ME02389B - Supstituisani imidazopiridazini - Google Patents
Supstituisani imidazopiridaziniInfo
- Publication number
- ME02389B ME02389B MEP-2016-63A MEP6316A ME02389B ME 02389 B ME02389 B ME 02389B ME P6316 A MEP6316 A ME P6316A ME 02389 B ME02389 B ME 02389B
- Authority
- ME
- Montenegro
- Prior art keywords
- amino
- imidazo
- pyridazin
- cyclopropyl
- methylbenzamide
- Prior art date
Links
- 150000005233 imidazopyridazines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 150000001204 N-oxides Chemical class 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 6
- -1 or HO- Chemical group 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 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 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 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 230000024932 T cell mediated immunity Effects 0.000 claims 3
- 230000010261 cell growth Effects 0.000 claims 3
- 230000004663 cell proliferation Effects 0.000 claims 3
- 230000001413 cellular effect Effects 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 230000028709 inflammatory response Effects 0.000 claims 3
- 230000004083 survival effect Effects 0.000 claims 3
- PINYRFDOIAXNSD-UHFFFAOYSA-N 4-[6-(2-amino-3-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=C(F)C=CC=4)N)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 PINYRFDOIAXNSD-UHFFFAOYSA-N 0.000 claims 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 2
- RRXBLWQGRZAPSP-UHFFFAOYSA-N 4-[6-(2-amino-5-fluorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=CC=C(F)C=4)N)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 RRXBLWQGRZAPSP-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- YNBJPBVAMFNGIR-UHFFFAOYSA-N 4-[6-(3-chlorophenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(Cl)C=CC=4)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 YNBJPBVAMFNGIR-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims 2
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims 2
- 206010027476 Metastases Diseases 0.000 claims 2
- 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 2
- 229930012538 Paclitaxel Natural products 0.000 claims 2
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 2
- 208000037841 lung tumor Diseases 0.000 claims 2
- PCISWPYCRMKBLE-UHFFFAOYSA-N n-(1-cyanocyclopropyl)-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)NC1(C#N)CC1 PCISWPYCRMKBLE-UHFFFAOYSA-N 0.000 claims 2
- DJCIZCNDGYVCJP-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(3-methylphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 DJCIZCNDGYVCJP-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- OIWOEEQCHWUNPX-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(4-methylphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound C1=CC(C)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 OIWOEEQCHWUNPX-UHFFFAOYSA-N 0.000 claims 2
- 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 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 2
- 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 2
- CGAOOKGKZZXMAO-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-5-methylphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 CGAOOKGKZZXMAO-UHFFFAOYSA-N 0.000 claims 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
- 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 2
- 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 2
- 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 2
- CRTKOUIDKLSOAT-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-methoxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 CRTKOUIDKLSOAT-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- QCNDQTRMFKWHMC-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-4-methoxyphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(OC)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 QCNDQTRMFKWHMC-UHFFFAOYSA-N 0.000 claims 2
- MRKNAOQMMPSMSK-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-5-methylphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(F)=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 MRKNAOQMMPSMSK-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 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
- FMHHQGZBELCBMG-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-fluoro-2-methylphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 FMHHQGZBELCBMG-UHFFFAOYSA-N 0.000 claims 2
