JP2014524475A5

JP2014524475A5 -

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Publication number: JP2014524475A5
Authority: JP; Japan
Prior art keywords: amino; pyridazin; phenyl; oxo; dihydropyrimido
Prior art date: 2012-08-23
Legal status : Granted

Application number

JP2014527282A

Other languages

English (en)

Japanese (ja)

Other versions

JP5993010B2 (ja

JP2014524475A (ja

Filing date

2012-08-23

Publication date

2015-10-15

2012-08-23 Application filed filed Critical

2012-08-23 Priority claimed from PCT/US2012/051980 external-priority patent/WO2013028818A1/en

2014-09-22 Publication of JP2014524475A publication Critical patent/JP2014524475A/ja

2015-10-15 Publication of JP2014524475A5 publication Critical patent/JP2014524475A5/ja

2016-09-14 Application granted granted Critical

2016-09-14 Publication of JP5993010B2 publication Critical patent/JP5993010B2/ja

Status Active legal-status Critical Current

2032-08-23 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims 65
-1 R 46 Chemical compound 0.000 claims 25
229910052799 carbon Inorganic materials 0.000 claims 21
125000000623 heterocyclic group Chemical group 0.000 claims 19
229910052739 hydrogen Inorganic materials 0.000 claims 17
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
239000002253 acid Substances 0.000 claims 8
229910052736 halogen Inorganic materials 0.000 claims 8
125000001072 heteroaryl group Chemical group 0.000 claims 8
150000002367 halogens Chemical class 0.000 claims 7
125000000753 cycloalkyl group Chemical group 0.000 claims 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
239000008194 pharmaceutical composition Substances 0.000 claims 5
150000003839 salts Chemical class 0.000 claims 5
CICPLKAJEGYYGM-UHFFFAOYSA-N 3h-pyridazin-4-one Chemical compound O=C1CN=NC=C1 CICPLKAJEGYYGM-UHFFFAOYSA-N 0.000 claims 4
235000011054 acetic acid Nutrition 0.000 claims 4
125000004432 carbon atom Chemical group C* 0.000 claims 4
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 4
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
TUCUGMSPHGMPOI-UHFFFAOYSA-N 6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1=NC=C2C(=O)NN=CC2=N1 TUCUGMSPHGMPOI-UHFFFAOYSA-N 0.000 claims 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims 3
101710112791 Tyrosine-protein kinase JAK2 Proteins 0.000 claims 3
125000005605 benzo group Chemical group 0.000 claims 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
229910052760 oxygen Inorganic materials 0.000 claims 3
125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 3
BXACYAKZBAFEIV-UHFFFAOYSA-N 2-[1-[4-[(2-cycloheptyl-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(C2CCCCCC2)=NC2=C1C(=O)NN=C2 BXACYAKZBAFEIV-UHFFFAOYSA-N 0.000 claims 2
JCVVHKQMKLNYPK-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]acetic acid Chemical compound C1C(C)OC(C)CN1C1=NC(NC=2C=CC(=CC=2)N2CCC(CC(O)=O)CC2)=C2C(=O)NN=CC2=N1 JCVVHKQMKLNYPK-UHFFFAOYSA-N 0.000 claims 2
YBTVYOBZIFTKHY-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]acetic acid Chemical compound C1C(C)CC(C)CN1C1=NC(NC=2C=CC(=CC=2)N2CCC(CC(O)=O)CC2)=C2C(=O)NN=CC2=N1 YBTVYOBZIFTKHY-UHFFFAOYSA-N 0.000 claims 2
ZLJJGDNOJCDNKD-UHFFFAOYSA-N 2-[1-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-3-yl]acetic acid Chemical compound C1C(CC(=O)O)CCCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 ZLJJGDNOJCDNKD-UHFFFAOYSA-N 0.000 claims 2
JHCFYMYSDATETA-UHFFFAOYSA-N 2-[1-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetonitrile Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=C1)=CC=C1N1CCC(CC#N)CC1 JHCFYMYSDATETA-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
JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 claims 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
239000005973 Carvone Substances 0.000 claims 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 claims 2
125000003118 aryl group Chemical group 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
125000002950 monocyclic group Chemical group 0.000 claims 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
229910052717 sulfur Inorganic materials 0.000 claims 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
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
GWYVDNLLCWVVLH-UHFFFAOYSA-N 1-[5-oxo-4-[4-(piperazin-1-ylmethyl)anilino]-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C1=NC(NC=2C=CC(CN3CCNCC3)=CC=2)=C2C(=O)NN=CC2=N1 GWYVDNLLCWVVLH-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
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
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
ZQVDOALFJLMVJY-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-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(C=2C=C3OCOC3=CC=2)=NC=1NC(C=C1)=CC=C1CN1CCNCC1 ZQVDOALFJLMVJY-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
KFHYJLQWOOBWIW-UHFFFAOYSA-N 2-(4-methylpiperidin-1-yl)-4-[4-(2-piperazin-1-ylethoxy)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one;hydrochloride Chemical compound Cl.C1CC(C)CCN1C1=NC(NC=2C=CC(OCCN3CCNCC3)=CC=2)=C2C(=O)NN=CC2=N1 KFHYJLQWOOBWIW-UHFFFAOYSA-N 0.000 claims 1
IZJDDAXLNVWKQV-UHFFFAOYSA-N 2-(6-azaspiro[2.5]octan-6-yl)-4-(4-morpholin-4-ylanilino)-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(N2CCC3(CC3)CC2)=NC=1NC(C=C1)=CC=C1N1CCOCC1 IZJDDAXLNVWKQV-UHFFFAOYSA-N 0.000 claims 1
ODVAGCHOBKZNJO-UHFFFAOYSA-N 2-(azepan-1-yl)-4-(2h-benzotriazol-5-ylamino)-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound N=1C(NC=2C=C3N=NNC3=CC=2)=C2C(=O)NN=CC2=NC=1N1CCCCCC1 ODVAGCHOBKZNJO-UHFFFAOYSA-N 0.000 claims 1
XWTPGDYKOXRGGS-UHFFFAOYSA-N 2-(azepan-1-yl)-4-(4-fluoroanilino)-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1=CC(F)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 XWTPGDYKOXRGGS-UHFFFAOYSA-N 0.000 claims 1
RQVSTZRYEAVRET-UHFFFAOYSA-N 2-(azepan-1-yl)-4-(4-methylsulfonylanilino)-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 RQVSTZRYEAVRET-UHFFFAOYSA-N 0.000 claims 1
