Platelet-derived growth factor receptor tyrosine kinase inhibitors: A review of the recent patent literature

Expert Opinion on Therapeutic Patents

Volumn 20, Issue 7, 2010, Pages 885-897

  Dai, Yujia ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

Cancer; Fibrosis; Kinases; PDGF signaling; PDGFR inhibitors; Vascular diseases

Indexed keywords

1 CYCLOPROPYL 3 [3 (5 MORPHOLINOMETHYL 1H BENZIMIDAZOL 2 YL) 1H PYRAZOL 4 YL]UREA; AXITINIB; BENZIMIDAZOLE DERIVATIVE; CEDIRANIB; DASATINIB; DOVITINIB; FLT3 LIGAND; IMATINIB; INDOLE DERIVATIVE; LINIFANIB; MOTESANIB; NAPHTHALENE DERIVATIVE; NAPHTHYRIDINE DERIVATIVE; NILOTINIB; PAZOPANIB; PLATELET DERIVED GROWTH FACTOR; PLATELET DERIVED GROWTH FACTOR ALPHA RECEPTOR; PLATELET DERIVED GROWTH FACTOR BETA RECEPTOR; PROTEIN TYROSINE KINASE INHIBITOR; PYRAZOLE DERIVATIVE; PYRIMIDINE DERIVATIVE; QUINAZOLINE DERIVATIVE; RAF PROTEIN; SORAFENIB; STEM CELL FACTOR; SUNITINIB; UNCLASSIFIED DRUG; UNINDEXED DRUG; VASCULOTROPIN RECEPTOR 1; VASCULOTROPIN RECEPTOR 2; VASCULOTROPIN RECEPTOR 3; ANTINEOPLASTIC AGENT; PLATELET DERIVED GROWTH FACTOR RECEPTOR; PROTEIN KINASE INHIBITOR;

ANTINEOPLASTIC ACTIVITY; ATYPICAL CHRONIC MYELOID LEUKEMIA; CANCER THERAPY; DERMATOFIBROSARCOMA PROTUBERANS; DRUG EFFICACY; DRUG POTENCY; DRUG SELECTIVITY; ENZYME INHIBITION; GASTROINTESTINAL STROMAL TUMOR; GLIOBLASTOMA; HUMAN; NONHUMAN; PATENT; REVIEW; SIGNAL TRANSDUCTION; ANIMAL; ANTAGONISTS AND INHIBITORS; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG EFFECTS; NEOPLASMS; PATHOPHYSIOLOGY;

ANIMALS; ANTINEOPLASTIC AGENTS; DRUG DELIVERY SYSTEMS; DRUG DESIGN; HUMANS; NEOPLASMS; PATENTS AS TOPIC; PROTEIN KINASE INHIBITORS; RECEPTORS, PLATELET-DERIVED GROWTH FACTOR; SIGNAL TRANSDUCTION;

EID: 77953767123     PISSN: 13543776     EISSN: None     Source Type: Journal    
DOI: 10.1517/13543776.2010.493559     Document Type: Review

References (97)

