1-methyl-2-(2-nitro-trans-styryl)-pyridinium; iodide | 43027-22-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-methyl-2-(2-nitro-trans-styryl)-pyridinium; iodide
• 英文别名: 1-Methyl-2-(2-nitro-trans-styryl)-pyridinium; Jodid；1-methyl-2-[(E)-2-(2-nitrophenyl)ethenyl]pyridin-1-ium;iodide
• CAS: 43027-22-1
• 化学式: C₁₄H₁₃N₂O₂*I
• 分子量: 368.174
• InChiKey: SRPFLMQPQQXFHX-RRABGKBLSA-M

物化性质

• 熔点：
  229-230 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.41
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-2-(2-nitro-trans-styryl)-pyridinium; iodide 在 platinum on activated charcoal 、 氢气 、 sodium hydroxide 作用下， 以 甲醇 、 MeOH 为溶剂， 生成 (S)-[2-(o-aminophenethyl)-1-methylpiperidine dibenzoyl-L-tartrate]
  参考文献：
  名称：

  Development of a Scalable Synthesis of a Serotonin Receptor Antagonist

  摘要：

  An efficient process was developed for the manufacture of MSA100, a serotonin receptor antagonist, via a five-step synthetic route furnishing a high quality of active pharmaceutical ingredient. Highlights of this synthesis include: (1) replacing carcinogenic methyl iodide with methyl p-toluenesulfonate as the methylating reagent; (2) a hydrogenation protocol with optimized temperature, pressure, and mass-transfer conditions that avoided one side product and reduced the other one effectively; (3) chemical resolution employing D-camphoric acid in a mixed-solvent system; (4) amidation under anhydrous conditions for controlling a Michael adduct impurity; and (5) plausible mechanisms for the formation of side products.

  DOI：

  10.1021/op5003402
• 作为产物：
  描述：

  (E)-2-(2-nitrostyryl)pyridine 在 碘甲烷 作用下， 以 丙酮 为溶剂， 以80%的产率得到1-methyl-2-(2-nitro-trans-styryl)-pyridinium; iodide
  参考文献：
  名称：

  Development of a Scalable Synthesis of a Serotonin Receptor Antagonist

  摘要：

  An efficient process was developed for the manufacture of MSA100, a serotonin receptor antagonist, via a five-step synthetic route furnishing a high quality of active pharmaceutical ingredient. Highlights of this synthesis include: (1) replacing carcinogenic methyl iodide with methyl p-toluenesulfonate as the methylating reagent; (2) a hydrogenation protocol with optimized temperature, pressure, and mass-transfer conditions that avoided one side product and reduced the other one effectively; (3) chemical resolution employing D-camphoric acid in a mixed-solvent system; (4) amidation under anhydrous conditions for controlling a Michael adduct impurity; and (5) plausible mechanisms for the formation of side products.

  DOI：

  10.1021/op5003402

文献信息

• [EN] METHODS AND COMPOSITIONS FOR TREATING INTERNAL AND EXTERNAL HEMORRHOIDS<br/>[FR] PROCÉDÉS ET COMPOSITIONS POUR TRAITEMENT D'HÉMORROÏDES INTERNES ET EXTERNES
  申请人：SAM AMER & CO INC

  公开号：WO2012026914A1

  公开（公告）日：2012-03-01

  The present invention relates to compositions and methods for treatment of internal and/or external hemorrhoids, wherein the treatment includes topically administering to a subject a composition comprising from 0.3% to 0.7% of S-2'- [2-(l-methyl-2- piperidyl) ethyl] cinnamanilide, wherein the S-2'- [2-(l-methyl-2-piperidyl) ethyl] cinnamanilide not only treats the hemorrhoidal symptoms but delays or inhibits the recurrence of hemorrhoids and/or symptoms thereof.

  本发明涉及用于治疗内部和/或外部痔疮的组合物和方法，其中治疗包括局部给予受试者一种含有0.3%至0.7%的S-2'-[2-(l-甲基-2-哌啶基)乙基]肉桂酰亚胺的组合物，其中S-2'-[2-(l-甲基-2-哌啶基)乙基]肉桂酰亚胺不仅治疗痔疮症状，还延迟或抑制痔疮的复发和/或其症状。
• [EN] METHODS AND COMPOSITIONS FOR TREATING HEMORRHOIDS WHILE PROVIDING LOCAL ANESTHETIC AND ANTI-INFLAMMATORY EFFECTS<br/>[FR] MÉTHODES ET COMPOSITIONS DE TRAITEMENT DES HÉMORROÏDES À EFFETS ANESTHÉSIQUES ET ANTI-INFLAMMATOIRES LOCAUX
  申请人：VENTRUS BIOSCIENCES INC

  公开号：WO2013070236A1

  公开（公告）日：2013-05-16

  The present invention relates to compositions and methods for treatment of internal and/or external hemorrhoids, wherein the treatment includes topically administering to a subject a composition comprising from 0.3% to 0.7% of S-2'- [2-(1-methyl-2- piperidyl) ethyl] cinnamanilide, wherein the S-2'- [2-(1-methyl-2-piperidyl) ethyl] cinnamanilide not only treats the hemorrhoidal symptoms but exhibits a local anesthetic effect while controlling inflammation in the area of treatment.

