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4-((4-(2, 3, 4-trimethoxy-benzyl)piperazine-1-yl)methyl)-3-nitro-benzoyl guanidine tartrate

A technology of tartaric acid and anhydrous methanol, applied in the preparation of carboxylate, organic chemistry, etc., can solve the problems of poor water solubility, poor water solubility and fluidity of hydrochloride, and inconvenience

Inactive Publication Date: 2013-12-04
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 4-((4-(2,3,4-Trimethoxybenzyl)piperazin-1-yl)methyl)-3-nitrobenzoylguanidine (II) is a novel NHE-1 inhibitor The NHE-1 inhibitory activity of II is 18 times that of the positive drug cariboride, and its protective effect on myocardial ischemia-reperfusion injury in rats is slightly stronger than that of cariboride, stronger than trimetazidine, But the water solubility of II is poor
According to previous experience, we made II hydrochloride, but the test results showed that the hydrochloride of II was poor in water solubility and fluidity, which brought a lot of inconvenience to the follow-up research of compound II

Method used

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  • 4-((4-(2, 3, 4-trimethoxy-benzyl)piperazine-1-yl)methyl)-3-nitro-benzoyl guanidine tartrate

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Embodiment 1

[0015] Preparation of 4-((4-(2,3,4-trimethoxybenzyl)piperazin-1-yl)methyl)-3-nitrobenzoylguanidine tartrate (I)

[0016] Weigh 1.5g (3.1mmol) of II, dissolve it with 5ml of ethyl acetate, stir it electromagnetically, and weigh 0.5g (3.1mmol) of tartaric acid, dissolve it with 5ml of methanol, and add it dropwise to the ethyl acetate solution of II , add 15ml of ethyl acetate, stir overnight, filter and dry to obtain 1.9g (96.8%) of light yellow tartrate. m.p.130~132℃.

[0017] 1 HNMR (300MHz, CDCl 3 ), δ (ppm): 2.20~2.65 (8H, m, piperazine), 3.74 (3H, s, OCH 3 ),3.78(6H,s,OCH 3 ),3.54(2H,s,CH 2 ),4.24(2H,d,2CH),4.27(2H,s,CH 2 ),6.78(1H,d,J=8.7Hz,ArH),7.00(1H,d,J=8.6Hz,ArH),7.2(4H,bs,NH),7.66(1H,d,J=8.1Hz, ArH),8.0(2H,bs,NH),8.24(1H,d,J=8.0Hz,ArH),8.46(1H,s,ArH).

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Abstract

The invention relates to the field of drug synthesis, in particular to compound for myocardial Ischemia-reperfusion injury, namely 4-((4-(2, 3, 4-trimethoxy-benzyl)piperazine-1-yl)methyl)-3-nitro-benzoyl guanidine tartrate, having a formula (I), and a preparation method thereof. The compound is good in water solubility, fluidity and the like.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to the compound 4-((4-(2,3,4-trimethoxybenzyl)piperazin-1-yl)methyl)-3-nitrate against myocardial ischemia-reperfusion injury Tartrate salt (I) of benzoylguanidine and its preparation method. Background technique [0002] 4-((4-(2,3,4-Trimethoxybenzyl)piperazin-1-yl)methyl)-3-nitrobenzoylguanidine (II) is a novel NHE-1 inhibitor The NHE-1 inhibitory activity of II is 18 times that of the positive drug cariboride, and its protective effect on myocardial ischemia-reperfusion injury in rats is slightly stronger than that of cariboride, stronger than trimetazidine, But II has poor water solubility. According to previous experience, we prepared II as a hydrochloride, but the test results showed that the hydrochloride of II had poor water solubility and fluidity, which brought a lot of inconvenience to the follow-up research of compound II. [0003] Contents of the invention [0004]...

Claims

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Application Information

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IPC IPC(8): C07D295/155C07C59/255C07C51/41
Inventor 徐云根靳璐姜向敏颜天华
Owner CHINA PHARM UNIV