(S)-methyl 2-(4-chloro-2,6-dimethylphenoxy)-4-(1-hydroxybutan-2-ylamino)-6-methylnicotinate | 351422-30-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-methyl 2-(4-chloro-2,6-dimethylphenoxy)-4-(1-hydroxybutan-2-ylamino)-6-methylnicotinate
• 英文别名: 2-(4-chloro-2,6-dimethyl-phenoxy)-4-(S)-(1-hydroxymethyl-propylamino)-6-methyl-nicotinic acid methyl ester；methyl 2-(4-chloro-2,6-dimethylphenoxy)-4-{[(2S)-1-hydroxybutan-2-yl]amino}-6-methylpyridine-3-carboxylate；methyl 2-(4-chloro-2,6-dimethylphenoxy)-4-[[(2S)-1-hydroxybutan-2-yl]amino]-6-methylpyridine-3-carboxylate
• CAS: 351422-30-5
• 化学式: C₂₀H₂₅ClN₂O₄
• 分子量: 392.882
• InChiKey: IWNVXQFPEPXFQP-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  80.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(4-chloro-2,6-dimethylphenoxy)-4-(1-hydroxybutan-2-ylamino)-6-methylnicotinate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 生成 2-(4-Chloro-2,6-dimethyl-phenoxy)-4-(S)-(1-hydroxymethyl-propylamino)-6-methyl-nicotinic acid
  参考文献：
  名称：

  Corticotropin releasing factor antagonists

  摘要：

  抗皮质释放因子（CRF）拮抗剂具有下列结构式，其中虚线、A、B、Y、Z、G、R3、R4、R5、R6、R16和R17如申请中所定义，并且制备它们的方法。这些化合物及其药用盐在治疗包括中枢神经系统和与压力相关的疾病中是有用的。

  公开号：

  US06956047B1
• 作为产物：
  描述：

  4-chloro-6-methyl-2-(4-chloro-2,6-dimethylphenoxy)-1-nicotinic acid methyl ester 、 (S)-(+)-2-氨基-1-丁醇 以 N-甲基吡咯烷酮 为溶剂， 以6.684 g的产率得到(S)-methyl 2-(4-chloro-2,6-dimethylphenoxy)-4-(1-hydroxybutan-2-ylamino)-6-methylnicotinate
  参考文献：
  名称：

  2-Aryloxy-4-alkylaminopyridines: Discovery of Novel Corticotropin-Releasing Factor 1 Antagonists

  摘要：

  An orally active clinical candidate of corticotropin-releasing factor 1 (CRF(1)) antagonist 1 showed a significant positive food effect in dog and human after oral administration. Efforts to address the food effect issue led us to explore and discover compounds in series 2 as orally active CRF(1) receptor antagonists, in which some compounds showed improved physicochemical properties while retaining desired pharmacological properties. Compound 3a (CP-376395) was selected for further development, due not only to its reduced food effects but also its greater efficacy in CNS models. Compound 3a was advanced to the clinic. The synthesis of representative potential candidates and their in vitro, ex vivo, and in vivo data are described.

  DOI：

  10.1021/jm070579c

文献信息

• CORTICOTROPIN RELEASING FACTOR ANTAGONISTS
  申请人：Pfizer Products Inc.

  公开号：EP1263732A1

  公开（公告）日：2002-12-11
• US6833378B2
  申请人：——

  公开号：US6833378B2

  公开（公告）日：2004-12-21
• US6844351B1
  申请人：——

  公开号：US6844351B1

  公开（公告）日：2005-01-18
• US6956047B1
  申请人：——

  公开号：US6956047B1

  公开（公告）日：2005-10-18
• US7067664B1
  申请人：——

  公开号：US7067664B1

  公开（公告）日：2006-06-27