JP2010502716A5 - - Google Patents
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- Publication number
- JP2010502716A5 JP2010502716A5 JP2009527436A JP2009527436A JP2010502716A5 JP 2010502716 A5 JP2010502716 A5 JP 2010502716A5 JP 2009527436 A JP2009527436 A JP 2009527436A JP 2009527436 A JP2009527436 A JP 2009527436A JP 2010502716 A5 JP2010502716 A5 JP 2010502716A5
- Authority
- JP
- Japan
- Prior art keywords
- imidazo
- pyridazin
- pyran
- tetrahydro
- amine
- 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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- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000002723 alicyclic group Chemical group 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 39
- -1 amino, hydroxy Chemical group 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 11
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 102100036342 Interleukin-1 receptor-associated kinase 1 Human genes 0.000 claims 7
- 101710199015 Interleukin-1 receptor-associated kinase 1 Proteins 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 208000035475 disorder Diseases 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 229940124530 sulfonamide Drugs 0.000 claims 3
- 150000003456 sulfonamides Chemical group 0.000 claims 3
- DTUZIVBPPQTBFT-UHFFFAOYSA-N 1-[3-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 DTUZIVBPPQTBFT-UHFFFAOYSA-N 0.000 claims 2
- JSBGWDNSENOORN-UHFFFAOYSA-N 2-[4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetonitrile Chemical compound C1=CC(CC#N)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 JSBGWDNSENOORN-UHFFFAOYSA-N 0.000 claims 2
- FCPWNKFKADKUNF-UHFFFAOYSA-N 3-(2-methoxyphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=CC=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 FCPWNKFKADKUNF-UHFFFAOYSA-N 0.000 claims 2
- QPAUPGQSDSAKRY-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 QPAUPGQSDSAKRY-UHFFFAOYSA-N 0.000 claims 2
- SPSXRVIHUDPXQZ-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(F)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 SPSXRVIHUDPXQZ-UHFFFAOYSA-N 0.000 claims 2
- QDEOYNAMUXJSHH-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 QDEOYNAMUXJSHH-UHFFFAOYSA-N 0.000 claims 2
- KVOCFEBFKVEVIQ-UHFFFAOYSA-N 3-(5-methoxypyridin-3-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=CN=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 KVOCFEBFKVEVIQ-UHFFFAOYSA-N 0.000 claims 2
- KGDVXQORBWBIHS-UHFFFAOYSA-N 4-[6-(3-hydroxypropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(NCCCO)C=CC3=NC=2)=C1 KGDVXQORBWBIHS-UHFFFAOYSA-N 0.000 claims 2
- KOXVNSVKNGZIHN-UHFFFAOYSA-N 4-[6-(3-hydroxypropylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound N12N=C(NCCCO)C=CC2=NC=C1C1=CC=C(O)C=C1 KOXVNSVKNGZIHN-UHFFFAOYSA-N 0.000 claims 2
- OPKXXSDVMPBIOF-UHFFFAOYSA-N 4-[6-(furan-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=C2N1N=C(NCC=1OC=CC=1)C=C2 OPKXXSDVMPBIOF-UHFFFAOYSA-N 0.000 claims 2
- NXPFHUPKORDOHQ-UHFFFAOYSA-N 4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 NXPFHUPKORDOHQ-UHFFFAOYSA-N 0.000 claims 2
- PHLHEYALRJOPMB-UHFFFAOYSA-N 4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 PHLHEYALRJOPMB-UHFFFAOYSA-N 0.000 claims 2
