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

2008-05-13

2008-05-13

Desai, Rita (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C549S336000

Reexamination Certificate

active

07371778

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), Zitter et al.
patent: 5216175 (1993-06-01), Avery et al.
patent: 5219880 (1993-06-01), Thornfeldt
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), Lal 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.
patent: 6825230 (2004-11-01), Vennerstrom et al.
patent: 6906205 (2005-06-01), Vennerstrom
Stephen M. Bebge, Lyle D. Bighley and Donald C. Monkhouse “Pharmaceutical Salts” Journal of Pharmaceutical Sciences, 1977, 66, 1-19.
Wolff, Manfred E. “Burger's Medicinal Chemistry, 5ed, Part I”, John Wiley & Sons, 1995, pp. 975-977.
Banker, G.S. et al, “Modern Pharmaceutics, 3ed.”, Marcel Dekker, New York, 1996, pp. 451 and 596.
Carlos Franco-Paredes, José Ignacio Santos-Preciado “Problem pathogens: prevention of malaria in travelers” Lancet Infectuous Diseases 2006, 6, 139-49.
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-Blcyclo ′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-medlated 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.

Affiliated with

Also associated with

Rating

Spiro and dispiro 1,2,4-trioxolane antimalarials does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Spiro and dispiro 1,2,4-trioxolane antimalarials, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Spiro and dispiro 1,2,4-trioxolane antimalarials will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2769243