Preparation of carbocyclic compounds

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

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560169, 560170, C07C20504, C07C22908

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active

058862137

ABSTRACT:
The present invention provides new synthetic methods and compositions. In particular, new methods of preparing intermediates useful in the synthesis of neuraminidase inhibitors and compositions useful as intermediates that are themselves useful in the synthesis of neuraminidase inhibitors are provided.

REFERENCES:
patent: 4968788 (1990-11-01), Farquhar
patent: 5175273 (1992-12-01), Bischofberger et al.
patent: 5206400 (1993-04-01), Witiak et al.
patent: 5292938 (1994-03-01), Mease et al.
patent: 5360817 (1994-11-01), von Izstein et al.
patent: 5512596 (1996-04-01), Kim et al.
patent: 5514798 (1996-05-01), Bischofberger et al.
patent: 5536734 (1996-07-01), Mueller et al.
patent: 5556963 (1996-09-01), Liav et al.
patent: 5597933 (1997-01-01), Searle et al.
patent: 5602277 (1997-02-01), Babu et al.
patent: 5714509 (1998-02-01), Luo et al.
Funded Research Agreement, "Agreement between Gilead Sciences, Inc. and the University of California, Berkeley", 2 pages,, Dec. 7, 1995.
Stevens, Ray, "Letter from Assistant Prof. Ray Stevens to Dr. Choung Kim", 1 page,, Oct. 10, 1996.
Stevens, Ray, "Letter from Assistant Prof. Ray Stevens to Dr. Choung Kim", 2 pages,, Feb. 18, 1996.
Bamford et al., "Synthesis of 6-, 7- and 8-carbon sugar analogues of potent anti-influenza 2,3-didehydro-2,3-dideoxy-N-acetylneuraminic acid derivatives", pp. 1181-1187, J Chem Soc Perkin Trans I, 1995.
Bamford, Mark J., "Neuraminidase Inhibitors as Potential Anti-Influenza Drugs", 10:1-16, J Enzyme Inhibition, 1995.
Carless et al., "Synthesis of Pseudo-alpha-L-fucopyranose from Toluene", pp. 2447-2448, J Chem Soc (C), 1995.
Chandler et al., "Synthesis of the potent influenza neuraminidase inhibitor 4-guanidino Neu5Ac2en. X-Ray molecular structure of 5-acetamido-4-amino-2,6-anhydro-3,4,5-trideoxy-D-erythro-L-gluco-nononic acid", pp. 1173-1180, J Chem Soc Perkin Trans I, 1995.
Chandler et al., "Approaches to carbocyclic analogues of the potent neuraminidase inhibitor 4-guanidino-Neu5Ac2en. X-Ray molecular structure de", pp. 1189-1197, J Chem Soc Perkin Trans I, 1995.
Ciccotosto et al., "Synthesis of Methyl 5-Acetamido-3,4,5-trideoxy-4-Guanidinyl-D-glycero-D-galacto-2-nonulopyrano sidonic acid (4-deoxy-4-guanidino-Neu5Acalpha2Me)", 36(30):5405-5408, Tet Lett, 1995.
Colman, P.M., "Influenza virus neuraminidase: Structure, antibodies, and inhibitors", 3:1687-1696, Protein Science, 1994.
Douglas, R. Gordon, Jr., "Prophylaxis and Treatment of Influenza", 322(7):443-450, N Engl J Med, 15-Feb.-1990.
Ganem, Bruce, "Tetrahedron Report Number 59. From Glucose to Aromatics: Recent Developments in Natural Products of the Shikimic Acid Pathway", 34:3353-3383, Tetrahedron, 1978.
Hanessian et al., "Anomeric Deoxygenation of 2-Ulosonic Acids Using Sml2: Rapid Access to 2-Deoxy-KDO and 2-Deoxy-NANA", pp. 863-864, Synlett, Oct. 1994.
Hayden et al., "Safety and Efficacy of the Neuraminidase Inhibitor GG167 in Experimental Human Influenza", 275(4):295-299, JAMA, Jan. 1996.
Janakiraman et al., "Structure of Influenza Virus Neuraminidase B/Lee40 Complexed with Sialic Acid and a Dehydro Analog at 1.8-Angstrom Resolution: Implications for the Catalytic Mechanism", 33:8172-8179, Biochem, 1994.
