JP2013537174A5

JP2013537174A5 -

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Publication number: JP2013537174A5
Authority: JP; Japan
Prior art keywords: amino; imidazo; cyclopropyl; methylbenzamide; pyridazin
Prior art date: 2011-09-06
Legal status : Granted

Application number

JP2013527575A

Other languages

English (en)

Japanese (ja)

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JP2013537174A (ja

JP5824050B2 (ja

Filing date

2011-09-06

Publication date

2014-10-09

2011-09-06 Application filed filed Critical

2011-09-06 Priority claimed from PCT/EP2011/065368 external-priority patent/WO2012032031A1/en

2013-09-30 Publication of JP2013537174A publication Critical patent/JP2013537174A/ja

2014-10-09 Publication of JP2013537174A5 publication Critical patent/JP2013537174A5/ja

2015-11-25 Application granted granted Critical

2015-11-25 Publication of JP5824050B2 publication Critical patent/JP5824050B2/ja

Status Expired - Fee Related legal-status Critical Current

2031-09-06 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims description 37
239000000203 mixture Substances 0.000 claims description 11
238000000034 method Methods 0.000 claims description 7
-1 3-cyanophenoxy Chemical group 0.000 claims 90
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 57
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 34
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 18
125000005843 halogen group Chemical group 0.000 claims 16
125000001072 heteroaryl group Chemical group 0.000 claims 14
150000003839 salts Chemical class 0.000 claims 14
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 12
125000000592 heterocycloalkyl group Chemical group 0.000 claims 12
150000001204 N-oxides Chemical class 0.000 claims 10
239000012453 solvate Substances 0.000 claims 10
125000003396 thiol group Chemical group [H]S* 0.000 claims 10
125000003118 aryl group Chemical group 0.000 claims 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 5
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
201000010099 disease Diseases 0.000 claims 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
229910052739 hydrogen Inorganic materials 0.000 claims 4
239000001257 hydrogen Substances 0.000 claims 4
238000004519 manufacturing process Methods 0.000 claims 4
208000003174 Brain Neoplasms Diseases 0.000 claims 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
206010028980 Neoplasm Diseases 0.000 claims 3
230000010261 cell growth Effects 0.000 claims 3
230000004663 cell proliferation Effects 0.000 claims 3
230000001413 cellular effect Effects 0.000 claims 3
230000028709 inflammatory response Effects 0.000 claims 3
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
230000004083 survival effect Effects 0.000 claims 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 2
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 2
YXNUZAQXPPZNNU-UHFFFAOYSA-N 4-[6-(3-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)NC)=CC=C1C1=CN=C2N1N=C(OC=1C=C(F)C=CC=1)C=C2NCCC(F)(F)F YXNUZAQXPPZNNU-UHFFFAOYSA-N 0.000 claims 2
UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims 2
206010027476 Metastases Diseases 0.000 claims 2
206010059282 Metastases to central nervous system Diseases 0.000 claims 2
DMLIQHNMBZCNTR-UHFFFAOYSA-N N-cyclopropyl-4-[6-(4-fluoro-2-hydroxyanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C(=CC(F)=CC=4)O)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 DMLIQHNMBZCNTR-UHFFFAOYSA-N 0.000 claims 2
229930012538 Paclitaxel Natural products 0.000 claims 2
239000002253 acid Substances 0.000 claims 2
125000005418 aryl aryl group Chemical group 0.000 claims 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
KQGQNDIARMXUQS-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-hydroxy-2-methylanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(O)C=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 KQGQNDIARMXUQS-UHFFFAOYSA-N 0.000 claims 2
GXZASSUQCVVOFI-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(3-methoxyphenyl)sulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=CC(SC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 GXZASSUQCVVOFI-UHFFFAOYSA-N 0.000 claims 2
229960001592 paclitaxel Drugs 0.000 claims 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
OLBYYKSLVBXLGO-UHFFFAOYSA-N 2-[[3-[4-(cyclopropylcarbamoyl)-3-methylphenyl]-6-(3-fluorophenoxy)imidazo[1,2-b]pyridazin-8-yl]amino]ethanesulfonic acid Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCCS(O)(=O)=O)C3=NC=2)=CC=C1C(=O)NC1CC1 OLBYYKSLVBXLGO-UHFFFAOYSA-N 0.000 claims 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
DLHSWNMXXRQGQS-UHFFFAOYSA-N 4-[6-(2,3-difluorophenoxy)-8-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]-n,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)NC)=CC=C1C1=CN=C2N1N=C(OC=1C(=C(F)C=CC=1)F)C=C2NCCOC DLHSWNMXXRQGQS-UHFFFAOYSA-N 0.000 claims 1
PINYRFDOIAXNSD-UHFFFAOYSA-N 4-[6-(2-amino-3-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=C(F)C=CC=4)N)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 PINYRFDOIAXNSD-UHFFFAOYSA-N 0.000 claims 1
FDRAHQXLFJXXMK-UHFFFAOYSA-N 4-[6-(2-amino-4-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=CC(F)=CC=4)N)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 FDRAHQXLFJXXMK-UHFFFAOYSA-N 0.000 claims 1
CLGGPCCAPPVNKG-UHFFFAOYSA-N 4-[6-(2-amino-4-fluorophenyl)sulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C(=CC(F)=CC=4)N)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 CLGGPCCAPPVNKG-UHFFFAOYSA-N 0.000 claims 1
RRXBLWQGRZAPSP-UHFFFAOYSA-N 4-[6-(2-amino-5-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=CC=C(F)C=4)N)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 RRXBLWQGRZAPSP-UHFFFAOYSA-N 0.000 claims 1
SWQCDUBHQPDGQE-UHFFFAOYSA-N 4-[6-(2-chloro-3-fluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=C(F)C=CC=4)Cl)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 SWQCDUBHQPDGQE-UHFFFAOYSA-N 0.000 claims 1
ZJUKQNUXHMFWIO-UHFFFAOYSA-N 4-[6-(2-chloro-4-fluoroanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C(=CC(F)=CC=4)Cl)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 ZJUKQNUXHMFWIO-UHFFFAOYSA-N 0.000 claims 1
XGQWYPIFCYTMOI-UHFFFAOYSA-N 4-[6-(2-fluoro-4-hydroxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)NC)=CC=C1C1=CN=C2N1N=C(OC=1C(=CC(O)=CC=1)F)C=C2NCCC(F)(F)F XGQWYPIFCYTMOI-UHFFFAOYSA-N 0.000 claims 1
YSPRZSQNPRFXHI-UHFFFAOYSA-N 4-[6-(2-fluoro-4-methoxyphenoxy)-8-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]-n,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)NC)=CC=C1C1=CN=C2N1N=C(OC=1C(=CC(OC)=CC=1)F)C=C2NCCOC YSPRZSQNPRFXHI-UHFFFAOYSA-N 0.000 claims 1
AAERPMWCKNPAQN-UHFFFAOYSA-N 4-[6-(2-fluoro-4-methoxyphenoxy)-8-(2-morpholin-4-ylethylamino)imidazo[1,2-b]pyridazin-3-yl]-N,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)NC)=CC=C1C1=CN=C2N1N=C(OC=1C(=CC(OC)=CC=1)F)C=C2NCCN1CCOCC1 AAERPMWCKNPAQN-UHFFFAOYSA-N 0.000 claims 1
UMRKLWSOZZOFGO-UHFFFAOYSA-N 4-[6-(2-fluoro-4-methoxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)NC)=CC=C1C1=CN=C2N1N=C(OC=1C(=CC(OC)=CC=1)F)C=C2NCCC(F)(F)F UMRKLWSOZZOFGO-UHFFFAOYSA-N 0.000 claims 1
ZRCXCZVUNMPIAU-UHFFFAOYSA-N 4-[6-(2-fluoro-4-methoxyphenoxy)-8-(oxan-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-n,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)NC)=CC=C1C1=CN=C2N1N=C(OC=1C(=CC(OC)=CC=1)F)C=C2NCC1CCOCC1 ZRCXCZVUNMPIAU-UHFFFAOYSA-N 0.000 claims 1
