Novel TACE inhibitors in drug discovery: a review of patented compounds

Bibliography

• Cerretti DP. Characterization of the tumour necrosis factor alpha converting enzyme, TACE/ADAM17. Biochem Soc Trans 1999;27:219-23
   PubMed Web of Science ®Google Scholar
• Vassalli P. The pathophysiology of tumor necrosis factors. Annu Rev Immunol 1992;10:411-52
   PubMed Web of Science ®Google Scholar
• Van AG, Rutgeerts P. Anti-TNF agents in Crohn's disease. Exp Opin Invest Drugs 2000;9:103–11
   PubMed Web of Science ®Google Scholar
• Nelson FC, Zask A. The therapeutic potential of small molecule TACE inhibitors. Exp Opin Invest Drugs 1999;8:383-92
   PubMedGoogle Scholar
• Doggrell SA. TACE inhibition a new approach to treating inflammation. Exp Opin Invest Drugs 2002;11:1003-06
   PubMed Web of Science ®Google Scholar
• Hasegawa A, Takasaki W, Greene MI, Murali R. Modifying TNF alpha for therapeutic use: a perspective on the TNF receptor system. Mini Rev Med Chem 2001;1:5-16
   PubMedGoogle Scholar
• Moss ML, Tavron LS, Nedelman R. Drug Insight: tumor necrosis factor-converting enzyme as a pharmaceutical target for rheumatoid arthritis. Nat Clin Prac Rheum 2008;4:300-9
   PubMedGoogle Scholar
• Kriegler M, Perez C, DeFay K, A novel form of TNF/cachectin is a cell surface cytotoxic transmembrane protein: ramifications for the complex physiology of TNF. Cell 1988;53:45-53
   PubMed Web of Science ®Google Scholar
• Black RA, Rauch CT, Kozlosky CJ, A metalloproteinase disintegrin that releases tumour necrosis factor-alpha from cells. Nature 1997;385:729-33
   PubMed Web of Science ®Google Scholar
• Moss ML, Jin SL, Milla ME, Cloning of a disintegrin metalloproteinase that processes precursor tumour-necrosis factor- alpha. Nature 1997;385:733-36
   PubMed Web of Science ®Google Scholar
• Dasgupta S, Murumkar PR, Giridhar R, Yadav MR. Current perspective of TACE inhibitors: a review. Bioorg Med Chem 2009;17:444-59
   PubMed Web of Science ®Google Scholar
• Newton RC, Solomon KA, Covington MB, Biology of TACE inhibition. Ann Rheum Dis 2001;60:25-32
   Web of Science ®Google Scholar
• Moss ML, White JM, Lambert MH, Andrews RC. TACE and other ADAM proteases as targets for drug discovery. Drug Disco Today 2001;6:417-26
   PubMed Web of Science ®Google Scholar
• Newton RC, Decicco CP. Therapeutic potential and strategies for inhibiting tumor necrosis factor-alpha. J Med Chem 1999;42:2295-314
   PubMed Web of Science ®Google Scholar
• Maskos K, Fernandez-Catalan C, Huber R, Crystal structure of the catalytic domain of human tumor necrosis factor-alpha-converting enzyme. Proc Natl Acad Sci USA 1998;95:3408-12
   PubMed Web of Science ®Google Scholar
• Murumkar PR, Giridhar R, Yadav MR. 3D-Quantitative structure–activity relationship studies on benzothiadiazepine hydroxamates as inhibitors of tumor necrosis factor-alpha converting enzyme. Chem Biol Drug Des 2008;71:363-73
   PubMed Web of Science ®Google Scholar
• Murumkar PR, Dasgupta SD, Zambre VP, Development of predictive 3D-QSAR CoMFA and CoMSIA models for-aminohydroxamic acid-derived tumor necrosis factor-alpha converting enzyme inhibitors. Chem Biol Drug Des 2009;73:97-107
   PubMed Web of Science ®Google Scholar
• Dasgupta S, Murumkar PR, Giridhar R, Yadav MR. Studies on novel 2-imidazolidinones and tetrahydropyrimidin-2(1H)-ones as potential TACE inhibitors: design, synthesis, molecular modeling, and preliminary biological evaluation. Bioorg Med Chem 2009;17:3604-617
   PubMed Web of Science ®Google Scholar
