JP2014528482A5

JP2014528482A5 -

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Publication number: JP2014528482A5
Authority: JP; Japan
Prior art keywords: benzo; methyl; amino; thiazol; cyclohexanol
Prior art date: 2012-10-12
Legal status : Granted

Application number

JP2014535928A

Other languages

English (en)

Japanese (ja)

Other versions

JP2014528482A (ja

JP6162130B2 (ja

Filing date

2012-10-12

Publication date

2015-12-03

2012-10-12 Application filed filed Critical

2012-10-12 Priority claimed from PCT/US2012/059983 external-priority patent/WO2013056070A2/en

2014-10-27 Publication of JP2014528482A publication Critical patent/JP2014528482A/ja

2015-12-03 Publication of JP2014528482A5 publication Critical patent/JP2014528482A5/ja

2017-07-12 Application granted granted Critical

2017-07-12 Publication of JP6162130B2 publication Critical patent/JP6162130B2/ja

Status Expired - Fee Related legal-status Critical Current

2032-10-12 Anticipated expiration legal-status Critical

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125000000217 alkyl group Chemical group 0.000 claims 168
125000001188 haloalkyl group Chemical group 0.000 claims 122
229910052739 hydrogen Inorganic materials 0.000 claims 117
239000001257 hydrogen Substances 0.000 claims 117
125000001072 heteroaryl group Chemical group 0.000 claims 91
125000000753 cycloalkyl group Chemical group 0.000 claims 90
125000003118 aryl group Chemical group 0.000 claims 88
125000000623 heterocyclic group Chemical group 0.000 claims 88
125000005843 halogen group Chemical group 0.000 claims 78
125000003342 alkenyl group Chemical group 0.000 claims 77
125000000304 alkynyl group Chemical group 0.000 claims 76
-1 cyano, oxo, thioxo Chemical group 0.000 claims 76
125000000392 cycloalkenyl group Chemical group 0.000 claims 75
125000002768 hydroxyalkyl group Chemical group 0.000 claims 70
125000004475 heteroaralkyl group Chemical group 0.000 claims 54
125000004415 heterocyclylalkyl group Chemical group 0.000 claims 54
150000002431 hydrogen Chemical class 0.000 claims 53
125000004103 aminoalkyl group Chemical group 0.000 claims 52
125000003710 aryl alkyl group Chemical group 0.000 claims 52
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 52
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 51
229910052805 deuterium Inorganic materials 0.000 claims 51
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 47
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 30
150000001875 compounds Chemical class 0.000 claims 30
229910052757 nitrogen Inorganic materials 0.000 claims 29
125000004183 alkoxy alkyl group Chemical group 0.000 claims 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 17
239000000203 mixture Substances 0.000 claims 16
125000002947 alkylene group Chemical group 0.000 claims 14
125000003545 alkoxy group Chemical group 0.000 claims 13
125000004043 oxo group Chemical group O=* 0.000 claims 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 12
229910052760 oxygen Inorganic materials 0.000 claims 12
229910052717 sulfur Inorganic materials 0.000 claims 12
125000000262 haloalkenyl group Chemical group 0.000 claims 11
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
239000008194 pharmaceutical composition Substances 0.000 claims 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 8
125000004450 alkenylene group Chemical group 0.000 claims 8
125000004966 cyanoalkyl group Chemical group 0.000 claims 8
229910052736 halogen Inorganic materials 0.000 claims 8
150000002367 halogens Chemical class 0.000 claims 8
125000004433 nitrogen atom Chemical group N* 0.000 claims 8
150000003839 salts Chemical class 0.000 claims 8
239000012453 solvate Substances 0.000 claims 8
125000000464 thioxo group Chemical group S=* 0.000 claims 8
125000004429 atom Chemical group 0.000 claims 6
201000010099 disease Diseases 0.000 claims 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
125000005605 benzo group Chemical group 0.000 claims 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
208000003476 primary myelofibrosis Diseases 0.000 claims 5
125000001424 substituent group Chemical group 0.000 claims 5
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 4
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
229910052799 carbon Inorganic materials 0.000 claims 4
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 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
150000003536 tetrazoles Chemical class 0.000 claims 4
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 4
HFRXZOMXIRZSIM-UHFFFAOYSA-N 2-[[6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(F)C=C2N=C1 HFRXZOMXIRZSIM-UHFFFAOYSA-N 0.000 claims 3
208000023275 Autoimmune disease Diseases 0.000 claims 3
101000916644 Homo sapiens Macrophage colony-stimulating factor 1 receptor Proteins 0.000 claims 3
101000932478 Homo sapiens Receptor-type tyrosine-protein kinase FLT3 Proteins 0.000 claims 3
102100028198 Macrophage colony-stimulating factor 1 receptor Human genes 0.000 claims 3
102100020718 Receptor-type tyrosine-protein kinase FLT3 Human genes 0.000 claims 3
201000008736 Systemic mastocytosis Diseases 0.000 claims 3
208000011580 syndromic disease Diseases 0.000 claims 3
PUVQFLMKPIJFNU-OXQOHEQNSA-N (1r,2r)-2-[[6-[(5-methoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(OC)=CC=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O PUVQFLMKPIJFNU-OXQOHEQNSA-N 0.000 claims 2
XOBQVDDQWMYTBG-YLJYHZDGSA-N (1r,2r)-2-[[6-[(6-methoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C12=CC(OC)=CC=C2N=CN1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O XOBQVDDQWMYTBG-YLJYHZDGSA-N 0.000 claims 2
ITMSHBOVWAHKQS-UHFFFAOYSA-N 1-[[6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound OC1CC2=CC=CC=C2C1NC(SC1=C2)=NC1=CC=C2CN1C=NC2=C1C=C(OC)C(OC)=C2 ITMSHBOVWAHKQS-UHFFFAOYSA-N 0.000 claims 2
IEOQQVMRNSXWTB-UHFFFAOYSA-N 2-[[6-(benzimidazol-1-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=CC=C2N=C1 IEOQQVMRNSXWTB-UHFFFAOYSA-N 0.000 claims 2
YJNFYMGJVJTYHD-UHFFFAOYSA-N 2-[[6-(imidazo[4,5-b]pyridin-1-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=CN=C2N=C1 YJNFYMGJVJTYHD-UHFFFAOYSA-N 0.000 claims 2
PUVQFLMKPIJFNU-UHFFFAOYSA-N 2-[[6-[(5-methoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(OC)=CC=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O PUVQFLMKPIJFNU-UHFFFAOYSA-N 0.000 claims 2
XOBQVDDQWMYTBG-UHFFFAOYSA-N 2-[[6-[(6-methoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C12=CC(OC)=CC=C2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O XOBQVDDQWMYTBG-UHFFFAOYSA-N 0.000 claims 2
WIOFWJYJELBMFO-UHFFFAOYSA-N 2-[[6-[[6-(1-methyltetrazol-5-yl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound CN1N=NN=C1C1=CN=C(N(CC=2C=C3SC(NC4C(CCCC4)O)=NC3=CC=2)C=N2)C2=C1 WIOFWJYJELBMFO-UHFFFAOYSA-N 0.000 claims 2
BUWOUFAEWFFRQO-UHFFFAOYSA-N 3-[[6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexane-1,2-diol Chemical compound OC1C(O)CCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(F)C=C2N=C1 BUWOUFAEWFFRQO-UHFFFAOYSA-N 0.000 claims 2
MQONQWPDEZEDBP-UHFFFAOYSA-N 4-[[6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(F)C=C2N=C1 MQONQWPDEZEDBP-UHFFFAOYSA-N 0.000 claims 2
206010003210 Arteriosclerosis Diseases 0.000 claims 2
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
206010009900 Colitis ulcerative Diseases 0.000 claims 2
208000032027 Essential Thrombocythemia Diseases 0.000 claims 2
201000003793 Myelodysplastic syndrome Diseases 0.000 claims 2
208000014767 Myeloproliferative disease Diseases 0.000 claims 2
201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 2
206010028980 Neoplasm Diseases 0.000 claims 2
208000008589 Obesity Diseases 0.000 claims 2
108091000080 Phosphotransferase Proteins 0.000 claims 2
206010035226 Plasma cell myeloma Diseases 0.000 claims 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
201000006704 Ulcerative Colitis Diseases 0.000 claims 2
208000017733 acquired polycythemia vera Diseases 0.000 claims 2
125000005336 allyloxy group Chemical group 0.000 claims 2
208000006673 asthma Diseases 0.000 claims 2
201000011510 cancer Diseases 0.000 claims 2
239000003795 chemical substances by application Substances 0.000 claims 2
208000021668 chronic eosinophilic leukemia Diseases 0.000 claims 2
125000004093 cyano group Chemical group *C#N 0.000 claims 2
230000004968 inflammatory condition Effects 0.000 claims 2
208000027866 inflammatory disease Diseases 0.000 claims 2
GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 2
201000006417 multiple sclerosis Diseases 0.000 claims 2
206010028537 myelofibrosis Diseases 0.000 claims 2
LSOGTXLGSZTVCW-UHFFFAOYSA-N n-(2-chlorocyclohexyl)-6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC2=CC(F)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1Cl LSOGTXLGSZTVCW-UHFFFAOYSA-N 0.000 claims 2
235000020824 obesity Nutrition 0.000 claims 2
102000020233 phosphotransferase Human genes 0.000 claims 2
208000037244 polycythemia vera Diseases 0.000 claims 2
125000003226 pyrazolyl group Chemical group 0.000 claims 2
201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
AWMZMSFXQYVJQV-SATBOSKTSA-N (1R,2R)-2-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol 2-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound N1=CN(C2=NC=CC=C21)CC2=CC1=C(N=C(S1)NC1C(CCCC1)O)C=C2.N2=CN(C1=NC=CC=C12)CC1=CC2=C(N=C(S2)N[C@H]2[C@@H](CCCC2)O)C=C1 AWMZMSFXQYVJQV-SATBOSKTSA-N 0.000 claims 1
WECXRAJFNLZUNF-UYAOXDASSA-N (1R,2R)-2-[[6-[[7-(N-hydroxy-C-methylcarbonimidoyl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C=1N=C2C=C(C(=NO)C)C=CN2C=1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O WECXRAJFNLZUNF-UYAOXDASSA-N 0.000 claims 1
YJCUGWGAIBEMHL-TZIWHRDSSA-N (1r,2r)-1-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NC2=CC=CN=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1C2=CC=CC=C2C[C@H]1O YJCUGWGAIBEMHL-TZIWHRDSSA-N 0.000 claims 1
ZBMYRYUDIGRWGL-TZIWHRDSSA-N (1r,2r)-1-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzoxazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NC2=CC=CN=C2N1CC(C=C1O2)=CC=C1N=C2N[C@@H]1C2=CC=CC=C2C[C@H]1O ZBMYRYUDIGRWGL-TZIWHRDSSA-N 0.000 claims 1
ITUWHPCBXIFQRB-UYAOXDASSA-N (1r,2r)-1-[[6-(purin-9-ylmethyl)-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NC2=CN=CN=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1C2=CC=CC=C2C[C@H]1O ITUWHPCBXIFQRB-UYAOXDASSA-N 0.000 claims 1
ITMSHBOVWAHKQS-PXDATVDWSA-N (1r,2r)-1-[[6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C([C@H]1O)C2=CC=CC=C2[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C=NC2=C1C=C(OC)C(OC)=C2 ITMSHBOVWAHKQS-PXDATVDWSA-N 0.000 claims 1
