CAS: 111406-87-2; 1-(1-(Benzo[b]Thiophen-2-yl)Ethyl)-1-Hydroxyurea

该化合物是一种合成化合物,被归类为脂素合成抑制剂,主要用于治疗哮喘,其作用是抑制对生产利库特里安的欧洲强能煽动性调解器至关重要的酶脂液氧甘油,它有助于肠道收缩和气道炎.Zileuton一般是口服的,以其降低哮喘袭击频率和改善肺功能的能力为名.该物质在水中的溶解性相对较低,并往往被配制为治疗用药片.常见副作用可能包括肝酶升高,胃肠紊乱和头痛.由于其行动机制,Zileuton对患有与过敏触发有关的哮喘症状的病人特别有利.建议治疗期间监测肝功能,因为肝中毒可能发生.总的来说,Zileuton代表一种针对哮喘管理的定向方法,重点是该疾病涉及的炎道.

结构式图片

相似化合物

737800-51-0 22720-75-8 171370-49-3

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

trimethylsilyl is°Cyanate 1-(N-hydroxyamino)-1-(benzothien-2-yl)ethane 22H23NO5SC22H23NO5S thien-2-ylethyl)hydroxylamineN,O-bis(phenoxycarbonyl)-N-(1-benzothien-2-ylethyl)hydroxylamineN-hydroxy-N-(1-benzo[b]thien-2-ylethyl) urea sodium salt(6R,7R)-6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,1-jk][1]-benzazepin-2[1H]-one acetone (6S,7S)-4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methylethyl)amino]imidazo[4,5,1-jk][1]benzazepin-2(1H)-one 5,6-dihydroimidazo[4,5,1-jk][1]benzazepin-2,7-[1H,4H]-dione

合成工艺路线路线简述

    N-[2-(Benzenesulfonyl)-1-(1-Benzothiophen-2-yl)Ethyl]Hydroxylamine置于sodium Amalgam体系中,用 四氢呋喃,水 用作溶剂,化学反应 2.0H,反应生成齐留通
    参考文献:取代杂环的合成.引入n-羟基脲官能团的简单方法
    标题:取代杂环的合成.引入n-羟基脲官能团的简单方法
    摘要:已经开发出一种用于引入n-羟基脲官能团的简单方法.这涉及将羟胺共轭加成到乙烯基砜底物上.该方法已成功用于5-脂氧合酶抑制剂zileuton和a-69412的简便合成.
    Doi:10.1016/0040-4039(94)88063-8

    海关参考信息

    专利信息


    专利号:WO-2025081225-A1
    优先权日:2023-10-17
    标 题 :Synthesis of polyphenols
    发明人:TURLAND CADE LACHLAN; GROLMAN DAVID; BEHRENDORFF JAMES BRUCE YARNTON HAYCOCK; MORADI SHAYLI VARASTEH; THOMSON RAINE ELIZABETH STURT
    权利人:Delica Therapeutics Pty Ltd
    摘要:The present disclosure relates to polyphenols, including flavonoids, flavones and cannflavins, and methods of synthesising polyphenols. The present disclosure provides methods, enzymes and compositions that may be useful in the synthesis of polyphenols.

