methyl 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-r-1-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-r-1-carboxylate
• 英文别名: methyl 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-1-carboxylate
• 化学式: C₂₁H₂₇NO₄
• 分子量: 357.45
• InChiKey: WUSGLEFPBNJHCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-r-1-carboxylate 在 silica gel 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 cilomilast
  参考文献：
  名称：

  A Practical Synthesis of the PDE4 Inhibitor, SB-207499, from a Cyclohexanone Precursor

  摘要：

  The synthesis of SB-207499 is described. Investigation and development of new strategies for the homologation of ketone, 4-cyano-4-[3-(cyclopentyloxy)-4-(methoxyphenyl)]-cyclohexan-1-one 2 are described which produce SB-207499. Our ultimate route of synthesis to SB-207499 is robust and operationally simple and produces the final drug substance in good yield and purity.

  DOI：

  10.1021/op025584z
• 作为产物：
  描述：

  1-[3-(环戊基氧基)-4-甲氧基苯基]-4-氧代环己烷甲腈 在 正丁基锂 、 高氯酸 、 mercury dichloride 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-r-1-carboxylate 、 methyl 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-r-1-carboxylate
  参考文献：
  名称：

  A Practical Synthesis of the PDE4 Inhibitor, SB-207499, from a Cyclohexanone Precursor

  摘要：

  The synthesis of SB-207499 is described. Investigation and development of new strategies for the homologation of ketone, 4-cyano-4-[3-(cyclopentyloxy)-4-(methoxyphenyl)]-cyclohexan-1-one 2 are described which produce SB-207499. Our ultimate route of synthesis to SB-207499 is robust and operationally simple and produces the final drug substance in good yield and purity.

  DOI：

  10.1021/op025584z

文献信息

• Compounds useful for treating allergic and inflammatory diseases
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0919544A1

  公开（公告）日：1999-06-02

  Novel compounds of Formula (I) are described herein. These compounds inhibit the production of Tumor Necrosis Factor and are useful in the treatment of disease states mediated or exacerbated by TNF production. The compounds of the present invention are also useful in the mediation or inhibition of enzymatic or catalytic activity of phosphodiesterase IV and are therefore useful in the treatment of disease states in need of mediation or inhibition thereof.

  式 (I) 的新型化合物 描述。这些化合物能抑制肿瘤坏死因子的产生，可用于治疗由 TNF 产生介导或加剧的疾病状态。本发明的化合物还可用于调解或抑制磷酸二酯酶 IV 的酶活性或催化活性，因此可用于治疗需要调解或抑制的疾病状态。
• Compounds usefulfor treating allergic and inflammatory diseases
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1420011A1

  公开（公告）日：2004-05-19

  Certain compounds of formulae (I) and (IA) are disclosed for use in the treatment and prophylaxis of arthritic conditions.

  式 (I) 和 (IA) 的某些化合物 公开了用于治疗和预防关节炎的化合物。
• Pharmaceutical composition of a pde4 or a pde3/4 inhibitor and a histamine receptor antagonist
  申请人：Nycomed GmbH

  公开号：EP1849468A2

  公开（公告）日：2007-10-31

  The invention relates to the combined administration of PDE4 or PDE3/4 inhibitors and histamine receptor antagonists for the treatment of respiratory diseases.

  本发明涉及联合使用 PDE4 或 PDE3/4 抑制剂和组胺受体拮抗剂治疗呼吸系统疾病。
• COMPOUNDS USEFUL FOR TREATING ALLERGIC AND INFLAMMATORY DISEASES
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0633776B1

  公开（公告）日：2001-05-09
• METHOD FOR TREATING MULTIPLE SCLEROSIS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1043994A1

  公开（公告）日：2000-10-18