Azo-benzoic acid type compound as well as preparation method and applications thereof

A technology of azobenzoic acid and benzoic acid, applied in organic chemistry, drug combination, cardiovascular system diseases, etc., can solve undiscovered problems

Active Publication Date: 2016-10-05
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The GPR35 agonists that have been discovered so far include: antiasthmatic drugs chromylic acid and dicoumarin, diuretics bumetanide and furosemide, catechol transferase inhibitor drugs entacapone for the treatment of Parkinson's disease, The analgesic agent niflumic acid; some abundant phytochemicals such as: myricetin, morin, gallic acid, and gallic acid also have a moderate activation effect on GPR35; however, a better drug targeting GPR35 has not yet been found

Method used

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  • Azo-benzoic acid type compound as well as preparation method and applications thereof
  • Azo-benzoic acid type compound as well as preparation method and applications thereof
  • Azo-benzoic acid type compound as well as preparation method and applications thereof

Examples

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preparation example Construction

[0029] The present invention also provides a method for preparing the compound of the structure represented by formula (1), wherein the method includes:

[0030] (1) In the presence of inorganic acid, the formula (2) The compound of the structure shown and the diazotizing agent undergo a diazotization reaction;

[0031] (2) In the presence of an alkali metal hydroxide, contacting the product mixture obtained from the diazotization reaction with salicylic acid;

[0032] (3) Acidifying the product mixture after the contact reaction;

[0033]

[0034] Where R 1 Is hydrogen, C 1 -C 4 The alkyl group, C 1 -C 4 The alkoxy, halogen, nitro or carboxyl group; R 2 , R 3 And R 4 Each independently is hydrogen, C 1 -C 4 The alkyl group, C 1 -C 4 的alkoxy, C 1 -C 4 The hydroxyalkyl, halogen, nitro or carboxyl group; and R 1 , R 2 , R 3 And R 4 It is not hydrogen at the same time.

[0035] According to the present invention, in the above preparation method, R 1 , R 2 , R 3 And R 4 The preferred combi...

Embodiment 1

[0059] This example is used to illustrate the azobenzoic acid compound of the present invention and the preparation method thereof.

[0060] Stir and mix 5-amino-2-methylbenzoic acid (1.51g, 10mmol) and 6mL of aqueous hydrochloric acid (6mol / L). Add 3.8g of NaNO dropwise while stirring at 0°C 2 Aqueous solution (20% by weight), control the dropping rate so that the temperature does not exceed 10°C, react for 30min to obtain the diazonium salt solution after the addition is complete; continue to add the diazonium salt solution dropwise to the salicylic acid (1.24 g, 9mmol) 10% by weight NaOH aqueous solution (16mL), control the dropping rate so that the temperature does not exceed 10℃, and continue to react at 0℃ for 2h, then add 6mol / L hydrochloric acid aqueous solution to the reaction system until the reaction The pH of the system was 1, filtered, and the filter cake was washed with water to obtain the compound of the formula (1-1) (1.21 g, yield 90%) as a yellow solid. Mp: 295°...

Embodiment 2

[0062] This example is used to illustrate the azobenzoic acid compound of the present invention and the preparation method thereof.

[0063] Stir and mix 4-amino-phthalic acid (0.97g, 5mmol) and 3mL of hydrochloric acid aqueous solution (6mol / L), add 2g of NaNO dropwise while stirring at 0℃ 2 Aqueous solution (20% by weight), control the dropping rate so that the temperature does not exceed 10°C, react for 40 minutes after the addition to obtain the diazonium salt solution; continue to add the diazonium salt solution to the salicylic acid (0.69 g, 10mmol) 10 wt% NaOH aqueous solution (15mL), control the dropping rate so that the temperature does not exceed 10 ℃, and continue to react at 0 ℃ for 3.5h, and then add 5mol / L hydrochloric acid aqueous solution to the reaction system to The pH of the reaction system was 2, filtered, and the filter cake was washed with water to obtain the compound of the formula (1-2) (1.14 g, yield 69%) as a yellow solid. Mp: 298-299°C (decomposition). ...

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Abstract

The invention relates to an azo-benzoic acid type compound. The compound has a structure shown by a formula (1). The invention also provides a preparation method of the compound with the structure shown by the formula (1). The invention also provides an application of the azo-benzoic acid type compound or a pharmaceutically acceptable salt and a medicine complex thereof in serving as an agonist for a G-protein coupled receptor 35. The invention also provides an application of the azo-benzoic acid type compound or the pharmaceutically acceptable salt and the medicine complex thereof in preparation of medicines for preventing and/or treating inflammation, asthma, Parkinson's disease, angiocardiopathy and intestinal cancer. The azo-benzoic acid type compound provided by the invention has a relatively high targeting property for the G-protein coupled receptor 35.

Description

Technical field [0001] The invention relates to azobenzoic acid compounds, and a preparation method and application thereof. Background technique [0002] GPR35 (G-protein coupled receptor 35) is a type of G protein coupled receptor containing 309 amino acids. It is used in various organs such as stomach, gastrointestinal tissue, obese cells, basophils, and eosinophils. Cells etc. are all expressed. GPR35 plays an important role in many diseases, such as hypertension, coronary artery disease, asthma, pain, inflammatory bowel disease and cancer. Studies have found that human obese cells under the action of IGE antibodies, human macrophages under the action of pyrene, defective heart cells, and gastric cancer cells can all be found to increase (up-regulate) GPR35. Therefore, searching for GPR35 ligands is very important for elucidating the physiological and pathological effects of GPR35. The GPR35 agonists that have been discovered are: antiasthmatic drugs cromolyn and dicoumari...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/08A61P29/00A61P11/06A61P25/16A61P9/00A61P35/00
Inventor 俞初一贾月梅李意羡郭斯阳
Owner INST OF CHEM CHINESE ACAD OF SCI
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