1. Kelly JD, Haldeman BA, Grant FJ, et al. Platelet-derived growth factor (PDGF) stimulates PDGF receptor subunit dimerization and intrasubunit trans-phosphorylation. J Biol Chem 1991;266:8987-8992
2. Kazlauskas A, Cooper JA. Autophosphorylation of the PDGF receptor in the kinase insert region regulates interactions with cell proteins. Cell 1989;58:1121-1133
3. Lechleider RJ, Sugimoto S, Bennett AM, et al. Activation of the SH2-containing phosphotyrosine phosphatase SH-PTP2 by its binding site, phosphotyrosine 1009, on the human platelet-derived growth factor receptor. J Biol Chem 1993;268:21478-21481
4. Heuchel R, Berg A, Tallquist M, et al. Platelet-derived growth factor beta receptor regulates interstitial fluid homeostasis through phosphatidylinositol-3¢ kinase signaling. Proc Natl Acad Sci USA 1999;96:11410-11415
5. Raines EW. PDGF and cardiovascular disease. Cytokine Growth Factor Rev 2004;15:237-254
6. Bonner JC. Regulation of PDGF and its receptors in fibrotic disease. Cytokine Growth Factor Rev 2004;15:255-273
7. Pietras K, Sjoblom T, Rubin K, et al. PDGF receptor as cancer drug targets. Cancer Cell 2003;3:439-443
8. Ostman A. PDGF receptors-mediators of autocrine tumor growth and regulators of tumor vasculature and stroma. Cytokine Growth Factor Rev 2004;15:275-286
9. Oseini AM, Roberts LR. PDGFRa: a new therapeutic target in the treatment of hepatocellular carcinoma? Expert Opin Ther Targets 2009;13:443-454
10. Hermanson M, Funa K, Hartman M, et al. Platelet-derived growth factor and its receptors in human glioma tissue: expression of messenger RNA and protein suggests the presence of autocrine and paracrine loops. Cancer Res 1992;52:3213-3219
11. Lokker NA, Sullivan CM, Hollenbach SJ, et al. Platelet-derived growth factor (PDGF) autocrine signaling regulates survival and mitogenic pathways in glioblastom cells: evidence that the novel PDGF-C and PDGF-D ligands may play a role in the development of brain tumors. Cancer Res 2002;62:3729-3735
12. Heinrich MC, Corless CL, Duensing A, et al. PDGFRA activating mutations in gastrointestinal stromal tumors. Science 2003;299:708-710
13. Forsberg K, Valyi-Nagy I, Heldin CH, et al. Platelet-derived growth factor (PDGF) in oncogenesis: development of a vascular connective tissue stroma in xenotransplanted human melanoma producing PDGF-BB. Proc Natl Acad Sci 1993;90:393-397
14. Skobe M, Fusenig NE. Tumorigenic conversion of immortal human keratinocytes through stromal cell activation. Proc Natl Acad Sci 1998;95:1050-1055
15. Shao ZM, Nguyen M, Barsky SH. Human breast carcinoma desmoplasia is PDGF initiated. Oncogene 2000;19:4337-4345
16. Jain RK, Booth MF. What brings pericytes to tumor vessels? J Clin Invest 2003;112:1134-1136
17. Abramsson A, Lindblom P, Betsholtz C. Endothelial and nonendothelial sources of PDGF-B regulate pericyte recruitment and influence vascular pattern formation in tumors. J Clin Invest 2003;112:1142-1151
18. Furuhashi M, Sjoblom T, Abramsson A, et al. Platelet-derived growth factor production by B16 melanoma cells leads to increased pericyte abundance in tumors and an associated increase in tumor growth rate. Cancer Res 2004;64:2725-2733
19. Bergers G, Song S, Meyer-Morse N, et al. Benefits of targeting both pericytes and endothelial cells in the tumor vasculature with kinase inhibitors. J Clin Invest 2003;111:1287-1295
20. Pietras K, Hanahan D. A multitargeted, metronomic, and maximum-tolerated dose "chemo-switch" regimen is antiangiogenic, producing objective responses and survival benefit in a mouse model of cancer. J Clin Oncol 2005;23:939-952
21. Crawford Y, kasman I, Yu L, et al. PDGF-C mediates the angiogenic and tumorigenic properties of fibroblasts associated with tumors refractory to anti-VEGF treatment. Cancer Cell 2009;15:21-34
22. Anderberg C, Li H, Fredriksson L, et al. Paracrine signaling by platelet-derived growth factor-CC promotes tumor growth by recruitment of cancer-associated fibroblasts. Cancer Res 2009;69:369-378
23. Andrae J, Gallini R, Betscholtz C. Role of platelet-derived growth factors in physiology and medicine. Genes Dev 2008;22:1276-1312
24. Ross R. Artherosclerosis-an inflammatory disease. N Engl J Med 1999;340:115-126
25. Hansson GK. Inflammation, atherosclerosis, and coronary artery disease. N Engl J Med 2005;352:1685-1695
26. Schermuly RT, Dony E, Ghofrani HA, et al. Reversal of experimental pulmonary hypertension by PDGF inhibition. J Clin Invest 2005;115:2811-2821
