Erratum:N-(Cycloalkylamino)acyl-2-aminothiazole Inhibitors of Cyclin-Dependent Kinase 2. N-[5-[[[5-(1,1-Dimethylethyl)-2-oxazolyl]methyl]thio]-2-thiazolyl]-4-piperidinecarboxamide (BMS-387032), a Highly Efficacious and Selective Antitumor Agent(Journal of Medicinal Chemistry (2004) 47 (1719-1728) DOI: 10.1021/jm0305568);N-(Cycloalkylamino)acyl-2-aminothiazole Inhibitors of Cyclin-Dependent Kinase 2. N-[5-[[[5-(1,1-Dimethylethyl)-2-oxazolyl]methyl]thio]-2-thiazolyl] -4-piperidinecarboxamide (BMS-387032), a Highly Efficacious and Selective Antitumor Agent

Journal of Medicinal Chemistry

Volumn 47, Issue 7, 2004, Pages 1719-1728

  Misra, Raj N ^a,b   Xiao, Hai Yun ^a   Kim, Kyoung S ^a   Lu, Songfeng ^a   Han, Wen Ching ^a   Barbosa, Stephanie A ^a   Hunt, John T ^a   Rawlins, David B ^a,c   Shan, Weifang ^a   Ahmed, Syed Z ^a,d   Qian, Ligang ^a   Chen, Bang Chi ^a   Zhao, Rulin ^a   Bednarz, Mark S ^a,c   Kellar, Kristen A ^a,c   Mulheron, Janet G ^a,c   Batorsky, Roberta ^a   Roongta, Urvashi ^a   Kamath, Amrita ^a   Marathe, Punit ^a   Ranadive, Sunanda A ^a   Sack, John S ^a   Tokarski, John S ^a   Pavletich, Nikola P ^a,f   Lee, Francis Y F ^a   Webster, Kevin R ^a,e   Kimball, S David ^a,c   more..

^a BRISTOL MYERS SQUIBB PHARMACEUTICAL RESEARCH INSTITUTE   (United States)

^b Lexicon Pharmaceuticals ^*  (United States)

^c Lexicon Pharmaceutical Corporation   (United States)

^d FMC CORPORATION   (United States)

^e ASTRAZENECA   (United Kingdom)

^f MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOTHIAZOLE; ANTINEOPLASTIC AGENT; CYCLIN DEPENDENT KINASE 1; CYCLIN DEPENDENT KINASE 2; CYCLIN DEPENDENT KINASE 4; CYCLIN DEPENDENT KINASE INHIBITOR; FLAVOPIRIDOL; N [5 (5 TERT BUTYL 2 OXAZOLYLMETHYLTHIO) 2 THIAZOLYL]ISONIPECOTAMIDE; N [5 [[[5 (1,1 DIMETHYLETHYL) 2 OXAZOLYL]METHYL]THIO] 2 THIAZOLYL] 4 PIPERIDINECARBOXAMIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; CELL FREE SYSTEM; CELL MEDIATED CYTOTOXICITY; CONTROLLED STUDY; DOG; DRUG BIOAVAILABILITY; DRUG CLEARANCE; DRUG EFFICACY; DRUG METABOLISM; DRUG PROTEIN BINDING; DRUG STRUCTURE; HUMAN; HUMAN CELL; MAXIMUM TOLERATED DOSE; MOUSE; NONHUMAN; OVARY CARCINOMA; PLASMA HALF LIFE; RAT; STRUCTURE ACTIVITY RELATION; TUMOR MODEL; TUMOR XENOGRAFT;

EID: 12144285797     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b01294     Document Type: Erratum

References (36)

