Methylenedioxyanilino-quinazolines and -cyanoquinolines as inhibitors of MEK and/or Src

Expert Opinion on Therapeutic Patents

Volumn 14, Issue 7, 2004, Pages 1095-1100

[No Author Info available]

Author keywords

Cancer; Mitogen activated protein kinase (MAPK) extracellular signal regulated kinase (ERK) kinase (MEK) inhibitor; Oncology; Src kinase inhibitor

Indexed keywords

2 (2 CHLORO 4 IODOANILINO) N CYCLOPROPYLMETHOXY 3,4 DIFLUOROBENZAMIDE; [4 [2 CYCLOPENTYL 9 (3 HYDROXYPHENETHYL)PURIN 6 YLAMINO]PHENYL]DIMETHYLPHOSPHINE OXIDE; ANILINE DERIVATIVE; ANTINEOPLASTIC AGENT; AZD 0530; AZD 6244; DASATINIB; GEFITINIB; METHYLENEDIOXYANILINOCYANOQUINOLINE DERIVATIVE; METHYLENEDIOXYANILINOQUINAZOLINE DERIVATIVE; MITOGEN ACTIVATED PROTEIN KINASE; MITOGEN ACTIVATED PROTEIN KINASE INHIBITOR; N (2,3 DIHYDROXYPROPOXY) 3,4 DIFLUORO 2 (2 FLUORO 4 IODOANILINO)BENZAMIDE; PROTEIN TYROSINE KINASE; PROTEIN TYROSINE KINASE INHIBITOR; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CLINICAL TRIAL; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; MOUSE; NONHUMAN; PATENT; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 3543088502     PISSN: 13543776     EISSN: None     Source Type: Journal    
DOI: 10.1517/13543776.14.7.1095     Document Type: Article

References (39)

