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Novel method for preparing Nevirapine

A technology of methyl and compound, applied in the new field of preparation of nevirapine, can solve the problems of high reaction temperature, high production cost, difficult recovery, etc., and achieve the effects of high yield, reduced energy consumption, and less dosage

Active Publication Date: 2009-11-25
ZHEJIANG HUAHAI PHARMACEUTICAL CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods all have great shortcomings, such as in order to avoid the volatilization of cyclopropylamine, the condensation process of compound (II) and cyclopropylamine needs to be carried out in an autoclave; the reaction temperature is as high as 140 ° C, not only the energy consumption required for the production process is high, And there is a certain risk; Diethylene glycol dimethyl ether is used as a solvent, and recovery is difficult; thus the production cost is relatively high

Method used

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  • Novel method for preparing Nevirapine
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add 22.5 g of compound (II), 0.8 g of cuprous chloride, 11 g of sodium carbonate, and 400 ml of toluene into a 1000 ml three-neck reaction flask in sequence, add 18 g of cyclopropylamine under electromagnetic stirring, and stir at 25°C for 15 hours.

[0018] The reaction solution was filtered, the filtrate was dried with anhydrous magnesium sulfate, filtered, the solvent in the filtrate was evaporated to dryness under reduced pressure to obtain a light brown solid, which was compound (III), and the HPLC detection content was 92%, which was directly used in the next step reaction . The obtained compound (III) was dissolved in 100 ml of diethylene glycol dimethyl ether for use.

[0019] Add 11 grams of NaH into a 500 ml dry three-necked flask, then add 100 ml of diethylene glycol dimethyl ether, stir and raise the temperature to 120°C, then add the obtained compound (III) diethylene glycol dimethyl ether solution dropwise, dropwise After the addition, continue to keep st...

Embodiment 2

[0021] Add 22.5 g of compound (II), 1.0 g of cuprous bromide, 11 g of sodium carbonate, and 400 ml of toluene into a 1000 ml three-necked reaction flask in sequence, add 18 g of cyclopropylamine under electromagnetic stirring, and stir at 25°C for 15 hours.

[0022] The reaction solution was filtered, the filtrate was dried with anhydrous magnesium sulfate, filtered, and the solvent in the filtrate was evaporated to dryness under reduced pressure to obtain a light brown solid, which was compound (III), which was directly used in the next reaction. The obtained compound (III) was dissolved in 100 ml of diethylene glycol dimethyl ether for use.

[0023] Add 11 grams of NaH into a 500 ml dry three-necked flask, then add 100 ml of diethylene glycol dimethyl ether, stir and raise the temperature to 120°C, then add the obtained compound (III) diethylene glycol dimethyl ether solution dropwise, dropwise After the addition, continue to keep stirring for 1 hour. Lower the temperature ...

Embodiment 3

[0025] Add 22.5 g of compound (II), 1.2 g of cuprous iodide, 11 g of sodium carbonate, and 400 ml of toluene into a 1000 ml three-necked reaction flask in sequence, add 18 g of cyclopropylamine under electromagnetic stirring, and stir at 25°C for 15 hours.

[0026] The reaction solution was filtered, the filtrate was dried with anhydrous magnesium sulfate, filtered, and the solvent in the filtrate was evaporated to dryness under reduced pressure to obtain a light brown solid, which was compound (III), which was directly used in the next reaction. The obtained compound (III) was dissolved in 100 ml of diethylene glycol dimethyl ether for use.

[0027] Add 11 grams of NaH into a 500 ml dry three-necked flask, then add 100 ml of diethylene glycol dimethyl ether, stir and raise the temperature to 120°C, then add the obtained compound (III) diethylene glycol dimethyl ether solution dropwise, dropwise After the addition, continue to keep stirring for 1 hour. Lower the temperature o...

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Abstract

The invention relates to a novel method for preparing Nevirapine and discloses a novel method for preparing 11-cyclopropyl-5,11-dihydrogen-4-methyl-6H-II naphthyridine (3,2-b:2',3'-e)(1,4) azatropylidene (I) starting from 2-chlorin-N-(2-chlorin-4-methyl-3-pyridyl)-3-pyridine carboxamide (II). The method comprises the steps: a compound (II) reacts with cyclopropylamine under the existence of organic solvent and alkali and the catalysis of cupric salt under normal temperature and pressure to produce a compound (III), and the obtained compound (III) produces 11-cyclopropyl-5,11-dihydrogen-4-methyl-6H-II naphthyridine (3,2-b:2',3'-e)(1,4) azatropylidene (I) after intramolecular cyclization under the action of a certain organic solvent and the alkali. The method has low cost, environmental protection and wild reaction condition, thereby being suitable for commercial process.

Description

technical field [0001] The invention relates to a preparation method of nevirapine, a medicine for treating AIDS. Background technique [0002] Nevirapine, the English name is Nevirapine, the chemical name is 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1 , 4] Diazepines are non-nucleoside reverse transcriptase inhibitors developed by Boehringer Ingelheim, Germany. They were approved by the US FDA in September 1996. The trade name is Viramune, and they are now on the market in many countries. This product can bind near the catalytic site of the enzyme, act directly on reverse transcriptase, inhibit its activity, inhibit HIV replication, and is clinically used to inhibit mother-to-child transmission of AIDS. A 1999 study confirmed that nevirapine was far more effective than the older AIDS drug zidovudine in preventing vertical infection of newborns with HIV from the mother. Initial results showed that nevirapine was almost twice as effective as zidovudine...

Claims

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Application Information

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IPC IPC(8): C07D471/14A61P31/18
Inventor 竺伟胡永安马大为甘立新
Owner ZHEJIANG HUAHAI PHARMACEUTICAL CO LTD
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