RU2635917C2 - Имидазо[1, 2-b]пиридазиновые производные как ингибиторы киназ - Google Patents

Info

Publication number

RU2635917C2

RU2635917C2 RU2014153627A RU2014153627A RU2635917C2 RU 2635917 C2 RU2635917 C2 RU 2635917C2 RU 2014153627 A RU2014153627 A RU 2014153627A RU 2014153627 A RU2014153627 A RU 2014153627A RU 2635917 C2 RU2635917 C2 RU 2635917C2

Authority

RU

Russia

Prior art keywords

group

cancer

compound according

imidazo

phenyl

Prior art date

2012-06-04

Links

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• 150000004942 imidazo[1,2-b]pyridazines Chemical class 0.000 title 1
• 229940043355 kinase inhibitor Drugs 0.000 title 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 578
• 150000003839 salts Chemical class 0.000 claims abstract description 81
• 101000686031 Homo sapiens Proto-oncogene tyrosine-protein kinase ROS Proteins 0.000 claims abstract description 74
• 102100023347 Proto-oncogene tyrosine-protein kinase ROS Human genes 0.000 claims abstract description 73
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 72
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 26
• 230000002255 enzymatic effect Effects 0.000 claims abstract description 22
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 13
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
• 238000000034 method Methods 0.000 claims description 133
• -1 amino, hydroxy Chemical group 0.000 claims description 118
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 71
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
• 108090000623 proteins and genes Proteins 0.000 claims description 46
• 229910052757 nitrogen Inorganic materials 0.000 claims description 39
• 230000014509 gene expression Effects 0.000 claims description 37
• 230000004927 fusion Effects 0.000 claims description 36
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 29
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 28
• 125000005843 halogen group Chemical group 0.000 claims description 28
• 201000011510 cancer Diseases 0.000 claims description 25
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 24
• 239000004480 active ingredient Substances 0.000 claims description 23
• 125000003277 amino group Chemical group 0.000 claims description 23
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
• 101150035397 Ros1 gene Proteins 0.000 claims description 21
• 239000003814 drug Substances 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 125000001931 aliphatic group Chemical group 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 16
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 15
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
• 229940124597 therapeutic agent Drugs 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 239000003112 inhibitor Substances 0.000 claims description 9
• ROFHSOCMQNVNGI-IBGZPJMESA-N (4s)-4-amino-1-[4-[6-[(3-fluorophenyl)methyl-methylamino]imidazo[1,2-b]pyridazin-3-yl]phenyl]pyrrolidin-2-one Chemical compound C1=CC2=NC=C(C=3C=CC(=CC=3)N3C(C[C@H](N)C3)=O)N2N=C1N(C)CC1=CC=CC(F)=C1 ROFHSOCMQNVNGI-IBGZPJMESA-N 0.000 claims description 8