HHEUSPPWGQNLGQ-ZJSXRUAMSA-N (1r,2r)-1-[[6-[(5-bromo-6-methoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C([C@H]1O)C2=CC=CC=C2[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C(C=C(C(=C2)Br)OC)=C2N=C1 HHEUSPPWGQNLGQ-ZJSXRUAMSA-N 0.000 claims 1
PQQFPFIZXHGNCD-WIYYLYMNSA-N (1r,2r)-1-[[6-[(5-bromoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NC2=CC=C(Br)N=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1C2=CC=CC=C2C[C@H]1O PQQFPFIZXHGNCD-WIYYLYMNSA-N 0.000 claims 1
JFDUFWIBEMLENB-TZIWHRDSSA-N (1r,2r)-1-[[6-[(6-bromoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NC2=CC(Br)=CN=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1C2=CC=CC=C2C[C@H]1O JFDUFWIBEMLENB-TZIWHRDSSA-N 0.000 claims 1
VNELNXBWSGYFIQ-TZIWHRDSSA-N (1r,2r)-1-[[6-[(6-bromoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzoxazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NC2=CC(Br)=CN=C2N1CC(C=C1O2)=CC=C1N=C2N[C@@H]1C2=CC=CC=C2C[C@H]1O VNELNXBWSGYFIQ-TZIWHRDSSA-N 0.000 claims 1
JCCHRBKBEPVEOJ-TZIWHRDSSA-N (1r,2r)-1-[[6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NC2=CC(F)=CN=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1C2=CC=CC=C2C[C@H]1O JCCHRBKBEPVEOJ-TZIWHRDSSA-N 0.000 claims 1
CCDKJIGULMTAMW-FYYLOGMGSA-N (1r,2r)-1-[[6-[[4-(1-methylpyrazol-4-yl)imidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NN(C)C=C1C(N=C1)=CN1CC1=CC=C(N=C(N[C@@H]2C3=CC=CC=C3C[C@H]2O)S2)C2=C1 CCDKJIGULMTAMW-FYYLOGMGSA-N 0.000 claims 1
GOUATKXBFMOMLD-FYYLOGMGSA-N (1r,2r)-1-[[6-[[5-(1-methylpyrazol-4-yl)imidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NN(C)C=C1C1=CN=CN1CC1=CC=C(N=C(N[C@@H]2C3=CC=CC=C3C[C@H]2O)S2)C2=C1 GOUATKXBFMOMLD-FYYLOGMGSA-N 0.000 claims 1
NWGWISADWXWMJJ-UKRRQHHQSA-N (1r,2r)-2-[[4,7-difluoro-6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2F)=NC1=C(F)C=C2CN1C2=NC=CC=C2N=C1 NWGWISADWXWMJJ-UKRRQHHQSA-N 0.000 claims 1
ZDNKFBJHRLAMBS-GDBMZVCRSA-N (1r,2r)-2-[[4-bromo-6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=C(Br)C=C2CN1C2=NC=CC=C2N=C1 ZDNKFBJHRLAMBS-GDBMZVCRSA-N 0.000 claims 1
ZTQGTDSHYYJPOK-RTBURBONSA-N (1r,2r)-2-[[4-chloro-6-[(6-morpholin-4-ylimidazo[1,2-b]pyridazin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=C(Cl)C=C2CC1=CN=C2N1N=C(N1CCOCC1)C=C2 ZTQGTDSHYYJPOK-RTBURBONSA-N 0.000 claims 1
SFXVOEKNFDNRKW-RHSMWYFYSA-N (1r,2r)-2-[[5-fluoro-6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC(F)=C2CN1C2=NC=CC=C2N=C1 SFXVOEKNFDNRKW-RHSMWYFYSA-N 0.000 claims 1
JVVGICYGJIFMQW-SJLPKXTDSA-N (1r,2r)-2-[[6-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CNC2=NC=CC=C12 JVVGICYGJIFMQW-SJLPKXTDSA-N 0.000 claims 1
DRFSPYXJCMCENV-YLJYHZDGSA-N (1r,2r)-2-[[6-(4h-imidazo[1,2-a]benzimidazol-1-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C1=CC=CC=C1N2 DRFSPYXJCMCENV-YLJYHZDGSA-N 0.000 claims 1
IEOQQVMRNSXWTB-VQIMIIECSA-N (1r,2r)-2-[[6-(benzimidazol-1-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=CC=C2N=C1 IEOQQVMRNSXWTB-VQIMIIECSA-N 0.000 claims 1
KKLRZTOURONSON-NVXWUHKLSA-N (1r,2r)-2-[[6-(imidazo[1,2-a]pyrazin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CN=C2 KKLRZTOURONSON-NVXWUHKLSA-N 0.000 claims 1
OFQLITHDMDHVSS-SJLPKXTDSA-N (1r,2r)-2-[[6-(imidazo[1,2-a]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC=C2 OFQLITHDMDHVSS-SJLPKXTDSA-N 0.000 claims 1
OVFFQTKQASXSAI-NVXWUHKLSA-N (1r,2r)-2-[[6-(imidazo[1,2-b]pyridazin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1N=CC=C2 OVFFQTKQASXSAI-NVXWUHKLSA-N 0.000 claims 1
AUPOBUMNCNWITJ-NVXWUHKLSA-N (1r,2r)-2-[[6-(imidazo[1,2-b]pyridazin-3-ylmethyl)-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(OC1=C2)=NC1=CC=C2CC1=CN=C2N1N=CC=C2 AUPOBUMNCNWITJ-NVXWUHKLSA-N 0.000 claims 1
SRUQFXJKNIHZSV-GDBMZVCRSA-N (1r,2r)-2-[[6-(imidazo[2,1-b][1,3]thiazol-5-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CS2 SRUQFXJKNIHZSV-GDBMZVCRSA-N 0.000 claims 1
YJNFYMGJVJTYHD-RHSMWYFYSA-N (1r,2r)-2-[[6-(imidazo[4,5-b]pyridin-1-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=CN=C2N=C1 YJNFYMGJVJTYHD-RHSMWYFYSA-N 0.000 claims 1
BOOWGQXDGUSFLL-WIYYLYMNSA-N (1r,2r)-2-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]-1-methylcyclohexan-1-ol Chemical compound C[C@@]1(O)CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=CC=C2N=C1 BOOWGQXDGUSFLL-WIYYLYMNSA-N 0.000 claims 1
KESGXXFUJIJCGR-SATBOSKTSA-N (1r,2r)-2-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol;methanesulfonic acid Chemical compound CS(O)(=O)=O.O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=CC=C2N=C1 KESGXXFUJIJCGR-SATBOSKTSA-N 0.000 claims 1
XHSWOKDJKWWDEB-RHSMWYFYSA-N (1r,2r)-2-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(OC1=C2)=NC1=CC=C2CN1C2=NC=CC=C2N=C1 XHSWOKDJKWWDEB-RHSMWYFYSA-N 0.000 claims 1
VWMPIAAFVQRGLF-UKRRQHHQSA-N (1r,2r)-2-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-[1,3]thiazolo[4,5-b]pyridin-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=NC=C2CN1C2=NC=CC=C2N=C1 VWMPIAAFVQRGLF-UKRRQHHQSA-N 0.000 claims 1
KMGFNQOVZAISHI-RDTXWAMCSA-N (1r,2r)-2-[[6-(imidazo[4,5-c]pyridin-1-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=NC=C2N=C1 KMGFNQOVZAISHI-RDTXWAMCSA-N 0.000 claims 1
NMMIEKGAWCDNKW-CRAIPNDOSA-N (1r,2r)-2-[[6-(imidazo[4,5-c]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CN=CC=C2N=C1 NMMIEKGAWCDNKW-CRAIPNDOSA-N 0.000 claims 1
DKZAYADRKHFCHT-CZUORRHYSA-N (1r,2r)-2-[[6-(purin-9-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=NC=C2N=C1 DKZAYADRKHFCHT-CZUORRHYSA-N 0.000 claims 1
NMJLYCAYGPSTEZ-CZUORRHYSA-N (1r,2r)-2-[[6-(purin-9-ylmethyl)-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(OC1=C2)=NC1=CC=C2CN1C2=NC=NC=C2N=C1 NMJLYCAYGPSTEZ-CZUORRHYSA-N 0.000 claims 1
TVRMVNUMMKEJOB-CZUORRHYSA-N (1r,2r)-2-[[6-[(2-aminoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound NC1=NC2=CC=CN=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O TVRMVNUMMKEJOB-CZUORRHYSA-N 0.000 claims 1
BEKDUIWQBTWKAP-CZUORRHYSA-N (1r,2r)-2-[[6-[(5,6-dichloroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC(Cl)=C(Cl)C=C2N=C1 BEKDUIWQBTWKAP-CZUORRHYSA-N 0.000 claims 1
AQJHHSHCKOFLIN-DNVCBOLYSA-N (1r,2r)-2-[[6-[(5,6-difluorobenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC(F)=C(F)C=C2N=C1 AQJHHSHCKOFLIN-DNVCBOLYSA-N 0.000 claims 1
QLCATMIVQMNKCQ-DNVCBOLYSA-N (1r,2r)-2-[[6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O QLCATMIVQMNKCQ-DNVCBOLYSA-N 0.000 claims 1
SWZBKJOIZWDPCK-RDTXWAMCSA-N (1r,2r)-2-[[6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclopentan-1-ol Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCC[C@H]1O SWZBKJOIZWDPCK-RDTXWAMCSA-N 0.000 claims 1
XEKRTDGSFPRMAS-DNVCBOLYSA-N (1r,2r)-2-[[6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1CC(C=C1O2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O XEKRTDGSFPRMAS-DNVCBOLYSA-N 0.000 claims 1
VQXWKQQMEPXYRJ-DYESRHJHSA-N (1r,2r)-2-[[6-[(5,6-dimethylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=2C=C(C)C(C)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O VQXWKQQMEPXYRJ-DYESRHJHSA-N 0.000 claims 1
DKAMBEGYXQVVBS-CRAIPNDOSA-N (1r,2r)-2-[[6-[(5,7-difluorobenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=C(F)C=C(F)C=C2N=C1 DKAMBEGYXQVVBS-CRAIPNDOSA-N 0.000 claims 1
CMEVTXHVHBLBPN-YLJYHZDGSA-N (1r,2r)-2-[[6-[(5,7-dimethylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(C)=CC(C)=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O CMEVTXHVHBLBPN-YLJYHZDGSA-N 0.000 claims 1
YOLNVXYHRKRYCZ-DNVCBOLYSA-N (1r,2r)-2-[[6-[(5-bromo-6-methoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC=2C=C(Br)C(OC)=CC=2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O YOLNVXYHRKRYCZ-DNVCBOLYSA-N 0.000 claims 1
ALMRJRXXXGYEAP-CRAIPNDOSA-N (1r,2r)-2-[[6-[(5-bromo-7-fluorobenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=C(F)C=C(Br)C=C2N=C1 ALMRJRXXXGYEAP-CRAIPNDOSA-N 0.000 claims 1
SEGMAVYWLRSBGK-VQIMIIECSA-N (1r,2r)-2-[[6-[(5-bromo-7-methylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=2C(C)=CC(Br)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O SEGMAVYWLRSBGK-VQIMIIECSA-N 0.000 claims 1
GSEOFMYVPLQFHN-DNVCBOLYSA-N (1r,2r)-2-[[6-[(5-bromobenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(Br)C=C2N=C1 GSEOFMYVPLQFHN-DNVCBOLYSA-N 0.000 claims 1
LDWXEHSKWJSURY-CZUORRHYSA-N (1r,2r)-2-[[6-[(5-bromoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC(Br)=CC=C2N=C1 LDWXEHSKWJSURY-CZUORRHYSA-N 0.000 claims 1
OYFDTFWCVGOWOF-YLJYHZDGSA-N (1r,2r)-2-[[6-[(5-ethenyl-7-fluorobenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=C(F)C=C(C=C)C=C2N=C1 OYFDTFWCVGOWOF-YLJYHZDGSA-N 0.000 claims 1
PMLGUUZCYHJIDW-DYESRHJHSA-N (1r,2r)-2-[[6-[(5-ethenylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C=C)C=C2N=C1 PMLGUUZCYHJIDW-DYESRHJHSA-N 0.000 claims 1
IPKXGJGSTJVKJC-DYESRHJHSA-N (1r,2r)-2-[[6-[(5-ethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(OCC)=CC=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O IPKXGJGSTJVKJC-DYESRHJHSA-N 0.000 claims 1
UIMZLUFSWMHYFO-DYESRHJHSA-N (1r,2r)-2-[[6-[(5-ethynylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C#C)C=C2N=C1 UIMZLUFSWMHYFO-DYESRHJHSA-N 0.000 claims 1
MZEWZNHLWHFFJB-DNVCBOLYSA-N (1r,2r)-2-[[6-[(5-fluorobenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(F)C=C2N=C1 MZEWZNHLWHFFJB-DNVCBOLYSA-N 0.000 claims 1
QUXSIXJDIWJADA-NVXWUHKLSA-N (1r,2r)-2-[[6-[(5-fluoroimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C(F)=CC=C2 QUXSIXJDIWJADA-NVXWUHKLSA-N 0.000 claims 1
YCIIELOLIWYVEH-XMSQKQJNSA-N (1r,2r)-2-[[6-[(5-imidazol-1-ylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(N3C=NC=C3)C=C2N=C1 YCIIELOLIWYVEH-XMSQKQJNSA-N 0.000 claims 1
ZVNKVLIYQDHLOP-OXQOHEQNSA-N (1r,2r)-2-[[6-[(5-methoxybenzimidazol-1-yl)methyl]-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(OC)=CC=C2N1CC(C=C1O2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O ZVNKVLIYQDHLOP-OXQOHEQNSA-N 0.000 claims 1
PCCSOHBSSCCHJF-RHSMWYFYSA-N (1r,2r)-2-[[6-[(5-methoxyimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C12=NC(OC)=CC=C2N=CN1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O PCCSOHBSSCCHJF-RHSMWYFYSA-N 0.000 claims 1
NRUODIJXQLWQCB-OXQOHEQNSA-N (1r,2r)-2-[[6-[(5-methylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(C)=CC=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O NRUODIJXQLWQCB-OXQOHEQNSA-N 0.000 claims 1
LFXDRQGIXDOYOB-OXQOHEQNSA-N (1r,2r)-2-[[6-[(5-methylsulfonylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(S(=O)(=O)C)=CC=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O LFXDRQGIXDOYOB-OXQOHEQNSA-N 0.000 claims 1
XNEIAVOFSZLYNR-RHSMWYFYSA-N (1r,2r)-2-[[6-[(5-methylsulfonylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C12=NC(S(=O)(=O)C)=CC=C2N=CN1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O XNEIAVOFSZLYNR-RHSMWYFYSA-N 0.000 claims 1
