(αR)-α-(aminomethyl)-α-methylcyclopropanemethanol | 912454-48-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (αR)-α-(aminomethyl)-α-methylcyclopropanemethanol
• 英文别名: (R)-α-(acetyloxy)-α-methyl-cyclopropaneacetonitrile；(R)-1-amino-2-cyclopropyl-propan-2-ol；(R)-α-(aminomethyl)-α-methyl-cyclopropanemethanol；(R)-alpha-(aminomethyl)-alpha-methyl-cyclopropanemethanol；(2R)-1-amino-2-cyclopropylpropan-2-ol
• CAS: 912454-48-9
• 化学式: C₆H₁₃NO
• 分子量: 115.175
• InChiKey: PSDJRLLXPKWQLH-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (αR)-α-(aminomethyl)-α-methylcyclopropanemethanol 、 5-(4-氯苯基)-6-(环丙基甲氧基)-3-吡啶羧酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以94%的产率得到5-(4-chlorophenyl)-N-[(2R)-2-cyclopropyl-2-hydroxypropyl]-6-(cyclopropylmethoxy)-3-pyridine carboxamide
  参考文献：
  名称：

  6-Alkoxy-5-aryl-3-pyridinecarboxamides, a New Series of Bioavailable Cannabinoid Receptor Type 1 (CB1) Antagonists Including Peripherally Selective Compounds

  摘要：

  We identified 6-alkoxy-5-aryl-3-pyridinecarboxamides as potent CB1 receptor antagonists with high selectivity over CB2 receptors. The series was optimized to reduce lipophilicity compared to rimonabant to achieve peripherally active molecules with minimal central effects. Several compounds that showed high plasma exposures in rats were evaluated in vivo to probe the contribution of central vs peripheral CB1 agonism to metabolic improvement. Both rimonabant and 14g, a potent brain penetrant CB1 receptor antagonist, significantly reduced the rate of body weight gain. However, 14h, a molecule with markedly reduced brain exposure, had no significant effect on body weight. PK studies confirmed similarly high exposure of both 14h and 14g in the periphery but 10-fold lower exposure in the brain for 14h. On the basis of these data, which are consistent with reported effects in tissue-specific CB1 receptor KO mice, we conclude that the metabolic benefits of CB1 receptor antagonists are primarily centrally mediated as originally believed.

  DOI：

  10.1021/jm4010708
• 作为产物：
  描述：

  (R)-α-(acetyloxy)-α-methyl-cyclopropaneacetonitrile 在 lithium aluminium tetrahydride 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (αR)-α-(aminomethyl)-α-methylcyclopropanemethanol
  参考文献：
  名称：

  3-Pyridinecarboxamide derivatives as HDL-cholesterol raising agents

  摘要：

  本发明涉及一种提高HDL胆固醇的方法，包括向需要的患者施用以下公式的化合物： 其中A、G、R1至R8和R17如描述中所定义。

  公开号：

  US20080085906A1

文献信息

• [EN] PYRIDIN- 2 -AMIDES USEFUL AS CB2 AGONISTS<br/>[FR] PYRIDIN-2-AMIDES UTILES COMME AGONISTES DE CB2
  申请人：HOFFMANN LA ROCHE

  公开号：WO2012168350A1

  公开（公告）日：2012-12-13

  The invention relates to a compound of formula (I) wherein R1 to R4 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.

  本发明涉及式(I)的化合物，其中R1至R4的定义如描述和权利要求中所述。式(I)的化合物可以用作药物。
• NOVEL PYRIDINE DERIVATIVES
  申请人：Bissantz Caterina

  公开号：US20120316147A1

  公开（公告）日：2012-12-13

  The invention relates to a compound of formula (I) wherein R 1 to R 4 are defined as in the description and in the claims. The compound of formula (I) can be used as a medicament.

  本发明涉及一种公式(I)的化合物 其中R1至R4定义如描述和权利要求中所述。公式(I)的化合物可作为药物使用。
• Pyrazinecarboxamide derivatives as CB1 antagonists
  申请人：Hebeisen Paul

  公开号：US20070293509A1

  公开（公告）日：2007-12-20

  The present invention relates to compounds of the formula I: wherein R 1 to R 8 are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with the modulation of CB1 receptors, such as obesity.

  本发明涉及以下式I的化合物： 其中R1至R8如描述和索赔中定义，并且其药学上可接受的盐。这些化合物对于治疗和/或预防与调节CB1受体相关的疾病，如肥胖症，是有用的。
• Pyridine-3-carboxamide derivatives as CB1 inverse agonists
  申请人：Hebeisen Paul

  公开号：US20060229326A1

  公开（公告）日：2006-10-12

  The present invention relates to compounds of the formula wherein X and R 1 to R 8 are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with the modulation of CB1 receptors, such as obesity.

  本发明涉及以下式中的化合物，其中X和R1至R8如描述和索赔中所定义，并且其药学上可接受的盐。这些化合物可用于治疗和/或预防与CB1受体调节相关的疾病，如肥胖症。
• 5-PHENYL-NICOTINAMIDE DERIVATIVES
  申请人：Hebeisen Paul

  公开号：US20080070931A1

  公开（公告）日：2008-03-20

  The present invention relates to compounds of the formula wherein R 1 to R 8 are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with the modulation of CB1 receptors.

  本发明涉及公式中的化合物，其中R1至R8如描述和索赔中定义，并且其药用盐。这些化合物可用于治疗和/或预防与CB1受体调节相关的疾病。