6-chloro-3-cyclopropylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide | 53413-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 英文名称: 6-chloro-3-cyclopropylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide
• 英文别名: (6-chloro-1,1-dioxo-1,2(4)-dihydro-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-cyclopropyl-amine；6-chloro-N-cyclopropyl-1,1-dioxo-4H-1lambda6,2,4-benzothiadiazin-3-imine；6-chloro-N-cyclopropyl-1,1-dioxo-4H-1λ6,2,4-benzothiadiazin-3-imine
• CAS: 53413-81-3
• 化学式: C₁₀H₁₀ClN₃O₂S
• 分子量: 271.727
• InChiKey: LCKONDXHSFPLKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-chloro-3-methylsulfanyl-4H-1,2,4-benzothiadiazine 1,1-dioxide 、 环丙胺 以74%的产率得到6-chloro-3-cyclopropylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide
  参考文献：
  名称：

  氯取代的3-烷基氨基-4 H -1,2,4-苯并噻二嗪1,1-二氧化物作为ATP敏感的钾通道活化剂：氯原子在芳环上的位置对活性和组织选择性的影响

  摘要：

  描述了5-氯-，6-氯-和8-氯取代的3-烷基氨基/环烷基氨基-4 H -1,2,4-苯并噻二嗪1,1-二氧化物的合成。将它们对胰岛素释放过程的抑制作用及其血管舒张活性与先前报道的7-氯-3-烷基氨基/环烷基氨基-4 H -1,2,4-苯并噻二嗪1,1-二氧化物进行了比较。发现“ 5-氯”化合物对胰岛素分泌和平滑肌细胞均基本无活性。相反，发现“ 8-氯”和“ 6-氯”化合物在分泌胰岛素的细胞上具有活性，其中“ 6-氯”衍生物是最有效的药物。此外，“ 6-氯”类似物比“ 7-氯”对应物表现出更少的髓鞘松弛活性。8-氯-3-异丙基氨基-4 H-1,2,4-苯并噻二嗪1,1-二氧化物（25b）和6-氯-3-环丁基氨基-4 H -1,2,4-苯并噻二嗪1,1-二氧化物（19e）被进一步确定为K ATP通道通过对胰岛素分泌细胞进行放射性同位素测量的开环剂。同样，目前在表达人SUR1 / Kir6.2

  DOI：

  10.1021/jm9010093

文献信息

• Therapeutics for the treatment of glaucoma
  申请人：MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH

  公开号：US10981951B2

  公开（公告）日：2021-04-20

  The present invention provides benzothiadiazine and chroman derivatives and particularly diazoxide and cromakalim derivatives for use in treating glaucoma, retinopathy, treating age related macular degeneration, treating, stabilizing and/or inhibiting blood and lymph vascularization, and reducing intraocular pressure by administering a pharmaceutically effective amount of a prodrug disposed in an ophthalmically acceptable carrier to the eye, wherein the prodrug specifically modulates a KATP channel to reduce an intraocular pressure.

  本发明提供苯并噻二嗪和色苷衍生物，特别是用于治疗青光眼、视网膜病变、治疗年龄相关性黄斑变性、治疗、稳定和/或抑制血液和淋巴血管生成，并通过向眼睛内给予药学有效量的前药，其中前药特异性调节KATP通道以降低眼内压力。
• Raffa; Di Bella; Ferrari, Farmaco, Edizione Scientifica, 1974, vol. 29, # 6, p. 411 - 423
  作者：Raffa、Di Bella、Ferrari、Rinaldi、Ferrari

  DOI：——

  日期：——
• 1,2,4-BENZOTHIADIAZINE DERIVATIVES, THEIR PREPARATION AND USE
  申请人：Université de Liège

  公开号：EP0906297B1

  公开（公告）日：2004-02-25
• USE OF DIAZOXIDE FOR SUPPRESSING THE PLASMA INSULIN LEVEL IN A MAMMAL
  申请人：De Boer Johannes Mathijs Maria

  公开号：US20100234362A1

  公开（公告）日：2010-09-16

  The present invention relates to the use of a potassium channel activator in the manufacture of a medicament for suppressing the fasting plasma insulin level and/or postabsorptive insulin level in a mammal in need thereof, wherein the fasting and/or postabsorptive plasma insulin level is reduced to about 5 mU/l or less. The present invention also relates to the use of a potassium channel activator in the manufacture of a medicament for suppressing the fasting plasma insulin level and/or postabsorptive insulin level in a mammal in need thereof for treating or preventing obesity, obesity related disorders and conditions and other disorders and conditions related to weight gain in a mammal in need thereof, said method comprising orally administering to said mammal in need thereof a daily dosage of about 5 mg to about 1200 mg, calculated on a Diazoxide active weight basis.
• USE OF A COMBINATION OF DIAZOXIDE AND METFORMIN FOR TREATING OBESITY OR OBESITY RELATED DISORDERS
  申请人：De Boer Johannes Marthijs Maria

  公开号：US20120053172A1

  公开（公告）日：2012-03-01

  The present invention relates to a method for suppressing the fasting plasma insulin level and/or postabsorptive insulin level in a mammal in need thereof, said method comprising administering to said mammal a pharmaceutically effective amount of a combination of a potassium channel activator and an anti-diabetic drug. The present invention also relates to a method for treating or preventing obesity, obesity related disorders and conditions and other disorders and conditions related to weight gain in a mammal in need thereof, said method comprising administering to said mammal a pharmaceutically effective amount of a combination of a potassium channel activator and an anti-diabetic drug.