MLWMQOQVMDQGDC-UHFFFAOYSA-N 2-(azepan-1-yl)-4-(4-morpholin-4-ylanilino)-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=C1)=CC=C1N1CCOCC1 MLWMQOQVMDQGDC-UHFFFAOYSA-N 0.000 claims 1
FNMSNCOGAKUVDX-UHFFFAOYSA-N 2-(azepan-1-yl)-4-(4-piperidin-4-yloxyanilino)-6h-pyrimido[4,5-d]pyridazin-5-one;hydrochloride Chemical compound Cl.C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=C1)=CC=C1OC1CCNCC1 FNMSNCOGAKUVDX-UHFFFAOYSA-N 0.000 claims 1
ISAKNYJSENHFTQ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[3-(hydroxymethyl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound OCC1=CC=CC(NC=2C=3C(=O)NN=CC=3N=C(N=2)N2CCCCCC2)=C1 ISAKNYJSENHFTQ-UHFFFAOYSA-N 0.000 claims 1
PLNZRHOWESHDLZ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(1-hydroxy-2-methylpropan-2-yl)oxyanilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1=CC(OC(C)(CO)C)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 PLNZRHOWESHDLZ-UHFFFAOYSA-N 0.000 claims 1
CZMLJVGPETYKEJ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(2-ethyltetrazol-5-yl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound CCN1N=NC(C=2C=CC(NC=3C=4C(=O)NN=CC=4N=C(N=3)N3CCCCCC3)=CC=2)=N1 CZMLJVGPETYKEJ-UHFFFAOYSA-N 0.000 claims 1
OAKFEOPDFIPHNK-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(2-hydroxyethoxy)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1=CC(OCCO)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 OAKFEOPDFIPHNK-UHFFFAOYSA-N 0.000 claims 1
RXIZXXKJRDEVMI-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(2-hydroxyethyl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1=CC(CCO)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 RXIZXXKJRDEVMI-UHFFFAOYSA-N 0.000 claims 1
MESFFTSCLYFQNJ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(2-methoxyethoxy)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1=CC(OCCOC)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 MESFFTSCLYFQNJ-UHFFFAOYSA-N 0.000 claims 1
YKKVLDDNAYHXNZ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(2-morpholin-4-ylethoxy)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=C1)=CC=C1OCCN1CCOCC1 YKKVLDDNAYHXNZ-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
FWSXXCBEKWMASQ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(2-piperazin-1-ylethoxy)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one;hydrochloride Chemical compound Cl.C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=C1)=CC=C1OCCN1CCNCC1 FWSXXCBEKWMASQ-UHFFFAOYSA-N 0.000 claims 1
LFMMFFXSMFPZCC-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(2-piperazin-1-ylethyl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=C1)=CC=C1CCN1CCNCC1 LFMMFFXSMFPZCC-UHFFFAOYSA-N 0.000 claims 1
TWQCCZUFZBJSER-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(3-hydroxypiperidin-1-yl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1C(O)CCCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 TWQCCZUFZBJSER-UHFFFAOYSA-N 0.000 claims 1
RQGSMFTVLOIWDI-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(3-hydroxypropoxy)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1=CC(OCCCO)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 RQGSMFTVLOIWDI-UHFFFAOYSA-N 0.000 claims 1
HKNMOTLQXYDGCC-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(3-hydroxypropyl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1=CC(CCCO)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 HKNMOTLQXYDGCC-UHFFFAOYSA-N 0.000 claims 1
RIHAPCPVSFCDSQ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(3-piperazin-1-ylpropoxy)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=C1)=CC=C1OCCCN1CCNCC1 RIHAPCPVSFCDSQ-UHFFFAOYSA-N 0.000 claims 1
BGYRXGQWAZXEDS-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(3-piperazin-1-ylpropyl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=C1)=CC=C1CCCN1CCNCC1 BGYRXGQWAZXEDS-UHFFFAOYSA-N 0.000 claims 1
PLMRZLPLJGKPMQ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(4,4-difluoropiperidin-1-yl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CC(F)(F)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 PLMRZLPLJGKPMQ-UHFFFAOYSA-N 0.000 claims 1
MUKBSXUWZHPJBE-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(4-hydroxypiperidin-1-yl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CC(O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 MUKBSXUWZHPJBE-UHFFFAOYSA-N 0.000 claims 1
JUFNJDGTOSTABG-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-(morpholine-4-carbonyl)anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=1C=C(NC=2C=3C(=O)NN=CC=3N=C(N=2)N2CCCCCC2)C=CC=1C(=O)N1CCOCC1 JUFNJDGTOSTABG-UHFFFAOYSA-N 0.000 claims 1
UEUZWOPDWCJLFL-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(1,4-diazepan-1-yl)ethoxy]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=C1)=CC=C1OCCN1CCCNCC1 UEUZWOPDWCJLFL-UHFFFAOYSA-N 0.000 claims 1
ZLKXZPXDOZIMOT-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(3-oxopiperazin-1-yl)ethoxy]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CNC(=O)CN1CCOC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 ZLKXZPXDOZIMOT-UHFFFAOYSA-N 0.000 claims 1
LQQOXQAYDYXSRD-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(4-ethylpiperazin-1-yl)-2-oxoethoxy]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(CC)CCN1C(=O)COC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 LQQOXQAYDYXSRD-UHFFFAOYSA-N 0.000 claims 1
DCSJUPXLDMJOJR-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(4-ethylpiperazin-1-yl)ethoxy]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(CC)CCN1CCOC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 DCSJUPXLDMJOJR-UHFFFAOYSA-N 0.000 claims 1
WGDFDNOMSGBBJS-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(4-ethylpiperazin-1-yl)ethyl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(CC)CCN1CCC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 WGDFDNOMSGBBJS-UHFFFAOYSA-N 0.000 claims 1
