Publications Robert M.

Rydzewski

Book Real World Drug Discovery: A Chemists Guide to Biotech and Pharmaceutical Research, Robert M. Rydzewski; Elsevier, Oxford; 2008.

Book Chapters Maag, H., Gutierrez, A.J., Prisbe, E.J., Rydzewski, R.M., Verheyden, J.P.H. 4'Substituted Nucleosides as Antiviral Agents in Antibiotics and Antiviral Compounds, Chemical Synthesis and Modification, Krohn, K., Kirst, H.A., Maag, H., Eds.; VCH Press Weinheim; 1993, pp 421-438. Prisbe, E.J., Maag, H., Verheyden, J.P.H., Rydzewski, R.M. Structure-Activity Relationships Among HIV Inhibitory 4'-Substituted Nucleosides. In Nucleosides and Nucleotides as Antitumor and Antiviral Agents; Chu, C.K., Baker, D.C., Eds.; Plenum Press: New York, 1993; pp 101-113.

Patents Prasit, P.; Bayly, C. I.; Robichaud, J. S.; Black, W. C.; Setti, E. L.; Rydzewski, R. M.; Palmer, J. T. Cathepsin Cysteine Protease Inhibitors. U. S. Patent 7,012,075, filed 28 August 2003 and issued 14 March, 2006. Okamoto, O.; Falgueyret, J.-P.; Oballa, R. M.; Prasit, P.; Rydzewski, R. Cathepsin cysteine protease inhibitors. U. S. Patent 6,835,727, filed 23 August 2002 and issued 28 December, 2004. Bryant, C. M.; Palmer, J. T.; Rydzewski, R. M.; Setti, E. L.; Tian, Z.-Q.; Venkatraman, S.; Wang, D.-X. Compounds and compositions as protease inhibitors. U. S. Patent 6,593,327, filed 14 December 2001 and issued 15 July 2003. Bryant, C. M.; Palmer, J. T.; Rydzewski, R. M.; Setti, E. L.; Tian, Z.-Q.; Venkatraman, S.; Wang, D.-X. Compounds and compositions as protease inhibitors. U. S. Patent 6,476,026, filed 15 March 2000 and issued 05 November 2002.

Patent Applications Palmer, J.: Rydzewski, R.M. Reversible Inhibitors of Cathepsin B. International Patent Application WO 2006/042103, filed 05 October 2005. Broder, S. E.; Rydzewski, R. M. Diabetes and metabolic syndrome therapy utilizing cathepsin B inhibitors. International Patent Application WO 2005/097103, filed 01 April 2005.

Burrill II, L. C.; Palmer, J. T.; Rydzewski, R. M. 3-(3, 5-Disubstituted-4hydroxyphenyl)propionamide derivatives as cathepsin B inhibitors. U.S. Patent Application 20050282871, filed 17 March 2005. Burrill II, L. C.; Mendonca, R. V.; Palmer, J. T.; Rydzewski, R. M. Proteasome inhibitors. International Patent Application WO 2004/014882, filed 08 August 2003. Burrill II, L. C.; Palmer, J. T.; Rydzewski, R. M. 3-(3, 5-Disubstituted-4hydroxyphenyl)propionamide derivatives as cathepsin B inhibitors. International Patent Application WO 2004/026851, filed 01 April 2004. Bryant, C. M.; Palmer, J. T.; Rydzewski, R. M.; Setti, E. L.; Tian, Z.-Q.; Venkatraman, S.; Wang, D.-X. Novel compounds and compositions as protease inhibitors. U. S. Patent Application 20030119788, filed 09 September 2002. Prasit, P.; Bayly, C. I.; Robichaud, J. S.; Black, W. C.; Setti, E. L.; Rydzewski, R. M.; Palmer, J. T. Cathepsin cysteine protease inhibitors. International Patent Application WO 02/069901, filed 01 March 2002. Prasit, P.; Falgueyret, J.-P.; Oballa, R.; Rydzewski, R.; Okamoto, O. Cathepsin cysteine protease inhibitors. International Patent Application WO 01/77073, filed 04 April 2001.