LBMWATWTAPWNJR-AUSIDOKSSA-N (1r,2r)-2-[[6-[(5-morpholin-4-ylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(N3CCOCC3)C=C2N=C1 LBMWATWTAPWNJR-AUSIDOKSSA-N 0.000 claims 1
YOSCZGSKADBKJH-XMSQKQJNSA-N (1r,2r)-2-[[6-[(5-pyrazol-1-ylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(N3N=CC=C3)C=C2N=C1 YOSCZGSKADBKJH-XMSQKQJNSA-N 0.000 claims 1
NWDDKKFPATVNQZ-DNVCBOLYSA-N (1r,2r)-2-[[6-[(6-bromo-5-methoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=2C=C(Br)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O NWDDKKFPATVNQZ-DNVCBOLYSA-N 0.000 claims 1
BWCCVZDKIIPWCL-RHSMWYFYSA-N (1r,2r)-2-[[6-[(6-bromo-5-methoxyimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC=2C=C(Br)C(OC)=NC=2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O BWCCVZDKIIPWCL-RHSMWYFYSA-N 0.000 claims 1
NIRYQGBZTDCLFE-VQIMIIECSA-N (1r,2r)-2-[[6-[(6-bromobenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC(Br)=CC=C2N=C1 NIRYQGBZTDCLFE-VQIMIIECSA-N 0.000 claims 1
DGFSZEZXUIYAMO-GDBMZVCRSA-N (1r,2r)-2-[[6-[(6-bromoimidazo[1,2-b]pyridazin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1N=C(Br)C=C2 DGFSZEZXUIYAMO-GDBMZVCRSA-N 0.000 claims 1
LYUIRJQDPBKHQL-RHSMWYFYSA-N (1r,2r)-2-[[6-[(6-bromoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(Br)C=C2N=C1 LYUIRJQDPBKHQL-RHSMWYFYSA-N 0.000 claims 1
RJXTZKYLWHVCEZ-RHSMWYFYSA-N (1r,2r)-2-[[6-[(6-bromoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(OC1=C2)=NC1=CC=C2CN1C2=NC=C(Br)C=C2N=C1 RJXTZKYLWHVCEZ-RHSMWYFYSA-N 0.000 claims 1
PASNSACSNNWLEM-GDBMZVCRSA-N (1r,2r)-2-[[6-[(6-chloroimidazo[1,2-b]pyridazin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1N=C(Cl)C=C2 PASNSACSNNWLEM-GDBMZVCRSA-N 0.000 claims 1
WKYZEANVYDCMTP-RHSMWYFYSA-N (1r,2r)-2-[[6-[(6-chloroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(Cl)C=C2N=C1 WKYZEANVYDCMTP-RHSMWYFYSA-N 0.000 claims 1
BNQPXMXPCACSIB-YLJYHZDGSA-N (1r,2r)-2-[[6-[(6-cyclopropylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C3CC3)C=C2N=C1 BNQPXMXPCACSIB-YLJYHZDGSA-N 0.000 claims 1
GSSHIQPGDOQXQP-VQIMIIECSA-N (1r,2r)-2-[[6-[(6-ethenylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C=C)C=C2N=C1 GSSHIQPGDOQXQP-VQIMIIECSA-N 0.000 claims 1
ZNJRLENSVYPIFL-VQIMIIECSA-N (1r,2r)-2-[[6-[(6-ethylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(CC)=CN=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O ZNJRLENSVYPIFL-VQIMIIECSA-N 0.000 claims 1
DVBVNNPDIHVEMW-WIYYLYMNSA-N (1r,2r)-2-[[6-[(6-ethynylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC(C#C)=CC=C2N=C1 DVBVNNPDIHVEMW-WIYYLYMNSA-N 0.000 claims 1
HFRXZOMXIRZSIM-RHSMWYFYSA-N (1r,2r)-2-[[6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(F)C=C2N=C1 HFRXZOMXIRZSIM-RHSMWYFYSA-N 0.000 claims 1
USXOAMUOUBJHSC-RHSMWYFYSA-N (1r,2r)-2-[[6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(OC1=C2)=NC1=CC=C2CN1C2=NC=C(F)C=C2N=C1 USXOAMUOUBJHSC-RHSMWYFYSA-N 0.000 claims 1
ZTXPCPFDGSXYCJ-RHSMWYFYSA-N (1r,2r)-2-[[6-[(6-iodoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(I)C=C2N=C1 ZTXPCPFDGSXYCJ-RHSMWYFYSA-N 0.000 claims 1
NVIQYEFOKOJNKG-YLJYHZDGSA-N (1r,2r)-2-[[6-[(6-methoxybenzimidazol-1-yl)methyl]-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound C12=CC(OC)=CC=C2N=CN1CC(C=C1O2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O NVIQYEFOKOJNKG-YLJYHZDGSA-N 0.000 claims 1
VJBUHJCEPZQLKK-IEBWSBKVSA-N (1r,2r)-2-[[6-[(6-methoxyimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound N12C=C(OC)C=CC2=NC=C1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O VJBUHJCEPZQLKK-IEBWSBKVSA-N 0.000 claims 1
NRGBVKJJUHGNBE-NVXWUHKLSA-N (1r,2r)-2-[[6-[(6-methoxyimidazo[1,2-b]pyridazin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound N12N=C(OC)C=CC2=NC=C1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O NRGBVKJJUHGNBE-NVXWUHKLSA-N 0.000 claims 1
QOLYAGXAGUVIJY-CRAIPNDOSA-N (1r,2r)-2-[[6-[(6-methylsulfanylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(SC)=CN=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O QOLYAGXAGUVIJY-CRAIPNDOSA-N 0.000 claims 1
MTLGTTATHZIGLM-YLJYHZDGSA-N (1r,2r)-2-[[6-[(6-methylsulfonylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C12=CC(S(=O)(=O)C)=CC=C2N=CN1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O MTLGTTATHZIGLM-YLJYHZDGSA-N 0.000 claims 1
LJKDHKNHGWLVOW-UYAOXDASSA-N (1r,2r)-2-[[6-[(6-morpholin-4-ylimidazo[1,2-b]pyridazin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1N=C(N1CCOCC1)C=C2 LJKDHKNHGWLVOW-UYAOXDASSA-N 0.000 claims 1
ANMFHHANRBXAHJ-WIYYLYMNSA-N (1r,2r)-2-[[6-[(6-morpholin-4-ylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(N3CCOCC3)C=C2N=C1 ANMFHHANRBXAHJ-WIYYLYMNSA-N 0.000 claims 1
UYTXSEQLFKUCLP-TZIWHRDSSA-N (1r,2r)-2-[[6-[(6-pyrazol-1-ylimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=C(N1N=CC=C1)C=C2 UYTXSEQLFKUCLP-TZIWHRDSSA-N 0.000 claims 1
FPFGJZQIELQRRM-YLJYHZDGSA-N (1r,2r)-2-[[6-[(6-pyrazol-1-ylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(N3N=CC=C3)C=C2N=C1 FPFGJZQIELQRRM-YLJYHZDGSA-N 0.000 claims 1
OWSYRBBGVYDNEV-DENIHFKCSA-N (1r,2r)-2-[[6-[(6-pyridin-3-ylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C=3C=NC=CC=3)C=C2N=C1 OWSYRBBGVYDNEV-DENIHFKCSA-N 0.000 claims 1
GVAWUOXCYPOHSC-UYAOXDASSA-N (1r,2r)-2-[[6-[(7-ethenylimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(C=C)=C2 GVAWUOXCYPOHSC-UYAOXDASSA-N 0.000 claims 1
QPZHSFXYOLNLFR-TZIWHRDSSA-N (1r,2r)-2-[[6-[(7-imidazol-1-ylimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(N1C=NC=C1)=C2 QPZHSFXYOLNLFR-TZIWHRDSSA-N 0.000 claims 1
YOLZHHCXDQWJAZ-IEBWSBKVSA-N (1r,2r)-2-[[6-[(7-methoxyimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C=1N=C2C=C(OC)C=CN2C=1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O YOLZHHCXDQWJAZ-IEBWSBKVSA-N 0.000 claims 1
FSYDGSBLWQOAOT-IFMALSPDSA-N (1r,2r)-2-[[6-[(7-morpholin-4-ylimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(N1CCOCC1)=C2 FSYDGSBLWQOAOT-IFMALSPDSA-N 0.000 claims 1
IWSMPKPDHBTJQQ-TZIWHRDSSA-N (1r,2r)-2-[[6-[(7-pyrazol-1-ylimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(N1N=CC=C1)=C2 IWSMPKPDHBTJQQ-TZIWHRDSSA-N 0.000 claims 1
NBMVGLGACQEAGS-IUODEOHRSA-N (1r,2r)-2-[[6-[[2-(trifluoromethyl)purin-9-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC(C(F)(F)F)=NC=C2N=C1 NBMVGLGACQEAGS-IUODEOHRSA-N 0.000 claims 1
PFFVLZFLNGFWCS-VQIMIIECSA-N (1r,2r)-2-[[6-[[4-(1-methylpyrazol-4-yl)imidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NN(C)C=C1C(N=C1)=CN1CC1=CC=C(N=C(N[C@H]2[C@@H](CCCC2)O)S2)C2=C1 PFFVLZFLNGFWCS-VQIMIIECSA-N 0.000 claims 1
QXJPMXSQBYXTMC-VQIMIIECSA-N (1r,2r)-2-[[6-[[4-(1-methylpyrazol-4-yl)imidazol-1-yl]methyl]-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NN(C)C=C1C(N=C1)=CN1CC1=CC=C(N=C(N[C@H]2[C@@H](CCCC2)O)O2)C2=C1 QXJPMXSQBYXTMC-VQIMIIECSA-N 0.000 claims 1
YBYGVDRRNDUZAR-HYBUGGRVSA-N (1r,2r)-2-[[6-[[5-(1,2,3,6-tetrahydropyridin-4-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C=3CCNCC=3)C=C2N=C1 YBYGVDRRNDUZAR-HYBUGGRVSA-N 0.000 claims 1
KHWOGIBFKBMEMB-DYESRHJHSA-N (1r,2r)-2-[[6-[[5-(1,2,4-triazol-1-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(N3N=CN=C3)C=C2N=C1 KHWOGIBFKBMEMB-DYESRHJHSA-N 0.000 claims 1
SCHHIURSXLJOJD-XMSQKQJNSA-N (1r,2r)-2-[[6-[[5-(1h-pyrazol-5-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C3=NNC=C3)C=C2N=C1 SCHHIURSXLJOJD-XMSQKQJNSA-N 0.000 claims 1
TUAHPMBQYLDNLM-DYESRHJHSA-N (1r,2r)-2-[[6-[[5-(2-hydroxyethoxy)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(OCCO)=CC=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O TUAHPMBQYLDNLM-DYESRHJHSA-N 0.000 claims 1
DHULSKZLTBPDMT-OXQOHEQNSA-N (1r,2r)-2-[[6-[[5-(2-methyltetrazol-5-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound CN1N=NC(C=2C=C3N=CN(CC=4C=C5SC(N[C@H]6[C@@H](CCCC6)O)=NC5=CC=4)C3=CC=2)=N1 DHULSKZLTBPDMT-OXQOHEQNSA-N 0.000 claims 1
TZPZDQPRKNFVFD-PXDATVDWSA-N (1r,2r)-2-[[6-[[5-(2-morpholin-4-ylethoxy)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(OCCN3CCOCC3)C=C2N=C1 TZPZDQPRKNFVFD-PXDATVDWSA-N 0.000 claims 1
GGFFOKSWIRUSBH-DYESRHJHSA-N (1r,2r)-2-[[6-[[5-(3,3,3-trifluoroprop-1-en-2-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C(=C)C(F)(F)F)C=C2N=C1 GGFFOKSWIRUSBH-DYESRHJHSA-N 0.000 claims 1
BRFVKZHLBDEXON-NFBKMPQASA-N (1r,2r)-2-[[6-[[5-(3,6-dihydro-2h-pyran-4-yl)-7-fluorobenzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=C(F)C=C(C=3CCOCC=3)C=C2N=C1 BRFVKZHLBDEXON-NFBKMPQASA-N 0.000 claims 1
AYOVJIOUBUCUIO-HYBUGGRVSA-N (1r,2r)-2-[[6-[[5-(3,6-dihydro-2h-pyran-4-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C=3CCOCC=3)C=C2N=C1 AYOVJIOUBUCUIO-HYBUGGRVSA-N 0.000 claims 1
VIWRIEUBXDNHKO-PXDATVDWSA-N (1r,2r)-2-[[6-[[5-(cyclohexen-1-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C=3CCCCC=3)C=C2N=C1 VIWRIEUBXDNHKO-PXDATVDWSA-N 0.000 claims 1
MBOWAMBYGZLHMR-XMSQKQJNSA-N (1r,2r)-2-[[6-[[5-(oxetan-3-yloxy)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(OC3COC3)C=C2N=C1 MBOWAMBYGZLHMR-XMSQKQJNSA-N 0.000 claims 1
VQNDUYIKUOKUHV-DNVCBOLYSA-N (1r,2r)-2-[[6-[[5-(trifluoromethoxy)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(OC(F)(F)F)C=C2N=C1 VQNDUYIKUOKUHV-DNVCBOLYSA-N 0.000 claims 1
VJNDUIFDHUIZCF-DNVCBOLYSA-N (1r,2r)-2-[[6-[[5-(trifluoromethyl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C(F)(F)F)C=C2N=C1 VJNDUIFDHUIZCF-DNVCBOLYSA-N 0.000 claims 1
OHCCZARVEWQRKP-XMSQKQJNSA-N (1r,2r)-2-[[6-[[5-[1-methyl-3-(trifluoromethyl)pyrazol-4-yl]benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound FC(F)(F)C1=NN(C)C=C1C1=CC=C(N(CC=2C=C3SC(N[C@H]4[C@@H](CCCC4)O)=NC3=CC=2)C=N2)C2=C1 OHCCZARVEWQRKP-XMSQKQJNSA-N 0.000 claims 1
XBVXMKBQERTXDV-VQIMIIECSA-N (1r,2r)-2-[[6-[[6-(1,2,4-triazol-1-yl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(N3N=CN=C3)C=C2N=C1 XBVXMKBQERTXDV-VQIMIIECSA-N 0.000 claims 1
CNVJZPRWHLOWAZ-WIYYLYMNSA-N (1r,2r)-2-[[6-[[6-(1-methylpyrazol-4-yl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NN(C)C=C1C1=CN=C(N(CC=2C=C3SC(N[C@H]4[C@@H](CCCC4)O)=NC3=CC=2)C=N2)C2=C1 CNVJZPRWHLOWAZ-WIYYLYMNSA-N 0.000 claims 1
FYTUZUJHDDNATD-VQIMIIECSA-N (1r,2r)-2-[[6-[[6-(2-hydroxypropan-2-yl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(C(C)(O)C)=CN=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O FYTUZUJHDDNATD-VQIMIIECSA-N 0.000 claims 1
YINHMVICOHXZSR-CRAIPNDOSA-N (1r,2r)-2-[[6-[[6-(2-methyltetrazol-5-yl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound CN1N=NC(C=2C=C3N=CN(CC=4C=C5SC(N[C@H]6[C@@H](CCCC6)O)=NC5=CC=4)C3=NC=2)=N1 YINHMVICOHXZSR-CRAIPNDOSA-N 0.000 claims 1
GANWDCBZWPJSTP-RHSMWYFYSA-N (1r,2r)-2-[[6-[[6-(2h-tetrazol-5-yl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C3=NNN=N3)C=C2N=C1 GANWDCBZWPJSTP-RHSMWYFYSA-N 0.000 claims 1
ZRGZRWVXOLSCJY-TZIWHRDSSA-N (1r,2r)-2-[[6-[[6-(4-methylpiperazin-1-yl)imidazo[1,2-b]pyridazin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1CN(C)CCN1C1=NN2C(CC=3C=C4SC(N[C@H]5[C@@H](CCCC5)O)=NC4=CC=3)=CN=C2C=C1 ZRGZRWVXOLSCJY-TZIWHRDSSA-N 0.000 claims 1
