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Diphenyl heptanone compound, its production and use

A technology of diphenylheptanone and compounds, applied in the preparation of organic compounds, chemical instruments and methods, and preparation of carboxylic acid esters, can solve the problems of poor patient tolerance, large side effects, curative effect and application impact, etc., and achieve strong Therapeutic effect, significant effect

Inactive Publication Date: 2006-08-16
沈斌彬
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, for the treatment of Hp infection at home and abroad, the general treatment principle is based on antibiotics, supplemented by acid suppressant (bismuth), commonly used antibiotics such as amoxicillin, gentamicin, clarithromycin and amoxicillin, However, due to the need for multi-drug combination, the side effects are large, the patient's tolerance is poor, and antibiotics are prone to drug resistance, the curative effect and application are affected

Method used

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  • Diphenyl heptanone compound, its production and use
  • Diphenyl heptanone compound, its production and use
  • Diphenyl heptanone compound, its production and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Example 1 Synthesis of compound 1 [5-acetoxy-1-(3'-methoxy-4'-hydroxyphenyl)-7-(4"-methoxyphenyl)-3-heptanone]

[0071] The synthetic route of compound 1 is as follows:

[0072]

[0073] Synthesis of 4-methoxycinnamic acid (II):

[0074] 25g (180mmol) of p-methoxybenzaldehyde, 32g of malonic acid and 25ml of pyridine were mixed, and 1ml of hexahydropyridine was added. Stir the reaction at 85-120°C for 6 hours, cool the reactant, add 120g of 25% potassium carbonate solution, stir for 15min, filter, and acidify the filtrate with concentrated hydrochloric acid to PH<1, the crude product is precipitated, and the crude product is recrystallized by ethanol to obtain white Crystal, product 30.4g, yield 95%.

[0075] Synthesis of 4-methoxyphenylpropionic acid (III):

[0076] Dissolve 2.38g (13.4mmol) of compound II in 30ml of methanol, add 0.15g of 5% Pd / C, feed hydrogen, stir at room temperature, check the progress of the reaction by TLC, the reaction is complete after a...

Embodiment 2

[0093] Example 2 Synthesis of Compound 2 [5-Acetoxy-1-(3′,4′-dimethoxy-phenyl)-7-(4″-methoxyphenyl)-3-heptanone]

[0094] The synthetic route of compound 2 is as follows:

[0095]

[0096] The synthesis of 4-methoxyphenylpropan-3-aldehyde (VI) is with embodiment 1.

[0097] 3, the synthesis of 4-dimethoxybenzaldehyde (VIII):

[0098] Dissolve 1.52g (10mmol) of 3-methoxy-4-hydroxybenzaldehyde VII in 30ml of anhydrous acetone, add anhydrous K 2 CO 3 1.8g, stirred vigorously at room temperature, added dropwise CH 3 I (14.0mmol), reacted at room temperature for 4 hours, after the reaction was complete, filtered K 2 CO 3 , 1.50 g of a yellow oily liquid was obtained, and the yield was 90%.

[0099] 3, the synthesis of 4-dimethoxybuten-3-one (IX):

[0100] Dissolve 1.66 g (10 mmol) of compound VIII in 20 ml of acetone, slowly add 25 ml of 1% NaOH in an ice-water bath, then remove the ice bath, react at room temperature, check the progress of the reaction by TLC, complete t...

Embodiment 3

[0106] Example 3 Compound 3[5-acetoxy-1-(3'-methoxy-4'-acetoxy-phenyl)-7-(4"-methoxyphenyl)-3-heptanone ]Synthesis

[0107] The synthetic route of compound 3 is as follows:

[0108]

[0109] The synthesis of 1-(3'-methoxyl-4'benzyloxyphenyl)-7-(4"-methoxyphenyl)-5-hydroxyl-3-ketone-1-heptene (X) is the same as Example 1

[0110] Synthesis of 5-acetoxy-1-(3'-acetoxy-4'-methoxy-phenyl)-7-(4"-methoxyphenyl)-3-heptanone (3):

[0111] Dissolve 223 mg (0.5 mmol) of compound X in 20 ml of anhydrous methanol, add 0.15 g of Pd / C, pass through hydrogen, stir at room temperature for about 24 hours, TLC detects that the reaction is complete, filter under reduced pressure, evaporate the solvent, and the silica gel column layer Analysis, petroleum ether: acetone = 4: 1 elution gave 1149 mg of yellow powdery crystals, yield 83%. Dissolve 358mg (1mmol) in 8ml of pyridine, add 0.5ml of acetic anhydride after complete dissolution, complete reaction after 1 hour, evaporate the solvent to ...

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PUM

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Abstract

A diphenyl heptanone compound, its production and use in pharmaceutical industry are disclosed. It can be used for reactivation gastritis, stomach erosio, gastric ulcer and duodenal ulcer.

Description

field of invention [0001] The invention belongs to the field of medicines, and in particular relates to a new class of diphenylheptanone compounds, their preparation methods and applications in the field of pharmacy, especially in the preparation of anti-Helicobacter pylori (Helicobacter pylori, referred to as Hp) and treatment Drug application in gastric ulcer-related diseases. Background of the invention [0002] Helicobacter pylori (HP) was first successfully isolated from the gastric mucosal biopsy tissue of patients with chronic active gastritis in 1983, and is the only microbial species known to survive in the human stomach. Gastritis, peptic ulcer, lymphoproliferative gastric lymphoma and gastric cancer are diseases that seriously endanger human health and life. Medical research has confirmed that the above diseases are all related to Helicobacter pylori (Hp) infection. Statistics show that more than 50% of the world's population is infected with Helicobacter pylori,...

Claims

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Application Information

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IPC IPC(8): C07C69/12C07C67/08A61K31/22A61K9/20A61K9/08A61K9/48A61K9/14A61P31/04
Inventor 金耀刘展欣
Owner 沈斌彬
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