JP2002532490A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2002532490A5 JP2002532490A5 JP2000588166A JP2000588166A JP2002532490A5 JP 2002532490 A5 JP2002532490 A5 JP 2002532490A5 JP 2000588166 A JP2000588166 A JP 2000588166A JP 2000588166 A JP2000588166 A JP 2000588166A JP 2002532490 A5 JP2002532490 A5 JP 2002532490A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- lower alkyl
- dihydro
- methylene
- cycloalkyl
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 description 104
- 125000000623 heterocyclic group Chemical group 0.000 description 66
- 125000000753 cycloalkyl group Chemical group 0.000 description 60
- 229910052736 halogen Inorganic materials 0.000 description 28
- 125000001072 heteroaryl group Chemical group 0.000 description 28
- 229910052739 hydrogen Inorganic materials 0.000 description 24
- 239000001257 hydrogen Substances 0.000 description 24
- 125000003118 aryl group Chemical group 0.000 description 22
- 150000002367 halogens Chemical class 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 18
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 13
- -1 4-chloro-2-methylsulfanylmethoxy-phenyl Chemical group 0.000 description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 125000003107 substituted aryl group Chemical group 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 3
- CNELYFGFVRCQQO-ATVHPVEESA-N (3z)-3-(1h-pyrrol-2-ylmethylidene)-5-(2-thiophen-2-ylethynyl)-1h-indol-2-one Chemical compound O=C1NC2=CC=C(C#CC=3SC=CC=3)C=C2\C1=C\C1=CC=CN1 CNELYFGFVRCQQO-ATVHPVEESA-N 0.000 description 2
- YJCIDAJKFWKYCS-OWBHPGMISA-N (3z)-4-[3-hydroxy-3-(3-methoxythiophen-2-yl)prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C4=C(C=CS4)OC)C=CC=C3NC\2=O)=C1OC YJCIDAJKFWKYCS-OWBHPGMISA-N 0.000 description 2
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- LLTZGYZYWGAACV-HKVBYMSFSA-N (3z)-1-[(e)-2-phenylethenyl]-3-(1h-pyrrol-2-ylmethylidene)indol-2-one Chemical compound C12=CC=CC=C2\C(=C\C=2NC=CC=2)C(=O)N1\C=C\C1=CC=CC=C1 LLTZGYZYWGAACV-HKVBYMSFSA-N 0.000 description 1
- ZTAYJHNUGMKDAC-TVYBWHDCSA-N (3z)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1-[(e)-2-phenylethenyl]indol-2-one Chemical compound C1=CNC(\C=C/2C3=CC=CC=C3N(\C=C\C=3C=CC=CC=3)C\2=O)=C1OC ZTAYJHNUGMKDAC-TVYBWHDCSA-N 0.000 description 1
- LFSKVYQOHAAGQB-VKAVYKQESA-N (3z)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-4-(2-phenylethynyl)-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC=4C=CC=CC=4)C=CC=C3NC\2=O)=C1OC LFSKVYQOHAAGQB-VKAVYKQESA-N 0.000 description 1
- SOQYSQMXYLSISO-SSZFMOIBSA-N (3z)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-4-(2-pyridin-2-ylethynyl)-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC=4N=CC=CC=4)C=CC=C3NC\2=O)=C1OC SOQYSQMXYLSISO-SSZFMOIBSA-N 0.000 description 1
- LBRHIACYAJUKFX-VBKFSLOCSA-N (3z)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-4-(2-pyridin-3-ylethynyl)-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC=4C=NC=CC=4)C=CC=C3NC\2=O)=C1OC LBRHIACYAJUKFX-VBKFSLOCSA-N 0.000 description 1
- SOYFKPDKCDIHMW-SSZFMOIBSA-N (3z)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-4-(2-pyridin-4-ylethynyl)-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC=4C=CN=CC=4)C=CC=C3NC\2=O)=C1OC SOYFKPDKCDIHMW-SSZFMOIBSA-N 0.000 description 1
