1,2-苯异噁唑-3-甲烷磺酰氯 | 73101-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并异恶唑
• 中文名称: 1,2-苯异噁唑-3-甲烷磺酰氯
• 中文别名: 唑尼沙胺氯
• 英文名称: 1,2-benzoxazol-3-ylmethanesulfonyl chloride
• 英文别名: benzo[d]isoxazol-3-yl-methanesulfonyl chloride；1,2-benzisoxazole-3-methane-sulfonyl chloride；1,2-benzisoxazole-3-methanesulfonoyl chloride；1,2-benzisoxazole-3-methanesulfonyl chloride；benzisoxazole-methanesulfonylchloride
• CAS: 73101-65-2
• 化学式: C₈H₆ClNO₃S
• mdl: MFCD07367669
• 分子量: 231.66
• InChiKey: ZREYTLWEJMYKRX-UHFFFAOYSA-N

物化性质

• 沸点：
  395.7±25.0 °C(Predicted)
• 密度：
  1.562±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（少许）、氯仿（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-苯异噁唑-3-甲烷磺酰氯 在 氨 、 potassium carbonate 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 生成 (benzo[d]isoxazol-3-yl-methanesulfonyl)-carbamic acid ethyl ester
  参考文献：
  名称：

  Studies on 3-substituted 1,2-benzisoxazole derivatives. 6. Syntheses of 3-(sulfamoylmethyl)-1,2-benzisoxazole derivatives and their anticonvulsant activities

  摘要：

  Several 3-(sulfamoylmethyl)-1,2-benzisoxazole derivatives were synthesized from 3-(bromomethyl)-1,2-benzisoxazole by the reaction with sodium bisulfite followed by chlorination and amination. Some of them displayed marked anticonvulsant activity in mice. The introduction of a halogen atom to the 5 position of the benzisoxazole ring caused increased activity and neurotoxicity; the substitution of a sulfamoyl group caused decreased activity. The activity of monoalkylated compounds might be the result of biotransformation. Among these compounds, 3-(sulfamoylmethyl)-1,2-benzisoxazole (1a) was thought to be the most promising as an anticonvulsant from the ratio of NTD50 and ED50.

  DOI：

  10.1021/jm00188a011
• 作为产物：
  描述：

  1,2-benzisoxazole-3-methanesulfonic acid sodium salt 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 生成 1,2-苯异噁唑-3-甲烷磺酰氯
  参考文献：
  名称：

  Method for preparing benzisoxazole methane sulfonyl chloride and its amidation to form zonisamide

  摘要：

  本发明涉及一种制备苯并异噁唑甲烷磺酸氯化物（BOS-Cl）作为唑尼沙米德中间体的过程，通过对苯并异噁唑甲烷磺酸盐进行氯化而得到。本发明还公开了一种通过BOS-Cl酰胺化制备唑尼沙米德的过程。更具体地，本发明提供了制备唑尼沙米德的过程，包括以下步骤：a）用SOCl2在有机溶剂和/或催化剂存在下氯化BOS、其盐或酯，形成BOS-Cl；和b）在选自双相系统中的水氨、掩蔽氨和干氨的氨存在下，使BOS-Cl酰胺化，形成唑尼沙米德。

  公开号：

  US20040014983A1

文献信息

• [EN] AMIDOPYRAZOLE INHIBITORS OF INTERLEUKIN RECEPTOR-ASSOCIATED KINASES<br/>[FR] INHIBITEURS DE KINASES ASSOCIÉES AUX RÉCEPTEURS D'INTERLEUKINE À BASE D'AMIDOPYRAZOLE
  申请人：MERCK SHARP & DOHME

  公开号：WO2012129258A1

  公开（公告）日：2012-09-27

  This invention relates to amidopyrazole compounds that are inhibitors of Interleukin receptor-associated kinases, in particular IRAK-4, and are useful in the treatment of cellular proliferative diseases, for example, cancer, hyperplasia, restenosis, cardiac hypertrophy, immune disorders and inflammation.

  这项发明涉及抗干扰素受体相关激酶（特别是IRAK-4）的抑制剂——amidopyrazole化合物，可用于治疗细胞增殖性疾病，例如癌症、增生、再狭窄、心肌肥大、免疫紊乱和炎症。
• [EN] IMPROVED PROCESS FOR THE PREPARATION OF INTERMEDIATES USEFUL FOR THE PREPARATION OF ZONISAMIDE<br/>[FR] PROCEDE AMELIORE DE FABRICATION D'INTERMEDIAIRES UTILISES POUR L'OBTENTION DE ZONISAMIDE
  申请人：SUVEN LIFE SCIENCES LTD

