JP2017519760A - 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 - Google Patents
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 Download PDFInfo
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- JP2017519760A JP2017519760A JP2016573534A JP2016573534A JP2017519760A JP 2017519760 A JP2017519760 A JP 2017519760A JP 2016573534 A JP2016573534 A JP 2016573534A JP 2016573534 A JP2016573534 A JP 2016573534A JP 2017519760 A JP2017519760 A JP 2017519760A
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- alkyl
- phenyl
- substituted
- dihydropyrido
- dimethyl
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- 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 5
- 125000001033 ether group Chemical group 0.000 title abstract description 5
- 108091052242 Bromo- and Extra-Terminal domain (BET) family Proteins 0.000 title description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 45
- 201000010099 disease Diseases 0.000 claims abstract description 44
- 239000003814 drug Substances 0.000 claims abstract description 29
- 230000001613 neoplastic effect Effects 0.000 claims abstract description 16
- 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 11
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 11
- 208000036142 Viral infection Diseases 0.000 claims abstract description 8
- 230000004770 neurodegeneration Effects 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
- 230000003143 atherosclerotic effect Effects 0.000 claims abstract description 6
- 230000001629 suppression Effects 0.000 claims abstract description 5
- -1 C 1 -C 4 -alkyl- Chemical group 0.000 claims description 517
- 150000001875 compounds Chemical class 0.000 claims description 280
- 229910052739 hydrogen Inorganic materials 0.000 claims description 91
- 239000001257 hydrogen Substances 0.000 claims description 91
- 229910052731 fluorine Inorganic materials 0.000 claims description 85
- 239000011737 fluorine Substances 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 81
- 239000000460 chlorine Substances 0.000 claims description 79
- 229910052801 chlorine Inorganic materials 0.000 claims description 78
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 78
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 76
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 70
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 68
- 150000002431 hydrogen Chemical class 0.000 claims description 49
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 40
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 37
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 36
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 34
- 125000001153 fluoro group Chemical group F* 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 27
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 25
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 25
- 229910052794 bromium Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 125000004043 oxo group Chemical group O=* 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 15
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 14
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 150000001721 carbon Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 230000002265 prevention Effects 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 9
- 125000006568 (C4-C7) heterocycloalkyl 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
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 5
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 2
- 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 description 2
- 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 description 2
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
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- 229960001712 testosterone propionate Drugs 0.000 description 1
- 229940085503 testred Drugs 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
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- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 229950002376 tirapazamine Drugs 0.000 description 1
- ORYDPOVDJJZGHQ-UHFFFAOYSA-N tirapazamine Chemical compound C1=CC=CC2=[N+]([O-])C(N)=N[N+]([O-])=C21 ORYDPOVDJJZGHQ-UHFFFAOYSA-N 0.000 description 1
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- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 1
- 229960005267 tositumomab Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000005029 transcription elongation Effects 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 229960000575 trastuzumab Drugs 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229960000434 triptorelin acetate Drugs 0.000 description 1
- 229960000294 triptorelin pamoate Drugs 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229960000875 trofosfamide Drugs 0.000 description 1
- UMKFEPPTGMDVMI-UHFFFAOYSA-N trofosfamide Chemical compound ClCCN(CCCl)P1(=O)OCCCN1CCCl UMKFEPPTGMDVMI-UHFFFAOYSA-N 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 208000017997 tumor of parathyroid gland Diseases 0.000 description 1
- 229950009811 ubenimex Drugs 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 206010046885 vaginal cancer Diseases 0.000 description 1
- 208000013139 vaginal neoplasm Diseases 0.000 description 1
- 229960000653 valrubicin Drugs 0.000 description 1
- ZOCKGBMQLCSHFP-KQRAQHLDSA-N valrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC(OC)=C4C(=O)C=3C(O)=C21)(O)C(=O)COC(=O)CCCC)[C@H]1C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O1 ZOCKGBMQLCSHFP-KQRAQHLDSA-N 0.000 description 1
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- 108010082372 valspodar Proteins 0.000 description 1
- 229960000241 vandetanib Drugs 0.000 description 1
- UHTHHESEBZOYNR-UHFFFAOYSA-N vandetanib Chemical compound COC1=CC(C(/N=CN2)=N/C=3C(=CC(Br)=CC=3)F)=C2C=C1OCC1CCN(C)CC1 UHTHHESEBZOYNR-UHFFFAOYSA-N 0.000 description 1
- 229960002730 vapreotide Drugs 0.000 description 1
- 108700029852 vapreotide Proteins 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 229960003862 vemurafenib Drugs 0.000 description 1
- GPXBXXGIAQBQNI-UHFFFAOYSA-N vemurafenib Chemical compound CCCS(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC(=CN=C3NC=2)C=2C=CC(Cl)=CC=2)=C1F GPXBXXGIAQBQNI-UHFFFAOYSA-N 0.000 description 1
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 235000005074 zinc chloride Nutrition 0.000 description 1
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- ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/16—Masculine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Rheumatology (AREA)
- Psychiatry (AREA)
- Virology (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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 true JP2017519760A (ja) | 2017-07-20 |
| JP2017519760A5 JP2017519760A5 (enExample) | 2018-07-12 |
Family
ID=50972563
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 |
|---|---|
| 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
Also Published As
| Publication number | Publication date |
|---|---|
| HK1232226A1 (zh) | 2018-01-05 |
| CN106573931A (zh) | 2017-04-19 |
| US20170121322A1 (en) | 2017-05-04 |
| WO2015193219A1 (de) | 2015-12-23 |
| CA2952526A1 (en) | 2015-12-23 |
| EP3157919A1 (de) | 2017-04-26 |
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