Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2011-05-17
2011-05-17
Havlin, Robert (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C514S690000
Reexamination Certificate
active
07943800
ABSTRACT:
The present invention provides compounds having formula (I), and additionally provides methods for the synthesis thereof, compositions thereof, and methods for the use thereof in the treatment of various disorders including cancer, metastasis and disorders involving increased angiogenesis, wherein R1—R6, Ra—Rc, Q, Y1, Y2and n are as defined herein.
REFERENCES:
patent: 2529825 (1950-11-01), Stoll
patent: 3227742 (1966-01-01), Lafont et al.
patent: 4472435 (1984-09-01), Branca et al.
patent: 6326349 (2001-12-01), Helmlinger et al.
patent: 2002/0119937 (2002-08-01), Khosla et al.
patent: 2002/0128480 (2002-09-01), Haneda et al.
patent: 2004/0062817 (2004-04-01), Peshoff
patent: 2006/0173205 (2006-08-01), Yasuhisa
patent: 2007/0037783 (2007-02-01), Huang et al.
patent: 2007/0037852 (2007-02-01), Danishefsky et al.
patent: 2009/0054488 (2009-02-01), Danishefsky et al.
patent: 2009/0124662 (2009-05-01), Danishefsky et al.
patent: 374445 (1990-06-01), None
patent: 1264594 (2002-12-01), None
patent: 1380579 (2004-01-01), None
patent: 989476 (1965-04-01), None
patent: 1036084 (1966-07-01), None
patent: 56-34655 (1981-04-01), None
patent: 56-34656 (1981-04-01), None
patent: 61-56146 (1986-03-01), None
patent: 7-138257 (1995-05-01), None
patent: 00-178223 (2000-06-01), None
patent: 01 078793 (2001-03-01), None
patent: 01 081088 (2001-03-01), None
patent: 02-519396 (2002-07-01), None
patent: 03-171335 (2003-06-01), None
patent: WO99/22722 (1999-05-01), None
patent: WO00/01648 (2000-01-01), None
patent: WO01/46451 (2001-06-01), None
patent: WO2004/009380 (2004-01-01), None
patent: WO2004/052359 (2004-06-01), None
patent: WO2004/083164 (2004-09-01), None
patent: WO2005019181 (2005-03-01), None
patent: WO2009070244 (2009-06-01), None
Singh et al. (Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (2002), 41B(2), 423-426).
Kubinyi (3D QSAR in Drug Design: Ligand-Protein Interactions and Molecular Similarity, vol. 2-3, Springer, 1998, 800 pages). TOC and pp. 243-244 provided.
Isogai et al. (STN Abstract of JP 07138257 A).
Bundgaard (Design and application of prodrugs, In a Textbook of Drug Design and Development, (1991), p. 113-191).
Nakamura (STN abstract of: Journal of Antibiotics (2002), 55(4), 442-444).
Gaul et al. (STN abstract of: Tetrahedron Letters (2002), 43(50), 9039-9042).
Gaul et al. (STN abstract of: Journal of the American Chemical Society (2003),125(20), 6042-6043).
Isogai (STN abstract of JP 07138257 A).
Gaul, et al. “Synthesis of the Macrolide Core of Migrastatin”Tetrahedron Letters43: 9039-9042, 2002.
Nakae, et al., “Migrastatin, a Novel 14-Membered Lactone”Journal of Antibiotics53(10): 1228-1230, 2000.
Nakamura, et al., “Absolute Configuration of Migrastatin, A Novel 14-Membered Ring Macrolide”Journal of Antibiotics55(4): 442-444, 2002.
Takemoto, et al., “Migrastatin, A Novel 14-Membered Ring Macrolide, Inhibits Anchorage-Independent Growth of Human Small Cell Lung Carcinoma Ms-1 Cells”Journal of Antibiotics54(12): 2001.
Woo, et al., “Migrastatin and a New Compound, Isomigrastatin, From Streptomyces Platensis”Journal of Antibiotics55(2): 141-146, 2002.
International Search Report Corresponding to PCT Appl. No. PCT/US2004/009571.
