(E)-2-[[3,4-bis(difluoromethoxy)phenyl-1-oxo-2-propenyl]amino]benzoic acid | 1164144-88-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2-[[3,4-bis(difluoromethoxy)phenyl-1-oxo-2-propenyl]amino]benzoic acid
• 英文别名: 2-[(2E)-3-[3,4-bis(difluoromethoxy)phenyl]prop-2-enamido]benzoic acid；3',4'-bis-difluoromethoxycinnamoylanthranilate；(E)-2-[[3-(3,4-bis(difluoromethoxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid；(E)-2-[[3,4-bis(difluommethoxy)phenyl-1-oxo-2-propenyl]amino]benzoic acid；2-[[(E)-3-[3,4-bis(difluoromethoxy)phenyl]prop-2-enoyl]amino]benzoic acid
• CAS: 1164144-88-0
• 化学式: C₁₈H₁₃F₄NO₅
• 分子量: 399.299
• InChiKey: JOZKKPMJNMGHOQ-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (E)-2-[[3,4-bis(difluoromethoxy)phenyl-1-oxo-2-propenyl]amino]benzoic acid 在 乙酸酐 作用下， 反应 3.0h， 以86%的产率得到(E)-2-(3,4-bis(difluommethoxy)styryl)-4H-benzo[d][1,3]oxazin-4-one
  参考文献：
  名称：

  [EN] FUSED RING ANALOGUES OF ANTI-FIBROTIC AGENTS
  [FR] ANALOGUES À CYCLES CONDENSÉS D'AGENTS ANTI-FIBROTIQUES

  摘要：

  本发明涉及可能用作抗纤维化剂的芳基羰基和杂芳基羰基蒽酰胺化合物。本发明还涉及它们的制备方法、含有这些化合物的药物组合物以及这些化合物在治疗疾病中的用途。

  公开号：

  WO2011047432A1
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 哌啶 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.5h， 生成 (E)-2-[[3,4-bis(difluoromethoxy)phenyl-1-oxo-2-propenyl]amino]benzoic acid
  参考文献：
  名称：

  3′,4′-Bis-difluoromethoxycinnamoylanthranilate (FT061): An orally-active antifibrotic agent that reduces albuminuria in a rat model of progressive diabetic nephropathy

  摘要：

  Cinnamoylanthranilates including tranilast have been identified as promising antifibrotics that can reduce fibrosis occurring in the kidney during diabetes, thereby delaying and/or preventing kidney dysfunction. Structure-activity relationships aimed at improving potency and metabolic stability have led to the discovery of FT061. This compound, which bears a bis-difluoromethoxy catechol, attenuates TGF-beta-stimulated production of collagen in cultured renal mesangial cells (approx 50% at 3 mu M). When dosed orally at 20 mg/kg to male Sprague Dawley rats, FT061 exhibited a high bioavailability (73%), C-max of 200 mu M and T-max of 150 min, and a half-life of 5.4 h. FT061 reduced albuminuria when orally dosed in rats at 200 mg kg/day in a late intervention study of a rat model of progressive diabetic nephropathy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.100

文献信息

• [EN] HALOGENATED ANALOGUES OF ANTI-FIBROTIC AGENTS<br/>[FR] ANALOGUES HALOGÉNÉS D'AGENTS ANTIFIBROTIQUES
  申请人：FIBROTECH THERAPEUTICS PTY LTD

  公开号：WO2009079692A1

  公开（公告）日：2009-07-02

  The present invention relates to halogenated compounds of formula (I) with the substituents as described within the specification. The compounds may be useful as anti-fibrqtic agents. The present invention also relates to methods for their preparation.

  本发明涉及具有规定的取代基的式(I)的卤代化合物。这些化合物可能作为抗纤维化剂有用。本发明还涉及它们的制备方法。
• FUSED RING ANALOGUES OF ANTI-FIBROTIC AGENTS
  申请人：Fibrotech Therapeutics PTY LTD

  公开号：US20150266893A1

  公开（公告）日：2015-09-24

  The present invention relates to arylcarbonyl and heteroarylcarbonyl anthranilate compounds that may be useful as anti-fibrotic agents. The present invention also relates to methods for their preparation, pharmaceutical compositions containing these compounds and uses of these compounds in the treatment disorders.

  本发明涉及芳基羰基和杂环芳基羰基蒽酰胺化合物，这些化合物可能有用作为抗纤维化剂。本发明还涉及其制备方法、含有这些化合物的药物组合物以及这些化合物在治疗疾病方面的用途。
• METHODS OF TREATING EYE DISEASES ASSOCIATED WITH INFLAMMATION AND VASCULAR PROLIFERATION
  申请人：OccuRx Pty Ltd

  公开号：EP3485883A1

  公开（公告）日：2019-05-22

  Methods for treating eye diseases associated with inflammation and / or vascular proliferation in subjects are disclosed. The methods include administering therapeutically effective amounts of a tranilast compound, in particular (E)-2-[[3-(3-Methoxy-4-propargyloxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid or (E)-2-[[3,4-Bis(difluoromethoxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid or pharmaceutically acceptable salts or solvates thereof.

  本发明公开了治疗与受试者炎症和/或血管增生相关的眼部疾病的方法。这些方法包括给药治疗有效量的氨替司特化合物，特别是(E)-2-[[3-(3-甲氧基-4-丙炔氧基)苯基)-1-氧代-2-丙烯基]氨基]苯甲酸或(E)-2-[[3,4-双(二氟甲氧基)苯基)-1-氧代-2-丙烯基]氨基]苯甲酸或其药学上可接受的盐或溶液。
• Methods of treating eye diseases associated with inflammation and vascular proliferation
  申请人：Occurx Pty Ltd

  公开号：US10695353B2

  公开（公告）日：2020-06-30

  Methods for treating eye diseases associated with inflammation and/or vascular proliferation in subjects are disclosed. The methods include administering therapeutically effective amounts of a tranilast compound, in particular (E)-2-[[3-(3-Methoxy-4-propargyloxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid or (E)-2-[[3,4-Bis(difluoromethoxy)phenyl)-1-oxo-2-propenyl]amino]benzoic acid or pharmaceutically acceptable salts or solvates thereof.

  本发明公开了治疗与受试者炎症和/或血管增生相关的眼部疾病的方法。这些方法包括给药治疗有效量的氨替司特化合物，特别是(E)-2-[[3-(3-甲氧基-4-丙炔氧基)苯基)-1-氧代-2-丙烯基]氨基]苯甲酸或(E)-2-[[3,4-双(二氟甲氧基)苯基)-1-氧代-2-丙烯基]氨基]苯甲酸或其药学上可接受的盐或溶液。
• HALOGENATED ANALOGUES OF ANTI-FIBROTIC AGENTS
  申请人：Fibrotech Therapeutics PTY LTD

  公开号：EP2220028B1

  公开（公告）日：2016-03-09