• Murumkar PR, Dasgupta SD, Zambre VP, Development of predictive pharmacophore model for in silico screening and 3D-QSAR CoMFA and CoMSIA studies for lead optimization for designing of potent tumor necrosis factor alpha converting enzyme inhibitors. J Comp Mol Design 2009; Communicated (in press)
   Google Scholar
• Mohler KM, Sleath PR, Fitzner JN, Protection against a lethal dose of endotoxin by an inhibitor of tumour necrosis factor processing. Nature 1994;370:218-20
   PubMed Web of Science ®Google Scholar
• McGeehan GM, Becherer JD, Bast RC Jr, Regulation of tumour necrosis factor-alpha processing by a metalloproteinase inhibitor. Nature 1994;370:558-61
   PubMed Web of Science ®Google Scholar
• Leung D, Giovanni A, Fairlie DP. Protease inhibitors: current status and future prospectus. J Med Chem 2000;43:305-41
   PubMed Web of Science ®Google Scholar
• Shrivastava PK, Dastidar SG, Ray A. Chronic obstructive pulmonary disease: role of matrix mettaloprotease and future challenge of drug therapy. Exp Opin Invest Drugs 2007;16:1069-78
   PubMed Web of Science ®Google Scholar
• Schering Corporation. Compounds for the treatment of inflammatory disorders. US7524842; 2009
   Google Scholar
• Wyeth Holding Corporation. Allenic aryl sulphonamide hydroxamic acid as MMP and TACE inhibitors. US7282496; 2007
   Google Scholar
• Wyeth Holding Corporation. Acetylenic aryl sulfonate hydroxamic acid and TACE and matrixmetalloproteinase inhibitors. US7199155; 2007
   Google Scholar
• Wyeth Holding Corporation. Preparation and use of acetylenic ortho-sulfonamido and phosphinic acid amido bicyclic heteroaryl hydroxamic acids as TACE Inhibitors. US6946473; 2005
   Google Scholar
• Wyeth Holding Corporation. Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic TACE inhibitors. US6762178; 2004
   Google Scholar
• Wyeth Holding Corporation. Acetylenic alpha-amino acid-based sulfonamide hydroxamic acid TACE inhibitors. US6716833; 2004
   Google Scholar
• Wyeth. Preparation and use of ortho-sulfonamido aryl hydoxamic acids as marix metalloproteinase inhibitors. US6465508; 2002
   Google Scholar
• Wyeth. Alkynyl-containing tryptophan derivative inhibitors of TACE/matrix metalloproteinase. US7576222; 2009
   Google Scholar
• Park K, Gopalsamy A, Aplasca A, Synthesis and activity of tryptophan sulphonamide derivatives as novel non-hydroxamate TNF-alpha converting enzyme (TACE) inhibitors. Bioorg Med Chem 2009;17(11):3857-65
   PubMed Web of Science ®Google Scholar
• American Home Products Corporation. N-Hydroxy-2-(alkyl, aryl, or heteroaryl sufanyl, sulfinyl or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors. US6331563; 2001
   Google Scholar
• American Home Products Corporation. N-Hydroxy-2-(alkyl, aryl, or heteroaryl sufanyl, sulfinyl or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors. US6462073; 2002
   Google Scholar
• American Home Products Corporation. N-Hydroxy-2-(alkyl, aryl, or heteroaryl sufanyl, sulfinyl or sulfonyl)-3-substituted alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors. US6444704; 2002
   Google Scholar
• American Cynamid Company. Preparation and use of ortho-sulfonamido heteroaryl hydroxamic acids as matrix metalloproteinase and TACE inhibitors. US6197795; 2001
   Google Scholar
• American Cynamid Company. Preparation and use of ortho-sulfonamido bicyclic heteroaryl hydroxamic acids as matrix metalloproteinase and TACE inhibitors. US6498167; 2002
   Google Scholar
• American Cynamid Company. Preparation and use of ortho-sulfonamido bicyclic heteroaryl hydroxamic acids as matrix metalloproteinase and TACE inhibitors. US6548524; 2003
   Google Scholar
