CA2385817C - Substituted pyridines and pyridazines with angiogenesis inhibiting activity - Google Patents

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Publication number

CA2385817C

CA2385817C CA2385817A CA2385817A CA2385817C CA 2385817 C CA2385817 C CA 2385817C CA 2385817 A CA2385817 A CA 2385817A CA 2385817 A CA2385817 A CA 2385817A CA 2385817 C CA2385817 C CA 2385817C

Authority

CA

Canada

Prior art keywords

cndot

substituted

alkyl

methyl

optionally substituted

Prior art date

1999-09-28

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 - Lifetime

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• 230000033115 angiogenesis Effects 0.000 title claims abstract description 24
• 150000004892 pyridazines Chemical class 0.000 title abstract description 7
• 150000003222 pyridines Chemical class 0.000 title abstract description 6
• 230000002401 inhibitory effect Effects 0.000 title abstract description 4
• 238000000034 method Methods 0.000 claims abstract description 114
• 125000001424 substituent group Chemical group 0.000 claims abstract description 69
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
• 125000003118 aryl group Chemical group 0.000 claims abstract description 19
• 241000124008 Mammalia Species 0.000 claims abstract description 10
• 230000008569 process Effects 0.000 claims abstract description 10
• 230000002159 abnormal effect Effects 0.000 claims abstract description 8
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
• 150000001875 compounds Chemical class 0.000 claims description 140
• 125000003282 alkyl amino group Chemical group 0.000 claims description 125
• 125000000217 alkyl group Chemical group 0.000 claims description 85
• 125000001072 heteroaryl group Chemical group 0.000 claims description 73
• 125000004429 atom Chemical group 0.000 claims description 66
• 125000000623 heterocyclic group Chemical group 0.000 claims description 64
• 229910052717 sulfur Inorganic materials 0.000 claims description 47
• -1 nitro, amidino, guanidino, mercapto, sulfo Chemical group 0.000 claims description 43
• 125000003545 alkoxy group Chemical group 0.000 claims description 40
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 35
• 229910052760 oxygen Inorganic materials 0.000 claims description 33
• 125000004414 alkyl thio group Chemical group 0.000 claims description 31
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
• 229910052736 halogen Inorganic materials 0.000 claims description 25
• 125000004432 carbon atom Chemical group C* 0.000 claims description 24
• 150000002367 halogens Chemical class 0.000 claims description 24
• 229920006395 saturated elastomer Polymers 0.000 claims description 23
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
• 230000015572 biosynthetic process Effects 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 15
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 15
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
• 125000003277 amino group Chemical group 0.000 claims description 13
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 13
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 12
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 12
• 125000005843 halogen group Chemical group 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 206010038923 Retinopathy Diseases 0.000 claims description 10
