(2-Amino-6-chloro-3-nitro-pyridin-4-yl)-(6-methyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester | 947146-81-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (2-Amino-6-chloro-3-nitro-pyridin-4-yl)-(6-methyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester
• 英文别名: (2-Amino-6-chloro-3-nitropyridin-4-yl)-(6-methylpyridin-3-ylmethyl)-carbamic acid ethyl ester；ethyl N-(2-amino-6-chloro-3-nitropyridin-4-yl)-N-[(6-methylpyridin-3-yl)methyl]carbamate
• CAS: 947146-81-8
• 化学式: C₁₅H₁₆ClN₅O₄
• 分子量: 365.776
• InChiKey: NIPAYINZFNWVBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2-Amino-6-chloro-3-nitro-pyridin-4-yl)-(6-methyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester 在 palladium on carbon 、 氢气 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 乙腈 为溶剂， 40.0~80.0 ℃ 、275.8 kPa 条件下， 生成 4-amino-1-(6-methyl-pyridin-3-ylmethyl)-6-(tetrahydro-pyran-4-ylmethoxy)-1,3-dihydro-imidazo[4,5-c]pyridin-2-one
  参考文献：
  名称：

  Design and optimisation of orally active TLR7 agonists for the treatment of hepatitis C virus infection

  摘要：

  The synthesis and structure-activity relationships of a series of novel interferon inducers are described. Pharmacokinetic studies and efficacy assessment of a series of 8-oxo-3-deazapurine analogues led to the identification of compound 33, a potent and selective agonist of the TLR7 receptor with an excellent in vivo efficacy profile in a mouse model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.092
• 作为产物：
  描述：

  4-氨基-2,6-二氯吡啶 在 硫酸 、 Me-THF 、 氨 、 硝酸 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 (2-Amino-6-chloro-3-nitro-pyridin-4-yl)-(6-methyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester
  参考文献：
  名称：

  Design and optimisation of orally active TLR7 agonists for the treatment of hepatitis C virus infection

  摘要：

  The synthesis and structure-activity relationships of a series of novel interferon inducers are described. Pharmacokinetic studies and efficacy assessment of a series of 8-oxo-3-deazapurine analogues led to the identification of compound 33, a potent and selective agonist of the TLR7 receptor with an excellent in vivo efficacy profile in a mouse model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.092

文献信息

• NOVEL PHARMACEUTICALS
  申请人：Jones Peter

  公开号：US20070197478A1

  公开（公告）日：2007-08-23

  The present invention relates to immune response modifiers of formula (I), which act selectively through agonism, of Toll-Like Receptors (TLRs), uses thereof, processes for the preparation thereof, intermediates used in the preparation thereof and compositions containing said inhibitors. These inhibitors have utility in a variety of therapeutic areas including the treatment of infectious disease such as Hepatitis (e.g. HCV, HBV), genetically related viral infection and cancer.

  本发明涉及公式（I）的免疫应答调节剂，通过对Toll样受体（TLRs）的激动作用具有选择性，其用途，其制备方法，用于其制备的中间体以及含有所述抑制剂的组合物。这些抑制剂在包括治疗传染病（如肝炎（例如HCV，HBV），遗传相关病毒感染和癌症在内的各种治疗领域中具有用途。
• Imidazopyridinones
  申请人：Jones Peter H.

  公开号：US20110039884A1

  公开（公告）日：2011-02-17

  The invention relates to imidazopyridinones, to their use in medicine, to compositions containing them, to processes for their preparation and to intermediates used in such processes. By activating TLRs, it should be possible to induce or stimulate immune cells to mount an immune response. In particular, the TLR7 has been implicated in viral infections (such as HCV or HBV), cancers and tumours, and T2 Helper cell (TH2) mediated diseases, and hence TLR7 agonists are potentially useful in the treatment of such diseases. We have now found a series of imidazopyridinones which are agonists of TLR7. According, there is provided a compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof, wherein R 1 is 3- to 8-membered saturated heterocyclic group wherein one ring member is —O—; and R 2 is phenyl or pyridinyl, each optionally substituted by C 1 -C 6 alkyl.

