3-phenoxy-1-azetidinecarboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-phenoxy-1-azetidinecarboxamide
• 英文别名: 3-(phenoxy)-1-azetidinecarboxamide；3-phenoxyazetidine-1-carboxamide
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: XQHOIPJEWVQKGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-phenoxyazetidine oxalate 、 硝基脲 在 三乙胺 作用下， 以 水 、 丙酮 为溶剂， 生成 3-phenoxy-1-azetidinecarboxamide
  参考文献：
  名称：

  Method of treating muscular tension, muscle spasticity and anxiety with

  摘要：

  披露了一种利用具有以下结构式的新型和已知的3-芳氧基和3-芳硫基氮杂环丙酰胺来治疗动物以获得肌肉松弛和/或缓解焦虑的方法：##STR1## 其中Z是氧或硫；B是氧或硫；Ar是吡啶基或卤代吡啶基，苯基或取代苯基；R.sup.1和R.sup.2是氢、较低烷基、芳基、烯丙基、丙炔基、环烷基、较低烷基环烷基、环烷基较低烷基、芳基较低烷基和二较低烷氨基烷基，当R.sup.1和R.sup.2与相邻的氮原子一起时，可能形成杂环胺基；R.sup.3是氢、较低烷基、芳基或芳基较低烷基，以及它们的几何异构体和可能的药用盐和水合物。

  公开号：

  US05068231A1

文献信息

• 3-aryloxy and 3-arylthioazetidinecarboxamides as anticonvulsants and
  申请人：A. H. Robins Company, Inc.

  公开号：US04956359A1

  公开（公告）日：1990-09-11

  Novel 3-aryloxy and 3-arylthioazetidinecarboxamides having utility in a method of treating convulsions and epilepsy and compositions therefor are disclosed having the formula: ##STR1## wherein Z is oxygen or sulfur; B is oxygen or sulfur; Ar is pyridyl or halo-substituted-pyridyl, phenyl or substituted phenyl; R.sup.1 and R.sup.2 are selected from hydrogen, loweralkyl, aryl, allyl, substituted allyl, propargyl, cycloalkyl, loweralkylcycloalkyl, cycloalkylloweralkyl, arylloweralkyl, diloweralkylaminoloweralkyl, and R.sup.1 and R.sup.2 when taken with the adjacent nitrogen atom may form a heterocyclic radical; R.sup.3 is hydrogen, loweralkyl, aryl or arylloweralkyl, and the geometrical isomers thereof, excepting that when R.sup.3 is hydrogen, Z is oxygen, B is oxygen, and Ar is phenyl or phenyl substituted by trifluoromethyl or aminocarbonyl, then R.sup.1 and R.sup.2 cannot be a combination of hydrogen and loweralkyl, and the further exception that when R.sup.3 is hydrogen, Z is oxygen, B is oxygen, and Ar is phenyl or phenyl substituted by fluoro, loweralkyl, loweralkoxy, trifluoromethyl, acetyl, or aminocarbonyl, then R.sup.1 and R.sup.2 cannot both be hydrogen.

  揭示了在治疗癫痫和癫痫发作的方法中具有实用性的新型3-芳氧基和3-芳硫基氮杂环丙酮酰胺及其组合物，其化学式为：##STR1## 其中Z为氧或硫；B为氧或硫；Ar为吡啶基或卤代吡啶基、苯基或取代苯基；R.sup.1和R.sup.2选自氢、较低烷基、芳基、烯丙基、取代烯丙基、丙炔基、环烷基、较低烷基环烷基、环烷基较低烷基、芳基较低烷基、二较低烷基氨基较低烷基，且当R.sup.1和R.sup.2与相邻的氮原子结合时可形成杂环基；R.sup.3为氢、较低烷基、芳基或芳基较低烷基及其几何异构体，但当R.sup.3为氢时，Z为氧，B为氧，Ar为苯基或三氟甲基或氨基羰基取代的苯基时，R.sup.1和R.sup.2不能同时为氢和较低烷基的组合，另外当R.sup.3为氢时，Z为氧，B为氧，Ar为苯基或氟代、较低烷基、较低氧烷基、三氟甲基、乙酰基或氨基羰基取代的苯基时，R.sup.1和R.sup.2不能同时为氢。
• N-formyl and n-hydroxymethyl-3-phenoxy-1-azetidinecarboxamides and their preparation and use
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0102740A1

  公开（公告）日：1984-03-14

  N-Formyl and N-hydroxymethy)-3-phenoxy-1-azetidinecarboxamides having the formula: wherein R is selected from formyl and hydroxymethyl and R' is selected from hydrogen, fluoro, loweralkyl, lower-alkoxy, trifluoromethyl, acetyl, N-formylcarboxamido or N-hydroxymethylcarboxamido having anticonvulsant activity are disclosed.

