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Bisulfamide compounds as well as preparation method and use thereof

A compound and low-level technology, applied to bissulfonamide compounds, its preparation method and in the fields of medicine and medicine, can solve the problems such as insufficient activity, side effects and physicochemical properties of benzoazepine compounds, and achieve obvious antagonistic effect.

Active Publication Date: 2014-07-23
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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  • Bisulfamide compounds as well as preparation method and use thereof
  • Bisulfamide compounds as well as preparation method and use thereof
  • Bisulfamide compounds as well as preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055]

[0056] II-1 (50g, 161mmol) was placed in a 1000mL reaction bottle, and CH was added 2 Cl 2 (300mL) stirred to dissolve, added triethylamine (49g, 483mmol), stirred at room temperature, added intermediate III-1 (35.7g, 161mmol) in batches, kept the temperature and stirred for 6h, TLC detection showed that the reaction was completed ( Developing agent ethyl acetate:petroleum ether=1:3).

[0057] The reaction solution was poured into 200ml 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 77.6 g of white solid. Purity 98.5% (HPLC normalization method), yield 97.2%. ESI-MS: 496.1.

Embodiment 2

[0059]

[0060]

[0061] Put 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 the temperature and stir At 12h, TLC detection showed that the reaction was complete (developing agent ethyl acetate:petroleum ether=1:3).

[0062] The reaction solution was poured into 4500ml of cold water, stirred, and solids were precipitated. After filtering, the filter cake was washed with water and dried to obtain a dark yellow solid crude product. The crude product was recrystallized from ethanol to obtain 76.7 g of a yellow solid. Purity 98.9% (HPLC normalization method), yield 96.0%. ESI-MS: 496.1.

Embodiment 3

[0064]

[0065] II-2 (20g, 72mmol) was placed in a 250mL reaction bottle, and CHCl was added 3 (100mL) stirred to dissolve, added pyridine (11.4g, 144mmol), stirred at 60°C, added intermediate III-3 (17.1g, 72mmol) 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).

[0066] 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 resulting crude product was purified by silica gel column chromatography to obtain 26.8 g of a 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 invention belongs to the technical field of medicine, more specifically, relates to a class of bissulfonamide compounds, 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 c...

Claims

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Application Information

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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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