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Method for separating tropicamide raceme

A racemate, tropicamide technology, applied in the direction of organic racemization, organic chemical methods, chemical instruments and methods, etc., to achieve the effect of precise medication

Inactive Publication Date: 2015-02-18
NEW FOUNDER HLDG DEV LLC +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Tropicamide is a chiral mixture, and there is no literature report on its chiral resolution

Method used

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  • Method for separating tropicamide raceme
  • Method for separating tropicamide raceme

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Add 10g tropicamide racemate (35mmol) to 35ml (R)-(+)-1-phenylethanol, stir to dissolve, add dropwise 10ml from 1g(S)-(+)-ammonium lactate and 1.6 g(18.3mmol) (S)-(+)-lactic acid prepared into a methanol solution, after dripping, the temperature was raised to 65°C, and the methanol was distilled off. Let stand, lower the temperature to 18°C ​​for crystallization, and filter.

[0058] The filter cake was dissolved in 20ml of water, 15ml of chloroform was added, the pH was adjusted to 9-10 with 3N sodium hydroxide solution while stirring, the layers were separated, the organic phase was washed twice with 10ml of water, and the chloroform was recovered by distillation. Dry under reduced pressure at 60°C for 2h to obtain 4.1g of pure (S)-(-)-topecaramide, [α]=-54.3°.

[0059] Add 30ml of water and 30ml of chloroform to the filtrate, adjust the pH to 1-2 with 2N sulfuric acid, separate the layers, and then extract and wash the aqueous phase twice with 10ml of chloroform. Add 25...

Embodiment 2

[0061] Add 10g tropicamide racemate (35mmol) to 30ml (R)-(+)-1-phenylethanol, stir to dissolve, add dropwise 10ml from 1g(S)-(+)-ammonium lactate and 1.6 g(18.3mmol) (S)-(+)-lactic acid prepared into a methanol solution, after dripping, the temperature was raised to 65°C, and the methanol was distilled off. Let stand, lower the temperature to 20°C for crystallization, and filter.

[0062] The filter cake was dissolved in 20ml water, 15ml chloroform was added, pH was adjusted to 9-10 with 3N sodium hydroxide solution while stirring, the layers were separated, the organic phase was washed twice with 10ml water, the chloroform was recovered by distillation, and dried under reduced pressure at 60℃ In 2h, 4.5 g of pure (S)-(-)-topecaramide was obtained, [α]=-49.7°.

[0063] Add 30ml of water and 25ml of chloroform to the filtrate, adjust the pH to 1-2 with 2N sulfuric acid, separate the layers, and then extract and wash the aqueous phase twice with 10ml of chloroform. Add 25ml of chlo...

Embodiment 3

[0065] Add 10g tropecaramide racemate (35mmol) to 40ml (R)-(+)-1-phenylethanol, stir to dissolve, add dropwise 10ml of 1g(S)-(+)-ammonium lactate and 1.6 g(18.3mmol) (S)-(+)-lactic acid prepared into a methanol solution, after dripping, the temperature was raised to 65°C, and the methanol was distilled off. Let stand, cool to 17°C for crystallization, and filter.

[0066] The filter cake was dissolved in 20ml water, 15ml chloroform was added, pH was adjusted to 9-10 with 3N sodium hydroxide solution while stirring, the layers were separated, the organic phase was washed twice with 10ml water, the chloroform was recovered by distillation, and dried under reduced pressure at 60℃ In 2h, 3.9g of pure (S)-(-)-topecaramide was obtained, [α]=-56.3°.

[0067] Add 30ml of water and 30ml of chloroform to the filtrate, adjust the pH to 1-2 with 2N sulfuric acid, separate the layers, and wash the aqueous phase twice with 10ml of chloroform respectively. Add 25ml of chloroform to the water ph...

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Abstract

The invention provides a method for separating tropicamide raceme. The method comprises the steps of (1) reacting the tropicamide raceme and a chiral separation agent in a chiral solvent, so as to make the tropicamide raceme form two chiral salts with different solubleness; and (2) separating the two chiral salts with different solubleness by a crystallization method and obtaining optically active isomers separated from each other through alkaline treatment. The chiral separation agent has the same optical activity with the chiral solvent; and the chiral separation agent lactic acid. With the method provided by the invention, (S)-(-)-tropicamide and (R)-(+)-tropicamide can be obtained efficiently and successfully. By the chiral separation of the drug tropicamide, the drug can be taken more accurately and healthily.

Description

Technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to a method for resolving the racemate of tropicamide. Background technique [0002] Toppicamide is a mydriatic drug. It is used for mydriatic examination and optometry, and can also be used to prevent and treat juvenile pseudomyopia. Toppicamide is an anticholinergic drug that can block the excitement of the iris sphincter and ciliary muscles caused by acetylcholine. Its 0.5% solution can cause mydriasis, and 1% solution can cause ciliary muscle palsy and mydriasis. [0003] Toppicamide is a synthetic derivative of tropic acid. It has a low dissociation constant, good intraocular permeability, strong tissue diffusion, rapid onset and short maintenance time. After instilling the eye with 0.5%, 1% tropicamide solution, the pupil dilated within 20-30 minutes, and the paralysis effect reached a peak. Subsequently, its effect gradually decreases, regulating paralysis (residual...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/40C07B57/00
Inventor 彭平郭萍张洪兰王先文
Owner NEW FOUNDER HLDG DEV LLC
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