LBWDZKUIXZGMRC-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(4-hydroxy-4-methylpiperidin-1-yl)ethoxy]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CC(C)(O)CCN1CCOC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 LBWDZKUIXZGMRC-UHFFFAOYSA-N 0.000 claims 1
OGSQWLDZPCKFBL-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(4-hydroxy-4-methylpiperidin-1-yl)ethyl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CC(C)(O)CCN1CCC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 OGSQWLDZPCKFBL-UHFFFAOYSA-N 0.000 claims 1
HYHWPPVSNVMQKG-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(4-hydroxypiperidin-1-yl)ethoxy]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CC(O)CCN1CCOC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 HYHWPPVSNVMQKG-UHFFFAOYSA-N 0.000 claims 1
CQCJOABXZPVPFA-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(4-hydroxypiperidin-1-yl)ethyl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CC(O)CCN1CCC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 CQCJOABXZPVPFA-UHFFFAOYSA-N 0.000 claims 1
RSVRQLHDWFVQCL-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(4-methylpiperazin-1-yl)-2-oxoethoxy]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(C)CCN1C(=O)COC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 RSVRQLHDWFVQCL-UHFFFAOYSA-N 0.000 claims 1
DECWCGJHVBGDPC-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(4-methylpiperazin-1-yl)ethoxy]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(C)CCN1CCOC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 DECWCGJHVBGDPC-UHFFFAOYSA-N 0.000 claims 1
PYLOBWHIDAVZTO-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(diethylamino)ethoxy]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 PYLOBWHIDAVZTO-UHFFFAOYSA-N 0.000 claims 1
GBMAQXAAFUMFMD-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(dimethylamino)ethoxy]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 GBMAQXAAFUMFMD-UHFFFAOYSA-N 0.000 claims 1
ARFUBOBMDOPZSH-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-(hydroxymethyl)-6-azaspiro[2.5]octan-6-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound OCC1CC11CCN(C=2C=CC(NC=3C=4C(=O)NN=CC=4N=C(N=3)N3CCCCCC3)=CC=2)CC1 ARFUBOBMDOPZSH-UHFFFAOYSA-N 0.000 claims 1
CISVPDHPAHVGKD-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethoxy]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(CCO)CCN1CCOC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 CISVPDHPAHVGKD-UHFFFAOYSA-N 0.000 claims 1
OOWPOJNZCSHXJD-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(CCO)CCN1CCC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 OOWPOJNZCSHXJD-UHFFFAOYSA-N 0.000 claims 1
BAPVGKRYXAZESI-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[3-(2-hydroxyethyl)piperidin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1C(CCO)CCCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 BAPVGKRYXAZESI-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
ZVHURPCTFRIVDT-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(2,3-dihydroxypropyl)piperazin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(CC(O)CO)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 ZVHURPCTFRIVDT-UHFFFAOYSA-N 0.000 claims 1
AUCSMJREAGEEBJ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(2-fluoroethyl)piperazin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(CCF)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 AUCSMJREAGEEBJ-UHFFFAOYSA-N 0.000 claims 1
CNPKPHSSRROGJX-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(2-fluoroethyl)piperidin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CC(CCF)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 CNPKPHSSRROGJX-UHFFFAOYSA-N 0.000 claims 1
AGWDZMOUZQZVIK-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(2-hydroxy-2-methylpropanoyl)piperazin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(C(=O)C(C)(O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 AGWDZMOUZQZVIK-UHFFFAOYSA-N 0.000 claims 1
QBRFMRDBOKTIJD-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(2-hydroxyethyl)-1,4-diazepan-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(CCO)CCCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 QBRFMRDBOKTIJD-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
YJRXHACLAZOJMV-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(2-hydroxyethyl)piperidin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CC(CCO)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 YJRXHACLAZOJMV-UHFFFAOYSA-N 0.000 claims 1
OHKAPGVTPJBHMW-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CC(C(C)(O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 OHKAPGVTPJBHMW-UHFFFAOYSA-N 0.000 claims 1
ZWDHHDQLIIZORJ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(2-methoxyethyl)piperazin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(CCOC)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 ZWDHHDQLIIZORJ-UHFFFAOYSA-N 0.000 claims 1
XSPVBRTUDJLQHT-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(2h-tetrazol-5-ylmethyl)piperidin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=C1)=CC=C1N(CC1)CCC1CC=1N=NNN=1 XSPVBRTUDJLQHT-UHFFFAOYSA-N 0.000 claims 1
CIXIYNWZBIBNPJ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(3-hydroxypropyl)piperazin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(CCCO)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 CIXIYNWZBIBNPJ-UHFFFAOYSA-N 0.000 claims 1
JNGDMXQJQQFQCZ-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[4-(3-hydroxypropyl)piperidin-1-yl]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CC(CCCO)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 JNGDMXQJQQFQCZ-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
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 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
