JP6174583B2 - アミノ置換イミダゾピリダジン - Google Patents

Info

Publication number

JP6174583B2

JP6174583B2 JP2014528955A JP2014528955A JP6174583B2 JP 6174583 B2 JP6174583 B2 JP 6174583B2 JP 2014528955 A JP2014528955 A JP 2014528955A JP 2014528955 A JP2014528955 A JP 2014528955A JP 6174583 B2 JP6174583 B2 JP 6174583B2

Authority

JP

Japan

Prior art keywords

group

imidazo

benzofuran

pyridazin

oxy

Prior art date

2011-09-06

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• -1 Amino-substituted imidazopyridazine Chemical class 0.000 title claims description 285
• 150000001875 compounds Chemical class 0.000 claims description 289
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 169
• 239000000203 mixture Substances 0.000 claims description 167
• 125000001424 substituent group Chemical group 0.000 claims description 120
• 238000000034 method Methods 0.000 claims description 117
• 125000005843 halogen group Chemical group 0.000 claims description 94
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 80
• 125000003118 aryl group Chemical group 0.000 claims description 78
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 74
• 150000003839 salts Chemical class 0.000 claims description 70
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 62
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 52
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 48
• 125000001072 heteroaryl group Chemical group 0.000 claims description 47
• 239000012453 solvate Substances 0.000 claims description 46
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 44
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 41
• 125000004432 carbon atom Chemical group C* 0.000 claims description 41
• 201000010099 disease Diseases 0.000 claims description 40
• 206010028980 Neoplasm Diseases 0.000 claims description 39
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 35
• 150000001204 N-oxides Chemical class 0.000 claims description 31
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
• 238000011282 treatment Methods 0.000 claims description 23
• 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 21
• 239000003814 drug Substances 0.000 claims description 21
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
• 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 18
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 16
• 230000001413 cellular effect Effects 0.000 claims description 16
• 229910052801 chlorine Inorganic materials 0.000 claims description 16
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
• 229910052740 iodine Inorganic materials 0.000 claims description 16
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
• 239000004480 active ingredient Substances 0.000 claims description 15
• 206010027476 Metastases Diseases 0.000 claims description 14
• 230000004083 survival effect Effects 0.000 claims description 14
• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical group OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 14
• 230000004663 cell proliferation Effects 0.000 claims description 13
• 230000010261 cell growth Effects 0.000 claims description 12
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 12
• 230000024932 T cell mediated immunity Effects 0.000 claims description 10
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
• 208000026310 Breast neoplasm Diseases 0.000 claims description 8
• 206010025323 Lymphomas Diseases 0.000 claims description 8
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• 208000032839 leukemia Diseases 0.000 claims description 8
• 230000001404 mediated effect Effects 0.000 claims description 8
• 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 8
• 230000037361 pathway Effects 0.000 claims description 8
• 208000002699 Digestive System Neoplasms Diseases 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 7
• 230000009401 metastasis Effects 0.000 claims description 7
• 206010006187 Breast cancer Diseases 0.000 claims description 6
