JP2007503450A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2007503450A5 JP2007503450A5 JP2006524818A JP2006524818A JP2007503450A5 JP 2007503450 A5 JP2007503450 A5 JP 2007503450A5 JP 2006524818 A JP2006524818 A JP 2006524818A JP 2006524818 A JP2006524818 A JP 2006524818A JP 2007503450 A5 JP2007503450 A5 JP 2007503450A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- phenyl
- dihydro
- ylmethyl
- 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.)
- Withdrawn
Links
- -1 —OR 3 Chemical group 0.000 claims 443
- 125000000623 heterocyclic group Chemical group 0.000 claims 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 53
- 150000001875 compounds Chemical class 0.000 claims 50
- 125000001424 substituent group Chemical group 0.000 claims 30
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 125000005843 halogen group Chemical group 0.000 claims 22
- 125000002757 morpholinyl group Chemical group 0.000 claims 19
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 16
- 125000004043 oxo group Chemical group O=* 0.000 claims 16
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 12
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 11
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 10
- 239000003795 chemical substances by application Substances 0.000 claims 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 10
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 10
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 10
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 8
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 8
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 8
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 8
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 6
- 125000005956 isoquinolyl group Chemical group 0.000 claims 6
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 6
- 125000003418 alkyl amino alkoxy group Chemical group 0.000 claims 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 5
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 4
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 4
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 4
- 125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims 3
- 125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 claims 3
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 3
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 3
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 3
- 125000005493 quinolyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 238000006467 substitution reaction Methods 0.000 claims 3
- KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims 2
- OHKXAAYXNGNVSQ-UHFFFAOYSA-N 2-(1-acetyl-3,3-dimethyl-2h-indol-6-yl)-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C1=C2N(C(=O)C)CC(C)(C)C2=CC=C1N(C(C1=2)=O)CC1=CC=CC=2NCC1=CC=NC=C1 OHKXAAYXNGNVSQ-UHFFFAOYSA-N 0.000 claims 2
- AMMJYZHEPBAGLM-UHFFFAOYSA-N 2-(3,3-dimethyl-1,2-dihydroindol-6-yl)-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C=1C=C2C(C)(C)CNC2=CC=1N(C(C1=2)=O)CC1=CC=CC=2NCC1=CC=NC=C1 AMMJYZHEPBAGLM-UHFFFAOYSA-N 0.000 claims 2
- NTYRKOGMBINLQW-UHFFFAOYSA-N 2-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C=1C=C2C(C)(C)CNCC2=CC=1N(C(C1=2)=O)CC1=CC=CC=2NCC1=CC=NC=C1 NTYRKOGMBINLQW-UHFFFAOYSA-N 0.000 claims 2
- BMBGBJAMLUTSGP-UHFFFAOYSA-N 2-(4,4-dimethyl-2,3-dihydro-1h-isoquinolin-7-yl)-7-(quinolin-6-ylmethylamino)-3h-isoindol-1-one Chemical compound N1=CC=CC2=CC(CNC=3C=CC=C4CN(C(C4=3)=O)C=3C=C4CNCC(C4=CC=3)(C)C)=CC=C21 BMBGBJAMLUTSGP-UHFFFAOYSA-N 0.000 claims 2
- MQRHEYRJEXDUDI-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-1-hydroxy-4-(pyridin-4-ylmethylamino)-1h-pyrrolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NCC=3C=CN=CC=3)N=CC=C2C1O MQRHEYRJEXDUDI-UHFFFAOYSA-N 0.000 claims 2
- CBURCKKGVXITEV-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-(pyridin-4-ylmethylamino)-1h-pyrrolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NCC=3C=CN=CC=3)N=CC=C2C1 CBURCKKGVXITEV-UHFFFAOYSA-N 0.000 claims 2
- MBZYLCLZNWJXFM-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-[[2-(methylamino)pyrimidin-4-yl]methylamino]-1h-pyrrolo[3,4-c]pyridin-3-one Chemical compound CNC1=NC=CC(CNC=2C=3C(=O)N(CC=3C=CN=2)C=2C=CC(=CC=2)C(C)(C)C)=N1 MBZYLCLZNWJXFM-UHFFFAOYSA-N 0.000 claims 2
- UIYWWRCGMKAGAZ-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-7-(1h-pyrrolo[2,3-b]pyridin-3-ylmethylamino)-3h-isoindol-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NCC=3C4=CC=CN=C4NC=3)C=CC=C2C1 UIYWWRCGMKAGAZ-UHFFFAOYSA-N 0.000 claims 2
