Process for the synthesis of bis-aryl diamidoxime compounds

Details Process for the synthesis of bis-aryl diamidoxime compounds Process for the synthesis of bis-aryl diamidoxime compounds

2006-07-04

2006-07-04

Solola, Taofiq (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S074000, C549S491000

Reexamination Certificate

active

07071338

ABSTRACT:
Bis-aryl diamidoxime compounds, such as 2,5-bis [4-hydroxy and 4-O-alkylamidinophenyl] furans, can be prepared from 2,5-bis tri-alkylstannanes via a one step palladium-catalyzed cross reaction. Bis-aryl diamidoxime compounds, such as 2,5-bis [4-hydroxy and 4-O-alkylamidinophenyl]furans, are useful as therapeutic compounds. The disclosed process is scalable, simpler, more economic and more feasible than other presently known methods of preparing 2,5-bis [4-hydroxy and 4-O-alkylamidinophenyl]furans and other bis-aryl diamidoxime compounds.

REFERENCES:
patent: 5594138 (1997-01-01), Dykstra et al.
patent: 5602172 (1997-02-01), Boykin et al.
patent: 5843980 (1998-12-01), Hall et al.
patent: 6025398 (2000-02-01), Hall et al.
patent: 6326395 (2001-12-01), Tidwell et al.
patent: 6423737 (2002-07-01), Hall et al.
patent: 6635668 (2003-10-01), Tidwell et al.
International Preliminary Examination Report corresponding PCT Appl. No. PCT/US03/37788 dated on Jul. 8, 2004.
Ansede et al., “O- Alkoxuamidine Prodrugs of Furamidine: In Vitro Transport and Microsomal Metabolism as Indicators of in Vivo Efficacy in a Mouse Model ofTrypanosoma brucei rhodesienseInfection”,Journal of Medical Chemistry, 47:4335-4338, 2004.
Boykin et al., “Anti-Pneumocystis Activity of Bis-Amidoximes and Bis-O-Alkylamidoximes Prodrugs”,Bioorganic&Medical Chemistry Letters, vol. 6, No. 24, pp. 3017-3020, (1996).
Zhou et al., “Enhanced Permeability of the Antimicrobial Agent 2,5-Bis (4-Amidinophenyl) Furan across Caco-2 Cell Monolayers via Its Methylamidoxime Prodrug”,Pharmaceutical Research, vol. 19, No. 11, pp. 1689-1695, (Nov. 2002).
Anbazhagan et al., “Palladium-Catalyzed N-arylation of O-methylamidoximes”,Elsevier Science Ltd., pp. 4221-4224, (2002).
Das et al., “Synthesis and Antiprotozal Activity of 2,5-Bix (4-guanylphenyl)furans”,Journal of Medicinal Chemistry, vol. 20, No. 4, pp. 531-536, (1977).
Tidwell et al., “Dicationic DNA Minor Grove Binders as Antimicrobial Agents”, inSmall Molecules DNA and RNA Binders: From Synthesis to Nucleic Acid Complexes(Demeunynck et al.,eds.) Wiley-VCH: 416-460, New York, Dec., 2002.

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