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Bis-sulfonamide compound and its preparation method and use

A compound and pharmaceutical technology, which is applied in its preparation method and in the fields of medicine, bissulfonamide compounds, and medicine, can solve the problems of benzazepine compound activity and insufficient physical and chemical properties of side effects, and achieve obvious antagonistic effects

Active Publication Date: 2016-01-20
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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  • Bis-sulfonamide compound and its preparation method and use
  • Bis-sulfonamide compound and its preparation method and use
  • Bis-sulfonamide compound and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055]

[0056] II-1 (50g, 161mmol) is placed in a 1000mL reaction flask, and CH is added 2 Cl 2 (300mL) Stir to dissolve, add triethylamine (49g, 483mmol), stir at room temperature, add Intermediate III-1 (35.7g, 161mmol) in batches, keep the temperature and stir for 6h, TLC detection shows that the reaction is complete ( Developing agent ethyl acetate: petroleum ether=1:3).

[0057] Pour the reaction solution into 200 ml of cold water, fully shake the layer, divide the organic layer, and wash with water three times in this way. The organic layer was dried with anhydrous sodium sulfate and left overnight. Filter and evaporate the solvent under reduced pressure to obtain a crude light yellow solid. The obtained crude product was recrystallized from ethanol to obtain 77.6 g of white solid. The purity is 98.5% (HPLC normalization method), and the yield is 97.2%. ESI-MS: 496.1.

Embodiment 2

[0059]

[0060]

[0061] Place II-1 (50g, 161mmol) in a 250mL reaction flask, add pyridine (150mL), stir to dissolve, stir at -5°C, add Intermediate III-2 (35.7g, 161mmol) in batches, keep stirring at temperature 12h, TLC detection showed that the reaction was over (developing solvent ethyl acetate: petroleum ether = 1:3).

[0062] The reaction liquid was poured into 4500 ml of cold water and stirred, and a solid precipitated out. Filter, wash the filter cake with water, and dry to obtain a crude dark yellow solid. This crude product was recrystallized from ethanol to obtain 76.7 g of a yellow solid. The purity is 98.9% (HPLC normalization method), and the yield is 96.0%. ESI-MS: 496.1.

Embodiment 3

[0064]

[0065] II-2 (20g, 72mmol) is placed in a 250mL reaction flask, and CHCl is added 3 (100mL) Stir to dissolve, add pyridine (11.4g, 144mmol), stir at 60℃, add Intermediate III-3 (17.1g, 72mmol) in batches, keep the temperature and stir for 5h, TLC detection shows that the reaction is complete (expanded Ethyl acetate: petroleum ether = 1:3).

[0066] The reaction solution was poured into 100 ml of cold water, fully shaken to separate into layers, and the organic layer was separated and washed three times in succession. The organic layer was dried with anhydrous sodium sulfate and left to stand overnight. Filter and evaporate the solvent under reduced pressure to obtain a crude light yellow solid. The obtained crude product was purified by silica gel column chromatography to obtain 26.8 g of white solid. The purity is 99.1% (HPLC normalization method), and the yield is 78.2%. ESI-MS: 476.2.

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Abstract

The invention relates to bisulfamide compounds as well as a preparation method and use thereof, and specifically relates to bisulfamide compounds having the structure as shown in a formula I and pharmaceutically acceptable salts thereof as well as a preparation method of the bisulfamide compounds, pharmaceutical compositions with the bisulfamide compounds having the structure as shown in the formula I and the pharmaceutically acceptable salts thereof as active effective constituents and use of the pharmaceutical compositions in preventing or treating diseases associated with an arginine vasopressin V1a receptor, an arginine vasopressin V1b receptor, an arginine vasopressin V2 receptor, the sympathetic nervous system or the renin-angiotensin-aldosterone system; the formula I is as shown in the specification.

Description

Technical field [0001] The present invention belongs to the field of medical technology, and more specifically, relates to a class of bissulfonamide compounds, a preparation method thereof, and application in the medical field. Background technique [0002] Arginine vasopressin (arginine vasopressin, AVP), also known as antidiuretic hormone, vasopressin, is a peptide hormone secreted by the pituitary gland, through the receptor-G protein-second messenger pathway, it regulates the body fluid balance And many other functions. AVP plays an important role in regulating the reabsorption of human free water, the isotonic concentration of body fluids, blood volume, blood pressure, cell contraction, cell proliferation and the 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04A61K31/4545A61K31/635A61P9/12A61P25/00A61P15/00A61P15/06A61P5/38A61P25/24A61P9/04A61P1/16A61P7/00
CPCC07D401/04
Inventor 刘颖刘登科穆帅岳南张士俊谭初兵邹美香
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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