JP5824050B2 - 置換イミダゾピリダジン類 - Google Patents

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Publication number

JP5824050B2

JP5824050B2 JP2013527575A JP2013527575A JP5824050B2 JP 5824050 B2 JP5824050 B2 JP 5824050B2 JP 2013527575 A JP2013527575 A JP 2013527575A JP 2013527575 A JP2013527575 A JP 2013527575A JP 5824050 B2 JP5824050 B2 JP 5824050B2

Authority

JP

Japan

Prior art keywords

alkyl

amino

imidazo

cyclopropyl

pyridazin

Prior art date

2010-09-10

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.)

Expired - Fee Related

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• 150000005233 imidazopyridazines Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 574
• -1 1,1,1-trifluoroethyl group Chemical group 0.000 claims description 481
• 125000005843 halogen group Chemical group 0.000 claims description 317
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 287
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 229
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 197
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 129
• 229910052799 carbon Inorganic materials 0.000 claims description 128
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 109
• 239000000203 mixture Substances 0.000 claims description 108
• 239000001257 hydrogen Substances 0.000 claims description 87
• 229910052739 hydrogen Inorganic materials 0.000 claims description 87
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 80
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 56
• 150000003839 salts Chemical class 0.000 claims description 49
• 238000000034 method Methods 0.000 claims description 46
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
• 239000012453 solvate Substances 0.000 claims description 31
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 24
• 150000001204 N-oxides Chemical class 0.000 claims description 23
• 239000002253 acid Substances 0.000 claims description 18
• 238000002360 preparation method Methods 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 230000008569 process Effects 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 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 description 8
• 125000005620 boronic acid group Chemical group 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 5
• 239000003795 chemical substances by application Substances 0.000 claims description 5
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
• 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 description 4
• 229930012538 Paclitaxel Natural products 0.000 claims description 4
• 229940079593 drug Drugs 0.000 claims description 4
• 229960001592 paclitaxel Drugs 0.000 claims description 4
• 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 description 4
• VEFZDJHWJIPNKA-UHFFFAOYSA-N 4-[6-(4-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=CC(Cl)=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 VEFZDJHWJIPNKA-UHFFFAOYSA-N 0.000 claims description 3
• 229940123237 Taxane Drugs 0.000 claims description 3
• WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 claims description 3
• 229930013356 epothilone Natural products 0.000 claims description 3
• HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical class C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 claims description 3
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
• GWJPOUNGPRLVIB-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,3-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=CC=4)F)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 GWJPOUNGPRLVIB-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 2
• 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 description 2
• 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 description 2
• RPKMLDXUNAJFCS-UHFFFAOYSA-N 4-[6-(3-cyanophenoxy)-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(C=CC=4)C#N)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 RPKMLDXUNAJFCS-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• OFRNYEFBUSPDRM-UHFFFAOYSA-N 4-[6-(4-chlorophenoxy)-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=CC(Cl)=CC=4)C=C(NCC4CCSCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 OFRNYEFBUSPDRM-UHFFFAOYSA-N 0.000 claims description 2
• PNQZGZZHULYUDT-UHFFFAOYSA-N 4-[6-(4-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=CC(Cl)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 PNQZGZZHULYUDT-UHFFFAOYSA-N 0.000 claims description 2
• GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims description 2
• GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 claims description 2
• PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 claims description 2
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 2
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 2
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 2
• JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 2
• 229940009456 adriamycin Drugs 0.000 claims description 2
• 230000002280 anti-androgenic effect Effects 0.000 claims description 2
• 239000000051 antiandrogen Substances 0.000 claims description 2
• 229960001467 bortezomib Drugs 0.000 claims description 2
• GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 claims description 2
• 229960004117 capecitabine Drugs 0.000 claims description 2
• JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims description 2
• 229960004630 chlorambucil Drugs 0.000 claims description 2
• 229960000684 cytarabine Drugs 0.000 claims description 2
• 229960003957 dexamethasone Drugs 0.000 claims description 2
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• 229960003668 docetaxel Drugs 0.000 claims description 2
• 229960004679 doxorubicin Drugs 0.000 claims description 2
• 229960001842 estramustine Drugs 0.000 claims description 2
• FRPJXPJMRWBBIH-RBRWEJTLSA-N estramustine Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 FRPJXPJMRWBBIH-RBRWEJTLSA-N 0.000 claims description 2
• 229960000390 fludarabine Drugs 0.000 claims description 2
• GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 claims description 2
• 229960002949 fluorouracil Drugs 0.000 claims description 2
• 229960000485 methotrexate Drugs 0.000 claims description 2
• 229960001156 mitoxantrone Drugs 0.000 claims description 2
• KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims description 2
• DAOROHJNNPQZPI-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(4-propan-2-yloxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound C1=CC(OC(C)C)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 DAOROHJNNPQZPI-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
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