- MCPKAZGMSPNARI-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 MCPKAZGMSPNARI-UHFFFAOYSA-N 0.000 claims 2
- QZLCBACRZQPASX-UHFFFAOYSA-N 2-(5-tert-butyl-1h-pyrazol-3-yl)-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound N1N=C(C(C)(C)C)C=C1N1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 QZLCBACRZQPASX-UHFFFAOYSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- QLWPUIYXTHKZLF-UHFFFAOYSA-N 4-[(2-aminopyridin-4-yl)methylamino]-2-(4-tert-butylphenyl)-1h-pyrrolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NCC=3C=C(N)N=CC=3)N=CC=C2C1 QLWPUIYXTHKZLF-UHFFFAOYSA-N 0.000 claims 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000005877 1,4-benzodioxanyl group Chemical group 0.000 claims 1
- ZYEXXLASDABUPX-UHFFFAOYSA-N 2-(2-phenylethyl)-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C1C2=CC=CC(NCC=3C=CN=CC=3)=C2C(=O)N1CCC1=CC=CC=C1 ZYEXXLASDABUPX-UHFFFAOYSA-N 0.000 claims 1
- BTBOMRLNHNZBBU-UHFFFAOYSA-N 2-(3-chlorophenyl)-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound ClC1=CC=CC(N2C(C3=C(NCC=4C=CN=CC=4)C=CC=C3C2)=O)=C1 BTBOMRLNHNZBBU-UHFFFAOYSA-N 0.000 claims 1
- KBALXVGDUJNLLE-UHFFFAOYSA-N 2-(3-methylphenyl)-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound CC1=CC=CC(N2C(C3=C(NCC=4C=CN=CC=4)C=CC=C3C2)=O)=C1 KBALXVGDUJNLLE-UHFFFAOYSA-N 0.000 claims 1
- FORARFUZEXMMNJ-UHFFFAOYSA-N 2-(3-tert-butylphenyl)-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound CC(C)(C)C1=CC=CC(N2C(C3=C(NCC=4C=CN=CC=4)C=CC=C3C2)=O)=C1 FORARFUZEXMMNJ-UHFFFAOYSA-N 0.000 claims 1
- AJIBKXDARQXECE-UHFFFAOYSA-N 2-(4-butan-2-ylphenyl)-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 AJIBKXDARQXECE-UHFFFAOYSA-N 0.000 claims 1
- JVQNOBVPNMKRMH-UHFFFAOYSA-N 2-(4-butan-2-ylphenyl)-7-[(2-methoxypyridin-4-yl)methylamino]-3h-isoindol-1-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=C(NCC=3C=C(OC)N=CC=3)C=CC=C2C1 JVQNOBVPNMKRMH-UHFFFAOYSA-N 0.000 claims 1
- PYKPRWVUSABCJJ-UHFFFAOYSA-N 2-(4-butan-2-ylphenyl)-7-[(4-fluorophenyl)methylamino]-3h-isoindol-1-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(=O)C2=C(NCC=3C=CC(F)=CC=3)C=CC=C2C1 PYKPRWVUSABCJJ-UHFFFAOYSA-N 0.000 claims 1
- JJLDBGSGVOCULM-UHFFFAOYSA-N 2-(4-methylphenyl)-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C1=CC(C)=CC=C1N1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 JJLDBGSGVOCULM-UHFFFAOYSA-N 0.000 claims 1
- PIQOJBXOWOQKTG-UHFFFAOYSA-N 2-(4-phenoxyphenyl)-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C=12C(=O)N(C=3C=CC(OC=4C=CC=CC=4)=CC=3)CC2=CC=CC=1NCC1=CC=NC=C1 PIQOJBXOWOQKTG-UHFFFAOYSA-N 0.000 claims 1
- SJRUEPKVLFHWID-UHFFFAOYSA-N 2-(4-phenoxyphenyl)-7-(quinolin-6-ylmethylamino)-3h-isoindol-1-one Chemical compound C1C2=CC=CC(NCC=3C=C4C=CC=NC4=CC=3)=C2C(=O)N1C(C=C1)=CC=C1OC1=CC=CC=C1 SJRUEPKVLFHWID-UHFFFAOYSA-N 0.000 claims 1
- CPGJXHGLZOOISC-UHFFFAOYSA-N 2-(4-phenyl-1,3-thiazol-2-yl)-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C=12C(=O)N(C=3SC=C(N=3)C=3C=CC=CC=3)CC2=CC=CC=1NCC1=CC=NC=C1 CPGJXHGLZOOISC-UHFFFAOYSA-N 0.000 claims 1
- SPYMLDYBWRGZHY-UHFFFAOYSA-N 2-(4-phenylphenyl)-4-(pyridin-4-ylmethylamino)-1h-pyrrolo[3,4-c]pyridin-3-one Chemical compound C=12C(=O)N(C=3C=CC(=CC=3)C=3C=CC=CC=3)CC2=CC=NC=1NCC1=CC=NC=C1 SPYMLDYBWRGZHY-UHFFFAOYSA-N 0.000 claims 1
- IXWUZSMDRFSELS-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-3-hydroxy-3-methyl-7-(pyridin-4-ylmethylamino)isoindol-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(O)(C)C(C=CC=C2NCC=3C=CN=CC=3)=C2C1=O IXWUZSMDRFSELS-UHFFFAOYSA-N 0.000 claims 1
- FCVVOQIBIJMINM-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-3-methyl-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound CC1N(C=2C=CC(=CC=2)C(C)(C)C)C(=O)C2=C1C=CC=C2NCC1=CC=NC=C1 FCVVOQIBIJMINM-UHFFFAOYSA-N 0.000 claims 1
- BXPUHWFOLYYJRL-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-(1h-indazol-6-ylamino)-1h-pyrrolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NC=3C=C4NN=CC4=CC=3)N=CC=C2C1 BXPUHWFOLYYJRL-UHFFFAOYSA-N 0.000 claims 1
- QQLWIWSUUHVNRZ-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-[(4-fluorophenyl)methylamino]-1h-pyrrolo[3,4-c]pyridin-3-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NCC=3C=CC(F)=CC=3)N=CC=C2C1 QQLWIWSUUHVNRZ-UHFFFAOYSA-N 0.000 claims 1
- UZQVJYCBNKOQAK-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-7-(2-pyridin-2-ylethenyl)-3h-isoindol-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(C=CC=3N=CC=CC=3)C=CC=C2C1 UZQVJYCBNKOQAK-UHFFFAOYSA-N 0.000 claims 1
- SADUCGRXUAGJSU-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-7-(2-pyridin-3-ylethylamino)-3h-isoindol-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NCCC=3C=NC=CC=3)C=CC=C2C1 SADUCGRXUAGJSU-UHFFFAOYSA-N 0.000 claims 1
