Correction: Discovery of Entrectinib: A New 3-Aminoindazole as a Potent Anaplastic Lymphoma Kinase (ALK), c-ros Oncogene 1 Kinase (ROS1), and Pan-Tropomyosin Receptor Kinases (Pan-TRKs) inhibitor (Journal of Medicinal Chemistry (2016) 59: 7 (3392-3408) DOI: 10.1021/acs.jmedchem.6b00064);Discovery of Entrectinib: A New 3-Aminoindazole As a Potent Anaplastic Lymphoma Kinase (ALK), c-ros Oncogene 1 Kinase (ROS1), and Pan-Tropomyosin Receptor Kinases (Pan-TRKs) inhibitor

Journal of Medicinal Chemistry

Volumn 59, Issue 7, 2016, Pages 3392-3408

  Menichincheri, Maria ^a   Ardini, Elena ^a   Magnaghi, Paola ^a   Avanzi, Nilla ^a   Banfi, Patrizia ^a   Bossi, Roberto ^a,c   Buffa, Laura ^a   Canevari, Giulia ^a   Ceriani, Lucio ^a   Colombo, Maristella ^a   Corti, Luca ^a   Donati, Daniele ^a   Fasolini, Marina ^a   Felder, Eduard ^a   Fiorelli, Claudio ^a,d   Fiorentini, Francesco ^b   Galvani, Arturo ^a   Isacchi, Antonella ^a   Borgia, Andrea Lombardi ^a   Marchionni, Chiara ^a   Nesi, Marcella ^a   Orrenius, Christian ^a   Panzeri, Achille ^a   Pesenti, Enrico ^b   Rusconi, Luisa ^a   Saccardo, Maria Beatrice ^a   Vanotti, Ermes ^a   Perrone, Ettore ^a   Orsini, Paolo ^a   more..

^a NERVIANO MEDICAL SCIENCES   (Italy)

^b Accelera   (Italy)

^c Cernusco sul Naviglio   (Italy)

^d CHIESI FARMACEUTICI S P A   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 [4 [[5 (3,5 DIFLUOROBENZYL) 1H INDAZOL 3 YL]CARBAMOYL] 3 (TETRAHYDRO 2H PYRAN 4 YLAMINO)BENZYL]PIPERIDINE; ANAPLASTIC LYMPHOMA KINASE; ANAPLASTIC LYMPHOMA KINASE INHIBITOR; ENTRECTINIB; N 1 [5 (3,5 DIFLUOROBENZYL) 1H INDAZOL 3 YL] N 4 [2 (DIMETHYLAMINO)ETHYL] N 4 METHYL 2 (TETRAHYDRO 2H PYRAN 4 YLAMINO)BENZENE 1,4 DICARBOXAMIDE; N [5 (3,5 DIFLUORO BENZYL) 1H INDAZOL 3 YL] 2 (2 FLUORO ETHYLAMINO) 4 (4 METHYL PIPERAZIN 1 YL) BENZAMIDE; N [5 (3,5 DIFLUOROBENZYL) 1H INDAZOL 3 YL] 4 (PIPERAZIN 1 YL) 2 (TETRAHYDRO 2H PYRAN 4 YLAMINO)BENZAMIDE; N [5 (3,5 DIFLUOROBENZYL) 1H INDAZOL 3 YL] 4 [(1 METHYLPIPERIDIN 4 YL)OXY] 2 (TETRAHYDRO 2H PYRAN 4 YLAMINO)BENZAMIDE; PROTEIN TYROSINE KINASE; TYROSINE KINASE ROS1; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; BENZAMIDE DERIVATIVE; BRAIN DERIVED NEUROTROPHIC FACTOR RECEPTOR; INDAZOLE DERIVATIVE; NEUROTROPHIN 3 RECEPTOR; ONCOPROTEIN; PROTEIN KINASE INHIBITOR; PROTEIN TYROSINE KINASE A; ROS1 PROTEIN, HUMAN;

