JPWO2020132197A5 - - Google Patents
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- JPWO2020132197A5 JPWO2020132197A5 JP2021535854A JP2021535854A JPWO2020132197A5 JP WO2020132197 A5 JPWO2020132197 A5 JP WO2020132197A5 JP 2021535854 A JP2021535854 A JP 2021535854A JP 2021535854 A JP2021535854 A JP 2021535854A JP WO2020132197 A5 JPWO2020132197 A5 JP WO2020132197A5
- Authority
- JP
- Japan
- Prior art keywords
- alkylene
- independently selected
- alkyl
- cycloalkyl
- membered heterocycloalkyl
- Prior art date
- 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.)
- Granted
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- 125000002947 alkylene group Chemical group 0.000 claims description 442
- 125000000217 alkyl group Chemical group 0.000 claims description 365
- -1 aminosulfonylamino Chemical group 0.000 claims description 256
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 245
- 125000001424 substituent group Chemical group 0.000 claims description 237
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 149
- 229910052799 carbon Inorganic materials 0.000 claims description 127
- 125000003118 aryl group Chemical group 0.000 claims description 116
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 92
- 150000001875 compounds Chemical class 0.000 claims description 88
- 125000005843 halogen group Chemical group 0.000 claims description 82
- 125000000304 alkynyl group Chemical group 0.000 claims description 78
- 125000004432 carbon atom Chemical group C* 0.000 claims description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 72
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 61
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- 229910052717 sulfur Inorganic materials 0.000 claims description 45
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 30
- 125000005842 heteroatom Chemical group 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 11
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 10
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000003003 spiro group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 102100034111 Activin receptor type-1 Human genes 0.000 claims description 4
- 101000799140 Homo sapiens Activin receptor type-1 Proteins 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 208000014767 Myeloproliferative disease Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 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 3