- 229960001592 paclitaxel Drugs 0.000 claims 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 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 claims 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- VOXBZHOHGGBLCQ-UHFFFAOYSA-N 2-amino-3,7-dihydropurine-6-thione;hydrate Chemical compound O.N1C(N)=NC(=S)C2=C1N=CN2.N1C(N)=NC(=S)C2=C1N=CN2 VOXBZHOHGGBLCQ-UHFFFAOYSA-N 0.000 claims 1
- IAZDIPNNMVZSAK-UHFFFAOYSA-N 4-[6-(3-chloro-4-fluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(Cl)C(F)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 IAZDIPNNMVZSAK-UHFFFAOYSA-N 0.000 claims 1
- LCKCCPOQSOZOLF-UHFFFAOYSA-N 4-[6-(3-chlorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(Cl)C=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 LCKCCPOQSOZOLF-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- PUJNZOKOQINFFP-UHFFFAOYSA-N 4-[6-(4-chloro-3-fluorophenoxy)-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C(Cl)=CC=4)C=C(NCC4CCSCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 PUJNZOKOQINFFP-UHFFFAOYSA-N 0.000 claims 1
- XHZFEEZRJSIXPK-UHFFFAOYSA-N 4-[6-(4-chloro-3-fluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C(Cl)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 XHZFEEZRJSIXPK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 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 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
- KGEVTZSWCINJPA-UHFFFAOYSA-N 4-[8-(2-cyanoethylamino)-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)C3=NC=2)=CC=C1C(=O)NC1CC1 KGEVTZSWCINJPA-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
- WQILQAUMNYTSKG-UHFFFAOYSA-N 4-[8-(3-aminopropylamino)-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(NCCCN)C3=NC=2)=CC=C1C(=O)NC1CC1 WQILQAUMNYTSKG-UHFFFAOYSA-N 0.000 claims 1
- QMOWVVWSORAWFE-UHFFFAOYSA-N 4-[8-(azetidin-3-ylmethylamino)-6-phenoxyimidazo[1,2-b]pyridazin-3-yl]-n-cyclopropyl-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=CC=CC=4)C=C(NCC4CNC4)C3=NC=2)=CC=C1C(=O)NC1CC1 QMOWVVWSORAWFE-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
- NWFOZDJJFHJZKL-UHFFFAOYSA-N 4-[8-[(2-amino-2-methylpropyl)amino]-6-(4-chlorophenoxy)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)N)C3=NC=2)=CC=C1C(=O)NC1CC1 NWFOZDJJFHJZKL-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
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 108010006654 Bleomycin Proteins 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 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 claims 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 claims 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 claims 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims 1
- 208000002699 Digestive System Neoplasms Diseases 0.000 claims 1
- 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims 1
- 208000009849 Female Genital Neoplasms Diseases 0.000 claims 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 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 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 102000043136 MAP kinase family Human genes 0.000 claims 1
- 108091054455 MAP kinase family Proteins 0.000 claims 1
- 206010059282 Metastases to central nervous system Diseases 0.000 claims 1
- 201000003793 Myelodysplastic syndrome Diseases 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
- 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
- OHUVLLOLALORLB-UHFFFAOYSA-N N-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[2-(4-methylpiperazin-1-yl)ethylamino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1CN(C)CCN1CCNC1=CC(OC=2C=C(F)C=CC=2)=NN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 OHUVLLOLALORLB-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
- YFOJNWGULHBGHG-UHFFFAOYSA-N N-cyclopropyl-4-[6-(5-fluoro-2-methylphenoxy)-8-(2-morpholin-4-ylethylamino)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(NCCN2CCOCC2)=C1 YFOJNWGULHBGHG-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
- ZKJZIJITUMDFAW-UHFFFAOYSA-N N-cyclopropyl-4-[8-(2,2-difluoroethylamino)-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(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 ZKJZIJITUMDFAW-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
- UPOQRCOMNJUCLS-UHFFFAOYSA-N N-cyclopropyl-4-[8-[(4,4-difluorocyclohexyl)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(NCC4CCC(F)(F)CC4)C3=NC=2)=CC=C1C(=O)NC1CC1 UPOQRCOMNJUCLS-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
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims 1
