盐酸加兰他敏 | 5072-47-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 中文名称: 盐酸加兰他敏
• 英文名称: Galantamine hydrochloride
• 英文别名: galanthamine hydrochloride；(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol;hydrochloride
• CAS: 5072-47-9
• 化学式: C₁₇H₂₁NO₃*ClH
• 分子量: 323.82
• InChiKey: USUHXXKCHSBMOS-XPSHAMGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  41.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  盐酸加兰他敏 在 ammonium hydroxide 、 间氯过氧苯甲酸 、 ferrous(II) sulfate heptahydrate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 以73 %的产率得到N-去甲基加兰它敏氢溴酸盐
  参考文献：
  名称：

  CN116082352

  摘要：

  公开号：

文献信息

• [EN] SYNTHESIS OF MORPHINE AND RELATED DERIVATIVES<br/>[FR] SYNTHÈSE DE LA MORPHINE ET DE DÉRIVÉS ASSOCIÉS
  申请人：UNIV TEXAS

  公开号：WO2010132570A1

  公开（公告）日：2010-11-18

  The present invention relates to methods for the synthesis of galanthamine, morphine, intermediates, salts and derivatives thereof, wherein the starting compound is biphenyl.

  本发明涉及一种合成迷迭香碱、吗啡、中间体、盐和衍生物的方法，其中起始化合物为联苯。
• [EN] METHOD FOR PREPARATION OF PURIFIED GALANTAMINE HYDROBROMIDE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE BROMHYDRATE DE GALANTAMINE PURIFIÉ
  申请人：SOPHARMA AD

  公开号：WO2019222817A1

  公开（公告）日：2019-11-28

  The invention concerns a method for preparation of purified galantamine hydrobromide, i.e. extraction of galantamine from plant raw material, its conversion into hydrobromide and its purification. The method consists of extraction from Leucojum aestivum or Narcissus Carlon cv in aqueous medium or in medium of low alcohol, alkalized with calcium hydroxide to pH 9 - 12 at a temperature of 30 - 40°C of galantamine base, after filtration and concentration it is extracted 2 to 4 times with methyl isobutyl ketone, ethyl acetate or butyl acetate or with n-butanol in a ratio of extract/extractant of 8:1 during the extractions in water medium, and respectively 2:1 during the extractions in the presence of simple alcohol. Concentration of the collected organic extracts from 1/20 to 1/30 of the initial volume and replacement of the solvent with ethanol. Conversion of the obtained galantamine base during treatment with hydrobromic acid to galantamine hydrobromide which at a temperature of 80 - 85°C in aqueous medium is purified with activated carbon. Filtration of the purified solution, cooling down to 20-25°C and alkalization with ammonium hydroxide to pH 9-12. Extraction of the obtained galantamine base 2-4 times with methyl isobutyl ketone, ethyl acetate or butyl acetate in a ratio of alkaline water solution/organic solvent of 2:1 to 3:1 and after concentration from 1/5 to 1/10 of the initial volume, cooling and treating with selective reagent for N-desmethyl galantamine under stirring for 7-10 hours, followed by extraction with mineral acid to pH 2-3 in aqueous medium, alkalization of the acid water extract of the galantamine salt at pH 9-12, extraction of the released galantamine base with methyl isobutyl ketone, ethyl acetate or butyl acetate in a ratio of aqueous solution/organic solvent of 2:1 to 3:1, replacement of the solvent with ethanol and processing with hydrobromic acid and obtaining galantamine hydrobromide with HPLC grade more than 99% and high yield of about 90 - 92% of the content of Galantamine hydrobromide in the technical product.

  该发明涉及一种制备纯化溴化加兰他明的方法，即从植物原料中提取加兰他明，将其转化为溴化物并进行纯化。该方法包括在水性介质或低醇介质中从夏雪花或卡尔隆水仙中提取加兰他明碱，将其碱化至pH值为9-12，温度为30-40°C，经过过滤和浓缩后，使用甲基异丁基酮、乙酸乙酯、丁酸丁酯或正丁醇进行2-4次萃取，在水介质中的萃取比为8:1，简单醇存在时的萃取比为2:1。收集的有机萃取物浓缩至初始体积的1/20至1/30，并用乙醇替换溶剂。将获得的加兰他明碱在氢溴酸处理过程中转化为溴化加兰他明，然后在80-85°C的水性介质中用活性炭进行纯化。过滤纯化溶液，冷却至20-25°C并用氢氧化铵碱化至pH值为9-12。将获得的加兰他明碱用甲基异丁基酮、乙酸乙酯或丁酸丁酯进行2-4次萃取，碱性水溶液/有机溶剂比为2:1至3:1，浓缩至初始体积的1/5至1/10，冷却后加入选择性试剂对去甲基加兰他明进行搅拌处理7-10小时，随后在水性介质中用矿酸萃取至pH值为2-3，将得到的加兰他明盐水提取液碱化至pH值为9-12，用甲基异丁基酮、乙酸乙酯或丁酸丁酯萃取释放的加兰他明碱，用乙醇替换溶剂，用氢溴酸处理并获得高效液相色谱等级超过99%的溴化加兰他明，产率高达90-92%。
• Efficient Synthesis Of Morphine And Codeine
  申请人：Magnus Philip D.

  公开号：US20100292475A1

  公开（公告）日：2010-11-18

  The present invention relates to methods for the synthesis of morphine, intermediates, salts and derivatives thereof. In preferred embodiments, the invention relates to methods for improving the efficiency and overall yield of said morphine, morphine related derivatives and intermediates thereof. In further embodiments, the invention relates to methods for improving the efficiency and overall yield of galanthamine and intermediates thereof.

  本发明涉及吗啡、中间体、盐和衍生物的合成方法。在优选实施例中，本发明涉及改善吗啡、吗啡相关衍生物和中间体的效率和总产量的方法。在进一步实施例中，本发明涉及改善迷迭香碱及其中间体的效率和总产量的方法。
• Efficient Synthesis Of Galanthamine
  申请人：Magnus Philip D.

  公开号：US20100292466A1

  公开（公告）日：2010-11-18

  The present invention relates to methods for the synthesis of galanthamine, morphine, intermediates, salts and derivatives thereof. In preferred embodiments, the invention relates to methods for improving the efficiency and overall yield of said morphine, morphine related derivatives and intermediates thereof. In further embodiments, the invention relates to methods for improving the efficiency and overall yield of galanthamine and intermediates thereof.

  本发明涉及合成迷达唑啉、吗啡、中间体、盐和衍生物的方法。在优选实施例中，本发明涉及提高吗啡、吗啡相关衍生物和中间体的效率和总产率的方法。在进一步的实施例中，本发明涉及提高迷达唑啉及其中间体的效率和总产率的方法。
• Isolation of Galanthamine From Biological Material
  申请人：Cvak Ladislav

  公开号：US20080262223A1

  公开（公告）日：2008-10-23

  The subject matter of present invention relates to the process for isolation and purification of galanthamine and its derivatives produced by numerous plants.

  本发明涉及一种用于从许多植物中分离和纯化白及碱及其衍生物的过程。