JP6166289B2 - 置換イミダゾピリダジン - Google Patents
置換イミダゾピリダジン Download PDFInfo
- Publication number
- JP6166289B2 JP6166289B2 JP2014561391A JP2014561391A JP6166289B2 JP 6166289 B2 JP6166289 B2 JP 6166289B2 JP 2014561391 A JP2014561391 A JP 2014561391A JP 2014561391 A JP2014561391 A JP 2014561391A JP 6166289 B2 JP6166289 B2 JP 6166289B2
- Authority
- JP
- Japan
- Prior art keywords
- cyclopropyl
- imidazo
- trifluoropropyl
- 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.)
- Expired - Fee Related
Links
- 150000005233 imidazopyridazines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 441
- -1 hydroxy - Chemical class 0.000 claims description 338
- 125000005843 halogen group Chemical group 0.000 claims description 158
- 239000000203 mixture Substances 0.000 claims description 124
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 85
- 238000000034 method Methods 0.000 claims description 82
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 68
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 65
- 150000003839 salts Chemical class 0.000 claims description 63
- 229910052799 carbon Inorganic materials 0.000 claims description 56
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 50
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 45
- 206010028980 Neoplasm Diseases 0.000 claims description 40
- 201000010099 disease Diseases 0.000 claims description 39
- 239000003814 drug Substances 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 28
- 230000004663 cell proliferation Effects 0.000 claims description 26
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 25
- 238000004519 manufacturing process Methods 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 230000010261 cell growth Effects 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 230000004083 survival effect Effects 0.000 claims description 20
- 206010027476 Metastases Diseases 0.000 claims description 19
- 229940079593 drug Drugs 0.000 claims description 19
- 230000024932 T cell mediated immunity Effects 0.000 claims description 18
- 230000028709 inflammatory response Effects 0.000 claims description 18
- 230000001413 cellular effect Effects 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 16
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 13
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 8
- 230000037361 pathway Effects 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 7
- 229960004641 rituximab Drugs 0.000 claims description 7
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 6
- PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 claims description 6
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 6
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 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 description 6
- 229960002949 fluorouracil Drugs 0.000 claims description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 5
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 5
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 5
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 5
- 229960004397 cyclophosphamide Drugs 0.000 claims description 5
- 229960004679 doxorubicin Drugs 0.000 claims description 5
- 229930013356 epothilone Natural products 0.000 claims description 5
- 229960001101 ifosfamide Drugs 0.000 claims description 5
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- 229960001924 melphalan Drugs 0.000 claims description 5
- 229960000485 methotrexate Drugs 0.000 claims description 5
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims description 5
- 229960001156 mitoxantrone Drugs 0.000 claims description 5
- CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 claims description 5
- 229960000624 procarbazine Drugs 0.000 claims description 5
- 229960003048 vinblastine Drugs 0.000 claims description 5
- 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 description 5
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- WYWHKKSPHMUBEB-UHFFFAOYSA-N 6-Mercaptoguanine Natural products N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 claims description 4
- 108010006654 Bleomycin Proteins 0.000 claims description 4
- 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 description 4
- 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 description 4
- GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 claims description 4
- 229960001467 bortezomib Drugs 0.000 claims description 4
