4-[(2R)-2-(3-环戊基氧基-4-甲氧基苯基)-2-苯基乙基]吡啶 | 162542-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-[(2R)-2-(3-环戊基氧基-4-甲氧基苯基)-2-苯基乙基]吡啶
• 英文名称: R-(+)-4-(2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethyl)pyridine
• 英文别名: (R)-(+)-4-[2-(3-Cyclopentyloxy-4-methoxyphenyl)-2-phenylethyl]pyridine；CDP 840；R-(+)-4-[2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethyl] pyridine；CDP840；(R)-CDP-840；4-(2-(3-(Cyclopentyloxy)-4-methoxyphenyl)-2-phenylethyl)pyridine；4-[(2R)-2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenylethyl]pyridine
• CAS: 162542-90-7
• 化学式: C₂₅H₂₇NO₂
• 分子量: 373.495
• InChiKey: UTUUPXBCDMQYRR-HSZRJFAPSA-N

物化性质

• 沸点：
  489.9±45.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)
• 溶解度：
  <40.99mg/ml，溶于 DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

制备方法与用途

CDP-840(GR259653X)是一种高效、选择性且具有口服活性的磷酸二酯酶IV(PDE IV)抑制剂。研究显示，它能够有效抑制抗原诱导的清醒松鼠猴早期和晚期支气管收缩。

反应信息

• 作为反应物：
  描述：

  4-[(2R)-2-(3-环戊基氧基-4-甲氧基苯基)-2-苯基乙基]吡啶 在 过氧乙酸 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到2DG4Lmg5UL
  参考文献：
  名称：

  CDP840. A prototype of a novel class of orally active anti-Inflammatory phosphodiesterase 4 inhibitors

  摘要：

  The discovery, synthesis and biological activity of a series of triarylethane phosphodiesterase 4 inhibitors is described. Structure-activity relationship studies are presented for CDP840 29), a potent, chiral, selective inhibitor of PDE 4 (IC50 4nM). CDP840 is non-emetic in the ferret at 30 mg kg(-1) (po), active in models of inflammation and reverses ozone-induced bronchial hyperreactivity in the guinea pig. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00202-0
• 作为产物：
  描述：

  (1S,2R)-2-(3-cyclopentyloxy-4-methoxyphenyl)-2-phenyl-1-pyridin-4-ylethanol 在 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 10.5h， 生成 4-[(2R)-2-(3-环戊基氧基-4-甲氧基苯基)-2-苯基乙基]吡啶
  参考文献：
  名称：

  Asymmetric Synthesis of CDP840 by Jacobsen Epoxidation. An Unusual Syn Selective Reduction of an Epoxide

  摘要：

  An asymmetric synthesis of the PDE IV inhibitor, CDP840 (3) is reported. The absolute stereochemistry was controlled by a Jacobsen epoxidation of the Z triaryl olefin 8 (89% ee) or the E triaryl olefin 9 (48% ee). The disparate results in stereocontrol were interpreted in terms of the "skewed side-on approach model" proposed by Jacobsen. LiBK4 . BH3 reduction of the epoxides was found to proceed with retention of configuration.

  DOI：

  10.1021/jo971476c

文献信息

• [EN] PYRROLOTRIAZINONE DERIVATIVES AS PI3K INHIBITORS<br/>[FR] DÉRIVÉS DE PYRROLOTRIAZINONE EN TANT QU'INHIBITEURS DES PI3K
  申请人：ALMIRALL SA

  公开号：WO2014060432A1

  公开（公告）日：2014-04-24

  New pyrrolotriazinone derivatives having the chemical structure of formula (I), are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Phosphoinositide 3-Kinases (PI3Ks)

  新的吡咯三唑酮衍生物具有化学结构式（I），公开；以及它们的制备方法，包括它们的药物组合物和它们作为磷脂酰肌醇3-激酶（PI3Ks）抑制剂在治疗中的应用。
• New CRTh2 antagonists
  申请人：Almirall, S.A.

  公开号：EP2548876A1

  公开（公告）日：2013-01-23

  The present invention relates to compounds of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.

  本发明涉及式(I)的化合物，制备这种化合物的方法以及它们在治疗病理状况或疾病中的应用，该病理状况或疾病容易通过CRTh2拮抗活性得到改善。
• Modulators of Cystic Fibrosis Transmembrane Conductance Regulator
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：US20160095858A1

  公开（公告）日：2016-04-07

  The present invention features a compound of formula I: or a pharmaceutically acceptable salt thereof, where R 1 , R 2 , R 3 , W, X, Y, Z, n, o, p, and q are defined herein, for the treatment of CFTR mediated diseases, such as cystic fibrosis. The present invention also features pharmaceutical compositions, method of treating, and kits thereof.

  本发明涉及一种具有以下化学式I的化合物： 或其药用可接受的盐，其中R 1 ，R 2 ，R 3 ，W，X，Y，Z，n，o，p和q在此处定义，用于治疗CFTR介导的疾病，如囊性纤维化。本发明还涉及药物组合物、治疗方法和相关工具包。
• SUBSTITUTED PYRIDINYL-PYRIMIDINES AND THEIR USE AS MEDICAMENTS
  申请人：Dahmann Georg

  公开号：US20130023502A1

  公开（公告）日：2013-01-24

  The invention relates to new substituted pyridinyl-pyrimidines of formula 1 wherein ring A is a five-membered saturated or unsaturated carbocyclic ring which optionally comprises one, two or three heteroatoms each independently from each other selected from the group N, S and O, wherein R 1 , R 2 , R 4 , R 3 , R 5 and R 6 are defined as in claim 1 and wherein ring A is further optionally substituted by one or two further substituents and the pharmaceutically acceptable salts, diastereomers, enantiomers, racemates, hydrates and solvates of the aforementioned compounds.

  该发明涉及公式1中的新取代吡啶基嘧啶化合物， 其中环A是一个含有五个成员的饱和或不饱和碳环，该环可选地包含一个、两个或三个异原子，每个异原子独立地选自N、S和O组成， 其中R1、R2、R4、R3、R5和R6如权利要求书中所定义，并且环A进一步可选地被一个或两个进一步取代基取代，以及上述化合物的药用盐、二对映体、对映体、消旋体、水合物和溶剂化合物。
• Pyrazole derivatives as jak inhibitors
  申请人：Almirall, S.A.

  公开号：EP2360158A1

  公开（公告）日：2011-08-24

  New pyrazole derivatives having the chemical structure of formula (I) are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Janus Kinases (JAK).

  新的吡唑衍生物具有化学结构式（I），公开了它们的制备方法，包括它们的制药组合物以及它们作为Janus激酶（JAK）抑制剂在治疗中的用途。