2-Hydroxy-3-[(2-methoxy-3,4-dioxo-1-cyclobuten-1-yl)amino]-N,N-dimethylbenzamide | 473732-10-4

• 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: 2-Hydroxy-3-[(2-methoxy-3,4-dioxo-1-cyclobuten-1-yl)amino]-N,N-dimethylbenzamide
• 英文别名: 2-hydroxy-3-[(2-methoxy-3,4-dioxocyclobuten-1-yl)amino]-N,N-dimethylbenzamide
• CAS: 473732-10-4
• 化学式: C₁₄H₁₄N₂O₅
• 分子量: 290.276
• InChiKey: ZANPDJIGQKJUDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-3-[(2-methoxy-3,4-dioxo-1-cyclobuten-1-yl)amino]-N,N-dimethylbenzamide 、 (R)-1-(5-methylfuran-2-yl)propan-1-amine 以 2-甲基四氢呋喃 为溶剂， 反应 5.0h， 生成 squaramide
  参考文献：
  名称：

  [EN] PROCESS AND INTERMEDIATES FOR THE SYNTHESIS OF 1,2-SUBSTITUTED 3,4-DIOXO-1-CYCLOBUTENE COMPOUNDS
  [FR] PROCÉDÉ ET INTERMÉDIAIRES DE SYNTHÈSE DE COMPOSÉS DE 3,4-DIOXO-1-CYCLOBUTÈNE 1,2-SUBSTITUÉS

  摘要：

  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。

  公开号：

  WO2009005801A1
• 作为产物：
  描述：

  3-硝基水杨酸 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 2-Hydroxy-3-[(2-methoxy-3,4-dioxo-1-cyclobuten-1-yl)amino]-N,N-dimethylbenzamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 3,4-diaminocyclobut-3-ene-1,2-dione CXCR2 antagonists

  摘要：

  A novel series of 3,4-diaminocyclobut-3-ene-1,2-diones was prepared and found to show potent inhibitory activity of CXCR2 binding and IL-8-mediated chemotaxis of a CXCR2-expressing cell line. Microsome stability and Caco2 studies were subsequently used to show that compounds of this chemotype are predicted to have good oral bioavailability and are thus suitable for pharmaceutical development. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.082

文献信息

• 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands
  申请人：Schering Corporation

  公开号：US20040106794A1

  公开（公告）日：2004-06-03

  There are disclosed compounds of the formula 1 or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.

  这里公开了用于治疗诸如急性和慢性炎症性疾病以及癌症的趋化因子介导疾病的公式1化合物或其药用可接受的盐或溶剂。
• NOVEL DISUBSTITUTED 3,4-DIAMINO-3-CYCLOBUTENE-1,2-DIONE COMPOUNDS FOR USE IN THE TREATMENT OF CHEMOKINE-MEDIATED DISEASES
  申请人：GALDERMA RESEARCH & DEVELOPMENT

  公开号：US20140296254A1

  公开（公告）日：2014-10-02

  Disubstituted 3,4-diamino-3-cyclobutene-1,2-dione compounds are described that correspond to general formula (I). Also described, are pharmaceutical compositions that include these compounds and methods of using these compounds and compositions for the treatment of chemokine-mediated diseases.

  描述了符合一般式(I)的二取代3,4-二氨基-3-环丁烯-1,2-二酮化合物。还描述了包括这些化合物的药物组合物以及使用这些化合物和组合物治疗趋化因子介导的疾病的方法。
• [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。
• 3,4-DI-SUBSTITUTED CYCLOBUTENE-1,2-DIONES AS CXC-CHEMOKINE RECEPTOR LIGANDS
  申请人：Chao Jianhua

  公开号：US20080045489A1

  公开（公告）日：2008-02-21

  Disclosed are novel cyclobutenedione Compounds 1 to 18 comprising a cyclobutenedione ring, a substituted phenyl ring, and a —CH(C 2 H 5 )-furan moiety. The phenyl ring and the —CH(C 2 H 5 )-furan moiety are each bound to the cyclobutenedione ring through a —NH— moiety. Also disclosed are methods of treating chemokine mediated diseases (e.g., cancer, COPD, acute and chronic inflammatory disorders, psoriasis, cystic fibrosis, and asthma) using the novel Compounds 1 to 18.

  本发明涉及一种新型环丁烯二酮化合物1到18，包括一个环丁烯二酮环、一个取代苯环和一个—CH（C2H5）-呋喃基团。苯环和—CH（ ）-呋喃基团分别通过—NH—基团与环丁烯二酮环相连。本发明还涉及使用这些新化合物1到18治疗趋化因子介导的疾病的方法（例如癌症、COPD、急性和慢性炎症性疾病、牛皮癣、囊性纤维化和哮喘）。
• 3,4-Di-Substituted Cyclobutene-1,2-Diones as CXC-Chemokine Receptor Ligands
  申请人：Taveras Arthur G.

  公开号：US20110213029A1

  公开（公告）日：2011-09-01

  There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.

  公开了以下式的化合物，或其药学上可接受的盐或溶剂，它们可用于治疗由趋化因子介导的疾病，如急性和慢性炎症性疾病和癌症。