JP2004518669A5 - - Google Patents
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- JP2004518669A5 JP2004518669A5 JP2002556186A JP2002556186A JP2004518669A5 JP 2004518669 A5 JP2004518669 A5 JP 2004518669A5 JP 2002556186 A JP2002556186 A JP 2002556186A JP 2002556186 A JP2002556186 A JP 2002556186A JP 2004518669 A5 JP2004518669 A5 JP 2004518669A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- phenyl
- methyl
- dimethyl
- indole
- 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.)
- Pending
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- 229910005965 SO 2 Inorganic materials 0.000 claims 67
- 125000000217 alkyl group Chemical group 0.000 claims 54
- 125000000623 heterocyclic group Chemical group 0.000 claims 29
- -1 —COR 12 Chemical group 0.000 claims 28
- 125000003118 aryl group Chemical group 0.000 claims 27
- 125000003342 alkenyl group Chemical group 0.000 claims 25
- 125000000304 alkynyl group Chemical group 0.000 claims 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 201000010099 disease Diseases 0.000 claims 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 11
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 8
- 102000001253 Protein Kinase Human genes 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 108060006633 protein kinase Proteins 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 230000003197 catalytic effect Effects 0.000 claims 4
- OMBFUKZWGIHJDZ-IAGOWNOFSA-N 3-[[3-[(3R,5R)-3,5-dimethylpiperazine-1-carbonyl]-5-methyl-1H-pyrrol-2-yl]methylidene]-4-(3-fluorophenyl)-1H-indol-2-one Chemical compound C1[C@@H](C)N[C@H](C)CN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(F)C=CC=2)NC(C)=C1 OMBFUKZWGIHJDZ-IAGOWNOFSA-N 0.000 claims 3
- YNQYKQKNMVRPNW-IAGOWNOFSA-N 3-[[4-[(3R,5R)-3,5-dimethylpiperazine-1-carbonyl]-3,5-dimethyl-1H-pyrrol-2-yl]methylidene]-4-(3-methoxyphenyl)-1H-indol-2-one Chemical compound COC1=CC=CC(C=2C=3C(=CC4=C(C(C(=O)N5C[C@@H](C)N[C@H](C)C5)=C(C)N4)C)C(=O)NC=3C=CC=2)=C1 YNQYKQKNMVRPNW-IAGOWNOFSA-N 0.000 claims 3
- SLYDLEPXGOJXRI-IAGOWNOFSA-N 3-[[4-[(3R,5R)-3,5-dimethylpiperazine-1-carbonyl]-3,5-dimethyl-1H-pyrrol-2-yl]methylidene]-4-(4-methoxyphenyl)-1H-indol-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C)C(C(=O)N2C[C@@H](C)N[C@H](C)C2)=C(C)N1 SLYDLEPXGOJXRI-IAGOWNOFSA-N 0.000 claims 3
- CARQSIFVDPCMTO-IAGOWNOFSA-N 4-(4-chlorophenyl)-3-[[3-[(3R,5R)-3,5-dimethylpiperazine-1-carbonyl]-5-methyl-1H-pyrrol-2-yl]methylidene]-1H-indol-2-one Chemical compound C1[C@@H](C)N[C@H](C)CN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(Cl)=CC=2)NC(C)=C1 CARQSIFVDPCMTO-IAGOWNOFSA-N 0.000 claims 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 claims 3
- 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Chemical group 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 229910052740 iodine Chemical group 0.000 claims 3
- 239000011630 iodine Chemical group 0.000 claims 3
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims 3
- 108091008598 receptor tyrosine kinases Proteins 0.000 claims 3
- 102000027426 receptor tyrosine kinases Human genes 0.000 claims 3
- VRDZWSOXVUAKHZ-UHFFFAOYSA-N 2,4-dimethyl-5-[[2-oxo-4-[3-(trifluoromethyl)phenyl]-1h-indol-3-ylidene]methyl]-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2CCCC2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=CC(C(F)(F)F)=C1 VRDZWSOXVUAKHZ-UHFFFAOYSA-N 0.000 claims 2
