JP2006501273A5 - - Google Patents
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- JP2006501273A5 JP2006501273A5 JP2004537020A JP2004537020A JP2006501273A5 JP 2006501273 A5 JP2006501273 A5 JP 2006501273A5 JP 2004537020 A JP2004537020 A JP 2004537020A JP 2004537020 A JP2004537020 A JP 2004537020A JP 2006501273 A5 JP2006501273 A5 JP 2006501273A5
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- Japan
- Prior art keywords
- group
- alkyl
- amino
- substituted
- alkoxy
- Prior art date
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- -1 C 1-3 -alkoxy Chemical group 0.000 claims 106
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 98
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 70
- 125000006842 cycloalkyleneimino group Chemical group 0.000 claims 51
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 38
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 34
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 34
- 125000000217 alkyl group Chemical group 0.000 claims 29
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 26
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 25
- 125000004434 sulfur atom Chemical group 0.000 claims 24
- 229910052717 sulfur Inorganic materials 0.000 claims 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 19
- 229910052760 oxygen Inorganic materials 0.000 claims 19
- 239000001301 oxygen Substances 0.000 claims 19
- 125000004430 oxygen atom Chemical group O* 0.000 claims 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 18
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 17
- 229910052801 chlorine Inorganic materials 0.000 claims 17
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 15
- 229910052757 nitrogen Inorganic materials 0.000 claims 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 14
- 229910052731 fluorine Inorganic materials 0.000 claims 14
- 239000011737 fluorine Substances 0.000 claims 14
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 12
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 11
- 239000000460 chlorine Substances 0.000 claims 11
- 125000004076 pyridyl group Chemical group 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 10
- 125000003277 amino group Chemical group 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 125000006563 (C1-3) alkylaminocarbonyl group Chemical group 0.000 claims 9
- 150000001721 carbon Chemical group 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical group N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 229910052740 iodine Inorganic materials 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000006576 di-(C1-C3-alkyl)-aminocarbonyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 6
- 239000000651 prodrug Substances 0.000 claims 6
- 229940002612 prodrug Drugs 0.000 claims 6
- 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 claims 5
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000006239 protecting group Chemical group 0.000 claims 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 4
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims 4
- 150000003951 lactams Chemical group 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 239000007790 solid phase Substances 0.000 claims 4