DIWWYJAAGSRFJU-UHFFFAOYSA-N 4-[6-(3,4-difluorophenoxy)-8-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]-n,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)NC)=CC=C1C1=CN=C2N1N=C(OC=1C=C(F)C(F)=CC=1)C=C2NCCOC DIWWYJAAGSRFJU-UHFFFAOYSA-N 0.000 claims 1
QMTNGOQRFRBBKN-UHFFFAOYSA-N 4-[6-(3,4-difluorophenoxy)-8-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]-n-ethyl-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCC)=CC=C1C1=CN=C2N1N=C(OC=1C=C(F)C(F)=CC=1)C=C2NCCOC QMTNGOQRFRBBKN-UHFFFAOYSA-N 0.000 claims 1
OBCWHNVDLJFRLX-UHFFFAOYSA-N 4-[6-(3,4-difluorophenoxy)-8-(2-morpholin-4-ylethylamino)imidazo[1,2-b]pyridazin-3-yl]-N,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)NC)=CC=C1C1=CN=C2N1N=C(OC=1C=C(F)C(F)=CC=1)C=C2NCCN1CCOCC1 OBCWHNVDLJFRLX-UHFFFAOYSA-N 0.000 claims 1
OPYORPFHSAPHGP-UHFFFAOYSA-N 4-[6-(3,4-difluorophenoxy)-8-(2-morpholin-4-ylethylamino)imidazo[1,2-b]pyridazin-3-yl]-n-ethyl-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCC)=CC=C1C1=CN=C2N1N=C(OC=1C=C(F)C(F)=CC=1)C=C2NCCN1CCOCC1 OPYORPFHSAPHGP-UHFFFAOYSA-N 0.000 claims 1
IAZDIPNNMVZSAK-UHFFFAOYSA-N 4-[6-(3-chloro-4-fluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(Cl)C(F)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 IAZDIPNNMVZSAK-UHFFFAOYSA-N 0.000 claims 1
CGXAAERYILCNDB-UHFFFAOYSA-N 4-[6-(3-chloroanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=C(Cl)C=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 CGXAAERYILCNDB-UHFFFAOYSA-N 0.000 claims 1
OROBSHOBYGKVLJ-UHFFFAOYSA-N 4-[6-(3-chloroanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=C(Cl)C=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 OROBSHOBYGKVLJ-UHFFFAOYSA-N 0.000 claims 1
YNBJPBVAMFNGIR-UHFFFAOYSA-N 4-[6-(3-chlorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(Cl)C=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 YNBJPBVAMFNGIR-UHFFFAOYSA-N 0.000 claims 1
LCKCCPOQSOZOLF-UHFFFAOYSA-N 4-[6-(3-chlorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(Cl)C=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 LCKCCPOQSOZOLF-UHFFFAOYSA-N 0.000 claims 1
FNWLIIZNPHJQMU-UHFFFAOYSA-N 4-[6-(3-fluoro-4-methoxyphenoxy)-8-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]-N,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)NC)=CC=C1C1=CN=C2N1N=C(OC=1C=C(F)C(OC)=CC=1)C=C2NCCOC FNWLIIZNPHJQMU-UHFFFAOYSA-N 0.000 claims 1
VATUYCOQZPNBMZ-UHFFFAOYSA-N 4-[6-(3-fluoro-4-methoxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)NC)=CC=C1C1=CN=C2N1N=C(OC=1C=C(F)C(OC)=CC=1)C=C2NCCC(F)(F)F VATUYCOQZPNBMZ-UHFFFAOYSA-N 0.000 claims 1
KRQZDPRGVSCZIV-UHFFFAOYSA-N 4-[6-(3-fluoro-4-methoxyphenoxy)-8-(oxan-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-n,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)NC)=CC=C1C1=CN=C2N1N=C(OC=1C=C(F)C(OC)=CC=1)C=C2NCC1CCOCC1 KRQZDPRGVSCZIV-UHFFFAOYSA-N 0.000 claims 1
PXRGQELQOMRONE-UHFFFAOYSA-N 4-[6-(3-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(C(N)=O)C(C)=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=C1 PXRGQELQOMRONE-UHFFFAOYSA-N 0.000 claims 1
SNENIFJNYLLFEG-UHFFFAOYSA-N 4-[6-(3-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-(1-methoxycyclopropyl)-2-methylbenzamide Chemical compound C=1C=C(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)C=C(C)C=1C(=O)NC1(OC)CC1 SNENIFJNYLLFEG-UHFFFAOYSA-N 0.000 claims 1
ONKGLTSWGJXKRG-UHFFFAOYSA-N 4-[6-(4-chloro-2-fluoroanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C(=CC(Cl)=CC=4)F)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 ONKGLTSWGJXKRG-UHFFFAOYSA-N 0.000 claims 1
MGYMYBLKQDGOBJ-UHFFFAOYSA-N 4-[6-(4-chloro-2-fluoroanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C(=CC(Cl)=CC=4)F)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 MGYMYBLKQDGOBJ-UHFFFAOYSA-N 0.000 claims 1
JMSKOZNZXNTWNR-UHFFFAOYSA-N 4-[6-(4-chloro-3-fluoroanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-N-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=C(F)C(Cl)=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 JMSKOZNZXNTWNR-UHFFFAOYSA-N 0.000 claims 1
BVLXSTWFIOSTRF-UHFFFAOYSA-N 4-[6-(4-chloro-3-fluoroanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=C(F)C(Cl)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 BVLXSTWFIOSTRF-UHFFFAOYSA-N 0.000 claims 1
PUJNZOKOQINFFP-UHFFFAOYSA-N 4-[6-(4-chloro-3-fluorophenoxy)-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C(Cl)=CC=4)C=C(NCC4CCSCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 PUJNZOKOQINFFP-UHFFFAOYSA-N 0.000 claims 1
XHZFEEZRJSIXPK-UHFFFAOYSA-N 4-[6-(4-chloro-3-fluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C(Cl)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 XHZFEEZRJSIXPK-UHFFFAOYSA-N 0.000 claims 1
NHNWFZAOZMEVPI-UHFFFAOYSA-N 4-[6-(4-chloroanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=CC(Cl)=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 NHNWFZAOZMEVPI-UHFFFAOYSA-N 0.000 claims 1
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JAYPJRQAIXAGJX-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,3-difluorophenoxy)-8-(2-methylsulfonylethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=C(F)C=CC=4)F)C=C(NCCS(C)(=O)=O)C3=NC=2)=CC=C1C(=O)NC1CC1 JAYPJRQAIXAGJX-UHFFFAOYSA-N 0.000 claims 1
FKEYZRMTYOUZHZ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,3-difluorophenoxy)-8-(2-morpholin-4-ylethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=C(F)C=CC=4)F)C=C(NCCN4CCOCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 FKEYZRMTYOUZHZ-UHFFFAOYSA-N 0.000 claims 1
LDCLEHWGXRNODE-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,3-difluorophenoxy)-8-(methylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NC)=CC=1OC1=CC=CC(F)=C1F LDCLEHWGXRNODE-UHFFFAOYSA-N 0.000 claims 1
RPYZFOPOKJTIAH-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,3-difluorophenoxy)-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=C(F)C=CC=4)F)C=C(NCC4CCSCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 RPYZFOPOKJTIAH-UHFFFAOYSA-N 0.000 claims 1
RLGBVWDZTHNIMA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,3-difluorophenoxy)-8-[(1-methylazetidin-3-yl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1N(C)CC1CNC1=CC(OC=2C(=C(F)C=CC=2)F)=NN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 RLGBVWDZTHNIMA-UHFFFAOYSA-N 0.000 claims 1
WGDVEJRCLSAPKN-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,3-difluorophenoxy)-8-[(1-methylpiperidin-4-yl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1CN(C)CCC1CNC1=CC(OC=2C(=C(F)C=CC=2)F)=NN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 WGDVEJRCLSAPKN-UHFFFAOYSA-N 0.000 claims 1
SJFBZRHPPXOKBO-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,3-difluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=C(F)C=CC=4)F)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 SJFBZRHPPXOKBO-UHFFFAOYSA-N 0.000 claims 1
XLTKKASCMCFYHB-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,4-difluoroanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C(=CC(F)=CC=4)F)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 XLTKKASCMCFYHB-UHFFFAOYSA-N 0.000 claims 1
SYDRQFDYCUHGII-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,5-difluorophenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C(=CC=C(F)C=4)F)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 SYDRQFDYCUHGII-UHFFFAOYSA-N 0.000 claims 1
