EA037112B1 - Ингибиторы tgf- - Google Patents

Info

Publication number

EA037112B1

EA037112B1 EA201791955A EA201791955A EA037112B1 EA 037112 B1 EA037112 B1 EA 037112B1 EA 201791955 A EA201791955 A EA 201791955A EA 201791955 A EA201791955 A EA 201791955A EA 037112 B1 EA037112 B1 EA 037112B1

Authority

EA

Eurasian Patent Office

Prior art keywords

fluorophenyl

imidazol

imidazo

pyridazine

carbonitrile

Prior art date

2015-03-02

Links

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• 239000003112 inhibitor Substances 0.000 title description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 256
• 238000000034 method Methods 0.000 claims abstract description 112
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 56
• 150000003839 salts Chemical class 0.000 claims abstract description 45
• 201000010099 disease Diseases 0.000 claims abstract description 38
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
• 230000001404 mediated effect Effects 0.000 claims abstract description 3
• -1 3-hydroxycyclobutyl Chemical group 0.000 claims description 619
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 252
• PJESVVYWPFAJCS-UHFFFAOYSA-N pyridazine-3-carbonitrile Chemical compound N#CC1=CC=CN=N1 PJESVVYWPFAJCS-UHFFFAOYSA-N 0.000 claims description 160
• DMYLUKNFEYWGCH-UHFFFAOYSA-N pyridazine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=N1 DMYLUKNFEYWGCH-UHFFFAOYSA-N 0.000 claims description 84
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 83
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 69
• 125000000217 alkyl group Chemical group 0.000 claims description 61
• 229910052736 halogen Inorganic materials 0.000 claims description 59
• 150000002367 halogens Chemical class 0.000 claims description 59
• YLXWTAXPOOYRSL-UHFFFAOYSA-N imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound C1=CC=NN2C(C#N)=CN=C21 YLXWTAXPOOYRSL-UHFFFAOYSA-N 0.000 claims description 52
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 239000001257 hydrogen Substances 0.000 claims description 49
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 49
• 239000003795 chemical substances by application Substances 0.000 claims description 45
• 125000001188 haloalkyl group Chemical group 0.000 claims description 34
• 102000004887 Transforming Growth Factor beta Human genes 0.000 claims description 33
• 108090001012 Transforming Growth Factor beta Proteins 0.000 claims description 33
• ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 claims description 33
• YCLUMBJQKREDFM-UHFFFAOYSA-N imidazo[1,2-b]pyridazine-3-carboxamide Chemical compound C1=CC=NN2C(C(=O)N)=CN=C21 YCLUMBJQKREDFM-UHFFFAOYSA-N 0.000 claims description 31
• 125000003118 aryl group Chemical group 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• 201000011510 cancer Diseases 0.000 claims description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 17
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 16
• 229910052717 sulfur Chemical group 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 230000002401 inhibitory effect Effects 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 239000002246 antineoplastic agent Substances 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 11
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 10
• 125000003545 alkoxy group Chemical group 0.000 claims description 10
• 125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 claims description 10
• 125000004122 cyclic group Chemical group 0.000 claims description 9
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 8
• 239000001301 oxygen Chemical group 0.000 claims description 8
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 7
• 229940127089 cytotoxic agent Drugs 0.000 claims description 7
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 6
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• VZZBCNXVZFAIQX-UHFFFAOYSA-N bms-986260 Chemical compound ClC=1C=C(C=CC=1F)C=1N=CN(C=1C=1C=CC=2N(N=1)C(=CN=2)C#N)CCO VZZBCNXVZFAIQX-UHFFFAOYSA-N 0.000 claims description 6
• 239000011593 sulfur Chemical group 0.000 claims description 6
