5-(4-hydroxy-phenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile | 84462-84-0

• 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: 5-(4-hydroxy-phenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
• 英文别名: 5-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile；5-(4-hydroxyphenyl)-6-methyl-2-oxohydropyridine-3-carbonitrile；1,2-dihydro-5-(4-hydroxyphenyl)-6-methyl-2-oxonicotinonitrile；5-(4-hydroxyphenyl)-6-methyl-2-oxo-1H-pyridine-3-carbonitrile
• CAS: 84462-84-0
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: XUXGMIWDGMXMNT-UHFFFAOYSA-N

物化性质

• 沸点：
  481.7±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  73.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-hydroxy-phenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile 生成 5-(4-hydroxyphenyl)-6-methyl-2(1H)-pyridinone
  参考文献：
  名称：

  LESHER, G. Y.;OPALKA, CH. J.;PAGE, D. F.;MCGARRY, R. M.

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(4-甲氧基苯基)-6-甲基-2-氧代-1H-吡啶-3-腈 在 三溴化硼 、 氯化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 7.0h， 以46%的产率得到5-(4-hydroxy-phenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  [EN] DIHYDROPYRIDINE COMPOUNDS HAVING SIMULTANEOUS ABILITY TO BLOCK L-TYPE CALCIUM CHANNELS AND TO INHIBIT PHOSPHODIESTERASE TYPE 3 ACTIVITY
  [FR] COMPOSES DE DIHYDROPYRIDINE PRESENTANT A LA FOIS LA CAPACITE DE BLOQUER DES CANAUX CALCIQUES DE TYPE L ET LA CAPACITE D'INHIBER L'ACTIVITE DE TYPE 3 DE LA PHOSPHODIESTERASE

  摘要：

  本发明提供了具有对PDE-3和L型钙通道具有抑制活性的化合物。本发明还提供了包含这些化合物的药物组合物以及使用这些化合物治疗心血管疾病、中风、癫痫、眼科疾病或偏头痛的方法。

  公开号：

  WO2004033444A1

文献信息

• 5-(Hydroxy- and/or amino-phenyl)-6-(lower-alkyl)-2-(1H)-pyridinones,
  申请人：Sterling Drug Inc.

  公开号：US04465686A1

  公开（公告）日：1984-08-14

  Disclosed and claimed is the cardiotonic use of 1-R.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (II), where R.sub.1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is lower-alkyl or hydrogen, and, R' and R" are each hydrogen, amino or hydroxy, at least one of R' or R" being other than hydrogen, or where R' is nitro when R" is hydroxy, or pharmaceutically acceptable acid-addition salts thereof where at least one of R' and R" is amino. Also disclosed and claimed are 1-R.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (I), where R.sub.1, R' and R" are defined as above and R is lower-alkyl and acid-addition salts thereof where at least one of R' and R" is amino. Also shown and claimed is the process which comprises reacting 1-R.sub.1 -1,2-dihydro-2-oxo-5-(3-R'-4-R"-phenyl)-6-R-nicotinonitrile, where R.sub.1 and R are defined as above for II, R' is hydrogen, hydroxy, methoxy or amino and R" is hydroxy, methoxy or hydrogen, preferably at least one of R' and R" being methoxy, or where R' is nitro and R" is hydrogen or methoxy, preferably methoxy, with 85% phosphoric acid to produce 1-R.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinone.

  揭示和声明了1-R.sub.1 -5-(3-R'-4-R"-苯基)-6-R-2(1H)-吡啶酮（II）的强心作用，其中R.sub.1为氢、低烷基或低羟基烷基，R为低烷基或氢，R'和R"分别为氢、氨基或羟基，其中至少有一个R'或R"不是氢，或者当R"为羟基时，R'为硝基，或其药学上可接受的酸加合物盐，其中至少一个R'和R"为氨基。还揭示和声明了1-R.sub.1 -5-(3-R'-4-R"-苯基)-6-R-2(1H)-吡啶酮（I），其中R.sub.1、R'和R"的定义如上所述，R为低烷基，以及其药学上可接受的酸加合物盐，其中至少一个R'和R"为氨基。还显示和声明了一种过程，包括将1-R.sub.1 -1,2-二氢-2-氧代-5-(3-R'-4-R"-苯基)-6-R-烟酸腈与85%磷酸反应，其中R.sub.1和R的定义如上所述用于II，R'为氢、羟基、甲氧基或氨基，R"为羟基、甲氧基或氢，最好是R'和R"中至少一个为甲氧基，或者当R'为硝基且R"为氢或甲氧基时，最好为甲氧基，以产生1-R.sub.1 -5-(3-R'-4-R"-苯基)-6-R-2(1H)-吡啶酮。
• 3-Amino-5-(hydroxy- and/or
  申请人：Sterling Drug Inc.