KBVIPCSBPGOWBL-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,6-difluorophenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C(=CC=CC=4F)F)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 KBVIPCSBPGOWBL-UHFFFAOYSA-N 0.000 claims 1
DSSYFYRKOOMSBH-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-3-methylsulfanylphenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CSC1=CC=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1F DSSYFYRKOOMSBH-UHFFFAOYSA-N 0.000 claims 1
JFKCTKMMFMTQKJ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-4-methoxyphenoxy)-8-(2-methylsulfonylethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound FC1=CC(OC)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCS(C)(=O)=O)=C1 JFKCTKMMFMTQKJ-UHFFFAOYSA-N 0.000 claims 1
SQAVLMZWPSPVBJ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-4-methoxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound FC1=CC(OC)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 SQAVLMZWPSPVBJ-UHFFFAOYSA-N 0.000 claims 1
NVPCBOQJOOAJTG-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-4-methoxyphenoxy)-8-(oxan-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound FC1=CC(OC)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC2CCOCC2)=C1 NVPCBOQJOOAJTG-UHFFFAOYSA-N 0.000 claims 1
LRSXQJWVMCJFBA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-4-methylphenyl)sulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound FC1=CC(C)=CC=C1SC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 LRSXQJWVMCJFBA-UHFFFAOYSA-N 0.000 claims 1
DWADCDQYDRXWRV-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-4-methylphenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound FC1=CC(C)=CC=C1SC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 DWADCDQYDRXWRV-UHFFFAOYSA-N 0.000 claims 1
JRZOKMQNVMRJMT-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-5-methylanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 JRZOKMQNVMRJMT-UHFFFAOYSA-N 0.000 claims 1
ZLHPFJJGLHTLJA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-5-methylanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 ZLHPFJJGLHTLJA-UHFFFAOYSA-N 0.000 claims 1
CGAOOKGKZZXMAO-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-5-methylphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 CGAOOKGKZZXMAO-UHFFFAOYSA-N 0.000 claims 1
CUERSJUVWODDIV-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-5-methylphenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 CUERSJUVWODDIV-UHFFFAOYSA-N 0.000 claims 1
ANLXHYDFMMZICO-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoroanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C(=CC=CC=4)F)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 ANLXHYDFMMZICO-UHFFFAOYSA-N 0.000 claims 1
VXJBPMYPAZYZNR-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoroanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C(=CC=CC=4)F)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 VXJBPMYPAZYZNR-UHFFFAOYSA-N 0.000 claims 1
WQQFXRBEZQKZFI-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=CC=CC=4)F)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 WQQFXRBEZQKZFI-UHFFFAOYSA-N 0.000 claims 1
XKBJPGKHHKSNLO-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluorophenoxy)-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=CC=CC=4)F)C=C(NCC4CCSCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 XKBJPGKHHKSNLO-UHFFFAOYSA-N 0.000 claims 1
UIIBZLYLRDUCBY-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=CC=CC=4)F)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 UIIBZLYLRDUCBY-UHFFFAOYSA-N 0.000 claims 1
OQFZVJYENWMKEJ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluorophenyl)sulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C(=CC=CC=4)F)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 OQFZVJYENWMKEJ-UHFFFAOYSA-N 0.000 claims 1
LMIPHEDIIOSBCT-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluorophenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C(=CC=CC=4)F)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 LMIPHEDIIOSBCT-UHFFFAOYSA-N 0.000 claims 1
BIWBYNZZGMUILD-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-hydroxy-3-propan-2-ylphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC(C)C1=CC=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1O BIWBYNZZGMUILD-UHFFFAOYSA-N 0.000 claims 1
XITDDHPTQKIAHT-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-hydroxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=CC=CC=4)O)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 XITDDHPTQKIAHT-UHFFFAOYSA-N 0.000 claims 1
JYXLDUXXLRWNEY-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-hydroxyphenyl)sulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C(=CC=CC=4)O)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 JYXLDUXXLRWNEY-UHFFFAOYSA-N 0.000 claims 1
MUNLNCZGBDNFFX-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-hydroxyphenyl)sulfanyl-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C(=CC=CC=4)O)C=C(NCC4CCSCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 MUNLNCZGBDNFFX-UHFFFAOYSA-N 0.000 claims 1
QXDTVUDZULCANS-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-methoxy-3-propan-2-ylphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=CC=C(C(C)C)C(OC)=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 QXDTVUDZULCANS-UHFFFAOYSA-N 0.000 claims 1
CXUYTPKUGYIPMO-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-methoxyanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=CC=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 CXUYTPKUGYIPMO-UHFFFAOYSA-N 0.000 claims 1
CRTKOUIDKLSOAT-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-methoxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 CRTKOUIDKLSOAT-UHFFFAOYSA-N 0.000 claims 1
YKTOBYGMBTXNFB-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-methoxyphenyl)sulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=CC=C1SC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 YKTOBYGMBTXNFB-UHFFFAOYSA-N 0.000 claims 1
LBVPUWPUOIELIN-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,4-difluoroanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=C(F)C(F)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 LBVPUWPUOIELIN-UHFFFAOYSA-N 0.000 claims 1
ANMATZBITLZDNB-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,4-difluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C(F)=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 ANMATZBITLZDNB-UHFFFAOYSA-N 0.000 claims 1
WMCOKEBNQSACSX-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,4-difluorophenoxy)-8-(methylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NC)=CC=1OC1=CC=C(F)C(F)=C1 WMCOKEBNQSACSX-UHFFFAOYSA-N 0.000 claims 1
KDBGHFSTGHMLCA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,4-difluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C(F)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 KDBGHFSTGHMLCA-UHFFFAOYSA-N 0.000 claims 1
GVCVEPCWDJOSSA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,4-difluorophenoxy)-8-[2-(dimethylamino)ethylamino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCN(C)C)=CC=1OC1=CC=C(F)C(F)=C1 GVCVEPCWDJOSSA-UHFFFAOYSA-N 0.000 claims 1
