去氢巴尼地平 | 172331-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 去氢巴尼地平
• 英文名称: 2,6-Dimethyl-4-(3-nitro-phenyl)-pyridine-3,5-dicarboxylic acid 3-((S)-1-benzyl-pyrrolidin-3-yl) ester 5-methyl ester
• 英文别名: Dehydro Barnidipine；3-O-[(3S)-1-benzylpyrrolidin-3-yl] 5-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate
• CAS: 172331-68-9
• 化学式: C₂₇H₂₇N₃O₆
• 分子量: 489.528
• InChiKey: DFWOMDUVXAUTRY-QFIPXVFZSA-N

物化性质

• 沸点：
  594.8±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  巴尼地平 在 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 以74.6%的产率得到去氢巴尼地平
  参考文献：
  名称：

  二氢吡啶类化合物脱氢芳构化方法及在药品 检测中的用途

  摘要：

  涉及二氢吡啶类化合物脱氢芳构化方法及在药品检测中的用途，化合物例如硝苯地平、氨氯地平、西尼地平、拉西地平、非洛地平、尼卡地平、尼群地平、尼莫地平与巴尼地平等，该方法在酸性水溶液中在含镍催化剂存在下进行氧化反应接着纯化而实现的。该方法可制备用于该类药物检测和质量监控的杂质对照品，还可用于为药品质量检测过程中所用仪器如溶出度仪的设计提供参考，为药物合成工艺以及制剂生产工艺的设计提供参考，以避免杂质通过工艺渠道引入，此外还可以为二氢吡啶类化合物的相关合成工艺路线提供设计提供参考。反应可在酸性水溶液中，以适宜的氧化剂(如空气)为氧化剂，在镍存在下，常温常压进行脱氢芳构化反应，反应条件温和，目标化合物转化率高，操作简便，副产物少且对环境污染小，完全是一种环境友好型的制备工艺。

  公开号：

  CN109020875B

文献信息

• [EN] POLYMORPH OF BARNIDIPINE HYDROCHLORIDE AND PROCESSES FOR ITS PREPARATION<br/>[FR] POLYMORPHE DE CHLORHYDRATE DE BARNIDIPINE ET PROCÉDÉS POUR SA PRÉPARATION
  申请人：LUSOCHIMICA SPA

  公开号：WO2013143967A1

  公开（公告）日：2013-10-03

  The present invention relates to a novel crystalline form of barnidipine hydrochloride and processes for its preparation.

  本发明涉及一种新的盐酸贝尼地平的晶型及其制备方法。
• Examination of metabolic pathways and identification of human liver cytochrome P450 isozymes responsible for the metabolism of barnidipine, a calcium channel blocker
  作者：T. TERAMURA*、Y. FUKUNAGA、E. J. VAN HOOGDALEM、T. WATANABE、S. HIGUCHI

  DOI：10.1080/004982597240064

  日期：1997.1

  1. In a human liver microsomal system, barnidipine was converted into three primary metabolites, an N-debenzylated product (M-1), a hydrolyzed product of the benzylpyrrolidine ester (M-3) and an oxidized product of the dihydropyridine ring (M-8).2. Involvement of CYP3A in the three primary metabolic pathways was revealed by the following studies: (a) inhibition of CYP3A, (b) a correlation study using 10 individual human liver microsomes and (c) cDNA-expression studies. The secondary metabolites, M-2 and M-4 (pyridine forms of M-1 and M-3), were most likely generated from M-8 but were unlikely from M-1 or M-3. Involvement of CYP3A in the secondary pathways of metabolism is also suggested.3.0 The possibility of interactions between barnidipine and coadministered drugs was examined in vitro. The formation rate of the primary metabolites was little affected by warfarin, theophylline, phenytoin, diclofenac and amitriptyline al concentrations of 200 mu M, but was inhibited by glibenclamide, simvastatin and cyclosporin A. IC50 for the latter drugs was estimated to be > 200, 200 and 20 mu M respectively, which was roughly > 200, 6000 and 50 times higher than their respective therapeutic plasma levels, suggesting that interactions with cyclosporin A, a CYP3A inhibitor, are of possible clinical relevance.
• Different photodegradation behavior of barnidipine under natural and forced irradiation
  作者：Giuseppina Ioele、Filomena Oliverio、Inmaculada Andreu、Michele De Luca、Miguel A. Miranda、Gaetano Ragno

  DOI：10.1016/j.jphotochem.2010.08.019

  日期：2010.9

  An in depth study on photodegradation of barnidipine, a new 1,4-dihydropyridine antihypertensive drug, was performed by exposing the drug to natural and stressing light irradiation. A different degradation process and distribution of photoproducts under different light sources and irradiation power were demonstrated. Degradation kinetics, reactive excited states involved, transient species and photoproducts generated-were investigated. Exposure of barnidipine to forced irradiation caused a complex degradation pathway. Kinetics of this process was stitched by HPLC and spectrophotometry, demonstrating the formation of several by-products In contrast, the drug, under direct or indirect sunlight, underwent oxidation generating the pyridine derivative as the main photodegradation product, according to most of the drug congeners HPLC and derivative spectrophotometric methods were defined for the simultaneous assay of the drug and its pyridinic by-product, useful as a routine control method of the drug formulations (C) 2010 Elsevier B V All rights reserved
• POLYMORPH OF BARNIDIPINE HYDROCHLORIDE AND PROCESSES FOR ITS PREPARATION
  申请人：Lusochimica S.p.A.

  公开号：EP2831058B1

  公开（公告）日：2016-02-24