406
Views
9
CrossRef citations to date
0
Altmetric
Reviews

Update on lymphocyte specific kinase inhibitors: a patent survey

, PhD & , PhD
Pages 1573-1593 | Published online: 10 Sep 2010

Bibliography

  • Kane LP, Lin J, Weiss A. Signal transduction by the TCR for antigen. Curr Opin Immunol 2000;12:242-9
  • Bolen JB, Brugge JS. Leukocyte protein tyrosine kinases: potential targets for drug discovery. Annu Rev Immunol 1997;15:371-404
  • Lowell CA, Soriano P. Knockouts of Src-family kinases: stiff bones, wimpy T cells, and bad memories. Genes Dev 1996;10:1845-57
  • Marth JD, Lewis DB, Cooke MP, Lymphocyte activation provokes modification of a lymphocyte specific protein tyrosine kinase (p56lck). J Immunol 1989;142:2430-7
  • Groves T, Smiley P, Cooke MP, Fyn can partially substitute for Lck in T lymphocyte development. Immunity 1996;5:417-28
  • Palacios EH, Weiss A. Function of the Src-family kinases, Lck and Fyn, in T-cell development and activation. Oncogene 2004;23:7990-8000
  • Salmond RJ, Filby A, Qureshi I, T-cell receptor proximal signaling via the Src-family kinases, Lck and Fyn, influences T-cell activation, differentiation, and tolerance. Immunol Rev 2009;228:9-22
  • Molina TJ, Kishihara K, Siderovskid DP, Profound block in thymocyte development in mice lacking p56lck. Nature 1992;357:161-4
  • Levin SD, Anderson SJ, Forbush KA, Perlmutter RM. A dominant-negative transgene defines a role for p56lck in thymopoiesis. EMBO J 1993;12:1671-80
  • Seddon B, Zamoyska R. TCR signals mediated by Src family kinases are essential for the survival of naive T cells. J Immunol 2002;169:2997-3005
  • Straus DB, Weiss A. Genetic evidence for the involvement of the lck tyrosine kinase in signal transduction through the T cell antigen receptor. Cell 1992;70:585-93
  • Goldman FD, Ballas ZK, Schutte BC, Defective expression of p56lck in an infant with severe combined immunodeficiency. J Clin Invest 1998;102:421-9
  • Hubert P, Bergeron F, Ferreirea V, Defective p56lck activity in T cells from an adult patient with idiopathic CD4+ lymphocytopenia. Int Immunol 2000;12:449-57
  • Meyn MA III, Smithgall TE. Small molecule inhibitors of Lck: the search for specificity within a kinase family. Mini Rev Med Chem 2008;8:628-37
  • Bhagwat S. Kinase inhibitors for the treatment of inflammatory and autoimmune disorders. Purinergic Signal 2009;5:107-15
  • Dowden J, Ward SG. Inhibitors of p56lck: assessing their potential as tools for manipulating T-lymphocyte activation. Expert Opin Ther Patents 2001;11:295-306
  • Parang K, Sun G. Recent advances in the discovery of Src kinase inhibitors. Expert Opin Ther Patents 2005;15:1183-207
  • Zhu X, Kim JL, Newcomb JR, Structural analysis of the lymphocyte-specific kinase Lck in complex with non-selective and Src family selective kinase inhibitors. Structure 1999;7:651-61
  • Yamaguchi H, Hendrickson WA. Structural basis for activation of human lymphocyte kinase Lck upon tyrosine phosphorylation. Nature 1996;388:484-9
  • Xu W, Harrison SC, Eck MJ. Three-dimensional structure of the tyrosine kinase c-Src. Nature 1997;385:595-602
  • Sicheri F, Moarefi I, Kuriyan J. Crystal structure of the Src family tyrosine kinase Hck. Nature 1997;385:602-9
  • Noble MEM, Endicott JA, Johnson LN. Protein kinase inhibitors: insights into drug design from structure. Science 2004;303:1800-5
