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Salicylic acid berberine type alkaloid quaternary ammonium salt and application in preparation of medicines

A technology of quaternary ammonium salt compound and berberine, applied in the field of medicine, can solve problems such as limited clinical benefit, and achieve the effects of remarkable safety, remarkable practical value and excellent solubility

Active Publication Date: 2020-09-15
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But current anti-ulcerative colitis drugs have limited clinical benefit

Method used

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  • Salicylic acid berberine type alkaloid quaternary ammonium salt and application in preparation of medicines
  • Salicylic acid berberine type alkaloid quaternary ammonium salt and application in preparation of medicines
  • Salicylic acid berberine type alkaloid quaternary ammonium salt and application in preparation of medicines

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preparation example Construction

[0060] The preparation process and structural identification data of the active compounds of the present invention, wherein the compound number corresponds to the specific compound number in the content of the present invention.

[0061] 1. Experimental example of compound preparation of the present invention

experiment example (1

[0062] Experimental example (1): Synthesis and structure identification data of compound 1 of the present invention

[0063] Take by weighing berberine chloride quaternary ammonium salt (2.00g, 5.62mmol) in the reaction flask, add 5N aqueous sodium hydroxide solution (12ml), then add acetone (4ml, 54.27mmol) dropwise, stir at room temperature for 4h, the raw material reaction completely. The reaction mixture was suction-filtered, and the filter cake was washed with water until it became neutral to obtain 1.99 g of 8-acetonyl dihydrocopterine as a light yellow solid, with a yield of 93.87%.

[0064] Weigh 5-aminosalicylic acid (43mg, 0.28mmol) in a reaction flask, add DMSO (3ml), sonicate until completely dissolved, then add 8-acetonyldihydrocoptisine (100mg, 0.26mmol) under stirring at room temperature, After the addition, the reaction was carried out at 25°C for 5.5h until the raw materials were completely reacted; adding tetrahydrofuran (6ml) to the reaction mixture to dilu...

experiment example (2

[0065] Experimental example (2): Synthesis and structural identification data of compound 2 of the present invention

[0066] Weigh the quaternary ammonium salt of berberine chloride (3.84g, 10.80mmol) in a reaction flask, add 5N aqueous sodium hydroxide solution (100ml), then add acetone (10ml, 0.14mol) dropwise, and heat and stir at 50°C for 4h , the raw material reacted completely. The reaction mixture was suction filtered, and the filter cake was washed with water until neutral. Obtain the light yellow solid crude product, then recrystallize with a mixed solvent of acetone and water (acetone:water=3:1, v / v) to obtain 2.26g of yellow granular crystals of 8-acetonyl dihydroisocortisine, yield 55.52%.

[0067] Weigh 5-aminosalicylic acid (43mg, 0.28mmol) in a reaction flask, add DMSO (3ml), sonicate until completely dissolved, then add 8-acetonyl dihydroisoberisine (100mg, 0.26mmol) under stirring at room temperature After the addition, the reaction was carried out at 25°C...

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Abstract

The invention discloses a salicylic acid berberine type alkaloid quaternary ammonium salt compound represented by a general formula I, a preparation method, a solubility characteristic and a pharmaceutical composition thereof, and application of the salicylic acid berberine type alkaloid quaternary ammonium salt compound in preparation of medicinal products. According to the invention, the salicylic acid berberine type alkaloid quaternary ammonium salt compound represented by the general formula I can be prepared by an organic synthesis method, shows obvious alcohol-water mixed solvent solubility, can be conveniently prepared on a large scale, has remarkable ulcerative colitis resisting activity, has the characteristics of no toxicity or low toxicity, and can be used for preventing, relieving and / or treating ulcerative colitis.

Description

technical field [0001] The invention relates to a salicylic acid berberine type alkaloid quaternary ammonium compound synthesized by taking salicylic acid aromatic organic acid and various acid radicals other than salicylic acid radicals as berberine type alkaloid quaternary ammonium compounds Salt compound, preparation method of the compound of the present invention, pharmaceutical composition containing the compound of the present invention and pharmaceutical use of the compound of the present invention against ulcerative colitis. The compound of the present invention shows remarkable effectiveness in the drug effect experiment of treating ulcerative colitis disease; The compound of the present invention shows remarkable safety in the toxicology experiment; The compound of the present invention has excellent performance in 60% ethanol water mixed solvent solubility. The above-mentioned properties of the compound of the present invention are obviously outstanding. Therefore,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D455/03A61K31/4375A61P1/04A61P1/00
CPCC07D455/03A61P1/04A61P1/00A61K31/4375A61P29/00A61K31/04Y02A50/30
Inventor 秦海林吴练秋李景张海婧邓安珺唐晓楠李想王与菲李志宏王文杰
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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