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4-azo salicylic acid derivative and process for producing the same and uses

A technology of azosalicylic acid and aminosalicylic acid is applied in the field of 4-azosalicylic acid derivatives and their preparation, and can solve the problems of unreachable treatment purpose, low colon concentration and the like

Inactive Publication Date: 2009-03-11
SHANXI MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, there are research reports that 4-ASA is different from 5-ASA in the site of action and the principle of action, but the same as 5-ASA is: direct oral administration, because most of the proximal small intestine is absorbed, the concentration in the colon is low, reaching 5-ASA. less than therapeutic purpose

Method used

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  • 4-azo salicylic acid derivative and process for producing the same and uses
  • 4-azo salicylic acid derivative and process for producing the same and uses
  • 4-azo salicylic acid derivative and process for producing the same and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] Embodiment 1, a kind of 4-azosalicylic acid derivative

[0092]

[0093] Among them: R stands for:

[0094] R=—COOH,——NO 2 ,—CN,—H,—CHO,—CH 3 ,—OCH 3 ,—F,—Cl,—Br,—I,—CONHCH 2 COOH.

[0095] The preparation steps are:

[0096] A method for preparing 4-azosalicylic acid derivatives, the steps are,

[0097] One, the synthesis of 4-(N-benzyloxyformyl) aminosalicylic acid,

[0098] 4-Aminosalicylic acid (4-ASA) is started, first added to a saturated sodium bicarbonate solution under alkaline conditions to form a uniform suspension, then added dropwise with benzyl chloroformate, stirred in an ice bath for 10 hours to react, and reacted After the end, filter, wash the filtrate with ether (three times), discard the ether layer, adjust the pH value of the solution to acidity, produce off-white solid matter, extract three times with ethyl acetate, combine the organic phases, add desiccant to dry, and organic The phase was evaporated to dryness under reduced pressure to...

Embodiment 2

[0108] Embodiment 2: the steps are the same as in Example 1, specifically in step 1, stirring in an ice bath for 12 hours, the filtrate was washed five times with ether, extracted five times with ethyl acetate,

[0109] In step 2, stir the reaction for 36 hours

[0110] In step 3, the pressure in the autoclave is 0.4MPa and the time is that catalytic hydrogenation reaction occurs under 10 hours

[0111] In step 4, continue to react for 1.5 hours after dropping

[0112] In step 6, acetone-methanol (volume ratio 1:1), alkaline pH=10-11 conditions (potassium hydroxide solution can be used), hydrolysis reaction (time within 2 hours).

Embodiment 3

[0114] The steps are the same as in Example 1, specifically in step 1, stirring in an ice bath for 10 hours, washing the filtrate once with ether, and extracting once with ethyl acetate,

[0115] In step 2, stir the reaction for 48 hours

[0116] In step 3, the pressure in the autoclave is 0.6MPa and the time is that catalytic hydrogenation reaction occurs under 15 hours

[0117] In step 4, continue to react for 2 hours after dropping

[0118] In step 6, acetone-methanol (volume ratio 3:1), alkaline pH=10-11 conditions (can be sodium hydroxide solution), hydrolysis reaction (time within 6 hours).

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Abstract

The invention discloses a 4-azo salicylate derivant and making method and application, which comprises the following steps: synthesizing 4-(N-formyl benzyloxy) amino salicylic acid, 4-(N-formyl benzyloxy) amino-2-aceto salicylic acid, 4-amino-2-aceto salicylic acid, 4-diazo-2-aceto salicylic acid hydrochlorate; reacting to do azo reaction under weak alkali condition; hydrolyzing to obtain terminal product; fitting for making inflammatory enteropathy. R is -COOH,-NO2,-CN, -H,-CHO,-CH3,-OCH3,-F,-Cl,-Br,-I,-CONHCH2COOH.

Description

technical field [0001] The invention relates to a salicylic acid derivative, in particular to a 4-azosalicylic acid derivative and a preparation method and application thereof. Background technique [0002] Inflammatory bowel disease (IBD) is a group of chronic intestinal inflammatory diseases, including ulcerative colitis (ulcerative colitis, UC) and Crohn's disease (Crohn's Disease, CD). At present, the pathogenesis of the disease is considered to be that factors such as immunity, infection, and diet act on the genetically susceptible population to make the immune response hyperactive. However, it is not clear whether this excessively hyperactive immune response is caused by continuous stimulation of antigens or abnormal immune regulation. Among them, immune factors play an important role in the pathogenesis. The prevalence of IBD in western developed countries is relatively high, about 1‰~2‰, and the incidence rate in my country is also increasing year by year, about 0.1...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C245/08A61K31/60A61P1/04
Inventor 赵正保刘锐玲魏元贵刘江郭璟曲婷丽
Owner SHANXI MEDICAL UNIV