CA2846187A1 - Pyrimido-pyridazinone compounds and use thereof - Google Patents

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Publication number

CA2846187A1

CA2846187A1 CA2846187A CA2846187A CA2846187A1 CA 2846187 A1 CA2846187 A1 CA 2846187A1 CA 2846187 A CA2846187 A CA 2846187A CA 2846187 A CA2846187 A CA 2846187A CA 2846187 A1 CA2846187 A1 CA 2846187A1

Authority

CA

Canada

Prior art keywords

pyridazin

amino

phenyl

oxo

dihydropyrimido

Prior art date

2011-08-23

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.)

Pending

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• Global Dossier
• CIPO
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• VSGHANRHWUFOHC-UHFFFAOYSA-N 2h-pyrimido[5,4-c]pyridazin-3-one Chemical class N1=CN=CC2=NNC(=O)C=C21 VSGHANRHWUFOHC-UHFFFAOYSA-N 0.000 title abstract description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 197
• -1 pyrimido-pyridazinone compound Chemical class 0.000 claims abstract description 152
• 206010061218 Inflammation Diseases 0.000 claims abstract description 57
• 230000004054 inflammatory process Effects 0.000 claims abstract description 57
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 295
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 264
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 240
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 190
• 125000000217 alkyl group Chemical group 0.000 claims description 102
• 229910052757 nitrogen Inorganic materials 0.000 claims description 78
• 125000000623 heterocyclic group Chemical group 0.000 claims description 73
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 64
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 51
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 48
• 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims description 44
• 125000003545 alkoxy group Chemical group 0.000 claims description 43
• 125000001072 heteroaryl group Chemical group 0.000 claims description 41
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 40
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 34
• 125000003118 aryl group Chemical group 0.000 claims description 34
• 229910052799 carbon Inorganic materials 0.000 claims description 30
• 229910052736 halogen Inorganic materials 0.000 claims description 29
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
• 230000005764 inhibitory process Effects 0.000 claims description 27
• 150000002367 halogens Chemical class 0.000 claims description 25
• 239000002253 acid Substances 0.000 claims description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
• 125000002950 monocyclic group Chemical group 0.000 claims description 14
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 14
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 13
• 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims description 12
• 125000004429 atom Chemical group 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 10
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 9
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 9
• 235000019260 propionic acid Nutrition 0.000 claims description 9
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 150000002148 esters Chemical class 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
• 229920006395 saturated elastomer Polymers 0.000 claims description 7
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
• 101710112791 Tyrosine-protein kinase JAK2 Proteins 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 150000003053 piperidines Chemical class 0.000 claims description 4
• 229930192474 thiophene Natural products 0.000 claims description 4
• 125000006664 (C1-C3) perfluoroalkyl group Chemical group 0.000 claims description 3
• QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical class C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 claims description 3
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• 230000037361 pathway Effects 0.000 claims description 3
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 2
• IOOLIHWRFJAGAW-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[[4-(2h-tetrazol-5-yl)piperidin-1-yl]methyl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=C1)=CC=C1CN(CC1)CCC1C=1N=NNN=1 IOOLIHWRFJAGAW-UHFFFAOYSA-N 0.000 claims description 2
• FQXFKRRYNPIDCF-UHFFFAOYSA-N 2-morpholin-4-yl-4-[4-(piperazin-1-ylmethyl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one;hydrochloride Chemical compound Cl.C=12C(=O)NN=CC2=NC(N2CCOCC2)=NC=1NC(C=C1)=CC=C1CN1CCNCC1 FQXFKRRYNPIDCF-UHFFFAOYSA-N 0.000 claims description 2
• 229920001774 Perfluoroether Polymers 0.000 claims description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims description 2
• UZHXFPYZNTWGCX-UHFFFAOYSA-N methyl 4-[5-oxo-4-[4-(piperazin-1-ylmethyl)anilino]-6h-pyrimido[4,5-d]pyridazin-2-yl]benzoate;hydrochloride Chemical compound Cl.C1=CC(C(=O)OC)=CC=C1C1=NC(NC=2C=CC(CN3CCNCC3)=CC=2)=C2C(=O)NN=CC2=N1 UZHXFPYZNTWGCX-UHFFFAOYSA-N 0.000 claims description 2
• 150000002780 morpholines Chemical class 0.000 claims description 2
• ITZWDHUUXWCUHN-UHFFFAOYSA-N OC(=O)CC1CCC(CC1)c1ccc(NC2NC(NC3CNNC(=O)C23)N2CCCCCC2)cc1 Chemical compound OC(=O)CC1CCC(CC1)c1ccc(NC2NC(NC3CNNC(=O)C23)N2CCCCCC2)cc1 ITZWDHUUXWCUHN-UHFFFAOYSA-N 0.000 claims 3
• CXHRVKJRPLIMIO-UHFFFAOYSA-N 2-[1-[4-[[2-(azepan-1-yl)-5-carbamoyl-6-methanimidoylpyrimidin-4-yl]amino]phenyl]piperidin-3-yl]acetic acid Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCCC(CC(O)=O)C1 CXHRVKJRPLIMIO-UHFFFAOYSA-N 0.000 claims 2
• BDIYBAQRVGMTLJ-UHFFFAOYSA-N 2-[1-[5-[[2-[4-(cyanomethyl)piperidin-1-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]pyridin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C=12C(=O)NN=CC2=NC(N2CCC(CC#N)CC2)=NC=1NC(C=N1)=CC=C1N1CCC(CC#N)CC1 BDIYBAQRVGMTLJ-UHFFFAOYSA-N 0.000 claims 2
• PVVUHUDTHNJOIO-UHFFFAOYSA-N CC1CC(C)CN(C1)C1NC2CNNC(=O)C2C(Nc2ccc(cc2)N2CCC(CC(O)=O)CC2)N1 Chemical compound CC1CC(C)CN(C1)C1NC2CNNC(=O)C2C(Nc2ccc(cc2)N2CCC(CC(O)=O)CC2)N1 PVVUHUDTHNJOIO-UHFFFAOYSA-N 0.000 claims 2
• XYXYSKFQMSYDOY-UHFFFAOYSA-N CC1CN(CC(C)O1)C1NC2CNNC(=O)C2C(Nc2ccc(cc2)N2CCC(CC(O)=O)CC2)N1 Chemical compound CC1CN(CC(C)O1)C1NC2CNNC(=O)C2C(Nc2ccc(cc2)N2CCC(CC(O)=O)CC2)N1 XYXYSKFQMSYDOY-UHFFFAOYSA-N 0.000 claims 2