QGLLUUYSGRORPB-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,4-difluorophenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=C(F)C(F)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 QGLLUUYSGRORPB-UHFFFAOYSA-N 0.000 claims 1
ZMXUCUPYHBVTFY-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,5-difluoroanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=C(F)C=C(F)C=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 ZMXUCUPYHBVTFY-UHFFFAOYSA-N 0.000 claims 1
ZERKWWBTNONCCE-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,5-difluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=C(F)C=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 ZERKWWBTNONCCE-UHFFFAOYSA-N 0.000 claims 1
DIGALEXYONTKIS-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,5-difluorophenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=C(F)C=C(F)C=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 DIGALEXYONTKIS-UHFFFAOYSA-N 0.000 claims 1
DTGCZEAGSDIYFM-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,5-dimethylphenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C)=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 DTGCZEAGSDIYFM-UHFFFAOYSA-N 0.000 claims 1
FRKWCTRCMCHEFT-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-ethenylanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=C(C=C)C=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 FRKWCTRCMCHEFT-UHFFFAOYSA-N 0.000 claims 1
NREHQOOKBKDNPA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-2-methylphenyl)sulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C(=C(F)C=CC=4)C)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 NREHQOOKBKDNPA-UHFFFAOYSA-N 0.000 claims 1
LNQUOVAXPUZSOK-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-4-methoxyanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(OC)=CC=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 LNQUOVAXPUZSOK-UHFFFAOYSA-N 0.000 claims 1
UKWDUQDUUUSSPA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-4-methoxyanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(OC)=CC=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 UKWDUQDUUUSSPA-UHFFFAOYSA-N 0.000 claims 1
SKVHLRDWBPFLDJ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-4-methoxyphenoxy)-8-(2-methylsulfonylethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(OC)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCS(C)(=O)=O)=C1 SKVHLRDWBPFLDJ-UHFFFAOYSA-N 0.000 claims 1
QCNDQTRMFKWHMC-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-4-methoxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(OC)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 QCNDQTRMFKWHMC-UHFFFAOYSA-N 0.000 claims 1
TZCDBTQIJVPYCH-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-4-methylphenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(C)=CC=C1SC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 TZCDBTQIJVPYCH-UHFFFAOYSA-N 0.000 claims 1
LAJNBGGUEPHFEZ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-5-methylanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(F)=CC(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 LAJNBGGUEPHFEZ-UHFFFAOYSA-N 0.000 claims 1
MRKNAOQMMPSMSK-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-5-methylphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(F)=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 MRKNAOQMMPSMSK-UHFFFAOYSA-N 0.000 claims 1
XCHLKOYBBLFTME-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-5-methylphenoxy)-8-(4,4,4-trifluorobutylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(F)=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCCC(F)(F)F)=C2)=C1 XCHLKOYBBLFTME-UHFFFAOYSA-N 0.000 claims 1
ZJPYPUOKBZKBIN-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-5-methylphenoxy)-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(F)=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC3CCSCC3)=C2)=C1 ZJPYPUOKBZKBIN-UHFFFAOYSA-N 0.000 claims 1
XODNYIVQIRRXRE-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-5-methylphenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(F)=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 XODNYIVQIRRXRE-UHFFFAOYSA-N 0.000 claims 1
VTBOLWKVAZOVQY-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-5-methylphenyl)sulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(F)=CC(SC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 VTBOLWKVAZOVQY-UHFFFAOYSA-N 0.000 claims 1
PUCXOWUKDRVJGR-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-5-methylphenyl)sulfanyl-8-(4,4,4-trifluorobutylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(F)=CC(SC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCCC(F)(F)F)=C2)=C1 PUCXOWUKDRVJGR-UHFFFAOYSA-N 0.000 claims 1
NATSWSNSBBFYKO-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-5-methylphenyl)sulfanyl-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(F)=CC(SC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC3CCSCC3)=C2)=C1 NATSWSNSBBFYKO-UHFFFAOYSA-N 0.000 claims 1
UVVGMFVFUSCRCT-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-5-methylphenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(F)=CC(SC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 UVVGMFVFUSCRCT-UHFFFAOYSA-N 0.000 claims 1
PTDGBWNXBKRINS-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoroanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=C(F)C=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 PTDGBWNXBKRINS-UHFFFAOYSA-N 0.000 claims 1
HQIKRGYWVOQEFV-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(1h-pyrazol-5-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCC4=NNC=C4)C3=NC=2)=CC=C1C(=O)NC1CC1 HQIKRGYWVOQEFV-UHFFFAOYSA-N 0.000 claims 1
AQNSRKMCVMCYHS-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(2,2,2-trifluoroethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 AQNSRKMCVMCYHS-UHFFFAOYSA-N 0.000 claims 1
YLASFKKWWVWGPB-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(2-hydroxyethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCCO)C3=NC=2)=CC=C1C(=O)NC1CC1 YLASFKKWWVWGPB-UHFFFAOYSA-N 0.000 claims 1
SMOOINCGSZGKFP-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCOC)=CC=1OC1=CC=CC(F)=C1 SMOOINCGSZGKFP-UHFFFAOYSA-N 0.000 claims 1
GBHCSNZBRSOJMI-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(2-morpholin-4-ylethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCCN4CCOCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 GBHCSNZBRSOJMI-UHFFFAOYSA-N 0.000 claims 1
KUORWNYCYLJPCJ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(2-piperidin-1-ylethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCCN4CCCCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 KUORWNYCYLJPCJ-UHFFFAOYSA-N 0.000 claims 1
UICZQHUJEIPITP-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 UICZQHUJEIPITP-UHFFFAOYSA-N 0.000 claims 1
KNRBZVUJPHSLBD-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(3-piperidin-1-ylpropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCCCN4CCCCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 KNRBZVUJPHSLBD-UHFFFAOYSA-N 0.000 claims 1
KOMFVSHZKYSMRR-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(methylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NC)=CC=1OC1=CC=CC(F)=C1 KOMFVSHZKYSMRR-UHFFFAOYSA-N 0.000 claims 1
YGCFYGZQSYILQJ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(oxan-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCC4CCOCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 YGCFYGZQSYILQJ-UHFFFAOYSA-N 0.000 claims 1