HSYCUJSCOUQBFG-SJLPKXTDSA-N (1r,2r)-2-[[6-[[6-(hydroxymethyl)imidazo[1,2-b]pyridazin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound N12N=C(CO)C=CC2=NC=C1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O HSYCUJSCOUQBFG-SJLPKXTDSA-N 0.000 claims 1
JSOLSAVZJMUNSX-VQIMIIECSA-N (1r,2r)-2-[[6-[[6-(methylsulfanylmethyl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(CSC)=CN=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O JSOLSAVZJMUNSX-VQIMIIECSA-N 0.000 claims 1
GAXMSUGQADXPDK-RHSMWYFYSA-N (1r,2r)-2-[[6-[[6-(trifluoromethyl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C(F)(F)F)C=C2N=C1 GAXMSUGQADXPDK-RHSMWYFYSA-N 0.000 claims 1
AFYAYLVQQVFFLO-AUSIDOKSSA-N (1r,2r)-2-[[6-[[6-methoxy-5-(1-methylpyrazol-4-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC=2C=C(C3=CN(C)N=C3)C(OC)=CC=2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O AFYAYLVQQVFFLO-AUSIDOKSSA-N 0.000 claims 1
CCMTXBVIGROOOG-UYAOXDASSA-N (1r,2r)-2-[[6-[[7-(1,2,4-triazol-1-yl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(N1N=CN=C1)=C2 CCMTXBVIGROOOG-UYAOXDASSA-N 0.000 claims 1
QIBKVAMZUMXSOT-UYAOXDASSA-N (1r,2r)-2-[[6-[[7-(2-hydroxyethoxy)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C=1N=C2C=C(OCCO)C=CN2C=1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O QIBKVAMZUMXSOT-UYAOXDASSA-N 0.000 claims 1
TUBXOBXPCOWDMQ-TZIWHRDSSA-N (1r,2r)-2-[[6-[[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O TUBXOBXPCOWDMQ-TZIWHRDSSA-N 0.000 claims 1
ANIUPCVLIORXEA-FYYLOGMGSA-N (1r,2r)-2-[[6-[[7-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1CN(C)CCN1C1=CC2=NC=C(CC=3C=C4SC(N[C@H]5[C@@H](CCCC5)O)=NC4=CC=3)N2C=C1 ANIUPCVLIORXEA-FYYLOGMGSA-N 0.000 claims 1
NLOHZMBGHWIEBX-TZIWHRDSSA-N (1r,2r)-2-[[6-[[7-(n-methoxy-c-methylcarbonimidoyl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C=1N=C2C=C(C(C)=NOC)C=CN2C=1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O NLOHZMBGHWIEBX-TZIWHRDSSA-N 0.000 claims 1
JQXWQIXHCUIHMD-UYAOXDASSA-N (1r,2r)-2-[[6-[[7-(triazol-1-yl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(N1N=NC=C1)=C2 JQXWQIXHCUIHMD-UYAOXDASSA-N 0.000 claims 1
HADGQQBSDGCSQD-UYAOXDASSA-N (1r,2r)-2-[[6-[[7-(triazol-2-yl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(N1N=CC=N1)=C2 HADGQQBSDGCSQD-UYAOXDASSA-N 0.000 claims 1
YCJPECKKCSFKFG-PGBVBIMESA-N (1r,2r)-2-[[6-[methoxy(1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C=1NC2=NC=CC=C2C=1C(OC)C(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O YCJPECKKCSFKFG-PGBVBIMESA-N 0.000 claims 1
JJKMXXZEHUJYON-CZUORRHYSA-N (1r,2r)-2-[[7-fluoro-6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2F)=NC1=CC=C2CN1C2=NC=CC=C2N=C1 JJKMXXZEHUJYON-CZUORRHYSA-N 0.000 claims 1
ITMSHBOVWAHKQS-SQJMNOBHSA-N (1r,2s)-1-[[6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C([C@@H]1O)C2=CC=CC=C2[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C=NC2=C1C=C(OC)C(OC)=C2 ITMSHBOVWAHKQS-SQJMNOBHSA-N 0.000 claims 1
XRHBJZDMGZZWBO-ZNLUXHQJSA-N (1r,2s,3r)-3-[[6-[(5-ethenylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexane-1,2-diol Chemical compound O[C@@H]1[C@H](O)CCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C=C)C=C2N=C1 XRHBJZDMGZZWBO-ZNLUXHQJSA-N 0.000 claims 1
MSJYLMCRIKGLEQ-BSIFCXSSSA-N (1r,2s,3r)-3-[[6-[(5-methoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexane-1,2-diol Chemical compound C1=NC2=CC(OC)=CC=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCC[C@@H](O)[C@H]1O MSJYLMCRIKGLEQ-BSIFCXSSSA-N 0.000 claims 1
AGRAKNMYKAASSB-CKUXNOBLSA-N (1r,2s,3r)-3-[[6-[(5-morpholin-4-ylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexane-1,2-diol Chemical compound O[C@@H]1[C@H](O)CCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(N3CCOCC3)C=C2N=C1 AGRAKNMYKAASSB-CKUXNOBLSA-N 0.000 claims 1
BUWOUFAEWFFRQO-KYJSFNMBSA-N (1r,2s,3r)-3-[[6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexane-1,2-diol Chemical compound O[C@@H]1[C@H](O)CCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(F)C=C2N=C1 BUWOUFAEWFFRQO-KYJSFNMBSA-N 0.000 claims 1
ICNOGOOVAJXUPV-BSIFCXSSSA-N (1r,2s,3r)-3-[[6-[[5-(2-methyltetrazol-5-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexane-1,2-diol Chemical compound CN1N=NC(C=2C=C3N=CN(CC=4C=C5SC(N[C@H]6[C@@H]([C@H](O)CCC6)O)=NC5=CC=4)C3=CC=2)=N1 ICNOGOOVAJXUPV-BSIFCXSSSA-N 0.000 claims 1
ASWPTVQVILCEGY-AAIMPIBUSA-N (1r,2s,3r)-3-[[6-[[5-(oxetan-3-yloxy)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexane-1,2-diol Chemical compound O[C@@H]1[C@H](O)CCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(OC3COC3)C=C2N=C1 ASWPTVQVILCEGY-AAIMPIBUSA-N 0.000 claims 1
QVZIOQTUFYZNFY-POAQFYNOSA-N (1r,2s,3r)-3-[[6-[[6-(1,2,4-triazol-1-yl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexane-1,2-diol Chemical compound O[C@@H]1[C@H](O)CCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(N3N=CN=C3)C=C2N=C1 QVZIOQTUFYZNFY-POAQFYNOSA-N 0.000 claims 1
FZZPGEYDFNSSEV-KNKQGSTJSA-N (1r,2s,3r)-3-[[6-[[7-(triazol-2-yl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexane-1,2-diol Chemical compound O[C@@H]1[C@H](O)CCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(N1N=CC=N1)=C2 FZZPGEYDFNSSEV-KNKQGSTJSA-N 0.000 claims 1
BOOWGQXDGUSFLL-NQIIRXRSSA-N (1s,2r)-2-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]-1-methylcyclohexan-1-ol Chemical compound C[C@]1(O)CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=CC=C2N=C1 BOOWGQXDGUSFLL-NQIIRXRSSA-N 0.000 claims 1
HFRXZOMXIRZSIM-PBHICJAKSA-N (1s,2r)-2-[[6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(F)C=C2N=C1 HFRXZOMXIRZSIM-PBHICJAKSA-N 0.000 claims 1
BUWOUFAEWFFRQO-UWWQBHOKSA-N (1s,2r,3r)-3-[[6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexane-1,2-diol Chemical compound O[C@H]1[C@@H](O)CCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(F)C=C2N=C1 BUWOUFAEWFFRQO-UWWQBHOKSA-N 0.000 claims 1
IEOQQVMRNSXWTB-LPHOPBHVSA-N (1s,2s)-2-[[6-(benzimidazol-1-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@H]1CCCC[C@@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=CC=C2N=C1 IEOQQVMRNSXWTB-LPHOPBHVSA-N 0.000 claims 1
HFRXZOMXIRZSIM-YOEHRIQHSA-N (1s,2s)-2-[[6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound O[C@H]1CCCC[C@@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(F)C=C2N=C1 HFRXZOMXIRZSIM-YOEHRIQHSA-N 0.000 claims 1
UNGODVRJDXRURZ-CQSZACIVSA-N (2r)-2-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-one Chemical compound O=C1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=CC=C2N=C1 UNGODVRJDXRURZ-CQSZACIVSA-N 0.000 claims 1
POROCIZVRRQUBL-IBGZPJMESA-N (2r)-2-cyclohexyl-2-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]ethanol Chemical compound C1([C@@H](NC=2SC3=CC(CN4C5=NC=CC=C5N=C4)=CC=C3N=2)CO)CCCCC1 POROCIZVRRQUBL-IBGZPJMESA-N 0.000 claims 1
POROCIZVRRQUBL-LJQANCHMSA-N (2s)-2-cyclohexyl-2-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]ethanol Chemical compound C1([C@H](NC=2SC3=CC(CN4C5=NC=CC=C5N=C4)=CC=C3N=2)CO)CCCCC1 POROCIZVRRQUBL-LJQANCHMSA-N 0.000 claims 1
GOWBITABVGUPRO-JXMROGBWSA-N (e)-3-[1-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]benzimidazol-5-yl]prop-2-enoic acid Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(\C=C\C(O)=O)C=C2N=C1 GOWBITABVGUPRO-JXMROGBWSA-N 0.000 claims 1
GOWBITABVGUPRO-RBQDFUJGSA-N (e)-3-[1-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]benzimidazol-5-yl]prop-2-enoic acid Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(\C=C\C(O)=O)C=C2N=C1 GOWBITABVGUPRO-RBQDFUJGSA-N 0.000 claims 1
RMAKXNCOMFRKEN-UHFFFAOYSA-N 1-[1-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]benzimidazol-5-yl]ethanone Chemical compound C1=NC2=CC(C(=O)C)=CC=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O RMAKXNCOMFRKEN-UHFFFAOYSA-N 0.000 claims 1
DHIVZVFUEVWQEG-UHFFFAOYSA-N 1-[1-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]benzimidazol-5-yl]piperidin-2-one Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(N3C(CCCC3)=O)C=C2N=C1 DHIVZVFUEVWQEG-UHFFFAOYSA-N 0.000 claims 1
RMAKXNCOMFRKEN-DYESRHJHSA-N 1-[1-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]benzimidazol-5-yl]ethanone Chemical compound C1=NC2=CC(C(=O)C)=CC=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O RMAKXNCOMFRKEN-DYESRHJHSA-N 0.000 claims 1
DHIVZVFUEVWQEG-AUSIDOKSSA-N 1-[1-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]benzimidazol-5-yl]piperidin-2-one Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(N3C(CCCC3)=O)C=C2N=C1 DHIVZVFUEVWQEG-AUSIDOKSSA-N 0.000 claims 1
XJNFXIHZEGIEQO-UHFFFAOYSA-N 1-[3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]benzimidazol-5-yl]ethanone Chemical compound C12=CC(C(=O)C)=CC=C2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O XJNFXIHZEGIEQO-UHFFFAOYSA-N 0.000 claims 1
CMEGIKPTICZQSK-UHFFFAOYSA-N 1-[3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]imidazo[1,2-a]pyridin-7-yl]ethanone Chemical compound C=1N=C2C=C(C(=O)C)C=CN2C=1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O CMEGIKPTICZQSK-UHFFFAOYSA-N 0.000 claims 1
XIRGGJUKJWKWFM-UHFFFAOYSA-N 1-[3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]imidazo[1,2-a]pyridin-7-yl]piperidin-4-ol Chemical compound C1CC(O)CCN1C1=CC2=NC=C(CC=3C=C4SC(NC5C(CCCC5)O)=NC4=CC=3)N2C=C1 XIRGGJUKJWKWFM-UHFFFAOYSA-N 0.000 claims 1
WPMPYJZYVUXIPP-UHFFFAOYSA-N 1-[3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridin-5-yl]ethanone Chemical compound C12=NC(C(=O)C)=CC=C2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O WPMPYJZYVUXIPP-UHFFFAOYSA-N 0.000 claims 1
INJSHQKSWLODFL-UHFFFAOYSA-N 1-[3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridin-6-yl]ethanone Chemical compound C1=NC2=CC(C(=O)C)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O INJSHQKSWLODFL-UHFFFAOYSA-N 0.000 claims 1
XJNFXIHZEGIEQO-WIYYLYMNSA-N 1-[3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]benzimidazol-5-yl]ethanone Chemical compound C12=CC(C(=O)C)=CC=C2N=CN1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O XJNFXIHZEGIEQO-WIYYLYMNSA-N 0.000 claims 1
CMEGIKPTICZQSK-UYAOXDASSA-N 1-[3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]imidazo[1,2-a]pyridin-7-yl]ethanone Chemical compound C=1N=C2C=C(C(=O)C)C=CN2C=1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O CMEGIKPTICZQSK-UYAOXDASSA-N 0.000 claims 1
XIRGGJUKJWKWFM-FYYLOGMGSA-N 1-[3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]imidazo[1,2-a]pyridin-7-yl]piperidin-4-ol Chemical compound C1CC(O)CCN1C1=CC2=NC=C(CC=3C=C4SC(N[C@H]5[C@@H](CCCC5)O)=NC4=CC=3)N2C=C1 XIRGGJUKJWKWFM-FYYLOGMGSA-N 0.000 claims 1
JOEXWZJCVRPLQM-UHFFFAOYSA-N 1-[4-[[6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]piperidin-1-yl]ethanone Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCN(C(C)=O)CC1 JOEXWZJCVRPLQM-UHFFFAOYSA-N 0.000 claims 1