• American Cynamid Company. Acetylenic beta-sulfonamido and phosphinic acid amide hydroxamic acid TACE inhibitors. US6326516; 2001
   Google Scholar
• American Cynamid Company. Acetylenic sulfonamide thiol TACE inhibitors. US6313123; 2001
   Google Scholar
• American Cynamid Company. Heteroaryl acetylenic sulphonamide and phosphinic acid amide hydroxamic acid TACE inhibitors. US6200996; 2001
   Google Scholar
• American Cynamid Company. Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid TACE inhibitors. US6277885; 2001
   Google Scholar
• Darwin Discovery Ltd. Hydroxamic and carboxylic acid derivatives having MMP and TNF inhibitory activity. WO00187844; 2001
   Google Scholar
• Darwin Discovery Ltd. Hydroxamic and carboxylic acid derivatives having MMP and TNF inhibitory activity. WO00187883; 2001
   Google Scholar
• Baxter AD, Bhogal R, Bird J. Arylsulphonyl hydroxamic acids: potent and selective matrix metalloproteinase inhibitors. Bioorg Med Chem Lett 2001;11:1465-68
   PubMed Web of Science ®Google Scholar
• Watson RJ, Batty D, Baxter AD, An enantioselective synthesis of sulphonamide hydroxamic acids as matrix metalloprotease inhibitors. Tetrahedron Lett 2002;43:683-85
   Web of Science ®Google Scholar
• Darwin Discovery Ltd. Hydroxamic acid derivatives as matrix metalloproteinase (MMP) inhibitors. WO00144188; 2001
   Google Scholar
• Darwin Discovery Ltd. Hydroxamic acid derivatives as matrix metalloproteinase (MMP) inhibitors. WO00144189; 2001
   Google Scholar
• Watson B. TNF inhibitors: a review of the recent patent literature. I Drugs 2002;5:1151-62
   PubMedGoogle Scholar
• Bristol-Myers Squibb Company. Cyclic beta-amino acid derivatives as inhibitors of matrix metalloproteinases and TNF-alpha. WO00170673; 2001
   Google Scholar
• Bristol-Myers Squibb Company. beta-amino acid derivatives as inhibitors of matrix metalloproteinases and TNF-alpha. WO00170734; 2001
   Google Scholar
• Bristol-Myers Squibb Company. Novel lactam metalloproteinases inhibitors. WO00204416; 2002
   Google Scholar
• Bristol-Myers Squibb Company. Barbituric acid derivatives as inhibitors of TNF-alpha converting enzyme (TACE) and/or matrix metalloproteinases. US7294624; 2007
   Google Scholar
• Bristol-Myers Squibb Company. Barbituric acid derivatives as inhibitors of TNF-alpha converting enzyme (TACE) and/or matrix metalloproteinases. US6936620; 2005
   Google Scholar
• Duan J, Chen L, Lu Z, Discovery of low nanomolar non-hydroxamate inhibitors of tumor necrosis factor-alpha converting enzyme (TACE). Bioorg Med Chem Lett 2007;17:266-71
   PubMed Web of Science ®Google Scholar
• Bristol-Myers Squibb Company. Hydantoin derivatives as inhibitors of tumor necrosis factor-alpha converting enzyme (TACE). US7132432; 2006
   Google Scholar
• Bristol-Myers Squibb Company. Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE). US7041693; 2006
   Google Scholar
• Sheppeck J, Gilmore J, Tebben A, Hydantoins, triazolones, and imidazolones as selective non-hydroxamate inhibitors of tumor necrosis factor-a converting enzyme (TACE) Bioorg Med Chem Lett 2007;17:2769-74
   PubMed Web of Science ®Google Scholar
• Bristol-Myers Squibb Company. Hydantoins and related heterocycles as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE). US6906053; 2005
   Google Scholar
• Bristol-Myers Squibb Company. Hydantoins and related heterocycles as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE). US7482372; 2009
   Google Scholar
• Sheppeck J, Gilmore J, Yang A, Discovery of novel hydantoins as selective non-hydroxamate inhibitors of tumor necrosis factor-alpha converting enzyme (TACE ) Bioorg Med Chem Lett 2007;17:1413-17
