Silanol enzyme inhibitors

Details Silanol enzyme inhibitors Silanol enzyme inhibitors

2005-11-01

2005-11-01

Weber, Jon (Department: 1653)

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

Organic compounds

Silicon containing

C556S411000, C556S413000, C556S418000, C556S419000, C556S425000, C556S436000, C562S553000, C514S063000

Reexamination Certificate

active

06960678

ABSTRACT:
Compounds of formula (I, II or III), wherein X is OH; Y is OH, H, lower alkyl of one to six carbons or heteroatoms or F; Z and Z′ are independently H, lower alkyl or Q3Si where Q is lower alkyl or aryl; n is 3-50; n′ is 2-50; A and B are independently a) alkyl of one to ten carbons or heteroatoms, b) aryl of four to seven carbons or heteroatoms, c) cyclic of three to ten carbons or heteroatoms, or moieties of the formulas (d, e, or f); R1-R11groups are each independently hydrogen, alkyl of one to ten carbons or heteroatoms, aryl of 4 to 14 carbons or heteroatoms, arylalkyl of five to twenty carbons or heteroatoms; unsubstituted carbonyl or substituted carbonyl. Heteroatoms are nitrogen, oxygen, silicon or sulfur. At least one of A or B, or both A and B are d), e), or f). The compounds of formula (I) inhibit protease enzymes and can be used as pharmaceuticals.

