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Substituted pyrazole compound, preparation method, pharmaceutical composition and applications thereof

A compound, pyrazole technology, applied in the field of substituted pyrazole compounds, can solve problems such as undeveloped and large population base

Active Publication Date: 2020-03-03
江苏万高药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a rare disease, although the incidence rate of ALS is very low, my country has a large population base. According to incomplete statistics, the number of patients with this disease in my country is about 100,000-200,000, and the current drug that can cure the disease has not yet been successfully developed.

Method used

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  • Substituted pyrazole compound, preparation method, pharmaceutical composition and applications thereof
  • Substituted pyrazole compound, preparation method, pharmaceutical composition and applications thereof
  • Substituted pyrazole compound, preparation method, pharmaceutical composition and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-12

[0115] Synthetic route 1:

[0116]

[0117] Wherein starting material acid chloride can be prepared by corresponding carboxylic acid, route is as follows:

[0118]

[0119] General synthetic method 1:

[0120] Step 1: Dissolve anhydrous acetaldehyde and a catalytic amount of anhydrous zinc chloride in dry dichloromethane (10 mL) at 0°C, then slowly add compound (C), and heat to 50°C, react for 2.5h. After the reaction was completed, 100 mL of dichloromethane was added to the reaction liquid, and then washed with saturated aqueous sodium bicarbonate (1×50 mL), the aqueous phase was extracted with dichloromethane (2×25 mL), and the organic phases were combined. The organic phase was washed successively with distilled water and saturated sodium chloride solution, then dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography to obtain compound (B).

[0121] Step 2: Edaravone (...

Embodiment 3

[0123] The preparation of embodiment 3 isobutyric acid-1-(3-methyl-1-phenylpyrazole) oxyethyl ester

[0124]

[0125] Prepared by general synthetic method 1, a yellow oily liquid was obtained with a yield of 31.17%.

[0126] 1 H NMR (400MHz, CDCl 3 )δ7.68–7.62(m,2H),7.41(t,J=7.9Hz,2H),7.29–7.23(m,1H),6.46(q,J=5.3Hz,1H),5.58(s,1H ),2.53(dt,J=14.0,7.0Hz,1H),2.26(s,3H),1.59(d,J=5.3Hz,3H),1.14(dd,J=9.4,7.0Hz,6H).

[0127] ESI-MS(m / z):[M]+289.20

Embodiment 4

[0128] The preparation of embodiment 4 pivalic acid-1-(3-methyl-1-phenylpyrazole) oxyethyl ester

[0129]

[0130] Prepared by general synthetic method 1, a white solid was obtained with a yield of 34.28%.

[0131] 1 H NMR (400MHz, CDCl 3 )δ7.65(d, J=7.6Hz, 2H), 7.41(t, J=7.9Hz, 2H), 7.33–7.19(m, 1H), 6.45(q, J=5.3Hz, 1H), 5.57( s,1H),2.26(s,3H),1.58(d,J=5.3Hz,3H),1.16(s,9H).

[0132] ESI-MS(m / z):[M]+303.30

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Abstract

The invention discloses a substituted pyrazole compound represented by a formula I, and a preparation method, a pharmaceutical composition and applications thereof, wherein the compound has characteristics of good stability, excellent solubility, low cytotoxicity and remarkable neuroprotective effect, can effectively prevent and treat nerve cell injury, and is an ideal medicinal compound for preventing or treating cerebral stroke, cerebral embolism, cerebral stroke sequelae, cerebral stroke dyskinesia, mitochondrial encephalomyopathy and amyotrophic lateral sclerosis of spinal cord.

Description

technical field [0001] The present invention relates to a substituted pyrazole compound, its preparation method, pharmaceutical composition and application. Background technique [0002] Cerebrovascular disease is known for its high incidence, high disability rate, high mortality rate and high recurrence rate. my country is a country with a high incidence of cerebrovascular diseases, and stroke (or cerebral infarction or cerebral apoplexy) is the most important clinical cerebrovascular disease. "China Stroke Prevention Report-2015" statistics show that there are as many as 7 million stroke patients in my country, and more than 1.3 million patients die each year due to stroke, which has become the number one cause of death in my country. Moreover, the number of new stroke patients in my country exceeds 2 million each year, and continues to increase at a rate of nearly 9% per year. At present, the incidence of stroke in men in my country ranks third in the world, and the inci...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/26C07H17/02C07H1/00A61K31/415A61K31/7056A61P9/10A61P25/14A61P21/00
CPCC07D231/26C07H17/02C07H1/00A61P9/10A61P25/14A61P21/00A61K31/415A61K31/7056C07D231/22A61K31/4152C07D401/04
Inventor 韩建斌温翔李泽东杨金娜杨柳
Owner 江苏万高药业股份有限公司
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