- NXJVZCGZQIIFEV-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-7-(2-pyridin-4-ylethyl)-3h-isoindol-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(CCC=3C=CN=CC=3)C=CC=C2C1 NXJVZCGZQIIFEV-UHFFFAOYSA-N 0.000 claims 1
- YPMOHLZXMKQJQG-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-7-(ethylamino)-3h-isoindol-1-one Chemical compound O=C1C=2C(NCC)=CC=CC=2CN1C1=CC=C(C(C)(C)C)C=C1 YPMOHLZXMKQJQG-UHFFFAOYSA-N 0.000 claims 1
- NQJGAVLSTQFTDE-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-7-(pyridin-3-ylamino)-3h-isoindol-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NC=3C=NC=CC=3)C=CC=C2C1 NQJGAVLSTQFTDE-UHFFFAOYSA-N 0.000 claims 1
- ZFYQRIGZQJCIGZ-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-7-(pyridin-4-ylamino)-3h-isoindol-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NC=3C=CN=CC=3)C=CC=C2C1 ZFYQRIGZQJCIGZ-UHFFFAOYSA-N 0.000 claims 1
- DBPFYZDHXXIPDK-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-7-(pyridin-4-ylmethoxy)-3h-isoindol-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(OCC=3C=CN=CC=3)C=CC=C2C1 DBPFYZDHXXIPDK-UHFFFAOYSA-N 0.000 claims 1
- RFAPCXHRPFYPCN-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-7-(quinolin-5-ylamino)-3h-isoindol-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NC=3C4=CC=CN=C4C=CC=3)C=CC=C2C1 RFAPCXHRPFYPCN-UHFFFAOYSA-N 0.000 claims 1
- CPMISOZJIBELRO-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-7-(quinolin-6-ylamino)-3h-isoindol-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NC=3C=C4C=CC=NC4=CC=3)C=CC=C2C1 CPMISOZJIBELRO-UHFFFAOYSA-N 0.000 claims 1
- AYDQUOXRGBIOQK-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-7-(quinolin-6-ylmethylamino)-3h-isoindol-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C2=C(NCC=3C=C4C=CC=NC4=CC=3)C=CC=C2C1 AYDQUOXRGBIOQK-UHFFFAOYSA-N 0.000 claims 1
- ZRFIAPFXVAQONQ-QGZVFWFLSA-N 2-(4-tert-butylphenyl)-7-[(1r)-1-pyridin-4-ylethoxy]-3h-isoindol-1-one Chemical compound O([C@H](C)C=1C=CN=CC=1)C(C=1C2=O)=CC=CC=1CN2C1=CC=C(C(C)(C)C)C=C1 ZRFIAPFXVAQONQ-QGZVFWFLSA-N 0.000 claims 1
- ZRFIAPFXVAQONQ-KRWDZBQOSA-N 2-(4-tert-butylphenyl)-7-[(1s)-1-pyridin-4-ylethoxy]-3h-isoindol-1-one Chemical compound O([C@@H](C)C=1C=CN=CC=1)C(C=1C2=O)=CC=CC=1CN2C1=CC=C(C(C)(C)C)C=C1 ZRFIAPFXVAQONQ-KRWDZBQOSA-N 0.000 claims 1
- JXVWBWUXRBTLEL-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-7-[(2-methoxypyridin-4-yl)methylamino]-3h-isoindol-1-one Chemical compound C1=NC(OC)=CC(CNC=2C=3C(=O)N(CC=3C=CC=2)C=2C=CC(=CC=2)C(C)(C)C)=C1 JXVWBWUXRBTLEL-UHFFFAOYSA-N 0.000 claims 1
- OOKJUROAWAVZSX-QGZVFWFLSA-N 2-(4-tert-butylphenyl)-7-[[(1r)-1-pyridin-4-ylethyl]amino]-3h-isoindol-1-one Chemical compound N([C@H](C)C=1C=CN=CC=1)C(C=1C2=O)=CC=CC=1CN2C1=CC=C(C(C)(C)C)C=C1 OOKJUROAWAVZSX-QGZVFWFLSA-N 0.000 claims 1
- OOKJUROAWAVZSX-KRWDZBQOSA-N 2-(4-tert-butylphenyl)-7-[[(1s)-1-pyridin-4-ylethyl]amino]-3h-isoindol-1-one Chemical compound N([C@@H](C)C=1C=CN=CC=1)C(C=1C2=O)=CC=CC=1CN2C1=CC=C(C(C)(C)C)C=C1 OOKJUROAWAVZSX-KRWDZBQOSA-N 0.000 claims 1
- YGNPYFDHDYUVBN-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-7-[[2-(methylamino)pyrimidin-4-yl]methylamino]-3h-isoindol-1-one Chemical compound CNC1=NC=CC(CNC=2C=3C(=O)N(CC=3C=CC=2)C=2C=CC(=CC=2)C(C)(C)C)=N1 YGNPYFDHDYUVBN-UHFFFAOYSA-N 0.000 claims 1
- SRJRDBJYGSHTOH-UHFFFAOYSA-N 2-(5-tert-butyl-1h-pyrazol-3-yl)-7-[(2-methoxypyridin-4-yl)methylamino]-3h-isoindol-1-one Chemical compound C1=NC(OC)=CC(CNC=2C=3C(=O)N(CC=3C=CC=2)C=2NN=C(C=2)C(C)(C)C)=C1 SRJRDBJYGSHTOH-UHFFFAOYSA-N 0.000 claims 1
- XBNFTEZLUSZPAZ-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound COC1=CC=CC(CN2C(C3=C(NCC=4C=CN=CC=4)C=CC=C3C2)=O)=C1 XBNFTEZLUSZPAZ-UHFFFAOYSA-N 0.000 claims 1
- DNWOUYOVYJRYQW-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]-7-(quinolin-6-ylmethylamino)-3h-isoindol-1-one Chemical compound COC1=CC=CC(CN2C(C3=C(NCC=4C=C5C=CC=NC5=CC=4)C=CC=C3C2)=O)=C1 DNWOUYOVYJRYQW-UHFFFAOYSA-N 0.000 claims 1
- ASWDUSMUTUCNMQ-UHFFFAOYSA-N 2-[2-(2,4-dichlorophenyl)ethyl]-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound ClC1=CC(Cl)=CC=C1CCN1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 ASWDUSMUTUCNMQ-UHFFFAOYSA-N 0.000 claims 1
- AKWQUEJOKBUSBB-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)ethyl]-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound ClC1=CC=CC=C1CCN1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 AKWQUEJOKBUSBB-UHFFFAOYSA-N 0.000 claims 1
- BAYXUJIEYJOGME-UHFFFAOYSA-N 2-[2-(2-fluorophenyl)ethyl]-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound FC1=CC=CC=C1CCN1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 BAYXUJIEYJOGME-UHFFFAOYSA-N 0.000 claims 1
