2-(trifluoromethyl)-3-(hydroxymethyl)-8-(phenylmethoxy)imidazo<1,2-a>pyridine | 96428-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2-(trifluoromethyl)-3-(hydroxymethyl)-8-(phenylmethoxy)imidazo<1,2-a>pyridine
• 英文别名: 3-(hydroxymethyl)-8-(phenylmethoxy)-2-(trifluoromethyl)imidazo<1,2-a>pyridine；3-hydroxymethyl-2-trifluoromethyl-8-benzyloxyimidazo-[1,2-a]pyridine；3-(hydroxymethyl)-8-(phenylmethoxy)-2-(trifluoromethyl)imidazo[1,2-a]pyridine；[8-Phenylmethoxy-2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]methanol
• CAS: 96428-78-3
• 化学式: C₁₆H₁₃F₃N₂O₂
• 分子量: 322.287
• InChiKey: CFXRHRWZXJWQKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(trifluoromethyl)-3-(hydroxymethyl)-8-(phenylmethoxy)imidazo<1,2-a>pyridine 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Antiulcer Agents. 6. Analysis of the in Vitro Biochemical and in Vivo Gastric Antisecretory Activity of Substituted Imidazo[1,2-a]pyridines and Related Analogues Using Comparative Molecular Field Analysis and Hypothetical Active Site Lattice Methodologies

  摘要：

  A number of substituted imidazo[1,2-a]pyridines land related analogues were selected for analysis of their in vitro biochemical and in vivo gastric antisecretory activity using comparative molecular field analysis (CoMFA) and hypothetical active site lattice (HASL) methodologies. The training set of compounds selected included those that were also chosen for an extensive molecular modeling study initiated, using the active analog approach, to define the pharmacophore by means of which I and its analogues interact with the gastric proton pump enzyme, H+/K+-ATPase. Using either CoMFA or HASL, it was possible to identify an optimal alignment paradigm of-the proposed bioactive conformation for this series to reasonably predict the in vitro H+/K+-ATPase inhibitory potency in the purified enzyme model and the in vivo intravenous gastric antisecretory activity for compounds outside of the training set. Furthermore, the steric and electrostatic effects suggested by these two independent methods and their influence on determining biological activity were consistent and complementary to each other.

  DOI：

  10.1021/jm950700s
• 作为产物：
  描述：

  8-Benzyloxy-2-trifluoromethyl-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以76%的产率得到2-(trifluoromethyl)-3-(hydroxymethyl)-8-(phenylmethoxy)imidazo<1,2-a>pyridine
  参考文献：
  名称：

  抗溃疡药。1.取代的咪唑并[1,2-a]吡啶的胃抗分泌和细胞保护特性。

  摘要：

  描述了新型的抗溃疡剂，取代的咪唑并[1,2-a]吡啶。本发明的化合物既不是组胺（H 2）受体拮抗剂，也不是前列腺素类似物，但它们既具有胃分泌作用又具有细胞保护作用。胃抗分泌活性的机制可能涉及抑制H + / K + -ATPase酶。结构活性研究导致鉴定出3-（氰基甲基）-2-甲基-8-（苯甲氧基）咪唑并[1,2-a]吡啶，SCH 28080（27），已被选择用于进一步开发和临床评价。

  DOI：

  10.1021/jm00145a006

文献信息

• Pharmaceutical preparation comprising an active dispersed on a matrix
  申请人：——

  公开号：US20040058896A1

  公开（公告）日：2004-03-25

  The present invention relates to the field of pharmaceutical technology and describes a novel advantageous preparation for an active ingredient. The novel preparation is suitable for producing a large number of pharmaceutical dosage forms. In the new preparation an active ingredient is present essentially uniformly dispersed in an excipient matrix composed of one or more excipients selected from the group of fatty alcohol, triglyceride, partial glyceride and fatty acid ester.

