SK287417B6 - Substituované pyridíny a pyridazíny s inhibičným účinkom na angiogenézu a ich použitie - Google Patents

Info

Publication number

SK287417B6

SK287417B6 SK591-2002A SK5912002A SK287417B6 SK 287417 B6 SK287417 B6 SK 287417B6 SK 5912002 A SK5912002 A SK 5912002A SK 287417 B6 SK287417 B6 SK 287417B6

Authority

SK

Slovakia

Prior art keywords

group

substituted

alkyl

optionally substituted

methyl

Prior art date

1999-09-28

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• 230000033115 angiogenesis Effects 0.000 title claims abstract description 26
• 150000004892 pyridazines Chemical class 0.000 title abstract description 5
• 150000003222 pyridines Chemical class 0.000 title abstract description 5
• 230000002401 inhibitory effect Effects 0.000 title abstract description 3
• 125000001424 substituent group Chemical group 0.000 claims abstract description 77
• 125000003118 aryl group Chemical group 0.000 claims abstract description 48
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 45
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
• 230000002159 abnormal effect Effects 0.000 claims abstract description 12
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
• 241000124008 Mammalia Species 0.000 claims abstract description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 321
• 125000003282 alkyl amino group Chemical group 0.000 claims description 236
• 150000001875 compounds Chemical class 0.000 claims description 166
• 229910052717 sulfur Inorganic materials 0.000 claims description 114
• 229910052760 oxygen Inorganic materials 0.000 claims description 113
• 125000000623 heterocyclic group Chemical group 0.000 claims description 92
• 229910052757 nitrogen Inorganic materials 0.000 claims description 91
• 125000004429 atom Chemical group 0.000 claims description 83
• 125000004432 carbon atom Chemical group C* 0.000 claims description 80
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 78
• 125000001072 heteroaryl group Chemical group 0.000 claims description 77
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 75
• -1 mercapto, sulfo Chemical group 0.000 claims description 71
• 229910052736 halogen Inorganic materials 0.000 claims description 66
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 61
• 150000002367 halogens Chemical class 0.000 claims description 60
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 56
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 46
• 125000003545 alkoxy group Chemical group 0.000 claims description 45
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 45
• 125000004414 alkyl thio group Chemical group 0.000 claims description 43
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 42
• 125000003107 substituted aryl group Chemical group 0.000 claims description 37
• 125000003277 amino group Chemical group 0.000 claims description 34
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
• 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 31
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 30
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
• 125000003342 alkenyl group Chemical group 0.000 claims description 29
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 27
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 26
• 125000005842 heteroatom Chemical group 0.000 claims description 26
• 230000008878 coupling Effects 0.000 claims description 21
• 238000010168 coupling process Methods 0.000 claims description 21
