Method for preparing delmadinone acetate

The technology of horse progesterone acetate and dexamethasone is applied in the field of preparation of steroid hormone drugs, and can solve the problems of many side reactions, many impurities and high production cost

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

Examples

Experimental program
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Effect test

Embodiment 1

[0055] A: Preparation of Hydroxycyanide

[0056] 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%.

[0057] B: Preparation of 1,6-didehydro-17a-hydroxyprogesterone

[0058] In a 1000ml three-neck flask, add 35g of magnesium powder a...

Embodiment 2

[0067] A: Preparation of Hydroxycyanide

[0068] 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%.

[0069] B: Preparation of 1,6-didehydro-17a-hydroxyproge...

Embodiment 3

[0079] A: Preparation of Hydroxycyanide

[0080] 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%.

[0081] B: Preparation of 1,6-didehydro-17a-hydroxyprogesterone...

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Abstract

The invention provides a method for preparing delmadinone acetate. The method comprises the following steps that 1,6-didehydro-17a-hydroxyprogesterone is adopted as a raw material to first synthesizea 6-position epoxide, then the epoxide is heated, refluxed, discolored and re-crystallized by using active carbon in lower alcohol of C4 or less to obtain an epoxide product, then the epoxide productis used as a raw material to synthesize a 6-position chloride to obtain delmadinone, and finally by virtue of 17-position esterification, the delmadinone acetate can be obtained. Compared with a traditional synthetic method of the delmadinone acetate, the method of the invention has the advantages of simple process operation, economical and environment-friendly production, high synthetic total yield, good product quality, low 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 method for preparing the progesterone drug diamagestrol acetate and its 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 tetrachlorobenzoq...

Claims

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Application Information

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IPC IPC(8): C07J7/00C12P33/00C12R1/32C12R1/77C12R1/07
CPCC07J7/0045C12P33/00
Inventor 甘红星吴来喜胡爱国
Owner HUNAN KEREY BIOTECH
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