3-amino-2-carbamoyl-6-methyl-thieno[2,3-b]pyridine-4-carboxylic acid | 635731-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 3-amino-2-carbamoyl-6-methyl-thieno[2,3-b]pyridine-4-carboxylic acid
• 英文别名: 3-amino-2-carbamoyl-6-methylthieno[2,3-b]pyridine-4-carboxylic acid
• CAS: 635731-85-0
• 化学式: C₁₀H₉N₃O₃S
• 分子量: 251.266
• InChiKey: ZFXCZHOONZKJKL-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C
• 沸点：
  525.3±45.0 °C(Predicted)
• 密度：
  1.610±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  148
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-amino-2-carbamoyl-6-methyl-thieno[2,3-b]pyridine-4-carboxylic acid 在 lithium aluminium tetrahydride 、 cerium(III) chloride 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 8.0h， 生成 3-amino-4-(hydroxyphenylmethyl)-6-methylthieno[2,3-b]pyridine-2-carboxylic acid amide
  参考文献：
  名称：

  [EN] SUBSTITUTED 3-AMINO-THIENO[2,3-b]PYRIDINE-2-CARBOXYLIC ACID AMIDE COMPOUNDS AND PROCESSES FOR PREPARING AND THEIR USES
  [FR] COMPOSES AMIDE D'ACIDE 3-AMINO-THIENO[2,3-b]PYRIDINE-2-CARBOXYLIQUE SUBSTITUES ET PROCESSUS DE PREPARATION ET D'UTILISATION DE CES COMPOSES

  摘要：

  公开的是式(I)的化合物，其中R1和R2如本文所定义，这些化合物可用作IκB激酶（IKK）复合物激酶活性的抑制剂。因此，这些化合物在治疗IKK介导的疾病，包括自身免疫疾病、炎症性疾病和癌症方面是有用的。还公开了包含这些化合物的药物组合物以及制备这些化合物的方法。

  公开号：

  WO2003103661A1
• 作为产物：
  描述：

  乙酰丙酮酸乙酯 在 lithium hydroxide 、 水 、 四丁基碘化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 3.58h， 生成 3-amino-2-carbamoyl-6-methyl-thieno[2,3-b]pyridine-4-carboxylic acid
  参考文献：
  名称：

  [EN] SUBSTITUTED 3-AMINO-THIENO[2,3-b]PYRIDINE-2-CARBOXYLIC ACID AMIDE COMPOUNDS AND PROCESSES FOR PREPARING AND THEIR USES
  [FR] COMPOSES AMIDE D'ACIDE 3-AMINO-THIENO[2,3-b]PYRIDINE-2-CARBOXYLIQUE SUBSTITUES ET PROCESSUS DE PREPARATION ET D'UTILISATION DE CES COMPOSES

  摘要：

  公开的是式(I)的化合物，其中R1和R2如本文所定义，这些化合物可用作IκB激酶（IKK）复合物激酶活性的抑制剂。因此，这些化合物在治疗IKK介导的疾病，包括自身免疫疾病、炎症性疾病和癌症方面是有用的。还公开了包含这些化合物的药物组合物以及制备这些化合物的方法。

  公开号：

  WO2003103661A1

文献信息

• Substituted 3-amino-thieno[2,3-b]pyridine-2-carboxylic acid amide compounds and processes for preparing and their uses
  申请人：Cywin L. Charles

  公开号：US20050288285A1

  公开（公告）日：2005-12-29

  Disclosed are compounds of formula (I): wherein R 1 and R 2 are defined herein, which are useful as inhibitors of the kinase activity of the IκB kinase (IKK) complex. The compounds are therefore useful in the treatment of IKK mediated diseases including autoimmune diseases inflammatory diseases and cancer. Also disclosed are pharmaceutical compositions comprising these compounds and processes for preparing these compounds.

