Unlock instant, AI-driven research and patent intelligence for your innovation.

Compound with antitumor activity and preparation method thereof

An anti-tumor drug and compound technology, applied in the field of compounds with anti-tumor activity and their preparation, can solve the problems of precipitation, inconvenience in use, high toxicity and the like of the preparation, and achieve enhanced immunomodulatory activity, improved pharmacodynamic index, good water soluble effect

Active Publication Date: 2013-08-21
CHENGDU SHENGNUO BIOTEC CO LTD
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are still many patients with life-threatening hypersensitivity symptoms in clinical practice. In addition, patients with hypertension, diabetes, ulcer disease and anaphylaxis cannot use ordinary paclitaxel drugs, so they can only see the loss of the best treatment opportunity
[0004] In addition, during clinical administration, precipitation will occur when the preparation is diluted with water, and a 0.22 μm microporous membrane filtration device needs to be added during intravenous infusion, which is inconvenient to use
At present, paclitaxel preparations have been studied at home and abroad, and the process of paclitaxel liposomes for injection is relatively complicated and unstable.
Paclitaxel microemulsion formulations use a large amount of surfactants and are highly toxic

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Compound with antitumor activity and preparation method thereof
  • Compound with antitumor activity and preparation method thereof
  • Compound with antitumor activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0051] The preparation method of the compound of the present invention, it is by the compound shown in formula (II) and the Thymopentin C-terminal carboxyl group of protection in the presence of condensation reagent, the product that obtains after condensation reaction deprotects with deprotection reagent, purifies, freeze-dried,

[0052]

[0053] Further, paclitaxel pentapeptide and docetaxel pentapeptide are formed by reacting the 2'-hydroxyl group of paclitaxel or docetaxel and the protected thymopentin C-terminal carboxyl group in the presence of a condensation reagent to generate protected paclitaxel pentapeptide Or docetaxel pentapeptide, deprotected by deprotection reagent, purified by high performance liquid chromatography and freeze-dried.

[0054] The protected thymopentin used in the above preparation method is selected from the following protected thymopentin structures, and the preferred structure is protected thymopentin structure III.

[0055] Protect thymop...

Embodiment 1

[0062] Embodiment 1 prepares paclitaxel pentapeptide

[0063] Take protected thymopentin structure I [Fmoc-Arg(Pbf)-Lys(Boc)-Asp(OtBu)-Val-Tyr(tBu)-OH] 32.8g (24mmol), paclitaxel 10.2g (12mmol), 1-hydroxy -Benzo-triazole 3.3g (24mmol) and 4-dimethylaminopyridine 0.15g (1.2mmol), dissolved with 50ml N,N-dimethylformamide, stirred and added dropwise N,N-diisopropyl Carbodiimide 3.7ml, stirred at room temperature and reacted overnight, poured the reaction solution into 500ml of ice water, stirred well, collected the precipitate by filtration, and washed with water 3 times.

[0064] Add 50ml of 20% piperidine / N,N-dimethylformamide to the precipitate, stir and react at room temperature for 1 hour, pour the reaction solution into 500ml of ice water, stir well, collect the precipitate by filtration, and wash with water 3 times, 40 °C and dried under reduced pressure overnight.

[0065] Add 300ml of deprotecting agent (trifluoroacetic acid: triisopropylsilane: dimercaptoethylene gly...

Embodiment 2

[0066] Embodiment 2 prepares paclitaxel pentapeptide

[0067] Take protected thymopentin structure II [Fmoc-Arg-Lys(Boc)-Asp(OtBu)-Val-Tyr(tBu)-OH] 26.7g (24mmol), paclitaxel 10.2g (12mmol), 1-hydroxy-benzo - Triazole 3.3g (24mmol) and 4-dimethylaminopyridine 0.15g (1.2mmol), dissolved with 50ml N,N-dimethylformamide, stirred dropwise N,N-diisopropylcarbodiethylene Add 3.7ml of amine, stir at room temperature overnight, pour the reaction solution into 500ml of ice water, stir well, collect the precipitate by filtration, and wash with water 3 times.

[0068] Add 50ml of 20% piperidine / N,N-dimethylformamide to the precipitate, stir and react at room temperature for 1 hour, pour the reaction solution into 500ml of ice water, stir well, collect the precipitate by filtration, and wash with water 3 times, 40 °C and dried under reduced pressure overnight.

[0069] Add 300ml of deprotecting agent (trifluoroacetic acid: triisopropylsilane: dimercaptoethylene glycol: water = 94:2:2:2)...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a novel compound with antitumor activity and a preparation method thereof, and belongs to the field of chemical pharmacy. The compound provided by the invention has a structure as shown in Formula (I), has good water-solubility and therapeutical targeting, has high pharmacodynamic index and low drug toxicity, and is used to provide a new way of thought for the preparationof antitumor drugs.

Description

technical field [0001] The invention relates to a novel compound with antitumor activity and a preparation method thereof, belonging to the field of chemical pharmacy. Background technique [0002] Taxol (Paclitaxel, trade name Taxol) is a tetracyclic diterpenoid compound with anticancer activity extracted from Taxus plants. The preparation of American Bumai-Squibb Company-Paclitaxel Concentrated Injection (Taxol) has been approved by FDA , was approved to go public in December 1992. For the treatment of ovarian cancer. The latest survey data show that paclitaxel ranks first among the world's best-selling anticancer drugs. The National Cancer Institute of the United States speculates that paclitaxel will still be the most important anticancer drug in the world in the next 15 years. At present, there are several domestic enterprises producing paclitaxel injection. [0003] Because paclitaxel is insoluble in water, paclitaxel preparations at home and abroad all adopt the sa...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07K7/06C07K1/02A61K38/08A61P35/00
Inventor 文永均谢期林王晓莉韩玉
Owner CHENGDU SHENGNUO BIOTEC CO LTD