CA2952526A1 - Bet-protein inhibiting 3,4-dihydropyrido[2,3-b]pyrazinones with meta-substituted aromatic amino- or ether groups - Google Patents

Info

Publication number

CA2952526A1

CA2952526A1 CA2952526A CA2952526A CA2952526A1 CA 2952526 A1 CA2952526 A1 CA 2952526A1 CA 2952526 A CA2952526 A CA 2952526A CA 2952526 A CA2952526 A CA 2952526A CA 2952526 A1 CA2952526 A1 CA 2952526A1

Authority

CA

Canada

Prior art keywords

alkyl

phenyl

unsubstituted

dihydropyrido

pyrazin

Prior art date

2014-06-18

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• HIGOCZJARKJCGG-UHFFFAOYSA-N 3,4-dihydro-1h-pyrido[2,3-b]pyrazin-2-one Chemical class C1=CC=C2NC(=O)CNC2=N1 HIGOCZJARKJCGG-UHFFFAOYSA-N 0.000 title abstract description 8
• 125000001033 ether group Chemical group 0.000 title abstract description 6
• 230000002401 inhibitory effect Effects 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 336
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 48
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 11
• 208000036142 Viral infection Diseases 0.000 claims abstract description 8
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 8
• 230000009385 viral infection Effects 0.000 claims abstract description 8
• 230000035558 fertility Effects 0.000 claims abstract description 7
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 7
• 230000003143 atherosclerotic effect Effects 0.000 claims abstract description 6
• -1 phenyl- Chemical group 0.000 claims description 529
• 229910052739 hydrogen Inorganic materials 0.000 claims description 92
• 239000001257 hydrogen Substances 0.000 claims description 91
• 239000011737 fluorine Substances 0.000 claims description 85
• 229910052731 fluorine Inorganic materials 0.000 claims description 85
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 84
• 239000000460 chlorine Substances 0.000 claims description 80
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 78
• 229910052801 chlorine Inorganic materials 0.000 claims description 77
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 76
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 73
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 69
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 65
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 65
• 229910052757 nitrogen Inorganic materials 0.000 claims description 47
• 208000035475 disorder Diseases 0.000 claims description 43
• 150000003839 salts Chemical class 0.000 claims description 41
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
• 229910052799 carbon Inorganic materials 0.000 claims description 33
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 31
• 150000002367 halogens Chemical class 0.000 claims description 30
• 238000011321 prophylaxis Methods 0.000 claims description 29
