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Polycrystal substance of acetyl chloride levocarnitine

A technology for acetyl chloride and drugs, which is applied in the field of acetyl levocarnitine chloride crystal form and its preparation, and can solve the problems of high processing cost and the like

Inactive Publication Date: 2012-07-11
南京海辰药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the degradation properties of acetyl L-carnitine chloride, these powders need to be prepared and processed at low temperature
Such processing is expensive as it requires special equipment and operations

Method used

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  • Polycrystal substance of acetyl chloride levocarnitine
  • Polycrystal substance of acetyl chloride levocarnitine
  • Polycrystal substance of acetyl chloride levocarnitine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation of embodiment 1 type I chloride acetyl levocarnitine

[0023] In a 2L reaction flask, add 500mL of glacial acetic acid and 250g of levocarnitine respectively, stir and dissolve at about 50-60°C, and add 215g of acetyl chloride dropwise at a temperature of 50-60°C. After dripping, keep warm for 2-3 hours. After the solvent was recovered under reduced pressure, 1250 mL of isopropanol was added. After the addition was complete, the temperature was raised to reflux to dissolve the liquid, and then the temperature was lowered to below 15° C. and stirred for 1 hour for crystallization. Filter, wash with 300 mL of isopropanol, suck dry, and dry in vacuo to obtain 338 g of white crystalline solid. The yield is 90.9%. Purity expressed by HPLC area %: 98.6%, levocarnitine 0.5%, 3-carboxyallyl-N,N,N-trimethylammonium chloride 0.5%, enantiomer 0.2%.

Embodiment 2

[0024] The preparation of embodiment 2 type II chloride acetyl levocarnitine

[0025] In a 2L reaction flask, add 500mL of glacial acetic acid and 250g of levocarnitine respectively, stir and dissolve at about 50-60°C, and add 215g of acetyl chloride dropwise at a temperature of 50-60°C. After dripping, keep warm for 2-3 hours. After the solvent was recovered under reduced pressure, 500 mL of absolute ethanol was added. After the addition was complete, the temperature was controlled below 15°C and the crystallization was stirred for 1 h. Filter, wash with absolute ethanol, suck dry, and vacuum dry to obtain 320 g of white crystalline solid. Yield 86.1%. Purity expressed by HPLC area %: 99.3%, levocarnitine 0.1%, 3-carboxyallyl-N,N,N-trimethylammonium chloride 0.1%, enantiomer 0.1%. The obtained solid was identified by X-ray powder diffraction as Form II acetyl-levocarnitine chloride.

Embodiment 3

[0026] The preparation of embodiment 3 type III chloride acetyl levocarnitine

[0027] Add 100g of acetyl levocarnitine chloride prepared in Example 1 into 200mL of glacial acetic acid, heat to 50-60°C, stir to dissolve and filter, drop the filtrate into 200mL of acetone, cool to below 10°C and stir to analyze crystallized for 1 h, filtered, washed with acetone, and dried in vacuo to obtain 78 g of white crystalline solid with a yield of 78%. Purity expressed by HPLC area %: 99.4%, levocarnitine 0%, 3-carboxyallyl-N,N,N-trimethylammonium chloride 0%, enantiomer 0%. The obtained solid was identified by X-ray powder diffraction as Form III acetyl-levocarnitine chloride.

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Abstract

The invention provides new crystal solid forms of acetyl chloride levocarnitine, namely acetyl chloride levocarnitine of type II and type III, and a composition comprising the crystal solid forms and a method for preparing the crystal solid forms.

Description

technical field [0001] The invention relates to a crystal form of acetyl levocarnitine chloride and a preparation method thereof. Background technique [0002] The chemical name of acetyl levocarnitine chloride (ALC) is (2R)-2-acetoxy-3-carboxypropyl-N,N,N-trimethylammonium chloride, and its structure is as follows: [0003] [0004] ALC is synthesized catalyzed by ALC transferase in the human brain, liver, and kidney. ALC can promote mitochondrial absorption of acetyl-CoA during fatty acid oxidation, increase the production of acetylcholine, and stimulate the synthesis of proteins and membrane phospholipids. ALC is structurally similar to acetylcholine, and can also exert cholinergic effects. ALC has been shown to play a role in Alzheimer's disease, depression in the elderly, HIV infection, peripheral neuropathy, cerebral ischemia-reperfusion injury, and several cognitive dysfunctions. [0005] The literature Helvetica Chimica Acta, 1987, 70: 2085-2064 reported the sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/22C07C227/18A61K31/197A61P25/28A61P25/24A61P31/18A61P25/02A61P15/00A61P25/32A61P1/16A61P9/10
Inventor 冯明声李建情韩爱霞汪宗华林家红刘志芳郁博媛曹于平
Owner 南京海辰药业股份有限公司
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