CA2592007C - Triazolophthalazines - Google Patents

Info

Publication number

CA2592007C

CA2592007C CA2592007A CA2592007A CA2592007C CA 2592007 C CA2592007 C CA 2592007C CA 2592007 A CA2592007 A CA 2592007A CA 2592007 A CA2592007 A CA 2592007A CA 2592007 C CA2592007 C CA 2592007C

Authority

CA

Canada

Prior art keywords

phenyl

alkyl

methoxy

triazolo

phthalazin

Prior art date

2005-01-05

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

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• 150000001875 compounds Chemical class 0.000 claims abstract description 271
• -1 1-4C-alkoxycarbonyl Chemical class 0.000 claims description 164
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
• 229910052757 nitrogen Inorganic materials 0.000 claims description 74
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 65
• 150000003839 salts Chemical class 0.000 claims description 53
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 51
• 125000004573 morpholin-4-yl group Chemical class N1(CCOCC1)* 0.000 claims description 46
• 229910052740 iodine Inorganic materials 0.000 claims description 44
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
• 239000001257 hydrogen Substances 0.000 claims description 40
• 229910052739 hydrogen Inorganic materials 0.000 claims description 40
• 229910052736 halogen Inorganic materials 0.000 claims description 33
• 150000002367 halogens Chemical class 0.000 claims description 33
• 125000004076 pyridyl group Chemical group 0.000 claims description 33
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
• 101100177165 Caenorhabditis elegans har-1 gene Proteins 0.000 claims description 29
• 238000011282 treatment Methods 0.000 claims description 25
• 125000001544 thienyl group Chemical group 0.000 claims description 24
• 239000000460 chlorine Substances 0.000 claims description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims description 23
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 22
• 125000005842 heteroatom Chemical group 0.000 claims description 22
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 21
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
• 239000005864 Sulphur Chemical group 0.000 claims description 21
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
• 229910052760 oxygen Inorganic materials 0.000 claims description 21
• 239000001301 oxygen Chemical group 0.000 claims description 21
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 19
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 19
• 125000002950 monocyclic group Chemical group 0.000 claims description 18
• 125000004299 tetrazol-5-yl group Chemical class [H]N1N=NC(*)=N1 0.000 claims description 17
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 16
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 16
• ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 16
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
• SGTXILTYXULEQD-UHFFFAOYSA-N 2H-triazolo[4,5-f]phthalazine Chemical group N1=NC=C2C3=NNN=C3C=CC2=C1 SGTXILTYXULEQD-UHFFFAOYSA-N 0.000 claims description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
• 125000003277 amino group Chemical group 0.000 claims description 11
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 10
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 10
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 10
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 230000000694 effects Effects 0.000 claims description 10
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
• 208000035475 disorder Diseases 0.000 claims description 9
• 239000011737 fluorine Substances 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 206010029113 Neovascularisation Diseases 0.000 claims description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• BUYUFJZVMVFQLQ-UHFFFAOYSA-N 4-[2-(5,5,8,8-tetramethyl-6,7-dihydroquinoxalin-2-yl)ethynyl]benzoic acid Chemical compound CC1(C=2N=CC(=NC=2C(CC1)(C)C)C#CC1=CC=C(C(=O)O)C=C1)C BUYUFJZVMVFQLQ-UHFFFAOYSA-N 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 230000001771 impaired effect Effects 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 6
