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Cetirizine derivatives, and composition and application thereof

A composition and compound technology, which is applied in the direction of drug combination, respiratory system diseases, skin diseases, etc., can solve the problems of low transdermal efficiency, difficult to achieve effective blood drug concentration, and no guarantee of therapeutic effect, and achieve the effect of improving efficiency

Inactive Publication Date: 2011-09-21
杨利
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, in clinical use, it is generally believed that cetirizine and eflurazine can only be taken orally
Because of its low transdermal efficiency, it is difficult to achieve the effective blood drug concentration after transdermal administration, and the therapeutic effect cannot be guaranteed.

Method used

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  • Cetirizine derivatives, and composition and application thereof
  • Cetirizine derivatives, and composition and application thereof
  • Cetirizine derivatives, and composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] The preparation of embodiment 1 compound

[0084](1) Preparation of 2-[2-[4-[(4-chlorophenyl)benzyl]-1-piperazinyl]ethoxy]diethylaminoethyl acetate

[0085] 38.89 g of cetirizine was dissolved in 100 ml of chloroform, and the mixture was cooled to 0°C. 20.63 g of 1,3-dicyclohexylcarbodiimide (DCC) was added to the reaction mixture, and stirred at 0° C. for 30 minutes. 11.72 g of 2-diethylaminoethanol was added to the reaction mixture, and stirred at room temperature for 3 hours. 6.01 g of acetic acid was added to the reaction mixture with stirring. The solid by-product was removed by filtration, washed three times with 50 ml of chloroform, and the organic phase was evaporated. After drying, 50.04 g of the hygroscopic target product were obtained. 1 H-NMR (400MHz, CDCL 3 ): δ: 1.56(t, 6H), 2.20(s, 3H), 2.51(t, 2H), 2.71(s, 8H), 3.28(q, 4H), 3.52(t, 2H), 3.60(t, 2H), 4.33(s, 2H), 4.52(t, 2H), 5.14(s, 1H), 6.95(s, 1H), 7.17(s, 2H), 7.26(s, 1H), 7.35(m, 6H ).

[008...

Embodiment 2

[0096] Embodiment 2 tests in vivo and measures transdermal rate

[0097] 1. Preparation of test solution

[0098] Need test solution 1: be dissolved in the 10% (W / V) cetirizine suspension of 1ml isopropanol;

[0099] Test solution 2: 10% (W / V) 2-[2-[4-[(4-chlorophenyl)benzyl]-1-piperazinyl]ethoxy in 1ml of isopropanol ] diethylaminoethyl acetate solution;

[0100] Test solution 3: 10% (W / V) 2-[2-[4-[(4-chlorophenyl)benzyl]-1-piperazinyl]ethoxy in 1ml of isopropanol ] dimethylaminoethyl acetate solution;

[0101] Need test solution 4: be dissolved in the levocetirizine suspension of 10% (W / V) of 1ml isopropanol;

[0102] Test solution 5: 10% (W / V) (R)-2-[2-[4-[(4-chlorophenyl)benzyl]-1-piperazinyl dissolved in 1ml isopropanol ]ethoxyl]acetate diethylaminoethyl acetate solution;

[0103] Test solution 6: 10% (W / V) (R)-2-[2-[4-[(4-chlorophenyl)benzyl]-1-piperazinyl dissolved in 1ml isopropanol ] Ethoxyl] diethylaminoethylthioacetate hydrochloride solution;

[0104] Test s...

Embodiment 3

[0115] The mensuration of embodiment 3 antihistamine efficacy

[0116] (1) Effects on rat skin vascular permeability

[0117]Get 80 white SD rats, divide them into 10 groups at random, cut their hair at 1.5cm on both sides of the back midline of the rats, 2 points on each side, with an interval of 2cm, and administer 5mg / kg (body weight) cetirizine percutaneously the next day , levocetirizine, eflurizine (normal saline suspension containing 10% ethanol), 6 kinds of compounds of general formula 1 prepared in Example 1 (normal saline solution containing 10% ethanol), and 10ml / kg (body weight) normal saline containing 10% ethanol. One hour after the administration, intradermally inject 0.1ml of histamine phosphate saline solution (containing 50 μg of histamine), inject 2 points, and simultaneously inject 1% (W / V) Evans blue normal saline solution 1ml / kg into the tail vein ( Body weight), the animals were killed after 30 minutes, the blue-stained skin was removed and cut into p...

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Abstract

The invention discloses cetirizine derivatives disclosed as a general formula 1, and a preparation method thereof. The compounds have greatly higher efficiency of passing through biomembranes, and have antihistamine activity in vivo after percutaneous absorption. The invention also relates to a pharmaceutical composition comprising the compounds, and application of the compounds in preparation of medicaments for treating allergic diseases. General formula 1.

Description

technical field [0001] The invention relates to a derivative of cetirizine, a preparation method and application thereof, and a pharmaceutical composition using the derivative as an active ingredient. Background technique [0002] With the deepening of human industrialization, allergic diseases have become a kind of disease with high incidence, serious harm and great social impact. In 2005, the World Allergy Organization (WAO) announced the results of an epidemiological investigation of allergic diseases in 30 countries: 22% of the 1.2 billion people in these countries suffer from various allergic diseases mediated by IgE. In developed countries, allergic diseases have jumped to the sixth largest chronic disease due to their high incidence, and about 15-20% of the population suffer from various allergic diseases. Among various allergic diseases, allergic asthma and allergic rhinitis are the most harmful to human physical and mental health. Recurrent attacks of allergic ast...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/088A61K31/495A61P37/08A61P11/02A61P11/06A61P17/00A61P27/14
Inventor 杨利
Owner 杨利
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