- CIBQBCXWQYRSFJ-SDXDJHTJSA-N (3z)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-4-(3-phenoxyprop-1-ynyl)-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CCOC=4C=CC=CC=4)C=CC=C3NC\2=O)=C1OC CIBQBCXWQYRSFJ-SDXDJHTJSA-N 0.000 description 1
- HHYIPICNMBTBHU-PTNGSMBKSA-N (3z)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-5-nitro-4-(2-pyridin-3-ylethynyl)-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC=4C=NC=CC=4)C(=CC=C3NC\2=O)[N+]([O-])=O)=C1OC HHYIPICNMBTBHU-PTNGSMBKSA-N 0.000 description 1
- XWDAYWGNKHFMGK-GDNBJRDFSA-N (3z)-3-[(5-methyl-1h-imidazol-4-yl)methylidene]-5-(2-trimethylsilylethynyl)-1h-indol-2-one Chemical compound N1=CNC(\C=C/2C3=CC(=CC=C3NC\2=O)C#C[Si](C)(C)C)=C1C XWDAYWGNKHFMGK-GDNBJRDFSA-N 0.000 description 1
- POLVGKSHMPRQIF-SDXDJHTJSA-N (3z)-4-(3-hydroxy-3-phenylbut-1-ynyl)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(C)(O)C=4C=CC=CC=4)C=CC=C3NC\2=O)=C1OC POLVGKSHMPRQIF-SDXDJHTJSA-N 0.000 description 1
- IZXHJFBVDXOSDL-VKAVYKQESA-N (3z)-4-(3-hydroxy-3-phenylprop-1-ynyl)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=CC=CC=4)C=CC=C3NC\2=O)=C1OC IZXHJFBVDXOSDL-VKAVYKQESA-N 0.000 description 1
- PXCCQARRVLKNIM-SQFISAMPSA-N (3z)-4-(3-hydroxy-3-pyridin-2-ylprop-1-ynyl)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4N=CC=CC=4)C=CC=C3NC\2=O)=C1OC PXCCQARRVLKNIM-SQFISAMPSA-N 0.000 description 1
- GIGNTIVPOROLOI-VBKFSLOCSA-N (3z)-4-(3-hydroxy-3-pyridin-3-ylprop-1-ynyl)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=NC=CC=4)C=CC=C3NC\2=O)=C1OC GIGNTIVPOROLOI-VBKFSLOCSA-N 0.000 description 1
- RGVWLPQHWJEXQI-OWBHPGMISA-N (3z)-4-(3-hydroxy-3-thiophen-2-ylprop-1-ynyl)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4SC=CC=4)C=CC=C3NC\2=O)=C1OC RGVWLPQHWJEXQI-OWBHPGMISA-N 0.000 description 1
- MUMWQVXWSSNTMM-PTNGSMBKSA-N (3z)-4-(3-hydroxy-3-thiophen-3-ylprop-1-ynyl)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C4=CSC=C4)C=CC=C3NC\2=O)=C1OC MUMWQVXWSSNTMM-PTNGSMBKSA-N 0.000 description 1
- WPAMZQZOUUBLDX-HNMBUVAWSA-N (3z)-4-[(e)-2-(2-chlorophenyl)ethenyl]-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-2-one Chemical compound ClC1=CC=CC=C1\C=C\C1=CC=CC(NC\2=O)=C1C/2=C/C1=CC=CN1 WPAMZQZOUUBLDX-HNMBUVAWSA-N 0.000 description 1
- YYQIGYCJNSROAA-IUWFAXKNSA-N (3z)-4-[(e)-2-(3,4-dimethoxyphenyl)ethenyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(\C=C\C=4C=C(OC)C(OC)=CC=4)C=CC=C3NC\2=O)=C1OC YYQIGYCJNSROAA-IUWFAXKNSA-N 0.000 description 1
- IEMHQFOFIAWLHH-VAVYRGOBSA-N (3z)-4-[(e)-2-(4-methoxyphenyl)ethenyl]-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-2-one Chemical compound C1=CC(OC)=CC=C1\C=C\C1=CC=CC(NC\2=O)=C1C/2=C/C1=CC=CN1 IEMHQFOFIAWLHH-VAVYRGOBSA-N 0.000 description 1
- DTCDOONGFRBLDF-PAAQWSFZSA-N (3z)-4-[(e)-2-(4-methoxyphenyl)ethenyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(\C=C\C=4C=CC(OC)=CC=4)C=CC=C3NC\2=O)=C1OC DTCDOONGFRBLDF-PAAQWSFZSA-N 0.000 description 1
- COGFBJXZPOJDJS-JXAWBTAJSA-N (3z)-4-[2-(4-methoxyphenyl)ethynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC=4C=CC(OC)=CC=4)C=CC=C3NC\2=O)=C1OC COGFBJXZPOJDJS-JXAWBTAJSA-N 0.000 description 1
