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Method for preparing 2-deoxidized-2, 2-hydrochloric acid difluoro deoxycytidine

A technology of difluorodeoxycytidine hydrochloride and salt formation, which is applied in the field of preparation of antitumor active compounds, can solve the problems of harsh reaction conditions, unsuitable for industrial production, high price, etc., and achieves mild reaction conditions, easy operation, and reduced effect of steps

Inactive Publication Date: 2012-08-01
JIANGSU HANSOH PHARMA CO LTD
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Problems solved by technology

[0006] Osamu Kitagawa tried to use iododifluoroacetate as a raw material, and added trialkylchlorosilane in the reaction to improve the selectivity of cis-trans products, (Tetrahdron Lett., 1988, 29, 1803), Yasushi Matsumra, etc. People take (R)-2,3-O-cyclohexanone-glyceraldehyde as raw material, add Titanocene catalyst in reaction system, and then improve the selectivity of cis-trans product (J.Flurine chem., 1992,57,203 ), but these methods have used more expensive reagents, and the reaction conditions are harsh, and are still not suitable for industrial production

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  • Method for preparing 2-deoxidized-2, 2-hydrochloric acid difluoro deoxycytidine
  • Method for preparing 2-deoxidized-2, 2-hydrochloric acid difluoro deoxycytidine
  • Method for preparing 2-deoxidized-2, 2-hydrochloric acid difluoro deoxycytidine

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Embodiment Construction

[0032] In order to describe the contents and advantages of the present invention more specifically, the present invention will be further described below in conjunction with specific examples, but the scope of the present invention is not limited to the specific embodiments.

[0033] 1 Preparation of Intermediate A

[0034] Under the protection of nitrogen, the activated Zn powder (261.5g, 4.00mol), trimethylchlorosilane (51mL, 0.4mol), THF (600mL, dried over 4A molecular sieves) were mixed in a 3L three-necked flask, and stirred at room temperature. Weigh ethyl difluorobromoacetate (369.1g, 1.82mol), S-glyceraldehyde acetonide (260.0g, 2.00mol), THF (400ml, dried with 4A molecular sieve), mix thoroughly and drop a small amount of this solution to the In the three-necked bottle of Zn powder, after heating and triggering with a hair dryer, add the remaining solution dropwise, control the rate of addition to keep the system slightly boiling, and continue the heat preservation re...

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Abstract

The invention relates to a 2-deoxidized-2, 2-hydrochloric acid difluoro deoxycytidine compound as shown in a formula (I), and discloses a method for preparing gemcitabine hydrochloride. The method is simple in process, high in yield and quite suitable for industrial production, the purity of a product is fine, and harsh reaction conditions are omitted.

Description

technical field [0001] The invention relates to the preparation of an anti-tumor active compound, in particular to a preparation method of 2-deoxy-2,2-difluorodeoxycytidine hydrochloride compound. Background technique [0002] Gemcitabine hydrochloride is a cell cycle-specific anti-metabolite drug. It is used as an anti-tumor compound. In 1996, the US FDA approved gemcitabine hydrochloride produced by Eli Lilly and Company as a first-line drug for the treatment of pancreatic cancer. In 1998, it was approved as a drug for the treatment of non-small cell lung cancer. . [0003] Gemcitabine hydrochloride mainly acts on tumor cells in the DNA synthesis phase, that is, cells in the S phase. Under certain conditions, it can prevent the progression from the G1 phase to the S phase; it has obvious cytotoxic activity on various cultured human and mouse tumors. At non-lethal doses, it has good anticancer activity against various tumors in mice. [0004] Most of the synthesis of gemc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/073C07H1/00
Inventor 洪承杰杨宝海
Owner JIANGSU HANSOH PHARMA CO LTD
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