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Thiourea kind compund with inhibiting virus capsid protain activity and its preparation process and application thereof

A compound, sulfur-based technology, applied in organic active ingredients, active ingredients of heterocyclic compounds, organic chemistry, etc., can solve problems such as drug resistance, treatment measures, and adverse effects of disease outcomes

Inactive Publication Date: 2006-06-28
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to mutations in the structure of the enzyme, the HIV virus is prone to drug resistance to this class of drugs, thereby causing significant adverse effects on treatment measures and disease outcomes

Method used

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  • Thiourea kind compund with inhibiting virus capsid protain activity and its preparation process and application thereof
  • Thiourea kind compund with inhibiting virus capsid protain activity and its preparation process and application thereof
  • Thiourea kind compund with inhibiting virus capsid protain activity and its preparation process and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Example 1 Preparation of 3-chloro-4-methyl-phenylisothiocyanate

[0066] Cool in an ice-salt bath, under mechanical stirring, add 3-chloro-4-methylaniline dissolved in an appropriate amount of methanol dropwise into 4.3ml of carbon disulfide and 9.0ml of ammonia water, stir for about 1 hour, then let stand for 2 hours (no ice-salt bath). Add appropriate amount of water and heat slightly to dissolve it. Pour this solution into a saturated copper sulfate solution of 24 g of copper sulfate pentahydrate, and stir for a certain period of time. The upper product was suction filtered, and the filter residue was dried naturally.

[0067] Add an appropriate amount of toluene to the dried filter residue, stir mechanically for 3 hours, remove insoluble matter by filtration, and evaporate the filtrate to remove the solvent under reduced pressure. Distilled under reduced pressure to obtain 5.21 g of 3-chloro-4-methyl-phenylisothiocyanate as a pale yellow liquid.

Embodiment 2

[0068] Example 2 Preparation of 2-[(dimethylamino)-methyl]-5-hydroxymethyl-furan

[0069] Put 20 g of furfuryl alcohol, 19.8 g of dimethylamine hydrochloride, and 4.6 g of paraformaldehyde in a reaction vessel, heat to reflux for 1 hour with electromagnetic stirring, add 3.1 g of paraformaldehyde, heat to reflux for 1 hour, and evaporate the solvent under reduced pressure. Adjust to strong alkalinity with concentrated sodium hydroxide solution (0.1g / ml), extract with 100ml of anhydrous ether three times, and dry the extract with anhydrous sodium sulfate. The solvent was evaporated from the extract under reduced pressure, and 16.7 g of 2-[(dimethylamino)-methyl]-5-hydroxymethyl-furan was obtained by distillation under reduced pressure.

Embodiment 3

[0070] Example 3 Preparation of 2-[({5-[(dimethylamino)-methyl]-2-furan}-methyl)-thio]-ethylamine

[0071] Under cooling and stirring in an ice bath, add 16.7 g of 2-[(dimethylamino)-methyl]-5-hydroxymethyl-furan obtained in Example 2 dropwise into 12 g of cysteamine hydrochloride and 40 ml of concentrated hydrochloric acid at 0°C Reaction 18h. Sodium carbonate and sodium hydroxide powder were added to the reaction system to adjust the pH to strong alkalinity, extracted three times with 100 ml of anhydrous ether, and the extract was dried over anhydrous sodium sulfate. The solvent was evaporated from the extract under reduced pressure, and 2-[({5-[(dimethylamino)-methyl]-2-furan}-methyl)-thio]-ethylamine was obtained by distillation under reduced pressure.

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Abstract

The invention relates to a compound that is made up by chemical compounding method. R1, R2, and R3 represent one or several radical of hydrogen, alkyl, halogen and alkoxy and they could be same or different; R4 represents ({5-[(dimethylin)-methyl]-2-furan}-methyl-slfur, 4-(2-lignocaine-6-alkyl-5-nitryl-pyridine)-amidogen, 4-(2-lignocaine-6-alkyl- pyridine)-amidogen; n represents 1, 2, 3, 4, 5, 6. The pharmacy could accept acid or alkali to form addition salt. The acid includes hydrochloric acid, vitriol, hydrobromic acid, phosphoric acid, carbonic acid, formic acid, acetic acid, citric acid, lactic acid, fumaric acid, tartaric acid and gluconic acid. The alkali includes sodium hydroxide, potassium hydroxide, spasmolytol and ert-butylamine. The compound has good inhibitory effect to HIV virus.

Description

technical field [0001] The present invention relates to a series of new thiourea compounds and their pharmaceutically acceptable acid or base salts; the present invention also relates to the preparation method and production method of this series of new compounds; the present invention also relates to the production of this series of compounds Use on antiviral drugs. Background technique [0002] Human immunodeficiency virus (HIV) has the characteristics of rapid mutation and lack of effective therapeutic drugs, resulting in the rapid spread of AIDS all over the world, so the development of effective drugs for the treatment of HIV infection has become the most challenging problem in the world. Most of the anti-HIV drugs currently used in clinical and research are enzyme inhibitors targeting reverse transcriptase (RT), protease (PR) and integrase (IN). Due to the mutation of the structure of the enzyme, the HIV virus is prone to develop drug resistance to these drugs, thus c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C335/16A61K31/145A61K31/34A61K31/505A61P31/12C07D239/24C07D307/34
Inventor 杨铭何山杉袁德凯
Owner PEKING UNIV
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