• 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims description 6
• 208000009849 Female Genital Neoplasms Diseases 0.000 claims description 6
• 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 6
• 206010029098 Neoplasm skin Diseases 0.000 claims description 6
• 201000011523 endocrine gland cancer Diseases 0.000 claims description 6
• 239000002246 antineoplastic agent Substances 0.000 claims description 5
• 201000004477 skin sarcoma Diseases 0.000 claims description 4
• 230000001225 therapeutic effect Effects 0.000 claims description 4
• CMDIADSAZCFCCT-LLVKDONJSA-N (2r)-2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxypropan-1-amine Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)O[C@@H](CN)C)=CC2=C1 CMDIADSAZCFCCT-LLVKDONJSA-N 0.000 claims description 3
• 230000000973 chemotherapeutic effect Effects 0.000 claims description 3
• 230000006806 disease prevention Effects 0.000 claims description 3
• 125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 claims description 3
• DQQCXFUUJRYTMD-KRWDZBQOSA-N (1r)-2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-1-phenylethanamine Chemical compound C1([C@H](COC2=NN3C(C=4OC5=CC=CC=C5C=4)=CN=C3C=C2)N)=CC=CC=C1 DQQCXFUUJRYTMD-KRWDZBQOSA-N 0.000 claims description 2
• QLRAZPPSOATMKB-RHSMWYFYSA-N (1r,2r)-2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxycyclohexan-1-amine Chemical compound N[C@@H]1CCCC[C@H]1OC1=NN2C(C=3OC4=CC=CC=C4C=3)=CN=C2C=C1 QLRAZPPSOATMKB-RHSMWYFYSA-N 0.000 claims description 2
• CJXDHBGTYIJIMW-QGZVFWFLSA-N (1s)-2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-1-(4-chlorophenyl)ethanamine Chemical compound C1([C@@H](COC2=NN3C(C=4OC5=CC=CC=C5C=4)=CN=C3C=C2)N)=CC=C(Cl)C=C1 CJXDHBGTYIJIMW-QGZVFWFLSA-N 0.000 claims description 2
• IOEOIUAIUIBLAV-QGZVFWFLSA-N (1s)-2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-1-(4-fluorophenyl)ethanamine Chemical compound C1([C@@H](COC2=NN3C(C=4OC5=CC=CC=C5C=4)=CN=C3C=C2)N)=CC=C(F)C=C1 IOEOIUAIUIBLAV-QGZVFWFLSA-N 0.000 claims description 2
• DQQCXFUUJRYTMD-QGZVFWFLSA-N (1s)-2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-1-phenylethanamine Chemical compound C1([C@@H](COC2=NN3C(C=4OC5=CC=CC=C5C=4)=CN=C3C=C2)N)=CC=CC=C1 DQQCXFUUJRYTMD-QGZVFWFLSA-N 0.000 claims description 2
• FUYXHVQCWYCHDO-QGZVFWFLSA-N (1s)-2-[3-(4-fluoro-1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-1-phenylethanamine Chemical compound C1([C@@H](COC2=NN3C(C=4OC5=CC=CC(F)=C5C=4)=CN=C3C=C2)N)=CC=CC=C1 FUYXHVQCWYCHDO-QGZVFWFLSA-N 0.000 claims description 2
• NSQSAXGFNPZJMA-QGZVFWFLSA-N (1s)-2-[3-(5-chloro-1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-1-phenylethanamine Chemical compound C1([C@@H](COC2=NN3C(C=4OC5=CC=C(Cl)C=C5C=4)=CN=C3C=C2)N)=CC=CC=C1 NSQSAXGFNPZJMA-QGZVFWFLSA-N 0.000 claims description 2
• BCUZWVGODXHEOL-XJKSGUPXSA-N (1s,2r)-2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxycyclopentan-1-amine Chemical class N[C@H]1CCC[C@H]1OC1=NN2C(C=3OC4=CC=CC=C4C=3)=CN=C2C=C1 BCUZWVGODXHEOL-XJKSGUPXSA-N 0.000 claims description 2
• BCUZWVGODXHEOL-BBRMVZONSA-N (1s,2s)-2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxycyclopentan-1-amine Chemical compound N[C@H]1CCC[C@@H]1OC1=NN2C(C=3OC4=CC=CC=C4C=3)=CN=C2C=C1 BCUZWVGODXHEOL-BBRMVZONSA-N 0.000 claims description 2
• PHYSAVSMINAZFZ-LLVKDONJSA-N (2r)-1-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxypropan-2-amine Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)OC[C@H](N)C)=CC2=C1 PHYSAVSMINAZFZ-LLVKDONJSA-N 0.000 claims description 2
• KBPFAMOXCADQID-SNVBAGLBSA-N (2r)-1-[3-(5-chloro-1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxypropan-2-amine Chemical compound ClC1=CC=C2OC(C3=CN=C4C=CC(=NN43)OC[C@H](N)C)=CC2=C1 KBPFAMOXCADQID-SNVBAGLBSA-N 0.000 claims description 2
• JOLVRVLCKKGOQJ-FQEVSTJZSA-N (2r)-2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-2-phenylethanamine Chemical compound C1([C@@H](OC2=NN3C(C=4OC5=CC=CC=C5C=4)=CN=C3C=C2)CN)=CC=CC=C1 JOLVRVLCKKGOQJ-FQEVSTJZSA-N 0.000 claims description 2
