HIV integrase inhibitors, pharmaceutical compositions and...

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

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C546S064000, C540S521000, C514S215000

Reexamination Certificate

active

07138408

ABSTRACT:
Beta-carboline hydroxamic acid compounds represented by formula (I)are described. The beta-carboline hydroxamic acid compounds and compositions containing those compounds may be used to inhibit or modulate the activity of HIV integrase enzyme and to treat HIV integrase-mediated diseases and conditions.

REFERENCES:
patent: 4371536 (1983-02-01), Braestrup et al.
patent: 5010077 (1991-04-01), Braestrup et al.
patent: 6057297 (2000-05-01), Politi et al.
patent: 6075021 (2000-06-01), Evanno et al.
patent: 0 030 254 (1980-08-01), None
patent: 1 209 158 (2000-11-01), None
patent: 1 086 101 (2001-03-01), None
patent: 1 375 486 (2004-01-01), None
patent: 2 209 032 (1989-04-01), None
patent: 2003119137 (2003-04-01), None
patent: 2003171381 (2003-06-01), None
patent: WO 99/64420 (1999-12-01), None
patent: WO 02/070491 (2002-09-01), None
patent: WO 03/033496 (2003-04-01), None
patent: WO 03/035076 (2003-05-01), None
patent: WO 03/035076 (2003-05-01), None
patent: WO 03/047564 (2003-06-01), None
patent: WO 03/049690 (2003-06-01), None
patent: WO 03/062204 (2003-07-01), None
patent: WO 03/077850 (2003-09-01), None
patent: WO 2004/039803 (2004-05-01), None
patent: WO 2004/067531 (2004-08-01), None
Ho, B., et al., “Inhibitors of Monoamine Oxidase: Influence of Methyl Substitution on the Inhibiting Activity of Beta-Carbolines,”J. Pharm. Sci., vol. 57, p. 269-274 (Feb. 1968), at p. 270, Table II (cmpd XX, XXII); and col. 1, line 21 et seq.
Ho, B., et al., “Inhibitors of Monoamine Oxidase III: 9-Substituted beta-Carbolines,”J. Pharm. Sci., vol. 58(2), pp. 219-221 (Feb. 1969), at p. 219, col. 1, lines 1-8, et seq.
Batch, A., and Dodd, R., “Ortho-Directed Metalation of 3-Carboxy-beta-carbolines,”J. Org. Chem., vol. 63, pp. 872-877 (1998), especially p. 872, cmpds 2 and 5.
Schlecker, W., et al., “Synthesis of 4-arylpyridines and Substituted beta-carbolines,”Tetrahedron, vol. 51(35), pp. 9531-9542 (1995), especially p. 9535, cmpds 21, 22.
Mehta, A., and Dodd, R., “Ortho-Directed Lithiation Studies of 3-Carboxy-Beta-carbolines,”J.Org. Chem., vol. 58, pp. 7587-7590 (1993), especially at p. 7588, compounds 8,9,18, and 19.
U.S. Appl. No. 10/699,068, filed Oct. 30, 2003, Agouron Pharmaceuticals, Inc.
Abdel-Magid, et al., “Reductive Amination of Aldehydes And Ketones With Sodium Triacetoxyborohydride. Studies On Direct And Indirect Reductive Amination Procedures,”Journal of Organic Chemistry, 1996, p. 3849-3862, vol. 61.
Bagshawe, K. et. al., “Antibody-Directed Enzyme Prodrug Therapy: A Review,”Drug. Development Research, 1995, p. 220-230, vol. 34.
Barbier, C., et al., “Preparation of Lavendamycin Analogues,”Heterocycles, 2000, p. 37-48, vol. 53, No. 1.
Bertolini, G. et. al., “A New Rational Hypothesis for the Pharmacophore of the Active Metabolite of Lefluonomide, a Potent Immunosuppressive Drug,”J. Med. Chem., 1997, p. 2011-2016, vol. 40.
Biere, H., et al., “Eine Neue und Besonders Einfache Synthese Von Zentralaktiven β-Carbolin-Derivaten,”Liebigs Ann. Chem., 1986, p. 1749-1764 (see English abstract).
Bodor, N, “Novel Approaches to the Design of Safer Drugs: Soft Drugs and Site-Specific Chemical Delivery Systems,”Advances in Drug Research, 1984, p. 255-331, vol. 13.
Bundgaard, et al.,Design of Prodrugs, 1985, Elsevier Press.
Bundgaard, H. “Design and Application of Prodrugs”,Drug Design Application and Development, 1991.
Butler, S.L., et al., “A Quantitative Assay for HIV DNA IntegrationIn Vivo,” Nature Medicine, May 2001, p. 631-634, vol. 7, No. 5.
Campbell, K.N., et al., “The Preparation of Unsymmetrical Secondary Aliphatic Amines,”J. Am. Chem. Soc., 1944, p. 82-84, vol. 66.