IAQKGUUHZWQLJG-UHFFFAOYSA-N 1-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]-3-(1-methylpyrazol-4-yl)pyrazin-2-one Chemical compound C1=NN(C)C=C1C(C1=O)=NC=CN1CC1=CC=C(N=C(NC2C(CCCC2)O)S2)C2=C1 IAQKGUUHZWQLJG-UHFFFAOYSA-N 0.000 claims 1
FCULQFBVFMIPMT-UHFFFAOYSA-N 1-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]-3-morpholin-4-ylpyrazin-2-one Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C(=O)C(N2CCOCC2)=NC=C1 FCULQFBVFMIPMT-UHFFFAOYSA-N 0.000 claims 1
HGZPHHYHVJVEER-UHFFFAOYSA-N 1-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]-6-methoxybenzimidazole-5-carbonitrile Chemical compound C1=NC=2C=C(C#N)C(OC)=CC=2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O HGZPHHYHVJVEER-UHFFFAOYSA-N 0.000 claims 1
NOXQAUBYFBKCEQ-UHFFFAOYSA-N 1-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]-n-methylbenzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NC)=CC=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O NOXQAUBYFBKCEQ-UHFFFAOYSA-N 0.000 claims 1
IQKICWDAQKBGOL-UHFFFAOYSA-N 1-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]-n-methylimidazole-4-carboxamide Chemical compound C1=NC(C(=O)NC)=CN1CC1=CC=C(N=C(NC2C(CCCC2)O)S2)C2=C1 IQKICWDAQKBGOL-UHFFFAOYSA-N 0.000 claims 1
IHHYCKKPQCLKEL-UHFFFAOYSA-N 1-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]benzimidazol-5-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(O)C=C2N=C1 IHHYCKKPQCLKEL-UHFFFAOYSA-N 0.000 claims 1
HMXUYUWRQNNZCN-UHFFFAOYSA-N 1-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]benzimidazole-5-carbonitrile Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C#N)C=C2N=C1 HMXUYUWRQNNZCN-UHFFFAOYSA-N 0.000 claims 1
IAQKGUUHZWQLJG-SJLPKXTDSA-N 1-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]-3-(1-methylpyrazol-4-yl)pyrazin-2-one Chemical compound C1=NN(C)C=C1C(C1=O)=NC=CN1CC1=CC=C(N=C(N[C@H]2[C@@H](CCCC2)O)S2)C2=C1 IAQKGUUHZWQLJG-SJLPKXTDSA-N 0.000 claims 1
FCULQFBVFMIPMT-SJLPKXTDSA-N 1-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]-3-morpholin-4-ylpyrazin-2-one Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C(=O)C(N2CCOCC2)=NC=C1 FCULQFBVFMIPMT-SJLPKXTDSA-N 0.000 claims 1
HGZPHHYHVJVEER-OXQOHEQNSA-N 1-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]-6-methoxybenzimidazole-5-carbonitrile Chemical compound C1=NC=2C=C(C#N)C(OC)=CC=2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O HGZPHHYHVJVEER-OXQOHEQNSA-N 0.000 claims 1
NOXQAUBYFBKCEQ-OXQOHEQNSA-N 1-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]-n-methylbenzimidazole-5-carboxamide Chemical compound C1=NC2=CC(C(=O)NC)=CC=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O NOXQAUBYFBKCEQ-OXQOHEQNSA-N 0.000 claims 1
IQKICWDAQKBGOL-CZUORRHYSA-N 1-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]-n-methylimidazole-4-carboxamide Chemical compound C1=NC(C(=O)NC)=CN1CC1=CC=C(N=C(N[C@H]2[C@@H](CCCC2)O)S2)C2=C1 IQKICWDAQKBGOL-CZUORRHYSA-N 0.000 claims 1
IHHYCKKPQCLKEL-DNVCBOLYSA-N 1-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]benzimidazol-5-ol Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(O)C=C2N=C1 IHHYCKKPQCLKEL-DNVCBOLYSA-N 0.000 claims 1
HMXUYUWRQNNZCN-OXQOHEQNSA-N 1-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]benzimidazole-5-carbonitrile Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C#N)C=C2N=C1 HMXUYUWRQNNZCN-OXQOHEQNSA-N 0.000 claims 1
BEJXWBQFZKZMMM-OXQOHEQNSA-N 1-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzoxazol-6-yl]methyl]benzimidazole-5-carbonitrile Chemical compound O[C@@H]1CCCC[C@H]1NC(OC1=C2)=NC1=CC=C2CN1C2=CC=C(C#N)C=C2N=C1 BEJXWBQFZKZMMM-OXQOHEQNSA-N 0.000 claims 1
ITUWHPCBXIFQRB-UHFFFAOYSA-N 1-[[6-(purin-9-ylmethyl)-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NC2=CN=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1C2=CC=CC=C2CC1O ITUWHPCBXIFQRB-UHFFFAOYSA-N 0.000 claims 1
HHEUSPPWGQNLGQ-UHFFFAOYSA-N 1-[[6-[(5-bromo-6-methoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound OC1CC2=CC=CC=C2C1NC(SC1=C2)=NC1=CC=C2CN1C(C=C(C(=C2)Br)OC)=C2N=C1 HHEUSPPWGQNLGQ-UHFFFAOYSA-N 0.000 claims 1
PQQFPFIZXHGNCD-UHFFFAOYSA-N 1-[[6-[(5-bromoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NC2=CC=C(Br)N=C2N1CC(C=C1S2)=CC=C1N=C2NC1C2=CC=CC=C2CC1O PQQFPFIZXHGNCD-UHFFFAOYSA-N 0.000 claims 1
JFDUFWIBEMLENB-UHFFFAOYSA-N 1-[[6-[(6-bromoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NC2=CC(Br)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1C2=CC=CC=C2CC1O JFDUFWIBEMLENB-UHFFFAOYSA-N 0.000 claims 1
VNELNXBWSGYFIQ-UHFFFAOYSA-N 1-[[6-[(6-bromoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzoxazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NC2=CC(Br)=CN=C2N1CC(C=C1O2)=CC=C1N=C2NC1C2=CC=CC=C2CC1O VNELNXBWSGYFIQ-UHFFFAOYSA-N 0.000 claims 1
JCCHRBKBEPVEOJ-UHFFFAOYSA-N 1-[[6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NC2=CC(F)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1C2=CC=CC=C2CC1O JCCHRBKBEPVEOJ-UHFFFAOYSA-N 0.000 claims 1
CCDKJIGULMTAMW-UHFFFAOYSA-N 1-[[6-[[4-(1-methylpyrazol-4-yl)imidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NN(C)C=C1C(N=C1)=CN1CC1=CC=C(N=C(NC2C3=CC=CC=C3CC2O)S2)C2=C1 CCDKJIGULMTAMW-UHFFFAOYSA-N 0.000 claims 1
GOUATKXBFMOMLD-UHFFFAOYSA-N 1-[[6-[[5-(1-methylpyrazol-4-yl)imidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound C1=NN(C)C=C1C1=CN=CN1CC1=CC=C(N=C(NC2C3=CC=CC=C3CC2O)S2)C2=C1 GOUATKXBFMOMLD-UHFFFAOYSA-N 0.000 claims 1
ONBRPHRGZDAUNZ-UHFFFAOYSA-N 1-[[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]methyl]cyclohexan-1-ol Chemical compound N=1C2=CC=C(CN3C4=NC=CC=C4N=C3)C=C2SC=1NCC1(O)CCCCC1 ONBRPHRGZDAUNZ-UHFFFAOYSA-N 0.000 claims 1
PVBLJPCMWKGTOH-UHFFFAOYSA-N 1-aminocyclohexan-1-ol Chemical compound NC1(O)CCCCC1 PVBLJPCMWKGTOH-UHFFFAOYSA-N 0.000 claims 1
NWVGXXPWOYZODV-UHFFFAOYSA-N 1h-imidazole-5-carbonitrile Chemical compound N#CC1=CN=CN1 NWVGXXPWOYZODV-UHFFFAOYSA-N 0.000 claims 1
UMTWSSRZFWIKIJ-UHFFFAOYSA-N 2-(dimethylamino)-1-[3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridin-6-yl]ethanone Chemical compound C1=NC2=CC(C(=O)CN(C)C)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O UMTWSSRZFWIKIJ-UHFFFAOYSA-N 0.000 claims 1
UMTWSSRZFWIKIJ-YLJYHZDGSA-N 2-(dimethylamino)-1-[3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridin-6-yl]ethanone Chemical compound C1=NC2=CC(C(=O)CN(C)C)=CN=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O UMTWSSRZFWIKIJ-YLJYHZDGSA-N 0.000 claims 1
IGHXEHXQOZIDTD-UHFFFAOYSA-N 2-[1-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]benzimidazol-5-yl]oxyacetonitrile Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(OCC#N)C=C2N=C1 IGHXEHXQOZIDTD-UHFFFAOYSA-N 0.000 claims 1
IGHXEHXQOZIDTD-DYESRHJHSA-N 2-[1-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]benzimidazol-5-yl]oxyacetonitrile Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(OCC#N)C=C2N=C1 IGHXEHXQOZIDTD-DYESRHJHSA-N 0.000 claims 1
NWGWISADWXWMJJ-UHFFFAOYSA-N 2-[[4,7-difluoro-6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2F)=NC1=C(F)C=C2CN1C2=NC=CC=C2N=C1 NWGWISADWXWMJJ-UHFFFAOYSA-N 0.000 claims 1
ZDNKFBJHRLAMBS-UHFFFAOYSA-N 2-[[4-bromo-6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=C(Br)C=C2CN1C2=NC=CC=C2N=C1 ZDNKFBJHRLAMBS-UHFFFAOYSA-N 0.000 claims 1
ZTQGTDSHYYJPOK-UHFFFAOYSA-N 2-[[4-chloro-6-[(6-morpholin-4-ylimidazo[1,2-b]pyridazin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=C(Cl)C=C2CC1=CN=C2N1N=C(N1CCOCC1)C=C2 ZTQGTDSHYYJPOK-UHFFFAOYSA-N 0.000 claims 1
SFXVOEKNFDNRKW-UHFFFAOYSA-N 2-[[5-fluoro-6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC(F)=C2CN1C2=NC=CC=C2N=C1 SFXVOEKNFDNRKW-UHFFFAOYSA-N 0.000 claims 1
JVVGICYGJIFMQW-UHFFFAOYSA-N 2-[[6-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CNC2=NC=CC=C12 JVVGICYGJIFMQW-UHFFFAOYSA-N 0.000 claims 1
DRFSPYXJCMCENV-UHFFFAOYSA-N 2-[[6-(4h-imidazo[1,2-a]benzimidazol-1-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C1=CC=CC=C1N2 DRFSPYXJCMCENV-UHFFFAOYSA-N 0.000 claims 1
KKLRZTOURONSON-UHFFFAOYSA-N 2-[[6-(imidazo[1,2-a]pyrazin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound N=1C=C(N2C1C=NC=C2)CC2=CC1=C(N=C(S1)NC1C(CCCC1)O)C=C2 KKLRZTOURONSON-UHFFFAOYSA-N 0.000 claims 1
OFQLITHDMDHVSS-UHFFFAOYSA-N 2-[[6-(imidazo[1,2-a]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC=C2 OFQLITHDMDHVSS-UHFFFAOYSA-N 0.000 claims 1
OVFFQTKQASXSAI-UHFFFAOYSA-N 2-[[6-(imidazo[1,2-b]pyridazin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1N=CC=C2 OVFFQTKQASXSAI-UHFFFAOYSA-N 0.000 claims 1
AUPOBUMNCNWITJ-UHFFFAOYSA-N 2-[[6-(imidazo[1,2-b]pyridazin-3-ylmethyl)-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(OC1=C2)=NC1=CC=C2CC1=CN=C2N1N=CC=C2 AUPOBUMNCNWITJ-UHFFFAOYSA-N 0.000 claims 1
SRUQFXJKNIHZSV-UHFFFAOYSA-N 2-[[6-(imidazo[2,1-b][1,3]thiazol-5-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CS2 SRUQFXJKNIHZSV-UHFFFAOYSA-N 0.000 claims 1
BOOWGQXDGUSFLL-UHFFFAOYSA-N 2-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]-1-methylcyclohexan-1-ol Chemical compound CC1(O)CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=CC=C2N=C1 BOOWGQXDGUSFLL-UHFFFAOYSA-N 0.000 claims 1
UNGODVRJDXRURZ-UHFFFAOYSA-N 2-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-one Chemical compound O=C1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=CC=C2N=C1 UNGODVRJDXRURZ-UHFFFAOYSA-N 0.000 claims 1
XHSWOKDJKWWDEB-UHFFFAOYSA-N 2-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(OC1=C2)=NC1=CC=C2CN1C2=NC=CC=C2N=C1 XHSWOKDJKWWDEB-UHFFFAOYSA-N 0.000 claims 1
VWMPIAAFVQRGLF-UHFFFAOYSA-N 2-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-[1,3]thiazolo[4,5-b]pyridin-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=NC=C2CN1C2=NC=CC=C2N=C1 VWMPIAAFVQRGLF-UHFFFAOYSA-N 0.000 claims 1
KMGFNQOVZAISHI-UHFFFAOYSA-N 2-[[6-(imidazo[4,5-c]pyridin-1-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=NC=C2N=C1 KMGFNQOVZAISHI-UHFFFAOYSA-N 0.000 claims 1
NMMIEKGAWCDNKW-UHFFFAOYSA-N 2-[[6-(imidazo[4,5-c]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CN=CC=C2N=C1 NMMIEKGAWCDNKW-UHFFFAOYSA-N 0.000 claims 1
DKZAYADRKHFCHT-UHFFFAOYSA-N 2-[[6-(purin-9-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=NC=C2N=C1 DKZAYADRKHFCHT-UHFFFAOYSA-N 0.000 claims 1
NMJLYCAYGPSTEZ-UHFFFAOYSA-N 2-[[6-(purin-9-ylmethyl)-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(OC1=C2)=NC1=CC=C2CN1C2=NC=NC=C2N=C1 NMJLYCAYGPSTEZ-UHFFFAOYSA-N 0.000 claims 1
TVRMVNUMMKEJOB-UHFFFAOYSA-N 2-[[6-[(2-aminoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound NC1=NC2=CC=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O TVRMVNUMMKEJOB-UHFFFAOYSA-N 0.000 claims 1