- LWQLXIVRQVHGKJ-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)ethyl]-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1CCN1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 LWQLXIVRQVHGKJ-UHFFFAOYSA-N 0.000 claims 1
- CJFSOGKBWHUNBT-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)ethyl]-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C1=C(OC)C(OC)=CC=C1CCN1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 CJFSOGKBWHUNBT-UHFFFAOYSA-N 0.000 claims 1
- HVOFNIQRPHKSCC-UHFFFAOYSA-N 2-[2-(3-fluorophenyl)ethyl]-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound FC1=CC=CC(CCN2C(C3=C(NCC=4C=CN=CC=4)C=CC=C3C2)=O)=C1 HVOFNIQRPHKSCC-UHFFFAOYSA-N 0.000 claims 1
- LXUFWAPEIBGFMY-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)ethyl]-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C1=CC(Cl)=CC=C1CCN1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 LXUFWAPEIBGFMY-UHFFFAOYSA-N 0.000 claims 1
- DCVHBKIMVDXWSD-UHFFFAOYSA-N 2-[2-(4-methoxyphenyl)ethyl]-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C1=CC(OC)=CC=C1CCN1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 DCVHBKIMVDXWSD-UHFFFAOYSA-N 0.000 claims 1
- SDRIZYCOOBGYNT-UHFFFAOYSA-N 2-[2-(4-methylphenyl)ethyl]-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C1=CC(C)=CC=C1CCN1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 SDRIZYCOOBGYNT-UHFFFAOYSA-N 0.000 claims 1
- FHUHHYXTSDUUJT-UHFFFAOYSA-N 2-[3-(oxolan-2-ylmethoxy)-5-(trifluoromethyl)phenyl]-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C=1C(N2C(C3=C(NCC=4C=CN=CC=4)C=CC=C3C2)=O)=CC(C(F)(F)F)=CC=1OCC1CCCO1 FHUHHYXTSDUUJT-UHFFFAOYSA-N 0.000 claims 1
- UAMCWQXBRGVRRS-UHFFFAOYSA-N 2-[3-(oxolan-3-yloxy)-5-(trifluoromethyl)phenyl]-7-(pyridin-4-ylamino)-3h-isoindol-1-one Chemical compound C=1C(N2C(C3=C(NC=4C=CN=CC=4)C=CC=C3C2)=O)=CC(C(F)(F)F)=CC=1OC1CCOC1 UAMCWQXBRGVRRS-UHFFFAOYSA-N 0.000 claims 1
- OJUGOSJEXYZHLB-UHFFFAOYSA-N 2-[3-(oxolan-3-yloxy)-5-(trifluoromethyl)phenyl]-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C=1C(N2C(C3=C(NCC=4C=CN=CC=4)C=CC=C3C2)=O)=CC(C(F)(F)F)=CC=1OC1CCOC1 OJUGOSJEXYZHLB-UHFFFAOYSA-N 0.000 claims 1
- DZBPFYYQQHDEGK-UHFFFAOYSA-N 2-[3-(oxolan-3-yloxy)-5-(trifluoromethyl)phenyl]-7-(quinolin-6-ylmethylamino)-3h-isoindol-1-one Chemical compound C=1C(N2C(C3=C(NCC=4C=C5C=CC=NC5=CC=4)C=CC=C3C2)=O)=CC(C(F)(F)F)=CC=1OC1CCOC1 DZBPFYYQQHDEGK-UHFFFAOYSA-N 0.000 claims 1
- XBGDDZSIYKGORW-UHFFFAOYSA-N 2-[4,4-dimethyl-2-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1,3-dihydroisoquinolin-7-yl]-7-(1h-pyrrolo[2,3-b]pyridin-3-ylamino)-3h-isoindol-1-one Chemical compound C1=CC=C2C(NC=3C=CC=C4CN(C(C4=3)=O)C=3C=C4CN(CC=5C6=CC=CN=C6NC=5)CC(C4=CC=3)(C)C)=CNC2=N1 XBGDDZSIYKGORW-UHFFFAOYSA-N 0.000 claims 1
- RWSOCBFYMLFILM-UHFFFAOYSA-N 2-[4-(1,1,2,2,2-pentafluoroethyl)phenyl]-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C1=CC(C(F)(F)C(F)(F)F)=CC=C1N1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 RWSOCBFYMLFILM-UHFFFAOYSA-N 0.000 claims 1
- AHOIZGBJPPOICZ-UHFFFAOYSA-N 2-[4-(1-methoxy-2-methylpropan-2-yl)phenyl]-7-(pyridin-4-ylmethylamino)-3h-isoindol-1-one Chemical compound C1=CC(C(C)(C)COC)=CC=C1N1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 AHOIZGBJPPOICZ-UHFFFAOYSA-N 0.000 claims 1
- NWDDWYIBHUYZDX-UHFFFAOYSA-N 2-[4-(1-methoxy-2-methylpropan-2-yl)phenyl]-7-(quinolin-6-ylmethylamino)-3h-isoindol-1-one Chemical compound C1=CC(C(C)(C)COC)=CC=C1N1C(=O)C2=C(NCC=3C=C4C=CC=NC4=CC=3)C=CC=C2C1 NWDDWYIBHUYZDX-UHFFFAOYSA-N 0.000 claims 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical group C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims 1
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims 1
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims 1
- LSRUUXJPPSZOMQ-UHFFFAOYSA-N 7-(2,3-dihydro-1-benzofuran-5-ylmethylamino)-2-[3-(oxolan-2-ylmethoxy)-5-(trifluoromethyl)phenyl]-3h-isoindol-1-one Chemical compound C=1C(N2C(C3=C(NCC=4C=C5CCOC5=CC=4)C=CC=C3C2)=O)=CC(C(F)(F)F)=CC=1OCC1CCCO1 LSRUUXJPPSZOMQ-UHFFFAOYSA-N 0.000 claims 1
- SVISVCDNFLAIJL-UHFFFAOYSA-N 7-(oxan-4-ylamino)-2-[3-(oxolan-2-ylmethoxy)-5-(trifluoromethyl)phenyl]-3h-isoindol-1-one Chemical compound C=1C(N2C(C3=C(NC4CCOCC4)C=CC=C3C2)=O)=CC(C(F)(F)F)=CC=1OCC1CCCO1 SVISVCDNFLAIJL-UHFFFAOYSA-N 0.000 claims 1
- ORBXSYMMNIBWCS-UHFFFAOYSA-N 7-(pyridin-4-ylmethylamino)-2-[2-[3-(trifluoromethyl)phenyl]ethyl]-3h-isoindol-1-one Chemical compound FC(F)(F)C1=CC=CC(CCN2C(C3=C(NCC=4C=CN=CC=4)C=CC=C3C2)=O)=C1 ORBXSYMMNIBWCS-UHFFFAOYSA-N 0.000 claims 1
