methyl 5-(5-methyl-1,2,4-oxadiazol-3-yl)-2-thiophenecarboxylate | 133380-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: methyl 5-(5-methyl-1,2,4-oxadiazol-3-yl)-2-thiophenecarboxylate
• 英文别名: methyl 5-(5-methyl-1,2,4-oxadiazol-3-yl)thiophene-2-carboxylate
• CAS: 133380-62-8
• 化学式: C₉H₈N₂O₃S
• 分子量: 224.24
• InChiKey: WQIRCRDOHVDOGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  93.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-(5-methyl-1,2,4-oxadiazol-3-yl)-2-thiophenecarboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以88%的产率得到5-(5-methyl-1,2,4-oxadiazol-3-yl)-2-thiophenecarboxylic acid
  参考文献：
  名称：

  5-杂芳基-2-噻吩羧酸：恶唑和恶二唑

  摘要：

  报道了带有烷基和芳基取代的恶唑和恶二唑环的新型噻吩-2-羧酸的合成。关键前体5-甲酰基-2-噻吩羧酸的顺序官能化提供了中间体羧酸酯，其通过碱性裂解被转化为所需的酸。

  DOI：

  10.1002/jhet.5570280104
• 作为产物：
  描述：

  5-醛基-2-噻吩甲酸 在 吡啶 、 盐酸羟胺 、 sodium acetate 、 乙酸酐 、 sodium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 27.0h， 生成 methyl 5-(5-methyl-1,2,4-oxadiazol-3-yl)-2-thiophenecarboxylate
  参考文献：
  名称：

  5-杂芳基-2-噻吩羧酸：恶唑和恶二唑

  摘要：

  报道了带有烷基和芳基取代的恶唑和恶二唑环的新型噻吩-2-羧酸的合成。关键前体5-甲酰基-2-噻吩羧酸的顺序官能化提供了中间体羧酸酯，其通过碱性裂解被转化为所需的酸。

  DOI：

  10.1002/jhet.5570280104

文献信息

• 3-substituted-2-oxindole derivatives
  申请人：Pfizer Inc.

  公开号：US05047554A1

  公开（公告）日：1991-09-10

  This invention relates to novel 3-substituted-2-oxindole derivatives which are inhibitors of prostaglandin H.sub.2 synthase, 5-lipoxygenase and interleukin-1 biosynthesis. The compounds of the invention are useful as inhibitors of prostaglandin H.sub.2 synthase and interleukin-1 biosynthesis, per se, and as analgesic, antiinflammatory and antiarthritic agents in the treatment of chronic inflammatory diseases. This invention also relates to pharmaceutical compositions comprising said 3-substituted-2-oxindole derivatives; to methods of inhibiting prostaglandin H.sub.2 synthase and biosynthesis of interleukin-1; and to treating chronic inflammatory diseases in a mammal with said compounds. Further, this invention relates to certain novel carboxylic acids useful as intermediates in the preparation of the 3-substituted-2-oxindole derivatives of this invention and to a process for the preparation of the 3-substituted-2-oxindole derivatives.

  这项发明涉及新型的3-取代-2-噁唑烷酮衍生物，这些衍生物是前列腺素H.sub.2合酶、5-脂氧合酶和白细胞介素-1生物合成的抑制剂。该发明的化合物在慢性炎症性疾病的治疗中可用作前列腺素H.sub.2合酶和白细胞介素-1生物合成的抑制剂，本身也可作为镇痛、抗炎和抗关节炎药物。本发明还涉及包含所述3-取代-2-噁唑烷酮衍生物的药物组合物；抑制前列腺素H.sub.2合酶和白细胞介素-1生物合成的方法；以及使用这些化合物治疗哺乳动物的慢性炎症性疾病。此外，本发明还涉及某些新型羧酸，可用作本发明的3-取代-2-噁唑烷酮衍生物的合成中间体，以及一种制备这些衍生物的方法。
• 2-carboxy-thiophene derivatives
  申请人：Pfizer Inc.

  公开号：US05300655A1

  公开（公告）日：1994-04-05

  This invention relates to novel 3-substituted-2-oxindole derivatives which are inhibitors of prostaglandin H.sub.2 synthase, 5-lipoxygenase and interleukin-1 biosynthesis. The compounds of the invention are useful as inhibitors of prostaglandin H.sub.2 synthase and interleukin-1 biosynthesis, per se, and as analgesic, antiinflammatory and antiarthritic agents in the treatment of chronic inflammatory diseases. This invention also relates to pharmaceutical compositions comprising said 3-substituted-2-oxindole derivatives; to methods of inhibiting prostaglandin H.sub.2 synthase and biosynthesis of interleukin-1; and to treating chronic inflammatory diseases in a mammal with said compounds. Further, this invention relates to certain novel carboxylic acids useful as intermediates in the preparation of the 3-substituted-2-oxindole derivatives of this invention and to a process for the preparation of the 3-substituted-2-oxindole derivatives.