- 206010029098 Neoplasm skin Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 229940123237 Taxane Drugs 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims 1
- 229940009456 adriamycin Drugs 0.000 claims 1
- 230000002280 anti-androgenic effect Effects 0.000 claims 1
- 239000000051 antiandrogen Substances 0.000 claims 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 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- 229960000997 bicalutamide Drugs 0.000 claims 1
- 229960001561 bleomycin Drugs 0.000 claims 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 claims 1
- 125000005620 boronic acid group Chemical group 0.000 claims 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 claims 1
- 229960001467 bortezomib Drugs 0.000 claims 1
- 229960004117 capecitabine Drugs 0.000 claims 1
- 229960004562 carboplatin Drugs 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 210000000038 chest Anatomy 0.000 claims 1
- 229960004630 chlorambucil Drugs 0.000 claims 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 1
- 229960004316 cisplatin Drugs 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 229960004397 cyclophosphamide Drugs 0.000 claims 1
- 229960000978 cyproterone acetate Drugs 0.000 claims 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 claims 1
- 229960000684 cytarabine Drugs 0.000 claims 1
- 229960000975 daunorubicin Drugs 0.000 claims 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 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 229960003957 dexamethasone Drugs 0.000 claims 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 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 229960003668 docetaxel Drugs 0.000 claims 1
- 229960004679 doxorubicin Drugs 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 201000011523 endocrine gland cancer Diseases 0.000 claims 1
- 229930013356 epothilone Natural products 0.000 claims 1
- 150000003883 epothilone derivatives Chemical class 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 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 claims 1
- 229960001842 estramustine Drugs 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 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 claims 1
- 229960005420 etoposide Drugs 0.000 claims 1
- 229960000390 fludarabine Drugs 0.000 claims 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 claims 1
- 229960002949 fluorouracil Drugs 0.000 claims 1
- 229960002074 flutamide Drugs 0.000 claims 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 claims 1
- 229910052736 halogen Chemical group 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 208000019691 hematopoietic and lymphoid cell neoplasm Diseases 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 229960000908 idarubicin Drugs 0.000 claims 1
- 229960001101 ifosfamide Drugs 0.000 claims 1
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 229960001924 melphalan Drugs 0.000 claims 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 claims 1
- 229960000485 methotrexate Drugs 0.000 claims 1
- 229960001156 mitoxantrone Drugs 0.000 claims 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 claims 1
- IPPXHWMLSOMYBA-UHFFFAOYSA-N n-cyclopropyl-2-methyl-4-[6-(2-methylphenoxy)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide Chemical compound CC1=CC=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 IPPXHWMLSOMYBA-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- SJFBZRHPPXOKBO-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,3-difluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=C(F)C=CC=4)F)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 SJFBZRHPPXOKBO-UHFFFAOYSA-N 0.000 claims 1
- DSSYFYRKOOMSBH-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-3-methylsulfanylphenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CSC1=CC=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1F DSSYFYRKOOMSBH-UHFFFAOYSA-N 0.000 claims 1
- JFKCTKMMFMTQKJ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-4-methoxyphenoxy)-8-(2-methylsulfonylethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound FC1=CC(OC)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCS(C)(=O)=O)=C1 JFKCTKMMFMTQKJ-UHFFFAOYSA-N 0.000 claims 1
- NVPCBOQJOOAJTG-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-4-methoxyphenoxy)-8-(oxan-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound FC1=CC(OC)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC2CCOCC2)=C1 NVPCBOQJOOAJTG-UHFFFAOYSA-N 0.000 claims 1
