The development of HKI-272 and related compounds for the treatment of cancer

Archiv der Pharmazie

Volumn 341, Issue 8, 2008, Pages 465-477

  Wissner, Allan ^a   Mansour, Tarek S ^a  

^a WYETH RESEARCH   (United States)

Author keywords

EKB 569; HKI 272; Irreversible kinase inhibitors; Neratinib

Indexed keywords

4 (3 BROMOANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 [3 CHLORO 4 (2 PYRIDINYLMETHOXY)ANILINO] 3 CYANO 6 (4 DIMETHYLAMINOCROTONAMIDO) 7 ETHOXYQUINOLINE; ANTINEOPLASTIC AGENT; CANERTINIB; CYSTEINE; EKI 785; EPIDERMAL GROWTH FACTOR RECEPTOR; EPIDERMAL GROWTH FACTOR RECEPTOR 2; ERLOTINIB; FLUOROURACIL; FOLINIC ACID; GEFITINIB; IRINOTECAN; N [4 (3 BROMOANILINO) 6 QUINAZOLINYL]ACRYLAMIDE; OXALIPLATIN; PELITINIB; QUINAZOLINE DERIVATIVE; RAPAMYCIN; TRASTUZUMAB; UNCLASSIFIED DRUG; AMINOQUINOLINE DERIVATIVE; ANILINE DERIVATIVE; N (4 (3 CHLORO 4 (2 PYRIDINYLMETHOXY)ANILINO) 3 CYANO 7 ETHOXY 6 QUINOLYL) 4 (DIMETHYLAMINO) 2 BUTENAMIDE; N-(4-(3-CHLORO-4-(2-PYRIDINYLMETHOXY)ANILINO)-3-CYANO-7-ETHOXY-6-QUINOLYL)-4-(DIMETHYLAMINO)-2-BUTENAMIDE; QUINOLINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ASTHENIA; BREAST CANCER; CLINICAL TRIAL; COLON CANCER; DIARRHEA; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG EFFICACY; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG TOLERABILITY; ENZYME INACTIVATION; HUMAN; LUNG NON SMALL CELL CANCER; NAUSEA; NEUTROPENIA; NONHUMAN; PRIORITY JOURNAL; PROTEIN INTERACTION; PROTEIN TARGETING; REVIEW; SOMATIC MUTATION; STRUCTURE ACTIVITY RELATION; TUMOR RESISTANCE; BREAST TUMOR; COLON TUMOR; DRUG ANTAGONISM; DRUG SCREENING; FEMALE; LUNG TUMOR; METABOLISM; NEOPLASM; SYNTHESIS; TUMOR CELL LINE;

AMINOQUINOLINES; ANILINE COMPOUNDS; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE, TUMOR; COLONIC NEOPLASMS; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; LUNG NEOPLASMS; NEOPLASMS; QUINOLINES; RECEPTOR, EPIDERMAL GROWTH FACTOR; RECEPTOR, ERBB-2;

EID: 53149132043     PISSN: 03656233     EISSN: 15214184     Source Type: Journal    
DOI: 10.1002/ardp.200800009     Document Type: Review

References (65)

