Bisheterocycle tandem compounds useful as antiviral agents,...

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

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C548S202000, C548S203000, C548S204000

Reexamination Certificate

active

07741348

ABSTRACT:
The present invention provides small molecule compounds of bisheterocycle in tandem having the structural formula of P1-P2, and the use thereof as well as a composition containing the compounds, each of P1 and P2 is an unsaturated 5-member heterocyclic ring having one or two heteroatoms. This compound may effectively inhibit the replication of influenza virus, the DNA replication of hepatitis B virus (HBV), and the formation of HBsAg and HBeAg. These compounds can be used for the preparation of a medicament for viral diseases, and may overcome the limitations of the known nucleosides drugs, including cytotoxicity, the requirement of other drugs having different structures for against the drug-resistant virus variants induced by long-term therapy. The structure of the compounds according to the invention is relatively simple and easy to be prepared.

REFERENCES:
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patent: WO 00/56724 (2000-03-01), None
patent: 00/56724 (2000-09-01), None
Cited ref—STN—11886593—preliminary—04282009.
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Kaiser et al. “X-ray structures and ab initio study of the conformational properties of novel oxazole and thiazole containing di- and tripeptide mimetics” J. Chem. Soc. Perkin Trans. 2:1081-1085 (2000).
Li et al. “Synthesis of a directly connected thiazole-oxazole ring system present in microcin B17” J. Org. Chem. 61:778-780 (1996).
Videnov et al. “Synthesis of naturally occurring, conformationally restricted oxazaole and thiazole containing di- and tripeptide mimetics” Angewandte Chemie, International Ed. in English 35:1503-1506 (1996).
Kaiser et al., “X-Ray structures and ab initio study of the conformational properties of novel oxazole and thiazole containing di- and tripeptide mimetics,” J. Chem. Soc., Perkin Trans. 2 (2000), (5), 1081-1085, compound 8.
Videnov et al., “Synthesis of naturally occurring, conformationally restricted oxazole- and thiazole-containing di- and tripeptide mimetics,” Angewandte Chemie, International Edition in English (1996), 35 (13/14), 1503-1506, compounds 16-17.
Li et al., “Synthesis of a Directly Connected Thiazole-Oxazole Ring System Present in Microcin B17,” Journal of Organic Chemistry (1996), 61(2), 778-80, compound 8.
Wang et al., “First total synthesis of Leucamide A,” Journ. of organic chemistry 68 (4): 1636-1639, Feb. 21, 2003, compounds 4, 8 and 9.
Wang et al., “Synthesis and biological evaluation of novel bisheterocycle-containing compounds as potential anti-influenza virus agents,” Bioorganic & Medicinal Chemistry Letters, Dec. 1, 2005, 15(23), 5284-5287, the whole document.
International Search Report for PCT/CN2006/000124 mailed May 18, 2006.
International Search Report; PCT/CN2006/000124; 7 pages.
“Synthesis of Naturally Occurring, Conformationally Restricted oxazole- and thiazole-containing di- and tripeptide Mimetics”; Videnov, Georgi et al.; Angewandte Chemie, International Edition in English (1996), 35 (13/414), 1503-1506, pp. 1503-1506.
“X-Ray structures and ab initio study of the conformational properties of novel oxazole and thiazole containing di- and tripeptide mimetics”; Kaiser, Dietmar et al.; J. Chem. So., Perkin Trans. 2 (2000), pp. 1081-1085.
“Synthesis of a Directly Connected Thiazole-Oxazole Ring System Present in Microcin B17”; Li, Gang et al.; J. Org. Che., 1996, 61, pp. 778-780.
“First Total Synthesis of Leucamide A”; Wang Wenlong et al.; J. Org. Chem., 2003, 68, pp. 1636-1639.
“Synthesis and biological evaluation of novel bisheterocycle-containing compounds as potential anti-influenza virus agents”; Wang Wen-Long et al.; Bioorganic & Medicinal Chemistry Letters 2005; pp. 5284-5287.

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