ANIMAL EXPERIMENT; ANTIPROLIFERATIVE ACTIVITY; AREA UNDER THE CURVE; ARTICLE; BLOOD BRAIN BARRIER; CACO 2 CELL LINE; CANINE MODEL; CELL MEMBRANE PERMEABILITY; CELL PROLIFERATION; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG BRAIN LEVEL; DRUG DESIGN; DRUG EFFICACY; DRUG HALF LIFE; DRUG PENETRATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; IN VIVO STUDY; LIVER MICROSOME; MAXIMUM PLASMA CONCENTRATION; MOUSE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; TIME TO MAXIMUM PLASMA CONCENTRATION; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMISTRY; CRYSTALLIZATION; DOG; DRUG DEVELOPMENT; DRUG EFFECTS; DRUG SCREENING; LUNG NEOPLASMS; METABOLISM; NUDE MOUSE; ORAL DRUG ADMINISTRATION; PATHOLOGY; SCID MOUSE; TUMOR CELL CULTURE; WESTERN BLOTTING; WISTAR RAT; X RAY CRYSTALLOGRAPHY;

ADMINISTRATION, ORAL; ANIMALS; ANTINEOPLASTIC AGENTS; BENZAMIDES; BLOOD-BRAIN BARRIER; BLOTTING, WESTERN; CELL MEMBRANE PERMEABILITY; CELL PROLIFERATION; CRYSTALLIZATION; CRYSTALLOGRAPHY, X-RAY; DOGS; DRUG DISCOVERY; HUMANS; INDAZOLES; LUNG NEOPLASMS; MICE; MICE, NUDE; MICE, SCID; MICROSOMES, LIVER; PROTEIN KINASE INHIBITORS; PROTEIN-TYROSINE KINASES; PROTO-ONCOGENE PROTEINS; RATS; RATS, WISTAR; RECEPTOR PROTEIN-TYROSINE KINASES; RECEPTOR, TRKA; RECEPTOR, TRKB; RECEPTOR, TRKC; TUMOR CELLS, CULTURED; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84966377269     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.9b01259     Document Type: Erratum

References (49)

1. Deininger, M.; Buchdunger, E.; Druker, B. J. The development of imatinib as a therapeutic agent for chronic myeloid leukemia Blood 2005, 105, 2640-2653 10.1182/blood-2004-08-3097
2. Tsao, M. S.; Sakurada, A.; Cutz, J. C.; Zhu, C. Q.; Kamel-Reid, S.; Squire, J.; Lorimer, I.; Zhang, T.; Liu, N.; Daneshmand, M.; Marrano, P.; da Cunha Santos, G.; Lagarde, A.; Richardson, F.; Seymour, L.; Whitehead, M.; Ding, K.; Pater, J.; Shepherd, F. A. Erlotinib in lung cancer-molecular and clinical predictors of outcome N. Engl. J. Med. 2005, 353, 133-144 10.1056/NEJMoa050736
3. Shaw, A. T.; Engelman, J. A. ALK in lung cancer: past, present, and future J. Clin. Oncol. 2013, 31, 1105-1111 10.1200/JCO.2012.44.5353
4. Mossé, Y. P.; Wood, A.; Maris, J. M. Inhibition of ALK signalling for cancer therapy Clin. Cancer Res. 2009, 15, 5609-5614 10.1158/1078-0432.CCR-08-2762
5. Morris, S. W.; Kirstein, M. N.; Valentine, M. B.; Dittmer, K. G.; Shapiro, D. N.; Saltman, D. L.; Look, A. T. Fusion of a kinase gene ALK, to a nucleolar protein gene, NPM, in non-Hodgkin's Science 1994, 263, 1281-1284 10.1126/science.8122112
6. Griffin, C. A.; Hawkins, A. L.; Dvorak, C.; Henkle, C.; Ellingham, T.; Perlman, E. J. Recurrent involvement of 2p23 in inflammatory myofibroblastic tumours Cancer Res. 1999, 59, 2776-2780