Papers Dang, Q.; Rydzewski, R.M.; Cashion, D.K.; Erion, M.D. An unexpected cyclization discovered during the synthesis of 8-substituted purines from a 4,5-diaminopyrimidine. Tetrahedron. Lett. 2008, 49, 2143-2145. Dang, Q.; Liu, Y.; Rydzewski, R.M.; Brown, B.S.; Robinson, E.; van Poilje, P.D.; Colby, T.J.; Erion, M.D. Bis[(para-methoxy)benzyl] phosphonate prodrugs with improved stability and enhanced cell penetration. Bioorg. Med. Chem. Lett. 2007, 17, 3412-3416. Palmer, J.T.; Rydzewski, R.M.; Mendonca, R.V.; Sperandio, D.; Spencer, J.R.; Hirschbein, B.L.; Lohman, J.; Beltman, J.; Nguyen, M.; Liu, L. Design and synthesis of selective keto-1,2,4-oxadiazole-based tryptase inhibitors. Bioorg. Med. Chem. Lett. 2006, 16, 3434-3439. Rydzewski, R. M.; Burrill, L.; Mendonca, R.; Palmer, J. T.; Rice, M.; Tahilramani, R.; Bass, K. E.; Leung, L.; Gjerstad, E.; Janc, J. W.; Pan, L. Optimization of Subsite Binding to the 5 subunit of the Human 20S Proteasome Using Vinyl Sulfones and 2-Keto-1,3,4Oxadiazoles: Syntheses and Cellular Properties of Potent, Selective Proteasome Inhibitors. J. Med. Chem. 2006, 49, 2953-2968. Palmer, J. T.; Bryant, C.; Wang, D.-X.; Davis, D. E.; Setti, E. L.; Rydzewski, R. M.; Venkatraman, S.; Tian, Z.-Q.; Burrill, L. C.; Mendonca, R. V.; Springman, E.; McCarter, J.; Chung, T.; Cheung, H.; Janc, J. W.; McGrath, M.; Somoza, J. R.; Enriquez, P.; Yu, Z. W.; Strickley, R. M.; Liu, L.; Venuti, M. C.; Percival, M. D.; Falgueyret, J.-P.; Prasit, P.; Oballa, R.; Riendeau, D.; Young, R. N.; Wesolowski, G.; Rodan, S. B.; Johnson, C.; Kimmel, D. B.; Rodan, G. Design and Synthesis of Tri-Ring P3 Benzamide-Containing