• HREVFRVAWVUZAQ-UHFFFAOYSA-N O=C1NNCC2NC(NC(Nc3ccc(cc3)N3CCC(C[N+]#[C-])CC3)C12)N1CCCCCC1 Chemical compound O=C1NNCC2NC(NC(Nc3ccc(cc3)N3CCC(C[N+]#[C-])CC3)C12)N1CCCCCC1 HREVFRVAWVUZAQ-UHFFFAOYSA-N 0.000 claims 2
• SMXDYVVLQHNNRX-UHFFFAOYSA-N OC(=O)C1CCN(Cc2ccc(NC3NC(NC4CNNC(=O)C34)N3CCC(C[N+]#[C-])CC3)cc2)CC1 Chemical compound OC(=O)C1CCN(Cc2ccc(NC3NC(NC4CNNC(=O)C34)N3CCC(C[N+]#[C-])CC3)cc2)CC1 SMXDYVVLQHNNRX-UHFFFAOYSA-N 0.000 claims 2
• YTPJXSKCIJBFDO-UHFFFAOYSA-N OC(=O)CC1CCN(CC1)c1ccc(NC2NC(NC3CNNC(=O)C23)C2CCCCCC2)cc1 Chemical compound OC(=O)CC1CCN(CC1)c1ccc(NC2NC(NC3CNNC(=O)C23)C2CCCCCC2)cc1 YTPJXSKCIJBFDO-UHFFFAOYSA-N 0.000 claims 2
• DQHMEQRQZRKNGU-UHFFFAOYSA-N 1-[4-[(2-cycloheptyl-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(C2CCCCCC2)=NC2=C1C(=O)NN=C2 DQHMEQRQZRKNGU-UHFFFAOYSA-N 0.000 claims 1
• CQYPQRMXAKUQDG-UHFFFAOYSA-N 1-[4-[(5-oxo-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(C=C1)=CC=C1NC1C2C(=O)NNCC2NC(C=2C=CC=CC=2)N1 CQYPQRMXAKUQDG-UHFFFAOYSA-N 0.000 claims 1
• APWHCVIFCONOHD-UHFFFAOYSA-N 1-[4-[[2-(1,4-diazepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCNCCC2)=NC2=C1C(=O)NN=C2 APWHCVIFCONOHD-UHFFFAOYSA-N 0.000 claims 1
• LSJWIHQXXITFPD-UHFFFAOYSA-N 1-[4-[[2-(3-cyanopiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(N2CC(CCC2)C#N)=NC2=C1C(=O)NN=C2 LSJWIHQXXITFPD-UHFFFAOYSA-N 0.000 claims 1
• HLHVAQQHTFARIE-UHFFFAOYSA-N 1-[4-[[2-(4-cyanopiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC2)C#N)=NC2=C1C(=O)NN=C2 HLHVAQQHTFARIE-UHFFFAOYSA-N 0.000 claims 1
• NOQWJTHUTPXLSH-UHFFFAOYSA-N 1-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 NOQWJTHUTPXLSH-UHFFFAOYSA-N 0.000 claims 1
• MAGUPVPCRXCUNA-UHFFFAOYSA-N 1-[4-[[2-[1-(2-cyanoacetyl)piperidin-4-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(C2CCN(CC2)C(=O)CC#N)=NC2=C1C(=O)NN=C2 MAGUPVPCRXCUNA-UHFFFAOYSA-N 0.000 claims 1
• ZAVSNMRCVDTTFP-UHFFFAOYSA-N 1-[4-[[2-[4-(2-cyanoacetyl)piperazin-1-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCN(CC2)C(=O)CC#N)=NC2=C1C(=O)NN=C2 ZAVSNMRCVDTTFP-UHFFFAOYSA-N 0.000 claims 1
• MOHMAGNNOSHYJH-UHFFFAOYSA-N 1-[4-[[2-[4-(cyanomethyl)piperazin-1-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCN(CC#N)CC2)=NC2=C1C(=O)NN=C2 MOHMAGNNOSHYJH-UHFFFAOYSA-N 0.000 claims 1
• IGUXJMHNKADNMJ-UHFFFAOYSA-N 1-[5-oxo-4-[4-[[4-(2h-tetrazol-5-yl)piperidin-1-yl]methyl]anilino]-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidine-3-carbonitrile Chemical compound C=12C(=O)NN=CC2=NC(N2CC(CCC2)C#N)=NC=1NC(C=C1)=CC=C1CN(CC1)CCC1C=1N=NNN=1 IGUXJMHNKADNMJ-UHFFFAOYSA-N 0.000 claims 1
• PCTWVGOAOSCKTF-UHFFFAOYSA-N 1-[5-oxo-4-[4-[[4-(2h-tetrazol-5-ylmethyl)piperidin-1-yl]methyl]anilino]-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidine-3-carbonitrile Chemical compound C=12C(=O)NN=CC2=NC(N2CC(CCC2)C#N)=NC=1NC(C=C1)=CC=C1CN(CC1)CCC1CC=1N=NNN=1 PCTWVGOAOSCKTF-UHFFFAOYSA-N 0.000 claims 1
• LRYJICZRPINRKO-UHFFFAOYSA-N 1-[5-oxo-4-[4-[[4-(2h-tetrazol-5-ylmethyl)piperidin-1-yl]methyl]anilino]-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidine-4-carbonitrile Chemical compound C=12C(=O)NN=CC2=NC(N2CCC(CC2)C#N)=NC=1NC(C=C1)=CC=C1CN(CC1)CCC1CC=1N=NNN=1 LRYJICZRPINRKO-UHFFFAOYSA-N 0.000 claims 1
• UTQAEKMSXQKRGW-UHFFFAOYSA-N 1-[[4-[(2-cycloheptyl-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1NC1=NC(C2CCCCCC2)=NC2=C1C(=O)NN=C2 UTQAEKMSXQKRGW-UHFFFAOYSA-N 0.000 claims 1
• YIPVVOKGILKIDL-UHFFFAOYSA-N 1-[[4-[(5-oxo-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1NC1C2C(=O)NNCC2NC(C=2C=CC=CC=2)N1 YIPVVOKGILKIDL-UHFFFAOYSA-N 0.000 claims 1
• GFQABYWIGQDNAT-UHFFFAOYSA-N 1-[[4-[[2-(1,4-diazepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1NC1=NC(N2CCNCCC2)=NC2=C1C(=O)NN=C2 GFQABYWIGQDNAT-UHFFFAOYSA-N 0.000 claims 1
• JMHAMKLPFNGCOY-UHFFFAOYSA-N 1-[[4-[[2-(3-cyanopiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1NC1=NC(N2CC(CCC2)C#N)=NC2=C1C(=O)NN=C2 JMHAMKLPFNGCOY-UHFFFAOYSA-N 0.000 claims 1
• RDRKXVZADSMSRV-UHFFFAOYSA-N 1-[[4-[[2-(4-cyanopiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1NC1=NC(N2CCC(CC2)C#N)=NC2=C1C(=O)NN=C2 RDRKXVZADSMSRV-UHFFFAOYSA-N 0.000 claims 1
• GMRSRJJOLZHHEG-UHFFFAOYSA-N 1-[[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 GMRSRJJOLZHHEG-UHFFFAOYSA-N 0.000 claims 1
• BRTVFTOHSYFRAX-UHFFFAOYSA-N 1-[[4-[[2-[1-(2-cyanoacetyl)piperidin-4-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1NC1=NC(C2CCN(CC2)C(=O)CC#N)=NC2=C1C(=O)NN=C2 BRTVFTOHSYFRAX-UHFFFAOYSA-N 0.000 claims 1
• RHEJAFIJMIXTRZ-UHFFFAOYSA-N 1-[[4-[[2-[4-(2-cyanoacetyl)piperazin-1-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1NC1=NC(N2CCN(CC2)C(=O)CC#N)=NC2=C1C(=O)NN=C2 RHEJAFIJMIXTRZ-UHFFFAOYSA-N 0.000 claims 1
• GODQDEZAPIGXQP-UHFFFAOYSA-N 1-[[4-[[2-[4-(cyanomethyl)piperazin-1-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1NC1=NC(N2CCN(CC#N)CC2)=NC2=C1C(=O)NN=C2 GODQDEZAPIGXQP-UHFFFAOYSA-N 0.000 claims 1
• TYXUMIXYFXBMAE-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-4-[4-(piperazin-1-ylmethyl)anilino]-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C12C(=O)NNCC2NC(C=2C=C3OCOC3=CC=2)NC1NC(C=C1)=CC=C1CN1CCNCC1 TYXUMIXYFXBMAE-UHFFFAOYSA-N 0.000 claims 1
• PWQYFIGYNKXMGO-UHFFFAOYSA-N 2-(2,6-dimethylmorpholin-4-yl)-4-[4-(piperazin-1-ylmethyl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1C(C)OC(C)CN1C1=NC(NC=2C=CC(CN3CCNCC3)=CC=2)=C2C(=O)NN=CC2=N1 PWQYFIGYNKXMGO-UHFFFAOYSA-N 0.000 claims 1
• QZYIENPQSUGNJJ-UHFFFAOYSA-N 2-(2,6-dimethylmorpholin-4-yl)-4-[4-[4-(2-hydroxy-2-methylpropanoyl)piperidin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1C(C)OC(C)CN1C1=NC(NC=2C=CC(=CC=2)N2CCC(CC2)C(=O)C(C)(C)O)=C2C(=O)NN=CC2=N1 QZYIENPQSUGNJJ-UHFFFAOYSA-N 0.000 claims 1
• FOKIZMPMKWLBFN-UHFFFAOYSA-N 2-(2,6-dimethylpiperidin-1-yl)-4-[4-(piperazin-1-ylmethyl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound CC1CCCC(C)N1C1=NC(NC=2C=CC(CN3CCNCC3)=CC=2)=C2C(=O)NN=CC2=N1 FOKIZMPMKWLBFN-UHFFFAOYSA-N 0.000 claims 1
• PQBUWKLREGFKPV-UHFFFAOYSA-N 2-(2,6-dimethylpiperidin-1-yl)-4-[4-[4-(2-hydroxy-2-methylpropanoyl)piperazin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound CC1CCCC(C)N1C1=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(=O)C(C)(C)O)=C2C(=O)NN=CC2=N1 PQBUWKLREGFKPV-UHFFFAOYSA-N 0.000 claims 1
• ALGAGCOMWWNTFS-UHFFFAOYSA-N 2-(2-methylpiperidin-1-yl)-4-[4-(piperazin-1-ylmethyl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound CC1CCCCN1C1=NC(NC=2C=CC(CN3CCNCC3)=CC=2)=C2C(=O)NN=CC2=N1 ALGAGCOMWWNTFS-UHFFFAOYSA-N 0.000 claims 1
