6-[(2-甲基-3-吡啶)氧基]-3-吡啶胺 | 181633-42-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-[(2-甲基-3-吡啶)氧基]-3-吡啶胺
• 中文别名: 6-((2-甲基吡啶-3-基)氧基)吡啶-3-胺；3-氨基-2-吡啶基,6-((2-甲基-3-吡啶基))醚
• 英文名称: [6-(2-methylpyridin-3-yloxy)pyridin-3-yl]amine
• 英文别名: 6-(2-methylpyridin-3-yloxy)-pyridin-3-ylamine；6-[(2-methyl-3-pyridinyl)oxy]-3-pyridinamine；5-amino-2-[(2-methyl-3-pyridyl)oxy]pyridine；3-amino-6-(2-methyl-pyridin-3-yloxy)pyridine；6-[(2-methylpyridin-3-yl)oxy]pyridin-3-amine；3-amino-6-(2-methyl-3-pyridyloxy)pyridine；6-((2-Methylpyridin-3-yl)oxy)pyridin-3-amine；6-(2-methylpyridin-3-yl)oxypyridin-3-amine
• CAS: 181633-42-1
• 化学式: C₁₁H₁₁N₃O
• 分子量: 201.228
• InChiKey: VNTXBOJIESFBJS-UHFFFAOYSA-N

物化性质

• 熔点：
  70-72 °C
• 沸点：
  382.7±42.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  6-[(2-甲基-3-吡啶)氧基]-3-吡啶胺 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 SB 242084双盐酸盐 水合物
  参考文献：
  名称：

  Biarylcarbamoylindolines Are Novel and Selective 5-HT_2C Receptor Inverse Agonists:  Identification of 5-Methyl-1-[[2-[(2-methyl-3-pyridyl)oxy]- 5-pyridyl]carbamoyl]-6-trifluoromethylindoline (SB-243213) as a Potential Antidepressant/Anxiolytic Agent

  摘要：

  The evolution, synthesis, and biological activity of a novel series of 5-HT2C receptor inverse agonists are reported. Biarylcarbamoylindolines have been identified with excellent 5-HT2C affinity and selectivity over 5-HT2A receptors. In addition, (pyridyloxypyridyl)carbamoylindolines have been discovered with additional selectivity over the closely related 5-HT2B receptor. Compounds from this series are inverse agonists at the human cloned 5-HT2C receptor, completely abolishing basal activity in a functional assay. The new series have reduced P450 inhibitory liability compared to a previously described series of 1-(3-pyridylcarbamoyl)indolines (Bromidge et al. J. Med. Chem. 1998, 41, 1598) from which they evolved. Compounds from this series showed excellent oral activity in a rat mCPP hypolocomotion model and in animal models of anxiety. On the basis of their favorable biological profile, 32 (SB-228357) and 40 (SB-243213) have been selected for further evaluation to determine their therapeutic potential for the treatment of CNS disorders such as depression and anxiety.

  DOI：

  10.1021/jm990388c
• 作为产物：
  描述：

  2-氯-5-硝基吡啶 在 盐酸 、 tin(II) chloride dihdyrate 、 sodium hydride 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 6.0h， 生成 6-[(2-甲基-3-吡啶)氧基]-3-吡啶胺
  参考文献：
  名称：

  吡啶氧基氧基吡啶基吲哚羧酰胺的合成和评估作为潜在的5-HT2C受体PET显像剂。

  摘要：

  合成了九种吡啶氧基氧基吡啶基吲哚羧酰胺，它们显示出对5-HT2C受体的高亲和力和对5-HT2A和5-HT2B的高选择性。其中，6-甲基-N- [6-[（2-甲基-3-吡啶基）氧基] -3-吡啶基] 1H-吲哚-3-羧酰胺（8）表现出最高的5-HT2C结合亲和力（Ki = 1.3 nM）和对5-HT2A（〜1000倍）和5-HT2B（〜140倍）的高选择性。[11C] 8是通过频哪醇硼酸酯16与[11C] CH3I之间的钯催化偶联反应合成的，平均放射化学产率为27±4％（n = 8，从[11C] CH3I合成结束时进行衰减校正）。在恒河猴中的MicroPET成像研究显示脉络丛中[11C] 8的区域摄取，而在所有其他脑区域中的结合均很低。通过给予0的阻断剂量可以确认脉络丛中的特异性结合。

  DOI：

  10.1021/acsmedchemlett.7b00443

文献信息

• N-coating heterocyclic compounds
  申请人：——

  公开号：US20030176454A1

  公开（公告）日：2003-09-18

  A compound of the formula (I): wherein A is a hydrogen atom, an optionally substituted, unsaturated, N-containing heterocyclic group or a group of the formula (a): wherein R is an optionally substituted aryl group or an optionally substituted heterocyclic group; M is —(CH 2 )n-, —(CH 2 )n-O—(CH 2 )m-or —(CH 2 )n-NH—(CH 2 )m-, wherein n and m are independently 0, 1 or 2; Q is an optionally substituted cycloalkylene group, an optionally substituted arylene group or an optionally substituted divalent heterocyclic group; and the moiety of the formula (b): is an optionally substituted, unsaturated, mono-, di-, tri- or tetra-cyclic, N-containing heterocyclic group which may contain additional hetero atom(s) selected from the group consisting of nitrogen, oxygen and sulfur atoms as the ring member(s), its prodrug or a pharmaceutically acceptable salt thereof.