UNOYSHGDZLAVLK-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[4-[bis(2-hydroxyethyl)amino]anilino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1=CC(N(CCO)CCO)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 UNOYSHGDZLAVLK-UHFFFAOYSA-N 0.000 claims 1
GVZMVIZFLAHGSP-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[[6-(2-piperazin-1-ylethoxy)pyridin-3-yl]amino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=N1)=CC=C1OCCN1CCNCC1 GVZMVIZFLAHGSP-UHFFFAOYSA-N 0.000 claims 1
YURDXNFXINHACP-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[[6-(3-hydroxypiperidin-1-yl)pyridin-3-yl]amino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1C(O)CCCN1C(N=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 YURDXNFXINHACP-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
DIGIWXYCKRCHGB-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[[6-[4-(2-hydroxy-2-methylpropanoyl)piperazin-1-yl]pyridin-3-yl]amino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CN(C(=O)C(C)(O)C)CCN1C(N=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 DIGIWXYCKRCHGB-UHFFFAOYSA-N 0.000 claims 1
YYZHLVMUOGPGFH-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[[6-[4-(2-hydroxyethyl)piperidin-1-yl]pyridin-3-yl]amino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CC(CCO)CCN1C(N=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 YYZHLVMUOGPGFH-UHFFFAOYSA-N 0.000 claims 1
XDZRLVAWZMEKTN-UHFFFAOYSA-N 2-(azepan-1-yl)-4-[[6-[4-(2h-tetrazol-5-ylmethyl)piperidin-1-yl]pyridin-3-yl]amino]-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=N1)=CC=C1N(CC1)CCC1CC=1N=NNN=1 XDZRLVAWZMEKTN-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
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-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
CIRUZMRIKHTPOG-UHFFFAOYSA-N 2-[1-[2-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenoxy]ethyl]piperidin-4-yl]acetic acid Chemical compound C1CC(CC(=O)O)CCN1CCOC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 CIRUZMRIKHTPOG-UHFFFAOYSA-N 0.000 claims 1
SXDILXCFYORZFS-UHFFFAOYSA-N 2-[1-[2-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]piperidin-1-yl]ethyl]piperidin-4-yl]acetonitrile Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(CC1)CCN1CCN1CCC(CC#N)CC1 SXDILXCFYORZFS-UHFFFAOYSA-N 0.000 claims 1
ONWQCRZBUOXITQ-UHFFFAOYSA-N 2-[1-[3-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenoxy]propyl]piperidin-4-yl]acetic acid Chemical compound C1CC(CC(=O)O)CCN1CCCOC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 ONWQCRZBUOXITQ-UHFFFAOYSA-N 0.000 claims 1
BMCOMLYRWROTIC-UHFFFAOYSA-N 2-[1-[4-(3,4-dimethoxyanilino)-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 BMCOMLYRWROTIC-UHFFFAOYSA-N 0.000 claims 1
VOCWEMFHZLOTHJ-UHFFFAOYSA-N 2-[1-[4-(3,5-dimethoxyanilino)-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound COC1=CC(OC)=CC(NC=2C=3C(=O)NN=CC=3N=C(N=2)N2CCC(CC#N)CC2)=C1 VOCWEMFHZLOTHJ-UHFFFAOYSA-N 0.000 claims 1
BCUZROOCSCJNDI-UHFFFAOYSA-N 2-[1-[4-(3-methoxyanilino)-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound COC1=CC=CC(NC=2C=3C(=O)NN=CC=3N=C(N=2)N2CCC(CC#N)CC2)=C1 BCUZROOCSCJNDI-UHFFFAOYSA-N 0.000 claims 1
YKIWKCHKWQGGES-UHFFFAOYSA-N 2-[1-[4-(4-fluoroanilino)-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=CC(F)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 YKIWKCHKWQGGES-UHFFFAOYSA-N 0.000 claims 1
MVXVCMDMYHRBPV-UHFFFAOYSA-N 2-[1-[4-(4-methylsulfonylanilino)-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 MVXVCMDMYHRBPV-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
KGMKDNMNJDEGKW-UHFFFAOYSA-N 2-[1-[4-[(5-oxo-2-phenyl-6h-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]piperidin-4-yl]acetonitrile Chemical compound C=12C(=O)NN=CC2=NC(C=2C=CC=CC=2)=NC=1NC(C=C1)=CC=C1N1CCC(CC#N)CC1 KGMKDNMNJDEGKW-UHFFFAOYSA-N 0.000 claims 1
ZZIPKXKOZASFNH-UHFFFAOYSA-N 2-[1-[4-[3-(hydroxymethyl)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound OCC1=CC=CC(NC=2C=3C(=O)NN=CC=3N=C(N=2)N2CCC(CC#N)CC2)=C1 ZZIPKXKOZASFNH-UHFFFAOYSA-N 0.000 claims 1
NSXLMTSVPFZQNQ-UHFFFAOYSA-N 2-[1-[4-[4-(1-hydroxy-2-methylpropan-2-yl)oxyanilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=CC(OC(C)(CO)C)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 NSXLMTSVPFZQNQ-UHFFFAOYSA-N 0.000 claims 1
JZNSOSHUGJVPCI-UHFFFAOYSA-N 2-[1-[4-[4-(2-aminoethoxy)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=CC(OCCN)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 JZNSOSHUGJVPCI-UHFFFAOYSA-N 0.000 claims 1
XMFADZKTTRIXAE-UHFFFAOYSA-N 2-[1-[4-[4-(2-ethyltetrazol-5-yl)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound CCN1N=NC(C=2C=CC(NC=3C=4C(=O)NN=CC=4N=C(N=3)N3CCC(CC#N)CC3)=CC=2)=N1 XMFADZKTTRIXAE-UHFFFAOYSA-N 0.000 claims 1
QKCMDGMFYDDNIU-UHFFFAOYSA-N 2-[1-[4-[4-(2-hydroxyethoxy)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=CC(OCCO)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 QKCMDGMFYDDNIU-UHFFFAOYSA-N 0.000 claims 1
SLWNSBACHGTCSL-UHFFFAOYSA-N 2-[1-[4-[4-(2-hydroxyethyl)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=CC(CCO)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 SLWNSBACHGTCSL-UHFFFAOYSA-N 0.000 claims 1
JLVJXSSGBIIFAL-UHFFFAOYSA-N 2-[1-[4-[4-(2-methoxyethoxy)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=CC(OCCOC)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 JLVJXSSGBIIFAL-UHFFFAOYSA-N 0.000 claims 1
STUXZVYNMDRZHE-UHFFFAOYSA-N 2-[1-[4-[4-(3-fluoropropyl)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=CC(CCCF)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 STUXZVYNMDRZHE-UHFFFAOYSA-N 0.000 claims 1
KBTZBNSTRFVKHX-UHFFFAOYSA-N 2-[1-[4-[4-(3-hydroxypropoxy)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=CC(OCCCO)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 KBTZBNSTRFVKHX-UHFFFAOYSA-N 0.000 claims 1
LHSAEXHLZCPBIR-UHFFFAOYSA-N 2-[1-[4-[4-(3-hydroxypropyl)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=CC(CCCO)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 LHSAEXHLZCPBIR-UHFFFAOYSA-N 0.000 claims 1
