Tyrosine kinase inhibitors. 10. Isomeric 4-[(3-bromophenyl)amino]pyrido[d]-pyrimidines are potent ATP binding site inhibitors of the tyrosine kinase function of the epidermal growth factor receptor

Journal of Medicinal Chemistry

Volumn 39, Issue 9, 1996, Pages 1823-1835

  Rewcastle, Gordon W ^a   Palmer, Brian D ^a   Thompson, Andrew M ^a   Bridges, Alexander J ^b   Cody, Donna R ^b   Zhou, Hairong ^b   Fry, David W ^b   McMichael, Amy ^b   Denny, William A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 (METHYLAMINO)PYRIDO[3,4 D]PYRIMIDINE; 7 (METHYLAMINO)PYRIDO[4,3 D]PYRIMIDINE; EPIDERMAL GROWTH FACTOR RECEPTOR; PROTEIN TYROSINE KINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; AUTOPHOSPHORYLATION; BINDING SITE; CANCER CELL CULTURE; DRUG ACTIVITY; DRUG SYNTHESIS; ENZYME BINDING; ENZYME INHIBITION; HUMAN; HUMAN CELL; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION;

HUMANS; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORYLATION; PYRIMIDINES; RECEPTOR, EPIDERMAL GROWTH FACTOR; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0029975029     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9508651     Document Type: Article

References (36)

