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Preparation method of feprazone and intermediate of feprazone

A non-plazone and system technology, applied in the field of non-plazone preparation, can solve the problems of high industrialization cost, long time, unsatisfactory product yield and the like, and achieves the effects of convenient operation, mild and easy control of reaction conditions

Inactive Publication Date: 2018-03-09
TIANJIN PACIFIC PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned two documents have a long history, and none of them discloses relevant data about the yield of non-prazone. The inventor prepared according to the method recorded therein, and the resulting product yield is not ideal (all less than 50%), and the industrialization cost is relatively high

Method used

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  • Preparation method of feprazone and intermediate of feprazone
  • Preparation method of feprazone and intermediate of feprazone
  • Preparation method of feprazone and intermediate of feprazone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Ligand screening test: Different phosphine ligands were used to catalyze the reaction to obtain different yields.

[0025] Under nitrogen protection, add 0.1 mmol of 3-methyl-2-butene bromide and 0.05 mmol of 1,2-diphenyl-3,5-dioxopyrazolidine and no Water toluene (5.0mL), add phosphine ligand (0.05mmol), Pd 2 (dba) 3 0.025mmol, cesium carbonate, 0.15mmol, heated to 70°C for 1h. After the reaction, the solvent was removed under reduced pressure, and the target product was obtained through column chromatography (ethyl acetate / petroleum ether=1 / 10, volume ratio). The target product had a melting point of 156°C.

[0026] Table 1 The reaction results of different ligand catalyzed reactions

[0027]

[0028] According to the reaction results in Table 1, it can be seen that the applicant selected different phosphine ligands, all of which successfully catalyzed the reaction to generate non-prazone, but the catalytic efficiency was different. Among them, 2-dicyclohexylph...

Embodiment 2

[0030] The only difference between this example and Example 1 is that 0.1 mmol 3-methyl-2-butene bromide is used, and 2-dicyclohexylphosphine-2',6'-diisopropoxy-1,1' is selected -Biphenyl is used as a catalyst to obtain a product with a yield of 90% and a melting point of 156°C.

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Abstract

The invention provides a method of preparing feprazone conveniently and efficiently from 3-methyl-2-butene chloride / bromide and 1,2-dipheyl-3,5-dioxo pyrazolidine and by use of a commercially easily available phosphine ligand, a new way is proposed. Meanwhile, the reaction conditions are mild and easy to control, the operation is convenient, and the yield of the product is higher than 90%.

Description

technical field [0001] The invention belongs to the field of pharmaceutical and chemical product production, and in particular relates to a preparation method of non-prazone. Background technique [0002] Fiprazone is a non-steroidal anti-inflammatory analgesic drug, its structural formula is: [0003] [0004] Its anti-inflammatory, antipyretic and analgesic effects are achieved by strongly inhibiting the synthesis of PG. The structural feature of fiprazone is the introduction of isopentenyl with anti-ulcer effect in the chemical structure, so that it not only retains the anti-inflammatory and analgesic effects, but also reduces toxic and side effects, especially avoiding the effects of similar drugs on the gastric mucosa. Adverse stimulant effect. The drug effect of nonprazone is about 10 times that of phenylbutazone and 30-50 times that of ibuprofen. Non-Plazon was first launched in Italy in the 1980s, and was subsequently produced in Britain and Japan. Indications...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/34
CPCC07D231/34
Inventor 宋德成
Owner TIANJIN PACIFIC PHARMA
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