(6aR,9R)-5-bromo-N-[(2S)-1-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 英文名称: (6aR,9R)-5-bromo-N-[(2S)-1-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• 化学式: C₂₀H₂₄BrN₃O₂
• 分子量: 418.3
• InChiKey: HLCJZEGQKUDFSA-BWACUDIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  68.4
• 氢给体数：
  3
• 氢受体数：
  3

文献信息

• NOVEL METHYSERGIDE DERIVATIVES
  申请人：MAP PHARMACEUTICALS, INC.

  公开号：US20140179730A1

  公开（公告）日：2014-06-26

  Provided herein are novel methysergide derivatives and compositions thereof. In other embodiments, provided herein are methods of treatment, prevention, or amelioration of a variety of medical disorders or symptoms thereof, such as, migraine and Parkinson's disease using the compounds and compositions disclosed herein. In still other embodiments, provided herein, such as, for example, are methods for antagonizing the 5-HT 2B receptor without agonizing the 5-HT 2B receptor using the compounds and compositions disclosed herein. In still other embodiments, provided herein such as, for example, are methods of agonizing the 5-HT 1A receptor using the compounds and compositions disclosed herein.

  本发明提供了新颖的美西麦角衍生物及其组合物。在其他实施例中，本发明提供了治疗、预防或缓解各种医疗疾病或其症状的方法，例如使用本文披露的化合物和组合物治疗偏头痛和帕金森病。在其他实施例中，本发明提供了例如使用本文披露的化合物和组合物拮抗5-HT2B受体而不激动5-HT2B受体的方法。在其他实施例中，本发明提供了例如使用本文披露的化合物和组合物激动5-HT1A受体的方法。
• Process of synthesizing 2-bromo-LSD
  申请人：Kirkland Justin

  公开号：US10377752B2

  公开（公告）日：2019-08-13

  A process of synthesizing 2-bromo-LSD or a salt or hydrate thereof comprising the steps of reacting methylergometrine with a brominating agent to produce [(1S)-1-(Hydroxymethyl)propylamino][(6aR,9R)-5-bromo-7-methyl-4,7-diaza-4,6,6a,7,8,9-hexahydroacephenanthrylen-9-yl]formaldehyde as a first intermediate, and then hydrolyzing [(1S)-1-(Hydroxymethyl)propylamino][(6aR,9R)-5-bromo-7-methyl-4,7-diaza-4,6,6a,7,8,9-hexahydroacephenanthrylen-9-yl]formaldehyde to yield bromo-lysergic acid as a second intermediate, wherein bromo-lysergic acid is then amidated to yield 2-bromo-LSD or a salt or hydrate thereof.

  一种合成 2-溴-LSD 或其盐或水合物的工艺，包括以下步骤：将甲基麦角新碱与溴化剂反应生成[(1S)-1-(羟甲基)丙基氨基][(6aR,9R)-5-溴-7-甲基-4,7-二氮杂-4,6,6a,7,8,9-六氢杂蒽-9-基]甲醛作为第一中间体、然后水解[(1S)-1-(羟甲基)丙基氨基][(6aR,9R)-5-溴-7-甲基-4,7-二氮杂-4,6,6a,7,8,9-六氢苯并蒽-9-基]甲醛，得到作为第二中间体的溴麦角酸，其中溴麦角酸随后被酰胺化，得到 2-溴-LSD 或其盐或水合物。
• US8895743B2
  申请人：——

  公开号：US8895743B2

  公开（公告）日：2014-11-25
• [EN] NOVEL METHYSERGIDE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS DE MÉTHYSERGIDE
  申请人：MAP PHARMACEUTICALS INC

  公开号：WO2014100354A1

  公开（公告）日：2014-06-26

  Provided herein are novel methysergide derivatives and compositions thereof. In other embodiments, provided herein are methods of treatment, prevention, or amelioration of a variety of medical disorders or symptoms thereof, such as, migraine and Parkinson's disease using the compounds and compositions disclosed herein. In still other embodiments, provided herein, such as, for example, are methods for antagonizing the 5-HT2B receptor without agonizing the 5-HT2B receptor using the compounds and compositions disclosed herein. In still other embodiments, provided herein such as, for example, are methods of agonizing the 5-HT1A receptor using the compounds and compositions disclosed herein.