MEUIVFUNEDFODR-UHFFFAOYSA-N 2-[1-[4-[4-(4,4-difluoropiperidin-1-yl)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CC(F)(F)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 MEUIVFUNEDFODR-UHFFFAOYSA-N 0.000 claims 1
CRTWTCGXTBFBRC-UHFFFAOYSA-N 2-[1-[4-[4-(4-ethyl-3-oxopiperazin-1-yl)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1C(=O)N(CC)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 CRTWTCGXTBFBRC-UHFFFAOYSA-N 0.000 claims 1
DGDKLFRWILUTRT-UHFFFAOYSA-N 2-[1-[4-[4-(4-fluoropiperidin-1-yl)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CC(F)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 DGDKLFRWILUTRT-UHFFFAOYSA-N 0.000 claims 1
ZZXDCXDYBQNAQO-UHFFFAOYSA-N 2-[1-[4-[4-(4-methoxypiperidin-1-yl)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CC(OC)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 ZZXDCXDYBQNAQO-UHFFFAOYSA-N 0.000 claims 1
AYVBENXNEMWXMU-UHFFFAOYSA-N 2-[1-[4-[4-(4-methylpiperazin-1-yl)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 AYVBENXNEMWXMU-UHFFFAOYSA-N 0.000 claims 1
NMQCMGVCKWRENS-UHFFFAOYSA-N 2-[1-[4-[4-(difluoromethoxy)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=CC(OC(F)F)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 NMQCMGVCKWRENS-UHFFFAOYSA-N 0.000 claims 1
NPSWKSAWDLUJLR-UHFFFAOYSA-N 2-[1-[4-[4-(hydroxymethyl)anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=CC(CO)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 NPSWKSAWDLUJLR-UHFFFAOYSA-N 0.000 claims 1
LLENPOKVIGSYRZ-UHFFFAOYSA-N 2-[1-[4-[4-[2-(4-hydroxy-4-methylpiperidin-1-yl)ethoxy]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CC(C)(O)CCN1CCOC(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 LLENPOKVIGSYRZ-UHFFFAOYSA-N 0.000 claims 1
NLXLMINLOOVCET-UHFFFAOYSA-N 2-[1-[4-[4-[2-(4-methylpiperazin-1-yl)-2-oxoethoxy]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CN(C)CCN1C(=O)COC(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 NLXLMINLOOVCET-UHFFFAOYSA-N 0.000 claims 1
CISLRSNPHVRCJG-UHFFFAOYSA-N 2-[1-[4-[4-[2-(diethylamino)ethoxy]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 CISLRSNPHVRCJG-UHFFFAOYSA-N 0.000 claims 1
FDTCETNNEBMDSI-UHFFFAOYSA-N 2-[1-[4-[4-[2-(hydroxymethyl)-6-azaspiro[2.5]octan-6-yl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound OCC1CC11CCN(C=2C=CC(NC=3C=4C(=O)NN=CC=4N=C(N=3)N3CCC(CC#N)CC3)=CC=2)CC1 FDTCETNNEBMDSI-UHFFFAOYSA-N 0.000 claims 1
UZVNTRNYZHBBRQ-UHFFFAOYSA-N 2-[1-[4-[4-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CN(CCO)CCN1CCC(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 UZVNTRNYZHBBRQ-UHFFFAOYSA-N 0.000 claims 1
IAQFWBGWLCTRFN-UHFFFAOYSA-N 2-[1-[4-[4-[2-[4-(hydroxymethyl)piperidin-1-yl]ethoxy]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CC(CO)CCN1CCOC(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 IAQFWBGWLCTRFN-UHFFFAOYSA-N 0.000 claims 1
GYZLMNXPXAYBMK-UHFFFAOYSA-N 2-[1-[4-[4-[3-(2-hydroxyethyl)piperidin-1-yl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1C(CCO)CCCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 GYZLMNXPXAYBMK-UHFFFAOYSA-N 0.000 claims 1
HCWZVRZKAROHBM-UHFFFAOYSA-N 2-[1-[4-[4-[3-(hydroxymethyl)piperidin-1-yl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1C(CO)CCCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 HCWZVRZKAROHBM-UHFFFAOYSA-N 0.000 claims 1
IQXLJBQAZJZPOZ-UHFFFAOYSA-N 2-[1-[4-[4-[4-(2,3-dihydroxypropyl)piperazin-1-yl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CN(CC(O)CO)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 IQXLJBQAZJZPOZ-UHFFFAOYSA-N 0.000 claims 1
AOSXWJLOQOHZLF-UHFFFAOYSA-N 2-[1-[4-[4-[4-(2-aminoethyl)piperazin-1-yl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CN(CCN)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 AOSXWJLOQOHZLF-UHFFFAOYSA-N 0.000 claims 1
VJANWUOQIRLQLV-UHFFFAOYSA-N 2-[1-[4-[4-[4-(2-fluoroethyl)piperazin-1-yl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CN(CCF)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 VJANWUOQIRLQLV-UHFFFAOYSA-N 0.000 claims 1
XVNUWBXCLRWCLO-UHFFFAOYSA-N 2-[1-[4-[4-[4-(2-fluoroethyl)piperidin-1-yl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CC(CCF)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 XVNUWBXCLRWCLO-UHFFFAOYSA-N 0.000 claims 1
VNEOFSRZUQNVIU-UHFFFAOYSA-N 2-[1-[4-[4-[4-(2-hydroxyethyl)-1,4-diazepan-1-yl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CN(CCO)CCCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 VNEOFSRZUQNVIU-UHFFFAOYSA-N 0.000 claims 1
RUXLYAGOXLTHIG-UHFFFAOYSA-N 2-[1-[4-[4-[4-(2-hydroxyethyl)piperazin-1-yl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CN(CCO)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 RUXLYAGOXLTHIG-UHFFFAOYSA-N 0.000 claims 1
VGWZWARUYOJGFS-UHFFFAOYSA-N 2-[1-[4-[4-[4-(2-hydroxyethyl)piperidin-1-yl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CC(CCO)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 VGWZWARUYOJGFS-UHFFFAOYSA-N 0.000 claims 1
LXSFMSJRSBGNET-UHFFFAOYSA-N 2-[1-[4-[4-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CC(C(C)(O)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 LXSFMSJRSBGNET-UHFFFAOYSA-N 0.000 claims 1
QKALHAYRECPYNX-UHFFFAOYSA-N 2-[1-[4-[4-[4-(2-methoxyethyl)piperazin-1-yl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CN(CCOC)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 QKALHAYRECPYNX-UHFFFAOYSA-N 0.000 claims 1
FYJRMCOKVMYLQJ-UHFFFAOYSA-N 2-[1-[4-[4-[4-(3-hydroxypropyl)piperazin-1-yl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CN(CCCO)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 FYJRMCOKVMYLQJ-UHFFFAOYSA-N 0.000 claims 1
RDEDVVUPPSUAIU-UHFFFAOYSA-N 2-[1-[4-[4-[4-(cyanomethyl)piperazin-1-yl]anilino]-5-oxo-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=C1N1CCN(CC#N)CC1 RDEDVVUPPSUAIU-UHFFFAOYSA-N 0.000 claims 1
