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Method for preparing delmadinone acetate product

A technology of horse progesterone acetate and dexamethasone, which is applied in the directions of organic chemistry, steroids, organic chemistry, etc., can solve the problems of many impurities, high production cost, low product purity and the like

Inactive Publication Date: 2019-02-22
HUNAN KEREY BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When preparing Dimagestrol acetate at last, adopt DDQ to make Dimagestrol acetate 1-position dehydrogenation in dioxane, environmental protection is also difficult to handle, there is side effect in the whole process. There are many problems such as many reactions, many impurities, low product purity, difficult environmental protection treatment, high production cost, etc.

Method used

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  • Method for preparing delmadinone acetate product
  • Method for preparing delmadinone acetate product
  • Method for preparing delmadinone acetate product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] A: Preparation of Hydroxycyanide

[0053] In a 1000ml three-neck flask, add 100g of starting material IDD and 250ml of acetone cyanohydrin, control the temperature to 40-45°C, stir to completely dissolve IDD, then control the temperature at 20-25°C, and slowly add 2% carbonic acid dropwise Sodium alkali aqueous solution, about 2-2.5 hours to drop, then keep warm at 25-30°C for 2-3 hours, TLC to confirm the reaction end point, after the reaction, concentrate under reduced pressure to recover 90-95% of the solvent acetone cyanohydrin, and the remaining Thing is cooled to 20~25 ℃, then adds 500ml tap water water analysis, filters, and filtrate is sent to waste water treatment station for processing, and filter cake is crystallized with 500ml 40% alcohol aqueous solution, obtains hydroxycyanide 98.6g, HPLC content 98.2%, weight yield 98.6%.

[0054] B: Preparation of 1,6-didehydro-17a-hydroxyprogesterone

[0055] In a 1000ml three-neck flask, add 35g of magnesium powder a...

Embodiment 2

[0064] A: Preparation of Hydroxycyanide

[0065] In a 1000ml three-neck flask, add 100g of starting material IDD, 50ml of acetone cyanohydrin, and 500ml of methanol, control the temperature to 40-45°C, stir to completely dissolve IDD, then control the temperature at 20-25°C, slowly add 2 % sodium hydroxide alkaline aqueous solution, drop it in about 2-2.5 hours, then keep warm at 25-30°C for 2-3 hours, TLC confirms the reaction end point, after the reaction, concentrate under reduced pressure to recover 90-95% methanol and acetone The mixed solvent of cyanohydrin was applied mechanically, the residue was cooled to 20-25° C., and then 500 ml of tap water was added for water analysis, filtered, and the filtrate was sent to the waste water treatment station for treatment. The filter cake was crystallized with 500 ml of 40% alcohol aqueous solution to obtain 97.8 g of hydroxycyanide. HPLC content 98.5%, weight yield 97.8%.

[0066] B: Preparation of 1,6-didehydro-17a-hydroxyproge...

Embodiment 3

[0076] A: Preparation of Hydroxycyanide

[0077] In a 1000ml three-necked flask, add 100g of starting materials IDD, 50ml of acetone cyanohydrin, and 500ml of DME, control the temperature to 40-45°C, stir to completely dissolve IDD, then control the temperature at 20-25°C, and slowly add 2% Triethylamine alkali aqueous solution, drop it in about 2-2.5 hours, then keep warm at 25-30°C for 2-3 hours, TLC confirms the reaction end point, after the reaction, concentrate under reduced pressure to recover 90-95% of DME and acetone cyanide The mixed solvent of alcohol was applied mechanically, the residue was cooled to 20-25°C, and then 500ml of tap water was added for water analysis, filtered, and the filtrate was sent to the waste water treatment station for treatment. The filter cake was crystallized with 500ml of 40% alcohol aqueous solution to obtain 96.2g of hydroxycyanide, HPLC Content 98.2%, weight yield 96.2%.

[0078] B: Preparation of 1,6-didehydro-17a-hydroxyprogesterone...

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Abstract

The invention provides a method for preparing a delmadinone acetate product. The method comprises the following steps: by taking IDD (1,4-Androstadienedione) as a raw material, firstly, enabling 17-site ketone in IDD molecules to react with acetone cyanohydrins in a first organic solvent under catalysis of an alkali, and introducing beta-hydroxyl and alpha-cyan into the 17-site so as to obtain hydroxyl cyanogens; preparing 1,6-bidehydrogenation-17a-hydroxyl progesterone from the hydroxyl cyanogens in the presence of methyl magnesium halide, a second organic solvent and an acid; further synthesizing a 6-site epoxy substance, further synthesizing 6-site chloride so as to obtain delmadinone, and finally carrying out 17-site esterification so as to obtain delmadinone acetate; and further carrying out heating backflow decoloring and recrystalization on the obtained delmadinone acetate with activated carbon in lower-carbon alcohol with the carbon number of smaller than 4, thereby obtaining the delmadinone acetate product. Compared with a conventional synthesis method, the method provided by the invention has multiple advantages of being simple and convenient in process operation, economic and environmental-friendly in production, high in total synthesis yield, high in product quality, low in production cost, and the like.

Description

technical field [0001] The invention belongs to the preparation process of steroid hormone drugs, and in particular relates to a preparation method of a progesterone drug diamagestrol acetate product and an intermediate diamagestrol. Background technique [0002] Dimagestrol acetate, chemical name: 6-chloro-17a-acetoxy-pregna-1,4,6-,triene-3,20-dione, is a high-efficiency progestogen drug with Strong milk-excretion effect, clinically mainly used for breast-feeding women with poor milk excretion to promote milk excretion during breast-feeding. It is most widely used in cattle and sheep breeding to promote milk excretion of dairy cows and milk sheep. Due to its good effect and low side effects, the market application prospect is broad. The traditional production method of dimaprogesterone acetate is to use 17a hydroxyprogesterone as a raw material, diacetylate through acetic anhydride, chlorinate bleaching powder, etherify triethyl orthoformate, and remove DDQ (or tetrachloro...

Claims

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Application Information

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IPC IPC(8): C07J7/00C07J41/00C07J71/00
CPCC07B2200/07C07J7/0045C07J41/0094C07J71/001
Inventor 谢来宾吴来喜胡爱国
Owner HUNAN KEREY BIOTECH
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