Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heavy metal containing doai
Reexamination Certificate
2006-02-07
2006-02-07
Nazario-Gonzalez, Porfirio (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heavy metal containing doai
C556S071000, C556S077000, C556S078000, C556S080000, C424S629000
Reexamination Certificate
active
06995188
ABSTRACT:
Arsenic trioxide, an inorganic compound, is commercially available anti-cancer agent but it carries significant toxicity. Organic arsenicals, on the other hand, are much less toxic, to the extent that the methylation of inorganic arsenic in vivo into organic arsenicals has been considered a detoxification reaction. New organic arsenic derivatives have been synthesized, including S-dimethylarsino-glutathione, S-dimethylarsino-thiosuccinic acid and S-dimethylarsino-thiobenzoic acid, and established its potent in vitro cytotoxic activity against numerous human tumor cell lines, both of solid and hematological origin, as well as against malignant blood cells from patients with leukemia. Results form a basis for the development of S-dimethylarsino-glutathione, S-dimethylarsino-thiosuccinic acid, S-dimethylarsino-thiobenzoic acid, and other organic arsenicals as an anti-cancer therapy, combining high efficacy with very low, if any, toxicity.
REFERENCES:
patent: 6191123 (2001-02-01), Uckun et al.
patent: 2004/0028750 (2004-02-01), Lu
patent: 1002537 (1998-10-01), None
patent: WO 99/24029 (1998-11-01), None
American Conference of Governmental Industrial Hygienists, Inc. (ACGIH). Arsenic and soluble compounds, including arsine. Documentation of the Threshold Limit Values and Biological Exposure Indices, sixth edition, 1991.
Bachleitner-Hofmann et al., “Arsenic trioxide and ascorbic acid: synergy with potential implications for the treatment of acute myeloid leukaemia,”Br. J. Haematol., 112(3):783-786, 2001.
Banks et al., “Biomolecules bearing the S- or SeAsMe2 function: amino acid and steroid derivatives,”J. Medicinal Chem. 22:572-575, 1979.
Beliles, “The Metals,” InPatty's Industrial Hygiene and Toxicology, fourth editionG.D. Clayton and F.E. Clayton, eds. John Wiley & Sons, Inc.: New York. pp. 1913-1925, 1994.
Calleja and Warrell, “Differentiating agents in pediatric malignancies: all-trans-retinoic acid and arsenic in acute promyelocytic leukemia,”Curr. Oncol. Rep., 2:519-523, 2000.
Chen et al., “6-thio- and —seleno-alpha-D-glucose esters of dimethylarsinous acid,”Carb. Res. 50:53-62, 1976.
Chen et al., “Synthesis of 1-and 6-S-and 1-and 6-Se-derivatives of 2-amino-2-deoxy-alpha/beta-D-glucopyranose,”J. Chemical Soc, Perkin Trans. 1:2287-2293, 1980.
Cuzick et al., “Medicinal arsenic and internal malignancies,”Br. J. Cancer, 45:904-911, 1982.
Daniel and Zingaro “Dimethylarsinous acid esters of 1-thio- and -seleno- galactose. A new class of potential carcinostatic agents,”Phosphorus and Sulfur4:179-185, 1978.
Forkner and McNair-Scott, “Arsenic as a therapeutic agent in chronic myeloid leukemia,”JAMA97(1):3-6, 1931.
Geissler et al., “In vivo effects of arsenic trioxide in refractory acute myeloid leukemia other than acute promyelocytic leukemia,”Blood94:4230a. 1999.
Goyer, “Toxic effects of metals” InCasarett and Doull's Toxicology: The Basic Science of Poisons, 5thedition. C.D. Klassen, ed, McGraw-Hill: New York. pp. 691-698, 1996.
Grignani et al., “The acute promyelocytic leukemia-specific PML-RAR alpha fusion protein inhibits differentiation and promotes survival of myeloid precursor cells,”Cell, 74:423-431, 1993.
Hughes and Kenyon, “Dose-dependent effects on the disposition of monomethylarsonic acid and dimethylarsinic acid in the mouse after intravenous administration,”J. Toxicol. Environ. Health, 53(2):95-112, 1998.
IARC. Some metals and metallic compounds. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. vol. 23:39-141, 1980.
Kitamura et al., “New retinoids and arsenic compounds for the treatment of refractory acute promyelocytic leukemia: clinical and basic studies for the next generation,”Cancer Chemother Pharmacol., 40 (Suppl):S36-S41, 1997.
Knock et al., “The use of selected sulfhydryl inhibitors in a preferential drug attack on cancer,”Surg. Gynecol. Obstet. 133:458-466, 1971.
