西他列汀Defuoro杂质5 | 486460-31-5

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 西他列汀Defuoro杂质5
• 英文名称: 7-[(3R)-3-amino-4-(2,5-difluorophenyl)butanoyl]-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine
• 英文别名: (2R)-4-oxo-4-[3-(trifluoromethyl)-5.6-dihydro[1,2,4]triazolo[4,3-α]pyrazin-7(8H)-yl]-1-(2,5-difluorophenyl)butan-2-amine；(3R)-3-amino-4-(2,5-difluorophenyl)-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]butan-1-one
• CAS: 486460-31-5
• 化学式: C₁₆H₁₆F₅N₅O
• 分子量: 389.328
• InChiKey: ABTMQWQGGARRSK-LLVKDONJSA-N

物化性质

• 沸点：
  530.3±60.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (R)-3-[(1,1-dimethylethoxycarbonyl)amino]-1-diazo-4-(2,5-difluorophenyl)butan-2-one 在 盐酸 、 lithium hydroxide 、 silver benzoate 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.5h， 生成 西他列汀Defuoro杂质5
  参考文献：
  名称：

  (2R)-4-Oxo-4-[3-(Trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin- 7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine:  A Potent, Orally Active Dipeptidyl Peptidase IV Inhibitor for the Treatment of Type 2 Diabetes

  摘要：

  A novel series of beta-amino amides incorporating fused heterocycles, i.e., triazolopiperazines, were synthesized and evaluated as inhibitors of dipeptidyl peptidase IV (DPP-IV) for the treatment of type 2 diabetes. (2R)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (1) is a potent, orally active DPP-IV inhibitor (IC(50) = 18 nM) with excellent selectivity over other proline-selective peptidases, oral bioavailability in preclinical species, and in vivo efficacy in animal models. MK-0431, the phosphate salt of compound 1, was selected for development as a potential new treatment for type 2 diabetes.

  DOI：

  10.1021/jm0493156

文献信息

• Pyrazole derivatives, compositions containing such compounds and methods of use
  申请人：Parmee R. Emma

  公开号：US20070088070A1

  公开（公告）日：2007-04-19

  Pyrazoles having a naphthyl group attached are disclosed. The compounds are useful for treating type 2 diabetes and related conditions. Pharmaceutical compositions and methods of treatment are also included.

  含有萘基团的吡唑类化合物已被披露。这些化合物对治疗2型糖尿病及相关疾病有用。同时还包括了药物组合物和治疗方法。
• BETA-AMINO HETEROCYCLIC DIPEPTIDYL PEPTIDASE INHIBITORS FOR THE TREATMENT OR PREVENTION OF DIABETES
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20150359793A1

  公开（公告）日：2015-12-17

  The present invention is directed to compounds 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.

  本发明涉及一种抑制二肽基肽酶-IV酶（“DP-IV抑制剂”）的化合物，该化合物在治疗或预防二肽基肽酶-IV酶参与的疾病中具有用途，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，以及在预防或治疗二肽基肽酶-IV酶参与的这类疾病中使用这些化合物和组合物。
• [EN] GLUCAGON RECEPTOR ANTAGONIST COMPOUNDS<br/>[FR] COMPOSÉS ANTAGONISTES DU RÉCEPTEUR DU GLUCAGON
  申请人：MERCK SHARP & DOHME

  公开号：WO2010071750A1

  公开（公告）日：2010-06-24

  Glucagon receptor antagonist compounds are disclosed. The compounds are useful for treating type 2 diabetes and related conditions. Pharmaceutical compositions and methods of treatment are also included.

  葡萄糖素受体拮抗剂化合物已经被披露。这些化合物可用于治疗2型糖尿病及相关疾病。同时还包括药物组合和治疗方法。
• Glucagon receptor antagonist compounds, compositions containing such compounds and methods of use
  申请人：Stelmach E. John

  公开号：US20080085926A1

  公开（公告）日：2008-04-10

  Glucagon receptor antagonist compounds are disclosed. The compounds are useful for treating type 2 diabetes and related conditions. Pharmaceutical compositions and methods of treatment are also included.

  葡萄糖素受体拮抗剂化合物已被披露。这些化合物对治疗2型糖尿病及相关疾病有用。还包括药物组合物和治疗方法。
• SITAGLIPTIN, SALTS AND POLYMORPHS THEREOF
  申请人：Sathe Dhananjay Govind

  公开号：US20130158265A1

  公开（公告）日：2013-06-20

  The present invention relates to an improved process for preparation of Sitagliptin or pharmaceutically acceptable salts thereof. The present invention further relates to novel polymorphs of Sitagliptin salts and process for preparation thereof.

  本发明涉及一种改进的Sitagliptin或其药用可接受盐的制备方法。本发明还涉及Sitagliptin盐的新型多形态和其制备方法。