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Bisamide compounds as well as preparation method and use thereof

A compound and low-level technology, applied in the field of medicine, can solve the problems of insufficient physical and chemical properties of benzoazepine compounds such as activity and side effects, and achieve obvious antagonistic effects

Inactive Publication Date: 2015-03-18
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] As drugs for the treatment of the above-mentioned diseases, benzazepine compounds still have certain deficiencies in terms of activity, side effects and physicochemical properties.

Method used

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  • Bisamide compounds as well as preparation method and use thereof
  • Bisamide compounds as well as preparation method and use thereof
  • Bisamide compounds as well as preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055]

[0056] II-1 (100g, 322mmol) was placed in a 2000mL reaction bottle, and CH was added 2 Cl 2 (1000mL) stirred to dissolve, added triethylamine (50g, 490mmol), stirred at room temperature, added intermediate III-1 (59.8g, 322mmol) in batches, kept the temperature and stirred for 8h, TLC detection showed that the reaction was completed ( Developing agent ethyl acetate:petroleum ether=1:3).

[0057] The reaction solution was poured into 500ml of cold water, fully shaken to separate the layers, and the organic layer was separated and washed three times in succession. The organic layer was dried over anhydrous sodium sulfate and left overnight. After filtration, the solvent was evaporated to dryness under reduced pressure to obtain a light yellow solid crude product. The obtained crude product was recrystallized from ethanol to obtain 140.2 g of light yellow solid. Purity 98.9% (HPLC normalization method), yield 94.7%. ESI-MS: 460.1.

Embodiment 2

[0059]

[0060] II-1 (20g, 64mmol) was placed in a 250mL reaction bottle, and CHCl was added 3 (100mL) stirred to dissolve, added pyridine (7.8g, 98mmol), stirred at 50°C, added intermediate III-2 (12.5g, 67mmol) in batches, kept the temperature and stirred for 5h, TLC detection showed that the reaction was complete (expanded Agent ethyl acetate: petroleum ether = 1:3).

[0061] The reaction solution was poured into 100ml of cold water, fully shaken to separate the layers, and the organic layer was separated and washed three times in succession. The organic layer was dried over anhydrous sodium sulfate and allowed to stand overnight. After filtration, the solvent was evaporated to dryness under reduced pressure to obtain a light yellow solid crude product. The obtained crude product was purified by silica gel column chromatography to obtain 23.7 g of a white solid. The purity is 99.9% (HPLC normalization method), and the yield is 80.6%. ESI-MS: 460.1.

Embodiment 3

[0063]

[0064] Put II-2 (20g, 72mmol) in a 250mL reaction flask, add pyridine (60mL), stir to dissolve, stir at -5°C, add intermediate III-3 (15.2g, 76mmol) in batches, keep the temperature and stir After 24 hours, TLC detection showed that the reaction was complete (developing agent ethyl acetate:petroleum ether=1:3).

[0065] The reaction solution was poured into 300ml of cold water, stirred, and solids were precipitated. After filtering, the filter cake was washed with water and dried to obtain a yellow crude product. The crude product was recrystallized from ethanol to obtain 29.5 g of white solid. The purity is 98.3% (HPLC normalization method), and the yield is 93.1%. ESI-MS: 440.2.

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Abstract

The invention relates to compounds with two amido bonds as well as a preparation method and use of the compounds, and particularly relates to compounds with two amido bonds having structures as shown in the formula I, pharmaceutically acceptable salts of the compounds, preparation methods of the pharmaceutically acceptable salts and the compounds, a pharmaceutical composition of the compounds with the two amido bonds having the structures as shown in the formula I and the pharmaceutically acceptable salts as effective components, and use of the pharmaceutical composition in prevention or treatment of diseases related to an arginine vasopressin V1a receptor, an arginine vasopressin V1b receptor, an arginine vasopressin V2 receptor, a sympathetic nervous system or a rennin-angiotensin-aldosterone system.

Description

technical field [0001] The invention belongs to the technical field of medicine, more specifically, relates to a compound with two amide bonds, its preparation method and its application in the field of medicine. Background technique [0002] Arginine vasopressin (AVP), also known as antidiuretic hormone and vasopressin, is a peptide hormone secreted by the pituitary gland. It regulates body fluids through the receptor-G protein-second messenger pathway. Balance and other functions. AVP plays an important role in regulating the reabsorption of free water in the human body, the isotonic concentration of body fluids, blood volume, blood pressure, cell contraction, cell proliferation, and secretion of adrenal cortex hormones. [0003] Arginine vasopressin exerts various physiological effects by binding to vasopressin receptors. Vasopressin receptors can be divided into three subtypes, V1a, V1b and V2. V1a receptors are distributed in vascular smooth muscle, muscle cells and ...

Claims

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Application Information

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IPC IPC(8): C07D401/04A61K31/4545A61P9/12A61P15/00A61P15/06A61P5/38A61P25/24A61P9/04A61P1/16A61P3/12
CPCC07D401/04
Inventor 刘登科穆帅龚珉刘颖解晓帅郑学敏孔维苓周植星刘昌孝
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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