KMST isoeugenol derivatives and pharmaceutical activity

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

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C544S394000

Reexamination Certificate

active

06887878

ABSTRACT:
A compound having the following formula I:where R1is an alkyl group or an alkenyl group, X representsR2is selected from the group consisting of a halogen (o, m, p) group such as F, Cl, Br or I, —NH2, —NO2and a hydrogen group, R3is a hydrogen group or OH. The compound has pharmacologically α2-adrenergic/5-HT2Aantagonist activity, 5-HT re-uptake activity, and anti-oxidant activity. The compound is produced by preparing 4-epoxy isoeugenol, mixing piperazine dissolved in methanol with the 4-epoxy isoeugenol to reflux at 100° C. for approximately 2 to approximately 6 hours, removing the methanol, passing the mixture through a silica gel column chromatography after the removing step, eluting the passed mixture with n-hexane and ethyl acetate, drying the eluted mixture, and crystallizing the dried mixture with methanol.

REFERENCES:
patent: 966493 (1964-08-01), None
Gupta et al. Arzneim.-Forsch./Drug Res. 28(1), p. 241-246 (1978).*
Dunn et al., Bibliographic record of “The reductions in sweetened milk intake induced byinterleukin-1 and endotoxin are not prevented by chronic antidepressant treatment,” http://www.hint.org.tw/cgi-bin/ovidweb/ovidweb.cgi., 2001.
Girard et al., “A New Synthetic Flavonoid Protects Endothelium Derived Relaxing Factor-induced Relaxation in Rabbit Arteries in Vitro: Evidence for Superoxide Scavenging,” Biochemical Pharmacology, vol. 49, No. 10, pp. 1553-1539, 1995.
Altavilla et al., “The Lazaroid, U-74389G, inhibits inducible nitric oxide synthase activity, reverses vascular failure and protects against endotoxin shock,”European Journal of Pharmacology, vol. 369, pp. 49-55, 1999.
Aubriot et al., “New Series of Aryloxpropanolamines with Both Human β3-Adrenoceptor Agonistic Activity and Free Radical Scavenging Properties ,” Bioorganic&Medical Chemistry Letters, vol. 12, pp. 209-212, 2002.
Cohen et al., “Evidence that Blood Pressure Reduction by Serotonin Antagonists is Related to Alpha Receptor Blockade in Spontaneously Hypertensive Rats,” Hypertension vol. 5, No. 5, pp. 676-681, Sep.-Oct., 1983.
Correa et al., “Central α1-Adrenoceptors Mediate the Pressor Response to Intracerebroventricular Injection of Noradrenaline in Unanesthetized Rats,” Neuropharmacology vol. 34, No. 7, pp. 793-798, 1995.
Curro et al., “Interaction Between Alpha Adrenergic and Serotonergic Activation of Canine Saphenous Veins,” The Journal of Pharmacology and Experimental Therapeutics vol. 207, pp. 936-949, 1978.
Diaz-Cabiale et al., “Galanin/alpha2-receptor interactions in central cardiovascular control,” Neuropharmacology vol. 39, pp. 1377-1385, 2000.
Dobrucki et al., “Central Hypotensive Action of Clonidine Requires Nitric Oxide,” Circulation, vol. 104, pp. 1884-1886, Oct. 16, 2001.
Duan et al., “Enhancement of Clonidine-Induced Analgesia by Lesions Induced with Spinal and Intracerbroventricular Administration of 5, 7-Dihydroxytryptamine,” Neuropharmacology vol. 26, No. 4, pp. 323-329, 1987.
Duka et al., “Role of the Postsynaptic α2-adrenergic receptor subtypes in catecholamine-induced vasoconstriction,” General Pharmacology vol. 34, pp. 101-106, 2000.
Elenkov et al., “Modulation of lipopolysaccharide-induced tumor necrosis factor-αproduction by selective α-and β-adrenergic drugs in mice,” Journal of Neuroimmunology vol. 61, pp. 123-131, 1995.
Fujimoto et al., “Denopamine as an α1H-adrenoceptor antagonist in isolated blood vessels,” European Journal of Pharmacology vol. 280, pp. 143-147, 1995.
Glaser et al., Bibliographic record of “Stress depresses interferon production by leukocytes concomitant with a decrease in natural killer cell activity, ”http://www.int/org.tw/cgi-bin/ovidweb/ovidweb/cgi.
