3-butylamino-2-phenoxy-5-phenylaminomethyl benzenesulfonamide | 62275-23-4

• 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-butylamino-2-phenoxy-5-phenylaminomethyl benzenesulfonamide
• 英文别名: 5-(anilinomethyl)-3-(butylamino)-2-phenoxybenzenesulfonamide；BUM-13；bumepamine；(3-n-Butylamino-4-phenoxy-5-sulfamylbenzyl)aniline
• CAS: 62275-23-4
• 化学式: C₂₃H₂₇N₃O₃S
• 分子量: 425.552
• InChiKey: YFQFGDKUFNMHSK-UHFFFAOYSA-N

物化性质

• 沸点：
  614.3±65.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-butylamino-2-phenoxy-5-phenylaminomethyl benzenesulfonamide 、 二甲氨基氯乙烷盐酸 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以38.3%的产率得到5-(anilinomethyl)-3-(butylamino)-N-[2-(dimethylamino)ethyl]-2-phenoxybenzenesulfonamide
  参考文献：
  名称：

  WO2019193159A5

  摘要：

  公开号：

  WO2019193159A5
• 作为产物：
  描述：

  3-(butylamino)-5-(hydroxymethyl)-2-phenoxybenzenesulfonamide 在 吡啶 、 chromium(VI) oxide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 3-butylamino-2-phenoxy-5-phenylaminomethyl benzenesulfonamide
  参考文献：
  名称：

  DE2630637

  摘要：

  公开号：

文献信息

• Bumepamine, a brain-permeant benzylamine derivative of bumetanide, does not inhibit NKCC1 but is more potent to enhance phenobarbital's anti-seizure efficacy
  作者：Claudia Brandt、Patricia Seja、Kathrin Töllner、Kerstin Römermann、Philip Hampel、Markus Kalesse、Andi Kipper、Peter W. Feit、Kasper Lykke、Trine Lisberg Toft-Bertelsen、Pauliina Paavilainen、Inkeri Spoljaric、Martin Puskarjov、Nanna MacAulay、Kai Kaila、Wolfgang Löscher

  DOI：10.1016/j.neuropharm.2018.09.025

  日期：2018.12

  use as a diuretic in humans. This prompted us to search for a bumetanide derivative that more easily penetrates into the brain. Here we show that bumepamine, a lipophilic benzylamine derivative of bumetanide, exhibits much higher brain penetration than bumetanide and is more potent than the parent drug to potentiate phenobarbital's anticonvulsant effect in two rodent models of chronic difficult-to-treat

  基于Na-K-Cl协同转运蛋白（NKCC）在癫痫性癫痫发作中的潜在作用，已测试了阻断NKCC1亚型NKCC1和NKCC2的利尿剂布美他尼与苯巴比妥作为抑制癫痫发作的辅助剂。然而，由于布美他尼的理化特性，它只能穿透血脑屏障。因此，当使用的剂量（0.1–0.5 mg / kg）在批准用作人类利尿剂的剂量范围内时，未达到抑制海马和新皮质神经元中NKCC1所需的浓度。这促使我们寻找更容易渗透到大脑中的布美他尼衍生物。在这里，我们显示了布美他尼，一种布美他尼的亲脂性苄胺衍生物，比布美他尼具有更高的大脑渗透能力，并且比母体药物对苯巴比妥更有效。在慢性难治性癫痫的两种啮齿动物模型，大鼠杏仁核点燃和小鼠毛果芸香碱模型中具有抗惊厥作用。然而，布美他命抑制新生大鼠海马切片中NKCC1依赖性巨去极化电位（GDPs）的效果比布美他尼低得多，并且不抑制GABA诱导的Ca2+切片中出现瞬态现象，表明布美帕明不抑制NK
• Compositions and methods for the treatment of hypertension or oedemas
  申请人：Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik

  公开号：US04247550A1

  公开（公告）日：1981-01-27

  The invention relates to a series of new compounds, salts thereof and to methods for the preparation of the compounds which have the general formula ##STR1## in which R.sub.1 stands for an unsubstituted or substituted phenoxy, phenylthio, benzyl, phenylsulfinyl, or anilino radical; R.sub.2 stands for a --YR.sub.2 ' radical, in which Y represents --O--, --S--, or --NH--, and R.sub.2 ' represents C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl or -alkynyl; or methyl or ethyl substituted with phenyl, furyl, thienyl or pyridyl; R.sub.3 and R.sub.4 which can be the same or different, and unsubstituted or substituted, stand for hydrogen or for a straight or branched C.sub.1 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl or -alkynyl radical, a C.sub.5 -C.sub.7 -cycloalkyl, a phenyl, or a 5-, 6- or 7-membered heterocyclic ring system containing not more than two hetero atoms selected from the group consisting of oxygen, sulphur and nitrogen, or for a C.sub.1 -C.sub.3 alkyl radical substituted with phenyl or with a 5-, 6- or 7-membered heterocyclic ring system containing not more than two hetero atoms selected from the group consisting of oxygen, sulphur and nitrogen; and R.sub.4 furthermore stands for a lower carbalkoxy radical, a C.sub.1 -C.sub.6 alkanoyl radical, or a benzoyl radical; and salts thereof with pharmaceutically acceptable acids. The compounds of the invention possess a pronounced diuretic and/or saluretic activity with a very low excretion of potassium ions. The low toxicity also makes the present compounds particularly valuable in human and veterinary practice.

