Method for synthesizing cisatracurium besilate

A technology for cisatracurium besylate and a compound, which is applied in the field of pharmaceutical synthesis, can solve the problems of complex steps, low product yield, low product purity, etc., to improve yield and purity, reduce synthesis cost, and ensure optical purity. Effect

Inactive Publication Date: 2020-10-16
SHANDONG RUIAN PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Method 3 determines the spatial structure during the reaction and avoids the formation of isomers, but the steps are more complicated
Moreover, the problems of low product yield and low product purity all exist in the above-mentioned synthetic methods, which cause the cost of medicines to fall.
In addition, atracurium besylate contains multiple isomers, and it is difficult to maintain the chiral center of cis atracurium besylate during the synthesis process.

Method used

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  • Method for synthesizing cisatracurium besilate
  • Method for synthesizing cisatracurium besilate
  • Method for synthesizing cisatracurium besilate

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Experimental program
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Embodiment 1

[0038] Embodiment 1: the synthesis of besylate cisatracurium

[0039] (1) Synthesis of compound T473-02:

[0040]

[0041] Anhydrous DMF (0.6 L) and acrylic acid (129.7 g, 1.8 mol) were added to a round bottom flask, potassium carbonate (273.6 g, 1.98 mol) was added in batches, and the temperature was controlled below 45°C. Then T473-02A (227.9 g, 1.8 mol) was added and after the addition was complete, the mixture was stirred at 100° C. for 3 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and 1.0 L of pentane was added. The organic layer was washed with water (3×300 mL) and saturated brine (1×300 mL). The organic layer was collected, dried over anhydrous magnesium sulfate, filtered and distilled under reduced pressure to obtain 288.1 g of a colorless oily substance, namely T473-02, with a yield of 98.8%.

[0042] 1 H NMR (CDCl 3 , 300Hz): δ7.36-7.28 (m, 5H), 6.43 (dd, J 1=5.4Hz,J 2 = 10.8Hz, 1H), 6.13(dd, J 1 = 4.2Hz,J...

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Abstract

The invention discloses a method for synthesizing cisatracurium besilate. The method comprises the following steps of: reacting a compound shown as formula I, a compound shown as formula II and oxalicacid dihydrate to generate a compound shown as formula III; reacting the compound shown as formula III under the catalysis of Pd/C to generate a compound shown as formula IV; reacting the compound shown as formula IV with 1, 5-pentanediol to generate a compound shown as formula V; and reacting the compound shown as formula V with methyl benzenesulfonate to prepare cisatracurium besilate; whereinthe compounds shown as the formula I, the formula II, the formula III, the formula IV and the formula V are respectively represented as the specification. The synthesis method provided by the invention can significantly improve the yield and purity of cisatracurium besilate and reduce the synthesis cost of cisatracurium besilate.

Description

[0001] 1. Technical field [0002] The invention relates to the technical field of medicine synthesis, in particular to a method for synthesizing cisatracurium besylate. [0003] 2. Background technology [0004] Cisatracurium besylate is the latest generation of muscle relaxants, widely used in tracheal intubation, liver and kidney dysfunction, cardiovascular surgery and other fields. Cisatracurium besylate has the characteristics of being metabolized through non-hepatic and non-kidney pathways and has cardiovascular protection. It has advantages over similar drugs, and its muscle relaxation effect is 3 times stronger than that of commonly used clinical atracurium besylate. Cisatracurium besylate is mainly suitable for general anesthesia, and can be widely used in endotracheal intubation, liver and kidney dysfunction, cardiovascular surgery and elderly and pediatric patients. Since the drug was first launched in the UK in 1996, it has gradually replaced vecuronium bromide and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/20C07C303/32C07C309/29
CPCC07C303/32C07D217/20C07C309/29
Inventor 张焕刘宗银钱林艺董鑫菊
Owner SHANDONG RUIAN PHARMA CO LTD
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