3-(3-fluorophenyl)azetidine | 1203798-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: 3-(3-fluorophenyl)azetidine
• CAS: 1203798-80-4
• 化学式: C₉H₁₀FN
• mdl: MFCD20528820
• 分子量: 151.184
• InChiKey: ZXSOUXUQIJCRTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-amino-3,4-dimethylthieno[2,3-c]pyridazine-6-carboxylic acid 、 3-(3-fluorophenyl)azetidine 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (5-Amino-3,4-dimethylthieno[2,3-c]pyridazin-6-yl)-[3-(3-fluorophenyl)azetidin-1-yl]methanone
  参考文献：
  名称：

  Challenges in the development of an M 4 PAM preclinical candidate: The discovery, SAR, and biological characterization of a series of azetidine-derived tertiary amides

  摘要：

  Herein we describe the continued optimization of M-4 positive allosteric modulators (PAMs) within the 5-amino-thieno[2,3-c] pyridazine series of compounds. In this letter, we disclose our studies on tertiary amides derived from substituted azetidines. This series provided excellent CNS penetration, which had been challenging to consistently achieve in other amide series. Efforts to mitigate high clearance, aided by metabolic softspot analysis, were unsuccessful and precluded this series from further consideration as a preclinical candidate. In the course of this study, we found that potassium tetrafluoroborate salts could be engaged in a tosyl hydrazone reductive cross coupling reaction, a previously unreported transformation, which expands the synthetic utility of the methodology. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.10.053
• 作为产物：
  描述：

  tert-butyl 3-(3-fluorophenyl)azetidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-(3-fluorophenyl)azetidine
  参考文献：
  名称：

  Challenges in the development of an M 4 PAM preclinical candidate: The discovery, SAR, and biological characterization of a series of azetidine-derived tertiary amides

  摘要：

  Herein we describe the continued optimization of M-4 positive allosteric modulators (PAMs) within the 5-amino-thieno[2,3-c] pyridazine series of compounds. In this letter, we disclose our studies on tertiary amides derived from substituted azetidines. This series provided excellent CNS penetration, which had been challenging to consistently achieve in other amide series. Efforts to mitigate high clearance, aided by metabolic softspot analysis, were unsuccessful and precluded this series from further consideration as a preclinical candidate. In the course of this study, we found that potassium tetrafluoroborate salts could be engaged in a tosyl hydrazone reductive cross coupling reaction, a previously unreported transformation, which expands the synthetic utility of the methodology. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.10.053

文献信息

• COMPOUNDS AND USES THEREOF
  申请人：Yumanity Therapeutics, Inc.

  公开号：US20190330198A1

  公开（公告）日：2019-10-31

  The present invention features compounds useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.

  本发明涉及用于治疗神经系统疾病的化合物。本发明的化合物可以单独或与其他药用活性剂结合使用，用于治疗或预防神经系统疾病。
• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2019034702A1

  公开（公告）日：2019-02-21

  The invention relates to compounds of Formula (I) and their use in therapy, for example in the treatment of mycobacterial infections or in the treatment of diseases caused by mycobacterium, such as tuberculosis

  这项发明涉及到式（I）化合物及其在治疗中的应用，例如在治疗分枝杆菌感染或治疗由分枝杆菌引起的疾病，如结核病。
• [EN] SUBSTITUTED AZETIDINE DIHYDROTHIENOPYRIMIDINES AND THEIR USE AS PHOSPHODIESTERASE INHIBITORS<br/>[FR] DIHYDROTHIÉNOPYRIMIDINES D'AZÉTIDINE SUBSTITUÉES ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE LA PHOSPHODIESTÉRASE
  申请人：LEO PHARMA AS

  公开号：WO2019115774A1

  公开（公告）日：2019-06-20

  The present invention relates to novel substituted azetidine dihydrothienopyrimidines with phosphodiesterase inhibitory activity, and to their use in therapy, and to pharmaceutical compositions comprising the compounds and to methods of treating diseases with the compounds (I).

  本发明涉及一种具有磷酸二酯酶抑制活性的新型取代的氮杂四元二氢噻唑嘧啶化合物，并涉及它们在治疗中的应用，以及包含该化合物的制药组合物和使用该化合物治疗疾病的方法（I）。
• Compounds and uses thereof
  申请人：Yumanity Therapeutics, Inc.

  公开号：US10919885B2

  公开（公告）日：2021-02-16

  The present invention features compounds useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.

  本发明的特点是化合物可用于治疗神经系统疾病。本发明的化合物可单独使用，也可与其他药物活性剂结合使用，用于治疗或预防神经系统疾病。
• Compounds
  申请人：GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED

  公开号：US11253499B2

  公开（公告）日：2022-02-22

  The invention relates to compounds of Formula (I) and their use in therapy, for example in the treatment of mycobacterial infections or in the treatment of diseases caused by Mycobacterium, such as tuberculosis.

  本发明涉及式（I）化合物及其在治疗中的应用，例如用于治疗分枝杆菌感染或治疗由分枝杆菌引起的疾病，如结核病。