JP2015513559A5 - - Google Patents
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- Publication number
- JP2015513559A5 JP2015513559A5 JP2014561391A JP2014561391A JP2015513559A5 JP 2015513559 A5 JP2015513559 A5 JP 2015513559A5 JP 2014561391 A JP2014561391 A JP 2014561391A JP 2014561391 A JP2014561391 A JP 2014561391A JP 2015513559 A5 JP2015513559 A5 JP 2015513559A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclopropyl
- trifluoropropyl
- imidazo
- amino
- methylbenzamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 53
- -1 hydroxy - Chemical class 0.000 claims 15
- 125000005843 halogen group Chemical group 0.000 claims 14
- 238000000034 method Methods 0.000 claims 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 3
- 229920002554 vinyl polymer Polymers 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 230000024932 T cell mediated immunity Effects 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 230000010261 cell growth Effects 0.000 claims 2
- 230000004663 cell proliferation Effects 0.000 claims 2
- 230000001413 cellular effect Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 230000028709 inflammatory response Effects 0.000 claims 2
- PARIRJREEMEWST-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,3-difluorobenzoyl)-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(=O)C=2C(=C(F)C=CC=2)F)=CC=C1C(=O)NC1CC1 PARIRJREEMEWST-UHFFFAOYSA-N 0.000 claims 2
- XKGGQGQPVFWTOO-UHFFFAOYSA-N n-cyclopropyl-4-[6-(2,5-difluorobenzoyl)-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(=O)C=2C(=CC=C(F)C=2)F)=CC=C1C(=O)NC1CC1 XKGGQGQPVFWTOO-UHFFFAOYSA-N 0.000 claims 2
- RRJAROULOCCCAF-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-2-methoxybenzoyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=C(F)C=CC=C1C(=O)C1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 RRJAROULOCCCAF-UHFFFAOYSA-N 0.000 claims 2
- WVPNNDAQCJXQPT-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluoro-4-methoxybenzoyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(OC)=CC=C1C(=O)C1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 WVPNNDAQCJXQPT-UHFFFAOYSA-N 0.000 claims 2
- HJKXTKURGJYYPT-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-fluorobenzoyl)-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(=O)C=2C=C(F)C=CC=2)=CC=C1C(=O)NC1CC1 HJKXTKURGJYYPT-UHFFFAOYSA-N 0.000 claims 2
- FXMKHYPZZXYEFF-UHFFFAOYSA-N n-cyclopropyl-4-[6-[(2,5-difluorophenyl)-hydroxymethyl]-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(O)C=2C(=CC=C(F)C=2)F)=CC=C1C(=O)NC1CC1 FXMKHYPZZXYEFF-UHFFFAOYSA-N 0.000 claims 2
- CWJWUMXUCUVBJG-UHFFFAOYSA-N n-cyclopropyl-4-[6-[(3-fluoro-4-methoxyphenyl)-hydroxymethyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(OC)=CC=C1C(O)C1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 CWJWUMXUCUVBJG-UHFFFAOYSA-N 0.000 claims 2
- CNLZBROVLMNAQQ-UHFFFAOYSA-N n-cyclopropyl-4-[6-[1-(2,5-difluorophenyl)ethenyl]-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(=C)C=2C(=CC=C(F)C=2)F)=CC=C1C(=O)NC1CC1 CNLZBROVLMNAQQ-UHFFFAOYSA-N 0.000 claims 2
- SNRVXEOBBVXVIN-UHFFFAOYSA-N n-cyclopropyl-4-[6-[2-(4-methoxyphenyl)-1,3-dithiolan-2-yl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=CC(OC)=CC=C1C1(C2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)SCCS1 SNRVXEOBBVXVIN-UHFFFAOYSA-N 0.000 claims 2