• 229910052736 halogen Inorganic materials 0.000 claims description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 24
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
• 229910052794 bromium Inorganic materials 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 239000003814 drug Substances 0.000 claims description 22
• 238000002560 therapeutic procedure Methods 0.000 claims description 22
• 150000001721 carbon Chemical group 0.000 claims description 21
• 125000004043 oxo group Chemical group O=* 0.000 claims description 19
• 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 17
• 125000001153 fluoro group Chemical group F* 0.000 claims description 15
• 230000001613 neoplastic effect Effects 0.000 claims description 15
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 13
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 13
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
• 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 9
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 206010061218 Inflammation Diseases 0.000 claims description 7
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• 230000004054 inflammatory process Effects 0.000 claims description 7
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 239000013543 active substance Substances 0.000 claims description 3
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims 13
• LNYRUUVXYKSERY-OAHLLOKOSA-N (3R)-1,3-dimethyl-4-(1-methylpiperidin-4-yl)-6-(3-methylsulfonylanilino)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C[C@H]1N(C2CCN(C)CC2)C2=NC(NC3=CC(=CC=C3)S(C)(=O)=O)=CC=C2N(C)C1=O LNYRUUVXYKSERY-OAHLLOKOSA-N 0.000 claims 1
• GIMWVXKMKDZLFY-QGZVFWFLSA-N (3R)-1,3-dimethyl-4-(1-methylpiperidin-4-yl)-6-(3-propan-2-ylsulfonylanilino)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C(C)(C)S(=O)(=O)C=1C=C(C=CC=1)NC=1C=CC2=C(N([C@@H](C(N2C)=O)C)C2CCN(CC2)C)N=1 GIMWVXKMKDZLFY-QGZVFWFLSA-N 0.000 claims 1
• TZYQXDHGNRRZOT-MRXNPFEDSA-N (3R)-1,3-dimethyl-4-(1-methylpiperidin-4-yl)-6-[5-propan-2-ylsulfonyl-2-(trifluoromethoxy)anilino]-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C(C)(C)S(=O)(=O)C=1C=CC(=C(C=1)NC=1C=CC2=C(N([C@@H](C(N2C)=O)C)C2CCN(CC2)C)N=1)OC(F)(F)F TZYQXDHGNRRZOT-MRXNPFEDSA-N 0.000 claims 1
• KNWBQJRDNFRLLC-MRXNPFEDSA-N (3R)-1,3-dimethyl-4-(oxan-4-yl)-6-(3-propan-2-ylsulfonylanilino)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound CC(C)S(=O)(=O)C1=CC=CC(NC2=CC=C3N(C)C(=O)[C@@H](C)N(C4CCOCC4)C3=N2)=C1 KNWBQJRDNFRLLC-MRXNPFEDSA-N 0.000 claims 1
• DEUARJFJONJXTK-CYBMUJFWSA-N (3R)-1,3-dimethyl-4-(oxan-4-yl)-6-[3-(trifluoromethyl)anilino]-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound CN1C2=C(N([C@@H](C1=O)C)C1CCOCC1)N=C(C=C2)NC1=CC(=CC=C1)C(F)(F)F DEUARJFJONJXTK-CYBMUJFWSA-N 0.000 claims 1
