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Method for preparing high-purity fatty acid derivative

A technology of fatty acid derivatives and long-chain fatty acids, which is applied in the field of biomedicine and can solve problems such as difficulties in the preparation of fatty acid derivatives, environmental pollution by by-products, and reduced yields.

Pending Publication Date: 2020-11-10
江苏万邦医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the prior art, it is difficult to prepare high-purity fatty acid derivatives. The carboxyl group of glutamic acid terminal protected by methyl group will hydrolyze the active ester at the same time during alkaline hydrolysis, and the carboxyl group of glutamic acid protected by tert-butyl When acetic acid is hydrolyzed, it is also easy to destroy the active ester, and it is easy to produce other by-products and seriously pollute the environment
The preparation of high-purity fatty acid derivatives requires the purification of intermediates in each step, which greatly reduces the yield and increases the economic cost

Method used

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  • Method for preparing high-purity fatty acid derivative
  • Method for preparing high-purity fatty acid derivative
  • Method for preparing high-purity fatty acid derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0064] 1. Preparation of succinimidyl palmitate

[0065]

[0066] Palmitic acid (100g, 390.0mmol) was suspended in N,N-dimethylformamide (2000ml), and N-hydroxysuccinimide (49.3g, 429.0mmol) and dicyclohexyl carbon were added at -10°C Diimine (88.5 g, 429.0 mmol), continued to react at -10°C for 2 hours, then returned to room temperature (25°C) and stirred overnight. Suction filtration, the filtrate was concentrated under reduced pressure, 2000 mL of dichloromethane was added to the concentrated residue, washed successively with 1000 mL of saturated sodium bicarbonate, 3 times with 1000 mL of water, 1000 mL of saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was Dichloromethane was removed by pressure distillation to obtain a white solid residue, to which n-heptane was added for recrystallization, the filter cake was collected by filtration, the filter cake was washed with n-heptane (300ml), and the filter cake (being succinimide palmitate) w...

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Abstract

The invention provides a method for preparing a fatty acid derivative. The preparation method comprises the following specific steps: firstly, reacting long-chain fatty acid with Nhydroxysuccinimide to obtain long-chain fatty acid succinimide ester; then reacting with Lglutamic acid 1benzyl ester to obtain long-chain fatty acyl-Glu(OSus)-OBn; and finally, removing benzyl of the long-chain fatty acyl-Glu(OSus)-OBn to obtain the high-purity long-chain fatty acid derivative. The route of the method has the following advantages: (1) the reaction conditions are mild, and the reaction efficiency ishigh; (2) the operation is simple and convenient, the cost is low, the purification is easy, and the method is more suitable for preparing GLP1 analogues.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a method for preparing high-purity fatty acid derivatives. Background technique [0002] With the improvement of living standards and changes in lifestyle, the incidence of diabetes in my country has been increasing year by year in recent years. Type 2 diabetes is mainly treated by oral or subcutaneous injection. There are many types of hypoglycemic drugs for type 2 diabetes, including metformin, sulfonylureas, glucagon-like peptide (GLP-1) receptor agonists, etc., GLP -1. GLP-1 analogs and their fragments are especially effective in the treatment of type 2 diabetes. Glucagon-like peptide 1 (GLP-1) receptor agonists are a new class of drugs for the treatment of diabetes, which not only reduce It has beneficial metabolic effects such as blood sugar, weight loss, blood pressure reduction, and improvement of blood lipid profile, and it also has protective effects on cardiovascu...

Claims

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Application Information

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IPC IPC(8): C07D207/46C07C231/02C07C233/47
CPCC07D207/46C07C231/02C07C233/47
Inventor 文良柱梅丽崔杉许培源冯聪
Owner 江苏万邦医药科技有限公司
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