  • Liu Y, Gray NS. Rational design of inhibitors that bind to inactive kinase conformations. Nat Chem Biol 2006;2:358-64
  • DiMauro EF, Newcomb J, Nunes JJ, Discovery of aminoquinazolines as potent, orally bioavailable inhibitors of Lck: synthesis, SAR, and in vivo anti-inflammatory activity. J Med Chem 2006;49:5671-86
  • Zuccotto F, Ardini E, Casale E, Angiolini M. Through the “Gatekeeper Door”: exploiting the active kinase conformation. J Med Chem 2010;53:2681-94
  • Morphy R. Selectively nonselective kinase inhibition: strking the right balance. J Med Chem 2010;53:1413-37
  • Newton R, Holden N. Inhibitors of p38 mitogen-activated protein kinase: potential as anti-inflammatory agents in asthma? BioDrugs 2003;17:113-29
  • Ferrara N, Gerber H, LeCouter J. The biology of VEGF and its receptor. Nat Med 2003;9:669-76
  • Podder H, Kahan BD. Janus kinase 3: a novel target for selective transplant immunosuppression. Expert Opin Ther Targets 2004;8:613-29
  • Thurston G. Role of angiopoietins and Tie receptor tyrosine kinases in angiogenesis and lymphangiogenesis. Cell Tissue Res 2003;34:61-8
  • Pfizer, Inc. Preparation of 4-aminopyrazolo[3,4-d]pyrimidines and 4-aminopyrazolo[3,4-d]pyridines as tyrosine kinase inhibitors. US5593997; 1997
  • Hanke JH, Gardner JP, Dow RL, Discovery of a novel, potent, and Src family-selective tyrosine kinase inhibitor. Study of Lck- and FynT-dependent T cell activation. J Biol Chem 1996;271(2):695-701
  • Arnold LD, Calderwood DJ, Dixon RW, Pyrrolo[2,3-d]pyrimidines containing an extended 5-substituent as potent and selective inhibitors of Lck I. Bioorg Med Chem Lett 2000;10:2167-70
  • Burchat AF, Calderwood DJ, Hirst GC, Pyrrolo[2,3-d]pyrimidines containing an extended 5-substituent as potent and selective inhibitors of Lck II. Bioorg Med Chem Lett 2000;10:2171-4
  • Calderwood DJ, Johnston DN, Munschauer R, Pyrrolo[2,3-d]pyrimidines containing diverse N-7 substituents as potent inhibitors of Lck. Bioorg Med Chem Lett 2002;12:1683-6
  • Burchat AF, Calderwood DJ, Friedman MM, Pyrazolo[3,4-d]pyrimidines containing an extended 3-substituent as potent inhibitors of Lck–a selectivity insight. Bioorg Med Chem Lett 2002;12:1687-90
  • Abbott Laboratories. Method of treating transplant rejection. US20050008640; 2005
  • Borhani DW, Calderwood DJ, Friedman MM, A-420983: a potent, orally active inhibitor of Lck with efficacy in a model of transplant rejection. Bioorg Med Chem Lett 2004;14:2613-16
  • Burchat A, Borhani DW, Calderwood DJ, Discovery of A-770041, a Src-family selective orally active Lck inhibitor that prevents organ allograft rejection. Bioorg Med Chem Lett 2006;16:118-22
  • Stachlewitz RF, Hart MA, Bettencourt B, A-770041, a novel and selective small-molecule inhibitor of Lck, prevents heart allograft rejection. J Pharm Exp Ther 2005;315:36-41
  • Abbott L, Betschmann P, Burchat A, Discovery of thienopyridines as Src-family selective Lck inhibitors. Bioorg Med Chem Lett 2007;17:1167-71
  • Abbott Laboratories. Thienopyridine kinase inibitors. US20050020619; 2005
  • Abbott Laboratories. Thienopyridine and furopyridine kinase inhibitors. US20050026944; 2005
  • Abbott Laboratories. Thienopyridine and furopyridine kinase inhibitors. WO05010009; 2005
  • Abbott Laboratories. Thienopyridine and furopyridine kinase inhibitors. US2005043347; 2005
  • Abbott Laboratories. Thienopyridine and furopyridine kinase inhibitors. US7202363; 2007