• PHWLNRKQZNCWAU-OAHLLOKOSA-N (3R)-1,3-dimethyl-6-(2-methyl-5-methylsulfonylanilino)-4-(oxan-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C[C@H]1N(C2CCOCC2)C2=NC(NC3=C(C)C=CC(=C3)S(C)(=O)=O)=CC=C2N(C)C1=O PHWLNRKQZNCWAU-OAHLLOKOSA-N 0.000 claims 1
• WKSQSQJMHMBFFI-CQSZACIVSA-N (3R)-1,3-dimethyl-6-(3-methylsulfonylanilino)-4-(oxan-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C[C@H]1N(C2CCOCC2)C2=NC(NC3=CC(=CC=C3)S(C)(=O)=O)=CC=C2N(C)C1=O WKSQSQJMHMBFFI-CQSZACIVSA-N 0.000 claims 1
• UEHVDENYFNAOKA-GOSISDBHSA-N (3R)-1,3-dimethyl-6-(3-propan-2-ylsulfonylanilino)-4-[1-(3,3,3-trifluoropropyl)piperidin-4-yl]-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound CC(C)S(=O)(=O)C1=CC=CC(NC2=CC=C3N(C)C(=O)[C@@H](C)N(C4CCN(CCC(F)(F)F)CC4)C3=N2)=C1 UEHVDENYFNAOKA-GOSISDBHSA-N 0.000 claims 1
• UVXJALBOSUAELJ-CQSZACIVSA-N (3R)-1,3-dimethyl-6-[(2-methylpyridin-4-yl)amino]-4-(oxan-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C[C@H]1N(C2CCOCC2)C2=NC(NC3=CC(C)=NC=C3)=CC=C2N(C)C1=O UVXJALBOSUAELJ-CQSZACIVSA-N 0.000 claims 1
• MJVPBYMBDFPFGX-GOSISDBHSA-N (3R)-1,3-dimethyl-6-[3-(4-methylpiperazin-1-yl)anilino]-4-(oxan-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C[C@H]1N(C2CCOCC2)C2=NC(NC3=CC(=CC=C3)N3CCN(C)CC3)=CC=C2N(C)C1=O MJVPBYMBDFPFGX-GOSISDBHSA-N 0.000 claims 1
• KFVQYVOQJOSFCN-QGZVFWFLSA-N (3R)-4-[1-(2,2-difluoroethyl)piperidin-4-yl]-6-(2-methoxy-5-propan-2-ylsulfonylanilino)-1,3-dimethyl-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound COC1=C(NC2=CC=C3N(C)C(=O)[C@@H](C)N(C4CCN(CC(F)F)CC4)C3=N2)C=C(C=C1)S(=O)(=O)C(C)C KFVQYVOQJOSFCN-QGZVFWFLSA-N 0.000 claims 1
• LUKNGCDGWLGWCV-MRXNPFEDSA-N (3R)-4-cycloheptyl-1,3-dimethyl-6-(3-methylsulfonylanilino)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C[C@H]1N(C2CCCCCC2)C2=NC(NC3=CC(=CC=C3)S(C)(=O)=O)=CC=C2N(C)C1=O LUKNGCDGWLGWCV-MRXNPFEDSA-N 0.000 claims 1
• BVNKMEOGYOFLKB-CQSZACIVSA-N (3R)-6-(2-methoxy-5-methylsulfonylanilino)-1,3-dimethyl-4-(oxan-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound COC1=C(NC2=CC=C3N(C)C(=O)[C@@H](C)N(C4CCOCC4)C3=N2)C=C(C=C1)S(C)(=O)=O BVNKMEOGYOFLKB-CQSZACIVSA-N 0.000 claims 1
• OVDHMLGXXGXDSD-CQSZACIVSA-N (3R)-6-(2-methoxy-5-methylsulfonylanilino)-1,3-dimethyl-4-piperidin-4-yl-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound COC1=C(NC2=CC=C3N(C)C(=O)[C@@H](C)N(C4CCNCC4)C3=N2)C=C(C=C1)S(C)(=O)=O OVDHMLGXXGXDSD-CQSZACIVSA-N 0.000 claims 1
• BSRNTZOPOJMVBP-CYBMUJFWSA-N (3R)-6-(2-methoxy-5-methylsulfonylanilino)-1,3-dimethyl-4-propan-2-yl-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound COC1=C(NC2=CC=C3N(C)C(=O)[C@@H](C)N(C(C)C)C3=N2)C=C(C=C1)S(C)(=O)=O BSRNTZOPOJMVBP-CYBMUJFWSA-N 0.000 claims 1
