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Method for preparing (R)-4-hydroxy-2-oxo-1-pyrrolidineacetamide crystal form

A technology of pyrrolidine acetamide, -4-, applied in the directions of organic chemistry, organic chemistry, etc., can solve the problems of disclosure of preparation method, less research on preparation method and crystal form of pyrrolidine acetamide, etc.

Inactive Publication Date: 2018-07-20
CHONGQING RUNZE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the preparation method and crystal form of (R)-4-hydroxy-2-oxo-1-pyrrolidineacetamide are less studied, and there is no (R)-4-hydroxyl-2-oxo-1-pyrrolidineacetamide crystal Type of preparation method disclosed

Method used

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  • Method for preparing (R)-4-hydroxy-2-oxo-1-pyrrolidineacetamide crystal form
  • Method for preparing (R)-4-hydroxy-2-oxo-1-pyrrolidineacetamide crystal form
  • Method for preparing (R)-4-hydroxy-2-oxo-1-pyrrolidineacetamide crystal form

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] In 150mL of methanol, add 10g of (R)-4-hydroxy-2-oxo-1-pyrrolidineacetamide, stir continuously, heat to 50°C, dissolve completely, add 0.5g of activated carbon and stir for 30 minutes, filter to obtain methanol solution, the methanol solution was concentrated to a total volume of 20ml to obtain a saturated methanol solution, 30ml of ethanol was added, stirred and crystallized at 5°C, and filtered to obtain colorless sand-like crystals. Identified by the method of Example 2, it is (R)-4-hydroxy-2-oxo-1-pyrrolidineacetamide crystal form I.

Embodiment 2

[0048] The (R)-4-hydroxyl-2-oxo-1-pyrrolidineacetamide colorless sand granular crystal obtained in Example 1 is subjected to crystal parameter measurement, including powder diffraction measurement, infrared spectrum measurement, differential calorimetry measurement, Thermogravimetric assay. Test instrument conditions: The test uses a DX2500 X-ray diffractometer (Danfang Yuan Instrument, Liaoning) to analyze the pre-oxidized body and carbonized particles in each stage of the thermal stabilization process. Ni filter, CuKα as radiation source, X-ray wavelength λ=0.1541nm, acceleration voltage and current intensity are 40kV and 50mA respectively. Set the scanning interval to 0.02°, the scanning speed to 3° / min, and the scanning range to 5° to 45°. The crystals prepared in Example 1 have diffraction angles 2θ of 12.423, 14.928, 16.285, 16.465, 17.344, 19.198, 20.459, 20.707, 21.548, 21.889, 23.203, 25.054, 26.117, 29.913, 30.49, 35.1369, 37° peak, powder diffraction results as f...

Embodiment 3

[0064] In 150mL of methanol, add 8g of (R)-4-hydroxy-2-oxo-1-pyrrolidineacetamide, stir continuously, heat to 30°C, dissolve completely, add 0.4g of activated carbon and stir for 20 minutes, filter to obtain methanol solution, the methanol solution was concentrated to a total volume of 20ml to obtain a saturated methanol solution, 20ml of ethanol was added, stirred and crystallized at 4°C, and filtered to obtain colorless sand-like crystals. Identified by the method of Example 2, it is (R)-4-hydroxy-2-oxo-1-pyrrolidineacetamide crystal form I.

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Abstract

The invention provides a method for preparing an (R)-4-hydroxy-2-oxo-1-pyrrolidineacetamide crystal form. The (R)-4-hydroxy-2-oxo-1-pyrrolidineacetamide crystal form has diffraction peaks at 2theta of12.423 + / - 0.2 DEG, 16.465 + / - 0.2 DEG, 17.344 + / - 0.2 DEG, 21.889 + / - 0.2 DEG and 25.054 + / - 0.2 DEG. The (R)-4-hydroxy-2-oxo-1-pyrrolidineacetamide crystal form can promote the synthesis of phosphorylcholine and o-acylethanolamine, promote brain metabolism, has a stimulation effect on the specific central nervous pathway through blood brain barrier, and has special bioactivity in calming and anti-epilepsy fields. The peak melting temperature of the (R)-4-hydroxy-2-oxo-1-pyrrolidineacetamide crystal form is 133.1 + / - 2 DEG C, and the (R)-4-hydroxy-2-oxo-1-pyrrolidineacetamide crystal form has a fast dissolution rate in water, has a solubility in water of 100 mg / mL or more, has a high bioavailability, a good stability and a good particle fluidity, and is suitable for being applied to theproduction of medicinal preparations, storage and transportation. The preparation method is simple, and is suitable for industrial production.

Description

technical field [0001] The present invention relates to (R)-4-hydroxyl-2-oxo-1-pyrrolidineacetamide crystal form, in particular to a preparation of (R)-4-hydroxyl-2-oxo-1-pyrrolidineacetamide crystal form method. Background technique [0002] (R)-4-Hydroxy-2-oxo-1-pyrrolidineacetamide (CAS No. 68252-28-8), the dextrorotatory version of the nootropic drug 4-hydroxy-2-oxo-1-pyrrolidineacetamide body. The latest research shows that this compound has special biological activities in the fields of sedation and anti-epileptic, and it has low toxicity and wide range of drug safety. It is expected to become a substitute for the existing highly toxic anti-epileptic drugs. The specific structure of (R)-4-hydroxyl-2-oxo-1-pyrrolidineacetamide is as follows: [0003] [0004] To effectively develop (R)-4-hydroxy-2-oxo-1-pyrrolidineacetamide into pharmaceuticals, a solid state form with ease of manufacture and acceptable chemical and physical stability is required to facilitate its...

Claims

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Application Information

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IPC IPC(8): C07D207/273
CPCC07B2200/13C07D207/273
Inventor 叶雷
Owner CHONGQING RUNZE PHARM CO LTD
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