Bcr-Abl tyrosine kinase inhibitors: A patent review

Expert Opinion on Therapeutic Patents

Volumn 25, Issue 4, 2015, Pages 397-412

  Desogus, Andrea ^a   Schenone, Silvia ^a   Brullo, Chiara ^a   Tintori, Cristina ^b   Musumeci, Francesca ^a  

^a UNIVERSITY OF GENOA   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

Author keywords

Breakpoint cluster region Abl tyrosine kinase; Chronic myeloid leukemia; Inhibitors; Mutation; T315I; Tyrosine kinase

Indexed keywords

ABELSON KINASE; BCR ABL PROTEIN; BCR ABL TYROSINE KINASE INHIBITOR; BOSUTINIB; DANUSERTIB; DASATINIB; IMATINIB; NILOTINIB; PONATINIB; PROTEIN TYROSINE KINASE INHIBITOR; REBASTINIB; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; PROTEIN KINASE INHIBITOR;

ANTIPROLIFERATIVE ACTIVITY; CANCER CHEMOTHERAPY; CHRONIC MYELOID LEUKEMIA; DRUG STRUCTURE; ENZYMATIC ASSAY; HUMAN; IC50; PATENT; REVIEW; ANIMAL; ANTAGONISTS AND INHIBITORS; DRUG DESIGN; DRUG RESISTANCE; ENZYMOLOGY; LEUKEMIA, MYELOGENOUS, CHRONIC, BCR-ABL POSITIVE; METABOLISM;

ANIMALS; ANTINEOPLASTIC AGENTS; DRUG DESIGN; DRUG RESISTANCE, NEOPLASM; FUSION PROTEINS, BCR-ABL; HUMANS; IMATINIB MESYLATE; LEUKEMIA, MYELOGENOUS, CHRONIC, BCR-ABL POSITIVE; PATENTS AS TOPIC; PROTEIN KINASE INHIBITORS;

EID: 84924986299     PISSN: 13543776     EISSN: 17447674     Source Type: Journal    
DOI: 10.1517/13543776.2015.1012155     Document Type: Review

References (84)

