/38001) dated Mar. 18, 2003.
Isobe et al, “Synthesis and Structure-Activity Relationships of 2-Substituted-8-hydroxyadenin Derivatives as Orally Available Interferon Inducers without Emetic Side Effects”,Bioorganic&Medicinal Chemistry, 2003, 11:3641-3647.
Ito et al., “Roles of Toll-Like Receptors in Natural Interferon-Producing Cells as Sensors in Immune Surveillance”,Hum. Immunol., 2002, 63(12):1120-1125.
Jarrossay, “Specialization and complementarity in microbial molecule recognition by human myeloid and plasmacytoid dendritic cells”,Eur. J. Immunol., 2001, 31(11):3388-3393.
Jurk et al., “Human TLR7 or TLR8 independently confer responsiveness to the antiviral compound R-848”,Nat. Immunol., 2002, 3(6):499.
Kerr et al, “Isatoribine, a Toll Like Receptor 7 Agonist, Significantly Reduced Plasma Viral Load in a Proof-of-Concept Study in Patients with Chronic Hepatitis C Virus Infection”.
Kini et al., “Synthesis and Antiviral Activity of Certain Guanosine Analogues in the Thiazolo[4,5-d]pyrimidine Ring System”,J. Med. Chem., 1991, 34:3006-3010.
Krenitsky et al., “6-Deoxyacyclovir: A xanthjne oxidase-activated prodrug of acyclovir”, Proc. Natl. Acad. Sci., 81:3209-3213 (1984).
Kurimoto et al., “Prodrugs of 9-Benzyl-8-hydroxy-2-(2-hydroxyethylthio)adenine: Potent Interferon Inducing Agents in Monkeys”,Chem. Pharm. Bull., 2004, 52(4):466-469.
Kurimoto et al., “Synthesis and evaluation of 2-substituted 8-hydroxyadenines as potent inferferon inducers with improved oral bioavailabilities”,Bioorg. Med. Chem., 20

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