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N,N*-2[fluoroform (oxygen) group] substituted phenyl derivant of 4-methoxy-1,3-benzene diamide and uses of the same

A technology of trifluoromethylphenyl and trifluoromethoxyphenyl, which is applied in the field of anti-platelet aggregation and anti-inflammatory drugs, and can solve problems that have not yet been seen

Inactive Publication Date: 2008-05-07
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the existing literature, there have been no reports of 4-methoxy-1,3-phthalic acid derivatives and their structural analogues involved in the present invention so far and their use in anti-platelet aggregation, anti-inflammation, antipyretic and analgesic the use of

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: 4-methoxy-N, N'-bis(3-trifluoromethoxyphenyl)-1,3-benzenedisulfonamide (C 21 h 16 f 6 N 2 o 7 S 2 )Synthesis

[0036] Dissolve 1.5g (8.5mmol) of 3-trifluoromethoxyaniline in 15mL of tetrahydrofuran, add it to a 100mL round-bottomed flask, and dissolve 1.0g (3.3mmol) of 4-methoxy-1,3-benzenedisulfonyl chloride Dissolved in 10 mL of tetrahydrofuran and added dropwise to the above reaction flask to react for 7 hours. The solvent was distilled off, and a large amount of white solid precipitated out. Recrystallized from ethanol to obtain 1.0 g of white crystals. Yield: 62.2%, mp: 145-147°C.

[0037] The group number of the compound in the rabbit platelet aggregation reaction experiment is 5e.

[0038] Infrared spectroscopy (IR) and nuclear magnetic resonance spectroscopy ( 1 H-NMR) confirmed the structure of 5e: IR(KBr)cm -1 : 3420.5, 3262.1(υ NH ), 1615.2, 1593.8, 1487.2 (υ C＝C ), 1262.3(υ C-O-C ), 1339.3, 1171.4 (υ SO2 ), 1217.5, 1006.6 (υ CF ); ...

Embodiment 2

[0039]Example 2: 4-methoxy-N, N'-bis(4-trifluoromethoxyphenyl)-1,3-benzenedisulfonamide (C 21 h 16 f 6 N 2 o 7 S 2 )Synthesis

[0040] Dissolve 1.4g (9.6mmol) of 4-trifluoromethoxyaniline in 15mL of tetrahydrofuran, add it to a 100mL round-bottomed flask, and dissolve 1.0g (3.3mmol) of 4-methoxy-1,3-benzenedisulfonyl chloride Dissolve in 10mL tetrahydrofuran and react for 5 hours. The solvent was evaporated to precipitate an orange solid. Recrystallized from ethanol to obtain 1.2 g of orange solid. Yield: 62.2%, mp: 168-170°C.

[0041] The group number of the compound in the rabbit platelet aggregation reaction experiment is 6f.

[0042] Infrared spectroscopy (IR) and nuclear magnetic resonance spectroscopy ( 1 H-NMR) confirmed the structure of 6f: IR(KBr)cm -1 : 3260.4(υ NH ), 1593.2, 1508.9, 1467.8, 1402.7 (υ C＝C ), 1286.2(υ C-N ), 1068.4(υ C-O-C ), 1329.0, 1170.6 (υ SO2 ), 1224.1, 1109.6, 1017.7 (υ CF ), 853.8, 822.8, 670.5 (υ CH ); 1 H-NMR (CDCl 3 )δ (p...

Embodiment 3

[0043] Example 3: 4-methoxy-N, N'-bis(3-trifluoromethoxyphenyl)-1,3-benzenedicarboxamide (C 23 h 16 f 6 N 2 o 5 )Synthesis

[0044] Dissolve 1.2g (6.8mmol) of 3-trifluoromethoxyaniline in 10mL of tetrahydrofuran, add it to a 100mL round-bottomed flask, and 0.7g (3.0mmol) of 4-methoxy-1,3-phthaloyl chloride Dissolve in 10 mL of tetrahydrofuran and add dropwise to the above reaction flask, and react for 6 hours. The solvent was evaporated under reduced pressure. Recrystallized from 50% ethanol to obtain 1.0 g of white needle-like crystals. Yield: 69.9%, mp: 170-171°C.

[0045] The group number of the compound in the rabbit platelet aggregation reaction experiment is 7g.

[0046] Infrared spectroscopy (IR) and nuclear magnetic resonance spectroscopy ( 1 H-NMR) confirmed the structure of 7g: IR (KBr) cm -1 : 3351.2(υ NH ), 1681.4, 1660.2 (υ C＝O ), 1605.5, 1541.6, 1495.4, 1438.6 (υ C＝C ), 1321.0(υ CF3 ), 1262.8(υ C-N ), 1014.5(υ C-O-C ), 755.8, 702.6, 679.0 (υ CH )...

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PUM

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Abstract

The invention discloses N, -2 substituted phenyl derivates of 4-methoxyl-1, 3-phenylene acyl diamine, and the usage thereof. A compound provided by the invention has the activity for inhibiting the collection of blood platelet, and is applicable for the diseases such as miocardial infarction, cerebrovascular disorder, pulmonary embolism, atherosclerosis, and so on. Moreover, the compound also has the activities of antifebrile, pain killing, inflammation resisting, and so on.

Description

【Technical field】 [0001] The invention belongs to the field of anti-platelet aggregation and anti-inflammatory drugs, in particular a kind of N,N'-di[trifluoromethyl (oxygen) group of 4-methoxy-1,3-phthalamide with anti-platelet aggregation activity ] Substituted phenyl derivatives or pharmaceutically acceptable salts, compositions and uses thereof. 【Background technique】 [0002] Thromboembolic disease is one of the main causes of human disability and death in modern civilized society. Platelet aggregation is the main factor causing various (heart, brain, lung, etc.) thrombi. Therefore, the research on antithrombotic drugs has been focusing on the field of anti-platelet aggregation. 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 format...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/64C07C231/02C07C311/29C07C303/38A61K31/167A61K31/18A61P29/00A61P7/02
Inventor 刘秀杰王松青
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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