JP2006503010A - 数種の新規なイミダゾピリジンおよびその使用 - Google Patents

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Publication number

JP2006503010A

JP2006503010A JP2004529004A JP2004529004A JP2006503010A JP 2006503010 A JP2006503010 A JP 2006503010A JP 2004529004 A JP2004529004 A JP 2004529004A JP 2004529004 A JP2004529004 A JP 2004529004A JP 2006503010 A JP2006503010 A JP 2006503010A

Authority

JP

Japan

Prior art keywords

imidazo

pyridin

bromo

phenyl

phenoxy

Prior art date

2002-08-14

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

Withdrawn

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• 150000005232 imidazopyridines Chemical class 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 341
• 150000003839 salts Chemical class 0.000 claims abstract description 62
• 238000000034 method Methods 0.000 claims abstract description 43
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 32
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 20
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 20
• 239000003814 drug Substances 0.000 claims abstract description 15
• 238000004519 manufacturing process Methods 0.000 claims abstract description 14
• 230000000694 effects Effects 0.000 claims abstract description 13
• 230000005764 inhibitory process Effects 0.000 claims abstract description 10
• 230000009286 beneficial effect Effects 0.000 claims abstract description 7
• 230000006806 disease prevention Effects 0.000 claims abstract description 4
• 239000000126 substance Substances 0.000 claims abstract description 4
• -1 methoxyphenyl Chemical group 0.000 claims description 481
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 179
• 125000000217 alkyl group Chemical group 0.000 claims description 147
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 140
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 88
• 125000001072 heteroaryl group Chemical group 0.000 claims description 88
• 229910052736 halogen Inorganic materials 0.000 claims description 82
• 125000005842 heteroatom Chemical group 0.000 claims description 81
• 229910052760 oxygen Inorganic materials 0.000 claims description 79
• 150000002367 halogens Chemical class 0.000 claims description 78
• 229910052717 sulfur Inorganic materials 0.000 claims description 78
• 229910052799 carbon Inorganic materials 0.000 claims description 74
• 150000001412 amines Chemical class 0.000 claims description 69
• 229910052757 nitrogen Inorganic materials 0.000 claims description 69
• 229910052739 hydrogen Inorganic materials 0.000 claims description 57
• 125000003545 alkoxy group Chemical group 0.000 claims description 47
• 229920006395 saturated elastomer Polymers 0.000 claims description 41
• 201000010099 disease Diseases 0.000 claims description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
• 125000001041 indolyl group Chemical group 0.000 claims description 30
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 28
• 125000000623 heterocyclic group Chemical group 0.000 claims description 25
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 23
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
• 125000001424 substituent group Chemical group 0.000 claims description 22
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 18
• 125000004076 pyridyl group Chemical group 0.000 claims description 18
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 15
• 125000000335 thiazolyl group Chemical group 0.000 claims description 15
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 14
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 14
