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Reviews

Cathepsin S inhibitors: 2004 – 2010

, PhD, & , PhD
Pages 311-337 | Published online: 23 Feb 2011

Bibliography

  • Vasiljeva O, Reinheckel T, Peters C, Emerging roles of cysteine cathepsins in disease and their potential as drug targets. Curr Pharm Des 2007;13(4):387-403
  • Gupta S, Singh RK, Dastidar S, Ray A. Cysteine cathepsin S as an immunomodulatory target: present and future trends. Expert Opin Ther Targets 2008;12(3):291-9
  • Wiener JJM, Sun S, Thurmond RL. Recent advances in the design of cathepsin S inhibitors. Curr Top Med Chem 2010;10(7):717-32
  • Nakagawa TY, Brissette WH, Lira PD, Impaired invariant chain degradation and antigen presentation and diminished collagen-induced arthritis in cathepsin S null mice. Immunity 1999;10(2):207-17
  • Shi G-P, Villadangos JA, Dranoff G, Cathepsin S required for normal MHC class II peptide loading and germinal center development. Immunity 1999;10(2):197-206
  • Podolin PL, Bolognese BJ, Carpenter DC, Inhibition of invariant chain processing, antigen-induced proliferative responses, and the development of collagen-induced arthritis and experimental autoimmune encephalomyelitis by a small molecule cysteine protease inhibitor. J Immunol 2008;180(12):7989-8003
  • Biroc SL, Gay S, Hummel K, Cysteine protease activity is up-regulated in inflamed ankle joints of rats with adjuvant-induced arthritis and decreases with in vivo administration of a vinyl sulfone cysteine protease inhibitor. Arthritis Rheum 2001;44(3):703-11
  • Riese RJ, Mitchell RN, Villadangos JA, Cathepsin S activity regulates antigen presentation and immunity. J Clin Invest 1998;101(11):2351-63
  • Clark AK, Yip PK, Grist J, Inhibition of spinal microglial cathepsin S for the reversal of neuropathic pain. Proc Natl Acad Sci USA 2007;104(25):10655-60
  • Teupser D, Pavlides S, Tan M, Major reduction of atherosclerosis in fractalkine (CX3CL1)-deficient mice is at the brachiocephalic artery, not the aortic root. Proc Natl Acad Sci USA 2004;101(51):17795-800
  • Sukhova GK, Zhang Y, Pan J-H, Deficiency of cathepsin S reduces atherosclerosis in LDL receptor–deficient mice. J Clin Invest 2003;111(6):897-906
  • Shi G-P, Suknhova GK, Kuzuya M, Deficiency of the cysteine protease cathepsin S impairs microvessel growth. Circ Res 2003;92(5):493-500
  • Wang B, Sun J, Kitamoto S, Cathepsin S controls angiogenesis and tumor growth via matrix-derived angiogenic factors. J Biol Chem 2006;281(9):6020-9
  • Pauly TA, Sulea T, Ammirati M, Specificity determinants of human cathepsin S revealed by crystal structures of complexes. Biochemistry 2003;42(11):3203-13
  • Gauthier JY, Black WC, Courchesne I, The identification of potent, selective, and bioavailable cathepsin S inhibitors. Bioorg Med Chem Lett 2007;17(17):4929-33
  • Cai J, Bennett DJ, Rankovic Z, 2-Phenyl-9H-purine-6-carbonitrile derivatives as selective cathepsin S inhibitors. Bioorg Med Chem Lett 2010;20(15):4447-50
  • Irie O, Ehara T, Iwasaki A, Discovery of selective and nonpeptidic cathepsin S inhibitors. Bioorg Med Chem Lett 2008;18(14):3959-62
  • Liu H, Tully DC, Epple R, Design and synthesis of arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 1. Bioorg Med Chem Lett 2005;15(22):4979-84
  • Leroy V, Thurairatnam S. Cathepsin S inhibitors. Expert Opin Ther Patents 2004;14(3):301-11
  • Thurmond RL, Sun S, Karlsson L, Edwards JP. Cathepsin S inhibitors as novel immunomodulators. Curr Opin Investig Drugs 2005;6(5):473-82
  • Link JO, Zipfel S. Advances in cathepsin S inhibitor design. Curr Opin Drug Discov Dev 2006;9(4):471-82
  • Maryanoff BE, Costanzo MJ. Inhibitors of proteases and amide hydrolases that employ an alpha-ketoheterocycle as a key enabling functionality. Bioorg Med Chem 2008;16(4):1562-95