  公开号：WO2005030738A1

  公开（公告）日：2005-04-07

  The invention relates to an improved process for the preparation of 1,2-benzisoxazole-3­-methane sulfonates and a novel compound 4-oximino-2,3-dihydrobenzoxathiin-2, 2­-dioxides. The 1,2-benzisoxazole-2-methane sulfonates and 4-oximino-2, 3-­dihydrobenzoxathiin-2, 2-dioxides prepared by the processes of the present invention have the general formula (2) & (3) respectively . The compounds of the formulae (2) and (3) are important intermediates for the preparation of Zonisamide of the formula (1) (an anticonvulsant drug). The compounds of the formula (2) is prepared from hitherto unknown compound 4-oximino-2,3-dihydrobenzoxathiin-2, 2-dioxides of the formula (3) using strong bases with suitable solvents. The novel compounds of the formula (3) is prepared by the intramolecular Cyclocondensation of the compound of the formula (4) to get the compound of the formula (5) and subsequent reaction with hydroxylamine hydrochloride to get the novel intermediates of the formula (3). In the above mentioned formulae R1 to R4 - may be the same or different and represents hydrogen, alkyl, (with carbons, 2-5), chloro, bromo, S- alkyl, o- alkyl, NO2, N- Me2, CF3. and where X represents Na or K.

  本发明涉及一种改进的制备1,2-苯并异噁唑-3-甲烷磺酸盐和新型化合物4-肟基-2,3-二氢苯并噁噻英-2,2-二氧化物的方法。通过本发明的方法制备的1,2-苯并异噁唑-2-甲烷磺酸盐和4-肟基-2,3-二氢苯并噁噻英-2,2-二氧化物分别具有通式(2)和(3)。通式(2)和(3)的化合物是制备通式(1)的唑尼沙胺（一种抗惊厥药物）的重要中间体。通式(2)的化合物是通过使用强碱和适当溶剂从未知化合物通式(3)的4-肟基-2,3-二氢苯并噁噻英-2,2-二氧化物制备的。新型化合物通式(3)是通过化合物通式(4)的分子内环化反应得到化合物通式(5)，随后与盐酸羟胺反应得到新型中间体通式(3)。上述通式中R1至R4可以是相同或不同的，代表氢、烷基（碳数2-5）、氯、溴、硫代烷基、氧代烷基、硝基、二甲基氨基、三氟甲基，其中X代表钠或钾。
• [EN] N-HYDROXYMETHANESULFONAMIDE NITROXYL DONORS<br/>[FR] DONNEURS DE NITROXYLE N-HYDROXYMETHANESULFONAMIDE
  申请人：CARDIOXYL PHARMACEUTICALS INC

  公开号：WO2015109210A1

  公开（公告）日：2015-07-23

  The disclosed subject matter provides N-hydroxymethanesulfonamide compounds, pharmaceutical compositions and kits comprising such compounds, and methods of using such compounds or pharmaceutical compositions. In particular, the disclosed subject matter provides methods of using such compounds or pharmaceutical compositions for treating heart failure.

  公开的主题提供了N-羟甲磺酰胺化合物、包含这种化合物的制药组合物和试剂盒，以及使用这种化合物或制药组合物的方法。特别地，公开的主题提供了使用这种化合物或制药组合物治疗心力衰竭的方法。
• N-HYDROXYMETHANESULFONAMIDE NITROXYL DONORS
  申请人：Cardioxyl Pharmaceuticals, Inc.

  公开号：US20160046569A1

  公开（公告）日：2016-02-18

  The disclosed subject matter provides N-hydroxymethanesulfonamide compounds, pharmaceutical compositions and kits comprising such compounds, and methods of using such compounds or pharmaceutical compositions. In particular, the disclosed subject matter provides methods of using such compounds or pharmaceutical compositions for treating heart failure.

  所披露的主题提供了N-羟甲磺酰胺化合物、包含这种化合物的制药组合物和试剂盒以及使用这种化合物或制药组合物的方法。特别地，所披露的主题提供了使用这种化合物或制药组合物治疗心力衰竭的方法。
• [EN] A PROCESS FOR THE MANUFACTURE OF ZONISAMIDE<br/>[FR] PROCEDE DE FABRICATION DE ZONISAMIDE
  申请人：WOCKHARDT LTD

  公开号：WO2005044808A1

  公开（公告）日：2005-05-19

  The present invention describes an improved process for the preparation of 1,2Benzisoxazole-3-methanesulphonamide (Zonisamide), a well known anti-epileptic agent which possesses anti-convulsant and anti-neurotoxic effects. Other aspect of this invention are isolation of a key intermediate, viz., crystalline sodium chloride associated 1,2Benzisoxazole-3-methane sodium sulfonate (BOS-Na:NaCl). The isolated crude BOSNa:NaCl is directly converted to Zonisamide using controlled molar ratio of chlorosulfonic acid to avoid the disulfonated side products. The analytical characteristics like IR and XRD data of the BOS-Na:NaCl are also reported to confirm its nature.

  本发明描述了一种改进的制备1,2苯并异噁唑-3-甲磺酰胺（左尼嗪）的方法，该药物是一种广为人知的抗癫痫药物，具有抗惊厥和抗神经毒性作用。本发明的其他方面包括分离关键中间体，即结晶氯化钠相关的1,2苯并异噁唑-3-甲烷磺酸钠（BOS-Na:NaCl）。分离的粗BOSNa:NaCl直接转化为左尼嗪，使用控制的氯磺酸摩尔比避免二磺化副产物。还报告了BOS-Na:NaCl的红外和XRD数据等分析特征以确认其性质。