Synthetic method of azacitidine

A synthesis method and technology of azacitidine are applied in the field of synthesis of azacitidine and can solve the problems of easy emulsification, inconvenience of emulsification, excessive metal tin of crude drug and the like.

Inactive Publication Date: 2014-01-22
TIANJIN JIUHAI MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0018] In order to overcome the deficiencies in the prior art, the purpose of the present invention is to provide a method for the synthesis of azacitidine with easy-to-obtain raw mate...

Method used

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  • Synthetic method of azacitidine
  • Synthetic method of azacitidine
  • Synthetic method of azacitidine

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Experimental program
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Embodiment 1

[0030] A kind of synthetic method of azacitidine of the present embodiment comprises the following steps:

[0031] In step 1, 5-azacytosine and tetraacetyl ribose are used as raw materials, and the compound with the structure of formula (1) is generated after trimethyl silicon protection; wherein, the molar ratio of 5-azacytosine to tetraacetyl ribose is 1:2.5.

[0032] Step 2, compound of formula (1) and 1,2,3,5-tetra-O-acetyl- β -D-ribose is docked into a glycoside of formula (2) under the catalysis of Lewis acid trimethylsilyl trifluoromethanesulfonate (TMSOTf);

[0033] Step 2: Azacitidine is obtained by recrystallization after the alcoholysis of the glycoside with the structure of the above formula (2) to remove the protecting group; in the present invention, the Lewis acid trimethylsilyl trifluoromethanesulfonate (TMSOTf) Instead of tin tetrachloride, its synthetic route is represented by the formula:

[0034]

[0035] In this embodiment, the alcoholysis under alka...

Embodiment 2

[0037] In this embodiment, the molar ratio of 5-azacytosine to tetraacetyl ribose is 1:2.0. Its processing method is identical with embodiment 1.

Embodiment 3

[0039] In this embodiment, the molar ratio of 5-azacytosine to tetraacetyl ribose is 1:3.5. Its processing method is identical with embodiment 1.

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Abstract

The invention discloses a synthetic method of azacitidine. The synthetic method comprises the following steps: with 5-azacytosine and tetraacetylribose as raw materials, protecting the raw materials by using trimethyl silicon, then performing butt joint on the raw materials together with 1,2,3,5-tetra-O-acetyl-beta-D-ribose under the catalysis of Lewis acid trimethylsilyl triflate to obtain glycoside, performing alcoholysis to remove protective groups, and performing recrystallization to obtain the azacitidine. According to the synthetic method disclosed by the invention, the 5-azacytosine and the tetraacetylribose are used as the raw materials, and in the reaction of obtaining the glycoside through butt joint, the Lewis acid trimethylsilyl triflate (TMSOTf) replaces tin tetrachloride, so that the problems that a crude metallic tin is overproof and after treatment causes emulsification easily and is inconvenient are avoided, process raw materials of the synthetic method are easy to obtain, and the synthetic method is simple in operation, high in yield, less in step, environment-friendly, and suitable for industrial production.

Description

technical field [0001] The invention relates to the field of medicine synthesis technology, in particular to a synthesis method of azacitidine. Background technique [0002] Myelodysplastic syndrome (MDS) is a clonal disease arising from damage at the level of hematopoietic stem or progenitor cells, characterized by refractory leukopenia and easy transformation to acute leukemia. New treatments aim to improve hematological parameters and hopefully halt disease progression. Azacitidine injection is not only an effective way in the new treatment, but also has a good effect on alleviating the extended symptoms. Therefore, carrying out clinical research and registration and marketing of azacitidine for injection can enable more patients with myelodysplastic syndrome to be effectively treated. For domestic enterprises, speeding up the introduction of new products will take the initiative in the market and win the first chance. If azacitidine for injection can be successfully d...

Claims

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Application Information

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IPC IPC(8): C07H19/12C07H1/00A61P35/02
CPCY02P20/55
Inventor 尹新明
Owner TIANJIN JIUHAI MEDICAL TECH
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