2-(2-Methoxy-phenyl)-3H-imidazo[4,5-c]pyridine; hydrochloride | 87359-18-0

• 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-(2-Methoxy-phenyl)-3H-imidazo[4,5-c]pyridine; hydrochloride
• 英文别名: 2-(2-Methoxyphenyl)-3H-imidazo[4,5-c]pyridine;hydrochloride
• CAS: 87359-18-0
• 化学式: C13H12ClN3O
• 分子量: 261.7
• InChiKey: PTZUHEQQCZTOQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-二氨基吡啶 、 邻甲氧基苯甲酸 生成 2-(2-Methoxy-phenyl)-3H-imidazo[4,5-c]pyridine; hydrochloride
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Cyclic nucleotide phosphodiesterase inhibition by imidazopyridines: analogs of sulmazole and isomazole as inhibitors of the cGMP specific phosphodiesterase
  作者：William J. Coates、Brendan Connolly、Dashyant Dhanak、Sean T. Flynn、Angela Worby

  DOI：10.1021/jm00062a011

  日期：1993.5

  The synthesis and phosphodiesterase (PDE) inhibitory profile of a series of imidazopyridines, including sulmazole and isomazole, on separated PDE isoenzymes are described. The results show that both sulmazole and isomazole are weak inhibitors of PDE III, and their inotropic activity is unlikely to be due to PDE III inhibition alone. Surprisingly, both compounds were found to be significant inhibitors

  描述了一系列咪唑并吡啶（包括舒马唑和异唑）对分离的PDE同工酶的合成和磷酸二酯酶（PDE）抑制谱。结果表明，舒马唑和异咪唑都是PDE III的弱抑制剂，它们的正性活性不太可能仅由于PDE III的抑制而引起。出乎意料的是，发现这两种化合物都是cGMP特异性同工酶PDE V的重要抑制剂，并且已经制备了一系列简单的2-取代的苯基咪唑并[4,5-b]吡啶用于研究PDE活性的SAR。已显示这对链长，极性和杂原子连接基团的性质敏感。已经确定了有效的PDE V抑制剂，其中许多也是PDE IV的重要抑制剂。
• Structure-activity relationships of arylimidazopyridine cardiotonics: discovery and inotropic activity of 2-[2-methoxy-4-(methylsulfinyl)phenyl]-1H-imidazo[4,5-c]pyridine
  作者：David W. Robertson、E. E. Beedle、Joseph H. Krushinski、G. Don Pollock、Harve Wilson、Virginia L. Wyss、J. Scott Hayes

  DOI：10.1021/jm00383a006

  日期：1985.6

  2-phenylimidazo[4,5-b]pyridines (e.g., sulmazole) or 8-phenylpurines. Furthermore, all imidazo[4,5-c]pyridine analogues we tested were orally active; in contrast, only one of the imidazo[4,5-b]pyridine derivatives, sulmazole, was significantly active. One of several highly active compounds in the [4,5-c] series was 50 (LY175326, 2-[2-methoxy-4-(methylsulfinyl)phenyl]-1H-imidazo[4,5-c]pyridine hydrochloride)

  最近，已经发现几种在实验动物和人体内具有正性和血管扩张活性的非儿茶酚胺，非糖苷强心药。原型化合物包括氨力农，舒马唑和芬诺酮。我们研究了一系列含有稠合到2-苯基咪唑的杂环的分子中最佳肌力活性所需的结构要求，发现2-苯基咪唑并[4,5-c]吡啶的效力通常比类似的2强5-10倍-苯基咪唑并[4，5-b]吡啶（例如，舒马唑）或8-苯基嘌呤。此外，我们测试的所有咪唑并[4,5-c]吡啶类似物均具有口服活性。相反，只有咪唑并[4,5-b]吡啶衍生物之一舒马唑具有明显的活性。[4,5-c]系列中几种高活性化合物之一是50（LY175326，2- [2-甲氧基-4-（甲基亚磺酰基）苯基] -1H-咪唑并[4，5-c]吡啶盐酸盐）。介绍了该系列的结构活性关系，并将其与咪唑并[4,5-b]吡啶和嘌呤系列进行了比较。
• Pyridine compounds
  申请人：ELI LILLY AND COMPANY

  公开号：EP0093593A2

  公开（公告）日：1983-11-09

  This invention provides compounds for use as positive inotropic agents, bronchodilators, vasodilators and anticoagulants of the formula: or a pharmaceutically acceptable salt thereof, wherein R, is hydrogen, C1-C4 alkyl, or chloro; R2 and R3 are independently hydrogen, C1-C4 alkyl, C1-C4 alkoxy, allyloxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, hydroxy, halo, cyano, nitro, amino, mono- or di-(C1-C4 alkyl)amino, trifluoromethyl, or C1-C4 alkoxy substituted with a group Z-Q-, wherein Q is oxygen, sulfur, sulfinyl, sulfonyl, or a bond, and Z is a C1-C4 alkyl, phenyl, or phenyl substituted with halo, C1-C4 alkyl, C1-C4 alkoxy, hydroxy, nitro, amino, C1-C4 alkylthio, C1-C4 alkylsulfinyl, or C1-C4 alkylsulfonyl; and R4 is hydrogen, C1-C4 alkyl, or C1-C4 alkoxy; with the provisions that: a) if R, and two of R2, R3, and R4 are all hydrogen, the other of R2, R3, and R4 is not hydrogen, halo, hydroxy, nitro, amino, di-(C,-C2 alkyl)amino, or C1-C2 alkoxy; b) if R, and one of R2, R3 and R4 are both hydrogen, and one of R2, R3 and R4 is C1-C2 alkoxy, the other of R2, R3 and R4 is not hydroxy or C1-C2 alkoxy; c) if R, is chloro and two of R2, R3, and R4 are all hydrogen, the other of R2, R3, and R4 is not hydrogen, halo, C1-C2 alkyl, or nitro; and d) if R, is chloro and R4 is hydrogen, R2 and R3 may not both be nitro.

