Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2006-12-05
2010-11-09
Seaman, D. Margaret (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S153000, C546S159000
Reexamination Certificate
active
07829578
ABSTRACT:
Aromatic ketones having an extended fluoro-alkyl or fluoro-alkoxy moiety are disclosed. In particular aspects, the compounds comprise substituted 9-acridone, 9-xanthone, 4(1H)-quinolone, 4(1H) pyridone, 1,4-naphthoquinone, 9,10-anthraquinone derivatives. These preparations possess potent pharmacological activity for inhibiting malaria and mosquito-borne (Plasmodium) diseases. The haloalkyl/alkoxy aromatic compounds possess significant pharmacological activity, with IC50values in the nanomolar and sub-nanomolar range, and reduced toxicity against host derived cells and tissues. Methods of using the fluoro-alkyl/alkoxy aromatic compounds in the treatment of malaria and other human and animal diseases are also disclosed. Agricultural uses of the fluoro-alkyl/alkoxy aromatic compounds, such as in control of fungal diseases and in the production of important commercial crops (apples, etc.), are also presented.
REFERENCES:
patent: 2647901 (1953-08-01), Archer
patent: 2709171 (1955-05-01), Stoughton
patent: 2732373 (1956-01-01), Steiger
patent: 2732374 (1956-01-01), Steiger
patent: 3981903 (1976-09-01), Hirano et al.
patent: 4250182 (1981-02-01), Gorvin
patent: 5977077 (1999-11-01), Winter et al.
patent: 6248891 (2001-06-01), Sharp et al.
patent: 6541483 (2003-04-01), Michejda et al.
patent: 6613797 (2003-09-01), Winter et al.
patent: 6686469 (2004-02-01), Eberle et al.
patent: 6703388 (2004-03-01), Miyamoto et al.
patent: 2002/0055644 (2002-05-01), Winter et al.
patent: 551 029 (1932-05-01), None
patent: 0 110 298 (1984-06-01), None
patent: WO 2008/064011 (2008-05-01), None
Ambroise-Thomas, P. “Antimalarial vaccines. Disappointments and hopes.”Bull Acad. Natl. Med., (1997), 181: 1637-50.
Atkinson, et al., “Ultrastructure of Malaria-Infected Rrythrocytes,”Blood Cells. (1990) 16: 351-368.
Bojang, et al., “Follow-up of Gambian Children Recruited to a Pilot Safety and Immunogenicity Study of the Malaria Vacinne SPf66,”Parasite Immunology, (1997): 19: 579-81.
Boudreau, et al., “Tolerability of Prophylactic Lariam® Regimens,”Trop. Med. Parasitol, 44, (1993): 257-265.
Brewer, et al., “Factors Relating to Neurotoxicity of Artemisinin Antimalarial Drugs Listening to Arteethe,”Med. Trop., (Mars) (1998), 58: 22-7.
Brewer, et al., “Neurotoxicity in Animals Due to Arteether and Artemether,”Transactions of the Royal Society of Tropical Medicine and Hygiene, (1994), 88 (Supp. 1); S33-6.
Broudy, et al., “Monocytes Stimulate Fibroblastoid Bone Marrow Stromal Cells to Produce Multilineage Hematopoietic Growth Factors,”Blood, (1986) vol. 68, No. 2, 530-534.
Clark, et al., “Developmental Toxicity of Artesunate and an Artesunate Combination in the Rat and Rabbit,” (2004),Birth Defects Research(Part B), 71: 380-394.
Coleman, et al., “Gametocytocidal and Sporontocidal Activity of Antmalarials AgainstPlasmodium berghei ankain ICR Mice andAnopheles stephensiMosquitoes,” (1992),Am. J. Trop. Med. Hyg.46: 169-82.
Croft, et al., “The Activity of Hydroxynaphthoquinones AgainstLeishmania donovani,” (1992),Journal of Antimicrobial Chemotherapy30: 827-832.
Doolan, et al., “DNA Vaccination as an Approach to Malaria Control: Current Status and Stragegies,” (1998),Curr. Top Microbiol. Immunol., 226: 37-56.
Fivelman, et al., “Modified Fixed-Ratio Isobologram Method for Studying in Vitro Interactions between Atovaquone and Progunanil or Dihydroartemisinin Against Drug-Resistant Strains ofPlasmodium falciparum,” (2004),Antimicrob. Agents Chemother., 48: 4097-102.
Fusetti, et al., “Meflochina ed ototossicità: descrizione di tre casi,” (1999)Clin. Ter.150: 379-382.
Guillouzo, André, “Liver Cell Models in in Vitro Toxicology,” (1998),Environ. Health Perspect., 106: (Suppl 2): 511-32.
Hudson, A., “Atovaquone-A Novel Broad-Spectrum Anti-Infective Drug,” (1993),Parasitol Today, 9: 66-8.