• 125000002947 alkylene group Chemical group 0.000 claims description 10
• 125000002619 bicyclic group Chemical group 0.000 claims description 10
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 8
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 8
• 125000004423 acyloxy group Chemical group 0.000 claims description 7
• 150000001412 amines Chemical class 0.000 claims description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
• 229940002612 prodrug Drugs 0.000 claims description 7
• 239000000651 prodrug Substances 0.000 claims description 7
• 125000006413 ring segment Chemical group 0.000 claims description 7
• 206010012441 Dermatitis bullous Diseases 0.000 claims description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• QFCXANHHBCGMAS-UHFFFAOYSA-N 4-[[4-(4-chloroanilino)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(Cl)=CC=3)=NN=2)=C1 QFCXANHHBCGMAS-UHFFFAOYSA-N 0.000 claims description 4
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 4
• 230000000302 ischemic effect Effects 0.000 claims description 4
• 208000002780 macular degeneration Diseases 0.000 claims description 4
• 208000004644 retinal vein occlusion Diseases 0.000 claims description 4
• 230000004614 tumor growth Effects 0.000 claims description 4
• 206010012468 Dermatitis herpetiformis Diseases 0.000 claims description 3
• 206010015218 Erythema multiforme Diseases 0.000 claims description 3
• 206010034277 Pemphigoid Diseases 0.000 claims description 3
• 208000000594 bullous pemphigoid Diseases 0.000 claims description 3
• 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 3
• UFJYSFZNZCNDQQ-UHFFFAOYSA-N 4-[[4-(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=CC(OC)=CC=3)=NN=2)=C1 UFJYSFZNZCNDQQ-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• OGUVJPFBEGGUHL-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-5-yl)-4-pyridin-4-ylsulfanylisoquinolin-1-amine Chemical compound C1=C2CCCC2=CC=C1NC(C1=CC=CC=C11)=NC=C1SC1=CC=NC=C1 OGUVJPFBEGGUHL-UHFFFAOYSA-N 0.000 claims description 2
• DIDIJDSQKHOKKS-UHFFFAOYSA-N n-(4-chlorophenyl)-4-pyridin-4-ylsulfanylisoquinolin-1-amine Chemical compound C1=CC(Cl)=CC=C1NC(C1=CC=CC=C11)=NC=C1SC1=CC=NC=C1 DIDIJDSQKHOKKS-UHFFFAOYSA-N 0.000 claims description 2
• VNRMXOPCEVMSCQ-UHFFFAOYSA-N n-(4-pyridin-4-ylsulfanylisoquinolin-1-yl)-1,3-benzothiazol-6-amine Chemical compound C=1C=C2N=CSC2=CC=1NC(C1=CC=CC=C11)=NC=C1SC1=CC=NC=C1 VNRMXOPCEVMSCQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 84
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims 16
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 12
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 12
• 208000017442 Retinal disease Diseases 0.000 claims 9
• 125000004430 oxygen atom Chemical group O* 0.000 claims 8
• 201000004681 Psoriasis Diseases 0.000 claims 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
• AMBMUMOJGMUOKD-UHFFFAOYSA-N 1-n,4-n-bis(1,3-benzothiazol-6-yl)phthalazine-1,4-diamine Chemical compound C12=CC=CC=C2C(NC=2C=C3SC=NC3=CC=2)=NN=C1NC1=CC=C(N=CS2)C2=C1 AMBMUMOJGMUOKD-UHFFFAOYSA-N 0.000 claims 1
• KDMMSLMWBGBBAX-UHFFFAOYSA-N 1-n-(1,3-benzothiazol-6-yl)-4-n-(2,2-difluoro-1,3-benzodioxol-5-yl)phthalazine-1,4-diamine Chemical compound C12=CC=CC=C2C(NC2=CC=C3OC(OC3=C2)(F)F)=NN=C1NC1=CC=C(N=CS2)C2=C1 KDMMSLMWBGBBAX-UHFFFAOYSA-N 0.000 claims 1
