CAS: 473727-83-2; (R)-2-Hydroxy-N,N-Dimethyl-3-((2-((1-(5-Methylfuran-2-yl)Propyl)Amino)-3,4-Dioxocyclobut-1-En-1-yl)Amino)Benzamide

该化合物是一个复杂的有机化合物,具有多功能结构特征.它具有一种苯丙胺核心,经过一种氢氧组和二甲基氨基组的修改,有助于其潜在的生物活动.二氧代基的环丁混合物的存在增加了其再活动性,并可能影响其与生物目标的相互作用.此外,加入一个呋喃环可能具有芳香相互作用的潜力,这在药物设计和分子识别方面可能具有重要意义.(R)配置表明的立体化学可能影响化合物的药理特性,包括其对特定受体或酶的结合性,选择性.

结构式图片

上下游产品

(R)-1-(5-methylfuran-2-yl)propan-1-amine 3-((2-ethoxy-3,4-diox°Cyclobut-1-en-1-yl)amino)-2-hydroxy-N,N-dimethylbenzamide 3-amino-2-hydroxy-N,N-dimethylbenzamide 5-Methylfurfural

合成工艺路线路线简述

    📜3-[(2-乙氧基-3,4-二氧代-1-环丁基-1-氨基]-2-羟基-N,N-二甲基-苄胺,1-(5-甲基呋喃-2-基)丙胺置于1-(5-甲基呋喃-2-基)丙胺体系中,用90的收率获得产物sch 527123; 3-[[3-[(二甲基氨基)羰基]-2-羟基苯基]氨基]-4-[[(R)-1-(5-甲基呋喃-2-基)丙基]氨基]-3-环丁烯-1,2-二酮
    参考文献:J. Med. Chem. 2006,49,7603-7606
    标题:J. Med. Chem. 2006,49,7603-7606

    海关参考信息

    专利信息


    专利号:US-8519168-B2
    优先权日:2007-07-03
    标 题 :Process and intermediates for the synthesis of 1,2-substituted 3,4-dioxo-1-cyclobutene compounds
    发明人:FU XIAOYONG; GUENTER FRANK BRUNO; KIM-MEADE AGNES S; MATTHEWS KENNETH STANLEY; MAUST MATHEW THOMAS; MCALLISTER TIMOTHY L; WERNE GERALD; WINTERS JASON L; YIN JIANGUO; ZHANG SHUYI
    权利人:FU XIAOYONG; GUENTER FRANK BRUNO; KIM-MEADE AGNES S; MATTHEWS KENNETH STANLEY; MAUST MATHEW THOMAS; WERNE GERALD; WINTERS JASON L; YIN JIANGUO; ZHANG SHUYI; MOLOZNIK DAVID J; MERCK SHARP & DOHME
    摘要:This application discloses a novel process for the preparation of 1,2-substituted 3,4-dioxo-1-cyclobutene compounds, which have utility, for example, in the treatment of CXC chemokine-mediated diseases, and intermediates useful in the synthesis thereof.

    专利号:US-8207221-B2
    优先权日:2004-01-30
    标 题:Crystalline polymorphs of a CXC-chemokine receptor ligand
    发明人:HU MENGWEI; YU YOUNONG; DWYER MICHAEL P; TAVERAS ARTHUR G; KIM-MEADE AGNES; YIN JIANGUO; FU XIAOYONG; MCALLISTER TIMOTHY L; ZHANG SHUYI; KLOPFER KEVIN
    权利人:HU MENGWEI; YU YOUNONG; DWYER MICHAEL P; TAVERAS ARTHUR G; KIM-MEADE AGNES; YIN JIANGUO; FU XIAOYONG; MCALLISTER TIMOTHY L; ZHANG SHUYI; KLOPFER KEVIN; SCHERING CORP
    摘要:The present invention relates to four distinct crystalline polymorphs of a monohydrate of Compound A having the following chemical structure: n n n n n n n n n n These four polymorphic forms, herein referred to as Forms I, II, III and IV are active as a CXC-chemokine receptor ligands. The invention is further directed to formulations, methods of treatment, and processes of synthesis of these polymorphic forms.

