Antiviral medicine and medicine composition thereof

A composition and drug technology, applied in the direction of antiviral agents, phosphorus organic compounds, pharmaceutical formulations, etc., can solve the problems of weakened control ability of preparations, and achieve significant pharmaceutical effects

Inactive Publication Date: 2015-05-20
HESI XIAN BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Although pharmaceutical workers have a strong ability in drug quality control to realize effective control of raw materials in drug manufacturers; Enterprise personnel (including logistics personnel, medical staff, patients, etc.) will greatly weaken the internal control ability of preparations

Method used

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  • Antiviral medicine and medicine composition thereof
  • Antiviral medicine and medicine composition thereof
  • Antiviral medicine and medicine composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0182] Embodiment 1: preparation tert-butyl 3-isopropyl-[(2R,3S)-2-hydroxy-3-(phenylmethoxycarbonyl)amino-4-phenylbutyl]carbazate

[0183] Step A: Preparation tert-Butyl 3-isopropylcarbazinate

[0184] The title compound can be prepared by the method of Dutta et al. (J.C: S.Perkin / 1975, 1712-1720) or by mixing 13.2 g (0.1 mol) tert-butyl carbazate and 6 g (0.103 mol) of acetone and 12.5g (0.1mol) of anhydrous magnesium sulfate in 100ml of dichloromethane was stirred for 12 hours, after the desiccant was removed by filtration, the filtrate was evaporated to dryness under reduced pressure, and after crystallization from cyclohexane, 16.9g (98% yield) The corresponding hydrazone has a melting point of 104-105°C. In a nitrogen atmosphere under a greenhouse, add 12ml (0.094mol) trimethylchlorosilane to a suspension of 2.04g (0.094mol) lithium borohydride in 100ml anhydrous tetrahydrofuran, and after 30 minutes, slowly add 13.45g (0.078 mol) hydrazone, and stirring was continu...

Embodiment 2

[0188] Embodiment 2: preparation tert-butyl 3-isopropyl-3-[(2R,3S)-2-hydroxy-3-(N-quinolinoyl-L-valyl)amino-4-phenylbutyl]carbazate

[0189] Step A: Preparation N-Quinolinoyl-L-valine

[0190] A mixture of 0.62 g (3.6 mmol) of quinolinic acid and 0.61 g (3.76 mmol) of 1,1'-carbonyldiimidazole in 1 ml of dry 1,4-dioxane was stirred for 30 minutes at room temperature. A solution of 0.43 g (3.7 mmol) of L-valine and 0.155 g (3.7 mmol) of lithium hydroxide in 1 ml of water was added thereto, and the resulting mixture was vigorously stirred at room temperature for about 4 hours. The mixture was diluted with water to 10 ml, cooled (ice-water bath), then acidified to pH ca. 3 with 1N hydrochloric acid and allowed to stand at 4°C for 2 hours. The crystals formed were removed by filtration, washed 3 times with 5 ml of cold water and dried over phosphorus pentoxide under high vacuum to give 0.75 g of product. Yield=76%; melting point is 134-136°C;

[0191] NMR (DMSO-d 6 ) 1.03 (...

Embodiment 3

[0196] Embodiment 3: preparation tert-Butyl 3-isopropyl-3-[(2R,3S)-2-hydroxy-3-(N-quinolinoyl-L-aspartoyl)amino-4-phenylbutyl]carbazate

[0197] Step A: Preparation N-quinolinoyl-L-aspartic acid

[0198] When aspartic acid was used instead of L-valine in Step A of Example 2, the title compound was obtained in the same manner, with a melting point of 200-203° C. and a yield of 85%.

[0199] NMR (DMSO-d 6 )3.0 (m, 2H, aSnCH 2 ); 5.0 (m, 1H, aSn CH-2); 6.3 (broad S, 1H, OH); 6.55 (broad 2, 1H, NH 2 ); 7.3 (wide S, 1H, NH 2 ); 7.55-8.6 (m, 6H, aromatic H); 9.22 (d, 1H, NH).

[0200] Step B: Preparation tert-butyl 3-isopropyl-3-[(2R,3s)-2-hydroxy-3-(N-quinolinoyl-L-aspartoyl)amino-4-phenylbutyl]carbazate

[0201] To the product of Step A (0.111g; 0.386mmol), the product of Step B of Example 2 (0.13022g; 0.386mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium fluorophosphate (0.205g 0.46mmol) and 1-hydroxybenzotriazole (0.052g; 0.384mmol) in 1ml of anhydrous dimet...

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Abstract

The invention relates to an antiviral medicine and a medicine composition thereof, in particular relates to an anti-human immunodeficiency virus (HIV) medicine and a medicine composition thereof, and especially relates to a medicine which can be taken as a retrovirus protease inhibitor. The retrovirus protease inhibitor has a chemical structure shown in a formula I.

Description

technical field [0001] The present invention relates to an antiviral drug and its pharmaceutical composition, in particular to an anti-human immunodeficiency virus (HIV) drug and its pharmaceutical composition, in particular to a drug that can be used as a retroviral protease inhibitor. The recording virus protease inhibitor has the chemical structure shown in formula I. Background technique [0002] Human immunodeficiency virus (HIV) is a pathogenic retrovirus that causes AIDS and related diseases. Since the discovery of HIV, the development of antiviral chemotherapy against AIDS has become the focus of active research. For research on the molecular targets of AIDS, see Mitsua et al. (Science, 1990, pp. 1533-154). HIV protease (HIV PR) and aspartyl protease were first considered by Kramer et al. (Science 231, 1580 (1986)) as possible targets for AIDS therapy. Since then, the potential use of HIV PR inhibitors as effective agents in the treatment of AIDS has been widely r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/60C07D215/48A61K31/675A61P31/18G01N30/02
CPCC07F9/60G01N30/02G01N30/06G01N2030/027
Inventor 夏桂民杨东元伊恩·雷诺兹杨洁
Owner HESI XIAN BIOTECH
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