6-chloro-N-isopentylpyridazine-3-carboxamide | 840488-86-0

• 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
• 英文名称: 6-chloro-N-isopentylpyridazine-3-carboxamide
• 英文别名: 6-chloropyridazine-3-carboxylic acid (3-methylbutyl)amide；6-chloro-N-(3-methylbutyl)pyridazine-3-carboxamide
• CAS: 840488-86-0
• 化学式: C₁₀H₁₄ClN₃O
• 分子量: 227.694
• InChiKey: KQBDDYSEVSDDMV-UHFFFAOYSA-N

物化性质

• 沸点：
  429.6±30.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• 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

反应信息

• 作为反应物：
  描述：

  6-chloro-N-isopentylpyridazine-3-carboxamide 在 偶氮二甲酸二叔丁酯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.83h， 生成 6-[4-(2-fluorophenoxy)piperidin-1-yl]-N-(3-methylbutyl)pyridazine-3-carboxamide
  参考文献：
  名称：

  Discovery of Potent, Selective, Orally Bioavailable Stearoyl-CoA Desaturase 1 Inhibitors

  摘要：

  Stearoyl-CoA desaturase 1 (SCD1) catalyzes the committed step in the biosynthesis of monounsaturated fatty acids from saturated, long-chain fatty acids. Studies with SCD1 knockout mice have established that these animals are lean and protected from leptin deficiency-induced and diet-induced obesity, with greater whole body insulin sensitivity than wild-type animals. In this work, we have discovered a series of potent, selective, orally bioavailable SCD1 inhibitors based on a known pyridazine carboxamide template. The representative lead inhibitor 28c also demonstrates excellent cellular activity in blocking the conversion of saturated long-chain fatty acid-CoAs (LCFA-CoAs) to monounsaturated LCFA-CoAs in HepG2 cells.

  DOI：

  10.1021/jm070219p
• 作为产物：
  描述：

  异戊胺 、 6-羟基-3-哒嗪甲酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以98%的产率得到6-chloro-N-isopentylpyridazine-3-carboxamide
  参考文献：
  名称：

  [EN] HETEROCYCLIC DERIVATIVES AND THEIR USE AS MEDIATORS OF STEAROYL-COA DESATURASE
  [FR] DERIVES HETEROCYCLIQUES ET LEUR UTILISATION EN TANT QUE MODULATEURS DE STEAROYLE-COA DESATURASE

  摘要：

  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。

  公开号：

  WO2006034338A1

文献信息

• 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。
• Heterocyclic Derivatives and Their Use as Mediators of Stearoyl-Coa Desaturase
  申请人：Kamboj Rajender

  公开号：US20070299081A1

  公开（公告）日：2007-12-27

  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, R 2 , R 3 , R 4 , 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.

  本发明揭示了治疗哺乳动物，特别是人类SCD介导的疾病或病状的方法，其中方法包括向需要该方法的哺乳动物施用式(I)的化合物：式(I)中x、y、G、J、L、M、V、W、R2、R3、R4、R5、R5a、R6、R6a、R7、R7a、R8和R8a如本文所定义。还揭示了包含式(I)的化合物的药物组合物。
• Heteroaromatic Compounds as Inhibitors of Stearoyl-Coenzyme a Delta-9 Desaturase
  申请人：Deschenes Denis

  公开号：US20090088431A1

  公开（公告）日：2009-04-02

  Heteroaromatic compounds of structural formula (I) are selective inhibitors of stearoyl-coenzyme A delta-9 desaturase (SCD1) relative to other known stearoyl-coenzyme A desaturases. The compounds of the present invention are useful for the prevention and treatment of conditions related to abnormal lipid synthesis and metabolism, including cardiovascular disease, such as atherosclerosis; lipid disorders; obesity; diabetes; neurological disease; metabolic syndrome; insulin resistance; fatty liver disease and cancer.

  结构式（I）的杂环芳香化合物相对于其他已知的硬脂酰辅酶A脱饱和酶（SCD1）是选择性抑制剂。本发明的化合物可用于预防和治疗与异常脂质合成和代谢有关的疾病，包括心血管疾病，如动脉粥样硬化；脂质紊乱；肥胖症；糖尿病；神经系统疾病；代谢综合症；胰岛素抵抗；脂肪肝病和癌症。
• PYRIDAZINE DERIVATIVES AND THEIR USE AS THERAPEUTIC AGENTS
  申请人：Bilich Andreas

  公开号：US20080280916A1

  公开（公告）日：2008-11-13

  Methods of treating an SCD-mediated skin disorder or condition in a mammal, preferably a human include administering to a mammal in need thereof a compound of formula (I): 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.

  治疗哺乳动物，特别是人类SCD介导的皮肤疾病或症状的方法包括向需要治疗的哺乳动物给予以下式子(I)的化合物：其中x，y，W，V，R2，R3，R4，R5，R6，R6a，R7，R7a，R8，R8a，R9和R9a在此处定义。
• Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase
  申请人：Xenon Pharmaceuticals Inc.

  公开号：US07951805B2

  公开（公告）日：2011-05-31

  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.

  本发明揭示了一种治疗哺乳动物（优选为人类）SCD介导的疾病或病状的方法，其中该方法包括向需要的哺乳动物中投与式（I）的化合物：式（I）其中x，y，G，J，L，M，V，W，R2，R3，R4，R5，R5a，R6，R6a，R7，R7a，R8和R8a在此被定义。本发明还揭示了包含式（I）化合物的制药组合物。