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Tetramethylpyrazine acidamides derivates, preparation method and medicament composition and application

A technology of ligustrazine amide and derivatives, applied in the field of derivative drugs, can solve the problems of low bioavailability, fast metabolism, increased side effects and the like

Inactive Publication Date: 2009-02-11
JIANGXI GROUNDIONG PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the low bioavailability, fast metabolism, and short half-life of ligustrazine in the body, multiple administrations are required clinically, which brings a lot of inconvenience to patients, and the peak and valley phenomenon of drug concentration is prone to appear in the blood, which increases the side effects

Method used

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  • Tetramethylpyrazine acidamides derivates, preparation method and medicament composition and application
  • Tetramethylpyrazine acidamides derivates, preparation method and medicament composition and application
  • Tetramethylpyrazine acidamides derivates, preparation method and medicament composition and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1: the preparation of 2-benzoyl-3,5,6-trimethylpyrazine (A1)

[0053] 0.755g, 0.005mol 2-methylamino-3,5,6 trimethylpyrazine and 0.4g, 0.0055mol pyridine were dissolved in about 30ml chloroform in a 150ml round bottom flask, benzoyl chloride (purchased pure product) 0.0775g, 0.0055mol was dissolved in about 30ml chloroform, and the latter solution was slowly dropped into the former solution in a constant pressure dropping funnel under the condition of an ice-water bath. Then the reaction solution was distilled under reduced pressure, and the obtained crude product was separated by a fast column (ethyl acetate:cyclohexane=4:1), and then recrystallized with 90-95% ethanol to obtain pure product 2-benzoyl-3,5 , 6-trimethylpyrazine (Al), white crystal, 0.66g, yield 52%, mp 115-116°C;

[0054] Spectral analysis data: IR(KBr, cm -1 ): 3279.86 (NH), 1652.95 (C=O), 1530.02, 1486.59, 1446.19, 1416.15 (C=N, C=C); 1 H-NMR (600MHz, CDCl 3 , δ ppm): 7.92 (s, 1H, NH), ...

Embodiment 2

[0055] Example 2: Preparation of 2-phenylacetyl-3,5,6-trimethylpyrazine (A2)

[0056] Prepared as described in Example 1, ethyl acetate:cyclohexane=4:1 fast column separation, yield 53%, yellow solid, mp 125-126°C;

[0057] Spectral analysis data: IR(KBr, cm -1 ): 3377.86 (NH), 1507.64, 1496.82, 1454.64 (C=N, C=C), 1662.40 (C=O); 1 H-NMR (600MHz, CDCl 3 , δ ppm): 7.17 (s, H, NH), 7.40-7.33 (m, 5H, Ar-H), 4.43 (d, 2H, CH 2 , J=4.1Hz), 2.46(s, 3H, CH 3 ), 2.42 (s, 3H, CH 3 ), 2.34 (s, 3H, CH 3 ); 13 C-NMR (150MHz, CDCl 3 , δ ppm): 171.13 (C=O), 144.57, 147.50, 147.73, 149.51 (pyrazine-C), 127.31, 128.97, 129.70, 134.91 (Benzene-C), 41.02, 43.84 (CH 2 ), 19.91, 21.21, 21.34 (CH 3 ); ESI-MS: 270.5 (M+H) + ;C 16 h 19 N 3 O.

Embodiment 3

[0058] Embodiment 3: Preparation of 2-m-chlorobenzamidomethyl-3,5,6-trimethylpyrazine (A3)

[0059] Prepared as described in Example 1, ethyl acetate:cyclohexane=4:1 fast column separation, yield 45%, white solid, mp 110-111°C;

[0060] Spectral analysis data: IR(KBr, cm -1 ): 3406.14 (NH), 1523.23, 1565.89, 1523.23 (C=N, C=C), 1671.43 (C=O); 1 H-NMR (600MHz, CDCl 3 , δ ppm): 7.98 (s, H, NH), 7.89 (t, H, Ar-H), 7.76 (dd, 1H, Ar-H, J 1 =1.11Hz,J 2 =7.73Hz), 7.50(m, 1H, Ar-H), 7.40(m, 1H, Ar-H), 4.67(d, 2H, CH 2 , J=4.51Hz), 2.54(s, 3H, CH 3 ), 2.54 (s, 3H, CH 3 ), 2.53 (s, 3H, CH 3 ); 13 C-NMR (150MHz, CDCl 3 , δ ppm): 165.99 (C=O), 144.61, 147.84, 148.00, 149.96 (pyrazine-C), 125.09, 127.55, 129.93, 133.14, 134.79, 136.15 (Benzene-C), 41.41 (CH 2 ), 20.00, 21.40, 21.49 (CH 3 ); ESI-MS: 290.5 (M+H) + ;C 15 h 16 ClN 3 O.

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Abstract

The invention relates to ligustrazine amides derivatives and a preparation method, medical composition and applications thereof, belonging to the medical technical field of rhizoma ligustici wallichi derivatives. The derivatives can be shown by the structural general formula on the right; wherein, R is phenyl, p-hydroxyphenyl, o-hydroxy-phenyl, etc. The invention provides a method for preparing the ligustrazine amides derivatives and the medical composition of different dosage forms which are manufactured by the ligustrazine amides derivatives and pharmaceutic adjuvants, and are used for preparing drugs of cardiovascular and cerebrovascular diseases for curing ischemic, atherosclerosis and coronary heart disease, etc.

Description

technical field [0001] The invention relates to a derivative and a preparation method thereof, in particular to a ligustrazine amide derivative and a preparation method thereof, and to a pharmaceutical composition composed of the derivative and an auxiliary agent, belonging to the technical field of derivative drugs. Background technique [0002] Cardiovascular and cerebrovascular diseases are currently the number one killer that endangers human life and health worldwide, and are the "number one enemy" of world public health. The data show that the death caused by cardiovascular and cerebrovascular diseases has exceeded 50% of the total population. In my country, about 3 million people die of cardiovascular and cerebrovascular diseases every year. , cardiovascular and cerebrovascular diseases will still account for the first cause of death in my country. At present, there are many drugs for the treatment of cardiovascular and cerebrovascular diseases clinically. Although the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/12A61K31/4965A61P9/10
Inventor 刘新泳于芳
Owner JIANGXI GROUNDIONG PHARM CO LTD
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