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Preparation method of adenosine cyclophosphate oxide impurity

A technology for cyclic adenosine monophosphate and oxidation of impurities, applied in chemical instruments and methods, preparation of sugar derivatives, organic chemistry, etc., can solve the problems of less research on impurity preparation and higher requirements, and achieve the effect of simple operation and high product purity

Inactive Publication Date: 2017-04-26
NANTONG HONGCI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] There are many domestic studies on the synthesis of cyclic adenosine monophosphate, but less research on the preparation of its impurities, and the current drug declaration has higher requirements for impurity research

Method used

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  • Preparation method of adenosine cyclophosphate oxide impurity
  • Preparation method of adenosine cyclophosphate oxide impurity
  • Preparation method of adenosine cyclophosphate oxide impurity

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preparation example Construction

[0022] The preparation method of cyclic adenosine monophosphate oxidized impurities is characterized in that: the preparation method uses cyclic adenosine monophosphate and m-chloroperoxybenzoic acid as starting materials, reacts under the action of solvent and reagent, after reaction The product obtains the cyclic adenosine monophosphate oxidation impurity shown in formula (I) through purification again; Described reaction formula is:

[0023]

[0024] As the present invention, a more specific embodiment is that the solvent is tetrahydrofuran, benzene, methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,4-dioxane, acetone, butanone, Ethyl acetate, butyl acetate, propyl acetate, acetonitrile, propionitrile, N,N-dimethylformamide, dimethylsulfoxide, acetic acid, propionic acid, preferably N,N-dimethylformamide, di One or more of methyl sulfoxide, acetic acid, and propionic acid.

[0025] The reagent is m-chloroperoxybenzoic acid, hydrogen peroxide ox...

Embodiment

[0028] Cyclic adenosine monophosphate (3.29g, 10mmol) and m-chloroperoxybenzoic acid (2.03g, 10mmol, 85%) were thoroughly mixed in a round bottom bottle, and N,N-dimethylformamide (50ml) was added at room temperature , and the reactants were stirred at 40-50°C for 24 hours. After the reaction solution was stirred at room temperature for 4 days, the reaction solution was washed with water and saturated brine, dried over anhydrous sodium sulfate, and sucked dry to obtain a crude product. Compound A was obtained as a white solid (1.7 g, 5 mmol, 50% yield) by column chromatography. Spectral data:

[0029] 1 H NMR (500MHz,D 2 O)δ11.98(s,1H),7.48(s,1H),7.38(s,1H),4.35(d,1H),4.00(m,2H),3.20(m,1H),2.00-1.87( m,2H);

[0030] MS(ESI):345.05

[0031] Elemental analysis: C: 34.79%, H: 3.50%, N: 20.29%, O: 32.44%, P: 8.97% Spectral data:

[0032] 1 H NMR (500MHz,D 2 O)δ8.58(s,1H),8.35(s,1H),6.99(s,2H),6.16(dd,1H),4.75(m,1H),4.51(m,1H),4.40(m, 1H), 4.28(m, 2H), 3.58(m, 2H);

[00...

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Abstract

The invention relates to a preparation method of an adenosine cyclophosphate oxide impurity. The preparation method comprises the steps that adenosine cyclophosphate and meta-chloroperoxybenzoic acid serve as starting materials, reacting is conducted under the action of a solvent and a reagent, a product obtained after reacting is purified, and the adenosine cyclophosphate oxide impurity is obtained. The preparation method has the advantages of being easy and convenient to implement, high in purity of the product and suitable for medicine quality research.

Description

technical field [0001] The invention relates to a cyclic adenosine monophosphate specific oxidation impurity and a preparation method thereof. Background technique [0002] The compound of formula II shown below: cyclic adenosine monophosphate, namely: adenosine-3', 5'-cyclic phosphate, referred to as cAMP, it is one of the hot spots 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 and myoc...

Claims

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Application Information

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IPC IPC(8): C07H19/213C07H1/00
CPCC07H19/213C07H1/00
Inventor 陆誉升王兴宝
Owner NANTONG HONGCI PHARMA
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