5-Substituted pyrimidine derivatives of conformationally...

Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...

Reexamination Certificate

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C544S313000, C544S317000, C514S274000

Reexamination Certificate

active

07009050

ABSTRACT:
The embodiments described herein concern 5-substituted pyrimidine derivatives of conformationally locked nucleoside analogues and to the use of these derivatives as anti-viral and anti-cancer agents. The compounds are of the formula:wherein B is uracil-1-yl or cytosin-1-yl having a 5-substituent selected from halogen, alkyl, alkenyl, and alkynyl, with the proviso that where B is uracil-1-yl, the 5-substituent is not methyl. The compounds are useful in the treatment of Herpes simplex virus (HSV).

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patent: 5869666 (1999-02-01), Marquez et al.
patent: WO 95/08541 (1995-03-01), None
patent: WO 98/05662 (1998-02-01), None
“Fields Virology, Third Ed.”, B. N. Fields et al eds., Lippincott-Raven, Philadelphia, 1996 ,p. 431.
Salmon, S.E. et al “Principles of Cancer Therapy” in “Cecil Textbook of Medicine, 20th Edition”, W.B. Saunders, Philadelphia, 1996, pp. 1036-1049.
Balasubramanian, B.N. et al, “Recent Developments in Cancer Cytoxics” in “Annual Reports in Medicinal Chemistry, vol. 33”, Academic Press, San Diego, 1998, pp. 151-159.
Miller, D.M. “The Future of Oncology” in “Cecil Textbook of Medicine, 20th Edition”, W.B. Saunders, Philadelphia, 1996, pp. 1071-1077.
Grignet-Debrus et al., (2000)Comparative in vitro and in vivo cytotoxic activity of(E)-5-(2-bromovinyl)-2′-deoxyuridine(BVDU)and its arabinosyl derivative, (E)-5-(2-bromovinyl)-1-β-D-arabinofuranosyluracil(BvaraU),against tumor cells expressing either the Varicella zoster or the Herpes simplex virus thymidine kinase, Cancer Gene Therapy, vol. 7, No. 2, pp. 215-223.
Marquez et al., (1996)Nucleosides with a Twist. Can Fixed Forms of Sugar Ring Pucker Influence Biological Activity in Nucleosides and Oligonucleotides?, Journal of Medicinal Chemistry, vol. 39, No. 19, pp. 3739-3747.

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