BEKDUIWQBTWKAP-UHFFFAOYSA-N 2-[[6-[(5,6-dichloroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC(Cl)=C(Cl)C=C2N=C1 BEKDUIWQBTWKAP-UHFFFAOYSA-N 0.000 claims 1
AQJHHSHCKOFLIN-UHFFFAOYSA-N 2-[[6-[(5,6-difluorobenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC(F)=C(F)C=C2N=C1 AQJHHSHCKOFLIN-UHFFFAOYSA-N 0.000 claims 1
WWWOSLQKOUFWOR-UHFFFAOYSA-N 2-[[6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cycloheptan-1-ol Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCCCCC1O WWWOSLQKOUFWOR-UHFFFAOYSA-N 0.000 claims 1
QLCATMIVQMNKCQ-UHFFFAOYSA-N 2-[[6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O QLCATMIVQMNKCQ-UHFFFAOYSA-N 0.000 claims 1
SWZBKJOIZWDPCK-UHFFFAOYSA-N 2-[[6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclopentan-1-ol Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCCC1O SWZBKJOIZWDPCK-UHFFFAOYSA-N 0.000 claims 1
BTPUBELTJHXKIQ-UHFFFAOYSA-N 2-[[6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]phenol Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2NC1=CC=CC=C1O BTPUBELTJHXKIQ-UHFFFAOYSA-N 0.000 claims 1
XEKRTDGSFPRMAS-UHFFFAOYSA-N 2-[[6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1CC(C=C1O2)=CC=C1N=C2NC1CCCCC1O XEKRTDGSFPRMAS-UHFFFAOYSA-N 0.000 claims 1
VQXWKQQMEPXYRJ-UHFFFAOYSA-N 2-[[6-[(5,6-dimethylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=2C=C(C)C(C)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O VQXWKQQMEPXYRJ-UHFFFAOYSA-N 0.000 claims 1
DKAMBEGYXQVVBS-UHFFFAOYSA-N 2-[[6-[(5,7-difluorobenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=C(F)C=C(F)C=C2N=C1 DKAMBEGYXQVVBS-UHFFFAOYSA-N 0.000 claims 1
CMEVTXHVHBLBPN-UHFFFAOYSA-N 2-[[6-[(5,7-dimethylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(C)=CC(C)=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O CMEVTXHVHBLBPN-UHFFFAOYSA-N 0.000 claims 1
YOLNVXYHRKRYCZ-UHFFFAOYSA-N 2-[[6-[(5-bromo-6-methoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC=2C=C(Br)C(OC)=CC=2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O YOLNVXYHRKRYCZ-UHFFFAOYSA-N 0.000 claims 1
ALMRJRXXXGYEAP-UHFFFAOYSA-N 2-[[6-[(5-bromo-7-fluorobenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=C(F)C=C(Br)C=C2N=C1 ALMRJRXXXGYEAP-UHFFFAOYSA-N 0.000 claims 1
SEGMAVYWLRSBGK-UHFFFAOYSA-N 2-[[6-[(5-bromo-7-methylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=2C(C)=CC(Br)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O SEGMAVYWLRSBGK-UHFFFAOYSA-N 0.000 claims 1
GSEOFMYVPLQFHN-UHFFFAOYSA-N 2-[[6-[(5-bromobenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(Br)C=C2N=C1 GSEOFMYVPLQFHN-UHFFFAOYSA-N 0.000 claims 1
LDWXEHSKWJSURY-UHFFFAOYSA-N 2-[[6-[(5-bromoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC(Br)=CC=C2N=C1 LDWXEHSKWJSURY-UHFFFAOYSA-N 0.000 claims 1
OYFDTFWCVGOWOF-UHFFFAOYSA-N 2-[[6-[(5-ethenyl-7-fluorobenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=C(F)C=C(C=C)C=C2N=C1 OYFDTFWCVGOWOF-UHFFFAOYSA-N 0.000 claims 1
PMLGUUZCYHJIDW-UHFFFAOYSA-N 2-[[6-[(5-ethenylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C=C)C=C2N=C1 PMLGUUZCYHJIDW-UHFFFAOYSA-N 0.000 claims 1
IPKXGJGSTJVKJC-UHFFFAOYSA-N 2-[[6-[(5-ethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(OCC)=CC=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O IPKXGJGSTJVKJC-UHFFFAOYSA-N 0.000 claims 1
UIMZLUFSWMHYFO-UHFFFAOYSA-N 2-[[6-[(5-ethynylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C#C)C=C2N=C1 UIMZLUFSWMHYFO-UHFFFAOYSA-N 0.000 claims 1
MZEWZNHLWHFFJB-UHFFFAOYSA-N 2-[[6-[(5-fluorobenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(F)C=C2N=C1 MZEWZNHLWHFFJB-UHFFFAOYSA-N 0.000 claims 1
QUXSIXJDIWJADA-UHFFFAOYSA-N 2-[[6-[(5-fluoroimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C(F)=CC=C2 QUXSIXJDIWJADA-UHFFFAOYSA-N 0.000 claims 1
YCIIELOLIWYVEH-UHFFFAOYSA-N 2-[[6-[(5-imidazol-1-ylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(N3C=NC=C3)C=C2N=C1 YCIIELOLIWYVEH-UHFFFAOYSA-N 0.000 claims 1
ZVNKVLIYQDHLOP-UHFFFAOYSA-N 2-[[6-[(5-methoxybenzimidazol-1-yl)methyl]-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(OC)=CC=C2N1CC(C=C1O2)=CC=C1N=C2NC1CCCCC1O ZVNKVLIYQDHLOP-UHFFFAOYSA-N 0.000 claims 1
PCCSOHBSSCCHJF-UHFFFAOYSA-N 2-[[6-[(5-methoxyimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C12=NC(OC)=CC=C2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O PCCSOHBSSCCHJF-UHFFFAOYSA-N 0.000 claims 1
NRUODIJXQLWQCB-UHFFFAOYSA-N 2-[[6-[(5-methylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(C)=CC=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O NRUODIJXQLWQCB-UHFFFAOYSA-N 0.000 claims 1
LFXDRQGIXDOYOB-UHFFFAOYSA-N 2-[[6-[(5-methylsulfonylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(S(=O)(=O)C)=CC=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O LFXDRQGIXDOYOB-UHFFFAOYSA-N 0.000 claims 1
XNEIAVOFSZLYNR-UHFFFAOYSA-N 2-[[6-[(5-methylsulfonylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C12=NC(S(=O)(=O)C)=CC=C2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O XNEIAVOFSZLYNR-UHFFFAOYSA-N 0.000 claims 1
LBMWATWTAPWNJR-UHFFFAOYSA-N 2-[[6-[(5-morpholin-4-ylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(N3CCOCC3)C=C2N=C1 LBMWATWTAPWNJR-UHFFFAOYSA-N 0.000 claims 1
YOSCZGSKADBKJH-UHFFFAOYSA-N 2-[[6-[(5-pyrazol-1-ylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(N3N=CC=C3)C=C2N=C1 YOSCZGSKADBKJH-UHFFFAOYSA-N 0.000 claims 1
NWDDKKFPATVNQZ-UHFFFAOYSA-N 2-[[6-[(6-bromo-5-methoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=2C=C(Br)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O NWDDKKFPATVNQZ-UHFFFAOYSA-N 0.000 claims 1
BWCCVZDKIIPWCL-UHFFFAOYSA-N 2-[[6-[(6-bromo-5-methoxyimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC=2C=C(Br)C(OC)=NC=2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O BWCCVZDKIIPWCL-UHFFFAOYSA-N 0.000 claims 1
NIRYQGBZTDCLFE-UHFFFAOYSA-N 2-[[6-[(6-bromobenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC(Br)=CC=C2N=C1 NIRYQGBZTDCLFE-UHFFFAOYSA-N 0.000 claims 1
DGFSZEZXUIYAMO-UHFFFAOYSA-N 2-[[6-[(6-bromoimidazo[1,2-b]pyridazin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1N=C(Br)C=C2 DGFSZEZXUIYAMO-UHFFFAOYSA-N 0.000 claims 1
LYUIRJQDPBKHQL-UHFFFAOYSA-N 2-[[6-[(6-bromoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(Br)C=C2N=C1 LYUIRJQDPBKHQL-UHFFFAOYSA-N 0.000 claims 1
RJXTZKYLWHVCEZ-UHFFFAOYSA-N 2-[[6-[(6-bromoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(OC1=C2)=NC1=CC=C2CN1C2=NC=C(Br)C=C2N=C1 RJXTZKYLWHVCEZ-UHFFFAOYSA-N 0.000 claims 1
PASNSACSNNWLEM-UHFFFAOYSA-N 2-[[6-[(6-chloroimidazo[1,2-b]pyridazin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1N=C(Cl)C=C2 PASNSACSNNWLEM-UHFFFAOYSA-N 0.000 claims 1
WKYZEANVYDCMTP-UHFFFAOYSA-N 2-[[6-[(6-chloroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(Cl)C=C2N=C1 WKYZEANVYDCMTP-UHFFFAOYSA-N 0.000 claims 1
BNQPXMXPCACSIB-UHFFFAOYSA-N 2-[[6-[(6-cyclopropylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C3CC3)C=C2N=C1 BNQPXMXPCACSIB-UHFFFAOYSA-N 0.000 claims 1
GSSHIQPGDOQXQP-UHFFFAOYSA-N 2-[[6-[(6-ethenylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C=C)C=C2N=C1 GSSHIQPGDOQXQP-UHFFFAOYSA-N 0.000 claims 1
ZNJRLENSVYPIFL-UHFFFAOYSA-N 2-[[6-[(6-ethylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(CC)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O ZNJRLENSVYPIFL-UHFFFAOYSA-N 0.000 claims 1
DVBVNNPDIHVEMW-UHFFFAOYSA-N 2-[[6-[(6-ethynylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC(C#C)=CC=C2N=C1 DVBVNNPDIHVEMW-UHFFFAOYSA-N 0.000 claims 1
QHUAZXOWXYBXEY-UHFFFAOYSA-N 2-[[6-[(6-ethynylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C#C)C=C2N=C1 QHUAZXOWXYBXEY-UHFFFAOYSA-N 0.000 claims 1
USXOAMUOUBJHSC-UHFFFAOYSA-N 2-[[6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(OC1=C2)=NC1=CC=C2CN1C2=NC=C(F)C=C2N=C1 USXOAMUOUBJHSC-UHFFFAOYSA-N 0.000 claims 1
ZTXPCPFDGSXYCJ-UHFFFAOYSA-N 2-[[6-[(6-iodoimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(I)C=C2N=C1 ZTXPCPFDGSXYCJ-UHFFFAOYSA-N 0.000 claims 1
NVIQYEFOKOJNKG-UHFFFAOYSA-N 2-[[6-[(6-methoxybenzimidazol-1-yl)methyl]-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound C12=CC(OC)=CC=C2N=CN1CC(C=C1O2)=CC=C1N=C2NC1CCCCC1O NVIQYEFOKOJNKG-UHFFFAOYSA-N 0.000 claims 1
VJBUHJCEPZQLKK-UHFFFAOYSA-N 2-[[6-[(6-methoxyimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound N12C=C(OC)C=CC2=NC=C1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O VJBUHJCEPZQLKK-UHFFFAOYSA-N 0.000 claims 1
NRGBVKJJUHGNBE-UHFFFAOYSA-N 2-[[6-[(6-methoxyimidazo[1,2-b]pyridazin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound N12N=C(OC)C=CC2=NC=C1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O NRGBVKJJUHGNBE-UHFFFAOYSA-N 0.000 claims 1
QOLYAGXAGUVIJY-UHFFFAOYSA-N 2-[[6-[(6-methylsulfanylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(SC)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O QOLYAGXAGUVIJY-UHFFFAOYSA-N 0.000 claims 1
MTLGTTATHZIGLM-UHFFFAOYSA-N 2-[[6-[(6-methylsulfonylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C12=CC(S(=O)(=O)C)=CC=C2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O MTLGTTATHZIGLM-UHFFFAOYSA-N 0.000 claims 1
VTOINJGJYCTCDS-UHFFFAOYSA-N 2-[[6-[(6-methylsulfonylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(S(=O)(=O)C)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O VTOINJGJYCTCDS-UHFFFAOYSA-N 0.000 claims 1
LJKDHKNHGWLVOW-UHFFFAOYSA-N 2-[[6-[(6-morpholin-4-ylimidazo[1,2-b]pyridazin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1N=C(N1CCOCC1)C=C2 LJKDHKNHGWLVOW-UHFFFAOYSA-N 0.000 claims 1
ANMFHHANRBXAHJ-UHFFFAOYSA-N 2-[[6-[(6-morpholin-4-ylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(N3CCOCC3)C=C2N=C1 ANMFHHANRBXAHJ-UHFFFAOYSA-N 0.000 claims 1
UYTXSEQLFKUCLP-UHFFFAOYSA-N 2-[[6-[(6-pyrazol-1-ylimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=C(N1N=CC=C1)C=C2 UYTXSEQLFKUCLP-UHFFFAOYSA-N 0.000 claims 1
FPFGJZQIELQRRM-UHFFFAOYSA-N 2-[[6-[(6-pyrazol-1-ylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(N3N=CC=C3)C=C2N=C1 FPFGJZQIELQRRM-UHFFFAOYSA-N 0.000 claims 1
OWSYRBBGVYDNEV-UHFFFAOYSA-N 2-[[6-[(6-pyridin-3-ylimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C=3C=NC=CC=3)C=C2N=C1 OWSYRBBGVYDNEV-UHFFFAOYSA-N 0.000 claims 1
GVAWUOXCYPOHSC-UHFFFAOYSA-N 2-[[6-[(7-ethenylimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(C=C)=C2 GVAWUOXCYPOHSC-UHFFFAOYSA-N 0.000 claims 1
QPZHSFXYOLNLFR-UHFFFAOYSA-N 2-[[6-[(7-imidazol-1-ylimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(N1C=NC=C1)=C2 QPZHSFXYOLNLFR-UHFFFAOYSA-N 0.000 claims 1
YOLZHHCXDQWJAZ-UHFFFAOYSA-N 2-[[6-[(7-methoxyimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C=1N=C2C=C(OC)C=CN2C=1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O YOLZHHCXDQWJAZ-UHFFFAOYSA-N 0.000 claims 1
FSYDGSBLWQOAOT-UHFFFAOYSA-N 2-[[6-[(7-morpholin-4-ylimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(N1CCOCC1)=C2 FSYDGSBLWQOAOT-UHFFFAOYSA-N 0.000 claims 1
