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Abiraterone ester derivatives as well as preparation method and application thereof

A technology for drugs and compounds, applied in the field of medicine, can solve the problems of insufficient oral bioavailability, poor oral absorption, large oral dose, etc., and achieve the effect of improving oral bioavailability, high lipid solubility, and reducing oral dose.

Pending Publication Date: 2022-01-14
南京易腾药物研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the poor oral absorption of abiraterone acetate, the oral bioavailability is considered to be less than 10%, so the oral dose of abiraterone acetate is relatively large

Method used

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  • Abiraterone ester derivatives as well as preparation method and application thereof
  • Abiraterone ester derivatives as well as preparation method and application thereof
  • Abiraterone ester derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] [(3S,8R,9S,10R,13S,14S)-10,13-Dimethyl-17-(3-pyridyl)-2,3,4,7,8,9,11,12,14, Synthesis of 15-Decahydro-1H-Cyclopenta[a]phenanthrene-3-yl]octanoate (Compound 1)

[0047]

[0048] Add 2.16g of n-octanoic acid and 10g of N,N-dimethylformamide into a 25mL single-necked bottle, stir to dissolve, add 1.9g of diisopropylcarbodiimide, and stir for 10min to obtain an active ester solution. Take another 100mL three-neck bottle, add 20g of N,N-dimethylformamide, add 3.5g of abiraterone under stirring, add the aforementioned active ester solution dropwise to the obtained suspension, and add 1.84g of dimethicone Aminopyridine, stirred at room temperature. After the reaction was completed, the reaction solution was poured into 200 mL of water, and extracted three times with ethyl acetate. The organic phases were combined, washed three times with saturated aqueous sodium chloride solution, and then dried with anhydrous sodium sulfate. The crude product obtained after concentratio...

Embodiment 2

[0052] [(3S,8R,9S,10R,13S,14S)-10,13-Dimethyl-17-(3-pyridyl)-2,3,4,7,8,9,11,12,14, Synthesis of 15-Decahydro-1H-Cyclopenta[a]phenanthrene-3-yl]nonanoate (Compound 2)

[0053]

[0054] Referring to the synthesis method of Example 1, using n-nonanoic acid to react with abiraterone, compound 2 was prepared with a yield of 37%.

[0055] 1 H NMR (400MHz, Chloroform-d) δ8.64 (d, J = 2.0Hz, 1H), 8.48 (dd, J = 4.8, 1.5Hz, 1H), 7.66 (dt, J = 7.9, 1.9Hz, 1H) ,7.24(dd, J=7.9,4.8Hz,1H),6.01(dd,J=3.0,1.7Hz,1H),5.44(d,J=5.1Hz,1H),4.65(tdd,J=10.4,6.0 ,4.2Hz,1H),2.42–2.33(m,2H),2.33–2.25(m,3H),2.14–2.02(m,3H),1.94–1.42(m,12H),1.41–1.24(m,10H ),1.24–1.09(m,5H),1.07(s,3H),0.90(t,J=6.8Hz,3H).

[0056] MS(ESI)m / z=490.6[M+H] +

Embodiment 3

[0058] [(3S,8R,9S,10R,13S,14S)-10,13-Dimethyl-17-(3-pyridyl)-2,3,4,7,8,9,11,12,14, Synthesis of 15-Decahydro-1H-Cyclopenta[a]phenanthrene-3-yl]decanoate (Compound 3)

[0059]

[0060] Referring to the synthesis method of Example 1, using n-capric acid to react with abiraterone, compound 3 was prepared with a yield of 48%.

[0061] 1 H NMR (400MHz, Chloroform-d) δ8.64 (d, J = 1.9Hz, 1H), 8.48 (dd, J = 4.8, 1.4Hz, 1H), 7.67 (dt, J = 7.9, 1.8Hz, 1H) ,7.24(dd,J=7.9,4.8Hz,1H),6.01(dd,J=3.0,1.7Hz,1H),5.44(d,J=5.0Hz,1H),4.71–4.59(m,1H), 2.39–2.33(m,2H),2.33–2.25(m,3H),2.14–2.02(m,3H),1.94–1.85(m,2H),1.84–1.42(m,11H),1.40–1.24(m ,12H),1.24–1.09(m,5H),1.07(s,3H),0.90(t,J=6.8Hz,3H).

[0062] MS(ESI)m / z=504.6[M+H] +

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Abstract

The invention relates to abiraterone ester derivatives represented by a general formula I, a pharmaceutical composition containing the abiraterone ester derivatives and an application of the abiraterone ester derivatives and the pharmaceutical composition to treatment and / or prevention of tumors. The groups in the formula are defined in the specification.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to an abiraterone ester derivative, a stereoisomer or a pharmaceutically acceptable salt thereof, and an application thereof in preparing medicines related to the prevention and treatment of cancer. Background technique [0002] Prostate cancer is a common malignant and fatal cancer in men. Androgens are key factors in the development of prostate cancer. Enolone and progesterone are sequentially catalyzed by 17α-hydroxylase and C17,20-lyase to form DHEA and androstenedione. DHEA and androstenedione are the precursors of testosterone, which are then converted into testosterone and dihydrotestosterone through a multi-step catalytic process. CYP17 is a cytochrome P450 enzyme that catalyzes the activity of two independent regulators of steroid 17α-hydroxylase and C17,20 lyase, thereby regulating androgen synthesis. [0003] Abiraterone acetate is a prodrug of abiraterone, which is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J43/00A61P13/08A61P35/00A61K31/58
CPCC07J43/003A61P13/08A61P35/00
Inventor 王玉斌王亮张英
Owner 南京易腾药物研究院有限公司
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