• RRWODQALHOJALX-UHFFFAOYSA-N 2-[6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazin-3-yl]propan-2-ol Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C(C)(C)O)C1=CC=C(C=C1)F)F RRWODQALHOJALX-UHFFFAOYSA-N 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• CMSUIPSAXZVIEI-UHFFFAOYSA-N 1-[6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazin-3-yl]ethanol Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C(C)O)C1=CC=C(C=C1)F)F CMSUIPSAXZVIEI-UHFFFAOYSA-N 0.000 claims description 3
• AIWFGWNOBBUPGY-UHFFFAOYSA-N 2-[6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazin-3-yl]ethanol Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)CCO)C1=CC=C(C=C1)F)F AIWFGWNOBBUPGY-UHFFFAOYSA-N 0.000 claims description 3
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 3
• FFARGLZRLVWCLR-UHFFFAOYSA-N 5-[6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazin-3-yl]-1,3-oxazole Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C1=CN=CO1)C1=CC=C(C=C1)F)F FFARGLZRLVWCLR-UHFFFAOYSA-N 0.000 claims description 3
• RUFJJHLOWAYYNK-UHFFFAOYSA-N 6-[5-(4-fluorophenyl)-3-(3-hydroxy-3-methylbutyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC1=CC=C(C=C1)C=1N=CN(C=1C=1C=CC=2N(N=1)C(=CN=2)C#N)CCC(C)(C)O RUFJJHLOWAYYNK-UHFFFAOYSA-N 0.000 claims description 3
• MPJRDTOQAWNWAP-UHFFFAOYSA-N 6-[5-(4-fluorophenyl)-3-methylimidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC1=CC=C(C=C1)C=1N=CN(C=1C=1C=CC=2N(N=1)C(=CN=2)C#N)C MPJRDTOQAWNWAP-UHFFFAOYSA-N 0.000 claims description 3
• FLOGFPWWNWYVPN-UHFFFAOYSA-N 6-[5-(4-fluorophenyl)-3-propan-2-ylimidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC1=CC=C(C=C1)C=1N=CN(C=1C=1C=CC=2N(N=1)C(=CN=2)C#N)C(C)C FLOGFPWWNWYVPN-UHFFFAOYSA-N 0.000 claims description 3
• XHGJZPUFJXDWQS-UHFFFAOYSA-N [6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazin-3-yl]methanol Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)CO)C1=CC=C(C=C1)F)F XHGJZPUFJXDWQS-UHFFFAOYSA-N 0.000 claims description 3
• PVXOUGHWLCBJOW-UHFFFAOYSA-N azetidine-1-carboxamide Chemical compound NC(=O)N1CCC1 PVXOUGHWLCBJOW-UHFFFAOYSA-N 0.000 claims description 3
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• ZSWBOAJXCVKKMP-UHFFFAOYSA-N 1-[6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazin-3-yl]-2,2,2-trifluoroethanol Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C(C(F)(F)F)O)C1=CC=C(C=C1)F)F ZSWBOAJXCVKKMP-UHFFFAOYSA-N 0.000 claims description 2
• GUNDQCGSBHUTRO-UHFFFAOYSA-N 1-tert-butyl-3-[[6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazin-3-yl]methyl]urea Chemical compound C(C)(C)(C)NC(=O)NCC1=CN=C2N1N=C(C=C2)C1=C(N=CN1CC(F)F)C1=CC=C(C=C1)F GUNDQCGSBHUTRO-UHFFFAOYSA-N 0.000 claims description 2
• YFKVHWAIZLRGQD-UHFFFAOYSA-N 2-[5-(3-cyanoimidazo[1,2-b]pyridazin-6-yl)-1-(2,2-difluoroethyl)imidazol-4-yl]benzamide Chemical compound C(#N)C1=CN=C2N1N=C(C=C2)C1=C(N=CN1CC(F)F)C1=C(C(=O)N)C=CC=C1 YFKVHWAIZLRGQD-UHFFFAOYSA-N 0.000 claims description 2
• QDUBUKBLTBLKSO-UHFFFAOYSA-N 6-[3-(1-cyanocyclopropyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound C(#N)C1(CC1)N1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC=C(C=C1)F QDUBUKBLTBLKSO-UHFFFAOYSA-N 0.000 claims description 2
• GTXWZLVOHNLICQ-UHFFFAOYSA-N 6-[3-(1-fluorobutan-2-yl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound CCC(CF)n1cnc(c1-c1ccc2ncc(C#N)n2n1)-c1ccc(F)cc1 GTXWZLVOHNLICQ-UHFFFAOYSA-N 0.000 claims description 2
• BURMGIUZWPVWKC-UHFFFAOYSA-N 6-[3-(1-fluorobutan-2-yl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carboxamide Chemical compound CCC(CF)N1C=NC(=C1C1=NN2C(C=C1)=NC=C2C(N)=O)C1=CC=C(F)C=C1 BURMGIUZWPVWKC-UHFFFAOYSA-N 0.000 claims description 2
• BYNUJHIHRYVHIS-UHFFFAOYSA-N 6-[3-(2,2-difluoroethyl)-5-(2-hydroxyphenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=C(C=CC=C1)O)F BYNUJHIHRYVHIS-UHFFFAOYSA-N 0.000 claims description 2
• LKIOFJKRLNXCHM-UHFFFAOYSA-N 6-[3-(2,2-difluoroethyl)-5-(3-hydroxyphenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC(=CC=C1)O)F LKIOFJKRLNXCHM-UHFFFAOYSA-N 0.000 claims description 2