- WQPBSCLIBHMJJX-UHFFFAOYSA-N 2,4-dimethyl-5-[[2-oxo-4-[3-(trifluoromethyl)phenyl]-1h-indol-3-ylidene]methyl]-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2N=NC=C2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=CC(C(F)(F)F)=C1 WQPBSCLIBHMJJX-UHFFFAOYSA-N 0.000 claims 2
- AWQPLPDSGWJCFI-UHFFFAOYSA-N 2,4-dimethyl-5-[[2-oxo-4-[4-(trifluoromethoxy)phenyl]-1h-indol-3-ylidene]methyl]-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NCCN2N=NC=C2)=C(C)NC=1C=C(C=12)C(=O)NC2=CC=CC=1C1=CC=C(OC(F)(F)F)C=C1 AWQPLPDSGWJCFI-UHFFFAOYSA-N 0.000 claims 2
- CHEYEJGXQSHSFE-UHFFFAOYSA-N 2-(triazol-1-yl)ethanamine Chemical compound NCCN1C=CN=N1 CHEYEJGXQSHSFE-UHFFFAOYSA-N 0.000 claims 2
- WWFONFNTBIRHHQ-UHFFFAOYSA-N 2-[[4-(2-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C(=CC=CC=3)F)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1CCCC1 WWFONFNTBIRHHQ-UHFFFAOYSA-N 0.000 claims 2
- MPYXQHOXIXPUIY-UHFFFAOYSA-N 2-[[4-(2-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C(=CC=CC=3)F)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1C=CN=N1 MPYXQHOXIXPUIY-UHFFFAOYSA-N 0.000 claims 2
- LZWCQKJJTUNHNL-UHFFFAOYSA-N 2-[[4-(3-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=C(Br)C=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1CCCC1 LZWCQKJJTUNHNL-UHFFFAOYSA-N 0.000 claims 2
- UXOTVNCSRBHACK-UHFFFAOYSA-N 2-[[4-(3-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=C(Br)C=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1C=CN=N1 UXOTVNCSRBHACK-UHFFFAOYSA-N 0.000 claims 2
- QFBVFXVKRWTEDQ-UHFFFAOYSA-N 2-[[4-(3-chlorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=C(Cl)C=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1C=CN=N1 QFBVFXVKRWTEDQ-UHFFFAOYSA-N 0.000 claims 2
- MBYSYJLDYCWYFM-UHFFFAOYSA-N 2-[[4-(3-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound COC1=CC=CC(C=2C=3C(=CC4=C(C=C(C)N4)C(=O)NCCN4CCCC4)C(=O)NC=3C=CC=2)=C1 MBYSYJLDYCWYFM-UHFFFAOYSA-N 0.000 claims 2
- XUJAOXLHJLEGIP-UHFFFAOYSA-N 2-[[4-(3-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound COC1=CC=CC(C=2C=3C(=CC4=C(C=C(C)N4)C(=O)NCCN4N=NC=C4)C(=O)NC=3C=CC=2)=C1 XUJAOXLHJLEGIP-UHFFFAOYSA-N 0.000 claims 2
- ZBKZSYQZWMQECM-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=CC(Br)=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1CCCC1 ZBKZSYQZWMQECM-UHFFFAOYSA-N 0.000 claims 2
- KNNIAMMFXFIEET-UHFFFAOYSA-N 2-[[4-(4-bromophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=CC(Br)=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1C=CN=N1 KNNIAMMFXFIEET-UHFFFAOYSA-N 0.000 claims 2
- AMKILMQZHWJJCT-UHFFFAOYSA-N 2-[[4-(4-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-(3-pyrrolidin-1-ylpropyl)-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=CC(F)=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCCN1CCCC1 AMKILMQZHWJJCT-UHFFFAOYSA-N 0.000 claims 2
- KLPDZNJUFDCVSM-UHFFFAOYSA-N 2-[[4-(4-fluorophenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-[2-(triazol-1-yl)ethyl]-1h-pyrrole-3-carboxamide Chemical compound O=C1NC2=CC=CC(C=3C=CC(F)=CC=3)=C2C1=CC=1NC(C)=CC=1C(=O)NCCN1C=CN=N1 KLPDZNJUFDCVSM-UHFFFAOYSA-N 0.000 claims 2
- PAYQSBWVABTJPX-UHFFFAOYSA-N 2-[[4-(4-methoxyphenyl)-2-oxo-1h-indol-3-ylidene]methyl]-5-methyl-n-(2-pyrrolidin-1-ylethyl)-1h-pyrrole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C(=O)NCCN2CCCC2)C=C(C)N1 PAYQSBWVABTJPX-UHFFFAOYSA-N 0.000 claims 2