1. M. A. Olayioye, R. N. Neve, H. A. Lane, N. E. Hynes, EMBO J. 2000, 19, 3159-3167.
2. Y. Yarden, M. X. Sliwkowski, Nat. Rev. Mol. Cell Biol. 2001, 2, 127-137.
3. C. Kari, T. O. Chan, M. Rocha de Quadros, U. Rodeck, Cancer Res. 2003, 63, 1-5.
4. D. S. Salomon, R. Brandt, F. Ciadiello, N. Normanno, Crit. Rev. Oncol. Hematol. 1995, 19, 183-232.
5. W. J. Gullick, Br. Med. Bull. 1991, 47, 87-98.
6. J. R.Woodburn, Pharmacol. Ther. 1999, 82, 241-250.
7. N. E. Hynes, D. F. Stern, Biochim. Biophys. Acta 1994, 1198, 165-184.
8. D. R. Knighton, J. Zheng, L. F. T. Eyck, V. A. Ashford, et al., Science 1991, 253, 407-411.
9. D. R. Knighton, J. Zheng, L. F. Ten Eyck, S. S. Taylor, et al., Proc. Natl. Acad. Sci. 1993, 90, 5001-5005.
10. A. Levitzki, E. Mishani, Annu. Rev. Biochem. 2006, 75, 93-109.
11. P. Yaish, A. Gazit, C. Gilon, A. Levitzki, Science 1988, 242, 933-935.
12. P. M. Traxler, O. Wacker, H. L. Bach, J. F. Geissler, et al., J. Med. Chem. 1991, 34, 2328-2337.
13. A. Ricouart, J. C. Gesquiere, A. Tartar, C. Sergheraert, J. Med. Chem. 1991, 34, 73-78.
14. D. W. Fry, A. J. Kraker, A. McMichael, L. A. Ambroso, et al., Science 1994, 265, 1093-1095.
15. A. J. Barker, Zeneca Pharmaceuticals, EP566226A1, 1993.
16. For a review of EGFR kinase inhibitors that have been in the clinic see: A. E. Wakeling, Curr. Opin. Pharmacol. 2002, 2, 382-387.
17. M. S. Cohen, C. Zhang, K. M. Shokat, J. Taunton, Science 2005, 308, 1318-1321.
18. S. Andreas, K. Jonathan, M. Sumati, R. Ralph, V. S. Daniel, Proc. Natl. Acad. Sci. USA 2006, 103, 4234-4239.
19. W. A. Denny, Clin. Pharmacol. Ther. 2002, 93, 253-261.
20. A. Wissner, D. M. Berger, D. H. Boschelli, M. B. Floyd Jr., et al., J. Med. Chem. 2000, 43, 3244-3256.
21. J. Stamos, M. X. Sliwkowski, C. Eigenbrot, J. Biol. Chem. 2002, 277, 46265-46272.
22. A. Wissner, B. J. Johnson, M. B. Floyd, D. B. Bruce, American Cyanamid Co., EP87722A1, 1997.
23. A. J. Bridges, et al., Warner Lambert Co., WO9738983, 1997.
24. A. Wissner, B. J. Johnson, American Cyanamid Co., US5760041A, 1998.
25. D. W. Fry, A. J. Bridges, W. A. Denny, A. Doherty, et al., Proc. Natl. Acad. Sci. USA 1998, 95, 12022-12027.
26. C. M. Discafani, M. Carroll, M. B. Floyd Jr., I. J. Hollander, et al., Biochem. Pharmacol. 1999, 57, 917-925.
27. W. E. Sweeney, Y. Chen, K. Nakanishi, P. Frost, E. D. Avner, Kidney Int. 2000, 57, 339-340.
28. C. J. Torrance, P. E. Jackson, E. Montgomery, A. Wissner, et al., Nat. Med. 2000, 6, 1024-1028.
29. H.-R. Tsou, N. Mamuya, B. D. Johnson, M. F. Reich, et al., J. Med. Chem. 2001, 44, 2719-2734.
30. J. B. Smaill, G. W. Rewcastle, J. A. Loo, K. D. Greis, et al., J. Med. Chem. 2000, 43, 1380-1397.
31. L. F. Allen, P. F. Lenehan, I. A. Eiseman, W. L. Elliott, D. W. Fry, Semin. Oncol. 2002, 29, 11-21.
32. L. F. Allen, I. A. Eiseman, D. W. Fry, P. F. Lenehan, Semin. Oncol. 2003, 30, 65-78.
33. G. W. Rewcastle, W. A. Denny, A. J. Bridges, H. Zhou, et al., J. Med. Chem. 1995, 38, 3482-3487.
