Novel medicine of non peptide like angiotensin II receptor antagonism agent, their preparation and application

A solvate and pharmaceutical technology, applied in the field of novel non-peptide angiotensin II receptor antagonist drugs, can solve the problems of large dosage and low activity

Inactive Publication Date: 2005-06-08
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Angiotensin II receptor antagonists are a class of antihypertensive drugs. At present, there are many products on the market, such as losartan, valsartan, telmisartan, irbesartan, candesartan, etc., Europe Patent EP543263 describes a group of compounds including telmisartan. Although the toxic and side effects of such compounds are relatively small and the preparation route is relatively easy, judging from the characteristics of telmisartan already on the market, the product has a dosage large, low activity

Method used

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  • Novel medicine of non peptide like angiotensin II receptor antagonism agent, their preparation and application
  • Novel medicine of non peptide like angiotensin II receptor antagonism agent, their preparation and application
  • Novel medicine of non peptide like angiotensin II receptor antagonism agent, their preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0191] Example 1 3-methyl-4-nitro-benzoic acid methyl ester

[0192] Add compound Ia (1.81g), methanol (5ml) to the flask, then add concentrated H 2 SO 4 (0.5ml), after heating to reflux for about 2h, stop the reaction, cool to obtain a yellow solid, recrystallize the resulting yellow solid with methanol to obtain yellow needle-like crystal Ib (0.15g), the yield is about 74.3%, mp 78-79 ° C .1 H NMR (CDCl 3 , 500MHz) δ: 8.03 (br, 1H, Ar-H), 7.98 (m, 2H, Ar-H), 3.97 (s, 3H, CH 3 O), 2.63(s, 3H, PhCH 3 ).IR(KBr) v: 3005, 1740, 1620, 1590, 1520, 1350cm -1 .

Embodiment 2

[0193] Example 2 3-methyl-4-amino-benzoic acid methyl ester

[0194] The prepared Ib (0.20g) was dissolved in methanol (1.95ml), and about 0.1g of Raney nickel was added, followed by H 2 , after stirring at room temperature for about 4 h, the Raney nickel was filtered off, and the obtained filtrate was spin-dried to obtain a white solid Ic (0.15 g), the yield was about 92.1%, mp 181-121 ° C. 1 H NMR (CDCl 3 , 500MHz) δ: 7.76(s, 1H, Ar-H), 7.74(d, J=8.2Hz, 1H, Ar-H), 6.64(d, J=8.2Hz, 1H, Ar-H), 4.15( br,2H,NH 2 ), 3.85(s, 3H, CH 3 O), 2.17(s, 3H, PhCH 3 ).IR(KBr) v: 3470, 3380, 1700cm -1 .

Embodiment 3

[0195] Example 3 Methyl 4-(n-butylamido)-3-methylbenzoate

[0196] Add Ic (1.65g) in the there-necked flask, anhydrous MgSO 4 Dried CH 2 Cl 2 (7ml), redistilled triethylamine (4.3ml), then added dropwise 4.3ml of n-butyryl chloride, the temperature was controlled at 8°C to 10°C, stirred at room temperature for about 1h, suction filtered, and the filtrate was watered respectively (1.5ml×2) , saturated NaHCO 3 solution (1.5ml) and water (1ml×2), and the resulting organic phase was washed with anhydrous MgSO 4 After drying, the solvent was spun off to obtain a white solid, which was recrystallized from ethyl acetate to obtain Id (1.87g), with a yield of 79.6%, mp 125-127°C. 1 H NMR (CDCl 3 , 500MHz) δ: 8.37 (br, 1H, NH), 7.88 (m, 2H, Ar-H), 7.09 (s, 1H, Ar-H), 3.89 (s, 3H, CH 3 O), 2.41(t, J=7.3Hz, 2H, CH 2 CH 2 CH 3 ), 2.31(s, 3H, PhCH 3 ), 1.78 (m, 2H, CH 2 CH 2 CH 3 ), 1.04(t, J=7.4Hz, 3H, CH 2 CH 3 ).IR(KBr) v: 3300, 2950, ​​1730, 1670, 1530cm -1 .

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Abstract

A novel non-peptide angiotonin II receptor antagon kind of medicines, and their preparing process and application are disclosed.

Description

Technical field: [0001] The invention relates to a novel non-peptide angiotensin II receptor antagonist drug, their preparation and application. Background technique: [0002] Angiotensin II receptor antagonists are a class of antihypertensive drugs. At present, there are many products on the market, such as losartan, valsartan, telmisartan, irbesartan, candesartan, etc., Europe Patent EP543263 describes a group of compounds including telmisartan. Although the toxic and side effects of this type of compound are relatively small and the preparation route is relatively easy, judging from the characteristics of the already marketed telmisartan, the product has a dosage Large, low activity. Therefore, the present invention provides a compound similar in structure to telmisartan, which has strong activity and less side effects, and has the application prospect of replacing telmisartan. Invention content: [0003] The present invention provides a compound having the following ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/4184A61K31/423A61K31/428A61P9/12C07D403/04C07D403/14C07D413/04C07D413/14C07D417/04C07D417/14
Inventor 齐传民杨凌春张关心余惠
Owner BEIJING NORMAL UNIVERSITY
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