Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Abiraterone acetate oxalate and purification method of abiraterone acetate

A technology of abiraterone acetate and oxalate is applied in the purification field of abiraterone acetate oxalate and abiraterone acetate, can solve problems such as difficult operation, air pollution, equipment corrosion, etc. The effect of reducing production costs and equipment requirements

Active Publication Date: 2013-04-24
LIANYUNGANG RUNZHONG PHARMA CO LTD +1
View PDF4 Cites 11 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Abiraterone acetate trifluoromethanesulfonate obtained by the method has higher purity and better color than Abiraterone acetate mesylate, overcomes the defect in CN101044155, and simplifies the purification process, but because trifluoromethanesulfonic acid is expensive , easy to produce acid mist, so the reaction in CN102030798 can only be controlled below low temperature (5°C), which is unfavorable for operation, and trifluoromethanesulfonic acid is also highly corrosive, which seriously corrodes equipment, and post-processing and production operations are difficult , the air pollution is serious, so it is very unsuitable for large-scale industrial production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Abiraterone acetate oxalate and purification method of abiraterone acetate
  • Abiraterone acetate oxalate and purification method of abiraterone acetate
  • Abiraterone acetate oxalate and purification method of abiraterone acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation of embodiment 1 Abiraterone acetate crude product

[0031]

[0032] Dissolve 200 g of dehydroepiandrosterone acetate in 2 L of dry dichloromethane under stirring, and add Tf dropwise at 15-20°C 2 O 206g, after 0.5h dropwise, slowly add diisopropylethylamine (i-Pr 2 NEt) 96g, after 2h dripping, continue to react for 3h. Add ice water (1.5L) to quench, separate the layers, extract the aqueous phase with dichloromethane (500ml), combine the organic phases, wash with 2N hydrochloric acid and 1.5L of water successively, dry over anhydrous sodium sulfate, and concentrate to obtain a purple-black oil The product is about 280g (AB-2).

[0033]

[0034] AB-2(280g), THF(2L), Pd(PPh 3 ) 2 Cl 2 (3.7g), diethyl-(3-pyridine)borane (96g) and 2M Na 2 CO 3 (1L). Heat to an external temperature of 80°C, and react for 4 to 5 hours. Stand still to separate the liquids, extract the lower aqueous phase with ethyl acetate (1L), remove most of the THF from the up...

Embodiment 2

[0035] The preparation of embodiment 2 abiraterone acetate oxalate and the purification of abiraterone acetate

[0036] (1) Preparation of Abiraterone Acetate Oxalate

[0037]

[0038] Add 1.5 L of acetone to the crude product of abiraterone acetate (260 g), stir to dissolve, add 67 g of oxalic acid at 50 ° C, continue stirring for 1 h, then lower to room temperature and stir for 2 h. Suction filtration, the filter cake was rinsed with acetone, dried under reduced pressure to obtain off-white solid, i.e. abiraterone acetate oxalate 144.9g (AB-3), total yield 49.7% (calculated based on starting material AB-1 ), the HPLC purity detection is 96.1%.

[0039] Differential scanning thermogram analysis (DSC) of abiraterone acetate oxalate:

[0040] Instrument model: NETZSCH DSC 204S1

[0041] Experimental conditions: crucible type: standard aluminum crucible (needle piercing)

[0042] Sweep gas: N 2 20mL / min; protective gas: N 2 70mL / min.

[0043] Temperature range: 100--30...

Embodiment 3～8

[0058] The preparation of embodiment 3~8 abiraterone acetate oxalate and the purification of abiraterone acetate

[0059] Concrete operation is tested according to the method of embodiment 2, and reaction consumption and condition are operated by table 1.

[0060] Table 1

[0061]

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
purityaaaaaaaaaa
Login to View More

Abstract

The invention relates to an abiraterone acetate oxalate and a purification method of abiraterone acetate. Oxalate and an abiraterone acetate crude product are subjected to a reaction to obtain abiraterone acetate oxalate; and then the abiraterone acetate oxalate is subjected to a dissociation reaction to obtain abiraterone acetate.

Description

technical field [0001] The invention relates to a novel abiraterone acetate salt, a preparation method thereof, and a purification method of abiraterone acetate. Background technique [0002] Abiraterone acetate is a key enzyme in androgen synthesis, 17α-hydroxylase-C17, 20-lyase (also known as steroid 17α-monooxygenase inhibitor or human cytochrome P450 17α ) is a potent and selective oral inhibitor for the treatment of prostate cancer. On April 28, 2011, the FDA approved abiraterone acetate in combination with prednisone for the treatment of metastatic castration-resistant prostate cancer in patients previously treated with docetaxel chemotherapy. The chemical name of Abiraterone acetate is (3β)-17-(3-pyridyl)-androst-5,16-dien-3-ol acetate, and its structural formula is as follows: [0003] [0004] The synthetic method of abiraterone acetate has prior art disclosure (WO9320097, WO9509178, J.Med.Chem, 1995, Vo38 (13), 2463-2471, Org.Prep.Proced.Int., 1997,29 (1) , 1...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07J43/00C07C55/07C07C51/41
Inventor 郭猛王华张喜全
Owner LIANYUNGANG RUNZHONG PHARMA CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com