DEKPNEXWSBAWCK-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(oxetan-3-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCC4COC4)C3=NC=2)=CC=C1C(=O)NC1CC1 DEKPNEXWSBAWCK-UHFFFAOYSA-N 0.000 claims 1
MRXTVEOGKURJNP-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(oxolan-3-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCC4COCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 MRXTVEOGKURJNP-UHFFFAOYSA-N 0.000 claims 1
HESRLTXDFMIMTL-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCC4CCSCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 HESRLTXDFMIMTL-UHFFFAOYSA-N 0.000 claims 1
XKPHLXUQSUMFKA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[(1-methylpiperidin-4-yl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1CN(C)CCC1CNC1=CC(OC=2C=C(F)C=CC=2)=NN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 XKPHLXUQSUMFKA-UHFFFAOYSA-N 0.000 claims 1
YNRMAVIGZXICCY-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[(1-methylpyrazol-3-yl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCC4=NN(C)C=C4)C3=NC=2)=CC=C1C(=O)NC1CC1 YNRMAVIGZXICCY-UHFFFAOYSA-N 0.000 claims 1
UISCUPDKVBCQMK-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 UISCUPDKVBCQMK-UHFFFAOYSA-N 0.000 claims 1
NKUGPHCEYSJMID-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]benzenecarbothioamide Chemical compound N=1N2C(C=3C=CC(=CC=3)C(=S)NC3CC3)=CN=C2C(NCC(C)(O)C)=CC=1OC1=CC=CC(F)=C1 NKUGPHCEYSJMID-UHFFFAOYSA-N 0.000 claims 1
AKOHZMQPCSZUKA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[(3,3,3-trifluoro-2-hydroxypropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCC(O)C(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 AKOHZMQPCSZUKA-UHFFFAOYSA-N 0.000 claims 1
MNGUBSHTSKMYJC-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[(3-hydroxy-3-methylbutyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 MNGUBSHTSKMYJC-UHFFFAOYSA-N 0.000 claims 1
SNJSOIKEGVKRSG-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[3-[methyl(methylcarbamoyl)amino]propylamino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCCN(C)C(=O)NC)=CC=1OC1=CC=CC(F)=C1 SNJSOIKEGVKRSG-UHFFFAOYSA-N 0.000 claims 1
HDMWSZZBLIENJN-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenyl)sulfanyl-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=C(F)C=CC=4)C=C(NCC4CCSCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 HDMWSZZBLIENJN-UHFFFAOYSA-N 0.000 claims 1
HURVTMRCYVCXLS-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=C(F)C=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 HURVTMRCYVCXLS-UHFFFAOYSA-N 0.000 claims 1
YGACCNRMTXHMGU-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenyl)sulfanyl-8-[(3,3,3-trifluoro-2-hydroxypropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=C(F)C=CC=4)C=C(NCC(O)C(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 YGACCNRMTXHMGU-UHFFFAOYSA-N 0.000 claims 1
KFQSIQTXJFJIDI-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenyl)sulfinyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCCC(F)(F)F)C3=NC=2)S(=O)C=2C=C(F)C=CC=2)=CC=C1C(=O)NC1CC1 KFQSIQTXJFJIDI-UHFFFAOYSA-N 0.000 claims 1
QANSCOIGAZIDDM-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenyl)sulfonyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCCC(F)(F)F)C3=NC=2)S(=O)(=O)C=2C=C(F)C=CC=2)=CC=C1C(=O)NC1CC1 QANSCOIGAZIDDM-UHFFFAOYSA-N 0.000 claims 1
FLVPRKNROMCXLQ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-hydroxy-2-methylanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C(=C(O)C=CC=4)C)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 FLVPRKNROMCXLQ-UHFFFAOYSA-N 0.000 claims 1
GNQOTPROKQTWQR-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-hydroxyanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=C(O)C=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 GNQOTPROKQTWQR-UHFFFAOYSA-N 0.000 claims 1
RRUDAAISSVOPNQ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-hydroxyphenyl)sulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=C(O)C=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 RRUDAAISSVOPNQ-UHFFFAOYSA-N 0.000 claims 1
FMXLUSCLYSPAIF-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-methoxy-2-methylanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=CC(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1C FMXLUSCLYSPAIF-UHFFFAOYSA-N 0.000 claims 1
FFQOZRAGNHSXQW-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-methoxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 FFQOZRAGNHSXQW-UHFFFAOYSA-N 0.000 claims 1
AOUYWXVCYVNFEG-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluoro-2-methoxyanilino)-8-(4,4,4-trifluorobutylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC(F)=CC=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCCC(F)(F)F)=C1 AOUYWXVCYVNFEG-UHFFFAOYSA-N 0.000 claims 1
DKIRWSGCDAVRRN-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluoro-2-methoxyanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC(F)=CC=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 DKIRWSGCDAVRRN-UHFFFAOYSA-N 0.000 claims 1
BBBADJUMIOKWCS-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluoro-2-methylphenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(F)=CC=C1SC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 BBBADJUMIOKWCS-UHFFFAOYSA-N 0.000 claims 1
LSLDLTZNGVYIAB-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluoro-3-hydroxyanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=C(O)C(F)=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 LSLDLTZNGVYIAB-UHFFFAOYSA-N 0.000 claims 1
KHGZZVISNCZHGN-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluoro-3-methoxyanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(OC)=CC(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 KHGZZVISNCZHGN-UHFFFAOYSA-N 0.000 claims 1
WRJCVTKSIZGUBP-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluoro-3-methoxyanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(OC)=CC(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 WRJCVTKSIZGUBP-UHFFFAOYSA-N 0.000 claims 1
KVEJLBMHMUHTIL-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluoro-3-methylanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(C)=CC(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 KVEJLBMHMUHTIL-UHFFFAOYSA-N 0.000 claims 1
UXMUTYLLOWVJIQ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluoro-3-methylanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(C)=CC(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 UXMUTYLLOWVJIQ-UHFFFAOYSA-N 0.000 claims 1
ZUVNJWZHGOFNIA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluoro-3-methylphenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(C)=CC(SC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 ZUVNJWZHGOFNIA-UHFFFAOYSA-N 0.000 claims 1
RKMKRDFSVDQHTR-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluoroanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=CC(F)=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 RKMKRDFSVDQHTR-UHFFFAOYSA-N 0.000 claims 1
DQKUKUSTXITZCI-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluoroanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=CC(F)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 DQKUKUSTXITZCI-UHFFFAOYSA-N 0.000 claims 1