• 208000006673 asthma Diseases 0.000 claims description 12
• 125000003118 aryl group Chemical group 0.000 claims description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 230000002265 prevention Effects 0.000 claims description 10
• 125000001425 triazolyl group Chemical group 0.000 claims description 10
• 210000003630 histaminocyte Anatomy 0.000 claims description 9
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 125000003386 piperidinyl group Chemical group 0.000 claims description 9
• 230000008569 process Effects 0.000 claims description 9
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 7
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 7
• 239000002671 adjuvant Substances 0.000 claims description 7
• 210000003651 basophil Anatomy 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• YVPZMBWNDMKAFG-UHFFFAOYSA-N 2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-n-(oxolan-2-ylmethyl)ethanamine Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCNCC1CCCO1 YVPZMBWNDMKAFG-UHFFFAOYSA-N 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000001589 carboacyl group Chemical group 0.000 claims description 6
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 5
• JYDBGXIVWJGCCL-UHFFFAOYSA-N 1-[6-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-yl]pyrrolidin-3-amine Chemical compound C1C(N)CCN1C1=C(Cl)C=NC2=C1NC(C=1C=CC(OCCN3CCOCC3)=CC=1)=N2 JYDBGXIVWJGCCL-UHFFFAOYSA-N 0.000 claims description 5
• ORSZXLAEEIHIBA-UHFFFAOYSA-N 7-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound N=1C=2C(Cl)=C(C#N)C=NC=2NC=1C(C=C1)=CC=C1OCCN1CCOCC1 ORSZXLAEEIHIBA-UHFFFAOYSA-N 0.000 claims description 5
• MPMIHCIYDGMTLC-UHFFFAOYSA-N ClC=1C(=C2C(=NC1)N=C(N2)C=2C=CC(=C(N)C2)OCCN2CCOCC2)Cl.ClC=2C(=C1C(=NC2)N=C(N1)C1=CC(=C(C=C1)OCCN1CCOCC1)[N+](=O)[O-])Cl Chemical compound ClC=1C(=C2C(=NC1)N=C(N2)C=2C=CC(=C(N)C2)OCCN2CCOCC2)Cl.ClC=2C(=C1C(=NC2)N=C(N1)C1=CC(=C(C=C1)OCCN1CCOCC1)[N+](=O)[O-])Cl MPMIHCIYDGMTLC-UHFFFAOYSA-N 0.000 claims description 5
• 239000004593 Epoxy Substances 0.000 claims description 5
• APJYDQYYACXCRM-UHFFFAOYSA-N Tryptamine Natural products C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 claims description 5
• YCIFVSANVOFBMV-UHFFFAOYSA-N n-benzyl-6-chloro-n-methyl-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-amine Chemical compound ClC=1C=NC=2N=C(C=3C=CC(OCCN4CCOCC4)=CC=3)NC=2C=1N(C)CC1=CC=CC=C1 YCIFVSANVOFBMV-UHFFFAOYSA-N 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 5
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 4
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
• 201000010105 allergic rhinitis Diseases 0.000 claims description 4
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 4
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• YFWLOOOZFUSXRK-UHFFFAOYSA-N 1-[3-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-2-hydroxypropyl]pyrrolidin-3-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN1CCC(O)C1 YFWLOOOZFUSXRK-UHFFFAOYSA-N 0.000 claims description 3
• QAVCGRXNLMKXHJ-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-morpholin-4-ylpropan-2-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN1CCOCC1 QAVCGRXNLMKXHJ-UHFFFAOYSA-N 0.000 claims description 3
• CEFDJXPPCNJATN-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-piperidin-1-ylpropan-2-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN1CCCCC1 CEFDJXPPCNJATN-UHFFFAOYSA-N 0.000 claims description 3
