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Amide compound for treating stroke and preparation method thereof

An amide compound and compound technology, applied in the field of medicine, can solve problems such as damage to brain tissue, high time requirements, heart failure of heart disease patients, etc., and achieve the effect of promoting repair, simple operation, high product yield and purity

Active Publication Date: 2016-07-06
SHAANXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there is a lack of highly effective drugs for the treatment of stroke, and the therapeutic effects of clinically applied drugs for the treatment of stroke are not ideal. Thrombolysis is an effective method for the treatment of ischemic stroke, but thrombolytic drugs have a high time requirement. Less than 5% of patients are satisfied with the effect. In addition to thrombolytic drugs, the clinical drugs for ischemic stroke include: (1) vasodilators, which will make the blood in the lesion flow into the healthy brain tissue , damage healthy brain tissue; (2) drugs that expand blood volume, which can improve microcirculation, but have the risk of causing heart failure in heart patients; (3) anticoagulants and drugs that prevent platelet aggregation are currently only used as drugs Adjuvant drugs for hemorrhagic stroke
[0004] Modern medicine believes that stroke refers to the damage of local brain tissue and its nerve function due to the blockage of blood supply to the brain. drugs for neurological recovery

Method used

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  • Amide compound for treating stroke and preparation method thereof
  • Amide compound for treating stroke and preparation method thereof
  • Amide compound for treating stroke and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Taking the preparation of an amide compound with the following structural formula for treating stroke as an example, the specific preparation method is as follows:

[0024]

[0025] 1. Hydroxyl protection

[0026] 7.92g (40mmol) of (2R)-3-(3,4-hydroxyphenyl)-2-hydroxypropionic acid represented by formula I-1, 9.58g (122mmol) of acetyl chloride, and 40mL of dimethyl sulfoxide were added In a three-necked flask, stir at room temperature, and dropwise add 10 mL of dichloromethane solution containing 9.81 g (124 mmol) of pyridine at a rate of 4 to 5 mL / min. After the addition, react at room temperature for 2 hours, add 50 mL of distilled water, and separate the liquids. The aqueous phase was extracted three times with dichloromethane. After reclaiming the dichloromethane, the solid was purified by silica gel column chromatography (with the volume ratio of ethyl acetate and methanol being 20:1 mixed solution as the eluent), and the eluent was reclaimed. Obtain (2S)-triac...

Embodiment 2

[0034] Taking the preparation of an amide compound with the following structural formula for treating stroke as an example, the specific preparation method is as follows:

[0035]

[0036] In Example 1, (2R)-3-(3,4-hydroxyphenyl)-2-hydroxypropionic acid was used with equimolar (2S)-3-(3,4-hydroxyphenyl)-2- Hydroxypropionic acid is replaced, and other steps are identical with embodiment 1, obtains the amides compound that is used for the treatment of stroke, and its chemical designation is (2S)-3-(3,4-hydroxyphenyl)-2-hydroxypropionic acid-( 2S,3S,4S)-2-Amino-1,3,4-octadecanetriolamide.

Embodiment 3

[0038] Taking the preparation of an amide compound with the following structural formula for treating stroke as an example, the specific preparation method is as follows:

[0039]

[0040]In Example 1, (2S,3S,4S)-2-amino-1,3,4-octadecanetriol was used with equimolar (2R,3S,4S)-2-amino-1,3, 4-octadecanetriol is replaced, other steps are identical with embodiment 1, obtain the amides compound that is used for the treatment of apoplexy, its chemical name is (2R)-3-(3,4-hydroxyphenyl)-2-hydroxyl Propionic acid-(2R,3S,4S)-2-amino-1,3,4-octadecanetriolamide.

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Abstract

The invention discloses an amide compound for treating stroke and a preparation method thereof. A structural formula of the amide compound is shown as follows, wherein R1-R3 independently represent hydrogen or fluorine, R4 represents hydrogen or hydroxyl, R5 represents C1-C20 alkyl or C2-C20 alkenyl, n is an integer from 0 to 4, and respectively independent configuration representation of*1-*4 is R or S. The amide compound is synthesized through esterification reaction and ammonolysis reaction and is simple to operate and high in yield and purity. The amide compound has effects of thrombolysis and promoting recovery of brain tissue and nerve function, has obvious recovery effect on ischemic brain injury and nerve injury caused by a middle cerebral artery occlusion induced by a suture-occluded method, does not present toxic and side effect and can be used as a drug for treating stroke.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to an amide compound for treating stroke and a preparation method thereof. Background technique [0002] Stroke is an acute disease with the characteristics of high morbidity, high mortality, high disability rate, high recurrence rate, long treatment and recovery time, and many complications. It seriously endangers the physical and mental health and life safety of middle-aged and elderly people. It is the third leading cause of death after heart disease and cancer, accounting for 10% of all deaths worldwide, and 75% of stroke survivors have varying degrees of disability. Therefore, apoplexy is one of the main diseases that seriously affect the physical and mental health and quality of life of our people. [0003] At present, there is a lack of highly effective drugs for the treatment of stroke, and the therapeutic effects of clinically applied drugs for the treatment o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/34C07C231/12A61P9/10
CPCC07C67/14C07C231/02C07C231/12C07C69/21C07C235/34
Inventor 姜祎徐虹宋小妹邓翀张化为
Owner SHAANXI UNIV OF CHINESE MEDICINE
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