Novel aza-oxo-indoles for the treatment and prophylaxis of respiratory syncytial virus infection
a technology azaoxoindole, which is applied in the field of new azaoxoindole for the treatment and prophylaxis of respiratory syncytial virus infection, can solve the problems of limiting the ability of individuals to transmit respiratory syncytial virus within households, nursing homes and hospital settings to other hosts at high risk of complications, and bronchiolitis and pneumonia
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example 1
5-{5-Chloro-2-[(2′-oxospiro[cyclopropane-1,3′-pyrrolo[2,3-c]pyridin]-1′(2′H)-yl)methyl]-1H-benzimidazol-1-yl}pyridine-2-carbonitrile
[0171]Step 1: Preparation of 5-nitropyridine-2-carbonitrile
[0172]A mixture of 2-bromo-5-nitropyridine (12.0 g, 59.1 mmol, CAS No.: 4487-59-6) and copper (I) cyanide (7.94 g, 88.7 mmol) in N,N-dimethylformamide (50 mL) was heated under reflux for 16 hours. After being cooled down to room temperature, the reaction mixture was poured into water and then extracted with ethyl acetate (100 mL×3). The combined organic layer was washed with brine, and then dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford 8.0 g of 5-nitropyridine-2-carbonitrile (yield was 90.8%).
[0173]Step 2: Preparation of 5-aminopyridine-2-carbonitrile
[0174]To a solution of 5-nitropyridine-2-carbonitrile (7.0 g, 46.9 mmol) in methanol (150 mL) was added 10% palladium on carbon (2.0 g) and carbamic acid (7.0 g, 115 mmol). After being heated under reflux f...
example 2-1
1′-({5-Chloro-1-[2-(methylsufonyl)pyridin-4-yl]-1H-benzimidazol-2-yl}methyl)spiro[cyclopropane-1,3′-pyrrolo[2,3-c]pyridin]-2′(1′H)-one
[0195]Step 1: Preparation of 2,4-bis(methylsulfonyl)pyridine
[0196]A mixture of 2,4-dichloropyridine (1.68 g, 11.0 mmol, CAS No.: 26452-80-2), sodium methanesulfinate (3.96 g, 33.0 mmol, 85% purity, CAS No.: 20277-69-4) and tetrabutylammonium chloride (917 mg, 3.3 mmol) in N,N-dimethylformamide (10 mL) was heated at 150° C. under microwave irradiation for 1 hour. The resulting mixture was then stirred with water (20 mL). The precipitate was collected by filtration to afford 1.59 g of 2,4-bis(methylsulfonyl)pyridine as a light pale solid (yield was 61.5%).
[0197]Step 2: Preparation of N-(4-chloro-2-nitrophenyl)-2-(methylsulfonyl)pyridin-4-amine
[0198]A mixture of 2,4-bis(methylsulfonyl)pyridine (1.41 g, 6.0 mmol), 4-chloro-2-nitroaniline (1.03 g, 6.0 mmol, CAS No.: 89-63-4) and potassium carbonate (828 mg, 6.0 mmol) in N,N-dimethylformamide (10 mL) was he...
example 2-2
1′-({5-Chloro-1-[4-(ethylsulfonyl)pyridin-2-yl]-1H-benzimidazol-2-yl}methyl)spiro[cyclopropane-1,3′-pyrrolo[2,3-c]pyridin]-2′(1′H)-one
[0205]The title compound was prepared in analogy to Example 2-1 by using sodium ethanesulfinate (CAS No.:20035-59-4) instead of sodium methanesulfinate.
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