- VXRJEVHAMVAZTL-UHFFFAOYSA-N n-cyclopropyl-4-[6-formyl-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(C=O)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 VXRJEVHAMVAZTL-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 230000004083 survival effect Effects 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 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
- 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
- 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
- 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
- 102000043136 MAP kinase family Human genes 0.000 claims 1
- 108091054455 MAP kinase family Proteins 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- URLBQXJTRZJXMK-UHFFFAOYSA-N N-cyclopropyl-4-[6-[(3-fluorophenyl)-hydroxymethyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound Cc1cc(ccc1C(=O)NC1CC1)-c1cnc2c(NCCC(F)(F)F)cc(nn12)C(O)c1cccc(F)c1 URLBQXJTRZJXMK-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm 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
- 229940030495 antiandrogen sex hormone and modulator of the genital system 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
- 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
- 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
- 229960004397 cyclophosphamide 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
- 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
- 239000003085 diluting agent Substances 0.000 claims 1
- 229960004679 doxorubicin Drugs 0.000 claims 1
- 229940079593 drug Drugs 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
- 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
- 208000019691 hematopoietic and lymphoid cell neoplasm Diseases 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 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
- OXSABAZYSCHBEW-UHFFFAOYSA-N imidazo[1,2-b]pyridazine Chemical compound N1=C=CC=C2N=C[CH]N21 OXSABAZYSCHBEW-UHFFFAOYSA-N 0.000 claims 1
- 230000006698 induction Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 229960000485 methotrexate Drugs 0.000 claims 1
- FIRMDHDGJSBPDU-UHFFFAOYSA-N methyl 3-[4-(cyclopropylcarbamoyl)-3-methylphenyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazine-6-carboxylate Chemical compound N12N=C(C(=O)OC)C=C(NCCC(F)(F)F)C2=NC=C1C(C=C1C)=CC=C1C(=O)NC1CC1 FIRMDHDGJSBPDU-UHFFFAOYSA-N 0.000 claims 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims 1
- BDTMALFFRNYFLG-UHFFFAOYSA-N n-cyclopropyl-4-[6-(3-methoxybenzoyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=CC(C(=O)C2=NN3C(C=4C=C(C)C(C(=O)NC5CC5)=CC=4)=CN=C3C(NCCC(F)(F)F)=C2)=C1 BDTMALFFRNYFLG-UHFFFAOYSA-N 0.000 claims 1
- NIMHKWNTOQONKD-UHFFFAOYSA-N n-cyclopropyl-4-[6-(4-methoxybenzoyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 NIMHKWNTOQONKD-UHFFFAOYSA-N 0.000 claims 1
- LWHOYKWLVDGWRM-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-fluoro-2-methoxybenzoyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=C(F)C=C1C(=O)C1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 LWHOYKWLVDGWRM-UHFFFAOYSA-N 0.000 claims 1
- HJZHBNINUQKWSW-UHFFFAOYSA-N n-cyclopropyl-4-[6-(5-fluoro-2-phenylmethoxybenzoyl)-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(=O)C=2C(=CC=C(F)C=2)OCC=2C=CC=CC=2)=CC=C1C(=O)NC1CC1 HJZHBNINUQKWSW-UHFFFAOYSA-N 0.000 claims 1
