PATENT CLAIM ANALYSIS

Application Number: 16098244
Application Type: Utility
Filing Date: 2018-11
Publication Date: 2019-05
Patent Classification: ["514", "218000"]

Abstract:
The present invention relates to new compounds of general formula (I) that show great affinity and activity towards the subunit α2δ of voltage-gated calcium channels (VGCC), especially α2δ-1 subunit of voltage-gated calcium channels or dual activity towards subunit α2δ of voltage-gated calcium channels (VGCC), especially α2δ-1 subunit of voltage-gated calcium channels, and noradrenaline transporter (NET). The invention is also related to the process for the preparation of said compounds as well as to compositions comprising them, and to their use as medicaments.

Claim (Index 27):
The compound according to  claim 18 , which is selected from the following group:\n [148] 2-(Ethylamino)-9-methyl-6-(3-(3-(methylamino)-1-phenylpropoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [149] (R)-2-(ethylamino)-9-methyl-6-(3-(3-(methylamino)-1-phenylpropoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [150] (S)-2-(ethylamino)-9-methyl-6-(3-(3-(methylamino)-1-phenylpropoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [151] 9-methyl-6-(3-(3-(methylamino)-1-phenylpropoxy)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [152] (R)-9-methyl-6-(3-(3-(methylamino)-1-phenylpropoxy)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [153] (S)-9-methyl-6-(3-(3-(methylamino)-1-phenylpropoxy)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [154] 2-(ethylamino)-9-methyl-6-(3-(2-(methylamino)-1-phenylethoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [156] 6-(3-(2-amino-1-phenylethoxy)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [159] 2-(ethylamino)-9-methyl-6-(4-(2-(methylamino)-1-phenylethoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [160] 2-(ethylamino)-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [161] (R)-2-(ethylamino)-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [162] (S)-2-(ethylamino)-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [163] 9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [164] (R)-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [165] (S)-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [166] 2-(ethylamino)-9-methyl-6-(3-((2-(methylamino)-2-phenylethoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [167] 9-methyl-6-(3-((2-(methylamino)-2-phenylethoxy)methyl)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [169] 6-(3-(3-(benzylamino)propoxy)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [173] 2-(ethylamino)-9-methyl-6-(3-(2-methyl-1-(methylamino)propan-2-yl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [176] 2-(ethylamino)-9-methyl-6-(3-(((4-phenylpiperidin-4-yl)oxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [179] 9-methyl-2-(methylthio)-6-(3-(((4-phenylpiperidin-4-yl)oxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [182] 6-(3-(4-((benzylamino)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [183] 2-(ethylamino)-9-methyl-6-(3-(4-(2-(methylamino)ethyl)-1H-1,2,3-triazol-1-yl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [193] 2-(ethylamino)-9-methyl-6-(3-(3-(methylamino)-1-(pyridin-2-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [194] 2-(ethylamino)-9-methyl-6-(3-(3-(methylamino)-1-(pyridin-3-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [195] (R)-2-amino-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [196] (R)-2-(dimethylamino)-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [197] (R)-9-methyl-2-(methylamino)-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [198] 8-(ethylamino)-1-methyl-4-(3-(3-(methylamino)-1-phenylpropoxy)phenyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [199] 8-(ethylamino)-1-methyl-4-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [201] 2-(ethylamino)-9-methyl-6-(4-(2-(methylamino)-1-phenylethoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [203] (R)\u2014N-ethyl-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-2-amine; [204] (R)-2-methoxy-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [205] (R)-2-hydroxy-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [206] (R)-2,9-dimethyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [207] (R)-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [208] 9-Methyl-6-(3-((3-(methylamino)-1-(thiophen-2-yl)propoxy)methyl)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [209] (R)-9-methyl-6-(3-((3-(methylamino)-1-(thiophen-2-yl)propoxy)methyl)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [210] (S)-9-methyl-6-(3-((3-(methylamino)-1-(thiophen-2-yl)propoxy)methyl)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [211] 2-(ethylamino)-9-methyl-6-(3-((3-(methylamino)-1-(thiophen-2-yl)propoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [212] (R)-2-(ethylamino)-9-methyl-6-(3-((3-(methylamino)-1-(thiophen-2-yl)propoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [213] 2-(ethylamino)-9-methyl-6-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [214] 