1-(6-chloro-5-nitro-pyrimidin-4-yl)-piperidine-4-carboxylic acid ethyl ester | 733747-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(6-chloro-5-nitro-pyrimidin-4-yl)-piperidine-4-carboxylic acid ethyl ester
• 英文别名: Ethyl 1-(6-chloro-5-nitropyrimidin-4-yl)piperidine-4-carboxylate
• CAS: 733747-96-1
• 化学式: C₁₂H₁₅ClN₄O₄
• 分子量: 314.728
• InChiKey: MMBCFJRVLWLMEY-UHFFFAOYSA-N

物化性质

• 沸点：
  475.2±45.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(6-chloro-5-nitro-pyrimidin-4-yl)-piperidine-4-carboxylic acid ethyl ester 、 4-(1H-1,2,4-噻唑-1-基）苯胺 在 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.08h， 以55%的产率得到1-[5-nitro-6-(4-[1,2,4]triazol-1-yl-phenylamino)-pyrimidin-4-yl]-piperidine-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Discovery of the First Potent and Orally Efficacious Agonist of the Orphan G-Protein Coupled Receptor 119

  摘要：

  GPR119 is a rhodopsin-like GPCR expressed in pancreatic beta-cells and incretin releasing cells in the GI tract. As with incretins, GPR119 increase,; cAMP levels in these cell types. thus making it a highly attractive potential target for the treatment of diabetes. The discovery of the first reported potent agonist of GPR119, 2-fluoro-4-methanesulfonyl-phenyl)-{6-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-5-nitro-pyrimidin-4-yl}-amine (8g, AR231453), is described starting from an initial inverse agonist screening hit. Compound 8g showed in vivo activity in rodents and was active in an oral glucose tolerance test in mice following oral administration.

  DOI：

  10.1021/jm8006867
• 作为产物：
  描述：

  哌啶-4-甲酸乙酯 、 2,4-二氯-5 硝基嘧啶 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到1-(6-chloro-5-nitro-pyrimidin-4-yl)-piperidine-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Discovery of the First Potent and Orally Efficacious Agonist of the Orphan G-Protein Coupled Receptor 119

  摘要：

  GPR119 is a rhodopsin-like GPCR expressed in pancreatic beta-cells and incretin releasing cells in the GI tract. As with incretins, GPR119 increase,; cAMP levels in these cell types. thus making it a highly attractive potential target for the treatment of diabetes. The discovery of the first reported potent agonist of GPR119, 2-fluoro-4-methanesulfonyl-phenyl)-{6-[4-(3-isopropyl-[1,2,4]oxadiazol-5-yl)-piperidin-1-yl]-5-nitro-pyrimidin-4-yl}-amine (8g, AR231453), is described starting from an initial inverse agonist screening hit. Compound 8g showed in vivo activity in rodents and was active in an oral glucose tolerance test in mice following oral administration.

  DOI：

  10.1021/jm8006867

文献信息

• [EN] 1,2,3-TRISUBSTITUTED ARYL AND HETEROARYL DERIVATIVES AS MODULATORS OF METABOLISM AND THE PRPPHYLAXIS AND TREATMENT OF DISORDERS RELATED THERETO SUCH AS DIABETES AND HYPERGLYCEMIA<br/>[FR] DERIVES ARYLES ET HETEROARYLES TRI-SUBSTITUES EN POSITION 1,2,3 EN TANT QUE MODULATEURS DE METABOLISME ET PROPHYLAXIE ET TRAITEMENT DE TROUBLES LIES AU METABOLISME
  申请人：ARENA PHARM INC

  公开号：WO2004065380A1

  公开（公告）日：2004-08-05

  The present invention relates to certain 1,2,3-trisubstituted aryl and heteroaryl derivatives of Fomula (Ia) that are modulators of metabolism. Accordingly, compounds of the present invention are useful in the prophylaxis or treatment of metabolic disorders and complications thereof, such as, diabetes and obesity.

  本发明涉及某些Fomula（Ia）的1,2,3-三取代芳基和杂芳基衍生物，它们是代谢调节剂。因此，本发明的化合物在预防或治疗代谢紊乱及其并发症，如糖尿病和肥胖方面是有用的。
• 1,2,3-Trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
  申请人：Jones M. Robert

  公开号：US20060217379A1

  公开（公告）日：2006-09-28

  The present invention relates to certain 1,2,3-trisubstituted aryl and heteroaryl derivatives of Fomula (Ia) that are modulators of metabolism. Accordingly, compounds of the present invention are useful in the prophylaxis or treatment of metabolic disorders and complications thereof, such as, diabetes and obesity.

  本发明涉及某些1,2,3-三取代芳基和杂环芳基衍生物（Ia式）的代谢调节剂。因此，本发明的化合物在预防或治疗代谢性疾病及其并发症，如糖尿病和肥胖症方面是有用的。
• 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia
  申请人：Arena Pharmaceuticals, Inc.

  公开号：US08293751B2

  公开（公告）日：2012-10-23

  The present invention relates to certain 1,2,3-trisubstituted aryl and heteroaryl derivatives of Formula (Ia) that are modulators of metabolism. Accordingly, compounds of the present invention are useful in the prophylaxis or treatment of metabolic disorders and complications thereof, such as, diabetes and obesity.

  本发明涉及某些1,2,3-三取代芳基和杂环芳基衍生物的公式（Ia），它们是代谢调节剂。因此，本发明的化合物在预防或治疗代谢紊乱及其并发症，如糖尿病和肥胖症方面是有用的。
• 1,2,3-TRISUBSTITUTED ARYL AND HETEROARYL DERIVATIVES AS MODULATORS OF METABOLISM AND THE PROPHYLAXIS AND TREATMENT OF DISORDERS RELATED THERETO SUCH AS DIABETES AND HYPERGLYCEMIA
  申请人：Arena Pharmaceuticals, Inc.

  公开号：EP1599468B1

  公开（公告）日：2007-10-03
• US8293751B2
  申请人：——

  公开号：US8293751B2

  公开（公告）日：2012-10-23