  • Abbott Laboratories. Thienopyridine and furopyridine kinase inhibitors. US20070155776; 2007
  • Abbott Laboratories. Thienopyridine and furopyridine kinase inhibitors. US20100069371; 2010
  • Dai Y, Guo Y, Frey RR, Thienopyrimidine ureas as novel and potent multitargeted receptor tyrosine kinase inhibitors. J Med Chem 2005;48:6066-83
  • Heyman HR, Frey RR, Bousquet PF, Thienopyridine urea inhibitors of KDR kinase. Bioorg Med Chem Lett 2007;17:1246-9
  • Vertex Pharmaceuticals, Inc. Pyrrolo[3,2-c]pyridines useful as inhibitors of protein kinases. WO07095223; 2007
  • Vertex Pharmaceuticals, Inc. Pyrrolo[3,2-c]pyridines useful as inhibitors of protein kinases. US7659283; 2010
  • Amgen, Inc. Furanopyrimidines. WO06004658; 2006
  • DiMauro EF, Newcomb J, Nunes JJ, Discovery of 4-amino-5,6-biaryl-furo[2,3-d]pyrimidines as inhibitors of Lck: development of an expedient and divergent synthetic route and preliminary SAR. Bioorg Med Chem Lett 2007;17:2305-9
  • Manser E, Leung T, Salihuddin H, A non-receptor tyrosine kinase that inhibits the GTPase activity of p21cdc42. Nature 1993;363:364-7
  • Xiao S-H, Farrelly E, Anzola J, An ultrasensitive high-throughput electrochemiluminescence immunoassay for the Cdc42-associated protein tyrosine kinase ACK1. Anal Biochem 2007;367:179-89
  • Amgen, Inc. Furanopyridine derivatives and methods of use. WO06130160; 2006
  • Amgen, Inc. Furanopyridine derivatives and methods of use. US7674907; 2010
  • Martin MW, Newcomb J, Nunes JJ, Discovery of novel 2,3-diarylfuro[2,3-b]pyridin-4-amines as potent and selective inhibitors of Lck: synthesis, SAR, and pharmacokinetic properties. Bioorg Med Chem Lett 2007;17:2299-304
  • Amgen, Inc. Pyrrolo[2,3-d]pyrimidines that modulate ACK1 and Lck activity. WO06004703; 2006
  • Amgen, Inc. Pyrrolo[2,3-d]pyrimidines that modulate ACK1 activity. US7358250; 2008
  • Astra Zeneca AB. Quinazoline compounds with therapeutic use. US7223756; 2007
  • Astra Zeneca AB. Quinazoline compounds with therapeutic use. US20050009850; 2005
  • F. Hoffman-La Roche AG. Bicyclic nitrogen heterocycles. WO00024744; 2000
  • Kraker AJ, Hartl BG, Amam AM, Biochemical and cellular effects of c-Src kinase-selective pyrido[2,3-d]pyrimidine tyrosine kinase inhibitors. Biochem Pharmacol 2000;60:885-98
  • F. Hoffman-La Roche AG. Amino-substituted dihydropyrimido[4,5-d] pyrimidinone derivatives. US7091345; 2006
  • F. Hoffman-La Roche AG. Amide derivatives of 7-amino-3-phenyl-dihydropyrimido[4,5-d]pyrimidinones, their manufacture and use as pharmaceutical agents. WO06024487; 2006
  • F. Hoffman-La Roche AG. Pyrido[2,3-d]pyrimidine dichloro-phenyl derivatives. US7189732; 2007
  • F. Hoffman-La Roche AG. Novel dichloro-phenyl-pyrido[2,3-d]pyrimidine derivatives, their manufacture and use as pharmaceutical agents. WO05090344; 2005
  • F. Hoffman-La Roche AG. 6-(2-alkyl-phenyl)-pyrido[2,3-d]pyrimidines useful as protein kinase inhibitors. WO06032452; 2006
  • Amgen, Inc. Substituted heterocyclic compounds and methods of use. WO05042518; 2005
  • Martin MW, Newcomb J, Nunes JJ, Structure-based design of novel 2-Amino-6-phenylpyrimido[5′,4′:5,6]pyrimido[1,2-a]benzimidazol-5(6H)-ones as potent and orally active inhibitors of lymphocyte specific kinase (Lck): synthesis, SAR, and in vivo anti-inflammatory activity. J Med Chem 2008;51:1637-48
  • Amgen, Inc. Substituted heterocyclic compounds and methods of use. WO05021551; 2005