- CUERSJUVWODDIV-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluoro-5-methylphenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 CUERSJUVWODDIV-UHFFFAOYSA-N 0.000 claims 1
- XKBJPGKHHKSNLO-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluorophenoxy)-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=CC=CC=4)F)C=C(NCC4CCSCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 XKBJPGKHHKSNLO-UHFFFAOYSA-N 0.000 claims 1
- UIIBZLYLRDUCBY-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2-fluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C(=CC=CC=4)F)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 UIIBZLYLRDUCBY-UHFFFAOYSA-N 0.000 claims 1
- WMCOKEBNQSACSX-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,4-difluorophenoxy)-8-(methylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NC)=CC=1OC1=CC=C(F)C(F)=C1 WMCOKEBNQSACSX-UHFFFAOYSA-N 0.000 claims 1
- KDBGHFSTGHMLCA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,4-difluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C(F)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 KDBGHFSTGHMLCA-UHFFFAOYSA-N 0.000 claims 1
- GVCVEPCWDJOSSA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,4-difluorophenoxy)-8-[2-(dimethylamino)ethylamino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCN(C)C)=CC=1OC1=CC=C(F)C(F)=C1 GVCVEPCWDJOSSA-UHFFFAOYSA-N 0.000 claims 1
- ZERKWWBTNONCCE-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,5-difluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=C(F)C=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 ZERKWWBTNONCCE-UHFFFAOYSA-N 0.000 claims 1
- DTGCZEAGSDIYFM-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3,5-dimethylphenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C)=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 DTGCZEAGSDIYFM-UHFFFAOYSA-N 0.000 claims 1
- 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
- XCHLKOYBBLFTME-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-5-methylphenoxy)-8-(4,4,4-trifluorobutylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(F)=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCCC(F)(F)F)=C2)=C1 XCHLKOYBBLFTME-UHFFFAOYSA-N 0.000 claims 1
- ZJPYPUOKBZKBIN-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-5-methylphenoxy)-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(F)=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC3CCSCC3)=C2)=C1 ZJPYPUOKBZKBIN-UHFFFAOYSA-N 0.000 claims 1
- XODNYIVQIRRXRE-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-5-methylphenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(F)=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 XODNYIVQIRRXRE-UHFFFAOYSA-N 0.000 claims 1
- HQIKRGYWVOQEFV-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(1h-pyrazol-5-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCC4=NNC=C4)C3=NC=2)=CC=C1C(=O)NC1CC1 HQIKRGYWVOQEFV-UHFFFAOYSA-N 0.000 claims 1
- AQNSRKMCVMCYHS-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(2,2,2-trifluoroethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 AQNSRKMCVMCYHS-UHFFFAOYSA-N 0.000 claims 1
- YLASFKKWWVWGPB-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(2-hydroxyethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCCO)C3=NC=2)=CC=C1C(=O)NC1CC1 YLASFKKWWVWGPB-UHFFFAOYSA-N 0.000 claims 1
- SMOOINCGSZGKFP-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(2-methoxyethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCOC)=CC=1OC1=CC=CC(F)=C1 SMOOINCGSZGKFP-UHFFFAOYSA-N 0.000 claims 1
- GBHCSNZBRSOJMI-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(2-morpholin-4-ylethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCCN4CCOCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 GBHCSNZBRSOJMI-UHFFFAOYSA-N 0.000 claims 1
- KUORWNYCYLJPCJ-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-(2-piperidin-1-ylethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCCN4CCCCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 KUORWNYCYLJPCJ-UHFFFAOYSA-N 0.000 claims 1
- 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
- XKPHLXUQSUMFKA-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[(1-methylpiperidin-4-yl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1CN(C)CCC1CNC1=CC(OC=2C=C(F)C=CC=2)=NN2C1=NC=C2C(C=C1C)=CC=C1C(=O)NC1CC1 XKPHLXUQSUMFKA-UHFFFAOYSA-N 0.000 claims 1