  本发明涉及用于治疗内部和/或外部痔疮的组合物和方法，其中治疗包括局部给予受试者一种含有0.3％至0.7％的S-2'-[2-(1-甲基-2-哌啶基)乙基]肉桂酰亚胺的组合物，其中S-2'-[2-(1-甲基-2-哌啶基)乙基]肉桂酰亚胺不仅治疗痔疮症状，而且在治疗区域内具有局部麻醉作用，同时控制炎症。
• METHODS AND COMPOSITIONS FOR TREATING INTERNAL AND EXTERNAL HEMORRHOIDS
  申请人：Amer Moh Samir

  公开号：US20120046318A1

  公开（公告）日：2012-02-23

  The present invention relates to compositions and methods for treatment of internal and/or external hemorrhoids, wherein the treatment includes topically administering to a subject a composition comprising from 0.3% to 0.7% of S-2′-[2-(1-methyl-2-piperidyl)ethyl]cinnamanilide, wherein the S-2′-[2-(1-methyl-2-piperidyl)ethyl]cinnamanilide not only treats the hemorrhoidal symptoms but delays or inhibits the recurrence of hemorrhoids and/or symptoms thereof.

  本发明涉及用于治疗内部和/或外部痔疮的组合物和方法，其中治疗包括向受试者局部给药含有0.3％至0.7％S-2'-[2-(1-甲基-2-哌啶基)乙基]肉桂酰亚胺的组合物，其中S-2'-[2-(1-甲基-2-哌啶基)乙基]肉桂酰亚胺不仅可以治疗痔疮症状，还可以延迟或抑制痔疮和/或其症状的复发。
• [EN] S-2'-(2-(1-METHYL-2-PIPERIDYL) ETHYL) CINNAMANILIDE AS A 5-HT2 RECEPTOR ANTAGONIST<br/>[FR] S-2'-(2-(1-METHYL-2-PIPERIDYL)ETHYL)CINNAMANILIDE EN TANT QU'ANTAGONISTE DU RECEPTEUR DE 5-HT2
  申请人：AMER, Moh, Samir

  公开号：WO1998038165A1

  公开（公告）日：1998-09-03

  (EN) The 5HT2 receptor antagonizing effect of 2'-[2-(1-methyl-2-piperidyl) ethyl] cinnamanilide, a racemic mixture (R S-MPEC) of S-MPEC and R-MPEC isomers is found to be provided practically entirely by the S-MPEC isomer, the R-MPEC being effectively an impurity. Disclosed are pure S-MPEC, mixtures thereof with up to about 10 % of R-MPEC, a novel method of resolving the S-MPEC involving a novel intermediate compound, therapeutic compositions containing S-MPEC, and uses thereof for administration to animals, especially humans, in need of 5HT2 receptor blockage, as for hemorrhoids, varicose veins, venous and coronary insufficiencies, wound healing, and as analgesic or local anesthesic agents.(FR) L'effet antagoniste contre le récepteur de 5HT2, assuré par le 2'-(2-(1-méthyl-2-pipéridyl)éthyl)cinnamanilide, qui est un mélange racémique (R S-MPEC) d'isomères S-MPEC et R-MPEC, se trouve être pratiquement entièrement assuré par l'isomère S-MPEC, le R-MPEC étant effectivement une impureté. On décrit un isomère pur S-MPEC, des mélanges de celui-ci avec jusqu'à 10 % environ de R-MPEC, un nouveau procédé de séparation de S-MPEC impliquant l'utilisation d'un nouveau composé intermédiaire, des compositions thérapeutiques contenant S-MPEC, ainsi que des utilisations de ces compositions destinées à être administrées à des animaux, notamment à l'homme, lesquels nécessitent un blocage du récepteur de 5HT2, comme pour traiter des hémorroïdes, des veines variqueuses, des insuffisances veineuses et coronaires, pour cicatriser des blessures, et en tant qu'analgésiques ou anesthésiants locaux.

  2'-[2-(1-甲基-2-哌啶基)乙基]肉桂酰亚胺（S-MPEC和R-MPEC异构体的混合物（R S-MPEC））的5HT2受体拮抗作用实际上主要由S-MPEC异构体提供，R-MPEC有效地是杂质。本文披露了纯的S-MPEC，其中与R-MPEC混合的比例最高可达约10％，涉及一种新的分离S-MPEC的方法，其中包括一种新的中间化合物，含有S-MPEC的治疗组合物以及将其用于需要5HT2受体阻滞的动物，特别是人类，例如用于治疗痔疮，静脉曲张，静脉和冠状动脉不足，伤口愈合以及作为镇痛剂或局部麻醉剂的用途。
• Notes - Studies in cis- and trans-Stilbazoles
  作者：Lester Horwitz

  DOI：10.1021/jo01115a612

  日期：1956.9