• 238000005859 coupling reaction Methods 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 20
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 20
• 230000015572 biosynthetic process Effects 0.000 claims description 18
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 18
• 125000004434 sulfur atom Chemical group 0.000 claims description 17
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• 239000001301 oxygen Substances 0.000 claims description 16
• 229920006395 saturated elastomer Polymers 0.000 claims description 16
• 239000011593 sulfur Substances 0.000 claims description 16
• 125000002947 alkylene group Chemical group 0.000 claims description 14
• 125000002619 bicyclic group Chemical group 0.000 claims description 14
• 125000002837 carbocyclic group Chemical group 0.000 claims description 14
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 13
• 150000001409 amidines Chemical class 0.000 claims description 13
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 13
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 12
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 11
• 125000004423 acyloxy group Chemical group 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000006413 ring segment Chemical group 0.000 claims description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 9
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 125000002950 monocyclic group Chemical group 0.000 claims description 8
• 201000004624 Dermatitis Diseases 0.000 claims description 7
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 7
• 206010038903 Retinal vascular occlusion Diseases 0.000 claims description 7
• 206010038923 Retinopathy Diseases 0.000 claims description 7
• 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 7
• 230000000302 ischemic effect Effects 0.000 claims description 7
• 208000002780 macular degeneration Diseases 0.000 claims description 7
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
• 230000004614 tumor growth Effects 0.000 claims description 7
• 201000004681 Psoriasis Diseases 0.000 claims description 6
• 208000017442 Retinal disease Diseases 0.000 claims description 6
• 239000013256 coordination polymer Substances 0.000 claims description 6
• 239000001257 hydrogen Substances 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
• 150000001412 amines Chemical class 0.000 claims description 5
• 208000035475 disorder Diseases 0.000 claims description 5
• 206010015218 Erythema multiforme Diseases 0.000 claims description 4
• 206010034277 Pemphigoid Diseases 0.000 claims description 4
• 208000000594 bullous pemphigoid Diseases 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
• VXYQISXSMNDTSX-UHFFFAOYSA-N 7-n-(1,3-benzothiazol-6-yl)-4-n-(2,3-dihydro-1h-inden-5-yl)thieno[2,3-d]pyridazine-4,7-diamine Chemical compound C1=C2N=CSC2=CC(NC2=NN=C(C=3C=CSC=32)NC2=CC=C3CCCC3=C2)=C1 VXYQISXSMNDTSX-UHFFFAOYSA-N 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 3
• TXQXILXAUFGWDV-UHFFFAOYSA-N 4-[[4-(4-chloroanilino)thieno[2,3-d]pyridazin-7-yl]oxymethyl]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC(COC=2C=3SC=CC=3C(NC=3C=CC(Cl)=CC=3)=NN=2)=C1 TXQXILXAUFGWDV-UHFFFAOYSA-N 0.000 claims description 2
• JDYKOEGXSOYACK-UHFFFAOYSA-N 7-n-(1,3-benzothiazol-6-yl)-4-n-(4-chlorophenyl)thieno[2,3-d]pyridazine-4,7-diamine Chemical compound C1=CC(Cl)=CC=C1NC(C=1C=CSC=11)=NN=C1NC1=CC=C(N=CS2)C2=C1 JDYKOEGXSOYACK-UHFFFAOYSA-N 0.000 claims description 2
• PONAXVAFSSUYFZ-UHFFFAOYSA-N furo[2,3-d]pyridazine Chemical compound N1=NC=C2OC=CC2=C1 PONAXVAFSSUYFZ-UHFFFAOYSA-N 0.000 claims description 2
