(3S,2'R)-3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium bromide | 51186-83-5

• 物质功能分类: 原料药
• 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: (3S,2'R)-3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium bromide
• 英文别名: (3S,2'R )-3-[(cyclopentyl-hydroxyphenylacetyl)oxy]-1,1-dimethylpyrrolidinium bromide；erythro-Glycopyrronium bromide；[(3S)-1,1-dimethylpyrrolidin-1-ium-3-yl] (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetate;bromide
• CAS: 51186-83-5
• 化学式: Br*C₁₉H₂₈NO₃
• 分子量: 398.34
• InChiKey: VPNYRYCIDCJBOM-QQTWVUFVSA-M

物化性质

• 熔点：
  175℃
• 溶解度：
  易溶于水，溶于乙醇（96%），极微溶于二氯甲烷。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.54
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-环戊基-2-羟基苯乙酸 以 丙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 44.0h， 生成 吡咯烷正离子,3-[(环戊基羟基苯乙酰)氧代]-1,1-二甲基-,溴化,[R-(R*,S*)]- 、 (3S,2'R)-3-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium bromide
  参考文献：
  名称：

  Carry Over of Impurities: A Detailed Exemplification for Glycopyrrolate (NVA237)

  摘要：

  The original synthesis of glycopyrrolate (NVA237) was revised and shortened into an essentially one-pot process. Without isolating the intermediates, their purification became obsolete, thereby increasing the possibility of the carry over of impurities. For that reason, the actual, potential, and theoretical impurities of the starting materials cyclopentyl mandelic acid and 1-methyl-pyrrolidin-3-ol as well as byproducts which may occur during the synthesis were thoroughly investigated; furthermore, their transformation to possible impurities in the drug substance along the new synthetic route was performed to exclude them as actual impurities in the drug substance with certainty. The question is raised how detailed such investigation-which are fairly manageable for a simple product like glycopyrrolate-need to be.

  DOI：

  10.1021/op3001788

文献信息

• Verfahren zur Herstellung der 2'-(R)-Glycopyrronium-Enantiomere und deren Verwendung in Arzneimitteln
  申请人：Noe, Christian R.

  公开号：EP1371645A1

  公开（公告）日：2003-12-17

  Diese Erfindung betrifft Verfahren zur Herstellung von (3S,2'R)- und (3R,2'R)-3-[Cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-pyrrolidinium (= (3S,2'R)- und (3R,2'R)-Glycopyrronium) sowie die Verwendung von (3S,2'R)- Glycopyrronium bzw. seiner Salze in Arzneimitteln.

  本发明涉及 (3S,2'R)- 和 (3R,2'R)-3-[cyclopentylhydroxyphenylacetyl)oxy]-1,1-dimethyl-pyrrolidinium (= (3S,2'R)- 和 (3R,2'R)-glycopyrronium) 的制备工艺以及 (3S,2'R)-glycopyrronium 或其盐在药物中的用途。
• Pharmaceutical compositions for the treatment of inflammatory or obstructive airway diseases
  申请人：Novartis AG

  公开号：EP1894568A1

  公开（公告）日：2008-03-05

  Medicaments comprising (A) an antimuscarinic agent, (B) a beta-2 adrenoreceptor agonist and (C) a corticosteroid for the treatment of inflammatory or obstructive airways diseases.

  治疗炎症性或阻塞性气道疾病的药物，包括(A)抗心绞痛剂、(B)β-2 肾上腺素受体激动剂和(C)皮质类固醇。
• Pharmaceutical composition containing glycopyrrolate and a beta2 adrenoceptor agonist
  申请人：Novartis AG

  公开号：EP2228064A2

  公开（公告）日：2010-09-15

  A pharmaceutical composition containing (A) glycopyrrolane; and (B) a compound of formula I in free or salt or solvate form, wherein W, Rx, Ry, R1, R2, R3, R4, R5, R6 and R7 have the meanings as indicated in the specification, together with at least one pharmaceutically acceptable carrier. The composition is useful in the treatment of inflammatory or obstructive airways diseases.

  一种药物组合物，含有(A)甘氨酰吡咯烷；和(B)式 I 的化合物 其中 W、Rx、Ry、R1、R2、R3、R4、R5、R6 和 R7 的含义如说明书所示，并含有至少一种药学上可接受的载体。该组合物可用于治疗炎症性或阻塞性气道疾病。
• OIL IN WATER EMULSION
  申请人：Dr. August Wolff GmbH & Co. KG Arzneimittel

  公开号：EP3431072A1

  公开（公告）日：2019-01-23

  The present invention relates to an oil-in-water emulsion comprising a glycopyrronium salt and an emulsifier system comprising at least one macrogol glycerol fatty acid ester, at least one glycerol fatty acid ester and at least one fatty alcohol. Moreover, the present invention relates to such an emulsion for use as a medicament, in particular for treating and preventing diseases in conjunction with excessive sweating. In addition the present invention relates to the non-therapeutic use of such an oil-in-water emulsion for topical application on the skin of a mammal in order to reduce sweating.

  本发明涉及一种水包油型乳剂，该乳剂由甘草膦盐和乳化剂体系组成，乳化剂体系包括至少一种大环甘油脂肪酸酯、至少一种甘油脂肪酸酯和至少一种脂肪醇。此外，本发明涉及的乳液可用作药物，特别是用于治疗和预防与多汗症有关的疾病。此外，本发明还涉及这种水包油乳液的非治疗用途，即局部涂抹于哺乳动物的皮肤上，以减少出汗。
• PHARMACEUTICAL COMPOSITION CONTAINING GLYCOPYRROLATE AND A BETA2 ADRENOCEPTOR AGONIST
  申请人：Novartis AG

  公开号：EP3603634A1

  公开（公告）日：2020-02-05

  A pharmaceutical composition containing (A) glycopyrrolate; and (B) a compound of formula I in free or salt or solvate form, wherein W, Rx, Ry, R1, R2, R3, R4, R5, R6 and R7 have the meanings as indicated in the specification, together with at least one pharmaceutically acceptable carrier. The composition is useful in the treatment of inflammatory or obstructive airways diseases.

  一种药物组合物，含有 (A) 甘草酸苷；和 (B) 式 I 的化合物 其中 W、Rx、Ry、R1、R2、R3、R4、R5、R6 和 R7 的含义如说明书所示，并含有至少一种药学上可接受的载体。该组合物可用于治疗炎症性或阻塞性气道疾病。