Unlock instant, AI-driven research and patent intelligence for your innovation.

17aª‡-d-high valent alkyneestradiol-3-ethyl ester and its synthesis and preparation method, pharmaceutical composition using the said compound as active ingredient

A technology for homoethinyl estradiol and compounds, the application in medicine, the synthesis and preparation of chemically synthesized pharmaceutical monomer components, the field of synthesis and preparation of 17aα-D-homethinyl estradiol-3-ethyl ester, can solve the problem of synthesis long steps

Inactive Publication Date: 2006-05-03
INST OF RADIATION MEDICINE CHINESE ACADEMY OF MEDICAL SCI
View PDF1 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to improve the radiation protection potency of ethinyl estradiol and reduce its toxic and side effects, we carried out structural modification on it, designed and synthesized a compound in which the D-five-membered ring in the steroid hormone structure was extended to a six-membered ring——17aα-D-high Ethinyl estradiol-3-ethyl ester, longer synthetic steps

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
  • 17aª‡-d-high valent alkyneestradiol-3-ethyl ester and its synthesis and preparation method, pharmaceutical composition using the said compound as active ingredient

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0165] (1) Synthesis of estrone-3-ethyl ester (I):

[0166] Stir 100g of estrone, 66ml of pyridine, and 66ml of acetic anhydride at a constant temperature of 25°C for 6hrs, add a drying tube, slowly pour into 600ml of water, a white solid precipitates, leave it for 2hrs, filter it with suction, wash with a large amount of hot water until there is no pyridine smell, and dry it at 60°C Dry at °C, weight 110.0g, mp: 119-121 °C, monitored by thin layer chromatography as a single component. Yield 94.8%.

[0167] (2) Synthesis of 17-cyanoestradiol-3-ethyl ester (II):

[0168] Stir 110.0g (0.352mole) estrone-3-acetate, 220g KCN, 1830ml 95% ethanol, and 950ml glacial acetic acid at a constant temperature of 25°C for 24hrs, then at a constant temperature of 75°C for 1hr, remove and let cool, and pour into 6000ml of water , precipitated a white precipitate, suction filtered, rinsed with water, drained, dried at 60°C, and weighed 110.5g. TLC shows two components, the reaction is not c...

Embodiment 2

[0177] (1) Synthesis of estrone-3-ethyl ester (I):

[0178]Stir 100g (0.37mole) of estrone, 66ml of pyridine, and 66ml of acetic anhydride at a constant temperature of 25°C for 6hrs, add a drying tube, slowly pour into 600ml of water, a white solid precipitates, leave it for 2hrs, filter with suction, wash with a large amount of hot water until no pyridine is removed smell, dried at 60°C, weight 112.0g, mp: 119-121°C, yield 96.5%.

[0179] (2) Preparation of diazomethane:

[0180] In a 500ml flask, add 60ml of 50% NaOH solution and 200ml of ether, the mixture is cooled to 5°C, and 20.6g (0.2mole) of nitrosomethylurea is added, and stirred gently with a stirring bar for 4 hours, The ether layer was pale yellow, and the ether layer was removed with a separatory funnel, and directly proceeded to the next reaction.

[0181] (3) Synthesis of D-homoestrolone-3-ethyl ester (III):

[0182] Add 62.4g (0.20mole) into a 1000ml flask, add 300ml of ethanol and stir to dissolve, cool to ...

Embodiment 3

[0189] Take 50.0g of 17aα-D-homoethinyl estradiol-3-ethyl ester, 50.0g of medicinal starch, appropriate amount of 50% ethanol, granulate, granulate, dry, and put into 2# capsules, each containing 17aα-D- Homoethinyl estradiol-3-ethyl ester 0.1g.

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 discloses the synthesis, spectral analysis structure validation, stability research, female activity research, and application of the drug compound contained 17a alpha -D-homoethinyloestradiol -3-ethly ester, which is obtained by acetylizing, ring enlarging and ethinylating the material of estrophenolic ketone. The research shows: this compound has obvious anti-radiation and protecting hematopoiesis function as well as anticancer, and can be applied in opposite new drug.

Description

Technical field: [0001] The 17aα-D-homoethinyl estradiol-3-ethyl ester and its synthesis and preparation technology of the present invention belong to the synthesis and preparation technology of chemically synthesized drug monomer components in the field of medicine and chemical industry. In particular, it relates to the synthesis and preparation method of 17aα-D-homoethinyl estradiol-3-ethyl ester, and its application in the preparation of drugs for radiation protection, anti-tumor, and hematopoietic function protection. Background technique: [0002] Estrogenic compounds have been studied for decades and have certain biological effects, but their applications are often limited due to high estrogen activity and large side effects. Estrogenic compounds have good preventive and therapeutic effects on radiation injury. The research on estrogen as an anti-radiation drug has a history of nearly 60 years abroad. Since the 1870s in China, it has been discovered that ethinyl estra...

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): C07J63/00A61K9/08A61K9/20A61K9/28A61K9/48A61K9/52A61K31/56A61P17/16C07J75/00
Inventor 周则卫王月英李志旺王汝勤赵云庭沈秀刘培勋胡璧张良安
Owner INST OF RADIATION MEDICINE CHINESE ACADEMY OF MEDICAL SCI