De-methylated anethol trisulfide derivative as well as preparation method and application thereof

A technology of medicine and preparation, which is applied in the field of demethylanisyl trisulfide derivatives and its preparation, can solve the problems of survivors of cardiovascular and cerebrovascular accidents that they cannot fully take care of themselves, and achieve good application prospects and good water solubility

Active Publication Date: 2020-05-01
CHENGDU BIOBEL BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This new chemical entity described by this inventor solves problems with common medications that cause dry mouth or stingy throat symptoms such as xerosis (dryness caused due to lack of saliva) and hepatitis B virus. It also works well on treatments like these conditions without causing side effects from ingesting too much saltiness or acidity during its use.

Problems solved by technology

This patents discusses different types of medicine used to reduce inflammation associated with alcohol use such as nonstasy lobismus syndrome, sore neck, eye bone loss, etc., including medicines like amantadine hydroxylamidase injection therapies targeting these conditions. However, current pharmaceuticals have limitations: they may only work well when given concomitantly because their effects on other organs could result in complications.

Method used

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  • De-methylated anethol trisulfide derivative as well as preparation method and application thereof
  • De-methylated anethol trisulfide derivative as well as preparation method and application thereof
  • De-methylated anethol trisulfide derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1, the preparation of demethyl anetellityl trisulfide (ADT)

[0043]

[0044] Mix 20 grams of trithiopyridine (M1) and 58 grams of anhydrous pyridine hydrochloride evenly, under nitrogen protection, slowly heat to 220 degrees Celsius, all the solids dissolve into a homogeneous system, keep stirring at 220 degrees Celsius for 30 minutes, and naturally cool to room temperature. Add 200ml of ethyl acetate and 200ml of water, heat to 50 degrees Celsius and stir for 30 minutes, filter to remove insoluble matter, and the obtained filtrate is allowed to stand for stratification, take the ethyl acetate layer, wash twice with 40ml of water, add 50 grams of anhydrous sodium sulfate and 5 g of activated carbon was dried and decolorized overnight. On the second day, sodium sulfate and activated carbon were removed by filtration, concentrated until solids were precipitated, and 50 ml of petroleum ether was added to stir and crystallize. After the crystallization was c...

Embodiment 2

[0046] Embodiment 2, the preparation of compound I-1-1 of the present invention

[0047]

[0048]Dissolve 20 grams of demethylanisyltrithione (ADT) in 200 ml of dichloromethane, add 21 grams of pyridine, cool down to below -10 degrees Celsius, slowly add 27 grams of phosphorus oxychloride, and drop phosphorus oxychloride at -5 After 5 hours of reaction at ~0°C, the reaction of demethylanisyl trisulfide is complete. Add 200ml of ice water, stir for half an hour and let stand, the obtained crude compound I-1-1 sinks to the bottom of the bottle as an oily substance. The water and dichloromethane were poured off, and the residual oil was washed twice with 40 ml of 1N hydrochloric acid to remove pyridine hydrochloride. After pouring off the hydrochloric acid, the obtained product was dissolved in 100 ml of tetrahydrofuran, and dried by adding 30 g of anhydrous sodium sulfate. The sodium sulfate was removed by filtration and the tetrahydrofuran was concentrated to dryness to ob...

Embodiment 3

[0050] Embodiment 3, the preparation of compound I-1-2, I-1-3 of the present invention

[0051]

[0052]

[0053] 12 grams of compound I-1-1 was dissolved in 30 ml of absolute ethanol, and a saturated solution of sodium methoxide in methanol was slowly added dropwise with stirring at room temperature until the pH value was about 7.5, and about 2.5 grams of sodium methoxide was consumed. After the dropwise addition was completed, stirring was continued at room temperature for 30 minutes, and a reddish-brown solid was obtained by filtration and drying, that is, 11 g of crude compound I-1-2, with a yield of 80%.

[0054] 11 grams of crude product I-1-2 was dissolved with 44 grams of pure water heated to 70 degrees Celsius, cooled naturally to room temperature, slowly added with 88 grams of absolute ethanol, the product crystallized, continued to stir for 1 hour, filtered, and dried to obtain compound I-1 -2 Light red solid 7 g, yield 63.6%. The mass spectrogram of compound...

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Abstract

The invention provides a de-methylated anethol trisulfide derivative as well as a preparation method and application thereof. The de-methylated anethol trisulfide derivative is a compound shown as a formula (I), wherein R1 and R2 are respectively or simultaneously selected from H, alkali metal cations or organic amine cations; and X is selected from O, S or S=O. The compound provided by the invention has good water solubility, and has excellent effects in prevention and treatment of oral sicca syndrome, fatty liver, drug-induced liver disease, alcoholic liver disease, acute alcoholism, cerebral ischemia, cardiac ischemia, and the like. The compound disclosed by the invention can be used for preparing a medicine for treating the diseases mentioned above and has a good application prospect.

Description

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Claims

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Application Information

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Owner CHENGDU BIOBEL BIOTECHNOLOGY CO LTD
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