7. Soda, M.; Choi, Y. L.; Enomoto, M.; Takada, S.; Yamashita, Y.; Ishikawa, S.; Fujiwara, S.-I.; Watanabe, H.; Kurashina, K.; Hatanaka, H.; Bando, M.; Ohno, S.; Ishikawa, Y.; Aburatani, H.; Niki, T.; Sohara, Y.; Sugiyama, Y.; Mano, H. Identification of the transforming EML4-ALK fusion gene in non-small-cell lung cancer Nature 2007, 448, 561-566 10.1038/nature05945
8. Rikova, K.; Guo, A.; Zeng, O.; Possemato, A.; Yu, J.; Haack, H.; Nardone, J.; Lee, K.; Reeves, C.; Li, Y.; Hu, Y.; Tan, Z.; Stokes, M.; Sullivan, L.; Mitchell, J.; Wetzel, R.; MacNeill, J.; Ren, J. M.; Yuan, J.; Bakalarski, C. E.; Villen, J.; Kornhauser, J. M.; Smith, B.; Li, D.; Zhou, X.; Gygi, S. P.; Gu, T.-L.; Polakiewicz, R. D.; Rush, J.; Comb, M. J. Global survey of phosphotyrosine signalling identifies oncogenic kinases in lung cancer Cell 2007, 131, 1190-1203 10.1016/j.cell.2007.11.025
9. Mossé, Y. P.; Laudenslager, M.; Longo, L.; Cole, K. A.; Wood, A.; Attiyeh, E. F.; Laquaglia, M. J.; Sennett, R.; Lynch, J. E.; Perri, P.; Laureys, G.; Speleman, F.; Kim, C.; Hou, C.; Hakonarson, H.; Torkamani, A.; Schork, N. J.; Brodeur, G. M.; Tonini, G. P.; Rappaport, E.; Devoto, M.; Maris, J. M. Identification of ALK as a major familial neuroblastoma predisposition gene Nature 2008, 455, 930-935 10.1038/nature07261
10. Janoueix-Lerosey, I.; Lequin, D.; Brugières, L.; Ribeiro, A.; de Pontual, L.; Combaret, V.; Raynal, V.; Puisieux, A.; Schleiermacher, G.; Pierron, G.; Valteau-Couanet, D.; Frebourg, T.; Michon, J.; Lyonnet, S.; Amiel, J.; Delattre, O. Somatic and germline activating mutations of the ALK kinase receptor in neuroblastoma Nature 2008, 455, 967-970 10.1038/nature07398
11. Chen, Y.; Takita, J.; Choi, Y. L.; Kato, M.; Ohira, M.; Sanada, M.; Wang, L.; Soda, M.; Kikuchi, A.; Igarashi, T.; Nakagawara, A.; Hayashi, Y.; Mano, H.; Ogawa, S. Oncogenic mutations of ALK kinase in neuroblastoma Nature 2008, 455, 971-974 10.1038/nature07399
12. George, R. E.; Sanda, T.; Hanna, M.; Fröhling, S.; Luther, W., II; Zhang, J.; Ahn, Y.; Zhou, W.; London, W. B.; McGrady, P.; Xue, L.; Zozulya, S.; Gregor, V. E.; Webb, T. R.; Gray, N. S.; Gilliland, D. G.; Diller, L.; Greulich, H.; Morris, S. W.; Meyerson, M.; Look, A. T. Activating mutations in ALK provide a therapeutic target in neuroblastoma Nature 2008, 455, 975-978 10.1038/nature07397