- MZVYQYHRWZVFSS-UHFFFAOYSA-N n-cyclopropyl-4-[6-(hydroxymethyl)-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound CC1=CC(C=2N3N=C(CO)C=C(NCCC(F)(F)F)C3=NC=2)=CC=C1C(=O)NC1CC1 MZVYQYHRWZVFSS-UHFFFAOYSA-N 0.000 claims 1
- DSCYGDOLRIGYLN-HHHXNRCGSA-N n-cyclopropyl-4-[6-[(1r)-1-(3-fluoro-2-hydroxyphenyl)-1-hydroxyethyl]-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@](C)(O)C=2C(=C(F)C=CC=2)O)=CC=C1C(=O)NC1CC1 DSCYGDOLRIGYLN-HHHXNRCGSA-N 0.000 claims 1
- DSCYGDOLRIGYLN-MHZLTWQESA-N n-cyclopropyl-4-[6-[(1s)-1-(3-fluoro-2-hydroxyphenyl)-1-hydroxyethyl]-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@@](C)(O)C=2C(=C(F)C=CC=2)O)=CC=C1C(=O)NC1CC1 DSCYGDOLRIGYLN-MHZLTWQESA-N 0.000 claims 1
- BRHQGQVJLPRDBV-UHFFFAOYSA-N n-cyclopropyl-4-[6-[(2,3-difluorophenyl)-hydroxymethyl]-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(O)C=2C(=C(F)C=CC=2)F)=CC=C1C(=O)NC1CC1 BRHQGQVJLPRDBV-UHFFFAOYSA-N 0.000 claims 1
- XYWOGFYVZOWEAY-UHFFFAOYSA-N n-cyclopropyl-4-[6-[(2,5-difluorophenyl)-difluoromethyl]-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(F)(F)C=2C(=CC=C(F)C=2)F)=CC=C1C(=O)NC1CC1 XYWOGFYVZOWEAY-UHFFFAOYSA-N 0.000 claims 1
- RJXCRDVWWPSBIH-UHFFFAOYSA-N n-cyclopropyl-4-[6-[(3-fluoro-2-hydroxyphenyl)-hydroxymethyl]-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(O)C=2C(=C(F)C=CC=2)O)=CC=C1C(=O)NC1CC1 RJXCRDVWWPSBIH-UHFFFAOYSA-N 0.000 claims 1
- UIAHOKLBNILEDW-UHFFFAOYSA-N n-cyclopropyl-4-[6-[(3-fluoro-2-methoxyphenyl)-hydroxymethyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=C(F)C=CC=C1C(O)C1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 UIAHOKLBNILEDW-UHFFFAOYSA-N 0.000 claims 1
- RJXCRDVWWPSBIH-XMMPIXPASA-N n-cyclopropyl-4-[6-[(r)-(3-fluoro-2-hydroxyphenyl)-hydroxymethyl]-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@H](O)C=2C(=C(F)C=CC=2)O)=CC=C1C(=O)NC1CC1 RJXCRDVWWPSBIH-XMMPIXPASA-N 0.000 claims 1
- GWHGNRRUUCTBGS-XMMPIXPASA-N n-cyclopropyl-4-[6-[(r)-fluoro-(3-fluorophenyl)methyl]-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@H](F)C=2C=C(F)C=CC=2)=CC=C1C(=O)NC1CC1 GWHGNRRUUCTBGS-XMMPIXPASA-N 0.000 claims 1
- RJXCRDVWWPSBIH-DEOSSOPVSA-N n-cyclopropyl-4-[6-[(s)-(3-fluoro-2-hydroxyphenyl)-hydroxymethyl]-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@@H](O)C=2C(=C(F)C=CC=2)O)=CC=C1C(=O)NC1CC1 RJXCRDVWWPSBIH-DEOSSOPVSA-N 0.000 claims 1
- GWHGNRRUUCTBGS-DEOSSOPVSA-N n-cyclopropyl-4-[6-[(s)-fluoro-(3-fluorophenyl)methyl]-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@@H](F)C=2C=C(F)C=CC=2)=CC=C1C(=O)NC1CC1 GWHGNRRUUCTBGS-DEOSSOPVSA-N 0.000 claims 1
- YEIIAQASSRCJDI-UHFFFAOYSA-N n-cyclopropyl-4-[6-[1-(2,3-difluorophenyl)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)C2(CC2)C=2C(=C(F)C=CC=2)F)=CC=C1C(=O)NC1CC1 YEIIAQASSRCJDI-UHFFFAOYSA-N 0.000 claims 1
- ALUVPLUSUAPJFE-UHFFFAOYSA-N n-cyclopropyl-4-[6-[1-(2,3-difluorophenyl)ethenyl]-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(=C)C=2C(=C(F)C=CC=2)F)=CC=C1C(=O)NC1CC1 ALUVPLUSUAPJFE-UHFFFAOYSA-N 0.000 claims 1
- QQESFIBKLFQRKJ-UHFFFAOYSA-N n-cyclopropyl-4-[6-[1-(2,5-difluorophenyl)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)C2(CC2)C=2C(=CC=C(F)C=2)F)=CC=C1C(=O)NC1CC1 QQESFIBKLFQRKJ-UHFFFAOYSA-N 0.000 claims 1