- DFYXVCWJEDZGPJ-UHFFFAOYSA-N 4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 DFYXVCWJEDZGPJ-UHFFFAOYSA-N 0.000 claims 2
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- BWBYBKHRQMCAAS-VOTSOKGWSA-N n-(oxan-4-yl)-3-[(e)-2-phenylethenyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(\C=C\C=3C=CC=CC=3)=CN=C2C=C1 BWBYBKHRQMCAAS-VOTSOKGWSA-N 0.000 claims 2
- WXHHSNLRMCAIPE-UHFFFAOYSA-N n-[3-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 WXHHSNLRMCAIPE-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- CASKVJFIBGKPRI-CQSZACIVSA-N (2s)-2-[[3-(4-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]-3-methylbutan-1-ol Chemical compound N12N=C(N[C@H](CO)C(C)C)C=CC2=NC=C1C1=CC=C(F)C=C1 CASKVJFIBGKPRI-CQSZACIVSA-N 0.000 claims 1
- DQESXLDSAYDERW-INIZCTEOSA-N (2s)-2-amino-3-[4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]propanoic acid Chemical compound C1=CC(C[C@H](N)C(O)=O)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 DQESXLDSAYDERW-INIZCTEOSA-N 0.000 claims 1
- URSYIWDQINHOHD-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[3-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 URSYIWDQINHOHD-UHFFFAOYSA-N 0.000 claims 1
- QENZCKMDMMAVLU-VMPITWQZSA-N (e)-3-[3-[6-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]prop-2-enoic acid Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=CC(\C=C\C(O)=O)=C1 QENZCKMDMMAVLU-VMPITWQZSA-N 0.000 claims 1
- LIWNRPDZCPMYLF-VMPITWQZSA-N (e)-3-[3-[6-(3-hydroxypropylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]prop-2-enoic acid Chemical compound N12N=C(NCCCO)C=CC2=NC=C1C1=CC=CC(\C=C\C(O)=O)=C1 LIWNRPDZCPMYLF-VMPITWQZSA-N 0.000 claims 1
- FVEFSYLRXMQDTA-QPJJXVBHSA-N (e)-3-[3-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 FVEFSYLRXMQDTA-QPJJXVBHSA-N 0.000 claims 1
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical compound C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 claims 1
- BVFGOCCZLAFACJ-UHFFFAOYSA-N 1-[3-[6-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=CC(C(C)=O)=C1 BVFGOCCZLAFACJ-UHFFFAOYSA-N 0.000 claims 1
- NFFHTTGHKAWIHJ-UHFFFAOYSA-N 1-[3-[6-(cyclohexylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]-2-hydroxyethanone Chemical compound OCC(=O)C1=CC=CC(C=2N3N=C(NC4CCCCC4)C=CC3=NC=2)=C1 NFFHTTGHKAWIHJ-UHFFFAOYSA-N 0.000 claims 1
- YVFKGXUGCTVDRW-UHFFFAOYSA-N 1-[5-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]thiophen-2-yl]ethanone Chemical compound S1C(C(=O)C)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 YVFKGXUGCTVDRW-UHFFFAOYSA-N 0.000 claims 1
- QQJXVOYLYGFWKD-GFCCVEGCSA-N 1-[5-[6-[[(2s)-1-hydroxy-3-methylbutan-2-yl]amino]imidazo[1,2-b]pyridazin-3-yl]thiophen-2-yl]ethanone Chemical compound N12N=C(N[C@H](CO)C(C)C)C=CC2=NC=C1C1=CC=C(C(C)=O)S1 QQJXVOYLYGFWKD-GFCCVEGCSA-N 0.000 claims 1
- BUCQEBGZOUHFNE-UHFFFAOYSA-N 2-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzonitrile Chemical compound N#CC1=CC=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 BUCQEBGZOUHFNE-UHFFFAOYSA-N 0.000 claims 1
- OGCPTBHWWATXSG-UHFFFAOYSA-N 2-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound OC1=CC=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 OGCPTBHWWATXSG-UHFFFAOYSA-N 0.000 claims 1
