4-(furan-2-yl)-10-[2-(3-methyl-7,8-dihydro-5H-1,6-naphthyridin-6-yl)ethyl]-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine | 540534-93-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-(furan-2-yl)-10-[2-(3-methyl-7,8-dihydro-5H-1,6-naphthyridin-6-yl)ethyl]-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine
• CAS: 540534-93-8
• 化学式: C₂₁H₂₁N₉O
• 分子量: 415.457
• InChiKey: VKHRKRHXPXOULC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-(5-amino-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)ethyl 4-methylbenzenesulfonate 、 3-甲基-5,6,7,8-四氢-1,6-二氮杂萘 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(furan-2-yl)-10-[2-(3-methyl-7,8-dihydro-5H-1,6-naphthyridin-6-yl)ethyl]-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-7-amine
  参考文献：
  名称：

  Design, synthesis, and evaluation of fused heterocyclic analogs of SCH 58261 as adenosine A2A receptor antagonists

  摘要：

  SCH 58261 is a reported adenosine A(2A) receptor antagonist which is active in rat in vivo models of Parkinson's Disease upon ip administration. However, it has poor selectivity versus the A(1) receptor and does not demonstrate oral activity. Quinoline analogs have improved upon the selectivity and pharmacokinetics of SCH 58261, but were difficult to handle due to poor aqueous solubility. We report the design and synthesis of fused heterocyclic analogs of SCH 58261 with aqueous solubility as well as improved A(2A) receptor binding selectivity and pharmacokinetic properties. In particular, the tetrahydronaphthyridine 4s has excellent A(2A) receptor in vitro binding affinity and selectivity, is active orally in a rat in vivo model of Parkinson's Disease, and has aqueous solubility of 100 mu M at physiological pH. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.069

文献信息

• [EN] ADENOSINE A¿2a< RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR A2A D'ADENOSINE
  申请人：SCHERING CORP

  公开号：WO2003048165A1

  公开（公告）日：2003-06-12

  Disclosed herein are compounds having the structural formula (A) including pharmaceutically acceptable salts or solvates of said compound, wherein X, Y, Q and R are as defined in the specification; pharmaceutical compositions thereof; methods of treating central nervous system diseases by administering the compound of the present invention to a patient in need of such treatment, and processes for preparing the compound of this invention.

  本文揭示了具有结构式(A)的化合物，包括该化合物的药用可接受盐或溶剂，其中X，Y，Q和R如规范所定义;其制药组合物;通过向需要此类治疗的患者施用本发明的化合物治疗中枢神经系统疾病的方法，以及制备本发明化合物的方法。
• Adenosine A2a receptor antagonists for the treatment of extra-pyramidal syndrome and other movement disorders
  申请人：Schering Corporation

  公开号：US20040138235A1

  公开（公告）日：2004-07-15

  There is disclosed a method for the treatment or prevention of Extra Pyramidal syndrome (EPS), dystonia, restless leg syndrome (RLS) or periodic leg movement in sleep (PLMS) comprising the administration of an adenosine A2a receptor antagonist, alone or in combination with other agents useful for treating EPS, dystonia, RLS or PLMS.

  本发明公开了一种治疗或预防锥体外系综合征（EPS）、肌张力障碍、不安腿综合征（RLS）或睡眠中周期性腿部运动（PLMS）的方法，该方法包括单独或与其他用于治疗EPS、肌张力障碍、RLS或PLMS的药物联合使用腺苷A2a受体拮抗剂。
• ADENOSINE A2a RECEPTOR ANTAGONISTS
  申请人：Schering Corporation

  公开号：EP1448565B1

  公开（公告）日：2009-12-30
• ADENOSINE A2A RECEPTOR ANTAGONISTS FOR THE TREATMENT OF EXTRA-PYRAMIDAL SYNDROME AND OTHER MOVEMENT DISORDERS
  申请人：Grzelak Michael

  公开号：US20090029967A1

  公开（公告）日：2009-01-29

  There is disclosed a method for the treatment or prevention of Extra Pyramidal syndrome (EPS), dystonia, restless leg syndrome (RLS) or periodic leg movement in sleep (PLMS) comprising the administration of an adenosine A2a receptor antagonist, alone or in combination with other agents useful for treating EPS, dystonia, RLS or PLMS.
• US7414058B2
  申请人：——

  公开号：US7414058B2

  公开（公告）日：2008-08-19