  • Amgen, Inc. 2-Aminopyrimidine and 2-aminopyridine-4-carbamates for use in the treatment of autoimmune diseases. WO05009978; 2005
  • Martin MW, Newcomb J, Nunes JJ, Novel 2-aminopyrimidine carbamates as potent and orally active inhibitors of Lck: synthesis, SAR, and in vivo antiinflammatory activity. J Med Chem 2006;49:4981-91
  • Amgen, Inc. Substituted heterocyclic compounds and methods of use. US7442698; 2008
  • Amgen, Inc. Substituted heterocyclic compounds and methods of use. US7504396; 2009
  • Amgen, Inc. 2-Amino-4-hydroxy-5-pyrimidinecarboxamide derivatives and related compounds as inhibitors of T cell activation for the treatment of inflammatory diseases. WO05009443; 2005
  • Amgen, Inc. Pyrazolopyridine and pyrazolopyrimidine compounds useful as kinase enzymes modulators. WO07024680; 2007
  • IRM LLC. Pyrimidine-substituted benzimidazole derivatives as protein kinase inhibitors. WO07005673; 2007
  • Zhang G, Ren, P, Gray NS, Discovery of pyrimidine benzimidazoles as Lck inhibitors: part I. Bioorg Med Chem Lett 2008;18:5618-21
  • Zhang G, Ren, P, Gray NS, Discovery of pyrimidine benzimidazoles as Src-family selective Lck inhibitors: part II. Bioorg Med Chem Lett 2009;19:6691-5
  • Novartis Pharma GMBH. Pyrimidine urea derivatives as kinase inhibitors. WO06000420; 2006
  • Vertex Pharmaceuticals, Inc. Inhibitors of Src and Lck protein kinases. US20050049246; 2005
  • Vertex Pharmaceuticals, Inc. Inhibitors of C-Jun N-terminal kinases (JNK) and other protein kinases. US6949544; 2005
  • Vertex Pharmaceuticals, Inc. Inhibitors of C-Jun N-terminal kinases (JNK) and other protein kinases. US7084159; 2006
  • Hunt JA, Beresis RT, Goulet JL, Disubstituted pyrimidines as Lck inhibitors. Bioorg Med Chem Lett 2009;19:5440-3
  • Boehringer Ingelheim Pharmaceuticals, Inc. Heterocyclic compounds useful as inhibitors of tyrosine kinases. US6844435; 2005
  • Snow RJ, Cardozo MG, Morwick TM, Discovery of 2-phenylamino-imidazo[4,5-h]isoquinolin-9-ones: a new class of inhibitors of Lck kinase. J Med Chem 2002;45:3394-405
  • Goldberg DR, Butz T, Cardozo MG, Optimization of 2-phenylaminoimidazo[4,5-h] isoquinolin-9-ones: orally active inhibitors of Lck kinase. J Med Chem 2003;46:1337-49
  • Bristol Myers Squibb Co. Cyclic protein tyrosine kinase inhibitors. WO00062778; 2000
  • Bristol Myers Squibb Co. Cyclic Protein Tyrosine Kinase Inhibitors. US6979694; 2005
  • Bristol Myers Squibb Co. Cyclic Protein Tyrosine Kinase Inhibitors. US7091223; 2006
  • Bristol Myers Squibb Co. Cyclic Protein Tyrosine Kinase Inhibitors. US7125875; 2006
  • Bristol Myers Squibb Co. Cyclic Protein Tyrosine Kinase Inhibitors. US7153856; 2006
  • Bristol Myers Squibb Co. Cyclic Protein Tyrosine Kinase Inhibitors. US7189854; 2007
  • Chen P, Norris D, Das J, Discovery of novel 2-(heteroaryl)-thiazole-5-carboxamides as potent and orally active Src-family kinsae p56-Lck inhibitors. Bioorg Med Chem Lett 2004;14:6061-6
  • Das J, Chen P, Norris D, 2-Aminothiazole as a novel kinase inhibitor template. Structure-activity studies toward the discovery of N-(2-Chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]]-2-methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (Dasatinib, BMS-354825) as a potent pan-Src Kinase Inhibitor. J Med Chem 2006;49:6819-32
  • IRM LLC. Benzothiazole derivatives and their use as protein tyrosine kinase inhibitors. WO08124393; 2008
