Carbocyclic compounds

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

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514102, 514315, 514365, 514381, 514396, 514401, A61K 3135, A61K 3166, A61K 31445

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active

058666010

ABSTRACT:
Novel carbocyclic compounds are described. The compounds generally comprise an acidic group, a basic group, a substituted amino or N-acyl and a group having an optionally hydroxylated alkane moiety. Pharmaceutical compositions comprising the inhibitors of the invention are also described. Methods of inhibiting neuraminidase in samples suspected of containing neuraminidase are also described. Antigenic materials, polymers, antibodies, conjugates of the compounds of the invention with labels, and 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: 5622916 (1997-04-01), Kunisch et al.
patent: 5714509 (1998-02-01), Luo et al.
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.
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.
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.
Ulibarri et al., "Construction of the Bicyclic Core Structure of the Enediyne Antibiotic Esperamicin-A1 in Either Anantimeric Form from (-)-Quinic Acid", 60:2753-2761, J Org Chem, 1995.
Berger, Alfred, "Relation of Chemical Structure and Biological Activity", Medicinal Chemistry Third edition, part 1, pp. 73-75 (1979).
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).
Raner et al., Aust J Chem, 43:609-616 (1990).
Smith et al., "Novel Inhibitors of Influenza Sialidases Related to GG167," Bioorg Med Chem Lett 6(4):2931-2936 (1996).
Meindl et al., "2-Deoxy-2,3-dehydrosialic acids. 3. Inhibition of Vibrio 2-deoxy-2,3-dehydro-N-acetylneuraminic acid", 73:42027b, Chem Ab, 1970.
Bamford et al., "Synthesis of 6-,7-and 8-carbon sugar analogues of potent anti-influenza 2,3-didehydro-2,3-dideoxy-N-actylneuramine acid derivatives," J Chem Soc Perkin Trans I pp. 1181-1187 (1995).
Bamford, Mark J., "Neuraminidase inhibitors as Potential Anti-Infleunza Drugs," J Enzyme Inhibition 10:1-16 (1995).
Carless et al., "Synthesis of Pseudo-alpha-L-fucopyranose from Toluene," J Chem Soc (C) pp. 2447-2448 (1995).
Chandler et al., "Approaches to carbocyclic analogues of the potent neuraminidase inhibitor 4-quanidino-Neu5Ac2en. X-Ray molecular structure e," J Chem Soc Perkin Trans I pp. 1189-1197 (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-erthro-L-gluco-noninic acid," J Chem Soc Perkin Trans I pp. 1173-1180 (1995).
Ciccotosto et al., "Synthesis of Methyl 5-Actamido-3,4,5-trideoxy-4-Gluanidinyl-D-glycero-D-galacto-2-nonulopyrano sidonic acid (4-deoxy-4-guanidino-Neu5Acalpha2Me)," Tet Lett 36(30):5405-5408 (1995).
Colman, P.M., "Infleunza virus neuraminidase: Structure, antibodies, and inhibitors," Protein Science 3:1687-1696(1994).
Dernick, Rudolf, "Sterical Requirements for Inhibitors of Viral Neuraminidases," Chem Ab 96:256 (1982).
Douglas, R. Gordon, Jr., "Prophylaxis and Treatment of Infleunza," N Engl J Med 322(7):443-450 (Feb. 15, 1990).
Ganem, Bruce, "Tetrahedron Report No. 59. From Glucose to Aromatics: Recent Developments in Natural Products of the Shikimic Acid Pathway," Tetrahedron 34:3353-3383 (1978).
Grewe et al, "Abbau der Chinasaure nach Hunsdiecker," Chem Ber 98:104-110 (1965).
Grewe et al, "Darstellung und Eigenschaften des Chinaaldehyds," Liebigs Ann Chem 658:113-119 (1962).
Grewe et al, "Die Totalsythesis der Chinasaure," Chem Ber 87:793-802 (1954).