13. Christensen, J. G.; Zou, H. Y.; Arango, M. E.; Li, Q.; Lee, J. H.; McDonnell, S. R.; Yamazaki, S.; Alton, G. R.; Mroczkowski, B.; Los, G. Cytoreductive antitumor activity of PF-2341066, a novel inhibitor of anaplastic lymphoma kinase and c-Met, in experimental models of anaplastic large-cell lymphoma Mol. Cancer Ther. 2007, 6, 3314-3322 10.1158/1535-7163.MCT-07-0365
14. Cui, J. J.; Tran-Dube, M.; Shen, H.; Nambu, M.; Kung, P. P.; Pairish, M.; Jia, L.; Meng, J.; Funk, L.; Botrous, I.; McTigue, M.; Grodsky, N.; Ryan, K.; Padrique, E.; Alton, G.; Timofeevski, S.; Yamazaki, S.; Li, Q.; Zou, H.; Christensen, J.; Mroczkowski, B.; Bender, S.; Kania, R. S.; Edwards, M. P. Structure based drug design of crizotinib (PF-02341066), a potent and selective dual inhibitor of mesenchymal-epithelial transition factor (c-MET) kinase and anaplastic lymphoma kinase (ALK) J. Med. Chem. 2011, 54 (18) 6342-6363 10.1021/jm2007613
15. TM (Crizotinib), a potent and selective dual inhibitor of mesenchymal epithelial transition (MET) and anaplastic lymphoma kinase (ALK) for cancer treatment Annu. Rep. Med. Chem. 2013, 48, 421-434 10.1016/B978-0-12-417150-3.00025-9
16. Marsilje, T. H.; Pei, W.; Chen, B.; Lu, W.; Uno, T.; Jin, Y.; Jiang, T.; Kim, S.; Li, N.; Warmuth, M.; Sarkisova, Y.; Sun, F.; Steffy, A.; Pferdekamper, A. C.; Li, A. G.; Joseph, S. B.; Kim, Y.; Liu, B.; Tuntland, T.; Cui, X.; Gray, N. S.; Steensma, R.; Wan, Y.; Jiang, J.; Chopiuk, G.; Li, J.; Gordon, W. P.; Richmond, W.; Johnson, K.; Chang, J.; Groessl, T.; He, Y.-Q.; Phimister, A.; Aycinena, A.; Lee, C. C.; Bursulaya, B.; Karanewsky, D. S.; Seidel, H. M.; Harris, J. L.; Michellys, P.-Y. Synthesis, structure-activity relationships, and in vivo efficacy of the novel potent and selective anaplastic lymphoma kinase (ALK) inhibitor 5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)-phenyl)pyrimidine-2,4-diamine (LDK378) currently in phase 1 and phase 2 clinical trials J. Med. Chem. 2013, 56, 5675-5690 10.1021/jm400402q
17. Sakamoto, H.; Tsukaguchi, T.; Hiroshima, S.; Kodama, T.; Kobayashi, T.; Fukami, T. A.; Oikawa, N.; Tsukuda, T.; Ishii, N.; Aoki, Y. CH5424802, a selective ALK inhibitor capable of blocking the resistantgatekeeper mutant Cancer Cell 2011, 19, 679-690 10.1016/j.ccr.2011.04.004
18. Kinoshita, K.; Kobayashi, T.; Asoh, K.; Furuichi, N.; Ito, T.; Kawada, H.; Hara, S.; Ohwada, J.; Hattori, K.; Miyagi, T.; Hong, W.-S.; Park, M.-J.; Takanashi, K.; Tsukaguchi, T.; Sakamoto, H.; Tsukuda, T.; Oikawa, N. 9-Substituted 6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazoles as highly selective and potent anaplastic lymphoma kinase inhibitors J. Med. Chem. 2011, 54, 6286-5694 10.1021/jm200652u