IWSMPKPDHBTJQQ-UHFFFAOYSA-N 2-[[6-[(7-pyrazol-1-ylimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(N1N=CC=C1)=C2 IWSMPKPDHBTJQQ-UHFFFAOYSA-N 0.000 claims 1
NBMVGLGACQEAGS-UHFFFAOYSA-N 2-[[6-[[2-(trifluoromethyl)purin-9-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC(C(F)(F)F)=NC=C2N=C1 NBMVGLGACQEAGS-UHFFFAOYSA-N 0.000 claims 1
PFFVLZFLNGFWCS-UHFFFAOYSA-N 2-[[6-[[4-(1-methylpyrazol-4-yl)imidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NN(C)C=C1C(N=C1)=CN1CC1=CC=C(N=C(NC2C(CCCC2)O)S2)C2=C1 PFFVLZFLNGFWCS-UHFFFAOYSA-N 0.000 claims 1
QXJPMXSQBYXTMC-UHFFFAOYSA-N 2-[[6-[[4-(1-methylpyrazol-4-yl)imidazol-1-yl]methyl]-1,3-benzoxazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NN(C)C=C1C(N=C1)=CN1CC1=CC=C(N=C(NC2C(CCCC2)O)O2)C2=C1 QXJPMXSQBYXTMC-UHFFFAOYSA-N 0.000 claims 1
YBYGVDRRNDUZAR-UHFFFAOYSA-N 2-[[6-[[5-(1,2,3,6-tetrahydropyridin-4-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C=3CCNCC=3)C=C2N=C1 YBYGVDRRNDUZAR-UHFFFAOYSA-N 0.000 claims 1
KHWOGIBFKBMEMB-UHFFFAOYSA-N 2-[[6-[[5-(1,2,4-triazol-1-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(N3N=CN=C3)C=C2N=C1 KHWOGIBFKBMEMB-UHFFFAOYSA-N 0.000 claims 1
SCHHIURSXLJOJD-UHFFFAOYSA-N 2-[[6-[[5-(1h-pyrazol-5-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C3=NNC=C3)C=C2N=C1 SCHHIURSXLJOJD-UHFFFAOYSA-N 0.000 claims 1
TUAHPMBQYLDNLM-UHFFFAOYSA-N 2-[[6-[[5-(2-hydroxyethoxy)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(OCCO)=CC=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O TUAHPMBQYLDNLM-UHFFFAOYSA-N 0.000 claims 1
DHULSKZLTBPDMT-UHFFFAOYSA-N 2-[[6-[[5-(2-methyltetrazol-5-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound CN1N=NC(C=2C=C3N=CN(CC=4C=C5SC(NC6C(CCCC6)O)=NC5=CC=4)C3=CC=2)=N1 DHULSKZLTBPDMT-UHFFFAOYSA-N 0.000 claims 1
TZPZDQPRKNFVFD-UHFFFAOYSA-N 2-[[6-[[5-(2-morpholin-4-ylethoxy)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(OCCN3CCOCC3)C=C2N=C1 TZPZDQPRKNFVFD-UHFFFAOYSA-N 0.000 claims 1
GGFFOKSWIRUSBH-UHFFFAOYSA-N 2-[[6-[[5-(3,3,3-trifluoroprop-1-en-2-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C(=C)C(F)(F)F)C=C2N=C1 GGFFOKSWIRUSBH-UHFFFAOYSA-N 0.000 claims 1
BRFVKZHLBDEXON-UHFFFAOYSA-N 2-[[6-[[5-(3,6-dihydro-2h-pyran-4-yl)-7-fluorobenzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=C(F)C=C(C=3CCOCC=3)C=C2N=C1 BRFVKZHLBDEXON-UHFFFAOYSA-N 0.000 claims 1
AYOVJIOUBUCUIO-UHFFFAOYSA-N 2-[[6-[[5-(3,6-dihydro-2h-pyran-4-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C=3CCOCC=3)C=C2N=C1 AYOVJIOUBUCUIO-UHFFFAOYSA-N 0.000 claims 1
VIWRIEUBXDNHKO-UHFFFAOYSA-N 2-[[6-[[5-(cyclohexen-1-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C=3CCCCC=3)C=C2N=C1 VIWRIEUBXDNHKO-UHFFFAOYSA-N 0.000 claims 1
MBOWAMBYGZLHMR-UHFFFAOYSA-N 2-[[6-[[5-(oxetan-3-yloxy)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(OC3COC3)C=C2N=C1 MBOWAMBYGZLHMR-UHFFFAOYSA-N 0.000 claims 1
VQNDUYIKUOKUHV-UHFFFAOYSA-N 2-[[6-[[5-(trifluoromethoxy)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(OC(F)(F)F)C=C2N=C1 VQNDUYIKUOKUHV-UHFFFAOYSA-N 0.000 claims 1
VJNDUIFDHUIZCF-UHFFFAOYSA-N 2-[[6-[[5-(trifluoromethyl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C(F)(F)F)C=C2N=C1 VJNDUIFDHUIZCF-UHFFFAOYSA-N 0.000 claims 1
OHCCZARVEWQRKP-UHFFFAOYSA-N 2-[[6-[[5-[1-methyl-3-(trifluoromethyl)pyrazol-4-yl]benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound FC(F)(F)C1=NN(C)C=C1C1=CC=C(N(CC=2C=C3SC(NC4C(CCCC4)O)=NC3=CC=2)C=N2)C2=C1 OHCCZARVEWQRKP-UHFFFAOYSA-N 0.000 claims 1
DATMQZZRWABIPG-UHFFFAOYSA-N 2-[[6-[[5-methoxy-6-(1-methylpyrazol-4-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=2C=C(C3=CN(C)N=C3)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O DATMQZZRWABIPG-UHFFFAOYSA-N 0.000 claims 1
XBVXMKBQERTXDV-UHFFFAOYSA-N 2-[[6-[[6-(1,2,4-triazol-1-yl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(N3N=CN=C3)C=C2N=C1 XBVXMKBQERTXDV-UHFFFAOYSA-N 0.000 claims 1
BJXGWXSWPJOMJW-UHFFFAOYSA-N 2-[[6-[[6-(1-hydroxyethyl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(C(O)C)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O BJXGWXSWPJOMJW-UHFFFAOYSA-N 0.000 claims 1
CNVJZPRWHLOWAZ-UHFFFAOYSA-N 2-[[6-[[6-(1-methylpyrazol-4-yl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NN(C)C=C1C1=CN=C(N(CC=2C=C3SC(NC4C(CCCC4)O)=NC3=CC=2)C=N2)C2=C1 CNVJZPRWHLOWAZ-UHFFFAOYSA-N 0.000 claims 1
FYTUZUJHDDNATD-UHFFFAOYSA-N 2-[[6-[[6-(2-hydroxypropan-2-yl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(C(C)(O)C)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O FYTUZUJHDDNATD-UHFFFAOYSA-N 0.000 claims 1
YINHMVICOHXZSR-UHFFFAOYSA-N 2-[[6-[[6-(2-methyltetrazol-5-yl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound CN1N=NC(C=2C=C3N=CN(CC=4C=C5SC(NC6C(CCCC6)O)=NC5=CC=4)C3=NC=2)=N1 YINHMVICOHXZSR-UHFFFAOYSA-N 0.000 claims 1
GANWDCBZWPJSTP-UHFFFAOYSA-N 2-[[6-[[6-(2h-tetrazol-5-yl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C3=NNN=N3)C=C2N=C1 GANWDCBZWPJSTP-UHFFFAOYSA-N 0.000 claims 1
ZRGZRWVXOLSCJY-UHFFFAOYSA-N 2-[[6-[[6-(4-methylpiperazin-1-yl)imidazo[1,2-b]pyridazin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1CN(C)CCN1C1=NN2C(CC=3C=C4SC(NC5C(CCCC5)O)=NC4=CC=3)=CN=C2C=C1 ZRGZRWVXOLSCJY-UHFFFAOYSA-N 0.000 claims 1
MCDBPCCZIHTZGQ-UHFFFAOYSA-N 2-[[6-[[6-(aminomethyl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(CN)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O MCDBPCCZIHTZGQ-UHFFFAOYSA-N 0.000 claims 1
HSYCUJSCOUQBFG-UHFFFAOYSA-N 2-[[6-[[6-(hydroxymethyl)imidazo[1,2-b]pyridazin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound N12N=C(CO)C=CC2=NC=C1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O HSYCUJSCOUQBFG-UHFFFAOYSA-N 0.000 claims 1
IIZJMWUPABCNQB-UHFFFAOYSA-N 2-[[6-[[6-(hydroxymethyl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(CO)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O IIZJMWUPABCNQB-UHFFFAOYSA-N 0.000 claims 1
JSOLSAVZJMUNSX-UHFFFAOYSA-N 2-[[6-[[6-(methylsulfanylmethyl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC2=CC(CSC)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O JSOLSAVZJMUNSX-UHFFFAOYSA-N 0.000 claims 1
ARPTUKPUVFAFDP-UHFFFAOYSA-N 2-[[6-[[6-(morpholin-4-ylmethyl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(CN3CCOCC3)C=C2N=C1 ARPTUKPUVFAFDP-UHFFFAOYSA-N 0.000 claims 1
GAXMSUGQADXPDK-UHFFFAOYSA-N 2-[[6-[[6-(trifluoromethyl)imidazo[4,5-b]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C(F)(F)F)C=C2N=C1 GAXMSUGQADXPDK-UHFFFAOYSA-N 0.000 claims 1
AFYAYLVQQVFFLO-UHFFFAOYSA-N 2-[[6-[[6-methoxy-5-(1-methylpyrazol-4-yl)benzimidazol-1-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1=NC=2C=C(C3=CN(C)N=C3)C(OC)=CC=2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O AFYAYLVQQVFFLO-UHFFFAOYSA-N 0.000 claims 1
CCMTXBVIGROOOG-UHFFFAOYSA-N 2-[[6-[[7-(1,2,4-triazol-1-yl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(N1N=CN=C1)=C2 CCMTXBVIGROOOG-UHFFFAOYSA-N 0.000 claims 1
XPBUJTUNMWTHKF-UHFFFAOYSA-N 2-[[6-[[7-(1-hydroxyethyl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C=1N=C2C=C(C(O)C)C=CN2C=1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O XPBUJTUNMWTHKF-UHFFFAOYSA-N 0.000 claims 1
QIBKVAMZUMXSOT-UHFFFAOYSA-N 2-[[6-[[7-(2-hydroxyethoxy)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C=1N=C2C=C(OCCO)C=CN2C=1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O QIBKVAMZUMXSOT-UHFFFAOYSA-N 0.000 claims 1
TUBXOBXPCOWDMQ-UHFFFAOYSA-N 2-[[6-[[7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C=1N=C2C=C(OCCOC)C=CN2C=1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O TUBXOBXPCOWDMQ-UHFFFAOYSA-N 0.000 claims 1
ANIUPCVLIORXEA-UHFFFAOYSA-N 2-[[6-[[7-(4-methylpiperazin-1-yl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C1CN(C)CCN1C1=CC2=NC=C(CC=3C=C4SC(NC5C(CCCC5)O)=NC4=CC=3)N2C=C1 ANIUPCVLIORXEA-UHFFFAOYSA-N 0.000 claims 1
WECXRAJFNLZUNF-UHFFFAOYSA-N 2-[[6-[[7-(N-hydroxy-C-methylcarbonimidoyl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C=1N=C2C=C(C(=NO)C)C=CN2C=1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O WECXRAJFNLZUNF-UHFFFAOYSA-N 0.000 claims 1
NLOHZMBGHWIEBX-UHFFFAOYSA-N 2-[[6-[[7-(n-methoxy-c-methylcarbonimidoyl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C=1N=C2C=C(C(C)=NOC)C=CN2C=1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O NLOHZMBGHWIEBX-UHFFFAOYSA-N 0.000 claims 1
JQXWQIXHCUIHMD-UHFFFAOYSA-N 2-[[6-[[7-(triazol-1-yl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(N1N=NC=C1)=C2 JQXWQIXHCUIHMD-UHFFFAOYSA-N 0.000 claims 1
HADGQQBSDGCSQD-UHFFFAOYSA-N 2-[[6-[[7-(triazol-2-yl)imidazo[1,2-a]pyridin-3-yl]methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(N1N=CC=N1)=C2 HADGQQBSDGCSQD-UHFFFAOYSA-N 0.000 claims 1
YCJPECKKCSFKFG-UHFFFAOYSA-N 2-[[6-[methoxy(1h-pyrrolo[2,3-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound C=1NC2=NC=CC=C2C=1C(OC)C(C=C1S2)=CC=C1N=C2NC1CCCCC1O YCJPECKKCSFKFG-UHFFFAOYSA-N 0.000 claims 1
JJKMXXZEHUJYON-UHFFFAOYSA-N 2-[[7-fluoro-6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]cyclohexan-1-ol Chemical compound OC1CCCCC1NC(SC1=C2F)=NC1=CC=C2CN1C2=NC=CC=C2N=C1 JJKMXXZEHUJYON-UHFFFAOYSA-N 0.000 claims 1
POROCIZVRRQUBL-UHFFFAOYSA-N 2-cyclohexyl-2-[[6-(imidazo[4,5-b]pyridin-3-ylmethyl)-1,3-benzothiazol-2-yl]amino]ethanol Chemical compound N=1C2=CC=C(CN3C4=NC=CC=C4N=C3)C=C2SC=1NC(CO)C1CCCCC1 POROCIZVRRQUBL-UHFFFAOYSA-N 0.000 claims 1
GOWBITABVGUPRO-UHFFFAOYSA-N 3-[1-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]benzimidazol-5-yl]prop-2-enoic acid Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C=CC(O)=O)C=C2N=C1 GOWBITABVGUPRO-UHFFFAOYSA-N 0.000 claims 1
CZOTVPVOUYQFMO-UHFFFAOYSA-N 3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]-5-methoxyimidazo[4,5-b]pyridine-6-carbonitrile Chemical compound C1=NC=2C=C(C#N)C(OC)=NC=2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O CZOTVPVOUYQFMO-UHFFFAOYSA-N 0.000 claims 1
BOQFCZGOJNATHK-UHFFFAOYSA-N 3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]-6-methoxybenzimidazole-5-carbonitrile Chemical compound C1=2C=C(C#N)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O BOQFCZGOJNATHK-UHFFFAOYSA-N 0.000 claims 1
PWHWPHYEBPVHED-UHFFFAOYSA-N 3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]-n,n-dimethylimidazo[4,5-b]pyridine-6-carboxamide Chemical compound C1=NC2=CC(C(=O)N(C)C)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O PWHWPHYEBPVHED-UHFFFAOYSA-N 0.000 claims 1
IQAMFBVJCYAUBH-UHFFFAOYSA-N 3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]-n-methylimidazo[1,2-b]pyridazine-6-carboxamide Chemical compound N12N=C(C(=O)NC)C=CC2=NC=C1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O IQAMFBVJCYAUBH-UHFFFAOYSA-N 0.000 claims 1