27. Ostman A, Heldin CH. Involvement of platelet-derived growth factor in diseases: development of specific antagonists. Adv Cancer Res 2001;80:1-38
28. Buchdunger E, Cioffi CL, Law N, et al. Abl protein-tyrosine kinase inhibitor STI571 inhibits in vitro signal platelet-derived growth factor receptors. J Pharmacol Exp Ther 2000;295:139-145
29. Putkowski P, Van Glabbeke M, Rankin CJ, et al. Imatinib mesylate in advanced dermatofibrosarcoma protuberans: pooled analysis of two phase II clinical trials. J Clin Oncol 2010;28:1772-1779
30. Deininger MW. Nilotinib. Clin Cancer Res 2008;14:4027-4031
31. Lombardo LJ, Lee FY, Chen P, et al. Discovery of N-(2-chloro-6- methylphenyl)-2-(6-(4-(2-hydroxyethyl)- piperazin-1-y)-2-methylpyrimidin-4- ylamino)thiazole-5-carboxamide (BMS-354825), a dual Src/Abl kinase inhibitor with potent antitumor activity in preclinical assays. J Med Chem 2004;47:6658-6661
32. Mendel DB, Laird AD, Xin X, et al. In vivo antitumor activity of SU11248, a novel tyrosine kinase inhibitor targeting vascular endothelial growth factor and platelet-derived growth factor receptors: determination of a pharmacokinetic/ pharmacodynamic relationship. Clin Cancer Res 2003;9:327-337
33. Wilhelm SM, Carter C, Tang L, et al. BAY 43-9006 exhibits broad oral antitumor activity and targets the RAF/MEK/ERK pathway and receptor tyrosine kinase involved in tumor progression and angiogenesis. Cancer Res 2004;64:7099-7109
34. Kumar R, Knick VB, Rudolph SK, et al. Pharmacokinetic-pharmacodynamic correlation from mouse to human with pazopanib, a multikinase angiogenesis inhibitor with potent antitumor and antiangiogenic activity. Mol Cancer Ther 2007;6:2012-2021
35. Polverino A, Coxon A, Starnes C, et al. AMG 706, an oral, multikinase inhibitor that selectively targets vascular endothelial growth factor, platelet-derived growth factor, and kit receptors, potently inhibits angiogenesis and induces regression in tumor xenografts. Cancer Res 2006;66:8715-8721
36. Wedge SR, Kendrew J, Hennequin LF, et al. AZD2171: a highly potent, orally bioavalable, vascular endothelial growth factor receptor-2 tyrosine kinase inhibitor for the treatment of cancer. Cancer Res 2005;65:4389-4400
37. Choueiri TK. Axitinib, a novel anti-angiogenic drug with promising activity in various solid tumors. Curr Opin Investig Drugs 2008;9:658-671
38. Albert DH, Tapang P, Magoc TJ, et al. Precilical activity of ABT-869, a multitargeted receptor tyrosine kinase inhibitor. Mol Cancer Ther 2006;5:995-1006
39. Dai Y, Hartandi K, Ji Z, et al. Discovery of N-(4-(3-amino-1H-indazol-4- yl) phenyl)-N¢-(2-fluoro-5-methylphenyl) urea (ABT-869), a 3-aminoindazole-based orally active multi-targeted receptor tyrosine kinase inhibitor. J Med Chem 2007;50:1584-1597
40. Distler JHW, Distler O. Imatinib as a novel therapeutic approach for fibrotic disorders. Rheumatology 2009;48:2-4
41. Akhmetshina A, Venalis P, Dees C, et al. Treatment with imatinib prevents fibrosis in different preclinical models of systemic sclerosis and induces regression of established fibrosis. Arthritis Rheum 2009;60:219-224
42. Akhmetshina A, Dees C, Pileckyte M, et al. Dual inhibition of c-Abl and PDGF receptor signaling by dasatinib and nilotinib for the treatment of derma fibrosis. FASEB J 2008;22:2214-2222
43. Daniels CE, Wilkes MC, Edens M, et al. Imatinib mesylate inhibits the profibrogenic activity of TGF-beta and prevents bleomycin-mediated lung fibrosis. J Clin Invest 2004;114:1308-1316
44. Astex. Pharmaceutical compounds. WO077435; 2007
45. Howard S, Berdini V, Boulstridge JA, et al. Fragment-based discovery of the pyrazol-4-yl urea (AT9283), a multitargeted kinase inhibitor with potent aurora kinase activity. J Med Chem 2009;52:379-388
46. Astex. Bicyclic heterocyclic compounds as FGFR inhibitors. WO078091; 2008
47. Astex. Bicyclic heterocyclic compounds as protein tyrosine kinase inhibitors. WO047506; 2009
48. Astex. Bicyclic heterocyclic compounds as protein tyrosine kinase inhibitors. WO047522; 2009
49. AstraZeneca. Quinazoline derivatives. WO040520; 2006
50. AstraZeneca. Quinazoline derivatives for use against cancer. WO040526; 2006
51. AstraZeneca. Quinoline derivatives. WO099326; 2007
52. AstraZeneca. Qunoline derivatives. WO040522; 2006
53. AstraZeneca. Qunoline derivatives for targeting cancer. WO099335; 2007
