Synthetic process of decitabine

A technology of decitabine and its synthetic method, which is applied in the field of chemical drug synthesis, and can solve the problems that ammonia gas is not easy to control, etc.

Inactive Publication Date: 2008-11-19
GUIZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

1-(3,5-di-D-acetyl-2-deoxy-D-ribose)-5-azacytosine is passed through ammonia gas at room temperature in methanol, and the product is recrystall...

Method used

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  • Synthetic process of decitabine
  • Synthetic process of decitabine
  • Synthetic process of decitabine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0058] 1.3 5-Acetyl-2-methoxyacetylmethyl-3-methoxyacetyl-2-deoxy-D-ribose (2a)

[0059] Dissolve 292.29 g of 5-methoxy-2-methoxyacetylmethyl-3-methoxyacetyl-2-deoxy-D-ribose in 850 mL of glacial acetic acid and 425.4 mL of acetic anhydride. Under nitrogen protection, a mixed solution of 36.08 g of concentrated sulfuric acid and 50 mL of glacial acetic acid was slowly added dropwise at 5°C to 12°C, and the temperature was controlled at 12°C to 15°C. The dropwise addition was completed in about 45 minutes, and the reaction was continued for 15 minutes to 30 minutes (such as 15 minutes for blackening, 30 minutes for non-blackening). The resulting mixture was poured into 2 L of ice water with stirring, and extracted with dichloromethane (2000 mL×2). The organic phase was saturated with Na 2 CO 3 The pH of the aqueous solution was adjusted to 7-8, several layers were separated, and the aqueous layer was extracted with 1000 mL of dichloromethane. The organic layers were c...

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Abstract

The invention relates to a method for preparing Decitabine. The particular proposal for solving the technical problem is as follows: 2-deoxidtion-D-ribose, 10 percent of HCL methanol solution, methoxyacetic acetic anhydride, HMDS, acetic anhydride, tri-silicyl tri-fluorine methane sulfonic acid ester, acetic acid amine, etc. are adopted as raw materials to synthesize the Decitabine; the target product of the Decitabine is obtained through the five steps of reactions, namely, methylation, acylation, trimethyl silication, ammoniation and deacylation with a total yield of above 18.4 percent and a product purity of above 99.7 percent.

Description

technical field [0001] The invention relates to a synthetic method of chemical medicine, in particular to a synthetic method of decitabine. Background technique [0002] Decitabine, its drug name: Decitabine; registered name: Decitabine; drug alias: 5-azaCd, Azadc; trade name: Dacogen; chemical name: 4-amino-1-(2-deoxy-β-D-erythro Ribofuranose)-1,3,5-triazin-2(1H)-one. [0003] Decitabine is a 2'-deoxycytidine analogue developed by SuperGen Corporation of the United States, which can be converted into a 5'-monophosphate deoxycytidine analogue in vivo, and incorporated into DNA under the action of DNA polymerase to inhibit DNA synthesis And methylation, leading to cell differentiation or apoptosis, thereby inhibiting the growth of tumor cells, it can not inhibit DNA synthesis in vitro, but can cause hypomethylation in tumor cells, and maintain the related cell differentiation and proliferation control of genes function, and is currently undergoing clinical trials in refract...

Claims

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Application Information

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IPC IPC(8): C07H19/12A61P35/00
Inventor 范锦荣宋宝安薛伟陶书伟陈鹏利
Owner GUIZHOU UNIV
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