ES2960754T3 - Compuestos de naftiridinona sustituidos útiles como activadores de células t - Google Patents

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Publication number

ES2960754T3

ES2960754T3 ES19744923T ES19744923T ES2960754T3 ES 2960754 T3 ES2960754 T3 ES 2960754T3 ES 19744923 T ES19744923 T ES 19744923T ES 19744923 T ES19744923 T ES 19744923T ES 2960754 T3 ES2960754 T3 ES 2960754T3

Authority

ES

Spain

Prior art keywords

methyl

oxo

naphthyridine

dihydro

carbonitrile

Prior art date

2018-06-27

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• VHSIAYLBCLUAFT-UHFFFAOYSA-N n-[3-acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,8-naphthyridin-4-yl]acetamide Chemical class C=1C=C(Cl)C=CC=1C=1C=C2C(NC(=O)C)=C(C(C)=O)C(=O)N(C)C2=NC=1C1=CC=C(Cl)C=C1Cl VHSIAYLBCLUAFT-UHFFFAOYSA-N 0.000 title description 5
• 229940126530 T cell activator Drugs 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 254
• 150000003839 salts Chemical class 0.000 claims abstract description 106
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 33
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 28
• 201000011510 cancer Diseases 0.000 claims abstract description 22
• 238000011282 treatment Methods 0.000 claims abstract description 22
• 208000036142 Viral infection Diseases 0.000 claims abstract description 13
• 230000009385 viral infection Effects 0.000 claims abstract description 13
• -1 -OH Chemical group 0.000 claims description 401
• 125000000217 alkyl group Chemical group 0.000 claims description 264
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 222
• 229910052801 chlorine Inorganic materials 0.000 claims description 183
• 229910052731 fluorine Inorganic materials 0.000 claims description 181
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 166
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 144
• 125000001424 substituent group Chemical group 0.000 claims description 125
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 119
• 229910052799 carbon Inorganic materials 0.000 claims description 111
• 229910052794 bromium Inorganic materials 0.000 claims description 109
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 99
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 86
• 229910052739 hydrogen Inorganic materials 0.000 claims description 73
• 125000003545 alkoxy group Chemical group 0.000 claims description 72
• 125000000623 heterocyclic group Chemical group 0.000 claims description 69
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 63
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 61
• 125000004122 cyclic group Chemical group 0.000 claims description 56
• 125000004076 pyridyl group Chemical group 0.000 claims description 40
• 125000001072 heteroaryl group Chemical group 0.000 claims description 35
• 125000002757 morpholinyl group Chemical group 0.000 claims description 35
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 34
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 26
• 125000001425 triazolyl group Chemical group 0.000 claims description 24
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 22
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 21
• 125000001544 thienyl group Chemical group 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 20
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 19
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 19
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 18
• 125000000335 thiazolyl group Chemical group 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 17
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 17
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 16
• 125000001041 indolyl group Chemical group 0.000 claims description 15
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 15
• 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims description 14
• 125000002883 imidazolyl group Chemical group 0.000 claims description 14
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 14
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 13
• 125000002971 oxazolyl group Chemical group 0.000 claims description 13
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 13
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 13
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
• QBLJMEHOKNLCLR-VQSPDULUSA-N 8-[(2S,5R)-4-[(2-fluorophenyl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=CC=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F QBLJMEHOKNLCLR-VQSPDULUSA-N 0.000 claims description 12
• ZVROILBUAFTOJD-VQSPDULUSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F ZVROILBUAFTOJD-VQSPDULUSA-N 0.000 claims description 12
• RDYXNAYOGBPEBC-HFHQHIJTSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(4-methylphenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)C RDYXNAYOGBPEBC-HFHQHIJTSA-N 0.000 claims description 12
• 125000000304 alkynyl group Chemical group 0.000 claims description 12
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 201000001441 melanoma Diseases 0.000 claims description 11
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
• SQDBBZSIYKHBIU-XWZNDSGVSA-N 8-[(2S,5R)-4-[(3-chlorophenyl)-(5-methylpyridin-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC=1C=C(C=CC=1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=C(C=C1)C SQDBBZSIYKHBIU-XWZNDSGVSA-N 0.000 claims description 10
• ZPTNEZWBFQNQJP-CABCVRRESA-N 8-[(2S,5R)-4-[[2-fluoro-4-(trifluoromethoxy)phenyl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=CC(=C1)OC(F)(F)F)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C ZPTNEZWBFQNQJP-CABCVRRESA-N 0.000 claims description 10
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 10
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
• 125000000597 dioxinyl group Chemical group 0.000 claims description 9
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 8
• DCTWMSNLQFUZPF-UHFFFAOYSA-N 1,5-naphthyridine-2-carbonitrile Chemical compound N1=CC=CC2=NC(C#N)=CC=C21 DCTWMSNLQFUZPF-UHFFFAOYSA-N 0.000 claims description 8
• QBTXPCPOQVQZOB-ZWKOTPCHSA-N 4-[(2R,5S)-4-[bis(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-6-bromo-1-methyl-2-oxo-1,5-naphthyridine-3-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@H](N(C[C@@H]1C)C1=C(C(N(C2=CC=C(N=C12)Br)C)=O)C#N)C)C1=CC=C(C=C1)F QBTXPCPOQVQZOB-ZWKOTPCHSA-N 0.000 claims description 8
• DPIVAHMCELKSSH-RUZDIDTESA-N 4-[(3S)-4-[bis(4-fluorophenyl)methyl]-3-propan-2-ylpiperazin-1-yl]-6-bromo-1-methyl-2-oxo-1,5-naphthyridine-3-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1[C@H](CN(CC1)C1=C(C(N(C2=CC=C(N=C12)Br)C)=O)C#N)C(C)C)C1=CC=C(C=C1)F DPIVAHMCELKSSH-RUZDIDTESA-N 0.000 claims description 8
• ZYGSALGIXYZEOJ-UHFFFAOYSA-N 4-[4-[bis(4-fluorophenyl)methyl]-3-(hydroxymethyl)piperazin-1-yl]-6-bromo-1-methyl-2-oxo-1,5-naphthyridine-3-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C(CN(CC1)C1=C(C(N(C2=CC=C(N=C12)Br)C)=O)C#N)CO)C1=CC=C(C=C1)F ZYGSALGIXYZEOJ-UHFFFAOYSA-N 0.000 claims description 8
• QIGIILMBQPOMRJ-NYCGYEKWSA-N 8-[(2S,5R)-2,5-dimethyl-4-[pyridin-2-yl-[4-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)C(C1=CC=C(C=C1)OC(F)(F)F)C1=NC=CC=C1)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O QIGIILMBQPOMRJ-NYCGYEKWSA-N 0.000 claims description 8
• BRMGFDUSUGWXOA-BCSWVDANSA-N 8-[(2S,5R)-4-[(2,6-difluorophenyl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C(=CC=C1)F)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F BRMGFDUSUGWXOA-BCSWVDANSA-N 0.000 claims description 8
• PPRLKCHZDWAYJS-UWSFRVEYSA-N 8-[(2S,5R)-4-[(3,4-difluorophenyl)-pyridin-2-ylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC=1C=C(C=CC=1F)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=CC=C1 PPRLKCHZDWAYJS-UWSFRVEYSA-N 0.000 claims description 8
• CPVHFRYMNXCMJE-VQSPDULUSA-N 8-[(2S,5R)-4-[(3-fluorophenyl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC=1C=C(C=CC=1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F CPVHFRYMNXCMJE-VQSPDULUSA-N 0.000 claims description 8
• YDZPTTAVRKQNBV-XWZNDSGVSA-N 8-[(2S,5R)-4-[(3-fluorophenyl)-(6-methylpyridin-3-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC=1C=C(C=CC=1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C=1C=NC(=CC=1)C YDZPTTAVRKQNBV-XWZNDSGVSA-N 0.000 claims description 8
• SBFXTRNCOXYUGX-XWZNDSGVSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(5-methylpyridin-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=C(C=C1)C SBFXTRNCOXYUGX-XWZNDSGVSA-N 0.000 claims description 8
• HYVYVJKCUWGLKG-UWSFRVEYSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(2-methylpyrimidin-4-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC(=NC=C1)C HYVYVJKCUWGLKG-UWSFRVEYSA-N 0.000 claims description 8
• SOCABYBFBPXOQI-HFHQHIJTSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(4-methylphenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)C SOCABYBFBPXOQI-HFHQHIJTSA-N 0.000 claims description 8
• WVMNOHPYYHECBU-ABIZDYMHSA-N 8-[(2S,5R)-4-[1-(2,6-difluoro-4-hydroxyphenyl)-2,2,2-trifluoroethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C(=CC(=C1)O)F)C(C(F)(F)F)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C WVMNOHPYYHECBU-ABIZDYMHSA-N 0.000 claims description 8
• UGTVEDGUFKEUDU-YSPPHNQVSA-N 8-[(2S,5R)-4-[1-[2-fluoro-4-(trifluoromethyl)phenyl]ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=CC(=C1)C(F)(F)F)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C UGTVEDGUFKEUDU-YSPPHNQVSA-N 0.000 claims description 8