    专利号:US-8304409-B2
    优先权日:2002-07-03
    标 题:Nitrosated nonsteroidal antiinflammatory compounds, compositions and methods of use
    发明人:EARL RICHARD A; EZAWA MAIKO; FANG XINQIN; GARVEY DAVID S; GASTON RICKY D; KHANAPURE SUBHASH P; LETTS L GORDON; LIN CHIA-EN; RANATUNGE RAMANI R; RICHARDSON STEWART K; SCHROEDER JOSEPH D; STEVENSON CHERI A; WEY SHIOW-JYI
    权利人:EARL RICHARD A; EZAWA MAIKO; FANG XINQIN; GARVEY DAVID S; GASTON RICKY D; KHANAPURE SUBHASH P; LETTS L GORDON; LIN CHIA-EN; RANATUNGE RAMANI R; RICHARDSON STEWART K; SCHROEDER JOSEPH D; STEVENSON CHERI A; WEY SHIOW-JYI; NICOX SA
    摘要:The invention describes novel nitrosated nonsteroidal antiinflammatory drugs (NSAIDs) and pharmaceutically acceptable salts thereof, and novel compositions comprising at least one nitrosated NSAID, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or at least one therapeutic agent. The invention also provides novel compositions comprising at least one nitrosated NSAID, and at least one compound that donates, transfers or releases nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor, stimulates endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase and/or at least one therapeutic agent. The invention also provides novel kits comprising at least one nitrosated NSAID, and, optionally, at least one nitric oxide donor and/or at least one therapeutic agent. The invention also provides methods for treating inflammation, pain and fever; for treating gastrointestinal disorders; for facilitating wound healing; for treating and/or preventing gastrointestinal, renal and/or respiratory toxicities resulting from the use of nonsteroidal antiinflammatory compounds; for treating inflammatory disease states and/or disorders; and for treating and/or preventing ophthalmic diseases and/or disorders.

    专利号:US-2002183366-A1
    优先权日:2001-03-23
    标题:Cyclooxygenase-2 inhibitors, compositions and methods of use
    发明人:GARVEY DAVID S; SCHROEDER JOSEPH D
    摘要:This invention describes novel compounds that are cyclooxygenase 2 (COX-2) selective inhibitors and novel compositions comprising at least one cyclooxygenase 2 (COX-2) selective inhibitor, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or, optionally, at least one therapeutic agent. The invention also provides novel kits comprising at least one COX-2 selective inhibitor, and, optionally, at least one nitric oxide donor, and/or, optionally, at least one therapeutic agent. The novel cyclooxygenase 2 selective inhibitors of the invention can be optionally nitrosated and/or nitrosylated. The invention also provides methods for treating inflammation, pain and fever; for treating and/or improving the gastrointestinal properties of COX-2 selective inhibitors; for facilitating wound healing; for treating and/or preventing renal toxicity or other toxicities; for treating and/or preventing other disorders resulting from elevated levels of cyclooxygenase-2; and for improving the cardiovascular profile of COX-2 selective inhibitors.

    专利号:US-7211598-B2
    优先权日:2002-06-28
    标 题:Oxime and/or hydrozone containing nitrosated and/or nitrosylated cyclooxygenase-2 selective inhibitors, compositions and methods of use
    发明人:GARVEY DAVID S; RANATUNGE RAMANI R; RICHARDSON STEWART K
    权利人:NITROMED INC
    摘要:The invention describes novel cyclooxygenase 2 (COX-2) selective inhibitors having at least one oxime group or hydrazone group and novel compositions comprising at least one cyclooxygenase 2 (COX-2) selective inhibitor having at least one oxime group or hydrazone group, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or at least one therapeutic agent. The invention also provides novel kits comprising at least one COX-2 selective inhibitor having at least one oxime group or hydrazone group, optionally nitrosated and/or nitrosylated, and, optionally, at least one nitric oxide donor, and/or, optionally, at least one therapeutic agent. The novel cyclooxygenase 2 selective inhibitors of the invention having at least one oxime group or hydrazone group can be optionally nitrosated and/or nitrosylated. The invention also provides methods for treating inflammation, pain and fever; for treating and/or improving the gastrointestinal properties of COX-2 selective inhibitors; for facilitating wound healing; for treating and/or preventing renal and/or respiratory toxicity; for treating and/or preventing other disorders resulting from elevated levels of cyclooxygenase-2; and for improving the cardiovascular profile of COX-2 selective inhibitors.