- 125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- JTTYBEQWOFZMFP-RQZHXJHFSA-N (3z)-3-[1,3-benzodioxol-5-yl-[4-[(4-methylpiperazin-1-yl)methyl]anilino]methylidene]-6-chloro-1h-indol-2-one Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1N\C(C=1C=C2OCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O JTTYBEQWOFZMFP-RQZHXJHFSA-N 0.000 claims 2
- KWFUYECTBFRIRG-IZHYLOQSSA-N (3z)-3-[1,3-benzodioxol-5-yl-[4-[[ethyl(methyl)amino]methyl]anilino]methylidene]-6-chloro-1h-indol-2-one Chemical compound C1=CC(CN(C)CC)=CC=C1N\C(C=1C=C2OCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O KWFUYECTBFRIRG-IZHYLOQSSA-N 0.000 claims 2
- KSJXPOZSSRPFPB-IZHYLOQSSA-N (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-(ethylaminomethyl)anilino]methylidene]-6-fluoro-1h-indol-2-one Chemical compound C1=CC(CNCC)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(F)C=C2NC\1=O KSJXPOZSSRPFPB-IZHYLOQSSA-N 0.000 claims 2
- ODEQWQXGCAYNQS-IZHYLOQSSA-N (3z)-6-chloro-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-[(dimethylamino)methyl]anilino]methylidene]-1h-indol-2-one Chemical compound C1=CC(CN(C)C)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O ODEQWQXGCAYNQS-IZHYLOQSSA-N 0.000 claims 2
- YAJULHYYDWJESD-IZHYLOQSSA-N (3z)-6-chloro-3-[[4-[(dimethylamino)methyl]anilino]-(1-methylbenzimidazol-5-yl)methylidene]-1h-indol-2-one Chemical compound C1=CC(CN(C)C)=CC=C1N\C(C=1C=C2N=CN(C)C2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O YAJULHYYDWJESD-IZHYLOQSSA-N 0.000 claims 2
- LKURCHRXPCDQMT-IZHYLOQSSA-N (3z)-6-fluoro-3-[(1-methylbenzimidazol-5-yl)-[4-(1,2,4-triazol-1-ylmethyl)anilino]methylidene]-1h-indol-2-one Chemical compound C=1C=C2N(C)C=NC2=CC=1C(=C\1C2=CC=C(F)C=C2NC/1=O)\NC(C=C1)=CC=C1CN1C=NC=N1 LKURCHRXPCDQMT-IZHYLOQSSA-N 0.000 claims 2
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical group OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- IXJISIDVDXYLTI-RQZHXJHFSA-N methyl (3z)-3-[1,3-benzodioxol-5-yl-[4-(diethylaminomethyl)anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CN(CC)CC)=CC=C1N\C(C=1C=C2OCOC2=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O IXJISIDVDXYLTI-RQZHXJHFSA-N 0.000 claims 2
- YDJNGVGZHOABKD-IZHYLOQSSA-N methyl (3z)-3-[1,3-benzodioxol-5-yl-[4-[(dimethylamino)methyl]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCOC2=CC=1)\NC1=CC=C(CN(C)C)C=C1 YDJNGVGZHOABKD-IZHYLOQSSA-N 0.000 claims 2
- XUKMQAUQPSBMPQ-RQZHXJHFSA-N methyl (3z)-3-[1,3-benzodioxol-5-yl-[4-[2-(dimethylamino)ethyl-methylcarbamoyl]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCOC2=CC=1)\NC1=CC=C(C(=O)N(C)CCN(C)C)C=C1 XUKMQAUQPSBMPQ-RQZHXJHFSA-N 0.000 claims 2
- VZCBAERILCJERL-QPLCGJKRSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-(ethylaminomethyl)anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound C1=CC(CNCC)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(C(=O)OC)C=C2NC\1=O VZCBAERILCJERL-QPLCGJKRSA-N 0.000 claims 2
- DJNBIJXUUAGOGV-DQSJHHFOSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-(pyrrolidin-1-ylmethyl)anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCCOC2=CC=1)\NC(C=C1)=CC=C1CN1CCCC1 DJNBIJXUUAGOGV-DQSJHHFOSA-N 0.000 claims 2
- ISQFIECKXMSFOU-ZIADKAODSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-[(4-methylpiperazin-1-yl)methyl]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCCOC2=CC=1)\NC(C=C1)=CC=C1CN1CCN(C)CC1 ISQFIECKXMSFOU-ZIADKAODSA-N 0.000 claims 2
- HPODJPLRFPIIGJ-QPLCGJKRSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-[(dimethylamino)methyl]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCCOC2=CC=1)\NC1=CC=C(CN(C)C)C=C1 HPODJPLRFPIIGJ-QPLCGJKRSA-N 0.000 claims 2