HXAZIDNOTNMKQS-UHFFFAOYSA-N 2-[1-[4-[4-[4-(hydroxymethyl)piperidin-1-yl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CC(CO)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 HXAZIDNOTNMKQS-UHFFFAOYSA-N 0.000 claims 1
CLCVYZZSOVSICV-UHFFFAOYSA-N 2-[1-[4-[4-[4-[2-(dimethylamino)ethyl]piperazin-1-yl]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CN(CCN(C)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 CLCVYZZSOVSICV-UHFFFAOYSA-N 0.000 claims 1
YORPJVFFCMACGV-UHFFFAOYSA-N 2-[1-[4-[4-[bis(2-hydroxyethyl)amino]anilino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=CC(N(CCO)CCO)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 YORPJVFFCMACGV-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
NONFSTXUUVMGBF-UHFFFAOYSA-N 2-[1-[4-[[2-(3-methoxyphenyl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetonitrile Chemical compound COC1=CC=CC(C=2N=C3C(C(NN=C3)=O)=C(NC=3C=CC(=CC=3)N3CCC(CC#N)CC3)N=2)=C1 NONFSTXUUVMGBF-UHFFFAOYSA-N 0.000 claims 1
ITORKKLKAZVJBF-UHFFFAOYSA-N 2-[1-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]-2-methylpropanoic acid Chemical compound C1CC(C(C)(C)C(O)=O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 ITORKKLKAZVJBF-UHFFFAOYSA-N 0.000 claims 1
PGHYLBCWLPGZDH-UHFFFAOYSA-N 2-[1-[4-[[2-(azepan-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(N2CCCCCC2)=NC2=C1C(=O)NN=C2 PGHYLBCWLPGZDH-UHFFFAOYSA-N 0.000 claims 1
IJBKDGMSEDAMBN-UHFFFAOYSA-N 2-[1-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C1CCN(C=2C=CC(NC=3C=4C(=O)NN=CC=4N=C(N=3)N3CCCCCC3)=CC=2)CC1 IJBKDGMSEDAMBN-UHFFFAOYSA-N 0.000 claims 1
LENHGPBRXMASGO-UHFFFAOYSA-N 2-[1-[4-[[2-(azocan-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(N2CCCCCCC2)=NC2=C1C(=O)NN=C2 LENHGPBRXMASGO-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
BUWCWAIGJUCVTA-UHFFFAOYSA-N 2-[1-[4-[[2-[4-(2-cyanopropan-2-yl)piperidin-1-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetic acid Chemical compound C1CC(C(C)(C#N)C)CCN1C1=NC(NC=2C=CC(=CC=2)N2CCC(CC(O)=O)CC2)=C2C(=O)NN=CC2=N1 BUWCWAIGJUCVTA-UHFFFAOYSA-N 0.000 claims 1
GIVBOIPQEJTHPU-UHFFFAOYSA-N 2-[1-[4-[[2-[4-(cyanomethyl)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(CC#N)CC2)=NC2=C1C(=O)NN=C2 GIVBOIPQEJTHPU-UHFFFAOYSA-N 0.000 claims 1
CAADRCABWYRLNQ-UHFFFAOYSA-N 2-[1-[4-[[2-[4-(cyanomethyl)piperidin-1-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-3-yl]acetic acid Chemical compound C1C(CC(=O)O)CCCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 CAADRCABWYRLNQ-UHFFFAOYSA-N 0.000 claims 1
VJJUMDMQKUYLKE-UHFFFAOYSA-N 2-[1-[4-[[2-[4-(cyanomethyl)piperidin-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(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 VJJUMDMQKUYLKE-UHFFFAOYSA-N 0.000 claims 1
FUZONMXIBGUQPR-UHFFFAOYSA-N 2-[1-[4-[[2-[cyclohexyl(methyl)amino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]acetic acid Chemical compound N=1C(NC=2C=CC(=CC=2)N2CCC(CC(O)=O)CC2)=C(C(NN=C2)=O)C2=NC=1N(C)C1CCCCC1 FUZONMXIBGUQPR-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
AJXVRZSFKIWMPE-UHFFFAOYSA-N 2-[1-[4-[[6-(3-hydroxypiperidin-1-yl)pyridin-3-yl]amino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1C(O)CCCN1C(N=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 AJXVRZSFKIWMPE-UHFFFAOYSA-N 0.000 claims 1
KAZVWDLCKKDSPA-UHFFFAOYSA-N 2-[1-[4-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]-5-oxo-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 KAZVWDLCKKDSPA-UHFFFAOYSA-N 0.000 claims 1
OOLXTNYZCCEZJE-UHFFFAOYSA-N 2-[1-[5-[(5-oxo-2-phenyl-6h-pyrimido[4,5-d]pyridazin-4-yl)amino]pyridin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C=12C(=O)NN=CC2=NC(C=2C=CC=CC=2)=NC=1NC(C=N1)=CC=C1N1CCC(CC#N)CC1 OOLXTNYZCCEZJE-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
OVBVNXVTONKYRW-UHFFFAOYSA-N 2-[1-[5-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]pyridin-2-yl]piperidin-4-yl]acetic acid Chemical compound C1CC(CC(=O)O)CCN1C(N=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 OVBVNXVTONKYRW-UHFFFAOYSA-N 0.000 claims 1
SINXYUJLCYIKMA-UHFFFAOYSA-N 2-[1-[5-[[2-(azepan-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(N2CCCCCC2)=NC=1NC(C=N1)=CC=C1N1CCC(CC#N)CC1 SINXYUJLCYIKMA-UHFFFAOYSA-N 0.000 claims 1
UJFNGXNNRFLOJF-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-3-yl]acetic acid Chemical compound C1C(CC(=O)O)CCCN1C(N=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 UJFNGXNNRFLOJF-UHFFFAOYSA-N 0.000 claims 1
SFVSAJFMIQDDRE-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]acetic acid Chemical compound C1CC(CC(=O)O)CCN1C(N=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 SFVSAJFMIQDDRE-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
AEWNGOHLUNPQEQ-UHFFFAOYSA-N 2-[1-[5-oxo-4-(3,4,5-trimethoxyanilino)-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound COC1=C(OC)C(OC)=CC(NC=2C=3C(=O)NN=CC=3N=C(N=2)N2CCC(CC#N)CC2)=C1 AEWNGOHLUNPQEQ-UHFFFAOYSA-N 0.000 claims 1
AOMSNALEFNZLAY-UHFFFAOYSA-N 2-[1-[5-oxo-4-(4-piperazin-1-ylanilino)-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=C1N1CCNCC1 AOMSNALEFNZLAY-UHFFFAOYSA-N 0.000 claims 1
LFWPPUMWYUVLEU-UHFFFAOYSA-N 2-[1-[5-oxo-4-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)amino]-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=C2NC(=O)NC2=CC=C1NC(C=1C(=O)NN=CC=1N=1)=NC=1N1CCC(CC#N)CC1 LFWPPUMWYUVLEU-UHFFFAOYSA-N 0.000 claims 1
FJJYDXLMPWBGSK-UHFFFAOYSA-N 2-[1-[5-oxo-4-[(6-piperazin-1-ylpyridin-3-yl)amino]-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=N1)=CC=C1N1CCNCC1 FJJYDXLMPWBGSK-UHFFFAOYSA-N 0.000 claims 1
RYGOOQDQGBYSJO-UHFFFAOYSA-N 2-[1-[5-oxo-4-[4-(2-piperazin-1-ylethoxy)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=C1OCCN1CCNCC1 RYGOOQDQGBYSJO-UHFFFAOYSA-N 0.000 claims 1
FRTDJFPREPWBPC-UHFFFAOYSA-N 2-[1-[5-oxo-4-[4-(2-piperidin-4-ylethoxy)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=C1OCCC1CCNCC1 FRTDJFPREPWBPC-UHFFFAOYSA-N 0.000 claims 1
