Long chain n-alkyl compounds and oxa-derivatives thereof

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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C564S023000

Reexamination Certificate

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07816560

ABSTRACT:
Long chain N-alkyl amino and imino compounds, oxa-substituted derivatives thereof, and pharmaceutical compositions including such compounds are described. The long chain N-alkyl group is a C8-C16alkyl group. The long chain N-alkyl compounds and oxa-substituted derivatives thereof can be used in the treatment of viral infections, in particular hepatitis B virus or hepatitis C virus, in a cell or an individual. For example, the long chain N-alkyl compounds or oxa-substituted derivatives thereof can be derived from piperidines, pyrrolidines, phenylamines, pyridines, pyrroles, or amino acids.

REFERENCES:
patent: 4246345 (1981-01-01), Kinast et al.
patent: 4266025 (1981-05-01), Kinast et al.
patent: 4405714 (1983-09-01), Kinast et al.
patent: 4806650 (1989-02-01), Schröder et al.
patent: 4861892 (1989-08-01), Fleet
patent: 4894388 (1990-01-01), Fleet
patent: 4910310 (1990-03-01), Campbell et al.
patent: 4944572 (1990-07-01), Young
patent: 4996329 (1991-02-01), Fleet et al.
patent: 5011929 (1991-04-01), Fleet et al.
patent: 5013842 (1991-05-01), Fleet et al.
patent: 5017704 (1991-05-01), Fleet et al.
patent: 5043273 (1991-08-01), Scudder et al.
patent: 5100797 (1992-03-01), Fleet et al.
patent: 5103008 (1992-04-01), Scudder et al.
patent: 5200523 (1993-04-01), Fleet
patent: 5264356 (1993-11-01), Rohrschneider
patent: 5286877 (1994-02-01), Behling et al.
patent: 5310745 (1994-05-01), Partis et al.
patent: 5401645 (1995-03-01), Grabner et al.
patent: 5580884 (1996-12-01), Platt et al.
patent: 5596005 (1997-01-01), Wong et al.
patent: 5622972 (1997-04-01), Bryant et al.
patent: 5643888 (1997-07-01), Rohrschneider
patent: 6291657 (2001-09-01), Platt et al.
patent: 6355413 (2002-03-01), Gage et al.
patent: 6462197 (2002-10-01), Hollingsworth et al.
patent: 6465487 (2002-10-01), Block et al.
patent: 6465488 (2002-10-01), Butters et al.
patent: 6545021 (2003-04-01), Mueller et al.
patent: 6660749 (2003-12-01), Butters et al.
patent: 6689759 (2004-02-01), Jacob et al.
patent: 6809083 (2004-10-01), Mueller et al.
patent: 7256005 (2007-08-01), Zitzmann et al.
patent: 2006/0094671 (2006-05-01), Jacob et al.
patent: 2006/0106065 (2006-05-01), Jacob et al.
patent: 2006/0252918 (2006-11-01), Rowlands et al.
patent: 2006/0264468 (2006-11-01), Mueller et al.
patent: 0 367 747 (1990-05-01), None
patent: 0 445 098 (1991-02-01), None
patent: WO 92/00277 (1992-01-01), None
patent: WO 98/35685 (1998-08-01), None
patent: WO 99/24401 (1999-05-01), None
patent: WO 99/24401 (1999-05-01), None
patent: WO 99/40916 (1999-08-01), None
patent: WO 00/47198 (2000-08-01), None
patent: WO 01/60366 (2001-08-01), None
patent: WO 2004/005333 (2004-01-01), None
Mellor et al. “High-Performance Cation-Exchange Chromatrography and Pulsed Amperometric Detection for the Separation, Detection and Quantitation of N-Alkylated Imino Sugars in Biological Samples” Aug. 2000, Analytical Biochemistry, 284(1), 136-42.
van den Broek et al. (Synthesis of oxygen-substituted N-alkyl 1-deoxynojirimycin derivatives: aza sugar a-glucosidase inhibitors showing antiviral (HIV-1) and immunosuppressive activity, Recl. Trav. Chim. Pays-bas, 1994, vol. 113, pp. 507-5166).
Defoin et al. (6-Deoxy-Nojirimycin and 6-Deoxy-gulo-Nojirimycin in the racemic and D-series, D-Fuco-Nojirimycin and their 1-Deoxyderivatives via Hetero-Diels-Alder Cycloadditions, 1997, Tetrahedron, vol. 53, No. 40, pp. 13783-13796).
Acosta et al., “Agents for treating human immunodeficiency virus infection,” Am. J. Hosp. Pharm., Sep. 15, 1994, 51:2251-2267.
Berge et al., “Pharmaceutical Salts,” J. Pharm. Sci., Jan. 1977, 66(1):1-19.
Bergeron et al., “Calnexin: a membrane-bound chaperone of the endoplasmic reticulum,” TIBS Mar. 19, 1994, Elsevier Scient Ltd. 0968-0004/94 pp. 124-128.
