Adenosine receptor antagonists and uses thereof
a technology of adenosine receptor and antagonist, which is applied in the field of compounds, can solve problems such as difficulty in formulating in a manner that provides reproducible plasma
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example 1
of Exemplary Compound A
[0452]Compound A can be synthesized according to the scheme below.
[0453]Step 1. O-(chloromethyl)S-ethyl carbonothioate, sodium iodide and 18-crown-6 are dissolved in toluene and heated to about 100° C. for about 5 hours to yield S-ethyl O-(iodomethyl) carbonothioate. Step 2. n-Butyric acid and tetrabutyl ammonium bisulfate, sodium carbonate are added to a solution of chloro(chloromethoxy)methane in methylene chloride / water at room temperature and stirred overnight to afford solid (((ethylthio)carbonyl)oxy)methyl butyrate. Step 3.
[0454]Sulfuryl acid is added dropwise to a solution of (((ethylthio)carbonyl)oxy)methyl butyrate at about −30° C. The reaction mixture is allowed to warm to room temperature and stir for about 2 hours to yield a solution of ((chlorocarbonyl)oxy)methyl butyrate. Step 4. ((Chlorocarbonyl)oxy)methyl butyrate is added to a solution of compound 1 and sodium hydride in DMF at room temperature and allowed to stir for about 3 hours to yield Co...
example 2
of Exemplary Compound B
[0455]Compound B can be synthesized according the scheme below.
[0456]Step 1. O-(chloromethyl)S-ethyl carbonothioate, sodium iodide, and 18-crown-6 are dissolved in toluene and heated to 100° C. for 5 hours to form S-ethyl O-(iodomethyl) carbonothioate. Step 2. S-ethyl O-(iodomethyl) carbonothioate and dibenzyl hydrogen phosphate are reacted to form O-(((bis(benzyloxy)phosphoryl)oxy)methyl)S-ethyl carbonothioate. Step 3. Sulfuryl acid is added to a solution of O-(((bis(benzyloxy)phosphoryl)oxy)methyl)S-ethyl carbonothioate at −30° C. and allowed to warm to room temperature and stir for 2 hours to afford ((bis(benzyloxy)phosphoryl)oxy)methyl carbonochloridate. Step 4. To a DMF solution of ((bis(benzyloxy)phosphoryl)oxy)methyl carbonochloridate and compound 1 is added sodium hydride at room temperature. The solution is stirred for 3 hours. Pd / C in DMSO is added under H2 at room temperature, and the reaction mixture is allowed to stir for 5 hours to afford Compoun...
example 3
of Exemplary Compound C
[0457]Compound C was synthesized according to the steps below.
[0458]To a solution of compound 28 (50.0 g, 1650 mmol, 1.0 eq) and thionyl chloride (63.0 mL, 849.9 mmol, 0.5151 eq) was added zinc bromide (4.58 g, 19.99 mmol, 0.01212 eq) under nitrogen atmosphere. The resulting mixture was stirred at 80° C. for 24 h. The progress of the reaction mixture was monitored by 1H NMR. After completion of the reaction, the resulting mixture was isolated by distillation (b.p. 103-104° C.) to afford a mixture of slightly yellow oil and white solid. The mixture was filtered to afford compound 29 (51.645 g, 54%) as a slightly yellow oil.
[0459]To a solution of compound 29 (10.0 g, 87.72 mmol, 3.0 eq) in hexane (50 mL) was added sodium butyrate (3.2 g, 29.24 mmol, 1.0 eq) in a sealed tube. The resulting mixture was stirred at 80° C. for 16 h. The progress of the reaction mixture was monitored by 1H NMR. After completion of the reaction, the resulting mixture was filtered and t...
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