Adenosine receptor antagonists and methods of making and using the same
a technology of adenosine receptor and antagonist, which is applied in the field of adenosine receptor antagonists, can solve the problems of increased sodium excretion and glomerular filtration rate, and achieve the effects of minimizing the likelihood of side effects, broad medicinal utility, and convenient manufacturing
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example 1
8-(5-Oxo-tricyclo[2.2.1.02,6]hept-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione
[0062] Anti-3-oxotricyclo(2.2.1.02,6)heptane-7-carboxylic acid (837 mg) was taken in CH2Cl2 (20 ml) at 0° C. Triethyamine (1.74 ml), isobutylchloroformate (724 μl) were added and stirred at 0° C. for 15 min. 1,3-Dipropyl-5,6-diaminouracil·HCl was added and stirred at 0° C. for 30 min and at room temperature overnight. The next day, the reaction mixture was diluted with water (50 ml) and extracted with CH2Cl2 (3×25 ml). The combined organic layer was washed with stat NaHCO3, water, brine, and dried over Na2SO4. Concentration of the solvent gave a crude product, which was taken to next step without further purification. Mass (ES+ 361).
[0063] 5-Oxo-tricyclo[2.2.1.02,6]heptane-3-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide (360 mg) from step 1 was taken in 1:1 isopropanol:water (5 ml) and KOH (84 mg) was added. The reaction mixture was refluxed for one and half-...
example 2
Endo / exo 8-(5-Hydroxy-tricyclo[2.2.1.02,6]hept-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione
[0064] 8-(5-Oxo-tricyclo[2.2.1.02,6]hept-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (700 mg) was dissolved in MeOH (50 ml). NaBH4 (100 mg) was added at 0° C. and stirred for 5 min. Water was added and stirred for 30 min. MeOH was removed by rotavap under reduced pressure. The reaction mixture was extracted with ethyl acetate, washed with water, brine, and dried over MgSO4. Concentration gave 700 mg of a mixture of endo:exo alcohols in a 6:4 ratio.
example 3
8-(5-Methylene-tricyclo[2.2.1.02,6]hept-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione
[0065] Methyl-triphenyl-phosphonium bromide (2.08 g) was taken in THF (50 ml) at −78° C. nBuLi (3.66 ml, 1.6 M) was added slowly at −78° C. and stirred for 1 hr. 8-(5-Oxo-tricyclo[2.2.1.02,6]hept-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (Example 1) (1 g) was dissolved in THF and added to the reaction mixture at −78° C. slowly. After the addition was over, the reaction mixture was allowed to warmed to room temperature slowly and stirred at room temperature overnight. The next day, the reaction mixture was quenched with 1 N HCl and extracted with ethyl acetate (3×50 ml). The combined organic layer was washed with water, brine and dried over Na2SO4. After concentration the product was purified by silica gel column. Mass (ES+ 341).
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