Spiro and dispiro 1,2,4-trioxolane antimalarials

Details Spiro and dispiro 1,2,4-trioxolane antimalarials Spiro and dispiro 1,2,4-trioxolane antimalarials

2005-06-14

2005-06-14

Trinh, Ba K. (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C514S462000

Reexamination Certificate

active

06906205

ABSTRACT:
A means and method for treating malaria, schistosomiasis, and cancer using a spiro or dispiro 1,2,4-trioxolane is described. The preferred 1,2,4-trioxolanes include a spiroadamantane group on one side of the trioxolane group, and a spirocyclohexyl on the other side of the trioxolane group, whereby the spirocyclohexyl ring is preferably substituted at the 4-position. In comparison to artemisinin semisynthetic derivatives, the compounds of this invention are structurally simple, easy to synthesize, non-toxic, and potent against malarial parasites.

REFERENCES:
patent: 3621062 (1971-11-01), Archer et al.
patent: 3673222 (1972-06-01), Archer et al.
patent: 3682991 (1972-08-01), Tullar et al.
patent: 4816478 (1989-03-01), Thornfeldt
patent: 4978676 (1990-12-01), Thornfeldt
patent: 5053342 (1991-10-01), Lawrence
patent: 5171676 (1992-12-01), Ziffer et al.
patent: 5216175 (1993-06-01), Avery et al.
patent: 5219880 (1993-06-01), Thornfeldt
patent: 5264879 (1993-11-01), Shikama
patent: 5270344 (1993-12-01), Herman
patent: 5430148 (1995-07-01), Webber et al.
patent: 5510356 (1996-04-01), Vennerstrom
patent: 5559145 (1996-09-01), Jeffort
patent: 5578637 (1996-11-01), Lai et al.
patent: 5614178 (1997-03-01), Bloom et al.
patent: 5672624 (1997-09-01), Posner
patent: 5721209 (1998-02-01), Horwitz et al.
patent: 5780675 (1998-07-01), Royer et al.
patent: 5817692 (1998-10-01), Posner
patent: 5932591 (1999-08-01), Posner et al.
patent: 6486199 (2002-11-01), Vennerstrom et al.
Posner, “Antimalarial peroxides in the qinghaosu (artemisinin) and yingzhaosu families”,Exp. Opin. Ther. Patents8(11) 1487-1493 (1998) Ashley Publications Ltd. ISSN 1354-3776.
Jefford, “Peroxidic Antimalarials”,Advances in Drug Research, vol. 29:271-323 (ISBN 0-12-013329-6) copyright 1997 Academic Press Ltd.
De Almeida Barbosa, Luiz-Claudio, “The design, synthesis and biological evaluation of stable ozonides with antimalarial activity”,J. Chem. Soc., Perkin Trans. 1, 1101-1105 (1996).
De Almeida Barbosa, Luiz-Claudio, “Synthesis of some Stable Ozonides with Anti-malarial Activity”,J. Chem. Soc., Perkin Trans. 1, 3251 (1992).
Vennerstrom, et al., “Dispiro-1,2,4,5-tetraoxanes: A New Class of Antimalarial Peroxides”,J. Med. Chem.35(16):3023-3027 (1992).
Kuel, Helmut: “Uber Konstitution und Entstehung der Ozonide von Bis-adamantyliden und Bis-Bicyclo ′3.3.1lnon-9-yliden”Chemische Berichte, vol. 108, No. 4, 1975, pp. 1207-1217, XP002217805.
Tabuchi, T: “Ozonolysis of vinyl ethers in the presence of α-diketones and α-keto esters”,J. Org. Chem., vol. 56, 1991, pp. 6591-6595, XP001117555.
Dussault, P.J.: “Selectivity in Lewis acid-mediated fragmentations of peroxides and ozonides; application to the synthesis of alkenes, homoallylethers, and 1,2-dioxolanes”,Perkin Trans, vol. 1, 2000, pp. 3006-3013, XP001117556.
Griesbaum, Karl, “Diozonides from Coozonolyses of Suitable O-Methyl Oximes and Ketones”,Tetrahedron, Elsevier Science Publishers, Amsterdam, NL, vol. 53, No. 15, Apr. 14, 1997, pp. 5463-5470 XP004105588.
Meshnick, S:“Artemisinin and the Antimalarial Endoperoxides: From Herbal Remedy to Targeted Chemotherapy”,Microbiological Reviews, American Society for Microbiology, Washington, DC, US, vol. 60, No. 2, Jun. 1, 1996, pp. 301-315, XP002052313.

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