- VGNGCEOLEPSPNU-UHFFFAOYSA-N 3-[(3,5-dimethyl-1h-pyrrol-2-yl)methylidene]-4-(3-fluorophenyl)-1h-indol-2-one Chemical compound N1C(C)=CC(C)=C1C=C1C2=C(C=3C=C(F)C=CC=3)C=CC=C2NC1=O VGNGCEOLEPSPNU-UHFFFAOYSA-N 0.000 claims 2
- RCSCKFQMSMVNJE-UHFFFAOYSA-N 3-[(3,5-dimethyl-1h-pyrrol-2-yl)methylidene]-4-(3-methoxyphenyl)-1h-indol-2-one Chemical compound COC1=CC=CC(C=2C=3C(=CC4=C(C=C(C)N4)C)C(=O)NC=3C=CC=2)=C1 RCSCKFQMSMVNJE-UHFFFAOYSA-N 0.000 claims 2
- BHDNPWIGOZQIDE-UHFFFAOYSA-N 3-[(3,5-dimethyl-1h-pyrrol-2-yl)methylidene]-4-(4-fluorophenyl)-1h-indol-2-one Chemical compound N1C(C)=CC(C)=C1C=C1C2=C(C=3C=CC(F)=CC=3)C=CC=C2NC1=O BHDNPWIGOZQIDE-UHFFFAOYSA-N 0.000 claims 2
- CMOLXROSUKSQJU-UHFFFAOYSA-N 3-[(3,5-dimethyl-1h-pyrrol-2-yl)methylidene]-4-(4-methoxyphenyl)-1h-indol-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C)C=C(C)N1 CMOLXROSUKSQJU-UHFFFAOYSA-N 0.000 claims 2
- YVIDARGTGQKWAU-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-(3-fluorophenyl)-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(F)C=CC=2)=C1C YVIDARGTGQKWAU-UHFFFAOYSA-N 0.000 claims 2
- QJDXAJSEIJIGGZ-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-(3-methoxyphenyl)-1h-indol-2-one Chemical compound COC1=CC=CC(C=2C=3C(=CC4=C(C(C(=O)N5CCN(C)CC5)=C(C)N4)C)C(=O)NC=3C=CC=2)=C1 QJDXAJSEIJIGGZ-UHFFFAOYSA-N 0.000 claims 2
- NJSIYXJIHSXVLH-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-(4-fluorophenyl)-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(F)=CC=2)=C1C NJSIYXJIHSXVLH-UHFFFAOYSA-N 0.000 claims 2
- CCWBUISYAAUALO-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-(4-methoxyphenyl)-1h-indol-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C)C(C(=O)N2CCN(C)CC2)=C(C)N1 CCWBUISYAAUALO-UHFFFAOYSA-N 0.000 claims 2
- ZJDMBWHFQMJBPH-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-[3-(trifluoromethyl)phenyl]-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(C=CC=2)C(F)(F)F)=C1C ZJDMBWHFQMJBPH-UHFFFAOYSA-N 0.000 claims 2
- XJCSMRBRCNMPIL-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-[4-(trifluoromethoxy)phenyl]-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(OC(F)(F)F)=CC=2)=C1C XJCSMRBRCNMPIL-UHFFFAOYSA-N 0.000 claims 2
- VEMKJZMGZDCKEQ-UHFFFAOYSA-N 3-[[3,5-dimethyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-phenyl-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=C(C)NC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC=CC=2)=C1C VEMKJZMGZDCKEQ-UHFFFAOYSA-N 0.000 claims 2
- LJUXSADWDTYQAQ-LJQANCHMSA-N 3-[[3-[(3r)-3-(dimethylamino)pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(3-fluorophenyl)-1h-indol-2-one Chemical compound C1[C@H](N(C)C)CCN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(F)C=CC=2)NC(C)=C1 LJUXSADWDTYQAQ-LJQANCHMSA-N 0.000 claims 2
- ZGWWWHVRMOHQTD-LJQANCHMSA-N 3-[[3-[(3r)-3-(dimethylamino)pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(4-fluorophenyl)-1h-indol-2-one Chemical compound C1[C@H](N(C)C)CCN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(F)=CC=2)NC(C)=C1 ZGWWWHVRMOHQTD-LJQANCHMSA-N 0.000 claims 2
- IAMVCPKGFHJBJS-LJQANCHMSA-N 3-[[3-[(3r)-3-(dimethylamino)pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(4-methoxyphenyl)-1h-indol-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C(=O)N2C[C@@H](CC2)N(C)C)C=C(C)N1 IAMVCPKGFHJBJS-LJQANCHMSA-N 0.000 claims 2
