Crystal form of dydrogesterone intermediate and preparation method thereof

A kind of technology of dydrogesterone and intermediate, applied in the field of medicinal chemistry

Pending Publication Date: 2021-06-01
CHONGQING QIANTAI BIOLOGICAL MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] There is currently no relevant report on the crystal form of the compound of formula I. For the final use of this compound as a treatment or as an intermediate of dydrogesterone, it is desirable to obtain crystals with good stability and high purity. Therefore, it is necessary to Carry out comprehensive and systematic polymorphic screening to select suitable crystal forms for development

Method used

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  • Crystal form of dydrogesterone intermediate and preparation method thereof
  • Crystal form of dydrogesterone intermediate and preparation method thereof
  • Crystal form of dydrogesterone intermediate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0050] The preparation of the crystal form A of example 1 drogesterone intermediate

[0051] Add 20g of dydrogesterone intermediate, 5ml of dichloromethane, and 50ml of acetone into the reaction flask in sequence, raise the temperature to 50-60°C, keep the temperature at reflux for 1 hour, and slowly cool down to 0-10°C to crystallize for 6-8 hours. After suction filtration, the filter cake was washed with 10 ml of cooled acetone, and the filter cake was air-dried at 50-60° C. to constant weight to obtain 18 g of off-white crystals with a HPLC purity of 99.80% and a yield of 90%.

[0052] Gained crystal carries out X-ray powder diffraction (XRPD) analysis (see appendix figure 1 ), DSC analysis (see attached figure 2 ) and TGA analysis (attached image 3 ), is crystal form A.

example 2

[0053] The preparation of the crystal form A of example 2 drogesterone intermediate

[0054] Add 30g of dydrogesterone intermediate, 5ml of chloroform, and 50ml of acetone into the reaction flask in sequence, raise the temperature to 60-70°C, keep warm and reflux for 1 hour, and slowly cool down to 0-10°C to crystallize for 6-8 hours. After suction filtration, the filter cake was washed with 10 ml of cooled acetone, and the filter cake was air-dried at 50-60° C. to constant weight to obtain 17.2 g of off-white crystals with a HPLC purity of 99.85% and a yield of 86%. It was detected as crystal form A.

example 3

[0055]The preparation of the crystal form A of example 3 drogesterone intermediate

[0056] Add 30g of dydrogesterone intermediate, 5ml of tetrahydrofuran, and 70ml of acetone into the reaction flask in sequence, raise the temperature to 60-70°C, keep warm and reflux for 1 hour, and slowly cool down to 0-10°C to crystallize for 6-8 hours. After suction filtration, the filter cake was washed with 10 ml of cooled acetone, and the filter cake was air-dried at 50-60° C. to constant weight to obtain 18.2 g of off-white crystals with a HPLC purity of 99.91% and a yield of 91%. It was detected as crystal form A.

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Abstract

The invention provides a pregna-5, 7-diene-3, 20-diethylene glycol ketal crystal form and a preparation method thereof The crystal form provided by the invention is relatively stable under high temperature, high humidity and illumination, and can well avoid crystal transformation and product degradation in intermediate storage and subsequent use processes. The invention also provides a preparation method of the crystal form, and the method is simple, convenient, good in reproducibility and suitable for industrial production.

Description

Technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to a crystal form of dydrogesterone intermediate and a preparation method thereof. Background technique [0002] Dydrogesterone is 6-deshydroinverse progesterone, an oral progestin that can cause the endometrium to enter a complete secretory phase, thus preventing the risk of endometrial hyperplasia and cancer caused by estrogen. Its chemical structure is closest to natural progesterone and progesterone, but its biological activity in the body is higher than that of natural progesterone. It is effective when taken orally at a low dose and has no estrogen, androgen and adrenocorticoid effects. It does not produce heat and has no effect on lipid metabolism. impact, safety and tolerability. [0003] Pregnant-5,7-diene-3,20-diethylene glycol ketal is the key intermediate for the preparation of dydrogesterone, and its structural formula is as shown in formula (I): [0004]...

Claims

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Application Information

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IPC IPC(8): C07J21/00C07J7/00
CPCC07J21/006C07J7/002C07B2200/13
Inventor 徐进李敢张有理郭明袁建栋
Owner CHONGQING QIANTAI BIOLOGICAL MEDICINE
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