• UGXBRLSWMVWJBA-QGZVFWFLSA-N (3R)-6-(2-methoxy-5-propan-2-ylsulfonylanilino)-1,3-dimethyl-4-(1-methylpiperidin-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound COC1=C(NC2=CC=C3N(C)C(=O)[C@@H](C)N(C4CCN(C)CC4)C3=N2)C=C(C=C1)S(=O)(=O)C(C)C UGXBRLSWMVWJBA-QGZVFWFLSA-N 0.000 claims 1
• JXBWOTGDVFZTAZ-MRXNPFEDSA-N (3R)-6-(2-methoxy-5-propan-2-ylsulfonylanilino)-1,3-dimethyl-4-(oxan-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound COC1=C(NC2=CC=C3N(C)C(=O)[C@@H](C)N(C4CCOCC4)C3=N2)C=C(C=C1)S(=O)(=O)C(C)C JXBWOTGDVFZTAZ-MRXNPFEDSA-N 0.000 claims 1
• SIWMIJMPKDIOGZ-QGZVFWFLSA-N (3R)-6-(2-methoxy-5-propan-2-ylsulfonylanilino)-1,3-dimethyl-4-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C(C)(C)S(=O)(=O)C=1C=CC(=C(C=1)NC=1C=CC2=C(N([C@@H](C(N2C)=O)C)C2CCN(CC2)CC(F)(F)F)N=1)OC SIWMIJMPKDIOGZ-QGZVFWFLSA-N 0.000 claims 1
• MFQCWWODEYWRJW-GOSISDBHSA-N (3R)-6-(2-methoxy-5-propan-2-ylsulfonylanilino)-1,3-dimethyl-4-[1-(3,3,3-trifluoropropyl)piperidin-4-yl]-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C(C)(C)S(=O)(=O)C=1C=CC(=C(C=1)NC=1C=CC2=C(N([C@@H](C(N2C)=O)C)C2CCN(CC2)CCC(F)(F)F)N=1)OC MFQCWWODEYWRJW-GOSISDBHSA-N 0.000 claims 1
• AUAAMLKXISPBIK-MRXNPFEDSA-N (3R)-6-(2-methoxy-5-propan-2-ylsulfonylanilino)-1,3-dimethyl-4-piperidin-4-yl-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound COC1=C(NC2=CC=C3N(C)C(=O)[C@@H](C)N(C4CCNCC4)C3=N2)C=C(C=C1)S(=O)(=O)C(C)C AUAAMLKXISPBIK-MRXNPFEDSA-N 0.000 claims 1
• ILEHGOFEJWJLJE-OAHLLOKOSA-N (3R)-6-(2-methoxy-5-propan-2-ylsulfonylanilino)-1,3-dimethyl-4-propan-2-yl-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C(C)(C)N1C2=C(N(C([C@H]1C)=O)C)C=CC(=N2)NC1=C(C=CC(=C1)S(=O)(=O)C(C)C)OC ILEHGOFEJWJLJE-OAHLLOKOSA-N 0.000 claims 1
• XXWDJWZUYWREQD-OAHLLOKOSA-N (3R)-6-(3-cyclopropylsulfonylanilino)-1,3-dimethyl-4-(oxan-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C1(CC1)S(=O)(=O)C=1C=C(C=CC=1)NC=1C=CC2=C(N([C@@H](C(N2C)=O)C)C2CCOCC2)N=1 XXWDJWZUYWREQD-OAHLLOKOSA-N 0.000 claims 1
• NLTAQZBHFCQORB-CQSZACIVSA-N (3R)-6-(3-methoxy-5-methylsulfonylanilino)-1,3-dimethyl-4-(oxan-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound COC1=CC(=CC(NC2=CC=C3N(C)C(=O)[C@@H](C)N(C4CCOCC4)C3=N2)=C1)S(C)(=O)=O NLTAQZBHFCQORB-CQSZACIVSA-N 0.000 claims 1
• PNGFPYCFFCGRDT-MRXNPFEDSA-N (3R)-6-(5-cyclobutylsulfonyl-2-methoxyanilino)-1,3-dimethyl-4-(oxan-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C1(CCC1)S(=O)(=O)C=1C=CC(=C(C=1)NC=1C=CC2=C(N([C@@H](C(N2C)=O)C)C2CCOCC2)N=1)OC PNGFPYCFFCGRDT-MRXNPFEDSA-N 0.000 claims 1
• FXPKPXBCAHGADT-MRXNPFEDSA-N (3R)-6-(5-cyclopropylsulfonyl-2-methoxyanilino)-1,3-dimethyl-4-(1-methylpiperidin-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C1(CC1)S(=O)(=O)C=1C=CC(=C(C=1)NC=1C=CC2=C(N([C@@H](C(N2C)=O)C)C2CCN(CC2)C)N=1)OC FXPKPXBCAHGADT-MRXNPFEDSA-N 0.000 claims 1
