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Non-steroid antiandrogen compounds as well as preparation method and application thereof

An anti-androgen, compound technology, applied in the field of medicine, can solve the problem of expensive treatment, and achieve the effect of inhibiting tumor growth, large clinical application value, and high social benefits

Inactive Publication Date: 2014-07-02
沈江 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the patent of the drug is protected until 2026, and the treatment is expensive, costing 35,000 yuan per month. Therefore, it is urgent to develop a new generation of efficient and safe anti-androgen drugs with independent property rights in my country

Method used

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  • Non-steroid antiandrogen compounds as well as preparation method and application thereof
  • Non-steroid antiandrogen compounds as well as preparation method and application thereof
  • Non-steroid antiandrogen compounds as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Example 1: The new compound 5,5-dimethyl-1-(2-fluoro-3-hexanoyl)phenyl-3-(2-trifluoromethyl-3-cyano)phenyl-4-oxo -Synthesis of 2-thioimidazolidinone

[0039]

[0040] 1. Synthesis of Intermediate 2

[0041] At 0°C, the reactant 3-fluoro-4-iodoaniline (3-flouro-4-iodoaniline) (474mg, 2.0mmol) was added to a solution of acetone (116mg, 2.0mmol), AcOH (3.2ml) , keep the reaction at 0°C in the dark for 15-30min, add trimethylsilyl nitrile (TMSCN) (0.26ml, 2.0mmol) in the dark, react overnight at room temperature, add the reaction solution into ammonia water (ice bath) pH is alkaline , extracted three times with dichloromethane, combined the organic phases, washed the organic phases with water and brine, and anhydrous Na 2 SO 4 Dry, and remove solvent by rotary evaporation to obtain Intermediate 2;

[0042] 2. Synthesis of Intermediate 4

[0043] Intermediate 2 (617.9mg, 2.03mmol) was added to a microwave reaction vial, dried and freshly evaporated DMF (1ml), and the...

Embodiment 2

[0052] Embodiment 2: the pharmacological experiment of compound of the present invention:

[0053] 1. In vitro experiments to study the inhibitory effect of new drugs on prostate cancer epithelial cells

[0054] 1. Materials and reagents

[0055] Androgen-independent prostate cancer (LNCaP-AI) cells were donated by the Urology Department of Changhai Hospital Affiliated to the Second Military Medical University of the Chinese People's Liberation Army.

[0056] RPMI1640 culture medium (Hyclone company),

[0057] Activated carbon-treated fetal bovine serum, Charcoal Stripped Serum, CSS (Hyclone Company),

[0058] Elecsys total PSA reagent Kit (Roche Company, Cat.No.1731262),

[0059] Enzalutamide and Bicalutamide were purchased from Shanghai Hanxiang Biotechnology Co., Ltd.,

[0060] The new compound is 5,5-dimethyl-1-(2-fluoro-3-hexanoyl)phenyl-3-(2-trifluoromethyl-3-cyano)phenyl- 4-Oxo-2-thioimidazolinone (compound three).

[0061] 2. Experimental method

[0062] (1), MT...

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PUM

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Abstract

The invention relates to the technical field of medicines and provides novel non-steroid antiandrogen compounds as well as pharmaceutically acceptable salts thereof, wherein the structural formula of the compounds is as shown in formula (I). The invention further provides a preparation method of the compounds and application of the compounds in preparation of antiandrogen compounds and drugs for treating steriod-resistant prostatic cancer.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a non-steroidal antiandrogen compound and its preparation method and application. Background technique [0002] As a common disease in elderly men, prostate cancer has the highest incidence of male malignant tumors in the United States. It was not paid enough attention in my country's tumor spectrum because it was a small disease. In recent years, with the rapid development of my country's economy, aging population, social urbanization, changes in dietary structure, and advances in detection technology, the incidence of prostate cancer in my country has shown a significant upward trend. Among them, the incidence of male prostate cancer in Shanghai increased from 0.2 / 100,000 in the 1950s to 21 / 100,000 in 2008, ranking first among male genitourinary tumors, and we must pay attention to it. Early localized prostate cancer can achieve good curative effect by surgery and radiotherap...

Claims

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Application Information

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IPC IPC(8): C07D233/86A61K31/4166A61P5/28A61P35/00
CPCC07D233/86
Inventor 沈江杨华刘晔
Owner 沈江
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