- YNRMAVIGZXICCY-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[(1-methylpyrazol-3-yl)methylamino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCC4=NN(C)C=C4)C3=NC=2)=CC=C1C(=O)NC1CC1 YNRMAVIGZXICCY-UHFFFAOYSA-N 0.000 claims 1
- UISCUPDKVBCQMK-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 UISCUPDKVBCQMK-UHFFFAOYSA-N 0.000 claims 1
- 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
- JGYRKMWORQQRPO-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluorophenoxy)-8-(thian-4-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=CC(F)=CC=4)C=C(NCC4CCSCC4)C3=NC=2)=CC=C1C(=O)NC1CC1 JGYRKMWORQQRPO-UHFFFAOYSA-N 0.000 claims 1
- WDQGQXRVEBRSKH-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-fluorophenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=CC(F)=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 WDQGQXRVEBRSKH-UHFFFAOYSA-N 0.000 claims 1
- GOWNGRZYVGUVIV-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-fluoro-2-methylphenoxy)-8-(2-methylsulfonylethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCS(C)(=O)=O)=C1 GOWNGRZYVGUVIV-UHFFFAOYSA-N 0.000 claims 1
- YADUGVCQKYSQBL-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-fluoro-2-methylphenoxy)-8-[(2-hydroxy-2-methylpropyl)amino]imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=C(F)C=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 YADUGVCQKYSQBL-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- QTLFEEXOUPJCMD-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(3-methylphenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 QTLFEEXOUPJCMD-UHFFFAOYSA-N 0.000 claims 1
- ROXFZBULEMIWOR-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(3-propan-2-yloxyphenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC(C)OC1=CC=CC(OC2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCC(C)(C)O)=C2)=C1 ROXFZBULEMIWOR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KIZAHVVNHOVQPI-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(4-methoxyphenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=CC(OC)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 KIZAHVVNHOVQPI-UHFFFAOYSA-N 0.000 claims 1
- 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
- JMBBJYAAYUADKO-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-(4-propan-2-yloxyphenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=CC(OC(C)C)=CC=C1OC1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCC(C)(C)O)=C1 JMBBJYAAYUADKO-UHFFFAOYSA-N 0.000 claims 1
- IGYWWZFIEZDSTF-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(2-hydroxy-2-methylpropyl)amino]-6-phenoxyimidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=CC=CC=4)C=C(NCC(C)(C)O)C3=NC=2)=CC=C1C(=O)NC1CC1 IGYWWZFIEZDSTF-UHFFFAOYSA-N 0.000 claims 1
- MNOGBZVFRZWZRU-UHFFFAOYSA-N n-cyclopropyl-4-[8-[(3,3-difluorocyclobutyl)methylamino]-6-(3-fluorophenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(OC=4C=C(F)C=CC=4)C=C(NCC4CC(F)(F)C4)C3=NC=2)=CC=C1C(=O)NC1CC1 MNOGBZVFRZWZRU-UHFFFAOYSA-N 0.000 claims 1
- PYXFUEFJAVRMIU-UHFFFAOYSA-N n-cyclopropyl-4-[8-[2-(dimethylamino)ethylamino]-6-(3-fluorophenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCN(C)C)=CC=1OC1=CC=CC(F)=C1 PYXFUEFJAVRMIU-UHFFFAOYSA-N 0.000 claims 1
- IAYZNYHWGWOPSA-UHFFFAOYSA-N n-cyclopropyl-4-[8-[3-(dimethylamino)propylamino]-6-(3-fluorophenoxy)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound N=1N2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCCN(C)C)=CC=1OC1=CC=CC(F)=C1 IAYZNYHWGWOPSA-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003057 platinum Chemical class 0.000 claims 1
- 229960005205 prednisolone Drugs 0.000 claims 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 claims 1
- 229960000624 procarbazine Drugs 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 208000023958 prostate neoplasm Diseases 0.000 claims 1
- 229960004641 rituximab Drugs 0.000 claims 1
- 201000004477 skin sarcoma Diseases 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229960003087 tioguanine Drugs 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 claims 1
- 229960003048 vinblastine Drugs 0.000 claims 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine 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-XQKSVPLYSA-N 0.000 claims 1
- 229960004528 vincristine Drugs 0.000 claims 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 claims 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 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Cosmetics (AREA)