1. Colicelli J. ABL tyrosine kinases: evolution of function, regulation, and specificity. Sci Signal 2010;3:re6
2. Panjarian S, Iacob RE, Chen S, et al. Structure and dynamic regulation of Abl kinases. J Biol Chem 2013;288:5443-50
3. Nagar B, Hantschel O, Young MA, et al. Structural basis for the autoinhibition of c-Abl tyrosine kinase. Cell 2003;112:859-71
4. Hantschel O, Nagar B, Guettler S, et al. Myristoyl/phosphotyrosine switch regulates c-Abl. Cell 2003;112:845-57
5. Wisniewski D, Lambek CL, Liu C, et al. Characterization of potent inhibitors of the Bcr-Abl and the c-kit receptor tyrosine kinases. Cancer Res 2002;62:4244-55
6. Kurzrock R, Kantarjian HM, Druker BJ, Talpaz M. Philadelphia chromosomepositive leukemias: From basic mechanisms to molecular therapeutics. Ann Intern Med 2003;138:819-30
7. Zhang J, Yang PL, Gray NS. Targeting cancer with small molecule kinase inhibitors. Nat Rev Cancer 2009;9:28-39
8. Mol C, Fabbro D, Hosfield DJ. Structural insights into the conformational selectivity of STI-571 and related kinase inhibitors. Curr Opin Drug Discov Devel 2004;7:639-48
9. Rabiller M, Getlik M, Klüter S, et al. Proteus in the world of proteins: conformational changes in protein kinases. Arch Pharm (Weinheim) 2010;343:193-206
10. Fang Z, Grütter C, Rauh D. Strategies for the selective regulation of kinases with allosteric modulators: exploiting exclusive structural features. ACS Chem Biol 2013;8:58-70
11. Soverini S, Iacobucci I, Baccarani M, Martinelli G. Targeted therapy and the T315I mutation in Philadelphia-positive leukemias. Haematologica 2007;92:437-9
12. Goldman JM. How I treat chronic myeloid leukemia in the Imatinib era. Blood 2007;110:2828-37
13. Martinelli G, Soverini S, Rosti G, et al. New tyrosine kinase inhibitors in chronic myeloid leukemia. Haematologica 2005;90:534-41
14. Maekawa T, Ashihara E, Kimura S. The Bcr-Abl tyrosine kinase inhibitor imatinib and promising new agents against Philadelphia chromosome-positive leukemias. Int J Clin Oncol 2007;12:327-40
15. Schenone S, Brullo C, Botta M. New opportunities to treat the T315I-Bcr-Abl mutant in chronic myeloid leukaemia: tyrosine kinase inhibitors and molecules that act by alternative mechanisms. Curr Med Chem 2010;17:1220-45
16. Melo JV, Chuah C. Resistance to imatinib mesylate in chronic myeloid leukemia. Cancer Lett 2007;249:121-32
17. Mughal TJ, Goldman JM. Emerging strategies for the treatment of mutant Bcr-Abl T315I myeloid leukemia. Clin Lymphoma Myeloma 2007;7(Suppl 2):S81-4
18. Deininger M, Buchdunger E, Druker BJ. The development of Imatinib as a therapeutic agent for chronic myeloid leukemia. Blood 2005;105:2640-53
19. O'Hare T, Eide CA, Deininger MW. New Bcr-Abl inhibitors in chronic myeloid leukemia: keeping resistance in check. Expert Opin Investig Drugs 2008;17:865-78
20. Baran Y, Saydam G. Cumulative clinical experience from a decade of use: imatinib as first-line treatment of chronic myeloid leukemia. J Blood Med 2012;3:139-50
21. Ohanian M, Cortes J, Kantarjian H, Jabbour E. Tyrosine kinase inhibitors in acute and chronic leukemias. Expert Opin Pharmacother 2012;13:927-38
22. Schenone S, Bruno O, Radi M, Botta M. New insights into small-molecule inhibitors of Bcr-Abl. Med Res Rev 2011;31:1-41
23. Hantschel O, Rix U, Schmidt U, et al. The Btk tyrosine kinase is a major target of the Bcr-Abl inhibitor dasatinib. Proc Natl Acad Sci USA 2007;104:13283-8
24. Khan AM, Bixby DL. BCR-ABL inhibitors: updates in the management of patients with chronic-phase chronic myeloid leukemia. Hematology 2014;19:249-58
25. Syed YY, McCormack PL, Plosker GL. Bosutinib: a review of its use in patients with Philadelphia chromosome-positive chronic myelogenous leukemia. BioDrugs 2014;28:107-20
26. O'Hare T, Shakespeare WC, Zhu X, et al. AP24534, a pan-BCR-ABL inhibitor for chronic myeloid leukemia, potently inhibits the T315I mutant and overcomes mutation-based resistance. Cancer Cell 2009;16:401-12
27. Ariad Pharmaceuticals, Inc. Methods and compositions for treating cancer using multi-protein kinase inhibitor ponatinib. WO053938; 2011
