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Synthesis method of cilnidipine

A technology of cilnidipine and a synthesis method is applied in the field of calcium antagonist cilnidipine synthesis and calcium antagonist preparation, and can solve the problems of low yield and the like, and achieve the effect of improving yield

Inactive Publication Date: 2015-04-29
丹阳恒安化学科技研究所有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Chinese patent 200810038932.X has introduced a kind of preparation method of calcium antagonist cilnidipine, and this method is: in C 1 ~C 3 2-(3-nitrobenzylidene) acetoacetate 2-methoxyethyl ester and β-aminocrotonate cinnamyl ester were used for ring closure reaction in anhydrous alcohol solvent to obtain the crude product of cilnidipine, which was obtained after recrystallization Nidipine, no catalyst is used in this synthetic method, and the yield is low

Method used

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  • Synthesis method of cilnidipine

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preparation example Construction

[0015] The preparation method of the catalyst aluminum isobutoxide in the present invention is: in a 250ml there-necked bottle equipped with a reflux condenser and a thermometer, add excess isobutanol, an appropriate amount of aluminum particles, and a small amount of initiator, and reflux at a certain temperature until the aluminum The pellets were completely dissolved, and the excess isobutanol was removed under reduced pressure.

[0016] The cinnamyl β-aminocrotonate in the present invention is prepared by the preparation method described in the patent 200810038932.X, and then recrystallized.

Embodiment 1

[0018] Place 100 g of commercially available 2-(3-nitrobenzylidene) 2-methoxyethyl acetoacetate and 82 g of cinnamyl β-aminocrotonate in a reaction kettle, and add 250 mL of isobutanol solvent and Aluminum isobutoxide catalyst 0.16g, reflux for 3-4h; cool overnight and filter to obtain yellow crystals; wash with ethanol at 5-10°C, and recrystallize with absolute ethanol to obtain 130.4g of light yellow crystals, cilnidipine refined product, yield 75.3%.

Embodiment 2

[0020] Put 100 g of commercially available 2-(3-nitrobenzylidene) 2-methoxyethyl acetoacetate and 82 g of cinnamyl β-aminocrotonate in a reaction kettle, and add 200 mL of isobutanol solvent and Aluminum isobutoxide catalyst 0.33g, reflux for 3-4h; cool overnight and filter to obtain yellow crystals; wash with ethanol at 5-10°C, and recrystallize with absolute ethanol to obtain 132.0g of fine cilnidipine crystals, yield 76.2%.

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Abstract

The invention discloses a synthesis method of cilnidipine. The synthesis method comprises the following steps: putting methoxyethyl-2-(3-nitrobenzylidene)acetoacetate and beta-amino crotonic acid cinnamyl ester into a reaction kettle, and under the nitrogen protection, adding an isobutyl alcohol solvent and an isobutyl alcohol aluminum catalyst for reflux reaction; cooling and putting over night, and filtering to obtain a cilnidipine crude product; washing with ethanol at 5-10 DEG C, and recrystallizing by using anhydrous ethanol to obtain a cilnidipine fine product. In the synthesis method, the isobutyl alcohol is used as the solvent and the isobutyl alcohol aluminum is used as the catalyst; compared with the prior art, the synthesis method has the advantages as follows: the reaction process is simple and the reaction yield is increased.

Description

technical field [0001] The invention relates to a method for preparing a calcium antagonist, in particular to a method for synthesizing the calcium antagonist cilnidipine, which belongs to the field of pharmaceutical chemical synthesis. Background technique [0002] Cinidipine is also known as 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate 2-methoxyethyl cinnamyl ester. Cilnidipine is a lipophilic dihydropyridine calcium antagonist that can bind to the dihydropyridine site of the L-type calcium channel on the vascular smooth muscle cell membrane and inhibit Ca 2+ Through the transmembrane influx of L-type calcium channels, it relaxes and expands vascular smooth muscle, thereby reducing blood pressure. It also inhibits Ca 2+ Inhibits the release of noradrenaline and sympathetic nerve activity through the transmembrane influx of N-type calcium channels on the sympathetic nerve cell membrane. Combination of cilnidipine with other antihypertensive drugs ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/90
CPCC07D211/90
Inventor 陈国平夏方方杜成铭陈丽庆王霞张梁吴涛英荆吉仁夏新开王海大
Owner 丹阳恒安化学科技研究所有限公司
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