3-(2-cyano-4-pyridyl)-5-(2-chloro-4-pyridyl)-1,2,4-triazole | 577778-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(2-cyano-4-pyridyl)-5-(2-chloro-4-pyridyl)-1,2,4-triazole
• 英文别名: 4-[3-(2-chloropyridin-4-yl)-1H-1,2,4-triazol-5-yl]pyridine-2-carbonitrile
• CAS: 577778-84-8
• 化学式: C₁₃H₇ClN₆
• 分子量: 282.692
• InChiKey: LHHRYGILULYQQG-UHFFFAOYSA-N

物化性质

• 沸点：
  626.5±65.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-benzyloxymethyl-5-(2-cyano-pyridin-4-yl)-3-(2-chloro-pyridin-4-yl)-1,2,4-triazole 在 对甲苯磺酸 、 异丙醇 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 3-(2-cyano-4-pyridyl)-5-(2-chloro-4-pyridyl)-1,2,4-triazole
  参考文献：
  名称：

  EP1650204

  摘要：

  公开号：

文献信息

• Novel 1 2 4-triazole compound
  申请人：Nakamura Hiroshi

  公开号：US20050004175A1

  公开（公告）日：2005-01-06

  A novel 1,2,4-triazole compound which is useful as a therapeutic agent for hyperuricemia and gout due to hyperuricemia is provided. A compound is represented by the following general formula (1): wherein R 2 represents an unsubstituted or substituted pyridyl group, R 1 represents a similar pyridyl group, a pyridine-N-oxide group corresponding to these pyridyl groups, or a phenyl group, and R 3 represents hydrogen or a lower alkyl group substituted with pivaloyloxy group and R 3 bonds to a nitrogen atom in the ring. A process for production of a compound by reacting a nitrile and a hydrazide, and a therapeutic agent, particularly a xanthine oxidase inhibitor are also provided.

  提供了一种新型的1,2,4-三唑化合物，可用作治疗高尿酸血症和由高尿酸血症引起的痛风的治疗剂。该化合物由以下通式（1）表示：其中R2表示未取代或取代的吡啶基团，R1表示类似的吡啶基团，对应于这些吡啶基团的吡啶-N-氧化物基团或苯基团，而R3表示氢或取代有丁二酰氧基的低碳基团，且R3与环中的氮原子键合。还提供了通过反应腈和肼制备化合物的方法，以及治疗剂，特别是黄嘌呤氧化酶抑制剂。
• Process for producing 1,2,4-triazole compound and intermediate therefor
  申请人：Nakamura Hiroshi

  公开号：US20060189811A1

  公开（公告）日：2006-08-24

  Provided is a process for producing 1,2,4-triazole compound (5), or a salt or hydrate thereof which comprises reacting compound (1) with Rc-X (2) to give compound (3), reacting compound (3) with a nitrilization agent to give compound (4), and then removing the group Rc, as shown by the reaction scheme: (Wherein Ra, Rb and Rd represent a group, Rc represents a group which can be removed by an acid) A 1,2,4-triazole compound (5) having an optionally substituted 2-cyanopyridin-4-yl group at 3-position and an optionally substituted aromatic group at 5-position which inhibits a xanthine oxidase and is useful for treatment of gout and hyperuricemia can be obtained from compound (1) in a high yield without requiring isolation of reaction products in the course of reactions.

  提供一种生产1,2,4-三唑化合物(5)或其盐或水合物的方法，该方法包括将化合物(1)与Rc-X(2)反应得到化合物(3)，将化合物(3)与腈化试剂反应得到化合物(4)，然后去除Rc基团，如下反应方程所示:(其中，Ra、Rb和Rd代表一个基团，Rc代表可以通过酸去除的基团)从化合物(1)中可以高产得到一种1,2,4-三唑化合物(5)，其在3位具有可选取代的2-氰基吡啶-4-基基团，在5位具有可选取代的芳香基团，可以抑制黄嘌呤氧化酶，并且对于痛风和高尿酸血症的治疗有用，而不需要在反应过程中分离反应产物。
• PROCESS FOR PRODUCING 1,2,4-TRIAZOLE COMPOUND AND INTERMEDIATE THEREFOR
  申请人：Fujiyakuhin Co., Ltd.

  公开号：EP1650204A1

  公开（公告）日：2006-04-26

  Provided is a process for producing 1,2,4-triazole compound (5), or a salt or hydrate thereof which comprises reacting compound (1) with Rc-X (2) to give compound (3), reacting compound (3) with a nitrilization agent to give compound (4), and then removing the group Rc, as shown by the reaction scheme: (Wherein Ra, Rb and Rd represent a group, Rc represents a group which can be removed by an acid) A 1,2,4-triazole compound (5) having an optionally substituted 2-cyanopyridin-4-yl group at 3-position and an optionally substituted aromatic group at 5-position which inhibits a xanthine oxidase and is useful for treatment of gout and hyperuricemia can be obtained from compound (1) in a high yield without requiring isolation of reaction products in the course of reactions.

  本发明提供了一种生产 1，2，4-三唑化合物（5）或其盐或水合物的工艺，如反应方案所示，该工艺包括将化合物（1）与 Rc-X (2) 反应得到化合物（3），将化合物（3）与硝化剂反应得到化合物（4），然后除去基团 Rc： (其中 Ra、Rb 和 Rd 代表基团，Rc 代表可被酸去除的基团） 一种 1,2,4-三唑化合物(5)，在 3-位上有一个任选取代的 2-氰基吡啶-4-基团，在 5-位上有一个任选取代的芳香基团，可抑制黄嘌呤氧化酶，可用于治疗痛风和高尿酸血症，可以从化合物(1)高产率地得到，而不需要在反应过程中分离反应产物。
• Discovery of 3-(3-cyano-4-pyridyl)-5-(4-pyridyl)-1,2,4-triazole, FYX-051-a xanthine oxidoreductase inhibitor for the treatment of hyperuricemia
  作者：Takahiro Sato、Naoki Ashizawa、Koji Matsumoto、Takashi Iwanaga、Hiroshi Nakamura、Tsutomu Inoue、Osamu Nagata

  DOI：10.1016/j.bmcl.2009.08.091

  日期：2009.11

  Our previous study identified 2-[2-(2-methoxy-ethoxy)-ethoxy]-5-[5-(2-methyl-4-pyridyl)-1H-[1,2,4]-triazol-3-yl]-benzonitrile (2) as a safe and potent xanthine oxidoreductase (XOR) inhibitor for the treatment of hyperuricemia. Here, we synthesized a series of 3,5-dipyridyl-1,2,4-triazole derivatives and, in particular, examined their in vivo activity in lowering the serum uric acid levels in rats. As a result, we identified 3-(3-cyano-4-pyridyl)-5-(4-pyridyl)-1,2,4-triazole (FYX-051, compound 39) to be one of the most potent XOR inhibitors; it exhibited an extremely potent in vivo activity, weak CYP3A4-inhibitory activity and a better pharmacokinetic pro. le than compound 2. Compound 39 is currently being evaluated in a phase 2 clinical trial. (C) 2009 Elsevier Ltd. All rights reserved.
• NOVEL 1,2,4-TRIAZOLE COMPOUND
  申请人：Fuji Yakuhin Co., Ltd.

  公开号：EP1471065B1

  公开（公告）日：2008-02-27