- VQNAXDUXGQNSNT-NRFANRHFSA-N (2S)-4-[[4-[3-[7-(1-ethylimidazol-4-yl)-1,8-naphthyridin-4-yl]-6-methylimidazo[1,2-b]pyridazin-7-yl]phenyl]methyl]-2-methylmorpholine Chemical compound C(C)N1C=NC(=C1)C1=CC=C2C(=CC=NC2=N1)C1=CN=C2N1N=C(C(=C2)C1=CC=C(CN2C[C@@H](OCC2)C)C=C1)C VQNAXDUXGQNSNT-NRFANRHFSA-N 0.000 claims description 2
- BURXMNRNNBHPCO-UHFFFAOYSA-N (3,5-difluorophenyl)-[4-[6-methyl-7-(4-piperazin-1-ylphenyl)imidazo[1,2-b]pyridazin-3-yl]quinolin-7-yl]methanol Chemical compound FC=1C=C(C=C(C=1)F)C(O)C1=CC=C2C(=CC=NC2=C1)C1=CN=C2N1N=C(C(=C2)C1=CC=C(C=C1)N1CCNCC1)C BURXMNRNNBHPCO-UHFFFAOYSA-N 0.000 claims description 2
- WLFYGMMLMOZRQF-PMERELPUSA-N (3S)-3-methyl-1-[[4-[6-methyl-3-[7-(4-methyltriazol-2-yl)-1,8-naphthyridin-4-yl]imidazo[1,2-b]pyridazin-7-yl]phenyl]methyl]pyrrolidin-3-ol Chemical compound C[C@]1(CN(CC1)CC1=CC=C(C=C1)C1=CC=2N(N=C1C)C(=CN=2)C1=CC=NC2=NC(=CC=C12)N1N=CC(=N1)C)O WLFYGMMLMOZRQF-PMERELPUSA-N 0.000 claims description 2
- OWFXMEAGTPPEFW-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-[6-methyl-3-(7-pyridin-4-ylquinolin-4-yl)imidazo[1,2-b]pyridazin-7-yl]phenyl]methanone Chemical compound CC=1C(=CC=2N(N=1)C(=CN=2)C1=CC=NC2=CC(=CC=C12)C1=CC=NC=C1)C1=CC=C(C=C1)C(=O)N1CCN(CC1)C OWFXMEAGTPPEFW-UHFFFAOYSA-N 0.000 claims description 2
- DYWXFXUTZYZZQY-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-[6-methyl-7-(4-piperazin-1-ylphenyl)imidazo[1,2-b]pyridazin-3-yl]quinolin-7-yl]methanone Chemical compound CC=1C(=CC=2N(N=1)C(=CN=2)C1=CC=NC2=CC(=CC=C12)C(=O)N1CCN(CC1)C)C1=CC=C(C=C1)N1CCNCC1 DYWXFXUTZYZZQY-UHFFFAOYSA-N 0.000 claims description 2
- LPBOGUATLODVKG-UHFFFAOYSA-N 1-[4-[3-[7-(1-ethylimidazol-4-yl)-1,8-naphthyridin-4-yl]-6-methylimidazo[1,2-b]pyridazin-7-yl]phenyl]-N,N-dimethylmethanamine Chemical compound C(C)N1C=NC(=C1)C1=CC=C2C(=CC=NC2=N1)C1=CN=C2N1N=C(C(=C2)C1=CC=C(C=C1)CN(C)C)C LPBOGUATLODVKG-UHFFFAOYSA-N 0.000 claims description 2
- FYGOZHQWXDECIJ-UHFFFAOYSA-N 1-[4-[4-[6-methyl-7-(4-piperazin-1-ylphenyl)imidazo[1,2-b]pyridazin-3-yl]quinolin-7-yl]piperazin-1-yl]ethanone Chemical compound CC=1C(=CC=2N(N=1)C(=CN=2)C1=CC=NC2=CC(=CC=C12)N1CCN(CC1)C(C)=O)C1=CC=C(C=C1)N1CCNCC1 FYGOZHQWXDECIJ-UHFFFAOYSA-N 0.000 claims description 2
- VSYBKGGOZQUFOG-UHFFFAOYSA-N 1-[[4-[3-[7-(1-ethylimidazol-4-yl)-1,8-naphthyridin-4-yl]-6-methylimidazo[1,2-b]pyridazin-7-yl]phenyl]methyl]-4-methylpiperidin-4-ol Chemical compound C(C)N1C=NC(=C1)C1=CC=C2C(=CC=NC2=N1)C1=CN=C2N1N=C(C(=C2)C1=CC=C(CN2CCC(CC2)(O)C)C=C1)C VSYBKGGOZQUFOG-UHFFFAOYSA-N 0.000 claims description 2
