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Milrinone intermediate compound

A compound, milrinone technology, applied in the field of drug synthesis, can solve the problems of low safety, low overall yield, low production cost, etc., and achieve the effects of avoiding the use of highly toxic drugs, easy route operation, and saving production costs.

Active Publication Date: 2020-09-29
LUNAN PHARMA GROUP CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] (1) The milrinone prepared by the existing milrinone synthesis method is not high in purity and red in color, and it is difficult to achieve the predetermined effect through further refining means
[0016] (2) In the synthesis process of milrinone, there are generally longer reaction steps, resulting in a low overall yield
[0017] (3) The synthetic route of existing milrinone is relatively complicated, and reaction conditions are harsh, and some need to apply highly toxic potassium cyanide or malononitrile, which makes the process operation less safe and industrialized production is more difficult to realize
[0018] Summarizing the many problems existing in the prior art, it is still a problem to be solved at present to study and find a mild reaction condition, simple operation process, high product yield, high purity, and low production cost suitable for industrialized production of milrinone.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Under argon protection, at room temperature, the Pd(PPh 3 ) 4 (5.82g, 5.00mmol) was added in dimethyl sulfoxide (200mL), after stirring and mixing, a solution of KOAc (33.34g, 0.34mol) in water (50mL), α-bromoacetoacetaldehyde (SM-1X=Br, 16.48g, 0.10mol) and 4-pyridine boronic acid (SM-2R=OH, 14.74g, 0.12mol), stirring and reflux reaction, the reaction was completed, filtered, and the filtrate was added in purified water (800mL) , extracted with ethyl acetate (250mL×2), combined the organic phases, dried over anhydrous sodium sulfate, filtered, and concentrated the filtrate to dryness under reduced pressure to obtain 15.62g of milrinone intermediate compound I, with a yield of 95.8% and a purity of 99.96 %.

Embodiment 2

[0069] Under argon protection, at room temperature, the Pd(PPh 3 ) 4 (5.80g, 5.00mmol) was added in dimethyl sulfoxide (200mL), after stirring and mixing, a solution of KOAc (33.36g, 0.34mol) in water (50mL), α-bromoacetoacetaldehyde (SM-1X=Br, 16.51g, 0.10mol) and 4-pyridine boronic acid (SM-2R=OH, 12.92g, 0.105mol), stirring and reflux reaction, the reaction was completed, filtered, and the filtrate was added in purified water (800mL) , extracted with ethyl acetate (250mL×2), combined the organic phases, dried over anhydrous sodium sulfate, filtered, and concentrated the filtrate to dryness under reduced pressure to obtain 14.77g of milrinone intermediate compound I, with a yield of 90.6% and a purity of 99.92 %.

Embodiment 3

[0071] Under argon protection, at room temperature, the Pd(PPh 3 ) 4 (5.83g, 5.00mmol) was added in dimethyl sulfoxide (200mL), after stirring and mixing, a solution of KOAc (33.37g, 0.34mol) in water (50mL), α-bromoacetoacetaldehyde (SM-1X=Br, 16.52g, 0.10mol) and 4-pyridine boronic acid (SM-2R=OH, 12.27g, 0.10mol), stirring and reflux reaction, the reaction was completed, filtered, and the filtrate was added in purified water (800mL) , extracted with ethyl acetate (250mL×2), combined the organic phases, dried over anhydrous sodium sulfate, filtered, and concentrated the filtrate to dryness under reduced pressure to obtain 14.07g of milrinone intermediate compound I, with a yield of 87.5% and a purity of 99.86 %.

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Abstract

The invention provides a milrinone intermediate compound, discloses a preparation method of the milrinone intermediate compound, and belongs to the technical field of medicine synthesis. Alpha-substituted acetyl acetaldehyde (SM-1) reacts with 4-pyridylboronic acid (alkyl) (SM-2) so as to obtain the milrinone intermediate compound I. A method of using the milrinone intermediate compound to preparea milrinone agricultural product is simple and convenient to operate, high in safety, high in yield and suitable for industrial scale-up production, and the appearance and purity of the obtained high-purity milrinone finished product both reach the standards.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a milrinone intermediate compound. Background technique [0002] Milrinone, also known as cyanopyridone, its CAS number is: 78415-72-2, is 1,6-dihydro-2-methyl-6-oxo-[3,4'-linked The general name of pyridine]-5-carbonitrile was first successfully developed by Sterling Company of the United States. It was first approved by the FDA in the United States in 1987 and officially listed in the United States in 1992. It was subsequently sold in the United Kingdom, France, Germany, the Netherlands, Belgium and other countries. It is marketed in Brazil and other countries, and its lactate is used clinically. It is mainly suitable for the treatment of refractory heart failure and heart failure patients with digitalis poisoning. Recent studies have shown that milrinone can also be used for low cardiac output after extracorporeal circulation in cardiac surgery. Syndrom...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/50C07D213/85
CPCC07D213/50C07D213/85Y02P20/55
Inventor 鲍广龙高洁
Owner LUNAN PHARMA GROUP CORPORATION
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