2-(2-(3,4-bis(difluoromethoxy)phenyl)cyclopropanecarboxamido)benzoic acid

• 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: 2-(2-(3,4-bis(difluoromethoxy)phenyl)cyclopropanecarboxamido)benzoic acid
• 英文别名: 2-[[2-[3,4-Bis(difluoromethoxy)phenyl]cyclopropanecarbonyl]amino]benzoic acid
• 化学式: C₁₉H₁₅F₄NO₅
• 分子量: 413.325
• InChiKey: ITOPHTCFBLGYAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (E)-3-[3,4-bis(difluoromethoxy)phenyl]-2-propenoic acid 在 吡啶 、 草酰氯 、 硫酸 、 palladium diacetate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 2-(2-(3,4-bis(difluoromethoxy)phenyl)cyclopropanecarboxamido)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] ANALOGUES OF ANTI-FIBROTIC AGENTS<br/>[FR] ANALOGUES D'AGENTS ANTIFIBROTIQUES
  申请人：FIBROTECH THERAPEUTICS PTY LTD

  公开号：WO2010144959A1

  公开（公告）日：2010-12-23

  The present invention relates to analogues of anti-fibrotic agents having the formula (I) with the substituents as described within the specification. The present invention also relates to methods for their preparation.

  本发明涉及具有如规范中所述的取代基的抗纤维化剂的类似物，其化学式为(I)。本发明还涉及它们的制备方法。
• 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。
• US9839640B2
  申请人：——

  公开号：US9839640B2

  公开（公告）日：2017-12-12
• 3′,4′-Bis-difluoromethoxycinnamoylanthranilate (FT061): An orally-active antifibrotic agent that reduces albuminuria in a rat model of progressive diabetic nephropathy
  作者：Spencer J. Williams、Steven C. Zammit、Alison J. Cox、David M. Shackleford、Julia Morizzi、Yuan Zhang、Andrew K. Powell、Richard E. Gilbert、Henry Krum、Darren J. Kelly

  DOI：10.1016/j.bmcl.2013.09.100

  日期：2013.12

  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.