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New piperazine derivative and medical applications

A derivative, piperazine technology, applied in the field of new piperazine derivatives and their medical applications, can solve the problems of limited clinical application and low bioavailability

Inactive Publication Date: 2014-01-15
BEIJING MEIBEITA DRUG RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the influence of these factors, resveratrol, curcumin, andrographolide, dehydroandrographolide, puerarin, camptothecin and its derivatives, paclitaxel and its derivatives, docetaxel and its derivatives, water The low bioavailability of Fujilin and silybin, triptolide and its analogs, ginkgolide B and its analogs, propofol and other drugs limits their clinical application

Method used

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  • New piperazine derivative and medical applications
  • New piperazine derivative and medical applications
  • New piperazine derivative and medical applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1N-(resveratrol-4'-oxycarbonylpropionyl)-piperazine (Ia-1) and N-(resveratrol-3-oxycarbonylpropionyl)-piperazine (Ib-1) preparation of

[0054]

[0055] 1.1 Synthesis of resveratrol-4'-oxycarbonylpropionic acid and resveratrol-3-oxycarbonylpropionic acid

[0056] Add 10g (43.8mmol) of resveratrol to 200ml of dry dichloromethane, add 4.38g (43.8mmol) of succinic anhydride, add 5ml of anhydrous pyridine, and stir at 40°C for 12 hours. It was washed successively with 0.5N hydrochloric acid and saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residue was separated by silica gel column chromatography, eluted with a mixed solvent of ethyl acetate:petroleum ether:acetic acid (2:10:0.2), and the required components were collected respectively, and evaporated to dryness under reduced pressure to obtain resveratrol-4 4.1 g of '-oxycarbonylpropionic acid and ...

Embodiment 2

[0063] Example 2 N-(resveratrol-4'-oxycarbonyl butyryl)-piperazine (Ia-2) and N-(resveratrol-3-oxycarbonyl butyryl)-piperazine (Ib-2) preparation of

[0064]

[0065] 2.1 Synthesis of resveratrol-4′-oxycarbonyl butyric acid and resveratrol-3-oxycarbonyl butyric acid

[0066] Add 10g (43.8mmol) of resveratrol to 200ml of dry dichloromethane, add 5.0g (43.8mmol) of glutaric anhydride, add 5ml of anhydrous pyridine, and stir at 40°C for 12 hours. It was washed successively with 0.5N hydrochloric acid and saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residue was separated by silica gel column chromatography, eluted with a mixed solvent of ethyl acetate:petroleum ether:acetic acid (2:10:0.2), and the required components were collected respectively, and evaporated to dryness under reduced pressure to obtain resveratrol-4 4.0 g of '-oxycarbonyl butyric acid and 1.9 g...

Embodiment 3

[0071] Dissolve 0.56g of N-(resveratrol-3-oxycarbonylbutyryl)-piperazine (Ib-2) with the minimum amount of methanol, drop into the ether solution of hydrogen chloride until no precipitate precipitates; place overnight at 4°C, filter , and dried to obtain 0.3 g of the hydrochloride salt of Ib-2, with a melting point of 97-102° C., and its solubility in distilled water was determined to be 10 mg / ml. Embodiment 3N-(curcumin-4'-oxycarbonyl propionyl)-piperazine (Ic-1)

[0072]

[0073] Add 3.68g (10mmol) of curcumin to 100ml of dry dichloromethane, add 1.0g (10mmol) of succinic anhydride, add 1ml of anhydrous pyridine, and stir at 40°C for 12 hours. It was washed successively with 0.5N hydrochloric acid and saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residue was separated by silica gel column chromatography, eluted with a mixed solvent of ethyl acetate:petroleum ...

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Abstract

The invention relates to a piperazine derivative or pharmaceutically acceptable salts thereof represented by the formula I, pharmaceutical compositions containing the piperazine derivative or pharmaceutically acceptable salts thereof represented by the formula I as an active component, and applications of the piperazine derivative or pharmaceutically acceptable salts thereof represented by the formula I for preparing medicaments. Wherein, D represents a medicament base containing hydroxyl, R represents H or alkyl with 1-3 carbon atoms, and n represents an integer in a range of 1-4.

Description

technical field [0001] The present invention relates to piperazine derivatives represented by formula I or pharmaceutically acceptable salts thereof, and pharmaceutical compositions containing piperazine derivatives represented by formula I or pharmaceutically acceptable salts thereof as active ingredients, and formula The new piperazine derivative shown in I or its pharmaceutically acceptable salt is used for the purposes of preparing medicine. [0002] [0003] Wherein, D is a drug group containing a hydroxyl group, R is H or an alkyl group with 1-3 carbon atoms, and n is an integer of 1-4. Background technique [0004] Drug bioavailability is an important pharmacokinetic parameter affecting the effectiveness of oral drugs. Drug absorption is often limited by many barriers, including physiological (eg, endothelial cell density), biochemical (efflux transporters), and chemical (volume, lipid solubility, molecular weight, charge, etc.). Due to the influence of these fac...

Claims

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Application Information

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IPC IPC(8): C07D295/185C07D307/33C07D307/58C07D407/04C07D491/22C07D305/14C07D493/22A61K31/495A61K31/496A61P35/00A61P23/00A61P29/00A61P7/10A61P1/16A61P39/00
CPCC07D295/185C07D305/14C07D307/33C07D307/58C07D407/04C07D491/22C07D493/22
Inventor 陈蓉王建彬
Owner BEIJING MEIBEITA DRUG RES