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Novel use of porphyrin derivatives

a technology of porphyrin and derivatives, applied in the field of new porphyrin derivatives, to achieve the effect of superior cell cytotoxic activity and potent anticancer activity

Inactive Publication Date: 2006-06-15
TECHNOMART
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0049] The compound of the present invention has potent anticancer activity and therefore, the pharmaceutical composition of the present invention thus may be employed to treat or prevent various cancers such as colon cancer, cervical cancer, gastric cancer, or cystic cancer by way of reproducing singlet state oxygen radical and superior cell cytotoxic activity.

Problems solved by technology

However, above described clinically using porphyrin compounds as photosensitizer drugs have been reported to have several disadvantages such as too long retention time in human body delivering unfavorable photo-toxicity, which remains to be improved till now.

Method used

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  • Novel use of porphyrin derivatives

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of (13-diethylene glycol-oxycarbonyl)-pheophorbide a, methyl ester (2)

[0075] A solution of phephytin a 60 mg in dichloromethane (3 ml) was poured in 50 ml of flask and treated with diethyleneglycol (20 ml) with stirring. 1 ml of sulfuric acid was added thereto, stirred for 3 hrs and then sodium bicarbonate water solution was added thereto. The solution was extracted with chloroform and the collected chloroform layer was concentrated by removing organic solvent. Remaining residue was purified by column chromatography to isolate 39 mg of (13-diethylene glycol-oxycarbonyl)-pheophorbide a, methyl ester (2):

[0076]1H-NMR (500 MHz, CDCl3) δ: 9.51 (s, 1H, meso-H), 9.37(s, 1H, meso-H), 8.56(s, 1H, meso-H), 7.99(dd, 1H, J=6.2, 11.6 Hz, CH2═CH), 6.29 (d, 1H, J=17.8 Hz, CH2═CH), 6.28(s. 1H, CH), 6.18 (d, 1H, J=11.6 Hz CH2═CH), 4.48-4.41 (m, 1H, CH), 4.24-4.22 (m. 1H. CH), 4.19-4.04 (m, 2H, OCH2), 3.87 (s, 3H, OCH3), 3.71-3.66 (m, 2H, CH2), 3.68 (s, 3H, CH3), 3.64-3.42 (m, 6H, CH2O...

example 2

Preparation of (13- methoxytriethylene glycol-oxycarbonyl) pheophorbide a methyl ester (3)

[0077] 29 mg of (13- methoxytriethylene glycol -oxycarbonyl) pheophorbide a methyl ester (3) was prepared by the same procedure with that described in above Example 1 except using phephytin (60 mg) and methoxytriethyleneglycol (30 ml):

[0078]1H-NMR (500 MHz, CDCl3) δ: 9.45 (s, 1H, meso-H), 9.30(s, 1H, meso-H), 8.55(s, 1H, meso-H), 7.93(dd, 1H, J=6.2, 11.5 Hz, CH2═CH), 6.26 (s. 1H, CH), 6.25 (d, 1H, J=17.8 Hz CH═CH2), 6.14 (d, 1H, J=11.3 Hz CH═CH2), 4.49-4.44 (m, 1H, CH), 4.22-4.20 (m. 1H. CH), 4.15-4.02 (m, 2H, OCH2), 3.88 (s, 3H, OCH3), 3.67 (s, 3H, CH3), 3.60(q, 2H, CH3—CH2), 3.51-3.45 (m, 8H, CH2 OCH2 CH2 OCH2), 3.41-3.37 (m, 2H, CH2), 3.38 (s, 3H, CH3), 3.25 (s, 3H, OCH3), 3.16 (s, 3H, CH3), 2.65-2.18 (m, 4H, CH2CH2), 1.82 (d, 3H, J=7.2 Hz, CH3), 1.68-1.64 (m, 3H, CH3), 0.51 (br. s., 1H, N-H), -1.61 (br. s., 1H, N-H).

example 3

Preparation of 13-hydroxy-(13-methoxytriethylene glycoloxy carbonyl) pheophorbide a methyl ester (4)

[0079] 22 mg of 13-hydroxy-(13- methoxytriethylene glycoloxy carbonyl) pheophorbide a methyl ester (4) was prepared by the same procedure with that described in above Example 1 except using 10-hydroxyphephytin a (60 mg) and methoxytriethyleneglycol (20 ml):

[0080]1H-NMR (500 MHz, CDCl3) δ: 9.62 (s, 1H, meso-H), 9.49(s, 1H, meso-H), 8.65(s, 1H, meso-H), 8.03(dd, 1H, J=6.3, 11.4 Hz, CH2═CH), 6.31 (d, 1H, J=17.8 Hz, CH═CH2), 6.20(d, 1H, J=11.6 Hz, CH═CH2), 5.78 (s, 1H, OH), 4.52-4.47 (m, 1H, CH), 4.30-4.14 (m, 3H, CH and OCH2), 3.74 (s, 3H, OCH3), 3.74-3.70(m, 2H, CH2), 3.63-3.57 (m, 8H, CH2OCH2CH2OCH2), 3.60 (s, 3H, CH3), 3.47-3.46 (m, 2H, CH2), 3.43 (s, 3H, CH3), 3.29 (s, 3H, CH3), 3.27 (s, 3H, OCH3), 3.02-2.95, 2.64-2.57 and 2.35-2.21 (m, 4H, CH2CH2), 1.71 (t, 3H, J=7.5 Hz, CH3), 1.60 (d, 3H, J=7.1 Hz, CH3), 0.30 (br. s., 1H, N-H), -1.83 (br. s., 1H, N-H).

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Abstract

The present invention is related to novel use of photopyrin compounds useful as an anticancer agent by way of reproducing singlet state oxygen radical and the inventive compounds showed potent inhibition effect on colon cancer, cervical cancer, gastric cancer, cystic cancer or lung cancer. Accordingly, the porphyrin compound of the present invention can be useful in treating or preventing colon cancer, cervical cancer, gastric cancer, cystic cancer or lung cancer in human or mammal.

Description

CROSS REFERENCE TO RELATED APPLICATION [0001] This application is a continuation-in part of U.S. Ser. No. 10 / 718,734 filed on Nov. 20, 2003.DESCRIPTION [0002] 1. Technical Field [0003] The present invention relates to a method of treating or preventing colon cancer, cervical cancer, gastric cancer, or cystic cancer in a mammal said method comprises administering a therapeutically effective amount of porphyrin derivatives or their pharmaceutically acceptable salts thereof. [0004] 2. Background Art [0005] Photodynamic tumor therapy is one of therapeutic techniques to treat incurable diseases using by photosensitizer drugs having a selectivity and photoenhancing activity to cancer cells or various tumors without a surgical operation and complication occurring in Chemotherapy. [0006] The action mechanism of photosensitizer drugs is that for example, the drug is administrated intravenously to a patient and the optimum amount of light is irradiated thereto to form excited state of photose...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/555A61K31/409A61K41/00A61K49/00C07D487/22
CPCA61K31/409A61K31/555A61K49/0036C07D487/22A61K41/0071A61P35/00
Inventor WOO, NAM-TAEKANG, MIN-SUKLEE, WON-YOUNGLEE, CHANG-HEEKIM, YONG-ROKLEE, DAI-WOONWON, DONG-HOONKO, SI-HWAN
Owner TECHNOMART
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