VLPSGUKEPWQJDX-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=CC(F)=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 VLPSGUKEPWQJDX-UHFFFAOYSA-N 0.000 claims 1
JGYRKMWORQQRPO-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluorophenoxy)-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=CC(F)=CC=4)C=C(NCC4CCSCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 JGYRKMWORQQRPO-UHFFFAOYSA-N 0.000 claims 1
WDQGQXRVEBRSKH-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=CC(F)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 WDQGQXRVEBRSKH-UHFFFAOYSA-N 0.000 claims 1
CYNBBWUTNDUQKI-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluorophenyl)sulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=CC(F)=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 CYNBBWUTNDUQKI-UHFFFAOYSA-N 0.000 claims 1
LVPRNRRLWLGVFX-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluorophenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=CC(F)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 LVPRNRRLWLGVFX-UHFFFAOYSA-N 0.000 claims 1
ZIDVSJWMJNADRK-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-hydroxy-3-methylphenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(O)C(C)=CC(SC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 ZIDVSJWMJNADRK-UHFFFAOYSA-N 0.000 claims 1
DPDANNAASUSFTK-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-methoxyanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=CC(OC)=CC=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 DPDANNAASUSFTK-UHFFFAOYSA-N 0.000 claims 1
NEBDRACCUHZROA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-methoxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=CC(OC)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 NEBDRACCUHZROA-UHFFFAOYSA-N 0.000 claims 1
CAAUDXWQNSZFGZ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-methoxyphenyl)sulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=CC(OC)=CC=C1SC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 CAAUDXWQNSZFGZ-UHFFFAOYSA-N 0.000 claims 1
WUAJVEQSFQIGMI-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-fluoro-2-methylanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 WUAJVEQSFQIGMI-UHFFFAOYSA-N 0.000 claims 1
UTKSLUDVGOKRJY-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-fluoro-2-methylanilino)-8-(4,4,4-trifluorobutylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCCC(F)(F)F)=C1 UTKSLUDVGOKRJY-UHFFFAOYSA-N 0.000 claims 1
KHSSWPNWYZYWBF-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-fluoro-2-methylanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 KHSSWPNWYZYWBF-UHFFFAOYSA-N 0.000 claims 1
GOWNGRZYVGUVIV-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-fluoro-2-methylphenoxy)-8-(2-methylsulfonylethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCS(C)(=O)=O)=C1 GOWNGRZYVGUVIV-UHFFFAOYSA-N 0.000 claims 1
FMHHQGZBELCBMG-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-fluoro-2-methylphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 FMHHQGZBELCBMG-UHFFFAOYSA-N 0.000 claims 1
YADUGVCQKYSQBL-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-fluoro-2-methylphenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 YADUGVCQKYSQBL-UHFFFAOYSA-N 0.000 claims 1
SJOFAAWGHRDYPL-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-fluoro-2-methylphenyl)sulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C=C1SC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 SJOFAAWGHRDYPL-UHFFFAOYSA-N 0.000 claims 1
BSMHGSNIMCTWKT-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-fluoro-2-methylphenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C=C1SC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 BSMHGSNIMCTWKT-UHFFFAOYSA-N 0.000 claims 1
OWSCFNINYYPIBR-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-fluoropyridin-3-yl)oxy-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=NC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 OWSCFNINYYPIBR-UHFFFAOYSA-N 0.000 claims 1
UMOCWIBXOUGVNT-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-methoxy-2-methylanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=C(C)C(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 UMOCWIBXOUGVNT-UHFFFAOYSA-N 0.000 claims 1
MLJZXKSAVBMCFI-UHFFFAOYSA-N n-cyclopropyl-4-[6-(6-fluoropyridin-3-yl)oxy-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=NC(F)=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 MLJZXKSAVBMCFI-UHFFFAOYSA-N 0.000 claims 1
MDSYXYDJKMNYOH-UHFFFAOYSA-N n-cyclopropyl-4-[6-(6-fluoropyridin-3-yl)oxy-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=NC(F)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 MDSYXYDJKMNYOH-UHFFFAOYSA-N 0.000 claims 1
YIASAZMUIHTEFN-UHFFFAOYSA-N n-cyclopropyl-4-[6-(8-hydroxy-3,4-dihydro-2h-quinolin-1-yl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCCC(F)(F)F)C3=NC=2)N2C3=C(O)C=CC=C3CCC2)=CC=C1C(=O)NC1CC1 YIASAZMUIHTEFN-UHFFFAOYSA-N 0.000 claims 1
SBEMBTYCYIETHV-UHFFFAOYSA-N n-cyclopropyl-4-[6-[(3-fluoro-4-methoxyphenyl)methyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(OC)=CC=C1CC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 SBEMBTYCYIETHV-UHFFFAOYSA-N 0.000 claims 1
BBVBIXQHYFGCNP-UHFFFAOYSA-N n-cyclopropyl-4-[6-[(3-fluoro-4-methylphenyl)methyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(C)=CC=C1CC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 BBVBIXQHYFGCNP-UHFFFAOYSA-N 0.000 claims 1
CFLPLZYHWYKUBT-UHFFFAOYSA-N n-cyclopropyl-4-[6-[(6-fluoropyridin-3-yl)amino]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=NC(F)=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 CFLPLZYHWYKUBT-UHFFFAOYSA-N 0.000 claims 1
BNDXPLDMPMSUKN-UHFFFAOYSA-N n-cyclopropyl-4-[6-[(6-fluoropyridin-3-yl)amino]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=NC(F)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 BNDXPLDMPMSUKN-UHFFFAOYSA-N 0.000 claims 1
CBCUZEBMDWZTCF-UHFFFAOYSA-N n-cyclopropyl-4-[6-[(6-methoxypyridin-3-yl)amino]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=NC(OC)=CC=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 CBCUZEBMDWZTCF-UHFFFAOYSA-N 0.000 claims 1
WJVSFGBFDBEZJV-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(hydroxymethyl)anilino]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C(=CC=CC=4)CO)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 WJVSFGBFDBEZJV-UHFFFAOYSA-N 0.000 claims 1
BICAUVVHXBHWQM-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(hydroxymethyl)anilino]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C(=CC=CC=4)CO)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 BICAUVVHXBHWQM-UHFFFAOYSA-N 0.000 claims 1
LPRPCBYATFAECT-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(hydroxymethyl)phenyl]sulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C(=CC=CC=4)CO)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 LPRPCBYATFAECT-UHFFFAOYSA-N 0.000 claims 1
NSGJLAHXKOQZNX-UHFFFAOYSA-N n-cyclopropyl-4-[6-[3-(2-hydroxy-2-methylpropoxy)phenoxy]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(OCC(C)(C)O)C=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 NSGJLAHXKOQZNX-UHFFFAOYSA-N 0.000 claims 1
VQBHFUPNXVSCOT-UHFFFAOYSA-N n-cyclopropyl-4-[6-[4-(2-hydroxyethyl)anilino]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=CC(CCO)=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 VQBHFUPNXVSCOT-UHFFFAOYSA-N 0.000 claims 1