   PubMed Web of Science ®Google Scholar
• Bristol-Myers Squibb Company. Cyclic sulfone derivatives as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE). US7015217; 2006
   Google Scholar
• Bristol-Myers Squibb Company. Bicyclic lactum derivatives as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE). US6884806; 2005
   Google Scholar
• Bristol-Myers Squibb Company. Bicyclic hydroxamates as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE). US6770647; 2004
   Google Scholar
• Bristol-Myers Squibb Company. Cyclic hydroxamic acids as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE). US6740649; 2004
   Google Scholar
• Chen X, Ghavimi B, Corbett R, A new 4-(2-methylquinolin-4-ylmethyl)phenyl P1' group for the beta-amino hydroxamic acid derived TACE inhibitors. Bioorg Med Chem Lett 2007;17:1865-70
   PubMed Web of Science ®Google Scholar
• Bristol-Myers Squibb Pharma. Spiro-cyclic beta-amino acid derivatives as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE). US6720329; 2004
   Google Scholar
• Ott G, Asakawa N, Liu R, alpha,beta-Cyclic-beta-benzamido hydroxamic acids: Novel oxaspiro[4.4]nonane templates for the discovery of potent, selective, orally bioavailable inhibitors of tumor necrosis factor- alpha converting enzyme (TACE). Bioorg Med Chem Lett 2008;18:1288-92
   PubMed Web of Science ®Google Scholar
• Bristol-Myers Squibb Company. Isoxazoline derivatives as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme. US 7125870; 2006
   Google Scholar
• Bristol-Myers Squibb Company. Uracil derivatives as inhibitors of TNF-alpha converting enzyme (TACE) and matrix metalloproteinases. US 7101883; 2006
   Google Scholar
• Bristol-Myers Squibb Company. Triazolone and triazolethione derivatives as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme. US 7074810; 2006
   Google Scholar
• Gilmore J, King B, Asakawa N, Synthesis and structure–activity relationship of a novel, non-hydroxamate series of TNF-a converting enzyme inhibitors. Bioorg Med Chem Lett 2007;17:4678-82
   PubMed Web of Science ®Google Scholar
• Pfizer limited. TACE inhibitors. EP 1104412; 2005
   Google Scholar
• Pfizer Products. Selective inhibitors of aggrecanase in osteoarthritis treatment. EP 01081137; 2001
   Google Scholar
• Pfizer Products. 2-Oxo-imidazolidine-4-carboxylic acid aggrecanase in osteoarthritis treatment. EP01134215; 2001
   Google Scholar
• Pfizer Products. Pyrimidine-2,4,6-trione metalloproteinase inhibitors. WO00112611; 2001
   Google Scholar
• Glaxo Wellcome, Inc. Formamides as therapeutic agents. US6172064; 2001
   Google Scholar
• Glaxo Wellcome, Inc. Formamide compounds as therapeutic agents. US6191150; 2001
   Google Scholar
• Glaxo Wellcome, Inc. Formamide compounds as therapeutic agents. US6329400; 2001
   Google Scholar
• Vertex Pharmaceuticals, Inc. Inhibitors of TACE. US7485664; 2009
   Google Scholar
• Rao B, Bandarage U, Wang T, Novel thiol-based TACE inhibitors: rational design, synthesis, and SAR of thiol-containing aryl sulphonamides. Bioorg Med Chem Lett 2007;17:2250-53
   PubMed Web of Science ®Google Scholar
• Kaken Pharmaceutical Co., LtdReverse hydroxamic acid derivatives. US751114; 2009
   Google Scholar
• Brown PD. Ongoing trials with matrix metalloproteinase inhibitors.Exp Opin Invest Drugs 2000;9:2167-77
   PubMed Web of Science ®Google Scholar
• Shaw T, Nixon JS, Bottomley KM. Metalloproteinase inhibitors-New opportunities for the treatment of rheumatoid arthritis and osteoarthriris. Exp Opin Invest Drugs 2000;9:1469-78
   PubMed Web of Science ®Google Scholar