• LMNBXWZFGDZDPQ-UHFFFAOYSA-N 2-(3,5-dimethylpiperidin-1-yl)-4-[4-(piperazin-1-ylmethyl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1C(C)CC(C)CN1C1=NC(NC=2C=CC(CN3CCNCC3)=CC=2)=C2C(=O)NN=CC2=N1 LMNBXWZFGDZDPQ-UHFFFAOYSA-N 0.000 claims 1
• SWNARPWGNMZKTR-UHFFFAOYSA-N 2-(3,5-dimethylpiperidin-1-yl)-4-[4-[4-(2-hydroxy-2-methylpropanoyl)piperidin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1C(C)CC(C)CN1C1=NC(NC=2C=CC(=CC=2)N2CCC(CC2)C(=O)C(C)(C)O)=C2C(=O)NN=CC2=N1 SWNARPWGNMZKTR-UHFFFAOYSA-N 0.000 claims 1
• GEIUOZVZDHABJA-UHFFFAOYSA-N 2-(4-ethylpiperazin-1-yl)-4-[4-(piperazin-1-ylmethyl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one;hydrochloride Chemical compound Cl.C1CN(CC)CCN1C1=NC(NC=2C=CC(CN3CCNCC3)=CC=2)=C2C(=O)NN=CC2=N1 GEIUOZVZDHABJA-UHFFFAOYSA-N 0.000 claims 1
• QMOYHIVDMAJVPZ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-(4-carbamimidoylanilino)-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1=CC(C(=N)N)=CC=C1NC1=NC(N2CCCCCC2)=NC(C=N)=C1C(N)=O QMOYHIVDMAJVPZ-UHFFFAOYSA-N 0.000 claims 1
• RYZDJZFSIODRQX-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(2-piperazin-1-ylethoxy)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=C1)=CC=C1OCCN1CCNCC1 RYZDJZFSIODRQX-UHFFFAOYSA-N 0.000 claims 1
• ALFCNHMPDCHYPP-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(4-hydroxypiperidin-1-yl)anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCC(O)CC1 ALFCNHMPDCHYPP-UHFFFAOYSA-N 0.000 claims 1
• RMQBOFXIHGIZOP-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(4-ethylpiperazin-1-yl)ethyl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1CN(CC)CCN1CCC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC(C=N)=C1C(N)=O RMQBOFXIHGIZOP-UHFFFAOYSA-N 0.000 claims 1
• YRFHNXRTSFKGBP-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(4-hydroxy-4-methylpiperidin-1-yl)ethoxy]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1CC(C)(O)CCN1CCOC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC(C=N)=C1C(N)=O YRFHNXRTSFKGBP-UHFFFAOYSA-N 0.000 claims 1
• GBMUPBFMUIRRFL-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(4-hydroxy-4-methylpiperidin-1-yl)ethyl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1CC(C)(O)CCN1CCC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC(C=N)=C1C(N)=O GBMUPBFMUIRRFL-UHFFFAOYSA-N 0.000 claims 1
• WFBUSEXJHWRYGW-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(4-hydroxypiperidin-1-yl)ethyl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1CCN1CCC(O)CC1 WFBUSEXJHWRYGW-UHFFFAOYSA-N 0.000 claims 1
• PISMYVLZPKIKOM-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(hydroxymethyl)-6-azaspiro[2.5]octan-6-yl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N(CC1)CCC21CC2CO PISMYVLZPKIKOM-UHFFFAOYSA-N 0.000 claims 1
• PLRVOIGCBGTLTD-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethoxy]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1OCCN1CCN(CCO)CC1 PLRVOIGCBGTLTD-UHFFFAOYSA-N 0.000 claims 1
• NWQABPSTQALIAV-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1CCN1CCN(CCO)CC1 NWQABPSTQALIAV-UHFFFAOYSA-N 0.000 claims 1
• LMSSCXHJJQCITN-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-[4-(hydroxymethyl)piperidin-1-yl]ethoxy]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1OCCN1CCC(CO)CC1 LMSSCXHJJQCITN-UHFFFAOYSA-N 0.000 claims 1
• NXPMVEXTFYJLLS-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-[di(propan-2-yl)amino]ethoxy]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1=CC(OCCN(C(C)C)C(C)C)=CC=C1NC1=NC(N2CCCCCC2)=NC(C=N)=C1C(N)=O NXPMVEXTFYJLLS-UHFFFAOYSA-N 0.000 claims 1
• YTBOWIHSWMFGMZ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[3-(4-hydroxypiperidin-1-yl)propyl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CC(O)CCN1CCCC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 YTBOWIHSWMFGMZ-UHFFFAOYSA-N 0.000 claims 1
• CTFYZKXJZIFWJX-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(2-cyanoacetyl)piperazin-1-yl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCN(C(=O)CC#N)CC1 CTFYZKXJZIFWJX-UHFFFAOYSA-N 0.000 claims 1
• IWMALLGXJLQGJE-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(2-hydroxy-2-methylpropanoyl)piperazin-1-yl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C(C)(O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC(C=N)=C1C(N)=O IWMALLGXJLQGJE-UHFFFAOYSA-N 0.000 claims 1
• HMJOHRRHAANVNT-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(2-hydroxyethyl)piperazin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(CCO)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 HMJOHRRHAANVNT-UHFFFAOYSA-N 0.000 claims 1
• IQRBSVRSBKEVJP-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(2-hydroxyethyl)piperidin-1-yl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCC(CCO)CC1 IQRBSVRSBKEVJP-UHFFFAOYSA-N 0.000 claims 1
• SSJHNAHFNNQNDW-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(3-hydroxypropyl)piperazin-1-yl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCN(CCCO)CC1 SSJHNAHFNNQNDW-UHFFFAOYSA-N 0.000 claims 1
• WYVIZRQQTVTGTO-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(3-hydroxypropyl)piperidin-1-yl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCC(CCCO)CC1 WYVIZRQQTVTGTO-UHFFFAOYSA-N 0.000 claims 1
• NPNBSMGGHZNBOM-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(cyanomethyl)piperazin-1-yl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCN(CC#N)CC1 NPNBSMGGHZNBOM-UHFFFAOYSA-N 0.000 claims 1
• OYAPELWSINUPOM-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(hydroxymethyl)piperidin-1-yl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCC(CO)CC1 OYAPELWSINUPOM-UHFFFAOYSA-N 0.000 claims 1
• LSJRPFVCHIAVPU-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[[4-(2h-tetrazol-5-ylmethyl)piperidin-1-yl]methyl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=C1)=CC=C1CN(CC1)CCC1CC=1N=NNN=1 LSJRPFVCHIAVPU-UHFFFAOYSA-N 0.000 claims 1
• POSPGJWUEZLJAB-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[[1-[2-[4-(cyanomethyl)piperidin-1-yl]ethyl]piperidin-4-yl]amino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(CC1)CCN1CCN1CCC(CC#N)CC1 POSPGJWUEZLJAB-UHFFFAOYSA-N 0.000 claims 1
• RXIKMJWFBQWPGA-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[[6-(4-ethylpiperazin-1-yl)pyridin-3-yl]amino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1CN(CC)CCN1C(N=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC(C=N)=C1C(N)=O RXIKMJWFBQWPGA-UHFFFAOYSA-N 0.000 claims 1
