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Crisaborole prodrug and its preparation method and use

A pharmacy and CH2 technology, applied in chemical instruments and methods, antipyretics, drug combinations, etc., can solve problems such as side effects and depression, and achieve the effects of enhancing drug efficacy, good solubility, and high bioavailability

Active Publication Date: 2022-04-19
苏州东南药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the current clinical PDE4 inhibitors have a certain degree of side effects, such as nausea, vomiting and other gastrointestinal reactions, and even depression

Method used

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  • Crisaborole prodrug and its preparation method and use
  • Crisaborole prodrug and its preparation method and use
  • Crisaborole prodrug and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 8

[0058] Example 8 I-1~I-7Crisaborole prodrug compound in vitro stability test

[0059] 1. High performance liquid chromatography determination conditions

[0060] Liquid chromatograph: Waters 2489UV / Visible Detector, Waters 1525Binary HPLC Pump;

[0061] Chromatographic column: Kromasil 100-5-C18, Dim: 4.6x150mm, Part / Serial: M05CLA15 / E121514;

[0062] Mobile phase: acetonitrile (50%-80%) and water gradient elution;

[0063] Flow rate: 1mL / min Column temperature 25°C;

[0064] The detection wavelength is 254nm and the injection volume is 10 μL;

[0065] The retention time of Crisaborole is about 18min without interference from the mobile phase.

[0066] 2. Sample Preparation

[0067] The target compound was dissolved in DMSO solvent, and the concentration was converted to Crisaborole 120 mg / mL according to the concentration. Take 20 μL of this solution and add it to 1.18 mL of fresh rat blank plasma, and incubate at 37 ° C to obtain the sample.

[0068] 3. Sample pretreat...

Embodiment 9

[0079] The above data show that compounds I-1 to I-7 can be rapidly converted into the original drug Crisaborole in plasma. Embodiment 9 Compound I-1~I-7 transdermal drug release experiment

[0080] Tested with the single-compartment static chamber method, the back skin of guinea pigs three months old was taken out successively for the test, and the release pool with the experimental skin piece fixed was installed on the upper side of the single compartment, and the drug was placed on the isolated experimental skin. Constant temperature in a 32°C water bath for a certain period of time, absorb the stirred solution in the subcutaneous compartment of the experiment for measurement, use liquid chromatography and CR2Ax-2 microcomputer processor, liquid chromatography to determine the peak value of samples in the sample chamber and receiving chamber, CR2Ax -2 The microcomputer processor calculates the area of ​​the peak meter, monitors and calculates the drug penetration. The resu...

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Abstract

The present invention obtains a series of Crisaborole prodrugs represented by the general formula I by modifying the active site of Crisaborole: the compound designed by the present invention can be rapidly converted into the original drug Crisaborole in plasma, and compared with the original drug, it has better It has better solubility, higher bioavailability, enhanced efficacy, and is a new type of compound with PDE‑4 inhibitory activity.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis and medical application, and in particular relates to a prodrug of Crisaborole and its preparation method and application. Background technique [0002] Prodrugs, also known as prodrugs, drug precursors, prodrugs, etc., are mainly aimed at improving the bioavailability of drugs, increasing drug stability, reducing toxic and side effects, and promoting long-acting drugs. Prodrug is a very useful drug design method. After chemical structure modification, it is inactive or less active in vitro, and the active drug is released through enzymatic or non-enzymatic conversion in vivo to exert its medicinal effect. At present, clinical prodrugs have been widely used in the treatment of various diseases, and there is still a lot of room for development. In conclusion, prodrug strategies have become an integral part of drug design and delivery methods. [0003] Phosphodiesterases (PDEs) ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02A61P29/00A61P37/02A61P25/16A61P25/24A61P25/22A61P19/10A61P13/12A61P35/02A61P31/18A61P3/10A61P9/12A61P17/06A61P15/10A61P11/00
CPCC07F5/02A61P29/00A61P37/02A61P25/16A61P25/24A61P25/22A61P19/10A61P13/12A61P35/02A61P31/18A61P3/10A61P9/12A61P17/06A61P15/10A61P11/00
Inventor 宗玺吉民胡海燕
Owner 苏州东南药业股份有限公司
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