  • Huang S, Liu Z, Tian SS, Discovery of 2-amino-6-carboxamidobenzothiazoles as potent Lck inhinitors. Bioorg Med Chem Lett 2008;18:2324-8
  • Das J, Moquin R, Lin J, Discovery of 2-amino-heteroaryl-benzothiazole-6-anilides as potent p56-Lck inhibitors. Bioorg Med Chem Lett 2003;13:2587-90
  • Taisho Pharmaceutical Co. Ltd. Pyrrole derivative. WO05123671; 2005
  • Takayama T, Umemiya H, Amada H, Pyrrole derivatives as potent inhibitors of lymphocyte-specific kinase: Structure, synthesis, and SAR. Bioorg Med Chem Lett 2010;20:108-11
  • Taisho Pharmaceutical Co. Ltd. Ring-fused pyrrole derivative. WO07026720; 2007
  • Takayama T, Umemiya H, Amada H, Ring-fused pyrazole derivatives as potent inhibitors of lymphocyte-specific kinase (Lck): structure, synthesis, and SAR. Bioorg Med Chem Lett 2010;20:112-16
  • Vertex Pharmaceuticals, Inc. Thiazoles, imidazoles, and pyrazoles useful as inhibitors of protein kinases. WO07117692; 2007
  • Vertex Pharmaceuticals, Inc. Thiazoles, imidazoles, and pyrazoles useful as inhibitors of protein kinases. US20090306155; 2009
  • Vertex Pharmaceuticals, Inc. Thiazoles, imidazoles, and pyrazoles useful as inhibitors of protein kinases. US7589214; 2009
  • Novartis AG. Pyrazolo[1,5-a]pyrimidine derivatives and their therapeutic use. WO08037459; 2008
  • Novartis Institutes for Biomedical Research, Inc. Lck Inhibitors. US20100029636; 2010
  • Amgen, Inc. Aryl nitrogen-containing bicyclic compounds and methods of use. WO06039718; 2006
  • Amgen, Inc. Bis-aryl amide compounds and methods of use. WO07022380; 2007
  • DiMauro EF, Newcomb J, Nunes JJ, Structure-guided design of aminopyrimidine amides as potent, selective inhibitors of Lck: synthesis, SAR, and inhibition of in vivo T-cell activation. J Med Chem 2008;51:1681-94
  • Deak HL, Newcomb JR, Nunes JJ, N-(3-(Phenylcarbamoyl)arylpyrimidine)-5-carboxamides as potent and selective inhibitors of Lck: structure, synthesis and SAR. Bioorg Med Chem Lett 2008;18:1172-6
  • Amgen, Inc. Heteroaryl-substituted alkyne compounds and methods of use. WO06044823; 2006
  • Cee VJ, Albrecht BK, Geuns-Meyer S, Alkynylpyrimidine Amide derivatives as potent, selective, and orally active inhibitors of Tie-2 kinase. J Med Chem 2007;50:627-40
  • Amgen, Inc. Compounds and methods of use. WO05070891; 2005
  • Amgen, Inc. Compounds and methods of use. US7435823; 2008
  • Harmange JC, Weiss MM, Germain J, Naphthamides as novel and potent vascular endothelial growth factor receptor tyrosine kinase inhibitors: design, synthesis, and evaluation. J Med Chem 2008;51:1649-67
  • Weiss MM, Harmange JC, Polverino AJ, Evaluation of a series of naphthamides as potent, orally active vascular endothelial growth factor receptor-2 tyrosine kinase inhibitors. J Med Chem 2008;51:1668-80
  • Bhagwat SS. MAP kinase inhibitors in inflammation and autoimmune disorders. Ann Rep Med Chem 2007;42:265-78
  • Dominguez C, Powers DA, Tamayo N. P38 MAP kinase inhibitors: Many are made, but few are chosen. Curr Opin Drug Disc Dev 2005; 8:421-30
  • Genovese MC. Inhibition of p38: has the fat lady sung? Arthritis Rheum 2009;60:37-320
  • Stachlewitz R, Schwartz A, Bettencourt B, Toxicity of a selective inhibitor of Lck is due to inhibition of Lck and is not chemotype-related [poster 462]. Presented at the 44th Annual Meeting of the Society of Toxicology; March 2005; New Orleans, LA

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.