• GFKWHZAGPDLSPU-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[[6-(4-hydroxypiperidin-1-yl)pyridin-3-yl]amino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=N1)=CC=C1N1CCC(O)CC1 GFKWHZAGPDLSPU-UHFFFAOYSA-N 0.000 claims 1
• PSVHEFGNVHYOMZ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[[6-[4-(2-cyanoacetyl)piperazin-1-yl]pyridin-3-yl]amino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=N1)=CC=C1N1CCN(C(=O)CC#N)CC1 PSVHEFGNVHYOMZ-UHFFFAOYSA-N 0.000 claims 1
• OYPBTSFOPBMLJV-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[[6-[4-(2-hydroxy-2-methylpropanoyl)piperazin-1-yl]pyridin-3-yl]amino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C(C)(O)C)CCN1C(N=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC(C=N)=C1C(N)=O OYPBTSFOPBMLJV-UHFFFAOYSA-N 0.000 claims 1
• VDALILMQMHXDSL-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[[6-[4-(2-hydroxyethyl)piperidin-1-yl]pyridin-3-yl]amino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=N1)=CC=C1N1CCC(CCO)CC1 VDALILMQMHXDSL-UHFFFAOYSA-N 0.000 claims 1
• HSXOWAZAWNXKBH-UHFFFAOYSA-N 2-(azepan-1-yl)-4-methanimidoyl-6-(4-piperazin-1-ylanilino)pyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCNCC1 HSXOWAZAWNXKBH-UHFFFAOYSA-N 0.000 claims 1
• PLMLSHIYJOCZES-UHFFFAOYSA-N 2-(azepan-1-yl)-4-methanimidoyl-6-[(6-piperazin-1-ylpyridin-3-yl)amino]pyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=N1)=CC=C1N1CCNCC1 PLMLSHIYJOCZES-UHFFFAOYSA-N 0.000 claims 1
• GPGFCWXQUISDDZ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-methanimidoyl-6-[4-(2-piperazin-1-ylethyl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1CCN1CCNCC1 GPGFCWXQUISDDZ-UHFFFAOYSA-N 0.000 claims 1
• PABCNGWOZWUTJJ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-methanimidoyl-6-[4-[4-(2-methoxyethyl)piperazin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound C1CN(CCOC)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC(C=N)=C1C(N)=O PABCNGWOZWUTJJ-UHFFFAOYSA-N 0.000 claims 1
• XYRIWKWYDIPEIS-UHFFFAOYSA-N 2-[1-(2-isocyanoacetyl)piperidin-4-yl]-4-[4-[[4-(2H-tetrazol-5-ylmethyl)piperidin-1-yl]methyl]anilino]-6H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(C(C[N+]#[C-])=O)CCC1C1=NC(NC=2C=CC(CN3CCC(CC4=NNN=N4)CC3)=CC=2)=C2C(=O)NN=CC2=N1 XYRIWKWYDIPEIS-UHFFFAOYSA-N 0.000 claims 1
• MYWVHKINECQIOO-UHFFFAOYSA-N 2-[1-[4-[(5-oxo-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]piperidin-4-yl]acetic acid Chemical compound C1CC(CC(=O)O)CCN1C(C=C1)=CC=C1NC1C2C(=O)NNCC2NC(C=2C=CC=CC=2)N1 MYWVHKINECQIOO-UHFFFAOYSA-N 0.000 claims 1
• UECGWNPQIQAFDD-UHFFFAOYSA-N 2-[1-[4-[(5-oxo-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]piperidin-4-yl]acetonitrile Chemical compound C12C(=O)NNCC2NC(C=2C=CC=CC=2)NC1NC(C=C1)=CC=C1N1CCC(CC#N)CC1 UECGWNPQIQAFDD-UHFFFAOYSA-N 0.000 claims 1
• KYCAKYXRRPCJQX-UHFFFAOYSA-N 2-[1-[4-[[2-(1,4-diazepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetic acid Chemical compound C1CC(CC(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCNCCC2)=NC2=C1C(=O)NN=C2 KYCAKYXRRPCJQX-UHFFFAOYSA-N 0.000 claims 1
• NZRYFJRBXZZVSO-UHFFFAOYSA-N 2-[1-[4-[[2-(2,6-dimethylmorpholin-4-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetonitrile Chemical compound C1C(C)OC(C)CN1C1=NC(NC=2C=CC(=CC=2)N2CCC(CC#N)CC2)=C2C(=O)NN=CC2=N1 NZRYFJRBXZZVSO-UHFFFAOYSA-N 0.000 claims 1
• RGEYYDDEXORXFI-UHFFFAOYSA-N 2-[1-[4-[[2-(2,6-dimethylpiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetic acid Chemical compound CC1CCCC(C)N1C1=NC(NC=2C=CC(=CC=2)N2CCC(CC(O)=O)CC2)=C2C(=O)NN=CC2=N1 RGEYYDDEXORXFI-UHFFFAOYSA-N 0.000 claims 1
• XUINSQVJJOKGFK-UHFFFAOYSA-N 2-[1-[4-[[2-(2,6-dimethylpiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetonitrile Chemical compound CC1CCCC(C)N1C1=NC(NC=2C=CC(=CC=2)N2CCC(CC#N)CC2)=C2C(=O)NN=CC2=N1 XUINSQVJJOKGFK-UHFFFAOYSA-N 0.000 claims 1
• HSLWFLOZNCYFDT-UHFFFAOYSA-N 2-[1-[4-[[2-(2-methylpiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetic acid Chemical compound CC1CCCCN1C1=NC(NC=2C=CC(=CC=2)N2CCC(CC(O)=O)CC2)=C2C(=O)NN=CC2=N1 HSLWFLOZNCYFDT-UHFFFAOYSA-N 0.000 claims 1
• JSIZZJFYHMAVQZ-UHFFFAOYSA-N 2-[1-[4-[[2-(2-methylpiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetonitrile Chemical compound CC1CCCCN1C1=NC(NC=2C=CC(=CC=2)N2CCC(CC#N)CC2)=C2C(=O)NN=CC2=N1 JSIZZJFYHMAVQZ-UHFFFAOYSA-N 0.000 claims 1
• NJDZYNQTLIHVQV-UHFFFAOYSA-N 2-[1-[4-[[2-(3,5-dimethylpiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetonitrile Chemical compound C1C(C)CC(C)CN1C1=NC(NC=2C=CC(=CC=2)N2CCC(CC#N)CC2)=C2C(=O)NN=CC2=N1 NJDZYNQTLIHVQV-UHFFFAOYSA-N 0.000 claims 1
• CCMRPIXGONWHJS-UHFFFAOYSA-N 2-[1-[4-[[2-(3-cyanopiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetic acid Chemical compound C1CC(CC(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(N2CC(CCC2)C#N)=NC2=C1C(=O)NN=C2 CCMRPIXGONWHJS-UHFFFAOYSA-N 0.000 claims 1
• SYHVUACYJMSJSS-UHFFFAOYSA-N 2-[1-[4-[[2-[1-(2-cyanoacetyl)piperidin-4-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetic acid Chemical compound C1CC(CC(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(C2CCN(CC2)C(=O)CC#N)=NC2=C1C(=O)NN=C2 SYHVUACYJMSJSS-UHFFFAOYSA-N 0.000 claims 1
• UXNLRBOFQOPLMF-UHFFFAOYSA-N 2-[1-[4-[[2-[4-(2-cyanoacetyl)piperazin-1-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetic acid Chemical compound C1CC(CC(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCN(CC2)C(=O)CC#N)=NC2=C1C(=O)NN=C2 UXNLRBOFQOPLMF-UHFFFAOYSA-N 0.000 claims 1
• MIIOTDFKGTYXJX-UHFFFAOYSA-N 2-[1-[4-[[2-[di(propan-2-yl)amino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetic acid Chemical compound C1=NNC(=O)C=2C1=NC(N(C(C)C)C(C)C)=NC=2NC(C=C1)=CC=C1N1CCC(CC(O)=O)CC1 MIIOTDFKGTYXJX-UHFFFAOYSA-N 0.000 claims 1
• VFUVXZYJTJMVTP-UHFFFAOYSA-N 2-[1-[4-[[2-[di(propan-2-yl)amino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetonitrile Chemical compound C1=NNC(=O)C=2C1=NC(N(C(C)C)C(C)C)=NC=2NC(C=C1)=CC=C1N1CCC(CC#N)CC1 VFUVXZYJTJMVTP-UHFFFAOYSA-N 0.000 claims 1
• UOKPQTJIOGDORE-UHFFFAOYSA-N 2-[1-[5-[(5-oxo-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl)amino]pyridin-2-yl]piperidin-4-yl]acetamide Chemical compound C1CC(CC(=O)N)CCN1C(N=C1)=CC=C1NC1C2C(=O)NNCC2NC(C=2C=CC=CC=2)N1 UOKPQTJIOGDORE-UHFFFAOYSA-N 0.000 claims 1
