N-[1-(3-methylbenzyl)-4-methylhexahydro-1H-1,4-diazepin-6-yl]-1H-indazole-3-carboxamide | 129294-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: N-[1-(3-methylbenzyl)-4-methylhexahydro-1H-1,4-diazepin-6-yl]-1H-indazole-3-carboxamide
• 英文别名: N-[1-methyl-4-(3-methylbenzyl)hexahydro-1H-1,4-diazepin-6-yl]-1H-indazole-3-carboxamide；5-HT3 antagonist 1；N-[1-methyl-4-[(3-methylphenyl)methyl]-1,4-diazepan-6-yl]-1H-indazole-3-carboxamide
• CAS: 129294-09-3
• 化学式: C₂₂H₂₇N₅O
• 分子量: 377.489
• InChiKey: KDCVCMJTEQZMEL-UHFFFAOYSA-N

物化性质

• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.3
• 氢给体数：
  2
• 氢受体数：
  4

制备方法与用途

生物活性

5-HT3 antagonist 1 是一种有效的选择性 5-羟色胺 3 (5-HT3) 受体拮抗剂。

靶点

5-HT₃ Receptor

反应信息

• 作为反应物：
  描述：

  N-[1-(3-methylbenzyl)-4-methylhexahydro-1H-1,4-diazepin-6-yl]-1H-indazole-3-carboxamide 生成 (R)-N-[1-methyl-4-(3-methyl)benzylhexahydro-1,4-diazepin-6-yl]-1H-indazole-3-carboxamide
  参考文献：
  名称：

  Synthesis and resolution of (±)-N-[1-methyl-4-(3-methylbenzyl)hexahydro-1H-1,4-diazepin-6-yl]-1H-indazole-3-carboxamide by preferential crystallization

  摘要：

  (±)-N-[1-甲基-4-(3-甲基苯甲基)六氢-1H-1,4-二氮杂环庚-6-基]-1H-吲唑-3-甲酰胺 (±)-1 是由 N-甲基-N'-(3-甲基苯甲基)乙二胺 5 和 2-(1-苯甲氧基羰基-1H-吲唑-3-羰基氨基)丙烯醛 4 合成的，并被发现为外消旋混合物，这基于其熔点、溶解性、红外光谱和 X 射线衍射图。通过选择性结晶得到 (±).1 并从乙酸乙酯中进行后续重结晶，得到了光学纯的 (R)-异构体，其显示出对 5-HT3 受体的强效且选择性的拮抗活性。 © 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00248-6
• 作为产物：
  描述：

  2-[(3-甲基苯基)甲基氨基]乙醇 在 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 43.0h， 生成 N-[1-(3-methylbenzyl)-4-methylhexahydro-1H-1,4-diazepin-6-yl]-1H-indazole-3-carboxamide
  参考文献：
  名称：

  Synthesis and resolution of (±)-N-[1-methyl-4-(3-methylbenzyl)hexahydro-1H-1,4-diazepin-6-yl]-1H-indazole-3-carboxamide by preferential crystallization

  摘要：

  (±)-N-[1-甲基-4-(3-甲基苯甲基)六氢-1H-1,4-二氮杂环庚-6-基]-1H-吲唑-3-甲酰胺 (±)-1 是由 N-甲基-N'-(3-甲基苯甲基)乙二胺 5 和 2-(1-苯甲氧基羰基-1H-吲唑-3-羰基氨基)丙烯醛 4 合成的，并被发现为外消旋混合物，这基于其熔点、溶解性、红外光谱和 X 射线衍射图。通过选择性结晶得到 (±).1 并从乙酸乙酯中进行后续重结晶，得到了光学纯的 (R)-异构体，其显示出对 5-HT3 受体的强效且选择性的拮抗活性。 © 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00248-6

文献信息

• Indazole-3-carboxylic acid derivatives
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US05017573A1

  公开（公告）日：1991-05-21

  An indazole-3-carboxylic acid derivative represented by the following general formula (I) or its physiologically acceptable acid addition salt or quaternary ammonium salt, ##STR1## wherein Y represents --NH-- or --O--; R.sub.1 and R.sub.2 are identical or different and each represents a hydrogen atom, a lower alkyl group, a substituted lower alkyl group, a cycloalkyl group, a lower alkenyl group, a cycloalkenyl group, a lower alkynyl group, an unsubstituted or substituted aryl-lower alkyl group, a lower alkoxycarbonyl group, an unsubstituted or substituted aralkyloxycarbonyl group or an acyl group, or R.sub.1 and R.sub.2, taken together, form a lower alkylene group; R.sub.3 represents a hydrogen atom, a lower alkyl group, or a phenyl group; R.sub.4 represents a hydrogen atom, a lower alkyl group, a substituted lower alkyl group, a cycloalkyl group, a lower alkenyl group, a cycloalkenyl group, a lower alkynyl group, an unsubstituted or substituted aryl-lower alkyl group, a lower alkoxycarbonyl group, an unsubstituted or substituted aralkyloxycarbonyl group or an acyl group; R.sub.5 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a hydroxyl group, a trifluoromethyl group, a nitro group, an amino group or an acylamino group; m represents a number of 1, 2, 3 or 4; n represents a number of 1, 2 or 3; and p represents a number of 1, 2, 3 or 4. This compound is useful as a potent and selective antagonist of serotonin 3 (5--HT.sub.3) receptor.

  这种化合物是一种有效且选择性的5-羟色胺3（5-HT3）受体拮抗剂。
• 6-amino-1,4-hexahydro-1H-diazepine derivatives
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US05166341A1

  公开（公告）日：1992-11-24

  Indazole-3-carboxylic acid derivatives represented by the following general formula (I) and their physiologically acceptable acid addition salts or quaternary ammonium salts, ##STR1## are useful as a potent and selective antagonist of serotonin 3 (5-HT.sub.3) receptor. Also disclosed are compounds of the formula ##STR2## which are useful as intermediates in the production of the disclosed final product compounds.

  以下是通式（I）所代表的吲唑-3-羧酸衍生物及其生理上可接受的酸盐或季铵盐，##STR1## 作为一种有效和选择性的5-羟色胺3（5-HT.sub.3）受体拮抗剂。还公开了通式 ##STR2## 的化合物，它们在制备公开的最终产物化合物方面是有用的中间体。
• Use of 5-hydroxytryptamine-antagonists in the treatment of mental disorders originating in childhood
  申请人：GLAXO GROUP LIMITED

  公开号：EP0450757A2

  公开（公告）日：1991-10-09

  The invention relates to the use of a compound which acts as an antagonist of 5-HT at 5-HT₃ receptors in the treatment of autism or another disorder originating in childhood in which there is mental retardation.

  本发明涉及一种在 5-HT₃ 受体上作为 5-HT 拮抗剂的化合物在治疗自闭症或另一种源于儿童期的精神发育迟滞疾病中的应用。
• Tetrahedron Asymmetry 1997, 8, 2367-2374
  作者：

  DOI：——

  日期：——
• TWO-PHASE MATRIX FOR SUSTAINED RELEASE DRUG DELIVERY DEVICE
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：EP0662822B1

  公开（公告）日：2001-01-03