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4-ring end substituted 2-1,2,3-triazole phenylamines compound, preparation and purpose

A technology of triazole aniline and compound, applied in the fields of pharmacy, medicinal chemistry and pharmacology, can solve the problems of reversible transaminase rise, rash and vomiting, etc.

Inactive Publication Date: 2013-06-26
TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these drugs also have some disadvantages, such as cetuximab can cause myalgia, arthralgia, neutropenia and other toxicities; gefitinib not only has toxic side effects such as rash and vomiting, but also has adverse effects on the patient population. Selective, more effective for smoking women and the elderly; PKI16 increases reversible transaminases, rashes, etc.

Method used

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  • 4-ring end substituted 2-1,2,3-triazole phenylamines compound, preparation and purpose
  • 4-ring end substituted 2-1,2,3-triazole phenylamines compound, preparation and purpose
  • 4-ring end substituted 2-1,2,3-triazole phenylamines compound, preparation and purpose

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[0040] The starting materials used in the preparation of the compounds of the present invention are known, can be prepared according to known methods, or are commercially available.

[0041] The invention also relates to new intermediates and / or starting materials. Especially preferred are the same or similar reaction conditions and new intermediates as those mentioned in the examples.

[0042] Both the intermediate and the final product can be post-processed and / or purified according to conventional methods, including pH adjustment, extraction, filtration, drying, concentration, chromatography, grinding, crystallization, and the like.

[0043] In addition, the compounds of the present invention can also be prepared by various methods known in the art or variations of the methods described herein.

[0044] The following examples are only used to illustrate the present invention, and do not limit the present invention in any way.

Embodiment 1

[0045] Example 1, Preparation of 4-ring end substituted 2-1,2,3-triazole aniline compound 2-(1-(3-chloro-4-fluorophenyl)-1H-1,2,3-tri Azazol-4-yl)-5-methoxy-4-(3-morpholinopropoxy)aniline method

[0046]

[0047] It includes the following steps:

[0048] Step a: Preparation of tert-butyl (2-formyl-4-hydroxy-5-methoxyphenyl) aminobenzoate

[0049] 25ml three-necked round bottom flask, add 10ml dichloromethane, compound 2-amino-5-hydroxy-4-methoxybenzaldehyde (0.03g, 0.20mmol), TEA (0.27ml, 0.40mmol), Boc 2 O (0.05g, 0.24mmol), stirred at 0°C for 10 minutes, and then reacted at room temperature for 6 hours. TLC followed the progress of the reaction. After the reaction, use saturated KHSO 4 Adjust the PH value to 7, then extract the triethylamine salt with saturated brine, and the product is in the organic phase. The solvent was removed by rotary evaporation to obtain 0.05 g of the product. (Yield 83.41%). (MS: [M+H] + 268.11)

[0050] Step b: Preparation of tert-butyl(2-formyl-5-me...

Embodiment 2

[0059] Example 2, Preparation of 4-ring-terminally substituted 2-1,2,3-triazole aniline compound 4-(3-(1,3,4-oxothioazin-4-yl)propoxy)-2 -(1-(3-chloro-4-fluorophenyl)-1H-1,2,3-triazol-4-yl)-5-methoxyaniline method

[0060]

[0061] The preparation method is as shown in Example 1. The raw material in step b is 4-(3-chloropropyl)-1,3,4-oxythioazine, and the remaining steps are the same, and the final product is 0.07g.

[0062] MS: [M+H] + 480.12; 1 H NMR(400MHz, CDCl 3 ): δppm 7.79(s, 1H), 7.48(d, 1H), 7.33(d, 1H), 7.18(d, 1H), 7.00(s, 1H), 6.27(s, 1H), 6.13(s, 1H) ), 4.64(s, 2H), 4.06(t, 2H), 4.05(s, 1H), 3.83(s, 1H), 3.49(t, 2H), 2.72(t, 2H), 2.55(t, 2H) , 1.84 (m, 2H).

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Abstract

The invention relates to a 4-ring end substituted 2-1,2,3-triazole phenylamines compound, a preparation and a purpose, and concretely relates to the 4-ring end substituted 2-1,2,3-triazole phenylamines compound with a structure shown as a following general formula (I), the 4-ring end substituted 2-1,2,3-triazole phenylamines compound is a good tyrosinase inhibitor, and can better inhibit the viability and growth of lung carcinoma cells A549, H358, PC9 and HT-29, wherein R1 is selected from H and C1-4 alkyloxy; R2 is selected from a following structural unit:; and R3 is selected from a following structural unit:.

Description

Technical field [0001] The invention belongs to the fields of pharmacology, medicinal chemistry and pharmacology, and more specifically, relates to a method for preparing a new type of tyrosine kinase inhibitor 4-ring end substituted 2-1, 2, 3 triazole aniline compound and Use in the preparation of drugs for treating tumors. Background technique [0002] According to an investigation by the Ministry of Health, malignant tumors have become the leading cause of death for both urban and rural residents in our country, and the mortality rate is gradually rising, and the treatment of malignant tumors has become a hot topic. In the past 50 years, the incidence and mortality of lung cancer have risen rapidly in countries around the world, especially in industrialized developed countries. Among male patients who died of cancer, lung cancer has ranked first. Non-small cell lung cancer (NSCLC) accounts for about 80-85% of the total number of lung cancers. [0003] Among a variety of anti-t...

Claims

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Application Information

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IPC IPC(8): C07D249/06C07D419/12A61K31/5377A61K31/4192A61P35/00
Inventor 陈悦饶子和杨诚白翠改张伟潘成文孟凡菲王颂
Owner TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
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