Methyl 3-(4-cyanobenzyloxy)-5-isoxazolecarboxylate | 169605-37-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 3-(4-cyanobenzyloxy)-5-isoxazolecarboxylate
• 英文别名: Methyl 3-[(4-cyanophenyl)methoxy]-1,2-oxazole-5-carboxylate
• CAS: 169605-37-2
• 化学式: C₁₃H₁₀N₂O₄
• 分子量: 258.233
• InChiKey: WVLBDGSIRUGAIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 3-(4-cyanobenzyloxy)-5-isoxazolecarboxylate 在 lithium hydroxide 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-Butoxycarbonylamino-3-{[3-(4-cyano-benzyloxy)-isoxazole-5-carbonyl]-amino}-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis and antiplatelet effects of an isoxazole series of glycoprotein IIb/IIIa antagonists

  摘要：

  Despite the excellent in vitro potency of a series of benzamide glycoprotein IIb/IIIa antagonists, which have been reported previously, poor in vivo potency in the inhibition of platelet aggregation was observed when the most potent inhibitor XU057 was dosed intravenously to dogs. In this communication, we report that replacement of the benzamide in XU057 with an isoxazolecarboxamide resulted in significant improvement in in vivo potency. More importantly, the analogue XU065 showed an excellent oral antiplatelet effect in dogs. (C) 1998 The DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00637-4
• 作为产物：
  描述：

  对氰基溴化苄 、 3-羟基异恶唑-5-甲酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到Methyl 3-(4-cyanobenzyloxy)-5-isoxazolecarboxylate
  参考文献：
  名称：

  Synthesis and antiplatelet effects of an isoxazole series of glycoprotein IIb/IIIa antagonists

  摘要：

  Despite the excellent in vitro potency of a series of benzamide glycoprotein IIb/IIIa antagonists, which have been reported previously, poor in vivo potency in the inhibition of platelet aggregation was observed when the most potent inhibitor XU057 was dosed intravenously to dogs. In this communication, we report that replacement of the benzamide in XU057 with an isoxazolecarboxamide resulted in significant improvement in in vivo potency. More importantly, the analogue XU065 showed an excellent oral antiplatelet effect in dogs. (C) 1998 The DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00637-4

文献信息

• Aromatic compounds containing basic and acidic termini useful as
  申请人：The Dupont Merck Pharmaceutical Company

  公开号：US05563158A1

  公开（公告）日：1996-10-08

  This invention relates to novel compounds containing basic and acidic termini, pharmaceutical compositions containing such compounds, processes for preparing such compounds, and to methods of using these compounds, alone or in combination with other therapeutic agents, for the inhibition of platelet aggregation, as thrombolytics, and/or for the treatment of thromboembolic disorders.

  这项发明涉及含有碱性和酸性末端的新化合物，包含这些化合物的药物组合物，制备这些化合物的方法，以及使用这些化合物的方法，单独或与其他治疗剂结合，用于抑制血小板聚集，作为溶栓剂，和/或用于治疗血栓栓塞性疾病。
• [EN] COMPOUNDS CONTAINING BASIC AND ACIDIC TERMINI USEFUL AS FIBRINOGEN RECEPTOR ANTAGONISTS<br/>[FR] COMPOSES CONTENANT DES TERMINAISONS BASIQUES ET ACIDES UTILES EN TANT QU'ANTAGONISTES DES RECEPTEURS DE FIBRINOGENE
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：WO1995018111A1

  公开（公告）日：1995-07-06

  (EN) This invention relates to novel compounds containing basic and acidic termini, pharmaceutical compositions containing such compounds, processes for preparing such compounds, and to methods of using these compounds, alone or in combination with other therapeutic agents, for the inhibition of platelet aggregation, as thrombolytics, and/or for the treatment of thromboembolic disorders.(FR) Nouveaux composés contenant des terminaisons basiques et acides, compositions pharmaceutiques contenant lesdits composés, procédés pour préparer lesdits composés et procédés d'utilisation desdits composés, seuls ou en combinaison avec d'autres agents thérapeutiques, afin d'inhiber l'agrégation plaquettaire, afin de servir d'agents thrombolytiques, et/ou afin de traiter des troubles thromboemboliques.

  该发明涉及新型化合物，其含有碱性和酸性末端，含有这种化合物的制药组合物，制备这种化合物的方法，以及使用这些化合物的方法，单独或与其他治疗剂联合使用，用于抑制血小板聚集，作为溶栓剂以及治疗血栓栓塞性疾病。
• US5563158A
  申请人：——

  公开号：US5563158A

  公开（公告）日：1996-10-08
• US5691329A
  申请人：——

  公开号：US5691329A

  公开（公告）日：1997-11-25
• Synthesis and antiplatelet effects of an isoxazole series of glycoprotein IIb/IIIa antagonists
  作者：Chu-Biao Xue、John Roderick、Shaker Mousa、Richard E. Olson、William F. DeGrado

  DOI：10.1016/s0960-894x(98)00637-4

  日期：1998.12

  Despite the excellent in vitro potency of a series of benzamide glycoprotein IIb/IIIa antagonists, which have been reported previously, poor in vivo potency in the inhibition of platelet aggregation was observed when the most potent inhibitor XU057 was dosed intravenously to dogs. In this communication, we report that replacement of the benzamide in XU057 with an isoxazolecarboxamide resulted in significant improvement in in vivo potency. More importantly, the analogue XU065 showed an excellent oral antiplatelet effect in dogs. (C) 1998 The DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.