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Desloratadine derivatives, and preparation method and application thereof

A compound and low-level technology, applied to desloratadine derivatives, its preparation method and in the field of medicine and medicine, can solve the problems of benzazepine compounds' lack of activity and side effects and physical and chemical properties, and achieve receptor antagonism significant effect

Inactive Publication Date: 2013-02-13
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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  • Desloratadine derivatives, and preparation method and application thereof
  • Desloratadine derivatives, and preparation method and application thereof
  • Desloratadine derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058]

[0059] II-1 (20g, 64mmol) was placed in a 250mL reaction bottle, and CH 2 Cl 2 (100mL) was stirred to dissolve, added triethylamine (10g, 98mmol), stirred at -5°C, added dropwise intermediate III-1 (5.6g, 71mmol), kept stirring for 5h at the temperature, TLC detection showed that the reaction was complete ( Developing agent ethyl acetate:petroleum ether=1:3).

[0060] 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 left overnight. After filtration, the solvent was evaporated under reduced pressure to obtain a light yellow solid. The resulting product was purified by silica gel column chromatography to obtain 17.5 g of a white solid. The purity is 99.3% (HPLC normalization method), and the yield is 77.1%. ESI-MS: 353.1.

Embodiment 2

[0062]

[0063] II-1 (20g, 64mmol) was placed in a 250mL reaction bottle, and CHCl was added 3 (100mL) was stirred to dissolve, added pyridine (7.8g, 98mmol), stirred at 60°C, added dropwise intermediate III-2 (6.6g, 71mmol), kept stirring for 4h at the temperature, TLC detection showed that the reaction was complete (developer Ethyl acetate:petroleum ether=1:3).

[0064] 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. The resulting product was purified by silica gel column chromatography to obtain 5.4 g of a white solid. The purity is 98.8% (HPLC normalization method), and the yield is 22.9%. ESI-MS: 367.2.

Embodiment 3

[0066]

[0067] Put II-1 (10g, 32mmol) in a 250mL reaction flask, add tetrahydrofuran (80mL) and stir to dissolve it, add potassium tert-butoxide (5.5g, 49mmol), stir under an ice-water bath at 0°C, and add intermediate III dropwise -3 (3.8g, 36mmol), keep the temperature and stir for 3h, TLC detection shows that the reaction is complete (developing agent ethyl acetate:petroleum ether=1:3).

[0068] The reaction solution was filtered to remove solid insolubles, and the filtrate was poured into 200ml of cold water, stirred, and solids were precipitated. Filter, wash the filter cake with water, and dry to obtain the crude product as a brown-yellow solid. This crude product was purified by silica gel column chromatography to obtain 10.9 g of a white solid. The purity is 99.1% (HPLC normalization method), and the yield is 89.4%. ESI-MS: 381.2.

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Abstract

The invention relates to desloratadine derivatives, and a preparation method and application thereof, particularly desloratadine derivatives disclosed as Formula I and pharmaceutically acceptable salts thereof and a preparation method thereof, and application of the desloratadine derivatives disclosed as Formula I and pharmaceutically acceptable salts thereof as active effective ingredients of active pharmaceutical compositions in preventing and treating diseases related to arginine vasopressin V1a receptor, arginine vasopressin V1b receptor, arginine vasopressin V2 receptor, sympathetic nervous system or renin-angiotensin-aldosterone system.

Description

technical field [0001] The invention belongs to the technical field of medicine, more specifically, relates to a class of desloratadine 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 muscle, muscle ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04A61K31/4545A61P9/12A61P15/00A61P15/06A61P5/38A61P25/24A61P9/04A61P1/16A61P3/12
Inventor 刘登科穆帅刘颖解晓帅张大帅刘昌孝
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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