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WO2018163212A1 - Procédé de préparation de bromure d'uméclidinium et de ses intermédiaires - Google Patents

Procédé de préparation de bromure d'uméclidinium et de ses intermédiaires Download PDF

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Publication number
WO2018163212A1
WO2018163212A1 PCT/IN2018/050130 IN2018050130W WO2018163212A1 WO 2018163212 A1 WO2018163212 A1 WO 2018163212A1 IN 2018050130 W IN2018050130 W IN 2018050130W WO 2018163212 A1 WO2018163212 A1 WO 2018163212A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
solvent
mixture
umeclidinium bromide
preparation
Prior art date
Application number
PCT/IN2018/050130
Other languages
English (en)
Inventor
G. Nithun REDDY
G. Samhitha REDDY
G. Madaalasa REDDY
M Ramani
G. Pratap REDDY
Original Assignee
Gbr Laboratories Pvt. Ltd
Rachana Pharma Tech
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Gbr Laboratories Pvt. Ltd, Rachana Pharma Tech filed Critical Gbr Laboratories Pvt. Ltd
Publication of WO2018163212A1 publication Critical patent/WO2018163212A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems

Definitions

  • the objective of COPD therapy is mainly towards instant relief, symptoms reduction, as well as decreased risk of future adverse health events.
  • Bronchodilators are essential for management in COPD.
  • the choice between beta2-agonists, anticholinergic agents, theophylline, or combination therapy depends on availability of these drugs and patient response.
  • Two long-acting anticholinergic agents are approved for the long-term maintenance treatment of bronchospasm associated with COPD: tiotropium bromide and aclidinium bromide are the well known agents for effective treatment of respiratory disorders.
  • the present invention provides a process for preparation of umeclidinium bromide and intermediates thereof.
  • the process of the present invention is a synthetic, eco-friendly, non- hazardous and cost effective process.
  • a process for preparation of umeclidmium bromide and intermediates thereof comprises: i. mixing 4-bromoquinuclidine with a predefined quantity of a metal and a catalyst in a solvent to obtain a mixture of 4-bromoquinuclidine of Formula 2; ii. reacting the mixture of 4-bromoquinuclidine, of Formula 2 with benzophenone in a solvent, to form an intermediate of Formula 3;
  • the metal is selected from magnesium, zinc, indium, and lithium.
  • the catalyst is selected from iodine, ultrasound, and heat.
  • the solvents are selected from chloroform, dichloromethane, dichloroethane, acetonitrile, toluene, tetrahydrofuran (THF), dimethyl ether, and a combination thereof.
  • the process for the preparation of umeclidinium. bromide advantageously avoids .multiple numbers of steps of synthesis.
  • the process shows increase in % yield of umeclidinium bromide by about 20 % to 25%.
  • the process for the preparation of umeclidinium bromide advantageously involves simplified steps and advantageously avoids use of expensive reagents, solvents, chemicals, and the like. Further, the process for the preparation of umeclidinium bromide saves the processing time avoids use of hazardous chemicals.
  • the process of the present invention is suitable for the preparation of umeclidinium bromide on commercial scale, thereby reducing the manufacturing cost by around 20% to 30%.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé de préparation de bromure d'uméclidinium et de ses intermédiaires, la forme pure de bromure d'uméclidinium étant obtenue par un procédé en deux étapes dans des conditions modérées.
PCT/IN2018/050130 2017-03-08 2018-03-08 Procédé de préparation de bromure d'uméclidinium et de ses intermédiaires WO2018163212A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN201741008151 2017-03-08
IN201741008151 2017-03-08

Publications (1)

Publication Number Publication Date
WO2018163212A1 true WO2018163212A1 (fr) 2018-09-13

Family

ID=63447482

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2018/050130 WO2018163212A1 (fr) 2017-03-08 2018-03-08 Procédé de préparation de bromure d'uméclidinium et de ses intermédiaires

Country Status (1)

Country Link
WO (1) WO2018163212A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005104745A2 (fr) * 2004-04-27 2005-11-10 Glaxo Group Limited Antagonistes des récepteurs muscariniques de l'acétylcholine
CN105461710A (zh) * 2015-10-23 2016-04-06 安徽德信佳生物医药有限公司 一种芜地溴铵的制备方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005104745A2 (fr) * 2004-04-27 2005-11-10 Glaxo Group Limited Antagonistes des récepteurs muscariniques de l'acétylcholine
CN105461710A (zh) * 2015-10-23 2016-04-06 安徽德信佳生物医药有限公司 一种芜地溴铵的制备方法

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