Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2007-07-09
2010-06-29
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...
C514S314000, C514S408000, C514S438000, C514S471000, C514S491000, C548S577000, C549S071000, C549S472000, C549S491000
Reexamination Certificate
active
07745456
ABSTRACT:
The present invention relates to novel 2,5-bis{[alkyl (or aryl) imino] aminophenyl}furans and thiophenes of the general formulain which R1, R2, R3and R4are each independently selected from the group consisting of H, alkyl, alkoxy, halide, and alkylhalide groups; R5is H, alkyl or aryl; R6is H, alkyl, aryl, or NR7R8, in which R7and R8are each independently selected from the group consisting of H, alkyl and aryl; and X is O, S or NR9, in which R9is H or alkyl, and to the use of such compounds.
REFERENCES:
patent: 5594138 (1997-01-01), Dykstra et al.
patent: 6737440 (2004-05-01), Boykin et al.
patent: 7241795 (2007-07-01), Boykin et al.
patent: 7256203 (2007-08-01), Boykin et al.
patent: 2002/0156098 (2002-10-01), Werbovetz et al.
patent: 2003/0083362 (2003-05-01), Boykin et al.
patent: 2004/0235927 (2004-11-01), Boykin et al.
patent: 2007/0072877 (2007-03-01), Dykstra et al.
patent: WO2002/36588 (2002-05-01), None
patent: WO2002/055025 (2002-07-01), None
patent: WO2002/057224 (2002-07-01), None
patent: WO2003/017994 (2003-03-01), None
Apted, F.I.C., Present status of chemotherapy and chemopropylaxis of human trypanosomiasis in the Eastern Hemisphere.Pharmacology Ther. vol. 11, No. 2 pp. 391-413 (1980).
Australian Examiners Report corresponding to Australian Patent Application No. 2002246600 dated May 13, 2005.
Bailly et al., Relationships between topoisomerase II inhibition, sequence-specificity and DNA binding mode of dicationic diphenylfuran derivatives.Anti-Cancer Drug Design. vol. 14 pp. 47-60 (1999).
Bell, C.A., et al., Structure-Activity Relationships of Analogs of Pentamidine against Plasmodium falciparum and Leishmania mexicana amazonensis.Antimicrobial Agents and Chemotherapy. vol. 34, No. 7 pp. 1381-1386 (1990).
Bell, C.A., et al., Structure-Activity Relationships of Pentamidine Analogs against Giardia lamblia and Correlation of Antigiardial Activity with DNA-Binding Affinity.Antimicrobial Agents and Chemotherapy. vol. 35, No. 6 pp. 1099-1107 (1991).
Bell, C.A., et al., Structure-Activity Studies of Dicationically Substituted Bis-Benzimidazoles against Giardia lamblia: Correlation of Antigiardial Activity with DNA Binding Affinity and Giardial Topoisomerase II Inhibition.Antimicrobial Agents and Chemotherapy. vol. 37, No. 12 pp. 2668-2673 (1993).
Blagburn et al., Dicationic Furans Inhibit Development of Cryptosporidium Parvum in HSD/ICR Suckling Swiss Mice.Journal of Parasitology. vol. 84, No. 4 pp. 851-856 (1998).
Blagburn, et al., Inhibition of Cryptosporidium parvum in Neonatal Hsd: (ICR)BR Swiss Mice by Polyether Ionophores and Aromatic Amidines.Antimicrobial Agents and Chemotherapy. vol. 35, No. 7 pp. 1520-1523 (1991).
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).
Boykin, D.W., et al., Dicationic Diarylfurans as Anti-Pneumocystis carinii Agents.Journal of Medicinal Chemistry. vol. 38 pp. 912-916 (1995).
Bryceson, A.D.M., et al., Visceral leishmaniasis unresponsive to antimonial drugs II. Response to high dosage sodium stibogluconate or prolonged treatment with pentamidine.Transactions of the Royal Society of Tropical Medicine&Hygiene. vol. 79, No. 5 pp. 705-714 (1985).
Collins, L., et al., Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycrobacterium avium.Antimicrobial Agents and Chemotherapy. vol. 41, No. 5 pp. 1004-1009 (1997).
Communication pursuant to Article 96(2) EPC corresponding to European Patent Application No. 01 994 174.9-2117 dated Jan. 15, 2007.
Correspondence from foreign patent attorney regarding Official Action corresponding to Japanese Patent Application No. 2002-557905 dated Apr. 22, 2008.
Das, B.P., et al., Synthesis and Antiprotozoal Activity of 2,5-Bis(4-guanylphenyl)furans.Journal of Medicinal Chemistry. vol. 20, No. 4 pp. 531-536 (1977).
Del Poeta, M., et al., In-vitro activity of dicationic aromatic compounds and fluconazole against Cryptococcus neoformans and Candida spp.Journal of Antimicrobial Chemotherapy. vol. 44 pp. 223-228 (1999).
Dykstra, C.C., et al., Selective Inhibition of Topoisomerases from Pneumocystis carinii Compared with That of Topoisomerases from Mammalian Cells.Antimicrobial Agents and Chemotherapy. vol. 38, No. 9 pp. 1890-1898 (1994).