• HEVHTYMYEMEBPX-HZPDHXFCSA-N 3-[4-[(2r)-2-aminopropoxy]phenyl]-n-[(1r)-1-(3-fluorophenyl)ethyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(OC[C@H](N)C)=CC=C1C1=CN=C2N1N=C(N[C@H](C)C=1C=C(F)C=CC=1)C=C2 HEVHTYMYEMEBPX-HZPDHXFCSA-N 0.000 claims description 8
• 239000002246 antineoplastic agent Substances 0.000 claims description 8
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• 125000000217 alkyl group Chemical group 0.000 claims description 7
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• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 125000004434 sulfur atom Chemical group 0.000 claims description 7
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• 208000014018 liver neoplasm Diseases 0.000 claims description 6
• LLDWLXXSYWQNMD-UTKZUKDTSA-N n-[(1r)-1-(3-fluorophenyl)ethyl]-3-[4-[[(2s)-pyrrolidin-2-yl]methoxy]phenyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound N([C@H](C)C=1C=C(F)C=CC=1)C(=NN12)C=CC1=NC=C2C(C=C1)=CC=C1OC[C@@H]1CCCN1 LLDWLXXSYWQNMD-UTKZUKDTSA-N 0.000 claims description 6
• 208000016065 neuroendocrine neoplasm Diseases 0.000 claims description 6
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• 201000003120 testicular cancer Diseases 0.000 claims description 6
• 201000002510 thyroid cancer Diseases 0.000 claims description 6
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 6
• GEDXRUYMMKEYEI-BEFAXECRSA-N (3S)-1-[5-[6-[(1R)-1-(3-fluorophenyl)ethoxy]imidazo[1,2-b]pyridazin-3-yl]pyridin-2-yl]pyrrolidin-3-amine Chemical compound N[C@H]1CCN(C1)C1=NC=C(C=C1)C1=CN=C2N1N=C(C=C2)O[C@H](C)C1=CC(=CC=C1)F GEDXRUYMMKEYEI-BEFAXECRSA-N 0.000 claims description 5
• RDYDLGQKCZBWIJ-UZLBHIALSA-N 3-[4-[(3S)-3-aminopyrrolidin-1-yl]phenyl]-N-[(1R)-1-(3-fluorophenyl)ethyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound N[C@H]1CCN(C1)C1=CC=C(C=C1)C1=CN=C2N1N=C(C=C2)N[C@H](C)C1=CC(=CC=C1)F RDYDLGQKCZBWIJ-UZLBHIALSA-N 0.000 claims description 5
• 208000007860 Anus Neoplasms Diseases 0.000 claims description 5
• 206010008342 Cervix carcinoma Diseases 0.000 claims description 5
• 208000022072 Gallbladder Neoplasms Diseases 0.000 claims description 5
• 102000001253 Protein Kinase Human genes 0.000 claims description 5
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 5
• 125000003282 alkyl amino group Chemical group 0.000 claims description 5
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 5
• 201000011165 anus cancer Diseases 0.000 claims description 5
• 201000010881 cervical cancer Diseases 0.000 claims description 5
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 5
• 201000010175 gallbladder cancer Diseases 0.000 claims description 5
• 125000005842 heteroatom Chemical group 0.000 claims description 5
• 108060006633 protein kinase Proteins 0.000 claims description 5
• XIQJHAMJWILELX-SFHVURJKSA-N (4s)-4-amino-1-[4-[6-[(3-fluorophenyl)methyl-methylamino]imidazo[1,2-b]pyridazin-3-yl]-3-methoxyphenyl]pyrrolidin-2-one Chemical compound COC1=CC(N2C(C[C@H](N)C2)=O)=CC=C1C(N1N=2)=CN=C1C=CC=2N(C)CC1=CC=CC(F)=C1 XIQJHAMJWILELX-SFHVURJKSA-N 0.000 claims description 4
• HEVHTYMYEMEBPX-JKSUJKDBSA-N 3-[4-[(2s)-2-aminopropoxy]phenyl]-n-[(1r)-1-(3-fluorophenyl)ethyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(OC[C@@H](N)C)=CC=C1C1=CN=C2N1N=C(N[C@H](C)C=1C=C(F)C=CC=1)C=C2 HEVHTYMYEMEBPX-JKSUJKDBSA-N 0.000 claims description 4