• SPHKLOQBKCQQMI-MSOLQXFVSA-N 8-[(2S,5R)-4-[bis(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-7-bromo-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)Br)C)C1=CC=C(C=C1)F SPHKLOQBKCQQMI-MSOLQXFVSA-N 0.000 claims description 8
• MJPJKXAWIMBCGQ-FOEZPWHWSA-N 8-[(3R)-4-[(3-fluorophenyl)-(5-methylpyridin-2-yl)methyl]-3-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound FC=1C=C(C=CC=1)C(N1[C@@H](CN(CC1)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=NC=C(C=C1)C MJPJKXAWIMBCGQ-FOEZPWHWSA-N 0.000 claims description 8
• VGEXTLWWQPHOMG-UHFFFAOYSA-N 8-[4-[bis(4-fluorophenyl)methyl]-3-(hydroxymethyl)piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C(CN(CC1)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CO)C1=CC=C(C=C1)F VGEXTLWWQPHOMG-UHFFFAOYSA-N 0.000 claims description 8
• RDKAXDJPUUHECA-UHFFFAOYSA-N O=C1NC=2C=CC(=NC=2C=C1)C#N Chemical compound O=C1NC=2C=CC(=NC=2C=C1)C#N RDKAXDJPUUHECA-UHFFFAOYSA-N 0.000 claims description 8
• 125000004802 cyanophenyl group Chemical group 0.000 claims description 8
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 8
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 7
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 7
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
• LXWKDRNJLJWLGZ-GNXJLENFSA-N 8-[(2S,5R)-2,5-dimethyl-4-[1-(2,4,6-trifluorophenyl)ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)C(C)C1=C(C=C(C=C1F)F)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O LXWKDRNJLJWLGZ-GNXJLENFSA-N 0.000 claims description 6
• GIEAMMVMRCABGA-VQSPDULUSA-N 8-[(2S,5R)-4-[(2,6-difluorophenyl)-phenylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C(=CC=C1)F)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=CC=C1 GIEAMMVMRCABGA-VQSPDULUSA-N 0.000 claims description 6
• LBKDIUDSIHDZAC-NYCGYEKWSA-N 8-[(2S,5R)-4-[(3-fluorophenyl)-pyridin-2-ylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC=1C=C(C=CC=1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=CC=C1 LBKDIUDSIHDZAC-NYCGYEKWSA-N 0.000 claims description 6
• BNBGHWSVPQUGNW-NYCGYEKWSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-pyridin-2-ylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=CC=C1 BNBGHWSVPQUGNW-NYCGYEKWSA-N 0.000 claims description 6
• FTTLEGYKIQSIJH-HFHQHIJTSA-N 8-[(2S,5R)-4-[(4-cyanophenyl)-(5-methylpyridin-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=C(C=C1)C FTTLEGYKIQSIJH-HFHQHIJTSA-N 0.000 claims description 6
• DVUVMHLSHWJQRH-UWSFRVEYSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(2-methylpyrimidin-5-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C=1C=NC(=NC=1)C DVUVMHLSHWJQRH-UWSFRVEYSA-N 0.000 claims description 6
• SJWUYEUYBXBOHM-UWSFRVEYSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(5-fluoropyridin-3-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C=1C=NC=C(C=1)F SJWUYEUYBXBOHM-UWSFRVEYSA-N 0.000 claims description 6
• MBBVYAZCEDPAPL-XWZNDSGVSA-N 8-[(2S,5R)-4-[(5-chloropyridin-2-yl)-(4-methylphenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC=1C=CC(=NC=1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)C MBBVYAZCEDPAPL-XWZNDSGVSA-N 0.000 claims description 6
• BSFIFGRGJJYWPV-TURHTGMXSA-N 8-[(2S,5R)-4-[(5-ethylpyridin-2-yl)-(3-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)C=1C=CC(=NC=1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC(=CC=C1)F BSFIFGRGJJYWPV-TURHTGMXSA-N 0.000 claims description 6
• IOUXPOBFEDDMFT-XWZNDSGVSA-N 8-[(2S,5R)-4-[(5-fluoropyridin-3-yl)-(4-methylphenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC=1C=C(C=NC=1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)C IOUXPOBFEDDMFT-XWZNDSGVSA-N 0.000 claims description 6
• MIMSHWAQHZOTJK-ZQIYAJFXSA-N 8-[(2S,5R)-4-[1-(2,4-difluorophenyl)propyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=CC(=C1)F)C(CC)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C MIMSHWAQHZOTJK-ZQIYAJFXSA-N 0.000 claims description 6
• UQKFHHZGJBEGMM-ZYLKAMJESA-N 8-[(2S,5R)-4-[1-[4-(difluoromethoxy)phenyl]ethyl]-2-ethyl-5-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC(OC1=CC=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC)F UQKFHHZGJBEGMM-ZYLKAMJESA-N 0.000 claims description 6
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• ONTRTSUXIUYRHY-HFLPEKOISA-N 8-[(3R)-4-[(4-chlorophenyl)-(4-methylphenyl)methyl]-3-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1[C@@H](CN(CC1)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=CC=C(C=C1)C ONTRTSUXIUYRHY-HFLPEKOISA-N 0.000 claims description 6
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• FYHRFCHDKGHPEE-XZATXCMXSA-N 8-[(3R)-4-[(4-fluorophenyl)-[4-(trifluoromethyl)phenyl]methyl]-3-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound FC1=CC=C(C=C1)C(N1[C@@H](CN(CC1)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=CC=C(C=C1)C(F)(F)F FYHRFCHDKGHPEE-XZATXCMXSA-N 0.000 claims description 6
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• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 5
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• 125000005348 fluorocycloalkyl group Chemical group 0.000 claims description 5
• LPHZQNBYGJPBAJ-UHFFFAOYSA-N 3-chloro-4-[4-[(4-fluorophenyl)-phenylmethyl]piperazin-1-yl]-6-methoxy-1-methyl-1,5-naphthyridin-2-one Chemical compound ClC=1C(N(C2=CC=C(N=C2C=1N1CCN(CC1)C(C1=CC=CC=C1)C1=CC=C(C=C1)F)OC)C)=O LPHZQNBYGJPBAJ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
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• CPIDLCMMNUSOMR-UHFFFAOYSA-N 4-[4-[bis(4-fluorophenyl)methyl]-3-(fluoromethyl)piperazin-1-yl]-6-bromo-1-methyl-2-oxo-1,5-naphthyridine-3-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C(CN(CC1)C1=C(C(N(C2=CC=C(N=C12)Br)C)=O)C#N)CF)C1=CC=C(C=C1)F CPIDLCMMNUSOMR-UHFFFAOYSA-N 0.000 claims description 4
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• DGGPIZHCRAGQIQ-QGZVFWFLSA-N 5-methyl-8-[(3R)-3-methyl-4-(quinolin-2-ylmethyl)piperazin-1-yl]-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound CN1C=2C=CC(=NC=2C(=C(C1=O)C#N)N1C[C@H](N(CC1)CC1=NC2=CC=CC=C2C=C1)C)C#N DGGPIZHCRAGQIQ-QGZVFWFLSA-N 0.000 claims description 4
• WDOUDCFOWSJYAR-CYBMUJFWSA-N 5-methyl-8-[(3R)-3-methyl-4-[(2,4,6-trifluorophenyl)methyl]piperazin-1-yl]-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound CN1C=2C=CC(=NC=2C(=C(C1=O)C#N)N1C[C@H](N(CC1)CC1=C(C=C(C=C1F)F)F)C)C#N WDOUDCFOWSJYAR-CYBMUJFWSA-N 0.000 claims description 4
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• ITIQZSHOZSXJBM-OAHLLOKOSA-N 5-methyl-8-[(3R)-3-methyl-4-[[2-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound CN1C=2C=CC(=NC=2C(=C(C1=O)C#N)N1C[C@H](N(CC1)CC1=C(C=CC=C1)C(F)(F)F)C)C#N ITIQZSHOZSXJBM-OAHLLOKOSA-N 0.000 claims description 4
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• JDSGMIINKLWWQL-KBMIEXCESA-N 8-[(2R,5R)-4-[bis(4-fluorophenyl)methyl]-2-(methoxymethyl)-5-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)COC)C1=CC=C(C=C1)F JDSGMIINKLWWQL-KBMIEXCESA-N 0.000 claims description 4
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• ZFGNOIVUPPAIIR-KBMIEXCESA-N 8-[(2R,5R)-4-[bis(4-fluorophenyl)methyl]-5-(methoxymethyl)-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@H](N(C[C@@H]1COC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F ZFGNOIVUPPAIIR-KBMIEXCESA-N 0.000 claims description 4
• JYFWOMWZAHAQNL-CZUORRHYSA-N 8-[(2R,5R)-5-(hydroxymethyl)-2-methyl-4-[(2,4,6-trifluorophenyl)methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound OC[C@@H]1N(C[C@H](N(C1)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)CC1=C(C=C(C=C1F)F)F JYFWOMWZAHAQNL-CZUORRHYSA-N 0.000 claims description 4
• CXJNRUHVJZNVBB-RBUKOAKNSA-N 8-[(2R,5S)-4-[bis(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@H](N(C[C@@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=CC=C(C=C1)F CXJNRUHVJZNVBB-RBUKOAKNSA-N 0.000 claims description 4
• XKXKEJGUONTNBW-MOPGFXCFSA-N 8-[(2R,5S)-4-[bis(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@H](N(C[C@@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F XKXKEJGUONTNBW-MOPGFXCFSA-N 0.000 claims description 4
• NBXIJTCTPJFAFD-MSOLQXFVSA-N 8-[(2S,5R)-2,5-diethyl-4-[(3,4,5-trifluorophenyl)methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)CC1=CC(=C(C(=C1)F)F)F)CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O NBXIJTCTPJFAFD-MSOLQXFVSA-N 0.000 claims description 4
• PDBGASOJGGMBIS-LXDWCAIISA-N 8-[(2S,5R)-2,5-diethyl-4-[(3-fluorophenyl)-(5-methoxypyridin-2-yl)methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)C(C1=NC=C(C=C1)OC)C1=CC(=CC=C1)F)CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O PDBGASOJGGMBIS-LXDWCAIISA-N 0.000 claims description 4
• SUCIBGAMOQHGAV-BBCCDPPWSA-N 8-[(2S,5R)-2,5-diethyl-4-[(4-fluorophenyl)-(1,3-oxazol-4-yl)methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)C(C=1N=COC=1)C1=CC=C(C=C1)F)CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O SUCIBGAMOQHGAV-BBCCDPPWSA-N 0.000 claims description 4
• VUKPPIUFRXGKDV-QVRKZYGESA-N 8-[(2S,5R)-2,5-diethyl-4-[(4-fluorophenyl)-[2-(trifluoromethyl)-1,3-thiazol-4-yl]methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)C(C=1N=C(SC=1)C(F)(F)F)C1=CC=C(C=C1)F)CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O VUKPPIUFRXGKDV-QVRKZYGESA-N 0.000 claims description 4
