Preparation method of delmadinone

A technology of demagogesterone and equine progesterone, which is applied in the directions of steroids, organic chemistry, etc., can solve the problems of many side reactions, many impurities and high production costs

Inactive Publication Date: 2019-03-12
HUNAN KEREY BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 s...

Method used

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  • Preparation method of delmadinone
  • Preparation method of delmadinone
  • Preparation method of delmadinone

Examples

Experimental program
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Effect test

Embodiment 1

[0054] A: Preparation of Hydroxycyanide

[0055] 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%.

[0056] B: Preparation of 1,6-didehydro-17a-hydroxyprogesterone

[0057] In a 1000ml three-necked flask, add 35g of magnesium powder...

Embodiment 2

[0066] A: Preparation of Hydroxycyanide

[0067] 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%.

[0068] B: Preparation of 1,6-didehydro-17a-hydroxyproge...

Embodiment 3

[0078] A: Preparation of Hydroxycyanide

[0079] 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%.

[0080] B: Preparation of 1,6-didehydro-17a-hydroxyprogesterone...

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Abstract

The invention provides a preparation method of delmadinone. The preparation method comprises the steps: 1,4-androstadienedione, namely IDD is adopted as a raw material; firstly, 17-position ketone inIDD molecules reacts with acetone cyanohydrin in a first organic solvent under alkali catalysis, and beta-hydroxyl and alpha-cyan are introduced in the 17 position to obtain hydroxyl cyanide; then thehydroxyl cyanide is prepared under presence of methylmagnesium halide, a second organic solvent and acid to obtain 1,6-didehydro-17a-hydroxyprogesterone; and then 6-position epoxy is synthesized, andthen 6-position chloride is synthesized to obtain the delmadinone. Compared with a traditional synthesis method of delmadinone and delmadinone acetate, the preparation method has the multiple advantages that process operation is easy and convenient, production is economical and environmentally friendly, the total yield of synthesis is high, the product quality is good, and the production cost islow.

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 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 tetrachlorobenzoqui...

Claims

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Application Information

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IPC IPC(8): C07J7/00
CPCC07J7/0045
Inventor 左前进吴来喜羊向新
Owner HUNAN KEREY BIOTECH
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