- VLONLXDVIRSEGY-UHFFFAOYSA-N 2-[[3-(2-methoxy-5-propan-2-ylphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]-3-methylbutan-1-ol Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C2N1N=C(NC(CO)C(C)C)C=C2 VLONLXDVIRSEGY-UHFFFAOYSA-N 0.000 claims 1
- AMCQSNFXZVJXAV-UHFFFAOYSA-N 2-[[3-(4-fluorophenyl)imidazo[1,2-b]pyridazin-6-yl]amino]ethanol Chemical compound N12N=C(NCCO)C=CC2=NC=C1C1=CC=C(F)C=C1 AMCQSNFXZVJXAV-UHFFFAOYSA-N 0.000 claims 1
- MPBYAEDBVUNPJL-UHFFFAOYSA-N 2-[[4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]methyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CC(C=C1)=CC=C1C(N1N=2)=CN=C1C=CC=2NC1CCOCC1 MPBYAEDBVUNPJL-UHFFFAOYSA-N 0.000 claims 1
- ANAWTLNXCZEKNV-UHFFFAOYSA-N 2-fluoro-4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzohydrazide Chemical compound C1=C(F)C(C(=O)NN)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 ANAWTLNXCZEKNV-UHFFFAOYSA-N 0.000 claims 1
- SVTUXDXGOZWCSF-UHFFFAOYSA-N 2-fluoro-5-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound C1=C(C=O)C(F)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 SVTUXDXGOZWCSF-UHFFFAOYSA-N 0.000 claims 1
- BBMZBUUWXLYGPM-UHFFFAOYSA-N 2-fluoro-5-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]benzonitrile Chemical compound C1=C(C#N)C(F)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 BBMZBUUWXLYGPM-UHFFFAOYSA-N 0.000 claims 1
- UHOCSXUVXQGFLS-UHFFFAOYSA-N 2-hydroxy-1-[3-[6-(3-hydroxypropylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone Chemical compound N12N=C(NCCCO)C=CC2=NC=C1C1=CC=CC(C(=O)CO)=C1 UHOCSXUVXQGFLS-UHFFFAOYSA-N 0.000 claims 1
- GNKFLYCZFHBCNW-UHFFFAOYSA-N 2-hydroxy-1-[3-[6-(oxan-4-yloxy)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone Chemical compound OCC(=O)C1=CC=CC(C=2N3N=C(OC4CCOCC4)C=CC3=NC=2)=C1 GNKFLYCZFHBCNW-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- DIGMAWDYOFWXAX-UHFFFAOYSA-N 2-methoxy-4-[6-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound N12N=C(NCCOC)C=CC2=NC=C1C1=CC=C(O)C(OC)=C1 DIGMAWDYOFWXAX-UHFFFAOYSA-N 0.000 claims 1
- YTUUHCQHXXCOPL-UHFFFAOYSA-N 2-methoxy-4-[6-(oxan-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 YTUUHCQHXXCOPL-UHFFFAOYSA-N 0.000 claims 1
- GNSKGHQQFNMVSH-UHFFFAOYSA-N 2-methoxy-4-[6-(propylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound N12N=C(NCCC)C=CC2=NC=C1C1=CC=C(O)C(OC)=C1 GNSKGHQQFNMVSH-UHFFFAOYSA-N 0.000 claims 1
- WDROEHWYJIEEFT-UHFFFAOYSA-N 2-methoxy-4-[6-(thiophen-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(NCC=4SC=CC=4)C=CC3=NC=2)=C1 WDROEHWYJIEEFT-UHFFFAOYSA-N 0.000 claims 1
- IWUQKHWRRPDIRW-UHFFFAOYSA-N 2-methoxy-4-[6-[(3,4,5-trimethoxyphenyl)methylamino]imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=C(O)C(OC)=CC(C=2N3N=C(NCC=4C=C(OC)C(OC)=C(OC)C=4)C=CC3=NC=2)=C1 IWUQKHWRRPDIRW-UHFFFAOYSA-N 0.000 claims 1
- XEFUVQWKJMWQCK-UHFFFAOYSA-N 2-methoxy-4-[6-[(4-methoxyphenyl)methylamino]imidazo[1,2-b]pyridazin-3-yl]phenol Chemical compound C1=CC(OC)=CC=C1CNC1=NN2C(C=3C=C(OC)C(O)=CC=3)=CN=C2C=C1 XEFUVQWKJMWQCK-UHFFFAOYSA-N 0.000 claims 1
- SFDGJDBLYNJMFI-UHFFFAOYSA-N 3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC=NC2=C1 SFDGJDBLYNJMFI-UHFFFAOYSA-N 0.000 claims 1
- GCUWCTVRJNUNSB-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C2OCOC2=CC=C1C(N1N=2)=CN=C1C=CC=2NC1CCOCC1 GCUWCTVRJNUNSB-UHFFFAOYSA-N 0.000 claims 1
