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Pyrrole sulfonamide derivative, preparation method and medical application thereof

A pharmacy and compound technology, which is applied to pyrrole sulfonyl derivatives, their preparation and their application in medicine, can solve the problems of slow onset of acid breakthrough at night, instability, influence of administration time and the like

Inactive Publication Date: 2016-02-17
JIANGSU CAREFREE PHARM CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such as: the influence of administration time on drug efficacy; slow onset of acid breakthrough at night; instability under acidic conditions (need to be formulated into intestinal preparations); dependence on CYP450 enzymes (resulting in significant individual differences), etc.

Method used

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  • Pyrrole sulfonamide derivative, preparation method and medical application thereof
  • Pyrrole sulfonamide derivative, preparation method and medical application thereof
  • Pyrrole sulfonamide derivative, preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1: 1-(5-(Benzo[d][1,3]dioxol-5-yl)-1-(pyridin-3-yl-sulfonyl)-1H-pyrrole-3 - Preparation of -N-methylmethylamine (compound 1)

[0068]

[0069] 1) Preparation of 5-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrole-3-carbaldehyde (compound C)

[0070] 5-bromo-1H-pyrrole-3-carbaldehyde (compound A, 0.25g, 1.45mmol), benzo[d][1,3]dioxol-5-ylboronic acid (compound B, 0.3g ,1.81mmol), Pd(PPh 3 ) 4 (0.12g, 0.10mmol), Na 2 CO 3 (367mg, 3.46mmol), DME (5mL), and water (2mL) were added to a 25mL eggplant-shaped bottle, stirred, heated to reflux, and reacted for 2h. Stop the reaction, cool to room temperature naturally, pour into ice water (50mL), and extract with EA (50mL*3). The combined organic phases were dried, concentrated, and column chromatography (petroleum ether: ethyl acetate = 2:1) gave off-white solid compound C (38mg, 12.23%), MS (ESI) m / z: [M+H] + =216.1.

[0071] 2) 5-(Benzo[d][1,3]dioxol-5-yl)-1-(pyridin-3-yl-sulfonyl)-1H-pyrrol-3-ylcarbaldehyde (com...

Embodiment 2

[0076] Embodiment 2: 1-(5-(1H-indol-5-yl)-1-(pyridin-3-yl-sulfonyl)-1H-pyrrol-3-yl)-N-methylmethylamine (compound 2) Preparation

[0077]

[0078] Referring to the preparation method of compound 1, a white solid compound was obtained 2 , yield 30%. HPLC:98.1%; MS(ESI)m / z:[M+H] + =367.0; 1 H-NMR (400MHz, DMSO- d6 )δ:11.21(s,1H),8.78(d,1H),8.39(s,1H),7.72(d,1H),7.51(m,1H),7.39(m,3H),7.34(m,1H ), 6.87 (d, 1H), 6.43 (s, 1H), 6.20 (s, 1H), 3.45 (s, 2H), 2.32 (s, 3H) ppm.

Embodiment 3

[0079] Example 3: 1-(5-(2,3-dihydrobenzofuran-5-yl)-1-(pyridin-3-yl-sulfonyl)-1H-pyrrol-3-yl)-N-methyl Preparation of methylamine (compound 3)

[0080]

[0081] Referring to the preparation method of compound 1, a white solid compound was obtained 3 , yield 28%. HPLC:96.8%; MS(ESI)m / z:[M+H] + =370.0; 1 H-NMR (400MHz, DMSO- d6 )δ:8.82(d,1H),8.47(d,1H),7.76(d,1H),7.57(d,1H),7.35(s,1H),6.97(s,1H),6.87(d,1H ), 6.74 (d, 1H), 6.19 (s, 1H), 4.58 (t, 2H), 3.45 (s, 2H), 3.16 (t, 2H), 2.21 (s, 3H) ppm.

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PUM

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Abstract

The present invention relates to a pyrrole sulfonamide derivative, a preparation method and a medical application thereof. Concretely, the present invention relates to the pyrrole sulfonamide derivative shown in a formula (I), the preparation method for the derivative, a pharmaceutical composition comprising the derivative, and uses of same as therapeutic agents, and particularly as a gastric acid secretion inhibitor and potassium-competitive acid blockers (P-CABs), where each substituent of formula (I) is as defined in the description.

Description

technical field [0001] The present invention relates to a new class of pyrrolesulfonyl derivatives, their preparation methods and pharmaceutical combinations containing the derivatives and their use as therapeutic agents, especially as gastric acid secretion inhibitors and potassium ion competitive acid blockers (P-CABs )the use of. Background technique [0002] Since 1988, proton pump inhibitors represented by omeprazole have been widely used clinically to treat peptic ulcer, reflux esophagitis and Zoller-Ellison syndrome by inhibiting gastric acid secretion. Long-term clinical application has found that existing proton pump inhibitors still have limitations in terms of pharmacokinetics and pharmacodynamics. Such as: the effect of administration time on drug efficacy; slow onset of acid breakthrough at night; instability under acidic conditions (need to be formulated into intestinal preparations); dependence on CYP450 enzymes (resulting in significant individual difference...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D405/14C07D417/14C07D495/04C07D471/04C07D487/04C07D403/04C07D409/14A61K31/4439A61K31/4709A61K31/498A61K31/444A61K31/519A61K31/404A61K31/517A61K31/4985A61K31/4725A61P1/04A61P1/00A61P1/14A61P29/00A61P35/00A61P31/04
CPCA61K31/4439A61K31/4709A61K31/498C07D405/14C07D417/14C07D471/04C07D495/04
Inventor 秦引林金秋
Owner JIANGSU CAREFREE PHARM CO LTD
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