• QXKQZOIFCINSIA-UHFFFAOYSA-N 1-n-(1,3-benzothiazol-6-yl)-4-n-(3-bromophenyl)phthalazine-1,4-diamine Chemical compound BrC1=CC=CC(NC=2C3=CC=CC=C3C(NC=3C=C4SC=NC4=CC=3)=NN=2)=C1 QXKQZOIFCINSIA-UHFFFAOYSA-N 0.000 claims 1
• NGDNRUPUNURUKX-UHFFFAOYSA-N 1-n-(1,3-benzothiazol-6-yl)-4-n-(3-fluoro-4-methylphenyl)phthalazine-1,4-diamine Chemical compound C1=C(F)C(C)=CC=C1NC(C1=CC=CC=C11)=NN=C1NC1=CC=C(N=CS2)C2=C1 NGDNRUPUNURUKX-UHFFFAOYSA-N 0.000 claims 1
• OQCDAZJDVNSKEE-UHFFFAOYSA-N 1-n-(1,3-benzothiazol-6-yl)-4-n-(3-methoxyphenyl)phthalazine-1,4-diamine Chemical compound COC1=CC=CC(NC=2C3=CC=CC=C3C(NC=3C=C4SC=NC4=CC=3)=NN=2)=C1 OQCDAZJDVNSKEE-UHFFFAOYSA-N 0.000 claims 1
• AQQGWEGFROEBJZ-UHFFFAOYSA-N 1-n-(1,3-benzothiazol-6-yl)-4-n-(4-chlorophenyl)phthalazine-1,4-diamine Chemical compound C1=CC(Cl)=CC=C1NC(C1=CC=CC=C11)=NN=C1NC1=CC=C(N=CS2)C2=C1 AQQGWEGFROEBJZ-UHFFFAOYSA-N 0.000 claims 1
• JGVZVSBDIFHGQE-UHFFFAOYSA-N 1-n-(1,3-benzothiazol-6-yl)-4-n-(4-piperidin-1-ylphenyl)phthalazine-1,4-diamine Chemical compound C1CCCCN1C(C=C1)=CC=C1NC(C1=CC=CC=C11)=NN=C1NC1=CC=C(N=CS2)C2=C1 JGVZVSBDIFHGQE-UHFFFAOYSA-N 0.000 claims 1
• AOCIXJDVYRKKRE-UHFFFAOYSA-N 1-n-(1,3-benzothiazol-6-yl)-4-n-(4-propan-2-ylphenyl)phthalazine-1,4-diamine Chemical compound C1=CC(C(C)C)=CC=C1NC(C1=CC=CC=C11)=NN=C1NC1=CC=C(N=CS2)C2=C1 AOCIXJDVYRKKRE-UHFFFAOYSA-N 0.000 claims 1
• IIWJNZNJYWFKCL-UHFFFAOYSA-N 1-n-(1,3-benzothiazol-6-yl)-4-n-[4-[ethyl(propan-2-yl)amino]phenyl]phthalazine-1,4-diamine Chemical compound C1=CC(N(C(C)C)CC)=CC=C1NC(C1=CC=CC=C11)=NN=C1NC1=CC=C(N=CS2)C2=C1 IIWJNZNJYWFKCL-UHFFFAOYSA-N 0.000 claims 1
• VOHCDANIDWYGPS-UHFFFAOYSA-N 1-n-(3h-benzimidazol-5-yl)-4-n-(4-chlorophenyl)phthalazine-1,4-diamine Chemical compound C1=CC(Cl)=CC=C1NC(C1=CC=CC=C11)=NN=C1NC1=CC=C(N=CN2)C2=C1 VOHCDANIDWYGPS-UHFFFAOYSA-N 0.000 claims 1
• 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
• OHYAKZDLDRKXAP-UHFFFAOYSA-N 4-[[4-(1,3-benzodioxol-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=C4OCOC4=CC=3)=NN=2)=C1 OHYAKZDLDRKXAP-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
• WASAOGFKTQUPAD-UHFFFAOYSA-N 4-[[4-(2,3-dihydro-1-benzofuran-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=C4CCOC4=CC=3)=NN=2)=C1 WASAOGFKTQUPAD-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
• KSUBTPJTXVUWOE-UHFFFAOYSA-N 4-[[4-(3-chloro-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=C(Cl)C(F)=CC=3)=NN=2)=C1 KSUBTPJTXVUWOE-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
• YYWPNTUZTLEPKX-UHFFFAOYSA-N 4-[[4-(3-chloroanilino)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=CC=3)=NN=2)=C1 YYWPNTUZTLEPKX-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
• JLTRXMUHOLIDDV-UHFFFAOYSA-N 4-[[4-(4-bromoanilino)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(Br)=CC=3)=NN=2)=C1 JLTRXMUHOLIDDV-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
• BRBRAVUMEGGHJZ-UHFFFAOYSA-N 4-[[4-(4-chloroanilino)furo[2,3-d]pyridazin-7-yl]oxymethyl]-n-[2-(dimethylamino)ethyl]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NCCN(C)C)=CC(COC=2C=3OC=CC=3C(NC=3C=CC(Cl)=CC=3)=NN=2)=C1 BRBRAVUMEGGHJZ-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
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