• FQCGOBGLJQWKJA-UZLBHIALSA-N 3-[4-[[(2s)-azetidin-2-yl]methoxy]phenyl]-n-[(1r)-1-(3-fluorophenyl)ethyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound N([C@H](C)C=1C=C(F)C=CC=1)C(=NN12)C=CC1=NC=C2C(C=C1)=CC=C1OC[C@@H]1CCN1 FQCGOBGLJQWKJA-UZLBHIALSA-N 0.000 claims description 4
• 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• KEYUEZVISDYBTH-MRXNPFEDSA-N n-[(1r)-1-(3-fluorophenyl)ethyl]-3-[4-[2-(methylamino)ethoxy]phenyl]imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC(OCCNC)=CC=C1C1=CN=C2N1N=C(N[C@H](C)C=1C=C(F)C=CC=1)C=C2 KEYUEZVISDYBTH-MRXNPFEDSA-N 0.000 claims description 4
• FNVZGBFSYRZMSY-FYZYNONXSA-N (4s)-4-amino-1-[4-[6-[(3-fluorophenyl)methyl-methylamino]imidazo[1,2-b]pyridazin-3-yl]phenyl]pyrrolidin-2-one;benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1.C1=CC2=NC=C(C=3C=CC(=CC=3)N3C(C[C@H](N)C3)=O)N2N=C1N(C)CC1=CC=CC(F)=C1 FNVZGBFSYRZMSY-FYZYNONXSA-N 0.000 claims description 3
• BQHPPNPYUMQTPW-FYZYNONXSA-N (4s)-4-amino-1-[4-[6-[(3-fluorophenyl)methyl-methylamino]imidazo[1,2-b]pyridazin-3-yl]phenyl]pyrrolidin-2-one;hexanedioic acid Chemical compound OC(=O)CCCCC(O)=O.C1=CC2=NC=C(C=3C=CC(=CC=3)N3C(C[C@H](N)C3)=O)N2N=C1N(C)CC1=CC=CC(F)=C1 BQHPPNPYUMQTPW-FYZYNONXSA-N 0.000 claims description 3
• DORJQZDOULKINH-QNBGGDODSA-N 3-[4-[(2r)-2-aminopropoxy]phenyl]-n-[(1r)-1-(3-fluorophenyl)ethyl]imidazo[1,2-b]pyridazin-6-amine;hexanedioic acid Chemical compound OC(=O)CCCCC(O)=O.C1=CC(OC[C@H](N)C)=CC=C1C1=CN=C2N1N=C(N[C@H](C)C=1C=C(F)C=CC=1)C=C2 DORJQZDOULKINH-QNBGGDODSA-N 0.000 claims description 3
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 3
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• 206010046766 uterine cancer Diseases 0.000 claims description 3
• ZUGFMWBTUQRHSE-QNBGGDODSA-N 3-[4-[(2r)-2-aminopropoxy]phenyl]-n-[(1r)-1-(3-fluorophenyl)ethyl]imidazo[1,2-b]pyridazin-6-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1=CC(OC[C@H](N)C)=CC=C1C1=CN=C2N1N=C(N[C@H](C)C=1C=C(F)C=CC=1)C=C2 ZUGFMWBTUQRHSE-QNBGGDODSA-N 0.000 claims description 2
• ZGFLWZPQLIXFGY-PXPMWPIZSA-N Cl.N[C@H]1CCN(C1)C1=CC=C(C=C1)C1=CN=C2N1N=C(C=C2)O[C@H](C)C2=CC(=CC=C2)F Chemical compound Cl.N[C@H]1CCN(C1)C1=CC=C(C=C1)C1=CN=C2N1N=C(C=C2)O[C@H](C)C2=CC(=CC=C2)F ZGFLWZPQLIXFGY-PXPMWPIZSA-N 0.000 claims description 2
• 125000004432 carbon atom Chemical group C* 0.000 claims description 2
• 125000001425 triazolyl group Chemical group 0.000 claims 2
• ACNFQZFMWCSGRR-HOOCCGKBSA-N O.OS(=O)(=O)c1ccccc1.C[C@@H](Oc1ccc2ncc(-c3ccc(cc3)N3C[C@@H](N)CC3=O)n2n1)c1cccc(F)c1 Chemical compound O.OS(=O)(=O)c1ccccc1.C[C@@H](Oc1ccc2ncc(-c3ccc(cc3)N3C[C@@H](N)CC3=O)n2n1)c1cccc(F)c1 ACNFQZFMWCSGRR-HOOCCGKBSA-N 0.000 claims 1
• JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 claims 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
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• 230000000694 effects Effects 0.000 abstract description 25
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• VTVRXITWWZGKHV-UHFFFAOYSA-N imidazo[1,2-b]pyridazine Chemical group N1=CC=CC2=NC=CN21 VTVRXITWWZGKHV-UHFFFAOYSA-N 0.000 abstract description 3
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