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Novel nalmefene dimer as well as preparation method and application thereof

A dimer, opioid receptor technology, applied in the direction of medical preparations containing active ingredients, pharmaceutical formulations, organic active ingredients, etc., can solve the separation of nalmefene dimer compounds, structure confirmation and research on its use , prone to oxidation and other problems

Pending Publication Date: 2021-10-12
SICHUAN HAISCO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The structure of nalmefene is similar to that of morphine, there are phenolic hydroxyl groups, and it is prone to oxidation, and the related substances increase to a certain extent. So far, there is no separation, structural confirmation and use of the new nalmefene dimer compound of the present invention Research related reports

Method used

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  • Novel nalmefene dimer as well as preparation method and application thereof
  • Novel nalmefene dimer as well as preparation method and application thereof
  • Novel nalmefene dimer as well as preparation method and application thereof

Examples

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Embodiment 1

[0064] Embodiment 1 The preparation of new nalmefene dimer compound of the present invention

[0065] Nalmefene (3.39g, 10mmol), potassium tert-butoxide (0.56g, 5mmol), N,N-dimethylformamide (50ml) and diiodomethane (1.34g, 5mmol) were mixed and stirred, heated at 70°C React for 8 hours. Add the reaction solution to 200ml of water, extract with 100ml of ethyl acetate*3 times, combine the ethyl acetate phase; wash the ethyl acetate phase with 100ml of saturated brine; separate the ethyl acetate phase, and distill off the ethyl acetate under reduced pressure. The resulting residue is the crude product, and the sample is prepared by liquid phase (the chromatographic column is a carbon-octave bonded silica gel column, mobile phase A: 0.03% aqueous solution; B: acetonitrile, gradient elution, 10% ~ 40% B, 60 minutes; flow rate 80ml / min) to obtain 0.35g of the product with a purity of 97.7% by HPLC.

Embodiment 2

[0066] Embodiment 2 The preparation of new nalmefene dimer compound of the present invention

[0067] Nalmefene (3.39g, 10mmol), sodium methoxide (2.16g, 40mmol), N,N-dimethylformamide (50ml) and dichloromethane (84.93g, 1000mmol) were mixed and stirred, heated at 40°C for 24 Hour. Add the reaction solution to 200ml of water, extract with 100ml of dichloromethane*3 times, combine the dichloromethane phases; wash the dichloromethane phase with 100ml of saturated brine; separate the dichloromethane phase, and distill off the dichloromethane under reduced pressure. The resulting residue is the crude product, and the sample is prepared by liquid phase (the chromatographic column is a carbon-octave bonded silica gel column, mobile phase A: 0.03% aqueous solution; B: acetonitrile, gradient elution, 10% ~ 40% B, 60 minutes; flow rate 80ml / min) to obtain 0.22g of the product, with a HPLC purity of 96.4%.

Embodiment 3

[0068] Embodiment 3 The preparation of new nalmefene dimer compound of the present invention

[0069] Nalmefene (3.39g, 10mmol), sodium ethoxide (1.36g, 20mmol), tetrahydrofuran (50ml) and dibromomethane (8.69g, 50mmol) were mixed and stirred, and reacted at 0°C for 24 hours. Add the reaction solution to 200ml of water, extract with 100ml of ethyl acetate*3 times, combine the ethyl acetate phase; wash the ethyl acetate phase with 100ml of saturated brine; separate the ethyl acetate phase, and distill off the ethyl acetate under reduced pressure. The resulting residue is the crude product, and the sample is prepared by liquid phase (the chromatographic column is a carbon-octave bonded silica gel column, mobile phase A: 0.03% aqueous solution; B: acetonitrile, gradient elution, 10% ~ 40% B, 60 minutes; flow rate 80ml / min) to obtain 0.32g of the product with a purity of 96.0% by HPLC.

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Abstract

The invention relates to a novel nalmefene dimer compound with a structure as shown in a formula (I) or a salt thereof, and a preparation method and application of the compound, and the compound has a relatively strong inhibition effect on prostate cancer cell lines LNCaP and 22Rv1, and can be used for preparing drugs for resisting prostate cancer.

Description

technical field [0001] The invention relates to a compound and its preparation method and application, in particular to a new nalmefene dimer compound, its preparation method and application, and belongs to the field of medicinal chemistry. Background technique [0002] Nalmefene hydrochloride, synthesized in 1975, is another new pure opioid receptor antagonist synthesized after naloxone (NAL) and naltrexone (NTX). It can bind to opioid receptors μ, κ, and δ, and has the strongest binding effect on μ receptors. Nalmefene hydrochloride is a water-soluble derivative of naltrexone, its 6-methylene chemical structure makes it have a long action time, multiple drug routes, high bioavailability, less side effects, stronger physiological activity, and easier penetration Biofilm and other properties have varying degrees of effects on maintaining the normal functions of respiration, circulation, digestion, endocrine and nervous system. Currently, it has been used in the antagonism o...

Claims

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Application Information

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IPC IPC(8): C07D519/00A61K31/485A61P35/00A61P43/00
CPCC07D519/00A61P35/00A61P43/00
Inventor 程训官汪东海王利叶飞
Owner SICHUAN HAISCO PHARMA CO LTD
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