• Elliot S, Cawston T. The clinical potential of matrix metalloproteinase inhibitors in the rheumatic disorder. Drugs Aging 2001;18:87-99
   PubMed Web of Science ®Google Scholar
• Aranapakam V, Davis JM, Grosu GT, Synthesis and structure-activity relationship of N-substituted 4-arylsulfonylpiperidine-4-hydroxamic acids as novel, orally active matrix metalloproteinase inhibitors for the treatment of osteoarthritis. J Med Chem 2003;46:2376-96
   PubMed Web of Science ®Google Scholar
• Yocum SA, Lopresti-Monow L, Reeves LM, Mitchell PG. Inhibition of matrix metalloproteinases: therapeutic applications. In: Greenwald RA, Zucker S, Golub LM, editors. The New York Academy of Sciences: NY; 1999. p. 583-86
   Google Scholar
• Newton, RC, Solomon KA, Biology of TACE inhibition. Ann Rheum Dis 2001;60(Suppl 3):iii25-32
   PubMedGoogle Scholar
• Kamei N, Tanaka T, Kawai K, Reverse hydroxamate based selective TACE inhibitors. Bioorg Med Chem Lett 2004;14(11):2897-900
   PubMed Web of Science ®Google Scholar
• Conway JG, Andrews RC, Beaudet B, Inhibition of tumor necrosis factor alpha production and arthritis in rat by GW3333, a dual inhibitor of TNF-A converting enzyme and matrix metalloproteinases. J Pharm Exp Ther 2001;298(3):900-08
   PubMed Web of Science ®Google Scholar
• Robinson RP, Laird ER, Blake JF, Structure based design and synthesis of a potent matrix metalloproteinase-13 inhibitor based on a pyrrolidinone scaffold. J Med Chem 2000;43:2293-96
   PubMed Web of Science ®Google Scholar
• Musso DL, Anderson MW, Andrews RC, N-hydroxyformamide peptidomimetics as TACE/matrix metalloprotease inhibitors: oral activity via P1' isobutyl substitution. Bioorg Med Chem Lett 2001;11:2147-51
   PubMed Web of Science ®Google Scholar
• Venkatesan AM, Davis JM, Grosu GT, Synthesis and structure-activity relationships of 4-alkynyloxy phenyl sulfanyl, sulfinyl and sulfonyl alkyl hydroxamates as tumor necrosis factor-alpha converting enzyme and matrix metalloproteinase inhibitors. J Med Chem 2004;47(25):6255-69
   PubMed Web of Science ®Google Scholar
• Zhang Y, Xu J, Levin J, Identification & characterisation of 4-[[4-(2-Butynyloxy)phenyl]sulfonyl]-N-hydroxy-2,2-dimethyl-(3S)-thiomorphol- in carboxamide (TMI-1), a novel dual tumor necrosis factor-alpha converting enzyme/matrix metalloprotease inhibitor for the treatment of rheumatoid arthritis. J Pharmacol Exp Ther 2004;309:348-55
   PubMed Web of Science ®Google Scholar
• Duan JJW, Chen L, Wasserman ZR, Inhibition of potent and selective TACE inhibitors via the S1 pocket. J Med Chem 2002;45:4954-57
   PubMed Web of Science ®Google Scholar
• Wasserman ZR, Duan JJW, Voss ME, Identification of a selectivity determinant for the inhibition of tumor necrosis factor-alpha converting enzyme by comparative modelling. Chem Biol 2003;10:215-23
   PubMed Web of Science ®Google Scholar
• Freskos JN, Mischke BV, Decrescenzo GA, Discovery of novel series of selective matrix metalloproteinase inhibitors: identification of the gamma-sulfone thiols. Bio Med Chem Lett 1999;9:943-48
   PubMed Web of Science ®Google Scholar
• Kenny PA, Bissell MJ. Targeting TACE dependent EGFR ligand shedding in breast cancer. J Clin Invest 2007;117:337-45
   PubMed Web of Science ®Google Scholar
• Kenny PA. Tackling EGFR signaling with TACE antagonist: a rational target for metalloprotease inhibitors in cancer. Exp Opin Ther Targets 2007;11:1287-98
   PubMed Web of Science ®Google Scholar
• Kenny PA. TACE: a new target in epidermal growth factor receptor dependent tumors. Differentiation 2007;75:800-8
   PubMed Web of Science ®Google Scholar