- UJTOUXBEJIJABB-UHFFFAOYSA-N 1-[[4-[3-[7-(1-ethylimidazol-4-yl)-1,8-naphthyridin-4-yl]-6-methylimidazo[1,2-b]pyridazin-7-yl]phenyl]methyl]piperidin-4-ol Chemical compound C(C)N1C=NC(=C1)C1=CC=C2C(=CC=NC2=N1)C1=CN=C2N1N=C(C(=C2)C1=CC=C(CN2CCC(CC2)O)C=C1)C UJTOUXBEJIJABB-UHFFFAOYSA-N 0.000 claims description 2
- MVSQGLOPPGJURW-UHFFFAOYSA-N 1-[[4-[6-methyl-3-[7-(4-methyltriazol-2-yl)-1,8-naphthyridin-4-yl]imidazo[1,2-b]pyridazin-7-yl]phenyl]methyl]piperidin-4-ol Chemical compound CC=1C(=CC=2N(N=1)C(=CN=2)C1=CC=NC2=NC(=CC=C12)N1N=CC(=N1)C)C1=CC=C(CN2CCC(CC2)O)C=C1 MVSQGLOPPGJURW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- BHFXPKPIPBNKFI-UHFFFAOYSA-N 2,3,4,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-6-one Chemical compound C1NCCN2C(=O)CCC21 BHFXPKPIPBNKFI-UHFFFAOYSA-N 0.000 claims description 2
- YZNBWYAULANZSB-UHFFFAOYSA-N 2-(1-ethylimidazol-4-yl)-5-[6-methyl-7-(1-propan-2-ylpyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl]-1,8-naphthyridine Chemical compound C(C)N1C=NC(=C1)C1=NC2=NC=CC(=C2C=C1)C1=CN=C2N1N=C(C(=C2)C=1C=NN(C=1)C(C)C)C YZNBWYAULANZSB-UHFFFAOYSA-N 0.000 claims description 2
- SFMKNZRXYWCDHI-UHFFFAOYSA-N 2-(1-ethylimidazol-4-yl)-5-[6-methyl-7-[4-(pyrrolidin-1-ylmethyl)phenyl]imidazo[1,2-b]pyridazin-3-yl]-1,8-naphthyridine Chemical compound C(C)N1C=NC(=C1)C1=NC2=NC=CC(=C2C=C1)C1=CN=C2N1N=C(C(=C2)C1=CC=C(C=C1)CN1CCCC1)C SFMKNZRXYWCDHI-UHFFFAOYSA-N 0.000 claims description 2
- JYUIQCZRVLDPGT-UHFFFAOYSA-N 2-[4-[4-[6-methyl-3-(7-pyridin-4-ylquinolin-4-yl)imidazo[1,2-b]pyridazin-7-yl]phenyl]piperazin-1-yl]ethanol Chemical compound CC=1C(=CC=2N(N=1)C(=CN=2)C1=CC=NC2=CC(=CC=C12)C1=CC=NC=C1)C1=CC=C(C=C1)N1CCN(CC1)CCO JYUIQCZRVLDPGT-UHFFFAOYSA-N 0.000 claims description 2
- LNEDQHMHOQLLOE-UHFFFAOYSA-N 2-[4-[6-methyl-7-(4-piperazin-1-ylphenyl)imidazo[1,2-b]pyridazin-3-yl]quinolin-7-yl]-6-oxa-2-azaspiro[3.4]octane Chemical compound CC=1C(=CC=2N(N=1)C(=CN=2)C1=CC=NC2=CC(=CC=C12)N1CC2(C1)COCC2)C1=CC=C(C=C1)N1CCNCC1 LNEDQHMHOQLLOE-UHFFFAOYSA-N 0.000 claims description 2
- FYWQQHKKKZHBIX-UHFFFAOYSA-N 2-fluoro-4-[6-methyl-7-(1-piperidin-4-ylpyrazol-4-yl)imidazo[1,2-a]pyridin-3-yl]benzamide Chemical compound FC1=C(C(=O)N)C=CC(=C1)C1=CN=C2N1C=C(C(=C2)C=1C=NN(C=1)C1CCNCC1)C FYWQQHKKKZHBIX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 2
