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4-methoxyl-1,3-phthalamides compound and application thereof

A technology of phthalamide and dimethoxyphenethyl, which is applied in the field of high anti-platelet aggregation drugs, and achieves the effect of simple process and easy implementation

Inactive Publication Date: 2014-04-23
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are no related literature reports about the seven compounds

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] 4-Methoxy-N,N'-bis(3,4-dimethoxyphenethyl)-1,3-benzenedicarboxamide (C 29 h 34 o 7 N 2 ) preparation, the steps are as follows:

[0015] 1) Mix 1.43g (7.89mmol) of 3,4-dimethoxyphenethylamine and 0.92g (3.95mol) of 4-methoxy-1,3-phthaloyl chloride, and carry out the synthesis reaction at room temperature , the reaction time was 72h, and the target crude product was obtained;

[0016] 2) Recrystallization of the crude product of the target: add ethanol after drying the crude product of the above target, the ratio of ethanol to the crude product is 25ml: 1g, heat to boiling, cool to room temperature, filter and stand still, and the white crystalline target can be obtained Pure product 1.45g, yield 61.7%; mp: 202-204 o c.

[0017] The group number of the compound in the rabbit platelet aggregation reaction experiment is PN477.

[0018] Infrared spectroscopy (IR) and nuclear magnetic resonance spectroscopy ( 1 H-NMR) confirmed the structure of PN477: IR (KBr) cm -...

Embodiment 2

[0020] 4-Methoxy-N,N'-bis(2-chloro-4-trifluoromethylphenyl)-1,3-benzenedicarboxamide (C 23 h 14 o 3 N 2 f 6 Cl 2 ) preparation, the steps are as follows:

[0021] 1) Mix 2.0g (10.3mmol) of 2-chloro-4-trifluoromethylaniline and 1.20g (5.2mmol) of 4-methoxy-1,3-phthaloyl chloride, and carry out the synthesis reaction at room temperature , the reaction time was 72h, and the target crude product was obtained;

[0022] 2) According to the same method as in Example 1, the crude product of the target product was recrystallized to obtain 1.95 g of the pure product of the target product in the form of white crystals, with a yield of 60.9%; mp: 179-181 o c.

[0023] The group number of the compound in the rabbit platelet aggregation reaction experiment is PN478.

[0024] Infrared spectroscopy (IR) and nuclear magnetic resonance spectroscopy ( 1 H-NMR) confirmed the structure of PN478: IR (KBr) cm -1 : 3421.2, 3312.1 (υNH), 1685.9 (υC=O), 1595.8, 1542.7, 1500.7, 1477.3 (υC=C),...

Embodiment 3

[0026] 4-Methoxy-N,N'-bis(4-n-butylphenyl)-1,3-benzenedicarboxamide (C 29 h 24 o 3 N 2 ) preparation, the steps are as follows:

[0027] 1) Mix 1.78g (11.9mmol) of 4-n-butylaniline and 1.39g (5.95mmol) of 4-methoxy-1,3-phthaloyl chloride evenly, and carry out the synthesis reaction at room temperature, and the reaction time is 48h , to obtain the target crude product;

[0028] 2) According to the same method as in Example 1, the crude target product was recrystallized to obtain 1.3 g of the pure white crystalline target product, with a yield of 67.5%; mp: 254-257 o c.

[0029] The group number of the compound in the rabbit platelet aggregation reaction experiment is PN479.

[0030] Infrared spectroscopy (IR) and nuclear magnetic resonance spectroscopy ( 1 H-NMR) confirmed the structure of PN479: IR (KBr) cm -1 : 3240.1 (-NH), 2959.0 (-CH 3 ), 1591.3, 1507.4, 1485.2, 1461.8 (Ph), 2927.0 (-CH 2 ); 1 H-NMR(Acetone): 9.72 (s,1H, -NH-), 8.73 (s,1H, -NH-),7.93 (d,1H, be...

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Abstract

The invention provides a 4-methoxyl-1,3-phthalamides compound. The 4-methoxyl-1,3-phthalamides compound comprises 4-methoxyl-N,N'-di(3,4-dimethoxy phenethyl)-1,3-phthalamide, 4-methoxyl-N,N'-di(2-chloro-4-trifluoromethyl phenyl)-1,3-phthalamide, 4-methoxyl-N,N'-di(4-normal-butyl phenyl)-1,3-phthalamide, 4-methoxyl-N,N'-di(2,4-difluorophenyl)-1,3-phthalamide, 4-methoxyl-N,N'-di(3-isopropyl phenyl)-1,3-phthalamide, 4-methoxyl-N,N'-di(3-chloro-2-fluorophenyl)-1,3-phthalamide and 4-methoxyl-N,N'-di(3,4-difluorophenyl)-1,3-phthalamide. The seven compounds have an anti-platelet aggregation activity so that the 4-methoxyl-1,3-phthalamides compound explores a new way for researching novel anti-platelet aggregation medicines.

Description

technical field [0001] The invention relates to the field of highly anti-platelet aggregation drugs, in particular to 4-methoxy-1,3-benzenedicarboxamide compounds and applications thereof. Background technique [0002] Platelet aggregation is a key link in the normal coagulation mechanism, and the adhesion, aggregation and release reactions of platelets lead to thrombus formation. Anti-platelet aggregation drugs refer to drugs that can inhibit the adhesion and aggregation of platelets and inhibit the formation of thrombus, so they play an important role in the treatment of thrombosis. Oral antiplatelet drugs are currently the most commonly prescribed long-term preventive therapy. [0003] In recent years, in order to discover newer, more effective and broader-spectrum anti-platelet aggregation new drugs, the present invention has made further progress on 4-methoxy-N,N'-disubstituted phenyl-1,3-phthalamide compounds. Research. Seven compounds were found to have high anti-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/60C07C235/64C07C231/02A61P7/02
Inventor 刘秀杰李爱祥
Owner TIANJIN UNIVERSITY OF TECHNOLOGY