- NUCZORXTPQUVGZ-VBKFSLOCSA-N (3z)-4-[3-(1,3-benzodioxol-5-yl)-3-hydroxyprop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=C5OCOC5=CC=4)C=CC=C3NC\2=O)=C1OC NUCZORXTPQUVGZ-VBKFSLOCSA-N 0.000 description 1
- OYQFBEWTCTWNGC-VKAVYKQESA-N (3z)-4-[3-(2,3-dimethoxyphenyl)-3-hydroxyprop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C(=C(OC)C=CC=4)OC)C=CC=C3NC\2=O)=C1OC OYQFBEWTCTWNGC-VKAVYKQESA-N 0.000 description 1
- QOXYBCGXASWZIY-VKAVYKQESA-N (3z)-4-[3-(3,4-dimethoxyphenyl)-3-hydroxyprop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=C(OC)C(OC)=CC=4)C=CC=C3NC\2=O)=C1OC QOXYBCGXASWZIY-VKAVYKQESA-N 0.000 description 1
- WNSGLFJZOFFYTE-LGMDPLHJSA-N (3z)-4-[3-(3-aminophenyl)-3-hydroxyprop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=C(N)C=CC=4)C=CC=C3NC\2=O)=C1OC WNSGLFJZOFFYTE-LGMDPLHJSA-N 0.000 description 1
- LVZOBVTVBBIVMZ-LGMDPLHJSA-N (3z)-4-[3-(3-chlorophenyl)-3-hydroxyprop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=C(Cl)C=CC=4)C=CC=C3NC\2=O)=C1OC LVZOBVTVBBIVMZ-LGMDPLHJSA-N 0.000 description 1
- JIZBUYBBALMSAD-OWBHPGMISA-N (3z)-4-[3-(furan-2-yl)-3-hydroxyprop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4OC=CC=4)C=CC=C3NC\2=O)=C1OC JIZBUYBBALMSAD-OWBHPGMISA-N 0.000 description 1
- QZEXZSLTGGACSR-CYVLTUHYSA-N (3z)-4-[3-[4-(dimethylamino)phenyl]-3-hydroxyprop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=CC(=CC=4)N(C)C)C=CC=C3NC\2=O)=C1OC QZEXZSLTGGACSR-CYVLTUHYSA-N 0.000 description 1
- WXWYYUPZZCUBKY-PYCFMQQDSA-N (3z)-4-[3-[4-[3-(dimethylamino)propoxy]phenyl]-3-hydroxyprop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=CC(OCCCN(C)C)=CC=4)C=CC=C3NC\2=O)=C1OC WXWYYUPZZCUBKY-PYCFMQQDSA-N 0.000 description 1
- YRXDNKVXUTYODU-SQFISAMPSA-N (3z)-4-[3-hydroxy-3-(1-methylpyrrol-2-yl)prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4N(C=CC=4)C)C=CC=C3NC\2=O)=C1OC YRXDNKVXUTYODU-SQFISAMPSA-N 0.000 description 1
- PBNDYRBZMZOPIF-OWBHPGMISA-N (3z)-4-[3-hydroxy-3-(1h-pyrrol-2-yl)prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4NC=CC=4)C=CC=C3NC\2=O)=C1OC PBNDYRBZMZOPIF-OWBHPGMISA-N 0.000 description 1
- FLUWNHUCLAWPKG-ATVHPVEESA-N (3z)-4-[3-hydroxy-3-(2,4,5-trimethoxyphenyl)prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C(=CC(OC)=C(OC)C=4)OC)C=CC=C3NC\2=O)=C1OC FLUWNHUCLAWPKG-ATVHPVEESA-N 0.000 description 1
- FGWZGTXNTSYELB-VKAVYKQESA-N (3z)-4-[3-hydroxy-3-(2-methoxyphenyl)prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C(=CC=CC=4)OC)C=CC=C3NC\2=O)=C1OC FGWZGTXNTSYELB-VKAVYKQESA-N 0.000 description 1
- QOZJTHXUJVMUTK-SSZFMOIBSA-N (3z)-4-[3-hydroxy-3-(3-hydroxy-4-methoxyphenyl)prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=C(O)C(OC)=CC=4)C=CC=C3NC\2=O)=C1OC QOZJTHXUJVMUTK-SSZFMOIBSA-N 0.000 description 1
- JCNUEOJEPMPPIV-LGMDPLHJSA-N (3z)-4-[3-hydroxy-3-(3-hydroxyphenyl)prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=C(O)C=CC=4)C=CC=C3NC\2=O)=C1OC JCNUEOJEPMPPIV-LGMDPLHJSA-N 0.000 description 1
- YXGSOBZQGVSTRQ-JXAWBTAJSA-N (3z)-4-[3-hydroxy-3-(3-methoxyphenyl)prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=C(OC)C=CC=4)C=CC=C3NC\2=O)=C1OC YXGSOBZQGVSTRQ-JXAWBTAJSA-N 0.000 description 1
- SENKVSSHGZDFNW-LGMDPLHJSA-N (3z)-4-[3-hydroxy-3-(3-nitrophenyl)prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=C(C=CC=4)[N+]([O-])=O)C=CC=C3NC\2=O)=C1OC SENKVSSHGZDFNW-LGMDPLHJSA-N 0.000 description 1
