Condensed imidazole derivatives
a technology of condensed imidazole and derivatives, which is applied in the field of new drugs, can solve the problems of no known dppiv inhibitor having a hypoxanthine or imidazopyridazinone structure backbone, and achieve excellent dppiv-inhibiting activity
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Production Example 1
t-Butyl 4-[1-(2-butynyl)-6-methyl-7-oxo-6,7-dihydro-1H-imidazo[4,5-d]pyridazin-2-yl]piperazin-1-carboxylate
(a) t-Butyl 5-methyl-4-oxo-4,5-dihydroimidazo[4,5-d]pyridazine-1-carboxylate
[0597] A mixture consisting of 1.0 g of 5-methyl-3,5-dihydroimidazo[4,5-d]pyridazin-4-one, 16 mg of 4-dimethylaminopyridine, 1.6 g of di-t-butyl dicarbonate, and 5 ml of tetrahydrofuran was stirred at room temperature overnight. Then, a 0.5-ml tetrahydrofuran solution containing 300 mg of di-t-butyl dicarbonate was added to the solution, and the resulting mixture was stirred at room temperature for three hours. 5 ml of t-butyl methyl ether was added to the reaction mixture, and the mixture was cooled with ice. The resulting crystals were collected by filtration to give 1.63 g of the title compound.
[0598]1H-NMR (CDCl3) δ 1.72 (s, 9H), 3.93 (s, 3H), 8.38 (s, 1H), 8.54 (s, 1H).
(b) 2-Chloro-5-methyl-1,5-dihydroimidazo[4,5-d]pyridazin-4-one
[0599] 8.4 ml of lithium hexamethyldisila...
production example 2
t-Butyl 4-[7-(2-butynyl)-2,6-dichloro-7H-purin-8-yl]piperazine-1-carboxylate
(a) 7-(2-Butynyl)-3-methyl-3,7-dihydropurine-2,6-dione
[0605] 55.3 ml of 1-bromo-2-butyne and 84.9 g of anhydrous potassium carbonate were added to a mixture of 100 g of 3-methyl xanthine [CAS No. 1076-22-8] and 1000 ml of N,N-dimethylformamide. The resulting mixture was stirred at room temperature for 18 hours. 1000 ml of water was added to the reaction solution, and the mixture was stirred at room temperature for 1 hour. The resulting white precipitate was collected by filtration. The white solid was washed with water and then t-butyl methyl ether. Thus, 112 g of the title compound was obtained.
[0606]1H-NMR (DMSO-d6) δ 1.82 (t, J=2.2 Hz, 3H), 3.34 (s, 3H), 5.06 (q, J=2.2 Hz, 2H), 8.12 (s, 1H), 11.16 (br.s, 1H).
(b) 7-(2-Butynyl)-8-chloro-3-methyl-3,7-dihydropurine-2,6-dione
[0607] 112 g of 7-(2-butynyl)-3-methyl-3,7-dihydropurine-2,6-dione was dissolved in 2200 ml of N,N-dimethylformamide, and 75.3 g o...
example
Example 1
Ethyl [7-(2-chlorophenyl)-1-methyl-6-oxo-8-(piperazin-1-yl)-6,7-dihydro-1H-purin-2-yloxy]acetate trifluoroacetate
(a) [7-Benzyl-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl 2,2-dimethylpropionate
[0613] 8.66 g of 7-benzylxanthine was dissolved in 300 ml of N,N-dimethylformamide, and 1.57 g of sodium hydride and 7.7 ml of chloromethyl pivalate were added thereto. The resulting mixture was stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate, and washed with water and 1N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, then filtered. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography. Thus, 2.66 g of the title compound was obtained from the fraction eluted with hexane-ethyl acetate (1:1).
[0614]1H-NMR (CDCl3) δ 1.18 (s, 9H), 5.45 (s, 2H), 6.06 (s, 2H), 7.34-7.39 (m, 5H), 7.58 (s, 1H), 8.18 (s, 1H).
(b) [7-Benzyl-1-methyl-2,6-dioxo-1,2,6,7-tet...
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Abstract
- T1 represents a 4- to 12-membered heterocyclic group containing one or two nitrogen atoms in the ring, which is a monocyclic or bicyclic structure that may have one or more substituents;
- X represents a C1-6 alkyl group which may have one or more substituents, or such;
- Z1 and Z2 each independently represent a nitrogen atom or a group represented by the formula —CR2—;
- R1 and R2 independently represent a hydrogen atom, a C1-6 alkyl group which may have one or more substituents, or a C1-6 alkoxy group which may have one or more substituents, or such. These are novel compounds that exhibit an excellent DPPIV-inhibiting activity.
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