ODNKDIDXPUIXMO-UHFFFAOYSA-N 2-[1-[5-oxo-4-[4-(3-piperazin-1-ylpropyl)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=C1CCCN1CCNCC1 ODNKDIDXPUIXMO-UHFFFAOYSA-N 0.000 claims 1
BFUHTWSWTXIEJC-UHFFFAOYSA-N 2-[1-[5-oxo-4-[4-(piperazin-1-ylmethyl)anilino]-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetic acid;hydrochloride Chemical compound Cl.C1CC(CC(=O)O)CCN1C1=NC(NC=2C=CC(CN3CCNCC3)=CC=2)=C2C(=O)NN=CC2=N1 BFUHTWSWTXIEJC-UHFFFAOYSA-N 0.000 claims 1
QXCHIHIQFOYQGH-UHFFFAOYSA-N 2-[1-[5-oxo-4-[4-(trifluoromethoxy)anilino]-6h-pyrimido[4,5-d]pyridazin-2-yl]piperidin-4-yl]acetonitrile Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 QXCHIHIQFOYQGH-UHFFFAOYSA-N 0.000 claims 1
OWDALGIWVSYEOC-UHFFFAOYSA-N 2-[1-[5-oxo-4-[4-[4-(2h-tetrazol-5-ylmethyl)piperidin-1-yl]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=C1N(CC1)CCC1CC=1N=NNN=1 OWDALGIWVSYEOC-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
CMPDWEQQDRGLNH-UHFFFAOYSA-N 2-[1-[[4-[[2-(azepan-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(N2CCCCCC2)=NC2=C1C(=O)NN=C2 CMPDWEQQDRGLNH-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
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
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
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
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
FBASVZLYAFUGQZ-UHFFFAOYSA-N 2-[4-[2-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenoxy]ethyl]piperazin-1-yl]-2-methylpropanenitrile Chemical compound C1CN(C(C)(C#N)C)CCN1CCOC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 FBASVZLYAFUGQZ-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
CXXPNTGGRNQRLO-UHFFFAOYSA-N 2-[4-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenoxy]piperidin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCC1OC(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 CXXPNTGGRNQRLO-UHFFFAOYSA-N 0.000 claims 1
RRPYHFCTYGYGDP-UHFFFAOYSA-N 2-[4-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperazin-1-yl]-2-methylpropanamide Chemical compound C1CN(C(C)(C)C(N)=O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 RRPYHFCTYGYGDP-UHFFFAOYSA-N 0.000 claims 1
BUHQHAKCQJVJNR-UHFFFAOYSA-N 2-[4-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperazin-1-yl]-2-methylpropanenitrile Chemical compound C1CN(C(C)(C#N)C)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 BUHQHAKCQJVJNR-UHFFFAOYSA-N 0.000 claims 1
PGWIMNRICNCIBR-UHFFFAOYSA-N 2-[4-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-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(N2CCCCCC2)=NC2=C1C(=O)NN=C2 PGWIMNRICNCIBR-UHFFFAOYSA-N 0.000 claims 1
GYAKIFQKEUIRSB-UHFFFAOYSA-N 2-[4-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 GYAKIFQKEUIRSB-UHFFFAOYSA-N 0.000 claims 1
JAJPXOXMPWOKPD-UHFFFAOYSA-N 2-[4-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperazin-1-yl]acetonitrile Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCCC2)=NC=1NC(C=C1)=CC=C1N1CCN(CC#N)CC1 JAJPXOXMPWOKPD-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
YKMKSKQQPHLCCJ-UHFFFAOYSA-N 2-[4-[5-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]pyridin-2-yl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1C(N=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 YKMKSKQQPHLCCJ-UHFFFAOYSA-N 0.000 claims 1
QEHHYYYDYIPNSU-UHFFFAOYSA-N 2-[4-[5-oxo-4-[4-(2-piperazin-1-ylethoxy)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=C1OCCN1CCNCC1 QEHHYYYDYIPNSU-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
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
YZINQLLBHOCDGX-UHFFFAOYSA-N 2-methyl-2-[1-[4-[(5-oxo-2-phenyl-6h-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]piperidin-4-yl]propanenitrile Chemical compound C1CC(C(C)(C#N)C)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=NC2=C1C(=O)NN=C2 YZINQLLBHOCDGX-UHFFFAOYSA-N 0.000 claims 1
ODGXBLJUBMENDM-UHFFFAOYSA-N 2-methyl-2-[1-[4-[(5-oxo-2-phenyl-6h-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=C1NC1=NC(C=2C=CC=CC=2)=NC2=C1C(=O)NN=C2 ODGXBLJUBMENDM-UHFFFAOYSA-N 0.000 claims 1
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 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
XNOMOWJZGMEILF-UHFFFAOYSA-N 2-phenyl-4-[[1-(2-piperazin-1-ylethyl)pyrazol-4-yl]amino]-6h-pyrimido[4,5-d]pyridazin-5-one;hydrochloride Chemical compound Cl.C=12C(=O)NN=CC2=NC(C=2C=CC=CC=2)=NC=1NC(=C1)C=NN1CCN1CCNCC1 XNOMOWJZGMEILF-UHFFFAOYSA-N 0.000 claims 1
FPSCWKHRIRPRNQ-UHFFFAOYSA-N 3-[1-[4-[(5-oxo-2-phenyl-6h-pyrimido[4,5-d]pyridazin-4-yl)amino]phenyl]piperidin-4-yl]propanoic acid Chemical compound C1CC(CCC(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=NC2=C1C(=O)NN=C2 FPSCWKHRIRPRNQ-UHFFFAOYSA-N 0.000 claims 1
LERGMBDKQPLVFB-UHFFFAOYSA-N 3-[1-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]propanoic acid Chemical compound C1CC(CCC(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 LERGMBDKQPLVFB-UHFFFAOYSA-N 0.000 claims 1
WFSPIPHKSHGGFT-UHFFFAOYSA-N 3-[1-[4-[[2-[4-(cyanomethyl)piperidin-1-yl]-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperidin-4-yl]propanoic acid Chemical compound C1CC(CCC(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 WFSPIPHKSHGGFT-UHFFFAOYSA-N 0.000 claims 1
YFBIHTBFBBFRFC-UHFFFAOYSA-N 3-[4-[4-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]phenyl]piperazin-1-yl]propanoic acid Chemical compound C1CN(CCC(=O)O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 YFBIHTBFBBFRFC-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
JKTGTIZLZMFIRN-UHFFFAOYSA-N 3-[4-[5-[[2-(azepan-1-yl)-5-oxo-6h-pyrimido[4,5-d]pyridazin-4-yl]amino]pyridin-2-yl]piperazin-1-yl]-3-oxopropanenitrile Chemical compound C1CN(C(CC#N)=O)CCN1C(N=C1)=CC=C1NC1=NC(N2CCCCCC2)=NC2=C1C(=O)NN=C2 JKTGTIZLZMFIRN-UHFFFAOYSA-N 0.000 claims 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 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
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