  本发明涉及新型的3-取代-2-氧化吲哚衍生物，其是前列腺素H.sub.2合酶、5-脂氧合酶和白细胞介素-1生物合成的抑制剂。本发明中的化合物本身作为前列腺素H.sub.2合酶和白细胞介素-1生物合成的抑制剂以及作为治疗慢性炎症性疾病的镇痛、抗炎和抗关节炎药物是有用的。本发明还涉及包含所述3-取代-2-氧化吲哚衍生物的制药组合物；抑制前列腺素H.sub.2合酶和白细胞介素-1生物合成的方法；以及使用该化合物治疗哺乳动物的慢性炎症性疾病。此外，本发明还涉及某些新型羧酸，其作为制备本发明的3-取代-2-氧化吲哚衍生物的中间体，以及制备3-取代-2-氧化吲哚衍生物的过程。
• 3-substituted-2-oxindoles derivatives
  申请人：Pfizer Inc.

  公开号：US06174883B1

  公开（公告）日：2001-01-16

  This invention relates to novel 3-substituted-2-oxindole derivatives of the formula and the phamaceutically-accepted salts thereof which are inhibitors of prostaglandin H2 synthase, 5-lipoxygenase and interleukin-1 biosynthesis. The compounds of the invention are useful as inhibitors of prostaglandin H2 synthase and interleukin-1 biosynthesis, per se, and as analgesic, antiinflammatory and antiarthritic agents in the treatment of chronic inflammatory diseases. This invention also relates to pharmaceutical compositions comprising said 3-substituted-2-oxindole derivatives; to methods of inhibiting prostaglandin H2 synthase and biosynthesis of interleukin-1; and to treating chronic inflammatory diseases in a mammal with said compounds. Further, this invention relates to certain novel carboxylic acids useful as intermediates in the preparation of the 3-substituted-2-oxindole derivatives of this invention and to a process for the preparation of the 3-substituted-2-oxindole derivatives.

  本发明涉及一种新的3-取代-2-氧化吲哚衍生物及其药物接受的盐，它们是前列腺素H2合酶、5-脂氧合酶和白细胞介素-1生物合成的抑制剂。本发明的化合物本身就是前列腺素H2合酶和白细胞介素-1生物合成的抑制剂，可用于治疗慢性炎症性疾病的镇痛、抗炎和抗关节炎药物。本发明还涉及包括所述3-取代-2-氧化吲哚衍生物的制药组合物；抑制前列腺素H2合酶和白细胞介素-1的生物合成的方法；以及使用该化合物治疗哺乳动物的慢性炎症性疾病。此外，本发明还涉及一些新的羧酸，可用作制备本发明的3-取代-2-氧化吲哚衍生物的中间体，以及制备3-取代-2-氧化吲哚衍生物的方法。
• COMPOUNDS AND METHODS
  申请人：Baloglu Erkan

  公开号：US20130059883A1

  公开（公告）日：2013-03-07

  Disclosed are compounds having the formula: wherein X 1 , X 2 , X 3 , R 1 , R 2 , R 3 , R 4 , Y, A, Z, L and n are as defined herein, and methods of making and using the same.

  公开的化合物具有以下公式：其中X1，X2，X3，R1，R2，R3，R4，Y，A，Z，L和n的定义如下，以及制备和使用它们的方法。
• 3-substituted-2-oxindole derivatives as antiinflammatory agents
  申请人：PFIZER INC.

  公开号：EP0393936A1

  公开（公告）日：1990-10-24

  This invention relates to novel 3-substituted-2-oxindole derivatives which are inhibitors of prostaglandin H2 synthase, 5-lipoxygenase and interleukin-1 biosynthesis. The compounds of the invention are useful as inhibitors of prostaglandin H2 synthase and interleukin-1 biosynthesis, per se, and as analgesic, antiinflammatory and antiarthritic agents in the treatment of chronic inflammatory diseases. This invention also relates to pharmaceutical compositions comprising said 3-substituted-2-oxindole derivatives; to methods of inhibiting prostaglandin H2 synthase and biosynthesis of interleukin-1; and to treating chronic inflammatory diseases in a mammal with said compounds. Further, this invention relates to certain novel carboxylic acids useful as intermediates in the preparation of the 3-substituted-2-oxindole derivatives of this invention and to a process for the preparation of the 3-substituted-2-oxindole derivatives.

  本发明涉及新型 3-取代-2-氧化吲哚衍生物，它们是前列腺素 H2 合酶、5-脂氧合酶和白细胞介素-1 生物合成的抑制剂。本发明的化合物本身可用作前列腺素 H2 合酶和白细胞介素-1 生物合成的抑制剂，也可用作治疗慢性炎症性疾病的镇痛、抗炎和抗关节炎药物。本发明还涉及包含所述 3-取代-2-氧化吲哚衍生物的药物组合物；涉及抑制前列腺素 H2 合酶和白细胞介素-1 生物合成的方法；涉及用所述化合物治疗哺乳动物的慢性炎症疾病。此外，本发明还涉及某些可用作制备本发明 3-取代-2-吲哚衍生物中间体的新型羧酸，以及制备 3-取代-2-吲哚衍生物的工艺。