6-methyl-8β-(6-chloro-3-pyridazinyl-carbamoyl)-ergoline

• 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: 6-methyl-8β-(6-chloro-3-pyridazinyl-carbamoyl)-ergoline
• 英文别名: (6aR,9R,10aR)-N-(6-chloropyridazin-3-yl)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
• 化学式: C₂₀H₂₀ClN₅O
• 分子量: 381.865
• InChiKey: WNVXZCMENBYWES-XNRPHZJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  73.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  9,10-dihydrolysergic acid methyl ester 在 sodium hydroxide 、 2-氯-1-甲基吡啶碘化物 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-methyl-8β-(6-chloro-3-pyridazinyl-carbamoyl)-ergoline
  参考文献：
  名称：

  Serotonergic ergoline derivatives

  摘要：

  Novel classes of 13- and 14-tertbutyl-ergoline derivatives were prepared, and characterised in vitro for their affinity for adrenergic, dopaminergic and serotonergic binding sites. This study particularly examines the importance of the presence and the position of the tert-butyl group in conferring either significant 5-HT1A or 5-HT2 affinity and selectivity respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00166-8

文献信息

• 8-pyridazinylcarbamoyl ergolines
  申请人：Farmitala Carlo Erba S.p.A.

  公开号：US04675404A1

  公开（公告）日：1987-06-23

  Ergoline derivatives of formula: ##STR1## wherein n=0,1,2; R.sub.1 =H, CH.sub.3 ; R.sub.2 =H, CH.sub.3, halogen; R.sub.3 =H, OCH.sub.3 ; R.sub.4 =hydrocarbon group and R.sub.5 is a residue of general formula II, III, IV, V, VI, VII: ##STR2## wherein R.sub.6 =H, Cl, OCH.sub.3, NR.sub.11 R.sub.12, wherein R.sub.11 and R.sub.12 =H, lower alkyl; phenyl or are bonded together to form a heterocyclic ring, R.sub.7, R.sub.8 and R.sub.9 and R.sub.10 =H or C.sub.1 -C.sub.3 alkyl, with the proviso that if R.sub.5 is of formula II and R.sub.2 =R.sub.7 =R.sub.8 =H, then R.sub.4 is not methyl or n is not 0. Pharmaceutically acceptable acid addition salts are also provided. A method for their preparation is also provided. The compounds have anti-depressive, anti-hypertensive and antiprolactin activity.

  公式为：##STR1## 的Ergoline衍生物，其中n=0,1,2; R.sub.1 =H，CH.sub.3; R.sub.2 =H，CH.sub.3，卤素; R.sub.3 =H，OCH.sub.3; R.sub.4 =碳氢基团，R.sub.5 是通式II，III，IV，V，VI，VII的残基：##STR2## 其中R.sub.6 =H，Cl，OCH.sub.3，NR.sub.11R.sub.12，其中R.sub.11和R.sub.12 =H，低碳基；苯基或结合在一起形成杂环环，R.sub.7，R.sub.8和R.sub.9和R.sub.10 =H或C.sub.1-C.sub.3烷基，但如果R.sub.5是公式II且R.sub.2 =R.sub.7 =R.sub.8 =H，则R.sub.4不是甲基或n不是0。还提供了药学上可接受的酸盐。还提供了它们的制备方法。这些化合物具有抗抑郁、降压和抗催乳素活性。
• Ergoline derivatives, processes for their preparation and pharmaceutical compositions containing them
  申请人：FARMITALIA CARLO ERBA S.p.A.

  公开号：EP0070562A1

  公开（公告）日：1983-01-26

  Ergoline derivatives of the formula wherein n = 0, 1, 2; R, = H, CH3; R2 = H, CH3, halogen; R3 = H, OCH3; R4 = hydrocarbon group and R5 is a residue of the general formula (II), (III), (IV), (V), (VI), (VII) wherein R6 = H, Cl, OCH3, NR11H12, wherein R11 and R12 = H, lower alkyl; phenyl or are bonded together to form a heterocyclic ring, R7, R8, R9 and R10 = H or C1-3 alkyl, with the proviso that if R5 is of formula (II) and R2=R7=R8=H, then R4 is not methyl or n is not 0; pharmaceutically acceptable acid addition salts of said ergoline derivatives and a method for their preparation are provided. The compounds exhibit in the form of pharmaceutical preparations anti-depressive, anti-hypertensive and anti-prolactin activity.

  式中的麦角啉衍生物 其中 n = 0、1、2；R, = H、CH3；R2 = H、CH3、卤素；R3 = H、OCH3；R4 = 烃基和 R5 是通式（II）、（III）、（IV）、（V）、（VI）、（VII）的残基 其中 R6 = H、Cl、OCH3、NR11H12，其中 R11 和 R12 = H、低级烷基；苯基或键合在一起形成杂环，R7、R8、R9 和 R10 = H 或 C1-3 烷基，但如果 R5 为式（II）且 R2=R7=R8=H 时，则 R4 不是甲基或 n 不是 0；提供了所述麦角啉衍生物的药学上可接受的酸加成盐及其制备方法。 这些化合物以药物制剂的形式表现出抗抑郁、抗高血压和抗催乳素活性。
• US4675404A
  申请人：——

  公开号：US4675404A

  公开（公告）日：1987-06-23
• Serotonergic ergoline derivatives
  作者：Sergio Mantegani、Enzo Brambilla、Carla Caccia、Gabriele Damiani、Maria Gioia Fornaretto、Robert A. McArthur、Mario Varasi

  DOI：10.1016/s0960-894x(98)00166-8

  日期：1998.5

  Novel classes of 13- and 14-tertbutyl-ergoline derivatives were prepared, and characterised in vitro for their affinity for adrenergic, dopaminergic and serotonergic binding sites. This study particularly examines the importance of the presence and the position of the tert-butyl group in conferring either significant 5-HT1A or 5-HT2 affinity and selectivity respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.