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Indole and azaindole derivative and preparation method and application thereof in medicines

A compound and heteroaryl technology, applied in pharmaceutical formulations, antipyretics, antibacterials, etc., can solve the problems of slow onset of acid breakthrough at night, influence of administration time, instability, etc.

Active Publication Date: 2016-03-30
JIANGSU CAREFREE PHARM CO LTD +1
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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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  • Indole and azaindole derivative and preparation method and application thereof in medicines
  • Indole and azaindole derivative and preparation method and application thereof in medicines
  • Indole and azaindole derivative and preparation method and application thereof in medicines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Embodiment 1: 1-(6-(2-fluoro-phenyl)-1-(pyridin-3-yl-sulfonyl)-1H-indol-3-yl)-N-methylmethylamine (compound 1 ) preparation

[0067]

[0068] 1) 6-Bromo-1 H - Preparation of indole-3-carbaldehyde (compound B)

[0069] At 0°C, POCl 3 (2.0mL) was added dropwise to DMF (8.0mL), stirred for 30 minutes, then added dropwise the mixture of compound 1 (3.0g, 15.3mmol) and DMF (2.0ml), after the addition was completed, naturally warmed to room temperature and stirred for 2 hours . After the reaction, the reaction solution was poured into ice water, and the pH was adjusted to about 8 with a saturated sodium hydroxide solution. Filtration, the filtrate was collected, and concentrated under reduced pressure to obtain a light yellow solid compound B (1.60g, 47%).

[0070] 1 H-NMR (400M, DMSO- d6 ) δ :12.24(bs,1H),9.94(s,1H),8.33(s,1H),8.03(d,1H),7.72(d,1H),7.36(d,1H)ppm.

[0071] 2) 6-(2-fluoro-phenyl)-1 H - Preparation of indole-3-carbaldehyde (compound C)

[...

Embodiment 2

[0080] Example 2: Preparation of N-methyl-1-(1-(pyridin-3-yl-sulfonyl)-1H-indol-3-yl)methanamine (compound 2)

[0081]

[0082] Referring to the preparation method of Compound 1, Compound 2 was obtained as a white solid with a yield of 40%. HPLC:93.1%; MS(ESI)m / z:[M+H] + =302.0; 1 H-NMR (400MHz, DMSO- d6 )δ:9.17(d,1H),9.09(br,1H),8.85(m,1H),8.45(m,1H),8.11(s,1H),7.99(d,1H),7.86(d,1H ), 7.64 (m, 1H), 7.42 (t, 1H), 7.37 (t, 1H), 4.27 (s, 2H), 2.53 (s, 3H) ppm.

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PUM

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Abstract

The present invention relates to a novel indole and azaindole derivative and a preparation method and application thereof in medicines. Specifically, the present invention relates to an indole and azaindole derivative shown as the general formula (I) and a preparation method, a pharmaceutical composition containing the derivative, and application of the derivative as a therapeutic agent especially as a gastric acid secretion inhibition agent and potassium ion competitive acid blockers (P-CABs), wherein substituents in the general formula (I) are as defined in the specification.

Description

technical field [0001] The present invention relates to a new class of indole and azaindole derivatives, their preparation process 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) use. 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 differences)...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12C07D471/04A61K31/444A61K31/4439A61P1/04A61P1/00A61P29/00A61P35/00A61P31/04A61P1/14
Inventor 秦引林苏梅金秋陈涛蒋建华伍贤志
Owner JIANGSU CAREFREE PHARM CO LTD
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