6-chloro-7-methyl[1,2,4]triazolo[4,3-b]pyridazine | 58826-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并哒嗪类
• 英文名称: 6-chloro-7-methyl[1,2,4]triazolo[4,3-b]pyridazine
• 英文别名: 6-Chloro-7-methyl-[1,2,4]triazolo[4,3-b]pyridazine
• CAS: 58826-39-4
• 化学式: C₆H₅ClN₄
• 分子量: 168.585
• InChiKey: LQPOWKWRTDHADG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-7-methyl[1,2,4]triazolo[4,3-b]pyridazine 在 PPA 、 sodium hydride 作用下， 反应 25.0h， 生成 5-(2-Hydroxyethyl)-7-methyl-[1,2,4]triazolo[4,3-b]pyridazin-6-one
  参考文献：
  名称：

  Kosary, Judit, Heterocycles, 1992, vol. 34, # 5, p. 915 - 921

  摘要：

  DOI：
• 作为产物：
  描述：

  (6-氯-5-甲基哒嗪-3-基)肼 在 水 作用下， 生成 6-chloro-7-methyl[1,2,4]triazolo[4,3-b]pyridazine
  参考文献：
  名称：

  Takahayashi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 1242,1243

  摘要：

  DOI：

文献信息

• [EN] DERIVATIVES OF 6-SUBSTITUTED TRIAZOLOPYRIDAZINES AS REV-ERB AGONISTS<br/>[FR] DÉRIVÉS DE TRIAZOLOPYRIDAZINES 6-SUBSTITUÉES EN TANT QU'AGONISTES DE REV-ERB
  申请人：GENFIT

  公开号：WO2013045519A1

  公开（公告）日：2013-04-04

  The present invention provides novel 6-substituted [1,2,4]triazolo[4,3-b]pyridazines that are agonists of Rev-Erb. These compounds, and pharmaceutical compositions comprising the same, are suitable means for treating any disease wherein the activation of Rev-Erb has therapeutic effects, for instance in inflammatory and circadian rhythm-related disorders or cardiometabolic diseases.

  本发明提供了新颖的激动Rev-Erb的6-取代[1,2,4]三唑并[4,3-b]吡啶嗪化合物。这些化合物以及包含它们的药物组合物是治疗任何激活Rev-Erb具有治疗效果的疾病的合适手段，例如在炎症和昼夜节律相关疾病或心脏代谢疾病中。
• 3,6,7,8-Substituted-s-triazolo[4,3-b]pyridazines as bronchodilators
  申请人：The Dow Chemical Company

  公开号：US04526890A1

  公开（公告）日：1985-07-02

  3,6,7,8-Substituted-s-triazolo-pyridazine compounds such as 7,8-dimethyl-6-morpholino-3-methyl-s-triazolo[4,3-b]pyridazine or 7,8-dimethyl-6-(1-pyrrolidinyl)-3-(isopropyl)-s-triazolo-[4,3-b]pyridazine are prepared by the reaction of a carboxylic acid with a substituted 3-hydrazino-6-halo-pyridazine followed by the reaction of the resulting 6-halotriazolopyridazine with a corresponding base. The compounds have pharmacological activity as bronchodilators.

  3,6,7,8-取代-s-三唑吡啶化合物，如7,8-二甲基-6-吗啉基-3-甲基-s-三唑[4,3-b]吡啶或7,8-二甲基-6-(1-吡咯烷基)-3-(异丙基)-s-三唑-[4,3-b]吡啶，通过羧酸与取代的3-叠氮基-6-卤代吡啶的反应制备，然后通过所得的6-卤代三唑吡啶与相应的碱的反应制备。这些化合物具有支气管扩张剂的药理活性。
• Nucleophilic Substitution and Lipophilicity - Structure Relations in Methylazolopyridazines
  作者：Anna Katrusiak、Małgorzata Ratajczak-Sitarz、Urszula Skierska、Wiktoria Zinczenko

  DOI：10.1135/cccc20051372

  日期：——

  Syntheses of methyl[1,2,4]triazolo- or methyltetrazolopyridazine isomers, their separation and nucleophilic substitution with morpholine, dimethylamine and hydrazine have been described. The lipophilicity of the azolopyridazines has been measured and related to the number and sites of the methyl substituents. The structures of new methylated azolopyridazines have been characterized by ¹H NMR, MS spectra, and X-ray diffraction.

  合成了甲基[1,2,4]三唑基或甲基四唑基吡嗪的异构体，对它们进行了分离，并用吗啡啶、二甲胺和肼进行亲核取代。测量了吡唑吡啶的亲脂性，并与甲基取代基的数量和位置相关。新的甲基化吡唑吡啶的结构已通过1H NMR，MS光谱和X射线衍射表征。
• Vicarious nucleophilic substitution reactions in azolopyridazines controlled by methyl substituents
  作者：Anna Katrusiak

  DOI：10.1016/j.tetlet.2006.04.028

  日期：2006.6

  undergo annulation with simultaneous conventional ipso nucleophilic substitution of the chlorine at C6. Consequently, methyl substitution offers a convenient means of controlling the course of VNS carbanion substitution. These competitive reactions illustrate the role of charge distribution and steric hindrance for the course of the nucleophilic substitution, and the methylated azolopyridazines appear

  室温下，用溴甲基苯砜在DMSO– t -BuOK中用溴甲基苯砜处理时，偶氮哒嗪主要产生典型的VNS反应产物，而在相同条件下进行7-甲基偶氮哒嗪的环化反应则同时进行了C6处氯的常规ipso亲核取代。因此，甲基取代提供了控制VNS碳负离子取代过程的便捷方法。这些竞争性反应说明了电荷分布和空间位阻在亲核取代过程中的作用，甲基化的氮杂哒嗪类药物似乎是方便的底物，可用于在稠合的氮杂哒嗪系统中进行高效的建议环化反应。
• Triazolopyridazine derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05492909A1

  公开（公告）日：1996-02-20

  A compound of the formula: ##STR1## wherein R.sup.1 is a hydrogen atom, a lower alkyl group or a halogen atom; R.sup.2 and R.sup.3 are a hydrogen atom, a lower alkyl group or a 5- to 7-membered cyclic group formed together with the adjacent --C.dbd.C--; X is an oxygen atom, a sulfur atom or a methylene group; Y is an optionally substituted methylene group, a divalent 3- to 7-membered homo- or heterocyclic group; R.sup.6 and R.sup.7 are a hydrogen atom, a lower alkyl group, a cycloalkyl group, an aryl group, or a nitrogen-containing heterocyclic group formed together With the adjacent nitrogen atom; m is an integer of 0 to 4; and n is an integer of 0 to 4, or a salt thereof. Said compound has an excellent anti-PAF activity, antiallergic action, etc., thus is useful as an antiasthmatic agent.

  该化合物的化学式为：##STR1## 其中R.sup.1是氢原子、低碳基或卤素原子；R.sup.2和R.sup.3是氢原子、低碳基或与相邻的--C.dbd.C--一起形成的5-至7-成员环状基团；X是氧原子、硫原子或亚甲基基团；Y是可选取代的亚甲基基团、二价的3-至7-成员同源或异源环状基团；R.sup.6和R.sup.7是氢原子、低碳基、环状碳基、芳基或与相邻氮原子一起形成的含氮杂环基团；m是0至4的整数；n是0至4的整数，或其盐。该化合物具有优异的抗PAF活性、抗过敏作用等，因此可用作抗哮喘剂。