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3-pyrrole carboxylic acid derivatives, and preparing method and application thereof

A compound and unsaturated technology, applied to 3-pyrrolecarboxylic acid derivatives, medicine, its preparation method and in the field of medicine, can solve the problems such as insufficient activity and side effect physicochemical properties of benzoazepine compounds, and achieve obvious antagonistic effect. Effect

Inactive Publication Date: 2013-12-04
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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  • 3-pyrrole carboxylic acid derivatives, and preparing method and application thereof
  • 3-pyrrole carboxylic acid derivatives, and preparing method and application thereof
  • 3-pyrrole carboxylic acid derivatives, and preparing method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060]

[0061] II-1 (10g, 45 mmol) was placed in a 250mL reaction flask, and CH 2 Cl 2 (80mL) was stirred to dissolve, and intermediate III-1 (5.0g, 50mmol) was added in batches, followed by DMAP (6.2g, 50mmol) and HOBt (15g). After 0.5 h, DCC (15.8 g, 76.7 mmol) was added in batches to react for 16 h, and TLC detection showed that the reaction was complete (developer ethyl acetate).

[0062] The solvent was evaporated to dryness, ethyl acetate (50ml) was added, and the by-product DCU was removed by filtration. The filtrate was washed with saturated sodium carbonate and saline solution (50ml each), and the organic layers were combined, dried over anhydrous sodium sulfate, and left overnight. After filtration, the solvent was evaporated to dryness under reduced pressure to obtain a light yellow oil. The resulting product was purified by silica gel column chromatography to obtain 10.4 g of a white solid. The purity is 98.9% (HPLC normalization method), and the yield is 76...

Embodiment 2

[0064]

[0065] Put II-1 (10g, 45 mmol) in a 250mL reaction flask, add tetrahydrofuran (80mL) and stir to dissolve, add intermediate III-2 (6.5g, 50mmol) in batches, and then add DMAP (6.2g, 50mmol) and HOBt (15g), the reaction system turned light yellow after the addition, stirred at 60°C for 0.5h, added DCC (15.8g, 76.7mmol) in batches to continue the reaction for 12h, TLC detection showed that the reaction was complete (developer ethyl acetate).

[0066] The solvent was evaporated to dryness, ethyl acetate (50ml) was added, and the by-product DCU was removed by filtration. The filtrate was washed with saturated sodium carbonate and saline solution (50ml each), and the organic layers were combined, dried over anhydrous sodium sulfate, and left overnight. After filtration, the solvent was evaporated to dryness under reduced pressure to obtain a light yellow oil. The resulting product was purified by silica gel column chromatography to obtain 8.3 g of a white solid. The pu...

Embodiment 3

[0068]

[0069]

[0070] Put II-1 (10g, 45 mmol) in a 250mL reaction flask, add DMF (100mL) and stir to dissolve, add intermediate III-3 (8.1g, 50mmol) in batches, and then add DMAP (6.2g, 50mmol) and HOBt (15g), the reaction system turned light yellow after the addition, stirred at 80°C for 0.5h, added DCC (15.8g, 76.7mmol) in batches to continue the reaction for 6h, TLC detection showed that the reaction was complete (developer ethyl acetate).

[0071] The reaction solution was poured into 300ml of cold water, stirred, and a yellow solid was precipitated. Filter, dissolve the filter cake in ethyl acetate (50ml), filter to remove the insoluble by-product DCU, wash the filtrate with saturated sodium carbonate and saline solution (50ml each), combine the organic layers, dry over anhydrous sodium sulfate, and let stand overnight. After filtration, the solvent was evaporated to dryness under reduced pressure to obtain a light yellow oil. The obtained product was purified b...

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Abstract

The invention relates to 3-pyrrole carboxylic acid derivatives, and a preparing method and an application thereof, and particularly relates to the 3-pyrrole carboxylic acid derivatives having a structure represented by formula I and pharmaceutically acceptable salts thereof and the preparing method of the derivatives, pharmaceutical compositions with the 3-pyrrole carboxylic acid derivatives having the structure represented by the formula I and the pharmaceutically acceptable salts of the 3-pyrrole carboxylic acid derivatives as active ingredients, and applications of the pharmaceutical compositions in prevention or treatment of diseases related with an arginine vasopressin V1a receptor, an arginine vasopressin V1b receptor, an arginine vasopressin V2 receptor, a sympathetic nervous system or a renin-angiotensin-aldosterone system.

Description

technical field [0001] The invention belongs to the technical field of medicine, more specifically, relates to a class of 3-pyrrolecarboxylic acid derivatives, a preparation method thereof and an 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 musc...

Claims

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Application Information

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IPC IPC(8): C07D207/34C07D403/06A61K31/496A61P1/16A61P3/12A61P5/10A61P5/38A61P9/04A61P9/12A61P15/00A61P25/24
Inventor 刘登科穆帅刘颖牛端解晓帅张大帅刘昌孝
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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