Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2005-05-03
2005-05-03
Low, Christopher S. F. (Department: 1653)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S308000
Reexamination Certificate
active
06888033
ABSTRACT:
A compound having the formula (I) wherein the substituents are defined herein. Also provided are pharmaceutical compositions including a compound of formula (I) in a pharmaceutical carrier, for treating a disease caused by a picornavirus. Also provided is a method of treating a subject with a disease caused by a picornavirus, including a compound of formula (I) in a pharmaceutical carrier.
REFERENCES:
patent: 3657436 (1972-04-01), Berger
patent: 3666771 (1972-05-01), Hoefle et al.
patent: 3956375 (1976-05-01), Farkas et al.
patent: 4327088 (1982-04-01), Shinma et al.
patent: 4333941 (1982-06-01), Baratz
patent: 4503256 (1985-03-01), Fourie et al.
patent: 4578520 (1986-03-01), Fourie et al.
patent: 4605674 (1986-08-01), Fujiu et al.
patent: 4816487 (1989-03-01), Schewe et al.
patent: 5091171 (1992-02-01), Yu et al.
patent: 5100893 (1992-03-01), Stokbroekx et al.
patent: 5276058 (1994-01-01), Satoh et al.
patent: 5324743 (1994-06-01), Dillard et al.
patent: 5356620 (1994-10-01), Yamamoto
patent: 5359098 (1994-10-01), Erickson et al.
patent: 5514778 (1996-05-01), Hammond et al.
patent: 5545653 (1996-08-01), Miller
patent: 5643929 (1997-07-01), Diana
patent: 6017957 (2000-01-01), Skolnick et al.
patent: 6020371 (2000-02-01), Dragovich
patent: 6087374 (2000-07-01), Schladetzky
patent: 6248306 (2001-06-01), Schmitt-Willich et al.
patent: 6369057 (2002-04-01), Billhardt et al.
patent: 0004579 (1979-10-01), None
patent: 0154883 (1972-06-01), None
patent: 0161750 (1972-09-01), None
patent: 0167900 (1974-01-01), None
patent: 0189141 (1980-08-01), None
patent: 0183860 (1984-07-01), None
Singh, Tetrahedron Letters 32, 5279, 1991.*
Allaire, Nature 369, pp. 72-76, May 1994.*
Carthy, Clin. Exp. Pharm. Physiol. 24, 997-1003, Dec. 1997.*
Ando, R. & Isaka, Y., 1993. “A new class of proteinase inhibitor. Cyclopropenone-containing inhibitor of papain,”J. Am. Chem. Soc.115:1174-1175.
Arad, D., et al., 1990. “A simulation of the sulfur attack in the catalytic pathway for papain using molecular mechanics and semiempirical; quantum mechanics,”J. Am Chem Soc.112:491-502.
Arad, D. et al., 1993. “Structural and mechanistic aspects of 3C proteases from the picornavirus family,”J. Chem. Inf. Comput. Sci.33:345-349.
Asboth, B. and Polgar, L., 1983. “Transition-state stabilization at the oxyanion binding sites of serine and thiol proteinases: hydrolyses of thiono and oxygen esters,”Biochemistry.22:117-122.
Bromme, D., et al., 1996. “Peptidyl vinyl sulphones: a new class of potent and selective cysteine protease inhibitors,”Biochem. J.315:85-89.
Cordingley, et al. 1990. “Substrate requirements of human rhinovirus 3C protease for peptide cleavage in vitro,”J Biol Chem265:9062-9065.
De Meyer, N., et al., 1991. “4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity,”J. Med. Chem.34(2):736-746.
Greenaway, W., et al., 1992 “Analysis of phenolics of bud exudates ofPopulus koreana, Populus maximowiczii, andPopulus suaveolensby GC-MS,”Z. Naturforsch.47c:313-317.
Kreisberg, R. et., 1995 “Mechanistic and structural features of the picornaviral 3C protease,”Organic reactivity: Physical and Biological Aspects. pp. 110-122.
