5-[4-(三氟甲基)苯氧基]吡啶-2-羧酸 | 72133-40-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-[4-(三氟甲基)苯氧基]吡啶-2-羧酸
• 英文名称: 5-[4-(trifluoromethyl)phenoxy]pyridine-2-carboxylic acid
• 英文别名: 5-(p-trifluoromethylphenoxy)picolinic acid；Picolinic acid, 5-(alpha,alpha,alpha-trifluoro-p-tolyloxy)-
• CAS: 72133-40-5
• 化学式: C₁₃H₈F₃NO₃
• 分子量: 283.207
• InChiKey: JXPYTHDXGAGHBU-UHFFFAOYSA-N

物化性质

• 沸点：
  389.9±42.0 °C(Predicted)
• 密度：
  1.421±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-[4-(三氟甲基)苯氧基]吡啶-2-羧酸 在 草酰氯 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-[4-(trifluoromethyl)phenoxy]pyridine-2-carboxamide
  参考文献：
  名称：

  Identification of a novel hormone sensitive lipase inhibitor with a reduced potential of reactive metabolites formation

  摘要：

  Hormone sensitive lipase (HSL) has emerged as an attractive target for the treatment of dyslipidemia. We previously reported compound 1 as a potent and orally active HSL inhibitor. Although an attractive profile was demonstrated, subsequent studies revealed that compound 1 has a bioactivation liability. The oxygen-carbon linker in compound 1 was identified as being potentially responsible for reactive metabolite formation. By exchanging of this susceptible fragment was feasible, and a benzanilide derivative 6b with a decreased bioactivation liability was obtained. Further modification of the novel benzanilide scaffold resulted in the identification of compound 24b. Compound 24b exhibited potent HSL inhibitory activity (IC50 = 2 nM) with a significantly reduced bioactivation potential. Oral administration of compound 24b exhibited an antilipolytic effect on rats at 3 mg/kg. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.02.045
• 作为产物：
  描述：

  对三氟甲基苯酚 在 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 5-[4-(三氟甲基)苯氧基]吡啶-2-羧酸
  参考文献：
  名称：

  [EN] PYRIDINE CARBONYL DERIVATIVES AND THERAPEUTIC USES THEREOF AS TRPC6 INHIBITORS
  [FR] DÉRIVÉS DE PYRIDINE CARBONYLE ET LEURS UTILISATIONS THÉRAPEUTIQUES EN TANT QU'INHIBITEURS DE TRPC6

  摘要：

  该发明涉及式(I)的化合物及其药用盐，其中R1至R7，A，Y和L的定义如本文所述。该发明还涉及包含这些化合物的药物组合物，使用这些化合物治疗各种疾病和疾病的方法，制备这些化合物的过程以及在这些过程中有用的中间体。

  公开号：

  WO2019081637A1

文献信息

• [EN] PYRIDINE CARBONYL DERIVATIVES AND THERAPEUTIC USES THEREOF AS TRPC6 INHIBITORS<br/>[FR] DÉRIVÉS DE PYRIDINE CARBONYLE ET LEURS UTILISATIONS THÉRAPEUTIQUES EN TANT QU'INHIBITEURS DE TRPC6
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2019081637A1

  公开（公告）日：2019-05-02

  The invention relates to compounds of formula (I), and pharmaceutically acceptable salts thereof, wherein R1 to R7, A, Y and L are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

  该发明涉及式(I)的化合物及其药用盐，其中R1至R7，A，Y和L的定义如本文所述。该发明还涉及包含这些化合物的药物组合物，使用这些化合物治疗各种疾病和疾病的方法，制备这些化合物的过程以及在这些过程中有用的中间体。
• 5-Substituted picolinic acid derivatives and an anti-hypertensive
  申请人：Meuji Seika Kaisha Ltd.

  公开号：US04229448A1

  公开（公告）日：1980-10-21

  5-Substituted picolinic acid derivatives represented by the formula (I): ##STR1## wherein R.sub.1 represents a straight or branched chain halogen-substituted alkyl group having 2 to 6 carbon atoms or a substituted phenyl group having the formula ##STR2## wherein R.sub.3 and R.sub.4, which may be the same or different, each represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, an amino group, an N-alkyl-substituted amino group, an acylamino group, an acetyl group, an acyloxy group, a hydroxy group or a halogen-substituted alkyl group or R.sub.3 and R.sub.4, when taken together, represent a polymethylene chain; and R.sub.2 represents an --OM group wherein M represents a hydrogen, sodium, potassium, calcium, aluminium or magnesium atom, a straight or branched chain or cyclic alkoxy group having 1 to 6 carbon atoms, an aminoalkoxy group, a phenoxy group, a substituted phenoxy group, a 5-indanyloxy group, an acyloxyalkyloxy group having the formula ##STR3## wherein R.sub.5 represents a hydrogen atom or a methyl group and R.sub.6 represents a lower alkyl group having 1 to 6 carbon atoms, a phenyl group or a substituted phenyl group, or an amino group represented by the formula ##STR4## wherein R.sub.7 and R.sub.8, which may be the same or different, each represents a hydrogen atom, a lower alkyl group, or a phenyl group which are useful as anti-hypertensive agents, a process for preparing the above 5-substituted picolinic acid derivatives, and anti-hypertensive compositions containing the same.

  式(I)所表示的5-取代吡啶甲酸衍生物，其中R1表示具有2至6个碳原子的直链或支链卤素取代的烷基或具有以下式的取代苯基的衍生物： 其中R3和R4，它们可以相同也可以不同，每个表示氢原子，卤素原子，低碳基，低氧基，硝基，氨基，N-烷基取代的氨基，酰胺基，乙酰基，酰氧基，羟基或卤素取代的烷基或R3和R4在一起时表示聚亚甲基链；R2表示-OM基，其中M表示氢，钠，钾，钙，铝或镁原子，具有1至6个碳原子的直链或支链或环状氧基基团，氨基氧基基团，苯氧基，取代苯氧基，5-茚烯氧基基团，具有以下式的酰氧基烷氧基基团： 其中R5表示氢原子或甲基基团，R6表示具有1至6个碳原子的低碳基，苯基或取代苯基，或由以下式表示的氨基基团： 其中R7和R8，它们可以相同也可以不同，每个表示氢原子，低碳基或苯基，它们有用作抗高血压剂的作用，一种制备上述5-取代吡啶甲酸衍生物的方法，以及含有它们的抗高血压组合物。
• Inhibitors of TRPC6
  申请人：Boehringer Ingelheim International GmbH

  公开号：US10800757B2

  公开（公告）日：2020-10-13

  The invention relates to compounds of formula (I), and pharmaceutically acceptable salts thereof, wherein R1 to R7, A, Y and L are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

  本发明涉及式 (I) 化合物、 及其药学上可接受的盐，其中 R1 至 R7、A、Y 和 L 如本文所定义。本发明还涉及包含这些化合物的药物组合物、使用这些化合物治疗各种疾病和失调的方法、制备这些化合物的工艺以及在这些工艺中有用的中间体。
• PYRIDINE CARBONYL DERIVATIVES AND THERAPEUTIC USES THEREOF AS TRPC6 INHIBITORS
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP3700902A1

  公开（公告）日：2020-09-02
• EP3786160A1
  申请人：——

  公开号：EP3786160A1

  公开（公告）日：2021-03-03