• QTJYJMSQCUGYRB-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-pyrrolidin-1-ylpropan-2-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN1CCCC1 QTJYJMSQCUGYRB-UHFFFAOYSA-N 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000003287 1H-imidazol-4-ylmethyl group Chemical group [H]N1C([H])=NC(C([H])([H])[*])=C1[H] 0.000 claims description 3
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 3
• YQLCRRXQGXERBZ-UHFFFAOYSA-N 4-(6,7-dichloro-1h-imidazo[4,5-b]pyridin-2-yl)-n-(2-morpholin-4-ylethyl)aniline Chemical compound N=1C2=C(Cl)C(Cl)=CN=C2NC=1C(C=C1)=CC=C1NCCN1CCOCC1 YQLCRRXQGXERBZ-UHFFFAOYSA-N 0.000 claims description 3
• RXXAZAOOQHNXPX-UHFFFAOYSA-N 4-[2-[4-(6-chloro-7-methoxy-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]morpholine Chemical compound N=1C=2C(OC)=C(Cl)C=NC=2NC=1C(C=C1)=CC=C1OCCN1CCOCC1 RXXAZAOOQHNXPX-UHFFFAOYSA-N 0.000 claims description 3
• ORJAOCKIDKOPHY-UHFFFAOYSA-N 5-(6-chloro-7-methyl-1h-imidazo[4,5-b]pyridin-2-yl)-2-(4-methylpiperazin-1-yl)aniline Chemical compound C1CN(C)CCN1C1=CC=C(C=2NC3=NC=C(Cl)C(C)=C3N=2)C=C1N ORJAOCKIDKOPHY-UHFFFAOYSA-N 0.000 claims description 3
• LFJQIBWZHWLOGT-UHFFFAOYSA-N 6-bromo-2-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCCN1CCCC1 LFJQIBWZHWLOGT-UHFFFAOYSA-N 0.000 claims description 3
• YSVMAAIIFALTGL-UHFFFAOYSA-N 6-bromo-2-[4-[2-[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]ethoxy]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound ClC1=CC(C(F)(F)F)=CN=C1N1CCN(CCOC=2C=CC(=CC=2)C=2NC3=NC=C(Br)C=C3N=2)CC1 YSVMAAIIFALTGL-UHFFFAOYSA-N 0.000 claims description 3
• QBQUTQGXEHBFFO-UHFFFAOYSA-N 6-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-n-phenyl-1h-imidazo[4,5-b]pyridin-7-amine Chemical compound ClC1=CN=C2N=C(C=3C=CC(OCCN4CCOCC4)=CC=3)NC2=C1NC1=CC=CC=C1 QBQUTQGXEHBFFO-UHFFFAOYSA-N 0.000 claims description 3
• ANJGSAUNDPEGJJ-UHFFFAOYSA-N 6-chloro-n-(2-fluorophenyl)-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-amine Chemical compound FC1=CC=CC=C1NC1=C(Cl)C=NC2=C1N=C(C=1C=CC(OCCN3CCOCC3)=CC=1)N2 ANJGSAUNDPEGJJ-UHFFFAOYSA-N 0.000 claims description 3
• LSYCABNSFISCPY-UHFFFAOYSA-N 6-chloro-n-(3-ethylphenyl)-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-amine Chemical compound CCC1=CC=CC(NC=2C=3NC(=NC=3N=CC=2Cl)C=2C=CC(OCCN3CCOCC3)=CC=2)=C1 LSYCABNSFISCPY-UHFFFAOYSA-N 0.000 claims description 3
• YWSVZHHXLTVNBC-UHFFFAOYSA-N 6-chloro-n-(4-methylsulfonylphenyl)-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=C(Cl)C=NC2=C1NC(C=1C=CC(OCCN3CCOCC3)=CC=1)=N2 YWSVZHHXLTVNBC-UHFFFAOYSA-N 0.000 claims description 3
• REDLVGATARAVSA-UHFFFAOYSA-N 7-anilino-2-[4-[2-[2-methoxyethyl(methyl)amino]ethoxy]phenyl]-1h-imidazo[4,5-b]pyridine-6-carbonitrile Chemical compound C1=CC(OCCN(C)CCOC)=CC=C1C(NC1=NC=C2C#N)=NC1=C2NC1=CC=CC=C1 REDLVGATARAVSA-UHFFFAOYSA-N 0.000 claims description 3
• HGNNAMTXEXMNAL-UHFFFAOYSA-N ClC=1C(=C2C(=NC1)N=C(N2)C2=CC=C(C=C2)OCCN2CCOCC2)NC2=C(C=CC=C2)OC.ClC=2C(=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)OCCN1CCOCC1)Cl Chemical compound ClC=1C(=C2C(=NC1)N=C(N2)C2=CC=C(C=C2)OCCN2CCOCC2)NC2=C(C=CC=C2)OC.ClC=2C(=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)OCCN1CCOCC1)Cl HGNNAMTXEXMNAL-UHFFFAOYSA-N 0.000 claims description 3
• PZNKARPNXABWEQ-UHFFFAOYSA-N [3-[[6-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-yl]amino]phenyl]methanol Chemical compound OCC1=CC=CC(NC=2C=3N=C(NC=3N=CC=2Cl)C=2C=CC(OCCN3CCOCC3)=CC=2)=C1 PZNKARPNXABWEQ-UHFFFAOYSA-N 0.000 claims description 3
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 239000003795 chemical substances by application Substances 0.000 claims description 3
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
• 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims description 3