1. (a) Fantl, W. J.; Johnson, D. E.; Williams, L. T. Signalling by receptor tyrosine kinases. Annu. Rev. Biochem. 1993, 62, 453-481.
2. (b) Fry, D. W. Protein tyrosine kinases as therapeutic targets in cancer chemotherapy, and recent advances in the development of new inhibitors. Exp. Opin. Invest Drugs 1994, 3, 577-595.
3. Jardines, L.; Weiss, M.; Fowble, B.; Greene, M. Neu (c-erbB-2/HER2) and the epidermal growth factor receptor (EGFR) in breast cancer. Pathobiology 1993, 61, 268-282.
4. Lupu, R.; Lippmann, M. E. The role of erbB-2 signal transduction pathways in human breast cancer. Breast Cancer Res. Treat. 1993, 27, 83-93.
5. Fontana, X.; Ferrari, P.; Namer, M.; Peysson, R.; Salanon, C.; Bussiere, F. C-erb-B2 gene amplification and serum level of C-erb-B2 oncoprotein at primary breast cancer diagnosis. Anticancer Res. 1994, 14, 2099-2104.
6. Hickey, K.; Grehan, D.; Reid, I. M.; Obriain, S.; Walsh, T. N.; Hennessy, T. P. J. Expression of epidermal growth factor receptor and proliferating cell nuclear antigen predicts response of esophageal squamous cell carcinoma to chemoradiotherapy. Cancer 1994, 74, 1693-1698.
7. (a) El-Zayat, A. A. E.; Pingree, T. F.; Mock, P. M.; Clark, G. M.; Otto, R. A.; Von Hoff, D. D. Epidermal growth factor receptor amplification in head and neck cancer. Cancer J. 1991, 4, 375-380.
8. (b) Stanton, P.; Richards, S.; Reeves. J.; Nikolic, M.; Edington, K.; Clark, L; Robertson, G.; Souter, D.; Mitchell, R.; Hendler, F. J.; Cooke, T.; Parkinson, E. K.; Ozanne, B. W. Epidermal growth factor receptor expression by human squamous cell carcinomas of the head and neck, cell lines and xenografts. Br. J. Cancer 1994, 70, 427-433.
9. Levitzki, A.; Gazit, A. Tyrosine kinase inhibition: An approach to drug development. Science 1995, 267, 1782-1788
10. Palmer, B. D.; Rewcastle, G. W.; Thompson, A. M.; Boyd, M.; Showalter, H. D. H.; Sercel, A. D.; Fry, D. W.; Kraker, A. J.; Denny, W. A. Tyrosine kinase inhibitors. 4. Structure-activity relationships among N- and 3-substituted 2,2′-dithiobis(1H-indoles) for in vitro inhibition of receptor and nonreceptor protein tyrosine kinases. J. Med. Chem. 1995, 38, 58-67.
11. Burke, T. R. Protein-tyrosine kinase inhibitors. Drugs Future 1992, 17, 119-131.
12. Cushman, M.; Zhu, H; Geahlen, R. L.; Kraker, A. J. Synthesis and biochemical evaluation of a series of aminoflavones as potential inhibitors of protein-tyrosine kinases p56(lck), EGFr, and p60(v-src). J. Med. Chem. 1994, 37, 3353-3362.
13. Geissler, J. F.; Roesel, J. L.; Meyer, T.; Trinks, U. P.; Traxler, P.; Lydon, N. B. Benzopyranones and benzothiopyranones: a class of tyrosine protein kinase inhibitors with selectivity for the v-abl kinase. Cancer Res. 1992, 52, 4492-4498.
14. Trinks, U.; Buchdunger, E.; Furet, P.; Kump, W.; Mett, H.; Meyer, T.; Muller, M.; Regenass, U.; Rihs, G.; Lydon, N.; Traxler, P. Dianilinophthalimides: potent and selective, ATP-competitive inhibitors of the EGF-receptor protein tyrosine kinase. J. Med. Chem. 1994, 37, 1015-1027.
15. Ward, W. H. J.; Cook, P. N.; Slater, A. M.; Davies, D. H.; Holdgate, G. A.; Green, L. R. Epidermal growth factor receptor tyrosine kinase. Investigation of catalytic mechanism, structure-based searching and discovery of a potent inhibitor. Biochem. Pharmacol. 1994, 48, 659-666.
16. Fry, D. W.; Kraker, A. J.; McMichael, A.; Ambroso, L. A.; Nelson, J. M.; Leopold, W. R.; Connors, R. W.; Bridges, A. J. A specific inhibitor of the epidermal growth factor receptor tyrosine kinase. Science 1994, 265, 1093-1095.
17. Rewcastle, G. W.; Denny, W. A.; Bridges, A. J.; Zhou, H.; Cody, D. R.; McMichael, A.; Fry, D. W. Tyrosine kinase inhibitors. 5. Synthesis and structure-activity relationships for 4-(phenylmethyl)amino- and 4-phenylaminoquinazolines as potent adenosine 5′-triphosphate binding site inhibitors of the tyrosine kinase domain of the epidermal growth factor receptor. J. Med. Chem 1995, 38, 3482-3487.
18. Bridges, A. J.; Zhou, H.; Cody, D. R.; Rewcastle, G. W.; McMichael, A.; Showalter, H. D. H.; Fry, D. W.; Kraker, A. J.; Denny, W. A. Tyrosine kinase inhibitors. 8. An unusually steep structure activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxy-quinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor. J. Med. Chem. 1996, 39, 267-276.
19. Thompson, A. M.; Bridges, A. J.; Fry, D. W.; Kraker, A. J.; Denny, W. A. Tyrosine kinase inhibitors. 7. 7-Amino-4-(phenylamino)-and 7-amino-4-[(phenylmethyl)amino]pyrido[4,3-d]pyrimidines: a new class of inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor. J. Med. Chem. 1995, 38, 3780-3788.
20. Taylor, E. C.; Knopf, R. J.; Cogliano, J. A.; Barton, J. W.; Pfleiderer, W. A facile pyrimidine ring cleavage. J. Am. Chem. Soc. 1960, 82, 6058-6064.
21. Metzger, R.; Oberdorfer, J.; Schwager, C.; Thielecke, W.; Boldt, P. A one-step synthesis of 2,4-bis(sec-alkylamino)-6-halo-3-pyridinecarbonitriles. Liebigs Ann. Chem. 1980, 946-953.
22. (a) Roe, A.; Hawkins, G. F. The preparation of heterocyclic fluorine compounds by the Schiemann reaction. I. The monofluoropyridines. J. Am. Chem. Soc. 1947, 69, 2443-2444.
23. (b) Talik, T.; Talik, Z. 2-Fluoro-4-nitropyridine. Rocz. Chem. 1967, 41, 1721-1726; Chem. Abstr. 1968, 69, 2823u.
24. (b) Talik, T.; Talik, Z. 2-Fluoro-4-nitropyridine. Rocz. Chem. 1967, 41, 1721-1726; Chem. Abstr. 1968, 69, 2823u.
25. Gabriel, S.; Coleman, J. Abkommlinge der cinchomersaure. II. (Derivatives of cinchomeronic acid. II.) Chem. Ber. 1902, 35, 2831-2845.
26. Rewcastle, G. W.; Denny, W. A.; Showalter, H. D. H.; Winters, R. T.; Colbry, N. L. Synthesis of 6-substituted pyrido[3,4-d]-pyrimidin-4(3H)-ones via directed lithiation of 2-substituted 5-aminopyridine derivatives. Manuscript submitted to J. Org. Chem.
27. (a) Hackler, R. E.; Jourdan, G. P. Condensed pyrimidine derivatives and their use as fungicides, insecticides, and miticides. Eur. Pat. Appl. EP 414,386, 1991; Chem. Abstr. 1991, 115, 71630j.
28. (b) Aminopyridopyrimidine fungicides, Jpn. Pat. 80,108,806 1980: Chem. Abstr. 1981, 94, 1068f.
29. Stanovnik, B.; Tisler, M. Convenient cyclisation of o-difunctional heterocycles with N,N-dimethylformamide dimethyl acetal. Synthesis 1974, 120-122.
30. Radmov, R.; Chanev, C.; Haimova, M. Lithiation of polychloropyrimidines and dichloropyridines. J. Org. Chem. 1991, 56, 4793-4796.
31. Rogers, R. B.; Claus, J. S.; Egli, E. A. 2-Amino-6-fluoronicotinic acids, derivatives, and their herbicidal use. U.S. Pat. 4,383.851; Chem. Abstr. 1983, 99, 88059d.
32. Colbry, N. L.; Elslager, E. F.; Werbel, L. M. Synthesis and antimalarial properties of 2,4-diamino-6-[(aryl)thio, sulfinyl and sulfonyl]pyrido[3,2-d]pyrimidines. J. Heterocycl. Chem. 1984, 21, 1521-1525.
33. Armarego, W. L. F. Triazanaphthalenes. Part I. Covalent hydration in 1,3,5-, 1,3,6-, 1,3,7- and 1,3,8-triazanaphthalene. J. Chem. Soc. 1962, 4094-4103.
34. Price, C. C ; Curtin, D. Y. 4-Hydroxypyrido[3,2-d]pyrimidine. J. Am. Chem. Soc. 1946, 68, 914.
35. Gill, G. N.; Weber, W. Purification of functionally active epidermal growth factor receptor protein using a competitive antagonist monoclonal antibody and competitive elution with epidermal growth factor. Methods Enzymol. 1987, 146, 82-88.
36. Nishikawa, S.; Kumazawa, Z.; Kashimura, N.; Maki, S.; Nishikimi, Y. Synthesis and cytokinin activity of 4- and 2,4-substituted pyrido[3,4-d]pyrimidines. Agric. Biol. Chem. 1986, 50, 495-497.