5-吡啶-4-基-1H-吡啶-2-酮 | 62749-34-2

• 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
• 中文名称: 5-吡啶-4-基-1H-吡啶-2-酮
• 英文名称: 1,2-dihydro-2-oxo-5-(4-pyridinyl)-pyridine
• 英文别名: 5-(4-pyridinyl)-2(1H)-pyridone；3,4'-bipyridin-6(1H)-one；5-(4-pyridinyl)-2(1H)-pyridinone；[3,4'-Bipyridin]-6(1H)-one；5-pyridin-4-yl-1H-pyridin-2-one
• CAS: 62749-34-2
• 化学式: C₁₀H₈N₂O
• 分子量: 172.186
• InChiKey: JLEJXZDPNYUTIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-吡啶-4-基-1H-吡啶-2-酮 在 三氯氧磷 作用下， 生成 6-氯-3,4-联吡啶
  参考文献：
  名称：

  5-(Pyridinyl)pyridine-2-hydrazines, their preparation and their

  摘要：

  2-[R.sub.1 NHN(R)]-3-Q'-5-Py-6-Q-吡啶或其药学上可接受的酸盐是作为心脏强心剂有用的化合物，其中Q为氢或较低的烷基，PY为4-或3-吡啶基或具有一个或两个较低的烷基取代基的4-或3-吡啶基，Q'为氢或卤素，R为氢、较低的烷基或较低的羟基烷基，而R.sub.1为氢或当R不是氢时，R.sub.1与R相同。这些化合物是通过将2-卤代-3-Q'-5-PY-6-Q-吡啶与R.sub.1 NHNHR反应制备的，其中2-卤代为溴或氯。还显示了：所述2-[R.sub.1 NN(R)]-3-Q'-5-PY-6-Q-吡啶作为心脏强心剂的用途；以及中间体2,3-二卤代-5-PY-6-Q-吡啶和它们从3-硝基-5-PY-6-Q-2（1H）-吡啶酮的制备。

  公开号：

  US04331672A1
• 作为产物：
  描述：

  N-ethoxycarbonylpyridinium chloride 在 palladium on activated charcoal copper(l) iodide 、 正丁基锂 、 氢气 、 氧气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 5-吡啶-4-基-1H-吡啶-2-酮
  参考文献：
  名称：

  Fang, Woei-Ping; Shieh, Puh; Shiao, Min-Jen, Heterocycles, 1986, vol. 24, # 6, p. 1585 - 1588

  摘要：

  DOI：

文献信息

• COMPOUNDS AND METHODS FOR TREATING INFLAMMATORY AND FIBROTIC DISORDERS
  申请人：Kossen Karl

  公开号：US20090318455A1

  公开（公告）日：2009-12-24

  Disclosed are compounds and methods for treating inflammatory and fibrotic disorders, including methods of modulating a stress activated protein kinase (SAPK) system with an active compound, wherein the active compound exhibits low potency for inhibition of the p38 MAPK; and wherein the contacting is conducted at a SAPK-modulating concentration that is at a low percentage inhibitory concentration for inhibition of the p38 MAPK by the compound. Also disclosed are derivatives and analogs of pirfenidone, useful for modulating a stress activated protein kinase (SAPK) system.

  公开了用于治疗炎症和纤维化疾病的化合物和方法，包括用活性化合物调节应激活化蛋白激酶（SAPK）系统的方法，其中活性化合物对p38 MAPK的抑制效力较低；并且其中接触是在SAPK调节浓度下进行的，该浓度对化合物抑制p38 MAPK的抑制浓度百分比较低。还公开了吡非尼酮的衍生物和类似物，它们可用于调节应激活化蛋白激酶（SAPK）系统。
• 5-(Pyridinyl)-2(1H)-pyridinones
  申请人：Sterling Drug Inc.

  公开号：US04107315A1

  公开（公告）日：1978-08-15

  Compounds useful as cardiotonic agents are 1-R-3-Q-5-PY-2(1H)-pyridinones (I) where R is hydrogen, lower-alkyl or lower-hydroxyalkyl, Q is amino (preferred), lower-alkylamino, di-(lower-alkyl)amino or NHAc, Ac is lower-alkanoyl or lower-carbalkoxy, and PY is 4- or 3- or 2-pyridinyl or 4- or 3- or 2-pyridinyl having one or two lower-alkyl substituents. The corresponding compounds where Q is nitro, carbamyl, cyano, halo or hydrogen are useful as intermediates and those where Q is hydrogen or cyano also are useful as cardiotonic agents. Said compounds are prepared: by reacting .alpha.-PY-.beta.-(R.sub.1 R.sub.2 N)acrolein (II) with malonamide to produce 1,2-dihydro-2-oxo-5-PY-nicotinamide (Ia) and reacting Ia with a reagent capable of converting carbamyl to amino to produce 3-amino-5-PY-2(1H)-pyridinone (Ib); by reacting II or .alpha.-PY-malonaldehyde (II') with .alpha.-cyanoacetamide to produce 1,2-dihydro-2-oxo-5-PY-nicotinonitrile (III) and partially hydrolyzing III to produce Ia; and, by heating 1,2-dihydro-2-oxo-5-PY-nicotinic acid (IV) with a mixture of concentrated sulfuric acid and concentrated nitric acid to produce 3-nitro-5-PY-2(1H)-pyridinone (Ic) and then either reducing Ic to produce Ib or first reacting Ic with an alkylating agent to produce 1-R'-3-nitro-5-PY-2(1H)-pyridinone (Id) and reducing Id to produce 1-R'-3-amino-5-PY-2(1H)-pyridinone (Ib) where R' is lower-alkyl or lower-hydroxyalkyl. Other derivatives of I where Q is amino are shown.

