Prodrug based on gemcitabine structure and application thereof

A technology of gemcitabine and prodrugs, applied in the field of nucleoside drugs

Active Publication Date: 2015-10-07
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the defects of the above-mentioned commonly used gemcitabine hydrochloride in clinical treatment of tumors, researchers have designed corresponding gemcitabine prodrugs, but there is currently no prodrug linked to a long-chain phosphate at the 5-hydroxyl

Method used

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  • Prodrug based on gemcitabine structure and application thereof
  • Prodrug based on gemcitabine structure and application thereof
  • Prodrug based on gemcitabine structure and application thereof

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Embodiment Construction

[0034] Below in conjunction with the accompanying drawings and examples, the specific implementation of the present invention will be further described in detail, the following examples are used to illustrate the present invention, but not to limit the scope of the present invention.

[0035] 1. Synthesis and preparation of prodrugs based on gemcitabine structure.

[0036] The general structural formula of the prodrug based on the gemcitabine structure claimed in the present invention is shown in formula (I):

[0037]

[0038] where R is CH 2 or And m is an odd number of 13-17, and n is 0 or 1.

[0039] Five kinds of prodrugs conforming to the general formula are disclosed in this specific example, named respectively as compound-1, compound-2, compound-3, compound-4 and compound-5, the structural formulas of these five kinds of prodrugs and The preparation method is as follows.

[0040] Preparation of N-acetyl-4-acetyl-gemcitabine: Gemcitabine (3g, 10mmol) was dissolve...

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Abstract

The invention relates to designing and application of a prodrug based on a gemcitabine structure. According to the prodrug, a phosphate ester long-chain group is introduced to the position 5'-OH of a gemcitabine five-membered sugar ring, so fat-solubility and membrane permeability of the prodrug are improved. In tumors lacking nucleic acid transport protein, the fat-soluble prodrug can enter the tumors through passive diffusion and active transport to inhibit growth of the tumors. Moreover, the prodrug can be orally taken, thereby obtaining a better or same curative effect of tumor growth inhibition compared with intraperitoneal injection of gemcitabine.

Description

technical field [0001] The invention relates to a nucleoside drug, in particular to a prodrug based on a gemcitabine structure and the application of the drug in treating various cancer diseases. Background technique [0002] Prodrugs, also known as prodrugs, are a class of compounds that have no activity or very weak activity, and can be converted into active products through chemical or biological transformation in vivo. The parent drug is chemically modified into a prodrug, and after biotransformation in vivo, the active parent drug is released to play a therapeutic role. The prodrug scheme can overcome the shortcomings of various drugs by improving the physical and chemical properties and pharmacokinetic properties of the parent drug, such as poor water solubility of the drug, unstable chemical properties, poor oral absorption, low brain penetration, toxicity or local Great stimulation, etc. In addition, prodrugs can also improve the targeting selectivity of drugs. [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/10C07H1/00A61K31/7068A61P35/00
Inventor 张洪建祁慧昕
Owner SUZHOU UNIV
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