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Synthesis process of vecuronium bromide

A synthesis process and compound technology, which is applied in the direction of drug combination, steroids, anesthetics, etc., can solve the problems of high cost, inconvenient operation, and low yield, and achieve the effects of mild conditions, avoiding cumbersome operations, and high yield

Inactive Publication Date: 2010-03-31
XUZHOU NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Overcome the disadvantages of high cost, inconvenient operation and low yield in the background technology

Method used

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  • Synthesis process of vecuronium bromide
  • Synthesis process of vecuronium bromide
  • Synthesis process of vecuronium bromide

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Embodiment

[0028] 1), the preparation of compound epiandrosterone sulfonyl ester (III):

[0029] Dissolve epiandrosterone (II) (40.0g, 0.1379mol), p-toluenesulfonyl chloride (45.0g, 0.236mol) in pyridine (250ml), react at 40°C for 3h, pour the reaction solution into water (670ml), filter , a white solid was obtained, washed with water (3×20ml), and dried to obtain product (III) (58.6g, 95.7%), mp 163-165°C.

[0030] 2), 5α-androst-2-en-17-one (IV)

[0031] The compound epiandrosterone sulfonyl ester (III) (50.0g, 0.1125mol) was added to 2,4,6-collidine (100ml), heated to reflux for 4h, and the reaction solution was poured into 10% dilute sulfuric acid ( 150ml), a white solid was precipitated, filtered to obtain an off-white solid, washed with water (3×20ml), and dried to obtain product (IV) (24.5g, 80.0%), mp 108-110°C.

[0032] 3), 17-acetoxy-5α-androstane-2,16-diene (V)

[0033] (IV) (15.0g, 0.055mol), p-toluenesulfonic acid (1.5g, 0.009mol) and isopropenyl acetate (50ml) were heate...

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Abstract

The invention discloses a synthesis process of vecuronium bromide. The synthesis process comprises the following steps: generating epiandrosterone sulfonyl ester (III) by carrying out esterification reaction between epiandrosterone (II) and paratoluensulfonylchloride; generating 5Alpha-androst-2-alkene-17-ketone (IV) by carrying out elimination and dehydration reaction between the (III) and 2,6-lutidines; generating 17-acetoxyl-5Alpha-androstane-2,16-diene (V) by carrying out enolization and esterification reaction between the (IV) and isopropenyl acetate; generating (2Alpha, 3Alpha, 16Alpha,17Alpha)-diepoxy-17Beta-acetyl-5Alpha-androstane (VI) by epoxy reaction of the (V) under the effect of hydrogen peroxide; generating 2Beta, 16Beta-di(1-piperidyl)-5Alpha-androstane-3Alpha-hydroxyl-17-ketone (VII) by ring-opening and addition reaction of the (VI) under the effect of hexahydropyridine; generating 2Beta, 16Beta-di(1-piperidyl)-5Alpha-androstane-3Alpha,17Beta-diol (VIII) by the (VII)under the reduction of potassium borohydride; generating 2Beta, 16Beta-di(1-piperidyl)-3Alpha, 17Beta- acetoxyl-5Alpha-androstane (IX) by carrying out esterification reaction of the (VIII) under the acetylation of acetic anhydride; and generating vecuronium bromide (I) by carrying out quaternary ammonium salt reaction between the (IX) and bromomethane. The invention has the advantages of low cost,less pollution and high yield.

Description

Technical field [0001] The invention relates to a synthesis process of vecuronium bromide. Vecuronium bromide is a non-depolarizing diaminandrostane muscle relaxant. Background technique [0002] Vecuronium Bromide, chemical name 1-[3α,17β-diacetoxy2β-(1-piperidinyl)-5α-androstane-16β-yl]-1-methylpiperidine, It is a medium-effective non-depolarizing muscle relaxant of the monoquaternary ammonium steroid class. Its structure is similar to pancuronium bromide. It blocks the conduction between nerve endings and striated muscle by competing with acetylcholine for nicotinic receptors located on the motor end plate of striated muscle. . Unlike depolarizing neuromuscular blocking drugs, such as succinylcholine, this product does not cause muscle fiber fasciculation. It is mainly used as an auxiliary drug for general anesthesia, used for tracheal intubation during general anesthesia and muscle relaxation during surgery. This product has the characteristics of quick onset, no acc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J43/00A61P23/00
Inventor 蒋虹屠树江辜顺林陈玉芳
Owner XUZHOU NORMAL UNIVERSITY
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