  • Fusion Antibodies Limited. Therapy. WO2007128987; 2007
  • Fusion Antibodies Limited. Antibody and uses thereof. WO2008044076; 2008
  • Elie BT, Gocheva V, Shree T, Identification and pre-clinical testing of a reversible cathepsin protease inhibitor reveals anti-tumor efficacy in a pancreatic cancer model. Biochemie 2010;92(11):1618-24
  • Medivir UK Ltd & Peptimmune, Inc. Furanone derivatives as inhibitors of cathepsin S. WO200069855; 2000
  • Medivir UK Ltd & Peptimmune, Inc. C-5 substituted furanone dipeptide cathepin S inhibitors. WO2005082876; 2005
  • Medivir UK Ltd & Peptimmune, Inc. Cathepsin S inhibitors. WO2006064286; 2006
  • Ayesa S, Lindquist C, Agback T, Solid-phase parallel synthesis and SAR of 4-amidofuran-3-one inhibitors of cathepsin S: effect of sulfonamides P3 substituents on potency and selectivity. Bioorg Med Chem 2009;17(3):1307-24
  • Medivir AB. Bicyclic compounds useful as cathepsin S inhibitors. WO2007144379; 2007
  • Medivir AB. Protease inhibitors. WO2010034788; 2010
  • Medivir AB. Protease inhibitors. WO2010034789; 2010
  • Medivir AB. Protease inhibitors. WO2010034790; 2010
  • Medivir AB. Project Portfolio. Available from: http://www.medivir.se/v4/en/
  • Amura Therapeutics Limited. Furo[3,2-B]pyrrole-3-ones as cathepsin S inhibitors. WO2009112826; 2009
  • Amura Therapeutics Limited. Compounds. WO2009112839; 2009
  • Amura Therapeutics Limited. Tetrahydrofuro[3,2-B]pyrrole-3-one derivatives as inhibitors of cysteine proteases. WO2009144450; 2009
  • Amura reports antigen presentation study results. Available from: http://www.amura.co.uk/news.asp; April 7, 2009
  • Amura announces positive results in chronic neuropathic pain model. Available from: http://www.amura.co.uk/news.asp; April 7, 2009
  • Amura reports rheumatoid arthritis study results. Available from: http://www.amura.co.uk/news.asp; September 1, 2009
  • IRM LLC (Novartis Genomics Institute). Compounds and compositions as cathepsin S inhibitors. WO2005107464; 2005
  • IRM LLC (Novartis Genomics Institute). Inhibitors of cathepsin S. WO2005039496; 2005
  • Vertex Pharmaceuticals, Inc. Inhibitors of interleukin-1beta converting enzyme. US6103711; 2000
  • Cytovia, Inc. Caspase inhibitors and the use thereof. US6716818; 2004
  • Axys Pharmaceuticals, Inc. (Celera Genomics). Haloalkyl containing compounds as cysteine protease inhibitors. WO2005028454; 2005
  • Axys Pharmaceuticals, Inc. (Celera Genomics). Amidino compounds as cysteine protease inhibitors. WO2005063742; 2005
  • Axys Pharmaceuticals, Inc. (Celera Genomics). Silinane compounds as cysteine protease inhibitors. WO2005074904; 2005
  • Applera Corporation (Celera Genomics). Alpha ketoamide compounds as cysteine protease inhibitors. WO2006102243; 2006
  • Applera Corporation (Celera Genomics). Alpha ketoamide compounds as cysteine protease inhibitors. WO2006102423; 2006
  • Virobay, Inc. Compounds that inhibit protease cathepsin S and HCV replication. WO2009055467; 2009
  • 4SC AG. Inhibitors of cancer cell, T-cell and keratinocyte proliferation. WO2007017284; 2007
  • Wood WJL, Patterson AW, Tsuruoka H, Substrate activity screening: A fragment-based method for the rapid identification of nonpeptidic protease inhibitors. J Am Chem Soc 2005;127(44):15521-7
  • Patterson AW, Wood WJL, Ellman JA. Substrate activity screening (SAS): a general procedure for the preparation and screening of a fragment-based non-peptidic protease substrate library for inhibitor discovery. Nat Protocols 2007;2(2):424-33
  • Patterson AW, Wood WJL, Hornsby M, Identification of selective, nonpeptidic nitrile inhibitors of cathepsin S using the substrate activity screening method. J Med Chem 2006;49(21):6298-307
