Biphenyl sulfafurazole compound, synthesis method and application thereof

A technology of methyl biphenyl sulfonamide and isoxazole, which is applied in the field of medicine, can solve the problem of low efficacy of endothelin receptor antagonists, and achieves the effects of novel chemical structure and easy availability of raw materials

Inactive Publication Date: 2012-07-18
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to propose a [[(2-n-propyl-4-methyl-1H-benzene And imidazole)-6-yl]formamide-1-yl]methylbiphenylsulfaisoxazole compounds, synthesis method and application

Method used

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  • Biphenyl sulfafurazole compound, synthesis method and application thereof
  • Biphenyl sulfafurazole compound, synthesis method and application thereof
  • Biphenyl sulfafurazole compound, synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Intermediate 4'-{[N-(morpholine ethyl)-[(2-n-propyl-4-methyl-1H-benzimidazol)-6-yl]formamide-1-yl]methyl The preparation of}-N-(3,4-dimethyl-5-isoxazole)-N-methoxyethoxymethyl-[1,1'-biphenyl]-2-sulfonamide: to Add 1mL N,N-dimethylformamide (DMF), N-(morpholine ethyl)-[(2-n-propyl-4-methyl-1H-benzimidazole)-6 to a 10mL one-necked flask -yl]formamide 80.2mg (0.245mmol), add potassium tert-butoxide 30.1mg (0.282mmol) under ice-water bath conditions, warm up to room temperature, stir for 30 minutes, cool down to 0°C, add N-(3,4 -Dimethyl-5-isoxazole)-4'-bromomethyl-N-methoxyethoxymethyl-1-[1,1'-biphenyl]-2-sulfonamide 122.3mg (0.281 mmol), warming up to room temperature for 3h. After the reaction was completed, 10 mL of ethyl acetate was added for dilution, washed with saturated brine (3×10 mL), the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 122.1 mg of the product as a colorless viscous substance...

Embodiment 2

[0022] The conditions are the same as in Example 1, and the intermediate 4'-{[N-(4-methylpiperazin-1-yl)ethyl)-[(2-n-propyl-4-methyl-1H-benzo Imidazolium)-6-yl]formamide-1-yl]methyl}-N-(3,4-dimethyl-5-isoxazole)-N-methoxyethoxymethyl-[1, 1'-biphenyl]-2-sulfonamide. 120.1 mg of a colorless viscous substance was obtained with a yield of 59.5%. 1 H NMR (400MHz, CDCl 3 )δ: 0.95(t, J=7.20Hz, 3H), 1.74(m, 2H), 1.88(s, 3H), 2.15(s, 3H), 2.30(s, 3H), 2.46(t, J=7.25 Hz, 4H), 2.56(s, 3H), 2.67(t, J=7.22Hz, 4H), 2.78(t, J=7.16Hz, 2H), 2.83(t, J=7.15Hz, 2H), 3.32( s, 3H), 3.46(m, 2H), 3.48(m, 2H), 3.69(m, 2H), 4.21(s, 2H), 4.80(s, 2H), 7.06~7.91(m, 10H), 8.44 (s, 1H).

Embodiment 3

[0024]The conditions are the same as in Example 1, and the intermediate 4'-{[N-(piperidinyl)-[(2-n-propyl-4-methyl-1H-benzimidazole)-6-yl]formamide is prepared -1-yl]methyl}-N-(3,4-dimethyl-5-isoxazole)-N-methoxyethoxymethyl-[1,1'-biphenyl]-2 - sulfonamides. 123.2 mg of a colorless viscous substance was obtained with a yield of 61.4%. 1 H NMR (400MHz, CDCl 3 )δ: 0.94(t, J=7.24Hz, 3H), 1.58(m, 6H), 1.75(m, 2H), 1.89(s, 3H), 2.14(s, 3H), 2.40(t, J=7.19 Hz, 4H), 2.55(s, 3H), 2.78(t, J=7.22Hz, 2H), 2.85(t, J=7.15Hz, 2H), 3.32(s, 3H), 3.45(m, 2H), 3.49 (m, 2H), 3.67 (m, 2H), 4.22 (s, 2H), 4.81 (s, 2H), 7.10-7.94 (m, 10H), 8.45 (s, 1H).

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Abstract

The invention relates to [[(2-n-propyl-4-methyl-1H-benzimidazole)-6-yl] formamide-1-yl] methyl-biphenyl sulfafurazole compound, a synthesis method and application thereof, belonging to medical technology filed. The structural formula of the compound is that: M=H, K and Na, wherein, R1 is morpholine ethyl, (4-methyl piperazine-1-yl) ethyl, piperidine ethyl, pyrrolidine ethyl, n-propyl, isopropyl, normal butyl, tert-butyl, phenyl, 2-methoxyphenyl, benzyl, 2-methoxybenzyl, 3-methoxybenzyl, 4-methoxybenzyl, 3,4-methoxybenzyl, beta-phenethyl, alpha-phenethyl, 3-methoxy-beta-phenethyl, 4-methoxy-beta-phenethyl, 2,5-methoxy-beta-phenethyl, 3,4-methoxy-beta-phenethyl, 2-fluoro-beta-phenethyl or 4-fluoro-beta-phenethyl; and M is hydrogen, potassium or sodium. The compound can be used to prepare medicines for treating cardiovascular diseases.

Description

technical field [0001] The invention relates to the field of medical technology, and is a novel and simple [[(2-n-propyl-4-methyl-1H- Benzimidazole)-6-carboxamide-1-yl]methylbiphenylsulfaisoxazole compound and its synthesis method are used as medicine for treating cardiovascular and cerebrovascular diseases. Background technique [0002] Cardiovascular disease has a high incidence rate and many and serious complications, which seriously threaten human health. Non-peptide angiotensin AT1 receptor blockers (ARBs) are a new class of antihypertensive drugs that act on the renin-angiotensin system (RAS). Compared with angiotensin-converting enzyme inhibitors (ACEIs), The antihypertensive effect is more significant, the RAS is more selectively blocked, and the side effects are small, and it has been listed as one of the six major antihypertensive drugs. [0003] The renin-angiotensin system plays an important role in regulating blood pressure, body fluid balance and dielectric b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/12A61K31/5377A61K31/496A61K31/454A61K31/422A61P9/00
Inventor 周智明薛为哲章军何星
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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