• RBIIKVXVYVANCQ-CUWPLCDZSA-N (2s,4s,5s)-5-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-6-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-4-hydroxy-2-propan-2-ylhexanamide Chemical compound C1C(C)(C)N(C[C@H](N)[C@@H](O)C[C@@H](C(C)C)C(=O)NCC(C)(C)C(N)=O)CC(=O)N1C1=CC=CC=C1Cl RBIIKVXVYVANCQ-CUWPLCDZSA-N 0.000 claims description 5
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• 125000004432 carbon atom Chemical group C* 0.000 claims description 5
• 230000008497 endothelial barrier function Effects 0.000 claims description 5
• 230000003511 endothelial effect Effects 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• CQXHGLHIADVBQW-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-[3-(2h-tetrazol-5-yl)phenyl]-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(C=CC=1)C1=NNN=N1)C1=CC=CC=C12 CQXHGLHIADVBQW-UHFFFAOYSA-N 0.000 claims description 4
• BERRTEMAKLHCEH-UHFFFAOYSA-N 3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]-n,n-dimethylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(C=CC=1)S(=O)(=O)N(C)C)C1=CC=CC=C12 BERRTEMAKLHCEH-UHFFFAOYSA-N 0.000 claims description 4
• DMXZEAGYRDSWII-UHFFFAOYSA-N 3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]benzonitrile Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(C=CC=1)C#N)C1=CC=CC=C12 DMXZEAGYRDSWII-UHFFFAOYSA-N 0.000 claims description 4
• 206010040070 Septic Shock Diseases 0.000 claims description 4
• 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 4
• 201000010099 disease Diseases 0.000 claims description 4
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 4
• 230000036303 septic shock Effects 0.000 claims description 4
• 206010030113 Oedema Diseases 0.000 claims description 3
• 206010003246 arthritis Diseases 0.000 claims description 3
• 208000027866 inflammatory disease Diseases 0.000 claims description 3
• 125000002971 oxazolyl group Chemical group 0.000 claims description 3
• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• 230000002792 vascular Effects 0.000 claims description 3
• WZDBABZTOQSBOV-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(3-morpholin-4-ylsulfonylphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(C=CC=1)S(=O)(=O)N1CCOCC1)C1=CC=CC=C12 WZDBABZTOQSBOV-UHFFFAOYSA-N 0.000 claims description 2
• YDGXEJJOEYTQEP-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(3-pyrrolidin-1-ylsulfonylphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(C=CC=1)S(=O)(=O)N1CCCC1)C1=CC=CC=C12 YDGXEJJOEYTQEP-UHFFFAOYSA-N 0.000 claims description 2
• VPOLQETXLJRANO-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-(4-morpholin-4-ylsulfonylphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=CC(=CC=1)S(=O)(=O)N1CCOCC1)C1=CC=CC=C12 VPOLQETXLJRANO-UHFFFAOYSA-N 0.000 claims description 2
• IZVSFCVCPDZGGF-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-[3-(2-methyltetrazol-5-yl)phenyl]-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(C=CC=1)C1=NN(C)N=N1)C1=CC=CC=C12 IZVSFCVCPDZGGF-UHFFFAOYSA-N 0.000 claims description 2
• PWMOOKYAAOSNRU-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-[4-(2-methyltetrazol-5-yl)phenyl]-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=CC(=CC=1)C1=NN(C)N=N1)C1=CC=CC=C12 PWMOOKYAAOSNRU-UHFFFAOYSA-N 0.000 claims description 2
• OCYJKVRZVMCFDL-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-[4-(2h-tetrazol-5-yl)phenyl]-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=CC(=CC=1)C1=NNN=N1)C1=CC=CC=C12 OCYJKVRZVMCFDL-UHFFFAOYSA-N 0.000 claims description 2
• MNQOIDVWDBFRQX-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methyl]-n-(4-piperidin-1-ylsulfonylphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1CC1=NN=C2N1N=C(NC=1C=CC(=CC=1)S(=O)(=O)N1CCCCC1)C1=CC=CC=C12 MNQOIDVWDBFRQX-UHFFFAOYSA-N 0.000 claims description 2
• XTULLINHWGBJIS-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methyl]-n-[3-(2-methyltetrazol-5-yl)phenyl]-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1CC1=NN=C2N1N=C(NC=1C=C(C=CC=1)C1=NN(C)N=N1)C1=CC=CC=C12 XTULLINHWGBJIS-UHFFFAOYSA-N 0.000 claims description 2