- ARAMICXSYSETIU-SSZFMOIBSA-N (3z)-4-[3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=C(OC)C(O)=CC=4)C=CC=C3NC\2=O)=C1OC ARAMICXSYSETIU-SSZFMOIBSA-N 0.000 description 1
- RRCHGUVCSGQAPF-LGMDPLHJSA-N (3z)-4-[3-hydroxy-3-(4-hydroxyphenyl)prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=CC(O)=CC=4)C=CC=C3NC\2=O)=C1OC RRCHGUVCSGQAPF-LGMDPLHJSA-N 0.000 description 1
- RSYGPYSNRUOCKK-JXAWBTAJSA-N (3z)-4-[3-hydroxy-3-(4-methoxyphenyl)prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=CC(OC)=CC=4)C=CC=C3NC\2=O)=C1OC RSYGPYSNRUOCKK-JXAWBTAJSA-N 0.000 description 1
- DAZFZTIVXHLFQQ-NKFKGCMQSA-N (3z)-4-[3-hydroxy-3-(4-phenoxyphenyl)prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=CC(OC=5C=CC=CC=5)=CC=4)C=CC=C3NC\2=O)=C1OC DAZFZTIVXHLFQQ-NKFKGCMQSA-N 0.000 description 1
- NSIKGWYDIJARHZ-VBKFSLOCSA-N (3z)-4-[3-hydroxy-3-(7-methoxy-1,3-benzodioxol-5-yl)prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=C(OC)C=5OCOC=5C=4)C=CC=C3NC\2=O)=C1OC NSIKGWYDIJARHZ-VBKFSLOCSA-N 0.000 description 1
- GHRIUISNTDKVTN-QOCHGBHMSA-N (3z)-4-[3-hydroxy-3-[3-methoxy-4-(2-morpholin-4-ylethoxy)phenyl]prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=C(OC)C(OCCN5CCOCC5)=CC=4)C=CC=C3NC\2=O)=C1OC GHRIUISNTDKVTN-QOCHGBHMSA-N 0.000 description 1
- UJYFDCHHAWEECC-GXTSIBQPSA-N (3z)-4-[3-hydroxy-3-[3-methoxy-4-(2-morpholin-4-ylethoxy)phenyl]prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one;hydrochloride Chemical compound Cl.C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=C(OC)C(OCCN5CCOCC5)=CC=4)C=CC=C3NC\2=O)=C1OC UJYFDCHHAWEECC-GXTSIBQPSA-N 0.000 description 1
- BZTQDBKGIBAREQ-NMWGTECJSA-N (3z)-4-[3-hydroxy-3-[4-(2-morpholin-4-ylethoxy)phenyl]prop-1-ynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=CC(OCCN5CCOCC5)=CC=4)C=CC=C3NC\2=O)=C1OC BZTQDBKGIBAREQ-NMWGTECJSA-N 0.000 description 1
- DTBCCPGQXHCCJH-RGEXLXHISA-N (3z)-5-(2-phenylethynyl)-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=C(C#CC=3C=CC=CC=3)C=C2\C1=C\C1=CC=CN1 DTBCCPGQXHCCJH-RGEXLXHISA-N 0.000 description 1
- HEBQMEDMHXTFPG-AQTBWJFISA-N (3z)-5-(2-pyridin-2-ylethynyl)-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=C(C#CC=3N=CC=CC=3)C=C2\C1=C\C1=CC=CN1 HEBQMEDMHXTFPG-AQTBWJFISA-N 0.000 description 1
- LELVBSYVHOBCGR-PDGQHHTCSA-N (3z)-5-(2-pyridin-3-ylethynyl)-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=C(C#CC=3C=NC=CC=3)C=C2\C1=C\C1=CC=CN1 LELVBSYVHOBCGR-PDGQHHTCSA-N 0.000 description 1
- ZSXMOOAYMVIBSX-AQTBWJFISA-N (3z)-5-[2-(2-nitrophenyl)ethynyl]-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-2-one Chemical compound [O-][N+](=O)C1=CC=CC=C1C#CC1=CC=C(NC(=O)\C2=C/C=3NC=CC=3)C2=C1 ZSXMOOAYMVIBSX-AQTBWJFISA-N 0.000 description 1
- UMVXEEDGNPDOFC-UYRXBGFRSA-N (3z)-5-[2-(3-hydroxyphenyl)ethynyl]-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-2-one Chemical compound OC1=CC=CC(C#CC=2C=C3C(=C/C=4NC=CC=4)/C(=O)NC3=CC=2)=C1 UMVXEEDGNPDOFC-UYRXBGFRSA-N 0.000 description 1
- BGMXWZJIMIWZLP-UYRXBGFRSA-N (3z)-5-[2-(3-nitrophenyl)ethynyl]-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-2-one Chemical compound [O-][N+](=O)C1=CC=CC(C#CC=2C=C3C(=C/C=4NC=CC=4)/C(=O)NC3=CC=2)=C1 BGMXWZJIMIWZLP-UYRXBGFRSA-N 0.000 description 1
