cyclopropyl-(6,7-dichloro-1,1-dioxo-1,2(4)-dihydro-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-amine | 53413-86-8

• 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: cyclopropyl-(6,7-dichloro-1,1-dioxo-1,2(4)-dihydro-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-amine
• 英文别名: 6,7-dichloro-N-cyclopropyl-1,1-dioxo-4H-1lambda6,2,4-benzothiadiazin-3-imine；6,7-dichloro-N-cyclopropyl-1,1-dioxo-4H-1λ6,2,4-benzothiadiazin-3-imine
• CAS: 53413-86-8
• 化学式: C₁₀H₉Cl₂N₃O₂S
• 分子量: 306.172
• InChiKey: LIFGFDUZGAHMME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 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：

  2-氨基-4,5-二氯苯磺酰胺 反应 5.0h， 生成 cyclopropyl-(6,7-dichloro-1,1-dioxo-1,2(4)-dihydro-1λ⁶-benzo[1,2,4]thiadiazin-3-yl)-amine
  参考文献：
  名称：

  3-Alkylamino-4H-1,2,4-benzothiadiazine 1,1-Dioxides as ATP-Sensitive Potassium Channel Openers:  Effect of 6,7-Disubstitution on Potency and Tissue Selectivity

  摘要：

  A series of 6,7-disubstituted 4H-1,2,4-benzothiadiazine 1,1-dioxides bearing a short alkylamino side chain in the 3-position were synthesized. These compounds were tested on rat pancreatic islets and on rat aorta rings. In vitro data indicated that in most cases substitution in the 6 and the 7 positions increased their activity as inhibitors of insulin secretion, while the myorelaxant potency of the drugs was maintained or enhanced according to the nature of the substituent in the 7-position. The presence of either chlorine or bromine atoms in the 6 and 7 positions did not improve the apparent selectivity of the drugs for the pancreatic tissue. By contrast, the introduction of one or two fluorine atoms, as well as the presence of a methoxy group in the 7-position, generated potent and selective inhibitors of insulin release. Radioisotopic and fluorimetric experiments performed with the most potent compound inhibiting insulin release (34, BPDZ 259, 6-chloro-7-fluoro-3-isopropylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide) confirmed that the drug activated K-ATP channels. 34 was found to be one of the most potent and selective pancreatic potassium channel openers yet described.

  DOI：

  10.1021/jm0580050

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
• NOVEL THERAPEUTICS FOR THE TREATMENT OF GLAUCOMA
  申请人：Mayo Foundation for Medical Education and Research

  公开号：EP3099304A1

  公开（公告）日：2016-12-07
• 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.