(5-Chloro-2,3-dihydro-benzofuran-2-yl)-{4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-methanone | 384336-01-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (5-Chloro-2,3-dihydro-benzofuran-2-yl)-{4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-methanone
• 英文别名: (5-chloro-2,3-dihydro-1-benzofuran-2-yl)-[4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl]methanone
• CAS: 384336-01-0
• 化学式: C₂₂H₂₄ClN₅O₂
• 分子量: 425.918
• InChiKey: IYAFKKGFYHLLJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  74.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-氯-2,3-二氢-1-苯并呋喃-2-羧酸 、 N-methyl-N-((3S,4S)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以26%的产率得到(5-Chloro-2,3-dihydro-benzofuran-2-yl)-{4-methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-methanone
  参考文献：
  名称：

  Discovery of CP-690,550: A Potent and Selective Janus Kinase (JAK) Inhibitor for the Treatment of Autoimmune Diseases and Organ Transplant Rejection

  摘要：

  There is a critical need for safer and more convenient treatments for organ transplant rejection and autoimmune disorders such as rheumatoid arthritis. Janus tyrosine kinases (JAK1, JAK3) are expressed in lymphoid cells and are involved in the signaling of multiple cytokines important for various T cell functions. Blockade of the JAK1/JAK3-STAT pathway with a small molecule was anticipated to provide therapeutic immunosuppression/immunomodulation. The Pfizer compound library was screened against the catalytic domain of JAK3 resulting in the identification of a pyrrolopyrimidine-based series of inhibitors represented by CP-352,664 (2a). Synthetic analogues of 2a were screened against the JAK enzymes and evaluated in an IL-2 induced T cell blast proliferation assay. Select compounds were evaluated in rodent efficacy models of allograft rejection and destructive inflammatory arthritis. Optimization within this chemical series led to identification of CP-690,550 1, a potential first-in-class JAK inhibitor for treatment of autoimmune diseases and organ transplant rejection.

  DOI：

  10.1021/jm1004286

文献信息

• Pyrrolo[2,3-d]pyrimidine compounds
  申请人：——

  公开号：US20020068746A1

  公开（公告）日：2002-06-06

  A compound of the formula 1 wherein R 1 , R 2 and R 3 are as defined above, useful as inhibitors of protein kinases, such as the enzyme Janus Kinase 3.

  一种具有上述定义的R1、R2和R3的化合物，用作蛋白激酶抑制剂，例如酶Janus激酶3。
• Pyrrolo[2,3-D]pyrimidine compounds
  申请人：Blumenkopf A. Todd

  公开号：US20050197349A1

  公开（公告）日：2005-09-08

  A compound of the formula wherein R 1 , R 2 and R 3 are as defined above, useful as inhibitors of protein kinases, such as the enzyme Janus Kinase 3.

  一种化合物的公式，其中R1，R2和R3如上所定义，可用作蛋白激酶的抑制剂，例如酶Janus Kinase 3。
• PYRROLO¬2,3-D|PYRIMIDINE COMPOUNDS AS IMMUNOSUPPRESSIVE AGENTS
  申请人：Pfizer Products Inc.

  公开号：EP1294724B1

  公开（公告）日：2006-04-19
• Pyrrolo[2,3-d]pyrimidine compounds as immunosuppressive agents
  申请人：Pfizer Products Incorporated

  公开号：EP1686130B1

  公开（公告）日：2009-02-18
• US6696567B2
  申请人：——

  公开号：US6696567B2

  公开（公告）日：2004-02-24