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Metallocene derivatives with anticancer activity

A compound and mixture technology, applied in the field of metallocene derivatives, can solve the problem of low activity

Active Publication Date: 2016-09-28
巴黎科学与文学基金会
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] Molecule 4 also exhibits anti-proliferative activity against the same breast cancer cell lines (MCF-7, MDA-MB-231), but its activity is lower than that of molecule 2 (unsubstituted analogue)
[0016] Unfortunately, the aforementioned open molecules 1, 2, 3 and 4 are not yet optimal for proper R&D

Method used

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  • Metallocene derivatives with anticancer activity
  • Metallocene derivatives with anticancer activity
  • Metallocene derivatives with anticancer activity

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0100] Syrup or elixir dosage forms are prepared containing the active ingredient and sweetening, preservative, and flavoring and suitable coloring agents.

[0101] Water-dispersible powders or granules can contain the active ingredient in admixture with dispersing or wetting agents or suspending agents, and with taste regulators or sweeteners.

[0102] For rectal administration, suppositories may be employed, prepared with binders such as cocoa butter or polyethylene glycols which melt at rectal temperature.

[0103] For parenteral, intranasal or intraocular administration, aqueous suspensions, isotonic saline solutions or sterile solutions for injection containing pharmaceutically compatible dispersing and / or wetting agents are used.

[0104] The active ingredient can be further formulated in the form of microcapsules or nanocapsules, optionally with one or more additive carriers.

[0105] The compounds of the present invention can be used in a daily dose ranging between 0....

Embodiment

[0181] Abbreviations used:

[0182] CI chemical ionization

[0183] DCM dichloromethane

[0184] DMF Dimethylformamide

[0185] DMSO dimethyl sulfoxide

[0186] EI electron ionization

[0187] ESI electrospray ionization

[0188] Et ethyl

[0189] HRMS High Resolution Mass Spectrometry

[0190] IR infrared

[0191] Me methyl

[0192] MS mass spectrometry

[0193] NMR nuclear magnetic resonance

[0194] PE petroleum ether

[0195] THF Tetrahydrofuran

[0196] TLC thin layer chromatography

example 1

[0197] Example 1: Preparation of compounds of the present invention

[0198] 1.1. Preparation of ester derivatives

[0199]

[0200] where Alk=(C 1 -C 6 ) alkyl and n, R1 and R2 are as defined above.

[0201] General Flow (McMurray Reaction) :

[0202] Titanium chloride was added dropwise to a suspension of zinc powder dissolved in dry THF at 10 °C. The mixture was heated to reflux for 2 hours. A second solution was prepared by dissolving the corresponding ketone (equimolar) in dry THF. This latter solution was added dropwise to the first solution, followed by continued reflux for 2 hours or more. After cooling to room temperature, the mixture was stirred together with water and dichloromethane. The mixture was acidified using diluted hydrochloric acid until the black color disappeared and the mixture was decanted. The aqueous phase was extracted with dichloromethane, and the combination of organic phases was dried over magnesium sulfate. After concentration unde...

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PUM

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Abstract

The present invention relates to a compound of the following formula (I) or a pharmaceutically acceptable salt or solvate thereof, a stereoisomer or a mixture of stereoisomers in any ratio, or a water-soluble derivative, as well asto methods for preparing same and to the use thereof, in particular in the treatment of cancer.

Description

technical field [0001] The present invention relates to metallocene derivatives for the treatment of cancer, as well as processes for their preparation and their use as medicaments, especially in the treatment of cancer. Background technique [0002] Cancer, the leading cause of mortality in France, is affecting more and more people due to the increase in life expectancy. [0003] However, approximately 1 / 3 of cancers remain incurable due to the intrinsic resistance of cancer to pro-apoptotic stimuli and more than 85% of currently available cancer treatments are pro-apoptotic compounds such as DNA alkylating agents (Diagnosis have a mortality rate greater than 90% within the year). Such incurable cancers include, for example, glioma, melanoma, non-small cell lung cancer, ovarian cancer, esophageal cancer, pancreatic cancer, head and neck cancer, prostate cancer, and hormone-independent breast cancer, and they involve approximately 13.5 million patients . [0004] Therefor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02A61K31/7135A61P35/00
CPCA61K31/7135C07F17/02A61K31/295A61K31/555A61P35/00A61K2300/00
Inventor 热拉尔·雅乌安帕斯卡·皮金赛德恩·托弗
Owner 巴黎科学与文学基金会