- QXWPOMPJLIGNNQ-UHFFFAOYSA-N 7-(pyridin-4-ylmethylamino)-2-[3-(trifluoromethoxy)phenyl]-3h-isoindol-1-one Chemical compound FC(F)(F)OC1=CC=CC(N2C(C3=C(NCC=4C=CN=CC=4)C=CC=C3C2)=O)=C1 QXWPOMPJLIGNNQ-UHFFFAOYSA-N 0.000 claims 1
- UFSBARAWVPJYQQ-UHFFFAOYSA-N 7-(pyridin-4-ylmethylamino)-2-[4-(trifluoromethoxy)phenyl]-3h-isoindol-1-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 UFSBARAWVPJYQQ-UHFFFAOYSA-N 0.000 claims 1
- LYRWSTOEEHGLEP-UHFFFAOYSA-N 7-(pyridin-4-ylmethylamino)-2-[4-(trifluoromethyl)phenyl]-3h-isoindol-1-one Chemical compound C1=CC(C(F)(F)F)=CC=C1N1C(=O)C2=C(NCC=3C=CN=CC=3)C=CC=C2C1 LYRWSTOEEHGLEP-UHFFFAOYSA-N 0.000 claims 1
- BUWGPYSRDASNRP-UHFFFAOYSA-N 7-(pyridin-4-ylmethylamino)-2-[[3-(trifluoromethyl)phenyl]methyl]-3h-isoindol-1-one Chemical compound FC(F)(F)C1=CC=CC(CN2C(C3=C(NCC=4C=CN=CC=4)C=CC=C3C2)=O)=C1 BUWGPYSRDASNRP-UHFFFAOYSA-N 0.000 claims 1
- ZNGJAJDFCVQIQM-UHFFFAOYSA-N 7-(quinolin-4-ylmethylamino)-2-[4-(trifluoromethoxy)phenyl]-3h-isoindol-1-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1C(=O)C2=C(NCC=3C4=CC=CC=C4N=CC=3)C=CC=C2C1 ZNGJAJDFCVQIQM-UHFFFAOYSA-N 0.000 claims 1
- VHVGVXZEJSJSEK-UHFFFAOYSA-N 7-(quinolin-6-ylmethylamino)-2-[4-(trifluoromethoxy)phenyl]-3h-isoindol-1-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1C(=O)C2=C(NCC=3C=C4C=CC=NC4=CC=3)C=CC=C2C1 VHVGVXZEJSJSEK-UHFFFAOYSA-N 0.000 claims 1
- RLKNNEBKQBPJMX-UHFFFAOYSA-N 7-[(2-methoxypyridin-4-yl)methylamino]-2-(4-phenoxyphenyl)-3h-isoindol-1-one Chemical compound C1=NC(OC)=CC(CNC=2C=3C(=O)N(CC=3C=CC=2)C=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1 RLKNNEBKQBPJMX-UHFFFAOYSA-N 0.000 claims 1
- BNLITCSFMRHUIU-UHFFFAOYSA-N 7-[(2-methoxypyridin-4-yl)methylamino]-2-[4-(trifluoromethoxy)phenyl]-3h-isoindol-1-one Chemical compound C1=NC(OC)=CC(CNC=2C=3C(=O)N(CC=3C=CC=2)C=2C=CC(OC(F)(F)F)=CC=2)=C1 BNLITCSFMRHUIU-UHFFFAOYSA-N 0.000 claims 1
- URHVGXDDCVGQTG-UHFFFAOYSA-N 7-[(4-fluorophenyl)methylamino]-2-[3-(oxolan-2-ylmethoxy)-5-(trifluoromethyl)phenyl]-3h-isoindol-1-one Chemical compound C1=CC(F)=CC=C1CNC1=CC=CC2=C1C(=O)N(C=1C=C(C=C(OCC3OCCC3)C=1)C(F)(F)F)C2 URHVGXDDCVGQTG-UHFFFAOYSA-N 0.000 claims 1
- YYLBFGKJOYVILC-UHFFFAOYSA-N 7-[(4-fluorophenyl)methylamino]-2-[3-(oxolan-3-yloxy)-5-(trifluoromethyl)phenyl]-3h-isoindol-1-one Chemical compound C1=CC(F)=CC=C1CNC1=CC=CC2=C1C(=O)N(C=1C=C(C=C(OC3COCC3)C=1)C(F)(F)F)C2 YYLBFGKJOYVILC-UHFFFAOYSA-N 0.000 claims 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- JOBGRJWXMXTUOS-UHFFFAOYSA-N n-[2-tert-butyl-5-[3-oxo-4-(pyridin-4-ylmethylamino)-1h-isoindol-2-yl]phenyl]-2-(dimethylamino)acetamide Chemical compound C1=C(C(C)(C)C)C(NC(=O)CN(C)C)=CC(N2C(C3=C(NCC=4C=CN=CC=4)C=CC=C3C2)=O)=C1 JOBGRJWXMXTUOS-UHFFFAOYSA-N 0.000 claims 1
- XSRAAVIQYRQUKS-UHFFFAOYSA-N n-[2-tert-butyl-5-[3-oxo-4-(pyridin-4-ylmethylamino)-1h-isoindol-2-yl]phenyl]-2-morpholin-4-ylacetamide Chemical compound CC(C)(C)C1=CC=C(N2C(C3=C(NCC=4C=CN=CC=4)C=CC=C3C2)=O)C=C1NC(=O)CN1CCOCC1 XSRAAVIQYRQUKS-UHFFFAOYSA-N 0.000 claims 1
- USEOVUGFARCBRI-UHFFFAOYSA-N n-[2-tert-butyl-5-[3-oxo-4-(pyridin-4-ylmethylamino)-1h-isoindol-2-yl]phenyl]-2-piperidin-1-ylacetamide Chemical compound CC(C)(C)C1=CC=C(N2C(C3=C(NCC=4C=CN=CC=4)C=CC=C3C2)=O)C=C1NC(=O)CN1CCCCC1 USEOVUGFARCBRI-UHFFFAOYSA-N 0.000 claims 1
- UKYWTHPSSPVDSP-UHFFFAOYSA-N n-[2-tert-butyl-5-[3-oxo-4-(quinolin-6-ylmethylamino)-1h-isoindol-2-yl]phenyl]-2-morpholin-4-ylacetamide Chemical compound CC(C)(C)C1=CC=C(N2C(C3=C(NCC=4C=C5C=CC=NC5=CC=4)C=CC=C3C2)=O)C=C1NC(=O)CN1CCOCC1 UKYWTHPSSPVDSP-UHFFFAOYSA-N 0.000 claims 1
- CLLIUBAAZRNATA-UHFFFAOYSA-N n-[2-tert-butyl-5-[3-oxo-4-(quinolin-6-ylmethylamino)-1h-isoindol-2-yl]phenyl]-2-piperidin-1-ylacetamide Chemical compound CC(C)(C)C1=CC=C(N2C(C3=C(NCC=4C=C5C=CC=NC5=CC=4)C=CC=C3C2)=O)C=C1NC(=O)CN1CCCCC1 CLLIUBAAZRNATA-UHFFFAOYSA-N 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000004547 quinazolin-6-yl group Chemical group N1=CN=CC2=CC(=CC=C12)* 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims 1
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- XPDYOJKUTIYHCJ-UHFFFAOYSA-N tert-butyl 4,4-dimethyl-7-[3-oxo-4-(1h-pyrrolo[2,3-b]pyridin-3-ylmethylamino)-1h-isoindol-2-yl]-1,3-dihydroisoquinoline-2-carboxylate Chemical compound C1=CC=C2C(CNC=3C=CC=C4CN(C(C4=3)=O)C=3C=C4CN(CC(C)(C)C4=CC=3)C(=O)OC(C)(C)C)=CNC2=N1 XPDYOJKUTIYHCJ-UHFFFAOYSA-N 0.000 claims 1
- PVVDSCBZJGQDEG-UHFFFAOYSA-N tert-butyl 4,4-dimethyl-7-[3-oxo-4-(quinolin-6-ylmethylamino)-1h-isoindol-2-yl]-1,3-dihydroisoquinoline-2-carboxylate Chemical compound N1=CC=CC2=CC(CNC=3C=CC=C4CN(C(C4=3)=O)C=3C=C4CN(CC(C)(C)C4=CC=3)C(=O)OC(C)(C)C)=CC=C21 PVVDSCBZJGQDEG-UHFFFAOYSA-N 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 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 |