  公式(I)的化合物：其中A是氢原子，一个可选地取代的、不饱和的、含氮的杂环基团，或者公式(a)的基团：其中R是一个可选地取代的芳香族基团或者一个可选地取代的杂环基团；M是—(CH2)n-, —(CH2)n-O—(CH2)m-或—(CH2)n-NH—(CH2)m-，其中n和m各自为0、1或2；Q是一个可选地取代的环烷基烯基团、一个可选地取代的芳香族基团或者一个可选地取代的二价杂环基团；以及公式(b)的部分：是一个可选地取代的、不饱和的、单环、双环、三环或四环的、含氮的杂环基团，它可以包含作为环成员的额外杂原子，选自由氮、氧和硫原子组成的组，其前药或药用盐。
• NOVEL INDOL CARBOXYLIC ACID BISPYRIDYL CARBOXAMIDE DERIVATIVES, PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, PREPARATION METHOD AND COMPOSITION CONTAINING THE SAME AS AN ACTIVE INGREDIENT
  申请人：SEONG Churlmin

  公开号：US20090258876A1

  公开（公告）日：2009-10-15

  Disclosed herein are a new indole carboxylic acid bispyridyl carboxamide derivative, a preparation method thereof, and a composition for prevention or treatment of obesity, urinary disorders, and CNS disorders, containing the same as an active ingredient. Because the indole carboxylic acid bispyridyl carboxamide derivatives according to the present invention have high affinity for 5-HT 2c receptors, act selectively on the 5-HT 2c receptors, the derivatives rarely have adverse effects caused by other receptors. Because the derivatives effectively inhibit serotonin activity, they may be useful for treatment or prevention of obesity; urinary disorders such as urinary incontinence, premature ejaculation, erectile dysfunction, and prostatic hyperplasia; CNS disorders such as depression, anxiety, concern, panic disorder, epilepsy, obsessive-compulsive disorder, migraine, sleep disorder, withdrawal from drug abuse, Alzheimer's disease, and schizophrenia, associated with 5-HT 2c receptors.

  本公开涉及一种新的吲哚羧酸双吡啶羧酰胺衍生物，其制备方法，以及包含该衍生物作为活性成分的用于预防或治疗肥胖、泌尿系统疾病和中枢神经系统疾病的组合物。根据本发明的吲哚羧酸双吡啶羧酰胺衍生物具有高亲和力5-HT2c受体，对5-HT2c受体选择性作用，这些衍生物很少出现由其他受体引起的不良反应。由于这些衍生物有效抑制5-羟色胺活性，它们可能对治疗或预防肥胖；泌尿系统疾病，如尿失禁、早泄、勃起功能障碍和前列腺增生；以及与5-HT2c受体相关的中枢神经系统疾病，如抑郁症、焦虑症、关注症、恐慌症、癫痫、强迫症、偏头痛、睡眠障碍、戒毒、阿尔茨海默病和精神分裂症可能有用。
• Therapeutic compounds
  申请人：——

  公开号：US20030149024A1

  公开（公告）日：2003-08-07

  The present invention provides compounds of Formula I: 1 wherein X, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 have any of the values defined in the specification, as well as pharmaceutical compositions comprising the compounds. The invention also provides therapeutic methods as well as processes and intermediates useful for preparing compounds of Formula I.

  本发明提供了公式I的化合物：1其中X，R1，R2，R3，R4，R5和R6具有规范中定义的任何值，以及包含该化合物的制药组合物。该发明还提供了治疗方法以及用于制备公式I化合物的过程和中间体。
• 吲哚啉类化合物的制备方法
  申请人：都创（上海）医药科技有限公司

  公开号：CN106278987A

  公开（公告）日：2017-01-04

  本发明公开了一种由以下通式1表示的吲哚啉类化合物的制备方法，所述方法通过采用一氯化碘、乙炔基三甲基硅烷等反应试剂成功地通过4步骤反应以高收率获得了6‑氯‑5‑甲基吲哚啉。根据本发明的吲哚啉衍生物的合成方法相对于现有技术而言减少了反应步骤，同时提高了反应产率。另外，反应条件温和，易于控制，有利于大规模工业化生产。
• Indoline derivatives useful as 5-HT-2C receptor antagonists
  申请人：SmithKline Beecham p.l.c.

  公开号：US06369060B1

  公开（公告）日：2002-04-09

  The invention relates to compounds of formula (I) or a salt thereof wherein X is CH or N; R1 is hydrogen or C1-6 alkyl; R2 and R3 groups are independently C1-6 alkyl, or trifluoromethyl, having pharmacological activity, processes for their preparation, compositions containing them and to their use in the treatment of CNS disorders such as anxiety.

  本发明涉及公式（I）的化合物或其盐，其中X为CH或N；R1为氢或C1-6烷基；R2和R3基团独立地为C1-6烷基或三氟甲基，具有药理活性，其制备过程，含有它们的组合物以及它们在治疗中枢神经系统疾病如焦虑症中的应用。