  作为心力衰竭药物有用的化合物是1-R-3-Q-5-PY-2(1H)-吡啶酮（I），其中R是氢、低烷基或低羟基烷基，Q是氨基（首选）、低烷基氨基、二（低烷基）氨基或NHAc，Ac是低脂肪酰基或低羰基脂肪酸酯，PY是具有一个或两个低烷基取代基的4-或3-或2-吡啶基或4-或3-或2-吡啶基。Q为硝基、氨基甲酰基、氰基、卤素或氢的相应化合物可用作中间体，Q为氢或氰基的化合物也可用作心力衰竭药物。所述化合物的制备方法包括：通过将.alpha.-PY-.beta.-(R1R2N)丙烯醛（II）与马来酰胺反应，生成1,2-二氢-2-氧-5-PY-烟酰胺（Ia），然后将Ia与能够将氨基甲酰转化为氨基的试剂反应，生成3-氨基-5-PY-2(1H)-吡啶酮（Ib）；通过将II或.alpha.-PY-马隆醛（II'）与.alpha.-氰基乙酰胺反应，生成1,2-二氢-2-氧-5-PY-烟酰腈（III），然后部分水解III，生成Ia；通过将1,2-二氢-2-氧-5-PY-烟酸（IV）与浓硫酸和浓硝酸的混合物加热，生成3-硝基-5-PY-2(1H)-吡啶酮（Ic），然后将Ic还原生成Ib，或者首先将Ic与烷基化剂反应生成1-R'-3-硝基-5-PY-2(1H)-吡啶酮（Id），再将Id还原生成1-R'-3-氨基-5-PY-2(1H)-吡啶酮（Ib），其中R'是低烷基或低羟基烷基。显示了Q为氨基的I的其他衍生物。
• Compositions and their preparation
  申请人：Sterling Drug Inc.

  公开号：US04276293A1

  公开（公告）日：1981-06-30

  2-R.sub.2 -3-R.sub.3 -6-PY-5-Q-3H-imidazo[4,5-b]pyridines (I) or 1-R.sub.1 -2-R.sub.2 -6-PY-5-Q-1H-imidazo[4,5-b]pyridines (IA) or pharmaceutically-acceptable acid-addition salts thereof, where Q and R.sub.2 are each hydrogen or lower-alkyl, R.sub.1 and R.sub.3 are each hydrogen, lower-alkyl, lower-hydroxyalkyl, 2,3-dihydroxypropyl, lower-alkoxyalkyl or Y-NB where Y is lower-alkylene having at least two carbon atoms between its connecting linkages and NB is di-(lower-alkyl)amino or 4-morpholinyl, at least one of R.sub.1 or R.sub.3 being hydrogen, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, which are useful as cardiotonics, are prepared by reacting 2-R.sub.3 NH-3-R.sub.1 NH-5-PY-6-Q-pyridine (II) with a tri-(lower-alkyl) ortho-(lower-alkanoate). Also shown are: the use of I or IA or salts in cardiotonic compositions and a method for increasing cardiac contractility; and, the preparation of the intermediates II, as well as intermediates used to prepare II.

  2-R.sub.2 -3-R.sub.3 -6-PY-5-Q-3H-咪唑并[4,5-b]吡啶（I）或1-R.sub.1 -2-R.sub.2 -6-PY-5-Q-1H-咪唑并[4,5-b]吡啶（IA）或其药用可接受的酸盐，其中Q和R.sub.2分别为氢或低烷基，R.sub.1和R.sub.3分别为氢、低烷基、低羟基烷基、2,3-二羟基丙基、低烷氧基烷基或Y-NB，其中Y为至少在其连接链之间具有两个碳原子的低烷基，NB为二（低烷基）氨基或4-吗啉基，R.sub.1或R.sub.3中至少一个为氢，PY为4-或3-吡啶基或带有一个或两个低烷基取代基的4-或3-吡啶基，这些化合物可用作心力衰竭药物，通过将2-R.sub.3 NH-3-R.sub.1 NH-5-PY-6-Q-吡啶（II）与三（低烷基）邻-(低烷酸酯)反应制备。还显示了：在心力衰竭药物组合物中使用I或IA或盐以及增加心脏收缩力的方法；以及用于制备II的中间体II的制备，以及用于制备II的中间体。
• 5-(Pyridinyl)pyridine-2,3-diamines, preparation thereof and their
  申请人：Sterling Drug Inc.

