Sinomenine derivatives and preparation and uses thereof

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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C546S074000

Reexamination Certificate

active

07932264

ABSTRACT:
The present invention relates to the preparation and pharmacological use of sinomenine derivatives of formula I. The approach disclosed herein is the modification of D ring by-substituting for R. Additional substitutions in the other rings are also provided herein. Several of the sinomenine derivatives have significantly greater anti-inflammation activity when compared with the parent compound.

REFERENCES:
patent: 6372756 (2002-04-01), Christians et al.
patent: 7144710 (2006-12-01), Guyre et al.
patent: 2003/0215885 (2003-11-01), Guyre et al.
patent: 1153171 (1997-07-01), None
patent: 200680047418.1 (2008-06-01), None
patent: 101578101 (2009-11-01), None
patent: 06847694.4 (2008-06-01), None
patent: 1959956 (2008-08-01), None
patent: 2008-5458 (2008-06-01), None
patent: 2009519960 (2009-05-01), None
patent: WO 2004/048340 (2004-06-01), None
patent: WO 2007/070703 (2007-06-01), None
Liu, Liang; “Inhibition of lymphocyte proliferation by the anti-arthritic drug sinomenine.” International Journal of Immunopharmacology, 16(8), 685-91 1994 (abstract only).
Fang, Yongfei; “Effects and mechanism of sinomenine on signal transduction of synovial cell nuclear factor-κB in rats with adjuvant arthritis.” Zhongguo Linchuang Kangfu, 9(7), 204-205 2005 (abstract only).
Dorwald F. A. Side Reactions in Organic Synthesis, 2005, Wiley: VCH, Weinheim p. IX of Preface.
Candinas et. al. “Immunomodulatory Effects of the Alkaloid Sinomenine in the High Responder ACI-to-Lewis Cardiac Allograft Model 1” Transplantation Dec. 27, 1996 vol. 62(12), pp. 1855-1860.
PCT International Search Report issued Oct. 2, 2007 for NatureMed Group Corporation et al., International App'l No. PCT/US2006/048086, filed Dec. 15, 2006.
PCT Written Opinion of the International Searching Authority issued Oct. 2, 2007 for NatureMed Group Corporation et al., International App'l No. PCT/US2006/048086, filed Dec. 15, 2006.
Ju et al., 2010, “Protective Effect of Sinomenine on Cartilage Degradation and Chondrocytes Apoptosis”, Yakugaku Zasshi, vol. 130(8): 1053-1060.
Ou et al., 2010, “Sinomenine Reduces Invasion and Migration Ability in Fibrolast-like Synoviocytes Cells Co-cultured with activated human monocytic THP-1 cells by Inhibiting the Expression of MMP-2, MMP-9, CD147”, Rheumatol Int., Epub ahead of print.
Li et al., 2010, “Sinomenine, theophylline, cysteine, and levamisole: Comparisons of their kinetic effects on mineral formation induced by matrix vesicles”, J. Inorg Biochem, vol. 104(4): 446-454.
Li et al., 2010, “Development of Patch and Spray Formulations for Enhancing Topical Delivery of Sinomenine Hydrochloride”, J. Pharm. Sci. vol. 99(4): 1790-1799.
Ou et al., 2009, “Sinomenine Reduces Invasion and Migration Ability in Fibrolast-like Synoviocytes Cells Co-cultured with activated human monocytic THP-1 cells by Inhibiting the Expression of MMP-2, MMP-9, CD147”, Acta Pharmacol. Sin., vol. 30(4):435-441.
Zhou et al., 2008, “Sinomenine Ameliorates Arthritis via MMPs, TIMPs, and Cytokines in Rats”, Biochemical and Biophysical Research Communications, vol. 376(2):352-357.
Xu et al., 2008, “Sinomenine versus NSAIDs for the Treatment of Rheumatoid Arthritis: a Systematic Review and Meta-Analysis”, Planta Med., vol. 74(12):1423-1429.
Deng et al., 2008, “pH-dependent, Steroselective Dimerization of Sinomenine”, Org Left., vol. 10 (17):3879-3882.
Deng et al., 2008, “Biocatalyzed Cross-Coupling of Sinomenine and Guaiacol by Antrodiella”, Org Lett., vol. 10 (6):1119-1122.
Wang et al., 2007, “Voltammetric Determination of Sinomenine in Biological Gluid Using a Glassy Carbon Electrode Modified by a Composite Film of Polycysteic Acid and Carbon Nanotudes”, Comb Chem. High Throughput Screen, vol. 10(7):595-603.
