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Novel pyrroles derivative as well as preparation method and pharmaceutical application thereof

A technology of pyrrole and pyridine, which is applied in the field of preparation of therapeutic agents and potassium-competitive acid blockers (P-CABs), can solve the problems of slow onset, difficult gastric acid secretion, and large differences in efficacy.

Inactive Publication Date: 2017-02-22
HC SYNTHETIC PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still some limitations of PPIs that need to be further improved: ① All PPIs are acid-labile, so they need to be made into acid-protected dosage forms, such as enteric-coated tablets, etc., and their onset speed and efficacy are affected by gastric emptying. greater impact; ② PPIs require H + Activation transformation, slow onset, usually takes 3 to 5 days and multiple doses to achieve a stable maximum curative effect; ③Due to the genetic diversity of the liver CYP2C19 metabolic system in the population, the curative effect of PPIs varies greatly among different patients , and there may be drug metabolism interactions with other drugs; ④The drug effect is linearly related to the dose, and the metabolism in the plasma is faster. Even if it is administered twice a day, it is difficult for PPIs to continuously control gastric acid secretion for 24 hours

Method used

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  • Novel pyrroles derivative as well as preparation method and pharmaceutical application thereof
  • Novel pyrroles derivative as well as preparation method and pharmaceutical application thereof
  • Novel pyrroles derivative as well as preparation method and pharmaceutical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] [5-(2-fluorophenyl)-1-((4-methoxy-3,5-dimethyl-2-pyridine)-3-ylsulfonyl)-1H-pyrrol-3-yl]- N-Methylmethylamine (Ⅰ-1)

[0047]

[0048]

[0049] [2-(2-Fluorophenyl)-2-oxoethyl]malononitrile (2)

[0050] Dissolve 2-fluoroacetophenone (10.0g, 72.4mmol) in ethyl acetate (60ml), then add bromine (12.5g, 78.2mmol) in ethyl acetate (25ml) dropwise, and stir at room temperature for 2 hour, cool down to 0~5°C in an ice bath, slowly add aqueous sodium sulfite solution, continue to stir at room temperature for 1 hour, let stand to separate layers, wash the ethyl acetate layer with water (30ml×2), and then wash with saturated sodium bicarbonate solution (30ml) , and the ethyl acetate layer was collected. The ethyl acetate layer was added to the reaction flask, then malononitrile (4.93g, 74.6mmol) was added, the temperature was cooled to 0~5°C in an ice bath, triethylamine (8.28g, 81.8mmol) was slowly added dropwise, and stirred at room temperature for 3 Hour. Add 50ml of wat...

Embodiment 2

[0071] [5-(2-fluorophenyl)-1-((3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridine)-3-ylsulfonyl)-1H- Pyrrol-3-yl]-N-methylmethylamine (Ⅰ-2)

[0072] The specific operation is the same as that in Compound Example 1, compound (5) is added with 3-methyl-4-(2,2,2-trifluoroethoxypyridine)-2-sulfonyl chloride (6b) to obtain compound (I-2) Pale yellow solid.

[0073] MS (ESI) m / z: 458.1 (M+H) +

Embodiment 3

[0075] [5-(2-fluorophenyl)-1-((3,4-dimethoxy-2-pyridine)-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylformazan Amine (Ⅰ-3)

[0076] The specific operation is the same as that of Compound Example 1. Compound (5) is added with 3,4-dimethoxy-pyridine-2-sulfonyl chloride (6c) to obtain compound (I-3) as a pale yellow solid.

[0077] MS (ESI) m / z: 406.1 (M+H) +

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PUM

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Abstract

The invention relates to a novel pyrroles derivative as well as a preparation method and pharmaceutical application thereof. Specifically, the invention relates to the novel pyrroles derivative shown as a general formula (I) as well as pharmaceutically acceptable salt thereof or a pharmaceutical composition containing the novel pyrroles derivative, and a preparation method thereof. The invention further relates to application of the pyrroles derivative and the pharmaceutically acceptable salt thereof or the pharmaceutical composition containing the novel pyrroles derivative to preparation of a treatment agent, particularly application to a gastric acid secretion inhibitor and potassium competitive acid blockers (P-CABs), wherein the definition of each substituent group in the general formula (I) is the same as that in the description. (The general formula (I) is shown in the description.).

Description

technical field [0001] The invention relates to a new class of pyrrole derivatives and their pharmaceutically acceptable salts or pharmaceutical compositions containing them, and their preparation methods. The present invention further relates to the use of said azole derivatives and their pharmaceutically acceptable salts or pharmaceutical compositions containing them in the preparation of therapeutic agents, especially as gastric acid secretion inhibitors and potassium competitive acid blockers (P-CABs) use. Background technique [0002] Excessive gastric acid secretion can cause peptic ulcer, reflux esophagitis, and other gastric acid secretion-related diseases. Inhibition of gastric acid secretion is the main treatment for this type of disease. Clinically commonly used acid-suppressing drugs include histamine H 2 receptor antagonist (H 2 -Ras) and proton pump inhibitors (proton pump inhibitors, PPIs). h 2 -Ras is not as effective in treating reflux esophagitis and ...

Claims

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Application Information

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IPC IPC(8): C07D401/12A61P1/04
CPCC07D401/12
Inventor 杨成戚苏民陆华龙
Owner HC SYNTHETIC PHARMA CO LTD
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