BRGXCEQWZKVGAK-UHFFFAOYSA-N n-cyclopropyl-4-[6-[4-(2-hydroxyethyl)anilino]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=CC(CCO)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 BRGXCEQWZKVGAK-UHFFFAOYSA-N 0.000 claims 1
HAUCYLLFHFKNEG-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(1-methylpyrazol-4-yl)oxyimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC4=CN(C)N=C4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 HAUCYLLFHFKNEG-UHFFFAOYSA-N 0.000 claims 1
POTGSEYLSHIJHV-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(1h-1,2,4-triazol-5-ylsulfanyl)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4NC=NN=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 POTGSEYLSHIJHV-UHFFFAOYSA-N 0.000 claims 1
GVEQAFIWBZFRGS-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(1h-imidazol-2-ylsulfanyl)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4NC=CN=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 GVEQAFIWBZFRGS-UHFFFAOYSA-N 0.000 claims 1
SZVGCVSFSAHIFJ-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(1h-pyrazol-5-yloxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4NN=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 SZVGCVSFSAHIFJ-UHFFFAOYSA-N 0.000 claims 1
MWKWPEHPVDRFEW-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(2-hydroxyphenyl)sulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C(=CC=CC=4)O)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 MWKWPEHPVDRFEW-UHFFFAOYSA-N 0.000 claims 1
JHSXHOLAPBGKLO-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(2-methoxyanilino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=CC=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 JHSXHOLAPBGKLO-UHFFFAOYSA-N 0.000 claims 1
OQCFRFUEMRMCFB-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(2-methoxyphenyl)sulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=CC=C1SC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 OQCFRFUEMRMCFB-UHFFFAOYSA-N 0.000 claims 1
YQLJKEYROMGECQ-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(2-methylpyrazol-3-yl)oxyimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4N(N=CC=4)C)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 YQLJKEYROMGECQ-UHFFFAOYSA-N 0.000 claims 1
UYIXJODYWGFFCH-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(3-hydroxyphenyl)sulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=C(O)C=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 UYIXJODYWGFFCH-UHFFFAOYSA-N 0.000 claims 1
VDDGTRJJQIOAQH-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(3-methoxy-2-methylanilino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=CC(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1C VDDGTRJJQIOAQH-UHFFFAOYSA-N 0.000 claims 1
QEPYPYRXRQZZMU-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(3-methoxyanilino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=CC(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 QEPYPYRXRQZZMU-UHFFFAOYSA-N 0.000 claims 1
XQZLEUXTEKVGQB-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(3-methylanilino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=CC(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 XQZLEUXTEKVGQB-UHFFFAOYSA-N 0.000 claims 1
QTLFEEXOUPJCMD-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(3-methylphenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 QTLFEEXOUPJCMD-UHFFFAOYSA-N 0.000 claims 1
RATXOGVHPZSQTG-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(3-propan-2-ylanilino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC(C)C1=CC=CC(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 RATXOGVHPZSQTG-UHFFFAOYSA-N 0.000 claims 1
ROXFZBULEMIWOR-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(3-propan-2-yloxyphenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC(C)OC1=CC=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 ROXFZBULEMIWOR-UHFFFAOYSA-N 0.000 claims 1
GHOUXPRZODPDMI-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(3-propan-2-ylphenyl)sulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC(C)C1=CC=CC(SC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 GHOUXPRZODPDMI-UHFFFAOYSA-N 0.000 claims 1
OVSWTGAJLIXKDB-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(4-hydroxyphenyl)sulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=CC(O)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 OVSWTGAJLIXKDB-UHFFFAOYSA-N 0.000 claims 1
OQUCKRDYSFYWSC-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(4-methoxyanilino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=CC(OC)=CC=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 OQUCKRDYSFYWSC-UHFFFAOYSA-N 0.000 claims 1
KIZAHVVNHOVQPI-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(4-methoxyphenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=CC(OC)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 KIZAHVVNHOVQPI-UHFFFAOYSA-N 0.000 claims 1
SBHAMDXFLZCJOE-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(4-methoxyphenyl)sulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=CC(OC)=CC=C1SC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 SBHAMDXFLZCJOE-UHFFFAOYSA-N 0.000 claims 1
JMBBJYAAYUADKO-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(4-propan-2-yloxyphenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=CC(OC(C)C)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 JMBBJYAAYUADKO-UHFFFAOYSA-N 0.000 claims 1
JZFGCXJPQIGOCH-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(5-methoxy-2-methylanilino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=C(C)C(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 JZFGCXJPQIGOCH-UHFFFAOYSA-N 0.000 claims 1
GJVOOBPXFFZMJI-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(6-methylpyridin-3-yl)oxyimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=NC(C)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 GJVOOBPXFFZMJI-UHFFFAOYSA-N 0.000 claims 1
ABKXOSZAQVKKQX-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(pyridin-2-ylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4N=CC=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 ABKXOSZAQVKKQX-UHFFFAOYSA-N 0.000 claims 1
AUICETRGBAFHJS-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(pyridin-3-ylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=NC=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 AUICETRGBAFHJS-UHFFFAOYSA-N 0.000 claims 1
LNUPYBVDGOJQEV-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(pyridin-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=CN=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 LNUPYBVDGOJQEV-UHFFFAOYSA-N 0.000 claims 1
LIHORSKXSFKVNK-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-[(4-methyl-1,2,4-triazol-3-yl)sulfanyl]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4N(C=NN=4)C)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 LIHORSKXSFKVNK-UHFFFAOYSA-N 0.000 claims 1
ZCUPLMMNYNYHAV-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-[(5-methyl-1h-imidazol-2-yl)sulfanyl]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CNC(SC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=N1 ZCUPLMMNYNYHAV-UHFFFAOYSA-N 0.000 claims 1
MSAAWZOJOVCQSK-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-[(5-methyl-1h-pyrazol-3-yl)oxy]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N1C(C)=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=N1 MSAAWZOJOVCQSK-UHFFFAOYSA-N 0.000 claims 1
