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Preparation method of abacavir

A kind of amino, hydrochloride technology, applied in the field of medicine and chemical industry, can solve the problem of difficult to remove impurities

Inactive Publication Date: 2015-07-22
ZHEJIANG JIUZHOU PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The commonality of the methods reported in the above patents is that they all use (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-ylmethanol (hydrochloride) Reaction with cyclopropylamine, due to the same reaction mechanism, there is a problem that impurities are difficult to remove when preparing abacavir

Method used

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  • Preparation method of abacavir
  • Preparation method of abacavir
  • Preparation method of abacavir

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Embodiment 1: the preparation of abacavir dihydrochloride

[0039] (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-ylmethanol hydrochloride (30g, 0.1mol) and cyclopropylamine ( 22.6 g, 0.4 mol) into 180 g of ethanol, heated to reflux until the reaction was completed, then added sodium carbonate (11 g, 0.1 mol), evaporated part of the solvent, filtered while hot, concentrated the filtrate to dryness, added 200 g of fresh ethanol and heated to dissolve After clearing, cool down to 40-45°C, add 35.5% ethanol hydrochloride (20.5g, 0.2mol) dropwise, heat up to 50-55°C after dropping, keep warm for 0.5-1 hour, cool down to room temperature, and filter to obtain Abacavir dihydrochloride 32.6g, yield is 91.4%.

Embodiment 2

[0040] Embodiment 2: the preparation of abacavir dihydrobromide

[0041] (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-ylmethanol hydrochloride (30g, 0.1mol) and cyclopropylamine ( 22.6g, 0.4mol) into 180g of isopropanol, heated to reflux until the reaction was over, then put in sodium carbonate (11g, 0.1mol), evaporated part of the solvent, filtered while hot, concentrated the filtrate to dryness, and put in 200g of fresh isopropanol After the alcohol is heated until it dissolves, cool down to 40-45°C, add 25% isopropanol hydrobromide (64.8g, 0.2mol) dropwise, raise the temperature to 50-55°C after dropping, and keep warm for 0.5-1 hour , cooled to room temperature, and filtered to obtain 40.1 g of abacavir dihydrobromide, with a yield of 90.1%.

Embodiment 3

[0042] Embodiment 3: the preparation of abacavir dibenzoate

[0043] (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-ylmethanol hydrochloride (30g, 0.1mmol) and cyclopropylamine ( 22.6g, 0.4mol) into 180g of isopropanol, heated to reflux until the reaction is over, put in sodium carbonate (11g, 0.1mol), evaporate part of the solvent, filter while hot, concentrate the filtrate to dryness, put in 400g of fresh isopropanol After the alcohol is heated to dissolve, cool down to 40-45°C, add benzoic acid (24.4g, 0.2mol), raise the temperature to 50-55°C after dropping, keep warm for 0.5-1 hour, cool down to room temperature, filter to obtain Bacavir dibenzoate 48.76g, the yield is 92.6%.

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Abstract

The invention relates to a preparation method of abacavir. According to the preparation method, (1S,4R)-4-(2-amino-6-chloro-9H-purine-9-yl)cyclopentene-2-ene-1-yl methanol or a hydrochloride of (1S,4R)-4-(2-amino-6-chloro-9H-purine-9-yl)cyclopentene-2-ene-1-yl methanol is reacted with cyclopropylamine, and then an obtained product and an alcohols solvent of acid are subjected to salt forming reaction so as to obtain abacavir. Abacavir free alkali with high purity and properties can be obtained via simple dissociation. The preparation method is suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and in particular relates to a preparation method of abacavir. Background technique [0002] Abacavir, the chemical name is (1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentenyl-1-methanol. The structural formula is as follows: [0003] [0004] It belongs to nucleoside reverse transcriptase inhibitor anti-HIV drugs, and is a competitive inhibitor of HIV-1 RT substrates, inhibits RT activity, hinders proviral DNA synthesis, and due to the lack of hydroxyl groups in the 3' structure, when they combine When the 3' end of the proviral DNA chain is reached, the 5' to 3' phosphodiester bond can no longer be combined, terminating the elongation of the viral DNA chain. Through the above mechanism of action, it can inhibit HIV replication, and its affinity with HIV-1RT is much stronger than that with normal DNA polymerase in cells, so it has a certain therapeutic index....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/16
CPCC07D473/16
Inventor 叶美其徐巧巧朱天昊吴昊陈林国许全贵
Owner ZHEJIANG JIUZHOU PHARM CO LTD
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