• PZPFXNOFLVGPKQ-UHFFFAOYSA-N 6-[3-(2,2-difluoroethyl)-5-(3-methylsulfonylphenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC(=CC=C1)S(=O)(=O)C)F PZPFXNOFLVGPKQ-UHFFFAOYSA-N 0.000 claims description 2
• VBTGRKWAIXSXHJ-UHFFFAOYSA-N 6-[3-(2,2-difluoroethyl)-5-(4-fluoro-3-methoxyphenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC(=C(C=C1)F)OC)F VBTGRKWAIXSXHJ-UHFFFAOYSA-N 0.000 claims description 2
• CUZYUXWEQICOBS-UHFFFAOYSA-N 6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]-3-(difluoromethyl)imidazo[1,2-b]pyridazine Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C(F)F)C1=CC=C(C=C1)F)F CUZYUXWEQICOBS-UHFFFAOYSA-N 0.000 claims description 2
• HZXCIXSJCJHRJV-UHFFFAOYSA-N 6-[3-(2,2-difluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]-3-ethenylimidazo[1,2-b]pyridazine Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C=C)C1=CC=C(C=C1)F)F HZXCIXSJCJHRJV-UHFFFAOYSA-N 0.000 claims description 2
• NHLDFZIDIQCYDI-UHFFFAOYSA-N 6-[3-(2,2-difluoroethyl)-5-(4-methoxyphenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC=C(C=C1)OC)F NHLDFZIDIQCYDI-UHFFFAOYSA-N 0.000 claims description 2
• ZZDYBGUMEVRYOV-UHFFFAOYSA-N 6-[3-(2,2-difluoroethyl)-5-(4-propan-2-yloxyphenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC=C(C=C1)OC(C)C)F ZZDYBGUMEVRYOV-UHFFFAOYSA-N 0.000 claims description 2
• LCAOAERTWRJUNY-UHFFFAOYSA-N 6-[3-(2,2-difluoroethyl)-5-[3-(2-hydroxypropan-2-yl)phenyl]imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC(=CC=C1)C(C)(C)O)F LCAOAERTWRJUNY-UHFFFAOYSA-N 0.000 claims description 2
• HIZKQJCHZWYQGG-UHFFFAOYSA-N 6-[3-(2,2-difluoroethyl)-5-[3-(hydroxymethyl)phenyl]imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC(=CC=C1)CO)F HIZKQJCHZWYQGG-UHFFFAOYSA-N 0.000 claims description 2
• UGBGZGUCQHWFOS-UHFFFAOYSA-N 6-[3-(2,2-difluoroethyl)-5-[4-(trifluoromethyl)phenyl]imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC=C(C=C1)C(F)(F)F)F UGBGZGUCQHWFOS-UHFFFAOYSA-N 0.000 claims description 2
• QXOUAOPCYZFXSY-UHFFFAOYSA-N 6-[3-(2,2-difluoroethyl)-5-phenylimidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC=CC=C1)F QXOUAOPCYZFXSY-UHFFFAOYSA-N 0.000 claims description 2
• QDTOLPNMVRYFJM-UHFFFAOYSA-N 6-[3-(2,2-difluoropropyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC=C(C=C1)F)(C)F QDTOLPNMVRYFJM-UHFFFAOYSA-N 0.000 claims description 2
• DCZWNLFBLYYQNX-UHFFFAOYSA-N 6-[3-(2-fluoro-2-methylpropyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC(CN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC=C(C=C1)F)(C)C DCZWNLFBLYYQNX-UHFFFAOYSA-N 0.000 claims description 2
• VWDCDLVAWTZKJA-UHFFFAOYSA-N 6-[3-(2-fluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FCCN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC=C(C=C1)F VWDCDLVAWTZKJA-UHFFFAOYSA-N 0.000 claims description 2
• WZSHKAWTTZBHSJ-UHFFFAOYSA-N 6-[3-(2-fluoroethyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carboxamide Chemical compound FCCN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C(=O)N)C1=CC=C(C=C1)F WZSHKAWTTZBHSJ-UHFFFAOYSA-N 0.000 claims description 2
• YZXVJUAAFXYRNU-UHFFFAOYSA-N 6-[3-(3,3-difluorocyclobutyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC1(CC(C1)N1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC=C(C=C1)F)F YZXVJUAAFXYRNU-UHFFFAOYSA-N 0.000 claims description 2
• RFYREBLBAKCPTO-UHFFFAOYSA-N 6-[3-(3,3-difluorocyclopentyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carboxamide Chemical compound FC1(CC(CC1)N1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C(=O)N)C1=CC=C(C=C1)F)F RFYREBLBAKCPTO-UHFFFAOYSA-N 0.000 claims description 2
• FSAGRQILJJYGPQ-UHFFFAOYSA-N 6-[3-(3,3-difluoropropyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC(CCN1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC=C(C=C1)F)F FSAGRQILJJYGPQ-UHFFFAOYSA-N 0.000 claims description 2
• RMPYIDCKQIUJDI-UHFFFAOYSA-N 6-[3-(4,4-difluorocyclohexyl)-5-(4-fluorophenyl)imidazol-4-yl]imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound FC1(CCC(CC1)N1C=NC(=C1C=1C=CC=2N(N=1)C(=CN=2)C#N)C1=CC=C(C=C1)F)F RMPYIDCKQIUJDI-UHFFFAOYSA-N 0.000 claims description 2
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