- VDBPUKCYNGJKAD-CALCHBBNSA-N 3-[[3-[(3r,5s)-3,5-dimethylpiperazine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(2-fluorophenyl)-1h-indol-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C(=CC=CC=2)F)NC(C)=C1 VDBPUKCYNGJKAD-CALCHBBNSA-N 0.000 claims 2
- OMBFUKZWGIHJDZ-CALCHBBNSA-N 3-[[3-[(3r,5s)-3,5-dimethylpiperazine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(3-fluorophenyl)-1h-indol-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(F)C=CC=2)NC(C)=C1 OMBFUKZWGIHJDZ-CALCHBBNSA-N 0.000 claims 2
- LJUXSADWDTYQAQ-IBGZPJMESA-N 3-[[3-[(3s)-3-(dimethylamino)pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(3-fluorophenyl)-1h-indol-2-one Chemical compound C1[C@@H](N(C)C)CCN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(F)C=CC=2)NC(C)=C1 LJUXSADWDTYQAQ-IBGZPJMESA-N 0.000 claims 2
- ZGWWWHVRMOHQTD-IBGZPJMESA-N 3-[[3-[(3s)-3-(dimethylamino)pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(4-fluorophenyl)-1h-indol-2-one Chemical compound C1[C@@H](N(C)C)CCN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC(F)=CC=2)NC(C)=C1 ZGWWWHVRMOHQTD-IBGZPJMESA-N 0.000 claims 2
- IAMVCPKGFHJBJS-IBGZPJMESA-N 3-[[3-[(3s)-3-(dimethylamino)pyrrolidine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-(4-methoxyphenyl)-1h-indol-2-one Chemical compound C1=CC(OC)=CC=C1C1=CC=CC(NC2=O)=C1C2=CC1=C(C(=O)N2C[C@H](CC2)N(C)C)C=C(C)N1 IAMVCPKGFHJBJS-IBGZPJMESA-N 0.000 claims 2
- FKZDPHCNJSKHMY-CALCHBBNSA-N 3-[[3-[(3s,5r)-3,5-dimethylpiperazine-1-carbonyl]-5-methyl-1h-pyrrol-2-yl]methylidene]-4-[2-(trifluoromethyl)phenyl]-1h-indol-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C(=O)C1=C(C=C2C3=C(C=CC=C3NC2=O)C=2C(=CC=CC=2)C(F)(F)F)NC(C)=C1 FKZDPHCNJSKHMY-CALCHBBNSA-N 0.000 claims 2
- BLGCOODZQHTUFQ-UHFFFAOYSA-N 3-[[3-methyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-[3-(trifluoromethyl)phenyl]-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=CNC(C=C2C3=C(C=CC=C3NC2=O)C=2C=C(C=CC=2)C(F)(F)F)=C1C BLGCOODZQHTUFQ-UHFFFAOYSA-N 0.000 claims 2
- DZCAHMJKIBPTJQ-UHFFFAOYSA-N 3-[[3-methyl-4-(4-methylpiperazine-1-carbonyl)-1h-pyrrol-2-yl]methylidene]-4-phenyl-1h-indol-2-one Chemical compound C1CN(C)CCN1C(=O)C1=CNC(C=C2C3=C(C=CC=C3NC2=O)C=2C=CC=CC=2)=C1C DZCAHMJKIBPTJQ-UHFFFAOYSA-N 0.000 claims 2
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| PL1638941T3 (pl) * | 2003-05-22 | 2010-11-30 | Abbvie Bahamas Ltd | Indazolowe, benzizoksazolowe i benzizotiazolowe inhibitory kinaz |
| RU2365373C2 (ru) * | 2003-05-27 | 2009-08-27 | Роберт Пер Хэгерквист | Применение ингибитора тирозинкиназы для лечения диабета |
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-
2001
- 2001-12-20 PE PE2001001289A patent/PE20020776A1/es not_active Application Discontinuation
- 2001-12-20 EP EP01997065A patent/EP1349852A2/en not_active Withdrawn
- 2001-12-20 CA CA002432114A patent/CA2432114A1/en not_active Abandoned
- 2001-12-20 JP JP2002556186A patent/JP2004518669A/ja active Pending
- 2001-12-20 WO PCT/US2001/048564 patent/WO2002055517A2/en not_active Ceased
- 2001-12-20 AR ARP010105973A patent/AR035721A1/es unknown
- 2001-12-20 US US10/023,488 patent/US6677368B2/en not_active Expired - Fee Related
-
2003
- 2003-12-16 US US10/736,243 patent/US6861418B2/en not_active Expired - Fee Related
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