High-activity epirubicin derivative, preparation method thereof and application thereof

A preparation and reaction technology, applied in the field of derivatives of epirubicin, can solve problems such as heart failure, which can occur even weeks after cessation of treatment, and may not respond to corresponding drug therapy, increased cardiotoxicity, etc.

Active Publication Date: 2011-05-11
TIANJIN HEMAY BIO TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, cardiac function should still be closely monitored during EPI treatment to reduce the risk of heart failure (this heart failure can even occur several weeks after the termination of treatment, and may not respond to corresponding drug therapy); For patients with mediastinal and pericardial areas combined with radiotherapy, the potential risk of EPI cardiotoxicity may increase; and there will be myelosuppression, nausea, vomiting and other gastrointestinal reactions, skin reactions such as dermatitis and pigmentation, and toxicities such as phlebitis and cellulitis. side effects

Method used

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  • High-activity epirubicin derivative, preparation method thereof and application thereof
  • High-activity epirubicin derivative, preparation method thereof and application thereof
  • High-activity epirubicin derivative, preparation method thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13

[0118] Embodiment 13'-pyrrolyl epirubicin

[0119] Add 3.076 g of epirubicin (Epirubicin) hydrochloride, 300 ml of distilled water, 300 ml of 1,2-dichloroethane, 30 ml of 2,5-dimethoxytetrahydrofuran and 6 ml of glacial acetic acid into a 1 L three-neck flask. Under the protection of argon, it was heated to reflux for 45 minutes, and the reaction was completed. The reaction solution was cooled to room temperature, poured into 200ml of ice water, and allowed to stand for liquid separation. The organic phase was washed once with 200ml of saturated brine, dried over anhydrous magnesium sulfate, filtered and spin-dried; the aqueous phase was stirred in an ice bath by adding 100ml of 5% aqueous sodium bicarbonate solution, extracted with chloroform (50ml×3), combined the chloroform layers, and the chloroform layers Wash once with 100 ml of saturated brine, filter and spin off the solvent, combine the obtained crude product with the above obtained crude product, and purify by colum...

Embodiment 23

[0120] Embodiment 23'-pyrrolyl epirubicin

[0121] Add 3.076 g of epirubicin (Epirubicin) hydrochloride, 500 ml of distilled water, 30 ml of 2,5-dimethoxytetrahydrofuran, 6 ml of glacial acetic acid and 435 mg of sodium acetate into a 1 L three-necked flask. Under the protection of argon, the reaction was stirred at 50° C. for 4 hrs, and the reaction was completed. The reaction solution was cooled to room temperature, and suction filtered to obtain a filter cake. The target compound was obtained by recrystallization of the filter cake. MS: 592 (M-1)

Embodiment 33

[0122] Example 3 3'-pyrrolyl-4'-(pyran-2-yl) epirubicin MS: 677

[0123] With the method in embodiment 1 or embodiment 2, prepare with 4'-(pyran-2-yl) epirubicin as raw material.

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PUM

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Abstract

The invention relates to an epirubicin (EPI) derivative with anticancer activity, in particular to a compound shown as a formula (I) and salts or solvates thereof, a preparation method of the compound shown as the formula (I) and application of the compound serving as medicinal active ingredients. The epirubicin derivative provided by the invention has the equivalent activity and even higher than that of the epirubicin in a cellular level. The formula (I) is shown in the description.

Description

1. Technical field [0001] The present invention relates to a derivative of epirubicin with anticancer activity, its preparation method and its application in the preparation of medicine for treating tumor or cancer. 2. Technical background [0002] Epirubicin (EPI) is an anthracycline antitumor antibiotic synthesized by the Italian scholar Arcamone in 1975 through a semi-synthetic route. However, the subtle changes in the three-dimensional structure lead to a significant reduction in the toxicity of the heart and bone marrow. The main function of epirubicin is to intercalate directly between DNA base pairs, interfere with the transcription process, and prevent the formation of mRNA. EPI can inhibit the synthesis of DNA and RNA, so it has effects on all stages of the cell cycle, and is a non-specific drug for the cell cycle. EPI acts on both the cell membrane and the transport system, but the most important site of action is the nucleus. In addition, EPI also inhibits topo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/044C07H19/04C07H1/00A61K31/7056A61K31/706A61P35/00
CPCA61K31/06A61K31/122A61K31/395A61P35/00C07H15/252C07H17/02C07H19/04C07H19/044C07H19/048
Inventor 张和胜霍爱红
Owner TIANJIN HEMAY BIO TECH CO LTD
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