Kiefel et al., "Synthesis and Biological Evaluation of N-Acetylneuraminic Acid-Based Rotavirus Inhibitors", 39:1314-1320, J Med Chem, 1996.
Kong et al., "The First Synthesis of a C-7 Nitrogen-containing Sialic Acid Analogue, 5-Acetamido-7-azido-3,5,7-trideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (7-azido-7-deoxy-Neu5Ac)", 36(6):957-960, Tet Lett, 1995.
Kudo et al., "Synthesis of the Potent Inhibitors of Neuraminidase, N-(1,2-Dihydroxypropyl) Derivatives of Siastatin B and its 4-Deoxy Analogs", 46(2):300-309, J Antibiot, Feb.-1993.
McCauley et al., "4-Guanidino-Neu5Ac2en fails to protect chickens from infection with highly pathogenic avian influenza virus", 27:179-186, Antiviral Res, 1995.
McKimm-Breschkin et al., "Generation and Characterization of Variants of NWS/G70C Influenza Virus after In Vitro Passage in 4-Amino-Neu5Ac2en and 4-Guanidino-Neu5Ac2en", 40(1):40-46, Antimicro Ag & Chemo, Jan. 1996.
Nishimura et al., "Design of Potential Neuraminidase Inhibitors By Dehydration, Deoxygenation and Epimerization of Siastatin B", 1(1):39-44, Natural Product Letters, 1992.
Nishimura et al., "Synthesis of 3-Episiastatin B Analogues Having Anti-Influenza Virus Activity", 46(12):1883-1889, J Antibiot, Dec.-1993.
Ogawa et al., "Synthesis of carbocyclic analogues of 3-deoxy-D-manno-2-octulosonic acid and N-acetylneuraminic acid", 269:53-78, Carb Res, 1995.
Ogawa et al., "Synthesis of a Carbocyclic Analogue of N-Acetylneuraminic Acid (Pseudo-N-acetylneuraminic Acid)", pp. 406-408, J Chem Soc (C), 1992.
Raner et al., 43:609-616, Aust J Chem, 1990.
Ryan et al., "Inhibition of Influenza Virus Replication in Mice by GG167 (4-Guanidino-2,4-Dideoxy-2,3-Dehydro-N-Acetylneuraminic Acid) Is Consistent with Extracellular Activity of Viral Neuraminidase (Sialidase)", 38(10):2270-2275, Antimicro Ag & Chemo, Oct.-1994.
Saito et al., "Steps in Maturation of Influenza A Virus Neuraminidase", 69(8):5011-5017, J Virol, Aug.-1995.
Singh et al., "Structure-Based Inhibitors of Influenza Virus Sialidase. A Benzoic Acid Lead with Novel Interaction", 38:3217-3225, J Med Chem, 1995.
Smith et al., "Synthesis and influenza virus sialidase inhibitory activity of analogues of 4-guanidino-Neu5Ac2en (GG167) with modified 5-substituents", 31:143-150, Eur J Med Chem, 22-Jun.-1995.
Smith et al., "Novel Inhibitors of Influenza Sialidases Related to GG167", 6(24):2931-2936, Bioorg Med Chem Lett, 1996.
Sollis et al, "Novel Inhibitors of Influenza Sialidase Related to GG167", 6(15):1805-1808,Abstract, Table of Contents, Bioorg Med Chem Lett, 1996.
Starkey et al., "Synthesis and Influenza Virus Sialidase Inhibitory Activity of the 5-Desacetamido Analogue of 2,3-Didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acid", 36(2):299-302, Tet Lett, 1995.
Staschke et al., "Molecular Basis for the Resistance of Influenza Viruses to 4-Guanidino-Neu5Ac2en", 214:642-646, Virology, 1995.
Ulmer et al., "Heterologous Protection Against Influenza by Injection of DNA Encoding a Viral Protein", 259:1745-1749, Science, 19-Mar.-1993.
Wu et al., "Non-Sialate Inhibitor of Influenza A/WSN/33 Neuraminidase", 34:7154-7160, Biochem, 1995.
von Itzstein et al, "Rational design of potent sialidase-based inhibitors of influenza virus replication", 363:418-423, Nature, 1993.
von Itzstein et al., "A Study of the Active Site of Influenza Virus Sialidase: An Approach to the Rational Design of Novel Anti-influenza Drugs", 39:388-391, J Med Chem, 1996.

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