IL225058A

IL225058A - Converted imidazopyridazines, methods for their preparation and pharmaceutical preparations containing them

Converted imidazopyridazines, methods for their preparation and pharmaceutical preparations containing them

Info

Publication number: IL225058A
Authority: IL; Israel
Prior art keywords: amino; pyridazin; crc6; cyclopropyl; alkyl
Prior art date: 2010-09-10

Application number

IL225058A

Other languages

English (en)

Hebrew (he)

Original Assignee

Bayer Ip Gmbh

Priority date

2010-09-10

Filing date

2013-03-05

Publication date

2017-03-30

2013-03-05 Application filed by Bayer Ip Gmbh filed Critical Bayer Ip Gmbh

2017-03-30 Publication of IL225058A publication Critical patent/IL225058A/en

Links

238000000034 method Methods 0.000 title claims abstract description 59
239000008194 pharmaceutical composition Substances 0.000 title abstract description 13
150000005233 imidazopyridazines Chemical class 0.000 title abstract description 5
238000002360 preparation method Methods 0.000 title description 9
150000001875 compounds Chemical class 0.000 claims abstract description 708
-1 or a HO- Chemical group 0.000 claims description 446
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 300
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 254
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 247
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 187
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 132
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 123
125000005843 halogen group Chemical group 0.000 claims description 122
239000000203 mixture Substances 0.000 claims description 117
239000001257 hydrogen Substances 0.000 claims description 87
229910052739 hydrogen Inorganic materials 0.000 claims description 87
150000003839 salts Chemical class 0.000 claims description 47
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
239000012453 solvate Substances 0.000 claims description 29
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
HEFYOJVDTAFTJD-UHFFFAOYSA-N 4-[6-(3-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methyl-n-(1-methylcyclopropyl)benzamide 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)NC1(C)CC1 HEFYOJVDTAFTJD-UHFFFAOYSA-N 0.000 claims description 6
125000005620 boronic acid group Chemical group 0.000 claims description 6
238000010511 deprotection reaction Methods 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 4
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 description 4
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 4
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 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
PMRKHBMUYNHAFR-UHFFFAOYSA-N 4-[6-(2-aminophenoxy)-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=CC=4)N)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 PMRKHBMUYNHAFR-UHFFFAOYSA-N 0.000 claims description 3
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 3
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 description 3
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
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 3
DUTIKJXKJAEAKY-UHFFFAOYSA-N N-cyclopropyl-2-methyl-4-[6-phenoxy-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=CC=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 DUTIKJXKJAEAKY-UHFFFAOYSA-N 0.000 claims description 3
IZBOTABDXABHID-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(3-propan-2-yloxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC(C)OC1=CC=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 IZBOTABDXABHID-UHFFFAOYSA-N 0.000 claims description 3
XWFSLPKDRXOSRS-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-[2-(methylamino)phenoxy]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CNC1=CC=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 XWFSLPKDRXOSRS-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
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 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
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 description 3
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 description 3
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 description 3
LJCJRRKKAKAKRV-UHFFFAOYSA-N (2-amino-2-methylpropyl) 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical group CC(C)(N)COC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 LJCJRRKKAKAKRV-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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
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
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
BMHMHLXQEJEQIW-UHFFFAOYSA-N 4-[6-(4-chlorophenoxy)-8-[(1,1-dioxothian-4-yl)methylamino]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(NCC4CCS(=O)(=O)CC4)C3=NC=2)=CC=C1C(=O)NC1CC1 BMHMHLXQEJEQIW-UHFFFAOYSA-N 0.000 claims description 2
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
125000004185 ester group Chemical group 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
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 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
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 description 2
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 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
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
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 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
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 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
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 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
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 description 2
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 description 2
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 description 2
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 description 2
OTRLJOKVMOJRFG-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(1,1-dioxothian-4-yl)methylamino]-6-(2-fluorophenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=CC=CC=4)F)C=C(NCC4CCS(=O)(=O)CC4)C3=NC=2)=CC=C1C(=O)NC1CC1 OTRLJOKVMOJRFG-UHFFFAOYSA-N 0.000 claims description 2
HYJPDSVZWWUUOK-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(1,1-dioxothian-4-yl)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(NCC4CCS(=O)(=O)CC4)C3=NC=2)=CC=C1C(=O)NC1CC1 HYJPDSVZWWUUOK-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
HBLLQTQSVUFGBA-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(3-propan-2-ylphenoxy)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(NCC(C)(C)O)=C2)=C1 HBLLQTQSVUFGBA-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
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 description 2
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 2
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 2
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 2
125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 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
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
VEFITGNUTVJNHZ-UHFFFAOYSA-N 3-[[3-[4-(cyclopropylcarbamoyl)-3-methylphenyl]-6-(3-fluorophenoxy)imidazo[1,2-b]pyridazin-8-yl]amino]propane-1-sulfonic acid Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCCCS(O)(=O)=O)C3=NC=2)=CC=C1C(=O)NC1CC1 VEFITGNUTVJNHZ-UHFFFAOYSA-N 0.000 claims 1
FEVQGUVVMHKSLJ-UHFFFAOYSA-N 4-[6-(4-chlorophenoxy)-8-[2-(dimethylamino)ethylamino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-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(Cl)C=C1 FEVQGUVVMHKSLJ-UHFFFAOYSA-N 0.000 claims 1
LEHYJCDIBXRPSE-UHFFFAOYSA-N 4-[8-(2-acetamidoethylamino)-6-(3-fluorophenoxy)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCNC(=O)C)=CC=1OC1=CC=CC(F)=C1 LEHYJCDIBXRPSE-UHFFFAOYSA-N 0.000 claims 1
BXUJUYSMAXTKDZ-UHFFFAOYSA-N 4-[8-(3-acetamidopropylamino)-6-(3-fluorophenoxy)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCCNC(=O)C)=CC=1OC1=CC=CC(F)=C1 BXUJUYSMAXTKDZ-UHFFFAOYSA-N 0.000 claims 1
UARCDGBIDIEUHG-UHFFFAOYSA-N 4-[8-(azetidin-3-ylmethylamino)-6-(5-fluoro-2-methylphenoxy)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC=C(F)C=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC2CNC2)=C1 UARCDGBIDIEUHG-UHFFFAOYSA-N 0.000 claims 1
WEYGWYYIBYOQBZ-UHFFFAOYSA-N 4-[8-[(2-amino-2-methylpropyl)amino]-6-(3,4-difluorophenoxy)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C(F)=CC=4)C=C(NCC(C)(C)N)C3=NC=2)=CC=C1C(=O)NC1CC1 WEYGWYYIBYOQBZ-UHFFFAOYSA-N 0.000 claims 1
YATSLNPDPJNQGR-UHFFFAOYSA-N 4-[8-[(2-amino-2-methylpropyl)amino]-6-(3-fluorophenoxy)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)C=C(NCC(C)(C)N)C3=NC=2)=CC=C1C(=O)NC1CC1 YATSLNPDPJNQGR-UHFFFAOYSA-N 0.000 claims 1
GTJHPSHJNPXEDD-UHFFFAOYSA-N 4-[8-[(3-amino-3-oxopropyl)amino]-6-(3-fluorophenoxy)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)C=C(NCCC(N)=O)C3=NC=2)=CC=C1C(=O)NC1CC1 GTJHPSHJNPXEDD-UHFFFAOYSA-N 0.000 claims 1
CXIPPKWJXPDXLV-UHFFFAOYSA-N N-cyclopropyl-2-methyl-4-[6-[2-(methylamino)phenoxy]-8-(2-morpholin-4-ylethylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CNC1=CC=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCN2CCOCC2)=C1 CXIPPKWJXPDXLV-UHFFFAOYSA-N 0.000 claims 1
DIIHUPKICCVKFB-UHFFFAOYSA-N N-cyclopropyl-2-methyl-4-[8-(methylamino)-6-[2-(methylamino)phenoxy]imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CNC1=CC=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NC)=C1 DIIHUPKICCVKFB-UHFFFAOYSA-N 0.000 claims 1
XPRLINZSJSKLQF-UHFFFAOYSA-N N-cyclopropyl-4-[6-(2-fluoro-4-methoxyphenoxy)-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(OC)C=C1F XPRLINZSJSKLQF-UHFFFAOYSA-N 0.000 claims 1
GQGMDNODXYSARF-UHFFFAOYSA-N N-cyclopropyl-4-[6-(3,4-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(F)=CC=4)C=C(NCCN4CCOCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 GQGMDNODXYSARF-UHFFFAOYSA-N 0.000 claims 1
QHKJKAQBWQVWBI-UHFFFAOYSA-N N-cyclopropyl-4-[6-(3-fluoro-4-methoxyphenoxy)-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(OC)C(F)=C1 QHKJKAQBWQVWBI-UHFFFAOYSA-N 0.000 claims 1
IRJHKPURLIGHDP-UHFFFAOYSA-N N-cyclopropyl-4-[6-(3-fluorophenoxy)-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)C=C(NCCS(C)(=O)=O)C3=NC=2)=CC=C1C(=O)NC1CC1 IRJHKPURLIGHDP-UHFFFAOYSA-N 0.000 claims 1
INZBLSIDZVTFGG-UHFFFAOYSA-N N-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(2-pyrazol-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(NCCN4N=CC=C4)C3=NC=2)=CC=C1C(=O)NC1CC1 INZBLSIDZVTFGG-UHFFFAOYSA-N 0.000 claims 1
GCIURORLLBSRJU-UHFFFAOYSA-N N-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(2-pyrrolidin-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(NCCN4CCCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 GCIURORLLBSRJU-UHFFFAOYSA-N 0.000 claims 1
VEQGUOXRDBHJMV-UHFFFAOYSA-N N-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(2H-tetrazol-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(NCC=4NN=NN=4)C3=NC=2)=CC=C1C(=O)NC1CC1 VEQGUOXRDBHJMV-UHFFFAOYSA-N 0.000 claims 1
CTYAGBHXHDLDFI-UHFFFAOYSA-N N-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(3-methylsulfonylpropylamino)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(NCCCS(C)(=O)=O)C3=NC=2)=CC=C1C(=O)NC1CC1 CTYAGBHXHDLDFI-UHFFFAOYSA-N 0.000 claims 1
UHAJZVDTFRORSD-UHFFFAOYSA-N N-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(3-morpholin-4-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(NCCCN4CCOCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 UHAJZVDTFRORSD-UHFFFAOYSA-N 0.000 claims 1
FEOSZJCOOKXGGC-UHFFFAOYSA-N N-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(3-pyrrolidin-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(NCCCN4CCCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 FEOSZJCOOKXGGC-UHFFFAOYSA-N 0.000 claims 1
CDTNBQDJZACDTE-UHFFFAOYSA-N N-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[(2-methyl-2-morpholin-4-ylpropyl)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)N4CCOCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 CDTNBQDJZACDTE-UHFFFAOYSA-N 0.000 claims 1
MWEZIXUMOHLIPE-UHFFFAOYSA-N N-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[2-(2H-tetrazol-5-yl)ethylamino]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=4NN=NN=4)C3=NC=2)=CC=C1C(=O)NC1CC1 MWEZIXUMOHLIPE-UHFFFAOYSA-N 0.000 claims 1
PJKXHKXXJSWHLQ-UHFFFAOYSA-N N-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[[3-(hydroxymethyl)oxetan-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(CO)COC4)C3=NC=2)=CC=C1C(=O)NC1CC1 PJKXHKXXJSWHLQ-UHFFFAOYSA-N 0.000 claims 1
HQIZTHZPXFCPFY-UHFFFAOYSA-N N-cyclopropyl-4-[6-(5-fluoro-2-methylphenoxy)-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(F)=CC=C1C HQIZTHZPXFCPFY-UHFFFAOYSA-N 0.000 claims 1
UPWUIUXMCVXMAI-UHFFFAOYSA-N N-cyclopropyl-4-[8-(2,3-dihydroxypropylamino)-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(NCC(O)CO)C3=NC=2)=CC=C1C(=O)NC1CC1 UPWUIUXMCVXMAI-UHFFFAOYSA-N 0.000 claims 1
OABBXJWGUGAJQB-UHFFFAOYSA-N N-cyclopropyl-4-[8-[4-(dimethylamino)butylamino]-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(NCCCCN(C)C)=CC=1OC1=CC=CC(F)=C1 OABBXJWGUGAJQB-UHFFFAOYSA-N 0.000 claims 1
QEGJHGFVZOSDFP-UHFFFAOYSA-N N-cyclopropyl-4-[8-[[2-(dimethylamino)-2-methylpropyl]amino]-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(NCC(C)(C)N(C)C)=CC=1OC1=CC=CC(F)=C1 QEGJHGFVZOSDFP-UHFFFAOYSA-N 0.000 claims 1
JYGMWAIXMJZSPC-UHFFFAOYSA-N N-cyclopropyl-4-[8-[[3-(dimethylamino)-3-oxopropyl]amino]-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(NCCC(=O)N(C)C)=CC=1OC1=CC=CC(F)=C1 JYGMWAIXMJZSPC-UHFFFAOYSA-N 0.000 claims 1
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
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
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
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
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
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
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
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
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
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
RTDOEUXGOUJIII-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[(1-methyl-5-oxopyrrolidin-3-yl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1C(=O)N(C)CC1CNC1=CC(OC=2C=C(F)C=CC=2)=NN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 RTDOEUXGOUJIII-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
XONYHFIXMOYPHH-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(1,1-dioxothian-4-yl)methylamino]-6-(4-fluorophenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=CC(F)=CC=4)C=C(NCC4CCS(=O)(=O)CC4)C3=NC=2)=CC=C1C(=O)NC1CC1 XONYHFIXMOYPHH-UHFFFAOYSA-N 0.000 claims 1
KDSAUMNSZUFGLM-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(1,1-dioxothiolan-3-yl)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(NCC4CS(=O)(=O)CC4)C3=NC=2)=CC=C1C(=O)NC1CC1 KDSAUMNSZUFGLM-UHFFFAOYSA-N 0.000 claims 1
CDILJPGHIAKWLS-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(4-piperazin-1-ylphenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=CC(=CC=4)N4CCNCC4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 CDILJPGHIAKWLS-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
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 1
125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 29
201000010099 disease Diseases 0.000 abstract description 15
238000011282 treatment Methods 0.000 abstract description 13
238000011321 prophylaxis Methods 0.000 abstract description 8
239000003795 chemical substances by application Substances 0.000 abstract description 5
238000004519 manufacturing process Methods 0.000 abstract description 5
239000004480 active ingredient Substances 0.000 abstract description 4
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 abstract description 2
102000009516 Protein Serine-Threonine Kinases Human genes 0.000 abstract description 2
108010009341 Protein Serine-Threonine Kinases Proteins 0.000 abstract description 2
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 abstract description 2
230000033115 angiogenesis Effects 0.000 abstract 1
230000003463 hyperproliferative effect Effects 0.000 abstract 1
229940043355 kinase inhibitor Drugs 0.000 abstract 1
239000003757 phosphotransferase inhibitor Substances 0.000 abstract 1