  • Inagaki H, Tsuruoka H, Hornsby M, Characterization and optimization of selective, nonpeptidic inhibitors of cathepsin S with an unprecedented binding mode. J Med Chem 2007;50(11):2693-9
  • Aventis Pharmaceuticals, Inc. (Sanofi-aventis). Novel keto-oxadiazole derivatives as cathepsin inhibitors. WO2005040142; 2005
  • Sanofi-aventis. Spirocyclic nitriles as protease inhibitors. WO2007137738; 2007
  • Sanofi-aventis. Spirocyclic nitriles as protease inhibitors. US20090275523; 2009
  • Merck Frosst Canada & Axys Pharmaceuticals. Cathepsin cysteine protease inhibitors. WO2003075836; 2003
  • Merck Frosst Canada. Cathepsin cysteine protease inhibitors. WO2005019161; 2005
  • Merck Frosst Canada. Cathepsin inhibitors. WO2005021487; 2005
  • Merck Frosst Canada. Cathepsin cysteine protease inhibitors. WO2005056529; 2005
  • Merck Frosst Canada. Cathepsin cysteine protease inhibitors. WO2006056047; 2006
  • Gauthier JY, Chauret N, Cromlish W, The discovery of odanacatib (MK-0822), a selective inhibitor of cathepsin K. Bioorg Med Chem Lett 2008;18(3):923-8
  • Axys Pharmaceuticals, Inc. (Celera Genomics). Compounds and compositions as protease inhibitors. US6576630; 2003
  • Merck Frosst Canada. Prodrugs of inhibitors of cathepsin S. WO2008028301; 2008
  • Merck Frosst Canada. Fluoroalkylamines derivatives as cathepsin S inhibitors. WO2006128287; 2006
  • Axys Pharmaceuticals, Inc. (Celera Genomics). Haloalkyl containing compounds as cysteine protease inhibitors. WO2005028429; 2005
  • Axys Pharmaceuticals, Inc. (Celera Genomics). Polymorphs of the cysteine protease inhibitor N-(1-cyanocyclopropyl)-3-cyclopropylmethansulfonyl-2 (R)-(2,2,2-trifluoro-1 (S)-(4-fluorophenyl)-ethylamino) propionamide. WO2006034006; 2006
  • Axys Pharmaceuticals, Inc. (Celera Genomics). Processes and intermediates for preparing cysteine protease inhibitors. WO2006034004; 2006
  • Axys Pharmaceuticals, Inc. (Celera Genomics). Sulfonamide compounds as cysteine protease inhibitors. WO2006060810; 2006
  • Applera Corp. (Celera Genomics). Sulfonyl containing compounds as cysteine protease inhibitors. WO2006102535; 2006
  • Virobay, Inc. Di-fluoro containing compounds as cysteine protease inhibitors. WO2008042968; 2008
  • Axys Pharmaceuticals, Inc. (Celera Genomics). Haloalkyl containing compounds as cysteine protease inhibitors. WO2006060494; 2006
  • Celera Genomics initiates Phase I clinical trial for cathepsin S inhibitor for the treatment of psoriasis. Available from: https://www.celera.com/celera/pr_1127168705; September 20, 2005
  • Celera Genomics announces the sale of its cathepsin S inhibitor program to Schering AG. Available from: https://www.celera.com/celera/pr_1152570053; June 21, 2006
  • AstraZeneca AB. Novel compounds. WO2004000825; 2003
  • AstraZeneca AB. Cathepsin cysteine protease inhibitors and their use. WO2004054987; 2004
  • Asaad N, Bethel PA, Coulson MD, Dipeptidyl nitrile inhibitors of cathepsin L. Bioorg Med Chem Lett 2009;19(15):4280-3
  • Bethel PA, Gerhardt S, Jones EV, Design of selective cathepsin inhibitors. Bioorg Med Chem Lett 2009;19(16):4622-5
  • Boehringer Ingelheim Pharmaceuticals, Inc. Cathepsin S inhibitors. WO2004083182; 2004
  • Korea Research Institute of Chemical Technology. Novel carbonitrile compounds, process for preparing thereof, and pharmaceutical composition for treating or preventing articular rheumatism, osteoarthritis, Paget's disease, hypercalcemia of malignancy, metabolic bone disease and cancers comprising the same. KR2009005842; 2009
  • Song JH, Kim SG, No ZS, Discovery and synthesis of novel N-cyanopyrazolidine and N-cyanohexahydropyridazine derivatives as cathepsin inhibitors. Bull Korean Chem Soc 2008;29(8):1467-71
