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Acylaminoimidazole derivative and use thereof

A carboxamide and thiazole technology, applied in the field of amidoimidazole derivatives and their uses, can solve the problems of single dosage form, narrow antibacterial spectrum, drug interaction, etc.

Active Publication Date: 2016-05-04
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although azole drugs have an irreplaceable role in clinical practice, more and more shortcomings of this class of drugs have been exposed, such as narrow antibacterial spectrum, drug resistance, toxic and side effects, single dosage form, and drug interactions. Antifungal drugs with broad spectrum, high efficiency, low toxicity and diversified administration methods have always been an important topic of research in this field.

Method used

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  • Acylaminoimidazole derivative and use thereof
  • Acylaminoimidazole derivative and use thereof
  • Acylaminoimidazole derivative and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0330] Example 1: Preparation of (S)-2-(benzo[d]thiazole-2-carboxamido)-3-(1H-imidazol-1-yl)propionic acid methyl ester

[0331] Preparation of step A-12-oxo-2-phenylaminoacetic acid ethyl ester (1)

[0332] 5.00 g (53.8 mmol) of aniline was added to 20 mL of diethyl oxalate, and the temperature was controlled at 150° C. After 5 hours, TLC monitored that the reaction was complete. The reaction solution was cooled, 100 mL of petroleum ether was added, and a large amount of white solid was formed after stirring for 10 min, and 8.52 g of white solid was obtained by suction filtration, with a yield of 82.1%. MS[M+H]+ + (m / z): 194.

[0333] Preparation of step A-22-thio-2-phenylaminoacetic acid ethyl ester (2)

[0334] Add 2.00 g (10.4 mmol) of intermediate 1 (ethyl 2-oxo-2-phenylaminoacetate) and 2.10 g (5.2 mmol) of Lawson’s reagent into 30 mL of toluene, react at 70° C. for 3 h, and monitor the completion of the reaction by TLC. The solvent was concentrated under reduced pre...

Embodiment 2

[0346] Example 2 (S)-2-(benzo[d]thiazole-2-carboxamido)-3-(1H-imidazol-1-yl) ethyl propionate

[0347] ESI-MS[M+H] + (m / z):345;

Embodiment 3

[0348] Example 3 (S)-2-(benzo[d]thiazole-2-carboxamido)-3-(1H-imidazol-1-yl)propionic acid propyl ester

[0349] ESI-MS[M+H] +(m / z):359;

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Abstract

The invention belongs to the technical field of medicines and relates to an acylaminoimidazole derivative shown in the general formula I and its stereisomer and pharmaceutical acceptable salt, hydrate, solvate or prodrug. In the formula I, substituents R, R1, Ar, M and X are defined in the specification. The invention also relates to a method for preparing the compound shown in the formula I, a medicinal composition containing the compound and a use of the compound and the medicinal composition in preparation of drugs for treating and / or preventing cancers and other skin proliferative diseases. An antifungal experiment proves that the compound has strong resistance to shallow and deep fungi and can be used for preparation of an antibacterial drug.

Description

technical field [0001] The present invention relates to novel imidazole derivatives and their pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, their preparation methods and pharmaceutical compositions containing the compounds. The present invention relates to imidazole derivatives and pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof in the preparation and treatment of trans-retinoic acid (ATRA) metabolized too fast due to abnormally high expression of CYP26A1, so that trans-retinoic acid (ATRA) The use of retinoic acid for weakening the pharmacological activity, especially the use in the preparation of medicines for treating and / or preventing cancer. The present invention also relates to the use of imidazole derivatives and pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof in the preparation of medicines for treating various diseases caused by fungal infections. Background technique [0002] Cancer i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12C07D403/12C07D233/64A61K31/428A61K31/4178A61K31/417A61P35/00A61P31/10
CPCC07D233/61C07D233/64C07D403/12C07D417/12
Inventor 赵冬梅孙彬赵世振程卯生李凤荣赵立雨郝晨洲刘春池任金红
Owner SHENYANG PHARMA UNIVERSITY
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