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Preparation method of ipratropium bromide

A kind of technology of ipratropium bromide and new method, applied in directions such as organic chemistry, can solve the problems such as complicated operation, low photochemical reaction yield, unsuitable for industrialized production and the like

Inactive Publication Date: 2017-08-11
HANGZHOU BIO SINCERITY PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] In this route, the yield of photochemical reaction is low, the operation is cumbersome, and it is not suitable for industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] The preparation of embodiment 1 compound (II):

[0051] Weigh 10.0g of tropinol, add it to the reaction bottle, add 75ml of acetonitrile, stir, cool to 10°C, replace the air in the bottle with nitrogen, add -20°C pre-cooled methyl bromide 6.8g, seal the reaction for 12h, the reaction is completed, filter, After drying, 8.8 g of compound (II) was obtained with a molar yield of 58%.

Embodiment 2

[0052] The preparation of embodiment 2α-methyl formyl phenylacetate (Ⅳ):

[0053] Add 20g of methyl phenylacetate into the reaction flask, add 80mL of ethyl formate, stir at 25-30°C, cool the reaction solution to -5-0°C, add 50g of titanium tetrachloride into 40ml of dichloromethane, stir, Slowly add titanium tetrachloride dichloromethane solution dropwise to the reaction solution, keep the temperature at -5-0°C, add dropwise for 2 hours (titanium tetrachloride dropwise is an exothermic reaction, the dropping speed should be controlled), after the dropwise addition, put Slowly add 33.7g of triethylamine dropwise to the reaction solution, control the temperature -5-0°C, cool the reaction solution to 5-10°C, add 200ml of water and 100ml of DCM, stir for 15min, separate the organic phase, and extract the aqueous phase with 40ml of dichloromethane Twice, the organic phase was combined, and the organic phase was washed twice with 50 mL of brine, and the organic layer was distilled ...

Embodiment 3

[0054] The preparation of embodiment 3 compound (Ⅴ):

[0055] Add 60ml of toluene to the reaction bottle, add 0.132g of sodium methoxide at 25-23 degrees, heat the reaction to 109-115 degrees, distill 20ml of toluene, add 10g of compound (II), add 60ml of toluene, and take another 5.6g of α- Methyl formylphenylacetate, add 60ml of toluene to make a solution, double drop into the reaction bottle, after the dropwise addition, distill off the solvent, prepare 50ml of fresh toluene, slowly add dropwise, distill out the toluene from the reaction solution, react for 3 hours, distill out the toluene until 20ml of slurry solution remained, cooled to 25-30°C, stirred for 12h, filtered, and dried for 6h to obtain 10.4g of compound (Ⅴ), with a yield of 65%.

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Abstract

The invention discloses a preparation method of ipratropium bromide. The method comprises the following steps that as a starting material, methyl phenylacetate (III) undergoes the substitution reaction to produce alpha-formyl methyl phenylacetate (IV); tropic alcohol reacts with bromomethane to produce a compound (II); the compound (II) reacts with a compound (IV) to produce a compound (V); the compound (V) undergoes a reductive reaction to produce ipratropium bromide anhydrous substance, and then ipratropium bromide (VII) is produced through refining preparation. The method has the advantages of simple operation, high safety, a low cost and suitability for industrial production.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a novel method for preparing ipratropium bromide. Background technique [0002] The chemical name of ipratropium bromide is [(1R,5S)-8-methyl-8-isopropyl-8-azabicyclo[3.2.1]oct-3-yl]3-hydroxy-2-benzene Propionyl bromide, used as its monohydrate, the English chemical name is (1R,3r,5S,8r)-3-[[(2RS)-3-Hydroxy-2-phenylpropanoyl]oxy]-8-methyl -8-(1-methylethyl)-8-azoniabicyclo[3.2.1]octanebromide monohydrate, CAS No. 66985-17-9, its structural formula is as follows: [0003] . [0004] Ipratropium bromide is an anticholinergic drug, which has a strong relaxing effect on bronchial smooth muscle and has an antiasthmatic effect on chronic obstructive pulmonary disease. Pratropium bromide also has the effect of controlling the secretion of mucus glands and improving ciliary movement, thereby reducing sputum obstruction to improve ventilation, and the reduction of sputum also ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D451/10
CPCC07D451/10
Inventor 吴俊平罗瑾靳小舜陈晓萍曾智丽衣丽娜
Owner HANGZHOU BIO SINCERITY PHARMA TECH CO LTD
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