(3S)-1-[(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(6-oxo-1,6-dihydroypyridin-3-yl)phenyl]-1-oxobutanyl]-3-fluoropyrrolidine | 690257-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (3S)-1-[(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(6-oxo-1,6-dihydroypyridin-3-yl)phenyl]-1-oxobutanyl]-3-fluoropyrrolidine
• 英文别名: (3S)-1-[(2S,3S)-2-(tert-Butoxycarbonylamino)-3-[4-(6-oxo-1,6-dihydropyridin-3-yl)phenyl]-1-oxobutanyl]-3-fluoropyrrolidine；tert-butyl N-[(2S,3S)-1-[(3S)-3-fluoropyrrolidin-1-yl]-1-oxo-3-[4-(6-oxo-1H-pyridin-3-yl)phenyl]butan-2-yl]carbamate
• CAS: 690257-88-6
• 化学式: C₂₄H₃₀FN₃O₄
• 分子量: 443.518
• InChiKey: QCNLMTRANXSDOX-ZRCAFCQKSA-N

物化性质

• 沸点：
  683.2±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S)-1-[(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(6-oxo-1,6-dihydroypyridin-3-yl)phenyl]-1-oxobutanyl]-3-fluoropyrrolidine 在 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (3S)-1-[(2S,3S)-2-amino-3-[4-(1-methyl-6-oxo-1,6-dihydroypyridin-3-yl)phenyl]-1-oxobutanyl]-3-fluoropyrrolidine trifluoroacetic acid salt
  参考文献：
  名称：

  发现有效，选择性和口服生物利用的基于吡啶酮的二肽基肽酶4抑制剂。

  摘要：

  抗取代的β-甲基苯基丙氨酸衍生的酰胺已被证明是有效的DPP-IV抑制剂，对DPP8和DPP9均表现出优异的选择性。优化的化合物在三个临床前物种中表现出良好的药代动力学特征。

  DOI：

  10.1016/j.bmcl.2005.11.052
• 作为产物：
  描述：

  (3S)-1-[(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-(4-bromophenyl)-1-oxobutanyl]-3-fluoropyrrolidine 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 吡啶盐酸盐 、 sodium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 (3S)-1-[(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(6-oxo-1,6-dihydroypyridin-3-yl)phenyl]-1-oxobutanyl]-3-fluoropyrrolidine
  参考文献：
  名称：

  发现有效，选择性和口服生物利用的基于吡啶酮的二肽基肽酶4抑制剂。

  摘要：

  抗取代的β-甲基苯基丙氨酸衍生的酰胺已被证明是有效的DPP-IV抑制剂，对DPP8和DPP9均表现出优异的选择性。优化的化合物在三个临床前物种中表现出良好的药代动力学特征。

  DOI：

  10.1016/j.bmcl.2005.11.052

文献信息

• [EN] PHENYLALANINE DERIVATIVES AS DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES<br/>[FR] DERIVES DE PHENYLALANINE UTILISES COMME INHIBITEURS DE LA DIPEPTIDYL PEPTIDASE DANS LE TRAITEMENT OU LA PREVENTION DU DIABETE
  申请人：MERCK & CO INC

  公开号：WO2004043940A1

  公开（公告）日：2004-05-27

  The present invention is directed to phenylalanine derivatives which are inhibitors of the dipeptidyl peptidase-IV enzyme ('DP-IV inhibitors') and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及苯丙氨酸衍生物，这些衍生物是二肽基肽酶-IV酶（'DP-IV抑制剂'）的抑制剂，并且在治疗或预防涉及二肽基肽酶-IV酶的疾病中具有用处，如糖尿病，特别是2型糖尿病。该发明还涉及包含这些化合物的药物组合物以及在预防或治疗涉及二肽基肽酶-IV酶的这类疾病中使用这些化合物和组合物。
• Phenylalanine derivatives as depeptidyl peptidase inhibitors for the treatment or prevention of diabetes
  申请人：Colandrea J. Vincent

  公开号：US20050222140A1

  公开（公告）日：2005-10-06

  The present invention is directed to phenylalanine derivatives which are inhibitors of the dipeptidyl peptidase-IV enzyme (“DP-IV inhibitors”) and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及苯丙氨酸衍生物，它们是二肽酶-IV酶（“DP-IV抑制剂”）的抑制剂，可用于治疗或预防二肽酶-IV酶参与的疾病，如糖尿病，特别是2型糖尿病。本发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在预防或治疗二肽酶-IV酶参与的疾病中的使用。
• Phenylalanine derivatives as dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes
  申请人：Merck & Co., Inc.

  公开号：US07157490B2

  公开（公告）日：2007-01-02

  The present invention is directed to phenylalanine derivatives which are inhibitors of the dipeptidyl peptidase-IV enzyme (“DP-IV inhibitors”) and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及苯丙氨酸衍生物，它们是二肽基肽酶IV酶（“DP-IV抑制剂”）的抑制剂，并且在治疗或预防二肽基肽酶IV酶涉及的疾病，如糖尿病，特别是2型糖尿病中有用。本发明还涉及包含这些化合物的制药组合物以及在预防或治疗二肽基肽酶IV酶涉及的这些疾病中使用这些化合物和组合物。
• PHENYLALANINE DERIVATIVES AS DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES
  申请人：Merck & Co., Inc.

  公开号：EP1562925A1

  公开（公告）日：2005-08-17
• US7157490B2
  申请人：——

  公开号：US7157490B2

  公开（公告）日：2007-01-02