- VLXSAZOORSAKQP-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)-n-[(3-chlorophenyl)methyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC(CNC2=NN3C(C=4OC5=CC=CC=C5C=4)=CN=C3C=C2)=C1 VLXSAZOORSAKQP-UHFFFAOYSA-N 0.000 claims 1
- NKOBRSDHMMNMFS-UHFFFAOYSA-N 3-(1-benzofuran-5-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3C=C4C=COC4=CC=3)=CN=C2C=C1 NKOBRSDHMMNMFS-UHFFFAOYSA-N 0.000 claims 1
- NRODDGKCQJNZGR-UHFFFAOYSA-N 3-(1-methylindol-5-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C=1C=C2N(C)C=CC2=CC=1C(N1N=2)=CN=C1C=CC=2NC1CCOCC1 NRODDGKCQJNZGR-UHFFFAOYSA-N 0.000 claims 1
- YOHJXUCGTXNCQV-UHFFFAOYSA-N 3-(1H-indol-2-yl)-N-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3NC4=CC=CC=C4C=3)=CN=C2C=C1 YOHJXUCGTXNCQV-UHFFFAOYSA-N 0.000 claims 1
- AXOCFNVMBYJDJY-UHFFFAOYSA-N 3-(1h-indazol-6-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3C=C4NN=CC4=CC=3)=CN=C2C=C1 AXOCFNVMBYJDJY-UHFFFAOYSA-N 0.000 claims 1
- WOMZZJAJCKKGPF-UHFFFAOYSA-N 3-(1h-indol-5-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3C=C4C=CNC4=CC=3)=CN=C2C=C1 WOMZZJAJCKKGPF-UHFFFAOYSA-N 0.000 claims 1
- USQPQCUNDZGGKO-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound FC1=CC(F)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 USQPQCUNDZGGKO-UHFFFAOYSA-N 0.000 claims 1
- ILUKHUPYJKDDKX-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 ILUKHUPYJKDDKX-UHFFFAOYSA-N 0.000 claims 1
- LRMRSZOYWDATQW-UHFFFAOYSA-N 3-(2-fluorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound FC1=CC=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 LRMRSZOYWDATQW-UHFFFAOYSA-N 0.000 claims 1
- FARMWKAMFJACDP-UHFFFAOYSA-N 3-(2-methoxy-5-propan-2-ylphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=CC=C(C(C)C)C=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 FARMWKAMFJACDP-UHFFFAOYSA-N 0.000 claims 1
- VRWRCLFBELGLGR-UHFFFAOYSA-N 3-(2-methoxypyrimidin-5-yl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NC(OC)=NC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 VRWRCLFBELGLGR-UHFFFAOYSA-N 0.000 claims 1
- DUDQKNTVGVLEST-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 DUDQKNTVGVLEST-UHFFFAOYSA-N 0.000 claims 1
- QYKIWJHPGAYFMP-UHFFFAOYSA-N 3-(3,4-difluorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(F)C(F)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 QYKIWJHPGAYFMP-UHFFFAOYSA-N 0.000 claims 1
- ZJAHXEWFCQDCLN-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-n-(furan-2-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=C2N1N=C(NCC=1OC=CC=1)C=C2 ZJAHXEWFCQDCLN-UHFFFAOYSA-N 0.000 claims 1
- VINQLCSFJYLNIB-UHFFFAOYSA-N 3-(3,4-dimethylphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=C(C)C(C)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 VINQLCSFJYLNIB-UHFFFAOYSA-N 0.000 claims 1
- YVHJWFQOFXIJQJ-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound COC1=CC(OC)=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 YVHJWFQOFXIJQJ-UHFFFAOYSA-N 0.000 claims 1
- NRYQFUGOLUZWBC-UHFFFAOYSA-N 3-(3-aminophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound NC1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 NRYQFUGOLUZWBC-UHFFFAOYSA-N 0.000 claims 1
