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Capsaicin receptor antagonist for treating chronic inflammatory pain

A capsaicin receptor and antagonist technology, applied in the field of drug synthesis, can solve problems such as not entering clinical trials, and achieve the effects of short production cycle and simple operation

Inactive Publication Date: 2020-07-10
湖南博隽生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Disappointingly, however, none of these drug candidates entered clinical trials due to unpredictable side effects such as fever

Method used

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  • Capsaicin receptor antagonist for treating chronic inflammatory pain
  • Capsaicin receptor antagonist for treating chronic inflammatory pain
  • Capsaicin receptor antagonist for treating chronic inflammatory pain

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] A compound 2-(4-(5-((3-methoxyphenyl)amino)pyrazin-2-yl)piperazin-1-yl)benzamide can be used as capsaicin receptor antagonist For the treatment of chronic inflammatory pain, its structural formula is as follows:

[0035]

[0036] The synthetic method of capsaicin receptor antagonist 2-(4-(5-((3-methoxyphenyl) amino) pyrazin-2-yl) piperazin-1-yl) benzamide is:

[0037]

[0038] Wherein, the synthesis condition of 5-chloro-N-(3-methoxyphenyl)pyrazin-2-amine is:

[0039] Mix 2,5-dichloropyrazine (58.5g), 3-methoxyaniline (53.2g), potassium tert-butoxide (70.6g) and dimethylformamide (300mL), heat to 40°C, Stir for 2 hours; cool down to 15°C, add methyl tert-butyl ether (600mL) to the system, stir for 2 hours, and filter to obtain 5-chloro-N-(3-methoxyphenyl)pyrazine-2 - Amine (72.7 g, 74%).

[0040] 1 H NMR (CDCl 3 ,400MHz): δ(ppm)=8.22(s,1H),8.16(s,1H),7.31(t,1H),7.12-6.94(m,3H),5.29(brs,1H),4.44(s, 2H), 3.78(s, 3H); 13 C NMR (CDCl 3 ,100MHz): δ(ppm)=160.3,1...

Embodiment 2

[0045] A compound 2-(4-(5-((3-methoxyphenyl)amino)pyrazin-2-yl)piperazin-1-yl)benzamide can be used as capsaicin receptor antagonist For the treatment of chronic inflammatory pain, its structural formula is as follows:

[0046]

[0047] The synthetic method of capsaicin receptor antagonist 2-(4-(5-((3-methoxyphenyl) amino) pyrazin-2-yl) piperazin-1-yl) benzamide is:

[0048]

[0049] Wherein, the synthesis condition of 5-chloro-N-(3-methoxyphenyl)pyrazin-2-amine is:

[0050] Mix 2,5-dichloropyrazine (58.5g), 3-methoxyaniline (106.4g), diisopropylethylamine (141.2g) and N-methylpyrrolidone (600mL) and heat to 50 ℃, stirred for 3 hours; cooled to 20 ℃, added petroleum ether (900mL) to the system, stirred for 3 hours, filtered to obtain 5-chloro-N-(3-methoxyphenyl)pyrazine-2- Amine (80 g, 70%).

[0051] 1 H NMR (CDCl 3 ,400MHz): δ(ppm)=8.22(s,1H),8.16(s,1H),7.31(t,1H),7.12-6.94(m,3H),5.29(brs,1H),4.44(s, 2H), 3.78(s, 3H); 13 C NMR (CDCl 3 ,100MHz): δ(ppm)=160.3,155....

Embodiment 3

[0056] A compound 2-(4-(5-((3-methoxyphenyl)amino)pyrazin-2-yl)piperazin-1-yl)benzamide can be used as capsaicin receptor antagonist For the treatment of chronic inflammatory pain, its structural formula is as follows:

[0057]

[0058] The synthetic method of capsaicin receptor antagonist 2-(4-(5-((3-methoxyphenyl) amino) pyrazin-2-yl) piperazin-1-yl) benzamide is:

[0059]

[0060] Wherein, the synthesis condition of 5-chloro-N-(3-methoxyphenyl)pyrazin-2-amine is:

[0061] Mix 2,5-dichloropyrazine (58.5g), 3-methoxyaniline (159.6g), potassium hydroxide (211.8g), and dichloromethane (900mL), heat to 40-70°C, Stir for 4 hours; cool down to 22°C, add water (1200mL) to the system, stir for 4 hours, filter to obtain 5-chloro-N-(3-methoxyphenyl)pyrazin-2-amine (134g, 84%).

[0062] 1 H NMR (CDCl 3 ,400MHz): δ(ppm)=8.22(s,1H),8.16(s,1H),7.31(t,1H),7.12-6.94(m,3H),5.29(brs,1H),4.44(s, 2H), 3.78(s, 3H); 13 C NMR (CDCl 3 ,100MHz): δ(ppm)=160.3,155.8,144.7,141.2,139.4,136...

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Abstract

The invention discloses capsaicine receptor antagonist 2-(4-(5-((3-methoxyphenyl) amido) pyrazine-2-yl) piperazine-1-yl) benzamide for treating chronic inflammatory pain and a synthesis process thereof. The synthesis process comprises the following steps: carrying out substitution reaction on 2, 2, 5-dichloropyrazine and 3-methoxyaniline under the action of potassium tert-butoxide to obtain 5-chloro-N-(3-methoxyphenyl) pyrazine-2-amine; then, the 5-chloro-N-(3-methoxyphenyl) pyrazine-2-amine and 2-(piperazine-1-yl) benzamide are subjected to a Buchwald-Hartwig coupling reaction, and 2-(4-(5-((3-methoxyphenyl) amido) pyrazine-2-yl) piperazine-1-yl) benzamide is obtained. The substance can be used as a medicine for treating related diseases of chronic inflammatory pain.

Description

[0001] This invention is a divisional application of the Chinese patent "a capsaicin receptor antagonist for the treatment of chronic inflammatory pain and its synthesis process". The application date is July 9, 2018, and the application number is 201810744364.9. technical field [0002] The field of the invention belongs to the field of drug synthesis, and specifically relates to a capsaicin receptor antagonist for treating chronic inflammatory pain and a synthesis process thereof. Background technique [0003] According to pain pathology, chronic pain can be divided into nociceptive or inflammatory pain (appropriate response to painful stimuli) and neuropathic (pathological) pain (inappropriate response induced by damage to the nervous system). The International Association for the Study of Pain (IASP) defines pain as "an unpleasant sensory and emotional experience caused by real or potential tissue damage or similar conditions". Chronic pain usually refers to pain that pe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/20A61P29/00
CPCA61P29/00C07D241/20
Inventor 朱露晶万迎春邓生卫
Owner 湖南博隽生物医药有限公司
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