Abiko, A.; Liu, J. F.; Masamune, S.J. Am. Chem. Soc. 1997, 119, 2586.
Ahmar, M.; Duyck, C.; Fleming I.J. Chem. Soc., Perkin Trans. 1 1998, 2721.
Asami, Y.; Kakeya, H.; Onose, R.; Yoshida, A.; Matsuzaki, H.; Osada, H.Org. Lett. 2002, 4, 2845.
Aslakson, C. J., and Miller, F. R. 1992. Selective events in the metastatic process defined by analysis of the sequential dissemination of subpopulations of a mouse mammary tumor. Cancer Research 52: 1399-1405.
Biswas, K.; Lin, H.; Njardarson, J. T.; Chappell, M. D.; Chou, T. C.; Guan, Y.; Tong, W. P.; He, L.; Horwitz, S. B.; Danishefsky, S. J.J. Am. Chem. Soc. 2002, 124, 9825.
Blanchette et al.,Tet. Lett., 1984, 25, 2183.
Boden, E. P.; Keck, G. E.J. Org. Chem. 1985, 50, 2394.
Brower, V.Nat. Biotechnol. 1999, 17, 963.
Capitosti, S. M.; Hansen, T. P.; Brown, M. L.Bioorg. Med. Chem. 2004, 12, 327.
Carmeliet, P.Nat. Med. 2003, 9, 653.
Chan, J.; Jamison, T. F.J. Am. Chem. Soc. 2003, 125, 11514.
Chaomin, L.; Bardhan, S.; Pace, E. A.; Liang, M. C.; Gilmore, T. D.; Porco Jr. , J. A.Org. Lett. 2002, 4, 3267.
Chun, J.; Li, G.; Byun, H. S.; Bittman, R.J. Org. Chem. 2002, 67, 2600.
Cristofanilli, M.; Chamsangavej, C.; Hortobagyi, G. N.Nat. Rev. Drug Discovery2002, 1, 415.
Crystallographic data (excluding structural data) for compound 24 have been deposited with the Cambridge Crystallographic Data Centre (CCDC) as Deposition No. CCDC 230121.
D'Amato, R. J.; Loughnan, M. S.; Flynn, E.; Folkman,J. Proc. Natl. Acad. Sci. 1994, 91, 4082.
Danishefsky et al.,J. Am. Chem. Soc., 1985, 107, 1256.
Danishefsky, S. J.Aldrichimica Acta1986, 19, 59.
Danishefsky, S. J. et al.; J.J Am. Chem. Soc. 1979, 101, 7001.
Danishefsky, S. J., Kitahara, T.J. Am. Chem. Soc. 1974, 96, 7807.
Danishefsky, S. J.; Kato, N.; Askin, D.; Kerwin Jr. , J. F.J. Am. Chem. Soc. 1982, 104, 360.
Danishefsky, S. J.; Masters, J. J.; Young, W. B.; Link, J. T.; Snyder, L. B.; Magee, T. V.; Jung, D. K.; Isaacs, R. C. A.; Bornmann, W. G.; Alaimo, C. A.; Coburn, C. A. ; DiGrandi, M. J.J. Am. Chem. Soc. 1996, 118, 2843.
Danishefsky, S.J.Chemtracts1989, 2, 273 (Part I).
Danishefsky, S.J.Chemtracts1989, 2, 273 (Part II).
Deplanque, G ; Harris, A. L.Eur. J Cancer2000, 36, 1713.
Dess, D. B.; Martin, J. C.J. Am. Chem. Soc. 1991, 113, 7277.
Dixon, D. J.; Krause, L.; Ley, S. V.J. Chem. Soc., Perkin Trans. 1, 2001, 2516.
Dredge, K.; Dalgleish, A. G.; Marriott, J. B.Anti-Cancer Drugs2003, 14, 331.
Duffey, M. O.; LeTiran, A.; Morken, J. P.J. Am. Chem. Soc. 2003, 125, 1458.
Edmonds, M. K.; Abell, A. D.J. Org. Chem. 2001, 66, 3747.
Egawa, Y. et al.;Chem. Pharm. Bull. 1963, 11, 589.
