[2-(4-fluorophenyl)-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl]-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]amine | 1240608-91-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [2-(4-fluorophenyl)-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl]-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]amine
• 英文别名: 2-(4-fluorophenyl)-N-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-1-methyl-1H-imidazo[4,5-c]pyridin-4-amine；2-(4-fluorophenyl)-N-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-1-methylimidazo[4,5-c]pyridin-4-amine
• CAS: 1240608-91-6
• 化学式: C₂₄H₂₁FN₆O
• 分子量: 428.469
• InChiKey: GDJPLNOSDZIINK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-chloro-N-methyl-3-nitropyridin-4-amine 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium dithionite 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 乙醇 、 叔丁醇 为溶剂， 反应 21.5h， 生成 [2-(4-fluorophenyl)-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl]-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]amine
  参考文献：
  名称：

  Design and Synthesis of a Novel Series of Bicyclic Heterocycles As Potent γ-Secretase Modulators

  摘要：

  The design and the synthesis of several chemical subclasses of imidazole containing gamma-secretase modulators (GSMs) is described. Conformational restriction of pyridone 4 into bicyclic pyridone isosteres has led to compounds with high in vitro and in vivo potency. This has resulted, in the identification of benzimidazole 44a as a GSM with low nanomolar potency in vitro. In mouse, rat, and dog, this compound displayed the typical gamma-secretase modulatory profile by lowering A beta 42 and A beta 40 levels combined with an especially pronounced increase in A beta 38 and A beta 37 levels while leaving the total levels of amyloid peptides unchanged.

  DOI：

  10.1021/jm201710f

文献信息

• [EN] HETEROAROMATIC COMPOUNDS AND THEIR USE AS DOPAMINE D1 LIGANDS<br/>[FR] COMPOSES HETERO-AROMATIQUES ET LEUR UTILISATION COMME LIGANDS D1 DE LA DOPAMINE
  申请人：PFIZER

  公开号：WO2015162518A1

  公开（公告）日：2015-10-29

  The present invention provides, in part, compounds of Formula (I) and pharmaceutically acceptable salts thereof; processes for the preparation of; intermediates used in the preparation of; and compositions containing such compounds or salts, and their uses for treating D1-mediated (or D1 -associated) disorders including, e.g., schizophrenia (e.g., its cognitive and negative symptoms), schizotypal personality disorder, cognitive impairment (e.g., cognitive impairment associated with schizophrenia, AD, PD, or pharmacotherapy therapy), ADHD, Parkinson's disease, anxiety, and depression.

  本发明提供了部分符合Formula (I)的化合物及其药用盐；用于制备这些化合物的工艺；制备中使用的中间体；以及含有这些化合物或盐的组合物，以及它们用于治疗D1介导（或D1相关）疾病的用途，包括但不限于精神分裂症（例如其认知和消极症状）、偏执型人格障碍、认知障碍（例如与精神分裂症、阿尔茨海默病、帕金森病或药物治疗相关的认知障碍）、注意力缺陷多动障碍（ADHD）、帕金森病、焦虑和抑郁症。
• [EN] NOVEL SUBSTITUTED BENZOXAZOLE, BENZIMIDAZOLE, OXAZOLOPYRIDINE AND IMIDAZOPYRIDINE DERIVATIVES AS GAMMA SECRETASE MODULATORS<br/>[FR] NOUVEAUX DÉRIVÉS SUBSTITUÉS DU BENZOXAZOLE, DU BENZIMIDAZOLE, DE L'OXAZOLOPYRIDINE ET DE L'IMIDAZOPYRIDINE COMME MODULATEURS DE LA GAMMA-SECRÉTASE
  申请人：ORTHO MCNEIL JANSSEN PHARM

  公开号：WO2010094647A1

  公开（公告）日：2010-08-26

  The present invention is concerned with novel substituted benzoxazole, benzimidazole, oxazolopyridine and imidazopyridine derivatives of Formula (I) wherein R1, R2, R3, R4, X, A1, A2, A3, A4, Y1, Y2, Y3 and Z have the meaning defined in the claims. The compounds according to the present invention are useful as gamma secretase modulators. The invention further relates to processes for preparing such novel compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

  本发明涉及具有以下式（I）的新颖取代苯并噁唑、苯并咪唑、噁唑吡啶和咪唑吡啶衍生物，其中R1、R2、R3、R4、X、A1、A2、A3、A4、Y1、Y2、Y3和Z的含义如索赔中所定义。根据本发明的化合物可用作γ-分泌酶调节剂。本发明还涉及制备这种新化合物的方法、包含所述化合物作为活性成分的药物组合物以及将所述化合物用作药物的用途。
• NOVEL SUBSTITUTED BENZOXAZOLE, BENZIMIDAZOLE, OXAZOLOPYRIDINE AND IMIDAZOPYRIDINE DERIVATIVES AS GAMMA SECRETASE MODULATORS
  申请人：Janssen Pharmaceuticals, Inc.

  公开号：EP2398793B1

  公开（公告）日：2013-12-18
• HETEROAROMATIC COMPOUNDS AND THEIR USE AS DOPAMINE D1 LIGANDS
  申请人：Pfizer Inc.

  公开号：EP3134405B1

  公开（公告）日：2019-08-28
• US8772504B2
  申请人：——

  公开号：US8772504B2

  公开（公告）日：2014-07-08