- FKJVKOKLPGNKJE-UHFFFAOYSA-N 3-methyl-1-[[4-[6-methyl-3-[7-(4-methyltriazol-2-yl)-1,8-naphthyridin-4-yl]imidazo[1,2-b]pyridazin-7-yl]phenyl]methyl]azetidin-3-ol Chemical compound CC1(CN(C1)CC1=CC=C(C=C1)C1=CC=2N(N=C1C)C(=CN=2)C1=CC=NC2=NC(=CC=C12)N1N=CC(=N1)C)O FKJVKOKLPGNKJE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- KBBNHDCXAHOPTL-UHFFFAOYSA-N 4-[4-[6-methyl-7-(4-piperazin-1-ylphenyl)imidazo[1,2-b]pyridazin-3-yl]quinolin-7-yl]morpholine Chemical compound CC=1C(=CC=2N(N=1)C(=CN=2)C1=CC=NC2=CC(=CC=C12)N1CCOCC1)C1=CC=C(C=C1)N1CCNCC1 KBBNHDCXAHOPTL-UHFFFAOYSA-N 0.000 claims description 2
- GWYQYXZUUKPLQP-UHFFFAOYSA-N 4-[6-(methoxymethyl)-7-(4-piperazin-1-ylphenyl)imidazo[1,2-b]pyridazin-3-yl]-1H-quinolin-2-one Chemical compound COCC=1C(=CC=2N(N=1)C(=CN=2)C1=CC(NC2=CC=CC=C12)=O)C1=CC=C(C=C1)N1CCNCC1 GWYQYXZUUKPLQP-UHFFFAOYSA-N 0.000 claims description 2
- QOTFUAIFOLGHHR-UHFFFAOYSA-N 4-[6-methyl-7-(1-piperidin-4-ylpyrazol-4-yl)imidazo[1,2-a]pyridin-3-yl]-1H-quinolin-2-one Chemical compound CC=1C(=CC=2N(C=1)C(=CN=2)C1=CC(NC2=CC=CC=C12)=O)C=1C=NN(C=1)C1CCNCC1 QOTFUAIFOLGHHR-UHFFFAOYSA-N 0.000 claims description 2
- MUSYIJFNOSPOPL-UHFFFAOYSA-N 4-[6-methyl-7-(4-piperazin-1-ylphenyl)imidazo[1,2-b]pyridazin-3-yl]-1,8-naphthyridine Chemical compound CC=1C(=CC=2N(N=1)C(=CN=2)C1=CC=NC2=NC=CC=C12)C1=CC=C(C=C1)N1CCNCC1 MUSYIJFNOSPOPL-UHFFFAOYSA-N 0.000 claims description 2
- TXPAVLINRKJNDN-UHFFFAOYSA-N 4-[6-methyl-7-(4-piperazin-1-ylphenyl)imidazo[1,2-b]pyridazin-3-yl]-1H-quinolin-2-one Chemical compound CC=1C(=CC=2N(N=1)C(=CN=2)C1=CC(NC2=CC=CC=C12)=O)C1=CC=C(C=C1)N1CCNCC1 TXPAVLINRKJNDN-UHFFFAOYSA-N 0.000 claims description 2
- KJFINAWSOGEPBA-UHFFFAOYSA-N 4-[6-methyl-7-(4-piperazin-1-ylphenyl)imidazo[1,2-b]pyridazin-3-yl]-7-(1-methylpyrazol-3-yl)-1H-quinolin-2-one Chemical class CN1N=C(C=C1)C1=CC=C2C(=CC(NC2=C1)=O)C1=CN=C2N1N=C(C(=C2)C1=CC=C(C=C1)N1CCNCC1)C KJFINAWSOGEPBA-UHFFFAOYSA-N 0.000 claims description 2
- IRJRZJPLNYHXCJ-UHFFFAOYSA-N 4-[6-methyl-7-(4-piperazin-1-ylphenyl)imidazo[1,2-b]pyridazin-3-yl]-N-pyridin-3-ylquinolin-7-amine Chemical compound CC=1C(=CC=2N(N=1)C(=CN=2)C1=CC=NC2=CC(=CC=C12)NC=1C=NC=CC=1)C1=CC=C(C=C1)N1CCNCC1 IRJRZJPLNYHXCJ-UHFFFAOYSA-N 0.000 claims description 2
- FSYRJBUXMJESFK-UHFFFAOYSA-N 4-[6-methyl-7-(4-piperazin-1-ylphenyl)imidazo[1,2-b]pyridazin-3-yl]quinoline-7-carbonitrile Chemical compound CC=1C(=CC=2N(N=1)C(=CN=2)C1=CC=NC2=CC(=CC=C12)C#N)C1=CC=C(C=C1)N1CCNCC1 FSYRJBUXMJESFK-UHFFFAOYSA-N 0.000 claims description 2
- CMTGQIGVCMEEHQ-UHFFFAOYSA-N 4-[6-methyl-7-[1-(piperidin-4-ylmethyl)pyrazol-4-yl]imidazo[1,2-b]pyridazin-3-yl]-7-pyridin-4-yl-1H-quinolin-2-one Chemical compound CC=1C(=CC=2N(N=1)C(=CN=2)C1=CC(NC2=CC(=CC=C12)C1=CC=NC=C1)=O)C=1C=NN(C=1)CC1CCNCC1 CMTGQIGVCMEEHQ-UHFFFAOYSA-N 0.000 claims description 2