• RVLAFRCLNCDGNF-UHFFFAOYSA-N n-(4-methoxyphenyl)-7-(pyridin-4-ylmethoxy)furo[2,3-d]pyridazin-4-amine Chemical compound C1=CC(OC)=CC=C1NC(C=1C=COC=11)=NN=C1OCC1=CC=NC=C1 RVLAFRCLNCDGNF-UHFFFAOYSA-N 0.000 claims description 2
• 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
• DKUSPJDQVGZXQE-UHFFFAOYSA-N 4-[(4-anilinofuro[2,3-d]pyridazin-7-yl)oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=CC=CC=3)=NN=2)=C1 DKUSPJDQVGZXQE-UHFFFAOYSA-N 0.000 claims 1
• FAYKYGVTAZJBFA-UHFFFAOYSA-N 4-[[4-(1,3-benzodioxol-5-ylamino)thieno[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3SC=CC=3C(NC=3C=C4OCOC4=CC=3)=NN=2)=C1 FAYKYGVTAZJBFA-UHFFFAOYSA-N 0.000 claims 1
• ZHAAOKXIQJXHFV-UHFFFAOYSA-N 4-[[4-(1,3-benzothiazol-6-ylamino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=C4SC=NC4=CC=3)=NN=2)=C1 ZHAAOKXIQJXHFV-UHFFFAOYSA-N 0.000 claims 1
• IDLLLASUQRBCHK-UHFFFAOYSA-N 4-[[4-(1h-indazol-5-ylamino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=C4C=NNC4=CC=3)=NN=2)=C1 IDLLLASUQRBCHK-UHFFFAOYSA-N 0.000 claims 1
• VMVSIBSHVORCGB-UHFFFAOYSA-N 4-[[4-(2,3-dihydro-1-benzofuran-5-ylamino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=C4CCOC4=CC=3)=NN=2)=C1 VMVSIBSHVORCGB-UHFFFAOYSA-N 0.000 claims 1
• RCPHXEZEKHMLCD-UHFFFAOYSA-N 4-[[4-(2,3-dihydro-1h-inden-5-ylamino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=C4CCCC4=CC=3)=NN=2)=C1 RCPHXEZEKHMLCD-UHFFFAOYSA-N 0.000 claims 1
• GAFLGXSOLKTMJY-UHFFFAOYSA-N 4-[[4-(2,3-dihydro-1h-inden-5-ylamino)thieno[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3SC=CC=3C(NC=3C=C4CCCC4=CC=3)=NN=2)=C1 GAFLGXSOLKTMJY-UHFFFAOYSA-N 0.000 claims 1
• HMNSECOWULWJJW-UHFFFAOYSA-N 4-[[4-(2-methoxyanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C(=CC=CC=3)OC)=NN=2)=C1 HMNSECOWULWJJW-UHFFFAOYSA-N 0.000 claims 1
• PFUMBUZTNYEVKX-UHFFFAOYSA-N 4-[[4-(3,4-dichloroanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=C(Cl)C(Cl)=CC=3)=NN=2)=C1 PFUMBUZTNYEVKX-UHFFFAOYSA-N 0.000 claims 1
• BMHNJUQGRNQQHT-UHFFFAOYSA-N 4-[[4-(3,4-difluoroanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=C(F)C(F)=CC=3)=NN=2)=C1 BMHNJUQGRNQQHT-UHFFFAOYSA-N 0.000 claims 1
• CZWVTRMDVHNIAH-UHFFFAOYSA-N 4-[[4-(3,5-dimethylanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=C(C)C=C(C)C=3)=NN=2)=C1 CZWVTRMDVHNIAH-UHFFFAOYSA-N 0.000 claims 1
• QTBCALYQDPEUOG-UHFFFAOYSA-N 4-[[4-(3-chloro-4-methoxyanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=C(Cl)C(OC)=CC=3)=NN=2)=C1 QTBCALYQDPEUOG-UHFFFAOYSA-N 0.000 claims 1
• CLXHQSJIWSSXOC-UHFFFAOYSA-N 4-[[4-(3-methoxy-4-methylanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=C(OC)C(C)=CC=3)=NN=2)=C1 CLXHQSJIWSSXOC-UHFFFAOYSA-N 0.000 claims 1
• IPXJMLCTWUHZAN-UHFFFAOYSA-N 4-[[4-(3-methoxyanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=C(OC)C=CC=3)=NN=2)=C1 IPXJMLCTWUHZAN-UHFFFAOYSA-N 0.000 claims 1
• YXKLNJHBYAACTK-UHFFFAOYSA-N 4-[[4-(4-bromoanilino)thieno[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3SC=CC=3C(NC=3C=CC(Br)=CC=3)=NN=2)=C1 YXKLNJHBYAACTK-UHFFFAOYSA-N 0.000 claims 1
• XHSHOWRXRUPCIZ-UHFFFAOYSA-N 4-[[4-(4-chloroanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-(2-hydroxyethyl)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NCCO)=CC(COC=2C=3OC=CC=3C(NC=3C=CC(Cl)=CC=3)=NN=2)=C1 XHSHOWRXRUPCIZ-UHFFFAOYSA-N 0.000 claims 1
• XJRPVXSUODMGGO-UHFFFAOYSA-N 4-[[4-(4-chloroanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-cyclopropylpyridine-2-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(C=1C=COC=11)=NN=C1OCC1=CC=NC(C(=O)NC2CC2)=C1 XJRPVXSUODMGGO-UHFFFAOYSA-N 0.000 claims 1