Aminonitriles as Potent, Selective, Orally Effective Inhibitors of Cathepsin K. J. Med. Chem. 2005, 48, 7520-7534. Feldstein, A. E.; Werneburg, N. W.; Canbay, A.; Guicciardi, M. E.; Bronk, S. F.; Rydzewski, R.; Burgart, L. J.; Gores, G. J. Free Fatty Acids Promote Hepatic Lipotoxicity by Stimulating TNF- Expression via a Lysosomal Pathway. Hepatology 2004, 40, 185194. Canbay, A.; Guiccardi, M. E.; Higuchi, H.; Feldstein, A.; Bronk, S. F.; Rydzewski, R.; Taniai, M.; Gores, G. J. Cathepsin B inactivation attenuates hepatic injury and fibrosis during cholestasis. J. Clin. Invest. 2003, 112, 152-159. Cathers, B. E.; Barrett, C.; Palmer, J. T.; Rydzewski, R. M. pH Dependence of inhibitors targeting the occluding loop of cathepsin B. Bioorg. Chem. 2002, 30, 264-275. Rydzewski, R. M.; Bryant, C.; Oballa, R.; Wesolowski, G.; Rodan, S. B.; Bass, K. E.; Wong, D. H. Peptidic 1-Cyanopyrrolidines: Synthesis and SAR of a Series of Potent, Selective Cathepsin Inhibitors. Bioorg. Med. Chem. 2002, 10, 3277-3284. Falgueyret, J.-P.; Oballa, R. M.; Okamoto, O.; Wesolowski, G.; Aubin, Y.; Rydzewski, R. M.; Prasit, P.; Riendeau, D.; Rodan, S. B.; Percival, M. D. Novel, Nonpeptidic Cyanamides as Potent and Reversible Inhibitors of Human Cathepsins K and L. J. Med. Chem. 2001, 44, 94-104. Rydzewski, R. M.; Erion, M. D. 4-Substituted-5(3)-carbamoyl-3(5)-(2-deoxy- -Dribofuranosyl)pyrazoles. Application of Palladium Catalyzed Glycal Coupling Methodology to the Synthesis of Pyrazofurin Analogs. Nucleosides and Nucleotides 1997, 16, 315-337. Semple, J. E.; Rydzewski, R. M.; Gardner, G. An Efficient Synthetic Route to Ethyl 2Aryl-4-hydroxy-1,3(2H, 4H)-dioxoisoquinoline-4-carboxylates. J. Org. Chem. 1996, 61, 7967-7972. Maag, H.; Rydzewski, R. M. An Allylic Azide Route to 4'-Azido Carbocyclic Nucleosides. Synthesis of ()-(1',2',3')-1-[1-Azido-2-hydroxy-1-(hydroxymethyl)-3cyclopentyl]thymine. J. Org. Chem. 1992, 57, 5823-5831. Maag, H.; Rydzewski, R. M.; McRoberts, M. J.; Crawford-Ruth, D.; Verheyden, J. P. H.; Prisbe, E. J. Synthesis and Anti-HIV Activity of 4'-Azido- and 4'-Methoxynucleosides. J. Med. Chem. 1992, 35, 1440-1451. Maag, H.; Chu, N.; Crawford-Ruth, D.; Eugui, E.; McRoberts, M. J.; Mirkovich, A.; Pettibone, M.; Prisbe, E. J.; Rydzewski, R. M.; Verheyden, J. P. H. 4'-Azido-thymidine: Synthesis and in vitro Activity. Antiviral Res. 1991, Suppl.1, 10. Madhavan, G. V. B.; McGee, D. P. C.; Rydzewski, R. M.; Boehme, R.; Martin, J. C.; Prisbe, E. J. Synthesis and Antiviral Evaluation of 6'-Substituted Aristeromycins: Potential Mechanism-Based Inhibitors of S-Adenosylhomocysteine Hydrolase. J. Med. Chem. 1988, 31, 1798-1804.

Djuric, S. W.; Miyano, M.; Clare, M.; Rydzewski, R. M. A Stereocontrolled Synthesis of a Novel Prostacyclin Analog "Allene-Carbacyclin". Application of Molecular Mechanics Calculations to Organic Synthesis. Tetrahedron Lett. 1987, 28, 299-302. Chorvat, R. J.; Prodan, K. A.; Adelstein, G. W.; Rydzewski, R. M.; McLaughlin, K. T.; Stamm, M. H.; Frederick, L. G.; Schniepp, H. C.; Stickney, J. L. Synthesis and Structure-Activity Relationships of a New Series of Antiarrhythmic Agents: 4,4Disubstituted Hexahydro-3H-pyrido[1,2-c]pyrimidin-3-ones and Related Compounds. J. Med. Chem. 1985, 28, 1285-1291.

Posters and Presentations Bass, K. E.; Leung, L.; Gjerstad, E.; Burrill, C.; Janc, J.; Magill, C.; Rydzewski, R. Differential response of endothelial cells to proteasome inhibitors. Poster presented at the American Association for Cancer Research meeting, San Francisco, California, 2002. Wong, D. H.; Estevez, A.; Kantak, S.; Oeh, J.; Rajan, S.; Gosink, L.; Lapresca, P.; Feng, J.; Strickley, R.; Jejurkar, P.; Mordenti, J.; Cathers, B. E.; Barrett, C.; Palmer, J. T.; Rydzewski, R. M.; Bass, K. E.; Magill, C.; Babe, L.; Neri, A. Inhibition of cathepsins B and L has no effect on tumor progression in the B16F10 experimental metastasis model. Poster presented at the American Association for Cancer Research meeting, New Orleans, Louisiana, March 2001. Oballa, R.; Falgueyret, J.-P.; Prasit, P.; Percival, M. D.; Riendeau, D.; Okamoto, O.; Wesolowski, G.; Rodan, S.; Rydzewski, R.; Aubin, Y. Novel class of non-peptidic cyanamide inhibitors of human cathepsin K. Abstracts of Papers, 220th American Chemical Society National Meeting, Washington, D. C., August 2000.