54. AstraZeneca. Naphthyridine derivatives as anti-cancer agents. WO113565; 2007
55. AstraZeneca. Naphthyridine derivatives. WO113548; 2007
56. Hoffman-La Roche. Heteroaryl derivatives as protein kinase inhibitors. WO028617; 2008
57. Hoffman-La Roche. Pyrimidyl derivatives as proein kinase inhibitors. WO077548; 2008
58. Hoffman-La Roche. Benzimidazole amido derivatives as kinase inhibitors. WO000489; 2009
59. Hoffman-La Roche. Thieno[3,2-c] pyridine-7-carboxylic acid derivatives. WO017594; 2008
60. Hoffman-La Roche. 7H-pyrido[3,4-d] pyrimidin-8-ones, their manufacture and use as protein kinase inhibitors. WO088014; 2007
61. IRM LLC. Compositions and methods for modulating c-Kit and PDGFR receptors. US0176846; 2008
62. IRM LLC. Compounds and compositions as protein kinase inhibitors. WO124731; 2006
63. IRM LLC. Compounds and compositions as protein kinase inhibitors. US0113986; 2008
64. IRM LLC. Compounds and compositions as protein kinase inhibitors. US0188483; 2008
65. IRM LLC. Compounds and compositions as protein kinase inhibitors. US0105250; 2009
66. IRM LLC. Compounds and compositions as protein kinase inhibitors. US0221192; 2008
67. Novartis. Substituted benzimidazoles and methods of their use. US0161680; 2007
68. Novartis. Methods for treating drug resistant cancer. US0215793; 2009
69. Renhowe PA, Pecchi S, Shafer CM, et al. J Med Chem 2009;52:278-292
70. Novartis. Compounds and compositions as c-Kit and PDGFR kinase inhibitors. WO137794; 2008
71. Novartis. Compounds and compositions as protein kinase inhibitors. WO058037; 2008
72. Novartis. Pyrimidine urea derivatives as kinase inhibitors. WO000420; 2006
73. Novartis. Phenylacetamides suitable as protein kinase inhibitors. WO108640; 2006
74. Novartis. Derivatives of quinolines and quinoxalines as protein tyrosine kinase inhibitors. WO141386; 2009
75. Pfizer. Thienopyridine-phenylacetic amides and their derivatives useful as new anti-angiogenic agents. WO021554; 2005
76. Pfizer. Naphthalene carboxamides and their derivatives useful as new anti-angiogenic agents. WO021553; 2005
77. Sugen. Thiophene heteroaryl amines. US0293484; 2007
78. Sugen. Use of 8-amino-aryl-substituted imidazopyrazines as kinase inhibitors. US0009832; 2005
79. Sugen. Geometrically restricted 3-cyclopentane-1,3-dihydroindol-2-ones as potent protein kinase inhibitors. US0038066; 2005
80. Takeda. Fused heterocycle derivatives and use thereof. US0137595; 2009
81. Takeda. Fused heterocycle derivatives and use thereof. US0163488; 2009
82. Takeda. Fused heterocycle derivatives and use thereof. US0137580; 2009
83. Bayer. Fluoro substituted omega-carboxyaryl diphenyl urea for the treatment and prevention of disease and conditions. WO009961; 2005
84. Bayer. Treatment of cancers having resistance to chemotherapeutic agents. WO089388; 2008
85. 4SC. Thiazole analogues and uses thereof. WO054357; 2007
86. 4SG. 2,5- and 2,6-disubstituted benzazole derivatives useful as protein kinase inhibitors. WO066795; 2006
87. Scripps Research Institute. Alkoxy indolinone based protein kinase inhibitors. US0072934; 2007
88. Scripps Research Institute. Alkoxy indolinone based protein kinase inhibitors. US0305382; 2009
89. Bayer Schering Pharma. Alkynylaryl compounds and salts thereof, pharmaceutical compositions comprising same, methods of preparing same and uses of same. WO074260; 2009
90. Ambit. Amide derivatives as PDGFR modulators. US0171172; 2005
91. Cai X, Qian C, Gould S, et al. Tyrosine kinase inhibitors containing zinc binding moiety. US0125440; 2008
92. Qian C, Cai X, Zhai H. VEGFR inhibitors containing zinc binding moiety. US0076044; 2009
93. Morphy R, Ray C, Rankovic Z. Drug Discov Today 2004;9:641-651
94. Morphy R. Selectively nonselective kinase inhibition: striking the right balance. J Med Chem 2010;53:1413-1437
95. Cristofanili M, Morandi P, Krishnamurthy S, et al. Imatinib mesylate (Gleevec) in advanced breast cancer-expressing c-Kit or PDGFR-beta: clinical activity and biological correlations. Ann Oncol 2008;19(10):1713-1719
96. Pietras K, Ostman A, Sjoquist M, et al. Inhibition of platelet-derived growth factor receptors reduces interstitial hypertension and increases transcapillary transport in tumors. Cancer Res 2001;61:2929-2934
97. Pietras K, Rubin K, Sjoblom T, et al. Inhibition of PDGF receptor signaling in tumor stroma enhances antitumor effect of chemotherapy. Cancer Res 2002;62:5476-5484