19. Katayama, R.; Khan, T. M.; Benes, C.; Lifshits, E.; Ebi, H.; Rivera, V. M.; Shakespeare, W. C.; Iafrate, A. J.; Engelman, J. A.; Shaw, A. T. Therapeutic strategies to overcome crizotinib resistance in non-small cell lung cancers harboring the fusion oncogene EML4-ALK Proc. Natl. Acad. Sci. U. S. A. 2011, 108 (18) 7535-7540 10.1073/pnas.1019559108
20. Gainor, J. F.; Ou, S. H.; Logan, J.; Borges, L. F.; Shaw, A. T. The central nervous system as a sanctuary site in ALK-positive non-small-cell lung cancer J. Thorac. Oncol. 2013, 8, 1570-1573 10.1097/JTO.0000000000000029
21. Sasaki, T.; Okuda, K.; Zheng, W.; Butrynski, J.; Capelletti, M.; Wang, L.; Gray, N. S.; Wilner, K.; Christensen, J. G.; Demetri, G.; Shapiro, G. I.; Rodig, S. J.; Eck, M. J.; Jänne, P. A. The neuroblastoma-associated F1174L ALK mutation causes resistance to an ALK kinase inhibitor in ALK-translocated cancers Cancer Res. 2010, 70, 10038-10043 10.1158/0008-5472.CAN-10-2956
22. Choi, Y. L.; Soda, M.; Yamashita, Y.; Ueno, T.; Takashima, J.; Nakajima, T.; Yatabe, Y.; Takeuchi, K.; Hamada, T.; Haruta, H.; Ishikawa, Y.; Kimura, H.; Mitsudomi, T.; Tanio, Y.; Mano, H. ALK Lung Cancer Study Group. EML4-ALK mutations in lung cancer that confer resistance to ALK inhibitors N. Engl. J. Med. 2010, 363, 1734-1739 10.1056/NEJMoa1007478
23. Katayama, R.; Shaw, A. T.; Khan, T. M.; Mino-Kenudson, M.; Solomon, B. J.; Halmos, B.; Jessop, N. A.; Wain, J. C.; Yeo, A. T.; Benes, C.; Drew, L.; Saeh, J. C.; Crosby, K.; Sequist, L. V.; Iafrate, A. J.; Engelman, J. A. Mechanisms of acquired crizotinib resistance in ALK-rearranged lung Cancers Sci. Transl. Med. 2012, 4, 120ra17 10.1126/scitranslmed.3003316
24. Bergethon, K.; Shaw, T.; Ou, S. H. I.; Katayama, R.; Lovly, C. M.; McDonald, N. T.; Massion, P. P.; Siwak-Tapp, C.; Gonzalez, A.; Fang, R.; Mark, E. J.; Batten, J. M.; Chen, H.; Wilner, K. D.; Kwak, E. L.; Clark, J. W.; Carbone, D. P.; Ji, H.; Engelman, J. A.; Mino-Kenudson, M.; Pao, W.; Iafrate, A. J. ROS1 rearrangements define a unique molecular class of lung cancers J. Clin. Oncol. 2012, 30, 863-870 10.1200/JCO.2011.35.6345
25. Greco, A.; Miranda, C.; Pierotti, M. A. Rearrangements of NTRK1 gene in papillary thyroid carcinoma Mol. Cell. Endocrinol. 2010, 321, 44-49 10.1016/j.mce.2009.10.009
