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

Salt of 93beta)-17-(1H-benzimidazole-1-yl)androst-5,16-diene-3-ol and preparation method thereof

A technology of benzimidazole and androster, applied in the field of -17-androsta-5, can solve the problems of time-consuming, high dosage, complicated amorphous dispersion preparation process, etc., achieves strong economic value, high solubility, and is suitable for long-term storage and the effect of industrial production

Inactive Publication Date: 2016-07-06
CRYSTAL PHARMATECH CO LTD
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, even if free state amorphous preparations are used to improve the drug efficacy, the dose is still very high, and the amorphous form has the problem of crystal transformation during storage and transportation, and the preparation of amorphous dispersion preparations has many disadvantages such as complicated process and time-consuming. So finding a salt that can improve solubility and reduce dosage is of great significance

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
  • Salt of 93beta)-17-(1H-benzimidazole-1-yl)androst-5,16-diene-3-ol and preparation method thereof
  • Salt of 93beta)-17-(1H-benzimidazole-1-yl)androst-5,16-diene-3-ol and preparation method thereof
  • Salt of 93beta)-17-(1H-benzimidazole-1-yl)androst-5,16-diene-3-ol and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] The preparation method of the phosphate crystal form A of the compound of formula (I):

[0094] Suspend 206.1 mg of the compound of formula (I) in 10 mL of acetonitrile, add 0.044 mL of 35% phosphoric acid aqueous solution, stir and react at room temperature (25±2°C) for 12 hours, and collect the solid to obtain it.

[0095] It was detected that the obtained solid was crystal form A of phosphate, and its X-ray powder diffraction data included but not limited to the data in Table 1. Its XRPD pattern is as follows figure 1 , and its DSC graph is shown in figure 2 , and its TGA figure is shown in image 3 .

[0096] The crystal form A of the phosphate salt was placed at 5°C for 90 days and then subjected to X-ray powder diffraction test. The obtained XRPD pattern is as follows Figure 4 shown.

[0097] The crystalline form A of the phosphate was placed under the conditions of 25°C and 60% relative humidity for 90 days and then subjected to X-ray powder diffraction te...

Embodiment 2

[0103] The preparation method of formula (I) compound phosphate crystal form A:

[0104] Suspend 10.1 mg of the compound of formula (I) in 0.5 mL of ethyl acetate, add 0.002 mL of 35% phosphoric acid solution, stir and react at room temperature (25±2°C) for 12 hours, and collect the solid to obtain it.

[0105] It was detected that the obtained solid was crystal form A of phosphate, and its X-ray powder diffraction data included but not limited to the data in Table 2.

[0106] Table 2

[0107]

[0108]

[0109]

Embodiment 3

[0111] The preparation method of formula (I) compound tartrate crystal form A:

[0112] Suspend 10.5 mg of the compound of formula (I) in 0.5 mL of acetone, add 5.8 mg of tartaric acid, stir and react at room temperature (25±2° C.) for 12 hours, and collect the solid.

[0113] After testing, the obtained solid is crystal form A of tartrate salt, and its X-ray powder diffraction data include but not limited to the data in Table 3. Its XRPD pattern is as follows Figure 7 , and its DSC graph is shown in Figure 8 , and its TGA figure is shown in Figure 9 .

[0114] H of tartrate crystal form A 1 -NMR picture as Figure 10 As shown, NMR data show that the salt is a compound of formula (I) and tartaric acid in a molar ratio of 1:1.

[0115] The crystal form A of the tartrate salt was placed at 5°C for 90 days and then subjected to X-ray powder diffraction test. The obtained XRPD pattern is as follows Figure 11 shown.

[0116] The crystal form A of the tartrate salt was p...

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

No PUM Login to View More

Abstract

The invention relates to crystal forms of phosphate, tartrate and citrate of (3beta)-17-(1H-benzimidazole-1-yl)androst-5,16-diene-3-ol and a preparation method of the compound. The crystal forms of phosphate, tartrate and citrate of a compound shown in a formula (I) have beneficial properties of high solubility, low hygroscopicity, good stability, simple technology and easiness for operation, are applicable to storage and industrial production and have important value on optimization and development of the medicine in future. The formula (I) is described in the specification.

Description

technical field [0001] The invention relates to the field of chemistry and medicine, in particular to a salt of (3β)-17-(1H-benzimidazol-1-yl)androst-5,16-dien-3-ol and a preparation method thereof. Background technique [0002] Galeterone, whose chemical name is (3β)-17-(1H-benzimidazol-1-yl)androst-5,16-dien-3-ol, was developed by Japan Tokai Pharmaceutical Co., Ltd. Drugs for the treatment of castration resistant prostate cancer populations. Galeterone works by blocking the antigen receptor signaling pathway in prostate cancer. Antigen receptor signaling promotes prostate cancer growth. Typically, this signaling pathway is activated by the binding of androgen or androgens, such as testosterone or the more potent male androgen dihydrotestosterone (DHT), to the ligand-binding domain of the androgen receptor in prostate cancer cells. The drug is currently in clinical phase III, and its structure is shown in formula (I): [0003] [0004] At present, patent CN103813794...

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): C07J43/00A61K31/58A61P35/00
CPCC07B2200/13C07J43/003A61P13/08A61P35/00
Inventor 陈敏华张炎锋刁小娟
Owner CRYSTAL PHARMATECH 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