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Triazole phenyl amines compound preparation and application

A technology of triazole aniline and compound, applied in the fields of medicinal chemistry, pharmacology, and pharmacology, can solve the problems of rash and vomiting, reversible transaminase rise, 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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  • Triazole phenyl amines compound preparation and application
  • Triazole phenyl amines compound preparation and application
  • Triazole phenyl amines compound preparation and application

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[0038] 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.

[0039] The invention also relates to novel intermediates and / or starting materials. Particular preference is given to reaction conditions and novel intermediates which are the same or similar to those mentioned in the examples.

[0040] Both intermediates and final products can be worked up and / or purified according to conventional methods, including pH adjustment, extraction, filtration, drying, concentration, chromatography, trituration, crystallization, and the like.

[0041] In addition, the compounds of the present invention can be prepared by various methods known in the art or variations on the methods described herein.

[0042] The following examples are only used to illustrate the present invention and do not limit the present invention in any way.

Embodiment 1

[0043] Example 1 Preparation of 2-1,2,3 triazole aniline compound 2-(1-(3-ethynylphenyl)-1H-1,2,3-triazole-4-yl)-4, 5-bis(2-methoxyethoxy)aniline method

[0044]

[0045] Include the following steps:

[0046] Step a: Preparation of tert-butyl(2-cyano-4,4-bis(2-methoxyethoxy)phenyl)carbamate

[0047] 25ml three-neck round bottom flask, add 10ml dichloromethane, compound 2-amino-4,5-bis(2-methoxyethoxy)benzonitrile (0.05g, 0.20mmol), TEA (0.27ml, 0.40mmol), Boc 2 O (0.05g, 0.24mmol), stirred at 0°C for 10 minutes, then reacted at room temperature for 6 hours, and followed the reaction progress by TLC. After the reaction, with 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. Rotary evaporation removes solvent, obtains product 0.06g (productive rate 83.42%) (MS: [M+H] + 367.18).

[0048] Step b: Preparation of 2-((tert-butylcarbonyl)amino)-4,5-bis(2-methoxyethoxy)benzoic acid

...

Embodiment 2

[0063] Example 2 Preparation of 2-1,2,3 triazole aniline compounds: 4-((dimethylamino)methoxy)-2-(1-(3-fluorophenyl)-1H-1,2 , the method of 3-triazol-4-yl)-5-(2-methoxyethoxy)aniline

[0064]

[0065] The preparation method is as shown in Example 1. In step a, 2-amino-5-isobutoxy-4-bis(2-methoxyethoxy)benzonitrile is used as raw material, and in step g, 1-azide -3-fluorobenzene was used as the raw material, and the other steps were the same, and 0.06 g of the final product was obtained.

[0066] MS: [M+H] + 402.19; 1 H NMR (400MHz, CDCl 3 ): δppm 8.08(s, 1H), 7.43(t, 1H), 7.39(d, 1H), 7.24(d, 1H), 7.15(s, 1H), 7.00(s, 1H), 6.27(s, 2H ), 6.13 (s, 1H), 5.01 (s, 2H), 4.31 (t, 2H), 3.79 (t, 2H), 3.30 (s, 3H), 2.26 (s, 6H).

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Abstract

The invention relates to a 2-1,2,3 triazole phenyl amines compound preparation method and an application, and concretely provides a 2-1,2,3 triazole phenyl amines compound with a structure shown as a general formula (I), the compound is a good tyrosinase inhibitor, and can better inhibit the survival and growth of lung carcinoma cells of A549, H358, PC9 and HT-29. R1 is selected from H and C1-4 alkyloxy; R2 is selected from the following structural units; and R3 is selected from the following structures.

Description

technical field [0001] The invention belongs to the fields of pharmacy, medicinal chemistry and pharmacology, and more specifically relates to a preparation method of a novel tyrosine kinase inhibitor triazolidine compound and its use in the preparation of drugs for treating tumors. Background technique [0002] According to the survey by the Ministry of Health, malignant tumors have become the leading cause of death for both urban and rural residents in my country, and the mortality rate is gradually increasing. The treatment of malignant tumors has become a hot topic. Over the past 50 years, the morbidity and mortality of lung cancer have risen rapidly in countries all over the world, especially industrially developed countries, and lung cancer has ranked first among male patients who died of cancer. Non-small cell lung cancer (NSCLC) accounts for about 80-85% of the total number of lung cancers. [0003] Among various anti-tumor drugs, tyrosine kinase inhibitors are one ...

Claims

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Application Information

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IPC IPC(8): C07D249/06A61K31/4192A61P35/00
Inventor 饶子和陈悦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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