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims description 4
- 229960004630 chlorambucil Drugs 0.000 claims description 4
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 4
- 229960005420 etoposide Drugs 0.000 claims description 4
- 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 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 229960000908 idarubicin Drugs 0.000 claims description 4
- 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 description 4
- MNRILEROXIRVNJ-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=NC=N[C]21 MNRILEROXIRVNJ-UHFFFAOYSA-N 0.000 claims description 4
- 229960003087 tioguanine Drugs 0.000 claims description 4
- 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 claims description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
- GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 claims description 3
- 229940123237 Taxane Drugs 0.000 claims description 3
- 229960001561 bleomycin Drugs 0.000 claims description 3
- 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 description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 3
- 229960000975 daunorubicin Drugs 0.000 claims description 3
- 208000019691 hematopoietic and lymphoid cell neoplasm Diseases 0.000 claims description 3
- 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 description 3
- 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 description 3
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- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- VDAGWVKYXOJZCP-UHFFFAOYSA-N n-cyclopropyl-4-[6-[hydroxy-(4-methoxyphenyl)methyl]-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 VDAGWVKYXOJZCP-UHFFFAOYSA-N 0.000 claims description 3
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- 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 description 2
- 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 description 2
- 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 description 2
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- 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
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- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
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- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| EP13154139 | 2013-02-06 | ||
| EP13154139.3 | 2013-02-06 | ||
| PCT/EP2013/054841 WO2013135612A1 (en) | 2012-03-14 | 2013-03-11 | Substituted imidazopyridazines |
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| JP2015513559A JP2015513559A (ja) | 2015-05-14 |
| JP2015513559A5 JP2015513559A5 (enExample) | 2016-03-24 |
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| JP6166289B2 (ja) | 2012-03-14 | 2017-07-19 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 置換イミダゾピリダジン |
| CA2914745A1 (en) | 2013-06-11 | 2014-12-18 | Bayer Pharma Aktiengesellschaft | Prodrug derivatives of substituted triazolopyridines |
| AP2015008915A0 (en) * | 2013-06-13 | 2015-12-31 | Bayer Pharma AG | Combination of a imidazopyridazine derivative and a mitotic agent for the treatment of cancer |
| EP3283642B1 (en) | 2015-04-17 | 2023-10-11 | Netherlands Translational Research Center Holding B.V. | Prognostic biomarkers for ttk inhibitor chemotherapy |
| CN107847580B (zh) | 2015-07-07 | 2022-08-12 | 扬森疫苗与预防公司 | 针对rsv的疫苗 |
| GB201907616D0 (en) * | 2019-05-29 | 2019-07-10 | Galapagos Nv | Novel compounds and pharmaceutical compositons thereof for the treatment of diseases |
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| US5023252A (en) | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US5011472A (en) | 1988-09-06 | 1991-04-30 | Brown University Research Foundation | Implantable delivery system for biological factors |
| PL332040A1 (en) | 1996-08-28 | 1999-08-16 | Pfizer | Substitution 6,5-heterobicyclic derivatives |
| ES2235331T3 (es) | 1997-05-28 | 2005-07-01 | Aventis Pharmaceuticals Inc | Compuestos quinolina y quinoxalina que inhiben el factor de crecimiento derivado de plaquetas y/o tirosina quinasas p561ck. |
| US6514989B1 (en) | 2001-07-20 | 2003-02-04 | Hoffmann-La Roche Inc. | Aromatic and heteroaromatic substituted 1,2,4-triazolo pyridine derivatives |
| JP2004346016A (ja) | 2003-05-22 | 2004-12-09 | Otsuka Chemical Co Ltd | トリフルオロメチルキノキサリン化合物、その製造方法、及び有害生物防除剤 |
| JP4499721B2 (ja) | 2003-06-30 | 2010-07-07 | ヒフ バイオ，インク． | 化合物、組成物および方法 |
| EP1799680A2 (en) | 2004-10-07 | 2007-06-27 | Warner-Lambert Company LLC | Triazolopyridine derivatives as antibacterial agents |
