Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2011-05-31
2011-05-31
Loewe, Sun Jae Y (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S247000
Reexamination Certificate
active
07951827
ABSTRACT:
Novel dicationic 3,5-diphenylisoxazole compounds are described. Synthetic routes to these novel compounds are provided. Several of the compounds displayed in vitro activity versusTrypanosoma brucei bruceiandPlasmodium falciparumcomparable to that of furamidine. A majority of the novel compounds also were less toxic to VERO cells than furamidine.
REFERENCES:
patent: 5628984 (1997-05-01), Boucher, Jr.
patent: 6706754 (2004-03-01), Werbovetz et al.
patent: 2007/0021483 (2007-01-01), Chalifour et al.
patent: 2007/0088067 (2007-04-01), Tidwell et al.
patent: WO 96/40138 (1996-12-01), None
patent: WO02/36588 (2002-05-01), None
patent: WO03/103598 (2003-12-01), None
patent: WO 2005/025565 (2005-03-01), None
patent: WO2005/033065 (2005-04-01), None
Patrick et al., “Synthesis and in vitro antiprotozoal activities of dicationic 3,5-diphenylisoxazoles”, J. Med. Chem. 2007, 50, 2468-2485.
Partial European Search Report corresponding to European Patent Application No. 06009279.8 dated Aug. 1, 2006.
Dann et al.Trypanocide diamidine mit drei isolierten ringsystemen Justus Liebigs Annalen der Chemie. Verlag Chimie HMBH. Weinheim, DE, 1975, pp. 160-194 [Abstract in English].
Office Communication corresponding to an EP Application No. 06009279.8-2117 dated Feb. 15, 2007.
Bell et al. Structure-Activity Relationships of Analogs of Pentamidine AgainstPlasmodium falciparumandLeishmania mexicanaamazonensis.Antimicrobial Agents and Chemotherapy, vol. 34, No. 7, (1990), pp. 1381-1386.
Bell et al. Structure-Activity Relationships of Pentamidine Analogs againstGiardia lambliaand Correlation of Antigiardial Activity with DNA-Binding Affinity.Antimicrobial Agents and Chemotherapy, vol. 35, No. 6, (1991), pp. 1099-1107.
Blagburn et al. Inhibition ofCryptosporidium parvumin Neonatal Hsd:(ICR)BR Swiss Mice by Polyether Ionophores and Aromatic Amidines.Antimicrobial Agents and Chemotherapy, vol. 35, No. 7, (1991), pp. 1520-1523.
Boykin et al. 2,5-Bis[4-(N-alkylamidino)phenyl]furans as Anti-Pneumocystis cariniiAgents.Journal of Medicinal Chemistry, vol. 41, (1998), pp. 124-129.
Boykin et al. Dicationic Diarylfurans and Anti-Pneumocystis cariniiAgents.Journal of Medicinal Chemistry, vol. 38, (1995), pp. 912-916.
Das et al. Synthesis and Antiprotozoal Activity of 2,5-Bis(4-guanylphenyl)furans.Journal of Medicinal Chemistry, vol. 20, No. 4, (1977), pp. 531-536.
Del Poeta et al. In Vitro Antifungal Activities of a Series of Dication-Substituted Cabazoles, Furans, and Benzimidazoles.Antimicrobial Agents and Chemotherapy, vol. 42, No. 10, (1998), pp. 2503-2510.
Del Poeta et al. In-vitro activity of dicationic aromatic compounds and fluconazole againstCryptococcus neoformansandCandida. ssp.Journal of Antimicrobial Chemotherapy, vol. 44, (1999), pp. 223-228.
Del Poeta et al. Structure-in Vitro Activity Relationships of Pentamidine Analogues and Dication-Substituted Bis-Benzimidazoles as New Antifungal Agents.Antimicrobial Agents and Chemotherapy, vol. 42, No. 10, (1998), pp. 2495-2502.
Francesconi et al. 2,4-Diphenyl Furan Diamidines as Novel Anti-Pneumocystis cariniiPneumonia Agents.Journal of Medicinal Chemistry, vol. 42, (1999), pp. 2260-2265.
Ismail et al. Synthesis and Antiprotozoal Activity of Aza-Analogues of Furamidine.Journal of Medicinal Chemistry, vol. 46, No. 22, (2003), pp. 4761-4769.
Kumar et al. Palladium Catalyzed Cross-Coupling Reactions for the Synthesis of 2.5-disubstitutedfurans.Hetercyclic Communications, vol. 5, (1999), pp. 301-304.
Lindsay et al. Activity of Pentamidine and Pentamidine Analogs againstToxoplasma gondiiin Cell Cultures.Antimicrobial Agents and Chemotherapy, vol. 35, No. 9, (1991), pp. 1914-1916.
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-Pyffolediyl Nonaltemant Exchange Linkers.Journal of American Chemical Society, vol. 116, (1994), pp. 8784-8792.
Shearer et al. S-2-Naphthylmethyl Thioacetimidate Hydrobromide: A New Odorless Reagent for the Mild Synthesis of Substituted Acetamidines.Tetrahedron Letters, vol. 38, (1997), pp. 179-182.