34. A. Wissner, D. M. Berger, D. H. Boschelli, M. B. Floyd Jr., et al., J. Med. Chem. 2000, 43, 3244-3256.
35. L. Shewchuk, A. Hassell, B. Wisely, W. Rocque, et al., J. Med. Chem. 2000, 43, 133-138.
36. A. Wissner, M. B. Floyd, S. K. Rabindran, R. Nilakantan, et al., Bioorg. Med. Chem. Lett. 2002, 12, 2893-2897.
37. A. Wissner, E. Overbeek, M. F. Reich, M. B. Floyd, et al., J. Med. Chem. 2003, 46, 49-63.
38. H.-R. Tsou, E. G. Overbeek-Klumpers, W. A. Hallett, M. F. Reich, et al., J. Med. Chem. 2005, 48, 1107-1131.
39. S. K. Rabindran, C. M. Discafani, E. C. Rosfjord, M. Baxter, et al., Adv. Cancer Res. 2004, 64, 3958-3965.
40. K. M. Shokat, Nat. Chem. Biol. 2007, 3, 229-238.
41. K.-K. Wong, Clin. Cancer Res. 2007, 13, 4593-4596.
42. T. Cascone, E. Martinelli, M. P. Morelli, F. Morgillo, et al., Exp. Opin. Drug Discov. 2007, 2, 335-348.
43. H. Shaw, J. de Bono, Eur. J. Cancer 2007, 43, 481-489.
44. J. Settleman, J. M. Kurie, Cancer Cell 2007, 12, 6-8.
45. J. Baselga, J. Clin. Oncol. 2006, 24, 2225-2226.
46. J. G. Paez, P. A. Janne, J. C. Lee, S. Tracy, et al., Science 2004, 304, 1497-1500.
47. S. Kobayashi, T. J. Boggon, T. Dayaram, P. A. Jaenne, et al., N. Engl. J. Med. 2005, 352, 786-792.
48. J. E. Dowell, J. D. Minna, N. Engl. J. Med. 2007, 352, 830-832.
49. W. Pao, V. A. Miller, K. A. Politi, G. I. Riely, et al., Proc. Natl. Acad. Sci. USA 2004, 101, 13306-13311.
50. C.-H. Yun, T. J. Boggon, Y. Li, M. S. Woo, et al., Cancer Cell 2007, 11, 217-227.
51. H. Ji, Z. Hongbin, X. Zhao, Y. Yuza, et al., Proc. Natl. Acad. Sci. USA 2006, 103, 7817-7822.
52. H. Ji, D. Li, L. Chen, T. Shimamura, et al., Cancer Cell 2006, 9, 485-495.
53. M. S. Cohen, C. Zhang, K. M. Shokat, J. Taunton, Science 2005, 308, 1318-1321.
54. E. L. Kwak, R. Sordella, D. W. Bell, N. Godin-Heymann, et al., Proc. Natl. Acad. Sci. USA 2005, 102, 7665-7670.
55. Y. Minami, T. Shimamura, K. Shah, T. LaFramboise, et al., Oncogene 2007, 26, 5023-5027.
56. D. Li, T. Shimamura, H. Ji, L. Chen, et al., Cancer Cell 2007, 12, 81-93.
57. K. D. Carey, A. J. Garton, M. S. Romero, J. Kahler, et al., Adv. Cancer Res. 2006, 66, 8163-8171.
58. C.-H. Yun, M. S. Woo, H. Greulich, K.-K. Wong, et al., Cancer Cell 2007, 11, 217-227.
59. C.-H. Yun, K. E. Mengwasser, A. V. Toms, M. S. Woo, et al., Proc. Natl. Acad. Sci. USA 2008, 105, 2070-2075.
60. S. K. Rabindran, Cancer Lett. 2005, 227, 9-23.
61. A. P. Venook, Cancer 2005, 103, 2435-2446.
62. M. Hidalgo, C. Erlichman, E. E. Rowinski, J. Koepp-Norris, et al., Proc. Am. Soc. Clin. Oncol. 2002, 21, abstract 65.
63. S. Tepar, E. Van Cutsem, E. Gamelin, abstract 3579, Annual Meeting of the American Chemical Society of Clinical Oncology. June 5-8, 2004.
64. th Annual Meeting of the American Society of Clinical Oncology, New Orleans, LA, June 5-8, 2004.
65. th Annual San Antonio Breast Cancer Symposium, December 13-16, 2007.