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Preparation method for analgesic and antipyretic drug-analgin

Analgin, a synthetic method technology, applied in the field of drug synthesis, can solve the problems of polluting the environment, low yield, etc., and achieve great economic benefits and reduce environmental pollution

Active Publication Date: 2014-03-26
WUHAN WUYAO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield is low, and a large amount of sulfuric acid is used, which pollutes the environment

Method used

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  • Preparation method for analgesic and antipyretic drug-analgin
  • Preparation method for analgesic and antipyretic drug-analgin
  • Preparation method for analgesic and antipyretic drug-analgin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 Preparation of 4-N-desmethyl Sulpyrine

[0050] 20.3 g of 4-aminoantipyrine (AA) (0.1 mol), 10.4 g of sodium bisulfite (0.1 mol), 3 g of paraformaldehyde (0.1 mol) and 100 ml of 95% ethanol were added to a 250 ml reaction bottle, stirred and heated to reflux for 1 hour. After the reaction liquid was lowered to 45°C, solid 4-N-desmethyl sulpyrine was added to the reaction liquid to cause crystallization. After vigorously stirring for half an hour, the solid was collected by filtration to obtain 30.3 g of 4-N-desmethyl sulpyrine. The rate is 90%; melting point: 217°C; 1 H NMR (400MHz, DMSO-d 6 )δ: 2.18(s, 3H), 2.80(s, 3H), 3.78(d, J=6.96Hz, 2H), 4.00(m, 1H), 7.25(m, 1H), 7.45(m, 4H); 13CNMR (100MHz, DMSO-d 6 ) δ 161.8, 140.8, 135.4, 128.9(2), 125.3, 122.1(2), 120.0, 62.4, 37.7, 10.4.

Embodiment 2

[0051] Embodiment 2 The preparation of Sulpyrine crude product

[0052] 33 grams of 4-N-desmethyl sulpyrine (0.1mol) was dissolved in 100 milliliters of 95% ethanol, and 10 milliliters of 35% formaldehyde aqueous solution (0.13mol), 2 grams of 10% palladium carbon and 5 milliliters of pH6. 86 phosphate standard buffer solution (prepared by sodium dihydrogen phosphate and dipotassium hydrogen phosphate), vacuumize after transferring to the hydrogenation tank, then feed hydrogen, start stirring, and keep the hydrogen pressure at 0.1MPa to react for two hours, and the reaction temperature is controlled At 60-85° C., after the reaction was completed, the filtrate was heated and filtered, and the filtrate crystallized after cooling, and the solid was collected by filtration to obtain 34.5 g of a crude product of Sulpyrine, with a yield of 98%.

Embodiment 3

[0053] The preparation of embodiment 3 4-methylaminoantipyrine (MAA)

[0054] 33 gram Sulpyrine crude products (0.1mol) are dissolved in 50 milliliters of water, then add 5 milliliters of 10% sodium hydroxide, be heated to 50 ℃ of reaction 1 hour, separate after cooling and obtain MAA21.6 grams (yield 98% ).

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Abstract

The invention relates to a new preparation process for an analgesic and antipyretic drug-analgin. In the traditional analgin synthesis path from 4-aminoantipyrine (AA) to analgin, formylation reaction, methylation reaction, hydrolysis reaction and condensation reaction need to be carried out, the yield is low, a large amount of sulfuric acid needs to be used and the environment is polluted. While the new preparation process is as follows: firstly, directly condensing the 4-aminoantipyrine (AA), paraformaldehyde and sodium hydrogensulfite to obtain 4-N-demethylated analgin; secondly, hydrogenating the 4-N-demethylated analgin and formaldehyde in the presence of palladium carbon to generate an analgin crude product of the; thirdly, as the analgin crude product is difficultly purified, hydrolyzing the analgin crude product in alkali condition to obtain 4-methylaminoantipyrine (MAA); and lastly, condensing the 4-methylaminoantipyrine (MAA), the formaldehyde and the sodium hydrogensulfite to generate the analgin. According to the preparation process, the reaction condition is moderate, the yield is high, the sulfuric acid is not used and the three wastes are reduced.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a new synthesis method of analgin, an antipyretic and analgesic drug. technical background [0002] Analgin belongs to antipyretic and analgesic and non-steroidal anti-inflammatory analgesic drugs. It has been on the market for 100 years. It has definite curative effect, convenient use, various dosage forms and low price. It has played an important role in clinical medicine for many years. . It has a wide market in many countries in the world, especially in developing countries, where it is widely used and in great demand. It is mainly used to reduce fever, but also to treat acute arthritis, headache, rheumatic pain, toothache and muscle pain. [0003] At present, the production of most Analgin in China is to use pyrazolone as a raw material to generate antipyrine (AT) through methylation and hydrolysis; Ammonium sulfite reduction, hydrolysis with sulfur...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/48
Inventor 杨尚金皮金红董建强鄢卫魏金维谢国范
Owner WUHAN WUYAO PHARMA
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