Stephens et al. Diguanidino and “Reversed” Diamindino 2,5-Diarylfurans asn Antimicrobial Agents.Journal of Medicinal Chemistry, vol. 44, (2001), pp. 1741-1748.
Thompson et al. A General Synthesis of 5-Arylnicotinates.Journal of Organic Chemistry, vol. 49, (1984), pp. 5237-5243.
Trent et al. Targeting the Minor Groove of DNA: Crystal Structures of Two Complexes Between Furan Derivatives of Berenil and the DNA Dodecamer d(CGCGAATTCGCG)2.Journal of Medicinal Chemistry, vol. 39, No. 23, (1996), pp. 4554-4562.
Anbazhagan et al. Synthesis of metabolites of the prodrug 2, 5-bis(4-O-Methoxyamidinophenyl) furan.Heterocycles, vol. 60, No. 5, (2003), pp. 1133-1145.
Baumstark et al. A carbon-13 Nmr Assignment study of 3,5-diarylisoxazoles.Journal of Heterocylic Chemistry, vol. 17, (1980), pp. 1719-1721.
Bergeron et al. Total synthesis of (±)-15-deoxyspergualin.Journal of Organic Chemistry, vol. 52, (1987), pp. 1700-1703.
Chrisope et al. Substituent effects in heterocyclic systems by carbon-13 nuclear magnetic resonance. Isoxazoles.Journal of Heterocyclic Chemistry, vol. 18, No. 4, (1981), pp. 795-798.
Friedman et al. Dimethylformamide as a useful solvent in preparing nitriles from aryl halides and cuprous cyanide; improved isolation techniques.Journal of Organic Chemistry, vol. 26, (1961), pp. 2522-2524.
Ismail et al. Synthesis and antiprotozoal activity of aza-analogues of furamidine.Journal of Medicinal Chemistry, vol. 46, (2003), pp. 4761-4769.
Maduskuie et al. Rational design and synthesis of novel, potent Bis-phenylamidine carboxylate factor Xa inhibitors.Journal of Medicinal Chemistry, vol. 41, (1998), pp. 53-62.
Miyatake et al. New poly(arylene ether)s with pendant phosphonic acid groups.Journal of Polymer Science Part A: Polymer Chemistry, vol. 39, No. 21, (2001), pp. 3770-3779.
Moriya et al. Dehydrochlorination of hydroximic acid chlorides by the use of organotin compounds: an application for synthesis of isoxazolines and isoxazoles.Journal of the Chemical Society, Chemical Communications, (1991), pp. 17-18.
Moriya et al. Generation of nitrile oxides via O-tributylstannyl aldoximes; application to the synthesis of isoxazolines and isoxazoles.Journal of the Chemical Society, Perkin Transactions 1, (1994), pp. 413-417.
Popat et al. Synthesis and biological activity of 3-aryl-5-(3′-bromo/chlorophenyl) isoxazoles.Journal of Indian Chemical Society, vol. 80, (2003), pp. 707-708.
Rutan et al. On the preparation of aryl nitriles using tosyl cyanide.Journal of Organic Chemistry, vol. 60, (1995), pp. 2948-2950.
Suman et al. Synthesis and antifungal acrivity of 1,3-bis(4-methyl/4-bromo/3-nitrophenyl) propan-1, 3-diones and their 2-[(4-bromo/4-chloro/2-nitro/2-ethoxy/2, 4-dichlorophenyl)azo] analogs.Indian Journal of Chemistry, vol. 34B, (1995), pp. 743-746.
Sunshine et al. Preparation of linear m-polyphenyls from mono- and dichalcones.Journal of Organic Chemistry, vol. 28, No. 10, (1963), pp. 2517-2522.
Thomsen et al. Synthesis of simple quinoline alkaloids. A novel quinazoline synthesis.Acta Chemica Scandinavica, (B), (1998), pp. 319-313.
Tschaen et al. An improved procedure for aromatic cyanation.Synthetic Communications, vol. 24, No. 6, (1994), pp. 887-890.
Communication pursuant to Article 94(3) EPC corresponding to European Patent Application No. 06 009 279.8-2117 dated Jul. 9, 2008.
Ashley et al., “A Chemotherapeutic Comparison of the Trypanocidal Action of Some Aromatic Diamidines,” J. Chem. Soc. pp. 103-106 (1942).
Das et al., “Synthesis and Antitrypanosomal Activity of Some Bis(4-guanylphenyl) Five- and Six-Membered Ring Heterocycles,” Journal of Medicinal Chemistry. vol. 23 pp. 578-581 (1980).
Office Communication corresponding to European Patent Application No. 06 009 279.8-2117 dated Jul. 1, 2009.
Tidwell, R.R., and Boykin D.W., “Dicationic DNA Minor Groove Binders as Antimicrobial Agents”, in Small Molecule DNA + RNA Binde
Bakunov Stanislav
Bakunova Svetlana M.
Patrick Donald A.
Tidwell Richard R.
Jenkins Wilson Taylor & Hunt, P.A.
Loewe Sun Jae Y
The University of North Carolina at Chapel Hill
LandOfFree
Synthesis and antiprotozoal activity of 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 antiprotozoal activity of dicationic..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis and antiprotozoal activity of dicationic... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2633017