European Search Report for corresponding European Application No. 01994174.9 dated Jan. 10, 2005.
Fitzgerald, D.J., et al., Selective Nucleosome Disruption by Drugs That Bind the Minor Groove of DNA.The Journal of Biological Chemistry. vol. 274, No. 38 pp. 27128-27138 (1999).
Francesconi, I., et al., 2,4-Diphenyl Furan Diamidines as Novel Anti-Pneumocystis carinii Pneumonia Agents.Journal of Medicinal Chemistry. vol. 42 pp. 2260-2265 (1999).
Fulton, J.D., The course of Plasmodium relictum infection in canaries and treatment of bird and monkey malaria with synthetic bases.Annals of Tropical Medicine and Parasitology. vol. 34 pp. 53-66 (1940).
Guerri, A., et al., Visualisation of extensive water ribbons and networks in a DNA minor-groove drug complex.Nucleic Acids Research. vol. 26, No. 12 pp. 2873-2878 (1998).
Henderson et al., Molecular struggle for transcriptional control.Nature Medicine. vol. 1, No. 6 pp. 525-527 (1995).
Hughes, W.T., et al., Efficacy of Trimethoprim and Sulfamethoxazole in the Prevention and Treatment of Pneumocystis carinii Pneumonitis.Antimicrobial Agents and Chemotherapy. vol. 5, No. 3 pp. 289-293 (1974).
Ivady, V.G., et al. Ein neues behandlungsverfahren der interstitiellen plasmazelligen pneumonie ruhgeborener mit funfwertigem stibium und aromatischen diamidinen.Monatschr. Kinderheilkd., vol. 106 pp. 10-14 (1958).
King, H., et al., Studies in chemotherapy: XIX. Further report on new trypanocidal substances.Annals of Tropical Medicine and Parasitology. vol. 32, pp. 177-192 (1938).
Kirk, R., et al., The use of certain aromatic diamidines in the treatment of Kala-azar.Annals of Tropical Medicine and Parasitology. vol. 34 pp. 181-197 (1940).
Kravtsov et al., The19F NMR Spectra of Some Fluoroaryl Mercurials and the Electronic Effect of Mercury Substituents.Journal of Organometallic Chemistry. vol. 36 pp. 227-237 (1972).
Kumar et al., Palladium Catalyzed Cross-Coupling Reactions for the Synthesis of 2.5-Disubstitutedfurans.Hetercyclic Communications. vol. 5 pp. 301-304 (1999).
Laughton et al., A Crystallographic and Spectroscopic Study of the Complex between d(GCGCAATTCGCG)2and 2,5-Bis(4-guanylphenyl)furan, an Analogue of Berenil. Structural Origins of Enhanced DNA-Binding Affinity.Biochemistry. vol. 35, No. 18 pp. 5655-5661 (1996).
Lindsay, D.S. et al., Activity of Pentamidine and Pentamidine Analogs against Toxoplasma gondii in Cell Cultures.Antimicrobial Agents and Chemotherapy. vol. 35, No. 9 pp. 1914-1916 (1991).
Ling et al., Models for Intramolecular Exchange in Organic π-Conjugated Open-Shell Systems: 3-Nitrenophenyl and 4-Nitrenophenyl Units Connected by 2,5-Furandiyl, 2,5-Thiophenediyl, and 2,5-Pyrrolediyl Nonalternant Exchange Linkers.Journal of the American Chemical Society. vol. 116 pp. 8784-8792 (1994).
Lourie, E.M. et al., Studies in chemotherapy: XXI. The trypanocidal action of certain aromatic diamidines.Annals of Tropical Medicine and Parasitology. vol. 33 pp. 289-304 (1939).
Lourie, E.M. et al., Studies in Chemotherapy: XXII. The Action of Certain Aromatic Diamidines on Babesia Canis Infections of Puppies.Annals of Tropical Medicine and Parasitology. vol. 33 pp. 305-312 (1939).
Mazur et al., A thermodynamic and structural analysis of DNA minor-groove complex formation.Journal of Molecular Biology. vol. 300, No. 2 pp. 321-337 (2000).
Notice of Allowance corresponding to U.S. Appl. No. 10/008,535 dated Jan. 2, 2004.
Notice of Allowance corresponding to U.S. Appl. No. 10/791,425 dated Apr. 3, 2007.
Notification of Transmittal of the International Search Report or the Declaration corresponding to International Patent Application No. PCT/US01/47238 dated Sep. 11, 2002.
Official Action corresponding to a Canadian Patent Application No. 2,425,135 dat
Boykin David W.
Perfect John R.
Stephens Chad F.
Tidwell Richard R.
Wilson W. David
Duke University
Georgia State University Research Foundation, Inc.
Jenkins Wilson Taylor & Hunt, P.A.
Sackey Ebenezer
The University of North Carolina at Chapel Hill
LandOfFree
Synthesis and antimicrobial activity of novel dicationic... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Synthesis and antimicrobial activity of novel dicationic..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis and antimicrobial activity of novel dicationic... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4195904