239000000543 intermediate Substances 0.000 description 627
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 424
238000000746 purification Methods 0.000 description 393
238000005160 1H NMR spectroscopy Methods 0.000 description 357
125000001072 heteroaryl group Chemical group 0.000 description 237
125000004093 cyano group Chemical group *C#N 0.000 description 171
125000003118 aryl group Chemical group 0.000 description 158
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 133
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 88
125000005418 aryl aryl group Chemical group 0.000 description 77
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 73
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 61
239000000243 solution Substances 0.000 description 53
229910052717 sulfur Inorganic materials 0.000 description 52
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 46
LOZRYLSDXSNUMZ-UHFFFAOYSA-N 4-[6-bromo-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Br)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 LOZRYLSDXSNUMZ-UHFFFAOYSA-N 0.000 description 44
239000002904 solvent Substances 0.000 description 44
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
229910052736 halogen Inorganic materials 0.000 description 41
150000002367 halogens Chemical class 0.000 description 41
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
125000004366 heterocycloalkenyl group Chemical group 0.000 description 36
238000004587 chromatography analysis Methods 0.000 description 34
206010028980 Neoplasm Diseases 0.000 description 30
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 30
125000004432 carbon atom Chemical group C* 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
210000004027 cell Anatomy 0.000 description 23
229910052938 sodium sulfate Inorganic materials 0.000 description 23
235000011152 sodium sulphate Nutrition 0.000 description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 22
238000001914 filtration Methods 0.000 description 22
SVALSHAHFMBAEX-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide Chemical compound CC1=CC(B2OC(C)(C)C(C)(C)O2)=CC=C1C(=O)NC1CC1 SVALSHAHFMBAEX-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 20
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
CSFRKRKCGOHTJB-UHFFFAOYSA-N 8-bromo-6-chloro-3-iodoimidazo[1,2-b]pyridazine Chemical compound N1=C(Cl)C=C(Br)C2=NC=C(I)N21 CSFRKRKCGOHTJB-UHFFFAOYSA-N 0.000 description 18
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
229940126062 Compound A Drugs 0.000 description 16
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 16
QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 16
108091000080 Phosphotransferase Proteins 0.000 description 15
102000020233 phosphotransferase Human genes 0.000 description 15
150000002430 hydrocarbons Chemical group 0.000 description 14
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 14
239000012074 organic phase Substances 0.000 description 14
FHHJXOHKRXQGOB-UHFFFAOYSA-N 4-[6-bromo-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Br)C=C(NCC4CCSCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 FHHJXOHKRXQGOB-UHFFFAOYSA-N 0.000 description 13
208000035475 disorder Diseases 0.000 description 13
235000019439 ethyl acetate Nutrition 0.000 description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000012267 brine Substances 0.000 description 12
238000005859 coupling reaction Methods 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
230000004663 cell proliferation Effects 0.000 description 11
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
230000002062 proliferating effect Effects 0.000 description 11
ZDEUGINAVLMAET-UHFFFAOYSA-N 3-fluorobenzenethiol Chemical compound FC1=CC=CC(S)=C1 ZDEUGINAVLMAET-UHFFFAOYSA-N 0.000 description 10
HULPYSWCOQYXBS-UHFFFAOYSA-N 4-[6-chloro-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Cl)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 HULPYSWCOQYXBS-UHFFFAOYSA-N 0.000 description 10
LBUNNMJLXWQQBY-UHFFFAOYSA-N 4-fluorophenylboronic acid Chemical compound OB(O)C1=CC=C(F)C=C1 LBUNNMJLXWQQBY-UHFFFAOYSA-N 0.000 description 10
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
125000001424 substituent group Chemical group 0.000 description 10
HLXOVAMYQUFLPE-UHFFFAOYSA-N 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole Chemical compound CN1N=CC=C1B1OC(C)(C)C(C)(C)O1 HLXOVAMYQUFLPE-UHFFFAOYSA-N 0.000 description 9
CNLOFJKPLANCFV-UHFFFAOYSA-N 4-[6-chloro-8-(2-methylpropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=CC(Cl)=NN2C=1C(C=C1C)=CC=C1C(=O)NC1CC1 CNLOFJKPLANCFV-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
230000024932 T cell mediated immunity Effects 0.000 description 9
239000002585 base Substances 0.000 description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
230000010261 cell growth Effects 0.000 description 9
230000001413 cellular effect Effects 0.000 description 9
239000003814 drug Substances 0.000 description 9
230000004083 survival effect Effects 0.000 description 9
ITQAGWRCXRRJLY-UHFFFAOYSA-N 6-chloro-3-iodo-n-(2-methylpropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound CC(C)CNC1=CC(Cl)=NN2C(I)=CN=C12 ITQAGWRCXRRJLY-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
125000002619 bicyclic group Chemical group 0.000 description 8
230000028709 inflammatory response Effects 0.000 description 8
239000003112 inhibitor Substances 0.000 description 8
230000017205 mitotic cell cycle checkpoint Effects 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
CRQHLWUGEZWMFF-UHFFFAOYSA-N 1-[[6-chloro-3-[4-(1,3-dioxolan-2-yl)phenyl]imidazo[1,2-b]pyridazin-8-yl]amino]-2-methylpropan-2-ol Chemical compound C=1N=C2C(NCC(C)(O)C)=CC(Cl)=NN2C=1C(C=C1)=CC=C1C1OCCO1 CRQHLWUGEZWMFF-UHFFFAOYSA-N 0.000 description 7
BVXSGNHDNBVQNJ-UHFFFAOYSA-N 6,8-dibromo-3-iodoimidazo[1,2-b]pyridazine Chemical compound N1=C(Br)C=C(Br)C2=NC=C(I)N21 BVXSGNHDNBVQNJ-UHFFFAOYSA-N 0.000 description 7
241000282414 Homo sapiens Species 0.000 description 7
WCRPDYXXIVYAAJ-UHFFFAOYSA-N [4-(cyclopropylcarbamoyl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C(=O)NC1CC1 WCRPDYXXIVYAAJ-UHFFFAOYSA-N 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
230000014759 maintenance of location Effects 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
229940124597 therapeutic agent Drugs 0.000 description 7
OJUAZAZYZJBJBT-UHFFFAOYSA-N 1-[(6-chloro-3-iodoimidazo[1,2-b]pyridazin-8-yl)amino]-2-methylpropan-2-ol Chemical compound CC(C)(O)CNC1=CC(Cl)=NN2C(I)=CN=C12 OJUAZAZYZJBJBT-UHFFFAOYSA-N 0.000 description 6
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 6
DPGSPRJLAZGUBQ-UHFFFAOYSA-N 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OB(C=C)OC1(C)C DPGSPRJLAZGUBQ-UHFFFAOYSA-N 0.000 description 6
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 6
SJTBRFHBXDZMPS-UHFFFAOYSA-N 3-fluorophenol Chemical compound OC1=CC=CC(F)=C1 SJTBRFHBXDZMPS-UHFFFAOYSA-N 0.000 description 6
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
208000003174 Brain Neoplasms Diseases 0.000 description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
206010027476 Metastases Diseases 0.000 description 6
150000001204 N-oxides Chemical class 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
AFHOBSCDNXGFMO-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]boronic acid Chemical compound OCC1=CC=CC=C1B(O)O AFHOBSCDNXGFMO-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
229940095076 benzaldehyde Drugs 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
125000005842 heteroatom Chemical group 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
150000004942 imidazo[1,2-b]pyridazines Chemical class 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
238000001727 in vivo Methods 0.000 description 6
125000002950 monocyclic group Chemical group 0.000 description 6
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 6
238000000926 separation method Methods 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
GVZLAPQNXUIOMF-UHFFFAOYSA-N 1-[[6-chloro-3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]imidazo[1,2-b]pyridazin-8-yl]amino]-2-methylpropan-2-ol Chemical compound C=1N=C2C(NCC(C)(O)C)=CC(Cl)=NN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 GVZLAPQNXUIOMF-UHFFFAOYSA-N 0.000 description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
KRNCURCYWRLGSM-UHFFFAOYSA-N 4-[6-chloro-8-[(3,3,3-trifluoro-2-hydroxypropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Cl)C=C(NCC(O)C(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 KRNCURCYWRLGSM-UHFFFAOYSA-N 0.000 description 5
TUYVCQAAPPGTTR-UHFFFAOYSA-N 6-chloro-3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-n-(3,3,3-trifluoropropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C=1N=C2C(NCCC(F)(F)F)=CC(Cl)=NN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 TUYVCQAAPPGTTR-UHFFFAOYSA-N 0.000 description 5
VEBNDJHAGGCIIB-UHFFFAOYSA-N 6-chloro-3-iodo-n-(3,3,3-trifluoropropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound FC(F)(F)CCNC1=CC(Cl)=NN2C(I)=CN=C12 VEBNDJHAGGCIIB-UHFFFAOYSA-N 0.000 description 5
238000007792 addition Methods 0.000 description 5
125000004429 atom Chemical group 0.000 description 5
125000005605 benzo group Chemical group 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
125000004122 cyclic group Chemical group 0.000 description 5
238000009472 formulation Methods 0.000 description 5
150000002391 heterocyclic compounds Chemical class 0.000 description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
230000002503 metabolic effect Effects 0.000 description 5
125000004433 nitrogen atom Chemical group N* 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
229960001407 sodium bicarbonate Drugs 0.000 description 5
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
RPEPGIOVXBBUMJ-UHFFFAOYSA-N 2,3-difluorophenol Chemical compound OC1=CC=CC(F)=C1F RPEPGIOVXBBUMJ-UHFFFAOYSA-N 0.000 description 4
DSCJETUEDFKYGN-UHFFFAOYSA-N 2-Methoxybenzenethiol Chemical compound COC1=CC=CC=C1S DSCJETUEDFKYGN-UHFFFAOYSA-N 0.000 description 4
FCJHBXCQIOVMEM-UHFFFAOYSA-N 2-fluoro-4-methoxyphenol Chemical compound COC1=CC=C(O)C(F)=C1 FCJHBXCQIOVMEM-UHFFFAOYSA-N 0.000 description 4
VRRSYCJFFOUSFM-UHFFFAOYSA-N 3-fluoro-5-methylbenzenethiol Chemical compound CC1=CC(F)=CC(S)=C1 VRRSYCJFFOUSFM-UHFFFAOYSA-N 0.000 description 4
AYMBVFCWNCCREA-UHFFFAOYSA-N 3-fluoro-5-methylphenol Chemical compound CC1=CC(O)=CC(F)=C1 AYMBVFCWNCCREA-UHFFFAOYSA-N 0.000 description 4
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
XDRQLDYLYNLLGS-UHFFFAOYSA-N 4-[6-(3-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=C1 XDRQLDYLYNLLGS-UHFFFAOYSA-N 0.000 description 4
FDOWIRFKAHKIDS-UHFFFAOYSA-N 4-[6-bromo-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Br)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 FDOWIRFKAHKIDS-UHFFFAOYSA-N 0.000 description 4
JMPJBIFBYDKELV-UHFFFAOYSA-N 4-[8-[(2-amino-2-methylpropyl)amino]-6-chloroimidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Cl)C=C(NCC(C)(C)N)C3=NC=2)=CC=C1C(=O)NC1CC1 JMPJBIFBYDKELV-UHFFFAOYSA-N 0.000 description 4
VDBQQFUSXNTPKU-UHFFFAOYSA-N 6,8-dibromoimidazo[1,2-b]pyridazine Chemical compound N1=C(Br)C=C(Br)C2=NC=CN21 VDBQQFUSXNTPKU-UHFFFAOYSA-N 0.000 description 4
ASNCWFZNEXNXJP-UHFFFAOYSA-N 6-chloro-3-[4-(1,3-dioxolan-2-yl)phenyl]-n-(3,3,3-trifluoropropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C=1N=C2C(NCCC(F)(F)F)=CC(Cl)=NN2C=1C(C=C1)=CC=C1C1OCCO1 ASNCWFZNEXNXJP-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
201000011510 cancer Diseases 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
210000000349 chromosome Anatomy 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
230000000694 effects Effects 0.000 description 4
125000000524 functional group Chemical group 0.000 description 4
150000004677 hydrates Chemical class 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
208000032839 leukemia Diseases 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
230000011278 mitosis Effects 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
239000011734 sodium Substances 0.000 description 4
235000015424 sodium Nutrition 0.000 description 4
229940083542 sodium Drugs 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 3
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
YCCQGFYAVUTQFK-UHFFFAOYSA-N 2,3-difluoroaniline Chemical compound NC1=CC=CC(F)=C1F YCCQGFYAVUTQFK-UHFFFAOYSA-N 0.000 description 3
DVDXVDUMSBCCTP-UHFFFAOYSA-N 2-[4-(1,3-dioxolan-2-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C2OCCO2)C=C1 DVDXVDUMSBCCTP-UHFFFAOYSA-N 0.000 description 3
NGZVNONVXYLYQW-UHFFFAOYSA-N 3,3,3-trifluoropropan-1-amine Chemical compound NCCC(F)(F)F NGZVNONVXYLYQW-UHFFFAOYSA-N 0.000 description 3
AXNUZKSSQHTNPZ-UHFFFAOYSA-N 3,4-difluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1 AXNUZKSSQHTNPZ-UHFFFAOYSA-N 0.000 description 3
KQLUXUHTWARHJO-UHFFFAOYSA-N 3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-6-ethenyl-n-(3,3,3-trifluoropropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C=1N=C2C(NCCC(F)(F)F)=CC(C=C)=NN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 KQLUXUHTWARHJO-UHFFFAOYSA-N 0.000 description 3
QMVAZEHZOPDGHA-UHFFFAOYSA-N 3-methoxybenzenethiol Chemical compound COC1=CC=CC(S)=C1 QMVAZEHZOPDGHA-UHFFFAOYSA-N 0.000 description 3
MMLKBHQSNNDPHO-UHFFFAOYSA-N 4-[6-bromo-8-(2-hydroxyethylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Br)C=C(NCCO)C3=NC=2)=CC=C1C(=O)NC1CC1 MMLKBHQSNNDPHO-UHFFFAOYSA-N 0.000 description 3
YYZHAOJXENHDLL-UHFFFAOYSA-N 4-[6-chloro-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Cl)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 YYZHAOJXENHDLL-UHFFFAOYSA-N 0.000 description 3
VSYQNFCJQTUXOD-MRXNPFEDSA-N 4-[6-chloro-8-[[(2r)-oxolan-2-yl]methylamino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Cl)C=C(NC[C@@H]4OCCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 VSYQNFCJQTUXOD-MRXNPFEDSA-N 0.000 description 3
VSYQNFCJQTUXOD-INIZCTEOSA-N 4-[6-chloro-8-[[(2s)-oxolan-2-yl]methylamino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Cl)C=C(NC[C@H]4OCCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 VSYQNFCJQTUXOD-INIZCTEOSA-N 0.000 description 3
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 3
WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-UHFFFAOYSA-N 0.000 description 3
JLCDTNNLXUMYFQ-UHFFFAOYSA-N 5-fluoro-2-methylaniline Chemical compound CC1=CC=C(F)C=C1N JLCDTNNLXUMYFQ-UHFFFAOYSA-N 0.000 description 3
PCIQHGSRMDFYLI-UHFFFAOYSA-N 6-bromo-3-iodo-n-(3,3,3-trifluoropropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound FC(F)(F)CCNC1=CC(Br)=NN2C(I)=CN=C12 PCIQHGSRMDFYLI-UHFFFAOYSA-N 0.000 description 3
VXYXPKMZGLRVPC-UHFFFAOYSA-N 6-bromo-3-iodo-n-(oxan-4-ylmethyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C12=NC=C(I)N2N=C(Br)C=C1NCC1CCOCC1 VXYXPKMZGLRVPC-UHFFFAOYSA-N 0.000 description 3
LFFGBZDTWUFIDR-UHFFFAOYSA-N 6-chloro-3-iodo-n-(oxan-2-ylmethyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C12=NC=C(I)N2N=C(Cl)C=C1NCC1CCCCO1 LFFGBZDTWUFIDR-UHFFFAOYSA-N 0.000 description 3
VFTJLVYMSQLYIY-SSDOTTSWSA-N 6-chloro-3-iodo-n-[[(2r)-oxolan-2-yl]methyl]imidazo[1,2-b]pyridazin-8-amine Chemical compound C12=NC=C(I)N2N=C(Cl)C=C1NC[C@H]1CCCO1 VFTJLVYMSQLYIY-SSDOTTSWSA-N 0.000 description 3
VFTJLVYMSQLYIY-ZETCQYMHSA-N 6-chloro-3-iodo-n-[[(2s)-oxolan-2-yl]methyl]imidazo[1,2-b]pyridazin-8-amine Chemical compound C12=NC=C(I)N2N=C(Cl)C=C1NC[C@@H]1CCCO1 VFTJLVYMSQLYIY-ZETCQYMHSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
102100021752 Corticoliberin Human genes 0.000 description 3
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
206010025323 Lymphomas Diseases 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
206010059282 Metastases to central nervous system Diseases 0.000 description 3
241001024304 Mino Species 0.000 description 3
201000003793 Myelodysplastic syndrome Diseases 0.000 description 3
206010029098 Neoplasm skin Diseases 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YUROUWWCCSZTIP-UHFFFAOYSA-N [4-(cyclopropylcarbamoyl)-2-methoxyphenyl]boronic acid Chemical compound C1=C(B(O)O)C(OC)=CC(C(=O)NC2CC2)=C1 YUROUWWCCSZTIP-UHFFFAOYSA-N 0.000 description 3
CRDGQMHVPOLLDL-UHFFFAOYSA-N [4-(cyclopropylcarbamoyl)-3-methylphenyl]boronic acid Chemical compound CC1=CC(B(O)O)=CC=C1C(=O)NC1CC1 CRDGQMHVPOLLDL-UHFFFAOYSA-N 0.000 description 3