Eng, H. M. ; Myles, D. C.Tetrahedron Lett. 1999, 40, 2279.
Evans et al.,J. Am. Chem. Soc., 2002, 124, 392.
Evans, D.A., Aldrichimica Acta, 1982, 15, 23-32.
Fenteany, G.; Zhu, S.Curr. Top. Med. Chem. 2003, 3, 593.
Ferrier,J Chem. Soc., 1964, 5443.
Garbaccio, R. M.; Stachel, S. J.; Baeschlin, D. K.; Danishefsky, S. J.J. Am. Chem. Soc. 2001, 123, 10903.
Gaul, C. et al.;J. Am. Chem. Soc. 2003, 125, 6042.
Gaul, C. et al.;J. Am. Chem. Soc. 2004, 126(4), 1038-1040.
Gaul, C., et al., Tetrahedron Lett., 2002, 43, 9039-9042.
Harris, C. R.; Danishefsky, S. J.J. Org. Chem. 1999, 64, 8434.
Hayashi, Y.; Shoji, M.; Yamaguchi, J.; Sato, K.; Yamaguchi, S. ; Mukaiyama, T.; Sakai, K.; Asami, Y.; Kakeya, H.; Osada, H.J. Am. Chem. Soc. 2002, 124, 12078.
Hirai, K.; Ooi, H.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S.Org. Lett. 2003, 5, 857.
Hochlowski, J. E.; Whittern, D. N.; Hill, P.; McAlpine, J. B.J. Antibiot. 1994, 47, 870.
Inanaga et al.,Bull. Chem. Soc. Jpn., 1979, 52, 1989.
Jorgensen et al.,J. Org. Chem., 2001, 66, 4630.
Jung, H. J.; Lee, H. B.; Kim, C. J.; Rho, J. R.; Shin, J.; Kwon, H. J.J. Antibiot. 2003, 56, 492.
Kadam, S.; McAlpine, J.B.J. Antibiot. 1994, 47, 875.
Kakeya, H.; Onose, R.; Koshino, H.; Yoshida, A.; Kobayashi, K.; Kageyama, S. I.; Osada, H.J. Am. Chem. Soc. 2002, 124, 3496.
Kakeya, H.; Onose, R.; Yoshida, A.; Koshino, H.; Osada, H.J. Antibiot. 2002, 55, 829.
Kantarjian, H. M.Curr. Opin. Oncol. 2001, 12(6), 564-573.
Karwowski, J. P.; Jackson, M.; Sunga, G.; Sheldon, P.; Poddig, J. B.; Kohl, W. L.; Adam, S. J.Antibiot. 1994, 47, 862.
Katzenellenbogen, J. A. et al.;J. Chem. Soc., Perkin Trans. 1 1998, 2721.
Katzenellenbogen, J.A., et al., J. Am. Chem. Soc., 1976, 98, 4925.
Kerbel, R.; Folkman,J. Nat. Rev. Cancer2003, 2, 727.
Kitaori, K., Furukawa, Y., Yoshimoto, H.; Otera,J. Tetrahedron1999, 55, 14381.
Klohs, W. D.; Hamby, J. M.Curr. Opin. Biotechnol. 1999, 10, 544.
Kondo, H.; Oritani, T.; Kiyota, H.Eur. J. Org. Chem. 2000, 3459.
Lauffenburger, D. A.; Horwitz, A. F.Cell1996, 84, 359.
Lee, W. W.; Chang, S.Tetrahedron: Asymmetry1999, 10, 4473.
Li, D. R.; Xia, W. J.; Shi, L.; Tu, Y. Q.Synthesis2003, 41.
Lin, S. ; Danishefsky, S. J.Angew. Chem. Int. Ed. 2001, 40(10), 1967-1970.
Luche et al.,J. Am
Danishefsky Samuel J.
Gaul Christoph
Njardarson Jon T.
Choate Hall & Stewart LLP
Havlin Robert
Knight Julie Anne
Rearick John P.
Sloan-Kettering Institute for Cancer Research
LandOfFree
Migrastatin analogs and uses thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Migrastatin analogs and uses thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Migrastatin analogs and uses thereof will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2625446