JP2007503450A5 - - Google Patents
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- 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.)
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- -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
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| PCT/US2004/027595 WO2005021532A1 (en) | 2003-08-25 | 2004-08-25 | Substituted 2,3-dihydro-1h-isoindol-1-one derivatives and methods of use |
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|---|---|---|---|---|
| US7745641B2 (en) * | 2005-04-19 | 2010-06-29 | Kyowa Hakko Kirin Co., Ltd. | Nitrogen-containing heterocyclic compound |
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- 2004-08-24 US US10/926,238 patent/US7320992B2/en not_active Expired - Lifetime
- 2004-08-25 AT AT04782152T patent/ATE453636T1/de not_active IP Right Cessation
- 2004-08-25 MX MXPA06001923A patent/MXPA06001923A/es not_active Application Discontinuation
- 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 DE DE602004024900T patent/DE602004024900D1/de not_active Expired - Lifetime
- 2004-08-25 ES ES04782152T patent/ES2337062T3/es not_active Expired - Lifetime
- 2004-08-25 CA CA002534570A patent/CA2534570A1/en not_active Abandoned
- 2004-08-25 EP EP04782152A patent/EP1664027B1/en not_active Expired - Lifetime
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