Lau, C.K., et al., 1989. “Synthesis and structure -activity relationships of a novel class of 5-lipoxygenase inhibitors. 2-(Phenylmethyl)-4-hydroxy-3,5-dialkylbenzofurans: The development of L-656,224,”J. Med. Chem.32(6):1190-1197.
Lin, Y. and Welsh, W.J., 1996. “Molecular modeling of substrate -enzyme reactions for the cysteine protease papain,”J. Molecular Graphics.14:62-72.
Looker, J.H., et al., 1984. “5,8-Quinoflavone. Synthesis and addition reactions,”J. Org. Chem.49(4):645-649.
Masento, M.S., et al., 1988. “Differentiation-inducing factor from the slime mouldDictyostelium discoideumand its analogs,”Biochem. J.256:23-28.
Matthews, et al., 1994. “Structure of human rhinovirus 3 protease reveals a trypsin-like polypeptide fold, RNA-binding site, and means for cleaving precursor polyprotein,”Cell.77(5):761-771.
Menard, R. et al., 1991. “Contribution of the glutamine 19 side-chain to transition-state stabilization in the oxyanion hole of papain,”Biochemistry.30:8924-8928.
Morandini, P. , et al., 1995. “The proximal pathway of metabolism of the chlorinated signal molecule differentiation-inducing factor—1 (DIF-1) in the cellular slime mouldDictyostelium,”Biochemical Journal. 306:735-743.
Polgar, L. and Asboth, B., 1986. “The basic difference in catalyses by serine and cysteine proteinases resides in charge stabilization in the transition state,”J. Theor. Biol.121:323-326.
Rasnick, D. 1996. “Small synthetic inhibitors of cysteine proteases,”Perspectives in Drug Discovery and Design.6:47-63.
Schroder, E., et al., 1993. “X-ray crystallographic structure of a papain-leupeptin complex,”FEBS Lett.315:38-42.
Shokhen, M. and Arad, D., 1996. “The source for the difference between sulfhydryl and hydroxyl anions in their nucleophilic addition reaction to a carbonyl group: A DFT approach,”J. Moleculare Model.2:399-409.
Storer, A. C. and Menard, R., 1994. “Catalytic mechanism in papain family of cysteine peptidases,”Methods enzymol.244:486-500.
Vernet, T., et al., 1995. “Structural and functional roles of asparagine 175 in the cysteine protease papain,”J. Biol Chem.270:16645-16652.
The Merck Index.1989. “Salicylaldehyde,” S. Budavari, Ed., 11th Edition, Merck & Co., Inc., Rahway, N.J., p. 1323, No. 8295.
The Merck Index.1989. “Ethyl Salicylate,” S. Budavari, Ed., 11th Edition, Merck & Co. Inc., Rahway, N.J., p. 605, No. 3804.
The Merck Index.1989. “Benzyl Salicylate,” S. Budavari, Ed., 11th Edition, Merck & Co., Inc., Rahway, N.J., p. 179, No. 1160.
Kenny et al., 1985. “In Vitro and In Vivo Antipicornavirus Activity of Some Phenoxypyridinecarbonotrile”,Antimicrobial Agents and Chemotherapy.vol. 28, No. 6, pp. 745-750.
Morris et al. 1987. “Chemical Struture Of The Morphogen Differentiation Inducing Factor From Dictyostelium Discoideum,”Nature.vol. 328, No. 6133, pp. 811-814.
The Merck Index.1989. “Salicylic Acid,” S. Budavari, Ed., 11th Edition, Merck & Co., Inc., Rahway, N.J., p. 1324, No. 8301.
Arad Dorit
Elhanany Orna
Elias Yuval
Puzis Leopold
Shokhen Michael
Cytoclonal Pharmaceutics, Inc.
Low Christopher S. F.
Lukton David
Sidley Austin Brown & Wood LLP
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