- DSCYGDOLRIGYLN-UHFFFAOYSA-N n-cyclopropyl-4-[6-[1-(3-fluoro-2-hydroxyphenyl)-1-hydroxyethyl]-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(C)(O)C=2C(=C(F)C=CC=2)O)=CC=C1C(=O)NC1CC1 DSCYGDOLRIGYLN-UHFFFAOYSA-N 0.000 claims 1
- XWGFXERFSFMPBR-UHFFFAOYSA-N n-cyclopropyl-4-[6-[1-(3-fluoro-2-methoxyphenyl)-1-hydroxyethyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=C(F)C=CC=C1C(C)(O)C1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 XWGFXERFSFMPBR-UHFFFAOYSA-N 0.000 claims 1
- HBNSSPSUNYWQLD-UHFFFAOYSA-N n-cyclopropyl-4-[6-[1-(3-fluoro-4-methoxyphenyl)ethenyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(OC)=CC=C1C(=C)C1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 HBNSSPSUNYWQLD-UHFFFAOYSA-N 0.000 claims 1
- IARCVGSTOGKBTI-UHFFFAOYSA-N n-cyclopropyl-4-[6-[1-(5-fluoro-2-hydroxyphenyl)ethenyl]-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(=C)C=2C(=CC=C(F)C=2)O)=CC=C1C(=O)NC1CC1 IARCVGSTOGKBTI-UHFFFAOYSA-N 0.000 claims 1
- KGXREOONVRAUID-UHFFFAOYSA-N n-cyclopropyl-4-[6-[1-(5-fluoro-2-methoxyphenyl)ethenyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound COC1=CC=C(F)C=C1C(=C)C1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 KGXREOONVRAUID-UHFFFAOYSA-N 0.000 claims 1
- BEODXDOCLDSVAK-UHFFFAOYSA-N n-cyclopropyl-4-[6-[1-(5-fluoro-2-phenylmethoxyphenyl)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)C2(CC2)C=2C(=CC=C(F)C=2)OCC=2C=CC=CC=2)=CC=C1C(=O)NC1CC1 BEODXDOCLDSVAK-UHFFFAOYSA-N 0.000 claims 1
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- NBVPDUWARRWBKM-UHFFFAOYSA-N n-cyclopropyl-4-[6-[difluoro-(3-fluoro-4-methoxyphenyl)methyl]-8-(3,3,3-trifluoropropylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methylbenzamide Chemical compound C1=C(F)C(OC)=CC=C1C(F)(F)C1=NN2C(C=3C=C(C)C(C(=O)NC4CC4)=CC=3)=CN=C2C(NCCC(F)(F)F)=C1 NBVPDUWARRWBKM-UHFFFAOYSA-N 0.000 claims 1
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| TWI541243B (zh) | 2010-09-10 | 2016-07-11 | 拜耳知識產權公司 | 經取代咪唑并嗒 |
| CA2821817A1 (en) | 2010-12-17 | 2012-06-21 | Bayer Intellectual Property Gmbh | Substituted 6-imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| EP2651947B1 (en) | 2010-12-17 | 2014-12-10 | Bayer Intellectual Property GmbH | 6-thio-substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| RS54044B1 (sr) | 2011-04-21 | 2015-10-30 | Bayer Intellectual Property Gmbh | Triazolopiridini |
| EP3812387A1 (en) * | 2011-07-21 | 2021-04-28 | Sumitomo Dainippon Pharma Oncology, Inc. | Heterocyclic protein kinase inhibitors |
| WO2013135612A1 (en) | 2012-03-14 | 2013-09-19 | Bayer Intellectual Property Gmbh | Substituted imidazopyridazines |
-
2013
- 2013-03-11 WO PCT/EP2013/054841 patent/WO2013135612A1/en not_active Ceased
- 2013-03-11 US US14/384,828 patent/US9512126B2/en not_active Expired - Fee Related
- 2013-03-11 ES ES13710986.4T patent/ES2605946T3/es active Active
- 2013-03-11 CA CA 2867061 patent/CA2867061A1/en not_active Abandoned
- 2013-03-11 JP JP2014561391A patent/JP6166289B2/ja not_active Expired - Fee Related
- 2013-03-11 EP EP13710986.4A patent/EP2825540B1/en not_active Not-in-force
- 2013-03-11 CN CN201380024787.9A patent/CN104284896B/zh not_active Expired - Fee Related
- 2013-03-13 AR ARP130100808 patent/AR090323A1/es unknown
- 2013-03-14 UY UY0001034677A patent/UY34677A/es not_active Application Discontinuation
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