2-[(1R)-1-aminoethyl]-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4-one | 873333-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 2-[(1R)-1-aminoethyl]-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4-one
• CAS: 873333-69-8
• 化学式: C₁₇H₁₅F₃N₄O₂
• 分子量: 364.327
• InChiKey: QNHMGGCWWUZDLU-SNVBAGLBSA-N

物化性质

• 沸点：
  499.1±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[(1R)-1-aminoethyl]-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4-one 、 乙基乙烯基砜 以 甲醇 为溶剂， 生成 (R)-2-[1-(2-ethanesulfonyl-ethylamino)-ethyl]-3-[4-(2,2,2-trifluoro-ethoxy)-phenyl]-3H-pyrido[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  [EN] TETRAHYDROQUINAZOLIN-4(3H)-ONE-RELATED AND TETRAHYDROPYRIDO[2,3-D]PYRIMIDIN-4(3H)-ONE-RELATED COMPOUNDS, COMPOSITIONS AND METHODS FOR THEIR USE
  [FR] COMPOSES TETRAHYDROQUINAZOLINE-4(3H)-ONIQUES ET TETRAHYDROPYRIDO[2,3-D]PYRIMIDINE-4(3H)-ONIQUES, COMPOSITIONS, ET PROCEDES D'UTILISATION CORRESPONDANTS

  摘要：

  提供具有以下公式（I）的化合物，其中变量A1、A2、A3、A4、R1、R2、R3、R4、Q和L在此处描述。这些化合物可用于治疗炎症和免疫状况和疾病。还提供了使用这些化合物进行治疗的组合物和方法。例如，这些方法可用于治疗炎症和免疫紊乱和疾病，如多发性硬化症、类风湿关节炎、牛皮癣和炎症性肠病。

  公开号：

  WO2006004925A1
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-[(1R)-1-aminoethyl]-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  Optimization of a series of quinazolinone-derived antagonists of CXCR3

  摘要：

  The evaluation of the CXCR3 antagonist AMG 487 in clinic trials was complicated due to the formation of an active metabolite. In this Letter, we will discuss the further optimization of the quinazolinone series that led to the discovery of compounds devoid of the formation of the active metabolite that was seen with AMG 487. In addition, these compounds also feature increased potency and good pharmacokinetic properties. We will also discuss the efficacy of the lead compound 34 in a mouse model of cellular recruitment induced by bleomycin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.032

文献信息

• [EN] FUSED PYRIMIDINE DERIVATIVES AND COMPOSITIONS THEREOF AS CXCR3 RECEPTOR MODULATORS, USEFUL IN PREVENTION AND TREATMENT OF INFLAMMATORY AND IMMUNOREGULATORY DISORDERS AND DISEASES<br/>[FR] DERIVES DE PYRIMIDINE FUSIONNES ET COMPOSITIONS SUR LEUR BASE, UTILISES EN TANT QUE MODULATEURS DU RECEPTEUR DE CXCR3, UTILES DANS LA PREVENTION ET LE TRAITEMENT DE MALADIES ET TROUBLES INFLAMMATOIRES OU IMMUNOREGULATEURS
  申请人：AMGEN INC

  公开号：WO2006004915A1

  公开（公告）日：2006-01-12

  Compounds are provided having the formula: wherein variables Ra, R1, R2, R3, R4, A1, A4, L, Q, X and subscript n as described herein. The subject compounds are useful for treatment of inflammatory and immune conditions and diseases. Compositions and methods of treatment using the subject compounds are also provided. For example, the subject methods are useful for treatment of inflammatory and immune disorders and disease such as multiple sclerosis, rheumatoid arthritis, psoriasis, and inflammatory bowel disease.

  提供具有以下公式的化合物：其中变量Ra、R1、R2、R3、R4、A1、A4、L、Q、X和下标n如本文所述。所述化合物对于治疗炎症和免疫状况和疾病有用。还提供使用所述化合物的组合物和治疗方法。例如，所述方法对于治疗炎症和免疫紊乱和疾病如多发性硬化症、类风湿关节炎、银屑病和炎症性肠病有用。
• [EN] TETRAHYDROQUINAZOLIN-4(3H)-ONE-RELATED AND TETRAHYDROPYRIDO[2,3-D]PYRIMIDIN-4(3H)-ONE-RELATED COMPOUNDS, COMPOSITIONS AND METHODS FOR THEIR USE<br/>[FR] COMPOSES TETRAHYDROQUINAZOLINE-4(3H)-ONIQUES ET TETRAHYDROPYRIDO[2,3-D]PYRIMIDINE-4(3H)-ONIQUES, COMPOSITIONS, ET PROCEDES D'UTILISATION CORRESPONDANTS
  申请人：AMGEN SF LLC

  公开号：WO2006004925A1

  公开（公告）日：2006-01-12

  Compounds are provided having the formula (I) wherein variables A1, A2, A3, A4, R1, R2, R3, R4, Q and L are described herein. The subject compounds are useful for treatment of inflammatory and immune conditions and diseases. Compositions and methods of treatment using the subject compounds are also provided. For example, the subject methods are useful for treatment of inflammatory and immune disorders and disease such as multiple sclerosis, rheumatoid arthritis, psoriasis, and inflammatory bowel disease.

  提供具有以下公式（I）的化合物，其中变量A1、A2、A3、A4、R1、R2、R3、R4、Q和L在此处描述。这些化合物可用于治疗炎症和免疫状况和疾病。还提供了使用这些化合物进行治疗的组合物和方法。例如，这些方法可用于治疗炎症和免疫紊乱和疾病，如多发性硬化症、类风湿关节炎、牛皮癣和炎症性肠病。
• US7375102B2
  申请人：——

  公开号：US7375102B2

  公开（公告）日：2008-05-20
• US7939538B2
  申请人：——

  公开号：US7939538B2

  公开（公告）日：2011-05-10
• Optimization of a series of quinazolinone-derived antagonists of CXCR3
  作者：Jiwen Liu、Zice Fu、An-Rong Li、Michael Johnson、Liusheng Zhu、Andrew Marcus、Jay Danao、Tim Sullivan、George Tonn、Tassie Collins、Julio Medina

  DOI：10.1016/j.bmcl.2009.07.032

  日期：2009.9

  The evaluation of the CXCR3 antagonist AMG 487 in clinic trials was complicated due to the formation of an active metabolite. In this Letter, we will discuss the further optimization of the quinazolinone series that led to the discovery of compounds devoid of the formation of the active metabolite that was seen with AMG 487. In addition, these compounds also feature increased potency and good pharmacokinetic properties. We will also discuss the efficacy of the lead compound 34 in a mouse model of cellular recruitment induced by bleomycin. (C) 2009 Elsevier Ltd. All rights reserved.