Chen, B. et al., “Distinct Modes Of Human Immunodeficiency Virus Type 1 Proviral Latency Revealed By Superinfection Of Nonproductively Infected Cell Lines With Recombinant Luciferase-Encoding Viruses,”Journal of Virology, 1994, p. 654-660, vol. 68, No. 2.
Dear, G.J. et. al., “Mass Directed Peak Selection, an Efficient Method of Drug Metabolite Identification Using Directly Coupled Liquid Chromatography-Mass Spectrometry-Nuclear Magnetic Resonance Spectroscopy,”Journal of Chromatography B, 2000, p. 281-293, vol. 748.
Debyser, Z., et al., “Assays for the Evaluation of HIV-1 Integrase Inhibitors,” Methods in Molecular Biology 160, p. 139-155. Schein, C.H., Humana Press Inc., Totawa, NJ 2001.
Dekhane, M., et al., “A New Efficient Synthesis of Ethyl β-Carboline-3-Carboxylate (β-CCE) and Methyl 4-Methyl-β-Carboline-3-Carboxylate (4-Methyl-β-CCM) Starting From Indole-2 Carbolxaldehyde,”Tetrahedron, 1994, p. 6299-6306, vol. 50, No. 21.
Doyle, et al., “Nuclear Analogs of β-lactam Antibiotics. I. Synthesis of O-2-isocephams,”Can. J. Chem., 1977, p. 468-483, vol. 55.
Eberle, M., “Contribution To The Chemistry Of Indole. About The 5-(1-Indolyl)-2-Pentanone System,”Journal of Organic Chemistry, 1976, p. 633-636, vol. 41, No. 4.
Eliel, E.L., et al.,Stereochemistry of Organic Compounds, Wiley, New York, 1994.
Erofeev, Y.V., et al., “Introduction of 3-Indolymethyl Residues in Nitroacetic Acid Esters,”Khim. Get. Soed., 1978, p. 780.
Goldgur, Y., et al., “Structure Of The HIV-1 Integrase Catalytic Domain Complexed With An Inhibitor: A Platform For Antiviral Drug Design,”PNAS, Nov. 9, 1999, p. 13040-13043, vol. 96, No. 23.
Grobler, J. et al., “Diketo Acid Inhibitor Mechanism And HIV-1 Integrase: Implications For Metal Binding In The Active Site Of Phosphotransferase Enzymes,”PNAS, May 14, 2002, p. 6661-6666, vol. 99, No. 10.
Hansen, M.S., et al., “Integration Complexes Derived From HIV Vectors For Rapid Assays In Vitro,”Nature Biotechnology, Jun. 1999, p. 578-582, vol. 17, No. 6.
Hauser, C.R., et al.,Org. Synth. Coll., vol. 2, 1943, p. 67, John Wiley, New York.
Hazuda, D. et al., “Discovery And Analysis Of Inhibitors Of The Human Immunodeficiency Integrase,”Drug Design And Discovery, 1997, p. 17-24, vol. 15.
Jenkins, T.M., et al., “A Soluble Active Mutant of HIV-1 Integrase,”Journal of Biological Chemistry, 1996, p. 7712-7718, vol. 271, No. 13.
Kantlehner, W., et al., “Umsetzungen vontert-Butoxy-N,N,N′,N′-tetramethylmethandiamin mit Nh- und CH-aciden Verbindungen,”Liebigs Ann. Chem., 1980, p. 344 (see English abstract).
Lewin, S.R., et al., “Use of Real-Time PCR and Molecular Beacons to Detect Virus Replication in Human Immunodeficiency Virus Type 1-Infected Individuals on Prolonged Effective Antiretroviral Therapy,”Journal of Virology, Jul. 1999, p. 6099-6103, vol. 73, No. 7.
Lyttle, D.A., et al., “The Chemistry of Nitroacetic Acid and Its Esters. I. The Alkylation of Alkylnitroacetates with Gramine,”J. Am. Chem. Soc., 1947, p. 2118-2119, vol. 69.
March, Jerry,Advanced Organic Chemistry, 5thEdition, p. 508-511, John Wiley & Sons, 2001.
Neef, G., et al., “Synthesis of 4-Substituted β-Carbolines,”Heterocycles, 1983, p. 1295-1313, vol. 20, No. 7.
Pais, G., et al., “Structure Activity of 3-Aryl-1,3-diketo-Containing Compounds as HIV-1 Integrase Inhibitors,” Journal of Medicinal Chemistry, 2002, p. 3184-3194, vol. 45.
Prox, et. al., “Rapid Structure Elucidation of Drug Metabolites by Use of Stable Isotopes,”Xenobiotica, 1973, p. 103-112, vol. 3, No. 2.
Sandrin, J., et al., “Pictet-Spengler Condensations in Refluxing Benzene,”Heterocycles, 1976, p. 1101-1104, vol. 4, No. 6.
Sayasith, K., et al., “Targeting HIV-1 Integrase,”Expert Opin. Ther. Targets, 2001, p. 443-464, vol. 5, No. 4.
Settimj, et al., “β-Carbolines as Agonistic or Antagonistic Benzodiazepine Receptor Ligands. 1. Synthesis of some 5-, 6- and 7-Amino Derivatives of 3-Methoxycarbonyl-β-carboline (β-CCM) and of 3-Ethoxycarbonyl-β-Carbo

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