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Benzoic acid compounds and preparation method and application thereof

A technology for benzoic acids and compounds, applied in the field of medicinal chemistry, can solve problems such as increased mortality and affect the recovery of diseases, and achieve the effects of being easy to prepare, suitable for large-scale production, and reducing brain cell damage.

Active Publication Date: 2019-05-21
HENAN GENUINE BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although thrombolysis, coronary artery bypass grafting, percutaneous coronary intervention and other means can significantly alleviate ischemic heart and brain cell damage clinically, the death of heart and brain cells caused by acute myocardial infarction and cerebral infarction still seriously affects the disease, leading to increased mortality

Method used

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  • Benzoic acid compounds and preparation method and application thereof
  • Benzoic acid compounds and preparation method and application thereof
  • Benzoic acid compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the preparation of compound 8

[0041]

[0042] Starting material 6 (2.0g, 9.39mmol) and NBS (N-bromosuccinimide) (1.84g, 1.5mmol), AIBN (azobisisobutyronitrile) (154mg, 0.94mmol) were added to tetrachloride Carbon (30mL). The reaction mixture was refluxed for 2h, cooled to room temperature and filtered. The solvent was evaporated to obtain compound 7. Add water (10mL) and reflux for 1h, cool, add EtOAc (200mL) for extraction, the organic phase is washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the solvent is evaporated to obtain compound 8 (2.05g, 95%) without purification used directly in the next reaction.

Embodiment 2

[0043] Embodiment 2: the preparation of compound 10

[0044]

[0045] Magnesium bars (0.63g, 26.22mmol) were added to a three-necked flask, dry THF (tetrahydrofuran) (20mL) and a grain of iodine were added, and 4-bromo-1-butene (2.95 g, 21.83mmol) THF (2mL) solution to initiate the reaction, after the dropwise addition was completed, the reaction was refluxed for 2h. Compound 8 (1.0g, 4.37mmol) was dissolved in THF (10mL), under the protection of nitrogen, the newly prepared Grignard reagent was added dropwise at 0°C, after the addition was completed, it was raised to room temperature for 2h, and 1N HCl was added dropwise at 0°C to quench extinguished, evaporated THF, added DCM to dissolve, added 1N HCl to adjust the pH to 2, reacted at room temperature overnight, added EtOAc (100mL), separated the organic phase, dried over anhydrous sodium sulfate, filtered, evaporated the solvent, and the residue was used on a silica gel column Purification gave compound 9 (325 mg, 28%) ...

Embodiment 3

[0047] Embodiment 3: the preparation of compound 12

[0048]

[0049] Add magnesium strips (125mg, 5.22mmol) into a three-necked flask, add dry THF (5mL) and a grain of iodine, and gradually add (4-bromobutoxy)(tert-butyl) dropwise under nitrogen protection and heating. A solution of dimethylsilane (1.16g, 4.35mmol) in THF (4mL) initiated the reaction, after the dropwise addition was completed, the reaction was refluxed for 2h to obtain the Grignard reagent. Compound 8 (200mg, 0.87mmol) was dissolved in THF (5mL), under the protection of nitrogen, the newly prepared Grignard reagent was added dropwise at 0°C, after the addition was completed, it was raised to room temperature for 2h, and quenched by adding 1N HCl dropwise at 0°C , evaporate THF, add DCM (50mL) to dissolve, add 1N HCl to adjust the pH to 2, react at room temperature overnight, extract, separate the organic phase, dry over anhydrous sodium sulfate, filter, evaporate the solvent, and the residue is subjected t...

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Abstract

The invention belongs to the field of medicinal chemistry and relates to novel benzoic acid compounds I and II and application of the compounds in prevention and treatment or relieving in the aspectssuch as nrain ischemia or ischemia after acute and chronic myocardial infarction. In the structure of the compounds I and II, X is H, I, Br, Cl, F, CN, amidogen and a derivative thereof; R1 is alkyl of C2-10, except substituted C2-10 alkyl and a n-butane group; M is an organic amine ion or a metal ion. The compounds are shown in the description.

Description

technical field [0001] The present invention relates to a novel benzoic acid compound, relates to its application in preventing and treating or alleviating cerebral ischemia or ischemic diseases after acute and chronic myocardial infarction, and also relates to its application in preventing and treating or alleviating ALS or ALS The application of human disease (amyotrophic lateral sclerosis, ALS) belongs to the field of medicinal chemistry. Background technique [0002] Cardiovascular and cerebrovascular diseases, especially coronary atherosclerosis and the resulting ischemic heart and brain diseases are still common diseases that seriously plague human health. According to incomplete statistics, the annual death toll of cardiovascular and cerebrovascular diseases in the world accounts for 30% of the total death toll, of which ischemic cardiovascular and cerebrovascular diseases account for more than 40%. There are about 7 million stroke patients and about 2 million myocar...

Claims

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Application Information

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IPC IPC(8): C07D307/88C07C65/01A61P25/00A61P9/10A61P21/00
CPCA61P9/10A61P25/00C07D307/88A61P21/00C07C65/01A61K9/19A61K9/20A61K9/48A61K31/192A61K31/365A61P25/08C07D307/83C07C65/17C07C2601/02C07C67/307C07C67/343C07C69/78
Inventor 常俊标杜锦发朱凯凯王凯弋冬旭李建永张春霞高远王亚峰彭有梅刘冰洁
Owner HENAN GENUINE BIOTECH CO LTD
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