- Paper (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10176134 | 2010-09-10 | ||
| EP11075022 | 2011-02-04 | ||
| EP11170775 | 2011-06-21 | ||
| EP11170771 | 2011-06-21 | ||
| PCT/EP2011/065368 WO2012032031A1 (en) | 2010-09-10 | 2011-09-06 | Substituted imidazopyridazines |
| EP11751910.8A EP2614063B1 (en) | 2010-09-10 | 2011-09-06 | Substituted imidazopyridazines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ME02389B true ME02389B (me) | 2016-09-20 |
Family
ID=44545741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2016-63A ME02389B (me) | 2010-09-10 | 2011-09-06 | Supstituisani imidazopiridazini |
Country Status (38)
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI541243B (zh) | 2010-09-10 | 2016-07-11 | 拜耳知識產權公司 | 經取代咪唑并嗒 |
| WO2012088266A2 (en) | 2010-12-22 | 2012-06-28 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of fgfr3 |
| ES2671748T3 (es) | 2011-07-21 | 2018-06-08 | Tolero Pharmaceuticals, Inc. | Inhibidores heterocíclicos de proteína quinasas |
| US9512126B2 (en) | 2012-03-14 | 2016-12-06 | Bayer Intellectual Property Gmbh | Substituted imidazopyridazines |
| UA125503C2 (uk) | 2012-06-13 | 2022-04-13 | Інсайт Холдинґс Корпорейшн | Заміщені трициклічні сполуки як інгібітори fgfr |
| WO2014020043A1 (en) | 2012-08-02 | 2014-02-06 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer |
| WO2014020041A1 (en) | 2012-08-02 | 2014-02-06 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| AU2013344716B2 (en) | 2012-11-16 | 2018-03-01 | University Health Network | Pyrazolopyrimidine compounds |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| TW201437211A (zh) * | 2013-03-01 | 2014-10-01 | Bayer Pharma AG | 經取代咪唑并嗒□ |
| MY181497A (en) | 2013-04-19 | 2020-12-23 | Incyte Holdings Corp | Bicyclic heterocycles as fgfr inhibitors |
| AP2015008898A0 (en) | 2013-06-11 | 2015-12-31 | Bayer Pharma AG | Prodrug derivatives of substituted triazolopyridines |
| EP3007698A1 (en) * | 2013-06-13 | 2016-04-20 | Bayer Pharma Aktiengesellschaft | Combination of a imidazopyridazine derivative and a mitotic agent for the treatment of cancer |
| CN103360399B (zh) * | 2013-08-02 | 2016-03-02 | 北京大学 | 6-芳基取代-咪唑-[1,2-b]哒嗪类衍生物，其制备方法及用途 |
| GB201321734D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic Agents |
| JP6506313B2 (ja) * | 2014-02-21 | 2019-04-24 | フロスト バイオロジック，インコーポレーテッド | 癌及び増殖性疾患の治療のための抗有糸分裂性アミド |
| WO2015157955A1 (en) | 2014-04-17 | 2015-10-22 | Abbvie Inc. | Heterocyclic btk inhibit ors |
| TW201613927A (en) * | 2014-09-01 | 2016-04-16 | Bayer Pharma AG | Method for preparation of substituted imidazopyridazines |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| CR20170390A (es) | 2015-02-20 | 2017-10-23 | Incyte Holdings Corp | Heterociclos biciclicos como inhibidores de fgfr |
| JP6993233B2 (ja) | 2015-04-17 | 2022-01-13 | ネザーランズ トランスレーショナル リサーチ センター ビー．ブイ． | Ｔｔｋ阻害剤化学療法の為の予後バイオマーカー |
| WO2016187028A1 (en) * | 2015-05-15 | 2016-11-24 | Celgene Avilomics Research, Inc. | Heteroaryl compounds, synthesis thereof, and intermediates thereto |
| JP6778749B2 (ja) * | 2015-12-04 | 2020-11-04 | エクソンモービル リサーチ アンド エンジニアリング カンパニーＥｘｘｏｎ Ｒｅｓｅａｒｃｈ Ａｎｄ Ｅｎｇｉｎｅｅｒｉｎｇ Ｃｏｍｐａｎｙ | Ｅｍｍ−２８、新規合成結晶性材料、その製造および使用 |
| WO2018013430A2 (en) | 2016-07-12 | 2018-01-18 | Arisan Therapeutics Inc. | Heterocyclic compounds for the treatment of arenavirus infection |
| KR102700233B1 (ko) | 2016-07-18 | 2024-08-28 | 유니버시티 헬스 네트워크 | 고체 형태의 ttk 억제제 |
| EP3609547B1 (en) * | 2017-04-11 | 2021-10-06 | Straumann Holding AG | Dental implant |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| BR112020022392A2 (pt) | 2018-05-04 | 2021-02-02 | Incyte Corporation | formas sólidas de um inibidor de fgfr e processos para preparação das mesmas |
| PE20210919A1 (es) | 2018-05-04 | 2021-05-19 | Incyte Corp | Sales de un inhibidor de fgfr |
| HUE068695T2 (hu) | 2018-05-08 | 2025-01-28 | Nippon Shinyaku Co Ltd | Azabenzimidazol vegyületek és gyógyszerek |
| US12419865B2 (en) | 2018-12-06 | 2025-09-23 | Arisan Therapeutics Inc. | Compounds for the treatment of arenavirus infection |
| CA3127502A1 (en) | 2019-02-12 | 2020-08-20 | Sumitomo Dainippon Pharma Oncology, Inc. | Formulations comprising heterocyclic protein kinase inhibitors |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| CN111978325B (zh) * | 2019-05-22 | 2023-11-17 | 中国药科大学 | 咪唑并哒嗪类mnk1/mnk2激酶抑制剂及其制备方法和应用 |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US12122767B2 (en) | 2019-10-01 | 2024-10-22 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| GEP20247679B (en) | 2019-10-14 | 2024-10-10 | Incyte Corp | Bicyclic heterocycles as fgfr inhibitors |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| PE20221504A1 (es) | 2019-12-04 | 2022-09-30 | Incyte Corp | Derivados de un inhibidor de fgfr |