26. Vaishnavi, A.; Capelletti, M.; Le, A. T.; Kako, S.; Butaney, M.; Ercan, D.; Mahale, S.; Davies, K. D.; Aisner, D. L.; Pilling, A. B.; Berge, E. M.; Kim, J.; Sasaki, H.; Park, S. I.; Kryukov, G.; Garraway, L. A.; Hammerman, P. S.; Haas, J.; Andrews, S. W.; Lipson, D.; Stephens, P. J.; Miller, V. A.; Varella-Garcia, M.; Jänne, P. A.; Doebele, R. C. Oncogenic and drug-sensitive NTRK1 rearrangements in lung cancer Nat. Med. 2013, 19, 1469-1472 10.1038/nm.3352
27. Ardini, E.; Bosotti, R.; Borgia, A. L.; De Ponti, C.; Somaschini, A.; Cammarota, R.; Amboldi, N.; Raddrizzani, L.; Milani, A.; Magnaghi, P.; Ballinari, D.; Casero, D.; Gasparri, F.; Banfi, P.; Avanzi, N.; Saccardo, M. B.; Alzani, R.; Bandiera, T.; Felder, E.; Donati, D.; Pesenti, E.; Sartore-Bianchi, A.; Gambacorta, M.; Pierotti, M. A.; Siena, S.; Veronese, S.; Galvani, A.; Isacchi, A. The TPM3-NTRK1 rearrangement is a recurring event in colorectal carcinoma and is associated with tumor sensitivity to TRKA kinase inhibition Mol. Oncol. 2014, 8, 1495-1507 10.1016/j.molonc.2014.06.001
28. Wiesner, T.; He, J.; Yelensky, R.; Esteve-Puig, R.; Botton, T.; Yeh, I.; Lipson, D.; Otto, G.; Brennan, K.; Murali, R.; Garrido, M.; Miller, V. A.; Ross, J. S.; Berger, M. F.; Sparatta, A.; Palmedo, G.; Cerroni, L.; Busam, K. J.; Kutzner, H.; Cronin, M. T.; Stephens, P. J.; Bastian, B. C. Kinase fusions are frequent in Spitz tumours and spitzoid melanoma Nat. Commun. 2014, 5, 3116 10.1038/ncomms4116
29. Ross, J. S.; Wang, K.; Gay, L.; Al-Rohil, R.; Rand, J. V.; Jones, D. M.; Lee, H. J.; Sheehan, C. E.; Otto, G. A.; Palmer, G.; Yelensky, R.; Lipson, D.; Morosini, D.; Hawryluk, M.; Catenacci, D. V.; Miller, V. A.; Churi, C.; Ali, S.; Stephens, P. J. New routes to targeted therapy of intrahepatic cholangiocarcinomas revealed by next-generation sequencing Oncologist 2014, 19, 235-242 10.1634/theoncologist.2013-0352
30. Kim, J.; Lee, Y.; Cho, H. J.; Lee, Y. E.; An, J.; Cho, G. H.; Ko, Y. H.; Joo, K. M.; Nam, D. H. NTRK1 fusion in glioblastoma multiforme PLoS One 2014, 9, e91940 10.1371/journal.pone.0091940
31. Wu, G.; Diaz, A. K.; Paugh, B. S.; Rankin, S. L.; Ju, B.; Li, Y.; Zhu, X.; Qu, C.; Chen, X.; Zhang, J.; Easton, J.; Edmonson, M.; Ma, X.; Lu, C.; Nagahawatte, P.; Hedlund, E.; Rusch, M.; Pounds, S.; Lin, T.; Onar-Thomas, A.; Huether, R.; Kriwacki, R.; Parker, M.; Gupta, P.; Becksfort, J.; Wei, L.; Mulder, H. L.; Boggs, K.; Vadodaria, B.; Yergeau, D.; Russell, J. C.; Ochoa, K.; Fulton, R. S.; Fulton, L. L.; Jones, C.; Boop, F. A.; Broniscer, A.; Wetmore, C.; Gajjar, A.; Ding, L.; Mardis, E. R.; Wilson, R. K.; Taylor, M. R.; Downing, J. R.; Ellison, D. W.; Zhang, J.; Baker, S. J. The genomic landscape of diffuse intrinsic pontine glioma and pediatric non-brainstem high-grade glioma Nat. Genet. 2014, 46, 444-450 10.1038/ng.2938