NATXKNFGDCFBGO-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-[(6-methoxypyridin-3-yl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=NC(OC)=CC=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 NATXKNFGDCFBGO-UHFFFAOYSA-N 0.000 claims 1
LFWLTSKODBVINV-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-[4-(trifluoromethyl)phenyl]sulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=CC(=CC=4)C(F)(F)F)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 LFWLTSKODBVINV-UHFFFAOYSA-N 0.000 claims 1
IGYWWZFIEZDSTF-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-phenoxyimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=CC=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 IGYWWZFIEZDSTF-UHFFFAOYSA-N 0.000 claims 1
LZGHVQNONINQGC-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-phenoxyimidazo[1,2-b]pyridazin-3-yl]benzenecarbothioamide Chemical compound N=1N2C(C=3C=CC(=CC=3)C(=S)NC3CC3)=CN=C2C(NCC(C)(O)C)=CC=1OC1=CC=CC=C1 LZGHVQNONINQGC-UHFFFAOYSA-N 0.000 claims 1
WAFNAGQJOJKQNE-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-phenylsulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=CC=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 WAFNAGQJOJKQNE-UHFFFAOYSA-N 0.000 claims 1
WMSRWNHKWIWIDU-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-pyrazin-2-ylsulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4N=CC=NC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 WMSRWNHKWIWIDU-UHFFFAOYSA-N 0.000 claims 1
CRYKFNFMMPOFFW-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-pyridin-2-yloxyimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4N=CC=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 CRYKFNFMMPOFFW-UHFFFAOYSA-N 0.000 claims 1
VTAHDWHRDJVDCB-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-pyridin-2-ylsulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4N=CC=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 VTAHDWHRDJVDCB-UHFFFAOYSA-N 0.000 claims 1
AXCJLTLFYKHKNJ-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-pyridin-3-yloxyimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=NC=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 AXCJLTLFYKHKNJ-UHFFFAOYSA-N 0.000 claims 1
UQSYTCLGILKGTL-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-pyridin-4-yloxyimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=CN=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 UQSYTCLGILKGTL-UHFFFAOYSA-N 0.000 claims 1
QHINUQGPMDOKLT-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-pyridin-4-ylsulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=CN=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 QHINUQGPMDOKLT-UHFFFAOYSA-N 0.000 claims 1
KSYVXHVJULZNME-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-pyrimidin-5-yloxyimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=NC=NC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 KSYVXHVJULZNME-UHFFFAOYSA-N 0.000 claims 1
UYVWPPDIVOCMAT-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-quinolin-5-yloxyimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C5=CC=CN=C5C=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 UYVWPPDIVOCMAT-UHFFFAOYSA-N 0.000 claims 1
UPRVHPYNHAOSRA-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-quinolin-6-yloxyimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C5C=CC=NC5=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 UPRVHPYNHAOSRA-UHFFFAOYSA-N 0.000 claims 1
MNOGBZVFRZWZRU-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(3,3-difluorocyclobutyl)methylamino]-6-(3-fluorophenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCC4CC(F)(F)C4)C3=NC=2)=CC=C1C(=O)NC1CC1 MNOGBZVFRZWZRU-UHFFFAOYSA-N 0.000 claims 1
PYXFUEFJAVRMIU-UHFFFAOYSA-N n-cyclopropyl-4-[8-[2-(dimethylamino)ethylamino]-6-(3-fluorophenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCN(C)C)=CC=1OC1=CC=CC(F)=C1 PYXFUEFJAVRMIU-UHFFFAOYSA-N 0.000 claims 1
IAYZNYHWGWOPSA-UHFFFAOYSA-N n-cyclopropyl-4-[8-[3-(dimethylamino)propylamino]-6-(3-fluorophenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCCN(C)C)=CC=1OC1=CC=CC(F)=C1 IAYZNYHWGWOPSA-UHFFFAOYSA-N 0.000 claims 1
KUEHDEJXZATWKJ-UHFFFAOYSA-N n-ethyl-4-[6-(2-fluoro-4-methoxyphenoxy)-8-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCC)=CC=C1C1=CN=C2N1N=C(OC=1C(=CC(OC)=CC=1)F)C=C2NCCOC KUEHDEJXZATWKJ-UHFFFAOYSA-N 0.000 claims 1
FUIKSWQDCJPDCE-UHFFFAOYSA-N n-ethyl-4-[6-(2-fluoro-4-methoxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCC)=CC=C1C1=CN=C2N1N=C(OC=1C(=CC(OC)=CC=1)F)C=C2NCCC(F)(F)F FUIKSWQDCJPDCE-UHFFFAOYSA-N 0.000 claims 1
MCQXZGTYHYFHQR-UHFFFAOYSA-N n-ethyl-4-[6-(2-fluoro-4-methoxyphenoxy)-8-(oxan-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCC)=CC=C1C1=CN=C2N1N=C(OC=1C(=CC(OC)=CC=1)F)C=C2NCC1CCOCC1 MCQXZGTYHYFHQR-UHFFFAOYSA-N 0.000 claims 1
CGUBCKYEKJADDN-UHFFFAOYSA-N n-ethyl-4-[6-(3-fluoro-4-methoxyphenoxy)-8-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCC)=CC=C1C1=CN=C2N1N=C(OC=1C=C(F)C(OC)=CC=1)C=C2NCCOC CGUBCKYEKJADDN-UHFFFAOYSA-N 0.000 claims 1
IYRXLKBPZXBKEX-UHFFFAOYSA-N n-ethyl-4-[6-(3-fluoro-4-methoxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCC)=CC=C1C1=CN=C2N1N=C(OC=1C=C(F)C(OC)=CC=1)C=C2NCCC(F)(F)F IYRXLKBPZXBKEX-UHFFFAOYSA-N 0.000 claims 1
AMFGUKXQOZUZIX-UHFFFAOYSA-N n-ethyl-4-[6-(3-fluoro-4-methoxyphenoxy)-8-(oxan-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCC)=CC=C1C1=CN=C2N1N=C(OC=1C=C(F)C(OC)=CC=1)C=C2NCC1CCOCC1 AMFGUKXQOZUZIX-UHFFFAOYSA-N 0.000 claims 1
XDJKSWSKULSGCK-UHFFFAOYSA-N n-ethyl-4-[6-(4-methoxyphenoxy)-8-(2-morpholin-4-ylethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCC)=CC=C1C1=CN=C2N1N=C(OC=1C=CC(OC)=CC=1)C=C2NCCN1CCOCC1 XDJKSWSKULSGCK-UHFFFAOYSA-N 0.000 claims 1
HNPAFHKLJFYLKZ-UHFFFAOYSA-N n-ethyl-4-[6-(5-fluoro-2-methylphenoxy)-8-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCC)=CC=C1C1=CN=C2N1N=C(OC=1C(=CC=C(F)C=1)C)C=C2NCCOC HNPAFHKLJFYLKZ-UHFFFAOYSA-N 0.000 claims 1
DKMATOTUJNYMGO-UHFFFAOYSA-N n-ethyl-4-[6-(5-fluoro-2-methylphenoxy)-8-(2-morpholin-4-ylethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCC)=CC=C1C1=CN=C2N1N=C(OC=1C(=CC=C(F)C=1)C)C=C2NCCN1CCOCC1 DKMATOTUJNYMGO-UHFFFAOYSA-N 0.000 claims 1
XOVIVJGCKZYWRG-UHFFFAOYSA-N n-ethyl-4-[6-(5-fluoro-2-methylphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCC)=CC=C1C1=CN=C2N1N=C(OC=1C(=CC=C(F)C=1)C)C=C2NCCC(F)(F)F XOVIVJGCKZYWRG-UHFFFAOYSA-N 0.000 claims 1
GLGMKGWDIHUVOU-UHFFFAOYSA-N n-ethyl-4-[6-(5-fluoro-2-methylphenoxy)-8-(oxan-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCC)=CC=C1C1=CN=C2N1N=C(OC=1C(=CC=C(F)C=1)C)C=C2NCC1CCOCC1 GLGMKGWDIHUVOU-UHFFFAOYSA-N 0.000 claims 1
230000037361 pathway Effects 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
150000003057 platinum Chemical class 0.000 claims 1
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CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 claims 1
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150000003254 radicals Chemical class 0.000 claims 1
230000004044 response Effects 0.000 claims 1
229960004641 rituximab Drugs 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 claims 1
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JP2013527575A 2010-09-10 2011-09-06 置換イミダゾピリダジン類 Expired - Fee Related JP5824050B2 (ja)