WDCNOFNVHZOFOW-UHFFFAOYSA-N [4-fluoro-2-(hydroxymethyl)phenyl]boronic acid Chemical compound OCC1=CC(F)=CC=C1B(O)O WDCNOFNVHZOFOW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
230000033077 cellular process Effects 0.000 description 3
210000000038 chest Anatomy 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052804 chromium Inorganic materials 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
125000000392 cycloalkenyl group Chemical group 0.000 description 3
230000002124 endocrine Effects 0.000 description 3
230000002496 gastric effect Effects 0.000 description 3
201000010536 head and neck cancer Diseases 0.000 description 3
NAUOUPATZLZONR-UHFFFAOYSA-N imidazo[1,2-b]pyridazin-8-amine Chemical compound NC1=CC=NN2C=CN=C12 NAUOUPATZLZONR-UHFFFAOYSA-N 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
210000002415 kinetochore Anatomy 0.000 description 3
208000037841 lung tumor Diseases 0.000 description 3
230000001404 mediated effect Effects 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
230000000394 mitotic effect Effects 0.000 description 3
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 description 3
150000007524 organic acids Chemical class 0.000 description 3
BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
239000012071 phase Substances 0.000 description 3
229960003742 phenol Drugs 0.000 description 3
238000002953 preparative HPLC Methods 0.000 description 3
230000008569 process Effects 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
210000002307 prostate Anatomy 0.000 description 3
238000004366 reverse phase liquid chromatography Methods 0.000 description 3
150000003335 secondary amines Chemical class 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
201000004477 skin sarcoma Diseases 0.000 description 3
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
235000019345 sodium thiosulphate Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
KAKIJVTZFSELRI-UHFFFAOYSA-N tert-butyl n-(6-bromoimidazo[1,2-b]pyridazin-8-yl)-n-(3,3,3-trifluoropropyl)carbamate Chemical compound CC(C)(C)OC(=O)N(CCC(F)(F)F)C1=CC(Br)=NN2C=CN=C12 KAKIJVTZFSELRI-UHFFFAOYSA-N 0.000 description 3
150000003568 thioethers Chemical class 0.000 description 3
239000003643 water by type Substances 0.000 description 3
KZFZIALCFGIPRE-DTWKUNHWSA-N (1s)-2-[(6-chloro-3-iodoimidazo[1,2-b]pyridazin-8-yl)amino]-1-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol Chemical compound O1C(C)(C)OC[C@@H]1[C@@H](O)CNC1=CC(Cl)=NN2C1=NC=C2I KZFZIALCFGIPRE-DTWKUNHWSA-N 0.000 description 2
PTUMVGFMLYYJDW-UHFFFAOYSA-N (2-bromo-5-fluorophenyl)methoxy-tri(propan-2-yl)silane Chemical compound CC(C)[Si](C(C)C)(C(C)C)OCC1=CC(F)=CC=C1Br PTUMVGFMLYYJDW-UHFFFAOYSA-N 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
DECWLXUOZUMPBF-UHFFFAOYSA-N (4-cyano-3-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C(F)=C1 DECWLXUOZUMPBF-UHFFFAOYSA-N 0.000 description 2
VJTBYIVDTPQLIE-UHFFFAOYSA-N (5-chloro-2-sulfanylphenyl)methanol Chemical compound OCC1=CC(Cl)=CC=C1S VJTBYIVDTPQLIE-UHFFFAOYSA-N 0.000 description 2
CYEXXDYQJPRMIQ-UHFFFAOYSA-N (5-cyanopyridin-3-yl)boronic acid Chemical compound OB(O)C1=CN=CC(C#N)=C1 CYEXXDYQJPRMIQ-UHFFFAOYSA-N 0.000 description 2
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 2
AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
IUBHUSKSWSCXTM-UHFFFAOYSA-N 1-[(6-bromo-3-iodoimidazo[1,2-b]pyridazin-8-yl)amino]-2-methylpropan-2-ol Chemical compound CC(C)(O)CNC1=CC(Br)=NN2C(I)=CN=C12 IUBHUSKSWSCXTM-UHFFFAOYSA-N 0.000 description 2
AFTNBHGUHBQZGR-UHFFFAOYSA-N 1-[[3-[4-(1,3-dioxolan-2-yl)phenyl]-6-(3-fluorophenoxy)imidazo[1,2-b]pyridazin-8-yl]amino]-2-methylpropan-2-ol Chemical compound N=1N2C(C=3C=CC(=CC=3)C3OCCO3)=CN=C2C(NCC(C)(O)C)=CC=1OC1=CC=CC(F)=C1 AFTNBHGUHBQZGR-UHFFFAOYSA-N 0.000 description 2
DIWBPYQBESPNAG-UHFFFAOYSA-N 1-[[3-[4-(1,3-dioxolan-2-yl)phenyl]-6-(3-fluorophenyl)sulfanylimidazo[1,2-b]pyridazin-8-yl]amino]-2-methylpropan-2-ol Chemical compound N=1N2C(C=3C=CC(=CC=3)C3OCCO3)=CN=C2C(NCC(C)(O)C)=CC=1SC1=CC=CC(F)=C1 DIWBPYQBESPNAG-UHFFFAOYSA-N 0.000 description 2
QXLVWPSRZHYLLA-UHFFFAOYSA-N 1-[[3-[4-(1,3-dioxolan-2-yl)phenyl]-6-(4-fluorophenyl)imidazo[1,2-b]pyridazin-8-yl]amino]-2-methylpropan-2-ol Chemical compound C=1N=C2C(NCC(C)(O)C)=CC(C=3C=CC(F)=CC=3)=NN2C=1C(C=C1)=CC=C1C1OCCO1 QXLVWPSRZHYLLA-UHFFFAOYSA-N 0.000 description 2
XJYLHPSZFBVKOD-UHFFFAOYSA-N 1-[[3-[4-(1,3-dioxolan-2-yl)phenyl]-6-phenoxyimidazo[1,2-b]pyridazin-8-yl]amino]-2-methylpropan-2-ol Chemical compound N=1N2C(C=3C=CC(=CC=3)C3OCCO3)=CN=C2C(NCC(C)(O)C)=CC=1OC1=CC=CC=C1 XJYLHPSZFBVKOD-UHFFFAOYSA-N 0.000 description 2
MEKQMAMOSRPOIY-UHFFFAOYSA-N 1-[[6-(cyclohexen-1-yl)-3-[4-(1,3-dioxolan-2-yl)phenyl]imidazo[1,2-b]pyridazin-8-yl]amino]-2-methylpropan-2-ol Chemical compound C=1N=C2C(NCC(C)(O)C)=CC(C=3CCCCC=3)=NN2C=1C(C=C1)=CC=C1C1OCCO1 MEKQMAMOSRPOIY-UHFFFAOYSA-N 0.000 description 2
LXQMHOKEXZETKB-UHFFFAOYSA-N 1-amino-2-methylpropan-2-ol Chemical compound CC(C)(O)CN LXQMHOKEXZETKB-UHFFFAOYSA-N 0.000 description 2
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
HKAVADYDPYUPRD-UHFFFAOYSA-N 1h-pyrazine-2-thione Chemical compound SC1=CN=CC=N1 HKAVADYDPYUPRD-UHFFFAOYSA-N 0.000 description 2
CDZXJJOGDCLNKX-UHFFFAOYSA-N 2,2,3,3-tetrafluorobutane-1,4-diol Chemical compound OCC(F)(F)C(F)(F)CO CDZXJJOGDCLNKX-UHFFFAOYSA-N 0.000 description 2
PQRVQUXEBQKVEQ-UHFFFAOYSA-N 2,5-difluorobenzenethiol Chemical compound FC1=CC=C(F)C(S)=C1 PQRVQUXEBQKVEQ-UHFFFAOYSA-N 0.000 description 2
QXHDYMUPPXAMPQ-UHFFFAOYSA-N 2-(4-aminophenyl)ethanol Chemical compound NC1=CC=C(CCO)C=C1 QXHDYMUPPXAMPQ-UHFFFAOYSA-N 0.000 description 2
SXVRARBIVGEMRF-UHFFFAOYSA-N 2-[(6-bromo-3-iodoimidazo[1,2-b]pyridazin-8-yl)amino]ethanol Chemical compound OCCNC1=CC(Br)=NN2C(I)=CN=C12 SXVRARBIVGEMRF-UHFFFAOYSA-N 0.000 description 2
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
JHEKZGQIHWVRFW-UHFFFAOYSA-N 2-fluoro-4-[8-(2-methylpropylamino)-6-phenylimidazo[1,2-b]pyridazin-3-yl]benzonitrile Chemical compound C=1N=C2C(NCC(C)C)=CC(C=3C=CC=CC=3)=NN2C=1C1=CC=C(C#N)C(F)=C1 JHEKZGQIHWVRFW-UHFFFAOYSA-N 0.000 description 2
VLXWEUASWRQBAY-UHFFFAOYSA-N 2-fluoro-4-methylbenzenethiol Chemical compound CC1=CC=C(S)C(F)=C1 VLXWEUASWRQBAY-UHFFFAOYSA-N 0.000 description 2
QZUXMXZNVAJNSE-UHFFFAOYSA-N 2-fluoro-5-methylaniline Chemical compound CC1=CC=C(F)C(N)=C1 QZUXMXZNVAJNSE-UHFFFAOYSA-N 0.000 description 2
XEHPMVZYZDQLDN-UHFFFAOYSA-N 2-fluoro-5-methylphenol Chemical compound CC1=CC=C(F)C(O)=C1 XEHPMVZYZDQLDN-UHFFFAOYSA-N 0.000 description 2
FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 2
WJTZZPVVTSDNJJ-UHFFFAOYSA-N 2-fluorobenzenethiol Chemical compound FC1=CC=CC=C1S WJTZZPVVTSDNJJ-UHFFFAOYSA-N 0.000 description 2
HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 2
YZVWMFBVTTUSAW-UHFFFAOYSA-N 2-morpholin-4-ylethanethiol Chemical compound SCCN1CCOCC1 YZVWMFBVTTUSAW-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
YNNQPLHRDOMWNW-UHFFFAOYSA-N 3,3-dimethylbutane-1-thiol Chemical compound CC(C)(C)CCS YNNQPLHRDOMWNW-UHFFFAOYSA-N 0.000 description 2
BGVRHDQMTMPAEZ-UHFFFAOYSA-N 3,4-difluorobenzenethiol Chemical compound FC1=CC=C(S)C=C1F BGVRHDQMTMPAEZ-UHFFFAOYSA-N 0.000 description 2
BNPWVUJOPCGHIK-UHFFFAOYSA-N 3,4-difluorophenol Chemical compound OC1=CC=C(F)C(F)=C1 BNPWVUJOPCGHIK-UHFFFAOYSA-N 0.000 description 2
KQOIBXZRCYFZSO-UHFFFAOYSA-N 3,5-difluoroaniline Chemical compound NC1=CC(F)=CC(F)=C1 KQOIBXZRCYFZSO-UHFFFAOYSA-N 0.000 description 2
LFYVNHDFVIPZHV-UHFFFAOYSA-N 3,5-difluorobenzenethiol Chemical compound FC1=CC(F)=CC(S)=C1 LFYVNHDFVIPZHV-UHFFFAOYSA-N 0.000 description 2
TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
HKFNSPCPXRHIGW-UHFFFAOYSA-N 3,6,8-tribromoimidazo[1,2-b]pyridazine Chemical compound BrC1=CC(Br)=NN2C(Br)=CN=C21 HKFNSPCPXRHIGW-UHFFFAOYSA-N 0.000 description 2
IGIHESAFEHKUSR-UHFFFAOYSA-N 3-[4-(1,3-dioxolan-2-yl)phenyl]-6-(2-methylpyrazol-3-yl)-n-(3,3,3-trifluoropropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound CN1N=CC=C1C1=NN2C(C=3C=CC(=CC=3)C3OCCO3)=CN=C2C(NCCC(F)(F)F)=C1 IGIHESAFEHKUSR-UHFFFAOYSA-N 0.000 description 2
FJXBVCUNMIPAPD-UHFFFAOYSA-N 3-[4-(1,3-dioxolan-2-yl)phenyl]-n-(2-methylpropyl)-6-pyridin-4-ylimidazo[1,2-b]pyridazin-8-amine Chemical compound C=1N=C2C(NCC(C)C)=CC(C=3C=CN=CC=3)=NN2C=1C(C=C1)=CC=C1C1OCCO1 FJXBVCUNMIPAPD-UHFFFAOYSA-N 0.000 description 2
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 2
LJWAPDSCYTZUJU-UHFFFAOYSA-N 3-fluoro-4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1F LJWAPDSCYTZUJU-UHFFFAOYSA-N 0.000 description 2
DPHBKGYVIHTBDG-UHFFFAOYSA-N 3-fluoro-5-methylaniline Chemical compound CC1=CC(N)=CC(F)=C1 DPHBKGYVIHTBDG-UHFFFAOYSA-N 0.000 description 2
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
OPXLVWLFDKRYRB-UHFFFAOYSA-N 3-methoxy-2-methylaniline Chemical compound COC1=CC=CC(N)=C1C OPXLVWLFDKRYRB-UHFFFAOYSA-N 0.000 description 2
ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
XCCNRBCNYGWTQX-UHFFFAOYSA-N 3-propan-2-ylaniline Chemical compound CC(C)C1=CC=CC(N)=C1 XCCNRBCNYGWTQX-UHFFFAOYSA-N 0.000 description 2
VLJSLTNSFSOYQR-UHFFFAOYSA-N 3-propan-2-ylphenol Chemical compound CC(C)C1=CC=CC(O)=C1 VLJSLTNSFSOYQR-UHFFFAOYSA-N 0.000 description 2
GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
WCMLRSZJUIKVCW-UHFFFAOYSA-N 4-(trifluoromethyl)benzenethiol Chemical compound FC(F)(F)C1=CC=C(S)C=C1 WCMLRSZJUIKVCW-UHFFFAOYSA-N 0.000 description 2
OKIHXNKYYGUVTE-UHFFFAOYSA-N 4-Fluorothiophenol Chemical compound FC1=CC=C(S)C=C1 OKIHXNKYYGUVTE-UHFFFAOYSA-N 0.000 description 2
VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 2
BJQVCXRFJBMXMJ-UHFFFAOYSA-N 4-[6-(3-fluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound N=1N2C(C=3C=CC(C=O)=CC=3)=CN=C2C(NCC(C)(O)C)=CC=1OC1=CC=CC(F)=C1 BJQVCXRFJBMXMJ-UHFFFAOYSA-N 0.000 description 2
HSYXFEXCFMCNAO-UHFFFAOYSA-N 4-[6-(3-fluorophenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound N=1N2C(C=3C=CC(C=O)=CC=3)=CN=C2C(NCC(C)(O)C)=CC=1SC1=CC=CC(F)=C1 HSYXFEXCFMCNAO-UHFFFAOYSA-N 0.000 description 2
ZBDWQZKQCDFUBA-UHFFFAOYSA-N 4-[6-(4-fluorophenyl)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound C=1N=C2C(NCC(C)(O)C)=CC(C=3C=CC(F)=CC=3)=NN2C=1C1=CC=C(C=O)C=C1 ZBDWQZKQCDFUBA-UHFFFAOYSA-N 0.000 description 2
LCHBTPBTVLSBTP-UHFFFAOYSA-N 4-[6-bromo-8-(oxan-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropylbenzamide Chemical compound C12=NC=C(C=3C=CC(=CC=3)C(=O)NC3CC3)N2N=C(Br)C=C1NCC1CCOCC1 LCHBTPBTVLSBTP-UHFFFAOYSA-N 0.000 description 2
BXSUZZBUBWWDAT-UHFFFAOYSA-N 4-[6-bromo-8-[(1,1-dioxothian-4-yl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-N-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Br)C=C(NCC4CCS(=O)(=O)CC4)C3=NC=2)=CC=C1C(=O)NC1CC1 BXSUZZBUBWWDAT-UHFFFAOYSA-N 0.000 description 2
QYCYXTNXWTYUKA-UHFFFAOYSA-N 4-[6-chloro-8-(2-methylpropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-fluorobenzonitrile Chemical compound C=1N=C2C(NCC(C)C)=CC(Cl)=NN2C=1C1=CC=C(C#N)C(F)=C1 QYCYXTNXWTYUKA-UHFFFAOYSA-N 0.000 description 2
FZPXZSHVQSHOQD-UHFFFAOYSA-N 4-[6-chloro-8-(2-methylpropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=CC(Cl)=NN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 FZPXZSHVQSHOQD-UHFFFAOYSA-N 0.000 description 2
OUVQJGKKVIUVAD-UHFFFAOYSA-N 4-[6-chloro-8-(2-morpholin-4-ylsulfonylethylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Cl)C=C(NCCS(=O)(=O)N4CCOCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 OUVQJGKKVIUVAD-UHFFFAOYSA-N 0.000 description 2
CETMLJPSTRDABR-UHFFFAOYSA-N 4-[6-chloro-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzenecarbothioamide Chemical compound CC1=CC(C=2N3N=C(Cl)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=S)NC1CC1 CETMLJPSTRDABR-UHFFFAOYSA-N 0.000 description 2
YCSWBHPCCAPTKF-UHFFFAOYSA-N 4-[6-chloro-8-(oxan-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Cl)C=C(NCC4OCCCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 YCSWBHPCCAPTKF-UHFFFAOYSA-N 0.000 description 2
UQFBMLWKZCMDJH-UHFFFAOYSA-N 4-[6-chloro-8-[(2-methyloxolan-2-yl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Cl)C=C(NCC4(C)OCCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 UQFBMLWKZCMDJH-UHFFFAOYSA-N 0.000 description 2
QQVIINCRQLPUHL-UHFFFAOYSA-N 4-[6-chloro-8-[(2-methylpyrazol-3-yl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Cl)C=C(NCC=4N(N=CC=4)C)C3=NC=2)=CC=C1C(=O)NC1CC1 QQVIINCRQLPUHL-UHFFFAOYSA-N 0.000 description 2
NFVWOGCOBMFKNQ-UHFFFAOYSA-N 4-[6-chloro-8-[(4-methylmorpholin-2-yl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-N-cyclopropyl-2-methylbenzamide Chemical compound C1N(C)CCOC1CNC1=CC(Cl)=NN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 NFVWOGCOBMFKNQ-UHFFFAOYSA-N 0.000 description 2
KKKFBPVKGJCKBM-UHFFFAOYSA-N 4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-phenoxyimidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound N=1N2C(C=3C=CC(C=O)=CC=3)=CN=C2C(NCC(C)(O)C)=CC=1OC1=CC=CC=C1 KKKFBPVKGJCKBM-UHFFFAOYSA-N 0.000 description 2
KFPAYYHBMPHYHR-UHFFFAOYSA-N 4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-phenylsulfanylimidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound N=1N2C(C=3C=CC(C=O)=CC=3)=CN=C2C(NCC(C)(O)C)=CC=1SC1=CC=CC=C1 KFPAYYHBMPHYHR-UHFFFAOYSA-N 0.000 description 2
OJCAKOFFLWVGEA-UHFFFAOYSA-N 4-bromo-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(Br)=CC=C1C(=O)NC1CC1 OJCAKOFFLWVGEA-UHFFFAOYSA-N 0.000 description 2
CSFDTBRRIBJILD-UHFFFAOYSA-N 4-chloro-2-fluoroaniline Chemical compound NC1=CC=C(Cl)C=C1F CSFDTBRRIBJILD-UHFFFAOYSA-N 0.000 description 2
ACMJJQYSPUPMPN-UHFFFAOYSA-N 4-chloro-3-fluoroaniline Chemical compound NC1=CC=C(Cl)C(F)=C1 ACMJJQYSPUPMPN-UHFFFAOYSA-N 0.000 description 2
XLHYAEBESNFTCA-UHFFFAOYSA-N 4-chloro-3-fluorophenol Chemical compound OC1=CC=C(Cl)C(F)=C1 XLHYAEBESNFTCA-UHFFFAOYSA-N 0.000 description 2
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
BNRRMRUVYDETQC-UHFFFAOYSA-N 4-fluoro-2-methoxyaniline Chemical compound COC1=CC(F)=CC=C1N BNRRMRUVYDETQC-UHFFFAOYSA-N 0.000 description 2
XAACOEWSHBIFGJ-UHFFFAOYSA-N 4-fluoro-3-methoxyaniline Chemical compound COC1=CC(N)=CC=C1F XAACOEWSHBIFGJ-UHFFFAOYSA-N 0.000 description 2
NYMDPDNETOLVBS-UHFFFAOYSA-N 4-fluoro-3-methylaniline Chemical compound CC1=CC(N)=CC=C1F NYMDPDNETOLVBS-UHFFFAOYSA-N 0.000 description 2
WIYZIRGRLJSWNS-UHFFFAOYSA-N 4-fluoro-3-methylbenzenethiol Chemical compound CC1=CC(S)=CC=C1F WIYZIRGRLJSWNS-UHFFFAOYSA-N 0.000 description 2
RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 2
NIFAOMSJMGEFTQ-UHFFFAOYSA-N 4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1 NIFAOMSJMGEFTQ-UHFFFAOYSA-N 0.000 description 2
AGWWTUWTOBEQFE-UHFFFAOYSA-N 4-methyl-1h-1,2,4-triazole-5-thione Chemical compound CN1C=NN=C1S AGWWTUWTOBEQFE-UHFFFAOYSA-N 0.000 description 2
QEYQMWSESURNPP-UHFFFAOYSA-N 4-propan-2-yloxyphenol Chemical compound CC(C)OC1=CC=C(O)C=C1 QEYQMWSESURNPP-UHFFFAOYSA-N 0.000 description 2
SECLKVXODNUVIB-UHFFFAOYSA-N 5-(4-bromophenyl)-2-cyclopropyl-1h-imidazole Chemical compound C1=CC(Br)=CC=C1C1=CNC(C2CC2)=N1 SECLKVXODNUVIB-UHFFFAOYSA-N 0.000 description 2
AVPBPARCKGVYMH-UHFFFAOYSA-N 5-fluoro-2-methylbenzenethiol Chemical compound CC1=CC=C(F)C=C1S AVPBPARCKGVYMH-UHFFFAOYSA-N 0.000 description 2
CKJOSIHYVLHIER-UHFFFAOYSA-N 5-fluoro-2-methylphenol Chemical compound CC1=CC=C(F)C=C1O CKJOSIHYVLHIER-UHFFFAOYSA-N 0.000 description 2
RPJXLEZOFUNGNZ-UHFFFAOYSA-N 5-methoxy-2-methylaniline Chemical compound COC1=CC=C(C)C(N)=C1 RPJXLEZOFUNGNZ-UHFFFAOYSA-N 0.000 description 2
CRVNSRICWIACSB-UHFFFAOYSA-N 6-bromo-3-iodo-n-(4,4,4-trifluorobutyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound FC(F)(F)CCCNC1=CC(Br)=NN2C(I)=CN=C12 CRVNSRICWIACSB-UHFFFAOYSA-N 0.000 description 2
REGPMKCAOMWXJM-UHFFFAOYSA-N 6-bromo-n-(3,3,3-trifluoropropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound FC(F)(F)CCNC1=CC(Br)=NN2C=CN=C12 REGPMKCAOMWXJM-UHFFFAOYSA-N 0.000 description 2
HYFDBKBCUYTXJR-UHFFFAOYSA-N 6-chloro-3-[4-(1,3-dioxolan-2-yl)phenyl]-n-(2-methylpropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C=1N=C2C(NCC(C)C)=CC(Cl)=NN2C=1C(C=C1)=CC=C1C1OCCO1 HYFDBKBCUYTXJR-UHFFFAOYSA-N 0.000 description 2
DTUNMTZEFCSWLC-QGZVFWFLSA-N 6-chloro-3-[4-(2-cyclopropyl-1H-imidazol-5-yl)phenyl]-N-[[(2R)-oxolan-2-yl]methyl]imidazo[1,2-b]pyridazin-8-amine Chemical compound C12=NC=C(C=3C=CC(=CC=3)C=3NC(=NC=3)C3CC3)N2N=C(Cl)C=C1NC[C@H]1CCCO1 DTUNMTZEFCSWLC-QGZVFWFLSA-N 0.000 description 2
