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Alkyl-substituted quinolinone compound with side chains as well as preparation method, pharmaceutical composition and application thereof

The technology of a compound, quinolinone, is applied in the field of medicine to achieve the effects of enhanced proton pump inhibition, strong anti-Helicobacter pylori effect, and overcoming technical defects

Inactive Publication Date: 2013-05-22
CHONGQING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it cannot be used to solve the problem of treating digestive system diseases caused by Helicobacter pylori

Method used

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  • Alkyl-substituted quinolinone compound with side chains as well as preparation method, pharmaceutical composition and application thereof
  • Alkyl-substituted quinolinone compound with side chains as well as preparation method, pharmaceutical composition and application thereof
  • Alkyl-substituted quinolinone compound with side chains as well as preparation method, pharmaceutical composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1, preparation synthesis heptanolinone compound:

[0044] 1. Take 13mmol of o-aminopropiophenone and 20mmol of 4-methyl-octanoyl chloride, put them in a 250ml double-neck round bottom flask, add 18mmol of pyridine, 60-80ml of dichloromethane, stir and react at room temperature for 4-20 hours, and add saturation Ammonium chloride solution 60-100ml, take the organic phase, concentrate under reduced pressure, conduct silica gel column chromatography on the residue, collect the target object, concentrate under reduced pressure, and dry to obtain 4-methyl-octylaminopropiophenone;

[0045] 2. Put 11mmol of 4-methyl-octanoylaminopropiophenone in step (1) into a 250ml double-neck round bottom flask, add 30-40mmol of sodium tert-butyl alkoxide, 180-240ml of anhydrous organic solvent, and reflux for 4- After 36 hours, concentrate under reduced pressure to recover ethanol, add 100-200ml of water to elute once, and the residue is subjected to silica gel column chromatog...

Embodiment 2

[0049] Embodiment 2, the method for preparing heptanolinone tablet:

[0050] Taking the heptanolinone compound prepared in Example 1 as raw material, prepare heptanolinone tablet, the formula of 1000 tablets is as follows:

[0051] Heptanolone (as C 18 h 22 NO meter)

[0052] Mix the raw materials and auxiliary materials, grind them into fine powder, pass through a 100-mesh sieve, take the amount according to the formula, press into tablets, and pack.

Embodiment 3

[0053] Embodiment 3, the method for preparing heptanolone capsule:

[0054] Taking the heptanolinone compound prepared in Example 1 as raw material, prepare heptanolinone capsules, the formula of 1000 capsules is as follows:

[0055] Heptanolone (as C 18 h 22 NO meter)

Starch and other accessories

100

150

[0056] Mix the raw materials and auxiliary materials, grind them into fine powder, pass through a 100-mesh sieve, take the amount according to the formula, granulate and pack.

[0057] Biological test 1: Antibacterial effect of heptanolone:

[0058] According to the literature (Ibrahim M, Khan AA, Tiwari SK, et a1. Antimierobia activity of Sapindus mukorossi and Rheum emodi extracts against H. priori: in vitro and in vivo studies. World J Gastroenterol, 2006.14: 7136-7142.) method The effect of heptanolone against clinically isolated Helicobacter pylori SW-2 and standard strains was tested (Table 1). Linmycin.

[0059] Table 1 MIC ...

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Abstract

The invention provides an alkyl-substituted quinolinone compound with side chains. The alkyl-substituted quinolinone compound has a chemical structure represented by formula I, the name of the alkyl-substituted quinolinone compound is 2-(4'-methyl-)heptane-3-methyl-4(1H)-quinolinone, the chemical formula of the alkyl-substituted quinolinone compound is C18H22NO, and the alkyl-substituted quinolinone compound is named as heptanone. The invention further provides an application of pharmaceutical composition of the compound provided by the invention in preparation of drugs for prevention and / or treatment of gastritis caused by Helicobacter pylori. According to the alkyl-substituted quinolinone compound, a first-site N of the quinolinone is not hydroxylated, and a second-site of the quinolinone is substituted by 4-methyl-heptane; the quinolinone is prepared by utilizing total synthesis; and the compound, represented by the formula I and provided by the invention, has a relatively high selective inhibition effect on the Helicobacter pylori and is an efficient proton pump inhibitor, so that a possibility for developing a novel drug for treating the gastritis caused by the Helicobacter pylori is provided.

Description

technical field [0001] The invention provides an alkyl-substituted quinolinone compound with a side chain, a preparation method, a pharmaceutical composition and application thereof, and belongs to the technical field of medicine. Background technique [0002] Helicobacter pylori (Helicobacter pylori) is a Gram-negative Helicobacter that colonizes the gastric mucosa and is an important pathogenic factor causing chronic gastritis and peptic ulcer. Class I carcinogens in gastric mucosa-associated lymphoid tissue lymphoma and gastric adenocarcinoma. The chronic infection rate of H. pylori in the population of the world is as high as more than 50%, and the rate of infected people in developing countries even reaches 70-90%. The 2001-2004 epidemiological survey of the Digestive Disease Branch of the Chinese Medical Association showed that the infection rate of Helicobacter pylori in my country was 40%-90%, with an average of 59%; the infection rate of children was 25%-59%, with ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/233A61K31/438A61P1/04A61P31/04
Inventor 郑一敏胥秀英王锐刘红张心蕊
Owner CHONGQING UNIV OF TECH
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