28. Deininger M. The current status of ponatinib in the treatment of chronic myeloid leukemia. Clin Adv Hematol Oncol 2014;12:329-31
29. Zhou T, Commodore L, Huang WS, et al. Structural mechanism of the Pan-BCR-ABL inhibitor ponatinib (AP24534): lessons for overcoming kinase inhibitor resistance. Chem Biol Drug Des 2011;77:1-11
30. FDA Drug Safety Communication: FDA asks manufacturer of the leukemia drug Iclusig (ponatinib) to suspend marketing and sales. FDA Safety Communication. 2013-10-31 Available from: http://www.fda.gov/Drugs/DrugSafety/ucm373040.htm
31. FDA OK's Iclusig's return to market. Cancer Discov 2014;4:138
32. Naito H, Kimura S, Nakaya Y, et al. In vivo antiproliferative effect of NS-187, a dual Bcr-Abl/Lyn tyrosine kinase inhibitor, on leukemic cells harbouring Abl kinase domain mutations. Leuk Res 2006;30:1443-6
33. Deciphera Pharmaceuticals LLC. Preparation of urea derivatives as kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases. WO046003; 2008
34. Chan WW, Wise SC, Kaufman MD, et al. Conformational control inhibition of the BCR-ABL1 tyrosine kinase, including the gatekeeper T315I mutant, by the switch-control inhibitor DCC-2036. Cancer Cell 2011;19:556-68
35. Eide CA, Adrian LT, Tyner JW, et al. The ABL switch control inhibitor DCC-2036 is active against the chronic myeloid leukemia mutant BCR-ABLT 315I and exhibits a narrow resistance profile. Cancer Res 2011;71:3189-95
36. Meulenbeld HJ, Mathijssen RH, Verweij J, et al. Danusertib, an aurora kinase inhibitor. Expert Opin Investig Drugs 2012;21:383-93
37. Kimura S, Ando T, Kojima K. Ever-advancing chronic myeloid leukemia treatment. Int J Clin Oncol 2014;19:3-9
38. Jain P, Kantarjian H, Cortes J. Chronic myeloid leukemia: overview of new agents and comparative analysis. Curr Treat Options Oncol 2013;14:127-43
39. Carter TA, Wodicka LM, Shah NP, et al. Inhibition of drug-resistant mutants of ABL, KIT, and EGF receptor kinases. Proc Natl Acad Sci USA 2005;102:11011-16
40. Young MA, Shah NP, Chao LH, et al. Structure of the kinase domain of an imatinib-resistant Abl mutant in complex with the Aurora kinase inhibitor VX-680. Cancer Res 2006;66:1007-14
41. Giles FJ, Swords RT, Nagler A, et al. MK-0457, an Aurora kinase and BCR-ABL inhibitor, is active in patients with BCR-ABL T315I leukemia. Leukemia 2013;27:113-17
42. IRM LCC. Novel compounds and compositions as protein kinase inhibitors. WO089286; 2004
43. Curis, Inc. Tyrosine kinase inhibitors containing a zinc binding moiety. WO033746; 2008
44. Bali P, Pranpat M, Bradner J, et al. Inhibition of histone deacetylase 6 acetylates and disrupts the chaperone function of heat shock protein 90: a novel basis for antileukemia activity of histone deacetylase inhibitors. J Biol Chem 2005;280:26729-34
45. Vertex Pharmaceuticals, Inc. Aminopyrimidines useful as kinase inhibitors. WO115973; 2008
46. Vertex Pharmaceuticals, Inc. Aminopyrimidines useful as kinase inhibitors. WO128009; 2008
47. IRM LLC, Novartis AG. Preparation of pyrimidinylpyrazolamines as protein kinase inhibitors. WO042639; 2008
48. Novartis AG. Preparation of naphthalenecarboxylic acid and isoquinolinecarboxylic acid amides as tyrosine kinase inhibitors. WO125691; 2008
49. Natco Pharma Ltd. Preparation of phenylaminopyrimidine derivatives as inhibitors of BCR-ABL kinase for treating cancer. US0306100; 2008
50. Natco Pharma Ltd. Crystal form of phenylamino pyrimidine derivatives. WO109867; 2009
51. IRM LLC. Preparation of pyrrolo[2,3-b] pyridinecarboxamides as protein kinase inhibitors. WO144253; 2008
52. IRM LCC. Preparation of as protein kinase inhibitors. WO157131; 2008
53. 4SC AG. Preparation of bifunctional compounds as inhibitors of protein kinases and histone deacetylases. WO063054; 2009
54. Dana Farber Cancer Institute. Small molecule myristate inhibitors of Bcr-abl and methods of use. WO073153; 2009
55. Sun Pharma Advanced Research Company Ltd. Preparation of novel hydrazide containing tyrosine kinase inhibitors. WO109991; 2009
