Cyclopropyl-2-fluorobenzyl ketone | 1357945-50-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: Cyclopropyl-2-fluorobenzyl ketone
• 英文别名: 1,3-dicyclopropyl-1,3-bis(2-fluorophenyl)propan-2-one
• CAS: 1357945-50-6
• 化学式: C₂₁H₂₀F₂O
• 分子量: 326.4
• InChiKey: PRJHYLSXDZLKFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Cyclopropyl-2-fluorobenzyl ketone 、 双氧水 、 氢溴酸 在 水 、 乙酸乙酯 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 2-溴-2-(2-氟苯基)-1-环丙基乙酮
  参考文献：
  名称：

  PROCESS FOR THE PREPARATION OF PHARMACEUTICAL INTERMEDIATE

  摘要：

  本发明涉及一种制备通式（III）化合物的方法，其中R代表氟或氯原子，X代表氯或溴原子，通过对通式（II）的环丙基苯甲酮进行卤代反应得到，其中R代表氟或氯原子，并且在水溶性溶剂或相转移催化剂的存在下，在水合氢卤酸和水合过氧化氢混合物中进行卤代反应；或在硫酸和水合氢卤酸的碱金属盐混合物中进行卤代反应。该方法可在工业规模下进行。

  公开号：

  US20110040093A1

文献信息

• [EN] PROCESS FOR PREPARING PRASUGREL<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE PRASUGREL
  申请人：LESVI LABORATORIOS SL

  公开号：WO2013014295A1

  公开（公告）日：2013-01-31

  The present invention is directed to an improved process for preparing, prasugrel and maleate salt of Prasugrel and, optionally other pharmaceutically acceptable salts from, prasugrel and said maleate salt, in high yields and purity, which can be used at industrial scale. The process of the present invention comprises the steps of bromination, condensation, acetylating and optionally converting into maleate salt and, if desired, conversion into another pharmaceutically acceptable salt from it. The present process is advantageous in terms of productivity, efficacy, purity and also prevents the use of toxic substances.

  本发明涉及一种改进的制备过程，用于从prasugrel和prasugrel的maleate盐，以及可选地从prasugrel和该maleate盐中制备其他药用盐，高产率和纯度中制备，可用于工业规模。本发明的过程包括溴化、缩合、乙酰化以及可选地转化为maleate盐，并如有需要，从中转化为另一种药用盐。本过程在生产效率、功效、纯度方面具有优势，并且还能防止使用有毒物质。
• PROCESS FOR THE PREPARATION OF PRASUGREL AND SEVERAL NOVEL CRYSTALLINE FORMS OF PRASUGREL HYDROCHLORIDE
  申请人：Li Lijun

  公开号：US20140155351A1

  公开（公告）日：2014-06-05

  Disclosed herein are a process or method for the preparation of prasugrel and several novel crystalline forms of prasugrel hydrochloride. The process comprises preparation of prasugrel by acetylation in solvents which have low boiling point and/or low toxicity, and the process not only avoids using solvents which have high boiling point and/or high toxicity such as toluene, acetonitrile and so on, but also resolves the problem about thermal instability of prasugrel, and the loss of prasugrel is reduced, as well as the yield is raised. The yield of prasugrel is higher than 85% and the purity is higher than 99.5%. The process can prepare prasugrel and its pharmaceutically acceptable salts. The novel crystalline forms of prasugrel hydrochloride are crystalline form H1, H2 and H3, and their performance in oral absorbability, activating metabolism and inhibiting platelet aggregation is excellent. They have a low toxicity and good thermal stability, and are applicable to the preparation of a drug for preventing or treating diseases caused by thrombosis or embolism.

  本文揭示了一种制备普拉格雷（prasugrel）和几种新型盐酸普拉格雷晶型的方法或工艺。该工艺包括在具有低沸点和/或低毒性的溶剂中通过乙酰化制备普拉格雷，该工艺不仅避免使用甲苯、乙腈等高沸点和/或高毒性的溶剂，而且解决了普拉格雷的热稳定性问题，减少了普拉格雷的损失，同时提高了产率。普拉格雷的产率高于85％，纯度高于99.5％。该工艺可制备普拉格雷及其药用可接受的盐。普拉格雷盐酸盐的新型晶型包括晶型H1、H2和H3，其口服吸收性能、活化代谢和抑制血小板聚集的表现优异。它们毒性低，热稳定性好，适用于制备用于预防或治疗由血栓形成或栓塞引起的疾病的药物。
• PROCESSES FOR THE PREPARATION OF PRASUGREL , AND ITS SALTS AND POLYMORPHS
  申请人：Padi Pratap Reddy

  公开号：US20100261908A1

  公开（公告）日：2010-10-14

  Processes for the preparation of prasugrel and its pharmaceutically acceptable salts thereof. Also disclosed are polymorphic forms of prasugrel hydrochloride and processes for their preparation.

  制备prasugrel及其药用可接受盐的过程。还披露了prasugrel盐酸盐的多晶型和其制备过程。
• PROCESS FOR THE PREPARATION OF PHARMACEUTICAL INTERMEDIATES
  申请人：Mezei Tibor

  公开号：US20100274020A1

  公开（公告）日：2010-10-28

  The invention relates to a process for the preparation of cyclopropyl benzyl ketone compounds of formula (II) wherein R 1 represents fluorine or chlorine atom or C 1-4 alkoxy group, by the reaction of a Grignard reagent, obtained from the reaction of compound of formula (V), wherein X represents chlorine or fluorine atom, with the compound of formula (IV), wherein R 2 represents C 1-4 alkyl group, having a straight or branched chain. The process can be applied preferably on industrial scale. Compound of formula (II), wherein R represents a fluorine atom in position 2 is an intermediate of the preparation process of prasugrel, which is a platelet inhibitor used in the therapy.

  本发明涉及一种制备环丙基苯甲酮化合物的方法，其化学式为（II），其中R1代表氟或氯原子或C1-4烷氧基团，该方法通过将化学式为（V）的化合物（其中X代表氯或氟原子）与化学式为（IV）的化合物（其中R2代表直链或支链的C1-4烷基团）反应得到Grignard试剂，可在工业规模上进行。其中，化学式为（II），其中R代表2位的氟原子是prasugrel制备过程的中间体，prasugrel是一种用于治疗的血小板抑制剂。
• PROCESSES FOR THE PREPARATION OF PRASUGREL, AND ITS SALTS AND POLYMORPHS
  申请人：Dr. Reddy's Laboratories Ltd.

  公开号：EP2205611A2

  公开（公告）日：2010-07-14