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N,N'-difluorophenyl derivative of 4-methoxyl-1,3-phthalamide and use thereof

A technology of phthalamide and difluorophenyl is applied in the preparation of sulfonic acid amide, the preparation of carboxylic acid amide, the preparation of organic compounds, etc., and can solve the problems that have not yet been seen.

Inactive Publication Date: 2008-05-28
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 is no report of N, N'-difluoro-substituted phenyl derivatives and structural analogs thereof of 4-methoxy-1,3-phthalamide involved in the present invention and their use Anti-platelet aggregation, anti-inflammatory and antipyretic analgesic use

Method used

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  • N,N'-difluorophenyl derivative of 4-methoxyl-1,3-phthalamide and use thereof
  • N,N'-difluorophenyl derivative of 4-methoxyl-1,3-phthalamide and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0473] Example 1: 4-methoxy-N, N'-bis-(3,5-difluorophenyl)-1,3-benzenedicarboxamide (C 21 h 14 f 4 N 2 o 3 )Synthesis

[0474] Dissolve 1.3g (10.1mmol) of 3,5-difluoroaniline in 15mL of tetrahydrofuran, add it to a 100mL round bottom flask, and dissolve 1.0g (4.3mmol) of 4-methoxy-1,3-phthaloyl chloride React in 10mL tetrahydrofuran for 6 hours. The solvent was evaporated. The solid was successively recrystallized from ethanol to obtain 1.2 g of white needle-like crystals. Yield: 66.7%, mp: 248-250°C.

[0475] The group number of the compound in the rabbit platelet aggregation reaction experiment is 9i.

[0476] Infrared spectroscopy (IR) and nuclear magnetic resonance spectroscopy ( 1 H-NMR) confirmed the structure of 9i: IR(KBr)cm -1 : 3362.5, 3102.9 (υ NH ), 1685.7, 1668.5 (υ C＝O ), 1607.9, 1559.7, 1495.9, 1431.1 (υ C＝C ), 1311.3(υ C-N ), 1266.6, 1020.2 (υ C-O-C ), 1101.7(υ CF ), 843.6, 828.1, 669.5 (υ CH ); 1 H-NMR (Acetone) δ (ppm): 4.18 (s, 3H, -OCH 3 ...

Embodiment 2

[0477] Example 2: 4-methoxy-N, N'-bis(3,5-difluorophenyl)-1,3-benzenedisulfonamide (C 19 h 14 f 4 N 2 o 5 S 2 )Synthesis

[0478] Dissolve 1.0g (7.8mmol) of 3,5-difluoroaniline in 10mL of tetrahydrofuran, add it to a 100mL round bottom flask, add 1.0g (3.3mmol) of 4-methoxy-1,3-benzenedisulfonyl chloride React in the above-mentioned reaction bottle for 6 hours. The solvent was evaporated. The solid was recrystallized from ethanol to obtain 1.0 g of white crystals. Yield: 61.7%, mp: 212-214°C.

[0479] The group number of the compound in the rabbit platelet aggregation reaction experiment is 10j.

[0480] Infrared spectroscopy (IR) and nuclear magnetic resonance spectroscopy ( 1 H-NMR) confirmed the structure of 10j: IR (KBr) cm -1 : 3256.6, 3114.4 (υ NH ), 2953.0 (υ CH3 ), 1626.1, 1488.4, 1438.5, 1410.1 (υ C＝C ), 1285.8, 1064.1 (υ C-O-C ), 1350.9, 1185.3, 1163.3 (υ SO2 ), 1309.4(υ C-N ), 993.3(υ CF ), 892.8, 838.8, 708.7 (υ CH ); 1 H-NMR (Acetone) δ (ppm): ...

Embodiment 3

[0481] Example 3: 4-methoxy-N, N'-bis(3-trifluoromethyl-4-fluorophenyl)-1,3-benzenedicarboxamide (C 23 h 14 f 8 N 2 o 3 )Synthesis

[0482] Dissolve 1.0g (5.6mmol) of 3-trifluoromethyl-4-fluoroaniline in 10mL of tetrahydrofuran into a 100mL round-bottomed flask, and add 0.6g (2.6mmol) of 4-methoxy-1,3-benzenedimethoxy The acid chloride was dissolved in 10 mL of tetrahydrofuran and added to the above reaction flask to react for 6 hours. The solvent was evaporated. The solid was recrystallized from ethanol to obtain 1.0 g of taupe solid. Yield: 75.2%, mp: 224-226°C.

[0483] The group number of the compound in the rabbit platelet aggregation reaction experiment is 11k.

[0484] Infrared spectroscopy (IR) and nuclear magnetic resonance spectroscopy ( 1 H-NMR) confirmed the 11k structure: IR (KBr) cm -1 : 3357.0(υ NH), 1675.4, 1654.7 (υ C＝o ), 1552.0, 1505.3, 1427.2 (υ C＝C ), 1329.4(υ CF3 ), 1270.1(υ C-N ), 1250.0(υ C-N ), 1054.2(υ C-O-C ), 1125.0(υ CF ); 1 H-NM...

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Abstract

The invention discloses a N, N'-difluoro-substituted-phenyl derivative of 4-methoxyl-1, 3-phenyldiamide, and relative application, while the compound can restrain platelet aggregation activity, to treat the diseases as cardiac infarction, cerebrovascular disorder, pulmonary embolism and atherosclerosis, with antipyretic, analgesia, and antiphlogistic activities.

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'-difluoro-substituted phenyl derivatives of 4-methoxy-1,3-phthalamide with anti-platelet aggregation activity Or pharmaceutically acceptable salts, compositions and uses thereof. 【Background technique】 [0002] 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 formation of thrombus, so they play an important role in the treatment of thrombosis. Oral antiplatelet drugs are currently the most commonl...

Claims

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Application Information

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IPC IPC(8): C07C235/64C07C231/02C07C303/38C07C311/29
Inventor 刘秀杰王松青
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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