JP2017519760A5 - - Google Patents
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- JP2017519760A5 JP2017519760A5 JP2016573534A JP2016573534A JP2017519760A5 JP 2017519760 A5 JP2017519760 A5 JP 2017519760A5 JP 2016573534 A JP2016573534 A JP 2016573534A JP 2016573534 A JP2016573534 A JP 2016573534A JP 2017519760 A5 JP2017519760 A5 JP 2017519760A5
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- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- substituted
- dimethyl
- amino
- Prior art date
- 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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- -1 C 1 -C 4 -alkyl- Chemical group 0.000 claims 92
- 125000004093 cyano group Chemical group *C#N 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 15
- 229910052731 fluorine Inorganic materials 0.000 claims 15
- 239000011737 fluorine Substances 0.000 claims 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 13
- 229910052801 chlorine Inorganic materials 0.000 claims 13
- 239000000460 chlorine Substances 0.000 claims 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
- 208000036142 Viral infection Diseases 0.000 claims 3
- 230000003143 atherosclerotic effect Effects 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 230000035558 fertility Effects 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 230000001613 neoplastic effect Effects 0.000 claims 3
- 230000004770 neurodegeneration Effects 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- 230000009385 viral infection Effects 0.000 claims 3
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 230000003463 hyperproliferative effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 2
- 230000001629 suppression Effects 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 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
- NWZYECGSOWYJGE-OAHLLOKOSA-N (3R)-1,3-dimethyl-4-(oxan-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)C2CCOCC2)N=1)OC(F)(F)F NWZYECGSOWYJGE-OAHLLOKOSA-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
- CSBLEOGKCCTEHA-PWSAKUHLSA-N (3R)-1,3-dimethyl-6-[3-(methylsulfonimidoyl)anilino]-4-(oxan-4-yl)-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)S(=O)(=N)C CSBLEOGKCCTEHA-PWSAKUHLSA-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
- 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
- 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
- XXUXNYGQEWBEEL-GOSISDBHSA-N (3R)-6-[5-ethylsulfonyl-2-(4-fluorophenoxy)anilino]-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=C(C=C1)F XXUXNYGQEWBEEL-GOSISDBHSA-N 0.000 claims 1
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006532 (C3-C5) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- WQQJVNJLVMKTBC-UHFFFAOYSA-N 1,3-dimethyl-6-(3-methylsulfonylanilino)-4-phenyl-3H-pyrido[2,3-b]pyrazin-2-one Chemical compound CN1C2=C(N(C(C1=O)C)C1=CC=CC=C1)N=C(C=C2)NC1=CC(=CC=C1)S(=O)(=O)C WQQJVNJLVMKTBC-UHFFFAOYSA-N 0.000 claims 1
- IXQWZEIVSHAGBW-GOSISDBHSA-N 4-[3-[[(3R)-1,3-dimethyl-4-(oxan-4-yl)-2-oxo-3H-pyrido[2,3-b]pyrazin-6-yl]amino]phenyl]benzonitrile Chemical compound C[C@H]1N(C2CCOCC2)C2=NC(NC3=CC=CC(=C3)C3=CC=C(C=C3)C#N)=CC=C2N(C)C1=O IXQWZEIVSHAGBW-GOSISDBHSA-N 0.000 claims 1
- 241000238366 Cephalopoda Species 0.000 claims 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14173045 | 2014-06-18 | ||
| EP14173045.7 | 2014-06-18 | ||
| PCT/EP2015/063278 WO2015193219A1 (de) | 2014-06-18 | 2015-06-15 | Bet-proteininhibitorische 3,4-dihydropyrido[2,3-b]pyrazinone mit meta-substituierter aromatischer amino- oder ethergruppe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017519760A JP2017519760A (ja) | 2017-07-20 |
| JP2017519760A5 true JP2017519760A5 (enExample) | 2018-07-12 |
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Family Applications (1)
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| JP2016573534A Withdrawn JP2017519760A (ja) | 2014-06-18 | 2015-06-15 | ＢＥＴ−タンパク質を阻害するメタ位置換芳香族アミノ又はエーテル基を有する３，４−ジヒドロピリド［２，３−ｂ］ピラジノン類 |
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| EP (1) | EP3157919A1 (enExample) |
| JP (1) | JP2017519760A (enExample) |
| CN (1) | CN106573931A (enExample) |
| CA (1) | CA2952526A1 (enExample) |
| HK (1) | HK1232226A1 (enExample) |
| WO (1) | WO2015193219A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102017005091A1 (de) | 2016-05-30 | 2017-11-30 | Bayer Pharma Aktiengesellschaft | Substituierte 3,4-Dihydropyrido[2,3-b]pyrazin-2(1H)-one |
| DE102017005089A1 (de) | 2016-05-30 | 2017-11-30 | Bayer Pharma Aktiengesellschaft | Substitulerte 3,4-Dihydrochinoxalin-2(1H)-one |
| CR20200464A (es) | 2018-03-08 | 2021-04-14 | Incyte Corp | Compuestos diólicos de aminopirazina como inhibidores de pi3k-y |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| CN117279644A (zh) * | 2021-03-03 | 2023-12-22 | 拜耳股份有限公司 | 用于治疗肉瘤的取代的3,6-二氢-2h-1,3,4-噁二嗪-2-酮 |
| CN115322128B (zh) * | 2022-08-05 | 2024-06-18 | 南京师范大学 | 一种基于烷基卤代物合成C(sp3)-S键的有机硫化合物及其制备方法与应用 |
| KR20250008496A (ko) * | 2023-07-07 | 2025-01-14 | 주식회사 티움바이오 | 화합물 및 이를 포함하는 약학 조성물 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2010317096B2 (en) * | 2009-11-05 | 2015-03-26 | Glaxosmithkline Llc | Benzodiazepine bromodomain inhibitor |
| AR084070A1 (es) * | 2010-12-02 | 2013-04-17 | Constellation Pharmaceuticals Inc | Inhibidores del bromodominio y usos de los mismos |
| WO2012075456A1 (en) * | 2010-12-02 | 2012-06-07 | Constellation Pharmaceuticals | Bromodomain inhibitors and uses thereof |
| HK1211033A1 (en) * | 2012-12-20 | 2016-05-13 | Bayer Pharma Aktiengesellschaft | Bet-protein-inhibiting dihydroquinoxalinones |
| JP2016504990A (ja) * | 2012-12-20 | 2016-02-18 | バイエル ファーマ アクチエンゲゼルシャフト | Ｂｅｔタンパク質抑制性ジヒドロピリドピラジノン |
| ES2635003T3 (es) * | 2013-07-09 | 2017-10-02 | Bayer Pharma Aktiengesellschaft | Dihidroquinoxalinonas y dihidropiridopirazinonas modificadas inhibidoras de proteína BET |
-
2015
- 2015-06-15 CN CN201580044412.8A patent/CN106573931A/zh active Pending
- 2015-06-15 WO PCT/EP2015/063278 patent/WO2015193219A1/de not_active Ceased
- 2015-06-15 US US15/317,925 patent/US20170121322A1/en not_active Abandoned
- 2015-06-15 HK HK17105942.9A patent/HK1232226A1/zh unknown
- 2015-06-15 EP EP15729444.8A patent/EP3157919A1/de not_active Withdrawn
- 2015-06-15 JP JP2016573534A patent/JP2017519760A/ja not_active Withdrawn
- 2015-06-15 CA CA2952526A patent/CA2952526A1/en not_active Abandoned
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