- MXWVZQNZTKXKKO-DQSJHHFOSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-[2-(dimethylamino)ethyl-methylcarbamoyl]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCCOC2=CC=1)\NC1=CC=C(C(=O)N(C)CCN(C)C)C=C1 MXWVZQNZTKXKKO-DQSJHHFOSA-N 0.000 claims 2
- PAIOVUWLCWJFCV-DQSJHHFOSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-[2-(dimethylamino)ethyl-methylsulfonylamino]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCCOC2=CC=1)\NC1=CC=C(N(CCN(C)C)S(C)(=O)=O)C=C1 PAIOVUWLCWJFCV-DQSJHHFOSA-N 0.000 claims 2
- AOPHCTKRYHULCH-ZIADKAODSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-[3-(dimethylamino)propyl-methylcarbamoyl]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCCOC2=CC=1)\NC1=CC=C(C(=O)N(C)CCCN(C)C)C=C1 AOPHCTKRYHULCH-ZIADKAODSA-N 0.000 claims 2
- SXWOVUCGBCAXQL-DQSJHHFOSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-[[2-(dimethylamino)acetyl]-methylamino]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCCOC2=CC=1)\NC1=CC=C(N(C)C(=O)CN(C)C)C=C1 SXWOVUCGBCAXQL-DQSJHHFOSA-N 0.000 claims 2
- ODQMWYRZGUKRRX-KTMFPKCZSA-N methyl (3z)-3-[2,3-dihydro-1,4-benzodioxin-6-yl-[4-[methyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]anilino]methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCCOC2=CC=1)\NC(C=C1)=CC=C1N(C)C(=O)CN1CCN(C)CC1 ODQMWYRZGUKRRX-KTMFPKCZSA-N 0.000 claims 2
- NLWJTHWHZRNPHE-ZIADKAODSA-N methyl (3z)-3-[[4-[acetyl-[2-(dimethylamino)ethyl]amino]anilino]-(2,3-dihydro-1,4-benzodioxin-6-yl)methylidene]-2-oxo-1h-indole-6-carboxylate Chemical compound O=C1NC2=CC(C(=O)OC)=CC=C2\C1=C(C=1C=C2OCCOC2=CC=1)\NC1=CC=C(N(CCN(C)C)C(C)=O)C=C1 NLWJTHWHZRNPHE-ZIADKAODSA-N 0.000 claims 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 2
- YIFIFSOAJPIGIJ-DQSJHHFOSA-N n-[4-[[(z)-(6-chloro-2-oxo-1h-indol-3-ylidene)-(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]amino]phenyl]-n-[2-(dimethylamino)ethyl]acetamide Chemical compound C1=CC(N(C(C)=O)CCN(C)C)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O YIFIFSOAJPIGIJ-DQSJHHFOSA-N 0.000 claims 2
- LAUNLLGATPLKLE-RQZHXJHFSA-N n-[4-[[(z)-(6-chloro-2-oxo-1h-indol-3-ylidene)-(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]amino]phenyl]-n-[2-(dimethylamino)ethyl]methanesulfonamide Chemical compound C1=CC(N(CCN(C)C)S(C)(=O)=O)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O LAUNLLGATPLKLE-RQZHXJHFSA-N 0.000 claims 2
- LMCVWVYZMQAGJZ-ZIADKAODSA-N n-[4-[[(z)-(6-chloro-2-oxo-1h-indol-3-ylidene)-(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]amino]phenyl]-n-[2-(dimethylamino)ethyl]propanamide Chemical compound C1=CC(N(CCN(C)C)C(=O)CC)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O LMCVWVYZMQAGJZ-ZIADKAODSA-N 0.000 claims 2
- DVEVDZVUEOLBQR-ZIADKAODSA-N n-[4-[[(z)-(6-chloro-2-oxo-1h-indol-3-ylidene)-(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]amino]phenyl]-n-[3-(dimethylamino)propyl]acetamide Chemical compound C1=CC(N(C(C)=O)CCCN(C)C)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O DVEVDZVUEOLBQR-ZIADKAODSA-N 0.000 claims 2
- JDSVKRGOXWZTOV-FLWNBWAVSA-N n-[4-[[(z)-(6-chloro-2-oxo-1h-indol-3-ylidene)-(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]amino]phenyl]-n-[3-(dimethylamino)propyl]propanamide Chemical compound C1=CC(N(CCCN(C)C)C(=O)CC)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O JDSVKRGOXWZTOV-FLWNBWAVSA-N 0.000 claims 2