• BCZUPEQOXMAWPH-UHFFFAOYSA-N 2-[1-[5-[(5-oxo-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl)amino]pyridin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C12C(=O)NNCC2NC(C=2C=CC=CC=2)NC1NC(C=N1)=CC=C1N1CCC(CC#N)CC1 BCZUPEQOXMAWPH-UHFFFAOYSA-N 0.000 claims 1
• CXIFWMGGQKUFBH-UHFFFAOYSA-N 2-[1-[5-[[2-(2,6-dimethylmorpholin-4-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]pyridin-2-yl]piperidin-4-yl]acetic acid Chemical compound C1C(C)OC(C)CN1C1=NC(NC=2C=NC(=CC=2)N2CCC(CC(O)=O)CC2)=C2C(=O)NN=CC2=N1 CXIFWMGGQKUFBH-UHFFFAOYSA-N 0.000 claims 1
• SEDAOMWWLUBEOH-UHFFFAOYSA-N 2-[1-[5-[[2-(2,6-dimethylpiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]pyridin-2-yl]piperidin-4-yl]acetic acid Chemical compound CC1CCCC(C)N1C1=NC(NC=2C=NC(=CC=2)N2CCC(CC(O)=O)CC2)=C2C(=O)NN=CC2=N1 SEDAOMWWLUBEOH-UHFFFAOYSA-N 0.000 claims 1
• IYDSLTRZBAYIHH-UHFFFAOYSA-N 2-[1-[5-[[2-(2-methylpiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]pyridin-2-yl]piperidin-4-yl]acetic acid Chemical compound CC1CCCCN1C1=NC(NC=2C=NC(=CC=2)N2CCC(CC(O)=O)CC2)=C2C(=O)NN=CC2=N1 IYDSLTRZBAYIHH-UHFFFAOYSA-N 0.000 claims 1
• LNDYJUHBPAYKST-UHFFFAOYSA-N 2-[1-[5-[[2-(3,5-dimethylpiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]pyridin-2-yl]piperidin-4-yl]acetic acid Chemical compound C1C(C)CC(C)CN1C1=NC(NC=2C=NC(=CC=2)N2CCC(CC(O)=O)CC2)=C2C(=O)NN=CC2=N1 LNDYJUHBPAYKST-UHFFFAOYSA-N 0.000 claims 1
• SYJVDLBYTZZQRX-UHFFFAOYSA-N 2-[1-[5-[[2-[di(propan-2-yl)amino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]pyridin-2-yl]piperidin-4-yl]acetic acid Chemical compound C1=NNC(=O)C=2C1=NC(N(C(C)C)C(C)C)=NC=2NC(C=N1)=CC=C1N1CCC(CC(O)=O)CC1 SYJVDLBYTZZQRX-UHFFFAOYSA-N 0.000 claims 1
• GZCXKYVYBYNSMV-UHFFFAOYSA-N 2-[1-[5-oxo-4-[4-[[4-(2h-tetrazol-5-yl)piperidin-1-yl]methyl]anilino]-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C=12C(=O)NN=CC2=NC(N2CCC(CC#N)CC2)=NC=1NC(C=C1)=CC=C1CN(CC1)CCC1C=1N=NNN=1 GZCXKYVYBYNSMV-UHFFFAOYSA-N 0.000 claims 1
• LUBWRHMWWIENQO-UHFFFAOYSA-N 2-[1-[5-oxo-4-[4-[[4-(2h-tetrazol-5-ylmethyl)piperidin-1-yl]methyl]anilino]-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C=12C(=O)NN=CC2=NC(N2CCC(CC#N)CC2)=NC=1NC(C=C1)=CC=C1CN(CC1)CCC1CC=1N=NNN=1 LUBWRHMWWIENQO-UHFFFAOYSA-N 0.000 claims 1
• CCTORJYQUOCRBG-UHFFFAOYSA-N 2-[1-[[4-[(2-cycloheptyl-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]methyl]piperidin-4-yl]acetic acid Chemical compound C1CC(CC(=O)O)CCN1CC(C=C1)=CC=C1NC1=NC(C2CCCCCC2)=NC2=C1C(=O)NN=C2 CCTORJYQUOCRBG-UHFFFAOYSA-N 0.000 claims 1
• ULYXVCBTKBLXJO-UHFFFAOYSA-N 2-[1-[[4-[[2-(3-cyanopiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]methyl]piperidin-4-yl]acetic acid Chemical compound C1CC(CC(=O)O)CCN1CC(C=C1)=CC=C1NC1=NC(N2CC(CCC2)C#N)=NC2=C1C(=O)NN=C2 ULYXVCBTKBLXJO-UHFFFAOYSA-N 0.000 claims 1
• FIDJTOZKPQHRHQ-UHFFFAOYSA-N 2-[1-[[4-[[2-[1-(2-cyanoacetyl)piperidin-4-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]methyl]piperidin-4-yl]acetic acid Chemical compound C1CC(CC(=O)O)CCN1CC(C=C1)=CC=C1NC1=NC(C2CCN(CC2)C(=O)CC#N)=NC2=C1C(=O)NN=C2 FIDJTOZKPQHRHQ-UHFFFAOYSA-N 0.000 claims 1
• SKWJPUZGIZAAJN-UHFFFAOYSA-N 2-[1-[[4-[[2-[4-(2-cyanoacetyl)piperazin-1-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]methyl]piperidin-4-yl]acetic acid Chemical compound C1CC(CC(=O)O)CCN1CC(C=C1)=CC=C1NC1=NC(N2CCN(CC2)C(=O)CC#N)=NC2=C1C(=O)NN=C2 SKWJPUZGIZAAJN-UHFFFAOYSA-N 0.000 claims 1
• CRFPFKVKCCTUQG-UHFFFAOYSA-N 2-[1-[[4-[[2-[4-(cyanomethyl)piperazin-1-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]methyl]piperidin-4-yl]acetic acid Chemical compound C1CC(CC(=O)O)CCN1CC(C=C1)=CC=C1NC1=NC(N2CCN(CC#N)CC2)=NC2=C1C(=O)NN=C2 CRFPFKVKCCTUQG-UHFFFAOYSA-N 0.000 claims 1
• CBVHETGHTLRRNN-UHFFFAOYSA-N 2-[4-(2-isocyanoacetyl)piperazin-1-yl]-4-[4-[[4-(2H-tetrazol-5-ylmethyl)piperidin-1-yl]methyl]anilino]-6H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(C(C[N+]#[C-])=O)CCN1C1=NC(NC=2C=CC(CN3CCC(CC4=NNN=N4)CC3)=CC=2)=C2C(=O)NN=CC2=N1 CBVHETGHTLRRNN-UHFFFAOYSA-N 0.000 claims 1
• ZUDOKQORZXFTQY-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperazin-1-yl]-4-methanimidoyl-6-[4-(2-piperazin-1-ylethoxy)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(N2CCN(CC#N)CC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1OCCN1CCNCC1 ZUDOKQORZXFTQY-UHFFFAOYSA-N 0.000 claims 1
• VSJNCJFJORMKKU-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-[4-(4-ethylpiperazin-1-yl)anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC(C=N)=C1C(N)=O VSJNCJFJORMKKU-UHFFFAOYSA-N 0.000 claims 1
• LOHLQMZDHKALKA-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-[4-[2-(4-ethylpiperazin-1-yl)ethyl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1CN(CC)CCN1CCC(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC(C=N)=C1C(N)=O LOHLQMZDHKALKA-UHFFFAOYSA-N 0.000 claims 1
• WSMPCKSTTVSVQF-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-[4-[2-(diethylamino)ethoxy]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC(C=N)=C1C(N)=O WSMPCKSTTVSVQF-UHFFFAOYSA-N 0.000 claims 1
• HMZNUZIUDLPWGJ-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-[4-[2-(hydroxymethyl)-6-azaspiro[2.5]octan-6-yl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCC(CC#N)CC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N(CC1)CCC21CC2CO HMZNUZIUDLPWGJ-UHFFFAOYSA-N 0.000 claims 1
• KTPXXXTUVSXPIH-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-[4-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCC(CC#N)CC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1CCN1CCN(CCO)CC1 KTPXXXTUVSXPIH-UHFFFAOYSA-N 0.000 claims 1
• UYPKOPXCRRSNHM-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-[4-[2-[4-(hydroxymethyl)piperidin-1-yl]ethoxy]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCC(CC#N)CC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1OCCN1CCC(CO)CC1 UYPKOPXCRRSNHM-UHFFFAOYSA-N 0.000 claims 1
• OXSCRKLUUHJBDL-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-[4-[4-(2,3-dihydroxypropyl)piperazin-1-yl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCC(CC#N)CC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCN(CC(O)CO)CC1 OXSCRKLUUHJBDL-UHFFFAOYSA-N 0.000 claims 1
• OVQIQNNRBIZJJN-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-[4-[4-(2-hydroxy-2-methylpropanoyl)piperazin-1-yl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C(C)(O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC(C=N)=C1C(N)=O OVQIQNNRBIZJJN-UHFFFAOYSA-N 0.000 claims 1
