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Diarylamide compound and application thereof
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A compound, formamide technology, applied in the field of diuretics, can solve the problem of no increase in urine osmotic pressure
Active Publication Date: 2020-12-22
SUNSHINE LAKE PHARM CO LTD
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And after 5 days of strictly controlled fluid intake, their urine osmolality did not increase
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Embodiment 1
[0219] Example 1 N-(4-acetylaminophenyl)-4-nitrobenzamide
[0220]
[0221] Suspend p-nitrobenzoic acid (3-1a, 167mg, 1mmol) in dichloromethane (5mL), add 2 drops of DMF, and cool to 0°C in an ice-water bath. Oxalyl chloride (190mg, 0.13mL, 1.5mmol) was slowly added dropwise, and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated to remove the solvent and excess oxalyl chloride to obtain p-nitrobenzoyl chloride (3-2a), which was added to tetrahydrofuran (1 mL) for later use without further purification. Paracetaminoaniline (3-3a, 150 mg, 1 mmol) was dissolved in tetrahydrofuran (5 mL), triethylamine (152 mg, 1.5 mmol) was added, and the tetrahydrofuran solution of the above acid chloride 3-2a was added dropwise under ice bath. After dropping, react at room temperature to TLC (CH 2 Cl 2 :MeOH=15:1) showed that the reaction was complete. Add 30 mL of water to the reaction system, continue to stir for 10 minutes and then filter ...
[0229] Synthetic method is the same as embodiment 1. Orange solid, yield 80%, melting point 233-234°C.
[0230] 1 H NMR (400MHz, DMSO-d 6 )δ10.59(s,1H),9.97(s,1H),7.81(d,J=4.0Hz,1H),7.62-7.66(m,3H),7.57(d,J=8.8Hz,2H), 2.04(s,3H); 13 C NMR (101MHz, DMSO-d 6 )δ168.61, 154.79, 152.20, 148.56, 136.49, 133.32, 121.66, 119.71, 116.77, 113.97, 24.40. HRMS m / z: calcd for C 16 h 13 N 3 o 4 ,([M+H]+):285.08698,Found:285.08696.
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Abstract
The invention discloses a use of a diarylamide compound with a structure shown as a formula (I), and a pharmaceutically acceptable salt thereof in the preparation of a medicine serving as a ureatransporter inhibitor, and the novel diarylamide compound. The diarylamide compound has good ureatransporter inhibitor effects, can generate urea selective diuresisin vivo, and has no obvious toxic effects.
Description
technical field [0001] The invention relates to the field of diuretics, in particular to diarylamide compounds, their pharmaceutically acceptable salts and their use in the preparation of drugs as urea channel protein inhibitors. Background technique [0002] 1. Current applications and research and development hotspots of diuretics [0003] Diuretics act on the kidneys to increase water excretion. Clinically, it is mainly used to treat edema caused by various reasons, and it can also be used to treat some non-edematous diseases. For example, as a first-line drug, it can be used alone or in combination with other drugs to treat hypertension, reduce the incidence of cardiovascular and cerebrovascular diseases and mortality Rate. Diuretics can be divided into potassium-sparing diuretics, thiazide diuretics, loop diuretics, and carbonic anhydrase inhibitors according to their different sites of action. Potassium-sparing diuretics represented by amiloride and triamterene main...
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