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Adriacin derivative with anti-cancer activity

A drug active and neutral technology, applied in the field of doxorubicin derivatives with anticancer activity, can solve the problems of high cost and complex production process, and achieve high social and economic benefits

Inactive Publication Date: 2005-05-11
TIANJIN HEMAY BIO TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, monoclonal antibodies are prone to immunotoxicity in the human body, and their production process is complex and costly

Method used

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  • Adriacin derivative with anti-cancer activity
  • Adriacin derivative with anti-cancer activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1, the preparation of stearoyl-L-alanine-L-proline-doxorubicin (compound one)

[0054] Dissolve stearyl dipeptide (50mg, 110nmol) and N-hydroxysuccinimide (13mg, 110nmol) in 15ml of ethylene glycol dimethyl ether, cool the solution to 0-5°C, and add DCC (23mg, 120nmol), and then reacted at room temperature for 5h. Adriamycin hydrochloride (58 mg, 100 nmol), 0.2 ml of triethylamine, and 2 ml of DMF were added to the reaction system. React overnight at room temperature. Ethylene glycol dimethyl ether was removed by subtractive evaporation, 50ml of ethyl acetate was added to the residue, cyclohexylurea was removed by filtration, the ethyl acetate solution was washed once with 1N aqueous hydrochloric acid solution, once with saturated aqueous sodium chloride solution, and the aqueous layers were combined and washed with Back-extract once with 30 ml of ethyl acetate, combine the ethyl acetate layers, and dry over anhydrous sodium sulfate. Filter and evaporate t...

Embodiment 2

[0055] Embodiment 2, the preparation of oleoyl-L-alanine-L-proline-doxorubicin (compound 2)

[0056] Using the preparation method of Example 1, it is prepared by replacing stearoyl-L-alanine-L-proline with oleoyl-L-alanine-L-proline. 1 H NMR (CDCl 3 , ppm) δ13.94(s, 1H), 13.22(s, 1H), 8.02(d, 1H, J=7.6Hz), 7.77(dd, 1H, J=7.6, 8.4Hz), 7.37(d, 1H , J=8.4Hz), 6.94(d, 1H, J=7.2Hz), 6.62(d, 1H, J=8.0Hz), 6.33(brs, 1H), 5.48(s, 1H), 5.24-5.42(m , 2H), 5.24(s, 1H), 4.76(s, 2H), 4.62(brs, 1H), 4.40-4.50(m, 1H), 4.10-4.18(m, 3H), 4.05(s, 3H), 3.66(s, 1H), 3.26(d, 1H, J=18.8Hz), 3.00(d, 1H, J=18.8Hz), 2.75(d, 1H, J=6.4Hz), 2.74(d, 1H, J =6.4Hz), 2.33(d, 1H, J=14.48Hz), 2.10-2.23(m, 6H), 1.75-1.92(m, 2H), 1.52-1.62(m, 2H), 1.44(d, 3H, J=7.2Hz), 1.20-1.40 (m, 23H), 0.80-0.95 (m, 9H).

Embodiment 3

[0057] Embodiment three, the preparation of linoleoyl-L-alanine-L-proline-doxorubicin (compound three)

[0058] Using the preparation method of Example 1, it is prepared by replacing stearoyl-L-alanine-L-proline with linoleoyl-L-alanine-L-proline. 1 H NMR (CDCl 3 , ppm) δ13.95(s, 1H), 13.23(s, 1H), 8.02(d, 1H, J=7.6Hz), 7.77(dd, 1H, J=7.6, 8.4Hz), 7.37(d, 1H , J=8.4Hz), 6.94(d, 1H, J=7.2Hz), 6.62(d, 1H, J=8.0Hz), 6.33(brs, 1H), 5.48(s, 1H), 5.24-5.42(m , 4H), 5.24(s, 1H), 4.76(s, 2H), 4.62(brs, 1H), 4.40-4.50(m, 1H), 4.10-4.18(m, 3H), 4.05(s, 3H), 3.66(s, 1H), 3.26(d, 1H, J=18.8Hz), 3.00(d, 1H, J=18.8Hz), 2.75(d, 1H, J=6.4Hz), 2.74(d, 1H, J =6.4Hz), 2.33(d, 1H, J=14.48Hz), 2.10-2.23(m, 6H), 1.75-1.92(m, 2H), 1.52-1.62(m, 2H), 1.20-1.40(m, 22H), 0.80-0.95 (m, 9H).

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Abstract

This invention relates to farmiblastina derivatives, shown as formula, wherein: R1=H or OH, R2 and R3= H or C1-4 hydrocarbon, R4=H, C1-40 saturated or unsaturated hydrocarbon or XR5, wherein X=NH or O, R5=C1-40 saturated or unsaturated hydrocarbon, W=O or NH, R6=H, OH, or O(C1-4 hydrocarbon), R7=H or OH. The invention relates to its preparation and use as medicinal active component thereof.

Description

1. Technical field [0001] The present invention relates to compounds represented by formula (I) with anticancer activity, their preparation methods and their application as active ingredients of medicines. 2. Technical Background [0002] Doxorubicin (Doxorubicin) and daunorubicin (Daunorubicin) and other tetracyclic anthraquinones are widely used anticancer drugs, and daunorubicin is one of the most effective drugs for treating leukemia. It is effective in the treatment of many solid tumors, including: liver cancer, gastric cancer, breast cancer, lung cancer, ovarian cancer and various blood cancers. However, potential cardiotoxicity limits their clinical use (Doroshow J.H.N. Engl. J. Med. 1991, 324:843). So far, hundreds of their derivatives have been isolated or artificially synthesized in an attempt to find a new generation of anticancer drugs with low toxicity and high activity, but with little success. Subsequently, these drugs are linked to monoclonal antibodies to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/704A61P35/00C07H15/252
Inventor 张和胜
Owner TIANJIN HEMAY BIO TECH CO LTD
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