• KPQSMCDUDIFLMH-CJFSVXMISA-N 8-[(2S,5R)-2,5-diethyl-4-[(4-fluorophenyl)-[5-(trifluoromethyl)pyridin-2-yl]methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)C(C1=NC=C(C=C1)C(F)(F)F)C1=CC=C(C=C1)F)CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O KPQSMCDUDIFLMH-CJFSVXMISA-N 0.000 claims description 4
• IGFZKVHVNKXZGB-RRSSYJFLSA-N 8-[(2S,5R)-2,5-diethyl-4-[(4-fluorophenyl)-[6-(trifluoromethyl)pyridin-2-yl]methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)C(C1=NC(=CC=C1)C(F)(F)F)C1=CC=C(C=C1)F)CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O IGFZKVHVNKXZGB-RRSSYJFLSA-N 0.000 claims description 4
• OYSXYLHWBWWUFT-RTWAWAEBSA-N 8-[(2S,5R)-2,5-diethyl-4-[(4-fluorophenyl)methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)CC1=CC=C(C=C1)F)CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O OYSXYLHWBWWUFT-RTWAWAEBSA-N 0.000 claims description 4
• UYFQNBUSDPZSEZ-BEWYTNLXSA-N 8-[(2S,5R)-2,5-diethyl-4-[1-[2-fluoro-4-(trifluoromethoxy)phenyl]propyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)C(CC)C1=C(C=C(C=C1)OC(F)(F)F)F)CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O UYFQNBUSDPZSEZ-BEWYTNLXSA-N 0.000 claims description 4
• DSEPXCOFDZGBER-SJRAPUSDSA-N 8-[(2S,5R)-2,5-diethyl-4-[1-[4-(trifluoromethoxy)phenyl]ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)C(C)C1=CC=C(C=C1)OC(F)(F)F)CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O DSEPXCOFDZGBER-SJRAPUSDSA-N 0.000 claims description 4
• JXYGJTHWZJADAK-VXVSGHKGSA-N 8-[(2S,5R)-2,5-diethyl-4-[1-[4-(trifluoromethoxy)phenyl]propyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)C(CC)C1=CC=C(C=C1)OC(F)(F)F)CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O JXYGJTHWZJADAK-VXVSGHKGSA-N 0.000 claims description 4
• GWPUGNXRGQXEPL-RRNUJPESSA-N 8-[(2S,5R)-2,5-diethyl-4-[1-[4-(trifluoromethyl)phenyl]ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)C(C)C1=CC=C(C=C1)C(F)(F)F)CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O GWPUGNXRGQXEPL-RRNUJPESSA-N 0.000 claims description 4
• SVRCPFCAGLHQGO-MOPGFXCFSA-N 8-[(2S,5R)-2,5-diethyl-4-[[2-fluoro-4-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)CC1=C(C=C(C=C1)OC(F)(F)F)F)CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O SVRCPFCAGLHQGO-MOPGFXCFSA-N 0.000 claims description 4
• WWHWYLUZADGYPZ-UXHICEINSA-N 8-[(2S,5R)-2,5-diethyl-4-[[4-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)CC1=CC=C(C=C1)OC(F)(F)F)CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O WWHWYLUZADGYPZ-UXHICEINSA-N 0.000 claims description 4
• GQOCAUFPQNREHY-YTYFACEESA-N 8-[(2S,5R)-2,5-dimethyl-4-(1-quinolin-5-ylethyl)piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)C(C)C1=C2C=CC=NC2=CC=C1)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O GQOCAUFPQNREHY-YTYFACEESA-N 0.000 claims description 4
• MCPYVTBATOTZCW-CVEARBPZSA-N 8-[(2S,5R)-2,5-dimethyl-4-(oxan-4-ylmethyl)piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)CC1CCOCC1)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O MCPYVTBATOTZCW-CVEARBPZSA-N 0.000 claims description 4
• GVHAVUDSSISZFQ-SJORKVTESA-N 8-[(2S,5R)-2,5-dimethyl-4-[(1-methylindazol-4-yl)methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)CC1=C2C=NN(C2=CC=C1)C)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O GVHAVUDSSISZFQ-SJORKVTESA-N 0.000 claims description 4
• MFXJRECEENQWBP-KGLIPLIRSA-N 8-[(2S,5R)-2,5-dimethyl-4-[(3,4,5-trifluorophenyl)methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)CC1=CC(=C(C(=C1)F)F)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O MFXJRECEENQWBP-KGLIPLIRSA-N 0.000 claims description 4
• BCKDCAISZQUUTQ-MSOLQXFVSA-N 8-[(2S,5R)-2,5-dimethyl-4-[(3-phenyl-1,2-oxazol-5-yl)methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)CC1=CC(=NO1)C1=CC=CC=C1)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O BCKDCAISZQUUTQ-MSOLQXFVSA-N 0.000 claims description 4
• LMZJIQITMWNVDN-MOPGFXCFSA-N 8-[(2S,5R)-2,5-dimethyl-4-[(3-propan-2-yloxyphenyl)methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)(C)OC=1C=C(CN2C[C@@H](N(C[C@H]2C)C2=CC(N(C=3C=CC(=NC2=3)C#N)C)=O)C)C=CC=1 LMZJIQITMWNVDN-MOPGFXCFSA-N 0.000 claims description 4
• BJUJTMUXYBYZID-SJORKVTESA-N 8-[(2S,5R)-2,5-dimethyl-4-[(4-methyl-3-oxo-1,4-benzoxazin-5-yl)methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)CC1=CC=CC2=C1N(C(CO2)=O)C)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O BJUJTMUXYBYZID-SJORKVTESA-N 0.000 claims description 4
• VNSKJYSYJKVHAL-FINJQHJWSA-N 8-[(2S,5R)-2,5-dimethyl-4-[(4-methylphenyl)-(6-methylpyridin-2-yl)methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)C(C1=CC=C(C=C1)C)C1=NC(=CC=C1)C)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O VNSKJYSYJKVHAL-FINJQHJWSA-N 0.000 claims description 4
• SJSONHFOKFFIHL-MOPGFXCFSA-N 8-[(2S,5R)-2,5-dimethyl-4-[(4-propan-2-ylphenyl)methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)(C)C1=CC=C(CN2C[C@@H](N(C[C@H]2C)C2=CC(N(C=3C=CC(=NC2=3)C#N)C)=O)C)C=C1 SJSONHFOKFFIHL-MOPGFXCFSA-N 0.000 claims description 4
• QUMMKBWJTUNBMX-KGLIPLIRSA-N 8-[(2S,5R)-2,5-dimethyl-4-[(5-methyl-1,2-oxazol-3-yl)methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)CC1=NOC(=C1)C)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O QUMMKBWJTUNBMX-KGLIPLIRSA-N 0.000 claims description 4
• OJTWDWMZQZKZRX-CABCVRRESA-N 8-[(2S,5R)-2,5-dimethyl-4-[(5-propan-2-yl-1,2,4-oxadiazol-3-yl)methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)(C)C1=NC(=NO1)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C OJTWDWMZQZKZRX-CABCVRRESA-N 0.000 claims description 4
• RVCMWUKZJMOBFU-LFPSWIHMSA-N 8-[(2S,5R)-2,5-dimethyl-4-[1-(4-propan-2-ylphenyl)ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)(C)C1=CC=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C RVCMWUKZJMOBFU-LFPSWIHMSA-N 0.000 claims description 4
• CMJKYMWANGLHGP-CNYCQXTOSA-N 8-[(2S,5R)-2,5-dimethyl-4-[1-(5-methyl-1,2-oxazol-3-yl)ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)C(C)C1=NOC(=C1)C)C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N CMJKYMWANGLHGP-CNYCQXTOSA-N 0.000 claims description 4
• MMXWBWXVOHPNKU-GARXDOFDSA-N 8-[(2S,5R)-2,5-dimethyl-4-[1-[2-(trifluoromethoxy)phenyl]ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)C(C)C1=C(C=CC=C1)OC(F)(F)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O MMXWBWXVOHPNKU-GARXDOFDSA-N 0.000 claims description 4
• QLRSEPCFICVGFH-YTYFACEESA-N 8-[(2S,5R)-2,5-dimethyl-4-[1-[4-(1,2,4-triazol-1-yl)phenyl]ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound N1(N=CN=C1)C1=CC=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C QLRSEPCFICVGFH-YTYFACEESA-N 0.000 claims description 4
• QFAWBHKVBFPUMF-GARXDOFDSA-N 8-[(2S,5R)-2,5-dimethyl-4-[1-[4-(trifluoromethyl)phenyl]ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)C(C)C1=CC=C(C=C1)C(F)(F)F)C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N QFAWBHKVBFPUMF-GARXDOFDSA-N 0.000 claims description 4
• FSFDQYBMIOGDQL-YSPPHNQVSA-N 8-[(2S,5R)-2,5-dimethyl-4-[1-[5-(trifluoromethyl)pyridin-2-yl]ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)C(C)C1=NC=C(C=C1)C(F)(F)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O FSFDQYBMIOGDQL-YSPPHNQVSA-N 0.000 claims description 4
• USZBSOMSLQMJLH-FTAULWBTSA-N 8-[(2S,5R)-2,5-dimethyl-4-[2,2,2-trifluoro-1-(2-fluoro-4-hydroxyphenyl)ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)C(C(F)(F)F)C1=C(C=C(C=C1)O)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O USZBSOMSLQMJLH-FTAULWBTSA-N 0.000 claims description 4
• ZHOIBGZBQAGQOH-KYFQQJHYSA-N 8-[(2S,5R)-2,5-dimethyl-4-[2,2,2-trifluoro-1-(4-fluorophenyl)ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)C(C(F)(F)F)C1=CC=C(C=C1)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O ZHOIBGZBQAGQOH-KYFQQJHYSA-N 0.000 claims description 4
• PSEBMLIXPSXXHQ-SJORKVTESA-N 8-[(2S,5R)-2,5-dimethyl-4-[[2-methyl-4-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)CC1=C(C=C(C=C1)OC(F)(F)F)C)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O PSEBMLIXPSXXHQ-SJORKVTESA-N 0.000 claims description 4
• WRTIVXDXLOYPHE-CABCVRRESA-N 8-[(2S,5R)-2,5-dimethyl-4-[[2-methyl-6-(trifluoromethyl)pyridin-3-yl]methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)CC=1C(=NC(=CC=1)C(F)(F)F)C)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O WRTIVXDXLOYPHE-CABCVRRESA-N 0.000 claims description 4
• DTSHYSLOTZTVFB-CVEARBPZSA-N 8-[(2S,5R)-2,5-dimethyl-4-[[3-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)CC1=CC(=CC=C1)OC(F)(F)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O DTSHYSLOTZTVFB-CVEARBPZSA-N 0.000 claims description 4
• YVOQCCXTCWGDBU-CVEARBPZSA-N 8-[(2S,5R)-2,5-dimethyl-4-[[4-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)CC1=CC=C(C=C1)OC(F)(F)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O YVOQCCXTCWGDBU-CVEARBPZSA-N 0.000 claims description 4
• OPEODEFSCRPOIM-NEPJUHHUSA-N 8-[(2S,5R)-2,5-dimethyl-4-[[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)CC=1OC(=NN=1)C(F)(F)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O OPEODEFSCRPOIM-NEPJUHHUSA-N 0.000 claims description 4
• FMLFAJVPPYOSTO-CABCVRRESA-N 8-[(2S,5R)-2,5-dimethyl-4-[[6-(trifluoromethyl)pyridin-2-yl]methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)CC1=NC(=CC=C1)C(F)(F)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O FMLFAJVPPYOSTO-CABCVRRESA-N 0.000 claims description 4