32. Amatu, A.; Somaschini, A.; Cerea, G.; Bosotti, R.; Valtorta, E.; Buonandi, P.; Marrapese, G.; Veronese, S.; Luo, D.; Hornby, Z.; Multani, P.; Murphy, D.; Shoemaker, R.; Lauricella, C.; Giannetta, L.; Maiolani, M.; Vanzulli, A.; Ardini, E.; Galvani, A.; Isacchi, A.; Sartore-Bianchi, A.; Siena, S. Novel CAD-ALK gene rearrangement is drugable by entrectinib in colorectal cancer Br. J. Cancer 2015, 113, 1730-1734 10.1038/bjc.2015.401
33. Sartore-Bianchi, A.; Ardini, E.; Bosotti, R.; Amatu, A.; Valtorta, E.; Somaschini, A.; Raddrizzani, L.; Palmeri, L.; Banfi, P.; Bonazzina, E.; Misale, S.; Marrapese, G.; Leone, A.; Alzani, R.; Luo, D.; Hornby, Z.; Lim, J.; Veronese, S.; Vanzulli, A.; Bardelli, A.; Martignoni, M.; Davite, C.; Galvani, A.; Isacchi, A.; Siena, S. Sensitivity to entrectinib associated with a novel LMNA-NTRK1 gene fusion in metastatic colorectal cancer J. Natl. Cancer Inst. 2016, 108, djv306 10.1093/jnci/djv306
34. Orsini, P.; Menichincheri, M.; Vanotti, E.; Panzeri, A. Highly efficient synthesis of 5-benzyl-3-aminoindazoles Tetrahedron Lett. 2009, 50, 3098-3100 10.1016/j.tetlet.2009.04.024
35. Lombardi Borgia, A.; Menichincheri, M.; Orsini, P.; Panzeri, A.; Perrone, E.; Vanotti, E.; Nesi, M.; Marchionni, C. Substituted indazole derivatives active as kinase inhibitors. WO2009/013126 A1, 2009.
36. Bossi, R. T.; Saccardo, M. B.; Ardini, E.; Menichincheri, M.; Rusconi, L.; Magnaghi, P.; Orsini, P.; Avanzi, N.; Borgia, A. L.; Nesi, M.; Bandiera, T.; Fogliatto, G.; Bertrand, J. A. Crystal structure of anaplastic lymphoma kinase in complex with ATP competitive inhibitors Biochemistry 2010, 49, 6813-6825 10.1021/bi1005514
37. Fontana, D.; Ceccon, M.; Gambacorti-Passerini, C.; Mologni, L. Activity of second-generation ALK inhibitors against crizotinib-resistant mutants in an NPM-ALK model compared to EML4-ALK Cancer Med. 2015, 4, 953-965 10.1002/cam4.413
38. Ardini, E.; Menichincheri, M.; Banfi, P.; Bosotti, R.; De Ponti, C.; Pulci, R.; Ballinari, D.; Ciomei, M.; Texido, G.; Degrassi, A.; Avanzi, N.; Amboldi, N.; Saccardo, M. B.; Casero, D.; Orsini, P.; Bandiera, T.; Mologni, L.; Anderson, D.; Wei, G.; Harris, J.; Vernier, J.-M.; Li, G.; Felder, E.; Donati, D.; Isacchi, A.; Pesenti, E.; Magnaghi, P.; Galvani, A. Entrectinib, a pan-TRK, ROS1, and ALK inhibitor with activity in multiple molecularly defined cancer indications. Mol. Cancer Ther. 2016, DOI: 10.1158/1535-7163.MCT-15-0758.
