3-amino-6-chloro-2-hydroxy-N-methoxy-N-methylbenzene-1-sulfonamide | 276703-14-1

• 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: 3-amino-6-chloro-2-hydroxy-N-methoxy-N-methylbenzene-1-sulfonamide
• 英文别名: (N-methoxy-N-methyl)-3-amino-6chloro-2-hydroxybenzenesulfonamide；3-amino-6-chloro-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide；3-amino-6-chloro-2-hydroxy-N-methoxy-N-methylbenzenesulfonamide
• CAS: 276703-14-1
• 化学式: C₈H₁₁ClN₂O₄S
• 分子量: 266.705
• InChiKey: RYSGFKNYZFZUFK-UHFFFAOYSA-N

物化性质

• 沸点：
  407.4±55.0 °C(Predicted)
• 密度：
  1.532±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-amino-6-chloro-2-hydroxy-N-methoxy-N-methylbenzene-1-sulfonamide 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 7.5h， 生成 6-chloro-3-[2-(1-ethyl-propylamino)-3,4-dioxo-cyclobut-1-enylamino]-2-hydroxy-N-methoxy-N-methyl-benzenesulfonamide choline salt
  参考文献：
  名称：

  Early Process Development of a Squaramide-Based CXCR2 Receptor Antagonist

  摘要：

  The synthesis of a CXCR2 antagonist is presented, highlighting the process changes made from research synthesis to clinical supply. The target compound is the choline salt of a nonsymmetrical squaramide, and the modifications to the synthetic route which have effect on chemical purity are discussed with reference to the isolated byproducts. Although drug substance quality was shown to increase following optimization of the linear sequence, an alternative one-pot, convergent sequence was introduced, which makes dual use of choline hydroxide as both base and salt-forming agent. The overall benefits of the strategic change is discussed in terms of overall yield and economy.

  DOI：

  10.1021/acs.oprd.5b00072
• 作为产物：
  描述：

  6-氯-2-叔丁基-N-甲氧基-N-甲基-7-苯并恶唑磺酰胺 在 硫酸 、 水 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 生成 3-amino-6-chloro-2-hydroxy-N-methoxy-N-methylbenzene-1-sulfonamide
  参考文献：
  名称：

  ORGANIC COMPOUNDS

  摘要：

  本发明涉及以下式（I）的化合物 其中X，R1，R2，R3，R4和R5如本文所定义，这些化合物对于治疗对CXCR2受体介质有响应的疾病是有用的。还描述了含有这些化合物的药物组合物以及制备这些化合物的方法。

  公开号：

  US20100029670A1

文献信息

• [EN] HYDROXY DIPHENYL UREA SULFONAMIDES AS IL-8 RECEPTOR ANTAGONISTS<br/>[FR] SULFONAMIDES HYDROXYDIPHENYLUREE ANTAGONISTES DU RECEPTEUR D'IL-8
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2000035442A1

  公开（公告）日：2000-06-22

  The invention relates to novel hydroxy diphenylurea sulfonamides, compositions and intermediates thereof. The hydroxy diphenylurea sulfonamides are useful in the treatment of disease states mediated by the chemokine, Interleukin-8.

  该发明涉及新型羟基二苯基脲磺酰胺、其组合物和中间体。该羟基二苯基脲磺酰胺在治疗由趋化因子Interleukin-8介导的疾病状态中具有用途。
• Hydroxy diphenyl urea sulfonamides as IL-8 receptor antagonists
  申请人：SmithKline Beecham Corporation

  公开号：US20030109527A1

  公开（公告）日：2003-06-12

  The invention relates to novel hydroxy diphenylurea sulfonamides, compositions and intermediates thereof. The hydroxy diphenylurea sulfonamides are useful in the treatment of disease states mediated by the chemokine, Interleukin-8.

  本发明涉及新型羟基二苯脲磺酰胺、其组合物和中间体。这些羟基二苯脲磺酰胺在治疗由趋化因子白细胞介素-8介导的疾病状态中具有用途。
• Squaramide derivatives as CXCR2 antagonist
  申请人：Novartis AG

  公开号：US08288588B2

  公开（公告）日：2012-10-16

  The present invention relates to compounds of formula (I) wherein X, R1, R2, R3, R4 and R5 are as defined herein, which are useful for treating diseases which respond to CXCR2 receptor mediators. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.

  本发明涉及式（I）的化合物，其中X，R1，R2，R3，R4和R5如本文所定义，这些化合物对于治疗对CXCR2受体介质有反应的疾病是有用的。还描述了包含这些化合物的制药组合物以及制备这些化合物的过程。
• SQUARAMIDE DERIVATIVES AS CXCR2 ANTAGONIST
  申请人：Baettig Urs

  公开号：US20110251205A1

  公开（公告）日：2011-10-13

  The present invention relates to compounds of formula (I) wherein X, R 1 , R 2 , R 3 , R 4 and R 5 are as defined herein, which are useful for treating diseases which respond to CXCR2 receptor mediators. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.

  本发明涉及式(I)化合物，其中X、R1、R2、R3、R4和R5如本文所定义，该化合物可用于治疗对CXCR2受体介质有响应的疾病。还描述了含有该化合物的药物组合物以及制备该化合物的方法。
• EP1161232A4
  申请人：——

  公开号：EP1161232A4

  公开（公告）日：2002-09-18