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Method for producing 9-[2(hydroxyl)propyl] adenine

A technology of acetonyl adenine and adenine, which is applied in the fields of medicine and chemical industry, can solve the problems of harsh reaction conditions, complex process flow, and many reaction steps, and achieve the effects of mild reaction conditions, simple preparation process, and low cost

Inactive Publication Date: 2010-09-15
江苏八巨药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The present invention aims at the defects of many reaction steps in the prior art, complex process flow, harsh reaction conditions and high cost, and provides a production 9- [2(Hydroxy)propyl]adenine method

Method used

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  • Method for producing 9-[2(hydroxyl)propyl] adenine
  • Method for producing 9-[2(hydroxyl)propyl] adenine
  • Method for producing 9-[2(hydroxyl)propyl] adenine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] In a 250ml three-necked flask equipped with a stirrer, a thermometer, and a dropping funnel, add 150ml of dimethylformamide (DMF), 29g of potassium carbonate, and 13.5 grams of adenine, heat to 120°C under stirring, and heat and dissolve for 1 hour. After dissolving, lower the temperature to 5°C, add dropwise a solution made of 15g monochloroacetone and 20ml DMF, control the dropping temperature at 5°C-15°C, continue to react for 1 hour after the dropwise addition is completed, and filter while cold , the filter cake was washed with saturated brine, filtered and dried to obtain 16 g of 9-acetonyl adenine, the content was 99.0%, and the yield was 8.5%;

[0029] In a 250ml three-neck flask equipped with a stirrer, a thermometer, and a dropping funnel, add 9.5g of the above-prepared 9-acetonyl adenine and 100ml of water, and stir and dissolve at a temperature of 30°C for 1 hour. Add 9.5 g of sodium borohydride dissolved in a small amount of water dropwise at ~30°C; continu...

Embodiment 2

[0031] The device used is the same as in Example 1, and will not be described in detail; add 300g of dimethylformamide, 58g of potassium carbonate, and 27g of adenine, heat to 100°C under stirring, heat and dissolve for 2 hours, after the materials are dissolved, cool to 3°C, drop Add a mixed solution made of 46g of chloroacetone and 30ml of dimethylformamide, control the dropwise addition temperature at 5°C to 15°C, and continue to react for 1 hour after the dropwise addition is completed. After the reaction is completed, filter while cold and use the filter cake Washed with saturated brine, filtered and dried to obtain 34.4 g of 9-acetonyl adenine with a content of 99.1% and a yield of 90%;

[0032] The device used is the same as in Example 1, and will not be described in detail; add 19 g of 9-acetonyl adenine prepared above, 200 ml of water, stir and dissolve at a temperature of 20 ° C for 1 hour, and add a small amount of water dropwise at a temperature of 20 to 30 ° C Dis...

Embodiment 3

[0034]The device used is the same as in Example 1, and will not be described in detail; add 300g of dimethylacetamide, 58g of sodium carbonate, and 27g of adenine, heat to 130°C under stirring, heat and dissolve for 1 hour, after the materials are dissolved, cool to 12°C, drop Add a mixed solution made of 18.5g monochloroacetone and 20ml dimethylacetamide, control the dropwise addition temperature at 5°C-15°C, and continue to react for 1 hour after the dropwise addition is completed. After the reaction is completed, filter while cold, and the filter cake Wash with saturated brine, filter and dry to obtain 24.8 g of 9-acetonyl adenine, the content is 99.0%, and the yield is 65%;

[0035] The device used is the same as in Example 1, and will not be described in detail; add 19 g of 9-acetonyl adenine prepared above, 150 ml of ethanol, stir and dissolve at a temperature of 10 ° C for 2 hours, and add a small amount of water dropwise at a temperature of 20 to 30 ° C. Dissolved sodi...

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Abstract

The invention provides a method for producing a nucleoside medicine intermediate compound, namely, 9-(2 (hydroxyl) propyl adenine, and belongs to the medicineand chemical industry technical field. The method for producing the nucleoside medicine intermediate compound, namely, the 9- (2 (hydroxyl) propyl adenine comprises three steps, namely, condensation reaction, carbonyl reduction reaction, andpost treatment. The method for producing the 9-(2 (hydroxyl) propyl adenine adopts achiral material as the initial material, the technical process is simple, the reaction condition is temperate, and the cost is low.

Description

technical field [0001] The invention relates to a method for producing a drug intermediate, in particular to a method for producing a nucleoside drug intermediate 9-[2(hydroxyl)propyl]adenine; it belongs to the technical fields of medicine and chemical industry. Background technique [0002] 9-[2(hydroxy)propyl]adenine is an intermediate of anti-AIDS drug retroviral synthetase inhibitor (R)-9-[2(phosphorylmethoxy)propyl]adenine; [0003] The inhibitor was developed by GILEAD SCIENCES INC of the United States, which can effectively and selectively antagonize HIV and other retroviruses. It can effectively treat HIV-1 and HIV-2 viruses in human lymphocytes (MT-4), human monocytes, macrophages, etc., and is suitable for treating various immunodeficiency diseases. It is still in phase II clinical stage. The inhibitor intermediate 9-[2(hydroxy)propyl]adenine prepared by GILEAD SCIENCES INC in the United States is obtained from isobutanol lactate as a starting material through 5 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D473/04
Inventor 徐斌孙守湘吴六君李炳全郦观江陈恬
Owner 江苏八巨药业有限公司
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