König, A. et al., “Comparative activity of melarsoprol and arsenic trioxide in chronic B-cell leukemia lines,”Blood90:562-570, 1997.
Lallemand-Breitenbach et al., “Retinoic acid and arsenic synergize to eradicate leukemic cells in a mouse model of acute promyelocytic leukemia,”J. Exp. Med., 189:1043-1052, 1999.
Mountain et al., “Chemotherapy studies in an animal tumor spectrum: II. Sensitivity of tumors to fourteen antitumor chemicals,”Cancer Res. 26:181-206, 1966.
Rivi et al., “Organic arsenical melarsoprol shows growth suppressive activity via programmed cell death on myeloid and lymphoid leukemia derived cell lines,”Blood(Suppl.) 88:68a, 1996.
Rosenthal and Zingaro, “The synthesis and characterization of thio sugar esters of diorganylarsinous acids,”Phosphorus and Sulfor9:107-116, 1980.
Rousselot et al., “Use of arsenic trioxide (As2O3) in the treatment of chronic myelogenous leukemia: In vito and in vivo studies,”Blood94:4457a, 1999.
Soignet et al., “Clinical study of an organic arsenic melarsoprol, in patients with advanced leukemia,”Cancer Chemother. Pharmacol. 44:471-421, 1999.
Soignet et al., “Dose-ranging and clinical pharmacologic study of arsenic trioxide in patients with advanced hematologic cancers,”Blood94:1247a, 1999.
Tallman, “Therapy of acute promyelocytic leukemia: all-tans retinoic acid and beyond,”Leukemia, 12 (Suppl 1):S37-S40, 1998.
Wiernik et al., “Phase II trial of arsenic trioxide (As2O3) in patients with relapsed/refractory acute myeloid leukemia, blast crisis of CML or myelodysplasia,”Blood94:2283a, 1999.
Zhang et al., “Arsenic trioxide treated 72 cases of acute promyelocytic leukemia,”Chin. J. Hematol. 17:58-62, 1996.
Aslanidis et al., “Methylarsino-substituted hydroxy carboxylate esters,”Chemiker-Zeitung, 112(4):125-127, 1988.
Beckermann and Bernhard, “Determination of monovethylarsonic acid and dimethylarsinic acid by derivatization with thioglycolic acid methyl ester and gas-liquid chromatographic separation,”Analytica Chimica Acta, 135(1):77-84, 1982.
Cullen et al., “The metabolism of methylarsine oxide and sulfide,”Applied Organometallic Chemistry, 3(1):71-78, 1989.
Cullen et al., “The reaction of methylarsincals with thiols: some biological implications,” J. Inorganic Biochemistry, 21(3):179-194, 1984.
Emran et al., “Synthesis and biodistribution of radioarsenic labeled dimethylarsinothiols: derivatives of pennicillamine and mercaptoethanol,”International Journal of Nuclear Medicine and Biology, 11(3-4):259-261, 1984.
Hosain et al., “Synthesis of radioarsenic labeled dimethylchloroarsine for derivation of a new group of radiopharmceuticals,”International Journal of Applied Radiation and Isotopes, 33(12):1477-1478, 1982.
Ionov et al., “Reaction of tertiary arsine sulfides with alkyl chlorocarbonates,”Zhurnal Obshchei Khimii, 46(11):2555-2558, 1976.
Kala et al., “The MRP2/cMOAT transporter and arsenic-glutathione complex formation are required for bilary excretion of arsenic,”J. Biol. Chem., 275(43):33404-33408, 2000.
King and Ludford, “Relation between the constitution of arsenicals and their action on cell division,”Journal of the Chemical Society Abstracts, 2086-2088, 1950.
Lam et al., “Spectroscopic studies of arsenic (III) binding toEscherichia coliRI methyltransferase and to two mutants, C223S and W183F,”Biochemistry, 31(43):10438-10442, 1992.
Lin et al., “Methylarsenicals and arsinothiols are potent inhibitors of mouse liver thioredoxin reductase,”Chemical Research in Toxicology, 12(10):924-930, 1999.
Mester et al., “Specification of dimethylarsinic acid and monomethylarsonic acid by gas chromatography-mass spectrometry,”Journal of Chromatography, 832(1+2):183-190, 1999.
Schoene et al., “
Duzkale Hatice
Freireich Emil J.
Kantarjian Hagop
Sotelo-Lerma Merida
Verstovsek Srdan
Board of Regents , The University of Texas System
Fish & Neave IP Group Ropes & Gray LLP
Nazario-Gonzalez Porfirio
The Texas A&M University System
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