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- OEIWNDGDGDPXIO-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound ClC1=CC=CC(C=2N3N=C(NC4CCOCC4)C=CC3=NC=2)=C1 OEIWNDGDGDPXIO-UHFFFAOYSA-N 0.000 claims 1
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- PJPADMCOSXJIKA-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(Cl)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 PJPADMCOSXJIKA-UHFFFAOYSA-N 0.000 claims 1
- IMSLUXLFYQRYCU-UHFFFAOYSA-N 3-(4-ethenylphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(C=C)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 IMSLUXLFYQRYCU-UHFFFAOYSA-N 0.000 claims 1
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- BWRZPNZLUQKAFO-UHFFFAOYSA-N 3-(4-methylsulfonylphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 BWRZPNZLUQKAFO-UHFFFAOYSA-N 0.000 claims 1
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- DBSUBKDZKKKGDZ-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CN=C2N1N=C(NC1CCOCC1)C=C2 DBSUBKDZKKKGDZ-UHFFFAOYSA-N 0.000 claims 1
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- KDRFSAYDNRYPFC-UHFFFAOYSA-N 3-bromo-6-(furan-2-ylmethoxy)imidazo[1,2-b]pyridazine Chemical compound N=1N2C(Br)=CN=C2C=CC=1OCC1=CC=CO1 KDRFSAYDNRYPFC-UHFFFAOYSA-N 0.000 claims 1
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- DOPWTFXGWBIPOO-UHFFFAOYSA-N 3-bromo-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound N=1N2C(Br)=CN=C2C=CC=1NC1CCOCC1 DOPWTFXGWBIPOO-UHFFFAOYSA-N 0.000 claims 1
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- IEHKSBYALGYZHJ-UHFFFAOYSA-N 3-naphthalen-1-yl-n-(oxan-4-yl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1COCCC1NC1=NN2C(C=3C4=CC=CC=C4C=CC=3)=CN=C2C=C1 IEHKSBYALGYZHJ-UHFFFAOYSA-N 0.000 claims 1
- ZNIXBGSPJBGFNO-UHFFFAOYSA-N 3-naphthalen-2-yl-n-(2-pyridin-3-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C=C4C=CC=CC4=CC=3)N2N=C1NCCC1=CC=CN=C1 ZNIXBGSPJBGFNO-UHFFFAOYSA-N 0.000 claims 1
- FEJZJBDPYBAZQL-UHFFFAOYSA-N 3-naphthalen-2-yl-n-(pyridin-4-ylmethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C=3C=C4C=CC=CC4=CC=3)N2N=C1NCC1=CC=NC=C1 FEJZJBDPYBAZQL-UHFFFAOYSA-N 0.000 claims 1
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| GB0103926D0 (en) * | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
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| WO2006088246A1 (ja) * | 2005-02-18 | 2006-08-24 | Takeda Pharmaceutical Company Limited | Ｇｐｒ３４受容体機能調節剤 |
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| US7750007B2 (en) * | 2006-11-06 | 2010-07-06 | Supergen, Inc. | Imidazo[1,2-beta]pyridazine and pyrazolo[1,5-alpha]pyrimidine derivatives and their use as protein kinase inhibitors |
-
2007
- 2007-09-07 JP JP2009527436A patent/JP2010502716A/ja active Pending
- 2007-09-07 EP EP07837910A patent/EP2063962A2/en not_active Withdrawn
- 2007-09-07 US US12/440,154 patent/US20110021513A1/en not_active Abandoned
- 2007-09-07 AU AU2007292924A patent/AU2007292924A1/en not_active Abandoned
- 2007-09-07 CA CA002663091A patent/CA2663091A1/en not_active Abandoned
- 2007-09-07 CN CNA2007800414293A patent/CN101594909A/zh active Pending
- 2007-09-07 WO PCT/US2007/019577 patent/WO2008030579A2/en not_active Ceased
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