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 |
|---|---|---|---|
| EP14173045.7 | 2014-06-18 | ||
| EP14173045 | 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 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Country Status (7)
| Country | Link |
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| US (1) | US20170121322A1 (enExample) |
| 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 (6)
| 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 |
| PT3762368T (pt) | 2018-03-08 | 2022-05-06 | Incyte Corp | Compostos de aminopirazina diol como inibidores de pi3k-y |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| 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 |
| WO2025014200A1 (ko) * | 2023-07-07 | 2025-01-16 | 주식회사 티움바이오 | 화합물 및 이를 포함하는 약학 조성물 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3050885B1 (en) * | 2009-11-05 | 2017-10-18 | GlaxoSmithKline LLC | Benzodiazepine bromodomain inhibitor |
| WO2012075456A1 (en) * | 2010-12-02 | 2012-06-07 | Constellation Pharmaceuticals | Bromodomain inhibitors and uses thereof |
| AR084070A1 (es) * | 2010-12-02 | 2013-04-17 | Constellation Pharmaceuticals Inc | Inhibidores del bromodominio y usos de los mismos |
| WO2014095775A1 (de) * | 2012-12-20 | 2014-06-26 | Bayer Pharma Aktiengesellschaft | Bet-proteininhibitorische dihydrochinoxalinone |
| 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 |
| CN105518001A (zh) * | 2013-07-09 | 2016-04-20 | 拜耳制药股份公司 | Bet蛋白抑制性的改性的二氢喹喔啉酮类化合物和二氢吡啶并吡嗪酮类化合物 |
-
2015
- 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 JP JP2016573534A patent/JP2017519760A/ja not_active Withdrawn
- 2015-06-15 EP EP15729444.8A patent/EP3157919A1/de not_active Withdrawn
- 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 CA CA2952526A patent/CA2952526A1/en not_active Abandoned
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