| JP7720840B2 (ja) | 2019-12-04 | 2025-08-08 | インサイト・コーポレイション | Ｆｇｆｒ阻害剤としての三環式複素環 |
| WO2021146424A1 (en) | 2020-01-15 | 2021-07-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| TW202304459A (zh) | 2021-04-12 | 2023-02-01 | 美商英塞特公司 | 包含ｆｇｆｒ抑制劑及ｎｅｃｔｉｎ－４靶向劑之組合療法 |
| CA3220155A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| TW202313611A (zh) | 2021-06-09 | 2023-04-01 | 美商英塞特公司 | 作為ｆｇｆｒ抑制劑之三環雜環 |
| KR20240107189A (ko) * | 2021-12-15 | 2024-07-08 | 신라젠(주) | 신생물성 질환 치료에 사용하기 위한 약제학적 병용물 |
| EP4651948A1 (en) * | 2023-01-19 | 2025-11-26 | Skyhawk Therapeutics, Inc. | Compositions useful for modulating splicing |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ333302A (en) | 1996-08-28 | 2000-08-25 | Pfizer | Substituted 6,5-hetero-bicyclic derivatives for the prevention or inhibition of a disorder that can be treated by antagonising corticotropin releasing factor |
| CN1173975C (zh) | 2000-04-27 | 2004-11-03 | 山之内制药株式会社 | 咪唑并吡啶衍生物 |
| AR045697A1 (es) | 2003-07-14 | 2005-11-09 | Arena Pharm Inc | Aril y heteroaril derivados fusionados como moduladores del metabolismo y la prevencion y tratamiento de trastornos relacionados con el mismo |
| EP1713784A1 (en) | 2004-02-12 | 2006-10-25 | Neurogen Corporation | Imidazo-pyridazines, triazolo-pyridazines and related benzodiazepine receptor ligands |
| US7306631B2 (en) | 2004-03-30 | 2007-12-11 | The Procter & Gamble Company | Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof |
| WO2007025090A2 (en) | 2005-08-25 | 2007-03-01 | Kalypsys, Inc. | Heterobicyclic and - tricyclic inhibitors of mapk/erk kinase |
| US20070078136A1 (en) * | 2005-09-22 | 2007-04-05 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| US7723336B2 (en) | 2005-09-22 | 2010-05-25 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| BRPI0618520A2 (pt) * | 2005-11-10 | 2011-09-06 | Schering Corp | imidazopirazinas como inibidores de proteìna cinase |
| TW200840584A (en) * | 2006-12-26 | 2008-10-16 | Gilead Sciences Inc | Pyrido(3,2-d)pyrimidines useful for treating viral infections |
| WO2008130951A1 (en) * | 2007-04-17 | 2008-10-30 | Bristol-Myers Squibb Company | Fused heterocyclic 11-beta-hydroxysteroid dehydrogenase type i inhibitors |
| US20110046127A1 (en) | 2007-11-08 | 2011-02-24 | Paolo Pevarello | Imidazopyridazines for Use as Protein Kinase Inhibitors |
| US8389527B2 (en) | 2008-02-06 | 2013-03-05 | Bristol-Myers Squibb Company | Substituted imidazopyridazines useful as kinase inhibitors |
| TWI491610B (zh) | 2008-10-09 | 2015-07-11 | 必治妥美雅史谷比公司 | 作為激酶抑制劑之咪唑并嗒腈 |
| WO2010088518A2 (en) | 2009-01-31 | 2010-08-05 | Kalypsys, Inc. | Heterocyclic modulators of gpr119 for treatment of disease |
| WO2010124826A1 (en) | 2009-04-29 | 2010-11-04 | Bayer Schering Pharma Aktiengesellschaft | Substituted imidazoquinoxalines |
| TW201107329A (en) * | 2009-07-30 | 2011-03-01 | Oncotherapy Science Inc | Fused imidazole derivative having ttk inhibitory action |
| US9340528B2 (en) | 2009-09-04 | 2016-05-17 | Bayer Pharma Aktiengesellschaft | Substituted aminoquinoxalines as tyrosine threonine kinase inhibitors |
| EP2343295A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Triazolopyridine derivates |
| EP2343294A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Substituted triazolopyridines |
| EP2343297A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Triazolopyridines |
| ES2551407T3 (es) | 2010-03-18 | 2015-11-18 | Bayer Intellectual Property Gmbh | Imidazopirazinas |
| EP2576560B1 (en) | 2010-06-01 | 2015-09-30 | Bayer Intellectual Property GmbH | Substituted imidazopyrazines |
| TWI541243B (zh) | 2010-09-10 | 2016-07-11 | 拜耳知識產權公司 | 經取代咪唑并嗒 |
| US20140187548A1 (en) | 2010-12-17 | 2014-07-03 | Bayer Intellectual Property Gmbh | 6 substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| WO2012080229A1 (en) | 2010-12-17 | 2012-06-21 | Bayer Pharma Aktiengesellschaft | Imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment hyperproliferative disorders |