  公开号：US04297360A1

  公开（公告）日：1981-10-27

  2-R.sub.3 RN-3-R.sub.1 R'N-5-PY-6-Q-pyridines (I) or pharmaceutically-acceptable acid-addition salts thereof are useful as intermediates in the preparation of 1- or 3-substituted-1,3-dihydro-5-Q-6-PY-2H-imidazo[4,5-b]pyridin-2-ones or -2-thiones and also as intermediates for preparing 1- or 3-substituted-5-Q-6-PY-3H(or 1H)-imidazo[4,5-b]pyridines, where R.sub.1, R.sub.3, R, R', PY and Q are defined hereinbelow. Also shown are processes for preparing I and the following intermediates used therein: 2-halo-3-nitro-5-PY-6-Q-pyridines (III), 2-R.sub.3 RN-3-nitro-5-PY-6-Q-pyridines (V), 2-halo-5-PY-6-Q-pyridines (VII), 2-R.sub.3 RN-5-PY-6-Q-pyridines (VIII) and 2-R.sub.3 RN-3-halo-5-PY-6-Q-pyridines (IX) or salts thereof. Certain embodiments of II and VIII also are useful as cardiotonics and are shown as active components of cardiac compositions and methods for increasing cardiac contractility.

  2-R.sub.3 RN-3-R.sub.1 R'N-5-PY-6-Q-吡啶类化合物（I）或其药用可接受的酸盐在制备1-或3-取代-1,3-二氢-5-Q-6-PY-2H-咪唑[4,5-b]吡啶-2-酮或-2-硫酮以及制备1-或3-取代-5-Q-6-PY-3H（或1H）-咪唑[4,5-b]吡啶的中间体中是有用的，其中R.sub.1、R.sub.3、R、R'、PY和Q的定义如下。还显示了制备I及其中使用的以下中间体的过程：2-卤代-3-硝基-5-PY-6-Q-吡啶类化合物（III）、2-R.sub.3 RN-3-硝基-5-PY-6-Q-吡啶类化合物（V）、2-卤代-5-PY-6-Q-吡啶类化合物（VII）、2-R.sub.3 RN-5-PY-6-Q-吡啶类化合物（VIII）和2-R.sub.3 RN-3-卤代-5-PY-6-Q-吡啶类化合物（IX）或其盐。II和VIII的某些实施例也可用作强心剂，并显示为心脏组合物的活性成分和增加心脏收缩力的方法。
• 1,3-Dihydro-6-(pyridinyl)-2H-imidazo[4,5-b]pyridin-2-ones and
  申请人：Sterling Drug Inc.

  公开号：US04294837A1

  公开（公告）日：1981-10-13

  1,3-Dihydro-1-R.sub.1 -3-R.sub.3 -6-PY-5-Q-2H-imidazo[4,5-b]pyridin-2-ones or -2-thiones or pharmaceutically-acceptable acid-addition salts thereof, which are useful as cardiotonic agents, where Q is hydrogen or lower-alkyl, R.sub.1 and R.sub.3 are each hydrogen, lower-alkyl, lower-hydroxyalkyl, 2,3-dihydroxypropyl, lower-alkoxyalkyl or Y-NB where Y is lower-alkylene and NB is di-(lower-alkyl)amino or 4-morpholinyl, at least one of R.sub.1 and R.sub.3 being hydrogen, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two substituents, are prepared by reacting a 2-R.sub.3 NH-3-R.sub.1 NH-5-PY-6-Q-pyridine with urea or carbonyldiimidazole to produce said -2-one or with an alkali metal xanthate, thiourea or thiocarbonyldiimidazole to produce said -2-thione. Also shown and claimed are cardiotonic compositions and a method for increasing cardiac contractility using said cardiotonic agents. Also shown are processes for preparing said intermediate 2-R.sub.3 NH-3-R.sub.1 NH-5-PY-6-Q-pyridines and other intermediates used in said processes.

  1,3-二氢-1-R.sub.1-3-R.sub.3-6-PY-5-Q-2H-咪唑并[4,5-b]吡啶-2-酮或-2-硫酮或其药用可接受的酸加合物盐，可用作心力衰竭药物，其中Q为氢或较低烷基，R.sub.1和R.sub.3分别为氢、较低烷基、较低羟基烷基、2,3-二羟基丙基、较低烷氧基烷基或Y-NB，其中Y为较低烷基烯和NB为二-(较低烷基)氨基或4-吗啉基，R.sub.1和R.sub.3中至少有一个为氢，PY为4-或3-吡啶基或带有一个或两个取代基的4-或3-吡啶基，通过将2-R.sub.3 NH-3-R.sub.1 NH-5-PY-6-Q-吡啶与尿素或羰基二咪唑反应制备所述的-2-酮，或与碱金属黄原酸酯、硫脲或硫代羰基二咪唑反应制备所述的-2-硫酮。还显示并声称心力衰竭组合物和使用所述心力衰竭药物增加心脏收缩力的方法。还显示了制备所述中间体2-R.sub.3 NH-3-R.sub.1 NH-5-PY-6-Q-吡啶和所述过程中使用的其他中间体的方法。