|---|---|---|---|
| US49787803P | 2003-08-25 | 2003-08-25 | |
| US10/926,238 US7320992B2 (en) | 2003-08-25 | 2004-08-24 | Substituted 2,3-dihydro-1h-isoindol-1-one derivatives and methods of use |
| PCT/US2004/027595 WO2005021532A1 (en) | 2003-08-25 | 2004-08-25 | Substituted 2,3-dihydro-1h-isoindol-1-one derivatives and methods of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007503450A JP2007503450A (ja) | 2007-02-22 |
| JP2007503450A5 true JP2007503450A5 (OSRAM) | 2007-07-19 |
Family
ID=34228620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006524818A Withdrawn JP2007503450A (ja) | 2003-08-25 | 2004-08-25 | 置換２，３−ジヒドロ−１ｈ−イソインドル−１−オン誘導体及び使用方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7320992B2 (OSRAM) |
| EP (1) | EP1664027B1 (OSRAM) |
| JP (1) | JP2007503450A (OSRAM) |
| AT (1) | ATE453636T1 (OSRAM) |
| AU (1) | AU2004269000A1 (OSRAM) |
| CA (1) | CA2534570A1 (OSRAM) |
| DE (1) | DE602004024900D1 (OSRAM) |
| ES (1) | ES2337062T3 (OSRAM) |
| MX (1) | MXPA06001923A (OSRAM) |
| WO (1) | WO2005021532A1 (OSRAM) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2006237920A1 (en) * | 2005-04-19 | 2006-10-26 | Kyowa Hakko Kirin Co., Ltd. | Nitrogen-containing heterocyclic compound |
| WO2006134989A1 (ja) * | 2005-06-15 | 2006-12-21 | Kyowa Hakko Kogyo Co., Ltd. | 含窒素複素環化合物 |
| ES2434946T3 (es) * | 2005-08-31 | 2013-12-18 | Celgene Corporation | Compuestos de isoindol imida y composiciones que los comprenden y métodos para usarlo |
| US7989461B2 (en) | 2005-12-23 | 2011-08-02 | Amgen Inc. | Substituted quinazolinamine compounds for the treatment of cancer |
| US8110681B2 (en) | 2006-03-17 | 2012-02-07 | The United States Of America As Represented By The Secretary, Department Of Health And Human Services | Compounds for the treatment of spinal muscular atrophy and other uses |
| PE20080695A1 (es) * | 2006-04-27 | 2008-06-28 | Banyu Pharma Co Ltd | Derivados de dihidropirazolopirimidinona como inhibidores de quinasa weel |
| WO2008005910A2 (en) * | 2006-07-06 | 2008-01-10 | Bristol-Myers Squibb Company | Pyridone/hydroxypyridine 11-beta hydroxysteroid dehydrogenase type i inhibitors |
| NZ578096A (en) * | 2007-01-10 | 2011-11-25 | Albany Molecular Res Inc | 5-pyridinone substituted indazoles |
| US20110053953A1 (en) * | 2007-02-09 | 2011-03-03 | Abdelmalik Slassi | AZA-Isoindolones and Their Use as Metabotropic Glutamate Receptor Potentiators - 613 |
| AU2008229383B2 (en) | 2007-03-20 | 2013-09-05 | Celgene Corporation | 4'-O-substituted isoindoline derivatives and compositions comprising and methods of using the same |
| ES2382982T3 (es) * | 2007-07-21 | 2012-06-15 | Albany Molecular Research, Inc. | Indazoles sustituidos con 5-piridinona y composiciones farmacéuticas de los mismos |
| TW200918062A (en) * | 2007-09-12 | 2009-05-01 | Wyeth Corp | Azacyclylisoquinolinone and-isoindolinone derivatives as histamine-3 antagonists |
| EP2573080A1 (en) * | 2007-09-27 | 2013-03-27 | The United States of America, as Represented by the Secretary, Department of Health and Human Services | Isoindoline compounds for the treatment of spinal muscular atrophy and other uses |
| US8329711B2 (en) * | 2007-10-23 | 2012-12-11 | Msd K.K. | Pyridone-substituted-dihydropyrazolopyrimidinone derivative |
| KR101068835B1 (ko) * | 2007-10-26 | 2011-09-30 | 한국과학기술연구원 | 베타-아밀로이드 집적체 및 피브릴에 우수한 결합 친화도를가지는 이소인돌론 화합물 및 이의 제조 방법 |
| WO2009072581A1 (ja) * | 2007-12-05 | 2009-06-11 | Aska Pharmaceutical Co., Ltd. | ラクタム化合物又はその塩及びｐｐａｒ活性化剤 |
| US20110092452A1 (en) * | 2008-03-05 | 2011-04-21 | The Regents Of The University Of Michigan | Compositions and methods for diagnosing and treating pancreatic cancer |
| AU2009245791B2 (en) | 2008-05-08 | 2013-05-16 | Basf Se | Method for manufacturing aryl carboxamides |
| GB0811643D0 (en) | 2008-06-25 | 2008-07-30 | Cancer Rec Tech Ltd | New therapeutic agents |
| CN102369199A (zh) | 2009-04-01 | 2012-03-07 | 巴斯夫欧洲公司 | 用于防治无脊椎动物害虫的异*唑啉化合物 |
| WO2011006803A1 (en) * | 2009-07-14 | 2011-01-20 | Nerviano Medical Sciences S.R.L. | 3-0x0-2, 3, -dihydro-lh-isoindole-4-carboxamides with selective parp-1 inhibition |
| AU2010294209A1 (en) * | 2009-09-10 | 2012-03-29 | Irm Llc | Ether derivatives of bicyclic heteroaryls |
| AU2010303567B2 (en) * | 2009-10-06 | 2016-06-09 | Millennium Pharmaceuticals, Inc | Heterocyclic compounds useful as PDK1 inhibitors |
| US8440710B2 (en) | 2009-10-15 | 2013-05-14 | Hoffmann-La Roche Inc. | HSL inhibitors useful in the treatment of diabetes |