• QXVBZGXBMJYZHM-XWZNDSGVSA-N 8-[(2S,5R)-2,5-dimethyl-4-[phenyl-[4-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C[C@@H]1N(C[C@H](N(C1)C(C1=CC=C(C=C1)OC(F)(F)F)C1=CC=CC=C1)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O QXVBZGXBMJYZHM-XWZNDSGVSA-N 0.000 claims description 4
• VTNJLFUCOAFLJV-PWDJEIQTSA-N 8-[(2S,5R)-2-ethyl-4-[(4-fluorophenyl)-[5-(trifluoromethyl)pyridin-2-yl]methyl]-5-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)C(C1=NC=C(C=C1)C(F)(F)F)C1=CC=C(C=C1)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O VTNJLFUCOAFLJV-PWDJEIQTSA-N 0.000 claims description 4
• RNMFHDGCHKKMEY-ZPTFWOHHSA-N 8-[(2S,5R)-2-ethyl-4-[(4-fluorophenyl)-[6-(trifluoromethyl)pyridin-2-yl]methyl]-5-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)C(C1=NC(=CC=C1)C(F)(F)F)C1=CC=C(C=C1)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O RNMFHDGCHKKMEY-ZPTFWOHHSA-N 0.000 claims description 4
• LNVCLHSXWJVWMA-YREILILBSA-N 8-[(2S,5R)-2-ethyl-4-[1-[3-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-5-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)C(C)C1=CC(=CC(=C1)OC(F)(F)F)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O LNVCLHSXWJVWMA-YREILILBSA-N 0.000 claims description 4
• DADQYOQRLWEYLF-STGLDUPZSA-N 8-[(2S,5R)-2-ethyl-5-methyl-4-[1-(3,4,5-trifluorophenyl)ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)C(C)C1=CC(=C(C(=C1)F)F)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O DADQYOQRLWEYLF-STGLDUPZSA-N 0.000 claims description 4
• KASQKZRIRMEPEG-ZYLKAMJESA-N 8-[(2S,5R)-2-ethyl-5-methyl-4-[1-[4-(trifluoromethoxy)phenyl]ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)C(C)C1=CC=C(C=C1)OC(F)(F)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O KASQKZRIRMEPEG-ZYLKAMJESA-N 0.000 claims description 4
• GLOGUUZMNDSLEV-QIFHVCNWSA-N 8-[(2S,5R)-2-ethyl-5-methyl-4-[1-[4-(trifluoromethoxy)phenyl]propyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)[C@@H]1N(C[C@H](N(C1)C(CC)C1=CC=C(C=C1)OC(F)(F)F)C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O GLOGUUZMNDSLEV-QIFHVCNWSA-N 0.000 claims description 4
• HLWBXFLGTSBQEL-SJORKVTESA-N 8-[(2S,5R)-4-(3,4-dihydro-2H-1,4-benzoxazin-8-ylmethyl)-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound O1CCNC2=C1C(=CC=C2)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C HLWBXFLGTSBQEL-SJORKVTESA-N 0.000 claims description 4
• BKOVUYNIBLOHMQ-KGLIPLIRSA-N 8-[(2S,5R)-4-[(1-cyclopropyltetrazol-5-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)N1N=NN=C1CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C BKOVUYNIBLOHMQ-KGLIPLIRSA-N 0.000 claims description 4
• ULOYNRRHAMXBBH-NJNVLPOUSA-N 8-[(2S,5R)-4-[(1-tert-butyltetrazol-5-yl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)(C)(C)N1N=NN=C1C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F ULOYNRRHAMXBBH-NJNVLPOUSA-N 0.000 claims description 4
• ITSXSYKMRJAHCY-CABCVRRESA-N 8-[(2S,5R)-4-[(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1(OC2=C(O1)C=CC(=C2)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)F ITSXSYKMRJAHCY-CABCVRRESA-N 0.000 claims description 4
• JXEHRPZLMWTZPL-MAUKXSAKSA-N 8-[(2S,5R)-4-[(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]-5-ethyl-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1(OC2=C(O1)C=CC(=C2)CN1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)F JXEHRPZLMWTZPL-MAUKXSAKSA-N 0.000 claims description 4
• MZRMZFWISMNPAA-VQSPDULUSA-N 8-[(2S,5R)-4-[(2,3-difluorophenyl)-phenylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=CC=C1F)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=CC=C1 MZRMZFWISMNPAA-VQSPDULUSA-N 0.000 claims description 4
• HZUDVSMORFHTSN-WJDUPLLKSA-N 8-[(2S,5R)-4-[(2,4-difluorophenyl)-(5-fluoropyridin-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=CC(=C1)F)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=C(C=C1)F HZUDVSMORFHTSN-WJDUPLLKSA-N 0.000 claims description 4
• PPOBWDYGMKLOKO-VQSPDULUSA-N 8-[(2S,5R)-4-[(2,4-difluorophenyl)-phenylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=CC(=C1)F)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=CC=C1 PPOBWDYGMKLOKO-VQSPDULUSA-N 0.000 claims description 4
• BFXDLPPFUOTCKI-UWSFRVEYSA-N 8-[(2S,5R)-4-[(2,4-difluorophenyl)-pyridin-2-ylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=CC(=C1)F)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=CC=C1 BFXDLPPFUOTCKI-UWSFRVEYSA-N 0.000 claims description 4
• KATWFHVQTKHHFR-UXHICEINSA-N 8-[(2S,5R)-4-[(2,4-difluorophenyl)methyl]-2,5-diethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=CC(=C1)F)CN1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC KATWFHVQTKHHFR-UXHICEINSA-N 0.000 claims description 4
• SWWOXJDERAXVQP-CABCVRRESA-N 8-[(2S,5R)-4-[(2,5-difluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=C(C=C1)F)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C SWWOXJDERAXVQP-CABCVRRESA-N 0.000 claims description 4
• PFRHSKGTZLPZNL-CABCVRRESA-N 8-[(2S,5R)-4-[(2,6-dichlorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=C(C(=CC=C1)Cl)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C PFRHSKGTZLPZNL-CABCVRRESA-N 0.000 claims description 4
• AKIUJGLYGWDYSH-MOPGFXCFSA-N 8-[(2S,5R)-4-[(2,6-dimethylphenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound CC1=C(C(=CC=C1)C)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C AKIUJGLYGWDYSH-MOPGFXCFSA-N 0.000 claims description 4
• AVQBJUOEFICBKK-KGLIPLIRSA-N 8-[(2S,5R)-4-[(2-chloro-3,6-difluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=C(C(=CC=C1F)F)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C AVQBJUOEFICBKK-KGLIPLIRSA-N 0.000 claims description 4
• PETPVAQRLNLXGZ-ZUDGUFDASA-N 8-[(2S,5R)-4-[(2-chloro-4-fluorophenyl)-(5-methylpyridin-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound ClC1=C(C=CC(=C1)F)C(N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=NC=C(C=C1)C PETPVAQRLNLXGZ-ZUDGUFDASA-N 0.000 claims description 4
• GEBCVPVDNCJGLA-HNAYVOBHSA-N 8-[(2S,5R)-4-[(2-chloro-4-fluorophenyl)methyl]-5-ethyl-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=C(C=CC(=C1)F)CN1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C GEBCVPVDNCJGLA-HNAYVOBHSA-N 0.000 claims description 4
• FPFOIBPWFVPEMO-CVEARBPZSA-N 8-[(2S,5R)-4-[(2-chloro-6-cyanophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=C(C(=CC=C1)C#N)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C FPFOIBPWFVPEMO-CVEARBPZSA-N 0.000 claims description 4
• GRIWTSOATOAVIM-CABCVRRESA-N 8-[(2S,5R)-4-[(2-chloro-6-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=C(C(=CC=C1)F)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C GRIWTSOATOAVIM-CABCVRRESA-N 0.000 claims description 4
• XHPWMBFEYFMBLQ-CVEARBPZSA-N 8-[(2S,5R)-4-[(2-cyano-6-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(#N)C1=C(C(=CC=C1)F)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C XHPWMBFEYFMBLQ-CVEARBPZSA-N 0.000 claims description 4
• MJPDBLDQPPLPCY-QIXCQHHOSA-N 8-[(2S,5R)-4-[(2-cyclopropyl-1,3-thiazol-4-yl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound C1(CC1)C=1SC=C(N=1)C(N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=CC=C(C=C1)F MJPDBLDQPPLPCY-QIXCQHHOSA-N 0.000 claims description 4
• LCEKVJDVLWVFCY-UWSFRVEYSA-N 8-[(2S,5R)-4-[(2-cyclopropyl-1,3-thiazol-4-yl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)C=1SC=C(N=1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F LCEKVJDVLWVFCY-UWSFRVEYSA-N 0.000 claims description 4
• HRJLQFNQEDCPEQ-UWSFRVEYSA-N 8-[(2S,5R)-4-[(2-cyclopropyl-1,3-thiazol-5-yl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)C=1SC(=CN=1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F HRJLQFNQEDCPEQ-UWSFRVEYSA-N 0.000 claims description 4
• GWDQSHALENGDHL-LVQXAQMUSA-N 8-[(2S,5R)-4-[(2-ethoxy-4-fluorophenyl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)OC1=C(C=CC(=C1)F)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F GWDQSHALENGDHL-LVQXAQMUSA-N 0.000 claims description 4
• GWECHCIXMMZYOQ-LVQXAQMUSA-N 8-[(2S,5R)-4-[(2-ethyl-4-fluorophenyl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)C1=C(C=CC(=C1)F)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F GWECHCIXMMZYOQ-LVQXAQMUSA-N 0.000 claims description 4
• UROZMOYBKUCETA-SBCWPUQDSA-N 8-[(2S,5R)-4-[(2-ethylphenyl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound C(C)C1=C(C=CC=C1)C(N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=CC=C(C=C1)F UROZMOYBKUCETA-SBCWPUQDSA-N 0.000 claims description 4
• OKABFFCSTDORKO-XWZNDSGVSA-N 8-[(2S,5R)-4-[(2-fluorophenyl)-phenylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=CC=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=CC=C1 OKABFFCSTDORKO-XWZNDSGVSA-N 0.000 claims description 4
• PLOZKMYZHIUSMV-CVEARBPZSA-N 8-[(2S,5R)-4-[(2-hydroxyphenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound OC1=C(C=CC=C1)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C PLOZKMYZHIUSMV-CVEARBPZSA-N 0.000 claims description 4
• VIJVLEUBQKFYNR-XWZNDSGVSA-N 8-[(2S,5R)-4-[(2-tert-butylpyrimidin-4-yl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)(C)(C)C1=NC=CC(=N1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F VIJVLEUBQKFYNR-XWZNDSGVSA-N 0.000 claims description 4
• OZFHKHWKRGGDNP-CABCVRRESA-N 8-[(2S,5R)-4-[(3,4-difluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC=1C=C(C=CC=1F)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C OZFHKHWKRGGDNP-CABCVRRESA-N 0.000 claims description 4
