6-Methylergoline-8-carboxylic acid | 5878-43-3

• 物质功能分类: 医药中间体 - 原料药中间体
• 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-Methylergoline-8-carboxylic acid
• 英文别名: (6aR,9R)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxylic acid
• CAS: 5878-43-3
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.33
• InChiKey: ORBSYPFBZQJNJE-GYYYEOQOSA-N

物化性质

• 熔点：
  300 °C
• 沸点：
  517.3±50.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（微量）、甲醇（微量）、吡啶（微量）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  56.3
• 氢给体数：
  2
• 氢受体数：
  3

文献信息

• Novel ergoline derivatives, compositions containing them, their preparation and use as pharmaceuticals
  申请人：ELI LILLY AND COMPANY

  公开号：EP0026671A1

  公开（公告）日：1981-04-08

  Novel D-6-n-propylergolines of the formula: wherein Y is 0 or S and R1 is n-propyl, and pharmaceutically-acceptable acid addition salts thereof can be used to lower the prolactin level in mammals or for treating symptoms of Parkinson's syndrome in humans. A process of preparing the compounds is described which comprises reacting D-6-n-propyl-8a- mesyloxymethylergoline with the sodium salt of methylmercaptan or sodium methylate.

  式中 Y 为 0 或 S，R1 为正丙基的新型 D-6-n-propylergolines 及其药学上可接受的酸加成盐可用于降低哺乳动物的催乳素水平或治疗人类帕金森综合征的症状。 所述化合物的制备过程包括将 D-6-n-propyl-8a- mesyloxymethylergoline 与甲硫醇钠盐或甲酸钠反应。
• 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。
• Novel ergotanilides, their preparation and use
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0082805A2

  公开（公告）日：1983-06-29

  Compounds of the formula wherein X is hydrogen, fluorine, chlorine or bromine, or a pharmacologically acceptable acid addition salt thereof are antihypotonically effective. Moreover, ergotanilides of the formula C9 C10 is a C-C single or C=C double bond, R2 is hydrogen, chlorine, or bromine, R6 is C1-4 alkyl, and X is H, C1-4 alkyl, C1- 4 alkoxy, fluorine, chlorine, bromine, NH2, NHR' (R' = C1-4 alkyl or C1-4 acyl), NR'R" (R' = C1-4 alkyl or C1-4 acyl; R" = C1-4 saturated or unsaturated heterocyclic ring wherein a CH2- or CH-group thereof can be substituted by N, 0, or S), orSR" (R'" = C1-4 alkyl or phenyl), can be prepared by reacting the corresponding lysergic acid methyl esters or lysergic acid ethyl esters with a corresponding dimethylaluminum anilide in an inert solvent.

  式中的化合物 式中 X 是氢、氟、氯或溴，或其药理学上可接受的酸加成盐 具有抗热毒作用。 此外，式中的麦角酰苯胺 C9 C10 是 C-C 单键或 C=C 双键、 R2 是氢、氯或溴、 R6 是 C1-4 烷基，以及 X是氢、C1-4烷基、C1-4烷氧基、氟、氯、溴、NH2、NHR'（R'=C1-4烷基或C1-4酰基）、NR'R"（R'=C1-4烷基或C1-4酰基；R"=C1-4饱和或不饱和杂环，其中CH2-或CH-基团可被N、0或S取代）或SR"（R'"=C1-4烷基或苯基）、 可通过在惰性溶剂中使相应的麦角酸甲酯或麦角酸乙酯与相应的二甲基苯胺铝反应来制备。
• Ergoline derivatives, process for producing the ergoline derivatives and pharmaceutical compositions containing them
  申请人：FARMITALIA CARLO ERBA S.p.A.

  公开号：EP0091652A1

  公开（公告）日：1983-10-19

  There are provided ergoline derivatives of the formula (I) wherein R, represents a hydrogen atom or a methyl group, R2 represents a hydrogen or halogen atom or a methyl group, R3 represents a hydrogen atom or a methoxy group, R4 represents a hydrocarbon group having from 1 to 4 carbon atoms; each of X and W independently represents a hydrogen atom, a methyl group, a chlorine atom or a methoxy group, and n is 0, 1 or 2. A method for their preparation is also provided. The compounds have strong anti-prolactin activity.

  提供了式(I)的麦角啉衍生物 其中 R 代表氢原子或甲基，R2 代表氢原子、卤素原子或甲基，R3 代表氢原子或甲氧基，R4 代表具有 1 至 4 个碳原子的烃基；X 和 W 各自独立地代表氢原子、甲基、氯原子或甲氧基，n 为 0、1 或 2。 此外，还提供了一种制备方法。这些化合物具有很强的抗泌乳素活性。
• Esters of dihydrolysergic acid
  申请人：ELI LILLY AND COMPANY

  公开号：EP0219257A2

  公开（公告）日：1987-04-22

  Compounds of the formula wherein R is primary or secondary C₁-C₈ alkyl, C₂-C₄ alkenyl-CH₂, C₃-C₈ cycloalkyl or C₃-C₆ cycloalkyl-­substituted C₁-C₅ primary or secondary alkyl, the total number of carbon atoms in R not to exceed 8; R¹ is allyl, H, or C₁-C₄ straight chain alkyl, and R² is C₁-C₃ alkoxy-C₅-C₇ cycloalkyl; a primary or secondary C₁-C₃ alkoxy-C₂-C₆-alkyl or di(C₁-C₃ alkoxy)-C₂-C₆alkyl; C₃-C₇ ketoalkyl; or C₅-C₇ cycloalkyl or keto-substituted C₅-C₇ cycloalkyl; or 4-hydroxycyclohexyl; or a pharma­ceutically-acceptable salt thereof, are useful as 5HT₂ receptor antagonists.

  式中的化合物 其中 R 是伯或仲 C₁-C₈ 烷基、C₂-C₄ 烯基-CH₂、C₃-C₈ 环烷基或 C₃-C₆ 环烷基取代的 C₁-C₅ 伯或仲烷基，R 中的碳原子总数不超过 8；R¹ 是烯丙基、H 或 C₁-C₄ 直链烷基，R² 是 C₁-C₃ 烷氧基-C₅-C₇ 环烷基；C₁-C₃烷氧基-C₂-C₆烷基或二(C₁-C₃烷氧基)-C₂-C₆烷基； C₃-C₇酮烷基；或 C₅-C₇环烷基或酮取代的 C₅-C₇环烷基；或 4-羟基环己基；或其药学上可接受的盐，可用作 5HT₂ 受体拮抗剂。