Bufalin derivatives, pharmaceutical compositions and methods thereof

A compound and pharmaceutical technology, applied in the field of its pharmaceutical composition and bufalin derivatives, can solve the problems of poor solubility, narrow therapeutic index, limitation and the like

Active Publication Date: 2014-08-13
SUZHOU NEUPHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its clinical application is limited due to its poor solubility and narrow therapeutic index

Method used

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  • Bufalin derivatives, pharmaceutical compositions and methods thereof
  • Bufalin derivatives, pharmaceutical compositions and methods thereof
  • Bufalin derivatives, pharmaceutical compositions and methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0270] The following examples serve to more fully describe the manner of using the invention. These examples are provided for illustrative purposes and should not be used to limit the true scope of the invention.

[0271] In practicing the steps of the methods described herein, it will of course be understood that references to particular buffers, media, reagents, cells, culture conditions, etc., are not intended to be limiting, but are to be understood to include those that would be recognized by one of ordinary skill in the art when such references are made. All relevant material that is of interest or value in the particular context of the discussion. For example, it is often possible to substitute one buffer system or medium for another and still obtain similar, if not identical, results. Those skilled in the art have sufficient knowledge of such systems and methods to be able (without undue experimentation) to make such substitutions that best serve their purposes in usi...

Embodiment I

[0272] Example I: (R)-2-alanine (3S, 5R, 8R, 9S, 10S, 13R, 14S, 17R)-14-hydroxyl-10,13-dimethyl-17-(2-oxo Preparation of -2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3-yl ester

[0273]

[0274] (R)-2-aminopropionic acid (3S, 5R, 8R, 9S, 10S, 13R, 14S, 17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyridine Fyran-5-yl)hexadecahydro-1H-cyclopentadien[a]phenanthrene-3-yl ester

[0275]

[0276] To Boc-amino acid (11.3mg, 0.06mmol, 1.2eq), HOBT (9.7mg, 0.072mmol, 1.44eq), EDC (13.8mg, 0.072mmol, 1.44eq) and DMAP (16.8mg, 0.15mmol, 3eq) in CH 2 Cl 2 Bufalin (20 mg, 0.05 mmol) was added to the solution in . The mixture was stirred at 37 °C for 16 h, then purified by preparative TLC (PE / EA=1:1) to give (R)-2-((tert-butoxycarbonyl)amino)propanoic acid (3S, 5R, 8R, 9S, 10S, 13R, 14S, 17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopentadiene An[a]phenanthrene-3-yl ester (23 mg, 79.8%).

[0277]

[0278]At 0°C, to (R)-2-((tert-buto...

Embodiment II

[0279] Example II: (2-(pyrrolidin-1-yl)ethyl)carbonate (3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17 Preparation of -(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopentadien[a]phenanthrene-3-yl ester

[0280]

[0281] (2-(Pyrrolidin-1-yl)ethyl)carbonic acid (3S, 5R, 8R, 9S, 10S, 13R, 14S, 17R)-14-hydroxy-10,13-dimethyl-17-(2- Oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3-yl ester

[0282]

[0283] To 1 (60mg, 0.15mmol) and DMAP (16.8mg, 0.15mmol) in CH 2 Cl 2 To a solution in (10 mL) was added DIEA (77.4 mg, 0.6 mmol) and 4-nitrophenyl carbonochloridate (60.6 mg, 0.3 mmol). The mixture was stirred at 37 °C for 16 h, then purified by preparative TLC (PE / EA=1:1) to give 4-nitrophenylcarbonic acid (3S, 5R, 8R, 9S, 10S, 13R, 14S , 17R)-14-hydroxyl-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopentadiene[a]phenanthrene-3 -yl ester (72mg, 87.1%).

[0284]

[0285] To 4-nitrophenylcarbonic acid (3S, 5R, 8R, 9S, 10S, 13R, 14S, 17...

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Abstract

The invention provides bufalin derivatives described in formula 2, pharmaceutical compositions containting the same, and use of the same in treatment of cancer.

Description

[0001] This application is a divisional application of a Chinese patent application with the application number 201180000092.8 (international application number PCT / CN2011 / 000065), the application date is January 14, 2011, and the invention title is "certain compounds, compositions and methods" . [0002] This application claims the benefit of priority to US Provisional Application No. 61 / 295,177, filed January 15, 2010, which is hereby incorporated by reference in its entirety. field of invention [0003] The present invention relates to certain compounds and compositions thereof which are useful in the treatment of cancer. In particular, the present invention relates to bufalin derivatives, their pharmaceutical compositions and uses. Background technique [0004] Cancer can be viewed as a breakdown in communication between tumor cells and their environment, including their normal neighbors. Within tissues, growth-stimulatory and growth-inhibitory signals are commonly exc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00A61K31/585A61P35/00A61P35/02
CPCA61K31/585C07J51/00C07J17/00C07J43/003C07J41/0055A61P35/00A61P35/02A61K9/0019A61K9/0053A61K45/06
Inventor 钱向平
Owner SUZHOU NEUPHARMA CO LTD
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