• RPNJGIWHDNPALO-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-[4-[4-(2-hydroxyethyl)piperazin-1-yl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCC(CC#N)CC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCN(CCO)CC1 RPNJGIWHDNPALO-UHFFFAOYSA-N 0.000 claims 1
• GQRWHUYOCWHVPM-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-[4-[4-(2-hydroxyethyl)piperidin-1-yl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCC(CC#N)CC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCC(CCO)CC1 GQRWHUYOCWHVPM-UHFFFAOYSA-N 0.000 claims 1
• ATZFYVBJZLYNQV-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-[4-[4-(3-hydroxypropyl)piperazin-1-yl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCC(CC#N)CC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCN(CCCO)CC1 ATZFYVBJZLYNQV-UHFFFAOYSA-N 0.000 claims 1
• JZEQJJYKVZQHLI-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-[4-[4-(hydroxymethyl)piperidin-1-yl]anilino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCC(CC#N)CC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCC(CO)CC1 JZEQJJYKVZQHLI-UHFFFAOYSA-N 0.000 claims 1
• WWQRRHZTBFDFJY-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-[[6-[4-(2-diazenyl-2-iminoethyl)piperidin-1-yl]pyridin-3-yl]amino]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCC(CC#N)CC2)N=C(C=N)C(C(=O)N)=C1NC(C=N1)=CC=C1N1CCC(CC(=N)N=N)CC1 WWQRRHZTBFDFJY-UHFFFAOYSA-N 0.000 claims 1
• AKJJKLBDNXRNNX-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-methanimidoyl-6-(4-piperazin-1-ylanilino)pyrimidine-5-carboxamide Chemical compound N1=C(N2CCC(CC#N)CC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCNCC1 AKJJKLBDNXRNNX-UHFFFAOYSA-N 0.000 claims 1
• GPMVYVKVZNUFQF-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-methanimidoyl-6-[(6-piperazin-1-ylpyridin-3-yl)amino]pyrimidine-5-carboxamide Chemical compound N1=C(N2CCC(CC#N)CC2)N=C(C=N)C(C(=O)N)=C1NC(C=N1)=CC=C1N1CCNCC1 GPMVYVKVZNUFQF-UHFFFAOYSA-N 0.000 claims 1
• PMMAJXCZQPBWMB-UHFFFAOYSA-N 2-[4-(cyanomethyl)piperidin-1-yl]-4-methanimidoyl-6-[4-[4-(2-methoxyethyl)piperazin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound C1CN(CCOC)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC(C=N)=C1C(N)=O PMMAJXCZQPBWMB-UHFFFAOYSA-N 0.000 claims 1
• IKJGJDKBIUHBPU-UHFFFAOYSA-N 2-[4-(morpholin-4-ylmethyl)phenyl]-4-[4-(piperazin-1-ylmethyl)anilino]-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C12C(=O)NNCC2NC(C=2C=CC(CN3CCOCC3)=CC=2)NC1NC(C=C1)=CC=C1CN1CCNCC1 IKJGJDKBIUHBPU-UHFFFAOYSA-N 0.000 claims 1
• FTUTYOPDMHSCDE-UHFFFAOYSA-N 2-[4-[4-[(5-oxo-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]cyclohexyl]acetic acid Chemical compound C1CC(CC(=O)O)CCC1C(C=C1)=CC=C1NC1C2C(=O)NNCC2NC(C=2C=CC=CC=2)N1 FTUTYOPDMHSCDE-UHFFFAOYSA-N 0.000 claims 1
• RBSRPNFTFMGELL-UHFFFAOYSA-N 2-[4-[4-[(5-oxo-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1C(C=C1)=CC=C1NC1C2C(=O)NNCC2NC(C=2C=CC=CC=2)N1 RBSRPNFTFMGELL-UHFFFAOYSA-N 0.000 claims 1
• FISOYMNWGMVMAG-UHFFFAOYSA-N 2-[4-[4-[(5-oxo-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]piperidin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCC1C(C=C1)=CC=C1NC1C2C(=O)NNCC2NC(C=2C=CC=CC=2)N1 FISOYMNWGMVMAG-UHFFFAOYSA-N 0.000 claims 1
• CHDJUUAJRMMYHT-UHFFFAOYSA-N 2-[4-[4-[[5-carbamoyl-2-[4-(cyanomethyl)piperidin-1-yl]-6-methanimidoylpyrimidin-4-yl]amino]phenyl]piperazin-1-yl]-2-methylpropanoic acid Chemical compound C1CN(C(C)(C)C(O)=O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC(C=N)=C1C(N)=O CHDJUUAJRMMYHT-UHFFFAOYSA-N 0.000 claims 1
• YKFWNMINHNBPDH-UHFFFAOYSA-N 2-[4-[5-oxo-4-[4-[[4-(2h-tetrazol-5-yl)piperidin-1-yl]methyl]anilino]-6h-pyrimido[4,5-d]pyridazin-2-yl]piperazin-1-yl]acetonitrile Chemical compound C=12C(=O)NN=CC2=NC(N2CCN(CC#N)CC2)=NC=1NC(C=C1)=CC=C1CN(CC1)CCC1C=1N=NNN=1 YKFWNMINHNBPDH-UHFFFAOYSA-N 0.000 claims 1
• QGWGYGGLMYLUIC-UHFFFAOYSA-N 2-[4-[5-oxo-4-[4-[[4-(2h-tetrazol-5-ylmethyl)piperidin-1-yl]methyl]anilino]-6h-pyrimido[4,5-d]pyridazin-2-yl]piperazin-1-yl]acetonitrile Chemical compound C=12C(=O)NN=CC2=NC(N2CCN(CC#N)CC2)=NC=1NC(C=C1)=CC=C1CN(CC1)CCC1CC=1N=NNN=1 QGWGYGGLMYLUIC-UHFFFAOYSA-N 0.000 claims 1
• YNBDBXIEAYCZCT-UHFFFAOYSA-N 2-[5-[4-[[2-(azepan-1-yl)-5-carbamoyl-6-methanimidoylpyrimidin-4-yl]amino]phenyl]tetrazol-2-yl]acetic acid Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1C=1N=NN(CC(O)=O)N=1 YNBDBXIEAYCZCT-UHFFFAOYSA-N 0.000 claims 1
• UBHBYSLTIFKEQZ-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]-4-[4-(piperazin-1-ylmethyl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1=NNC(=O)C=2C1=NC(N(C(C)C)C(C)C)=NC=2NC(C=C1)=CC=C1CN1CCNCC1 UBHBYSLTIFKEQZ-UHFFFAOYSA-N 0.000 claims 1
• LUMWWUADHXJRBO-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]-4-[4-[4-(2-hydroxy-2-methylpropanoyl)piperidin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1=NNC(=O)C=2C1=NC(N(C(C)C)C(C)C)=NC=2NC(C=C1)=CC=C1N1CCC(C(=O)C(C)(C)O)CC1 LUMWWUADHXJRBO-UHFFFAOYSA-N 0.000 claims 1
• GOPKKOHXBALZJE-UHFFFAOYSA-N 2-cycloheptyl-4-[4-[[4-(2h-tetrazol-5-yl)piperidin-1-yl]methyl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(C2CCCCCC2)=NC=1NC(C=C1)=CC=C1CN(CC1)CCC1C=1N=NNN=1 GOPKKOHXBALZJE-UHFFFAOYSA-N 0.000 claims 1
• IBZQMGVSEURXBS-UHFFFAOYSA-N 2-cycloheptyl-4-[4-[[4-(2h-tetrazol-5-ylmethyl)piperidin-1-yl]methyl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(C2CCCCCC2)=NC=1NC(C=C1)=CC=C1CN(CC1)CCC1CC=1N=NNN=1 IBZQMGVSEURXBS-UHFFFAOYSA-N 0.000 claims 1
• SRUWWZYTTAMHMF-UHFFFAOYSA-N 2-methyl-2-[1-[4-[(5-oxo-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]piperidin-4-yl]propanoic acid Chemical compound C1CC(C(C)(C)C(O)=O)CCN1C(C=C1)=CC=C1NC1C2C(=O)NNCC2NC(C=2C=CC=CC=2)N1 SRUWWZYTTAMHMF-UHFFFAOYSA-N 0.000 claims 1
• BJTVZYGZPOJXBU-UHFFFAOYSA-N 2-phenyl-4-(4-piperazin-1-ylanilino)-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C12C(=O)NNCC2NC(C=2C=CC=CC=2)NC1NC(C=C1)=CC=C1N1CCNCC1 BJTVZYGZPOJXBU-UHFFFAOYSA-N 0.000 claims 1
• LGHYCNLIBKDMJF-UHFFFAOYSA-N 2-phenyl-4-[4-(2-piperazin-1-ylethoxy)anilino]-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C12C(=O)NNCC2NC(C=2C=CC=CC=2)NC1NC(C=C1)=CC=C1OCCN1CCNCC1 LGHYCNLIBKDMJF-UHFFFAOYSA-N 0.000 claims 1
• DEJRBJRLVAFXHD-UHFFFAOYSA-N 2-phenyl-4-[4-(piperazin-1-ylmethyl)anilino]-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C12C(=O)NNCC2NC(C=2C=CC=CC=2)NC1NC(C=C1)=CC=C1CN1CCNCC1 DEJRBJRLVAFXHD-UHFFFAOYSA-N 0.000 claims 1