2-(ethylamino)-9-methyl-6-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [215] (R)-2-(ethylamino)-9-methyl-6-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [216] (S)-2-(ethylamino)-9-methyl-6-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [217] 9-methyl-6-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [218] (R)-9-methyl-6-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [219] (S)-9-methyl-6-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [220] 2-(ethylamino)-6-(3-(3-((2-fluoroethyl)amino)-1-(thiophen-2-yl)propoxy)phenyl)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [221] 2-methoxy-9-methyl-6-(3-((3-(methylamino)-1-(thiophen-2-yl)propoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [222] 2-hydroxy-9-methyl-6-(3-((3-(methylamino)-1-(thiophen-2-yl)propoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [223] 2,9-dimethyl-6-(3-((3-(methylamino)-1-(thiophen-2-yl)propoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [224] 9-methyl-6-(3-((3-(methylamino)-1-(thiophen-2-yl)propoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [225] 2-(Ethylamino)-9-methyl-6-(3-((2-(methylamino)-1-phenylethoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [226] 9-methyl-6-(3-((2-(methylamino)-1-phenylethoxy)methyl)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [227] 8-(ethylamino)-1-methyl-4-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [229] 8-(dimethylamino)-1-methyl-4-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [230] 2-(dimethylamino)-9-methyl-6-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [231] 2,9-dimethyl-6-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [232] 9-methyl-6-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [236] (R)-6-(3-((3-(Dimethylamino)-1-phenylpropoxy)methyl)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [237] (S)-6-(3-((3-(dimethylamino)-1-phenylpropoxy)methyl)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [238] 6-(3-(3-(dimethylamino)-1-phenylpropoxy)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [239] 6-(3-(2-(dimethylamino)-1-phenylethoxy)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [240] 6-(3-(3-(benzyl(methyl)amino)propyl)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [241] 6-(3-(3-(dimethylamino)propyl)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [242] 6-(3-(4-((dimethylamino)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [243] 6-(3-(4-((benzyl(methyl)amino)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [244] 2-(ethylamino)-9-methyl-6-(3-(4-((methyl(phenethyl)amino)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [246] 6-(3-(4-(((cyclopropylmethyl)(methyl)amino)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [251] 6-(3-(4-((benzyl(methyl)amino)methyl)-1H-pyrazol-1-yl)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [252] 2-(ethylamino)-9-methyl-6-(3-(4-((methyl(phenethyl)amino)methyl)-1H-pyrazol-1-yl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [253] 6-(3-(4-((benzyl(methyl)amino)methyl)-1H-imidazol-1-yl)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [254] 2-(ethylamino)-9-methyl-6-(3-(4-((methyl(phenethyl)amino)methyl)-1H-imidazol-1-yl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [256] 6-(3-(3-(benzyl(methyl)amino)propoxy)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [261] 2-(ethylamino)-9-methyl-6-(3-(1-phenethylpiperidin-4-yl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [264] 6-(3-(2-(benzyl(methyl)amino)ethoxy)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [265] 2-(ethylamino)-9-methyl-6-(3-(2-(methyl(phenethyl)amino)ethoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [271] 9-methyl-6-(3-(((1-methyl-4-phenylpiperidin-4-yl)oxy)methyl)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [272] 2-(ethylamino)-9-methyl-6-(3-(((1-methyl-4-phenylpiperidin-4-yl)oxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [275] 2-(Ethylamino)-6-(3-(2-(4-(3-hydroxyphenyl)piperidin-1-yl)ethyl)phenyl)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [278] 2-(Ethylamino)-9-methyl-6-(3-(4-((4-phenylpiperidin-1-yl)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [279] 2-(ethylamino)-6-(3-(4-((4-(3-hydroxyphenyl)piperidin-1-yl)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [281] 2-(ethylamino)-9-methyl-6-(3-(4-(piperidin-1-ylmethyl)-1H-1,2,3-triazol-1-yl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [285] 6-(3-(4-(((cyclopropylmethyl)amino)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [287] 2-(ethylamino)-6-(3-(4-(((4-fluorobenzyl)(methyl)amino)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [288] 2-(ethylamino)-9-methyl-6-(3-(4-((methyl(pyridin-2-ylmethyl)amino)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [289] 2-(ethylamino)-9-methyl-6-(3-(4-((methyl(pyridin-3-ylmethyl)amino)methyl)-1H-1,2,3-triazol-1-yl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [304] (S)-8-amino-1-methyl-4-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [305] (S)-8-amino-1-methyl-4-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [307] 1,8-dimethyl-4-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [308] (S)-1,8-dimethyl-4-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [315] 