| DK2516434T3 (en) | 2009-12-23 | 2015-08-31 | Takeda Pharmaceutical | FUSED HETEROAROMATIC PYRROLIDINONS AS SICK INHIBITORS |
| WO2012177714A1 (en) | 2011-06-22 | 2012-12-27 | Takeda Pharmaceutical Company Limited | Substituted 6-aza-isoindolin-1-one derivatives |
| AR088320A1 (es) | 2011-10-14 | 2014-05-28 | Incyte Corp | Derivados de isoindolinona y pirrolopiridinona como inhibidores de akt |
| EP2821401B1 (en) | 2012-03-02 | 2020-09-09 | Takeda Pharmaceutical Company Limited | Dihydroquinolinone compounds as modulators of the muscarininc m1 receptor |
| EP2921480B1 (en) * | 2012-11-19 | 2017-10-11 | Takeda Pharmaceutical Company Limited | Nitrogen-containing heterocyclic compound |
| JP2016521259A (ja) * | 2013-03-20 | 2016-07-21 | バイエル・ファルマ・アクティエンゲゼルシャフト | 置換Ｎ−ビフェニル−３−アセチルアミノ−ベンズアミドおよびＮ−［３−（アセチルアミノ）フェニル］−ビフェニル−カルボキサミドならびにＷｎｔシグナル伝達経路の阻害剤としてのそれらの使用 |
| EP4019518A1 (en) * | 2014-02-28 | 2022-06-29 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
| EP3119757B1 (en) | 2014-03-17 | 2018-05-16 | Pfizer Inc | Diacylglycerol acyltransferase 2 inhibitors for use in the treatment of metabolic and related disorders |
| EP3144308B1 (en) * | 2014-05-16 | 2020-06-24 | Takeda Pharmaceutical Company Limited | Nitrogen-containing heterocyclic compound |
| US11071793B2 (en) * | 2014-08-29 | 2021-07-27 | Chdi Foundation, Inc. | Probes for imaging huntingtin protein |
| GB201517216D0 (en) | 2015-09-29 | 2015-11-11 | Cancer Res Technology Ltd And Astex Therapeutics Ltd | Pharmaceutical compounds |
| GB201517217D0 (en) | 2015-09-29 | 2015-11-11 | Astex Therapeutics Ltd And Cancer Res Technology Ltd | Pharmaceutical compounds |
| US20190060286A1 (en) | 2016-02-29 | 2019-02-28 | University Of Florida Research Foundation, Incorpo | Chemotherapeutic Methods |
| KR101789430B1 (ko) * | 2016-06-28 | 2017-10-25 | 동국대학교 산학협력단 | Smo 저해 활성을 갖는 신규 화합물 및 이를 유효성분으로 포함하는 암 예방 또는 치료용 조성물 |
| GB201704965D0 (en) | 2017-03-28 | 2017-05-10 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| GB201704966D0 (en) | 2017-03-28 | 2017-05-10 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| US10513515B2 (en) | 2017-08-25 | 2019-12-24 | Biotheryx, Inc. | Ether compounds and uses thereof |
| EP3743063A4 (en) * | 2018-01-26 | 2021-10-20 | Nurix Therapeutics, Inc. | CBL-B INHIBITORS AND THEIR METHODS OF USE |
| CA3106239A1 (en) | 2018-07-27 | 2020-01-30 | Biotheryx, Inc. | Bifunctional compounds as cdk modulators |
| AU2020272937B2 (en) | 2019-04-09 | 2024-09-26 | Nurix Therapeutics, Inc. | 3-substituted piperidine compounds for Cbl-b inhibition, and use of a Cbl-b inhibitor in combination with a cancer vaccine and/or oncolytic virus |
| JP7587528B2 (ja) | 2019-05-17 | 2024-11-20 | ニューリックス セラピューティクス，インコーポレイテッド | Ｃｂｌ－ｂ阻害のためのシアノシクロブチル化合物及びその使用 |
| CA3144450A1 (en) | 2019-06-26 | 2020-12-30 | Nurix Therapeutics, Inc. | Substituted benzyl-triazole compounds for cbl-b inhibition, and further uses thereof |
| WO2021032935A1 (en) * | 2019-08-21 | 2021-02-25 | Kalvista Pharmaceuticals Limited | Enzyme inhibitors |
| US12121540B2 (en) | 2019-09-24 | 2024-10-22 | Nurix Therapeutics, Inc. | CBL inhibitors and compositions for use in adoptive cell therapy |
| WO2021222150A2 (en) | 2020-04-28 | 2021-11-04 | Anwita Biosciences, Inc. | Interleukin-2 polypeptides and fusion proteins thereof, and their pharmaceutical compositions and therapeutic applications |
| MX2023011883A (es) | 2021-04-08 | 2023-11-09 | Nurix Therapeutics Inc | Terapias combinadas con compuestos inhibidores de cbl-b. |
| CN118201918A (zh) * | 2021-11-04 | 2024-06-14 | 莱德克斯制药公共有限公司 | 用于治疗癌症和纤维化疾病的ddr1和ddr2抑制剂 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990005722A1 (en) | 1988-11-21 | 1990-05-31 | Eastman Kodak Company | Phthalimide compounds for forming amorphous layers by vacuum deposition |
| US5032598A (en) | 1989-12-08 | 1991-07-16 | Merck & Co., Inc. | Nitrogens containing heterocyclic compounds as class III antiarrhythmic agents |
| JPH04445A (ja) | 1990-04-17 | 1992-01-06 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料の処理方法 |
| US5231099A (en) | 1991-04-15 | 1993-07-27 | Du Pont Merck Pharmaceutical Company | Use of sigma receptor antagonists to enhance the effects of antipsychotic drugs |
| US5324743A (en) | 1992-12-10 | 1994-06-28 | Eli Lilly And Company | Leukotriene B4 antagonists |
| NZ277556A (en) | 1993-12-27 | 1997-06-24 | Eisai Co Ltd | N-phenyl(alkyl)- and n-pyridyl(alkyl)anthranilic acid derivatives; intermediates |
| FR2717812B1 (fr) | 1994-03-28 | 1996-05-10 | Rhone Poulenc Rorer Sa | Indeno[1,2-e]pyrazine-4-ones, leur préparation et les médicaments les contenant. |