| WO2012080234A1 (en) | 2010-12-17 | 2012-06-21 | Bayer Pharma Aktiengesellschaft | Substituted 6-imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| CA2821837A1 (en) | 2010-12-17 | 2012-06-21 | Bayer Intellectual Property Gmbh | 2-substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| US20140135319A1 (en) | 2010-12-17 | 2014-05-15 | Bayer Intellectual Property Gmbh | 6-substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| CA2821827A1 (en) | 2010-12-17 | 2012-06-21 | Bayer Intellectual Property Gmbh | 6-thio-substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
-
2011
- 2011-08-25 TW TW100130542A patent/TWI541243B/zh not_active IP Right Cessation
- 2011-09-06 MX MX2013002713A patent/MX2013002713A/es active IP Right Grant
- 2011-09-06 HR HRP20160360TT patent/HRP20160360T1/hr unknown
- 2011-09-06 NZ NZ607904A patent/NZ607904A/en not_active IP Right Cessation
- 2011-09-06 SG SG2013016480A patent/SG188417A1/en unknown
- 2011-09-06 EP EP11751910.8A patent/EP2614063B1/en active Active
- 2011-09-06 EA EA201390339A patent/EA023420B1/ru not_active IP Right Cessation
- 2011-09-06 KR KR1020137009011A patent/KR20140032337A/ko not_active Ceased
- 2011-09-06 CA CA2810755A patent/CA2810755A1/en not_active Abandoned
- 2011-09-06 WO PCT/EP2011/065368 patent/WO2012032031A1/en not_active Ceased
- 2011-09-06 PE PE2013000392A patent/PE20131164A1/es not_active Application Discontinuation
- 2011-09-06 JP JP2013527575A patent/JP5824050B2/ja not_active Expired - Fee Related
- 2011-09-06 PL PL11751910T patent/PL2614063T3/pl unknown
- 2011-09-06 CN CN201180054217.5A patent/CN103370318B/zh not_active Expired - Fee Related
- 2011-09-06 PH PH1/2013/500454A patent/PH12013500454A1/en unknown
- 2011-09-06 HU HUE11751910A patent/HUE028771T2/en unknown
- 2011-09-06 CU CUP2013000033A patent/CU24187B1/es active IP Right Grant
- 2011-09-06 AP AP2013006790A patent/AP3607A/xx active
- 2011-09-06 ME MEP-2016-63A patent/ME02389B/me unknown
- 2011-09-06 US US13/822,175 patent/US9255100B2/en not_active Expired - Fee Related
- 2011-09-06 MY MYPI2013700375A patent/MY185139A/en unknown
- 2011-09-06 MA MA35720A patent/MA34516B1/fr unknown
- 2011-09-06 ES ES11751910.8T patent/ES2568220T3/es active Active
- 2011-09-06 AU AU2011298844A patent/AU2011298844B2/en not_active Ceased
- 2011-09-06 DK DK11751910.8T patent/DK2614063T3/en active
- 2011-09-06 RS RS20160221A patent/RS54661B1/sr unknown
- 2011-09-06 SI SI201130761A patent/SI2614063T1/sl unknown
- 2011-09-06 BR BR112013005679A patent/BR112013005679A2/pt not_active IP Right Cessation
- 2011-09-07 SA SA111320735A patent/SA111320735B1/ar unknown
- 2011-09-08 UY UY0001033598A patent/UY33598A/es unknown
- 2011-09-09 AR ARP110103294A patent/AR082946A1/es unknown
-
2013
- 2013-03-05 IL IL225058A patent/IL225058A/en active IP Right Grant
- 2013-03-07 ZA ZA2013/01756A patent/ZA201301756B/en unknown
- 2013-03-08 CR CR20130102A patent/CR20130102A/es unknown
- 2013-03-08 DO DO2013000054A patent/DOP2013000054A/es unknown
- 2013-03-08 EC ECSP13012752 patent/ECSP13012752A/es unknown
- 2013-03-08 CO CO13047157A patent/CO6720961A2/es active IP Right Grant
-
2016
- 2016-04-12 CY CY20161100294T patent/CY1117352T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ME02389B (me) | Supstituisani imidazopiridazini | |
| JP7278359B2 (ja) | Ｓｈｐ２の活性を阻害するための化合物および組成物 | |
| CN105899493B (zh) | 用于抑制shp2活性的1-(三嗪-3-基/哒嗪-3-基)-哌(-嗪)啶衍生物及其组合物 | |
| TWI657083B (zh) | 用於抑制ｓｈｐ２活性之化合物及組合物 | |
| JP6718889B2 (ja) | Ｓｈｐ２の活性を阻害するための化合物および組成物 | |
| CN106413716B (zh) | 通过jak和pi3k抑制剂组合治疗b细胞恶性肿瘤 | |
| CN103958502B (zh) | 作为丝氨酸/苏氨酸激酶抑制剂的喹唑啉化合物 | |
| JP2013537174A5 (OSRAM) | ||
| JP7012152B2 (ja) | Ｆｓｈｄの治療のためにｄｕｘ４および下流遺伝子発現を低減するｐ３８キナーゼ阻害剤 | |
| JP2017513942A (ja) | Ｍｅｒｔｋ特異的ピロロピリミジン化合物 | |
| CN107872977A (zh) | Irak4抑制剂与btk抑制剂的组合产品 | |
| TW201247674A (en) | Pyrrolotriazinone derivatives as PI3K inhibitors | |
| KR20150023752A (ko) | 암 및 자가면역 질환 치료에 유용한 가역적인 공유 피롤로- 또는 피라졸로피리미딘 | |
| CN108771681A (zh) | 作为dna-pk抑制剂的化合物及其氘化衍生物的共晶 | |
| JP2019048850A (ja) | メトホルミン及びジヒドロケルセチンを含む組み合わせ医薬、及びがんの治療のための使用 | |
| EP4219488A1 (en) | Method for the preparation of urea compounds as smarca2/brm-atpase inhibitors | |
| EP4013756B1 (en) | Mll1 inhibitors and anti-cancer agents | |
| KR20230051200A (ko) | Btk 및 이의 돌연변이체의 억제제를 포함하는 투여 형태 조성물 | |
| JP2022549449A (ja) | Ｍｌｌ１阻害剤及び抗癌剤 | |
| EP4077329A1 (en) | 1h-pyrazolo[3,4-d]pyrimidine compounds useful for the treatment of platinum-resistant cancer | |
| EP3195865A1 (de) | Kombinationen von irak4 inhibitoren und btk inhibitoren | |
| JP2024529485A (ja) | イミダゾ［１，２－ｂ］ピリダジニル化合物及びその使用 | |
| HK40045602A (en) | Urea compounds and compositions as smarca2/brm-atpase inhibitors |