REFERENCES:
patent: 3860709 (1975-01-01), Abbott et al.
patent: 4328216 (1982-05-01), Toyoshima et al.
patent: 4420475 (1983-12-01), Damon, II
patent: 4898977 (1990-02-01), Herold et al.
patent: 4927952 (1990-05-01), Gueyne et al.
patent: 4985405 (1991-01-01), Gueyne et al.
patent: 5037803 (1991-08-01), Gueyne et al.
patent: 5045537 (1991-09-01), Weidmann
patent: 5087452 (1992-02-01), Gueyne et al.
patent: 5142056 (1992-08-01), Kempe et al.
patent: 5215968 (1993-06-01), Nickel et al.
patent: 5401722 (1995-03-01), Juraszyk et al.
patent: 5545750 (1996-08-01), Kempf et al.
patent: 0402646 (1990-12-01), None
Andrianov Chem. Abstr. 55:9316h.
Golubkov Chem. Abstr. 54:16059b.
Wiberg Chem. Abstr. 53: 1204g.
Andrianov Chem. Abstr. 53: 1204b.
Otiashvili Chem. Abstr. 127: 220707s, 1997.
Otiashvili Soobshch. Akad. Nauk Gruz. 152(3), 531-536, 1995.
Kam, C.M., Wishino, N., Powers, J.C. “Inhibition of Thermolysin and Carboxypeptidase A by Phosphoramidates”.Biochemistry1979, 18, 3032-3038.
Amiri, P., Lindquist, R.N., Matteson, D.S., Sadhu, K.M. “Benzamidomethaneboronic Acid: Synthesis and Inhibition of Chymotrypsin”. Arch. Biochem Biophys. 1984, 234, 531-536.
Galardy, P.E., Kortylewicz, Z.P., “Inhibitors of Angiotensin-Converting Enzyme Containing a Tetrahedral Arsenic Atom”,Biochem. J., 1985, 226, 447-454.
Likiss, P.D., “The Synthesis and Structure of Organosilanois,”Adv. Inorg. Chem. 1995, 42, 147-262.
Freidberg, K.D., Schiller, E.Handbook on the Toxicity of Inorganic Compounds. Seiler, H.G. and Sigel, H., Eds, Marcel Dekker, New York, 1988, pp 595-617.
Schechter, I., Berger, A. “On the Active Site of Protease. III. Mapping The Active Site of Papain; Specific Peptide Inhibitors of Papain.”Biochem. Biophys. Res. Commun. 1968, 32, 898-902.
Schechter, I., Berger, A. “On the Size of the Active Site in Proteases. I. Papain”,Biochem. Biophys. Res Commun. 1967, 27, 157-162.
I. Fleming, “Organic Silicon Chemistry” inComprehensive Organic Chemistry. D. Barton, W.D. Ollis, Eds, Pergamon, New York 1979, vol. 3, pp. 576-579.
I. Ojima, “The Hydrosilation Reaction” inThe Chemistry of Organic Silicon Compounds. S. Patai and Z. Rappoport, Eds., Wiley, New York 1989, vol. 2, pp 1479-1525.
Murai, T., Oda, T., Kimura, F., Onishi, H., T. Kanda, Kato, S., “Rhodium (11) Acetate Catalysed Hydrosilation of Enamides and N-Vinylureas Leading to 1-(Trialkylsilyl) alkylamine Derivatives”,J. Chem. Soc. Chem. Commun. 1994, 2143-2144.
Beak, P., Zajdel, W.J. Reitz, D.S. “Metalation and Electrophilic Substitution of Amine Derivatives Adjacent to Nitrogen: α-Metallo Amine Synthetic Equivalents”,Chem. Rev. 1984, 84, 471-523.
Eaborn, C., “Cleavages of Aryl-Silicon and Related Bonds by Electrophiles”,J. Organomet. Chem. 1975, 100, 43-57.
DeVoss, J.J., Z. Sui, D. DeCamp, R. Salto, L. Babé, C. Craik, P. Ortiz de Monteliano “Haloperidol-Based Irreversible Inhibitors of the HIV-1 and HIV-2 Proteases”,J. Med. Chem. 1994, 37, 665-673.
Vacca, J.P., “Design of Tight-Binding Human Immunodeficiency Virus Type 1 Protease Inhibitors”,Methods Enzymol. 1994, 241, 311-334.
Matthews, B.W., “Structural Basis of the Action of Thermolysin And Related Zinc Peptidases”,Acc. Chem. Res. 1988, 21, 333-340.
Christianson, D.W., Lipscomb, W.M., “Carboxypeptidase A”,Acc. Chem Res. 1989, 22. 62-69.
Rich, D.H., “Peptidase Inhibitors”, inComprehensive Medicinal Chemistry. C. Hansh et al, Ed., Pergamon, New York 1990, pp 391-441.
Fischer, G., “Trends in Protease Inhibition”National Product Reports1988, 5, 465-495.
Gordon, E.M., S. Natarajan, J. Pluscec, H.W. Weller, J.D. Godfrey, M.S. Rom, E.F. Sabo, J. Engebrecht, D.W. Cushman, “Katomethyldipeptides II. Effect of Modification of the α-Aminoketone Portion on Inhibition of Angiotensin Converting Enzyme”,Biochem. Biophys. Res. Commun. 1984, 124, 148-155.
Bone, R., Sampson, M.S., Bartlett, P.A., Agard, D.A. “Crystal Structure of α-Lytic Protease Complexes With Irreversibly Bound Phosphonate Esters”,Biochemistry1991, 30, 2263-2272.
Govardhan, C.P., “Structure- Activity Studies of Fluroketone Inhibitors Abeles, R.H., of α-Lytic Protease and Human Leucocyte Elastase”,Arch. Biochem Biophys. 1990, 280, 137-146.
Corriu, R.J.P., Guérin, C., Moreau, J.J.E., “Stereochemistry at Silicon”,Topics In Stereochemistry1984, 15, 80-103.
R. Tacke, D. Reichel, M. Kropfgans, P.G. Jones, E. Mutschler, J. Gross, X. Hou, M. Waelbroeck, G. Lambrecht, “Biological Recognition of Enantiomeric Silanes: Syntheses And Antimuscarinic Properties of Optically Active (α-Aminoethyl)clyclohexyl(hydroxy methyl) phenylsilanes And Related Quaternary Ammonium Derivatives”,Organometallics1995, 14, 251-257.
F. Liebner, U. Bankwitz, Rühlmann, K., Synthese Von Fungicid Wirksamen (1H-α, 4-Triazol-1-yl-methyl) silanen Und—siloxanen,liebigs Ann. Chem. 1994, 145-150.
S. Thaisrivongs, “ HIV Protease Inhibitors”,Annual Reports In Medicinal Chemistry. ed. J.A. Bristol, Academic Press, Inc., New York 1994, 29, 133-144.
R. Bone, J.P. Vacca, P.S. Anderson, M.K. Holloway, “X-Ray Crystal Structure of the HIV Protease Complex with L-700, 417, An Inhibitor With Pseudo C2Symmetry”,Journal of the American Chemical Society. 1991, 113, 9382-9384.
J.P. Vacca, J.P. Guare, S.J. deSolms, W.M. Sanders, E.A. Giuliani, S.D. Young, P.L. Darke, J. Zugay, I.S. Sigal, W.A. Schleif, J.C. Quintero, E.A. Emini, P.S. Anderson, J.R. Huff, “Benzocycloalkyl Amines As Novel C-Termini For HIV Protease Inhibitors”,Journal of Medicinal Chemistry. 1991, 34, 228-1230.
I. Fleming, “the Electrophilic Substitution of Allysilanes And Vinylsilanes”,Organic Reactions. John Wiley & Sons, Inc., New York, 1989, 61.
J.Y. Corey, D.M., Kraichely, J.L. Huhmann, J. Braddock-Wilking, “Reactions of H(PhMeSi)3H With Triflic Acid: Evidence of Rearrangement Processes”,Organometallics1994, 13, 3408-3410.
W. Uhtig, “Zur Darstellung Neuer Organosiliciumpolymere Aus Spezieli Substituierten Silyltriflatderivaten”,Journal of Organometallic Chemistry1994, 476, 225-229.
H. Stüger, “Synthese 1,4-disubstitierter Tetrasilane Durch Selektive Spaitung Von Si-Phenyl Bindungen”,Journal of Organometallic Chemistry1992, 433, 11-19.
A.R. Bassindale, T. Stout, “The Synthesis Of Functionalized Silytriflates”,Journal of Organometallic Chemistry1984, 271, C1-C3.
C. Eaborn, “Organosilicon Compounds. Part I. The Formation Of Alkyliodosilanes”,Journal of the Chemical Society1949, 2755-2764.
Tacke, R., Linch, H., “Bioorganosilicon Chemistry” inThe Chemistry of Organic Silicon Compounds. S. Patai and Z. Rappaport, Eds, John Wiley, New York 1989, pp 1143-1206.

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