  这项发明提供了以下公式的化合物，用作正性肌力药物、支气管扩张剂、血管扩张剂和抗凝剂，或其药学上可接受的盐：其中R是氢、C1-C4烷基或氯；R2和R3独立地是氢、C1-C4烷基、C1-C4烷氧基、烯丙氧基、C1-C4烷硫基、C1-C4烷基亚砜基、C1-C4烷基磺酰基、羟基、卤素、氰基、硝基、氨基、单-或双-(C1-C4烷基)氨基、三氟甲基或C1-C4烷氧基取代的Z-Q-基团，其中Q是氧、硫、亚砜基、磺酰基或键，Z是C1-C4烷基、苯基或取代有卤素、C1-C4烷氧基、羟基、硝基、氨基、C1-C4烷硫基、C1-C4烷基亚砜基或C1-C4烷基磺酰基的苯基；和R4是氢、C1-C4烷基或C1-C4烷氧基；但需满足以下条件：a）如果R和R2、R3和R4中的两个都是氢，则R2、R3和R4中的另一个不是氢、卤素、羟基、硝基、氨基、双-(C1-C2烷基)氨基或C1-C2烷氧基；b）如果R和R2、R3和R4中的一个都是氢，而R2、R3和R4中的一个是C1-C2烷氧基，则R2、R3和R4中的另一个不是羟基或C1-C2烷氧基；c）如果R是氯，而R2、R3和R4中有两个都是氢，则R2、R3和R4中的另一个不是氢、卤素、C1-C2烷基或硝基；d）如果R是氯，而R4是氢，则R2和R3不能同时为硝基。
• New imidazo[4,5-c]pyridine derivatives, processes for their preparation and pharmaceutical formulations containing such compounds
  申请人：MERCK PATENT GmbH

  公开号：EP0079083A1

  公开（公告）日：1983-05-18

  Compounds of formula (I'), and compositions containing them: (wherein n is 1, 2 or 3, each R1 independently represents a halogen atom; a hydroxy, carboxyl or C1-4 alkyl group, a C2-4 alkenyloxy, phenyl or phenyl-C1-4 alkoxy group which may be optionally substituted by one or more halogen atoms; an .amino, mono- or dialkyl-amino, morpholino or piperazino group; a group of formula -S(O)xRa where x is 0, 1 or 2 and Ra is a C1-4 alkyl group; or a C1-4 alkoxy group which may be optionally substituted by one or more radicals selected from hydroxy, C1-4 alkoxy, amino, mono- or di- C1-4 alkylamino, (phenyl- C1-4 alkyl)amino, N,N-C1-4alkyl(phenyl-C1-4alkyl)-amino and N,N-(C1-4alkoxyphenyl-C1-4alkyl)C1-4 alkyl-amino; n is 1, 2 or 3; m is 0 or 1; R2 represents a C1-4 alkyl group in the 1- or 3-position of the imidazo ring; R3 represents a hydrogen or halogen (fluorine, chlorine, bromine or iodine) atom, or a hydroxy, amino or C1-4 alkyl or alkoxy group; and physiologically acceptable acid addition salts thereof and N-oxides of such compounds and salts. Formula (1') includes the alternative tautomeric form. The compounds and compositions are useful for treatment of the human or animal body by therapy, particularly for use in the treatment or prophylaxis of heart failure and myocardial insufficiency.

  式(I')化合物及含有它们的组合物： (其中 n 为 1、2 或 3，每个 R1 独立地代表卤素原子；羟基、羧基或 C1-4 烷基、C2-4 烯氧基、苯基或苯基-C1-4 烷氧基，可任选被一个或多个卤素原子取代；.氨基、单或二烷基氨基、吗啉基或哌嗪基；式 -S(O)xRa 的基团，其中 x 为 0、1 或 2，Ra 为 C1-4 烷基；或 C1-4 烷氧基，可任选被一个或多个基团取代，这些基团选自羟基、C1-4 烷氧基、氨基、单-或二-C1-4 烷基氨基、（苯基-C1-4 烷基）氨基、N,N-C1-4 烷基（苯基-C1-4 烷基）氨基和 N,N-（C1-4 烷氧基苯基-C1-4 烷基）C1-4 烷基氨基；n 为 1、2 或 3；m 为 0 或 1； R2 代表咪唑环 1 位或 3 位上的 C1-4 烷基； R3 代表氢原子或卤素（氟、氯、溴或碘）原子，或羟基、氨基或 C1-4 烷基或 烷氧基；及其生理上可接受的酸加成盐和此类化合物和盐的 N-氧化物。式（1'）包括另一种同分异构形式。这些化合物和组合物可用于人体或动物机体的治疗，特别是用于治疗或预防心力衰竭和心肌功能不全。
• ROBERTSON, D. W.;BEEDLE, E. E.;KRUSHINSKI, J. H.;DON, POLLOCK, G.;WILSON,+, J. MED. CHEM., 1985, 28, N 6, 717-727
  作者：ROBERTSON, D. W.、BEEDLE, E. E.、KRUSHINSKI, J. H.、DON, POLLOCK, G.、WILSON,+

  DOI：——

  日期：——