9-methyl-6-(4-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [316] 9-methyl-6-(4-(3-(methylamino)-1-phenylpropoxy)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [321] 9-methyl-6-(4-((2-(methylamino)-1-phenylethoxy)methyl)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [322] 9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-2-(trifluoromethyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [323] 1-methyl-4-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [325] (S)-8-(ethylamino)-1-methyl-4-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [326] (S)-1-methyl-4-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [327] (R)-1-methyl-4-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [328] 9-methyl-6-(4-((3-(methylamino)-1-(thiophen-2-yl)propoxy)methyl)phenyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [329] 9-methyl-6-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-2-(trifluoromethyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [330] 9-methyl-6-(3-((3-(methylamino)-1-(thiophen-2-yl)propoxy)methyl)phenyl)-2-(trifluoromethyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [331] (S)-8-methoxy-1-methyl-4-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [333] 2-(ethylamino)-9-methyl-6-(4-(3-(methylamino)-1-phenylpropoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [334] 2-(ethylamino)-9-methyl-6-(4-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [335] 2-(benzylamino)-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [336] 9-methyl-2-(methyl(pyridin-2-ylmethyl)amino)-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [340] 2-(ethylamino)-9-methyl-6-(4-((2-(methylamino)-1-phenylethoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [341] (R)-9-methyl-2-(methyl(pyridin-2-ylmethyl)amino)-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [342] (R)-9-methyl-2-(methyl(pyridin-3-ylmethyl)amino)-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [343] (R)-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-2-((pyridin-2-ylmethyl)amino)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [344] (R)-2-(((5-fluoropyridin-2-yl)methyl)(methyl)amino)-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one [347] (R)-2-amino-9-methyl-6-(3-((3-(methylamino)-1-(thiophen-2-yl)propoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [348] 2-(ethylamino)-9-methyl-6-(4-((3-(methylamino)-1-(thiophen-2-yl)propoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [349] 2-(ethylamino)-9-methyl-6-(3-(3-(methylamino)-1-(thiophen-3-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [350] (R)-2-(ethylamino)-9-methyl-6-(3-(3-(methylamino)-1-(thiophen-3-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [351] (S)-2-(ethylamino)-9-methyl-6-(3-(3-(methylamino)-1-(thiophen-3-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [352] (S)-2-amino-9-methyl-6-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [353] 2,9-dimethyl-6-(4-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [354] 2-ethyl-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [355] 2,9-dimethyl-6-(4-((2-(methylamino)-1-phenylethoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [356] (R)-2-ethyl-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [357] (R)-2,9-dimethyl-6-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [358] (S)-2,9-dimethyl-6-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [360] (R)-2,9-dimethyl-6-(3-((3-(methylamino)-1-(thiophen-2H)propoxy)methyl)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [364] (S)-9-methyl-6-(3-(3-(methylamino)-1-(thiophen-2-yl)propoxy)phenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [366] 9-methyl-6-(3-(3-(methylamino)-1-phenylpropoxy)benzyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [367] 9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)benzyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [368] 9-methyl-6-(4-((3-(methylamino)-1-phenylpropoxy)methyl)benzyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [369] 9-methyl-6-(4-(3-(methylamino)-1-phenylpropoxy)benzyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [372] 9-methyl-6-(3-((2-(methylamino)-1-phenylethoxy)methyl)benzyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [374] 9-methyl-6-(4-((2-(methylamino)-1-phenylethoxy)methyl)benzyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [375] (S)-2-methoxy-9-methyl-6-(4-(3-(methylamino)-1-phenylpropoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [378] 9-methyl-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [379] (S)-9-methyl-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [380] (R)-9-methyl-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-2-(methylthio)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [381] 1-methyl-4-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [382] (S)-1-methyl-4-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [383] (S)-8-(ethylamino)-1-methyl-4-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [384] (S)-8-(dimethylamino)-1-methyl-4-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [385] (S)-8-methoxy-1-methyl-4-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [386] (S)-9-methyl-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-2-(trifluoromethyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [387] 