- NGHNVCYNFAUQID-ZIADKAODSA-N n-[4-[[(z)-1,3-benzodioxol-5-yl-(6-chloro-2-oxo-1h-indol-3-ylidene)methyl]amino]phenyl]-n-methyl-2-(4-methylpiperazin-1-yl)acetamide Chemical compound C=1C=C(N\C(=C/2C3=CC=C(Cl)C=C3NC\2=O)C=2C=C3OCOC3=CC=2)C=CC=1N(C)C(=O)CN1CCN(C)CC1 NGHNVCYNFAUQID-ZIADKAODSA-N 0.000 claims 2
- NVIHLCZLWCZJBD-DQSJHHFOSA-N n-[4-[[(z)-2,3-dihydro-1,4-benzodioxin-6-yl-(6-fluoro-2-oxo-1h-indol-3-ylidene)methyl]amino]phenyl]-3-(dimethylamino)-n-methylpropanamide Chemical compound C1=CC(N(C)C(=O)CCN(C)C)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(F)C=C2NC\1=O NVIHLCZLWCZJBD-DQSJHHFOSA-N 0.000 claims 2
- MFYUMLZIDDEUAL-DQSJHHFOSA-N n-[4-[[(z)-2,3-dihydro-1,4-benzodioxin-6-yl-(6-fluoro-2-oxo-1h-indol-3-ylidene)methyl]amino]phenyl]-n-[2-(dimethylamino)ethyl]acetamide Chemical compound C1=CC(N(C(C)=O)CCN(C)C)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(F)C=C2NC\1=O MFYUMLZIDDEUAL-DQSJHHFOSA-N 0.000 claims 2
- VENAFAWDQVOHSC-RQZHXJHFSA-N n-[4-[[(z)-2,3-dihydro-1,4-benzodioxin-6-yl-(6-fluoro-2-oxo-1h-indol-3-ylidene)methyl]amino]phenyl]-n-[2-(dimethylamino)ethyl]methanesulfonamide Chemical compound C1=CC(N(CCN(C)C)S(C)(=O)=O)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(F)C=C2NC\1=O VENAFAWDQVOHSC-RQZHXJHFSA-N 0.000 claims 2
- TUSQYMMJEGRGEE-ZIADKAODSA-N n-[4-[[(z)-2,3-dihydro-1,4-benzodioxin-6-yl-(6-fluoro-2-oxo-1h-indol-3-ylidene)methyl]amino]phenyl]-n-[2-(dimethylamino)ethyl]propanamide Chemical compound C1=CC(N(CCN(C)C)C(=O)CC)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(F)C=C2NC\1=O TUSQYMMJEGRGEE-ZIADKAODSA-N 0.000 claims 2
- HRPALFYCQQDKHS-FLWNBWAVSA-N n-[4-[[(z)-2,3-dihydro-1,4-benzodioxin-6-yl-(6-fluoro-2-oxo-1h-indol-3-ylidene)methyl]amino]phenyl]-n-[3-(dimethylamino)propyl]propanamide Chemical compound C1=CC(N(CCCN(C)C)C(=O)CC)=CC=C1N\C(C=1C=C2OCCOC2=CC=1)=C/1C2=CC=C(F)C=C2NC\1=O HRPALFYCQQDKHS-FLWNBWAVSA-N 0.000 claims 2
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims 2
- 125000006850 spacer group Chemical group 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- NWXVVFGMDWXASW-VHXPQNKSSA-N (3z)-3-[1,3-benzodioxol-5-yl-[4-[(dimethylamino)methyl]anilino]methylidene]-6-chloro-1h-indol-2-one Chemical compound C1=CC(CN(C)C)=CC=C1N\C(C=1C=C2OCOC2=CC=1)=C/1C2=CC=C(Cl)C=C2NC\1=O NWXVVFGMDWXASW-VHXPQNKSSA-N 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 230000009435 amidation Effects 0.000 claims 1
- 238000007112 amidation reaction Methods 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- WWULUXRSBUVGLP-FLWNBWAVSA-N n-[4-[[(z)-(6-chloro-2-oxo-1h-indol-3-ylidene)-quinoxalin-6-ylmethyl]amino]phenyl]-n-methyl-2-(4-methylpiperazin-1-yl)acetamide Chemical compound C=1C=C(N\C(=C/2C3=CC=C(Cl)C=C3NC\2=O)C=2C=C3N=CC=NC3=CC=2)C=CC=1N(C)C(=O)CN1CCN(C)CC1 WWULUXRSBUVGLP-FLWNBWAVSA-N 0.000 claims 1
- ORCORJGKVRYZMU-ZIADKAODSA-N n-[4-[[(z)-1,3-benzodioxol-5-yl-(6-bromo-2-oxo-1h-indol-3-ylidene)methyl]amino]phenyl]-n-methyl-2-(4-methylpiperazin-1-yl)acetamide Chemical compound C=1C=C(N\C(=C/2C3=CC=C(Br)C=C3NC\2=O)C=2C=C3OCOC3=CC=2)C=CC=1N(C)C(=O)CN1CCN(C)CC1 ORCORJGKVRYZMU-ZIADKAODSA-N 0.000 claims 1
- AEKCMFSCXYBMTH-ZIADKAODSA-N n-[4-[[(z)-1,3-benzodioxol-5-yl-(6-fluoro-2-oxo-1h-indol-3-ylidene)methyl]amino]phenyl]-n-methyl-2-(4-methylpiperazin-1-yl)acetamide Chemical compound C=1C=C(N\C(=C/2C3=CC=C(F)C=C3NC\2=O)C=2C=C3OCOC3=CC=2)C=CC=1N(C)C(=O)CN1CCN(C)CC1 AEKCMFSCXYBMTH-ZIADKAODSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 238000005932 reductive alkylation reaction Methods 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 230000006103 sulfonylation Effects 0.000 claims 1