  N-甲酰基和 N-羟甲基）-3-苯氧基-1-氮杂环丁烷羧酰胺，其式如下 其中 R 选自甲酰和羟甲基，R'选自氢、氟、低级烷基、低级烷氧基、三氟甲基、乙酰基、N-甲酰基甲酰胺或 N-羟甲基甲酰胺，具有抗惊厥活性。
• Process for preparing 3-phenoxy-1-azetidines and carboxamide derivatives
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0131435A1

  公开（公告）日：1985-01-16

  A process for preparing 3-phenoxyazetidines uses a phase transfer catalyst to add the phenoxy group to azetidine blocked in the 1-position by a diphenylmethane group and uses a stabilizing tertiary amine base to prevent dimerization during hydrogenolysis to remove the blocking group. The crude product containing diphenylmethane may be used without purification to prepare 3-phenoxy-1-azetidine carboxamides.

  一种制备 3-苯氧基氮杂环丁烷的工艺使用相转移催化剂将苯氧基加到被二苯基甲烷基团封堵在 1 位的氮杂环丁烷上，并使用稳定叔胺碱防止在氢解过程中发生二聚反应以去除封堵基团。含有二苯基甲烷的粗产品无需纯化即可用于制备 3-苯氧基-1-氮杂环丁烷羧酰胺。
• 3-Aryl-oxyazetidinecarboxamides having anti-muscle tension, anti-muscle spasticity, anticonvulsant and antiepilectic activity
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0194112A1

  公开（公告）日：1986-09-10

  3-Aryloxyazetidinecarboxamides having the formula: wherein Z is oxygen or sulphur; Ar is pyridyl or halo substituted pyridyl, phenyl or substituted phenyl; R' and R2 are hydrogen, loweralkyl, aryl, allyl groups, propargyl, cycloalkyl, loweralkylcycloalkyl, cycloalkylloweralkyl, arylloweralkyl and diloweralkylshy aminoalkyl, and R' and R2 when taken together with the adjacent nitrogen atom may form a heterocyclic amine radical; R3 is hydrogen, loweralkyl, aryl, or arylloweralkyl, (including geometrical isomers thereof) and pharmaceutical salts thereof, when they are possible, have activity against muscle spasticity, muscle tension and anxiety. Certain of the compounds are new and have anticonvulsant activity.

  3-芳氧基氮杂环丁烷羧酰胺，其式如下 其中 Z 是氧或硫；Ar 是吡啶基或卤代吡啶基、苯基或取代苯基；R'和 R2 是氢、低级烷基、芳基、烯丙基、丙炔基、环烷基、低级环烷基、环烷低级烷基、芳低级烷基和稀低烷基氨基烷基，R'和 R2 与邻近的氮原子结合可形成杂环胺基；R3 是氢、低级烷基、芳基或芳基低级烷基（包括其几何异构体），其药物盐（如有可能）具有抗肌肉痉挛、肌肉紧张和焦虑的活性。其中某些化合物是新化合物，具有抗惊厥活性。
• Process for the synthesis of 3-phenoxy-1-azetidinecarboxamides
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0544475A1

  公开（公告）日：1993-06-02

  This invention relates to an improved process for the preparation of 3-phenoxy-1-azetidinecarboxamides of Formula I which are useful in the treatment of epileptic seizures. Under Formula I, n is 1 to 3, X is H, halogen, trifluoromethyl, C₁-C₄ alkyl, C₁-C₄ alkoxy, acetyl, or aminocarbonyl, and R is H or methyl. This process involves heating a 3-phenoxyazetidine with urea to obtain the Formula I compound. Urea is inexpensive and easily removed by washing the solid Formula I product with water.

  本发明涉及一种制备式 I 的 3-苯氧基-1-氮杂环丁烷羧酰胺的改进工艺，其用途如下 用于治疗癫痫发作。式 I 中，n 为 1 至 3，X 为 H、卤素、三氟甲基、C₁-C₄ 烷基、C₁-C₄ 烷氧基、乙酰基或氨基羰基，R 为 H 或甲基。该工艺包括将 3-苯氧基氮杂环丁烷与尿素一起加热，以获得式 I 化合物。尿素价格低廉，用水洗涤固态的式 I 产品即可轻松去除。