- JSGPXCXARKBPMS-UHFFFAOYSA-N 4-[6-methyl-7-[3-(4-methylpiperazin-1-yl)phenyl]imidazo[1,2-b]pyridazin-3-yl]-7-pyridin-4-yl-1H-quinolin-2-one Chemical compound CC=1C(=CC=2N(N=1)C(=CN=2)C1=CC(NC2=CC(=CC=C12)C1=CC=NC=C1)=O)C1=CC(=CC=C1)N1CCN(CC1)C JSGPXCXARKBPMS-UHFFFAOYSA-N 0.000 claims description 2
- WYYISNASXOYZRJ-HXUWFJFHSA-N 4-[7-[3-fluoro-4-[[(2R)-2-methylpyrrolidin-1-yl]methyl]phenyl]-6-methylimidazo[1,2-b]pyridazin-3-yl]-7-pyridin-4-yl-1H-quinolin-2-one Chemical compound FC=1C=C(C=CC=1CN1[C@@H](CCC1)C)C1=CC=2N(N=C1C)C(=CN=2)C1=CC(NC2=CC(=CC=C12)C1=CC=NC=C1)=O WYYISNASXOYZRJ-HXUWFJFHSA-N 0.000 claims description 2
- YGFUJNDMCCFCGS-UHFFFAOYSA-N 4-[[4-[3-[7-(1-ethylimidazol-4-yl)-1,8-naphthyridin-4-yl]-6-methylimidazo[1,2-b]pyridazin-7-yl]phenyl]methyl]morpholine Chemical compound C(C)N1C=NC(=C1)C1=CC=C2C(=CC=NC2=N1)C1=CN=C2N1N=C(C(=C2)C1=CC=C(CN2CCOCC2)C=C1)C YGFUJNDMCCFCGS-UHFFFAOYSA-N 0.000 claims description 2
- GSABXFYSBHTBER-UHFFFAOYSA-N 4-[[4-[6-methyl-3-[7-(5-methyl-1H-pyrazol-3-yl)-1,8-naphthyridin-4-yl]imidazo[1,2-b]pyridazin-7-yl]phenyl]methyl]morpholine Chemical compound CC=1C(=CC=2N(N=1)C(=CN=2)C1=CC=NC2=NC(=CC=C12)C1=NNC(=C1)C)C1=CC=C(CN2CCOCC2)C=C1 GSABXFYSBHTBER-UHFFFAOYSA-N 0.000 claims description 2
- LAKUSLPEDYBBFH-UHFFFAOYSA-N 4-[[4-[6-methyl-7-(4-piperazin-1-ylphenyl)imidazo[1,2-b]pyridazin-3-yl]quinolin-7-yl]methyl]morpholine Chemical compound CC=1C(=CC=2N(N=1)C(=CN=2)C1=CC=NC2=CC(=CC=C12)CN1CCOCC1)C1=CC=C(C=C1)N1CCNCC1 LAKUSLPEDYBBFH-UHFFFAOYSA-N 0.000 claims description 2
- MHWGVZYDNXKYMP-UHFFFAOYSA-N 4-methyl-1-[4-[6-methyl-3-(7-pyridin-4-ylquinolin-4-yl)imidazo[1,2-b]pyridazin-7-yl]phenyl]piperazin-2-one Chemical compound CN1CC(N(CC1)C1=CC=C(C=C1)C1=CC=2N(N=C1C)C(=CN=2)C1=CC=NC2=CC(=CC=C12)C1=CC=NC=C1)=O MHWGVZYDNXKYMP-UHFFFAOYSA-N 0.000 claims description 2
- MVPYQULZTLFLKO-UHFFFAOYSA-N 4-methyl-1-[[4-[6-methyl-3-[7-(4-methyltriazol-2-yl)-1,8-naphthyridin-4-yl]imidazo[1,2-b]pyridazin-7-yl]phenyl]methyl]piperidin-4-ol Chemical compound CC1(CCN(CC1)CC1=CC=C(C=C1)C1=CC=2N(N=C1C)C(=CN=2)C1=CC=NC2=NC(=CC=C12)N1N=CC(=N1)C)O MVPYQULZTLFLKO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- MDSFKBHRZHNHNY-UHFFFAOYSA-N 5-[6-methyl-7-(1-propan-2-ylpyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl]-2-(1-methylpyrazol-3-yl)-1,8-naphthyridine Chemical compound C(C)(C)N1N=CC(=C1)C1=CC=2N(N=C1C)C(=CN=2)C1=C2C=CC(=NC2=NC=C1)C1=NN(C=C1)C MDSFKBHRZHNHNY-UHFFFAOYSA-N 0.000 claims description 2