  本发明涉及化合物(I)的公开，其中R1和R2在此定义，这些化合物可用作IκB激酶（IKK）复合物的激酶活性抑制剂。因此，这些化合物可用于治疗由IKK介导的疾病，包括自身免疫性疾病、炎症性疾病和癌症。还公开了包含这些化合物的药物组合物和制备这些化合物的过程。
• Substituted 3-amino-thieno [2,3-b]pyridine-2-carboxylic acid amide compounds and processes for preparing and their uses
  申请人：Boehringer Ingelheim Pharmaceuticals, Inc.

  公开号：US20040053957A1

  公开（公告）日：2004-03-18

  Disclosed are compounds of formula (I): 1 wherein R 1 and R 2 are defined herein, which are useful as inhibitors of the kinase activity of the I&kgr;B kinase (IKK) complex. The compounds are therefore useful in the treatment of IKK mediated diseases including autoimmune diseases inflammatory diseases and cancer. Also disclosed are pharmaceutical compositions comprising these compounds and processes for preparing these compounds.

  本发明公开了式(I)的化合物：其中R1和R2在此定义，这些化合物可用作IκB激酶（IKK）复合物的激酶活性抑制剂。因此，这些化合物可用于治疗IKK介导的疾病，包括自身免疫性疾病、炎症性疾病和癌症。本发明还公开了包含这些化合物的制药组合物和制备这些化合物的过程。
• 3-amino-thieno[2,3-b]pyridine-2-carboxylic acid amides
  申请人：Boehringer Ingelheim Pharmaceuticals, Inc.

  公开号：EP2008654A1

  公开（公告）日：2008-12-31

  Disclosed are compounds of formula (I): wherein R1 and R2 are defined herein, which are useful as inhibitors of the kinase activity of the IκB kinase (IKK) complex. The compounds are therefore useful in the treatment of IKK mediated diseases including autoimmune diseases inflammatory diseases and cancer. Also disclosed are pharmaceutical compositions comprising these compounds and processes for preparing these compounds.

  所公开的是式 (I) 化合物： 其中 R1 和 R2 在此定义，可用作 IκB 激酶（IKK）复合物激酶活性的抑制剂。因此，这些化合物可用于治疗 IKK 介导的疾病，包括自身免疫性疾病、炎症性疾病和癌症。此外，还公开了包含这些化合物的药物组合物以及制备这些化合物的工艺。
• Evolution of the Thienopyridine Class of Inhibitors of IκB Kinase-β:  Part I:  Hit-to-Lead Strategies
  作者：Tina Morwick、Angela Berry、Janice Brickwood、Mario Cardozo、Katrina Catron、Molly DeTuri、Jonathan Emeigh、Carol Homon、Matt Hrapchak、Stephen Jacober、Scott Jakes、Paul Kaplita、Terence A. Kelly、John Ksiazek、Michel Liuzzi、Ronald Magolda、Can Mao、Daniel Marshall、Daniel McNeil、Anthony Prokopowicz、Christopher Sarko、Erika Scouten、Cynthia Sledziona、Sanxing Sun、Jane Watrous、Jiang Ping Wu、Charles L. Cywin

  DOI：10.1021/jm0510979

  日期：2006.5.1

  High-throughput screening is routinely employed as a method for the identification of novel hit structures. Large numbers of active compounds are typically procured in this way and must undergo a rigorous validation process. This process is described in detail for a collection of screening hits identified as inhibitors of I kappa B kinase-beta (IKK beta), a key regulatory enzyme in the nuclear factor-kappa B (NF-kappa B) pathway. From these studies, a promising hit series was selected. Subsequent lead generation activities included the development of a pharmacophore hypothesis and structure-activity relationship (SAR) for the hit series. This led to the exploration of related scaffolds offering additional opportunities, and the various structural classes were comparatively evaluated for enzyme inhibition, selectivity, and drug-like properties. A novel lead series of thienopyridines was thereby established, and this series advanced into lead optimization for further development.
• SUBSTITUTED 3-AMINO-THIENO(2,3-b) PYRIDINE-2-CARBOXYLIC ACID AMIDE COMPOUNDS ANDPROCESSES FOR PREPARING AND THEIR USES
  申请人：BOEHRINGER INGELHEIM PHARMACEUTICALS INC.

  公开号：EP1513516A1

  公开（公告）日：2005-03-16