• YXGNPZVPVBPXNE-IBGZPJMESA-N (2r)-2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-2-pyridin-3-ylethanamine Chemical compound C1([C@@H](OC2=NN3C(C=4OC5=CC=CC=C5C=4)=CN=C3C=C2)CN)=CC=CN=C1 YXGNPZVPVBPXNE-IBGZPJMESA-N 0.000 claims description 2
• FHHOEBQUJZRCTA-SNVBAGLBSA-N (2r)-2-[3-(5-chloro-1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxypropan-1-amine Chemical compound ClC1=CC=C2OC(C3=CN=C4C=CC(=NN43)O[C@@H](CN)C)=CC2=C1 FHHOEBQUJZRCTA-SNVBAGLBSA-N 0.000 claims description 2
• YKIQMKNAUBLRQP-GFCCVEGCSA-N (2r)-2-[3-(5-methyl-1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxypropan-1-amine Chemical compound CC1=CC=C2OC(C3=CN=C4C=CC(=NN43)O[C@@H](CN)C)=CC2=C1 YKIQMKNAUBLRQP-GFCCVEGCSA-N 0.000 claims description 2
• RMPRHZIGFOYGCP-SNVBAGLBSA-N (2r)-2-[3-(7-fluoro-1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxypropan-1-amine Chemical compound C1=CC(F)=C2OC(C3=CN=C4C=CC(=NN43)O[C@@H](CN)C)=CC2=C1 RMPRHZIGFOYGCP-SNVBAGLBSA-N 0.000 claims description 2
• INUVICLUXACYQF-SFHVURJKSA-N (2s)-1-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-3-phenylpropan-2-amine Chemical compound C([C@@H](COC1=NN2C(C=3OC4=CC=CC=C4C=3)=CN=C2C=C1)N)C1=CC=CC=C1 INUVICLUXACYQF-SFHVURJKSA-N 0.000 claims description 2
• PHYSAVSMINAZFZ-NSHDSACASA-N (2s)-1-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxypropan-2-amine Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)OC[C@@H](N)C)=CC2=C1 PHYSAVSMINAZFZ-NSHDSACASA-N 0.000 claims description 2
• IETGGGSZABQSKD-JTQLQIEISA-N (2s)-1-[3-(4-fluoro-1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxypropan-2-amine Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)OC[C@@H](N)C)=CC2=C1F IETGGGSZABQSKD-JTQLQIEISA-N 0.000 claims description 2
• CMDIADSAZCFCCT-NSHDSACASA-N (2s)-2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxypropan-1-amine Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)O[C@H](CN)C)=CC2=C1 CMDIADSAZCFCCT-NSHDSACASA-N 0.000 claims description 2
• USMIFXDDQHVDHD-UHFFFAOYSA-N 1-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-2-methylpropan-2-amine Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)OCC(C)(N)C)=CC2=C1 USMIFXDDQHVDHD-UHFFFAOYSA-N 0.000 claims description 2
• QETNJDQVIOIMDL-UHFFFAOYSA-N 1-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxymethyl]cyclopropan-1-amine Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1OCC1(N)CC1 QETNJDQVIOIMDL-UHFFFAOYSA-N 0.000 claims description 2
• OLUBNFKIAWVZDO-UHFFFAOYSA-N 1-cyclopropyl-2-[3-(4-methoxy-1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxyethanamine Chemical compound C=1C=2C(OC)=CC=CC=2OC=1C(N1N=2)=CN=C1C=CC=2OCC(N)C1CC1 OLUBNFKIAWVZDO-UHFFFAOYSA-N 0.000 claims description 2
• PRSSWDWEJRSSQB-UHFFFAOYSA-N 2-[2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxyethoxy]ethanamine Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)OCCOCCN)=CC2=C1 PRSSWDWEJRSSQB-UHFFFAOYSA-N 0.000 claims description 2
• RFOAGUBQMBBVNB-UHFFFAOYSA-N 2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-1-(oxan-4-yl)ethanamine Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1OCC(N)C1CCOCC1 RFOAGUBQMBBVNB-UHFFFAOYSA-N 0.000 claims description 2
• KCOJAJMFSMVAEL-UHFFFAOYSA-N 2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-1-pyridin-3-ylethanamine Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1OCC(N)C1=CC=CN=C1 KCOJAJMFSMVAEL-UHFFFAOYSA-N 0.000 claims description 2
• OSBGMACOIDTJTO-UHFFFAOYSA-N 2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-2-(oxolan-3-yl)ethanamine Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1OC(CN)C1CCOC1 OSBGMACOIDTJTO-UHFFFAOYSA-N 0.000 claims description 2
• ZQBPSJFVZVCZKU-UHFFFAOYSA-N 2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-2-cyclopropylethanamine Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1OC(CN)C1CC1 ZQBPSJFVZVCZKU-UHFFFAOYSA-N 0.000 claims description 2