- KOGNHFMGVOWGGH-UHFFFAOYSA-N 5-[6-methyl-7-(1-propan-2-ylpyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl]-2-(1-methylpyrazol-4-yl)-1,8-naphthyridine Chemical compound C(C)(C)N1N=CC(=C1)C1=CC=2N(N=C1C)C(=CN=2)C1=C2C=CC(=NC2=NC=C1)C=1C=NN(C=1)C KOGNHFMGVOWGGH-UHFFFAOYSA-N 0.000 claims description 2
- YBXPCJXCEKAEIA-UHFFFAOYSA-N 5-[6-methyl-7-(1-propan-2-ylpyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl]-2-(4-methyltriazol-2-yl)-1,8-naphthyridine Chemical compound C(C)(C)N1N=CC(=C1)C1=CC=2N(N=C1C)C(=CN=2)C1=C2C=CC(=NC2=NC=C1)N1N=CC(=N1)C YBXPCJXCEKAEIA-UHFFFAOYSA-N 0.000 claims description 2
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| CN114787160A (zh) | 2018-12-20 | 2022-07-22 | 因赛特公司 | 作为活化素受体样激酶-2的抑制剂的咪唑并哒嗪和咪唑并吡啶化合物 |
| WO2021252781A1 (en) | 2020-06-12 | 2021-12-16 | Incyte Corporation | Imidazopyridazine compounds with activity as alk2 inhibitors |
| CN118119619A (zh) * | 2021-10-18 | 2024-05-31 | 上海美悦生物科技发展有限公司 | Sik抑制剂及其组合物、制备方法和用途 |
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| BR0111747A (pt) | 2000-06-28 | 2003-07-08 | Smithkline Beecham Plc | Processo de moagem úmida |
| JP2005343889A (ja) | 2004-05-06 | 2005-12-15 | Taisho Pharmaceut Co Ltd | イミダゾピリジン誘導体 |
| US7528138B2 (en) | 2004-11-04 | 2009-05-05 | Vertex Pharmaceuticals Incorporated | Pyrazolo[1,5-a]pyrimidines useful as inhibitors of protein kinases |
| MX2009005144A (es) * | 2006-11-22 | 2009-05-27 | Incyte Corp | Imidazotriazinas e imidazopirimidinas como inhibidores de cinasa. |
| US8143253B2 (en) | 2007-07-26 | 2012-03-27 | Novartis Ag | Organic compounds |
| EA201000615A1 (ru) * | 2007-10-17 | 2010-12-30 | Новартис Аг | Производные имидазо[1,2-а]пиридина, применимые в качестве ингибиторов апк (активиноподобной киназы) |
| EP2453882A1 (en) | 2009-07-14 | 2012-05-23 | Beth Israel Deaconess Medical Center, Inc. | Methods of increasing liver proliferation |
| CN103384670B (zh) | 2010-07-28 | 2016-05-25 | 拜耳知识产权有限责任公司 | 取代的咪唑并[1,2-b]哒嗪 |
| SG11201503299YA (en) | 2012-09-28 | 2015-06-29 | Univ Vanderbilt | Fused heterocyclic compounds as selective bmp inhibitors |
| CN104768554B (zh) | 2012-11-07 | 2018-04-17 | 霍夫曼-拉罗奇有限公司 | 三唑并化合物 |
| US9682983B2 (en) * | 2013-03-14 | 2017-06-20 | The Brigham And Women's Hospital, Inc. | BMP inhibitors and methods of use thereof |
| MA52119A (fr) | 2015-10-19 | 2018-08-29 | Ncyte Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| SG10202004618TA (en) | 2015-11-19 | 2020-06-29 | Incyte Corp | Heterocyclic compounds as immunomodulators |