  本发明涉及制药技术领域，描述了一种新的有利的活性成分制备方法。这种新的制备方法适用于生产大量的药物剂型。在这种新的制备方法中，活性成分基本上均匀地分散在由脂肪醇、甘油三酯、部分甘油酯和脂肪酸酯等多种赋形剂中选择的一种或多种赋形剂组成的赋形剂基质中。
• Compositions useful for treating gastrointestinal motility disorders
  申请人：Landau B. Steven

  公开号：US20050059704A1

  公开（公告）日：2005-03-17

  The present invention relates to method of treating a gastrointestinal motility disorder in a subject in need of treatment comprising coadministering to said subject a first amount of a compound having 5-HT 3 receptor agonist activity or a pharmaceutically acceptable salt, hydrate or solvate thereof; and a second amount of at least one gastric acid suppressing agent (e.g., a proton pump inhibitor, an H 2 receptor antagonist or a pharmaceutically acceptable salt, hydrate or solvate thereof; or an acid pump antagonist or pharmaceutically acceptable salt, hydrate or solvate thereof) wherein the first and second amounts together comprise a therapeutically effective amount. In particular, the method is for treating GERD, including nocturnal GERD. The invention further relates to a method of treating nocturnal GERD comprising administering to a subject in need thereof a therapeutically effective amount of a compound having 5-HT 3 receptor agonist activity or a pharmaceutically acceptable salt, hydrate or solvate thereof. The invention further relates to a method of increasing esophageal motility in a subject in need thereof. The method of increasing esophageal motility can be achieved by administration of a compound having 5-HT 3 receptor agonist activity or a pharmaceutically acceptable salt, hydrate or solvate thereof. The coadministration can also be used to increase esophageal motility.

  本发明涉及治疗需要治疗的受试者胃肠道运动紊乱的方法，包括向所述受试者联合施用第一种量的具有 5-HT 3 受体激动剂活性的化合物或其药学上可接受的盐、水合物或溶液；以及第二种量的至少一种胃酸抑制剂（如质子泵抑制剂、H 2 受体拮抗剂或其药学上可接受的盐、水合物或溶液；或酸泵拮抗剂或其药学上可接受的盐、水合物或溶液），其中第一和第二量共同构成治疗有效量。特别是，该方法用于治疗胃食管反流病，包括夜间胃食管反流病。本发明进一步涉及一种治疗夜间胃食管反流病的方法，该方法包括向有需要的受试者施用治疗有效量的具有 5-HT 3 受体激动剂活性的化合物或其药学上可接受的盐、水合物或溶液。本发明进一步涉及一种增加需要者食管蠕动的方法。增加食管蠕动的方法可通过给予具有 5-HT 3 受体激动剂活性的化合物或其药学上可接受的盐、水合物或溶液。联合给药也可用于增加食管运动。
• Compositions useful for increasing lower esophageal sphincter pressure
  申请人：Landau B. Steven

  公开号：US20060189648A1

  公开（公告）日：2006-08-24

  The present invention relates to a method of increasing the pressure of the lower esophageal sphincter in a subject in need thereof comprising administering to said subject a specified amount of a compound having 5-HT 3 receptor agonist activity or a pharmaceutically acceptable salt, hydrate or solvate thereof. The subject in need of treatment is suffering from GERD, including nocturnal GERD.

  本发明涉及一种增加有需要的受试者食管下括约肌压力的方法，包括向所述受试者施用指定量的具有 5-HT 3 受体激动剂活性的化合物或其药学上可接受的盐、水合物或溶液。需要治疗的受试者患有胃食管反流病，包括夜间胃食管反流病。
• Imidazo(1,2-a)pyridines, processes for their preparation and pharmaceutical compositions containing them
  申请人：SCHERING CORPORATION

  公开号：EP0033094B1

  公开（公告）日：1984-10-10
• ORAL PHARMACEUTICAL COMPOSITIONS WITH DELAYED RELEASE OF REVERSIBLE PROTON PUMP INHIBITORS
  申请人：Byk Gulden Lomberg Chemische Fabrik GmbH

  公开号：EP0841904A1

  公开（公告）日：1998-05-20