• FENXEPQFNMTWMZ-ZUDGUFDASA-N 8-[(2S,5R)-4-[(3,5-difluorophenyl)-phenylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound FC=1C=C(C=C(C=1)F)C(N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=CC=CC=C1 FENXEPQFNMTWMZ-ZUDGUFDASA-N 0.000 claims description 4
• NBNJDCIZMWIIHM-VQSPDULUSA-N 8-[(2S,5R)-4-[(3,5-difluorophenyl)-phenylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=CC=C1 NBNJDCIZMWIIHM-VQSPDULUSA-N 0.000 claims description 4
• QLIXKASRJLEMQH-CABCVRRESA-N 8-[(2S,5R)-4-[(3,5-difluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C QLIXKASRJLEMQH-CABCVRRESA-N 0.000 claims description 4
• RUGUHSFRYPCYJP-KGLIPLIRSA-N 8-[(2S,5R)-4-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound CC1=NOC(=C1CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C RUGUHSFRYPCYJP-KGLIPLIRSA-N 0.000 claims description 4
• BBKKEROXPHROCC-HFHQHIJTSA-N 8-[(2S,5R)-4-[(3-chloro-4-methylphenyl)-(5-methylpyridin-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC=1C=C(C=CC=1C)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=C(C=C1)C BBKKEROXPHROCC-HFHQHIJTSA-N 0.000 claims description 4
• XOCQZOBZHLEGSR-TURHTGMXSA-N 8-[(2S,5R)-4-[(3-chlorophenyl)-(5-ethylpyridin-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC=1C=C(C=CC=1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=C(C=C1)CC XOCQZOBZHLEGSR-TURHTGMXSA-N 0.000 claims description 4
• CXKXRGPLVBYNSN-SYDXZMBCSA-N 8-[(2S,5R)-4-[(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-(4-fluorophenyl)methyl]-2,5-diethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)C1=NOC(=N1)C(N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC)C1=CC=C(C=C1)F CXKXRGPLVBYNSN-SYDXZMBCSA-N 0.000 claims description 4
• CKQNDVQKDZGZIW-VRBVYGAASA-N 8-[(2S,5R)-4-[(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound C1(CC1)C1=NOC(=N1)C(N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=CC=C(C=C1)F CKQNDVQKDZGZIW-VRBVYGAASA-N 0.000 claims description 4
• DRQXBRWVAUXQLI-IWEOPWJISA-N 8-[(2S,5R)-4-[(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-(4-fluorophenyl)methyl]-5-ethyl-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)C1=NOC(=N1)C(N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F DRQXBRWVAUXQLI-IWEOPWJISA-N 0.000 claims description 4
• HNJFAORLFWENCI-MSOLQXFVSA-N 8-[(2S,5R)-4-[(3-ethoxyphenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)OC=1C=C(CN2C[C@@H](N(C[C@H]2C)C2=CC(N(C=3C=CC(=NC2=3)C#N)C)=O)C)C=CC=1 HNJFAORLFWENCI-MSOLQXFVSA-N 0.000 claims description 4
• MTLRXVSRMANCAA-NOVWKWNWSA-N 8-[(2S,5R)-4-[(3-ethyl-1,2,4-oxadiazol-5-yl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)C1=NOC(=N1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F MTLRXVSRMANCAA-NOVWKWNWSA-N 0.000 claims description 4
• WAZQMJQFZUSYFH-VQSPDULUSA-N 8-[(2S,5R)-4-[(3-fluorophenyl)-(5-methoxypyridin-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC=1C=C(C=CC=1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=C(C=C1)OC WAZQMJQFZUSYFH-VQSPDULUSA-N 0.000 claims description 4
• UVPPBOKIQAPOKJ-NJNVLPOUSA-N 8-[(2S,5R)-4-[(3-tert-butyl-1,2,4-oxadiazol-5-yl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)(C)(C)C1=NOC(=N1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F UVPPBOKIQAPOKJ-NJNVLPOUSA-N 0.000 claims description 4
• NPZIIGBRBLFOFD-MSOLQXFVSA-N 8-[(2S,5R)-4-[(4-acetyl-2,3-dihydro-1,4-benzoxazin-8-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)(=O)N1CCOC2=C1C=CC=C2CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C NPZIIGBRBLFOFD-MSOLQXFVSA-N 0.000 claims description 4
• YUHDKBJHVXISCS-NOVWKWNWSA-N 8-[(2S,5R)-4-[(4-bromophenyl)-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound BrC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC(=NO1)C1CC1 YUHDKBJHVXISCS-NOVWKWNWSA-N 0.000 claims description 4
• MLVFJIZSBHAPLP-KGLIPLIRSA-N 8-[(2S,5R)-4-[(4-chloro-2,6-difluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC(=C(C(=C1)F)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)F MLVFJIZSBHAPLP-KGLIPLIRSA-N 0.000 claims description 4
• NZFVJQNFBJEIJR-BCSWVDANSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC2=C(OC(O2)(F)F)C=C1 NZFVJQNFBJEIJR-BCSWVDANSA-N 0.000 claims description 4
• NCZDACJAOOFBHM-LVQXAQMUSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(2-ethyl-4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=C(C=C(C=C1)F)CC NCZDACJAOOFBHM-LVQXAQMUSA-N 0.000 claims description 4
• GFTZQKJJKKTVAX-UWSFRVEYSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(2-methylpyrimidin-5-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C=1C=NC(=NC=1)C GFTZQKJJKKTVAX-UWSFRVEYSA-N 0.000 claims description 4
• VLGRWFDQWCVNBO-TURHTGMXSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(4-cyanophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)C#N VLGRWFDQWCVNBO-TURHTGMXSA-N 0.000 claims description 4
• VJRRXJJIVVSBDA-ACKJMCFBSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(4-fluorophenyl)methyl]-2,5-diethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC)C1=CC=C(C=C1)F VJRRXJJIVVSBDA-ACKJMCFBSA-N 0.000 claims description 4
• HPVQRAVOQJICGR-KUTNOTQMSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(4-fluorophenyl)methyl]-2-ethyl-5-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC)C1=CC=C(C=C1)F HPVQRAVOQJICGR-KUTNOTQMSA-N 0.000 claims description 4
• FLLPWINCRIAPBL-MYZDVQGESA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(4-fluorophenyl)methyl]-5-ethyl-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F FLLPWINCRIAPBL-MYZDVQGESA-N 0.000 claims description 4
• GBGTWXQDYNAKAB-UJPQDCQRSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(4-methylphenyl)methyl]-2-ethyl-5-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC)C1=CC=C(C=C1)C GBGTWXQDYNAKAB-UJPQDCQRSA-N 0.000 claims description 4
• DWPJFSCGDFHGRJ-XWZNDSGVSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(4-methylpyridin-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=CC(=C1)C DWPJFSCGDFHGRJ-XWZNDSGVSA-N 0.000 claims description 4
• LDWKVKLDMOPOEG-QIXCQHHOSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(5-fluoropyridin-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=NC=C(C=C1)F LDWKVKLDMOPOEG-QIXCQHHOSA-N 0.000 claims description 4
• DANBUJJQGKZDEF-PWDJEIQTSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(5-fluoropyridin-2-yl)methyl]-2-ethyl-5-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC)C1=NC=C(C=C1)F DANBUJJQGKZDEF-PWDJEIQTSA-N 0.000 claims description 4
• DXMINKCABUDLSH-IWPIYJETSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(5-fluoropyridin-2-yl)methyl]-5-ethyl-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=C(C=C1)F DXMINKCABUDLSH-IWPIYJETSA-N 0.000 claims description 4
• CIVOTAFHJFVZOK-XWZNDSGVSA-N 8-[(2S,5R)-4-[(4-chlorophenyl)-(6-methylpyridin-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC(=CC=C1)C CIVOTAFHJFVZOK-XWZNDSGVSA-N 0.000 claims description 4
• DBEVDUOCZIBUBL-CABCVRRESA-N 8-[(2S,5R)-4-[(4-cyano-2,6-difluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(#N)C1=CC(=C(C(=C1)F)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)F DBEVDUOCZIBUBL-CABCVRRESA-N 0.000 claims description 4
• RFGVBBWNEPKGFQ-CVEARBPZSA-N 8-[(2S,5R)-4-[(4-cyano-2-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(#N)C1=CC(=C(C=C1)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)F RFGVBBWNEPKGFQ-CVEARBPZSA-N 0.000 claims description 4
• KCYJMBSIDLDILW-TURHTGMXSA-N 8-[(2S,5R)-4-[(4-cyanophenyl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F KCYJMBSIDLDILW-TURHTGMXSA-N 0.000 claims description 4
• JEXKEEPSPTUERI-ZUDGUFDASA-N 8-[(2S,5R)-4-[(4-cyanophenyl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-7-fluoro-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)F)C)C1=CC=C(C=C1)F JEXKEEPSPTUERI-ZUDGUFDASA-N 0.000 claims description 4
• AMSOEXIGFRYMCY-RHZWIKIYSA-N 8-[(2S,5R)-4-[(4-cyanophenyl)-(4-fluorophenyl)methyl]-5-ethyl-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F AMSOEXIGFRYMCY-RHZWIKIYSA-N 0.000 claims description 4
• WGEWUMNUIHFQRS-AVNYNHNVSA-N 8-[(2S,5R)-4-[(4-cyanophenyl)-(4-methylphenyl)methyl]-2,5-dimethylpiperazin-1-yl]-7-fluoro-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)F)C)C1=CC=C(C=C1)C WGEWUMNUIHFQRS-AVNYNHNVSA-N 0.000 claims description 4
• WSMGOKNOXCYYMC-CABCVRRESA-N 8-[(2S,5R)-4-[(4-cyanothiophen-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(#N)C=1C=C(SC=1)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C WSMGOKNOXCYYMC-CABCVRRESA-N 0.000 claims description 4
• NYKBMMJLKZSPRY-CJFSVXMISA-N 8-[(2S,5R)-4-[(4-cyclopropyl-1,3-thiazol-2-yl)-(4-fluorophenyl)methyl]-2,5-diethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)C=1N=C(SC=1)C(N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC)C1=CC=C(C=C1)F NYKBMMJLKZSPRY-CJFSVXMISA-N 0.000 claims description 4
• RKHFHFJEKBRCAR-UWSFRVEYSA-N 8-[(2S,5R)-4-[(4-cyclopropyl-1,3-thiazol-2-yl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)C=1N=C(SC=1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F RKHFHFJEKBRCAR-UWSFRVEYSA-N 0.000 claims description 4
• RSGXLFNWTHLURX-SBCWPUQDSA-N 8-[(2S,5R)-4-[(4-ethylphenyl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound C(C)C1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=CC=C(C=C1)F RSGXLFNWTHLURX-SBCWPUQDSA-N 0.000 claims description 4
• NJUGUKSJWHEASY-MSOLQXFVSA-N 8-[(2S,5R)-4-[(4-fluoro-2-propan-2-yloxyphenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC(=C(CN2C[C@@H](N(C[C@H]2C)C2=CC(N(C=3C=CC(=NC2=3)C#N)C)=O)C)C=C1)OC(C)C NJUGUKSJWHEASY-MSOLQXFVSA-N 0.000 claims description 4
