Sch527123 | 473727-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Sch527123
• 英文别名: 2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide；2-hydroxy-N,N-dimethyl-3-[[2-[1-(5-methylfuran-2-yl)propylamino]-3,4-dioxocyclobuten-1-yl]amino]benzamide
• CAS: 473727-49-0
• 化学式: C₂₁H₂₃N₃O₅
• 分子量: 397.431
• InChiKey: RXIUEIPPLAFSDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  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 以 乙醇 为溶剂， 生成 Sch527123
  参考文献：
  名称：

  Synthesis and structure–activity relationships of heteroaryl substituted-3,4-diamino-3-cyclobut-3-ene-1,2-dione CXCR2/CXCR1 receptor antagonists

  摘要：

  Comprehensive SAR studies were undertaken in the 3,4-diaminocyclobut-3-ene-1,2-dione class of CXCR2/CXCR1 receptor antagonists to explore the role of the heterocycle on chemokine receptor binding affinities, functional activity, as well as oral exposure in rat. The nature of the heterocycle as well as the requisite substitution pattern around the heterocycle was shown to have a dramatic effect on the overall biological pro. le of this class of compounds. The furyl class, particularly the 4-halo adducts, was found to possess superior binding affinities for both the CXCR2 and CXCR1 receptors, functional activity, as well as oral exposure in rat versus other heterocyclic derivatives. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.024

文献信息

• N-SUBSTITUTED-DIOXOCYCLOBUTENYLAMINO-3-HYDROXY-PICOLINAMIDES USEFUL AS CCR6 INHIBITORS
  申请人：Pfizer Inc.

  公开号：US20200095239A1

  公开（公告）日：2020-03-26

  The present invention relates to N-substituted-dioxocyclobutenylamino-3-hydroxy-picolinamide compounds of Formulae (IA and 1B) or a pharmaceutically acceptable salt or hydrate thereof, that inhibit CC chemokine receptor 6 (CCR6), pharmaceutical compositions containing these compounds, and the use of these compounds for treating or preventing diseases, conditions, or disorders ameliorated by inhibition of CCR6.

  本发明涉及式(IA和1B)所示的N-取代-二氧环丁烯基氨基-3-羟基-吡咯烷酰胺化合物或其药用可接受盐或水合物，这些化合物抑制CC趋化因子受体6 (CCR6)，包含这些化合物的药物组合物，以及使用这些化合物来治疗或预防通过抑制CCR6而改善的疾病、状况或失调。
• Synthesis of 2-hydroxy-N,N-dimethyl-3-[[2-[1(R)-(5-methyl-2-furanyl)propyl]amino]-3,4-dioxo-1-cyclobuten-1-l]aminobenzamide
  申请人：Schering Corporation

  公开号：US20040209946A1

  公开（公告）日：2004-10-21

  Disclosed is a process for making the compound of formula I: 1 using the compounds of formulas II, Q, and XI or XII: 2 wherein 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.

  揭示了制备化合物I的过程： 使用化合物II、Q和XI或XII的公式： 其中A选自Br、Cl和I的组，其中Br为首选；R代表(C1-C10)烷基。还揭示了在所述过程中制备的中间化合物。
• [EN] PROCESS FOR CONTROLLED CRYSTAL SIZE IN 1,2-SUBSTITUTED 3,4-DIOXO-1-CYCLOBUTENE COMPOUNDS<br/>[FR] PROCÉDÉ POUR OBTENIR UNE TAILLE DE CRISTAUX CONTRÔLÉE DANS DES COMPOSÉS 3,4-DIOXO-1-CYCLOBUTÈNE 1,2-SUBSTITUÉS
  申请人：SCHERING CORP

  公开号：WO2009005802A1

  公开（公告）日：2009-01-08

  This application discloses a novel process for the preparation 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, which has utility, for example, in the treatment of CXC chemokine-mediated diseases.

  该应用程序披露了一种新颖的制备2-羟基-N，N-二甲基-3-[[2-[[1(R)-(5-甲基-2-呋喃基)丙基]氨基]-3,4-二氧杂环丁-1-基]氨基]苯甲酰胺的方法，该方法在治疗CXC趋化因子介导的疾病中具有实用性。
• [EN] PROCESS AND INTERMEDIATES FOR THE SYNTHESIS OF 1,2-SUBSTITUTED 3,4-DIOXO-1-CYCLOBUTENE COMPOUNDS<br/>[FR] PROCÉDÉ ET INTERMÉDIAIRES DE SYNTHÈSE DE COMPOSÉS DE 3,4-DIOXO-1-CYCLOBUTÈNE 1,2-SUBSTITUÉS
  申请人：SCHERING CORP

  公开号：WO2009005801A1

  公开（公告）日：2009-01-08

  This application discloses a novel process for the preparation of 1.2 - substituted 3, 4 - dioxo - 1 - cyclobutene compounds of formula (A), which have utility, for example, in the treatment of CXC chemokine -mediated diseases, and intermediates useful in the synthesis thereof.

  该应用程序披露了一种新颖的制备1,2-取代3,4-二氧基-1-环丁烯化合物（A）的过程，该化合物在治疗CXC趋化因子介导的疾病等方面具有用途，并且还披露了在其合成中有用的中间体。
• [EN] CXCR-2 INHIBITORS FOR TREATING CRYSTAL ARTHROPATHY DISORDERS<br/>[FR] INHIBITEURS DU CXCR-2 PERMETTANT DE TRAITER DES TROUBLES ASSOCIÉS À UNE ARTHROPATHIE CRISTALLINE
  申请人：ARDEA BIOSCIENCES INC

  公开号：WO2017156270A1

  公开（公告）日：2017-09-14

  N-(2-((2,3-difluorobenzyl)thio)-6-(((2R,3S)-3,4-dihydroxybutan-2-yl)oxy)pyrimidin-4-yl)azetidine-1-sulfonamide (compound 3) and N-(6-(((2R,3S)-3,4-dihydroxy butan-2-yl)oxy)-2-((4-fluoro benzyl)thio)pyrimidin-4-yl)-3-methylazetidine-1-sulfonamide(compound 4) are known chemokine modulators and are therefore useful in the treatment of diseases/conditions in which modulation of chemokine receptor activity is beneficial. In particular, provided herein are compositions and methods for the treatment and prevention of gout.

  N-(2-((2,3-二氟苄基)硫基)-6-(((2R,3S)-3,4-二羟基丁-2-基)氧基)嘧啶-4-基)氮杂环丙磺酰胺（化合物3）和N-(6-(((2R,3S)-3,4-二羟基丁-2-基)氧基)-2-((4-氟苄基)硫基)嘧啶-4-基)-3-甲基氮杂环丙磺酰胺（化合物4）是已知的化学调节剂，因此在调节趋化因子受体活性有益的疾病/症状的治疗中很有用。特别提供了用于痛风的治疗和预防的组合物和方法。