Wang et al., 2007, “Sinomenine Inhibits Activation of rat retinal microglia induced by advanced glycation end products”, Int. Immunopharmacol., vol. 7(12).1552-1558.
Kok et al., 2005, “The Anti-angiogenic Effect of Sinomenine”, Angiogenesis, vol. 8(1):3-12.
Liu et al., 2005, “Influence of Co-Administered Sinomenine on Pharmacokinetic Fate of Paeoniflorin in Unrestrained Conscious Rats”, J. Ethnopharmacol., vol. 99(1):61-67.
Zhang et al., 2009, “Research Advances of Mechanism of Sinomenine in Treating Rheumatoid Arthritis”, Journal of Chinese Integrative Medicine, vol. 7(8): 775-778. (w/English abstract).
Yu et al., 2009, “Effect of Sinomenine on the Expression of Chemokines and Chemokine Receptors in Dendritic Cells from Patients with Rheumatoid Arthritis”, Nan Fang Yi Ke Da Xue Xue Bao, vol. 29(4): 635-637. (abstract only).
Liu et al., 2005, “Immunopharmacological Action of Sinomenine, and Alkaloid Isolated from Sinomenium Acutum, and its Mechanism of action in Treating Rheumatoid Arthritis”, Yao Xue Xue Bao, vol. 40(2):127-131. (abstract only).
Tu et al., 1999, “Effect of Sinomenine on IL-8, IL-6, IL-2 Produced by Peripheral Blood Mononuclear Cells”, J. Tongji. Med. Univ., vol. 19(4):257-259.
Wang et al., 2002, “Study Progress in Sinomenine Acutum(Tunb.) Rehd. Et Wils”, Zhong Yao Cai, vol. 25(3): 209-211. (abstract only.
Okuda, et al., 1995, A Case of Drug Eruption Cause by the Crude Drug Boi (Sinomenium stem/Sinomeni Caulk et Rhizoma), Journal of DEmatology, vol. 22 (10):795-800. (abstract only).
Yamasaki, et al., 1976, “Pharmacology of Sinomenine, an Anti-Rheumatic Alkaloid from Sinomenium Acutum”, Acta. Med. Okayama., vol. 30(1):1-20.
Tang et al., Sep. 2006, “Synthesis and anti-Inflammatory activities investigation of sinomenine derivatives on ring”, C. Nat Prod Res. vol. 20(11):1015-23.
Ye et al., Mar. 2004, “Synthesis and anti-inflammatory analgesic activities of sinomenine derivatives”, Yao Xue Xue Bao, vol. 39(3):180-3. (w/English Abstract).
Chernoff et al., 1995, “A Randomized, Controlled Trial of IL-10 in Humans: Inhibition of Inflammatory Cytokine Production and Immune Responses”, The Journal of Immunology, vol. 154:5492-5499.
Diterich et al., Jul. 2003, “Borrelia Burgdorferi-Induced Tolerance as a Model of Persistence via Immunosupression”, Infection and Immunity, vol. 71(7):3979-3987.
Hamper et al., 1996, “Solid-Phase Synthesis of Proline Analogs via a Three Component 1,3-Dipolar Cycloaddition”, Tetrahedron Letters, vol. 37(21):3671-3674.
Hartman et al., 1995, “The effects of anti-inflammatory and antiallergic drugs on cytokine release after Stimulation of Human Whole Blood by Lipopolysaccharide and Zymosan A”, lnflamm. Res. vol. 44:269-274.
Hartung et al., 1995, “Effect of Granulocyte Colony-Stimulating Factor Treatment on Ex Vivo Blood Cytokine Response in Human Volunteers”, Blood, vol. 85(9):2482-2489.
Hartung et al., 2000, “Blood Cytokine Response of Low-Dose Molgramostim (rhGM-CSF)-Treated Patients”, Cytokine, vol. 12(10).1570-1574.
Hermann et al., 2003, “A Model of Human Whole Blood Lymphokine Release for in Vitro and ex Vitro Use”, Journal of Immunological Methods, vol. 275: 69-79.
Hitotsuyanagi et al., 1995, “Synthesis of Antitumor Morphinane Alkaloids, Sinococuline and 6-epi-, 7-epi-, and 6-epi-7-epi-Sinococuline, from Sinomenine”, Journal of Organic Chemistry, vol. 60:4549-4558.
Lagrelius et al., 2006, “Cytokine Detection by Multiplex Technology Useful for Assessing Antigen Specific Cytokine Profiles and Kinetics in Whole Blood Cultured up to Seven Days”, Cytokine, vol. 33:156-165.
Zhang et al., 2004, “Characterization of (2R, 3S)-2-({[4-(2-butynyloxy)phertyl]sulfonyl})-N,3-dihydroxybutanamide, a potent and selective inhibitor of TNF-α Converting Enzyme”, International Immunopharmacology, vol. 4:1845-1857.
Zhang et al., 2004, “Identification and Characterization of 4-[|4-(2-Butynyloxy)phenyl]sulfnoyl-N-hydroxy-2,2-dime

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