Organic compounds
A compound and drug technology, applied in the field of organic compounds, can solve problems such as cAMP and cGMP increase
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[0178] The preparation method of the compound of the present invention
[0179] Compounds of the invention, for example (6aR*,9aS*)-3-(phenylamino)-5-6a,7,8,9,9a-hexahydro-5-methyl-cyclopentadiene[4,5 ]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(1H or 2H)-one compounds, preferably 1- or 2-substituted (6aR,9aS)(phenylamino) -5-6a,7,8,9,9a-hexahydro-5-methyl-cyclopentadieno[4,5]imidazo[1,2-a]pyrazolo[4,3-e] Pyrimidin-4(1H or 2H)-ketone, any compound of formula Q or I such as 1.1-.56 or 1.5701.87 or compound of formula (X) and their pharmaceutically acceptable salts can be described and exemplified in the text and prepared by methods analogous thereto and methods known in the chemical arts. Such methods include, but are not limited to, those described below. If not commercially available, the starting materials used in these methods can be prepared by methods selected from the field of chemistry using similar or analogous techniques to the synthesis of known compounds. All refer...
Embodiment 1
[0319] (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-2-((tetrahydro-2H-pyran-4-yl) Methyl)-cyclopentadieno[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one
[0320]
[0321] (a) 7-(4-methoxybenzyl)-5-methyl-3-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H) - dione
[0322] Add phenylisothiocyanate (3.9 mL, 32.7 mmol) to 6-hydrazino-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione (0.45g, 1.6mmol) in DMF (12mL) suspension. The reaction mixture was heated at 120°C for 40 hours, then the solvent was evaporated under reduced pressure. The residue was washed with hexanes, then treated with MeOH (125 mL) and stored at -15 °C for 2 days to give a crystalline solid. the solid from CH 3 Recrystallization from OH-EtOAc afforded 2.5 g of product (yield: 61%). 1 H NMR (400MHz, DMSO-d 6 )δ3.21(s,3H),3.73(s,3H),5.01(s,2H),6.88-7.36(m,9H).MS(FAB)m / z 378.3[M+H] + .
[0323] (b) 5-Methyl-3-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione
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Embodiment 2
[0334] (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-1-((tetrahydro-2H-pyran-4-yl) Methyl)-cyclopentadieno[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(1H)-one
[0335]
[0336] (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-3-(phenylamino)-cyclopentadieno[4,5]imidazo[1, 2-a]pyrazolo[4,3-e]pyrimidin-4(2H)-one (50mg, 0.155mmol), 4-(iodomethyl)-tetrahydro-2H-pyran (70mg, 0.310mmol) and Cs 2 CO 3 (101 mg, 0.310 mmol) in DMF (1 mL) was heated in microwave at 140 °C for 30 min. After cooling, the mixture was filtered through a 0.45 μm millipore filter and the filtrate was purified by semi-preparative HPLC to give pure product as a white powder. MS(ESI)m / z 421.2[M+H] + .
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