| ES2916874T3 (es) | 2015-12-17 | 2022-07-06 | Incyte Corp | Derivados de N-fenil-piridina-2-carboxamida y su uso como moduladores de la interacción proteína/proteína PD-1/PD-L1 |
| US20170174679A1 (en) | 2015-12-22 | 2017-06-22 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2017192961A1 (en) | 2016-05-06 | 2017-11-09 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| TW201808902A (zh) | 2016-05-26 | 2018-03-16 | 美商英塞特公司 | 作為免疫調節劑之雜環化合物 |
| MD3472167T2 (ro) | 2016-06-20 | 2023-02-28 | Incyte Corp | Compuși heterociclici ca imunomodulatori |
| ES2930092T3 (es) | 2016-07-14 | 2022-12-07 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| DK3500571T3 (da) | 2016-08-17 | 2021-03-08 | Childrens Hospital Med Ct | Imidazo[1,2-a]pyridinforbindelser, sammensætninger omfattende disse, fremgangsmåder til behandling af sygdomme ved hjælp af disse og fremgangsmåder til fremstilling heraf |
| ES2941716T3 (es) | 2016-08-29 | 2023-05-25 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| EP3512834A4 (en) | 2016-09-14 | 2020-05-06 | Vanderbilt University | INHIBIT OF BMP SIGNALING, CONNECTIONS, COMPOSITIONS AND USES THEREOF |
| CA3047980A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Tetrahydro imidazo[4,5-c]pyridine derivatives as pd-l1 internalization inducers |
| WO2018119263A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds derivatives as pd-l1 internalization inducers |
| MX2019007416A (es) | 2016-12-22 | 2019-12-11 | Incyte Corp | Derivados de benzooxazol como inmunomoduladores. |
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| JP7303108B2 (ja) | 2016-12-22 | 2023-07-04 | インサイト・コーポレイション | 免疫調節剤としての二環式複素芳香環化合物 |
| ES2899402T3 (es) | 2016-12-22 | 2022-03-11 | Incyte Corp | Derivados de piridina como inmunomoduladores |
| US20200054643A1 (en) | 2017-01-18 | 2020-02-20 | Vanderbilt University | Fused heterocyclic compounds as selective bmp inhibitors |
| WO2018165569A1 (en) | 2017-03-10 | 2018-09-13 | Rutgers, The State University Of New Jersey | Therapeutic compounds and methods |
| RU2019133646A (ru) | 2017-03-30 | 2021-04-30 | Ф. Хоффманн-Ля Рош Аг | Изохинолины в качестве ингибиторов hpk1 |
| CN114787160A (zh) | 2018-12-20 | 2022-07-22 | 因赛特公司 | 作为活化素受体样激酶-2的抑制剂的咪唑并哒嗪和咪唑并吡啶化合物 |
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2022
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2023
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