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Production process capable of industrially synthesizing dydrogesterone

A production process, the technology of dydrogesterone, which is applied in the field of industrialized preparation of dydrogesterone raw materials, can solve the problems of progesterone imitation in regions where it cannot be imitated, it is not easy to scale up, and the yield is not high, and achieves important economic and social value, Easy to scale up production and less reaction by-products

Active Publication Date: 2020-02-21
GUANGXI NORMAL UNIV
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  • Application Information

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Problems solved by technology

However, some of the synthetic processes that have been disclosed all have defects such as low yield, large pollution, and especially not easy to scale up. As a result, except for Abbott in the United States, it has been able to monopolize the production of the drug, and domestic regions have not been able to achieve it due to technical reasons. The imitation of progesterone, so the development of a new process for the preparation of dydrogesterone that is easy to scale up has important economic and social value

Method used

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  • Production process capable of industrially synthesizing dydrogesterone
  • Production process capable of industrially synthesizing dydrogesterone
  • Production process capable of industrially synthesizing dydrogesterone

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preparation example Construction

[0076] The preparation method of this embodiment is shown in Scheme 10;

[0077]

[0078] Scheme 10

Embodiment 1

[0080] Weigh 2kg of progesterone (compound 2) into a 20L reaction tank, then add 4L of ethylene glycol, 5.5L of tetrahydrofuran, 0.1L of acetyl chloride in sequence, slowly add 2L of trimethyl orthoformate, and control the temperature at 35±5 ℃, react for 2 hours ± 10 minutes, add 0.2 L of pyridine to quench the reaction, cool at -10 °C ± 5 °C for 0.5 hours, filter, wash with 6 L of water and 3 L of acetone in turn, drain, and dry in vacuum below 40 ° C to obtain the compound 3 crude product.

[0081] Put the crude product of compound 3 into a 20L reaction tank, add 6L of acetone and 4ml of pyridine, heat in a water bath to reflux, stir for 1 hour, cool at -10°C±5°C for 0.5 hour, filter with suction, and dry in vacuo at 40°C overnight to obtain compound 3. Pure product, yield 91%.

Embodiment 2

[0083] Respectively replace tetrahydrofuran with methyl tert-butyl ether, isopropyl ether, glyme or glyme, others are the same as Example 1, and the productive rate of compound 3 is respectively 80%, 83%, 89% and 85% %.

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Abstract

The invention discloses a production process capable of industrially synthesizing dydrogesterone. Easily available progesterone is used as a raw material, and dydrogesterone is prepared through the steps of carbonyl protection, bromination, debromination, photochemical ring-opening reaction, photochemical ring-closing reaction, deprotection and double bond isomerization. The production process hasthe advantages of easily available initial raw materials, and easiness in implementation of each step and higher yield; the production process is simple and convenient to operate, is green and environment-friendly, and can be easily amplified to industrial production.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a process for the industrialized preparation of dydrogesterone bulk drug. Background technique [0002] Dydrogesterone 1, also known as dehydroprogesterone, chemically named 9β, 10α-pregna-4,6-diene-3,20-dione, CAS number: 152-62-5. Dydrogesterone is not only widely used in miscarriage protection and prevention of miscarriage, but also widely used in the treatment of various diseases caused by endogenous progesterone deficiency, such as: dysmenorrhea, endometriosis, secondary amenorrhea, irregular menstrual cycle uterine bleeding, premenstrual syndrome, threatened miscarriage or habitual miscarriage caused by progesterone deficiency, infertility caused by corpus luteum insufficiency Motong (Femoston Estradiol Tablets / Estradiol Dydrogesterone Tablets Composite Packaging) two dosage forms, originally developed by Solvay Pharmaceuticals in the Netherlands, launched globally ...

Claims

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Application Information

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IPC IPC(8): C07J7/00
CPCC07J7/002
Inventor 潘成学苏桂发于成龙覃江克李永怡杨倩方淑君
Owner GUANGXI NORMAL UNIV
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