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Sulfo-imidazole-diketone and imidazole-diketone compound and applications thereof

A kind of technology of compound and solvate, applied in the field of thioimidazole dione

Inactive Publication Date: 2016-11-23
CHENGDU BESTCHIRALBIO LIMITED LIABILITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, enzalutamide has some neurotoxicity, such as epilepsy, therefore, it is necessary to develop a safer and more effective androgen receptor antagonist

Method used

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  • Sulfo-imidazole-diketone and imidazole-diketone compound and applications thereof
  • Sulfo-imidazole-diketone and imidazole-diketone compound and applications thereof
  • Sulfo-imidazole-diketone and imidazole-diketone compound and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] 4-[3-(6-fluoro-3-oxo-2-(pyrimidin-2-yl)isoindolin-5-yl)-4,4-dimethyl-5-oxo-2- Thioimidazolidin-1-yl]-2-trifluoromethylbenzonitrile

[0093] Step 1: Preparation of 4-isothiocyanato-2-trifluoromethylbenzonitrile

[0094]

[0095] Thiophosgene (1.37ml, 17.97mmol) was added to water (22ml), stirred for 8 minutes, and then 4-amino-2-trifluoromethylbenzonitrile (2.23g, 11.98mmol) was slowly added to the above After the addition, the mixture was stirred at room temperature for 1.5h. The completion of the reaction was monitored by thin-layer chromatography, extracted with dichloromethane, the organic phases were combined, washed with saturated brine, filtered, and concentrated under reduced pressure to obtain 2.73 g of light yellow oily liquid with a yield of 99%. 1 H NMR (400MHz, CDCl 3 ): δ=7.86 (d, J=8.3Hz, 1H), 7.61 (d, J=1.4Hz, 1H), 7.51 (dd, J=8.3, 1.7Hz, 1H).

[0096] Step 2: Preparation of 2-bromo-4-fluoro-5-nitrobenzoic acid

[0097]

[0098] Under ice bath,...

Embodiment 2

[0121] 4-[3-(7-fluoro-3-oxo-2-(pyrimidin-2-yl)isoindolin-5-yl)-4,4-dimethyl-2,5-dioxo imidazolidin-1-yl]-2-trifluoromethylbenzonitrile

[0122]

[0123] Compound 2 is obtained by referring to the synthesis method of scheme 1 and scheme 2 for the compound of the present invention. ESI-MS m / z:524.8(M+H) + .

Embodiment 3

[0125] 4-[3-(7-fluoro-3-oxo-2-(pyrimidin-2-yl)isoindolin-5-yl)-4,4-dimethyl-5-oxo-2- Thioimidazolidin-1-yl]-2-trifluoromethylbenzonitrile

[0126]

[0127] The compound of the present invention was synthesized with reference to the synthesis method of Example 1 to obtain compound 3. ESI-MS m / z:540.7(M+H) + .

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PUM

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Abstract

The invention discloses a sulfo-imidazole-diketone and imidazole-diketone compound and applications thereof. The invention provides the formula (I) compound (please see the specification) or pharmaceutical salt, solvate, prodrug, stereoisomer, tautomer and metabolite thereof, wherein X, Y, Z, R1, R2, R3 and A are defined in the formula. The invention further provides a preparing method for the compound and applications of the compound serving as an androgen receptor antagonist to treating diseases related to an androgen receptor, such as prostatic cancer, prostatic hyperplasia, acne, feather-loss disorder, hair hyperplasia, breast cancer and poor male sexual function.

Description

technical field [0001] The present invention relates to a class of thioimidazole diketones and a class of imidazole diketones, methods for their synthesis and their use in the treatment of diseases or disorders associated with androgen receptors. Background technique [0002] Prostate cancer has become an important disease that threatens men's health. Prostate cancer is the most common male cancer in North America and Europe, and its mortality rate is second only to lung cancer. In China, the annual incidence of prostate cancer is also increasing at a rate of about 10%. The growth of prostate tumors depends almost entirely on the androgen receptor (AR) pathway, and the androgen receptor, as the target of androgen's biological effects, has become a research hotspot in the field of biomedicine. [0003] The androgen receptor (AR) belongs to the nuclear receptor family and consists of 918 amino acid residues, which form three important structural domains, namely DNA binding d...

Claims

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Application Information

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IPC IPC(8): C07D403/14C07D401/14C07D417/14C07D409/14C07D491/107C07D471/10C07D413/14C07D405/14A61K31/506A61K31/4439A61K31/427A61K31/497A61K31/4178A61K31/422A61K31/433A61P35/00A61P13/08A61P17/10A61P17/14A61P15/00
CPCC07D403/14C07D401/14C07D405/14C07D409/14C07D413/14C07D417/14C07D471/10C07D491/107
Inventor 李德群
Owner CHENGDU BESTCHIRALBIO LIMITED LIABILITY
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