WYLHWOVONMTEND-UHFFFAOYSA-N 6-chloro-3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-n-(oxan-2-ylmethyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C12=NC=C(C=3C=CC(=CC=3)C=3N=C(NC=3)C3CC3)N2N=C(Cl)C=C1NCC1CCCCO1 WYLHWOVONMTEND-UHFFFAOYSA-N 0.000 description 2
DTUNMTZEFCSWLC-KRWDZBQOSA-N 6-chloro-3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-n-[[(2s)-oxolan-2-yl]methyl]imidazo[1,2-b]pyridazin-8-amine Chemical compound C12=NC=C(C=3C=CC(=CC=3)C=3NC(=NC=3)C3CC3)N2N=C(Cl)C=C1NC[C@@H]1CCCO1 DTUNMTZEFCSWLC-KRWDZBQOSA-N 0.000 description 2
JUFWDTQQQULFFA-UHFFFAOYSA-N 6-chloro-3-iodo-n-(2-methoxy-2-methylpropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound COC(C)(C)CNC1=CC(Cl)=NN2C(I)=CN=C12 JUFWDTQQQULFFA-UHFFFAOYSA-N 0.000 description 2
GMOFZDDFUITZFW-UHFFFAOYSA-N 6-chloro-3-iodo-n-(2-morpholin-4-ylsulfonylethyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C12=NC=C(I)N2N=C(Cl)C=C1NCCS(=O)(=O)N1CCOCC1 GMOFZDDFUITZFW-UHFFFAOYSA-N 0.000 description 2
QGFDTPZYDXOOMZ-UHFFFAOYSA-N 6-chloro-3-iodo-n-[(2-methylpyrazol-3-yl)methyl]imidazo[1,2-b]pyridazin-8-amine Chemical compound CN1N=CC=C1CNC1=CC(Cl)=NN2C1=NC=C2I QGFDTPZYDXOOMZ-UHFFFAOYSA-N 0.000 description 2
UYVWOESWUGYANU-UHFFFAOYSA-N 6-chloro-3-iodo-n-[(4-methylmorpholin-2-yl)methyl]imidazo[1,2-b]pyridazin-8-amine Chemical compound C1N(C)CCOC1CNC1=CC(Cl)=NN2C1=NC=C2I UYVWOESWUGYANU-UHFFFAOYSA-N 0.000 description 2
DXFQGADLXCAIRO-UHFFFAOYSA-N 6-chloro-n-(1,4-dioxan-2-ylmethyl)-3-iodoimidazo[1,2-b]pyridazin-8-amine Chemical compound C12=NC=C(I)N2N=C(Cl)C=C1NCC1COCCO1 DXFQGADLXCAIRO-UHFFFAOYSA-N 0.000 description 2
NQKLZQUYDPBVPZ-UHFFFAOYSA-N 6-cyclopentyloxy-3-iodo-n-(3,3,3-trifluoropropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound N=1N2C(I)=CN=C2C(NCCC(F)(F)F)=CC=1OC1CCCC1 NQKLZQUYDPBVPZ-UHFFFAOYSA-N 0.000 description 2
YTHMOBMZVVFNBE-UHFFFAOYSA-N 6-fluoropyridin-3-amine Chemical compound NC1=CC=C(F)N=C1 YTHMOBMZVVFNBE-UHFFFAOYSA-N 0.000 description 2
HTRLNWYWOKWCLV-UHFFFAOYSA-N 6-fluoropyridin-3-ol Chemical compound OC1=CC=C(F)N=C1 HTRLNWYWOKWCLV-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
201000009030 Carcinoma Diseases 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 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 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
239000012425 OXONE® Substances 0.000 description 2
229930012538 Paclitaxel Natural products 0.000 description 2
102000001253 Protein Kinase Human genes 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
229940123237 Taxane Drugs 0.000 description 2
CBMCZKMIOZYAHS-NSCUHMNNSA-N [(e)-prop-1-enyl]boronic acid Chemical compound C\C=C\B(O)O CBMCZKMIOZYAHS-NSCUHMNNSA-N 0.000 description 2
CCXHEPSOPWJNJB-ONEGZZNKSA-N [(z)-but-2-en-2-yl]boronic acid Chemical compound C\C=C(/C)B(O)O CCXHEPSOPWJNJB-ONEGZZNKSA-N 0.000 description 2
KPKXGHISVNPSIV-UHFFFAOYSA-N [2-[3-[4-(1,3-dioxolan-2-yl)phenyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-6-yl]phenyl]methanol Chemical compound OCC1=CC=CC=C1C1=NN2C(C=3C=CC(=CC=3)C3OCCO3)=CN=C2C(NCCC(F)(F)F)=C1 KPKXGHISVNPSIV-UHFFFAOYSA-N 0.000 description 2
AEOJDQJSNRBDKQ-UHFFFAOYSA-N [3-[3-[4-(1,3-dioxolan-2-yl)phenyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-6-yl]phenyl]methanol Chemical compound OCC1=CC=CC(C2=NN3C(C=4C=CC(=CC=4)C4OCCO4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 AEOJDQJSNRBDKQ-UHFFFAOYSA-N 0.000 description 2
SPGPJDKIBHDACA-UHFFFAOYSA-N [4-chloro-2-(hydroxymethyl)phenyl]boronic acid Chemical compound OCC1=CC(Cl)=CC=C1B(O)O SPGPJDKIBHDACA-UHFFFAOYSA-N 0.000 description 2
UTCXJLROIZMSEK-UHFFFAOYSA-N [4-fluoro-2-[tri(propan-2-yl)silyloxymethyl]phenyl]boronic acid Chemical compound CC(C)[Si](C(C)C)(C(C)C)OCC1=CC(F)=CC=C1B(O)O UTCXJLROIZMSEK-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
150000001345 alkine derivatives Chemical class 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
230000031016 anaphase Effects 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
150000001649 bromium compounds Chemical class 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
230000030833 cell death Effects 0.000 description 2
230000032823 cell division Effects 0.000 description 2
238000004296 chiral HPLC Methods 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
229960001701 chloroform Drugs 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
XZWQKJXJNKYMAP-UHFFFAOYSA-N cyclohexen-1-ylboronic acid Chemical compound OB(O)C1=CCCCC1 XZWQKJXJNKYMAP-UHFFFAOYSA-N 0.000 description 2
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 2
238000001212 derivatisation Methods 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
238000003821 enantio-separation Methods 0.000 description 2
229930013356 epothilone Natural products 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
150000004694 iodide salts Chemical class 0.000 description 2
VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
239000002207 metabolite Substances 0.000 description 2
YSVZADAAWQNYCF-UHFFFAOYSA-N methylsulfanylmethane;sodium Chemical compound [Na].CSC YSVZADAAWQNYCF-UHFFFAOYSA-N 0.000 description 2
230000036456 mitotic arrest Effects 0.000 description 2
IPVAUQOZKBKERC-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-pyridin-3-yloxy-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=NC=CC=4)C=C(NCC4CCSCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 IPVAUQOZKBKERC-UHFFFAOYSA-N 0.000 description 2
KBHVRRMYZYKJBP-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[8-(2-methylpropylamino)-6-phenylsulfanylimidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)C)=CC=1SC1=CC=CC=C1 KBHVRRMYZYKJBP-UHFFFAOYSA-N 0.000 description 2
FHKHYJKWGYVFOU-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-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=C(F)C=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 FHKHYJKWGYVFOU-UHFFFAOYSA-N 0.000 description 2
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 description 2
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 description 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 description 2
NWSHNGZGICYCIZ-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(hydroxymethyl)phenyl]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)O)C3=NC=2)C=2C(=CC=CC=2)CO)=CC=C1C(=O)NC1CC1 NWSHNGZGICYCIZ-UHFFFAOYSA-N 0.000 description 2
NVKUYFKNPDWEEG-UHFFFAOYSA-N n-cyclopropyl-4-[8-(2-methylpropylamino)-6-methylsulfanylimidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound N12N=C(SC)C=C(NCC(C)C)C2=NC=C1C(C=C1)=CC=C1C(=O)NC1CC1 NVKUYFKNPDWEEG-UHFFFAOYSA-N 0.000 description 2
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 description 2
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 description 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 description 2
MLSONLILJQGSCW-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-methylsulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N12N=C(SC)C=C(NCC(C)(C)O)C2=NC=C1C(C=C1C)=CC=C1C(=O)NC1CC1 MLSONLILJQGSCW-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
229960001592 paclitaxel Drugs 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
108060006633 protein kinase Proteins 0.000 description 2
125000003226 pyrazolyl group Chemical group 0.000 description 2
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000011160 research Methods 0.000 description 2
FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000011593 sulfur Substances 0.000 description 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 description 2
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
MTEQAOQIRDWEES-UHFFFAOYSA-N tert-butyl N-(6-cyclopentyloxyimidazo[1,2-b]pyridazin-8-yl)-N-(3,3,3-trifluoropropyl)carbamate Chemical compound N=1N2C=CN=C2C(N(CCC(F)(F)F)C(=O)OC(C)(C)C)=CC=1OC1CCCC1 MTEQAOQIRDWEES-UHFFFAOYSA-N 0.000 description 2
VCRKOUPXSMOIQU-UHFFFAOYSA-N tert-butyl N-[6-(cyclopentylamino)imidazo[1,2-b]pyridazin-8-yl]-N-(3,3,3-trifluoropropyl)carbamate Chemical compound N=1N2C=CN=C2C(N(CCC(F)(F)F)C(=O)OC(C)(C)C)=CC=1NC1CCCC1 VCRKOUPXSMOIQU-UHFFFAOYSA-N 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
125000003396 thiol group Chemical group [H]S* 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
229940062627 tribasic potassium phosphate Drugs 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 2
PCEIEQLJYDMRFZ-UHFFFAOYSA-N (1-cyanocyclopropyl)azanium;chloride Chemical compound Cl.N#CC1(N)CC1 PCEIEQLJYDMRFZ-UHFFFAOYSA-N 0.000 description 1
GHILZUOTUJGCDH-UHFFFAOYSA-N (1-methylcyclopropyl)azanium;chloride Chemical compound Cl.CC1(N)CC1 GHILZUOTUJGCDH-UHFFFAOYSA-N 0.000 description 1
SOCAXRLFGRNEPK-IFZYUDKTSA-N (1r,3s,5r)-2-n-[1-carbamoyl-5-(cyanomethoxy)indol-3-yl]-3-n-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-2,3-dicarboxamide Chemical compound O=C([C@@H]1C[C@H]2C[C@H]2N1C(=O)NC1=CN(C2=CC=C(OCC#N)C=C21)C(=O)N)NCC1=CC=CC(Cl)=C1F SOCAXRLFGRNEPK-IFZYUDKTSA-N 0.000 description 1
MKDRHMDHWIBVRH-NTSWFWBYSA-N (1s)-2-amino-1-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol Chemical compound CC1(C)OC[C@H]([C@@H](O)CN)O1 MKDRHMDHWIBVRH-NTSWFWBYSA-N 0.000 description 1
XOLSMTBBIZDHSG-UHFFFAOYSA-N (2,2-difluorocyclopropyl)methanol Chemical compound OCC1CC1(F)F XOLSMTBBIZDHSG-UHFFFAOYSA-N 0.000 description 1
HXGZPMHPSBJMKB-UHFFFAOYSA-N (2-bromo-5-fluorophenyl)methanol Chemical compound OCC1=CC(F)=CC=C1Br HXGZPMHPSBJMKB-UHFFFAOYSA-N 0.000 description 1
QCSLIRFWJPOENV-UHFFFAOYSA-N (2-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1F QCSLIRFWJPOENV-UHFFFAOYSA-N 0.000 description 1
DLKKHCBCEHVVFW-UHFFFAOYSA-N (2-methyloxolan-2-yl)methanamine Chemical compound NCC1(C)CCCO1 DLKKHCBCEHVVFW-UHFFFAOYSA-N 0.000 description 1
XNTFQMKXUFFUQO-UHFFFAOYSA-N (2-methylpyrazol-3-yl)methanamine Chemical compound CN1N=CC=C1CN XNTFQMKXUFFUQO-UHFFFAOYSA-N 0.000 description 1
FYWFCRHZXORPFH-UHFFFAOYSA-N (2-sulfanylphenyl)methanol Chemical compound OCC1=CC=CC=C1S FYWFCRHZXORPFH-UHFFFAOYSA-N 0.000 description 1
DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-N 0.000 description 1
CUGDYSSBTWBKII-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(dimethylamino)hexane-1,2,3,4,5-pentol Chemical compound CN(C)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO CUGDYSSBTWBKII-LXGUWJNJSA-N 0.000 description 1
IKXCHOUDIPZROZ-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(ethylamino)hexane-1,2,3,4,5-pentol Chemical compound CCNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO IKXCHOUDIPZROZ-LXGUWJNJSA-N 0.000 description 1
FRKGSNOMLIYPSH-VKHMYHEASA-N (3s)-3-hydroxypyrrolidin-2-one Chemical compound O[C@H]1CCNC1=O FRKGSNOMLIYPSH-VKHMYHEASA-N 0.000 description 1
OYUDJHNYSVXVNK-UHFFFAOYSA-N (4-fluoro-2-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC(F)=CC=C1B(O)O OYUDJHNYSVXVNK-UHFFFAOYSA-N 0.000 description 1
IQMLIVUHMSIOQP-UHFFFAOYSA-N (4-fluoro-2-methylphenyl)boronic acid Chemical compound CC1=CC(F)=CC=C1B(O)O IQMLIVUHMSIOQP-UHFFFAOYSA-N 0.000 description 1
SOBFKNVNVLNAJQ-UHFFFAOYSA-N (4-methylmorpholin-2-yl)methanamine Chemical compound CN1CCOC(CN)C1 SOBFKNVNVLNAJQ-UHFFFAOYSA-N 0.000 description 1
HGRWHBQLRXWSLV-DEOSSOPVSA-N (4s)-3'-(3,6-dihydro-2h-pyran-5-yl)-1'-fluoro-7'-(3-fluoropyridin-2-yl)spiro[5h-1,3-oxazole-4,5'-chromeno[2,3-c]pyridine]-2-amine Chemical compound C1OC(N)=N[C@]21C1=CC(C=3COCCC=3)=NC(F)=C1OC1=CC=C(C=3C(=CC=CN=3)F)C=C12 HGRWHBQLRXWSLV-DEOSSOPVSA-N 0.000 description 1
125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 description 1
LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 description 1
UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
OPCJOXGBLDJWRM-UHFFFAOYSA-N 1,2-diamino-2-methylpropane Chemical compound CC(C)(N)CN OPCJOXGBLDJWRM-UHFFFAOYSA-N 0.000 description 1
XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 1
125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
VUMCUSHVMYIRMB-UHFFFAOYSA-N 1,3,5-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1 VUMCUSHVMYIRMB-UHFFFAOYSA-N 0.000 description 1
PREOONMJIVUPMI-UHFFFAOYSA-N 1,4-dioxan-2-ylmethanamine Chemical compound NCC1COCCO1 PREOONMJIVUPMI-UHFFFAOYSA-N 0.000 description 1
CYPYTURSJDMMMP-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 CYPYTURSJDMMMP-UHFFFAOYSA-N 0.000 description 1
CGMLIPSMGVCIIT-UHFFFAOYSA-N 1-[[3-[4-(1,3-dioxolan-2-yl)phenyl]-6-pyridin-4-ylimidazo[1,2-b]pyridazin-8-yl]amino]-2-methylpropan-2-ol Chemical compound C=1N=C2C(NCC(C)(O)C)=CC(C=3C=CN=CC=3)=NN2C=1C(C=C1)=CC=C1C1OCCO1 CGMLIPSMGVCIIT-UHFFFAOYSA-N 0.000 description 1
WPASTZVOBADJHL-UHFFFAOYSA-N 1-[[3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-6-(4-fluorophenyl)imidazo[1,2-b]pyridazin-8-yl]amino]-2-methylpropan-2-ol Chemical compound C=1N=C2C(NCC(C)(O)C)=CC(C=3C=CC(F)=CC=3)=NN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 WPASTZVOBADJHL-UHFFFAOYSA-N 0.000 description 1
RTTHXECCTVSYTD-UHFFFAOYSA-N 1-[[3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-6-pyridin-4-ylimidazo[1,2-b]pyridazin-8-yl]amino]-2-methylpropan-2-ol Chemical compound C=1N=C2C(NCC(C)(O)C)=CC(C=3C=CN=CC=3)=NN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 RTTHXECCTVSYTD-UHFFFAOYSA-N 0.000 description 1
ZGCHLAJIRWDGFE-UHFFFAOYSA-N 1-aminopropane-1,1-diol Chemical compound CCC(N)(O)O ZGCHLAJIRWDGFE-UHFFFAOYSA-N 0.000 description 1
125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical class CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
IEPAHAXVBXNSKS-UHFFFAOYSA-N 1-methoxycyclopropan-1-amine;hydrochloride Chemical compound [Cl-].COC1([NH3+])CC1 IEPAHAXVBXNSKS-UHFFFAOYSA-N 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
NEUWPDLMDVINSN-UHFFFAOYSA-N 1h-pyrazol-5-ylboronic acid Chemical compound OB(O)C=1C=CNN=1 NEUWPDLMDVINSN-UHFFFAOYSA-N 0.000 description 1
QYTSIBBNZWTHMZ-UHFFFAOYSA-N 2,3-difluorobenzenethiol Chemical compound FC1=CC=CC(S)=C1F QYTSIBBNZWTHMZ-UHFFFAOYSA-N 0.000 description 1
SQDUGGGBJXULJR-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-6-ylboronic acid Chemical compound O1CCOC2=CC(B(O)O)=CC=C21 SQDUGGGBJXULJR-UHFFFAOYSA-N 0.000 description 1
CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 description 1
PALORHWWZVBSLZ-UHFFFAOYSA-N 2,6-difluorobenzenethiol Chemical compound FC1=CC=CC(F)=C1S PALORHWWZVBSLZ-UHFFFAOYSA-N 0.000 description 1
JHKKTXXMAQLGJB-UHFFFAOYSA-N 2-(methylamino)phenol Chemical compound CNC1=CC=CC=C1O JHKKTXXMAQLGJB-UHFFFAOYSA-N 0.000 description 1
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
MAOTUJPKBAIACF-UHFFFAOYSA-N 2-amino-4-fluorobenzenethiol Chemical compound NC1=CC(F)=CC=C1S MAOTUJPKBAIACF-UHFFFAOYSA-N 0.000 description 1
IIDUNAVOCYMUFB-UHFFFAOYSA-N 2-amino-5-fluorophenol Chemical compound NC1=CC=C(F)C=C1O IIDUNAVOCYMUFB-UHFFFAOYSA-N 0.000 description 1
DGUVEYAZTOUCEJ-UHFFFAOYSA-N 2-aminoethanesulfonamide;hydron;chloride Chemical compound Cl.NCCS(N)(=O)=O DGUVEYAZTOUCEJ-UHFFFAOYSA-N 0.000 description 1
KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
FKJSFKCZZIXQIP-UHFFFAOYSA-N 2-bromo-1-(4-bromophenyl)ethanone Chemical compound BrCC(=O)C1=CC=C(Br)C=C1 FKJSFKCZZIXQIP-UHFFFAOYSA-N 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
FJKIADFDXOCBRV-UHFFFAOYSA-N 2-chloro-3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1Cl FJKIADFDXOCBRV-UHFFFAOYSA-N 0.000 description 1
XRAKCYJTJGTSMM-UHFFFAOYSA-N 2-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1Cl XRAKCYJTJGTSMM-UHFFFAOYSA-N 0.000 description 1
OXXHRLOTYJWMIW-UHFFFAOYSA-N 2-cyclopropyl-5-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1h-imidazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2NC(=NC=2)C2CC2)C=C1 OXXHRLOTYJWMIW-UHFFFAOYSA-N 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
XFAWPESFTAFNGT-UHFFFAOYSA-N 2-fluoro-4-[6-(3-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzonitrile Chemical compound FC1=CC=CC(OC2=NN3C(C=4C=C(F)C(C#N)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 XFAWPESFTAFNGT-UHFFFAOYSA-N 0.000 description 1
ZSTYQALWKOGXOV-UHFFFAOYSA-N 2-methoxy-2-methylpropan-1-amine Chemical compound COC(C)(C)CN ZSTYQALWKOGXOV-UHFFFAOYSA-N 0.000 description 1
JMYJYCLCOQMNOY-UHFFFAOYSA-N 2-methoxy-3-propan-2-ylphenol Chemical compound COC1=C(O)C=CC=C1C(C)C JMYJYCLCOQMNOY-UHFFFAOYSA-N 0.000 description 1
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
UMJGOCMSBZWCNY-UHFFFAOYSA-N 2-methyl-4-sulfanylphenol Chemical compound CC1=CC(S)=CC=C1O UMJGOCMSBZWCNY-UHFFFAOYSA-N 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