• DCDLWHGBVPCHMZ-NOVWKWNWSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(1,2-oxazol-3-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NOC=C1 DCDLWHGBVPCHMZ-NOVWKWNWSA-N 0.000 claims description 4
• JSYLPERFYOJTDW-NOVWKWNWSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(1,2-thiazol-4-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C=1C=NSC=1 JSYLPERFYOJTDW-NOVWKWNWSA-N 0.000 claims description 4
• MMOZUOPQJMKDIT-WAPIFTKLSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(1,3-oxazol-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C=1OC=CN=1 MMOZUOPQJMKDIT-WAPIFTKLSA-N 0.000 claims description 4
• IVUCNBUVNUNISM-WAPIFTKLSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(1,3-thiazol-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C=1SC=CN=1 IVUCNBUVNUNISM-WAPIFTKLSA-N 0.000 claims description 4
• IEMBHMGAEBJVIF-NOVWKWNWSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(1,3-thiazol-4-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C=1N=CSC=1 IEMBHMGAEBJVIF-NOVWKWNWSA-N 0.000 claims description 4
• CKOCGCCUOKLEQI-NJNVLPOUSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(1-methylimidazol-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C=1N(C=CN=1)C CKOCGCCUOKLEQI-NJNVLPOUSA-N 0.000 claims description 4
• YTOONUYMTBHCAX-RIGXQMBPSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(1-methylpyrazol-4-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C=1C=NN(C=1)C YTOONUYMTBHCAX-RIGXQMBPSA-N 0.000 claims description 4
• VBEFDVWYJXGLGE-KZKVIATDSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(2,4,6-trifluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=C(C=C(C=C1F)F)F VBEFDVWYJXGLGE-KZKVIATDSA-N 0.000 claims description 4
• FUFXTYUMKCCNCC-NYCGYEKWSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(2-methoxypyridin-3-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C=1C(=NC=CC=1)OC FUFXTYUMKCCNCC-NYCGYEKWSA-N 0.000 claims description 4
• PRRRUXOOLFKXAI-HFHQHIJTSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(2-propan-2-yloxypyridin-3-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C=1C(=NC=CC=1)OC(C)C PRRRUXOOLFKXAI-HFHQHIJTSA-N 0.000 claims description 4
• SAXUAWVQOZSJSH-TURHTGMXSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(3-methoxyphenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC(=CC=C1)OC SAXUAWVQOZSJSH-TURHTGMXSA-N 0.000 claims description 4
• BVZZCGYTIMPVTD-HFHQHIJTSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(3-methylphenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC(=CC=C1)C BVZZCGYTIMPVTD-HFHQHIJTSA-N 0.000 claims description 4
• DVBLEWXVRJCYNX-TURHTGMXSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(3-methylsulfonylphenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC(=CC=C1)S(=O)(=O)C DVBLEWXVRJCYNX-TURHTGMXSA-N 0.000 claims description 4
• CLGWMNGLEGMFRV-TURHTGMXSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(4-methoxyphenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)OC CLGWMNGLEGMFRV-TURHTGMXSA-N 0.000 claims description 4
• AVSGPZXBTBGSSF-AVNYNHNVSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(4-methylphenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=CC=C(C=C1)C AVSGPZXBTBGSSF-AVNYNHNVSA-N 0.000 claims description 4
• VVERAZAZACAHQI-KRXSAHMKSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(5-methyl-1,2-oxazol-3-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NOC(=C1)C VVERAZAZACAHQI-KRXSAHMKSA-N 0.000 claims description 4
• ICHFJCAVVHAWEN-XWZNDSGVSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(5-methylpyridin-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=C(C=C1)C ICHFJCAVVHAWEN-XWZNDSGVSA-N 0.000 claims description 4
• QRMKEQLWJWRGNA-NJNVLPOUSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(5-propan-2-yl-1,3,4-thiadiazol-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C=1SC(=NN=1)C(C)C QRMKEQLWJWRGNA-NJNVLPOUSA-N 0.000 claims description 4
• SDDGAOCYVDVJEG-FARGSTTKSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(6-methylpyridin-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=NC(=CC=C1)C SDDGAOCYVDVJEG-FARGSTTKSA-N 0.000 claims description 4
• VZUQIATWZHQVOA-XWZNDSGVSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(6-methylpyridin-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC(=CC=C1)C VZUQIATWZHQVOA-XWZNDSGVSA-N 0.000 claims description 4
• CJLGJXFDDSRFGF-OZPDNGTBSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(oxan-2-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1OCCCC1 CJLGJXFDDSRFGF-OZPDNGTBSA-N 0.000 claims description 4
• SEMTWQVJTCGGEY-XWZNDSGVSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-[3-(1-methylpiperidin-4-yl)-1,2,4-oxadiazol-5-yl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC(=NO1)C1CCN(CC1)C SEMTWQVJTCGGEY-XWZNDSGVSA-N 0.000 claims description 4
• RHQWMQYETVQITP-UWSFRVEYSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-[5-(trifluoromethyl)pyridin-2-yl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=C(C=C1)C(F)(F)F RHQWMQYETVQITP-UWSFRVEYSA-N 0.000 claims description 4
• VBFRAKHYJVYQIQ-FARGSTTKSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-phenylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=CC=CC=C1 VBFRAKHYJVYQIQ-FARGSTTKSA-N 0.000 claims description 4
• XVGOZSUMDTUMHH-RIGXQMBPSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-pyrazin-2-ylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=CN=C1 XVGOZSUMDTUMHH-RIGXQMBPSA-N 0.000 claims description 4
• LLUJPEOVECCVPL-TURHTGMXSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-pyrazolo[1,5-a]pyridin-3-ylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C=1C=NN2C=1C=CC=C2 LLUJPEOVECCVPL-TURHTGMXSA-N 0.000 claims description 4
• BGXSTLHECSNCHY-TURHTGMXSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-pyrazolo[1,5-a]pyridin-7-ylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=CC=2N1N=CC=2 BGXSTLHECSNCHY-TURHTGMXSA-N 0.000 claims description 4
• MLJFROKQMZSDID-RIGXQMBPSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-pyridazin-3-ylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C=1N=NC=CC=1 MLJFROKQMZSDID-RIGXQMBPSA-N 0.000 claims description 4
• BEXYDOPGIPAOSP-NJNVLPOUSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-pyrimidin-2-ylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=CC=N1 BEXYDOPGIPAOSP-NJNVLPOUSA-N 0.000 claims description 4
• OLAIBUNSMUATGM-RIGXQMBPSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-pyrimidin-4-ylmethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC=NC=C1 OLAIBUNSMUATGM-RIGXQMBPSA-N 0.000 claims description 4
• SHSOELOZQYMHIQ-CVEARBPZSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C SHSOELOZQYMHIQ-CVEARBPZSA-N 0.000 claims description 4
• DBSSDSJOFBCNDV-UWSFRVEYSA-N 8-[(2S,5R)-4-[(5-chloropyridin-2-yl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC=1C=CC(=NC=1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F DBSSDSJOFBCNDV-UWSFRVEYSA-N 0.000 claims description 4
• VFKNWNPTYCXHNQ-NOVWKWNWSA-N 8-[(2S,5R)-4-[(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)C1=NN=C(O1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F VFKNWNPTYCXHNQ-NOVWKWNWSA-N 0.000 claims description 4
• SLSLKBGKCYPIMA-NOVWKWNWSA-N 8-[(2S,5R)-4-[(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)C1=NN=C(S1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F SLSLKBGKCYPIMA-NOVWKWNWSA-N 0.000 claims description 4
• OEAGBAQZGIPNNX-RIGXQMBPSA-N 8-[(2S,5R)-4-[(5-cyclopropyl-2-methyl-1,2,4-triazol-3-yl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)C1=NN(C(=N1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F)C OEAGBAQZGIPNNX-RIGXQMBPSA-N 0.000 claims description 4
• WMGAGCIBEDNXLN-FARGSTTKSA-N 8-[(2S,5R)-4-[(5-fluoropyridin-2-yl)-(4-methylphenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound FC=1C=CC(=NC=1)C(N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=CC=C(C=C1)C WMGAGCIBEDNXLN-FARGSTTKSA-N 0.000 claims description 4
• NFTCDDFIIVHKLE-VQSPDULUSA-N 8-[(2S,5R)-4-[(5-tert-butyl-1,2-oxazol-3-yl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)(C)(C)C1=CC(=NO1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F NFTCDDFIIVHKLE-VQSPDULUSA-N 0.000 claims description 4
• PSGUYBCBGSVYFQ-YSPPHNQVSA-N 8-[(2S,5R)-4-[1-(2,2-difluoro-1,3-benzodioxol-4-yl)ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1(OC2=C(O1)C=CC=C2C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)F PSGUYBCBGSVYFQ-YSPPHNQVSA-N 0.000 claims description 4
• XGVPHGDBQVBGSF-OHAXFNJZSA-N 8-[(2S,5R)-4-[1-(2,2-difluoro-1,3-benzodioxol-5-yl)ethyl]-2,5-diethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1(OC2=C(O1)C=CC(=C2)C(C)N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC)F XGVPHGDBQVBGSF-OHAXFNJZSA-N 0.000 claims description 4
• ZEUPPKFYDVVOKK-LQUOLJLFSA-N 8-[(2S,5R)-4-[1-(2,4-difluorophenyl)ethyl]-2-ethyl-5-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=CC(=C1)F)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC ZEUPPKFYDVVOKK-LQUOLJLFSA-N 0.000 claims description 4
• OXIHXOWFDBAERN-SCVGIUIWSA-N 8-[(2S,5R)-4-[1-(2,4-difluorophenyl)ethyl]-5-ethyl-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=CC(=C1)F)C(C)N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C OXIHXOWFDBAERN-SCVGIUIWSA-N 0.000 claims description 4