• JSBXMSAVGLNZLR-UHFFFAOYSA-N 2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-3-(4-fluorophenyl)propan-1-amine Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1OC(CN)CC1=CC=C(F)C=C1 JSBXMSAVGLNZLR-UHFFFAOYSA-N 0.000 claims description 2
• CWBBPGMVFATOAS-UHFFFAOYSA-N 2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-3-morpholin-4-ylpropan-1-amine Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1OC(CN)CN1CCOCC1 CWBBPGMVFATOAS-UHFFFAOYSA-N 0.000 claims description 2
• HSVIIWOGDKRPON-UHFFFAOYSA-N 2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-3-pyridin-4-ylpropan-1-amine Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1OC(CN)CC1=CC=NC=C1 HSVIIWOGDKRPON-UHFFFAOYSA-N 0.000 claims description 2
• OTPOGFWDXGTVHV-UHFFFAOYSA-N 2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-4-methylpentan-1-amine Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)OC(CN)CC(C)C)=CC2=C1 OTPOGFWDXGTVHV-UHFFFAOYSA-N 0.000 claims description 2
• MZQPJGSTVGHBDD-UHFFFAOYSA-N 2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxyethanamine Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)OCCN)=CC2=C1 MZQPJGSTVGHBDD-UHFFFAOYSA-N 0.000 claims description 2
• NHLWOUMWXSZMNZ-UHFFFAOYSA-N 2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxyhex-5-en-1-amine Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)OC(CCC=C)CN)=CC2=C1 NHLWOUMWXSZMNZ-UHFFFAOYSA-N 0.000 claims description 2
• RQMSEQXVSMKOLK-UHFFFAOYSA-N 2-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxypropane-1,3-diamine Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)OC(CN)CN)=CC2=C1 RQMSEQXVSMKOLK-UHFFFAOYSA-N 0.000 claims description 2
• YCFARJHAUUFOKT-UHFFFAOYSA-N 2-[3-(4-methoxy-1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxyethanamine Chemical compound C1=CC(OCCN)=NN2C(C=3OC=4C=CC=C(C=4C=3)OC)=CN=C21 YCFARJHAUUFOKT-UHFFFAOYSA-N 0.000 claims description 2
• IJTRNKUOPXFLMC-UHFFFAOYSA-N 2-[3-(5-methoxy-1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxyethanamine Chemical compound C1=CC(OCCN)=NN2C(C=3OC4=CC=C(C=C4C=3)OC)=CN=C21 IJTRNKUOPXFLMC-UHFFFAOYSA-N 0.000 claims description 2
• TUHUFIDQZKLMBA-UHFFFAOYSA-N 3-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-2-methylpropan-1-amine Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)OCC(CN)C)=CC2=C1 TUHUFIDQZKLMBA-UHFFFAOYSA-N 0.000 claims description 2
• IKDQODNJXHFCKE-UHFFFAOYSA-N 3-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-2-phenylpropan-1-amine Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1OCC(CN)C1=CC=CC=C1 IKDQODNJXHFCKE-UHFFFAOYSA-N 0.000 claims description 2
• YXIBSMCVBWBETL-UHFFFAOYSA-N 3-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-3-(4-fluorophenyl)propan-1-amine Chemical compound C1=CC2=NC=C(C=3OC4=CC=CC=C4C=3)N2N=C1OC(CCN)C1=CC=C(F)C=C1 YXIBSMCVBWBETL-UHFFFAOYSA-N 0.000 claims description 2
• WBVUGALQOCVIOW-UHFFFAOYSA-N 3-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy-3-methylbutan-1-amine Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)OC(C)(CCN)C)=CC2=C1 WBVUGALQOCVIOW-UHFFFAOYSA-N 0.000 claims description 2
• FMXCWURHRBOMKG-UHFFFAOYSA-N 3-[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxypropan-1-amine Chemical compound C1=CC=C2OC(C3=CN=C4C=CC(=NN43)OCCCN)=CC2=C1 FMXCWURHRBOMKG-UHFFFAOYSA-N 0.000 claims description 2
• VVEIMWKFKVKOBM-UHFFFAOYSA-N 3-[3-(4-methoxy-1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxypropan-1-amine Chemical compound C1=CC(OCCCN)=NN2C(C=3OC=4C=CC=C(C=4C=3)OC)=CN=C21 VVEIMWKFKVKOBM-UHFFFAOYSA-N 0.000 claims description 2
• JANRDTYHHAVPLZ-UHFFFAOYSA-N 3-[3-(5-methoxy-1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxypropan-1-amine Chemical compound C1=CC(OCCCN)=NN2C(C=3OC4=CC=C(C=C4C=3)OC)=CN=C21 JANRDTYHHAVPLZ-UHFFFAOYSA-N 0.000 claims description 2
• DWGCHGNLBYWHMN-UHFFFAOYSA-N 3-[[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxymethyl]cyclobutan-1-amine Chemical compound C1C(N)CC1COC1=NN2C(C=3OC4=CC=CC=C4C=3)=CN=C2C=C1 DWGCHGNLBYWHMN-UHFFFAOYSA-N 0.000 claims description 2
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