OINANNBISYKCNE-UHFFFAOYSA-N 2-morpholin-4-ylsulfonylethanamine Chemical compound NCCS(=O)(=O)N1CCOCC1 OINANNBISYKCNE-UHFFFAOYSA-N 0.000 description 1
WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical class BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
IGOPOYHPIKTQSS-UHFFFAOYSA-N 3,3,3-trifluoropropan-1-amine;hydrochloride Chemical compound [Cl-].[NH3+]CCC(F)(F)F IGOPOYHPIKTQSS-UHFFFAOYSA-N 0.000 description 1
HJSSBIMVTMYKPD-UHFFFAOYSA-N 3,5-difluorophenol Chemical compound OC1=CC(F)=CC(F)=C1 HJSSBIMVTMYKPD-UHFFFAOYSA-N 0.000 description 1
ZFSXZJFCSFCJOX-UHFFFAOYSA-N 3,6-dibromo-n-(3,3,3-trifluoropropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound FC(F)(F)CCNC1=CC(Br)=NN2C(Br)=CN=C12 ZFSXZJFCSFCJOX-UHFFFAOYSA-N 0.000 description 1
FUAKUDUYSVHHPU-UHFFFAOYSA-N 3-(3-amino-1h-indazol-6-yl)-6-(3-fluorophenoxy)-n-(3,3,3-trifluoropropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C=1C=C2C(N)=NNC2=CC=1C(N1N=2)=CN=C1C(NCCC(F)(F)F)=CC=2OC1=CC=CC(F)=C1 FUAKUDUYSVHHPU-UHFFFAOYSA-N 0.000 description 1
NQIISOASJVNVFU-UHFFFAOYSA-N 3-(3-amino-1h-indazol-6-yl)-n-(2-methylpropyl)-6-phenylimidazo[1,2-b]pyridazin-8-amine Chemical compound N=1N2C(C=3C=C4NN=C(N)C4=CC=3)=CN=C2C(NCC(C)C)=CC=1C1=CC=CC=C1 NQIISOASJVNVFU-UHFFFAOYSA-N 0.000 description 1
YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
LKWDARKUZCSXNI-UHFFFAOYSA-N 3-[(6-chloro-3-iodoimidazo[1,2-b]pyridazin-8-yl)amino]-1,1,1-trifluoropropan-2-ol Chemical compound FC(F)(F)C(O)CNC1=CC(Cl)=NN2C(I)=CN=C12 LKWDARKUZCSXNI-UHFFFAOYSA-N 0.000 description 1
JJVMLZPKTIXMRQ-UHFFFAOYSA-N 3-[2-methyl-2-tri(propan-2-yl)silyloxypropoxy]phenol Chemical compound CC(C)[Si](C(C)C)(C(C)C)OC(C)(C)COC1=CC=CC(O)=C1 JJVMLZPKTIXMRQ-UHFFFAOYSA-N 0.000 description 1
PPKCUWDRZUVJKX-UHFFFAOYSA-N 3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-6-(4-fluorophenyl)-n-(3,3,3-trifluoropropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C1=CC(F)=CC=C1C1=NN2C(C=3C=CC(=CC=3)C=3NC(=NC=3)C3CC3)=CN=C2C(NCCC(F)(F)F)=C1 PPKCUWDRZUVJKX-UHFFFAOYSA-N 0.000 description 1
XBKHBIIZZMLSLD-UHFFFAOYSA-N 3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-6-pyridin-4-yl-n-(3,3,3-trifluoropropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C=1N=C2C(NCCC(F)(F)F)=CC(C=3C=CN=CC=3)=NN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 XBKHBIIZZMLSLD-UHFFFAOYSA-N 0.000 description 1
FWHPLDJOTXITEK-UHFFFAOYSA-N 3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-n-(2-methylpropyl)-6-pyridin-4-ylimidazo[1,2-b]pyridazin-8-amine Chemical compound C=1N=C2C(NCC(C)C)=CC(C=3C=CN=CC=3)=NN2C=1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 FWHPLDJOTXITEK-UHFFFAOYSA-N 0.000 description 1
PTDBVVVCFFYSNM-UHFFFAOYSA-N 3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-n-(oxan-2-ylmethyl)-6-pyridin-4-ylimidazo[1,2-b]pyridazin-8-amine Chemical compound C1CCCOC1CNC(C1=NC=2)=CC(C=3C=CN=CC=3)=NN1C=2C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 PTDBVVVCFFYSNM-UHFFFAOYSA-N 0.000 description 1
RRUGOLVLCMESIY-JOCHJYFZSA-N 3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-n-[[(2r)-oxolan-2-yl]methyl]-6-pyridin-4-ylimidazo[1,2-b]pyridazin-8-amine Chemical compound C([C@@H]1OCCC1)NC(C1=NC=2)=CC(C=3C=CN=CC=3)=NN1C=2C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 RRUGOLVLCMESIY-JOCHJYFZSA-N 0.000 description 1
RRUGOLVLCMESIY-QFIPXVFZSA-N 3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-n-[[(2s)-oxolan-2-yl]methyl]-6-pyridin-4-ylimidazo[1,2-b]pyridazin-8-amine Chemical compound C([C@H]1OCCC1)NC(C1=NC=2)=CC(C=3C=CN=CC=3)=NN1C=2C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 RRUGOLVLCMESIY-QFIPXVFZSA-N 0.000 description 1
NBRDIIGPFDBUFZ-UHFFFAOYSA-N 3-[4-(cyclopropylcarbamoyl)-3-methylphenyl]-n-(2-hydroxyethyl)-8-(2-methylpropylamino)imidazo[1,2-b]pyridazine-6-carboxamide Chemical compound C=1N=C2C(NCC(C)C)=CC(C(=O)NCCO)=NN2C=1C(C=C1C)=CC=C1C(=O)NC1CC1 NBRDIIGPFDBUFZ-UHFFFAOYSA-N 0.000 description 1
RISHBQWFBUTROQ-UHFFFAOYSA-N 3-amino-1,1,1-trifluoropropan-2-ol Chemical compound NCC(O)C(F)(F)F RISHBQWFBUTROQ-UHFFFAOYSA-N 0.000 description 1
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
ZQXLIXHVJVAPLW-UHFFFAOYSA-N 3-chloro-4-fluorophenol Chemical compound OC1=CC=C(F)C(Cl)=C1 ZQXLIXHVJVAPLW-UHFFFAOYSA-N 0.000 description 1
IFSSSYDVRQSDSG-UHFFFAOYSA-N 3-ethenylaniline Chemical compound NC1=CC=CC(C=C)=C1 IFSSSYDVRQSDSG-UHFFFAOYSA-N 0.000 description 1
SWXOGIWNHWXDBS-UHFFFAOYSA-N 3-fluoro-2-methylbenzenethiol Chemical compound CC1=C(F)C=CC=C1S SWXOGIWNHWXDBS-UHFFFAOYSA-N 0.000 description 1
NLIOVTBTQHQXHO-UHFFFAOYSA-N 3-fluoro-4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1F NLIOVTBTQHQXHO-UHFFFAOYSA-N 0.000 description 1
SGHBRHKBCLLVCI-UHFFFAOYSA-N 3-hydroxybenzonitrile Chemical compound OC1=CC=CC(C#N)=C1 SGHBRHKBCLLVCI-UHFFFAOYSA-N 0.000 description 1
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
AELUMDDQRLJQRX-UHFFFAOYSA-N 3-propan-2-ylbenzenethiol Chemical compound CC(C)C1=CC=CC(S)=C1 AELUMDDQRLJQRX-UHFFFAOYSA-N 0.000 description 1
QMGBIPKOKCSUCL-UHFFFAOYSA-N 3-propan-2-yloxyaniline Chemical compound CC(C)OC1=CC=CC(N)=C1 QMGBIPKOKCSUCL-UHFFFAOYSA-N 0.000 description 1
CBGJTIYHMKYCMR-UHFFFAOYSA-N 3-propan-2-yloxybenzenethiol Chemical compound CC(C)OC1=CC=CC(S)=C1 CBGJTIYHMKYCMR-UHFFFAOYSA-N 0.000 description 1
GZMVGNWHSXIDKT-UHFFFAOYSA-N 3-propan-2-yloxyphenol Chemical compound CC(C)OC1=CC=CC(O)=C1 GZMVGNWHSXIDKT-UHFFFAOYSA-N 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
YELMWJNXDALKFE-UHFFFAOYSA-N 3h-imidazo[4,5-f]quinoxaline Chemical class N1=CC=NC2=C(NC=N3)C3=CC=C21 YELMWJNXDALKFE-UHFFFAOYSA-N 0.000 description 1
LAXWLCVPJLBABV-UHFFFAOYSA-N 4,4,4-trifluorobutan-1-amine Chemical compound NCCCC(F)(F)F LAXWLCVPJLBABV-UHFFFAOYSA-N 0.000 description 1
LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 description 1
LNPMZQXEPNWCMG-UHFFFAOYSA-N 4-(2-aminoethyl)aniline Chemical compound NCCC1=CC=C(N)C=C1 LNPMZQXEPNWCMG-UHFFFAOYSA-N 0.000 description 1
AIPUNCFCQBDNDJ-UHFFFAOYSA-N 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CCNCC1 AIPUNCFCQBDNDJ-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 1
GUVPBROLELMWAW-UHFFFAOYSA-N 4-[6-(2-methylpyrazol-3-yl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound CN1N=CC=C1C1=NN2C(C=3C=CC(C=O)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 GUVPBROLELMWAW-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 1
KZMSAXMFRLBOPW-UHFFFAOYSA-N 4-[6-(4-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=CC(Cl)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 KZMSAXMFRLBOPW-UHFFFAOYSA-N 0.000 description 1
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 description 1
JGAZYWLFBRAOLX-UHFFFAOYSA-N 4-[6-(5-chloro-2-methylanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC=C(Cl)C=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 JGAZYWLFBRAOLX-UHFFFAOYSA-N 0.000 description 1
IIVFWJRRSYUWFU-UHFFFAOYSA-N 4-[6-(5-chloro-2-methylanilino)-8-(4,4,4-trifluorobutylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC=C(Cl)C=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCCC(F)(F)F)=C1 IIVFWJRRSYUWFU-UHFFFAOYSA-N 0.000 description 1
XANWKJZOPPBDHJ-UHFFFAOYSA-N 4-[6-(5-chloro-2-methylanilino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC=C(Cl)C=C1NC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 XANWKJZOPPBDHJ-UHFFFAOYSA-N 0.000 description 1
HERBRAOUQDOUQV-UHFFFAOYSA-N 4-[6-(5-cyanopyridin-3-yl)-8-(2-methylpropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=CC(C=3C=C(C=NC=3)C#N)=NN2C=1C(C=C1C)=CC=C1C(=O)NC1CC1 HERBRAOUQDOUQV-UHFFFAOYSA-N 0.000 description 1
ITUJASTWHLGGGT-UHFFFAOYSA-N 4-[6-(5-cyanopyridin-3-yl)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)O)C3=NC=2)C=2C=C(C=NC=2)C#N)=CC=C1C(=O)NC1CC1 ITUJASTWHLGGGT-UHFFFAOYSA-N 0.000 description 1
OSOBOKHEPJHWGU-UHFFFAOYSA-N 4-[6-(benzenesulfonyl)-8-(2-methylpropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound C=1N=C2C(NCC(C)C)=CC(S(=O)(=O)C=3C=CC=CC=3)=NN2C=1C(C=C1C)=CC=C1C(=O)NC1CC1 OSOBOKHEPJHWGU-UHFFFAOYSA-N 0.000 description 1
RLPHFEWJEGFJPV-UHFFFAOYSA-N 4-[6-(benzenesulfonyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCCC(F)(F)F)C3=NC=2)S(=O)(=O)C=2C=CC=CC=2)=CC=C1C(=O)NC1CC1 RLPHFEWJEGFJPV-UHFFFAOYSA-N 0.000 description 1
ZMFQZOCBCIXENP-UHFFFAOYSA-N 4-[6-(cyclohexen-1-yl)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropylbenzenecarbothioamide Chemical compound C=1N=C2C(NCC(C)(O)C)=CC(C=3CCCCC=3)=NN2C=1C(C=C1)=CC=C1C(=S)NC1CC1 ZMFQZOCBCIXENP-UHFFFAOYSA-N 0.000 description 1
XPJJQNLAYCUBPC-UHFFFAOYSA-N 4-[6-(cyclohexen-1-yl)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound C=1N=C2C(NCC(C)(O)C)=CC(C=3CCCCC=3)=NN2C=1C1=CC=C(C=O)C=C1 XPJJQNLAYCUBPC-UHFFFAOYSA-N 0.000 description 1
UUVYDXASDGPQAS-UHFFFAOYSA-N 4-[6-(cyclohexen-1-yl)-8-[(3,3,3-trifluoro-2-hydroxypropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(O)C(F)(F)F)C3=NC=2)C=2CCCCC=2)=CC=C1C(=O)NC1CC1 UUVYDXASDGPQAS-UHFFFAOYSA-N 0.000 description 1
JGCRHEBBVXXMGE-UHFFFAOYSA-N 4-[6-(cyclohexylamino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC4CCCCC4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 JGCRHEBBVXXMGE-UHFFFAOYSA-N 0.000 description 1
LIYWCGOAMJIFMR-UHFFFAOYSA-N 4-[6-(cyclopent-3-en-1-ylamino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC4CC=CC4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 LIYWCGOAMJIFMR-UHFFFAOYSA-N 0.000 description 1
JVBSBKLIAFERKK-UHFFFAOYSA-N 4-[6-(cyclopentylamino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC4CCCC4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 JVBSBKLIAFERKK-UHFFFAOYSA-N 0.000 description 1
MRDAFIXGKSEGCZ-UHFFFAOYSA-N 4-[6-(cyclopentylamino)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC4CCCC4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 MRDAFIXGKSEGCZ-UHFFFAOYSA-N 0.000 description 1
VJJQBYKRTQFOOB-LNKIKWGQSA-N 4-[6-[(e)-but-2-en-2-yl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound N12N=C(C(/C)=C/C)C=C(NCCC(F)(F)F)C2=NC=C1C(C=C1C)=CC=C1C(=O)NC1CC1 VJJQBYKRTQFOOB-LNKIKWGQSA-N 0.000 description 1
KOWPNYTWPZHHNA-GIDUJCDVSA-N 4-[6-[(e)-but-2-en-2-yl]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound N12N=C(C(/C)=C/C)C=C(NCC(C)(C)O)C2=NC=C1C(C=C1C)=CC=C1C(=O)NC1CC1 KOWPNYTWPZHHNA-GIDUJCDVSA-N 0.000 description 1
VDUPTHPKUCCAED-GIDUJCDVSA-N 4-[6-[(e)-but-2-en-2-yl]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-3-methoxybenzamide Chemical compound C=1C=C(C=2N3N=C(C=C(NCC(C)(C)O)C3=NC=2)C(\C)=C\C)C(OC)=CC=1C(=O)NC1CC1 VDUPTHPKUCCAED-GIDUJCDVSA-N 0.000 description 1
UFZFQYHYDQOVJZ-UHFFFAOYSA-N 4-[6-[2-(hydroxymethyl)phenyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound OCC1=CC=CC=C1C1=NN2C(C=3C=CC(C=O)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 UFZFQYHYDQOVJZ-UHFFFAOYSA-N 0.000 description 1
HYQQHKSETLNNJA-UHFFFAOYSA-N 4-[6-[3-(hydroxymethyl)phenyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound OCC1=CC=CC(C2=NN3C(C=4C=CC(C=O)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 HYQQHKSETLNNJA-UHFFFAOYSA-N 0.000 description 1
GREPGBWHHDFNOJ-UHFFFAOYSA-N 4-[6-[4-(2-aminoethyl)anilino]-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(CCN)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 GREPGBWHHDFNOJ-UHFFFAOYSA-N 0.000 description 1
QAVKSGTYTPHWQZ-UHFFFAOYSA-N 4-[6-[4-chloro-2-(hydroxymethyl)phenyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCCC(F)(F)F)C3=NC=2)C=2C(=CC(Cl)=CC=2)CO)=CC=C1C(=O)NC1CC1 QAVKSGTYTPHWQZ-UHFFFAOYSA-N 0.000 description 1
NLZVXWXKGSYDHT-UHFFFAOYSA-N 4-[6-[4-chloro-2-(hydroxymethyl)phenyl]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)O)C3=NC=2)C=2C(=CC(Cl)=CC=2)CO)=CC=C1C(=O)NC1CC1 NLZVXWXKGSYDHT-UHFFFAOYSA-N 0.000 description 1
QFZGOHPWUKWRPB-UHFFFAOYSA-N 4-[6-[4-chloro-2-(hydroxymethyl)phenyl]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(Cl)=CC=4)CO)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 QFZGOHPWUKWRPB-UHFFFAOYSA-N 0.000 description 1
XVTSJKAGQGVAQR-UHFFFAOYSA-N 4-[6-[4-chloro-2-(hydroxymethyl)phenyl]sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C(=CC(Cl)=CC=4)CO)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 XVTSJKAGQGVAQR-UHFFFAOYSA-N 0.000 description 1
XTWSCTSZPHXZLC-UHFFFAOYSA-N 4-[6-anilino-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=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 XTWSCTSZPHXZLC-UHFFFAOYSA-N 0.000 description 1
AIGUAKJNKXPQIV-UHFFFAOYSA-N 4-[6-bromo-8-(4,4,4-trifluorobutylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Br)C=C(NCCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 AIGUAKJNKXPQIV-UHFFFAOYSA-N 0.000 description 1
OFFVATUZVCGJEC-UHFFFAOYSA-N 4-[6-chloro-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-3-methoxybenzamide Chemical compound C=1C=C(C=2N3N=C(Cl)C=C(NCCC(F)(F)F)C3=NC=2)C(OC)=CC=1C(=O)NC1CC1 OFFVATUZVCGJEC-UHFFFAOYSA-N 0.000 description 1
IPXASTQCKWAPIP-UHFFFAOYSA-N 4-[6-chloro-8-(3-hydroxypropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(Cl)C=C(NCCCO)C3=NC=2)=CC=C1C(=O)NC1CC1 IPXASTQCKWAPIP-UHFFFAOYSA-N 0.000 description 1
KARORNTYIKTRNK-UHFFFAOYSA-N 4-[6-chloro-8-(thiophen-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1C1=CN=C2N1N=C(Cl)C=C2NCC1=CC=CS1 KARORNTYIKTRNK-UHFFFAOYSA-N 0.000 description 1
ZRXRHFSTXSPLDM-UHFFFAOYSA-N 4-[6-chloro-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-3-methoxybenzamide Chemical compound C=1C=C(C=2N3N=C(Cl)C=C(NCC(C)(C)O)C3=NC=2)C(OC)=CC=1C(=O)NC1CC1 ZRXRHFSTXSPLDM-UHFFFAOYSA-N 0.000 description 1
FLJPRGOWKMZTFI-RBUKOAKNSA-N 4-[6-chloro-8-[[(2s)-2-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethyl]amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropylbenzamide Chemical compound O1C(C)(C)OC[C@@H]1[C@@H](O)CNC1=CC(Cl)=NN2C1=NC=C2C1=CC=C(C(=O)NC2CC2)C=C1 FLJPRGOWKMZTFI-RBUKOAKNSA-N 0.000 description 1
YLRGUGFJMHIPKK-UHFFFAOYSA-N 4-[6-cyclopentyloxy-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC4CCCC4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 YLRGUGFJMHIPKK-UHFFFAOYSA-N 0.000 description 1
JXNABYABIAVWPE-UHFFFAOYSA-N 4-[8-(2-methylpropylamino)-6-pyridin-4-ylimidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound C=1N=C2C(NCC(C)C)=CC(C=3C=CN=CC=3)=NN2C=1C1=CC=C(C=O)C=C1 JXNABYABIAVWPE-UHFFFAOYSA-N 0.000 description 1
IZEVTBSFBDBQRD-UHFFFAOYSA-N 4-[8-[(2-amino-2-methylpropyl)amino]-6-(2-methylpyrazol-3-yl)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)N)C3=NC=2)C=2N(N=CC=2)C)=CC=C1C(=O)NC1CC1 IZEVTBSFBDBQRD-UHFFFAOYSA-N 0.000 description 1
ZIOBVRJYQOMREI-UHFFFAOYSA-N 4-[8-[(2-amino-2-methylpropyl)amino]-6-(3-fluorophenyl)sulfanylimidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=C(F)C=CC=4)C=C(NCC(C)(C)N)C3=NC=2)=CC=C1C(=O)NC1CC1 ZIOBVRJYQOMREI-UHFFFAOYSA-N 0.000 description 1
OONLZOGPSBJRMX-UHFFFAOYSA-N 4-[8-[(2-amino-2-methylpropyl)amino]-6-(4-fluorophenyl)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)N)C3=NC=2)C=2C=CC(F)=CC=2)=CC=C1C(=O)NC1CC1 OONLZOGPSBJRMX-UHFFFAOYSA-N 0.000 description 1
VOSIPRDUNIJFKX-UHFFFAOYSA-N 4-[8-[(2-amino-2-methylpropyl)amino]-6-[2-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)N)C3=NC=2)C=2C(=CC=CC=2)CO)=CC=C1C(=O)NC1CC1 VOSIPRDUNIJFKX-UHFFFAOYSA-N 0.000 description 1
QONYKJTZAAGKSS-UHFFFAOYSA-N 4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-pyridin-4-ylimidazo[1,2-b]pyridazin-3-yl]benzaldehyde Chemical compound C=1N=C2C(NCC(C)(O)C)=CC(C=3C=CN=CC=3)=NN2C=1C1=CC=C(C=O)C=C1 QONYKJTZAAGKSS-UHFFFAOYSA-N 0.000 description 1
XYWIPYBIIRTJMM-IBGZPJMESA-N 4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1-yl]butanoyl]amino]-2-fluorobenzamide Chemical compound CC[C@H](N1C=C(OC)C(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(N=N1)C(F)(F)F)C(=O)NC1=CC(F)=C(C=C1)C(N)=O XYWIPYBIIRTJMM-IBGZPJMESA-N 0.000 description 1
WIFPJDJJFUSIFP-UHFFFAOYSA-N 4-aminobutane-1,2,3-triol Chemical compound NCC(O)C(O)CO WIFPJDJJFUSIFP-UHFFFAOYSA-N 0.000 description 1
NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
ITWXOEQLYFYTJX-UHFFFAOYSA-N 4-borono-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1B(O)O ITWXOEQLYFYTJX-UHFFFAOYSA-N 0.000 description 1
RVCJOGNLYVNRDN-UHFFFAOYSA-N 4-bromo-2-methylbenzoic acid Chemical compound CC1=CC(Br)=CC=C1C(O)=O RVCJOGNLYVNRDN-UHFFFAOYSA-N 0.000 description 1
KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000001826 4H-pyranyl group Chemical group O1C(=CCC=C1)* 0.000 description 1
