Pharmaceutical composition having bicyclic nitrogen-containing aromatic heterocyclic amide compound as active component
A composition and compound technology are applied in the field of pharmaceutical compositions using bicyclic nitrogen-containing aromatic heterocyclic amide compounds as active ingredients, and can solve the problem of no cancer treatment and the like
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[0105] The production methods of Compound A, Compound B, Compound C, and Compound D will be described in detail below based on examples. In addition, the production methods of these raw material compounds are shown in the production examples. In addition, the production methods of compound A, compound B, compound C and compound D are not limited to the production methods of the specific examples shown below, and other combinations of these production methods or methods obvious to those skilled in the art can also be used. to manufacture.
[0106] In this specification, naming software such as ACD / Name (registered trademark, Advanced Chemistry Development, Inc.) may be used for naming compounds.
[0107] In addition, the concentration mol / l is expressed as M for convenience. For example, a 1M aqueous sodium hydroxide solution refers to a 1 mol / l aqueous sodium hydroxide solution.
[0108] Powder X-ray diffraction using RINT-TTRII (RIGAKU company), vacuum tube: Cu, tube curre...
manufacture example 1
[0111] In 5-bromo-1H-benzimidazole-2-carboxylic acid (1.0g), 1-[4-(trifluoromethyl)benzyl]piperazine (1.0g), 1-hydroxybenzotriazole (840mg) Add N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide hydrochloride to the mixture of N,N-dimethylformamide (10ml, hereinafter abbreviated as DMF) (1.2 g), stirred overnight at room temperature. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture, stirred at room temperature for 1 hour, and the resulting solid was collected by filtration and dried under reduced pressure. The obtained solid was dissolved in a mixture of chloroform (100 ml) and ethanol (1 ml) under heating to reflux. After cooling the mixture to room temperature, hexane (100ml) was added. After the resulting solid was collected by filtration and dried under reduced pressure, (5-bromo-1H-benzimidazol-2-yl){4-[4-(trifluoromethyl)benzyl]piperazine was obtained as a solid -1-yl}methanone (1.4 g).
manufacture example 2
[0113] (5-Bromo-1H-benzimidazol-2-yl){4-[4-(trifluoromethyl)benzyl]piperazin-1-yl}methanone (1.2g), 4-(4, 4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylic acid tert-butyl ester (1.6g), tetra (Triphenylphosphine) palladium (590mg), sodium carbonate (2.2g), di A mixture of alkanes (40ml) and water (10ml) was stirred at 95°C under an argon atmosphere for 24 hours, and then naturally cooled to room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, the desiccant was removed, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform-methanol) to obtain 4-[2-({4-[4-(trifluoromethyl)benzyl]piperazin-1-yl}carbonyl) as an oily substance -1H-benzimidazol-5-yl]-3,6-dihydropyridine-1(2H)-carboxylic acid tert-butyl ester (1.2 g).
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