Preparation method of ulipristal acetate bulk drug impurities

A technology of ulipristal acetate and raw materials, applied in the direction of steroids, organic chemistry, etc., can solve problems such as not involved, and achieve the effects of enhanced control, easy availability of raw materials, and easy control of reaction conditions

Active Publication Date: 2021-01-15
HUNAN NORCHEM PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The prior art does not refer to 17α-acetoxy-3-acetoxy-11β-[4-(N,N-dimethylamino)phenyl]estra-1,3,5(10)-triene-20 -Synthesis report of ketone

Method used

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  • Preparation method of ulipristal acetate bulk drug impurities
  • Preparation method of ulipristal acetate bulk drug impurities

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Under nitrogen protection, add 5g (0.01mol) of ulipristal acetate and 25ml of dichloromethane into a 100ml three-necked flask, stir to dissolve, add 1ml (0.01mol) of acetic anhydride, 2.4ml (0.032mol) of acetyl bromide, and React for 6 hours, pour into 100ml of water, add saturated sodium bicarbonate solution to react excess acetic anhydride and acetyl bromide, let stand to separate layers, extract the aqueous layer with dichloromethane, wash the organic phase with water, and evaporate to dryness to obtain an oily substance. The oily product was purified by column chromatography to obtain 4.6 g of off-white powdery solid with an HPLC purity of 97.6%. HR-ESI-Ms (M+H): 518.3. H-NMR (CDCl 3 ,400MHz)δ:0.87(s,3H,C 18 -Me),1.96(s,3H,C 21 -Me),2.11(s,3H,C 17 -Ac),2.27(s,3H,C 3 -Ac),3.06(s,6H,-N(CH 3 ) 3 ),

[0024] 1.09~2.35(m,10H), 2.73~3.19(m,4H), 6.55~6.67(m,3H, Benzene Ring), 6.76~6.81(m,4H, Benzene Ring).

Embodiment 2

[0026] Under nitrogen protection, add 5g (0.01mol) of ulipristal acetate and 25ml of dichloromethane into a 100ml three-necked flask, stir to dissolve, add 1ml (0.01mol) of acetic anhydride, 2.4ml (0.032mol) of acetyl bromide, and React for 6 hours, pour into 100ml of water, add saturated sodium bicarbonate solution to react excess acetic anhydride and acetyl bromide, let stand to separate layers, extract the aqueous layer with dichloromethane, wash the organic phase with water, and evaporate to dryness to obtain an oily substance. The oil was recrystallized from isopropyl ether to obtain 4.3 g of off-white powdery solid with an HPLC purity of 95.9%.

Embodiment 3

[0028] Under nitrogen protection, add 5 g (0.01 mol) of ulipristal acetate and 50 ml of dichloromethane into a 100 ml three-neck flask, stir to dissolve, add 1 ml (0.01 mol) of acetic anhydride, 2.5 ml (0.034 mol) of acetyl bromide, and React for 6 hours, pour into 100ml of water, add saturated sodium bicarbonate solution to react excess acetic anhydride and acetyl bromide, let stand to separate layers, extract the aqueous layer with dichloromethane, wash the organic phase with water, and evaporate to dryness to obtain an oily substance. The oil was recrystallized from isopropyl ether to obtain 4.5 g of off-white powdery solid with an HPLC purity of 96.8%.

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Abstract

The invention belongs to the technical field of steroid hormone drug preparation, and particularly relates to an ulipristal acetate bulk drug impurity preparation method, which comprises: dissolving ulipristal acetate in a solvent, carrying out a reaction under acetic anhydride and acetyl bromide conditions, and treating to obtain the ulipristal acetate bulk drug impurity, wherein the chemical name of the ulipristal acetate bulk drug impurity is 17 alpha-acetoxy-3-acetoxy-11beta-[4-(N,N-dimethylamino)phenyl]estra-1,3,5(10)-trien-20-one, the reaction process is defined in the specification, thesolvent is dichloromethane, and the mole number of acetic anhydride is 0.5-3 times that of ulipristal acetate. The product provided by the invention is high in purity and high in yield, and is used as a reference substance in an ulipristal acetate production process for controlling the quality of ulipristal acetate.

Description

technical field [0001] The invention belongs to the technical field of preparation of steroid hormone drugs, and in particular relates to a method for preparing ulipristal acetate crude drug impurities. Background technique [0002] Ulipristal acetate is a selective progesterone receptor modulator developed by French Laboratoire HRA Pharma, which can prevent progesterone from binding to its receptor, thereby inhibiting the normal gene transcription stimulated by progesterone, so that it cannot synthesize pregnancy Initiates and maintains the protein needed to inhibit or delay ovulation, thereby achieving contraceptive effects. Ulipristal acetate is the first drug researched, developed and marketed specifically for emergency contraception. Because it has a higher affinity to progesterone receptors than other contraceptive drugs, it is called the second-generation selective progesterone receptor. body regulator. [0003] Ulipristal acetate has not yet been recorded in the ph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00
CPCC07J41/0072
Inventor 谢祚宜曾春玲靳志忠吴斯宇刘喜荣
Owner HUNAN NORCHEM PHARMACEUTICAL CO LTD
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