ZKOFMMGFJURGCI-UHFFFAOYSA-N 5-[3-[4-(cyclopropylcarbamoyl)-3-methylphenyl]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-6-yl]oxypyridine-3-carboxamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(C=NC=4)C(N)=O)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 ZKOFMMGFJURGCI-UHFFFAOYSA-N 0.000 description 1
IUFLFKASIHPKNZ-UHFFFAOYSA-N 5-fluoropyridin-3-ol Chemical compound OC1=CN=CC(F)=C1 IUFLFKASIHPKNZ-UHFFFAOYSA-N 0.000 description 1
UIJCDEKRKCCYIF-UHFFFAOYSA-N 5-hydroxypyridine-3-carboxamide Chemical compound NC(=O)C1=CN=CC(O)=C1 UIJCDEKRKCCYIF-UHFFFAOYSA-N 0.000 description 1
WGVHNCAJPFIFCR-UHFFFAOYSA-N 5-methyl-1,2-dihydropyrazol-3-one Chemical compound CC1=CC(O)=NN1 WGVHNCAJPFIFCR-UHFFFAOYSA-N 0.000 description 1
YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 1
MJQSRSOTRPMVKB-UHFFFAOYSA-N 5h-imidazo[4,5-c]pyridazine Chemical compound C1=NNC2=NC=NC2=C1 MJQSRSOTRPMVKB-UHFFFAOYSA-N 0.000 description 1
OGWKCGZFUXNPDA-CFWMRBGOSA-N 5j49q6b70f Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C=O)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 OGWKCGZFUXNPDA-CFWMRBGOSA-N 0.000 description 1
WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 1
IOEAZSDEWKPTII-CRKCGEKBSA-N 6-[(e)-but-2-en-2-yl]-3-[4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]-n-(3,3,3-trifluoropropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound N12N=C(C(/C)=C/C)C=C(NCCC(F)(F)F)C2=NC=C1C(C=C1)=CC=C1C(N1)=CN=C1C1CC1 IOEAZSDEWKPTII-CRKCGEKBSA-N 0.000 description 1
USLMQUUBJVRUGX-UHFFFAOYSA-N 6-chloro-3-iodo-n-(thiophen-2-ylmethyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound C12=NC=C(I)N2N=C(Cl)C=C1NCC1=CC=CS1 USLMQUUBJVRUGX-UHFFFAOYSA-N 0.000 description 1
OTRFLZUSZAVLKP-UHFFFAOYSA-N 6-chloro-3-iodo-n-[(2-methyloxolan-2-yl)methyl]imidazo[1,2-b]pyridazin-8-amine Chemical compound C=1C(Cl)=NN2C(I)=CN=C2C=1NCC1(C)CCCO1 OTRFLZUSZAVLKP-UHFFFAOYSA-N 0.000 description 1
XXFLFPDHUCPEPP-UHFFFAOYSA-N 6-cyclopentyloxy-n-(3,3,3-trifluoropropyl)imidazo[1,2-b]pyridazin-8-amine Chemical compound N=1N2C=CN=C2C(NCCC(F)(F)F)=CC=1OC1CCCC1 XXFLFPDHUCPEPP-UHFFFAOYSA-N 0.000 description 1
UUVDJIWRSIJEBS-UHFFFAOYSA-N 6-methoxypyridin-3-amine Chemical compound COC1=CC=C(N)C=N1 UUVDJIWRSIJEBS-UHFFFAOYSA-N 0.000 description 1
DHLUJPLHLZJUBW-UHFFFAOYSA-N 6-methylpyridin-3-ol Chemical compound CC1=CC=C(O)C=N1 DHLUJPLHLZJUBW-UHFFFAOYSA-N 0.000 description 1
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 1
LZEJQXOCRMRVNP-UHFFFAOYSA-N 8-bromo-6-chloroimidazo[1,2-b]pyridazine Chemical compound N1=C(Cl)C=C(Br)C2=NC=CN21 LZEJQXOCRMRVNP-UHFFFAOYSA-N 0.000 description 1
ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
208000024827 Alzheimer disease Diseases 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
101100439662 Arabidopsis thaliana CHR5 gene Proteins 0.000 description 1
108010006654 Bleomycin Proteins 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
229910014585 C2-Ce Inorganic materials 0.000 description 1
101100326430 Caenorhabditis elegans bub-1 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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 description 1
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 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
102100025832 Centromere-associated protein E Human genes 0.000 description 1
108091060290 Chromatid Proteins 0.000 description 1
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 description 1
108010022152 Corticotropin-Releasing Hormone Proteins 0.000 description 1
241000938605 Crocodylia Species 0.000 description 1
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
206010059866 Drug resistance Diseases 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
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 description 1
125000002842 L-seryl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])O[H] 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
102000001291 MAP Kinase Kinase Kinase Human genes 0.000 description 1
102000043136 MAP kinase family Human genes 0.000 description 1
108091054455 MAP kinase family Proteins 0.000 description 1
108060006687 MAP kinase kinase kinase Proteins 0.000 description 1
102000029749 Microtubule Human genes 0.000 description 1
108091022875 Microtubule Proteins 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
208000031888 Mycoses Diseases 0.000 description 1
FEYNFHSRETUBEM-UHFFFAOYSA-N N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide Chemical compound COc1ccc(cc1)N1N=C(C)C(C(=O)Nc2cccc(c2)C(C)(F)F)C1=O FEYNFHSRETUBEM-UHFFFAOYSA-N 0.000 description 1
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
UALORLCYRCEIME-IBGZPJMESA-N N-cyclopropyl-2-methyl-4-[6-(2-methylpyrazol-3-yl)-8-[[(2S)-oxolan-2-yl]methylamino]imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NC[C@H]4OCCC4)C3=NC=2)C=2N(N=CC=2)C)=CC=C1C(=O)NC1CC1 UALORLCYRCEIME-IBGZPJMESA-N 0.000 description 1
JNNBAAUFKRFXHP-UHFFFAOYSA-N N-cyclopropyl-2-methyl-4-[8-[(2-methyloxolan-2-yl)methylamino]-6-pyridin-4-ylimidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC4(C)OCCC4)C3=NC=2)C=2C=CN=CC=2)=CC=C1C(=O)NC1CC1 JNNBAAUFKRFXHP-UHFFFAOYSA-N 0.000 description 1
GMOFUGLLPMZVFN-UHFFFAOYSA-N N-cyclopropyl-3-hydroxy-4-[6-phenylsulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound OC1=CC(C(=O)NC2CC2)=CC=C1C(N1N=2)=CN=C1C(NCCC(F)(F)F)=CC=2SC1=CC=CC=C1 GMOFUGLLPMZVFN-UHFFFAOYSA-N 0.000 description 1
CNSUPAYXOZACOU-UHFFFAOYSA-N N-cyclopropyl-3-hydroxy-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-phenylsulfanylimidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound N=1N2C(C=3C(=CC(=CC=3)C(=O)NC3CC3)O)=CN=C2C(NCC(C)(O)C)=CC=1SC1=CC=CC=C1 CNSUPAYXOZACOU-UHFFFAOYSA-N 0.000 description 1
QISDGGVOHVSRNQ-UHFFFAOYSA-N N-cyclopropyl-4-[6-(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=CC=4)O)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 QISDGGVOHVSRNQ-UHFFFAOYSA-N 0.000 description 1
YCVDQRSIDGEBNR-UHFFFAOYSA-N N-cyclopropyl-4-[6-(2-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(=CC=CC=4)O)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 YCVDQRSIDGEBNR-UHFFFAOYSA-N 0.000 description 1
ZGMSTIQIVPFMGN-UHFFFAOYSA-N N-cyclopropyl-4-[6-(3-fluorophenyl)sulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-3-hydroxybenzamide Chemical compound OC1=CC(C(=O)NC2CC2)=CC=C1C(N1N=2)=CN=C1C(NCCC(F)(F)F)=CC=2SC1=CC=CC(F)=C1 ZGMSTIQIVPFMGN-UHFFFAOYSA-N 0.000 description 1
UQJUYVTZNOCGMF-UHFFFAOYSA-N N-cyclopropyl-4-[6-(3-fluorophenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-3-hydroxybenzamide Chemical compound N=1N2C(C=3C(=CC(=CC=3)C(=O)NC3CC3)O)=CN=C2C(NCC(C)(O)C)=CC=1SC1=CC=CC(F)=C1 UQJUYVTZNOCGMF-UHFFFAOYSA-N 0.000 description 1
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 description 1
YRIFVGQSZKENTE-UHFFFAOYSA-N N-cyclopropyl-4-[8-[(1,1-dioxothian-4-yl)methylamino]-6-(3-fluorophenyl)sulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=C(F)C=CC=4)C=C(NCC4CCS(=O)(=O)CC4)C3=NC=2)=CC=C1C(=O)NC1CC1 YRIFVGQSZKENTE-UHFFFAOYSA-N 0.000 description 1
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 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
101100258328 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-2 gene Proteins 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
241001494479 Pecora Species 0.000 description 1
241000009328 Perro Species 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
241000283984 Rodentia Species 0.000 description 1
BFZKMNSQCNVFGM-UCEYFQQTSA-N Sagopilone Chemical compound O1C(=O)C[C@H](O)C(C)(C)C(=O)[C@H](CC=C)[C@@H](O)[C@@H](C)CCC[C@@]2(C)O[C@H]2C[C@H]1C1=CC=C(SC(C)=N2)C2=C1 BFZKMNSQCNVFGM-UCEYFQQTSA-N 0.000 description 1
206010039491 Sarcoma Diseases 0.000 description 1
108010077895 Sarcosine Proteins 0.000 description 1
238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 1
SWEDAZLCYJDAGW-UHFFFAOYSA-N Thiophene-2-thiol Chemical compound SC1=CC=CS1 SWEDAZLCYJDAGW-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
241000251539 Vertebrata <Metazoa> Species 0.000 description 1
229940122803 Vinca alkaloid Drugs 0.000 description 1
YNOGYQAEJGADFJ-RXMQYKEDSA-N [(2r)-oxolan-2-yl]methanamine Chemical compound NC[C@H]1CCCO1 YNOGYQAEJGADFJ-RXMQYKEDSA-N 0.000 description 1
YNOGYQAEJGADFJ-YFKPBYRVSA-N [(2s)-oxolan-2-yl]methanamine Chemical compound NC[C@@H]1CCCO1 YNOGYQAEJGADFJ-YFKPBYRVSA-N 0.000 description 1
XPUNXPPXMANQGF-UHFFFAOYSA-N [2-methyl-5-(trifluoromethyl)pyrazol-3-yl]boronic acid Chemical compound CN1N=C(C(F)(F)F)C=C1B(O)O XPUNXPPXMANQGF-UHFFFAOYSA-N 0.000 description 1
HGTDLKXUWVKLQX-UHFFFAOYSA-N [3-(hydroxymethyl)phenyl]boronic acid Chemical compound OCC1=CC=CC(B(O)O)=C1 HGTDLKXUWVKLQX-UHFFFAOYSA-N 0.000 description 1
QHMZFIHGASQDNZ-UHFFFAOYSA-N [4-(2-cyclopropyl-1h-imidazol-5-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CN=C(C2CC2)N1 QHMZFIHGASQDNZ-UHFFFAOYSA-N 0.000 description 1
QJYYVSIRDJVQJW-UHFFFAOYSA-N [4-(dimethylcarbamoyl)phenyl]boronic acid Chemical compound CN(C)C(=O)C1=CC=C(B(O)O)C=C1 QJYYVSIRDJVQJW-UHFFFAOYSA-N 0.000 description 1
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
230000004913 activation Effects 0.000 description 1
125000005042 acyloxymethyl group Chemical group 0.000 description 1
229940009456 adriamycin Drugs 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000004849 alkoxymethyl group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
208000036878 aneuploidy Diseases 0.000 description 1
231100001075 aneuploidy Toxicity 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
125000005427 anthranyl group Chemical group 0.000 description 1
230000002280 anti-androgenic effect Effects 0.000 description 1
239000000051 antiandrogen Substances 0.000 description 1
239000003080 antimitotic agent Substances 0.000 description 1
230000006907 apoptotic process Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
125000002393 azetidinyl group Chemical group 0.000 description 1
125000004931 azocinyl group Chemical group N1=C(C=CC=CC=C1)* 0.000 description 1
230000008901 benefit Effects 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
229960000997 bicalutamide Drugs 0.000 description 1
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
229960001561 bleomycin Drugs 0.000 description 1
OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
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 description 1
229960001467 bortezomib Drugs 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229960004117 capecitabine Drugs 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
VZSXFJPZOCRDPW-UHFFFAOYSA-N carbanide;trioxorhenium Chemical compound [CH3-].O=[Re](=O)=O VZSXFJPZOCRDPW-UHFFFAOYSA-N 0.000 description 1
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
229960004562 carboplatin Drugs 0.000 description 1
125000001721 carboxyacetyl group Chemical group 0.000 description 1
231100000504 carcinogenesis Toxicity 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
230000034303 cell budding Effects 0.000 description 1
230000022131 cell cycle Effects 0.000 description 1
230000023359 cell cycle switching, meiotic to mitotic cell cycle Effects 0.000 description 1
108010031379 centromere protein E Proteins 0.000 description 1
DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 1
239000013000 chemical inhibitor Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
235000013330 chicken meat Nutrition 0.000 description 1
229960004630 chlorambucil Drugs 0.000 description 1
JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
KQIADDMXRMTWHZ-UHFFFAOYSA-N chloro-tri(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)C(C)C KQIADDMXRMTWHZ-UHFFFAOYSA-N 0.000 description 1
210000004756 chromatid Anatomy 0.000 description 1
230000002759 chromosomal effect Effects 0.000 description 1
230000024321 chromosome segregation Effects 0.000 description 1
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
229960004316 cisplatin Drugs 0.000 description 1
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
238000002648 combination therapy Methods 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000006880 cross-coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
LJSBEPFUQWPNBZ-UHFFFAOYSA-N cyclopent-3-en-1-amine Chemical compound NC1CC=CC1 LJSBEPFUQWPNBZ-UHFFFAOYSA-N 0.000 description 1
XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
229960004397 cyclophosphamide Drugs 0.000 description 1
JRYOZJIRAVZGMV-UHFFFAOYSA-N cyclopropanecarboximidamide;hydron;chloride Chemical compound Cl.NC(=N)C1CC1 JRYOZJIRAVZGMV-UHFFFAOYSA-N 0.000 description 1
UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 description 1
229960000978 cyproterone acetate Drugs 0.000 description 1
229960000684 cytarabine Drugs 0.000 description 1
230000021953 cytokinesis Effects 0.000 description 1
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin 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(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 1
229960000975 daunorubicin Drugs 0.000 description 1
230000007423 decrease Effects 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000002950 deficient Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
229960003957 dexamethasone Drugs 0.000 description 1
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 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
125000005117 dialkylcarbamoyl group Chemical group 0.000 description 1
125000005959 diazepanyl group Chemical group 0.000 description 1
LMEDOLJKVASKTP-UHFFFAOYSA-N dibutyl sulfate Chemical compound CCCCOS(=O)(=O)OCCCC LMEDOLJKVASKTP-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 1
125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 description 1
125000005046 dihydronaphthyl group Chemical group 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 1
108700003601 dimethylglycine Proteins 0.000 description 1
GAFRWLVTHPVQGK-UHFFFAOYSA-N dipentyl sulfate Chemical class CCCCCOS(=O)(=O)OCCCCC GAFRWLVTHPVQGK-UHFFFAOYSA-N 0.000 description 1
GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
125000005883 dithianyl group Chemical group 0.000 description 1
229960003668 docetaxel Drugs 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229960004679 doxorubicin Drugs 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
238000000132 electrospray ionisation Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
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 description 1
HESCAJZNRMSMJG-HGYUPSKWSA-N epothilone A Natural products O=C1[C@H](C)[C@H](O)[C@H](C)CCC[C@H]2O[C@H]2C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C HESCAJZNRMSMJG-HGYUPSKWSA-N 0.000 description 1
QXRSDHAAWVKZLJ-PVYNADRNSA-N epothilone B Chemical compound C/C([C@@H]1C[C@@H]2O[C@]2(C)CCC[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 QXRSDHAAWVKZLJ-PVYNADRNSA-N 0.000 description 1
150000003883 epothilone derivatives Chemical class 0.000 description 1
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 description 1
229940031098 ethanolamine Drugs 0.000 description 1
VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
229960005420 etoposide Drugs 0.000 description 1
229960004979 fampridine Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
229960000390 fludarabine Drugs 0.000 description 1
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 description 1
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
229960002949 fluorouracil Drugs 0.000 description 1
MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
229960002074 flutamide Drugs 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
229960002442 glucosamine Drugs 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
229960001867 guaiacol Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229960000908 idarubicin Drugs 0.000 description 1
HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 1
229960001101 ifosfamide Drugs 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000007943 implant Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
230000006882 induction of apoptosis Effects 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
150000002485 inorganic esters Chemical class 0.000 description 1
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
FABUFPQFXZVHFB-CFWQTKTJSA-N ixabepilone Chemical compound C/C([C@@H]1C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@H](C)C(=O)C(C)(C)[C@H](O)CC(=O)N1)O)C)=C\C1=CSC(C)=N1 FABUFPQFXZVHFB-CFWQTKTJSA-N 0.000 description 1
