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Cholinolytic drug glycopyrronium bromide and composition

A technology of glycopyrronium bromide and composition, which is applied in the field of pharmaceutical compositions containing glycopyrronium bromide, and can solve problems such as no central anticholinergic activity

Inactive Publication Date: 2015-12-23
李兴惠
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Glycopyrronium bromide is a quaternary ammonium anticholinergic drug, which can inhibit the secretion of gastric juice and regulate gastrointestinal peristalsis; this product also has a stronger antisaliva secretion effect than atropine, but has no central anticholinergic activity

Method used

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  • Cholinolytic drug glycopyrronium bromide and composition
  • Cholinolytic drug glycopyrronium bromide and composition
  • Cholinolytic drug glycopyrronium bromide and composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0182] Embodiment 1: Preparation of glycopyrronium bromide bulk drug

[0183] Step (1), synthetic formula I compound and enantiomer thereof:

[0184] Make hydroxycyclopentyl mandelic acid methyl ester (MCPM) and N-methylpyrrolidin-3-alcohol (NMP) reaction according to the method in US2956062A to obtain glycopyrrolate base (GP base), then according to CN101133021B specification sheet [0015]- The method contained in section makes glycopyrronium base react with methyl bromide and then carries out recrystallization refining to gained product, obtains glycopyrronium bromide.

[0185] RRT0.89 content=4.63%, RRT1.14 content=1.78%, RRT2.68 content=1.14%.

[0186] Step (2), recrystallization refining:

[0187] At a temperature of 55-60°C, dissolve 1.5 g of the product obtained in step (1) in 10 ml of anhydrous ethanol-ethyl acetate mixed solvent (100:12, v / v), and slowly add 120 ml of methyl ethyl ether dropwise to it , standing at 4-5° to allow sufficient precipitation (about 24 h...

Embodiment 2

[0200] Embodiment 2: Preparation of glycopyrronium bromide bulk drug

[0201] Step (1), synthetic formula I compound and enantiomer thereof:

[0202] The crude product of glycopyrronium bromide was prepared according to the method in the specific embodiment part of the CN103159659A description, that is, the method described in paragraph [0010] to [0013], line 4 of the description. RRT0.89 content=4.76%, RRT1.14 content=1.61%, RRT2.68 content=1.21%.

[0203] Step (2), recrystallization refining:

[0204] The product obtained in the above step (1) was recrystallized according to the method of step (2) of Example 1 of the present invention (the recrystallization yield was 89.7%).

[0205] RRT0.89 content=0.83%, RRT1.14 content=0.34%, RRT2.68 content=0.20%. In this recrystallization purification, the content of RRT0.89 was reduced by 82%, the content of RRT1.14 was reduced by 79%, and the content of RRT2.68 was reduced by 83%.

[0206] Step (3), recrystallization refining ag...

Embodiment 3

[0214] Embodiment 3: Preparation of glycopyrronium bromide bulk drug

[0215] Step (1), synthetic formula I compound and enantiomer thereof:

[0216] Glycopyrronium bromide was prepared according to the method in the specific embodiment part of the CN102627595A description, that is, the method described in paragraphs [0043] to [0046] of the description. RRT0.89 content=4.13%, RRT1.14 content=1.36%, RRT2.68 content=1.03%.

[0217] Step (2), recrystallization refining:

[0218] The product obtained in the above step (1) was recrystallized according to the method of step (2) of Example 1 of the present invention (recrystallization yield 92.4%).

[0219] RRT0.89 content=0.70%, RRT1.14 content=0.24%, RRT2.68 content=0.16%. In this recrystallization and purification, the content of RRT0.89 was reduced by 83%, the content of RRT1.14 was reduced by 82%, and the content of RRT2.68 was reduced by 84%.

[0220] Step (3), recrystallization refining again:

[0221] The product obtai...

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Abstract

The invention relates to cholinolytic drug glycopyrronium bromide and a composition, in particular to a pharmaceutical drug and a preparation thereof. The drug contains a compound with the formula shown in the specification and an enantiomer of the compound. Serving as an anticholinergic drug, the drug and the preparation can be clinically applied to anesthesia, peptic ulcers, salivation and the like. The bulk drug or the preparation has the effects of restraining gastric secretion and regulating gastrointestinal peristalsis, has a stronger salivation resisting effect than atropine, but has no central anticholinergic activity. Generally, the drug or the preparation is clinically applied to gastric and duodenal ulcers, chronic gastritis, excessive gastric acid secretion and the like.

Description

technical field [0001] The invention belongs to the technical field of medicine and relates to a pharmaceutical composition as an anticholinergic agent, in particular to a pharmaceutical composition containing glycopyrronium bromide as an anticholinergic agent. Background technique [0002] Glycopyrronium bromide, its English name is Glycopyrronium Bromide or Glycopyrrolate, and its typical Chinese chemical name is: (3RS)-3-[(2SR)-(2-cyclopentyl-2-hydroxyl-2-phenylacetyl) Oxy]-1,1-dimethylpyrrolidinium bromide, the typical English chemical name is: (3RS)-3-[(2SR)-(2-Cyclopentyl-2-hydroxy-2-phenylacetyl)oxy] -1,1-dimethylpyrrolidiniumbromide, which has the formula C 19 h 28 BrNO 3 , the molecular weight is 398.3, and its typical chemical structural formula is: [0003] and its enantiomers [0004] That is, the glycopyrronium bromide used as medicine is (3R)-3-[(2S)-(2-cyclopentyl-2-hydroxy-2-phenylacetyl)oxy]-1,1-dimethyl ylpyrrolidinium bromide and (3S)-3-[(2R)-(2-cy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/12A61K31/40A61P1/04A61P23/00
CPCA61K31/40C07D207/12
Inventor 李兴惠
Owner 李兴惠
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