    专利号:US-7910775-B2
    优先权日:2003-04-18
    标题 :Synthesis of 2-Hydroxy-N,N-dimethyl-3-[[2-[[1(R)-(5-methyl-2-furanyl)propyl]amino]-3,4-dioxo-1-cyclobuten-1-yl]amino]benzamide
    发明人:YIN JIANGUO; FU XIAOYONG; ZHANG SHUYI; MCALLISTER TIMOTHY L; KIM-MEADE AGNES S; WINTERS JASON L; SUDHAKAR ANANTHA; SCHUMACHER DORIS P
    权利人:SCHERING CORP
    摘要:Disclosed is a process for making the compound of formula I: n nusing the compounds of formulas II, Q, and XI or XII:n n nwherein A is selected from the group consisting of Br, Cl and I (with Br being preferred); and R represents (C 1 -C 10 )alkyl. Also disclosed are intermediate compounds that are made in the disclosed process.

    专利号:US-2006205961-A1
    优先权日:2003-04-18
    标 题:Synthesis of 2-hydroxy-N,N-dimethyl-3-[[2-(1(R)-(5-methyl-2-furany)propyl]amino]-3,4-dioxo-1-cyclobuten-1-yl]amino]benzamide

    专利号:US-2009048458-A1
    优先权日:2003-04-18
    标题:Synthesis of 2-hydroxy-n,n-dimethyl-3-[[2-[[1(r)-(5-methyl-2-furanyl)propyl]amino]-3,4-dioxo-1-cyclobuten-1-yl]amino]benzamide

    专利号:EP-1615903-A2
    优先权日:2003-04-18
    标 题:Synthesis of 2-hydroxy-n,n-dimethyl-3- [[ 2-[ 1(r)-(5-methyl-2-furanyl)propyl] amino] -3,4-dioxo-1-cyclobuten- 1-yl] amino benzamide

    供应商参考报价(招募中)

    品牌试剂参考报价(招募中)

    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Mladic M, Scholten DJ, Niessen WM, Somsen GW, Smit MJ, Kool J. At-line coupling of LC-MS to bioaffinity and selectivity assessment for metabolic profiling of ligands towards chemokine receptors CXCR1 and CXCR2. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 1;1002:42-53. doi: 10.1016/j.jchromb.2015.08.004. Epub 2015 Aug 10. doi: 10.1164/rccm.201405-0992OC. doi: 10.1016/j.cyto.2015.01.002. Epub 2015 Feb 4. doi: 10.1586/1744666X.2014.894886. Epub 2014 Mar 29. doi: 10.1089/adt.2013.553. Epub 2014 Feb 28. doi: 10.1016/S2213-2600(13)70080-8. Epub 2013 May 31. doi: 10.1016/j.intimp.2013.05.029. Epub 2013 Jun 19. Safety and efficacy of a CXCR2 antagonist in patients with severe asthma and sputum neutrophils: a randomized, placebo-controlled clinical trial. Clin Exp Allergy. 2012 Jul;42(7):1097-103. doi: 10.1111/j.1365-2222.2012.04014.x. doi: 10.1016/j.intimp.2012.04.008. Epub 2012 May 2. doi: 10.1158/1535-7163.MCT-11-0915. Epub 2012 Mar 5. doi: 10.1182/blood-2011-05-347393. Epub 2011 Sep 7.
    12: Varney ML, Singh S, Li A, Mayer-Ezell R, Bond R, Singh RK. Small molecule antagonists for CXCR2 and CXCR1 inhibit human colon cancer liver metastases. Cancer Lett. 2011 Jan 28;300(2):180-8. doi: 10.1016/j.canlet.2010.10.004. Epub 2010 Oct 29.
    13: Salchow K, Bond ME, Evans SC, Press NJ, Charlton SJ, Hunt PA, Bradley ME. A common intracellular allosteric binding site for antagonists of the CXCR2 receptor. Br J Pharmacol. 2010 Apr;159(7):1429-39. doi: 10.1111/j.1476-5381.2009.00623.x. Epub 2010 Mar 3.

    合成参考文献


    摘要:S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
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