56. Università degli Studi di Milano-Bicocca, Université de Geneve, Université Claude Bernard Lyon I. Alfa-carboline inhibitors of NPM-ALK, Ret, and Bcr-Abl. WO025872; 2010
57. The Regents of the University of California. Preparation of pyrazolo[3,4-d] pyrimidine derivatives as kinase inhibitors. WO045542; 2010
58. Hanke JH, Gardner JP, Dow RL, et al. 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;271:695-701
59. Nova Decision, Azasynth. Derivatives of azaindoles as inhibitors of protein kinases Abl and Src. WO092489; 2010
60. Synthec Solution LLC. Amides as kinase inhibitors and as antitumor agents. WO096395; 2010
61. ArQule, Inc. Substituted dipyrido-pyrimido-diazepine and benzo-pyrido-pyrimido compounds. US249108; 2010
62. Deciphera Pharmaceuticals LLC. Kinase inhibitors useful for the treatment of myeloproliferative diseases and other proliferative diseases. US7790756; 2010
63. Zhang D. Preparation of fluoro-substituted compounds as kinase inhibitors. WO008788; 2011
64. Hanmi Holdings CO LTD, Korea Institute of Science and Technology and Catholic University Industry Academic Cooperation Foundation. Preparation of thienopyrimidine derivatives for use as protein kinase inhibitors. WO093684; 2011
65. Pyramal Life Sciences Ltd. Oxadiazole compounds, their preparation and use for treating cancer. WO104680; 2011
66. Novartis AG. Preparation of cyclic ether compounds useful as kinase inhibitors for treatment of cancer or autoimmune diseases. WO004217; 2012
67. Schenone S, Tintori C, Botta M. Using insights into Pim1 structure to design new anticancer drugs. Curr Pharm Des 2010;16:3964-78
68. F. Hoffmann-La Roche AG. Substituted 6,6-fused nitrogenous heterocyclic compounds as c-Abl kinase inhibitors and their preparation. WO080284; 2012
69. Pierre Fabre Medicament. Derivatives of azaindazole or diazaindazole type as medicament. WO101239; 2012
70. Università degli Studi di Padova. Biphenyl tricyclic quinazoline compounds. WO127012; 2012
71. Ho TH, Jonasch E. Axitinib in the treatment of metastatic renal cell carcinoma. Future Oncol 2011;7:1247-53
72. Musumeci F, Radi M, Brullo C, Schenone S. Vascular endothelial growth factor (VEGF) receptors: drugs and new inhibitors. J Med Chem 2012;55:10797-822
73. Pfizer, Inc. N-methyl-2-[3-((e)-2-pyridin-2-yl-vinyl)-1H-indazol-6-ylsulfanyl]-benzamide for the treatment of chronic myelogenous leukaemia. WO068909; 2013
74. Novartis AG. Preparation of benzamide compounds as ABL1, ABL2, and BCR-ABL1 inhibitors for treating cancer, viral infections, and CNS disorders. WO171641; 2013
75. Novartis AG. Preparation of benzamide derivatives for inhibiting the activity of ABL1, ABL2 and BCR-ABL1 for treating cancer. WO171639; 2013
76. Astar Biotech LLC. Preparation of ethynylbenzamide and piperdinecarboxamide compounds as protein kinase inhibitors. WO019338; 2014
77. Nanjing Sanhome Pharmaceutical Co., Ltd. Alkynyl heteroaromatic ring compounds ABL kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of cancer. WO040549; 2014
78. Nanjing Sanhome Pharmaceutical Co., Ltd. Preparation of heteroaryl alkynes as antitumor agents. WO082578; 2014
79. Nant Holdings Ip, Lic. Preparation of substituted indol-5-ol derivatives and their therapeutical applications. WO071378; 2014
80. Agency Science Tech & Res. Preparation of N-[4-(piperazinomethyl)phenyl] amides as MAP kinase interacting kinases 1 and 2 (MNK1 and MNK2) modulators and ABL and ABL (T3151) inhibitors. WO088519; 2014
81. Oribase Pharma. Azaindoles as protein kinase inhibitors and their preparation. WO102376; 2014
82. Oribase Pharma. Azaindole derivatives as inhibitors of protein kinases and their preparation. WO102378; 2014
83. Shanghai Pharmaceuticals Holding Co., Ltd. Deuterated 3-cyanoquinoline compounds as protein kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of cancer. WO086284; 2014
84. Terrabay Pharmaceuticals, Inc. Fluorocyclobutanylimidazole compounds as ABL tyrosine kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of cancers. WO108021; 2014