- FIXDPUBAPHNBIB-UYRXBGFRSA-N (3z)-5-[2-(4-aminophenyl)ethynyl]-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-2-one Chemical compound C1=CC(N)=CC=C1C#CC1=CC=C(NC(=O)\C2=C/C=3NC=CC=3)C2=C1 FIXDPUBAPHNBIB-UYRXBGFRSA-N 0.000 description 1
- OUIATLHATROJIS-UYRXBGFRSA-N (3z)-5-[2-(4-hydroxyphenyl)ethynyl]-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C#CC1=CC=C(NC(=O)\C2=C/C=3NC=CC=3)C2=C1 OUIATLHATROJIS-UYRXBGFRSA-N 0.000 description 1
- PGMLCEKECCEFAO-AQTBWJFISA-N (3z)-5-[2-(4-hydroxyphenyl)ethynyl]-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=CC(=CC=C3NC\2=O)C#CC=2C=CC(O)=CC=2)=C1OC PGMLCEKECCEFAO-AQTBWJFISA-N 0.000 description 1
- SUIUQQPGKUZEOX-ZHZULCJRSA-N (3z)-5-[2-(4-methoxyphenyl)ethynyl]-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-2-one Chemical compound C1=CC(OC)=CC=C1C#CC1=CC=C(NC(=O)\C2=C/C=3NC=CC=3)C2=C1 SUIUQQPGKUZEOX-ZHZULCJRSA-N 0.000 description 1
- YRAQZUQALGLTGH-UYRXBGFRSA-N (3z)-5-[2-(4-nitrophenyl)ethynyl]-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-2-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C#CC1=CC=C(NC(=O)\C2=C/C=3NC=CC=3)C2=C1 YRAQZUQALGLTGH-UYRXBGFRSA-N 0.000 description 1
- YHIFTRRHGPGDKD-PTNGSMBKSA-N (3z)-5-amino-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-4-(2-pyridin-3-ylethynyl)-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=C(C#CC=4C=NC=CC=4)C(N)=CC=C3NC\2=O)=C1OC YHIFTRRHGPGDKD-PTNGSMBKSA-N 0.000 description 1
- YLQAQZFUXVPZGQ-LCYFTJDESA-N (3z)-5-ethynyl-3-(1h-pyrrol-2-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=C(C#C)C=C2\C1=C\C1=CC=CN1 YLQAQZFUXVPZGQ-LCYFTJDESA-N 0.000 description 1
- GZSXMGUALNRWHL-XFXZXTDPSA-N (3z)-5-ethynyl-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1=CNC(\C=C/2C3=CC(=CC=C3NC\2=O)C#C)=C1OC GZSXMGUALNRWHL-XFXZXTDPSA-N 0.000 description 1
- IUCRERMPHUTDKU-GHXNOFRVSA-N (3z)-5-ethynyl-3-[(5-methyl-1h-imidazol-4-yl)methylidene]-1h-indol-2-one Chemical compound N1=CNC(\C=C/2C3=CC(=CC=C3NC\2=O)C#C)=C1C IUCRERMPHUTDKU-GHXNOFRVSA-N 0.000 description 1
- RSEGQJSFDGPSHB-LGMDPLHJSA-N 2-[4-[1-hydroxy-3-[(3z)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-2-oxo-1h-indol-4-yl]prop-2-ynyl]-2-methoxyphenoxy]acetic acid Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=C(OC)C(OCC(O)=O)=CC=4)C=CC=C3NC\2=O)=C1OC RSEGQJSFDGPSHB-LGMDPLHJSA-N 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- HSZQLJPSDFRYJD-LGMDPLHJSA-N 4-[1-hydroxy-3-[(3z)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-2-oxo-1h-indol-4-yl]prop-2-ynyl]benzoic acid Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=CC(=CC=4)C(O)=O)C=CC=C3NC\2=O)=C1OC HSZQLJPSDFRYJD-LGMDPLHJSA-N 0.000 description 1
- 102100039250 Essential MCU regulator, mitochondrial Human genes 0.000 description 1
- 101000813097 Homo sapiens Essential MCU regulator, mitochondrial Proteins 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000004367 cycloalkylaryl group Chemical group 0.000 description 1
- 125000005215 cycloalkylheteroaryl group Chemical group 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- FAFVKKUTZMVGHK-JXAWBTAJSA-N methyl 2-[4-[1-hydroxy-3-[(3z)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-2-oxo-1h-indol-4-yl]prop-2-ynyl]-2-methoxyphenoxy]acetate Chemical compound C1=C(OC)C(OCC(=O)OC)=CC=C1C(O)C#CC1=CC=CC(NC\2=O)=C1C/2=C/C1=C(OC)C=CN1 FAFVKKUTZMVGHK-JXAWBTAJSA-N 0.000 description 1