39. Colombo, M.; Sirtori, F. R.; Rizzo, V. A fully automated method for accurate mass determination using high-performance liquid chromatography with a quadrupole/orthogonal acceleration time-of-flight mass spectrometer Rapid Commun. Mass Spectrom. 2004, 18, 511-517 10.1002/rcm.1368
40. Felder, E. R.; Badari, A.; Disingrini, T.; Mantegani, S.; Orrenius, C.; Avanzi, N.; Isacchi, A.; Salom, B. The generation of purinome-targeted libraries as a means to diversify ATP-mimetic chemical classes for lead finding Mol. Diversity 2012, 16, 27-51 10.1007/s11030-012-9361-6
41. Winn, M. D.; Ballard, C. C.; Cowtan, K. D.; Dodson, E. J.; Emsley, P.; Evans, P. R.; Keegan, R. M.; Krissinel, E. B.; Leslie, A. G. W.; McCoy, A.; McNicholas, S. J.; Murshudov, G. N.; Pannu, N. S.; Potterton, E. A.; Powell, H. R.; Read, R. J.; Vagin, A.; Wilson, K. S. Overview of the CCP4 suite and current developments Acta Crystallogr., Sect. D: Biol. Crystallogr. 2011, D67, 235-242 10.1107/S0907444910045749
42. McCoy, A. J.; Grosse-Kunstleve, R. W.; Adams, P. D.; Winn, M. D.; Storoni, L. C.; Read, R. J. Phaser crystallographic software J. Appl. Crystallogr. 2007, 40, 658-674 10.1107/S0021889807021206
43. Emsley, P.; Cowtan, K. (2004) Coot: Model-building tools for molecular graphics Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, D60, 2126-2132 10.1107/S0907444904019158
44. Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Refinement of Macromolecular Structures by the Maximum-Likelihood method Acta Crystallogr., Sect. D: Biol. Crystallogr. 1997, D53, 240-255 10.1107/S0907444996012255
45. Delano, W. L. The PyMol Molecular Graphics System; DeLano Scientific LLC, Palo Alto, CA, 2008.
46. Pevarello, P.; Brasca, M. G.; Amici, R.; Orsini, P.; Traquandi, G.; Corti, L.; Piutti, C.; Sansonna, P.; Villa, M.; Pierce, B. S.; Pulici, M.; Giordano, P.; Martina, K.; Fritzen, E. L.; Nugent, R. A.; Casale, E.; Cameron, A.; Ciomei, M.; Roletto, F.; Isacchi, A.; Fogliatto, G.; Pesenti, E.; Pastori, W.; Marsiglio, A.; Leach, K. L.; Clare, P. M.; Fiorentini, F.; Varasi, M.; Vulpetti, A.; Warpehoski, M. A. 3-Aminopyrazole inhibitors of CDK2/Cyclin A as antitumor agents. 1. Lead finding J. Med. Chem. 2004, 47, 3367-3380 10.1021/jm031145u
47. Kerns, E. H.; Di, L.; Petusky, S.; Farris, M.; Ley, R.; Jupp, P. Combined application of parallel artificial membrane permeability assay and Caco-2 permeability assays in drug discovery J. Pharm. Sci. 2004, 93, 1440-1453 10.1002/jps.20075
48. Beria, I.; Ballinari, D.; Bertrand, J. A.; Borghi, D.; Bossi, R. T.; Brasca, M. G.; Cappella, P.; Caruso, M.; Ceccarelli, W.; Ciavolella, A.; Cristiani, C.; Croci, V.; De Ponti, A.; Fachin, G.; Ferguson, R. D.; Lansen, J.; Moll, J. K.; Pesenti, E.; Posteri, H.; Perego, R.; Rocchetti, M.; Storici, P.; Volpi, D.; Valsasina, B. Identification of 4,5-Dihydro-1H-pyrazolo[4,3-h]quinazoline Derivatives as a New Class of Orally and Selective Polo-Like Kinase 1 Inhibitors J. Med. Chem. 2010, 53, 3532-3551 10.1021/jm901713n
49. Bao, R.; Lai, C. J.; Qu, H.; Wang, D.; Yin, L.; Zifcak, B.; Atoyan, R.; Wang, J.; Samson, M.; Forrester, J.; DellaRocca, S.; Xu, G. X.; Tao, X.; Zhai, H. X.; Cai, X.; Qian, C. CUDC-305, a novel synthetic HSP90 inhibitor with unique pharmacologic properties for cancer therapy Clin. Cancer Res. 2009, 15, 4046-4057 10.1158/1078-0432.CCR-09-0152