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An antipyretic and analgesic ibuprofen-β-cyclodextrin first-side derivative and preparation method thereof

An antipyretic and analgesic, cyclodextrin technology, applied in antipyretics, drug combinations, pharmaceutical formulations, etc., can solve the problems of reducing ibuprofen antipyretic, analgesic time, hemolysis, and large fluctuations in blood drug concentration

Active Publication Date: 2021-12-10
NINGXIA MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, because ibuprofen is released too quickly in the human body, it reduces the antipyretic and analgesic time of ibuprofen in the human body, and because its half-life is longer, reaching 1.8-2 hours, it takes 2-3 times a day, causing The plasma concentration of ibuprofen in the human body fluctuates greatly, causing patients to often experience hemolysis after taking the drug, causing adverse reactions such as heartburn, stomach pain, nausea, and vomiting, and aggravating bleeding tendency, especially in hemophilia or other diseases. Ibuprofen should be used with caution in patients with bleeding disorders

Method used

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  • An antipyretic and analgesic ibuprofen-β-cyclodextrin first-side derivative and preparation method thereof
  • An antipyretic and analgesic ibuprofen-β-cyclodextrin first-side derivative and preparation method thereof
  • An antipyretic and analgesic ibuprofen-β-cyclodextrin first-side derivative and preparation method thereof

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preparation example Construction

[0025] A preparation method of the antipyretic and analgesic ibuprofen-β-cyclodextrin first derivative as described in any one of claims 1-2, comprising the following steps:

[0026] Step a), the synthesis of ibuprofen imidazolate, ibuprofen is dissolved in dichloromethane, N, N'-carbonyldiimidazole (CDI) is dissolved in dichloromethane, and then the dichloromethane of ibuprofen The methane solution is added dropwise into the dichloromethane solution of CDI through the dropping funnel, stirred evenly until the reaction is completed, and dried after acid-base extraction and n-hexane precipitation to obtain imidazolate ibuprofen;

[0027] The synthetic route of ibuprofen imidazolate is:

[0028]

[0029]Step b), the synthesis of the first derivative of ibuprofen-β-cyclodextrin, the ibuprofen imidazolate prepared in step a) is dissolved in N,N-dimethylformamide (DMF), To form a DMF solution of imidazolate ibuprofen, add β-cyclodextrin to the DMF solution of imidazolate ibupro...

Embodiment 1

[0044] The preparation of ibuprofen imidazolate: ibuprofen 0.01mol (2.06g) is dissolved in 30ml dichloromethane; CDI0.015mol (2.43g) is dissolved in 60ml dichloromethane; The dichloromethane solution of ibuprofen is passed through The dropping funnel was added dropwise into the dichloromethane solution of CDI, reacted for 12-24 hours, extracted with acid and alkali, precipitated with n-hexane and dried to obtain imidazolate ibuprofen (yield 80%).

[0045] The ibuprofen imidazolate that this embodiment makes, nuclear magnetic data is as follows:

[0046] R f =0.53; 1 H NMR (400MHz, DMSO-d 6 ):8.49,7.71,7.32,7.30,7.13,7.11, 7.01,4.76,4.74,2.51,2.39,2.37,1.82-1.72,1.49,1.47,0.82,0.80; 13 C NMR (400MHz, DMSO-d 6 ): 171.8, 140.88, 137.63, 130.75, 130.07, 127.53, 117.24, 44.61, 44.36, 40.60-39.44, 29.99, 22.59, 19.59.

[0047] Preparation of ibuprofen β-cyclodextrin first side derivative: β-cyclodextrin (2.55 g, 2.25 mmol) was added into a 250 ml round bottom flask, and then 80...

Embodiment 2

[0050] Preparation of the first side derivative of ibuprofen β cyclodextrin: β-cyclodextrin (2.25g, 2.00mmol) was added in a 250ml round bottom flask, and other steps were the same as in Example 1, thereby obtaining purified ibuprofen The first side derivative of fen β-cyclodextrin (yield 28%).

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Abstract

An antipyretic and analgesic ibuprofen-β-cyclodextrin first side derivative and its preparation method. In the invention, ibuprofen and N,N'-carbonyldiimidazole (CDI) are used as raw materials to prepare intermediate Product ibuprofen imidazolate, then ibuprofen imidazolate and β-cyclodextrin reaction, by adding NaOH, Na 2 CO 3 , NaHCO 3 By effectively activating the primary hydroxyl group on the first side of the β-cyclodextrin, the derivatives of the first side of the ibuprofen-β-cyclodextrin are prepared. Selectively modify the ibuprofen functional group on the hydroxyl group on the first side of β-cyclodextrin, greatly slow down the release rate of the ibuprofen functional group in the human body, improve the antipyretic and analgesic effects; The release is stable, avoiding the phenomenon of peaks and valleys of drug efficacy, so that patients will no longer experience hemolysis after taking the first derivative of ibuprofen-β-cyclodextrin, and avoid adverse reactions such as stomach burning, stomach pain, nausea, and vomiting.

Description

technical field [0001] The invention relates to the technical field of medicinal chemical synthesis, in particular to an antipyretic and analgesic ibuprofen-β-cyclodextrin first derivative and a preparation method thereof. Background technique [0002] β-cyclodextrin and its derivatives, as a drug molecular carrier with selective inclusion ability, play a role in pharmacy that is difficult for common excipients. Its molecular structure is a ring-shaped, hollow cylinder. Compared with other macrocyclic molecules, β-cyclodextrin is special in that it has a rigid conical cavity structure with a hydrophobic inner cavity and a hydrophilic outer cavity. The hydroxyl groups on the surface of cyclodextrin are mainly divided into two types, among which the primary hydroxyl group (ie, the 6-position hydroxyl group) constitutes the main surface (ie, the first surface) of the cyclodextrin cone-shaped cavity structure, and the secondary hydroxyl group (ie, the 2-position Hydroxyl and 3-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/16A61K47/69A61K31/192A61P29/00
CPCC08B37/0012A61K47/6951A61K31/192A61P29/00
Inventor 王志忠王玉营黄青褚慧敏魏世杰
Owner NINGXIA MEDICAL UNIV
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