- RZTFYTLJOXSQKQ-PAAQWSFZSA-N methyl 4-[(e)-2-[(3z)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-2-oxo-1h-indol-4-yl]ethenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1\C=C\C1=CC=CC(NC\2=O)=C1C/2=C/C1=C(OC)C=CN1 RZTFYTLJOXSQKQ-PAAQWSFZSA-N 0.000 description 1
- JYQHZYNJTJQVKS-JXAWBTAJSA-N methyl 4-[1-hydroxy-3-[(3z)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-2-oxo-1h-indol-4-yl]prop-2-ynyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(O)C#CC1=CC=CC(NC\2=O)=C1C/2=C/C1=C(OC)C=CN1 JYQHZYNJTJQVKS-JXAWBTAJSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- DKNKBLBPQHSVGJ-HKWRFOASSA-N n-[(3z)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-2-oxo-4-(2-pyridin-3-ylethynyl)-1h-indol-5-yl]-2-thiophen-2-ylacetamide Chemical compound C1=CNC(\C=C/2C3=C(C#CC=4C=NC=CC=4)C(NC(=O)CC=4SC=CC=4)=CC=C3NC\2=O)=C1OC DKNKBLBPQHSVGJ-HKWRFOASSA-N 0.000 description 1
- WNPUJTJJHQVVHZ-RGEXLXHISA-N n-[4-[1-hydroxy-3-[(3z)-3-[(3-methoxy-1h-pyrrol-2-yl)methylidene]-2-oxo-1h-indol-4-yl]prop-2-ynyl]phenyl]acetamide Chemical compound C1=CNC(\C=C/2C3=C(C#CC(O)C=4C=CC(NC(C)=O)=CC=4)C=CC=C3NC\2=O)=C1OC WNPUJTJJHQVVHZ-RGEXLXHISA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- WUWDLXZGHZSWQZ-WQLSENKSSA-N semaxanib Chemical compound N1C(C)=CC(C)=C1\C=C/1C2=CC=CC=C2NC\1=O WUWDLXZGHZSWQZ-WQLSENKSSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11258998P | 1998-12-17 | 1998-12-17 | |
| US60/112,589 | 1998-12-17 | ||
| US14148299P | 1999-06-29 | 1999-06-29 | |
| US60/141,482 | 1999-06-29 | ||
| PCT/EP1999/009578 WO2000035906A2 (en) | 1998-12-17 | 1999-12-07 | 4- and 5-alkynyloxindoles and 4- and 5-alkenyloxindoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002532490A JP2002532490A (ja) | 2002-10-02 |
| JP2002532490A5 true JP2002532490A5 (enExample) | 2007-08-16 |
Family
ID=26810125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000588166A Pending JP2002532490A (ja) | 1998-12-17 | 1999-12-07 | ４−および５−アルキニルオキシンドールと４−および５−アルケニルオキシンドール |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP1149092B1 (enExample) |
| JP (1) | JP2002532490A (enExample) |
| KR (1) | KR20010087421A (enExample) |
| CN (1) | CN1147486C (enExample) |
| AT (1) | ATE253062T1 (enExample) |
| AU (1) | AU771599B2 (enExample) |
| BR (1) | BR9916272A (enExample) |
| CA (1) | CA2354510A1 (enExample) |
| DE (1) | DE69912479T2 (enExample) |
| DK (1) | DK1149092T3 (enExample) |
| ES (1) | ES2209527T3 (enExample) |
| PT (1) | PT1149092E (enExample) |
| TR (1) | TR200101747T2 (enExample) |
| WO (1) | WO2000035906A2 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6569868B2 (en) | 1998-04-16 | 2003-05-27 | Sugen, Inc. | 2-indolinone derivatives as modulators of protein kinase activity |
| MY128450A (en) | 2000-05-24 | 2007-02-28 | Upjohn Co | 1-(pyrrolidin-1-ylmethyl)-3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives |
| JP2003535847A (ja) | 2000-06-02 | 2003-12-02 | スージェン・インコーポレーテッド | 蛋白質キナーゼ／ホスファターゼ阻害剤としてのインドリノン誘導体 |
| JP2004502686A (ja) | 2000-06-30 | 2004-01-29 | スージェン・インコーポレーテッド | ４−ヘテロアリール−３−ヘテロアリーリデニル−２−インドリノンおよび蛋白質キナーゼ阻害剤としてのその使用 |
