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Preparation method of praziquantel

A technology of praziquantel and compound, which is applied in the field of preparation of veterinary drug praziquantel, can solve the problems of high price and not very easy to obtain, and achieve the effects of reducing environmental pressure, simple operation and cost saving

Active Publication Date: 2013-04-17
迪嘉药业集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But some reagents used in the process, such as aminoacetyl halide hydrochloride, haloacetaldehyde acetal are not very easy to get, and the price is relatively high, there is still room for improvement

Method used

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  • Preparation method of praziquantel
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  • Preparation method of praziquantel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: the preparation of compound 12

[0037] Add 122g of phenylethylamine (1mol) and 92.4g of sodium bicarbonate (1.1mol) into 600mL of dichloromethane and stir, cool down to about 0°C in an ice bath, slowly add 124.3g of chloroacetyl chloride (1.1mol) and 120g of dichloromethane For the mixed solution of methyl chloride, after the dropwise addition, heat up to 25°C to continue the reaction for 3h, add 200mL of water to the reaction solution at 0-5°C, separate the organic layer, extract the aqueous layer with dichloromethane (100mL*2), and combine After the dichloromethane layer, dry it with anhydrous sodium sulfate, filter, and distill off the dichloromethane under reduced pressure to obtain 189 g of a white solid with a yield of 96% and a melting point of 120-125°C.

Embodiment 2

[0038] Embodiment 2: the preparation of compound 13

[0039] Add 19.7g (0.1mol) of compound 12 and 12.1g of triethylamine (0.12mol) to 100mL of methanol, stir for 10min, add 9g (0.12mol) of glycine, heat up and reflux and stir for 8h, evaporate the methanol under reduced pressure, and add to the residue Add 50mL of water and 100mL of dichloromethane and stir, let stand to separate layers, separate the dichloromethane layer, wash the water layer with dichloromethane (50mL*2), combine the dichloromethane phases, dry over anhydrous sodium sulfate, and filter with suction. The methylene chloride was distilled off to obtain a brown solid, which was recrystallized from acetone to obtain 20.1 g of an off-white solid with a yield of 85% and a melting point of 187-189°C.

Embodiment 3

[0040] Embodiment 3: the preparation of compound 14

[0041] ①Add 23.6g of compound 13 (0.1mol) and 20.7g of potassium carbonate (0.15mol) to 100g of water and 300mL of dichloromethane, cool to 0°C under stirring, add dropwise 17.5g (0.12mol) of cyclohexanecarbonyl chloride, After the dropwise addition was completed, the temperature was raised to room temperature and stirred for 3 h, the dichloromethane layer was separated, the water layer was extracted with dichloromethane (100 mL*2), the dichloromethane layers were combined, dried over anhydrous sodium sulfate, suction filtered, and the dichloromethane was evaporated under reduced pressure. Chloromethane, add 100mL of petroleum ether to the residue, stir at room temperature for 1h, and suction filter to obtain 30.5g of off-white solid, yield 88%, melting point: 166-168°C.

[0042] ②Add 23.6g of compound 13 (0.1mol) and 6g of sodium hydroxide (0.15mol) to a mixture of 250mL of dichloromethane and 100mL of water, cool to 0°C w...

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Abstract

The invention belongs to the field of medicine, and relates to a preparation method of a veterinary drug praziquantel, in particular to a novel method for preparing praziquantel. Raw materials such as chloracetyl chloride and glycin used in the method are low in cost and easy to obtain; the reaction is conventional; the operation is simple; the method has no special requirements on equipment; one step that a key intermediate 14 is subjected to intramolecular cyclization to form a compound 15 is designed in a reaction route; the design is brand-new and is not reported previously; the reaction yield is higher in the whole route; the total yield can reach 50%; most solvents used in a reaction process can be recovered, so that the cost is saved, and the environmental pressure is reduced; the cost is lowered extremely; and the route has a very good industrial application prospect.

Description

Technical field: [0001] The invention relates to a preparation method of veterinary drug praziquantcl, which belongs to the field of medicine. Background of the invention: [0002] Praziquantel, also known as ciclopraziquantel and 8440, is a broad-spectrum anti-parasitic drug that can kill Schistosoma japonicum, Schistosoma haematobium, and Schistosoma mansoni. In addition, it also has a killing effect on paragonimus (lung fluke), clonorchis sinensis, hydatid, cysticercosis, sparganus monstii, fasciola, tapeworm, etc. In addition to its use in humans, praziquantel is also widely used as an antiparasitic treatment for animals, poultry, and the like. [0003] Praziquantel was first synthesized by Seubere et al. in 1975, and two pharmaceutical companies, Merck and Bayer in Germany, successfully developed pharmaceutical preparations. In 1980, Merck of Germany took the lead in the market under the trade name "Cesol". Its effects are characterized by high curative effect, small ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
Inventor 李光跃李伟李宝忠蔡华军牛宗强孟学姜红波
Owner 迪嘉药业集团股份有限公司
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