GNOPSCBEOSUMGK-UHFFFAOYSA-N 4-[4-[2-(1,4-diazepan-1-yl)ethoxy]anilino]-2-piperidin-1-yl-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCC2)=NC=1NC(C=C1)=CC=C1OCCN1CCCNCC1 GNOPSCBEOSUMGK-UHFFFAOYSA-N 0.000 claims 1
KAFYDCJMMMLHRA-UHFFFAOYSA-N 4-[4-[2-(4-hydroxypiperidin-1-yl)ethoxy]anilino]-2-piperidin-1-yl-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1CC(O)CCN1CCOC(C=C1)=CC=C1NC1=NC(N2CCCCC2)=NC2=C1C(=O)NN=C2 KAFYDCJMMMLHRA-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
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
NJLDZCNGRFGZMB-RBUKOAKNSA-N 4-[4-[[(2s,5s)-5-(hydroxymethyl)-1,4-dioxan-2-yl]methoxy]anilino]-2-phenyl-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C1O[C@@H](CO)CO[C@@H]1COC(C=C1)=CC=C1NC1=NC(C=2C=CC=CC=2)=NC2=C1C(=O)NN=C2 NJLDZCNGRFGZMB-RBUKOAKNSA-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
OOBNVERUJKKRBQ-UHFFFAOYSA-N 4-[[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]amino]-2-phenyl-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(C=2C=CC=CC=2)=NC=1NC(=C1)C=NN1CCN1CCOCC1 OOBNVERUJKKRBQ-UHFFFAOYSA-N 0.000 claims 1
UEPCIYPCSUUHKN-UHFFFAOYSA-N 4-[[6-(2-piperazin-1-ylethoxy)pyridin-3-yl]amino]-2-piperidin-1-yl-6h-pyrimido[4,5-d]pyridazin-5-one Chemical compound C=12C(=O)NN=CC2=NC(N2CCCCC2)=NC=1NC(C=N1)=CC=C1OCCN1CCNCC1 UEPCIYPCSUUHKN-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
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
FHUNUEAFOCKJBZ-UHFFFAOYSA-N 6-[4-[(5-oxo-2-thiophen-3-yl-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)C3=CSC=C3)=CC=2)CC1 FHUNUEAFOCKJBZ-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
LACMQPQIGPVYDG-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;hydrochloride Chemical compound Cl.OC(=O)C1CC11CCN(C=2C=CC(NC=3C=4C(=O)NN=CC=4N=C(N=3)N3CCNCCC3)=CC=2)CC1 LACMQPQIGPVYDG-UHFFFAOYSA-N 0.000 claims 1
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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
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
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
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
BJFPPTIKXSPLBJ-UHFFFAOYSA-N 6-[5-[[2-[4-(cyanomethyl)piperidin-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)N3CCC(CC#N)CC3)=CC=2)CC1 BJFPPTIKXSPLBJ-UHFFFAOYSA-N 0.000 claims 1
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FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
AKXHGIZHOIWBRS-UHFFFAOYSA-M [O-]C(=O)C1CC11CCN(CC1)c1ccc(NC2NC(NC3CNNC(=O)C23)c2ccccc2)cc1 Chemical compound [O-]C(=O)C1CC11CCN(CC1)c1ccc(NC2NC(NC3CNNC(=O)C23)c2ccccc2)cc1 AKXHGIZHOIWBRS-UHFFFAOYSA-M 0.000 claims 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
229940092714 benzenesulfonic acid Drugs 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
235000015165 citric acid Nutrition 0.000 claims 1
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 1
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 1
QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical class C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 claims 1
125000004310 dioxan-2-yl group Chemical group [H]C1([H])OC([H])([H])C([H])(*)OC1([H])[H] 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
IIPMXKWCRYWFSW-UHFFFAOYSA-N ethyl 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-carboxylate Chemical compound CCOC(=O)C1CC11CCN(C=2C=CC(NC3C4C(=O)NNCC4NC(N3)C=3C=CC=CC=3)=CC=2)CC1 IIPMXKWCRYWFSW-UHFFFAOYSA-N 0.000 claims 1
239000001530 fumaric acid Substances 0.000 claims 1
235000011087 fumaric acid Nutrition 0.000 claims 1
NLFLXLJXEIUQDL-UHFFFAOYSA-N gusacitinib Chemical compound C1CC(O)CCN1C(C=C1)=CC=C1NC1=NC(N2CCC(CC#N)CC2)=NC2=C1C(=O)NN=C2 NLFLXLJXEIUQDL-UHFFFAOYSA-N 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000005842 heteroatom Chemical group 0.000 claims 1
125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
IRXWIGPNZAGTAI-UHFFFAOYSA-N hydroxymethyl 6-[4-[[2-(azepan-1-yl)-5-carbamoyl-6-methanimidoylpyrimidin-4-yl]amino]phenyl]-6-azaspiro[2.5]octane-2-carboxylate Chemical compound N1=C(N2CCCCCC2)N=C(C=N)C(C(=O)N)=C1NC(C=C1)=CC=C1N(CC1)CCC21CC2C(=O)OCO IRXWIGPNZAGTAI-UHFFFAOYSA-N 0.000 claims 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
230000004054 inflammatory process Effects 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 claims 1
230000005764 inhibitory process Effects 0.000 claims 1
239000004310 lactic acid Substances 0.000 claims 1
235000014655 lactic acid Nutrition 0.000 claims 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
239000011976 maleic acid Substances 0.000 claims 1
239000001630 malic acid Substances 0.000 claims 1
235000011090 malic acid Nutrition 0.000 claims 1
229960002510 mandelic acid Drugs 0.000 claims 1
229940098779 methanesulfonic acid Drugs 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
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 1
150000002780 morpholines Chemical class 0.000 claims 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims 1
229910017604 nitric acid Inorganic materials 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
POTQIHURRUDRCG-UHFFFAOYSA-N nonanoic acid;hydrochloride Chemical compound Cl.CCCCCCCCC(O)=O POTQIHURRUDRCG-UHFFFAOYSA-N 0.000 claims 1
230000037361 pathway Effects 0.000 claims 1
150000003053 piperidines Chemical class 0.000 claims 1
235000019260 propionic acid Nutrition 0.000 claims 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
229920006395 saturated elastomer Polymers 0.000 claims 1
239000011975 tartaric acid Substances 0.000 claims 1
235000002906 tartaric acid Nutrition 0.000 claims 1
229930192474 thiophene Natural products 0.000 claims 1
0 C*(CC1)CCC11*ON**1 Chemical compound C*(CC1)CCC11*ON**1 0.000 description 3
FWBLWCHBUNETHJ-UHFFFAOYSA-N CN(CC1)CCC1(CC(N1)=O)CC1=O Chemical compound CN(CC1)CCC1(CC(N1)=O)CC1=O FWBLWCHBUNETHJ-UHFFFAOYSA-N 0.000 description 1

JP2014527282A 2011-08-23 2012-08-23 ピリミド−ピリダジノン化合物及びその使用 Active JP5993010B2 (ja)