229960002014 ixabepilone Drugs 0.000 description 1
239000003446 ligand Substances 0.000 description 1
NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
BPHQBQAJVFDYRF-UHFFFAOYSA-M magnesium;ethenylbenzene;bromide Chemical compound [Mg+2].[Br-].C=[C-]C1=CC=CC=C1 BPHQBQAJVFDYRF-UHFFFAOYSA-M 0.000 description 1
230000036210 malignancy Effects 0.000 description 1
238000007726 management method Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 1
229960001924 melphalan Drugs 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229960000485 methotrexate Drugs 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
ATVCAUUSVKIWJW-UHFFFAOYSA-N methyl 2-[3-[4-(cyclopropylcarbamoyl)-3-methylphenyl]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-6-yl]-5-fluorobenzoate Chemical compound COC(=O)C1=CC(F)=CC=C1C1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 ATVCAUUSVKIWJW-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
210000004688 microtubule Anatomy 0.000 description 1
230000008880 microtubule cytoskeleton organization Effects 0.000 description 1
230000006618 mitotic catastrophe Effects 0.000 description 1
229960001156 mitoxantrone Drugs 0.000 description 1
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 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940078490 n,n-dimethylglycine Drugs 0.000 description 1
FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
VFBILHPIHUPBPZ-UHFFFAOYSA-N n-[[2-[4-(difluoromethoxy)-3-propan-2-yloxyphenyl]-1,3-oxazol-4-yl]methyl]-2-ethoxybenzamide Chemical compound CCOC1=CC=CC=C1C(=O)NCC1=COC(C=2C=C(OC(C)C)C(OC(F)F)=CC=2)=N1 VFBILHPIHUPBPZ-UHFFFAOYSA-N 0.000 description 1
DOWVMJFBDGWVML-UHFFFAOYSA-N n-cyclohexyl-n-methyl-4-(1-oxidopyridin-1-ium-3-yl)imidazole-1-carboxamide Chemical compound C1=NC(C=2C=[N+]([O-])C=CC=2)=CN1C(=O)N(C)C1CCCCC1 DOWVMJFBDGWVML-UHFFFAOYSA-N 0.000 description 1
OFPVNGDNAMSUHG-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(1-phenylethenyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCCC(F)(F)F)C3=NC=2)C(=C)C=2C=CC=CC=2)=CC=C1C(=O)NC1CC1 OFPVNGDNAMSUHG-UHFFFAOYSA-N 0.000 description 1
WNMZUFQOWFIXGW-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(2,2,3,3-tetrafluoro-4-hydroxybutoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(OCC(F)(F)C(F)(F)CO)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 WNMZUFQOWFIXGW-UHFFFAOYSA-N 0.000 description 1
DKTIRGIKIDKSAJ-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(2-methylpyrazol-3-yl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCCC(F)(F)F)C3=NC=2)C=2N(N=CC=2)C)=CC=C1C(=O)NC1CC1 DKTIRGIKIDKSAJ-UHFFFAOYSA-N 0.000 description 1
CANYVRITYBPCSP-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(2-methylpyrazol-3-yl)-8-[(3,3,3-trifluoro-2-hydroxypropyl)amino]imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(O)C(F)(F)F)C3=NC=2)C=2N(N=CC=2)C)=CC=C1C(=O)NC1CC1 CANYVRITYBPCSP-UHFFFAOYSA-N 0.000 description 1
UALORLCYRCEIME-LJQANCHMSA-N n-cyclopropyl-2-methyl-4-[6-(2-methylpyrazol-3-yl)-8-[[(2r)-oxolan-2-yl]methylamino]imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NC[C@@H]4OCCC4)C3=NC=2)C=2N(N=CC=2)C)=CC=C1C(=O)NC1CC1 UALORLCYRCEIME-LJQANCHMSA-N 0.000 description 1
LGDIKVFBMZOYMI-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(2-morpholin-4-ylethylsulfanyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(SCCN4CCOCC4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 LGDIKVFBMZOYMI-UHFFFAOYSA-N 0.000 description 1
YXCQVWFWOHCQKN-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(3-methylanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC=CC(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 YXCQVWFWOHCQKN-UHFFFAOYSA-N 0.000 description 1
FCZFRWCOTVFGBS-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(3-propan-2-ylanilino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC(C)C1=CC=CC(NC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 FCZFRWCOTVFGBS-UHFFFAOYSA-N 0.000 description 1
GXKSEQCLUVRCIW-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(pyridin-3-ylamino)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C=NC=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 GXKSEQCLUVRCIW-UHFFFAOYSA-N 0.000 description 1
GFNLLXMSXDIRMB-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-[(4-methyl-1,2,4-triazol-3-yl)sulfanyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(SC=4N(C=NN=4)C)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 GFNLLXMSXDIRMB-UHFFFAOYSA-N 0.000 description 1
JBMMAOWLEIVNJM-YBFXNURJSA-N n-cyclopropyl-2-methyl-4-[6-[(e)-2,3,3-trifluoro-4-hydroxybut-1-enoxy]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(O\C=C(\F)C(F)(F)CO)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 JBMMAOWLEIVNJM-YBFXNURJSA-N 0.000 description 1
NCYCTKIJPPGLBI-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-[4-(trifluoromethyl)phenyl]sulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=CC(=CC=4)C(F)(F)F)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 NCYCTKIJPPGLBI-UHFFFAOYSA-N 0.000 description 1
IDNQTCZTYUNJGY-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-methylsulfanyl-8-(2-morpholin-4-ylsulfonylethylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound C12=NC=C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)N2N=C(SC)C=C1NCCS(=O)(=O)N1CCOCC1 IDNQTCZTYUNJGY-UHFFFAOYSA-N 0.000 description 1
ASGTXDHKYSHFRS-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-methylsulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound N12N=C(SC)C=C(NCCC(F)(F)F)C2=NC=C1C(C=C1C)=CC=C1C(=O)NC1CC1 ASGTXDHKYSHFRS-UHFFFAOYSA-N 0.000 description 1
NLFTZWAMPZBBDC-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-methylsulfanyl-8-[(3,3,3-trifluoro-2-hydroxypropyl)amino]imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound N12N=C(SC)C=C(NCC(O)C(F)(F)F)C2=NC=C1C(C=C1C)=CC=C1C(=O)NC1CC1 NLFTZWAMPZBBDC-UHFFFAOYSA-N 0.000 description 1
RLBSJCXVCVKAOX-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-phenylsulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=CC=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 RLBSJCXVCVKAOX-UHFFFAOYSA-N 0.000 description 1
CEWRUGYCGXGDCJ-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-phenylsulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzenecarbothioamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=CC=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=S)NC1CC1 CEWRUGYCGXGDCJ-UHFFFAOYSA-N 0.000 description 1
URWCQYRJNVWADI-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-phenylsulfanyl-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=CC=CC=4)C=C(NCC4CCSCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 URWCQYRJNVWADI-UHFFFAOYSA-N 0.000 description 1
FDFTYSCILBZFPU-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-pyrazin-2-ylsulfanyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(SC=4N=CC=NC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 FDFTYSCILBZFPU-UHFFFAOYSA-N 0.000 description 1
UHEMBCPSXXTMKO-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-pyridin-4-yl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCCC(F)(F)F)C3=NC=2)C=2C=CN=CC=2)=CC=C1C(=O)NC1CC1 UHEMBCPSXXTMKO-UHFFFAOYSA-N 0.000 description 1
KNSCNGSTNBUZGW-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[8-(2-methylpropylamino)-6-(1h-pyrazol-5-yl)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=CC(C=3NN=CC=3)=NN2C=1C(C=C1C)=CC=C1C(=O)NC1CC1 KNSCNGSTNBUZGW-UHFFFAOYSA-N 0.000 description 1
XUEUCRPTCHXOQI-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[8-(2-methylpropylamino)-6-(2-methylpyrazol-3-yl)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=CC(C=3N(N=CC=3)C)=NN2C=1C(C=C1C)=CC=C1C(=O)NC1CC1 XUEUCRPTCHXOQI-UHFFFAOYSA-N 0.000 description 1
SSYGPINEHJALJE-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[8-(2-methylpropylamino)-6-(oxolan-2-ylmethylsulfanyl)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)C)=CC=1SCC1CCCO1 SSYGPINEHJALJE-UHFFFAOYSA-N 0.000 description 1
UCSDECHVQRMBBV-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[8-(2-methylpropylamino)-6-methylsulfanylimidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound N12N=C(SC)C=C(NCC(C)C)C2=NC=C1C(C=C1C)=CC=C1C(=O)NC1CC1 UCSDECHVQRMBBV-UHFFFAOYSA-N 0.000 description 1
SYXGHDYWQDFZJZ-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[8-(2-methylpropylamino)-6-propylsulfanylimidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound N12N=C(SCCC)C=C(NCC(C)C)C2=NC=C1C(C=C1C)=CC=C1C(=O)NC1CC1 SYXGHDYWQDFZJZ-UHFFFAOYSA-N 0.000 description 1
ZUEDKJFQTDYJRO-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[8-(oxan-2-ylmethylamino)-6-pyridin-4-ylimidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC4OCCCC4)C3=NC=2)C=2C=CN=CC=2)=CC=C1C(=O)NC1CC1 ZUEDKJFQTDYJRO-UHFFFAOYSA-N 0.000 description 1
ZCAUJYZBKNIOET-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[8-[(2-methylpyrazol-3-yl)methylamino]-6-methylsulfanylimidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound C12=NC=C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)N2N=C(SC)C=C1NCC1=CC=NN1C ZCAUJYZBKNIOET-UHFFFAOYSA-N 0.000 description 1
HKWKVEHNGKQPGI-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[8-[(4-methylmorpholin-2-yl)methylamino]-6-phenylsulfanylimidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound C1N(C)CCOC1CNC1=CC(SC=2C=CC=CC=2)=NN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 HKWKVEHNGKQPGI-UHFFFAOYSA-N 0.000 description 1
DTJLIMGDXVTLJY-OAQYLSRUSA-N n-cyclopropyl-2-methyl-4-[8-[[(2r)-oxolan-2-yl]methylamino]-6-pyridin-4-ylimidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NC[C@@H]4OCCC4)C3=NC=2)C=2C=CN=CC=2)=CC=C1C(=O)NC1CC1 DTJLIMGDXVTLJY-OAQYLSRUSA-N 0.000 description 1
DTJLIMGDXVTLJY-NRFANRHFSA-N n-cyclopropyl-2-methyl-4-[8-[[(2s)-oxolan-2-yl]methylamino]-6-pyridin-4-ylimidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NC[C@H]4OCCC4)C3=NC=2)C=2C=CN=CC=2)=CC=C1C(=O)NC1CC1 DTJLIMGDXVTLJY-NRFANRHFSA-N 0.000 description 1
NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
VTSMZDCBCYFERV-UHFFFAOYSA-N n-cyclopropyl-3-methoxy-4-[6-(2-methylpyrazol-3-yl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound COC1=CC(C(=O)NC2CC2)=CC=C1C(N1N=2)=CN=C1C(NCCC(F)(F)F)=CC=2C1=CC=NN1C VTSMZDCBCYFERV-UHFFFAOYSA-N 0.000 description 1
HYIISDRAVCTNTL-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,3-difluoroanilino)-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)F)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 HYIISDRAVCTNTL-UHFFFAOYSA-N 0.000 description 1
ZEXPCJVXYGXKFV-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,3-difluoroanilino)-8-(4,4,4-trifluorobutylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC=4C(=C(F)C=CC=4)F)C=C(NCCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 ZEXPCJVXYGXKFV-UHFFFAOYSA-N 0.000 description 1
AEYNNGACQVWQPP-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,3-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=CC=4)F)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 AEYNNGACQVWQPP-UHFFFAOYSA-N 0.000 description 1
ZTOKZZGJCXDBRP-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,3-difluorophenyl)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)F)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 ZTOKZZGJCXDBRP-UHFFFAOYSA-N 0.000 description 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 description 1
ZYHHNLOMNTWFLX-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,5-difluorophenyl)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=C(F)C=4)F)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 ZYHHNLOMNTWFLX-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
SQMYSSVJDUSMPP-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-4-methoxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound FC1=CC(OC)=CC=C1OC1=NN2C(C=3C=CC(=CC=3)C(=O)NC3CC3)=CN=C2C(NCCC(F)(F)F)=C1 SQMYSSVJDUSMPP-UHFFFAOYSA-N 0.000 description 1
XGGOILXUXRIANY-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-4-methoxyphenoxy)-8-(oxan-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound FC1=CC(OC)=CC=C1OC1=NN2C(C=3C=CC(=CC=3)C(=O)NC3CC3)=CN=C2C(NCC2CCOCC2)=C1 XGGOILXUXRIANY-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 1
ZEKKQMBCBLERGJ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluorophenyl)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)O)C3=NC=2)C=2C(=CC=CC=2)F)=CC=C1C(=O)NC1CC1 ZEKKQMBCBLERGJ-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
XUGGMPAODGQCLJ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-hydroxycyclohexyl)oxy-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC4C(CCCC4)O)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 XUGGMPAODGQCLJ-UHFFFAOYSA-N 0.000 description 1
KVEXUTPEPUOJCU-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-hydroxyethylsulfanyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SCCO)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 KVEXUTPEPUOJCU-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 1
ZWOVKZYEDKWKAV-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-methylpyrazol-3-yl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzenecarbothioamide Chemical compound CN1N=CC=C1C1=NN2C(C=3C=CC(=CC=3)C(=S)NC3CC3)=CN=C2C(NCCC(F)(F)F)=C1 ZWOVKZYEDKWKAV-UHFFFAOYSA-N 0.000 description 1
JPKPOUUAUJTTRU-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,3-dimethylbutylsulfanyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SCCC(C)(C)C)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 JPKPOUUAUJTTRU-UHFFFAOYSA-N 0.000 description 1
GTPQIXUIWBDJEU-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,3-dimethylbutylsulfanyl)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SCCC(C)(C)C)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 GTPQIXUIWBDJEU-UHFFFAOYSA-N 0.000 description 1
AMKKYTQGYPLNJO-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,4-difluoroanilino)-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(F)=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 AMKKYTQGYPLNJO-UHFFFAOYSA-N 0.000 description 1
KFQAPOJIIVUKHL-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,4-difluoroanilino)-8-(4,4,4-trifluorobutylamino)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(NCCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 KFQAPOJIIVUKHL-UHFFFAOYSA-N 0.000 description 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 description 1
XELNLIDYYQAKDW-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,4-difluorophenyl)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(F)=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 XELNLIDYYQAKDW-UHFFFAOYSA-N 0.000 description 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 description 1
FIGJQQYJEDVCHZ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,5-difluoroanilino)-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=C(F)C=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 FIGJQQYJEDVCHZ-UHFFFAOYSA-N 0.000 description 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 description 1
GVSNOJJMQKMUOP-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,5-difluorophenyl)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=C(F)C=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 GVSNOJJMQKMUOP-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 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 description 1
YZKGLZCDHCZPIY-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-5-methylanilino)-8-(3,3,3-trifluoropropylamino)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(NCCC(F)(F)F)=C2)=C1 YZKGLZCDHCZPIY-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 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 description 1
IVZUAYBIWHAZLH-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound FC1=CC=CC(OC2=NN3C(C=4C=CC(=CC=4)C(=O)NC4CC4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 IVZUAYBIWHAZLH-UHFFFAOYSA-N 0.000 description 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 description 1
QUJDHHPFEDLQSQ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenyl)sulfanyl-8-(2-hydroxyethylamino)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(NCCO)C3=NC=2)=CC=C1C(=O)NC1CC1 QUJDHHPFEDLQSQ-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