• FPABXUQFXXLLJT-UHFFFAOYSA-N 4-[[4-(4-chloroanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-ethylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NCC)=CC(COC=2C=3OC=CC=3C(NC=3C=CC(Cl)=CC=3)=NN=2)=C1 FPABXUQFXXLLJT-UHFFFAOYSA-N 0.000 claims 1
• PHCDKYZLKDULAY-UHFFFAOYSA-N 4-[[4-(4-chloroanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide;2-hydroxyethanesulfonic acid Chemical compound OCCS(O)(=O)=O.C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=CC(Cl)=CC=3)=NN=2)=C1 PHCDKYZLKDULAY-UHFFFAOYSA-N 0.000 claims 1
• XGMDBDDOXZCVRU-UHFFFAOYSA-N 4-[[4-(4-chloroanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide;4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1.C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=CC(Cl)=CC=3)=NN=2)=C1 XGMDBDDOXZCVRU-UHFFFAOYSA-N 0.000 claims 1
• JWLZQOHJYSOIAI-UHFFFAOYSA-N 4-[[4-(4-chloroanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=CC(Cl)=CC=3)=NN=2)=C1 JWLZQOHJYSOIAI-UHFFFAOYSA-N 0.000 claims 1
• NQHPPUGCFAAXNN-UHFFFAOYSA-N 4-[[4-(4-chloroanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide;hydrobromide Chemical compound Br.C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=CC(Cl)=CC=3)=NN=2)=C1 NQHPPUGCFAAXNN-UHFFFAOYSA-N 0.000 claims 1
• LCMLACPWPXITHP-UHFFFAOYSA-N 4-[[4-(4-chloroanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=CC(Cl)=CC=3)=NN=2)=C1 LCMLACPWPXITHP-UHFFFAOYSA-N 0.000 claims 1
• CQKVTMQOEANGGL-UHFFFAOYSA-N 4-[[4-(4-chloroanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide;nitric acid Chemical compound O[N+]([O-])=O.C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=CC(Cl)=CC=3)=NN=2)=C1 CQKVTMQOEANGGL-UHFFFAOYSA-N 0.000 claims 1
• LXSCWVMEOHJISZ-UHFFFAOYSA-N 4-[[4-(4-chloroanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide;sulfuric acid Chemical compound OS(O)(=O)=O.C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=CC(Cl)=CC=3)=NN=2)=C1 LXSCWVMEOHJISZ-UHFFFAOYSA-N 0.000 claims 1
• JSAXYHAKCHLJFE-UHFFFAOYSA-N 4-[[4-(4-fluoroanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=CC(F)=CC=3)=NN=2)=C1 JSAXYHAKCHLJFE-UHFFFAOYSA-N 0.000 claims 1
• XYMBNBOCISDYKU-UHFFFAOYSA-N 4-[[4-(4-fluoroanilino)thieno[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3SC=CC=3C(NC=3C=CC(F)=CC=3)=NN=2)=C1 XYMBNBOCISDYKU-UHFFFAOYSA-N 0.000 claims 1
• ZANUYXSDZRSTRI-UHFFFAOYSA-N 4-[[4-(4-hydroxyanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-N-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=CC(O)=CC=3)=NN=2)=C1 ZANUYXSDZRSTRI-UHFFFAOYSA-N 0.000 claims 1
• AMABXWIFLUQJRQ-UHFFFAOYSA-N 4-[[4-(4-methoxyanilino)thieno[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3SC=CC=3C(NC=3C=CC(OC)=CC=3)=NN=2)=C1 AMABXWIFLUQJRQ-UHFFFAOYSA-N 0.000 claims 1
• WFSITOFCDNLHHZ-UHFFFAOYSA-N 4-[[4-[4-[acetyl(methyl)amino]anilino]furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC(COC=2C=3OC=CC=3C(NC=3C=CC(=CC=3)N(C)C(C)=O)=NN=2)=C1 WFSITOFCDNLHHZ-UHFFFAOYSA-N 0.000 claims 1
• XTJNGXWXFNKTMG-UHFFFAOYSA-N 4-[[7-(pyridin-4-ylmethoxy)furo[2,3-d]pyridazin-4-yl]amino]phenol Chemical compound N1=CC=C(C=C1)COC=1N=NC(=C2C1OC=C2)NC2=CC=C(C=C2)O XTJNGXWXFNKTMG-UHFFFAOYSA-N 0.000 claims 1
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
• IUPNSXNAWRIANS-UHFFFAOYSA-N 4-n,7-n-bis(1h-indazol-5-yl)thieno[2,3-d]pyridazine-4,7-diamine Chemical compound C1=C2NN=CC2=CC(NC2=NN=C(C=3C=CSC=32)NC=2C=C3C=NNC3=CC=2)=C1 IUPNSXNAWRIANS-UHFFFAOYSA-N 0.000 claims 1
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