1. BOSCHELLI D: 4-Anilino-3-quinolinecarbonitriles: an emerging class of kinase inhibitors. Curr. Top. Med. Chem. (2002) 2:1051-1063.
2. BRIDGES AJ: Chemical inhibitors of protein kinases. Chem. Rev. (2001) 101:2541-2571.
3. LAIRD AD, CHERRINGTON JM: Small-molecule tyrosine kinase inhibitors: clinical development of anticancer drugs. Expert Opin. Investig. Drugs (2003) 12(1):51-64.
4. SAWYER TK: Cancer metastasis therapeutic targets and drug discovery: emerging small-molecule protein kinase inhibitors. Expert Opin. Investig. Drugs (2004) 13(1):1-19.
5. REDDY KB, NABHA SM, ATANASKOVA N: Role of MAP kinase in tumor progression and invasion. Cancer Metastasis Rev. (2004) 22:395-403.
6. BOLLAG G, FREEMAN S, LYONS JF, POST LE: Raf pathway inhibitors in oncology. Curr. Opin. Investig. Drugs (2003) 4(12):1436-1441.
7. CHANG F, STEELMAN LS, LEE JT et al.: Signal transduction mediated by the Ras/Raf/MEK/ERK pathway from cytokine receptors to transcription factors: potential targeting for therapeutic intervention. Leukemia (2003) 17:1263-1293.
8. LEE JT Jr, MCCUBREY JA: Targeting the Raf kinase cascade in cancer therapy-novel molecular targets and therapeutic strategies. Expert Opin. Ther. Targets (2002) 6(6):659-678.
9. KREPINSKY J, WU D, INGRAM A, SCHOLEY J, TANG D: Developments in mitogen-induced extracellular kinase-1 inhibitors and their use in the treatment of disease. Expert Opin. Ther. Patents (2002) 12(12):1795-1811.
10. ENGLISH JM, COBB MH: Pharmacological inhibitors of MAPK pathways. Trends Pharmacol. Sci. (2002) 23(1):40-45.
11. BERGER DM, MALLON R: Kinase components of the Ras-MAPK signaling cascade as potential targets for therapeutic intervention. Drugs Fut. (2003) 28(12):1211-1226.
12. PELLETIER J-P, FERNANDES JC, BRUNET J et al.: In vivo selective inhibition of mitogen-activated protein kinase kinase 1/2 in rabbit experimental osteoarthritis is associated with a reduction in the development of structural changes. Arthritis Rheum. (2003) 48(6):1582-1593.
13. CIRUELA A, DIXON AK, BRAMWEL LS, GONZALEZ MI, PINNOCK RD, LEE K: Identification of MEK1 as a novel target for the treatment of neuropathic pain. Br. J. Pharmacol. (2003) 138(5):751-756.
14. LEE AF, SEBOLDT-LEOPOLD J, MEYER MB: CI-1040 (PD184352), a targeted signal transduction inhibitor of MEK (MAPKK). Semin. Oncol. (2003) 30(5):105-116.
15. WATERHOUSE DM, RINEHART J, ADJEI A: A phase 2 study of an oral MEK inhibitor, CI-1040, in patients with advanced nonsmall-cell lung, breast, colon, or pancreatic cancer. Proc. Am. Soc. Clin. Oncol. (2003) 22:204 (Abstract 816).
16. SEBOLT-LEOPOLD JS, MERRIMAN R, OMER C et al.: The biological profile of PD-0325901: a second generation analogue of CI-1040 with improved pharmaceutical potential. Proc. Am. Assoc. Cancer Res. (2004) 45:Abstract 4003.
17. LYSSIKATOS J, YEH T, WALLACE E et al.: ARRY-142886, a potent and selective MEK inhibitor: ATP-independent inhibition results in high enzymatic and cellular activity. Proc. Am. Assoc. Cancer Res. (2004) 45:Abstract 3888.
18. MARTIN GS: The hunting of the Src. Nature Rev.: Mol. Cell. Bio. (2001) 2:467-475.
19. FRAME MC: Src in cancer: deregulation and consequences for cell behaviour. Biochim. Biophys. Acta (2002) 1602:114-130.
20. SUMMY JM, GALLICK GE: Src family kinases in tumor progression and metastasis. Cancer Metastasis Rev. (2003) 22:337-358.
21. RUSSELLO SV, SHORE SK: Src in human carcinogenesis. Front. Biosci. (2004) 9:139-144.
22. MIYAZAKI T, SANJAY A, NEFF L, TANAKA S, HORNE WC, BARON R: Src kinase activity is essential for osteoclast function. J. Biol. Chem. (2004) 279(17):17660-17666.
23. WARMUTH M, DAMOISEAUX R, LIU Y, FABBRO D, GRAY N: Src family kinases: potential targets for the treatment of human cancer and leukaemia. Curr. Pharm. Des. (2003) 9:2043-2059.
24. SAWYER T, BOYCE B, DALGARNO D, IULIUCCI J: Src inhibitors: genomics to therapeutics. Expert Opin. Investig. Drugs (2001) 10(7):1327-1344.
25. ŠUŠA M, MISSBACH M, GREEN J: Src inhibitors: drugs for the treatment of osteoporosis, cancer or both? Trends Pharmacol. Sci. (2000) 21:489-495.
26. BISKOBING DM: Novel therapies for osteoporosis. Expert Opin. Investig. Drugs (2003) 12(4):611-621.
27. WHEELER C, STEPHENS T, BUTH K et al.: Novel approaches in oncology at AstraZeneca. Eur. J. Cancer, Suppl. (2003) 1(8):5-10.
28. LEE FY, LOMBARDO L, BORZILLERI R et al.: BMS-354825 - a potent dual SRC/ABL kinase inhibitor possessing curative efficacy against Imatinib sensitive and resistant human CML models in vivo. Proc. Am. Assoc. Cancer. Res. (2004) 45:abstract 3987.
29. MOHAMMAD A, NARDI V, METCALF III CA, SHAKESPEARE WC, SAWYER TK, DALEY GQ: Anti-proliferative effect of a novel purine-template based dual Src/Abl tyrosine kinase inhibitor AP23464 on native and imatinib-resistant Bcr-Abl cell lines. Proc. Am. Assoc. Cancer. Res. (2004) 45:Abstract 4641.
30. PLÉ PA, GREEN TP, HENNEQUIN LF, et al.: Discovery of a new class of anilinoquinazolines inhibitors with high affinity and specificity for the tyrosine kinase domain of c-Src. J. Med. Chem. (2004) 47(4):871-887.
31. BOSCHELLI DH, WANG YD, JOHNSON S et al.: 7-Alkoxy-4-phenylamino-3-quinolinecarbonitriles as dual inhibitors of Src and Abl kinases. J. Med. Chem. (2004) 47:1599-1601.
32. BERGER D, DUTIA M, POWELL D et al.: Synthesis and evaluation of 4-anilino-6,7-dialkoxy-3-quinolinecarbonitriles as inhibitors of kinases of the Ras-MAPK signaling cascade. Bioorg. Med. Chem. Lett. (2003) 13:3031-3034.
33. OLIVER A, COSTELLO GF, FENNELL M et al.: Novel series of C5-substituted anilinoquinazolines with highly potent and selective inhibition of c-Src tyrosine kinase activity. 227th ACS National Meeting, (2004): abstract MEDI-039.
34. ZHANG N, WU B, POWELL D: Synthesis and structure-activity relationships of 3-cyano-4-(phenoxyanilino)quinolines as MEK (MAPKK) inhibitors. Bioorg. Med. Chem. Lett. (2000) 10:2825-2828.
35. HENNEQUIN LF, STOKES ES, THOMAS A, et al.: Novel 4-anilinoquinazolines with C-7 basic side chains: design and structure activity relationship of a series of potent, orally active, VEGF receptor tyrosine kinase inhibitors. J. Med. Chem. (2002) 45(6):1300-1312.
36. c-src by 4-anilinoquinazolines. Biochemistry (2001) 40(24):7084-7091.
37. MURRAY M: Mechanisms of inhibitory and regulatory effects of methylenedioxyphenyl compounds on cytochrome P450-dependent drug oxidation. Curr. Drug. Metab. (2000) 1:67-84.
38. FOROOZESH M, PRIMROSE G, GUO Z, BELL LC, ALWORTH WL, GUENGERICH FP: Aryl acetylenes as mechanism-based inhibitors of cytochrome P450-dependent monooxygenase enzymes. Chem. Res. Toxicol. (1997) 10(1):91-102.
39. ZHANG N, WU B, EUDY N et al.: MEK (MAPKK) inhibitors. Part 2: Structure-activity relationships of 4-anilino-3-cyano-6,7-dialkoxyquinolines. Bioorg. Med. Chem. Lett. (2001) 11:1407-1410.