  该发明涉及一系列新化合物、其盐以及制备该化合物的方法，其具有以下通式： ##STR1## 其中，R1代表未取代或取代的苯氧基、苯硫基、苄基、苯基亚磺酰基或苯胺基基团；R2代表--YR2'基团，其中Y代表--O--、--S--或--NH--，R2'代表C1-C6烷基、C2-C6烯基或-炔基；或被苯基、呋喃基、噻吩基或吡啶基取代的甲基或乙基；R3和R4可以相同或不同，未取代或取代，代表氢或直链或支链C1-C8烷基、C2-C8烯基或-炔基、C5-C7环烷基、苯基或含有不超过两个选自氧、硫和氮的杂原子的5、6或7元杂环环系，或被取代为含有不超过两个选自氧、硫和氮的杂原子的5、6或7元杂环环系的C1-C3烷基；R4还代表较低的碳酸烷氧基、C1-C6酰基或苯甲酰基；以及与药用酸盐的盐。该发明的化合物具有显著的利尿和/或盐利尿作用，同时钾离子的排泄非常低。低毒性也使得该化合物在人类和兽医实践中特别有价值。
• Sulphonamides, compositions containing the same and methods for using
  申请人：Leo Pharmaceutical Products Ltd.

  公开号：US04082851A1

  公开（公告）日：1978-04-04

  The invention relates to a series of new compounds, salts thereof and to methods for the preparation of the compounds which have the general formula ##STR1## in which R.sub.1 stands for an unsubstituted or substituted phenoxy, phenylthio, benzyl, phenylsulfinyl, or anilino radical; R.sub.2 stands for a -YR.sub.2 ' radical, in which Y represents -O-, -S-, or -NH-, and R.sub.2 ' represents C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl or -alkynyl; or methyl or ethyl substituted with phenyl, furyl, thienyl or pyridyl; R.sub.3 and R.sub.4 which can be the same or different, and unsubstituted or substituted, stand for hydrogen or for a straight or branched C.sub.1 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl or -alkynyl radical, a C.sub.5 -C.sub.7 -cycloalkyl, a phenyl, or a 5-, 6- or 7-membered heterocyclic ring system containing not more than two hetero atoms selected from the group consisting of oxygen, sulphur and nitrogen, or for a C.sub.1 -C.sub.3 alkyl radical substituted with phenyl or with a 5-, 6- or 7-membered heterocyclic ring system containing not more than two hetero atoms selected from the group consisting of oxygen, sulphur and nitrogen; and R.sub.4 furthermore stands for a lower carbalkoxy radical, a C.sub.1 -C.sub.6 alkanoyl radical, or a benzoyl radical; and Salts thereof with pharmaceutically acceptable acids. The compounds of the invention possess a pronounced diuretic and/or saluretic activity with a very low excretion of potassium ions. The low toxicity also makes the present compounds particularly valuable in human and veterinary practice.

  本发明涉及一系列新化合物及其盐，并涉及制备该化合物的方法，其具有以下通式： 其中，R1代表未取代或取代的苯氧基、苯硫基、苄基、苯基亚磺酰基或苯胺基基团；R2代表-YR2'基团，其中Y代表-O-、-S-或-NH-，R2'代表C1-C6烷基、C2-C6烯基或-炔基；或者被苯基、呋喃基、噻吩基或吡啶基取代的甲基或乙基；R3和R4可以相同或不同，未取代或取代，代表氢或直链或支链C1-C8烷基、C2-C8烯基或-炔基、C5-C7环烷基、苯基或不超过两个来自氧、硫和氮的杂原子的5、6或7元杂环环系统，或被苯基或不超过两个来自氧、硫和氮的杂原子的5、6或7元杂环环系统取代的C1-C3烷基；R4还代表较低的羰基烷氧基基团、C1-C6烷酰基基团或苯甲酰基基团；以及与药学上可接受的酸形成的盐。本发明化合物具有明显的利尿和/或利盐作用，且钾离子的排泄非常低。低毒性也使得本发明化合物在人类和兽医实践中特别有价值。
• BUMETANIDE DERIVATIVES FOR THE THERAPY OF HYPERHIDROSIS
  申请人：ZILENTIN AG

  公开号：EP3774763A1

  公开（公告）日：2021-02-17
• US4247550A
  申请人：——

  公开号：US4247550A

  公开（公告）日：1981-01-27