• BCMYUMDWTJACTO-YSPPHNQVSA-N 8-[(2S,5R)-4-[1-(2,6-difluorophenyl)ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound FC1=C(C(=CC=C1)F)C(C)N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C BCMYUMDWTJACTO-YSPPHNQVSA-N 0.000 claims description 4
• JSDWTOGDZIDOQE-YSPPHNQVSA-N 8-[(2S,5R)-4-[1-(2,6-difluorophenyl)ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C(=CC=C1)F)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C JSDWTOGDZIDOQE-YSPPHNQVSA-N 0.000 claims description 4
• DNXNYIMJHZTMBB-GARXDOFDSA-N 8-[(2S,5R)-4-[1-(2-fluorophenyl)ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound FC1=C(C=CC=C1)C(C)N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C DNXNYIMJHZTMBB-GARXDOFDSA-N 0.000 claims description 4
• UXWICJMKCVHZKN-SCVGIUIWSA-N 8-[(2S,5R)-4-[1-(3,4-difluorophenyl)ethyl]-5-ethyl-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC=1C=C(C=CC=1F)C(C)N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C UXWICJMKCVHZKN-SCVGIUIWSA-N 0.000 claims description 4
• KGYOHRSEPGCAOK-ZQIYAJFXSA-N 8-[(2S,5R)-4-[1-(3,4-difluorophenyl)propyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC=1C=C(C=CC=1F)C(CC)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C KGYOHRSEPGCAOK-ZQIYAJFXSA-N 0.000 claims description 4
• FJEOJMHGLZNKQO-GARXDOFDSA-N 8-[(2S,5R)-4-[1-(4-bromophenyl)ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound BrC1=CC=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C FJEOJMHGLZNKQO-GARXDOFDSA-N 0.000 claims description 4
• IHLAHHPOMYMHNV-YSPPHNQVSA-N 8-[(2S,5R)-4-[1-(4-chloro-2-fluorophenyl)ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC(=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)F IHLAHHPOMYMHNV-YSPPHNQVSA-N 0.000 claims description 4
• DKMROMRCVNXHSS-GARXDOFDSA-N 8-[(2S,5R)-4-[1-(4-chlorophenyl)ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound ClC1=CC=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C DKMROMRCVNXHSS-GARXDOFDSA-N 0.000 claims description 4
• TZFMASDGDFVDPW-UMJFLEMOSA-N 8-[(2S,5R)-4-[1-(4-cyanophenyl)ethyl]-5-ethyl-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C TZFMASDGDFVDPW-UMJFLEMOSA-N 0.000 claims description 4
• IPBUOVFFTHCEQB-DVKDBIPTSA-N 8-[(2S,5R)-4-[1-(4-cyclopropyl-2-fluorophenyl)ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)C1=CC(=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)F IPBUOVFFTHCEQB-DVKDBIPTSA-N 0.000 claims description 4
• AFUCJKBEDPBUII-DBRKUKIDSA-N 8-[(2S,5R)-4-[1-(4-cyclopropyl-2-fluorophenyl)propyl]-2,5-diethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)C1=CC(=C(C=C1)C(CC)N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC)F AFUCJKBEDPBUII-DBRKUKIDSA-N 0.000 claims description 4
• PFWXASYFBKWBAS-IHHKOXMGSA-N 8-[(2S,5R)-4-[1-(4-cyclopropyl-2-fluorophenyl)propyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)C1=CC(=C(C=C1)C(CC)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)F PFWXASYFBKWBAS-IHHKOXMGSA-N 0.000 claims description 4
• ASSLWFLPALLZKP-CFAJLAAASA-N 8-[(2S,5R)-4-[1-(4-cyclopropylphenyl)ethyl]-2,5-diethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)C1=CC=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC ASSLWFLPALLZKP-CFAJLAAASA-N 0.000 claims description 4
• RJCBOHSGVUVFDA-YTYFACEESA-N 8-[(2S,5R)-4-[1-(4-cyclopropylphenyl)ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)C1=CC=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C RJCBOHSGVUVFDA-YTYFACEESA-N 0.000 claims description 4
• ZVUKYDZMGUEISG-WEAPTXNRSA-N 8-[(2S,5R)-4-[1-(4-cyclopropylphenyl)propyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)C1=CC=C(C=C1)C(CC)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C ZVUKYDZMGUEISG-WEAPTXNRSA-N 0.000 claims description 4
• UYYXZZYVBOYHHS-GARXDOFDSA-N 8-[(2S,5R)-4-[1-(4-fluoro-2-methoxyphenyl)ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC(=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)OC UYYXZZYVBOYHHS-GARXDOFDSA-N 0.000 claims description 4
• RCJZALDKGXFXBQ-OKFXBHNASA-N 8-[(2S,5R)-4-[1-(4-fluorophenyl)-2-hydroxyethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(CO)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C RCJZALDKGXFXBQ-OKFXBHNASA-N 0.000 claims description 4
• FPDRLFJXTFUCCL-MSNHYEFBSA-N 8-[(2S,5R)-4-[1-(4-fluorophenyl)-2-methoxyethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(COC)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C FPDRLFJXTFUCCL-MSNHYEFBSA-N 0.000 claims description 4
• BBGMVOSONDSYDS-GARXDOFDSA-N 8-[(2S,5R)-4-[1-(4-fluorophenyl)ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound FC1=CC=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C BBGMVOSONDSYDS-GARXDOFDSA-N 0.000 claims description 4
• BANPUOKUCXLLSF-GARXDOFDSA-N 8-[(2S,5R)-4-[1-(4-fluorophenyl)ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C BANPUOKUCXLLSF-GARXDOFDSA-N 0.000 claims description 4
• JLTPBNDYZTVPFU-YSPPHNQVSA-N 8-[(2S,5R)-4-[1-(5-fluoropyridin-2-yl)ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC=1C=CC(=NC=1)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C JLTPBNDYZTVPFU-YSPPHNQVSA-N 0.000 claims description 4
• DFOHSYCZRDZHAN-GARXDOFDSA-N 8-[(2S,5R)-4-[1-(5-methoxypyridin-2-yl)ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound COC=1C=CC(=NC=1)C(C)N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C DFOHSYCZRDZHAN-GARXDOFDSA-N 0.000 claims description 4
• YMKHFUWZTICWCV-YSPPHNQVSA-N 8-[(2S,5R)-4-[1-[2-fluoro-3-(trifluoromethoxy)phenyl]ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=CC=C1OC(F)(F)F)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C YMKHFUWZTICWCV-YSPPHNQVSA-N 0.000 claims description 4
• CYRIDTYVHZIKOI-ZQIYAJFXSA-N 8-[(2S,5R)-4-[1-[2-fluoro-5-(trifluoromethoxy)phenyl]propyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=C(C=C1)OC(F)(F)F)C(CC)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C CYRIDTYVHZIKOI-ZQIYAJFXSA-N 0.000 claims description 4
• IENKAFYQZUKMCJ-YTYFACEESA-N 8-[(2S,5R)-4-[1-[4-(1-cyanocyclopropyl)-2-fluorophenyl]ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(#N)C1(CC1)C1=CC(=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)F IENKAFYQZUKMCJ-YTYFACEESA-N 0.000 claims description 4
• SKOPPPCMJOYYIC-YNHNLWNQSA-N 8-[(2S,5R)-4-[1-[4-(cyclopropylmethoxy)phenyl]propyl]-5-ethyl-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CC1)COC1=CC=C(C=C1)C(CC)N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C SKOPPPCMJOYYIC-YNHNLWNQSA-N 0.000 claims description 4
• WFFRPHRHUBYGTA-SJRAPUSDSA-N 8-[(2S,5R)-4-[1-[4-(difluoromethoxy)phenyl]ethyl]-2,5-diethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC(OC1=CC=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC)F WFFRPHRHUBYGTA-SJRAPUSDSA-N 0.000 claims description 4
• MKSMTKQXDIHPJB-GARXDOFDSA-N 8-[(2S,5R)-4-[1-[4-(difluoromethoxy)phenyl]ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound FC(OC1=CC=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)F MKSMTKQXDIHPJB-GARXDOFDSA-N 0.000 claims description 4
• BABKITASIGEYRO-GARXDOFDSA-N 8-[(2S,5R)-4-[1-[4-methoxy-3-(trifluoromethyl)phenyl]ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound COC1=C(C=C(C=C1)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C(F)(F)F BABKITASIGEYRO-GARXDOFDSA-N 0.000 claims description 4
• UZEQUWMXNQWWDS-YSPPHNQVSA-N 8-[(2S,5R)-4-[1-[5-(difluoromethoxy)pyridin-2-yl]ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC(OC=1C=CC(=NC=1)C(C)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)F UZEQUWMXNQWWDS-YSPPHNQVSA-N 0.000 claims description 4
• UJOYTLWLJJQQSL-RQJVYDMZSA-N 8-[(2S,5R)-4-[2-(4-fluorophenyl)-2-methoxyethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)OC UJOYTLWLJJQQSL-RQJVYDMZSA-N 0.000 claims description 4
• KQKUWFIVABQOAC-OKFXBHNASA-N 8-[(2S,5R)-4-[2-(difluoromethoxy)-1-(4-fluorophenyl)ethyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC(OCC(C1=CC=C(C=C1)F)N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)F KQKUWFIVABQOAC-OKFXBHNASA-N 0.000 claims description 4
• XWHSDJCWVFPUHZ-YWMJKKSCSA-N 8-[(2S,5R)-4-[2-cyclohexyl-1-[4-(trifluoromethoxy)phenyl]ethyl]-5-ethyl-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C1(CCCCC1)CC(C1=CC=C(C=C1)OC(F)(F)F)N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C XWHSDJCWVFPUHZ-YWMJKKSCSA-N 0.000 claims description 4
• INIYESDZGAJPCF-HNAYVOBHSA-N 8-[(2S,5R)-4-[[2,4-bis(trifluoromethyl)phenyl]methyl]-5-ethyl-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC(C1=C(C=CC(=C1)C(F)(F)F)CN1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)(F)F INIYESDZGAJPCF-HNAYVOBHSA-N 0.000 claims description 4
• RMSOVVQJHLVONE-CABCVRRESA-N 8-[(2S,5R)-4-[[2-(difluoromethyl)-4-fluorophenyl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC(C1=C(C=CC(=C1)F)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)F RMSOVVQJHLVONE-CABCVRRESA-N 0.000 claims description 4
• JABUXOLTXAVELR-CABCVRRESA-N 8-[(2S,5R)-4-[[2-chloro-4-(trifluoromethoxy)phenyl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=C(CN2C[C@@H](N(C[C@H]2C)C2=CC(N(C=3C=CC(=NC2=3)C#N)C)=O)C)C=CC(=C1)OC(F)(F)F JABUXOLTXAVELR-CABCVRRESA-N 0.000 claims description 4
• GYBZUBAUDSURSP-CVEARBPZSA-N 8-[(2S,5R)-4-[[2-cyano-4-(trifluoromethoxy)phenyl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(#N)C1=C(CN2C[C@@H](N(C[C@H]2C)C2=CC(N(C=3C=CC(=NC2=3)C#N)C)=O)C)C=CC(=C1)OC(F)(F)F GYBZUBAUDSURSP-CVEARBPZSA-N 0.000 claims description 4