2-methoxy-9-methyl-6-(4-(3-(methylamino)-1-(thiophen-3-yl)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [388] 2-methoxy-9-methyl-6-(4-(3-(methylamino)-1-(3-methylthiophen-2H)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [389] (S)-1-ethyl-8-methoxy-4-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [391] (S)-1-ethyl-4-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [392] 2-methoxy-9-methyl-6-(4-(3-(methylamino)-1-(5-methylthiophen-2H)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [394] (S)-6-(3-fluoro-4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-2-methoxy-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [395] S)-9-ethyl-2-methoxy-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [396] 2-methoxy-9-methyl-6-(4-(3-(methylamino)-1-(4-methylthiophen-2H)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [397] (S)-2-methoxy-9-methyl-6-(2-methyl-4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [398] (S)-9-ethyl-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [399] (S)-9-fluoro-1-methyl-4-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [400] (S)-9-chloro-1-methyl-4-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-1,2,3,4-tetrahydro-5H-pyrido[4,3-e][1,4]diazepin-5-one; [401] (S)-6-(2-fluoro-4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-2-methoxy-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [402] (S)-2-methoxy-9-methyl-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [405] 2-(ethylamino)-9-methyl-6-(4-((3-(methylamino)-1-phenylpropoxy)methyl)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [406] 2-(ethylamino)-9-methyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [408] 2-(ethylamino)-9-methyl-6-(4-(3-(methylamino)-1-phenylpropoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [411] 2-(ethylamino)-9-methyl-6-(3-((2-(methylamino)-1-phenylethoxy)methyl)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [413] 2-(ethylamino)-9-methyl-6-(4-((2-(methylamino)-1-phenylethoxy)methyl)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [414] (S)-2-(ethylamino)-9-methyl-6-(4-(3-(methylamino)-1-phenylpropoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [415] (R)-2-(ethylamino)-9-methyl-6-(4-(3-(methylamino)-1-phenylpropoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [416] 2-(ethylamino)-9-methyl-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [417] (S)-2-(ethylamino)-9-methyl-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [418] (R)-2-(ethylamino)-9-methyl-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [419] (S)-2-(dimethylamino)-9-methyl-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [420] (S)-2-amino-9-methyl-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [422] 2,9-dimethyl-6-(4-((3-(methylamino)-1-phenylpropoxy)methyl)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [423] 2,9-dimethyl-6-(3-((3-(methylamino)-1-phenylpropoxy)methyl)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [425] 2,9-dimethyl-6-(4-(3-(methylamino)-1-phenylpropoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [426] 2-ethyl-9-methyl-6-(4-(3-(methylamino)-1-phenylpropoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [427] (R)-2,9-dimethyl-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [428] (S)-2,9-dimethyl-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [430] 9-methyl-6-(4-(3-(methylamino)-1-phenylpropoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [433] (S)-9-methyl-6-(4-(3-(methylamino)-1-phenylpropoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [434] (R)-9-methyl-6-(4-(3-(methylamino)-1-phenylpropoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [435] 9-methyl-6-(4-(3-(methylamino)-1-(thiophen-2H)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [436] (S)-9-methyl-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one; [437] (R)-9-methyl-6-(4-(3-(methylamino)-1-(thiophen-2-yl)propoxy)benzyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one and [442] 6-(3-(5-((4-(dimethylamino)-4-(3-hydroxyphenyl)piperidin-1-yl)methyl)-1,3,4-oxadiazol-2-yl)phenyl)-2-(ethylamino)-9-methyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one.

Metadata:
- Claim Count in Document: 44.0
- Percentile: 98.0
- Lexical Diversity: 1.88235
- Patent Class: 514.0
- Transitional Phrase Type: none
- Component Type: 0
- Foreign Priority: True
- Related Applications: ['14820711', '12680353', '12485108', '13910349', '11828457']

Analysis Scores:
- 35 USC 101 Eligibility (BERT): 0.7925160431587325
- 35 USC 102 Novelty (BERT): 0.5387571650124828
- Combined Prediction Score: 0.7671401553441075
- Mean Citation Score: 342.51614000000006
- Max Citation Score: 362.67856
- Similarity Product: 282.16327012256625

Labels:
- Claim Label 101: 1
- Claim Label 102: 1
- Claim Label 103: 1
- Claim Label 112: 1
- Combined Label: 1
- Label 101 Adjusted: 1

Dataset: test