DPTJGSZOGMYGQP-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenyl)sulfanyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CC2)=CC=C1C(N1N=2)=CN=C1C(NCC(C)(C)O)=CC=2SC1=CC=CC(F)=C1 DPTJGSZOGMYGQP-UHFFFAOYSA-N 0.000 description 1
LFIFMUAVMQQIRB-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenyl)sulfanyl-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=1SC1=CC=CC(F)=C1 LFIFMUAVMQQIRB-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 1
LMIBPOONXQTZJD-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-hydroxyphenyl)sulfanyl-8-(thian-4-ylmethylamino)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(NCC4CCSCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 LMIBPOONXQTZJD-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
MOINPJAUCUUOPE-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluoro-2-methylphenyl)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)O)C3=NC=2)C=2C(=CC(F)=CC=2)C)=CC=C1C(=O)NC1CC1 MOINPJAUCUUOPE-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 1
OCJUNGZNQYXJFL-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluorophenyl)-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)C=2C=CC(F)=CC=2)=CC=C1C(=O)NC1CC1 OCJUNGZNQYXJFL-UHFFFAOYSA-N 0.000 description 1
RNNKRNRRFLGZDJ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluorophenyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CC2)=CC=C1C(N1N=2)=CN=C1C(NCCC(F)(F)F)=CC=2C1=CC=C(F)C=C1 RNNKRNRRFLGZDJ-UHFFFAOYSA-N 0.000 description 1
OAXILSCMYSFHIK-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluorophenyl)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)O)C3=NC=2)C=2C=CC(F)=CC=2)=CC=C1C(=O)NC1CC1 OAXILSCMYSFHIK-UHFFFAOYSA-N 0.000 description 1
JZTXJUABQDUWIL-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluorophenyl)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CC2)=CC=C1C(N1N=2)=CN=C1C(NCC(C)(C)O)=CC=2C1=CC=C(F)C=C1 JZTXJUABQDUWIL-UHFFFAOYSA-N 0.000 description 1
KFXMPTHGQFUILS-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluorophenyl)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)(O)C)=CC(C=3C=CC(F)=CC=3)=NN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 KFXMPTHGQFUILS-UHFFFAOYSA-N 0.000 description 1
UJEXLJPVWMLXCZ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluorophenyl)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]benzenecarbothioamide Chemical compound C=1N=C2C(NCC(C)(O)C)=CC(C=3C=CC(F)=CC=3)=NN2C=1C(C=C1)=CC=C1C(=S)NC1CC1 UJEXLJPVWMLXCZ-UHFFFAOYSA-N 0.000 description 1
MRJPPIAXYWTEPK-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluorophenyl)-8-[(4-methylmorpholin-2-yl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1N(C)CCOC1CNC1=CC(C=2C=CC(F)=CC=2)=NN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 MRJPPIAXYWTEPK-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 1
JHUAYRUMDIFJCK-UHFFFAOYSA-N n-cyclopropyl-4-[6-[(2,2-difluorocyclopropyl)methoxy]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OCC4C(C4)(F)F)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 JHUAYRUMDIFJCK-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 1
FSJLCXWWRDNWAU-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(diethylamino)ethylsulfanyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N12N=C(SCCN(CC)CC)C=C(NCCC(F)(F)F)C2=NC=C1C(C=C1C)=CC=C1C(=O)NC1CC1 FSJLCXWWRDNWAU-UHFFFAOYSA-N 0.000 description 1
BQLVEWBZELLHRJ-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(fluoromethyl)phenyl]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)O)C3=NC=2)C=2C(=CC=CC=2)CF)=CC=C1C(=O)NC1CC1 BQLVEWBZELLHRJ-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
LWMSYEFPCMQVGB-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(hydroxymethyl)phenyl]-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)C=2C(=CC=CC=2)CO)=CC=C1C(=O)NC1CC1 LWMSYEFPCMQVGB-UHFFFAOYSA-N 0.000 description 1
SJVJVSOIXIAFCS-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(hydroxymethyl)phenyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CC2)=CC=C1C(N1N=2)=CN=C1C(NCCC(F)(F)F)=CC=2C1=CC=CC=C1CO SJVJVSOIXIAFCS-UHFFFAOYSA-N 0.000 description 1
MKLXPSBHNPSULS-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(hydroxymethyl)phenyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzenecarbothioamide Chemical compound OCC1=CC=CC=C1C1=NN2C(C=3C=CC(=CC=3)C(=S)NC3CC3)=CN=C2C(NCCC(F)(F)F)=C1 MKLXPSBHNPSULS-UHFFFAOYSA-N 0.000 description 1
SDPJOMZKTQVEMZ-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(hydroxymethyl)phenyl]-8-[(2-methoxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C=1N=C2C(NCC(C)(C)OC)=CC(C=3C(=CC=CC=3)CO)=NN2C=1C(C=C1C)=CC=C1C(=O)NC1CC1 SDPJOMZKTQVEMZ-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
YEKQVCLABMLUOM-UHFFFAOYSA-N n-cyclopropyl-4-[6-[3-(hydroxymethyl)phenyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzenecarbothioamide Chemical compound OCC1=CC=CC(C2=NN3C(C=4C=CC(=CC=4)C(=S)NC4CC4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 YEKQVCLABMLUOM-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
RXKAUSYGRJGCFY-UHFFFAOYSA-N n-cyclopropyl-4-[6-[4-fluoro-2-(hydroxymethyl)phenyl]-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)C=2C(=CC(F)=CC=2)CO)=CC=C1C(=O)NC1CC1 RXKAUSYGRJGCFY-UHFFFAOYSA-N 0.000 description 1
OTSWUFHREJJWMK-UHFFFAOYSA-N n-cyclopropyl-4-[6-[4-fluoro-2-(hydroxymethyl)phenyl]-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)O)C3=NC=2)C=2C(=CC(F)=CC=2)CO)=CC=C1C(=O)NC1CC1 OTSWUFHREJJWMK-UHFFFAOYSA-N 0.000 description 1
DNYPVHNKIWEEPT-UHFFFAOYSA-N n-cyclopropyl-4-[6-cyclopropyl-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)C2CC2)=CC=C1C(=O)NC1CC1 DNYPVHNKIWEEPT-UHFFFAOYSA-N 0.000 description 1
ORJJXZHQVHHTKU-UHFFFAOYSA-N n-cyclopropyl-4-[6-ethenyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 ORJJXZHQVHHTKU-UHFFFAOYSA-N 0.000 description 1
YJMMXWVMQFWKIX-UHFFFAOYSA-N n-cyclopropyl-4-[6-ethenyl-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 YJMMXWVMQFWKIX-UHFFFAOYSA-N 0.000 description 1
QFLARDWDIRLBHR-UHFFFAOYSA-N n-cyclopropyl-4-[8-(1,4-dioxan-2-ylmethylamino)-6-pyridin-4-ylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC4OCCOC4)C3=NC=2)C=2C=CN=CC=2)=CC=C1C(=O)NC1CC1 QFLARDWDIRLBHR-UHFFFAOYSA-N 0.000 description 1
NBOSOSLGMGQVTG-UHFFFAOYSA-N n-cyclopropyl-4-[8-(2-methylpropylamino)-6-methylsulfonylimidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)C)=CC(S(C)(=O)=O)=NN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 NBOSOSLGMGQVTG-UHFFFAOYSA-N 0.000 description 1
PYCWYALYEPASEN-UHFFFAOYSA-N n-cyclopropyl-4-[8-(2-methylpropylamino)-6-pyridin-4-ylimidazo[1,2-b]pyridazin-3-yl]benzenecarbothioamide Chemical compound C=1N=C2C(NCC(C)C)=CC(C=3C=CN=CC=3)=NN2C=1C(C=C1)=CC=C1C(=S)NC1CC1 PYCWYALYEPASEN-UHFFFAOYSA-N 0.000 description 1
ZPCWWBPPLWBZFP-UHFFFAOYSA-N n-cyclopropyl-4-[8-(3-hydroxypropylamino)-6-(2-methylpyrazol-3-yl)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCCCO)C3=NC=2)C=2N(N=CC=2)C)=CC=C1C(=O)NC1CC1 ZPCWWBPPLWBZFP-UHFFFAOYSA-N 0.000 description 1
QGGCRIIVXKIVSI-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(1,1-dioxothian-4-yl)methylamino]-6-phenylsulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4C=CC=CC=4)C=C(NCC4CCS(=O)(=O)CC4)C3=NC=2)=CC=C1C(=O)NC1CC1 QGGCRIIVXKIVSI-UHFFFAOYSA-N 0.000 description 1
DOCLTOKSZLJTLR-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(1,1-dioxothian-4-yl)methylamino]-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(NCC4CCS(=O)(=O)CC4)C3=NC=2)=CC=C1C(=O)NC1CC1 DOCLTOKSZLJTLR-UHFFFAOYSA-N 0.000 description 1
ZSFRVDRNQIUTEA-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)O)C3=NC=2)C=2CCNCC=2)=CC=C1C(=O)NC1CC1 ZSFRVDRNQIUTEA-UHFFFAOYSA-N 0.000 description 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 description 1
CNZWNDBIJKIZRE-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(2,2,3,3-tetrafluoro-4-hydroxybutoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OCC(F)(F)C(F)(F)CO)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 CNZWNDBIJKIZRE-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
RCMILDLFLPBFFU-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(2-methylpyrazol-3-yl)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)O)C3=NC=2)C=2N(N=CC=2)C)=CC=C1C(=O)NC1CC1 RCMILDLFLPBFFU-UHFFFAOYSA-N 0.000 description 1
BMMCHRYDRJDICG-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(2-methylpyrazol-3-yl)imidazo[1,2-b]pyridazin-3-yl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CC2)=CC=C1C(N1N=2)=CN=C1C(NCC(C)(C)O)=CC=2C1=CC=NN1C BMMCHRYDRJDICG-UHFFFAOYSA-N 0.000 description 1
WNEAQYRBGWBJNM-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(2-morpholin-4-ylethylsulfanyl)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SCCN4CCOCC4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 WNEAQYRBGWBJNM-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 1
YPWXDFYFUUKRMT-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(pyrrolidin-3-ylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(NC4CNCC4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 YPWXDFYFUUKRMT-UHFFFAOYSA-N 0.000 description 1
VGERDUUGNCVKST-FQEVSTJZSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-[(3s)-2-oxopyrrolidin-3-yl]oxyimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(O[C@@H]4C(NCC4)=O)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 VGERDUUGNCVKST-FQEVSTJZSA-N 0.000 description 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 description 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 description 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 description 1
HVBRXLWSWOPZJG-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-methylsulfonylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)O)C3=NC=2)S(C)(=O)=O)=CC=C1C(=O)NC1CC1 HVBRXLWSWOPZJG-UHFFFAOYSA-N 0.000 description 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 description 1
XGRRQSZBLSQIGO-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-phenylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)O)C3=NC=2)C=2C=CC=CC=2)=CC=C1C(=O)NC1CC1 XGRRQSZBLSQIGO-UHFFFAOYSA-N 0.000 description 1
KLXHMRFXAGGFBA-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-phenylimidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound C=1N=C2C(NCC(C)(O)C)=CC(C=3C=CC=CC=3)=NN2C=1C(C=C1)=CC=C1C(=O)NC1CC1 KLXHMRFXAGGFBA-UHFFFAOYSA-N 0.000 description 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 description 1
MJRYLNDSTCSBGD-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-phenylsulfanylimidazo[1,2-b]pyridazin-3-yl]-3-methoxybenzamide Chemical compound COC1=CC(C(=O)NC2CC2)=CC=C1C(N1N=2)=CN=C1C(NCC(C)(C)O)=CC=2SC1=CC=CC=C1 MJRYLNDSTCSBGD-UHFFFAOYSA-N 0.000 description 1
GNDKINGRAQWKOO-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-phenylsulfanylimidazo[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=1SC1=CC=CC=C1 GNDKINGRAQWKOO-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
CIBIMHDQJNPXDX-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-pyridin-4-ylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=C(NCC(C)(C)O)C3=NC=2)C=2C=CN=CC=2)=CC=C1C(=O)NC1CC1 CIBIMHDQJNPXDX-UHFFFAOYSA-N 0.000 description 1
XFADNPZMEDGSFU-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-pyridin-4-ylimidazo[1,2-b]pyridazin-3-yl]benzenecarbothioamide Chemical compound C=1N=C2C(NCC(C)(O)C)=CC(C=3C=CN=CC=3)=NN2C=1C(C=C1)=CC=C1C(=S)NC1CC1 XFADNPZMEDGSFU-UHFFFAOYSA-N 0.000 description 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 description 1
JKXPLIMVCPTYIR-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-thiophen-2-ylsulfanylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(SC=4SC=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 JKXPLIMVCPTYIR-UHFFFAOYSA-N 0.000 description 1
MNRYUHYPKWWEKY-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-methoxy-2-methylpropyl)amino]-6-(2-methylpyrazol-3-yl)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C=1N=C2C(NCC(C)(C)OC)=CC(C=3N(N=CC=3)C)=NN2C=1C(C=C1C)=CC=C1C(=O)NC1CC1 MNRYUHYPKWWEKY-UHFFFAOYSA-N 0.000 description 1
QZHYLIMSSZBNCY-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-methoxy-2-methylpropyl)amino]-6-pyridin-4-ylimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C=1N=C2C(NCC(C)(C)OC)=CC(C=3C=CN=CC=3)=NN2C=1C(C=C1C)=CC=C1C(=O)NC1CC1 QZHYLIMSSZBNCY-UHFFFAOYSA-N 0.000 description 1
XVSKYOVKQRDXGH-BJKOFHAPSA-N n-cyclopropyl-4-[8-[[(2s)-2-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethyl]amino]-6-(2-methylpyrazol-3-yl)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CN1N=CC=C1C1=NN2C(C=3C=CC(=CC=3)C(=O)NC3CC3)=CN=C2C(NC[C@H](O)[C@@H]2OC(C)(C)OC2)=C1 XVSKYOVKQRDXGH-BJKOFHAPSA-N 0.000 description 1
125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000004770 neurodegeneration Effects 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
125000006574 non-aromatic ring group Chemical group 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
NYGCBQKDTGBHSC-UHFFFAOYSA-N oxan-2-ylmethanamine Chemical compound NCC1CCCCO1 NYGCBQKDTGBHSC-UHFFFAOYSA-N 0.000 description 1
IPBPLHNLRKRLPJ-UHFFFAOYSA-N oxan-4-ylmethanamine Chemical compound NCC1CCOCC1 IPBPLHNLRKRLPJ-UHFFFAOYSA-N 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000003585 oxepinyl group Chemical group 0.000 description 1
125000003566 oxetanyl group Chemical group 0.000 description 1
HZEQZXCNBJSQCS-UHFFFAOYSA-N oxolan-2-ylmethanethiol Chemical compound SCC1CCCO1 HZEQZXCNBJSQCS-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
230000037361 pathway Effects 0.000 description 1
229950007460 patupilone Drugs 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000009038 pharmacological inhibition Effects 0.000 description 1
125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
ZJSSCIORWSJOFW-UHFFFAOYSA-N phenoxy(pyrrolidin-2-yl)phosphinic acid Chemical compound C1CCNC1P(=O)(O)OC1=CC=CC=C1 ZJSSCIORWSJOFW-UHFFFAOYSA-N 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
150000003003 phosphines Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
150000003057 platinum Chemical class 0.000 description 1
LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
230000002265 prevention Effects 0.000 description 1
CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
229960000624 procarbazine Drugs 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 1
125000005551 pyridylene group Chemical group 0.000 description 1
LTXJLQINBYSQFU-UHFFFAOYSA-N pyrimidin-5-ol Chemical compound OC1=CN=CN=C1 LTXJLQINBYSQFU-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000001422 pyrrolinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
YOWAEZWWQFSEJD-UHFFFAOYSA-N quinoxalin-2-amine Chemical class C1=CC=CC2=NC(N)=CN=C21 YOWAEZWWQFSEJD-UHFFFAOYSA-N 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
229960004641 rituximab Drugs 0.000 description 1
229950008445 sagopilone Drugs 0.000 description 1
229940043230 sarcosine Drugs 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000011664 signaling Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
XVSFHIIADLZQJP-UHFFFAOYSA-M sodium;propane-1-thiolate Chemical compound [Na+].CCC[S-] XVSFHIIADLZQJP-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
230000024355 spindle assembly checkpoint Effects 0.000 description 1
230000019130 spindle checkpoint Effects 0.000 description 1
230000003019 stabilising effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000003826 tablet Substances 0.000 description 1
DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 1
YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
230000004797 therapeutic response Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
AWCWSADJWHZJOL-UHFFFAOYSA-N thian-4-ylmethanamine Chemical compound NCC1CCSCC1 AWCWSADJWHZJOL-UHFFFAOYSA-N 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000005556 thienylene group Chemical group 0.000 description 1
150000007944 thiolates Chemical class 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 description 1
229960003087 tioguanine Drugs 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
150000003852 triazoles Chemical group 0.000 description 1
OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
125000005455 trithianyl group Chemical group 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
238000004704 ultra performance liquid chromatography Methods 0.000 description 1
JXLYSJRDGCGARV-CFWMRBGOSA-N vinblastine Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-CFWMRBGOSA-N 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1