Compounds and methods for synthesis and therapy

Details Compounds and methods for synthesis and therapy Compounds and methods for synthesis and therapy

1998-12-10

2000-08-29

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

564123, C07C20500

Patent

active

061111325

ABSTRACT:
Novel compounds of Formula (I) are described. R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are described in this specification.
Synthetic intermediates and pharmaceutical compositions comprising the inhibitors of the invention are also described. Methods of inhibiting neuraminidase in samples suspected of containing neuraminidase are also described. Assay methods for detecting neuraminidase activity are also described.

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: 5428073 (1995-06-01), Kunisch 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: 5622916 (1997-04-01), Kunisch et al.
patent: 5633360 (1997-05-01), Bischofberger et al.
patent: 5714509 (1998-02-01), Luo et al.
patent: 5763483 (1998-06-01), Bischofberger et al.
patent: 5866601 (1999-02-01), Lew et al.
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.
Burger, Alfred, "Relation of Chemical Structure and Biological Activity", Third edition, part 1, pp. 73-75, Medicinal Chemistry, 1979.
Carless et al., "Synthesis of Pseudo-alpha-L-fucopyranose from Toluene", pp. 2447-2448, J Chem Soc (C), 1995.
Chahoua et al., "Synthesis of (-)-Shikimate and (-)-Quinate 3-Phosphates by Differentiation of the Hydroxyl Functions of (-)-Shikimic and (-)-Quinic Acids", 57:5798-5801, J Org Chem, 1992.
Chandler et al., "Synthesis of the potent influenza neuraminidase inhibitor 4-quanidino 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 of N-[(1S,2S,6R)-2-azido-6-benzyloxymethyl-4-formylcyclohex-3-enyl]acetami 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.
Dernick, Rudolf, "Sterical Requirements for Inhibitors of Viral Neuraminidases", 96:256, Chem Ab, 1982.
Douglas, R. Gordon, Jr., "Prophylaxis and Treatment of Influenza", 322(7):443-450, N Engl J Med, Feb. 15, 1990.
Fernandez et al., "New and Efficient Enantiospecific Synthesis of (-)-Methyl 5-epi-Shikimate and Methyl 5-epi-Quinate from (-)-Quinic Acid", 38(29):5225-5228, Tet Lett, 1997.
Funded Research Agreement, "Agreement between Gilead Sciences, Inc. and the University of California, Berkeley", 2 pages, , Dec. 7, 1995.
Ganem, Bruce, "Tetrahedron Report No. 59. From Glucose to Aromatics: Recent Developments in Natural Products of the Shikimic Acid Pathway", 34:3353-3383, Tetrahedron, 1978.
Grewe et al, "Eine einfache Synthese der Shikimisaure", 100:2546-2553, Chem Ber, 1967.
Grewe et al, "Synthese der Homochinasaure und des beta-Chino-athylamins", 575:1-17, Liebigs Ann Chem, 1952.
Grewe et al, "Darstellung und Eigenschaften des Chinaaldehyds", 658:113-119, Liebigs Ann Chem, 1962.
Grewe et al, "Uberfuhrung der Chinasaure in ungesattigte Verbindungen vom Typ der Shikimisaure", 69:61, Angew Chem Int Ed, 1957.
Grewe et al, "Die Uberfuhrung der Shikimisaure in Chinasaure", 86:928-938, Chem Ber, 1953.
Grewe et al, "Die Totalsynthese der Chinasaure", 87:793-802, Chem Ber, 1954.
Grewe et al, "Eine neue Synthese der Shikimisaure", 97:443-448, Chem Ber, 1964.
Grewe et al, "Abbau der Chinasaure nach Hunsdiecker", 98:104-110, Chem Ber, 1965.
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/Lee/40 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.
Kim et al., "Influenza Neuraminidase Inhibitors Possessing a Novel Hydrophobic Interaction in the Enzyme Active Site: Design, Synthesis, and Structural Analysis of Carbocyclic Sialic Acid Analogues with Potent Anti-Influenza Activity", 119:681-690, J Am Chem Soc, 1997.
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.
Kudo, et al., "Syntheses and Activities of N-Substituted Derivatives of Siastatin B", 45(10:1662-1668, The Journal of Antibiotidcs, Oct. 1992.
Lew et al., "Carbocyclic Compounds", U.S. Patent Application No. 08/395,245, , Filed Feb. 27, 1995.
Luo et al., "Abstract of Presentation C52: Designed Non-Carbohydrate Inhibitors or Influenza Virus Neuraminidase and Accompanying Notes", , International Antiviral Conference, Nice, France, Jun. 10, 1994.
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.
Meindl et al., "2-Deoxy-2,3-dehydrosialic acids. 3. Inhibition of Vibrio cholerae[comma]neuraminidase by oxidation products of 2-deoxy-2,3-dehydro-N-acetylneuraminic acid", 73:42027b, Chem Ab, 1970.
Microbial Chem Res Found, "Siastatin B Derivative as Novel Antiviral Substance and its Production", Publication No. 04089481, Patent Abstracts of Japan, Mar. 23, 1992.
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., "The First L-Iduronic Acid-Type 1-N-Iminosugars Having Inhibitory Activity of Experimental Metastasis", 118:3051-3052, J Am Chem Soc, 1996.
Nishimura et al., "Synthesis of 3-Episiastatin B Analogues Having Anti-Influenza Virus Activity", 46(12):1883-1889, J Antibiot, Dec. 1993.
Nishimura et al., "Totally Synthetic Analogues of Siastatin B. III. Trifluoroacetamide Analogues Having Inhibitory Activity for Tumor Metastasis", 47(1):101-107, The Journal of Antibiotics, Jan. 1994.
Nishimura, et al., "Potent Inhibition of Neuraminidase by N-(1,2-Dihydroxypropyl) Derivatives of Siastatin B and its Analogs", 1(1):33-38, Natural Product Letters, 1992.
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 Ext

Affiliated with

Also associated with

Rating

Compounds and methods for synthesis and therapy does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Compounds and methods for synthesis and therapy, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Compounds and methods for synthesis and therapy will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1251531