Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2011-06-21
2011-06-21
Wilson, James O (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S255000
Reexamination Certificate
active
07964619
ABSTRACT:
Disclosed herein are novel dicationic teraryl compounds and their aza analogues, including compounds of Formula (IIe):wherein p and q are each 0 and each A, Y and Z is CR4. An exemplary compound of Formula (IIe) is:Methods for combating microbial infections, such as parasiticLeishmaniaspecies, with novel dicationic terphenyl compounds and their aza analogues are included. Processes for synthesizing novel dicationic terphenyl compounds and their aza analogues are disclosed along with methods for evaluation of the compounds as potential anti-protozoan agents.
REFERENCES:
patent: 5521189 (1996-05-01), Boykin et al.
patent: 5550295 (1996-08-01), Hillhouse
patent: 5628984 (1997-05-01), Boucher, Jr.
patent: 2002/0082267 (2002-06-01), Gerusz et al.
patent: 2003/0119803 (2003-06-01), Stranix et al.
patent: 2005/0119481 (2005-06-01), Rehwinkel et al.
patent: 2005/0148646 (2005-07-01), Boykin et al.
patent: 2006/0293328 (2006-12-01), Tidwell et al.
patent: 2007/0037813 (2007-02-01), Aliagas-Martin et al.
patent: 2007/0037814 (2007-02-01), Rawson et al.
patent: 2007/0105858 (2007-05-01), Mabire et al.
patent: 2007/0197549 (2007-08-01), Johansson et al.
patent: 2007/0232586 (2007-10-01), Ohmoto et al.
patent: 1 736 466 (2006-12-01), None
patent: WO96/40138 (1996-12-01), None
patent: WO 2004/050018 (2004-06-01), None
patent: WO2005/025565 (2005-03-01), None
patent: WO 2005/033065 (2005-04-01), None
patent: WO2005/040132 (2005-05-01), None
Jordan, V. C. Nature Reviews: Drug Discovery, 2, 2003, p. 205.
Dörwald, F. Zaragoza. Side Reactions in Organic Synthesis: A Guide to Successful Synthesis Design, Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA, 2005, Preface.
Ashley, J. N., et al. A chemotherapeutic comparison of the trypanocidal action of some aromatic diamidines.Journal of the Chemical Society. pp. 103-116 (1942).
Bailly, C., et al., Relationship between topoisomerase II inhibition, sequence-specificity and DNA binding mode of dicationic diphenylfuran derivatives.Anti-Cancer Drug Design, vol. 14, No. 1, pp. 47-60 (1999).
Bouteille, B., et al., Treatment perspectives for human trypanosomiasis.Fundamental Clinical Pharmacology. vol. 17, pp. 171-181 (2003).
Boykin, D. W., et al., Dicationic Diarylfurans as Anti-Pneumocystis Carinii Agents.Journal of Medicinal Chemistry, vol. 38, pp. 912-916 (1995).
Boykin, D. W., et al., 2,5-Bis[4-(N-alkylamidino)phenyl]furans as Anti-Pneumocystis carinii Agents.Journal of Medicinal Chemistry, vol. 41, pp. 124-129 (1998).
Cory, M., et al., Structure and DNA Binding Activity of Analogues of 1,5-Bis(4-amidinophenoxy)pentane (Pentamidine).Journal of Medicinal Chemistry, vol. 35, pp. 431-438 (1992).
Czarny, A. D., et al., Analysis of van der Waals and Electrostatic Contributions in the Interactions of Minor Groove Binding Benzimidazoles with DNA.Journal of American Chemical Society, vol. 117, No. 16, pp. 4716-4717 (1995).
Dann, O., et al., Trypanocide Diamidine Mit Drei Isolierten Ringsystemen.Justus Liebigs Annalen der Chemie, pp. 160-194 (1975).
Das, B. P. and Boykin, D. W., Syntheis and Antiprotozoal Activity of 2,5-Bis(4-guanylphenyl)furans.Journal of Medicinal Chemistry, vol. 20, No. 4, pp. 531-536 (1976).
Das, B. P., et al., Synthesis and Antitrypanosomal Activity of Some Bis(4-guanylphenyl) Five- and Six-Membered Ring Heterocycles.Journal of Medicinal Chemistry, vol. 23, No. 5, pp. 578-581 (1980).
Dykstra, C. C., et al., Selective Inhibition of Topoisomerases fromPneumocystis cariniiCompound with That of Topoisomerases from Mammalian Cells.Antimicrobial Agents and Chemotherapy., vol. 38, No. 9, pp. 1890-1898 (1994).
European Search Report corresponding to European Patent Application No. 08150205.6-1211 dated Jul. 2, 2008.
Fairlamb, A. H., Chemotherapy of human African trypanosomiasis: current and future prospects.Trends in Parasitology, vol. 19, No. 11, pp. 488-494 (2003).
Fitzgerald, D. J. and J. N. Anderson, Selective Nucleotide Disruption by Drugs That Bind in the Minor Groove of DNA.The Journal of Biological Chemistry., vol. 274, No. 38, pp. 27128-27138 (1999).
Henderson, D. and L. H. Hurley, Molecular struggle for transcriptional control.Nature Medicine, vol. 1, pp. 525-527 (1995).