1. (a) Hunter, T.; Pines, J. Cyclins and Cancer II. Cyclin and cdk inhibitors come of age. Cell 1994, 79, 573-582.
2. (b) Sherr, C. Cancer cell cycles. Science (Washington, DC) 1996, 274, 1672-1677.
3. (b) Review: Pines, J. The cell cycle kinases. Semin. Cancer Biol. 1994, 5, 305-313.
4. (a) Kamb, A.; Gruis, N. A.; Weaver-Feldhaus, J.; Liu, Q.; Harshman, K.; Tavtigian, S. V.; Stockert, E.; Day, R. S., III; Johnson, B. E.; Skolnik, M. H. A Cell Cycle Regulators, Potentially Involved in Genesis of Many Tumor Types. Science 1994, 264, 436-440.
5. (b) Nobori, T.; Miura, K.; Wu, D. J.; Lois, A.; Takabayashi, K.; Carson, D. A. Deletions of the cyclin-dependent kinase-4 inhibitor gene in multiple human cancers. Nature (London) 1994, 368, 753-756.
6. (c) Pines, J. Cyclins, cdks and cancer. Semin. Cancer Biol. 1995, 6, 63-72.
7. (d) Hartwell, L. H.; Kastan, M. B. Cell cycle control and cancer. Science 1994, 266, 1821-1828.
8. KiP1 protein: prognostic implications in primary breast cancer. Nat. Med. 1997, 3, 227-230.
9. Kip1, a cyclin-dependent kinase inhibitor. Am. J. Pathol. 1998, 153, 175-182.
10. KiP1 gene expression in benign prostatic hyperplasia and prostatic carcinoma. J. Intl. Cancer Inst. 1998, 90, 1284-1291.
11. KiP1 levels with recurrence and survival in patients with staged C prostate carcinoma. J. Natl. Cancer Inst. 1998, 90, 916-920.
12. KiP1 in malignant melanoma: inverse correlation with disease-free survival. Am. J. Pathol. 1998, 153, 305-312.
13. For reviews, see: (a) Huwe, A.; Mazitschek, R.; Giannis, A. Small molecules as inhibitors of cyclin-dependent kinases. Angew. Chem., Int. Ed. 2003, 42, 2122-2138.
14. (b) Sausville, E. A. Complexities in the development of cyclin-dependent kinase inhibitor drugs. Trends Mol. Med. 2002, 8, S32-S37.
15. (c) Kimball S. D.; Webster K. R. Cell cycle kinases and checkpoint regulation in cancer. Annu. Rep. Med. Chem. 2001, 36, 139-148.
16. (d) Rosania, G. R.; Chang, Y.-T. Targeting hyperproliferative disorders with cyclin dependent kinase inhibitors. Exp. Opin. Ther. Pat. 2000, 10, 215-230.
17. (e) Webster, K. R. The therapeutic potential of targeting the cell cycle. Exp. Opin. Invest. Drugs 1998, 7, 1-23.
18. (a) Zhai, S.; Senderowicz, A. M.; Sausville, E. A.; Figg, W. D. Favopiridol, a novel cyclin-dependent kinase inhibitor, in clinical development. Ann. Pharmacother. 2002, 36, 905-911.
19. (b) Stadler W. M.; Vogelzang, N. J.; Amato, R.; Sosman, J.; Taber, D.; Liebowitz, D.; Vokes, E. E. Flavopiridol, a novel cyclin-dependent kinase inhibitor, in metastatic renal cancer: a University of Chicago phase II consortium study. J. Clin. Oncol. 2000, 18, 371-375.
20. (c) Senderowicz, A. M. Flavopiridol: the first cyclin-dependent kinase inhibitor in human clinical trials. Invest. New Drugs 1999, 17, 313-320.
21. (d) Senderowicz, A. M.; Headlee, D.; Stinson, S. F.; Lush, R. M.; Kalil, N.; Villalba, L.; Hill, K.; Steinberg, S. M.; Figg, W. D.; Tompkins, A.; Arbuck, S. G.; Sausville, E. A. Phase I trial of continuous infusion flavopiridol, a novel cyclin-dependent kinase inhibitor, in patients with refractory neoplasms. J. Clin. Oncol. 1998, 16, 2986-2999.
22. (e) Sedlacek, H. H.; Czech, J.; Naik, R.; Kaur, G.; Worland, P.; Losiewicz, M.; Parker, B.; Carlson, B.; Smith, A.; Senderowicz, A.; Sausville, E. A. Flavopiridol (L868275; NSC 649890), a new kinase inhibitor for tumor therapy. Int. J. Oncol. 1996, 9, 1143-1168.
