8-substituted styryl xanthine derivative and application thereof

An alkyl and group technology, which is applied in the direction of drug combinations, active ingredients of heterocyclic compounds, cardiovascular system diseases, etc., can solve problems such as distribution restrictions of adenosine A, achieve a good brain/plasma ratio, good clinical application prospects, stable effect

Active Publication Date: 2020-04-10
SUNSHINE LAKE PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This new compound described by this patented formula helps treat neurologically related conditions like Parkinsons Disease. It works well even at high doses but still shows promise because its structure makes them safe from side effecting healthy tissues while also being effective over time.

Problems solved by technology

In this patented technical problem addressed in this patents relates to finding novel chemical entities called substances which specifically target specific molecules involved in regulating signal transduction pathways such as cell membranes.

Method used

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  • 8-substituted styryl xanthine derivative and application thereof
  • 8-substituted styryl xanthine derivative and application thereof
  • 8-substituted styryl xanthine derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0269] Example 1 (E)-1,3-diethyl-7-methyl-8-(3-(oxetan-3-yloxy)styryl)-1H-purine-2,6( Synthesis of 3H,7H)-diketones

[0270]

[0271] Step 1) Synthesis of oxetan-3-yl 4-methylbenzenesulfonate

[0272] Add p-toluenesulfonyl chloride (1.0g, 5.2mmol) and triethylamine (2.2mL, 15.7mmol) into a 100mL single-necked flask at 25°C, add dichloromethane (10mL), and then add oxetane in batches Alkan-3-ol (0.5g, 6.7mmol), continue to react for 24 hours; add water (40mL), then add dichloromethane (20mL), separate the liquid, collect the organic phase, spin dry under reduced pressure, and separate by column chromatography Purification (petroleum ether / ethyl acetate (v / v)=10 / 1~5 / 1) gave the title compound as a pale yellow solid (1.02 g, 85.2%).

[0273] MS(ESI,pos.ion)m / z:229.1[M+H] + ;

[0274] 1 H NMR (400MHz, CDCl 3 )δ (ppm) 7.81 (d, J = 8.2Hz, 2H), 7.39 (d, J = 8.1Hz, 2H), 5.38–5.28 (m, 1H), 4.76–4.66 (m, 4H), 2.49 (s ,3H).

[0275] Step 2) Synthesis of 3-(oxetan-3-yloxy)b...

Embodiment 2

[0291] Example 2 (R, E)-1,3-diethyl-7-methyl-8-(3-((tetrahydrofuran-3-yl)oxy)styryl)-1H-purine-2,6 Synthesis of (3H,7H)-diketones

[0292]

[0293] Step 1) Synthesis of (S)-tetrahydrofuran-3-yl 4-methylbenzenesulfonate

[0294] The title compound of this step was prepared by referring to the method described in step 1 of Example 1, that is, p-toluenesulfonyl chloride (3.6g, 18.9mmol), (S)-tetrahydrofuran-3-ol (1.5g, 17.0mmol) and triethylamine (3.5mL, 24.9mmol) was prepared by reaction in dichloromethane (20mL). The crude product was separated and purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v)=20 / 1) to obtain the title compound as red Brown oil (2.8 g, 68.0%).

[0295] MS(ESI,pos.ion)m / z:265.0[M+Na] + ;

[0296]1 H NMR (400MHz, CDCl3) δ (ppm) 7.80 (d, J = 8.3Hz, 2H), 7.36 (d, J = 8.1Hz, 2H), 5.17–5.06 (m, 1H), 3.92–3.78 (m, 4H), 2.46(s,3H), 2.13–2.04(m,2H).

[0297] Step 2) Synthesis of (R)-3-((tetrahydrofuran-3-yl)oxy)benzaldehy...

Embodiment 3

[0315] Example 3 (S, E)-1,3-diethyl-7-methyl-8-(3-((tetrahydrofuran-3-yl)oxy)styryl)-1H-purine-2,6 Synthesis of (3H,7H)-diketones

[0316]

[0317] Step 1) Synthesis of (R)-tetrahydrofuran-3-yl 4-methylbenzenesulfonate

[0318] The title compound of this step was prepared by referring to the method described in Step 1 of Example 1, that is, p-toluenesulfonyl chloride (3.0 g, 16 mmol), (R)-tetrahydrofuran-3-ol (1.5 g, 17.0 mmol) and triethylamine ( 3.5mL, 24.9mmol) was prepared by reaction in dichloromethane (20mL). The crude product was separated and purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v)=20 / 1) to obtain the title compound as reddish brown Oil (2.2 g, 58.0%).

[0319] MS(ESI,pos.ion)m / z:265.2[M+Na] + ;

[0320] 1 H NMR (400MHz, CDCl 3 )δ (ppm) 7.80 (d, J = 8.3Hz, 2H), 7.36 (d, J = 8.1Hz, 2H), 5.17–5.06 (m, 1H), 3.89–3.81 (m, 4H), 2.46 (s ,3H),2.13–2.04(m,2H).

[0321] Step 2) Synthesis of (S)-3-((tetrahydrofuran-3-yl)ox...

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Abstract

The invention discloses an 8-substituted styryl xanthine derivative and application thereof, and particularly relates to a novel 8-substituted styryl xanthine derivative and a pharmaceutical composition containing the compound, and the 8-substituted styryl xanthine derivative can be used as a selective adenosine A2A receptor antagonist. The invention also relates to a method for preparing the compound and the pharmaceutical composition, and application of the compound and the pharmaceutical composition in preparation of drugs for treating adenosine A2A receptor related diseases, especially Parkinson's disease.

Description

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Claims

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Application Information

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Owner SUNSHINE LAKE PHARM CO LTD
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