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Taxoid-fatty acid conjugates and pharmaceutical compositions thereof

A technology of paclitaxel and conjugates, which can be used in drug combinations, active ingredients of heterocyclic compounds, anti-tumor drugs, etc., and can solve the problems of non-specific drugs for tumors and side effects.

Active Publication Date: 2007-01-24
THE RES FOUND OF STATE UNIV OF NEW YORK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] However, these highly potent second-generation paclitaxels are not tumor-specific
Therefore, various undesired side effects occur during clinical use

Method used

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  • Taxoid-fatty acid conjugates and pharmaceutical compositions thereof
  • Taxoid-fatty acid conjugates and pharmaceutical compositions thereof
  • Taxoid-fatty acid conjugates and pharmaceutical compositions thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] 2'-Docosahexaenoyl-3'-desphenyl-3'-(2-methyl-2-propyl)-10-(methoxycarbonyl)docetaxel (DHA-SB-T -1107):

[0088] 3'-Desphenyl-10-(methoxycarbonyl)-3'-(2-methyl-2-propyl)-2'-eco Add 4-dimethylaminopyridine (9 mg; 75 μmol), 1,3-dicyclohexylcarbodiimide to a solution of docetaxel (SB-T-1107) (63.9 mg; 75 μmol) (19mg, 150μmol), and DHA (27mg; 83μmol). The reaction mixture was stirred at room temperature for 1 h. After diluting with dichloromethane, the reaction mixture was washed with 5% hydrochloric acid, water, and brine. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under vacuum. The crude product was purified by chromatography on silica gel (ethyl acetate / hexane = 1 / 3 to 1 / 1) to give 78.5 mg (90% yield) of DHA-SB-T as a white solid -1107: melting point m.p.102-105°C, [α] D 22 -45.0 (c1.0, CHCl 3 ); 1 H NMR (400MHz, CDCl 3 )δ0.96(m, 9H), 1.14(s, 3H), 1.22(s, 3H), 1.30(s, 9H), 1.67(m, 3H), 1.69(s, 3H), 1.88(m, 1H ), 1.96(s, 3H), ...

Embodiment 2-9

[0090] Other DHA-paclitaxel was synthesized in the same manner as described in Example 1 for the synthesis of DHA-SB-T-1107. Characterization data for these DHA-paclitaxels are shown below.

Embodiment 2

[0092] 2’-Docosahexaenoyl-3’-desphenyl-3’-(2-methylpropyl)-10-propionyl docetaxel (DHA-SB-T-1103):

[0093] 75% yield; white solid; m.p. 94-98°C, [α] D 22 -37.9 (c 1.08, CHCl 3 ); 1 H NMR (400MHz, CDCl 3)δ0.97(m, 9H), 1.13(s, 3H), 1.22-1.27(m, 6H), 1.31(s, 9H), 1.56(s, 3H), 1.67(s, 3H), 1.90(m , 1H), 1.94(s, 3H), 2.08(m, 2H), 2.39(s, 3H), 2.40(m, 2H), 2.46-2.60(m, 7H), 2.85(m, 10H), 3.82( d, J=7.0Hz, 1H), 4.20(d, J=8.4Hz, 1H), 4.30(d, J=8.4Hz, 1H), 4.35(m, 1H), 4.46(dd, J=10.2, 6.7 Hz, 1H), 4.60(d, J=10.4Hz, 1H), 4.92(d, J=2.4Hz, 1H), 4.98(d, J=7.6Hz, 1H), 5.40(m, 12H), 5.67( d, J=7.6Hz, 1H), 6.23(m, 1H), 6.31(s, 1H), 7.48(t, J=7.6Hz, 2H), 7.60(t, J=7.6Hz, 1H), 8.12( d, J=7.6Hz, 2H); 13 C NMR (400MHz, CDCl 3 )δ9.0, 9.6, 14.1, 14.3, 14.8, 20.5, 21.9, 22.2, 22.4, 22.5, 22.6, 23.2, 24.5, 25.5, 25.6, 26.6, 27.5, 28.1, 28.3, 33.7, 35.5, 41.3, 43.2, 45.6 , 48.9, 58.8, 71.5, 72.2, 74.4, 75.2, 75.5, 76.4, 77.3, 79.3, 79.8, 81.0, 84.4, 127.0, 127.5, 127.8, 127.9, 128.0, 128.3...

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Abstract

The present invention relates to the second generation fatty acid conjugate and its pharmaceutical composition. The second generation fatty acid conjugates are useful in the treatment of cancer in humans in need thereof.

Description

[0001] The invention described in this application was made with support from the National Institutes of Health under grant numbers R01 GM427980 and R01 CA103314. The US Government has certain rights in this invention. [0002] This application claims priority to US Provisional Application Serial No. 60 / 515,783, filed October 30, 2003, the entire contents of which are hereby incorporated by reference. Background technique [0003] paclitaxel (purin or paclitaxel, paclitaxel) (Taxol  ) and docetaxel (Taxotere  ) are two of the most important antineoplastic drugs approved clinically for chemotherapy of human tumors. Paclitaxel is a naturally occurring taxane that was originally isolated from the bark of the Pacific yew tree (Taxus brevifolia). [0004] Docetaxel is a semisynthetic homologue of paclitaxel. Docetaxel was the first "paclitaxel," a paclitaxel-like compound, to be approved for clinical use by the FDA. [0005] These two first-generation taxane anticancer agent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/35C07D305/00A61KC07D305/14C07D493/04
CPCC07D305/14A61K47/48038C07D493/04A61K47/542A61P35/00
Inventor 伊瓦奥·奥吉马
Owner THE RES FOUND OF STATE UNIV OF NEW YORK
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