    专利号:US-7244753-B2
    优先权日:2002-07-29
    标 题:Cyclooxygenase-2 selective inhibitors, compositions and methods of use
    发明人:GARVEY DAVID S; KHANAPURE SUBHASH P; RANATUNGE RAMANI R; RICHARDSON STEWART K; SCHROEDER JOSEPH D
    权利人:NITROMED INC
    摘要:The invention describes novel cyclooxygenase 2 (COX-2) selective inhibitors and novel compositions comprising at least one cyclooxygenase 2 (COX-2) selective inhibitor, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or at least one therapeutic agent. The invention also provides novel kits comprising at least one COX-2 selective inhibitor, optionally nitrosated and/or nitrosylated, and, optionally, at least one nitric oxide donor, and/or, optionally, at least one therapeutic agent. The novel cyclooxygenase 2 selective inhibitors of the invention can be optionally nitrosated and/or nitrosylated. The invention also provides methods for treating inflammation, pain and fever; for treating and/or improving the gastrointestinal properties of COX-2 selective inhibitors; for facilitating wound healing; for treating and/or preventing renal and/or respiratory toxicity; for treating and/or preventing other disorders resulting from elevated levels of cyclooxygenase-2; and for improving the cardiovascular profile of COX-2 selective inhibitors.

    专利号:US-5663368-A
    优先权日:1993-07-14
    标 题:Synthesis of acid addition salts of hydroxylamines
    发明人:FLISAK JOSEPH R; ROSS STEPHEN TOREY
    权利人:SMITHKLINE BEECHAM CORP
    摘要:This invention relates to novel diastereomeric acid addition salts of homochiral hydroxylamines, to processes for obtaining such, to processes for the conversion thereof to the corresponding homochiral hydroxylamines, to certain novel homochiral hydroxylamines and the processes for using these as intermediates.
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    主要参考文献


    1: Kuvibidila S, Warrier RP, Haynes J, Baliga SB. Hydroxyurea and Zileuton Differentially Modulate Cell Proliferation and Interleukin-2 Secretion by Murine Spleen Cells: Possible Implication on the Immune Function and Risk of Pain Crisis in Patients with Sickle Cell Disease. Ochsner J. 2015 Fall;15(3):241-7.
    2: Silva BC, de Miranda AS, Rodrigues FG, Malheiros Silveira AL, de Souza Resende GH, Dutra Moraes MF, Pinheiro de Oliveira AC, Parreiras PM, da Silva Barcelos L, Teixeira MM, Machado FS, Teixeira AL, Rachid MA. The 5-lipoxygenase (5-LOX) Inhibitor Zileuton Reduces Inflammation and Infarct Size with Improvement in Neurological Outcome Following Cerebral Ischemia. Curr Neurovasc Res. 2015;12(4):398-403. doi: 10.1248/bpb.b15-00048. doi: 10.3797/scipharm.1402-19. eCollection 2014 Sep.
    6: Gounaris E, Heiferman MJ, Heiferman JR, Shrivastav M, Vitello D, Blatner NR, Knab LM, Phillips JD, Cheon EC, Grippo PJ, Khazaie K, Munshi HG, Bentrem DJ. Zileuton, 5-lipoxygenase inhibitor, acts as a chemopreventive agent in intestinal polyposis, by modulating polyp and systemic inflammation. PLoS One. 2015 Mar 6;10(3):e0121402. doi: 10.1371/journal.pone.0121402. eCollection 2015.

    合成参考文献


    参考文献:10.1016/j.vph.2011.07.003
    摘要:Chen L, Zhao Q, Wang XL, You R, Zhang YH, Ji H, Lai YS. ZLJ-6, a novel COX/5-LOX inhibitor, attenuates TNF-α-induced endothelial E-selectin, ICAM-1 and VCAM-1 expression and monocyte-endothelial interactions via a COX/5-LOX-independent mechanism. Vascul Pharmacol. 2011 Nov;55(5-6):135–42. doi: 10.1016/j.vph.2011.07.003.
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