| CA2440842A1 (en) | 2001-04-16 | 2002-10-24 | Eisai Co., Ltd. | Novel 1h-indazole compounds |
| US7018999B2 (en) | 2001-05-16 | 2006-03-28 | Cephalon, Inc. | Methods for the treatment and prevention of pain |
| AR036042A1 (es) | 2001-05-30 | 2004-08-04 | Sugen Inc | Derivados aralquilsufonil-3-(pirrol-2-ilmetiliden)-2-indolinona, sus composiciones farmaceuticas y metodo para la modulacion de la actividad catalitica de una proteina quinasa |
| IL159767A0 (en) | 2001-07-23 | 2004-06-20 | Applied Research Systems | Sulfonamide derivatives, their preparation and pharmacetuical compositions containing them |
| US6962922B2 (en) | 2001-10-12 | 2005-11-08 | Warner-Lambert Company Llc | Alkynylated quinazoline compounds |
| JP4164028B2 (ja) | 2001-10-12 | 2008-10-08 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | アルキンマトリックスメタロプロテイナーゼ阻害剤 |
| JP4388376B2 (ja) | 2002-02-28 | 2009-12-24 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 新規な縮合環インダゾール化合物 |
| US6894057B2 (en) | 2002-03-08 | 2005-05-17 | Warner-Lambert Company | Oxo-azabicyclic compounds |
| US6747147B2 (en) | 2002-03-08 | 2004-06-08 | Warner-Lambert Company | Oxo-azabicyclic compounds |
| TW200406385A (en) | 2002-05-31 | 2004-05-01 | Eisai Co Ltd | Pyrazole compound and pharmaceutical composition containing the same |
| CA2487948A1 (en) | 2002-06-14 | 2003-12-24 | Applied Research Systems Ars Holding N.V. | Azole methylidene cyanide derivatives and their use as protein kinase modulators |
| WO2005040116A2 (en) | 2003-10-24 | 2005-05-06 | Schering Aktiengesellschaft | Indolinone derivatives and their use in treating disease-states such as cancer |
| DE102004012070A1 (de) * | 2004-03-12 | 2005-09-29 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue cycloalkyl-haltige 5-Acylindolinone, deren Herstellung und deren Verwendung als Arzneimittel |
| US7803824B2 (en) | 2004-10-29 | 2010-09-28 | Alcon, Inc. | Use of inhibitors of Jun N-terminal kinases to treat glaucoma |
| US20060094753A1 (en) | 2004-10-29 | 2006-05-04 | Alcon, Inc. | Use of inhibitors of Jun N-terminal kinases for the treatment of glaucomatous retinopathy and ocular diseases |
| WO2006090698A1 (ja) * | 2005-02-22 | 2006-08-31 | Ono Pharmaceutical Co., Ltd. | キナーゼ阻害薬およびその用途 |
| KR20080044836A (ko) | 2005-07-15 | 2008-05-21 | 라보라뚜와르 세로노 에스. 에이. | 자궁내막증 치료용 ｊｎｋ 억제제 |
| BRPI0613042A2 (pt) | 2005-07-15 | 2010-12-14 | Serono Lab | inibidores de jnk para o tratamento de endometriose |
| CN1939922B (zh) * | 2005-09-27 | 2010-10-13 | 天津和美生物技术有限公司 | 可抑制细胞释放肿瘤坏死因子的5H-噻吩[3，4-c]吡咯-4，6-二酮衍生物 |
| BRPI0616655A2 (pt) | 2005-10-03 | 2011-06-28 | Ono Pharmaceutical Co | composto heterocìclico contendo nitrogênio e aplicação farmacêutica do mesmo |
| FR2962729B1 (fr) | 2010-07-13 | 2012-09-21 | Arkema France | Molecules porteuses de groupes associatifs |
| FR2962733B1 (fr) | 2010-07-13 | 2012-08-17 | Michelin Soc Tech | Polymere greffe par des molecules associatives azotees. |
| US20140205537A1 (en) * | 2011-06-24 | 2014-07-24 | Zenobia Therapeutics, Inc. | Lrrk2 inhibitors |
| CN112848815A (zh) | 2019-11-27 | 2021-05-28 | 财团法人工业技术研究院 | 发电感测传输装置 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9501567D0 (en) * | 1995-01-26 | 1995-03-15 | Pharmacia Spa | Hydrosoluble 3-arylidene-2-oxindole derivatives as tyrosine kinase inhibitors |