Block et al., “Secretion of human hepatitis B virus is inhibited by the imino sugar N-butyldeoxynojirimycin,” PNAS, Mar. 1994, 91:2235-2239.
Blum et al., “Antiviral therapy of hepatitis B virus infection: Blocking viral gene expression,” Advanced Drug Delivery Reviews, 1995, 17:321-331.
Branza-Nichita et al., “Antiviral of N-Butyledeoxynojirimycin against Bovine Viral Diarrhea Virus Coorelates with Misfolding of E2 Envelope Proteins and Impairment of Their Association into E1-E2 Heterodimers,” (2001) J. Virol. 75(8), pp. 3527-3536.
Bruss et al., The role of envelope proteins in hepatitis B virus assembly, PNAS, Feb. 1991, 88:1059-1063.
Carrère-Kremer et al., “Subcellular Localization and Topology of the p7 Polypeptide of Hepatitis C Virus,” Journal of Virology, Apr. 2002, 76(8) :3720-3730.
Choukhi et al., Involvement of Endoplasmic Reticulum Chaperones in the Folding of Hepatitus C Virus Glycoproteins, (1998) J. Virol., 72(5), pp. 3851-3858.
Coates et al., “Developments in viral hepatitis during 1994,” Exp. Opin. Ther. Patents, 1995, 5(8):747-756.
Courageot et al., “a-Glucosidase Inhibitors Reduce Dengue Virus Production by Affecting the Initial Steps of Virion Morphogenesis in the Endoplasmic Reticulum,” (2000) J. Virol., 74(1): pp. 564-572.
De Francesco et al., “Biochemical and immunologic properties of the nonstructural proteins of the hepatitis C virus: implications for development of antiviral agents and vaccines,” Semin. Liver Dis., 2000, 20(1):69-83, one page Abstract only.
Di Bisceglie, Adrian M., “Hepatitis C and Hepatocellular Carcinoma,” Hepatology, Sep. 1997, 26(3)Suppl. 1:345-350.
Doong et al., “Inhibition of the replication of hepatitis B virus in vitro by 2′,3′-dideoxy-3′-thiacytidine and related analogues,” PNAS, Oct. 1991, 88:8495-8499.
Duff et al., “The Transmembrane Domain of Influenza A M2 Protein Forms Amantadine-Sensitive Proton Channels in Planar Lipid Bilayers,” Virology 190, pp. 485-489 (1992) 0042-6822/92 Copyright 1992 by Academic Press, Inc.
Durantel et al., “Study of the Mechanism of Antiviral Action of Iminosugar Derivatives against Bovine Viral Diarrhea Virus,” (2001) J. Virol. 75(19): pp. 8987-8998.
Dwek, et al., “Targeting Glycosylation as a Therapeutic Approach,” Nature Reviews/Drug Discovery, vol. 1, Jan. 2002, pp. 65-75. Glycobiology Institute, Dept. of Biochemistry, University of Oxford, Oxford OX1 3QU, UK.
Elbein et al., “Inhibitors of the biosynthesis and processing of N-linked oligosaccharide chains,” Ann. Rev. Biochem., 1987, 56:497-534.
Esposito et al., “Synthesis of amphiphilic polyhydroxylated pyrrolidones as potential glycosidase inhibitors,” Tetrahedron Lett., 1998, 39(36):6543-6546.
Fischer et al., “Amantadine blocks channel activity of the transmembrane segment of the NB protein from influenza B,” Eur. Biophys J. (2001) 30: pp. 416-420, DOI 10.1007/s00240100157.
Fleet et al., “Enantiospecific synthesis of deoxymannojirimycin, fagomine and 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine from D-glucose,” Tetrahedron Letters, 1985, 26(11):1469-1472.
Fourel et al., “The Carbocyclic Analog of 2′-Deoxyguanosine Induces a Prolonged Inhibition of Duck Hepatitis B Virus DNA Synthesis in Primary Hepatocyte Cultures and in the Liver,” J. Virol., Feb. 1994, 68(2):1059-1065.
Gabrielson et al., “Synthesis and Antiviral Evaluation of N-Carboxamidine-Substituted Analogues of 1-β-D-Ribofuranosyl-1,2,4-triazole-3-carboxamidine Hydrochloride,” J. Med. Chem., 1992, 35:3231-3238.
Ganem, D., “Assembly ofHepadnaviral virionsand Subviral Particles,” Curr. Top. Microbiol. Immunol., 1991, 168:61-83.
Griffin et al., “A conserved basic loop in hepatitis C virus p7 protein is required for amantidine-sensitive ion channel activity in mammalian cells but is dispensable for localization to mitochondria,” Journal of General Virology, 2004, 85:451-461.
Griffin et al., “The p7 protein of hepatitis C virus forms an ion channel that is blocked by the antiviral drug, Amantadine,” FEBS Letters 535 (200

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