• OOAKALDEVQOXAU-UHFFFAOYSA-N 2-phenyl-4-[[1-(2-piperazin-1-ylethyl)pyrazol-4-yl]amino]-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C12C(=O)NNCC2NC(C=2C=CC=CC=2)NC1NC(=C1)C=NN1CCN1CCNCC1 OOAKALDEVQOXAU-UHFFFAOYSA-N 0.000 claims 1
• BTERNPAPFOIBIX-UHFFFAOYSA-N 3-[1-[4-[(5-oxo-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]piperidin-4-yl]propanoic acid Chemical compound C1CC(CCC(=O)O)CCN1C(C=C1)=CC=C1NC1C2C(=O)NNCC2NC(C=2C=CC=CC=2)N1 BTERNPAPFOIBIX-UHFFFAOYSA-N 0.000 claims 1
• ZBQUWXBJCNZQRD-UHFFFAOYSA-N 3-[4-[4-[[5-carbamoyl-2-[4-(cyanomethyl)piperidin-1-yl]-6-methanimidoylpyrimidin-4-yl]amino]phenyl]piperazin-1-yl]propanoic acid Chemical compound N1=C(N2CCC(CC#N)CC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCN(CCC(O)=O)CC1 ZBQUWXBJCNZQRD-UHFFFAOYSA-N 0.000 claims 1
• UDYSBBDEDMNXOU-UHFFFAOYSA-N 3-oxo-3-[4-[5-oxo-4-[4-[[4-(2h-tetrazol-5-yl)piperidin-1-yl]methyl]anilino]-6h-pyrimido[4,5-d]pyridazin-2-yl]piperazin-1-yl]propanenitrile Chemical compound C1CN(C(CC#N)=O)CCN1C1=NC(NC=2C=CC(CN3CCC(CC3)C3=NNN=N3)=CC=2)=C2C(=O)NN=CC2=N1 UDYSBBDEDMNXOU-UHFFFAOYSA-N 0.000 claims 1
• JJMXVZQBAVVQAC-UHFFFAOYSA-N 3-oxo-3-[4-[5-oxo-4-[4-[[4-(2h-tetrazol-5-yl)piperidin-1-yl]methyl]anilino]-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-1-yl]propanenitrile Chemical compound C1CN(C(CC#N)=O)CCC1C1=NC(NC=2C=CC(CN3CCC(CC3)C3=NNN=N3)=CC=2)=C2C(=O)NN=CC2=N1 JJMXVZQBAVVQAC-UHFFFAOYSA-N 0.000 claims 1
• LHLYRQXNLDJBEA-UHFFFAOYSA-N 4-(4-carbamimidoylanilino)-2-[4-(cyanomethyl)piperidin-1-yl]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1=CC(C(=N)N)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC(C=N)=C1C(N)=O LHLYRQXNLDJBEA-UHFFFAOYSA-N 0.000 claims 1
• LAFDLDWISTZONW-UHFFFAOYSA-N 4-(4-morpholin-4-ylanilino)-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C12C(=O)NNCC2NC(C=2C=CC=CC=2)NC1NC(C=C1)=CC=C1N1CCOCC1 LAFDLDWISTZONW-UHFFFAOYSA-N 0.000 claims 1
• BDKCJURYCPGCFH-UHFFFAOYSA-N 4-[4-(2-aminoethoxy)anilino]-2-(azepan-1-yl)-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1=CC(OCCN)=CC=C1NC1=NC(N2CCCCCC2)=NC(C=N)=C1C(N)=O BDKCJURYCPGCFH-UHFFFAOYSA-N 0.000 claims 1
• VPIFDONBDHAXSF-UHFFFAOYSA-N 4-[4-(2-aminoethoxy)anilino]-2-[4-(cyanomethyl)piperidin-1-yl]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1=CC(OCCN)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC(C=N)=C1C(N)=O VPIFDONBDHAXSF-UHFFFAOYSA-N 0.000 claims 1
• HPAVHRZUPZTCJR-UHFFFAOYSA-N 4-[4-(2-morpholin-4-ylethoxy)anilino]-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C12C(=O)NNCC2NC(C=2C=CC=CC=2)NC1NC(C=C1)=CC=C1OCCN1CCOCC1 HPAVHRZUPZTCJR-UHFFFAOYSA-N 0.000 claims 1
• VWYIJHIVDASGPH-UHFFFAOYSA-N 4-[4-(2-oxa-7-azaspiro[3.5]nonan-7-yl)anilino]-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C12C(=O)NNCC2NC(C=2C=CC=CC=2)NC1NC(C=C1)=CC=C1N(CC1)CCC21COC2 VWYIJHIVDASGPH-UHFFFAOYSA-N 0.000 claims 1
• VQXWOWIEIYQDJA-UHFFFAOYSA-N 4-[4-(2-oxa-7-azaspiro[3.5]nonan-7-ylmethyl)anilino]-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C12C(=O)NNCC2NC(C=2C=CC=CC=2)NC1NC(C=C1)=CC=C1CN(CC1)CCC21COC2 VQXWOWIEIYQDJA-UHFFFAOYSA-N 0.000 claims 1
• BLPCSYNEEROVPD-UHFFFAOYSA-N 4-[4-(2-oxo-1,7-diazaspiro[3.5]nonan-7-yl)anilino]-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound N1C(=O)CC11CCN(C=2C=CC(NC3C4C(=O)NNCC4NC(N3)C=3C=CC=CC=3)=CC=2)CC1 BLPCSYNEEROVPD-UHFFFAOYSA-N 0.000 claims 1
• AYRPBKTYPBQYSK-UHFFFAOYSA-N 4-[4-(4-ethylpiperazin-1-yl)anilino]-2-[4-(trifluoromethoxy)phenyl]-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1C2C(=O)NNCC2NC(C=2C=CC(OC(F)(F)F)=CC=2)N1 AYRPBKTYPBQYSK-UHFFFAOYSA-N 0.000 claims 1
• BEBYZOYXFUTCAH-UHFFFAOYSA-N 4-[4-(4-ethylpiperazin-1-yl)anilino]-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1C2C(=O)NNCC2NC(C=2C=CC=CC=2)N1 BEBYZOYXFUTCAH-UHFFFAOYSA-N 0.000 claims 1
• ICQWIHBLXGBATD-UHFFFAOYSA-N 4-[4-(morpholin-4-ylmethyl)anilino]-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C12C(=O)NNCC2NC(C=2C=CC=CC=2)NC1NC(C=C1)=CC=C1CN1CCOCC1 ICQWIHBLXGBATD-UHFFFAOYSA-N 0.000 claims 1
• VWXRNRYGLAGGLW-UHFFFAOYSA-N 4-[4-(morpholine-4-carbonyl)anilino]-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=1C=C(NC2C3C(=O)NNCC3NC(N2)C=2C=CC=CC=2)C=CC=1C(=O)N1CCOCC1 VWXRNRYGLAGGLW-UHFFFAOYSA-N 0.000 claims 1
• MGJNCBCDNVORJM-UHFFFAOYSA-N 4-[4-[(4-ethylpiperazin-1-yl)methyl]anilino]-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(CC)CCN1CC(C=C1)=CC=C1NC1C2C(=O)NNCC2NC(C=2C=CC=CC=2)N1 MGJNCBCDNVORJM-UHFFFAOYSA-N 0.000 claims 1
• DIEGSKARCJUTEK-UHFFFAOYSA-N 4-[4-[2-(4-hydroxy-4-methylpiperidin-1-yl)ethoxy]anilino]-2-[4-(isocyanomethyl)piperidin-1-yl]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound CC1(O)CCN(CCOC2=CC=C(NC3=NC(=NC(C=N)=C3C(N)=O)N3CCC(C[N+]#[C-])CC3)C=C2)CC1 DIEGSKARCJUTEK-UHFFFAOYSA-N 0.000 claims 1
• YFJSIQPGASYPNK-UHFFFAOYSA-N 4-[4-[2-(4-hydroxypiperidin-1-yl)ethoxy]anilino]-6-methanimidoyl-2-piperidin-1-ylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1OCCN1CCC(O)CC1 YFJSIQPGASYPNK-UHFFFAOYSA-N 0.000 claims 1
• BIVYYJSAAKYTHI-UHFFFAOYSA-N 4-[4-[4-(2-aminoacetyl)piperazin-1-yl]anilino]-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(C(=O)CN)CCN1C(C=C1)=CC=C1NC1C2C(=O)NNCC2NC(C=2C=CC=CC=2)N1 BIVYYJSAAKYTHI-UHFFFAOYSA-N 0.000 claims 1
• AYQCDTBDEQAVSX-UHFFFAOYSA-N 4-[4-[4-(2-aminoacetyl)piperazin-1-yl]anilino]-2-phenyl-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(C(=O)CN)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=NC2=C1C(=O)NN=C2 AYQCDTBDEQAVSX-UHFFFAOYSA-N 0.000 claims 1
• DQGDMJAJNUGIOC-UHFFFAOYSA-N 4-[4-[4-(2-aminoethyl)piperazin-1-yl]anilino]-2-[4-(cyanomethyl)piperidin-1-yl]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound C1CN(CCN)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC(C=N)=C1C(N)=O DQGDMJAJNUGIOC-UHFFFAOYSA-N 0.000 claims 1
• JPEFOUIVDWFKTF-UHFFFAOYSA-N 4-[4-[4-(2-cyanoacetyl)piperazin-1-yl]anilino]-2-[4-(cyanomethyl)piperidin-1-yl]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCC(CC#N)CC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N1CCN(C(=O)CC#N)CC1 JPEFOUIVDWFKTF-UHFFFAOYSA-N 0.000 claims 1
• ONKUJXAJVUMXKJ-UHFFFAOYSA-N 4-[4-[4-(2-hydroxy-2-methylpropanoyl)piperidin-1-yl]anilino]-2-(2-methylpiperidin-1-yl)-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound CC1CCCCN1C1=NC(NC=2C=CC(=CC=2)N2CCC(CC2)C(=O)C(C)(C)O)=C2C(=O)NN=CC2=N1 ONKUJXAJVUMXKJ-UHFFFAOYSA-N 0.000 claims 1