- 238000005694 sulfonylation reaction Methods 0.000 claims 1
- 125000005505 thiomorpholino group Chemical group 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2002142350 DE10242350A1 (de) | 2002-09-12 | 2002-09-12 | Heterocyclisch substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
| DE10252969A DE10252969A1 (de) | 2002-11-14 | 2002-11-14 | Heterocyclisch substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
| PCT/EP2003/009978 WO2004026829A2 (de) | 2002-09-12 | 2003-09-09 | Heterocyclisch substituierte indolinone und deren verwendung als rezeptor-tyrosinkinasen inhibitoren |
Publications (2)
| Publication Number | Publication Date |
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| JP2006501273A JP2006501273A (ja) | 2006-01-12 |
| JP2006501273A5 true JP2006501273A5 (enExample) | 2006-02-23 |
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| EP (1) | EP1551830B1 (enExample) |
| JP (1) | JP2006501273A (enExample) |
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| CA (1) | CA2498781A1 (enExample) |
| DE (1) | DE50311397D1 (enExample) |
| ES (1) | ES2324710T3 (enExample) |
| PE (1) | PE20041080A1 (enExample) |
| TW (1) | TW200407125A (enExample) |
| WO (1) | WO2004026829A2 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6982260B1 (en) | 1999-11-22 | 2006-01-03 | Warner-Lambert Company | Quinazolines and their use for inhibiting cyclin-dependent kinase enzymes |
| DE60144284D1 (de) | 2000-11-01 | 2011-05-05 | Millennium Pharm Inc | Stickstoffhaltige heterozyklische verbindungen und verfahren zu deren herstellung |
| US20040204458A1 (en) * | 2002-08-16 | 2004-10-14 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Use of Lck inhibitors for treatment of immunologic diseases |
| AU2004298448B2 (en) | 2003-12-18 | 2010-09-09 | Janssen Pharmaceutica N.V. | Pyrido- and pyrimidopyrimidine derivatives as anti- proliferative agents |
| KR100629713B1 (ko) * | 2004-04-10 | 2006-09-29 | (주)아모레퍼시픽 | 펜타에리스리톨 유도체와 이의 제조방법, 및 이를포함하는 액정베이스 |
| NI200700147A (es) | 2004-12-08 | 2019-05-10 | Janssen Pharmaceutica Nv | Derivados de quinazolina inhibidores de cinasas dirigidos a multip |
| PE20060777A1 (es) | 2004-12-24 | 2006-10-06 | Boehringer Ingelheim Int | Derivados de indolinona para el tratamiento o la prevencion de enfermedades fibroticas |
| CA2654583C (en) | 2006-07-13 | 2015-11-24 | Janssen Pharmaceutica N.V. | Mtki quinazoline derivatives |
| AU2007296740B2 (en) * | 2006-09-11 | 2012-09-27 | Curis, Inc. | Substituted 2-indolinone as PTK inhibitors containing a zinc binding moiety |
| EP2170827B1 (en) * | 2007-06-21 | 2013-08-14 | Janssen Pharmaceutica, N.V. | Indolin-2-ones and aza-indolin-2-ones |
| AU2008281849B2 (en) | 2007-07-27 | 2013-11-28 | Janssen Pharmaceutica Nv | Pyrrolopyrimidines |
| PE20091445A1 (es) * | 2007-12-03 | 2009-10-19 | Boehringer Ingelheim Int | Derivados de indolinona y procedimiento para su fabricacion |
| TR201802086T4 (tr) * | 2007-12-03 | 2018-03-21 | Boehringer Ingelheim Int | Bir indolinon türevinin imalatı için proses. |
| EP2235004A4 (en) * | 2007-12-21 | 2011-05-04 | Univ Health Network | INDAZOLYL, BENZIMIDAZOLYL, BENZOTRIAZOLYL-SUBSTITUTED INDOLUND DERIVATIVES AS A KINASE-HEMMER FOR CANCER TREATMENT |