  • AstraZeneca AB. New use of pyrimidine- or triazine-2-carbonitriles for treating diseases associated with cysteine protease activity and novel pyrimidine-2-carbonitrile derivatives. WO2004000819; 2003
  • AstraZeneca AB. Novel purine- or pyrrolol[2,3-d]pyrimidine-2-carbonitriles for treating diseases associated with cysteine protease activity. WO2004000843; 2003
  • AstraZeneca UK Limited. Pteridine derivatives and their use as cathepsin inhibitors. WO2007148064; 2007
  • Morley AD, Kenny PW, Burton B, 5-Aminopyrimidin-2-ylnitriles as cathepsin K inhibitors. Bioorg Med Chem Lett 2009;19(6):1658-61
  • Novartis-Pharma GMBH. Pyrrolo pyrimidines as agents for the inhibition of cysteine protease. WO2003020721; 2003
  • Novartis-Pharma GMBH. Spiro-substituted pyrrolopyrimidines. WO2004076455; 2004
  • Teno N, Miyake T, Ehara T, Novel scaffold for cathepsin K inhibitors. Bioorg Med Chem Lett 2007;17(22):6096-100
  • Novartis-Pharma GMBH. 2-Cyanopyrrolopyrimidines and pharmaceutical uses thereof. WO2004069256; 2004
  • Irie O, Kosaka T, Ehara T, Discovery of orally bioavailable cathepsin S inhibitors for the reversal of neuropathic pain. J Med Chem 2008;51(18):5502-5
  • Novartis-Pharma GMBH. Compounds and compositions useful as cathepsin S inhibitors. WO2006018284; 2006
  • Novartis-Pharma GMBH. Cysteine protease inhibitors with 2-cyano-4-amino-pyrimidine structure and cathepsin K inhibitory activity for the treatment of inflammations and other diseases. WO2003020278; 2003
  • Altmann E, Aichholz R, Betschart C, 2-Cyano-pyrimidines: a new chemotype for inhibitors of the cysteine protease cathepsin K. J Med Chem 2007;50(4):591-4
  • Irie O, Yokokawa F, Ehara T, 4-Amino-2-cyanopyrimidines: novel scaffold for nonpeptidic cathepsin S inhibitors. Bioorg Med Chem Lett 2008;18(16):4642-6
  • Irie O, Kosaka T, Kishida M, Overcoming hERG issues for brain-penetrating cathepsin S inhibitors: 2-cyanopyrimidines. Part 2. Bioorg Med Chem Lett 2008;18(19):5280-4
  • N.V. Organon. 4-Phenyl-pyrimidine-2-carbonitrile derivatives. WO2005121106; 2005
  • N.V. Organon. 4-Phenyl-6-substituted-pyrimidine-2-carbonitrile derivatives. WO2007039470; 2007
  • Rankovic Z, Cai J, Kerr J, Design and optimization of a series of novel 2-cyano-pyrimidines as cathepsin K inhibitors. Bioorg Med Chem Lett 2010;20(5):1524-7
  • Cai J, Fradera X, van Zeeland M, 4-(3-Trifluoromethylphenyl)-pyrimidine-2-carbonitrile as cathepsin S inhibitors: N3, not N1 is critically important. Bioorg Med Chem Lett 2010;20(15):4507-10
  • Falgueyret J-P, Desmarais S, Oballa R, Lysosomotropism of basic cathepsin K inhibitors contributes to increased cellular potencies against off-target cathepsins and reduced functional selectivity. J Med Chem 2005;48(24):7535-43
  • N.V. Organon. 6-Phenyl-1H-Imidazo[4, 5-C]pyridine-4-carbonitrile derivatives as cathepsin K and S inhibitors. WO2007080191; 2007
  • N.V. Organon. 6-Phenyl-1H-Imidazo[4, 5-C]pyridine-4-carbonitrile derivatives as cathepsin inhibitors. WO2009010491; 2009
  • Cai J, Baugh M, Black D, 6-Phenyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile as cathepsin S inhibitors. Bioorg Med Chem Lett 2010;20(15):4350-4
  • Oballa RM, Truchon J-F, Bayly CI, A generally applicable method for assessing the electrophilicity and reactivity of diverse nitrile-containing compounds. Bioorg Med Chem Lett 2007;17(4):998-1002
  • Sunesis Pharmaceuticals. Carbon-linked tetrahydro-pyrazolo-pyridine modulators of cathepsin S. WO2008100618; 2008
  • Sunesis Pharmaceuticals. Tetrahydro-pyrazolo-pyridine thioether modulators of cathepsin S. WO2008100621; 2008
