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Abiraterone precursor compound as well as preparation method and application thereof

A compound and drug technology, applied in the field of abiraterone precursor compounds and their preparation, can solve the problems of stimulating tumor growth, unable to inhibit androgen, etc., and achieve the effects of increasing AUC, excellent water solubility, and improving bioavailability

Pending Publication Date: 2021-10-22
SUZHOU AIHE PHARM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In men with prostate cancer, the hormone testosterone stimulates tumor growth. Castration therapy, including drugs or surgery, can reduce testosterone production or block the effects of testosterone, but this treatment does not suppress androgen production elsewhere in the body , prostate cancer can continue to grow

Method used

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  • Abiraterone precursor compound as well as preparation method and application thereof
  • Abiraterone precursor compound as well as preparation method and application thereof
  • Abiraterone precursor compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The synthesis of embodiment 1 compound LHY-AB614

[0045]

[0046] Take a dry 500ml round bottom flask, add abiraterone (10g, 28.6mmol, 1.0eq), and add 150mL of CH 2 Cl 2 Dissolve, add CDI (14g, 85.8mmol, 3.0eq) and react at room temperature. After 8 hours, the reaction was detected by TLC (PE:EA=1:1), and the raw materials disappeared completely. Concentrate the reaction solution, add 100 mL of dry THF, stir at room temperature for 30 min, filter with suction, and wash the filter cake with dry THF (50 mL*3). The solid was collected and dried to obtain compound Cpd-1 (10 g, 22.6 mmol) with a yield of 79%.

[0047] Take a dry 250mL round bottom flask, add compound Cpd-1 (10g, 22.6mmol, 1.0eq) and KOH (250mg, 4.5mmol, 0.2eq), add 100mL toluene, and finally add 2-[2-(dimethylamino ) Ethoxyl] ethanol (4.1mL, 29.4mmol, 1.3eq), react at 60°C overnight, TLC detects the reaction, and the raw material disappears completely. The solvent was spin-dried, and the resulting s...

Embodiment 2

[0050] The synthesis of embodiment 2 compound LHY-AB615

[0051] Dissolve formula I (1g) in 10mL ethyl acetate at room temperature, add an equivalent amount of phosphoric acid, after the reaction is complete, add 20mL petroleum ether, and the product LHY-AB615 is precipitated. Suction filtration and drying to obtain the crude product of LHY-AB615.

[0052] At room temperature, dissolve the crude product of LHY-AB615 (1g) in 1.2mL of methanol, slowly add 25mL of tetrahydrofuran dropwise, stir vigorously at room temperature, a white solid is precipitated, and the filter cake is dried after suction filtration to obtain relatively pure LHY-AB615 (820mg, purity 99.5%).

Embodiment 3

[0053] The synthesis of embodiment 3 compound LHY-AB616

[0054] Dissolve formula I (1 g) in 10 mL of ethyl acetate at room temperature, add an equivalent amount of methanesulfonic acid, after the reaction is complete, add 20 mL of petroleum ether, and the product LHY-AB616 is precipitated. Suction filtration and drying to obtain the crude product of LHY-AB616.

[0055] At room temperature, dissolve the crude product of LHY-AB616 (1g) in 1.2mL of methanol, slowly add 25mL of tetrahydrofuran dropwise, stir vigorously at room temperature, a white solid precipitates, and the filter cake is dried after suction filtration to obtain relatively pure LHY-AB616 (790mg, purity 99.7%).

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PUM

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Abstract

The invention discloses a precursor compound of a novel abiraterone medicine as well as a preparation method and application thereof. The structure of the compound is shown as a formula I in the specification. The invention further provides a preparation method of the compound shown in the formula I, hydrochloride of the compound shown in the formula I, a preparation method of the compound and hydrochloride and application of the compound and hydrochloride in the preparation of CYP17 enzyme inhibitor drugs. The compound provided by the invention provides improved oral bio-availability and pharmacokinetic characteristics, can be used as a human body CYP17 enzyme inhibitor, and can be used for treating urogenital or androgen-related diseases, such as cancers or other androgen-related diseases, including prostatic cancer, breast cancer, prostatic hyperplasia and the like.

Description

technical field [0001] The invention belongs to the field of precursor compounds, in particular to an abiraterone precursor compound and its preparation method and application. Background technique [0002] Prostate cancer is the most common malignant tumor worldwide, and its incidence increases with age. The current population aging trend has led to a rapid increase in the number of prostate cancer patients. Prostate cancer has grown rapidly in the past 10 years in our country, ranking sixth among men. In the United States, the incidence of males is the first, and the death rate is the second. About 218,000 men in the United States are diagnosed with prostate cancer each year, and 32,000 die from it, according to the American Cancer Society. [0003] In China, prostate cancer used to be a relatively rare disease, but the incidence of the disease has also shown an upward trend in recent years. Epidemiological data show that the incidence of prostate cancer in China increa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J43/00A61K31/58A61P35/00A61P13/08
CPCC07J43/003A61P35/00A61P13/08
Inventor 雷昊言
Owner SUZHOU AIHE PHARM TECH CO LTD
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