Hu et al., Azaterphenyl Diamidines as Antileishmanial Agents.Bioorganic&Medicinal Chemistry Letters, vol. 18, No. 1, pp. 247-251 (2008).
Ismail, M. A., et al. Synthesis and Antiprotozoal Activity of Aza-Analogues of Furamidine.Journal of Medicinal Chemistry, vol. 46, No. 22. pp. 4761-4769 (2003).
Ismail, M. A., et al., Synthesis, DNA Affinity, and Antiprotozoal Activity of Linear Dications: Terphenyl Diamidines and Analogues.Journal of Medicinal Chemistry. vol. 49, No. 17, pp. 5324-5332 (Aug. 24, 2006).
Kumar et al., Synthesis of dicationic diarylpyridines as nucleic-acid binding agents.European Journal of Medicinal Chemistry, vol. 30, No. 2, pp. 99-106 (1995).
Mazur, S. F., et al., A Thermodynamic and Structural Analysis of DNA Minor-Groove Complex Formation.Journal of Molecular Biology, vol. 300, pp. 321-337 (2000).
Office Communication corresponding to U.S. Appl. No. 11/436,045 dated Oct. 31, 2007.
Office Communication corresponding to U.S. Appl. No. 11/436,045 dated Jan. 24, 2008.
Office Communication corresponding to U.S. Appl. No. 11/436,045 dated Oct. 3, 2008.
Published Patent Application corresponding to Chinese Patent Application No. 20081000859.2 dated Sep. 24, 2008.
Shaikh, S. A., et al., A molecular thermodynamic view of DNA-drug interactions: a case study of 25 minor-groove binders.Archives of Biochemistry and Biophysics, vol. 429, No. 1, pp. 81-99 (2004).
Steck, E. A., et al.Leishmania donovani, Plasmodium berghei, Trypanosoma rhodesiense: Antiprotozoal Effects of Some AmidineTypes.Experimental Parasitology. vol. 52, No. 3. pp. 404-413 (1981).
Stephens, C. E., et al. The Activity of Diguanidino and ‘Reversed’ Diamidino 2,5-Diarylfurans versusTrypanosoma cruziandLeishmania donovani. Bioorganic and Medicinal Chemistry Letters, vol. 13, pp. 2065-2069 (2003).
Tidwell, R. R., Dicationic DNA Minor Groove Binders as Antimicrobial Agents.Small Molecule DNA and RNA Binders: From Synthesis to Nucleic Acid Complexes. vol. 2, pp. 414-460 (2003).
Wilson, W. D., et al., Nucleic Acid Interaction of Unfused Aromatic Cations: Evaluation of Proposed Minor-Groove, Major-Groove, and Intercalation Binding Modes.Journal of American Chemical Society, vol. 120, No. 40, pp. 10310-10321 (1998).
Garner, et al., The Benefits of Artemisinin Combination Therapy for Malaria Extend Beyond the Individual Patient.PLoS Medicine. vol. 2, No. 4 pp. 0287-0288 (2005).
Schmid, Caecilia, 10-Day Melarsoprol Treatment ofTrypanosoma bruceiGambiense Sleeping Sickness: From Efficacy to Effectiveness. Doctoral Dissertation. Universitat Basel (2004).
Altman et al., “Phenotypic Analysis of Antigen-Specific T Lymphocytes,” Science. vol. 274 pp. 94-96 (1996).
Ansede et al., “O-Alkoxyamidine Prodrugs of Furamidine: In Vitro Transport and Microsomal Metabolism as Indicators of in Vivo Efficacy in a Mouse Model ofTrypanosoma bruceiRhodesiense Infection,” J. Med. Chem. vol. 47 pp. 4335-4338 (2004).
Boykin et al., “Anti-Pneumocystis Activity of Bis-amidoximes and Bis-O-alkylamidoximes Prodrugs,” Bioorganic and Medicinal Chemistry Letters. vol. 6 p. 3017-3020 (1996).
Brun et al., “In Vitro Typanocidal Activities of NewS-Adenosylmethionine Decarboxylase Inhibitors,” Antimicrobial Agents and Chemotherapy. vol. 40, No. 6 pp. 1442-1447 (1996).
Ellingson et al., “Bromination of 2-amino-3-carbomethoxypyrazine,” Journal of the Amercian Chemical Society. vol. 71 pp. 2798-2800 (1949).
Hall et al., “Anti-PneumocystisActivity of Aromatic Diamidoxine Prodrugs,” Antimicrobial Agents and Chemotherapy. vol. 42, No. 3 pp. 666-674 (1998).
Jampilek et al., “Novel regioselective preparation of 5-chloropyrazine-2-carbonitrile from pyrazine-2-carboxamide and coupling study of substituted phenylsulfanylpyrazine-2-carboxylic acid derivatives,” Current Organic Chemistry. vol. 9, No. 1 pp. 49-60 (2005).
Kumar et al.,
Arafa Reem K.
Boykin David W.
Brun Reto
Hu Laixing
Ismail Mohamed A.
Georgia State University Research Foundation, Inc.
Jenkins Wilson Taylor & Hunt, P.A.
The University of North Carolina at Chapel Hill
Willis Douglas M
Wilson James O
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