Grewe et al, "Die Uberfuhrung der Shikimisaure in Chinasaure," Chem Ber 86:928-938 (1953).
Grewe et al, "Eine einfache Synthese der Shikimisaure," Chem Ber 100:2546-2553 (1967).
Grewe et al, "Eine neue Synthese der Shikimisaure," Chem Ber 97:443-448 (1964).
Grewe et al, "Synthese der Homochinasaure und des beta-Chino-athylamins," Liebigs Ann Chem 575:1-17 (1952).
Grewe et al, "Uberfuhrung der chinasaure in ungesattigte Verbindungen vom Typ der Shikimisaure," Angew Chem Int Ed 69:61 (1957).
Hanessian et al., "Anomeric Deoxygenation of 2-Ulosonic Acids Using Sm12: Rapid Access to 2-Deoxy-KDO and 2-Deoxy-NANA," Synlett pp. 863-864 (Oct. 1994).
Hayden et al., "Safety and Efficacy of the Neuraminidase Inhibitor GG167 in Experimental Human Infleunza," JAMA 275(4):295-299 (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," Biochem 33:8172-8179 (1994).
Kiefel et al., "Synthesis and Biological Evaluation ofN-Acetylneuraminic Acid-Based Rotavirus Inhibitors," J Med Chem 39:1314-1320 (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-deoxy-Neu5Ac)," Tet Lett 36(6):957-960 (1995).
Kudo et al., "Synthesis of the Potent Inhibitors of Neuraminidase, N-(1,2-Dihydroxypropyl) Derivatives of Siastain B and its 4-Deoxy Analogs," J Antibiot 46(2):300-309 (Feb. 1993).
McCauley et al., "4-Guanidino-Neu5Ac2en fails to protect chickens from infection with highly pathogenic avian influenza virus," Antiviral Res 27:179-186 (1995).
McKimm-Breschkin et al., "Generation and Characterization of Variants of NWS/G70C Infleunza Virus after In Vitro Passage in 4-Amino-Neu5Ac2en and 4-Guanidino-Neu4Ac2en," Antimicro Ag & Chemo 40(1):40-46 (Jan. 1996).
Nishimura et al., "Design of Potential Neuraminidase Inhibitors By Dehydration, Deoxygenation and Epimerization of Siastatin B," Natural Product Letters 1(1):39-44 (1992).
Nishimura et al., "Synthesis of 3-Episiastatin B Analogues Having Anti-Infleunza Virus Activity," J Antibiot 46(12):1883-1889 (Dec. 1993).
Ogawa et al., "Synthesis of a Carbocyclic Analogue of N-Acetylneuraminic Acid (Pseudo-N-acteylneuraminic Acid)," J Chem Soc (C) pp. 406-408 (1992).
Ogawa et al., "Synthesis of carbocyclic analogues of 3-deoxy-D-manno-2-octulosonic acid and N-acetylneuraminic acid," Caeb Res 269:53-78 (1995).
Ryan et al., "Inhibition of Infleunza Virus in Mice by GG167 (4-Guanidino-2,4-Dideoxy-2,3-Dehydro-N-Acetylneuraminic Acid) Is Consistent with Extracellular Activity of Viral Neuraminidase (Sialidase)," Antimicro Ag & Chemo 38(10):2270-2275 (Oct. 1994).
Saito et al., "Steps in Maturation of Infleunza A Virus Neuraminidase," J Virol 69(8):5011-5017 (Aug. 1995).
Singh et al., "Structure-Based Inhibitors of Infleunza Virus Sialidase. A Benzoic Acid Lead with Novel Interaction," J Med Chem 38:3217-3225 (1995).
Smith et al., "Synthesis and infleunza virus sialidase inhibitory activity of analogues of 4-guanidino-Neu5Ac2en (GG167) with modified 5-substituents," Eur J Med Chem 31:143-150 (Jun. 22, 1995).
Sollis et al, "Novel Inhibitors of Influenza Sialidase Related to GG167," Bioorg Med Chem Lett 6(15):1805-1808, Abstract, Table of Contents (1996).
Starkey et al., "Synthesis and influenza Virus Sialidase Inhibitory of the 5-Desacetamido Analogue of 2,3-Didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneutaminic acid," Tet Lett 36(2):299-302 (1995).
Staschke et al., "Molecular Basis for the Resistance of Influenza V

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