  公开号：US04515797A1

  公开（公告）日：1985-05-07

  1-R.sub.1 -3-amino-5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones or salts thereof, which are useful as cardiotonics, where R.sub.1 is hydrogen, lower-alkyl, or lower-hydroxyalkyl, R is hydrogen or lower-alkyl, and, R' and R" are each hydrogen, hydroxy or amino at least one of R' or R" being other than hydrogen, are prepared by reacting the corresponding 3-carbamyl compound with a reagent capable of converting carbamyl to amino or by first reacting the corresponding 3-carbamyl compound where R' and R" are each hydrogen, nitro or lower-alkoxy at least one of R' and R" being other than hydrogen with a reagent capable of converting carbamyl to amino and then reacting the resulting 3-amino compound where R' and/or R" are/is lower-alkoxy and/or nitro with a reagent capable of converting lower-alkoxy to hydroxy and/or with a reagent capable of converting nitro to amino. Preparation of the corresponding 3-carbamyl and 3-cyano compounds is shown, the latter including cardiotonically active novel 1-R.sub.1 -1,2-dihydro-5-(3-R.sub.2 -4-R.sub.3 -phenyl)-6-R-nicotinonitriles where R.sub.1 and R are defined as above, and R.sub.2 and R.sub.3 have the above given definitions for R' and R" or where R.sub.2 is nitro and R.sub.3 is hydroxy. Also shown are cardiotonic compositions and cardiotonic method of use of above-said compounds.

  1-R.sub.1 -3-氨基-5-(3-R'-4-R"-苯基)-6-R-2(1H)-吡啶酮或其盐，可用作心脏强心剂，其中R.sub.1是氢、低烷基或低羟基烷基，R是氢或低烷基，R'和R"分别是氢、羟基或氨基，其中R'或R"至少有一个不是氢，通过将相应的3-氨基甲酰化合物与能够将氨基甲酰转化为氨基的试剂反应制备，或者首先将R'和R"分别是氢、硝基或低烷氧基，其中R'和R"中至少有一个不是氢的相应的3-氨基甲酰化合物与能够将氨基甲酰转化为氨基的试剂反应，然后将所得的3-氨基化合物与能够将低烷氧基转化为羟基和/或能够将硝基转化为氨基的试剂反应，其中R'和/或R"是低烷氧基和/或硝基。显示了相应的3-氨基甲酰和3-氰基化合物的制备，后者包括具有心脏强心活性的新颖的1-R.sub.1 -1,2-二氢-5-(3-R.sub.2 -4-R.sub.3 -苯基)-6-R-烟酰腈，其中R.sub.1和R如上所定义，R.sub.2和R.sub.3具有上述给定的R'和R"的定义，或者其中R.sub.2是硝基，R.sub.3是羟基。还显示了心脏强心剂组合物和上述化合物的心脏强心方法的用途。
• Pyridone nitriles useful in treating cardiovascular disease
  申请人：Glaxo Inc.

  公开号：US05051431A1

  公开（公告）日：1991-09-24

  Pyridones of formula (I) for treating congestive heart failure: ##STR1## wherein: R.sup.1 and R.sup.2 are a variety of phenyl substituents, L is a divalent alkylene or amide containing alkylene linking group. Pharmaceutical composition, methods for their use in treating cardiovascular conditions, processes used in synthesis and intermediates used in such processes.

  公式（I）的吡啶酮化合物，用于治疗充血性心力衰竭：##STR1## 其中：R.sup.1和R.sup.2是各种苯基取代基，L是双价的烷基或含有烷基连接基的酰胺。制药组合物，用于治疗心血管疾病的方法，用于合成的过程和用于这些过程中的中间体。
• Compounds having simultaneous ability to block L-type calcium channels and to inhibit phosphodiesterase type 3 activity
  申请人：ARTESIAN THERAPEUTICS, INC.

  公开号：US20040242648A1

  公开（公告）日：2004-12-02

  The present invention provides compounds that possess inhibitory activity against PDE-3 and L-type calcium channels. The present invention further provides pharmaceutical compositions comprising such compounds and methods of using such compounds for treating cardiovascular disease, stroke, epilepsy, ophthalmic disorder or migraine.

  本发明提供了具有对PDE-3和L型钙通道的抑制活性的化合物。本发明还提供了包含这种化合物的药物组合物和使用这种化合物治疗心血管疾病、中风、癫痫、眼科疾病或偏头痛的方法。
• Dihydropyridine vasodilators agents
  申请人：Glaxo Inc.

  公开号：US05258519A1

  公开（公告）日：1993-11-02

  Compounds of the following formula (I): ##STR1## where R.sup.1 and R.sup.2 are alkyl or cycloalkyl, which may be substituted, R.sup.4 is aryl such as phenyl which may be substituted, L is a direct bond or an oxygen containing linking group, R is a hydrogen, alkyloxy, alkyl, halogen or haloalkyl and Het is a pyridinyl or pyridazinyl group. The compounds can be used antihypertensives or myocardial relaxants. Also part of the invention are pharmaceutical compositions, intermediates and methods of synthesis.

  以下式子（I）的化合物：##STR1##其中R.sup.1和R.sup.2是烷基或环烷基，可能被取代，R.sup.4是芳基，例如苯基，可能被取代，L是直接键或含氧连接基，R是氢、烷氧基、烷基、卤素或卤代烷基，Het是吡啶基或吡嗪基。这些化合物可用作降压剂或心肌松弛剂。此外，该发明还涉及制药组合物、中间体和合成方法。