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Rocuronium bromide enantiomeric impurity, or salt thereof and method for preparing rocuronium bromide enantiomeric impurity or salt

A technology of isomers and enantiomers, which is applied in the field of drug synthesis and can solve problems such as drug risks for patients

Inactive Publication Date: 2017-06-09
CHENGDU SINO STRONG PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] Aiming at the problem that the isomer impurity of rocuronium bromide may cause the risk of drug use to patients, the purpose of the present invention is to provide an isomer impurity or its salt that may exist in rocuronium bromide intermediates, raw materials and preparations and its preparation method to provide a basis for the follow-up quality research of rocuronium bromide

Method used

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  • Rocuronium bromide enantiomeric impurity, or salt thereof and method for preparing rocuronium bromide enantiomeric impurity or salt
  • Rocuronium bromide enantiomeric impurity, or salt thereof and method for preparing rocuronium bromide enantiomeric impurity or salt
  • Rocuronium bromide enantiomeric impurity, or salt thereof and method for preparing rocuronium bromide enantiomeric impurity or salt

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preparation example Construction

[0036] The preparation of embodiment 1 formula III compound

[0037]

[0038] In turn, 2.3g of the compound of formula IV (prepared according to the method of (Amino-steroids. Part 6. Stereospecific Syntheses of Eight, Isomeric, Steroidal Vicinal 2,3-Amino-alcohols, J.C.S.Perkin I, 1979, 2235-2247)), 10mL of water 15mL morpholine was added in the round-bottomed flask, stirred and reacted after being heated to reflux; TLC detected that the reaction was complete. Slowly add ice water to the reaction solution to quench the reaction, extract with ethyl acetate, separate layers, wash the organic layer with water, wash with saturated sodium chloride, dry, concentrate, and column chromatography of the residue gives the compound of formula III as a light yellow solid of about 2.3 g, yield: 80.5%. The obtained compound is subjected to single crystal diffraction, and its diffraction pattern is as follows figure 1 , proving that it is the configuration shown in Formula III.

[0039...

Embodiment 4

[0048] The preparation of embodiment 4 formula I compound

[0049] Add 1.5g of the compound of formula II prepared in Example 2 or 3 and 10mL of dichloromethane into a 50mL round bottom flask in turn, add 0.6mL of allyl bromide under stirring conditions, and react at room temperature. TLC monitored the completion of the reaction. Add 20 mL of diethyl ether to the reaction, precipitate a solid, filter, wash the filter cake with diethyl ether, collect about 1.5 g of the compound of formula I as the solid, yield: 80%.

[0050] 1 H-NMR (d 6 -DMSO, 400MHz): δ=10.11(s,1H), 6.18~6.10(m,1H), 5.64~5.59(m,2H), 5.08~5.06(m,1H), 3.99~3.88(m,7H) ,3.61(m,4H),3.39~3.19(m,5H),2.18(s,3H),2.10~1.75(m,10H),1.70~1.60(m,2H),1.54~1.45(m,4H) ,1.39(m,2H),1.29~1.26(m,2H),1.11~1.04(m,2H),0.90~0.76(m,8H)ppm.

[0051] HRMS-ESI(m / z):529.4008(M–Br) + .

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Abstract

The invention discloses a rocuronium bromide enantiomeric impurity, a salt, a solvate, an enantiomer or a diastereoisomer of the rocuronium bromide enantiomeric impurity and a method for preparing the same. The rocuronium bromide enantiomeric impurity is shown as a formula V. An R1 and an R2 in the formula V are independently selected from H and acetyl; an R3 is selected from N-pyrrolidyl and N-allyl pyrrolidyl. The invention further provides application of the rocuronium bromide enantiomeric impurity to detecting the quality of rocuronium bromide intermediates, crude drugs or preparations. The rocuronium bromide enantiomeric impurity, the salt, the solvate, the enantiomer or the diastereoisomer, the method and the application have the advantages that gaps in the aspect of research on rocuronium bromide impurities can be filled, and foundations and bases can be provided for controlling the quality of rocuronium bromide materials or drugs.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a rocuronium bromide isomer impurity or a salt thereof, and a preparation method thereof. Background technique [0002] Muscle relaxants are the main adjuvant drugs for general anesthesia, and are used during general anesthesia induction for tracheal intubation and intraoperative muscle relaxation maintenance. Rocuronium bromide, which was first listed in the United States in 1994, is a non-depolarizing neuromuscular blocking agent, which belongs to the non-depolarizing muscle relaxants of skeletal muscle relaxants, and it competes with motor nerve endings Binding to cholinergic receptors on the synapse to antagonize the action of acetylcholine. Routine endotracheal intubation is performed as an adjunct to general anesthesia and to allow skeletal muscle relaxation during the procedure. Rocuronium bromide has the characteristics of rapid onset of action, no accumulation...

Claims

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Application Information

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IPC IPC(8): C07J43/00
CPCC07B2200/13C07J43/003
Inventor 张善军关文捷王俊凯刘振平韩健
Owner CHENGDU SINO STRONG PHARMA
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