6-氯-N-(2-环丙基乙基)吡嗪-3-羧酰胺 | 840488-85-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 哒嗪类化合物
• 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: 6-氯-N-(2-环丙基乙基)吡嗪-3-羧酰胺
• 英文名称: 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide
• 英文别名: 6-chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide；6-CHLOROPYRIDAZINE-3-CARBOXYLIC ACID (2-CYCLOPROPYL-ETHYL)AMIDE；N-(2-Cyclopropylethyl)-6-chloropyridazine-3-carboxamide
• CAS: 840488-85-9
• 化学式: C₁₀H₁₂ClN₃O
• 分子量: 225.678
• InChiKey: ZNOCYNRWXAYNOU-UHFFFAOYSA-N

物化性质

• 沸点：
  466.6±30.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-氯-N-(2-环丙基乙基)吡嗪-3-羧酰胺 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.08h， 生成 6-[4-(4-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide
  参考文献：
  名称：

  Discovery of Piperazin-1-ylpyridazine-Based Potent and Selective Stearoyl-CoA Desaturase-1 Inhibitors for the Treatment of Obesity and Metabolic Syndrome

  摘要：

  Stearoyl-CoA desaturase-1 (SCD1) catalyzes de novo synthesis of monounsaturated fatty acids from saturated fatty acids. Studies have demonstrated that rodents lacking a functional SCD1 gene have an improved metabolic profile, including reduced weight gain, lower triglycerides, and improved insulin response. In this study, we discovered a series of piperazinylpyridazine-based highly potent, selective, and orally bioavailable compounds. Particularly, compound 49 (XEN103) was highly active in vitro (mSCD1 IC50 = 14 nM and HepG2 IC50 = 12 nM) and efficacious in vivo (ED50 = 0.8 mg/kg). It also demonstrated striking reduction of weight gain in a rodent model. Our findings with small-molecule SCD1 inhibitors confirm the importance of this target in metabolic regulation, describe novel models for assessing SCD1 inhibitors for efficacy and tolerability and demonstrate an opportunity to develop a novel therapy for metabolic disease.

  DOI：

  10.1021/jm301661h
• 作为产物：
  描述：

  环丙乙腈 在 lithium aluminium tetrahydride 、 硫酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 38.25h， 生成 6-氯-N-(2-环丙基乙基)吡嗪-3-羧酰胺
  参考文献：
  名称：

  Piperazine derivatives and their use as therapeutic agents

  摘要：

  公开号：

  EP2316827B1

文献信息

• [EN] HETEROCYCLIC DERIVATIVES AND THEIR USE AS MEDIATORS OF STEAROYL-COA DESATURASE<br/>[FR] DERIVES HETEROCYCLIQUES ET LEUR UTILISATION EN TANT QUE MODULATEURS DE STEAROYLE-COA DESATURASE
  申请人：XENON PHARMACEUTICALS INC

  公开号：WO2006034338A1

  公开（公告）日：2006-03-30

  Methods of treating an SCD-mediated disease or condition in a mammal, preferably a human, are disclosed, wherein the methods comprise administering to a mammal in need thereof a compound of formula (I): Formula (I) where x, y, G, J, L, M, V, W, R2, R3, R4, R5, R5a, R6, R6a, R7, R7a, R8 and R8a are defined herein. Pharmaceutical compositions comprising the compounds of formula (I) are also disclosed.

  本发明揭示了治疗哺乳动物，尤其是人类患有SCD介导的疾病或症状的方法，其中所述方法包括向需要的哺乳动物施用以下化合物（I）的方法：化合物（I）其中x、y、G、J、L、M、V、W、R2、R3、R4、R5、R5a、R6、R6a、R7、R7a、R8和R8a在此处被定义。还揭示了包含化合物（I）的药物组合物。
• Pyridazine Derivatives for Inhibiting Human Stearoyl-Coa-Desaturase
  申请人：Kamboj Rajender

  公开号：US20080207587A1

  公开（公告）日：2008-08-28

  Methods of treating an SCD-mediated disease or condition in a mammal, preferably a human, are disclosed, wherein the methods comprise administering to a mammal in need thereof a compound of formula (I) where x, y, G, J, K, L, M, Q, W, V, R2, R3, R5, R5a, R6, R6a, R7, R7a, R8 and R8a arc defined herein. Pharmaceutical compositions comprising the compounds of formula (I) are also disclosed.

  本发明揭示了治疗哺乳动物，尤其是人类患有SCD介导的疾病或病况的方法，其中所述方法包括向需要的哺乳动物投药化合物(I)的步骤，其中化合物(I)的公式为x、y、G、J、K、L、M、Q、W、V、R2、R3、R5、R5a、R6、R6a、R7、R7a、R8和R8a在此处被定义。还揭示了包含化合物(I)的制药组合物。
• 2-HETEROARYL-PYRROLO[3,4-C]PYRROLE DERIVATIVES AND THEIR USE AS SCD INHIBITORS
  申请人：ZOLLER Gerhard

  公开号：US20100144594A1

  公开（公告）日：2010-06-10

  The invention relates to heterocyclic derivatives of formula I wherein R, R1, A, B, D, M, L and n are as defined herein, or their physiologically compatible salts, their pharmaceutical compositions and their uses as SCD1 inhibitors.

  本发明涉及式I的杂环衍生物，其中R、R1、A、B、D、M、L和n的定义如本文所示，或其生理相容性盐，它们的制药组合物以及它们作为SCD1抑制剂的用途。
• Heterocyclic Derivatives and Their Use as Strearoyl-Coa Desaturase Inhibitors
  申请人：Kamboj Rajender

  公开号：US20080125434A1

  公开（公告）日：2008-05-29

  Methods of treating an SCD-mediated disease or condition in a mammal, preferably a human, are disclosed, wherein the methods comprise administering to a mammal in need thereof a compound of formula (I): where x, y, G, J, K, L, M, W, R 2 , R 3 , R 5 , R 5a , R 6 , R 6a , R 7 , R 7a , R 8 and R 8a are defined herein. Pharmaceutical compositions comprising the compounds of formula (I) are also disclosed.

  本发明揭示了一种治疗哺乳动物（优选为人类）SCD介导的疾病或病症的方法，其中该方法包括向需要治疗的哺乳动物施用化合物I的方法：其中x、y、G、J、K、L、M、W、R2、R3、R5、R5a、R6、R6a、R7、R7a、R8和R8a在此定义。本发明还揭示了包含化合物I的药物组合物。
• Pyridazine derivatives and their use as therapeutic agents
  申请人：Chakka Nagasree

  公开号：US20060009459A1

  公开（公告）日：2006-01-12

  Methods of treating an SCD-mediated disease or condition in a mammal, preferably a human, are disclosed, wherein the methods comprise administering to a mammal in need thereof a compound of formula (Ia): where x, y, W, V, R 2 , R 3 , R 4 , R 5 , R 6 , R 6a , R 7 , R 7a , R 8 , R 8a , R 9 and R 9a are defined herein. Pharmaceutical compositions comprising the compounds of formula (I) are also disclosed.

  本发明涉及一种治疗哺乳动物（优选为人类）SCD介导的疾病或病症的方法，其中所述方法包括向需要治疗的哺乳动物中给予式(Ia)的化合物，其中x、y、W、V、R2、R3、R4、R5、R6、R6a、R7、R7a、R8、R8a、R9和R9a如本文所定义。此外，本发明还涉及含有式(I)的化合物的制药组合物。