| GB9507298D0 (en) * | 1995-04-07 | 1995-05-31 | Pharmacia Spa | Substituted indolylmethylene-oxindale analogues as tyrosine kinase inhibitors |
| US5880141A (en) * | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
| GB9610964D0 (en) * | 1996-05-24 | 1996-07-31 | Pharmacia & Upjohn Spa | Substituted tetralylmethylen-oxindole analogues as tyrosine kinase inhibitors |
| WO1998007695A1 (en) * | 1996-08-23 | 1998-02-26 | Sugen, Inc. | Indolinone combinatorial libraries and related products and methods for the treatment of disease |
| ATE292623T1 (de) * | 1997-05-07 | 2005-04-15 | Sugen Inc | 2-indolinonderivate als modulatoren der proteinkinase-ativität |
-
1999
- 1999-12-07 KR KR1020017007552A patent/KR20010087421A/ko not_active Ceased
- 1999-12-07 JP JP2000588166A patent/JP2002532490A/ja active Pending
- 1999-12-07 CA CA002354510A patent/CA2354510A1/en not_active Abandoned
- 1999-12-07 TR TR2001/01747T patent/TR200101747T2/xx unknown
- 1999-12-07 DE DE69912479T patent/DE69912479T2/de not_active Expired - Fee Related
- 1999-12-07 AU AU15076/00A patent/AU771599B2/en not_active Ceased
- 1999-12-07 EP EP99957341A patent/EP1149092B1/en not_active Expired - Lifetime
- 1999-12-07 ES ES99957341T patent/ES2209527T3/es not_active Expired - Lifetime
- 1999-12-07 AT AT99957341T patent/ATE253062T1/de not_active IP Right Cessation
- 1999-12-07 WO PCT/EP1999/009578 patent/WO2000035906A2/en not_active Ceased
- 1999-12-07 CN CNB998146994A patent/CN1147486C/zh not_active Expired - Fee Related
- 1999-12-07 BR BR9916272-5A patent/BR9916272A/pt not_active IP Right Cessation
- 1999-12-07 DK DK99957341T patent/DK1149092T3/da active
- 1999-12-07 PT PT99957341T patent/PT1149092E/pt unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2002532490A5 (enExample) | ||
| ES2278685T3 (es) | Derivados de la isoindolina farmaceuticamente activos. | |
| RU2001130446A (ru) | Пиразолбензодиазепины в качестве ингибиторов CDK2 | |
| EP1149092B1 (en) | 4- and 5-alkynyloxindoles and 4- and 5-alkenyloxindoles | |
| JP2006528685A5 (enExample) | ||
| RU2469042C2 (ru) | Терапевтически активные триазолы и их использование | |
| RU2006142552A (ru) | Производные амино-5,5-дифенилимидазолона как ингибиторы b-секретазы | |
| JP2007513957A5 (enExample) | ||
| JP2004536869A5 (enExample) | ||
| JP2003523927A5 (enExample) | ||
| JP2020516671A5 (enExample) | ||
| RU2002133863A (ru) | Производные замещенного пирролопиридинона, пригодные в качестве ингибиторов фосфодиэстеразы | |
| JP2007513915A5 (enExample) | ||
| JP2010507602A5 (enExample) | ||
| JP2007516173A5 (enExample) | ||
| JP2003510359A5 (enExample) | ||
| JP2009520685A5 (enExample) | ||
| RU2006135927A (ru) | Бифенильные соединения, полезные в качестве антагонистов мускариновых рецепторов | |
| JP2004517049A5 (enExample) | ||
| RU2000125690A (ru) | Производные бензофурилпирона | |
| JP2003521514A5 (enExample) | ||
| JP2006528161A (ja) | ヒスタミンのアンタゴニストとしてのピペリジンのイミダゾール誘導体 | |
| RU2004128393A (ru) | Производные бензофурана и бензотиофена, примениемые при лечении гиперпролиферативных заболеваний | |
| JP2002521334A5 (enExample) | ||
| JP2009540009A5 (enExample) |