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4-ethoxy-1,3-phenylenedimethylene amide compounds as well as preparation methods and applications thereof
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A technology of phthalamide and phthaloyl chloride, which is applied in the field of preparation of anti-platelet aggregation drugs, and can solve problems such as the inability to meet the growing needs of clinical practice
Inactive Publication Date: 2013-10-30
TIANJIN UNIVERSITY OF TECHNOLOGY
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[0007] The main purpose of the present invention is to overcome the shortcoming that the existing similar drugs cannot meet the growing needs of the clinic, and provide a new 4-ethoxy-1,3-phthalamide compound with anti-platelet aggregation drug prospects and Its preparation contributes to the development of new anti-platelet aggregation drugs and the enrichment of clinical drug varieties
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Embodiment 1
[0027] Embodiment 1: 4-ethoxy-N, N'-diphenyl-1,3-benzenedicarboxamide (C 22 h 20 N 2 o 3 ) (PN311) preparation
[0028] Dissolve 20mmol of aniline in 15mL of tetrahydrofuran, add 10mmol of 4-ethoxy-1,3-phthaloyl chloride and 10ml of pyridine, mix well, and heat to reflux for 12 hours. The solvent was distilled off to obtain a yellow crude product. Methanol was recrystallized to obtain 0.70 g of white powder, yield: 73.7%; mp: 234-236°C. IR(KBr)cm -1 :: 3463.38, 3403.46, 3132.67, 1680.88, 1654.93, 1533.58, 1596.69, 1497.31, 1268.49, 1123.87; 1 H-NMR (CDCl) δ (ppm): 1.74 (t, 3H), 4.40 (q, 2H), 7.17 (m, 3H), 7.40 (m, 4H), 7.70 (m, 4H), 8.11 (s, 1H), 8.24(d, 1H), 8.77(s, 1H), 10.07(s, 1H)
Embodiment 2
[0029] Example 2: 4-ethoxy-N, N'-bis(2-iodophenyl)-1,3-benzenedicarboxamide (C 22 h 18 I 2 N 2 o 3 ) (PN313) preparation
[0030] Dissolve 20mmol of 2-iodoaniline in 15mL of tetrahydrofuran, add 12mmol of 4-ethoxy-1,3-phthaloyl chloride and 10ml of hexahydropyridine, mix well, and react for 2 hours. The solvent was distilled off under reduced pressure to obtain brown-yellow crystals, and recrystallized from ethanol to obtain 1.04 g of yellow crystals, yield: 52.5%; mp 234-236°C. IR(KBr)cm -1 : 3375.44, 3346.62, 1666.87, 1582.66, 1493.41, 1254.97, 749.11; 1 H-NMR (CDCl) δ (ppm): 1.40 (q, 3H), 4.25 (d, 2H), 7.25 (d, 1H), 6.92, 7.43, 7.87 (q, 6H), 7.25 (d, 1H), 8.29, 8.51(d, 2H), 8.42(d, 1H), 8.96(s, 1H), 10.15(s, 2H)
Embodiment 3
[0031] Embodiment 3: 4-ethoxy-N, N'-bis(3-fluorophenyl)-1,3-benzenedicarboxamide (C 22 h 18 f 2 N 2 o 3 ) (PN384) preparation
[0032] Dissolve 16mmol of 4-ethoxy-1,3-phthaloyl chloride in 50mL of dioxane, add 20mmol of 3-fluoroaniline and 2ml of tetrahydropyrrole, mix well, and heat to reflux for 60 hours. The solvent was distilled off under reduced pressure to obtain a light yellow crude product. Recrystallization from ethanol gave 0.40 g of white snowflake crystals, yield: 40.0%, mp: 188.8-190.4°C. IR(KBr)cm -1 : 3321.74, 3250.53, 1685.11, 1654.81, 1606.13, 1536.01, 1439.21, 1265.77, 933.36, 787.57; 1 H-NMR (CDCl 3 )δ(ppm): 10.13(s, 1H), 8.71(d, 1H), 8.33(s, 1H), 8.22(dd, 1H), 7.25(d, 1H), 7.71-6.83(m, 8H), 4.38(q,2H), 1.70(t,3H)
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Abstract
The invention relates to 23 amide compounds, and particularly relates to 23 4-ethoxy-1,3-phenylenedimethylene amide compounds. One preparation method of one of the 4-ethoxy-1,3-phenylenedimethylene amide compounds comprises the following steps of: dissolving an arylamine into a solvent, and adding an alkali, and adding 4-ethoxy-1,3-phenylenedimethylene acyl chloride; or dissolving the 4-ethoxy-1,3-phenylenedimethylene acyl chloride into the solvent, adding the arylamine, and adding the alkali; carrying out a reflux reaction at room temperature or through heating, distilling or distilling by reducing pressure to remove the solvent to obtain a crude product, and adding a corresponding solvent to recrystallize to obtain a pure target product. The 4-ethoxy-1,3-phenylenedimethylene amide compounds are used for preparing compound medicaments or active pharmaceutical ingredients of medicaments for resisting platelet aggregation. The compounds with high platelet-aggregation resisting activity are designed, synthesized and selected, and a good foundation is laid for the further study on the platelet-aggregation resisting medicaments.
Description
technical field [0001] The invention relates to the preparation of anti-platelet aggregation drugs, in particular to a 4-ethoxy-1,3-phthalamide compound and its preparation and application. 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 order to find more effective and broader-spectrum anti-platelet aggregation new drugs, the present invention, on the basis of previous work, designed and synthesized 4-ethoxy-1,3-benzenedicarboxamide compounds and studied their anti-platelet aggregation activity in vitro . Aspirin is...
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