[1-[5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl]-3-azabicyclo[3.1.0]hexan-3-yl]-[5-methylsulfonyl-2-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: [1-[5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl]-3-azabicyclo[3.1.0]hexan-3-yl]-[5-methylsulfonyl-2-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone
• 化学式: C₂₂H₂₄F₃N₃O₅S
• 分子量: 499.511
• InChiKey: MFWGHFCNGJQJHV-HMHBEAHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  102.6
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  (S)-2-(1-甲基-2,2,2-三氟乙氧基)-5-甲基磺酰基苯甲酸 、 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.17h， 以70%的产率得到[1-[5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-yl]-3-azabicyclo[3.1.0]hexan-3-yl]-[5-methylsulfonyl-2-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]methanone
  参考文献：
  名称：

  Phenyl-3-aza-bicyclo[3.1.0]hex-3-yl-methanones and the use thereof as medicament

  摘要：

  取代苯基-3-氮杂双环[3.1.0]己-3-基甲酮是甘氨酸转运蛋白-1（GlyT1）抑制剂。这些化合物对治疗精神分裂症、阿尔茨海默病和其他神经系统和精神疾病有用。

  公开号：

  US20130197011A1

文献信息

• [EN] PHENYL-3-AZA-BICYCLO[3.1.0]HEX-3-YL-METHANONES AND THE USE THEREOF AS MEDICAMENT<br/>[FR] PHÉNYL-3-AZA-BICYCLO[3.1.0]HEX-3-YL-MÉTHANONES ET LEUR UTILISATION EN TANT QUE MÉDICAMENT
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2013017657A1

  公开（公告）日：2013-02-07

  The present inventions relates to substituted phenyl-3-aza-bicyclo[3.1.0]hex-3-yl- methanones of general formula (I) wherein R1, R2, R3, R4, R5 and R6 are as herein described or salts thereof, preferably pharmaceutically acceptable salts thereof. The invention further relates to the manufacture of said compounds, pharmaceutical compositions comprising a compound according to general formula (I), and the use of said compounds for the treatment of various conditions such as conditions concerning positive and negative symptoms of schizophrenia as well as cognitive impairments associated with schizophrenia, Alzheimers Disease and other neurological and psychiatric disorders. The compounds of the invention show glycine transporter-1 (GlyT1) inhibiting properties.

  本发明涉及通式（I）所示的取代苯基-3-氮杂双环[3.1.0]己-3-基甲酮，其中R1、R2、R3、R4、R5和R6如本文所述或其盐，优选为其药学上可接受的盐。本发明还涉及所述化合物的制备，包含符合通式（I）的化合物的药物组合物，以及利用所述化合物治疗各种疾病的用途，如涉及精神分裂症的阳性和阴性症状以及与精神分裂症、阿尔茨海默病和其他神经和精神障碍相关的认知障碍。本发明的化合物显示甘氨酸转运蛋白-1（GlyT1）抑制性能。
• PHENYL-3-AZA-BICYCLO[3.1.0]HEX-3-YL-METHANONES AND THE USE THEREOF AS MEDICAMENT
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2739615B1

  公开（公告）日：2017-03-15
• METHODS OF TREATING ERYTHROPOIETIC PROTOPORPHYRIA, X-LINKED PROTOPORPHYRIA, OR CONGENITAL ERYTHROPOIETIC PORPHYRIA WITH GLYCINE TRANSPORT INHIBITORS
  申请人：Disc Medicine, Inc.

  公开号：US20210283129A1

  公开（公告）日：2021-09-16

  The present embodiments are directed to methods of using glycine transporter inhibitors, such as GlyT1 inhibitors, or pharmaceutically acceptable salts, solvates or prodrugs thereof, or pharmaceutical compositions thereof, for preventing or treating erythropoietic protoporphyria (EPP), X-linked protoporphyria (XLPP), and/or congenital erythropoietic porphyria (CEP), and related syndromes thereof.
• US9012489B2
  申请人：——

  公开号：US9012489B2

  公开（公告）日：2015-04-21
• Phenyl-3-aza-bicyclo[3.1.0]hex-3-yl-methanones and the use thereof as medicament
  申请人：GIOVANNINI Riccardo

  公开号：US20130197011A1

  公开（公告）日：2013-08-01

  Substituted phenyl-3-aza-bicyclo[3.1.0]hex-3-yl-methanones which are glycine transporter-1 (GlyT1) inhibitors. These are useful for the treatment of schizophrenia, Alzheimer's Disease and other neurological and psychiatric disorders.

  取代苯基-3-氮杂双环[3.1.0]己-3-基甲酮是甘氨酸转运蛋白-1（GlyT1）抑制剂。这些化合物对治疗精神分裂症、阿尔茨海默病和其他神经系统和精神疾病有用。