Benzamide derivatives, their preparation method and their application in medicine
A technology of phenyl and compound, applied in its preparation method and pharmaceutical composition containing the derivative, in the field of novel benzamide derivatives, which can solve the problem of FGF23 expression reduction and other problems
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Embodiment 1
[0188] N 1 -Methyl-N 1 -(2-morpholine ethyl)-N 3 -(3-(4-Phenylethylphenylcarbamoyl)-5,6,7,8-tetrahydronaphthalen-2-yl)isophthalamide
[0189]
[0190] first step
[0191] 3-Amino-5,6,7,8-tetrahydronaphthalene-2-carbonyl chloride
[0192] Dissolve 3-amino-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid 1a (65 mg, 0.34 mmol, prepared by the method disclosed in the patent application "WO2012065963") in 3 mL of thionyl chloride, and heat up to 70°C, and stirred for 1 hour. The reaction solution was concentrated under reduced pressure to obtain the crude title product 3-amino-5,6,7,8-tetrahydronaphthalene-2-carbonyl chloride 1b (71 mg, yellow oil). The product was directly subjected to the next reaction without purification.
[0193] second step
[0194] 3-Amino-N-(4-phenethylphenyl)-5,6,7,8-tetrahydronaphthalene-2-carboxamide
[0195] The crude 3-amino-5,6,7,8-tetrahydronaphthalene-2-formyl chloride 1b (71 mg, 0.34 mmol) was dissolved in 6 mL of dichloromethane, and 4-ph...
Embodiment 2
[0203] 4-(4-(3-(3-(Methyl(2-morpholineethyl)carbamoyl)benzamido)-5,6,7,8-tetrahydronaphthalene-2-carboxamido) Phenylethyl) methyl benzoate
[0204]
[0205]
[0206] first step
[0207] Methyl 4-(4-(3-amino-5,6,7,8-tetralin-2-carboxamido)phenethyl)benzoate
[0208] Crude 3-amino-5,6,7,8-tetrahydronaphthalene-2-carbonyl chloride 1b (110 mg, 0.52 mmol) was dissolved in 6 mL of dichloromethane and 4-(4-aminophenethyl)benzoic acid was added Methyl ester 2a (127mg, 0.47mmol, prepared by the method disclosed in the patent application "WO2013062065") and triethylamine (159mg, 1.57mmol) were stirred for 1 hour. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography with eluent system B to obtain the title product 4-(4-(3-amino-5,6,7,8-tetrahydronaphthalene-2-methanol Acylamino)phenethyl)methylbenzoate 2b (98 mg, pale yellow solid), yield: 48%.
[0209] MS m / z(ESI):429.4[M+1]
[0210] second s...
Embodiment 3
[0216] 4-(3-(4-(3-(3-(Methyl(2-morpholineethyl)carbamoyl)benzamido)-5,6,7,8-tetrahydronaphthalene-2-methanol Acylamino)phenyl)propyl)methylbenzoate
[0217]
[0218] first step
[0219] Methyl 4-(3-(4-(3-amino-5,6,7,8-tetrahydronaphthalene-2-carboxamido)phenyl)propyl)benzoate
[0220] The crude 3-amino-5,6,7,8-tetrahydronaphthalene-2-formyl chloride 1b (110 mg, 0.52 mmol) was dissolved in 6 mL of dichloromethane, and 4-(3-(4-aminophenyl) Propyl) methyl benzoate 3a (127mg, 0.47mmol, prepared by the method disclosed in the patent application "WO2013062065") and triethylamine (160mg, 1.57mmol), stirred and reacted for 12 hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography with eluent system B to obtain the title product 4-(3-(4-(3-amino-5,6,7,8-tetrahydronaphthalene- 2-Formylamino)phenyl)propyl)methylbenzoate 3b (60 mg, pale yellow solid), yield: 28.7%.
[0221] MS m / z(ESI):443.4[M...
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