CKIIHYWTCUAAOZ-UHFFFAOYSA-N 3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]-n-methylimidazo[4,5-b]pyridine-6-carboxamide Chemical compound C1=NC2=CC(C(=O)NC)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O CKIIHYWTCUAAOZ-UHFFFAOYSA-N 0.000 claims 1
OPBBGEMAKXBPJQ-UHFFFAOYSA-N 3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]benzimidazole-5-carbonitrile Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC(C#N)=CC=C2N=C1 OPBBGEMAKXBPJQ-UHFFFAOYSA-N 0.000 claims 1
IZOOCFRYSKIFNW-UHFFFAOYSA-N 3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]imidazo[1,2-a]pyridine-7-carbonitrile Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(C#N)=C2 IZOOCFRYSKIFNW-UHFFFAOYSA-N 0.000 claims 1
JWHLMCWOYWZLBH-UHFFFAOYSA-N 3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]imidazo[1,2-b]pyridazine-6-carbonitrile Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1N=C(C#N)C=C2 JWHLMCWOYWZLBH-UHFFFAOYSA-N 0.000 claims 1
COGBZRXSQDXSOR-UHFFFAOYSA-N 3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridine-5,6-dicarbonitrile Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC(C#N)=C(C#N)C=C2N=C1 COGBZRXSQDXSOR-UHFFFAOYSA-N 0.000 claims 1
FCSITBKXLSKSIB-UHFFFAOYSA-N 3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridine-5-carbonitrile Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC(C#N)=CC=C2N=C1 FCSITBKXLSKSIB-UHFFFAOYSA-N 0.000 claims 1
LKXWRKOWURMBEF-UHFFFAOYSA-N 3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C#N)C=C2N=C1 LKXWRKOWURMBEF-UHFFFAOYSA-N 0.000 claims 1
JUZCIYUGPLYVMR-UHFFFAOYSA-N 3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridine-6-carboxylic acid Chemical compound OC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C(O)=O)C=C2N=C1 JUZCIYUGPLYVMR-UHFFFAOYSA-N 0.000 claims 1
ANTCGVRJWRUCMF-UHFFFAOYSA-N 3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzoxazol-6-yl]methyl]imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound OC1CCCCC1NC(OC1=C2)=NC1=CC=C2CN1C2=NC=C(C#N)C=C2N=C1 ANTCGVRJWRUCMF-UHFFFAOYSA-N 0.000 claims 1
YVJYGOGREMEPPN-DLBZAZTESA-N 3-[[2-[[(1r,2r)-2-(hydroxymethyl)cyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound OC[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C#N)C=C2N=C1 YVJYGOGREMEPPN-DLBZAZTESA-N 0.000 claims 1
CZOTVPVOUYQFMO-CRAIPNDOSA-N 3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]-5-methoxyimidazo[4,5-b]pyridine-6-carbonitrile Chemical compound C1=NC=2C=C(C#N)C(OC)=NC=2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O CZOTVPVOUYQFMO-CRAIPNDOSA-N 0.000 claims 1
BOQFCZGOJNATHK-OXQOHEQNSA-N 3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]-6-methoxybenzimidazole-5-carbonitrile Chemical compound C1=2C=C(C#N)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O BOQFCZGOJNATHK-OXQOHEQNSA-N 0.000 claims 1
PWHWPHYEBPVHED-VQIMIIECSA-N 3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]-n,n-dimethylimidazo[4,5-b]pyridine-6-carboxamide Chemical compound C1=NC2=CC(C(=O)N(C)C)=CN=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O PWHWPHYEBPVHED-VQIMIIECSA-N 0.000 claims 1
IQAMFBVJCYAUBH-CRAIPNDOSA-N 3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]-n-methylimidazo[1,2-b]pyridazine-6-carboxamide Chemical compound N12N=C(C(=O)NC)C=CC2=NC=C1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O IQAMFBVJCYAUBH-CRAIPNDOSA-N 0.000 claims 1
CKIIHYWTCUAAOZ-CRAIPNDOSA-N 3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]-n-methylimidazo[4,5-b]pyridine-6-carboxamide Chemical compound C1=NC2=CC(C(=O)NC)=CN=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O CKIIHYWTCUAAOZ-CRAIPNDOSA-N 0.000 claims 1
OPBBGEMAKXBPJQ-YLJYHZDGSA-N 3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]benzimidazole-5-carbonitrile Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=CC(C#N)=CC=C2N=C1 OPBBGEMAKXBPJQ-YLJYHZDGSA-N 0.000 claims 1
IZOOCFRYSKIFNW-IEBWSBKVSA-N 3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]imidazo[1,2-a]pyridine-7-carbonitrile Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(C#N)=C2 IZOOCFRYSKIFNW-IEBWSBKVSA-N 0.000 claims 1
JWHLMCWOYWZLBH-SJLPKXTDSA-N 3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]imidazo[1,2-b]pyridazine-6-carbonitrile Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1N=C(C#N)C=C2 JWHLMCWOYWZLBH-SJLPKXTDSA-N 0.000 claims 1
COGBZRXSQDXSOR-DNVCBOLYSA-N 3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridine-5,6-dicarbonitrile Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC(C#N)=C(C#N)C=C2N=C1 COGBZRXSQDXSOR-DNVCBOLYSA-N 0.000 claims 1
FCSITBKXLSKSIB-CRAIPNDOSA-N 3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridine-5-carbonitrile Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC(C#N)=CC=C2N=C1 FCSITBKXLSKSIB-CRAIPNDOSA-N 0.000 claims 1
LKXWRKOWURMBEF-CRAIPNDOSA-N 3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C#N)C=C2N=C1 LKXWRKOWURMBEF-CRAIPNDOSA-N 0.000 claims 1
JUZCIYUGPLYVMR-RHSMWYFYSA-N 3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridine-6-carboxylic acid Chemical compound O[C@@H]1CCCC[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C(O)=O)C=C2N=C1 JUZCIYUGPLYVMR-RHSMWYFYSA-N 0.000 claims 1
ANTCGVRJWRUCMF-CRAIPNDOSA-N 3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzoxazol-6-yl]methyl]imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound O[C@@H]1CCCC[C@H]1NC(OC1=C2)=NC1=CC=C2CN1C2=NC=C(C#N)C=C2N=C1 ANTCGVRJWRUCMF-CRAIPNDOSA-N 0.000 claims 1
YVJYGOGREMEPPN-UHFFFAOYSA-N 3-[[2-[[2-(hydroxymethyl)cyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound OCC1CCCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=NC=C(C#N)C=C2N=C1 YVJYGOGREMEPPN-UHFFFAOYSA-N 0.000 claims 1
XRHBJZDMGZZWBO-UHFFFAOYSA-N 3-[[6-[(5-ethenylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexane-1,2-diol Chemical compound OC1C(O)CCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(C=C)C=C2N=C1 XRHBJZDMGZZWBO-UHFFFAOYSA-N 0.000 claims 1
MSJYLMCRIKGLEQ-UHFFFAOYSA-N 3-[[6-[(5-methoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexane-1,2-diol Chemical compound C1=NC2=CC(OC)=CC=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCC(O)C1O MSJYLMCRIKGLEQ-UHFFFAOYSA-N 0.000 claims 1
AGRAKNMYKAASSB-UHFFFAOYSA-N 3-[[6-[(5-morpholin-4-ylbenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexane-1,2-diol Chemical compound OC1C(O)CCCC1NC(SC1=C2)=NC1=CC=C2CN1C2=CC=C(N3CCOCC3)C=C2N=C1 AGRAKNMYKAASSB-UHFFFAOYSA-N 0.000 claims 1
GFKLQIPLTHBJAG-UHFFFAOYSA-N 3-[[6-[(7-pyrazol-1-ylimidazo[1,2-a]pyridin-3-yl)methyl]-1,3-benzothiazol-2-yl]amino]cyclohexane-1,2-diol Chemical compound OC1C(O)CCCC1NC(SC1=C2)=NC1=CC=C2CC1=CN=C2N1C=CC(N1N=CC=C1)=C2 GFKLQIPLTHBJAG-UHFFFAOYSA-N 0.000 claims 1
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BABJPMUHFVSIHW-UHFFFAOYSA-N n-(cyclohexylmethyl)-6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-amine Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2NCC1CCCCC1 BABJPMUHFVSIHW-UHFFFAOYSA-N 0.000 claims 1
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LSOGTXLGSZTVCW-HUUCEWRRSA-N n-[(1r,2r)-2-chlorocyclohexyl]-6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC2=CC(F)=CN=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1Cl LSOGTXLGSZTVCW-HUUCEWRRSA-N 0.000 claims 1
LSOGTXLGSZTVCW-LSDHHAIUSA-N n-[(1r,2s)-2-chlorocyclohexyl]-6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC2=CC(F)=CN=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@@H]1Cl LSOGTXLGSZTVCW-LSDHHAIUSA-N 0.000 claims 1
QJUBOSPIWKRZCK-INIZCTEOSA-N n-[(1s)-1-cyclohexylethyl]-6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-amine Chemical compound C1([C@H](C)NC2=NC3=CC=C(C=C3S2)CN2C=NC=3C=C(C(=CC=32)OC)OC)CCCCC1 QJUBOSPIWKRZCK-INIZCTEOSA-N 0.000 claims 1
ZOUDVUYMIUJXHG-IBGZPJMESA-N n-[(1s)-2,3-dihydro-1h-inden-1-yl]-6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-amine Chemical compound C1CC2=CC=CC=C2[C@H]1NC(SC1=C2)=NC1=CC=C2CN1C=NC2=C1C=C(OC)C(OC)=C2 ZOUDVUYMIUJXHG-IBGZPJMESA-N 0.000 claims 1
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ZTFQZFQNCYQJKN-UHFFFAOYSA-N n-[1-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]imidazol-4-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CN1CC1=CC=C(N=C(NC2C(CCCC2)O)S2)C2=C1 ZTFQZFQNCYQJKN-UHFFFAOYSA-N 0.000 claims 1
ZTFQZFQNCYQJKN-GDBMZVCRSA-N n-[1-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]imidazol-4-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CN1CC1=CC=C(N=C(N[C@H]2[C@@H](CCCC2)O)S2)C2=C1 ZTFQZFQNCYQJKN-GDBMZVCRSA-N 0.000 claims 1
VLTZTFIPWNJQHF-UHFFFAOYSA-N n-[[3-[[2-[(2-hydroxycyclohexyl)amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridin-6-yl]methyl]acetamide Chemical compound C1=NC2=CC(CNC(=O)C)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1O VLTZTFIPWNJQHF-UHFFFAOYSA-N 0.000 claims 1
VLTZTFIPWNJQHF-YLJYHZDGSA-N n-[[3-[[2-[[(1r,2r)-2-hydroxycyclohexyl]amino]-1,3-benzothiazol-6-yl]methyl]imidazo[4,5-b]pyridin-6-yl]methyl]acetamide Chemical compound C1=NC2=CC(CNC(=O)C)=CN=C2N1CC(C=C1S2)=CC=C1N=C2N[C@@H]1CCCC[C@H]1O VLTZTFIPWNJQHF-YLJYHZDGSA-N 0.000 claims 1
NVOFRXAUNDFMRZ-UHFFFAOYSA-N n-benzyl-6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-amine Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2NCC1=CC=CC=C1 NVOFRXAUNDFMRZ-UHFFFAOYSA-N 0.000 claims 1
TUNHOOMCAAAQAS-UHFFFAOYSA-N n-cyclohex-2-en-1-yl-6-[(6-fluoroimidazo[4,5-b]pyridin-3-yl)methyl]-1,3-benzothiazol-2-amine Chemical compound C1=NC2=CC(F)=CN=C2N1CC(C=C1S2)=CC=C1N=C2NC1CCCC=C1 TUNHOOMCAAAQAS-UHFFFAOYSA-N 0.000 claims 1
AWFGQXHTIPRBMG-UHFFFAOYSA-N n-cyclohexyl-6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-1,3-benzothiazol-2-amine Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2NC1CCCCC1 AWFGQXHTIPRBMG-UHFFFAOYSA-N 0.000 claims 1
HLOSIHPWXMDHAS-UHFFFAOYSA-N n-cyclohexyl-6-[(5,6-dimethoxybenzimidazol-1-yl)methyl]-n-methyl-1,3-benzothiazol-2-amine Chemical compound C1=2C=C(OC)C(OC)=CC=2N=CN1CC(C=C1S2)=CC=C1N=C2N(C)C1CCCCC1 HLOSIHPWXMDHAS-UHFFFAOYSA-N 0.000 claims 1
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201000002528 pancreatic cancer Diseases 0.000 claims 1
208000008443 pancreatic carcinoma Diseases 0.000 claims 1
239000008177 pharmaceutical agent Substances 0.000 claims 1
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125000004076 pyridyl group Chemical group 0.000 claims 1
208000037803 restenosis Diseases 0.000 claims 1
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201000000306 sarcoidosis Diseases 0.000 claims 1
201000011549 stomach cancer Diseases 0.000 claims 1
201000002510 thyroid cancer Diseases 0.000 claims 1
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208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
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JP2014535928A 2011-10-14 2012-10-12 Ｉｉｉ型受容体チロシンキナーゼの調節因子としての複素環式化合物及びその使用 Expired - Fee Related JP6162130B2 (ja)