• HHGFLUSSFPHFPY-UHFFFAOYSA-N n-[1-[6-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-yl]pyrrolidin-3-yl]formamide Chemical compound ClC1=CN=C2N=C(C=3C=CC(OCCN4CCOCC4)=CC=3)NC2=C1N1CCC(NC=O)C1 HHGFLUSSFPHFPY-UHFFFAOYSA-N 0.000 claims description 3
• KJLUYTCAIKAYIM-UHFFFAOYSA-N n-[3-[6-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C=3N=C(NC=3N=CC=2Cl)C=2C=CC(OCCN3CCOCC3)=CC=2)=C1 KJLUYTCAIKAYIM-UHFFFAOYSA-N 0.000 claims description 3
• GXRFSBVSAUKTBR-UHFFFAOYSA-N n-[4-(6-bromo-7-methyl-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]-4-(2-cyanoethoxy)benzenesulfonamide Chemical compound N1C=2C(C)=C(Br)C=NC=2N=C1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(OCCC#N)C=C1 GXRFSBVSAUKTBR-UHFFFAOYSA-N 0.000 claims description 3
• ZDFVDUXGNJAWMH-UHFFFAOYSA-N n-benzyl-4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)aniline Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1NCC1=CC=CC=C1 ZDFVDUXGNJAWMH-UHFFFAOYSA-N 0.000 claims description 3
• 230000003287 optical effect Effects 0.000 claims description 3
• 239000007800 oxidant agent Substances 0.000 claims description 3
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
• AATVNHFGOQFNAZ-UHFFFAOYSA-N 1-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]-n,n-dimethylpyrrolidin-3-amine Chemical compound C1C(N(C)C)CCN1CCOC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 AATVNHFGOQFNAZ-UHFFFAOYSA-N 0.000 claims description 2
• WPRYBCGWQBDPQL-UHFFFAOYSA-N 1-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethylamino]propan-2-ol Chemical compound C1=CC(OCCNCC(O)C)=CC=C1C1=NC2=CC(Br)=CN=C2N1 WPRYBCGWQBDPQL-UHFFFAOYSA-N 0.000 claims description 2
• SGIZUJXDBSCNTD-UHFFFAOYSA-N 1-[2-[[3-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-2-hydroxypropyl]amino]ethyl]imidazolidin-2-one Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CNCCN1CCNC1=O SGIZUJXDBSCNTD-UHFFFAOYSA-N 0.000 claims description 2
• FRVGUTJAGGXEQH-UHFFFAOYSA-N 1-[3-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-2-hydroxypropyl]-4-phenylpiperidin-4-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN(CC1)CCC1(O)C1=CC=CC=C1 FRVGUTJAGGXEQH-UHFFFAOYSA-N 0.000 claims description 2
• VBKMXWUNMYJLFJ-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-(1,3-thiazol-2-ylamino)propan-2-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CNC1=NC=CS1 VBKMXWUNMYJLFJ-UHFFFAOYSA-N 0.000 claims description 2
• PCNWIJAUTHPDOB-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-(2-morpholin-4-ylethylamino)propan-2-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CNCCN1CCOCC1 PCNWIJAUTHPDOB-UHFFFAOYSA-N 0.000 claims description 2
• DKRZCPMSDRPUKY-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-(2-pyridin-3-ylpiperidin-1-yl)propan-2-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN1CCCCC1C1=CC=CN=C1 DKRZCPMSDRPUKY-UHFFFAOYSA-N 0.000 claims description 2
• KDXGEYZJCDCCQS-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-(cyclopropylamino)propan-2-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CNC1CC1 KDXGEYZJCDCCQS-UHFFFAOYSA-N 0.000 claims description 2
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• AMLDURGYWOQNQE-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-[4-(hydroxymethyl)piperidin-1-yl]propan-2-ol Chemical compound C1CC(CO)CCN1CC(O)COC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 AMLDURGYWOQNQE-UHFFFAOYSA-N 0.000 claims description 2
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• 125000004429 atom Chemical group 0.000 claims description 2
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