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Azobenzoic acid compound and its preparation method and application

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

Active Publication Date: 2018-07-27
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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  • Azobenzoic acid compound and its preparation method and application
  • Azobenzoic acid compound and its preparation method and application
  • Azobenzoic acid compound and its preparation method and application

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preparation example Construction

[0029] The present invention also provides the preparation method of the compound of structure shown in formula (1), wherein, this method comprises:

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

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

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

[0033]

[0034] Among them, R 1 for hydrogen, C 1 -C 4 Alkyl, C 1 -C 4 Alkoxy, halogen, nitro or carboxyl; R 2 , R 3 and R 4 each independently hydrogen, C 1 -C 4 Alkyl, C 1 -C 4 Alkoxyl, C 1 -C 4 hydroxyalkyl, halo, nitro or carboxyl; and R 1 , R 2 , R 3 and R 4 Not simultaneously hydrogen.

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

Embodiment 1

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

[0060] 5-Amino-2-methylbenzoic acid (1.51g, 10mmol) and 6mL of hydrochloric acid aqueous solution (6mol / L) were stirred and mixed, and 3.8g of NaNO was added dropwise while stirring at 0°C. 2 aqueous solution (20% by weight), control the rate of addition so that the temperature is no more than 10°C, after the dropwise addition, react for 30min to obtain the diazonium salt solution; g, 9mmol) in 10% by weight NaOH aqueous solution (16mL), control the rate of addition so that the temperature does not exceed 10°C, and continue to react at 0°C for 2h, then add 6mol / L aqueous hydrochloric acid to the reaction system The pH of the system was 1, filtered, and the filter cake was washed with water to obtain the compound represented by formula (1-1) (1.21 g, yield 90%) as a yellow solid. Mp: 295°C (decomposition). 1 H NMR (300MHz, DMSO-d 6 )δ8.33(s,1H),8.23(s...

Embodiment 2

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

[0063] 4-Amino-phthalic acid (0.97g, 5mmol) and 3mL of aqueous hydrochloric acid (6mol / L) were stirred and mixed, and 2g of NaNO was added dropwise while stirring at 0°C. 2 aqueous solution (20% by weight), control the rate of addition so that the temperature is no more than 10°C, after the dropwise addition, react for 40min to obtain the diazonium salt solution; g, 10mmol) of 10% by weight NaOH aqueous solution (15mL), control the rate of addition so that the temperature is no more than 10°C, and continue to react at 0°C for 3.5h, then add 5mol / L aqueous hydrochloric acid to the reaction system The pH of the reaction system was 2, filtered, and the filter cake was washed with water to obtain the compound represented by formula (1-2) (1.14 g, yield 69%) as a yellow solid. Mp: 298-299°C (decomposition). 1 H-NMR (300MHz, DMSO-d 6 ): δ8.39(d, J=2.2Hz, 1H...

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Abstract

The invention relates to an azobenzoic acid compound, which is a compound with the structure shown in formula (1). The present invention also provides a preparation method of the compound represented by formula (1). The present invention also provides the application of the azobenzoic acid compound or its pharmaceutically acceptable salt and drug complex as G protein-coupled receptor 35 agonist. The present invention also provides the azobenzoic acid compound or its pharmaceutically acceptable salt and drug complex in the preparation of drugs for preventing and / or treating inflammation, asthma, Parkinson's disease, cardiovascular disease and intestinal cancer Applications. The azobenzoic acid compound provided by the present invention has higher G protein-coupled receptor 35 targeting.

Description

technical field [0001] The invention relates to an azobenzoic acid compound, a preparation method and application thereof. Background technique [0002] GPR35 (G-protein coupled receptor 35) is a class of G protein-coupled receptors containing 309 amino acids, in various organs such as: stomach, gastrointestinal tissue, obese cells, basophils, eosinophils expressed in cells. 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 the increase (upregulation) of GPR35 can be found in human obese cells under the action of IGE antibody, human macrophages under the action of pyrene, defective heart cells, and gastric cancer cells. Therefore, finding GPR35 ligands is very important for elucidating the physiological and pathological roles of GPR35. The GPR35 agonists that have been discovered so far include: antiasthmatic drugs chromylic acid and dicoumarin, diuret...

Claims

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Application Information

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Patent Type & Authority Patents(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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