• BJBOLFNHMLVZRT-UHFFFAOYSA-N 4-[4-[4-(3-hydroxypropyl)piperidin-1-yl]anilino]-2-[4-(isocyanomethyl)piperidin-1-yl]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound NC(=O)C1=C(C=N)N=C(N=C1NC1=CC=C(C=C1)N1CCC(CCCO)CC1)N1CCC(C[N+]#[C-])CC1 BJBOLFNHMLVZRT-UHFFFAOYSA-N 0.000 claims 1
• PCVWLJNMRSGOMU-UHFFFAOYSA-N 4-[4-[4-(cyanomethyl)piperazin-1-yl]anilino]-2-[4-(isocyanomethyl)piperidin-1-yl]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound NC(=O)C1=C(C=N)N=C(N=C1NC1=CC=C(C=C1)N1CCN(CC#N)CC1)N1CCC(C[N+]#[C-])CC1 PCVWLJNMRSGOMU-UHFFFAOYSA-N 0.000 claims 1
• PAALNJLSWGUETE-UHFFFAOYSA-N 4-[4-[[4-(2-hydroxy-2-methylpropanoyl)piperazin-1-yl]methyl]anilino]-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(C(=O)C(C)(O)C)CCN1CC(C=C1)=CC=C1NC1C2C(=O)NNCC2NC(C=2C=CC=CC=2)N1 PAALNJLSWGUETE-UHFFFAOYSA-N 0.000 claims 1
• DRPFCKWXHLVXLR-UHFFFAOYSA-N 4-[4-[bis(2-hydroxyethyl)amino]anilino]-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1=CC(N(CCO)CCO)=CC=C1NC1C2C(=O)NNCC2NC(C=2C=CC=CC=2)N1 DRPFCKWXHLVXLR-UHFFFAOYSA-N 0.000 claims 1
• ZPXQBVQJPHJQLN-UHFFFAOYSA-N 4-[[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]amino]-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C12C(=O)NNCC2NC(C=2C=CC=CC=2)NC1NC(=C1)C=NN1CCN1CCOCC1 ZPXQBVQJPHJQLN-UHFFFAOYSA-N 0.000 claims 1
• GMPJCYDTUDQOOT-UHFFFAOYSA-N 4-[[1-[2-(4-ethylpiperazin-1-yl)ethyl]pyrazol-4-yl]amino]-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(CC)CCN1CCN1N=CC(NC2C3C(=O)NNCC3NC(N2)C=2C=CC=CC=2)=C1 GMPJCYDTUDQOOT-UHFFFAOYSA-N 0.000 claims 1
• ZEYXAHFXOFENSJ-UHFFFAOYSA-N 4-[[1-[2-(4-methylpiperazin-1-yl)ethyl]pyrazol-4-yl]amino]-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(C)CCN1CCN1N=CC(NC2C3C(=O)NNCC3NC(N2)C=2C=CC=CC=2)=C1 ZEYXAHFXOFENSJ-UHFFFAOYSA-N 0.000 claims 1
• QMURQZVMMZFUEJ-UHFFFAOYSA-N 4-[[6-[4-(2-cyanoacetyl)piperazin-1-yl]pyridin-3-yl]amino]-2-[4-(cyanomethyl)piperidin-1-yl]-6-methanimidoylpyrimidine-5-carboxamide Chemical compound N1=C(N2CCC(CC#N)CC2)N=C(C=N)C(C(=O)N)=C1NC(C=N1)=CC=C1N1CCN(C(=O)CC#N)CC1 QMURQZVMMZFUEJ-UHFFFAOYSA-N 0.000 claims 1
• AKXHGIZHOIWBRS-UHFFFAOYSA-N 6-[4-[(5-oxo-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound OC(=O)C1CC11CCN(C=2C=CC(NC3C4C(=O)NNCC4NC(N3)C=3C=CC=CC=3)=CC=2)CC1 AKXHGIZHOIWBRS-UHFFFAOYSA-N 0.000 claims 1
• JTDBIHBPFWSBCG-UHFFFAOYSA-N 6-[4-[(5-oxo-2-pyridin-4-yl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound OC(=O)C1CC11CCN(C=2C=CC(NC3C4C(=O)NNCC4NC(N3)C=3C=CN=CC=3)=CC=2)CC1 JTDBIHBPFWSBCG-UHFFFAOYSA-N 0.000 claims 1
• VDNZSMASXFMFQB-UHFFFAOYSA-N 6-[4-[[2-(1,4-diazepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound OC(=O)C1CC11CCN(C=2C=CC(NC=3C=4C(=O)NN=CC=4N=C(N=3)N3CCNCCC3)=CC=2)CC1 VDNZSMASXFMFQB-UHFFFAOYSA-N 0.000 claims 1
• YNXLQJKBYQYQPC-UHFFFAOYSA-N 6-[4-[[2-(2,6-dimethylmorpholin-4-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound C1C(C)OC(C)CN1C1=NC(NC=2C=CC(=CC=2)N2CCC3(C(C3)C(O)=O)CC2)=C2C(=O)NN=CC2=N1 YNXLQJKBYQYQPC-UHFFFAOYSA-N 0.000 claims 1
• AOJDOBPLUQSZLO-UHFFFAOYSA-N 6-[4-[[2-(2,6-dimethylpiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound CC1CCCC(C)N1C1=NC(NC=2C=CC(=CC=2)N2CCC3(C(C3)C(O)=O)CC2)=C2C(=O)NN=CC2=N1 AOJDOBPLUQSZLO-UHFFFAOYSA-N 0.000 claims 1
• UEXYJSKDLCRWFG-UHFFFAOYSA-N 6-[4-[[2-(2-methoxyphenyl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound COC1=CC=CC=C1C1=NC(NC=2C=CC(=CC=2)N2CCC3(C(C3)C(O)=O)CC2)=C2C(=O)NN=CC2=N1 UEXYJSKDLCRWFG-UHFFFAOYSA-N 0.000 claims 1
• FDIDTRFZMYUWOZ-UHFFFAOYSA-N 6-[4-[[2-(2-methylpiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound CC1CCCCN1C1=NC(NC=2C=CC(=CC=2)N2CCC3(C(C3)C(O)=O)CC2)=C2C(=O)NN=CC2=N1 FDIDTRFZMYUWOZ-UHFFFAOYSA-N 0.000 claims 1
• PRIOUYKKTCCFQE-UHFFFAOYSA-N 6-[4-[[2-(3,5-dimethylpiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound C1C(C)CC(C)CN1C1=NC(NC=2C=CC(=CC=2)N2CCC3(C(C3)C(O)=O)CC2)=C2C(=O)NN=CC2=N1 PRIOUYKKTCCFQE-UHFFFAOYSA-N 0.000 claims 1
• XQFXAMVAKGOCOY-UHFFFAOYSA-N 6-[4-[[2-(3-cyanopiperidin-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound OC(=O)C1CC11CCN(C=2C=CC(NC=3C=4C(=O)NN=CC=4N=C(N=3)N3CC(CCC3)C#N)=CC=2)CC1 XQFXAMVAKGOCOY-UHFFFAOYSA-N 0.000 claims 1
• ASLSLGVLCIPXEE-UHFFFAOYSA-N 6-[4-[[2-(4-fluorophenyl)-5-oxo-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound OC(=O)C1CC11CCN(C=2C=CC(NC3C4C(=O)NNCC4NC(N3)C=3C=CC(F)=CC=3)=CC=2)CC1 ASLSLGVLCIPXEE-UHFFFAOYSA-N 0.000 claims 1
• XDMRJVMWLLUDFU-UHFFFAOYSA-N 6-[4-[[2-(4-methoxyphenyl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=NC(NC=2C=CC(=CC=2)N2CCC3(C(C3)C(O)=O)CC2)=C2C(=O)NN=CC2=N1 XDMRJVMWLLUDFU-UHFFFAOYSA-N 0.000 claims 1
• RKTRDBZCPLJMMO-UHFFFAOYSA-N 6-[4-[[2-[1-(2-cyanoacetyl)piperidin-4-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound OC(=O)C1CC11CCN(C=2C=CC(NC=3C=4C(=O)NN=CC=4N=C(N=3)C3CCN(CC3)C(=O)CC#N)=CC=2)CC1 RKTRDBZCPLJMMO-UHFFFAOYSA-N 0.000 claims 1
• KXHXYVVYIYEMJQ-UHFFFAOYSA-N 6-[4-[[2-[4-(2-cyanoacetyl)piperazin-1-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound OC(=O)C1CC11CCN(C=2C=CC(NC=3C=4C(=O)NN=CC=4N=C(N=3)N3CCN(CC3)C(=O)CC#N)=CC=2)CC1 KXHXYVVYIYEMJQ-UHFFFAOYSA-N 0.000 claims 1
• CQLNPNVGEIUICM-UHFFFAOYSA-N 6-[4-[[2-[di(propan-2-yl)amino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound C1=NNC(=O)C=2C1=NC(N(C(C)C)C(C)C)=NC=2NC(C=C1)=CC=C1N(CC1)CCC21CC2C(O)=O CQLNPNVGEIUICM-UHFFFAOYSA-N 0.000 claims 1
• ARVGQXNILMXTDH-UHFFFAOYSA-N 6-[5-[(5-oxo-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl)amino]pyridin-2-yl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound OC(=O)C1CC11CCN(C=2N=CC(NC3C4C(=O)NNCC4NC(N3)C=3C=CC=CC=3)=CC=2)CC1 ARVGQXNILMXTDH-UHFFFAOYSA-N 0.000 claims 1
• GXWLYDJPYDIHSY-UHFFFAOYSA-N 6-[5-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]pyridin-2-yl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound OC(=O)C1CC11CCN(C=2N=CC(NC=3C=4C(=O)NN=CC=4N=C(N=3)N3CCCCCC3)=CC=2)CC1 GXWLYDJPYDIHSY-UHFFFAOYSA-N 0.000 claims 1
• QGIGXDUSHYNVRC-UHFFFAOYSA-N 6-[[4-[(5-oxo-2-phenyl-2,3,4,4a,6,7,8,8a-octahydro-1H-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]methyl]-6-azaspiro[2.5]octane-2-carboxylic acid Chemical compound OC(=O)C1CC11CCN(CC=2C=CC(NC3C4C(=O)NNCC4NC(N3)C=3C=CC=CC=3)=CC=2)CC1 QGIGXDUSHYNVRC-UHFFFAOYSA-N 0.000 claims 1
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