| MX338047B (es) * | 2008-06-06 | 2016-03-31 | Boehringer Ingelheim Int | Combinacion farmaceutica útil para el tratamiento fr enfermedades que involucran proliferación celular, migración o apoptosis de células de mieloma, angiogéneisis o fibrosis. |
| AU2009275964A1 (en) | 2008-07-29 | 2010-02-04 | Boehringer Ingelheim International Gmbh | New compounds |
| WO2010115279A1 (en) | 2009-04-06 | 2010-10-14 | University Health Network | Kinase inhibitors and method of treating cancer with same |
| TWI516262B (zh) * | 2010-04-06 | 2016-01-11 | 健康網路大學 | 激酶抑制劑及以其治療癌症的方法 |
| WO2012048411A1 (en) * | 2010-10-13 | 2012-04-19 | University Health Network | Plk-4 inhibitors and method of treating cancer with same |
| WO2014086102A1 (zh) * | 2012-12-06 | 2014-06-12 | 山东亨利医药科技有限责任公司 | 作为酪氨酸激酶抑制剂的吲哚满酮衍生物 |
| CN103848814B (zh) * | 2012-12-06 | 2016-08-17 | 山东亨利医药科技有限责任公司 | 作为酪氨酸激酶抑制剂的取代吲哚满酮衍生物 |
| JP6239103B2 (ja) | 2013-06-20 | 2017-11-29 | 中国人民解放軍軍事医学科学院放射及び輻射医学研究所Ｉｎｓｔｉｔｕｔｅ Ｏｆ Ｒａｄｉａｔｉｏｎ Ｍｅｄｉｃｉｎｅ， Ａｃａｄｅｍｙ Ｏｆ Ｍｉｌｉｔａｒｙ Ｍｅｄｉｃａｌ Ｓｃｉｅｎｃｅｓ， Ｐｅｏｐｌｅ’Ｓ Ｌｉｂｒａｔｉｏｎ Ａｒｍｙ Ｏｆ Ｃｈｉｎａ | チロシンキナーゼ阻害活性を有する物質ならびにその調製方法および使用 |
| EA030089B1 (ru) | 2013-10-18 | 2018-06-29 | Юниверсити Хелс Нетуорк | Лечение рака поджелудочной железы |
| EP3564232B1 (en) | 2016-12-27 | 2022-01-26 | Riken | Bmp-signal-inhibiting compound |
| CN112174943A (zh) * | 2019-07-03 | 2021-01-05 | 四川大学 | 一种吲哚-2-酮类化合物在制备防治口腔细菌产品中的用途 |
| CN114213396B (zh) * | 2022-01-27 | 2023-03-24 | 深圳市乐土生物医药有限公司 | 一种吲哚-2-酮类化合物及其制备方法与用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1319090A (zh) * | 1998-09-25 | 2001-10-24 | 贝林格尔英格海姆法玛公司 | 新的取代的二氢吲哚酮、它们的制备方法和它们作为药物的用途 |
| WO2001016130A1 (de) | 1999-08-27 | 2001-03-08 | Boehringer Ingelheim Pharma Kg | Substituierte indolinone als tyrosinkinase inhibitoren |
| US6762180B1 (en) * | 1999-10-13 | 2004-07-13 | Boehringer Ingelheim Pharma Kg | Substituted indolines which inhibit receptor tyrosine kinases |
| DE19949209A1 (de) | 1999-10-13 | 2001-04-19 | Boehringer Ingelheim Pharma | In 5-Stellung substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
| UA75054C2 (uk) | 1999-10-13 | 2006-03-15 | Бьорінгер Інгельхайм Фарма Гмбх & Ко. Кг | Заміщені в положенні 6 індолінони, їх одержання та їх застосування як лікарського засобу |
| DE10117204A1 (de) * | 2001-04-06 | 2002-10-10 | Boehringer Ingelheim Pharma | In 6-Stellung substituierte Indolinone, ihre Herstellung und ihre Verwendung als Arzneimittel |
-
2003
- 2003-09-05 US US10/656,863 patent/US7148249B2/en not_active Expired - Lifetime
- 2003-09-09 ES ES03757806T patent/ES2324710T3/es not_active Expired - Lifetime
- 2003-09-09 CA CA002498781A patent/CA2498781A1/en not_active Abandoned
- 2003-09-09 DE DE50311397T patent/DE50311397D1/de not_active Expired - Lifetime
- 2003-09-09 JP JP2004537020A patent/JP2006501273A/ja active Pending
- 2003-09-09 AT AT03757806T patent/ATE427947T1/de not_active IP Right Cessation
- 2003-09-09 WO PCT/EP2003/009978 patent/WO2004026829A2/de not_active Ceased
- 2003-09-09 EP EP03757806A patent/EP1551830B1/de not_active Expired - Lifetime
- 2003-09-09 AU AU2003273842A patent/AU2003273842A1/en not_active Abandoned
- 2003-09-10 PE PE2003000915A patent/PE20041080A1/es not_active Application Discontinuation
- 2003-09-10 TW TW092125060A patent/TW200407125A/zh unknown
- 2003-09-12 AR ARP030103306A patent/AR041194A1/es unknown
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