6-chloro-3-cyclobutylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide

• 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-cyclobutylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide
• 英文别名: 6-Chloro-3-cyclobutylamino-4H-1,2,4-benzothiadiazine 1,1-dioxide；6-chloro-N-cyclobutyl-1,1-dioxo-4H-1lambda6,2,4-benzothiadiazin-3-imine；6-chloro-N-cyclobutyl-1,1-dioxo-4H-1λ6,2,4-benzothiadiazin-3-imine
• 化学式: C₁₁H₁₂ClN₃O₂S
• 分子量: 285.754
• InChiKey: AETOKTHGOLBNQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  环丁基胺 、 6-chloro-3-methylsulfanyl-4H-1,2,4-benzothiadiazine 1,1-dioxide 以 1,4-二氧六环 为溶剂， 以69%的产率得到6-chloro-3-cyclobutylamino-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。
• 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：US20170002040A1

  公开（公告）日：2017-01-05

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

  公开号：US20210040148A1

  公开（公告）日：2021-02-11

  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 K ATP channel to reduce an intraocular pressure.
• US6242443B1
  申请人：——

  公开号：US6242443B1

  公开（公告）日：2001-06-05