23. (f) Carlson, B. A.; Dubay, M. M.; Sausville, E. A.; Brizuela, L.; Worland, P. J. Flavopiridol induces g1 arrest with inhibition of cyclin-dependent kinase (cdk) 2 and cdk4 in human breast carcinoma cells. Cancer Res. 1996, 56, 2973-2978.
24. (g) Kaur, G.; Stetler-Stevenson, M.; Sebers, S.; Worland, P.; Sedlacek, H.; Myers, C.; Czeck, J.; Naik, R.; Sausville, E. Growth inhibition with reversible cell cycle arrest of carcinoma cells by flavone L86-8275. J. Nat. Cancer Inst. 1992, 84, 1736-1740.
25. (f) Kattige, S. L.; Naik, R. G.; Lakadawalla, A. D.; et al. US Patent 4,900,-727, February 13, 1990.
26. Kim, K. S.; Kimball, S. D.; Misra, R. N.; Rawlins, D. B.; Hunt, J. T.; Xiao, H.-Y.; Lu, S.; Qian, L.; Han, W.-C.; Shan, W.; Mitt, T.; Cai, Z.-W.; Poss, M. A.; Zhu, H.; Sack, J. S.; Tokarski, J. S.; Chang, C.-Y.; Pavletich, N.; Kamath, A.; Humphreys, W. G.; Marathe, P.; Bursuker, I.; Kellar, K. A.; Roongta, U.; Batorsky, R.; Mulheron, J. G.; Bol, D.; Fairchild, C. R.; Lee, F. Y.; Webster, K. R. Discovery of aminothiazole inhibitors of cyclin-dependent kinase 2. Synthesis, X-ray crystallographic analysis, and biological activities. J. Med. Chem. 2002, 45, 3905-3927.
27. (a) Presented in part: Misra, R. N.; Xiao, H.-Y.; Kim, K. S.; Lu, S.; Han, W.-C.; Rawlins, D. B.; Shan, W.; Ahmed, S. Z.; Qian, L.; Chen, B.-C.; Zhao, R.; Bednarz, M. S.; Bursuker, I.; Kellar, K. A.; Mulheron, J. G.; Batorsky, R. ; Roongta, U.; Sack, J. S.; Tokarski, J. S.; Lee, F. Y.; Bol, D. K.; Kamath, A. ; Humphreys, W. G.; Marathe, P.; Hunt, J. T.; Pavletich, N. P.; Kimball, S. D.; Webster, K. R. Abstracts of Papers 225th National Meeting of the American Chemical Society, New Orleans, LA, March 23-27, 2003; MEDI018.
28. (b) Misra, R. N.; Xiao, H. Y. US Patent 6,-515,004 B1, February 4, 2003.
29. Leysen, D. C.; Haemers, A.; Bollaert, W. Thiazolopyridine Analogues of Nalidixic Acid. 1. Thiazolo[5,4-b]pyridines. J. Heterocycl. Chem. 1984, 21, 401-406.
30. Schulze-Gahmen, U.; De Bondt, H. L.; Kim, S. H. High-resolution crystal structures of human cyclin-dependent kinase 2 with and without ATP: bound waters and natural ligand as guides for inhibitor design. J. Med. Chem. 1996, 39, 4540-4546.
31. For experimental protocols for in vivo experiments see: Lee, F. Y. F.; Borzilleri, R.; Fairchild, C. R.; Kim, S.-H.; Long, B. H.; Raventoz-Suarez, C.; Vite, G. D.; Rose, W. C.; Kramer, R. A. BMS-247550: a novel epothilone analogue with a mode of action similar to paclitaxel but possessing superior antitumor activity. Clin. Cancer Res. 2001, 7, 1429-1437.
32. Chiba, T.; Sakagami, H.; Murata, M.; Okimoto, M. Electrolytic oxidation of ketones in ammoniacal methanol in the presence of catalytic amounts of KI. J. Org. Chem. 1995, 60, 6764-6770.
33. Bonina, F. P.; Arenare, L.; Palagiano, F.; Salia, A.; Nava, F.; Trombetta, D.; Caprariis. Synthesis, stability, and pharmacological evaluation of nipecotic acid prodrugs. J. Pharm. Sci. 1999, 88, 561-567.
34. Abdel-Magid, A. F.; Carson, A. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures. J. Org. Chem. 1996, 61, 3849-3862.
35. 2. J. Org. Chem. 1986, 51, 1625-1627.
36. Long, B. H.; Wang, L.; Lorico, A.; Wang, R. R. C.; Brattain, M. G.; Casazza, A. M. Mechanisms of resistance to etoposide and teniposide in acquired resistant human colon and lung carcinoma cell lines. Cancer Res. 1991, 51, 5275-5284.