• YKQMVSZDYFMORE-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methyl]-n-[3-(2h-tetrazol-5-yl)phenyl]-[1,2,4]triazolo[3,4-a]phthalazin-6-amine Chemical compound C1=CC(OC)=CC=C1CC1=NN=C2N1N=C(NC=1C=C(C=CC=1)C1=NNN=N1)C1=CC=CC=C12 YKQMVSZDYFMORE-UHFFFAOYSA-N 0.000 claims description 2
• MCKIQHGKMFADRE-UHFFFAOYSA-N 3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(C=CC=1)S(N)(=O)=O)C1=CC=CC=C12 MCKIQHGKMFADRE-UHFFFAOYSA-N 0.000 claims description 2
• OSGBHVOGBRCXPP-UHFFFAOYSA-N 3-[[3-[(4-methoxyphenyl)methyl]-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]benzonitrile Chemical compound C1=CC(OC)=CC=C1CC1=NN=C2N1N=C(NC=1C=C(C=CC=1)C#N)C1=CC=CC=C12 OSGBHVOGBRCXPP-UHFFFAOYSA-N 0.000 claims description 2
• SCBFCULYXKHFII-UHFFFAOYSA-N 3-methoxy-n-[3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(NS(=O)(=O)C=3C=C(OC)C=CC=3)C=CC=1)C1=CC=CC=C12 SCBFCULYXKHFII-UHFFFAOYSA-N 0.000 claims description 2
• XEFMSBRORAXMMA-UHFFFAOYSA-N 3-methoxy-n-[4-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=CC(NS(=O)(=O)C=3C=C(OC)C=CC=3)=CC=1)C1=CC=CC=C12 XEFMSBRORAXMMA-UHFFFAOYSA-N 0.000 claims description 2
• YVTVAPZBSLMXCJ-UHFFFAOYSA-N 4-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=CC(=CC=1)S(N)(=O)=O)C1=CC=CC=C12 YVTVAPZBSLMXCJ-UHFFFAOYSA-N 0.000 claims description 2
• UXKSTFYIFOIWFA-UHFFFAOYSA-N 4-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]benzonitrile Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=CC(=CC=1)C#N)C1=CC=CC=C12 UXKSTFYIFOIWFA-UHFFFAOYSA-N 0.000 claims description 2
• PXAOPJAZZRRTMO-UHFFFAOYSA-N 4-acetyl-n-[3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(NS(=O)(=O)C=3C=CC(=CC=3)C(C)=O)C=CC=1)C1=CC=CC=C12 PXAOPJAZZRRTMO-UHFFFAOYSA-N 0.000 claims description 2
• AHLFWKLPHBBXKW-UHFFFAOYSA-N 4-methoxy-n-[3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(NS(=O)(=O)C=3C=CC(OC)=CC=3)C=CC=1)C1=CC=CC=C12 AHLFWKLPHBBXKW-UHFFFAOYSA-N 0.000 claims description 2
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
• RFHHWZJOKDIBTG-UHFFFAOYSA-N n,n-dimethyl-3-[[3-[2-(trifluoromethyl)phenyl]-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]benzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=CC(NC=2C3=CC=CC=C3C3=NN=C(N3N=2)C=2C(=CC=CC=2)C(F)(F)F)=C1 RFHHWZJOKDIBTG-UHFFFAOYSA-N 0.000 claims description 2
• XZZBXZDZDXAFHU-UHFFFAOYSA-N n-[3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=1)C1=CC=CC=C12 XZZBXZDZDXAFHU-UHFFFAOYSA-N 0.000 claims description 2
• HSTZBTQVBKVMPY-UHFFFAOYSA-N n-[3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]-1-phenylmethanesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(NS(=O)(=O)CC=3C=CC=CC=3)C=CC=1)C1=CC=CC=C12 HSTZBTQVBKVMPY-UHFFFAOYSA-N 0.000 claims description 2
• XKEMDWQSXAGUTA-UHFFFAOYSA-N n-[3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(NS(=O)(=O)C=3C=CC(C)=CC=3)C=CC=1)C1=CC=CC=C12 XKEMDWQSXAGUTA-UHFFFAOYSA-N 0.000 claims description 2
• UAIDXCPGNNUYBW-UHFFFAOYSA-N n-[3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]-6-morpholin-4-ylpyridine-3-sulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(NS(=O)(=O)C=3C=NC(=CC=3)N3CCOCC3)C=CC=1)C1=CC=CC=C12 UAIDXCPGNNUYBW-UHFFFAOYSA-N 0.000 claims description 2
• RAPCFZFAVBRMKO-UHFFFAOYSA-N n-[3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(NS(C)(=O)=O)C=CC=1)C1=CC=CC=C12 RAPCFZFAVBRMKO-UHFFFAOYSA-N 0.000 claims description 2
• HXRCMHKJOUPURX-UHFFFAOYSA-N n-[3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]morpholine-4-sulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(NS(=O)(=O)N3CCOCC3)C=CC=1)C1=CC=CC=C12 HXRCMHKJOUPURX-UHFFFAOYSA-N 0.000 claims description 2
• XUPZFHSSAUBMKF-UHFFFAOYSA-N n-[3-[[3-(4-methoxyphenyl)-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]thiophene-2-sulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NN=C2N1N=C(NC=1C=C(NS(=O)(=O)C=3SC=CC=3)C=CC=1)C1=CC=CC=C12 XUPZFHSSAUBMKF-UHFFFAOYSA-N 0.000 claims description 2
• OFPZTDFQPFJKDG-UHFFFAOYSA-N n-[3-[[3-[(4-methoxyphenyl)methyl]-[1,2,4]triazolo[3,4-a]phthalazin-6-yl]amino]phenyl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CC1=NN=C2N1N=C(NC=1C=C(NS(C)(=O)=O)C=CC=1)C1=CC=CC=C12 OFPZTDFQPFJKDG-UHFFFAOYSA-N 0.000 claims description 2
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