| US20070049591A1 (en) | 2005-08-25 | 2007-03-01 | Kalypsys, Inc. | 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 |
| WO2007065010A2 (en) | 2005-12-02 | 2007-06-07 | Hif Bio, Inc. | Anti-angiogenesis compounds |
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| CA2658725A1 (en) | 2006-08-16 | 2008-02-21 | Exelixis, Inc. | Using pi3k and mek modulators in treatments of cancer |
| JP5336375B2 (ja) | 2006-08-30 | 2013-11-06 | セルゾーム リミテッド | キナーゼ阻害剤としてのトリアゾール誘導体 |
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| TW200902008A (en) | 2007-05-10 | 2009-01-16 | Smithkline Beecham Corp | Quinoxaline derivatives as PI3 kinase inhibitors |
| CN101801966A (zh) | 2007-07-18 | 2010-08-11 | 诺瓦提斯公司 | 双环杂芳基化合物和它们作为激酶抑制剂的用途 |
| JP2010535804A (ja) | 2007-08-09 | 2010-11-25 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | Ｐｉ３キナーゼ阻害薬としてのキノキサリン誘導体 |
| EP2212326A1 (en) | 2007-08-23 | 2010-08-04 | AstraZeneca AB | 2-anilinopurin-8-ones as inhibitors of ttk/mps1 for the treatment of proliferative disorders |
| CA2691448A1 (en) | 2007-08-31 | 2009-03-05 | Dominique Swinnen | Triazolopyridine compounds and their use as ask inhibitors |
| GB0719803D0 (en) | 2007-10-10 | 2007-11-21 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| UA102828C2 (en) | 2007-11-27 | 2013-08-27 | Целльзом Лимитед | Amino triazoles as p13k inhibitors |
| JP5599783B2 (ja) | 2008-05-30 | 2014-10-01 | アムジエン・インコーポレーテツド | Ｐｉ３キナーゼの阻害薬 |
| 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 |
| WO2010092015A1 (en) | 2009-02-10 | 2010-08-19 | Cellzome Limited | Urea triazololo [1, 5-a] pyridine derivatives as pi3k inhibitors |
| EP2396324A1 (en) | 2009-02-13 | 2011-12-21 | Fovea Pharmaceuticals | Ý1, 2, 4¨triazolo ý1, 5 -a¨pyridines as kinase inhibitors |
| JP6168773B2 (ja) | 2009-04-29 | 2017-07-26 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 置換イミダゾキノキサリン |
| TW201107329A (en) | 2009-07-30 | 2011-03-01 | Oncotherapy Science Inc | Fused imidazole derivative having ttk inhibitory action |
| WO2011026579A1 (en) | 2009-09-04 | 2011-03-10 | Bayer Schering Pharma Aktiengesellschaft | Substituted aminoquinoxalines as tyrosine threonine kinase inhibitors |
| 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 |
| EP2343295A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Triazolopyridine derivates |
| PH12012501381A1 (en) | 2010-01-15 | 2012-10-22 | Janssen Pharmaceuticals Inc | Novel substituted bicyclic triazole derivatives as gamma secretase modulators |
| US20110190269A1 (en) | 2010-02-01 | 2011-08-04 | Karlheinz Baumann | Gamma secretase modulators |
| CN103038235B (zh) | 2010-06-01 | 2015-07-29 | 拜耳知识产权有限责任公司 | 取代的咪唑并吡嗪 |
| TWI541243B (zh) | 2010-09-10 | 2016-07-11 | 拜耳知識產權公司 | 經取代咪唑并嗒 |
| WO2012080228A1 (en) | 2010-12-17 | 2012-06-21 | Bayer Pharma Aktiengesellschaft | 6-thio-substituted imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders |
| US9284317B2 (en) | 2010-12-17 | 2016-03-15 | Bayer Intellectual Property Gmbh | Substituted imidazo[1,2-a]pyrazines as MPS-1 inhibitors |
| US20140120087A1 (en) | 2011-04-21 | 2014-05-01 | Bayer Intellectual Property Gmbh | Triazolopyridines |
| DK2734205T3 (en) * | 2011-07-21 | 2018-06-14 | Tolero Pharmaceuticals Inc | Heterocyclic Protein Kinase Inhibitors |
| JP6166289B2 (ja) | 2012-03-14 | 2017-07-19 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 置換イミダゾピリダジン |
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2013
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- 2013-03-11 ES ES13710986.4T patent/ES2605946T3/es active Active
- 2013-03-11 WO PCT/EP2013/054841 patent/WO2013135612A1/en not_active Ceased
- 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
- 2013-03-11 US US14/384,828 patent/US9512126B2/en not_active Expired - Fee Related
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Also Published As
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| HK1206022A1 (zh) | 2015-12-31 |
| CN104284896B (zh) | 2016-06-01 |
| AR090323A1 (es) | 2014-11-05 |
| US20150104526A1 (en) | 2015-04-16 |
| CN104284896A (zh) | 2015-01-14 |
| WO2013135612A1 (en) | 2013-09-19 |
| JP2015513559A (ja) | 2015-05-14 |
| EP2825540B1 (en) | 2016-09-14 |
| ES2605946T3 (es) | 2017-03-17 |
| EP2825540A1 (en) | 2015-01-21 |
| UY34677A (es) | 2013-10-31 |
| US9512126B2 (en) | 2016-12-06 |
| CA2867061A1 (en) | 2013-09-19 |
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