Heteroaryl-containing isoflavones as aromatase inhibitors

Details Heteroaryl-containing isoflavones as aromatase inhibitors Heteroaryl-containing isoflavones as aromatase inhibitors

2005-08-26

2009-08-11

Davis, Zinna N (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S400000, C549S401000

Reexamination Certificate

active

07572919

ABSTRACT:
Compounds and methods useful for treating and prevention of cancer, particularly hormone-dependent breast cancer. Provided are compounds of formula I:wherein X is selected from O, N, S, SO, SO2, and S(CH2)n, wherein n=1-10; R1and R2may be the same or different and are selected from H, OH, OCH3, OCH2CH3, OCH2C6H5, NH2, NHCH3, N(CH3)2, CH3, CH2CH3, CH2CH2CH3, CH(CH3)2, C(CH3)3, NO2, F, Cl, Br, CF3, SH, SCH3, SCH2CH3, OCOCH3, OCOC(CH3)3, OCOCH2COOH, and CN; and R3is a nitrogen-containing heterocyclic ring. Also provided are method for treating or preventing cancer in a subject by administering a therapeutically effective amount of a heteroaryl-containing isoflavone, or a pharmaceutically acceptable salt or prodrug thereof, to a subject in need of treatment. Also provided is a method for the synthesis of 2-substituted isoflavones by first reacting deoxybenzoins with a phase transfer catalyst to provide a 2-(alkylthio)isoflavone; second deprotecting the 2-(alkylthio)isoflavone; and third applying selective debenzylation to form the final compound.

REFERENCES:
patent: 2004/0087586 (2004-05-01), Brueggemeier et al.
International Search Report and Written Opinion from PCT/US05/30401, mailed Aug. 8, 2007.
Kim, Young-Woo, “Novel 2-Substituted Isoflavones: A Privileged Structure Approach to New Agents for Hormone-Dependent Breast Cancer,” PhD Dissertation, Aug. 2003, The Ohio State University, Columbus, OH.
Kim, Young-Woo et al., “Synthesis and Aromatase Ihibitory Activity of Novel Pyridine-Containing Isoflavones,” J. Med. Chem., Jul. 2, 2004, vol. 47, pp. 4032-4040, The Ohio State University, Columbus, OH.

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