  • Sunesis Pharmaceuticals. Biaryl substituted tetrahydro-pyrazolo-pyridine modulators of cathepsin S. WO2008100622; 2008
  • Sunesis Pharmaceuticals. Bicyclic aminopropyl tetrahydro-pyrazolo-pyridine modulators of cathepsin S. WO2008100620; 2008
  • Sunesis Pharmaceuticals. 1-[3-(Monocyclic amino)propyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-C]-pyridines as modulators of cathepsin S. WO2008100635; 2008
  • Ameriks MK, Axe FU, Bembenek SD, Pyrazole-based cathepsin S inhibitors with arylalkynes as P1 binding elements. Bioorg Med Chem Lett 2009;19(21):6131-4
  • Wiener DK, Lee-Dutra A, Bembenek S, Thioether acetamides as P3 binding elements for tetrhydropyrido-pyrazole cathepsin S inhibitors. Bioorg Med Chem Lett 2010;20(7):2379-82
  • Ameriks MK, Bembenek SD, Burdett MT, Diazinones as P2 replacements for pyrazole-based cathepsin S inhibitors. Bioorg Med Chem Lett 2010;20(14):4060-4
  • Ameriks MK, Cai H, Edwards JP, Pyrazole-based arylalkyne cathepsin S inhibitors. Part II: optimization of cellular potency. Bioorg Med Chem Lett 2009;19(21):6135-9
  • Lee-Dutra A, Wiener DK, Arienti KL, Discovery and SAR of novel pyrazole-based thioethers as cathepsin S inhibitors: Part 1. Bioorg Med Chem Lett 2010;20(7):2370-4
  • Wiener JJM, Wickboldt AT, Wiener DK, Discovery and SAR of novel pyrazole-based thioethers as cathepsin S inhibitors. Part 2: modification of P3, P4 and P5 regions. Bioorg Med Chem Lett 2010;20(7):2375-8
  • NCT00396422: study to investigate the safety, tolerability, absorption, distribution, metabolism, and elimination of RWJ-445380 administered to patients with plaque psoriasis. Available from: www.clinicaltrials.gov; November 2006
  • NCT00425321: safety and effectiveness study of RWJ-445380 cathepsin-S inhibitor in patients with active rheumatoid arthritis despite methotrexate therapy. Available from: www.clinicaltrials.gov; April 2007
  • Sunesis Pharmaceuticals announces milestone payment from inflammation collaboration. Available from: http://ir.sunesis.com/releasedetail.cfm?ReleaseID=295117; February 20, 2008
  • IRM L.L.C. (Novartis Genomics Institute). Inhibitors of cathepsin S. WO2004084842; 2004
  • IRM L.L.C. (Novartis Genomics Institute). Inhibitors of cathepsin S. WO2004084843; 2004
  • IRM L.L.C. (Novartis Genomics Institute). Inhibitors of cathepsin S. WO2004112709; 2004
  • Altmann E, Renaud J, Green J, Arylaminoethyl amides as novel non-covalent cathepsin K inhibitors. J Med Chem 2002;45(12):2352-4
  • Altmann E, Green J, Tintelnot-Blomley M. Arylaminoethyl amides as inhibitors of the cysteine protease cathepsin K—investigating P1' substituents. Bioorg Med Chem Lett 2003;13(12):1997-2001
  • Alper PB, Liu H, Chatterjee AK, Arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 2: optimization of P1 and N-aryl. Bioorg Med Chem Lett 2006;16(6):1486-90
  • Tully DC, Liu H, Alper PB, Synthesis and evaluation of arylaminoethyl amides as noncovalent inhibitors of cathepsin S. Part 3: Heterocyclic P3. Bioorg Med Chem Lett 2006;16(7):1975-80
  • IRM L.L.C. (Novartis Genomics Institute). Inhibitors of cathepsin S. WO2005018568; 2005
  • IRM L.L.C. (Novartis Genomics Institute). Inhibitors of cathepsin S. WO2005034848; 2005
  • Tully DC, Liu H, Chatterjee AK, Synthesis and SAR of arylaminoethyl amides as noncovalent inhibitors of cathepsin S: P3 cyclic ethers. Bioorg Med Chem Lett 2006;16(19):5112-17
  • Tully DC, Liu H, Chatterjee AK, Arylaminoethyl carbamates as a novel series of potent and selective cathepsin S inhibitors. Bioorg Med Chem Lett 2006;16(19):5107-11
  • Chatterjee AK, Liu H, Tully DC, Synthesis and SAR of succinamide peptidomimetic inhibitors of cathepsin S. Bioorg Med Chem Lett 2007;17(10):2899-903

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