| JPH10500402A (ja) | 1994-04-29 | 1998-01-13 | 武田薬品工業株式会社 | 縮合複素環化合物またはその塩、その製造法および用途 |
| US5789434A (en) | 1994-11-15 | 1998-08-04 | Bayer Corporation | Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors |
| HUT76640A (en) | 1995-08-17 | 1997-10-28 | Chinoin Gyogyszer Es Vegyeszet | Compounds of pharmaceutical activity cyclic amide derivatives, pharmaceutical compositions containing them, process for producing them and their use |
| AU1618697A (en) | 1996-02-06 | 1997-08-28 | Japan Tobacco Inc. | Novel compounds and pharmaceutical use thereof |
| US5932582A (en) | 1996-06-28 | 1999-08-03 | Merck & Co., Inc. | Fibrinogen receptor antagonist prodrugs |
| US5798368A (en) * | 1996-08-22 | 1998-08-25 | Celgene Corporation | Tetrasubstituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolines and method of reducing TNFα levels |
| HU228769B1 (en) | 1996-07-24 | 2013-05-28 | Celgene Corp | Substituted 2(2,6-dioxopiperidin-3-yl)phthalimides and -1-oxoisoindolines and their use for production of pharmaceutical compositions for mammals to reduce the level of tnf-alpha |
| DE19650975A1 (de) | 1996-12-09 | 1998-06-10 | Basf Ag | Neue heterocyclisch substituierte Benzamide und deren Anwendung |
| KR19980074060A (ko) | 1997-03-21 | 1998-11-05 | 김윤배 | 신규한 치환된 3,4-디알콕시페닐 유도체 |
| JP2001511448A (ja) | 1997-07-31 | 2001-08-14 | セルジーン コーポレイション | 置換アルカノヒドロキサム酸およびＴＮＦαレベルの減少方法 |
| AU1556299A (en) | 1997-12-17 | 1999-07-05 | Novo Nordisk A/S | Novel pyridine and pyrimidine derivatives |
| US20010006973A1 (en) | 1998-03-16 | 2001-07-05 | Hon-Wah Man | 1-oxo- and 1,3-dioxoisoindolines and method of reducing inflammatory cytokine levels |
| US6020358A (en) | 1998-10-30 | 2000-02-01 | Celgene Corporation | Substituted phenethylsulfones and method of reducing TNFα levels |
| US6667316B1 (en) | 1999-11-12 | 2003-12-23 | Celgene Corporation | Pharmaceutically active isoindoline derivatives |
| US6482951B2 (en) * | 2000-12-13 | 2002-11-19 | Hoffmann-La Roche Inc. | Isoindolin-1-one glucokinase activators |
| US20030045552A1 (en) * | 2000-12-27 | 2003-03-06 | Robarge Michael J. | Isoindole-imide compounds, compositions, and uses thereof |
-
2004
- 2004-08-24 US US10/926,238 patent/US7320992B2/en not_active Expired - Lifetime
- 2004-08-25 WO PCT/US2004/027595 patent/WO2005021532A1/en not_active Ceased
- 2004-08-25 ES ES04782152T patent/ES2337062T3/es not_active Expired - Lifetime
- 2004-08-25 MX MXPA06001923A patent/MXPA06001923A/es not_active Application Discontinuation
- 2004-08-25 AT AT04782152T patent/ATE453636T1/de not_active IP Right Cessation
- 2004-08-25 DE DE602004024900T patent/DE602004024900D1/de not_active Expired - Lifetime
- 2004-08-25 CA CA002534570A patent/CA2534570A1/en not_active Abandoned
- 2004-08-25 AU AU2004269000A patent/AU2004269000A1/en not_active Abandoned
- 2004-08-25 JP JP2006524818A patent/JP2007503450A/ja not_active Withdrawn
- 2004-08-25 EP EP04782152A patent/EP1664027B1/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2007504148A5 (OSRAM) | ||
| JP2006502112A5 (OSRAM) | ||
| CA2434178A1 (en) | Substituted amine derivatives and methods of use | |
| JP2004527499A5 (OSRAM) | ||
| AU2011297889B2 (en) | Pharmaceutically active compounds as Axl inhibitors | |
| WO2023051716A1 (zh) | 杂芳基衍生物parp抑制剂及其用途 | |
| JP6461118B2 (ja) | ブロモドメイン阻害剤としての新規の置換された二環式化合物 | |
| JP2004531473A5 (OSRAM) | ||
| CN107207474B (zh) | 被取代的杂环作为溴结构域抑制剂 | |
| CA2366857C (en) | Phthalazine derivatives for treating inflammatory diseases | |
| ES2260156T3 (es) | Derivados de (imidazol-5-il)metil-2-quinolinona como inhibidores de la proteina farnesil-transferasa. | |
| AU2003256481B2 (en) | Substituted anthranilic amide derivatives and methods of use | |
| JP2024514223A (ja) | Ｐａｒｐ１阻害薬及びその使用 | |
| JP4613130B2 (ja) | ベンゾイミダゾールキノリノンおよびそれらの使用 | |
| ES2261476T3 (es) | Derivados de quinolina y quinazolina que inhiben la farnesil-tranferasa como inhibidores de farnesil-tranferasa. | |
| JP2004531484A5 (OSRAM) | ||
| TW202122387A (zh) | Mta協同性之prmt5抑制劑 | |
| IL171480A (en) | Aza spiro alkane derivatives as inhibitors of metalloproteases and pharmaceutical compositions and uses thereof | |
| US20050256157A1 (en) | Combination therapy with CHK1 inhibitors | |
| AU2004269000A1 (en) | Substituted 2,3-dihydro-1H-isoindol-1-one derivatives and methods of use | |
| JP2008525498A5 (OSRAM) | ||
| JP2014500323A5 (OSRAM) | ||
| JP2016539146A5 (OSRAM) | ||
| CN109415367A (zh) | 用于治疗和预防乙型肝炎病毒感染的新的二氢吡咯并嘧啶类化合物 | |
| ES2260316T3 (es) | Derivados de quinazolina y quinolina 4-sustituidos que inhiben la farnesil transferasa. |