• XRRSGHNXHZZEFE-OAHLLOKOSA-N (3R)-6-(5-cyclopropylsulfonyl-2-methoxyanilino)-1,3-dimethyl-4-(oxan-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound COC1=C(NC2=CC=C3N(C)C(=O)[C@@H](C)N(C4CCOCC4)C3=N2)C=C(C=C1)S(=O)(=O)C1CC1 XRRSGHNXHZZEFE-OAHLLOKOSA-N 0.000 claims 1
• HTCOEVCGYBBSAQ-CQSZACIVSA-N (3R)-6-(5-cyclopropylsulfonyl-2-methoxyanilino)-1,3-dimethyl-4-propan-2-yl-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound COC1=C(NC2=CC=C3N(C)C(=O)[C@@H](C)N(C(C)C)C3=N2)C=C(C=C1)S(=O)(=O)C1CC1 HTCOEVCGYBBSAQ-CQSZACIVSA-N 0.000 claims 1
• OKEPPRINGSZIRP-HXUWFJFHSA-N (3R)-6-(5-ethylsulfonyl-2-phenoxyanilino)-1,3-dimethyl-4-(1-methylpiperidin-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C(C)S(=O)(=O)C=1C=CC(=C(C=1)NC=1C=CC2=C(N([C@@H](C(N2C)=O)C)C2CCN(CC2)C)N=1)OC1=CC=CC=C1 OKEPPRINGSZIRP-HXUWFJFHSA-N 0.000 claims 1
• CKNKZFVVXFDPFW-LJQANCHMSA-N (3R)-6-(5-ethylsulfonyl-2-phenoxyanilino)-1,3-dimethyl-4-(oxan-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C(C)S(=O)(=O)C=1C=CC(=C(C=1)NC=1C=CC2=C(N([C@@H](C(N2C)=O)C)C2CCOCC2)N=1)OC1=CC=CC=C1 CKNKZFVVXFDPFW-LJQANCHMSA-N 0.000 claims 1
• MWUVTRQXQHNZPZ-CQSZACIVSA-N (3R)-6-[(1,1-dioxo-2,3-dihydro-1-benzothiophen-6-yl)amino]-1,3-dimethyl-4-(oxan-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound O=S1(CCC2=C1C=C(C=C2)NC=1C=CC2=C(N([C@@H](C(N2C)=O)C)C2CCOCC2)N=1)=O MWUVTRQXQHNZPZ-CQSZACIVSA-N 0.000 claims 1
• SFNRTJNHNKKTMV-GOSISDBHSA-N (3R)-6-[2-methoxy-5-(oxan-4-ylsulfonyl)anilino]-1,3-dimethyl-4-(1-methylpiperidin-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound COC1=C(C=C(C=C1)S(=O)(=O)C1CCOCC1)NC=1C=CC2=C(N([C@@H](C(N2C)=O)C)C2CCN(CC2)C)N=1 SFNRTJNHNKKTMV-GOSISDBHSA-N 0.000 claims 1
• NCIQPRXZGWYGSQ-QGZVFWFLSA-N (3R)-6-[2-methoxy-5-(oxan-4-ylsulfonyl)anilino]-1,3-dimethyl-4-(oxan-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound COC1=C(C=C(C=C1)S(=O)(=O)C1CCOCC1)NC=1C=CC2=C(N([C@@H](C(N2C)=O)C)C2CCOCC2)N=1 NCIQPRXZGWYGSQ-QGZVFWFLSA-N 0.000 claims 1
• HRAHVDSNSXILBR-CQSZACIVSA-N (3R)-6-[2-methoxy-5-(trifluoromethylsulfonyl)anilino]-1,3-dimethyl-4-(1-methylpiperidin-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound COC1=C(NC2=CC=C3N(C)C(=O)[C@@H](C)N(C4CCN(C)CC4)C3=N2)C=C(C=C1)S(=O)(=O)C(F)(F)F HRAHVDSNSXILBR-CQSZACIVSA-N 0.000 claims 1
• RYMAHVHCPIDRMK-CYBMUJFWSA-N (3R)-6-[2-methoxy-5-(trifluoromethylsulfonyl)anilino]-1,3-dimethyl-4-(oxan-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound COC1=C(NC2=CC=C3N(C)C(=O)[C@@H](C)N(C4CCOCC4)C3=N2)C=C(C=C1)S(=O)(=O)C(F)(F)F RYMAHVHCPIDRMK-CYBMUJFWSA-N 0.000 claims 1
• TZEGSSVXEKVECD-LJQANCHMSA-N (3R)-6-[5-ethylsulfonyl-2-(4-fluorophenoxy)anilino]-1,3-dimethyl-4-(1-methylpiperidin-4-yl)-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound C(C)S(=O)(=O)C=1C=CC(=C(C=1)NC=1C=CC2=C(N([C@@H](C(N2C)=O)C)C2CCN(CC2)C)N=1)OC1=CC=C(C=C1)F TZEGSSVXEKVECD-LJQANCHMSA-N 0.000 claims 1
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