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A kind of substitute of glycopyrronium bromide and its preparation method and medical application

A technology of glycopyrronium bromide and substitutes, applied in the preparation of sulfate, sulfonate, antipyretic, etc., can solve problems such as identification difficulty, and achieve the effects of not easy to absorb moisture, suitable solubility, and excellent stability

Active Publication Date: 2022-03-08
ANHUI HEALSTAR PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Identification of suitable combinations of salt forms with multifaceted properties can be difficult

Method used

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  • A kind of substitute of glycopyrronium bromide and its preparation method and medical application
  • A kind of substitute of glycopyrronium bromide and its preparation method and medical application
  • A kind of substitute of glycopyrronium bromide and its preparation method and medical application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]Embodiment 1: the preparation of formula (I) 3-[(cyclopentyl hydroxyphenylacetyl) oxygen]-1,1-dimethylpyrrolidine methyl sulfate

[0033] a. In a dry 5L reaction kettle, add 400g (1.82mol) of cyclopentylmandelic acid and 2000ml of N,N-dimethylformamide, cool to 20±5°C, add 360g of N'N-carbonyldiimidazole ( 2.22mol), stirred for 20min, added 228g (2.25mol) of 3-hydroxy-1-methyltetrahydropyrrole, heated to 60±5°C within 50-60min, reacted for 22h, after the reaction was identified by TLC, cooled to 20°C , pumped into a 10L separator, added 2.8L of purified water and stirred, added 3.2L of toluene, stirred for 10 minutes, separated, the organic layer was washed with purified water 1440ml×5, concentrated to dryness under reduced pressure at 50°C, and an oily substance of about 580 g, used directly in the next step.

[0034] b. Add 580g (1.91mol) of the above product, add 3000ml of acetone, cool to 0-5°C, add 241g (1.91mol) of dimethyl sulfate, stir for 1h, filter, wash the s...

Embodiment 2

[0039] Embodiment 2: Preparation of formula (II) 3-[(cyclopentyl hydroxyphenylacetyl) oxygen]-1,1-dimethylpyrrolidine taurate

[0040] Preparation: In a dry 1000ml reactor, add 40g (0.182mol) of cyclopentylmandelic acid and 200ml of N,N-dimethylformamide, cool to 20±5°C, add 36g of N'N-carbonyldiimidazole ( 0.222mol), stirred for 20min, added 22.8g (0.225mol) of 3-hydroxy-1-methyltetrahydropyrrole, heated to 60±5°C within 50~60min, reacted for 24h, after TLC identified the reaction, cooled to 20 ℃, pump into a 5L liquid separator, add 280ml of purified water, stir, add 320ml of toluene, stir for 10 minutes, separate the liquids, wash the organic layer with 144ml of purified water x 5, concentrate to dryness at 50℃ under reduced pressure, and obtain about 59.2 grams of oily substance , used directly in the next step.

[0041] a. Add 59g (0.194mol) of the above product, 33g (0.194mol) methyl benzenesulfonate, and 450ml acetone into a 1000ml reactor, cool to 0°C, stir for 5 hour...

Embodiment 3

[0047] Embodiment 3: physicochemical property comparison

[0048] According to the four routine tests of the Chinese Pharmacopoeia 2015 edition.

[0049]

[0050]

[0051] Conclusion: The compounds of formula (I) and formula (II) of the present invention have suitable solubility and fluidity, and are not hygroscopic.

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Abstract

The invention discloses a glycopyrronium bromide substitute represented by formula (I) and formula (II), a preparation method thereof and a method for preparing a medicine for treating mydriasis, preparing a medicine for regulating cycloplegia, preparing a medicine for preventing, The medicine for treating and delaying juvenile myopia, and the medicine for preparing and treating chronic obstructive pulmonary disease (COPD), bronchitis or asthma. The compound of the present invention has excellent water solubility, powder fluidity and suitable pH value stability of ophthalmic preparations and injections, and is an excellent pharmaceutical alternative form of glycopyrronium bromide.

Description

1. Technical field [0001] The invention belongs to the technical field of medicine, and more specifically relates to a substitute for glycopyrronium bromide salt and a preparation method thereof, as well as medicines and drugs that can be used for the treatment or adjuvant treatment of mydriasis, regulation of cycloplegia, and delaying juvenile myopia. Use in a medicament for the treatment of chronic obstructive pulmonary disease (COPD), bronchitis or asthma. 2. Background technology [0002] Myopia is one of the eye diseases with the highest incidence rate in the world. The number of myopia patients in my country is nearly 300 million, and it is an out-and-out big country with myopia. The occurrence and development of myopia are closely related to the extension of the eye axis. However, as far as the current treatment methods are concerned, whether it is optometry or various refractive operations, although it can correct the visual abnormalities caused by myopia, it is not ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/12C07C305/06C07C303/24C07C303/32C07C309/14A61K31/40A61P27/08A61P27/10A61P11/00A61P11/06A61P29/00
CPCC07D207/12C07C305/06C07C303/24C07C303/32C07C309/14A61P27/08A61P27/10A61P11/00A61P11/06A61P29/00
Inventor 徐奎刘逸凡
Owner ANHUI HEALSTAR PHARM CO LTD