Hasko et al., “Differential effect of selective block of α2-adrenoreceptors on plasma levels of tumour necrosis factor-α, interleukin-6 and corticosterone induced by bacterial lipopolysaccharide in mice,” Journal of Endocrinology vol. 144, pp. 457-462, 1995.
Hasko et al., “Differential effect of selective block of α2-adrenoreceptors on plasma levels of tumour necrosis factor-α, interleukin-6 and corticosterone induced by bacterial lipopolysaccharide in mice,” Journal of Endocrinology vol. 144, pp. 457-462, 1995.
Hatanaka et al., “Biochemical Profile of YM992, a Novel Selective Serotonin Reuptake Inhibitor with 5-HT2AReceptor Antagonistic Activity,” Neuropharmacology vol. 35, No. 11, pp. 1621-1626, 1996.
Helmeste et al., “Inhibitation of Platelet Serotonin Uptake by Cytochrome P450 Inhibitors Miconazole and Econazole,” Life Sciences vol. 62, No. 24, pp. 2203-2208, 1998.
Hirata et al., “Effects of endothelin receptor antagonists on endothelin-1 and inducible nitric oxide synthase genes in a rat endotoxic model,” Clinical Science, pp. 332-335, 2002.
Huang et al., “Inhibitory effect of DCDC on lipopolysaccharide-induced nitric oxide synthesis in RAW 264.7 cells,” Life Sciences vol. 68, pp. 2435-2447, 2001.
Huang et al., “Ferulidiol : A Vasodilatory and Antioxidant Adrenoceptor and Calcium Entry Blocker, with Ancillary β2-Agonist Activity,” Drug Development Research 47:77-89 (1999).
Huang et al., “A New Aspect of View in Synthesizing New Type β-adrenoceptor Blockers with Ancillary Antioxidant Activities,” Bioorganic & Medicinal Chemistry vol. 9, pp. 1739-1746, 2001.
Ko et al., “β-Blocker Therapy and Symptoms of Depression, Fatigue, and Sexual Dysfunction,” JAMA vol. 288, No. 3, pp. 351-357, Jul. 17, 2002.
Koyama, “Participation of central α-receptors on hemodynamic response to E. Coil endotoxin,” American Journal Physiology vol. 247, pp. R655-R662, 1984.
Krege et al., “Affinity of trazodone for human penileα1--and α2-adrenoceptors,” BJU International vol. 85, pp. 959-961, 2000.
Kubo et al., “Cardiovascular effects in rats of alpha1and alpha2adrenergic agen injected into the nucleus tractus solitarii,” Naunyun-Schmiedeberg's Archives of Pharmacology vol. 335, pp. 274-277, 1987.
Lin et al., “Systemic Administration of Lipopolysaccharide Induces Release of Nitric Oxide and Glutamate and c-fos Expression in the Nucleus Tractus Solitarii of Rats,” Hypertension 33:1218-1224, 1999.
Llado et al., “The α2-adrenoceptor antagonist idazoxan is an agonist at 5-HT1Aautoreceptors modulating serotonin synthesis in the rat brainin vivo”, Neuroscience Letters vol. 218, pp. 111-114, 1996.
Loegering et al., “The Antioxidant, U74389, Ameliorates the Depression of Vascular Reactivity Caused by Lipopolysaccharide”, Life Sciences, vol. 57, No. 20, pp. 321-326, 1995.
Maitra et al., “Alterations in Tissue Glucose Uptake During the Hyperglycemic and Hypoglycemic Phases of Sepsis”, Hock vol. 13, No. 5, pp. 379-385, 2000.
Molina-Holgado et al., “Endotoxin Administration Induced Differential Neurochemical Activation of the Rat Brain Stem Nuclei,” Brain Research Bulletin, vol. 40, No. 3, pp. 151-156, 1996.
Murphy et al., “Characterization of Alpha-2 Adrenergic Receptors in the OK Cell, an Opossum Kidney Cell Line,” The Journal of Pharmacology and Experimental Therapeutics vol. 244, No. 2, pp. 571-578, 1987.
Nickola et al., “Antidepressant Drug-Induced Alterations in Neuron-Localized Tumor Necrosis Factor-αmRNA and α2-Adrenergic Receptor Sensitivity,” The Journal of Pharmacology and Experimental Therapeutics vol. 297, No. 2, pp. 680-687, 2001.
Owens et al., “Neurotransmitter Receptor and Transporter Binding Profile of Antidepressants and Their Metabolites,” The Journal of Pharmacology and Experimental Therapeutics vol. 283, No. 3, pp. 1305-1322, 1997.
Pitzalis et al., “Depression but not anxiety influence

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