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8DM derivative, and method for synthesizing mometasone furoate from 8DM derivative

A technology of mometasone furoate and synthetic method, which is applied in the direction of steroidal compounds and organic chemistry, and achieves the effects of mild reaction conditions, simple process and high quality

Active Publication Date: 2016-05-11
YANGTAI PHARMA SHANDONG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the many problems existing in the existing synthetic methods of mometasone furoate, the present invention provides a kind of 8DM derivative and the method for using it to synthesize mometasone furoate

Method used

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  • 8DM derivative, and method for synthesizing mometasone furoate from 8DM derivative
  • 8DM derivative, and method for synthesizing mometasone furoate from 8DM derivative
  • 8DM derivative, and method for synthesizing mometasone furoate from 8DM derivative

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Embodiment 1

[0041] (1) Preparation of compound 1

[0042] 50 g of 9β, 11β-epoxy-17α, 21-dihydroxy-16α-methyl-1,4-pregna (steroid)diene-3,2-dione and 300 ml of pyridine were added to the reaction flask. After the temperature of the reaction solution is lowered to -5~5°C, add 30g of p-toluenesulfonyl chloride into the reaction flask, and control the temperature at -5~5°C for 9 hours; pour the reaction solution into 3000ml of water, and stir to precipitate a solid. The water layer was discarded, and 380 ml of dichloromethane was added to the residue, stirred for 10 minutes, separated, and the water layer was extracted twice with 380 ml of dichloromethane. The organic phase was adjusted to pH = 6-7 with 1N hydrochloric acid, separated, and the organic phase was adjusted to pH = 7-8 with saturated sodium bicarbonate solution. The organic phase was washed with 400 ml of saturated brine. The organic phase was concentrated to dryness, 150ml of dichloromethane was added, 250ml of isopropyl ether...

Embodiment 2

[0049] (1) Preparation of compound 1

[0050] 50 g of 9β, 11β-epoxy-17α, 21-dihydroxy-16α-methyl-1,4-pregna (steroid)diene-3,2-dione and 300 ml of pyridine were added to the reaction flask. The temperature was lowered to -5~5°C, 15g of methanesulfonyl chloride was added into the reaction flask, and the temperature was controlled at -5~5°C for 9 hours. The reaction solution was poured into 3000ml of water, and the solid was precipitated by stirring. The water layer was discarded, and 380 ml of dichloromethane was added to the residue, stirred for 10 minutes, separated, and the water layer was extracted twice with 380 ml of dichloromethane. The organic phase was adjusted to pH = 6-7 with 1N hydrochloric acid, separated, and the organic phase was adjusted to pH = 7-8 with saturated sodium bicarbonate solution. The organic phase was washed with 400 ml of saturated brine. The organic phase was concentrated to dryness, 150ml of dichloromethane was added, 250ml of isopropyl ether ...

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Abstract

The invention relates to a 8DM derivative, and a method for synthesizing mometasone furoate from the 8DM derivative. The method comprises the following steps: carrying out an esterification reaction on a compound 1 and furoyl chloride to generate a compound 2 which is the 8DM derivative, and simultaneously carrying out a ring opening reaction and a 21th position chlorination reaction on the compound 2 in the presence of concentrated hydrochloric acid to generate a compound 3 which is mometasone furoate. The disadvantages of long route, complex reaction system and long time of original technologies are effectively solved in the invention. The method has the advantages of simple process, mild reaction conditions, high yield, low cost, high quality, cheap and easily available raw and auxiliary materials, and suitableness for industrial production.

Description

Technical field: [0001] The invention relates to an 8DM derivative and a method for synthesizing mometasone furoate using it. Background technique: [0002] Mometasone furoate is a half-synthesized glucocorticoid, which has anti-inflammatory, anti-allergic, vasoconstricting, reducing vascular permeability, inhibiting cell division, and antipruritic effects. It is characterized by increased action intensity and disproportionately increased side effects , and only use it once a day. Mometasone furoate has a good therapeutic effect on skin diseases that are effectively treated by corticosteroids, such as neurodermatitis, eczema, atopic dermatitis, seborrheic dermatitis and psoriasis caused by skin inflammation and pruritus. [0003] At present, most of the production of mometasone furoate is based on 9β, 11β-epoxy-17α, 21-dihydroxy-16α-methyl-1,4-pregna (steroid)diene-3,2-dione (8DM) The starting materials have disadvantages such as complicated process and long time consumpti...

Claims

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Application Information

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IPC IPC(8): C07J71/00C07J17/00
CPCC07J17/00C07J71/0015
Inventor 于勇冯永斌马春丽赵宗玉杨萍
Owner YANGTAI PHARMA SHANDONG
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