  本发明涉及咪唑吡啶酮及其在医药上的应用，包括含有它们的组合物、制备它们的过程以及用于这些过程中的中间体。通过激活TLRs，应该能够诱导或刺激免疫细胞产生免疫反应。特别是，TLR7已经被牵涉到病毒感染（如HCV或HBV）、癌症和肿瘤以及T2辅助细胞（TH2）介导的疾病，因此TLR7激动剂在这些疾病的治疗中具有潜在的用途。我们现在发现了一系列咪唑吡啶酮，它们是TLR7的激动剂。因此，提供了式（I）的化合物或其药学上可接受的盐或溶剂，其中R1是3-至8-成员的饱和杂环基团，其中一个环成员是—O—；R2是苯基或吡啶基，每个都可以选择地被C1-C6烷基取代。
• IMIDAZOPYRIDINONES
  申请人：JONES Peter H.

  公开号：US20090221631A1

  公开（公告）日：2009-09-03

  The invention relates to imidazopyridinones, to their use in medicine, to compositions containing them, to processes for their preparation and to intermediates used in such processes. By activating TLRs, it should be possible to induce or stimulate immune cells to mount an immune response. In particular, the TLR7 has been implicated in viral infections (such as HCV or HBV), cancers and tumours, and T2 Helper cell (TH2) mediated diseases, and hence TLR7 agonists are potentially useful in the treatment of such diseases. We have now found a series of imidazopyridinones which are agonists of TLR7. According, there is provided a compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof, wherein R 1 is 3- to 8-membered saturated heterocyclic group wherein one ring member is —O—; and R 2 is phenyl or pyridinyl, each optionally substituted by C 1 -C 6 alkyl.

  本发明涉及咪唑吡啶酮及其在医学上的应用，包括含有它们的组合物，制备这些化合物的过程以及用于这些过程的中间体。通过激活TLRs，可以诱导或刺激免疫细胞产生免疫反应。特别是，TLR7已被认为与病毒感染（如丙型肝炎病毒或乙型肝炎病毒）、癌症和肿瘤以及T2辅助细胞（TH2）介导的疾病有关，因此TLR7激动剂在治疗这些疾病方面具有潜在的用途。我们现在发现了一系列咪唑吡啶酮，它们是TLR7的激动剂。因此，提供了式（I）的化合物或其药学上可接受的盐或溶剂，其中R1是3-至8-成员的饱和杂环基团，其中一个环成员为—O—；而R2是苯基或吡啶基，每个基团都可以选择性地被C1-C6烷基取代。
• Pharmaceuticals
  申请人：Pfizer Inc.

  公开号：US07691877B2

  公开（公告）日：2010-04-06

  The present invention relates to immune response modifiers of formula (I), which act selectively through agonism, of Toll-Like Receptors (TLRs), uses thereof, processes for the preparation thereof, intermediates used in the preparation thereof and compositions containing said inhibitors. These inhibitors have utility in a variety of therapeutic areas including the treatment of infectious disease such as Hepatitis (e.g. HCV, HBV), genetically related viral infection and cancer.

  本发明涉及公式（I）的免疫应答调节剂，其通过Toll样受体（TLRs）的激动作用选择性地发挥作用，其应用，制备过程，制备中使用的中间体以及含有所述抑制剂的组合物。这些抑制剂在多种治疗领域中具有实用性，包括治疗传染性疾病，如肝炎（例如HCV，HBV），遗传相关的病毒感染和癌症。
• [EN] IMIDAZOPYRIDINONES<br/>[FR] IMIDAZOPYRIDINONES
  申请人：PFIZER LTD

  公开号：WO2009019553A3

  公开（公告）日：2009-04-02