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A compound for treating peptic ulcer, its preparation method and application

A compound and chemical structural formula technology, applied in the field of medicine, can solve problems such as poor water solubility of vonoprazan fumarate, achieve excellent therapeutic effect and improve water solubility

Active Publication Date: 2022-04-26
赛隆药业集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to solve the problem of poor water solubility of vonoprazan fumarate in the prior art, the present invention studies a new class of compounds with good water solubility

Method used

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  • A compound for treating peptic ulcer, its preparation method and application
  • A compound for treating peptic ulcer, its preparation method and application
  • A compound for treating peptic ulcer, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Synthesis of 5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrole-3-carbaldehyde (compound IV)

[0030]

[0031] At room temperature, add 30 g of 5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde (compound II), 100 ml of acetonitrile (CHCN), 29 g of N,N-diisopropylethyl Amine (DIEA) and 4g of 4-dimethylaminopyridine (DMAP), add 35g of pyridine-3-sulfonyl chloride (compound III) at room temperature, stir and react at room temperature for 30min, after the reaction is complete, add water to quench the reaction, use Adjust the pH to 5 with hydrochloric acid, cool down to room temperature, stir and crystallize, filter, and dry under reduced pressure to obtain compound (IV), which is 44 g of yellow powder with a yield of 84%.

[0032] 1H-NMR (CDCl 3 )δ: 9.90 (1H, s), 8.81 (1H, dd, J = 1.4, 4.8Hz), 8.59 (1H, d, J = 2.2Hz), 8.15 (1H, d, J = 1.8Hz), 7.71 ( 1H,dt,J=1.9,8.2Hz), 7.45(1H,m), 7.37(1H,dd,J=4.9,8.1Hz), 7.16(2H,m), δ7.01(1H,t,J= 8.9Hz), 6.67 (1H,d,J=1.7Hz). ...

Embodiment 2

[0033] Example 2 1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrol-3-yl]-N-propylene glycol methylamine monofumaric acid (compound Ⅰ) synthesis

[0034]

[0035] (1) At room temperature, add 43g of compound (IV) and 200ml of methanol to the reaction flask, add 15g of 3-amino-1,2-propanediol, stir for 0.5h, then add 2g of sodium borohydride in N, N-dimethylacetamide solution, stirred and reacted at room temperature for 0.5h, then added 350ml of water, adjusted the pH to 5 with hydrochloric acid, quenched the reaction, then adjusted the pH to 10 with ammonia water, added 450ml of ethyl acetate for extraction, and the organic phase was extracted with water Wash and concentrate under reduced pressure to obtain the free oily state, which is 1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrol-3-yl]-N-propylene glycol methylamine mono Free state of fumaric acid (compound V);

[0036] (2) Add 200ml of N,N-dimethylacetamide to compound V, stir to dissolve, add 14g of fum...

experiment example 1

[0044] Experimental Example 1 Water Solubility Evaluation

[0045] Sample: the compound shown in formula I and vonoprazan fumarate;

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Abstract

The present invention provides a compound shown in formula V or a salt thereof, the chemical structural formula of the compound is shown in formula V: wherein, R is C 1 -C 6 The polyhydroxyl group; The salt of described compound is selected from fumaric acid and / or hydrochloride and / or sulfate of compound shown in formula V; The water solubility of compound provided by the present invention and salt thereof is improved, to the Medication in emergencies shows more excellent therapeutic effect. It can be prepared into injection preparations, etc., and the administration in emergency situations can produce drug effects rapidly.

Description

technical field [0001] The invention belongs to the field of medicine, and particularly relates to a compound for treating peptic ulcer, its preparation method and application. Background technique [0002] The proton pump inhibitor vonoprazan fumarate can inhibit the secretion of gastric acid to treat peptic ulcer, and it has been widely used clinically. However, the existing vonoprazan fumarate has the problem of poor solubility in water. Specifically, due to the poor water solubility of vonoprazan fumarate, it cannot be formulated into injections, and it is often formulated into oral solid preparations. Because oral solid preparations generally take several hours to show therapeutic effects, it is not conducive to emergency treatment. Medication, therefore needs improvement. Contents of the invention [0003] In order to solve the problem of poor water solubility of vonoprazan fumarate in the prior art, the present invention studies a new class of compounds with good ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12A61P1/00A61K31/4439A61K9/08
CPCC07D401/12A61P1/00A61K9/0019A61K9/08
Inventor 蔡南桂
Owner 赛隆药业集团股份有限公司
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