• NFGYRZLAJAYCNB-CABCVRRESA-N 8-[(2S,5R)-4-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C(=CC=C1)C(F)(F)F)CN1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C NFGYRZLAJAYCNB-CABCVRRESA-N 0.000 claims description 4
• WWIRZVRDGKQBGH-CVEARBPZSA-N 8-[(2S,5R)-4-[[2-methoxy-4-(trifluoromethoxy)phenyl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound COC1=C(CN2C[C@@H](N(C[C@H]2C)C2=CC(N(C=3C=CC(=NC2=3)C#N)C)=O)C)C=CC(=C1)OC(F)(F)F WWIRZVRDGKQBGH-CVEARBPZSA-N 0.000 claims description 4
• JCXJKJSOWZQLES-CVEARBPZSA-N 8-[(2S,5R)-4-[[2-methoxy-5-(trifluoromethoxy)phenyl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound COC1=C(CN2C[C@@H](N(C[C@H]2C)C2=CC(N(C=3C=CC(=NC2=3)C#N)C)=O)C)C=C(C=C1)OC(F)(F)F JCXJKJSOWZQLES-CVEARBPZSA-N 0.000 claims description 4
• ZVILKZJSIBQPGS-KYFQQJHYSA-N 8-[(2S,5R)-4-[[3-(difluoromethyl)-1,2,4-oxadiazol-5-yl]-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC(C1=NOC(=N1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F)F ZVILKZJSIBQPGS-KYFQQJHYSA-N 0.000 claims description 4
• FZVYKKUSDQLCSH-MSOLQXFVSA-N 8-[(2S,5R)-4-[[3-(dimethylamino)phenyl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound CN(C=1C=C(CN2C[C@@H](N(C[C@H]2C)C2=CC(N(C=3C=CC(=NC2=3)C#N)C)=O)C)C=CC=1)C FZVYKKUSDQLCSH-MSOLQXFVSA-N 0.000 claims description 4
• DEOWEBAIRCZAFN-CABCVRRESA-N 8-[(2S,5R)-4-[[3-bromo-4-(trifluoromethoxy)phenyl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound BrC=1C=C(CN2C[C@@H](N(C[C@H]2C)C2=CC(N(C=3C=CC(=NC2=3)C#N)C)=O)C)C=CC=1OC(F)(F)F DEOWEBAIRCZAFN-CABCVRRESA-N 0.000 claims description 4
• XMKRIURFIYPXKZ-CABCVRRESA-N 8-[(2S,5R)-4-[[3-chloro-4-(trifluoromethoxy)phenyl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC=1C=C(CN2C[C@@H](N(C[C@H]2C)C2=CC(N(C=3C=CC(=NC2=3)C#N)C)=O)C)C=CC=1OC(F)(F)F XMKRIURFIYPXKZ-CABCVRRESA-N 0.000 claims description 4
• HGDVMHORDLCEDS-MOPGFXCFSA-N 8-[(2S,5R)-4-[[4-(1-cyanocyclopropyl)phenyl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(#N)C1(CC1)C1=CC=C(CN2C[C@@H](N(C[C@H]2C)C2=CC(N(C=3C=CC(=NC2=3)C#N)C)=O)C)C=C1 HGDVMHORDLCEDS-MOPGFXCFSA-N 0.000 claims description 4
• CHQVKHTUJPDVFQ-CABCVRRESA-N 8-[(2S,5R)-4-[[4-(difluoromethoxy)-2-fluorophenyl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC(OC1=CC(=C(CN2C[C@@H](N(C[C@H]2C)C2=CC(N(C=3C=CC(=NC2=3)C#N)C)=O)C)C=C1)F)F CHQVKHTUJPDVFQ-CABCVRRESA-N 0.000 claims description 4
• GZSOUSFMBWDNQD-CVEARBPZSA-N 8-[(2S,5R)-4-[[4-(difluoromethoxy)phenyl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC(OC1=CC=C(CN2C[C@@H](N(C[C@H]2C)C2=CC(N(C=3C=CC(=NC2=3)C#N)C)=O)C)C=C1)F GZSOUSFMBWDNQD-CVEARBPZSA-N 0.000 claims description 4
• PWYWGHBOQBBSNU-VQSPDULUSA-N 8-[(2S,5R)-4-[[4-(difluoromethyl)phenyl]-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC(C1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F)F PWYWGHBOQBBSNU-VQSPDULUSA-N 0.000 claims description 4
• WNXJGWOWQAIDJH-RBUKOAKNSA-N 8-[(2S,5R)-4-[bis(2-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=C(C=CC=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=C(C=CC=C1)F WNXJGWOWQAIDJH-RBUKOAKNSA-N 0.000 claims description 4
• RCPSPYJQBXNOFB-RBUKOAKNSA-N 8-[(2S,5R)-4-[bis(3-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC=1C=C(C=CC=1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC(=CC=C1)F RCPSPYJQBXNOFB-RBUKOAKNSA-N 0.000 claims description 4
• RIMCWXOVUSPLFO-IZZNHLLZSA-N 8-[(2S,5R)-4-[bis(4-chlorophenyl)methyl]-2,5-diethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC)C1=CC=C(C=C1)Cl RIMCWXOVUSPLFO-IZZNHLLZSA-N 0.000 claims description 4
• REURPYMYAHZMMX-RBUKOAKNSA-N 8-[(2S,5R)-4-[bis(4-chlorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)Cl REURPYMYAHZMMX-RBUKOAKNSA-N 0.000 claims description 4
• KSMFDQBLTFGYBC-CLOONOSVSA-N 8-[(2S,5R)-4-[bis(4-chlorophenyl)methyl]-2-ethyl-5-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC)C1=CC=C(C=C1)Cl KSMFDQBLTFGYBC-CLOONOSVSA-N 0.000 claims description 4
• UXHGZCHJAWWHOY-UQBPGWFLSA-N 8-[(2S,5R)-4-[bis(4-chlorophenyl)methyl]-5-ethyl-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1CC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)Cl UXHGZCHJAWWHOY-UQBPGWFLSA-N 0.000 claims description 4
• QZYZNSSLKYNBBO-RBUKOAKNSA-N 8-[(2S,5R)-4-[bis(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5,7-dimethyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C)C1=CC=C(C=C1)F QZYZNSSLKYNBBO-RBUKOAKNSA-N 0.000 claims description 4
• XKXKEJGUONTNBW-RBUKOAKNSA-N 8-[(2S,5R)-4-[bis(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F XKXKEJGUONTNBW-RBUKOAKNSA-N 0.000 claims description 4
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• LEGDMIQHAQVBKN-CLOONOSVSA-N 8-[(2S,5R)-4-[bis(4-fluorophenyl)methyl]-2-ethyl-5-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)CC)C1=CC=C(C=C1)F LEGDMIQHAQVBKN-CLOONOSVSA-N 0.000 claims description 4
• XMBADIQCUIFTMU-RBISFHTESA-N 8-[(2S,5R)-4-[bis(4-fluorophenyl)methyl]-2-methyl-5-(morpholin-4-ylmethyl)piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1CN1CCOCC1)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F XMBADIQCUIFTMU-RBISFHTESA-N 0.000 claims description 4
• NKPXJROMUHABBZ-RXFWQSSRSA-N 8-[(2S,5R)-4-[bis(4-fluorophenyl)methyl]-5-[(3-hydroxyazetidin-1-yl)methyl]-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1CN1CC(C1)O)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F NKPXJROMUHABBZ-RXFWQSSRSA-N 0.000 claims description 4
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• UHFRNNDJWAEAES-UUOWRZLLSA-N 8-[(2S,5S)-4-[bis(4-chlorophenyl)methyl]-5-(hydroxymethyl)-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound ClC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1CO)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)Cl UHFRNNDJWAEAES-UUOWRZLLSA-N 0.000 claims description 4
• KQHHBBXJWOHPEE-FNZWTVRRSA-N 8-[(2S,5S)-4-[bis(4-fluorophenyl)methyl]-5-(ethoxymethyl)-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1COCC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F KQHHBBXJWOHPEE-FNZWTVRRSA-N 0.000 claims description 4
• GQLHFNHPEUITTI-UUOWRZLLSA-N 8-[(2S,5S)-4-[bis(4-fluorophenyl)methyl]-5-(hydroxymethyl)-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1CO)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F GQLHFNHPEUITTI-UUOWRZLLSA-N 0.000 claims description 4
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• LHJQOWUIEDUYOG-HOFKKMOUSA-N 8-[(2S,5S)-4-[bis(4-methylphenyl)methyl]-5-(methoxymethyl)-2-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound CC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1COC)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)C LHJQOWUIEDUYOG-HOFKKMOUSA-N 0.000 claims description 4
• CJPSFIWWCZNHMC-NOAQKIQUSA-N 8-[(2S,5S)-5-(2-methoxyethoxymethyl)-2-methyl-4-[1-[4-(trifluoromethoxy)phenyl]ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound COCCOC[C@H]1N(C[C@@H](N(C1)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C(C)C1=CC=C(C=C1)OC(F)(F)F CJPSFIWWCZNHMC-NOAQKIQUSA-N 0.000 claims description 4
• LJWJLPOSEDYWMF-XBZLUXOVSA-N 8-[(2S,5S)-5-(ethoxymethyl)-2-methyl-4-[1-[4-(trifluoromethoxy)phenyl]ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)OC[C@H]1N(C[C@@H](N(C1)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C(C)C1=CC=C(C=C1)OC(F)(F)F LJWJLPOSEDYWMF-XBZLUXOVSA-N 0.000 claims description 4
• YDTWVKQTXICPFW-QLYZIHHJSA-N 8-[(2S,5S)-5-(hydroxymethyl)-2-methyl-4-[1-[4-(trifluoromethoxy)phenyl]ethyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound OC[C@H]1N(C[C@@H](N(C1)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C(C)C1=CC=C(C=C1)OC(F)(F)F YDTWVKQTXICPFW-QLYZIHHJSA-N 0.000 claims description 4
• ZQZXYJCXBOCZMM-YOEHRIQHSA-N 8-[(2S,5S)-5-(methoxymethyl)-2-methyl-4-[(3,4,5-trifluorophenyl)methyl]piperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound COC[C@H]1N(C[C@@H](N(C1)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)CC1=CC(=C(C(=C1)F)F)F ZQZXYJCXBOCZMM-YOEHRIQHSA-N 0.000 claims description 4
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• NBRRAOSWEBLFJF-MOJDWNGGSA-N 8-[(3R)-4-[(2,4-difluorophenyl)-(4-fluorophenyl)methyl]-3-methylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2,7-dicarbonitrile Chemical compound FC1=C(C=CC(=C1)F)C(N1[C@@H](CN(CC1)C1=C(C(N(C=2C=CC(=NC1=2)C#N)C)=O)C#N)C)C1=CC=C(C=C1)F NBRRAOSWEBLFJF-MOJDWNGGSA-N 0.000 claims description 4
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• 238000002560 therapeutic procedure Methods 0.000 claims description 4
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• BRBCCJVMUORTJW-RIGXQMBPSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-(3-methylimidazol-4-yl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CN=CN1C BRBCCJVMUORTJW-RIGXQMBPSA-N 0.000 claims description 2
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• SNHCGKJPXUYPQK-VQSPDULUSA-N 8-[(2S,5R)-4-[(4-fluorophenyl)-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound FC1=CC=C(C=C1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=NC(=NO1)C1=CC=C(C=C1)F SNHCGKJPXUYPQK-VQSPDULUSA-N 0.000 claims description 2
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• VTNNUZOPXAPMFU-NJNVLPOUSA-N 8-[(2S,5R)-4-[(5-tert-butyl-1,2,4-oxadiazol-3-yl)-(4-fluorophenyl)methyl]-2,5-dimethylpiperazin-1-yl]-5-methyl-6-oxo-1,5-naphthyridine-2-carbonitrile Chemical compound C(C)(C)(C)C1=NC(=NO1)C(N1C[C@@H](N(C[C@H]1C)C1=CC(N(C=2C=CC(=NC1=2)C#N)C)=O)C)C1=CC=C(C=C1)F VTNNUZOPXAPMFU-NJNVLPOUSA-N 0.000 claims description 2
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