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Preparation method of cyclic adenosine monophosphate

A cyclic adenosine monophosphate and reaction technology, applied in the field of preparation of cyclic adenosine monophosphate, can solve the problems of high environmental pressure, long production cycle, low product yield, etc. rate increase effect

Inactive Publication Date: 2016-08-10
NANTONG HONGCI PHARMA
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Problems solved by technology

[0007] However, in this process route, after the synthesis reaction, ion exchange resin is required for chromatographic separation, the production cycle is long, the product yield is low, and because a large amount of acid-base solution is required to process the resin, a large amount of industrial sewage is generated, and the pressure on environmental protection is relatively high.

Method used

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  • Preparation method of cyclic adenosine monophosphate
  • Preparation method of cyclic adenosine monophosphate
  • Preparation method of cyclic adenosine monophosphate

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Embodiment 1

[0031] The preparation of embodiment 1 double salt

[0032]

[0033] Dissolve DCC (26.6g, 100mmol) and morpholine (8.7g, 100mmol) in 100ml of ethanol, heat to dissolve, and then slowly cool down to 0-5°C. Filter, wash with a small amount of ethanol, and dry to obtain a double salt (26.37g, 90% yield), with a melting point of 104.2°C to 105.1°C.

Embodiment 2

[0034] The preparation of embodiment 2 cyclic adenosine monophosphate

[0035] Put 3.0g of adenosine acid, 2.73g of double salt, and 4.5g of DCC (2.5 chemical equivalents) into dissolved pyridine (500ml), raise the temperature to 110°C, and keep it warm for 3 hours to obtain a reaction dropwise solution. Add 4.5g (2.5 chemical equivalents) of DCC to 500ml of pyridine, heat up to boiling, add the above dropwise solution to the reaction, and the addition time is 2 hours. After the addition, keep the boiling point temperature and continue the reaction for 3 hours. Remove the solvent by distillation under reduced pressure. Add water (500ml) and diethyl ether (500ml) to wash, separate the layers, adjust the pH of the water layer to 1.5-2.0, filter, dry and recrystallize to obtain cyclic adenosine monophosphate 1.2g, with a total yield of 40% and a purity of 99.68%.

[0036] Spectral data: MS (ESI): 328.20

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Abstract

The invention relates to a preparation method of cyclic adenosine monophosphate. The main reaction step of the preparation method is to dissolve 5´-AMP, DCC and double salt at first, and then add the reacted product dropwise after the reaction is completed. The internal cyclization reaction is carried out in the pyridine solution of DCC to further inhibit the side reaction of esterification between molecules. The advantages of the present invention are: the preparation method of the present invention has simple operation and high product purity, and the route is suitable for large-scale industrial production and reduces the impact on the environment.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a preparation method of cyclic adenosine monophosphate. Background technique [0002] The compound of formula I shown below: cyclic adenosine monophosphate, that is: adenosine-3', 5'-cyclic phosphate, referred to as cAMP, it is one of the hotspots of current molecular biology research. [0003] [0004] cAMP is closely related to diseases such as psoriasis, coronary heart disease, asthma, hypertension, diabetes and malignant tumors. In the process of protein synthesis, gene transcription and translation are affected by cAMP. It controls genetic information, acts as a "second messenger", and affects the activity of many enzymes and metabolic processes in cells. Therefore, research work and medical clinical trials require a large amount of cAMP. Cyclic adenosine monophosphate is a nucleotide drug, which is mainly used clinically to treat cardiac insufficiency, angina pectoris an...

Claims

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Application Information

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IPC IPC(8): C07H19/213C07H1/00
CPCC07H19/213C07H1/00
Inventor 王兴宝卢建军陆誉升汪小江
Owner NANTONG HONGCI PHARMA
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