Hudson, A., “566C80: A Potent Broad Spectrum Anti-Infective Agent with Activity Against Malaria and Opportunistic Infections in AIDS Patients,” (1991),Drugs Exptl. Clin. Res.XV11(9) 427-435.
Ignatushchenko, et al., “Xanthones as Antimalarial Agents; Studies of a Possible Mode of Action,” (1997),FEBS, Lett., 409: 67-73. X.
Ignatushchenko, et al., “Xanthones as Antimalarial Agents: Stage Secificity,” (2000)Am. J. Trop. Med. Hyg., 62: 77-81.
Kelly, et al., “A Spectroscopic Investigation of the Binding Interactions Between 4,5-dihydroxyxanthone and heme,”Journal of Inorganic Biochemistry86 (2001) 617-625.
Kelly, et al. “Optimization of Xanthones for Antimalarial Activity: the 3,6-Bis-w-Diethylaminoalkoxyxanthone Series,”Antimicrobial Agents and Chemotherapy, 2002, 46: 144-50.
Kelly, et al., “The Kinetics of Uptake and Accumulation of 3,6—bis-ω-diethylamino-amyloxyxanthone by the Human Malaria ParasitePlasmodium falciparum,” (2002),Molecular&Biochemical Parasitology, 123: 47-54.
Kessl, et al., “CytochromebMutations That Modify the Ubiquinol-binding Pocket of the Cytochromebc1Complex and Confer Anti-malarial Drug Resistance inSaccharomyces cerevisiae,” The Journal of Biological Chemistry, (2005), vol. 280, No. 17, Apr. 28, pp. 17142-17148.
Kessl, et al., “Molecular Basisfor Atovaquone Resistance inPneumocystic jiroveciiModeled in the Cytochromebc1Complex ofSaccharomyces cerevisiae,” The Journal of Biological Chemistry, (2004), vol. 279, No. 4, Jan. 23, pp. 2817-2824.
Korsinczky, et al., “Mutations inPlasmodium falciparumCytochromebThat Are Associated with Atovaquone Resistance Are Located at a Putative Drug-Binding Site,”Antimicrobial Agents and Chemotherapy, Aug. 2001, pp. 2100-2108.
Krungkrai, J., “The multiple roles of the mitochondrion of the malarial parasite,”Parasitology, (2004), 129, 511-524.
Learngaramkul, et al., “Molecular Characterization of Mitochondria in Asexual and Sexual Blood Stages ofPlasmodium falciparum,” Molecular Cell Biology Research Communications(1999), 2, 15-20.
Li, et al., “Cryopreserved human hepatocytes: characterization of drug-metabolizing enzyme activities and applications in Higher Throughput Screening Assays for Hapatoxicity, Melabolic Stability, and Drug-Drug Interaction Potential,”Chemical-Biological Interaction(1999), 121, 17-35.
Low, L. K. “Metabolic Changes of Drugs and Related Organic Compounds,” Chapter 3, pp. 43-12 in J. N. Delgado and W.A. Remers (ed.),Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry, 10thedition, (1998) Raven Publishers, Philadelphia.
Luzzi, et al., “Adverse Effects of Antimalarials—An Update,”Drug Safety(1993) 8 (4); 295-311.
Madan, et al., “Effect of Cryopreservation onCytochrome P-450 Enzyme Induction in Cultured Rat Hepatocytes,”Drug Metabolism and Disposition, (1999),Drug Metabolism and Disposition(1999), 27: 327-35.
Makler, et al., “Detection ofPlasmodium falciparumInfection with the Fluorescent Dye, Benzothiocarboxypurine,”Am.J. Trop. Med. Hyg., (1991), 44(1), pp. 11-16 (90-191).
Meshnick, Steven R., “Multiple Cytochrome b Mutation May Cause Atovaquone Resistance,”The Journal of Infectious Diseases, (2005), 44: 11-6.
Milhous, W. K., “Development of New Drugs for Chemoprophylaxis of Malaria,”Med. Trop.(2001), 61: 48-50.
Olliaro, et al., “An Overview of Chemotherapeutic Targets for Antimalarial Drug Discovery,”Pharmacol Ther., (1999), 81: 91-110.
Pessina, et al., “Application of the CFU-GM Assay to Predict Acute Drug-Induced Neutropenia: AnInternational Blind Trial to Validate a Prediction Model for the Maximum Tolerated Dose (MTD) of Myelosuppressive Xenobiotics,”Toxicological Sciences, (2003) 75, 367.
Pessina, et al., “In Vitro Tests for Haematotoxicity: Prediction of Drug-Induced Myelosupresson by the CFU-GM Assay,”A
Hinrichs David J.
Kelly Jane X.
Riscoe Michael K.
Smilkstein Martin J.
Winter Rolf W.
Klarquist & Sparkman, LLP
Oregon Health & Science University
Seaman D. Margaret
U.S. Department of Veterans Affairs
LandOfFree
Aromatic ketones and uses thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Aromatic ketones and uses thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Aromatic ketones and uses thereof will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4243411