KR20060005333A - 특정의 신규한 이미다조피리딘 및 그의 용도 - Google Patents

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Publication number

KR20060005333A

KR20060005333A KR1020057002263A KR20057002263A KR20060005333A KR 20060005333 A KR20060005333 A KR 20060005333A KR 1020057002263 A KR1020057002263 A KR 1020057002263A KR 20057002263 A KR20057002263 A KR 20057002263A KR 20060005333 A KR20060005333 A KR 20060005333A

Authority

KR

South Korea

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Withdrawn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 356
• 239000000203 mixture Substances 0.000 claims abstract description 61
• 150000003839 salts Chemical class 0.000 claims abstract description 56
• 201000010099 disease Diseases 0.000 claims abstract description 35
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 35
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 30
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 20
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 20
• 238000011282 treatment Methods 0.000 claims abstract description 20
• 239000003814 drug Substances 0.000 claims abstract description 16
• 230000000694 effects Effects 0.000 claims abstract description 16
• 238000004519 manufacturing process Methods 0.000 claims abstract description 12
• 230000005764 inhibitory process Effects 0.000 claims abstract description 11
• 238000011321 prophylaxis Methods 0.000 claims abstract description 10
• 230000009286 beneficial effect Effects 0.000 claims abstract description 7
• -1 methoxyphenyl Chemical group 0.000 claims description 228
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 185
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 132
• 125000001072 heteroaryl group Chemical group 0.000 claims description 86
• 125000005842 heteroatom Chemical group 0.000 claims description 83
• 229910052736 halogen Inorganic materials 0.000 claims description 82
• 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
• 150000001412 amines Chemical class 0.000 claims description 76
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 74
• 229910052757 nitrogen Inorganic materials 0.000 claims description 68
• QREUAPHMIPBKSB-UHFFFAOYSA-N 4-[2-[4-(6,7-dichloro-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]morpholine Chemical compound N=1C2=C(Cl)C(Cl)=CN=C2NC=1C(C=C1)=CC=C1OCCN1CCOCC1 QREUAPHMIPBKSB-UHFFFAOYSA-N 0.000 claims description 65
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 55
• 238000000034 method Methods 0.000 claims description 55
• 125000000217 alkyl group Chemical group 0.000 claims description 51
• 229920006395 saturated elastomer Polymers 0.000 claims description 41
• 238000006243 chemical reaction Methods 0.000 claims description 32
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
• 125000001041 indolyl group Chemical group 0.000 claims description 30
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 29
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 27
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 23
• 229910052799 carbon Inorganic materials 0.000 claims description 22
• 125000001424 substituent group Chemical group 0.000 claims description 22
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 19
• 125000004076 pyridyl group Chemical group 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
• 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
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 14
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 14
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 12
• 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
• 125000001589 carboacyl group Chemical group 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 125000001309 chloro group Chemical group Cl* 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
• 125000003386 piperidinyl group Chemical group 0.000 claims description 9
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
• 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
• HGMKRZLUXLXGKO-UHFFFAOYSA-N 2-(4-aminophenyl)-6-chloro-n-phenyl-1h-imidazo[4,5-b]pyridin-7-amine Chemical compound C1=CC(N)=CC=C1C(NC1=NC=C2Cl)=NC1=C2NC1=CC=CC=C1 HGMKRZLUXLXGKO-UHFFFAOYSA-N 0.000 claims description 6
• 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
• GUKINAFDJCNOKF-UHFFFAOYSA-N 2-[benzyl-[6-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-yl]amino]ethanol Chemical compound ClC=1C=NC=2N=C(C=3C=CC(OCCN4CCOCC4)=CC=3)NC=2C=1N(CCO)CC1=CC=CC=C1 GUKINAFDJCNOKF-UHFFFAOYSA-N 0.000 claims description 6
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 6
• BWOOCQOEKQYBTE-UHFFFAOYSA-N 4-(6-bromo-7-methyl-1h-imidazo[4,5-b]pyridin-2-yl)aniline Chemical compound N1C=2C(C)=C(Br)C=NC=2N=C1C1=CC=C(N)C=C1 BWOOCQOEKQYBTE-UHFFFAOYSA-N 0.000 claims description 6
• SNZMUFNBBKAECJ-UHFFFAOYSA-N 4-[2-[4-(6,7-dichloro-1h-imidazo[4,5-b]pyridin-2-yl)-2-nitrophenoxy]ethyl]morpholine Chemical compound [O-][N+](=O)C1=CC(C=2NC3=C(Cl)C(Cl)=CN=C3N=2)=CC=C1OCCN1CCOCC1 SNZMUFNBBKAECJ-UHFFFAOYSA-N 0.000 claims description 6
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 6
• QUMPNVFDZNQPIX-UHFFFAOYSA-N 6-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-amine Chemical compound N1C=2C(N)=C(Cl)C=NC=2N=C1C(C=C1)=CC=C1OCCN1CCOCC1 QUMPNVFDZNQPIX-UHFFFAOYSA-N 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
• 239000004593 Epoxy Substances 0.000 claims description 5
• 206010039085 Rhinitis allergic Diseases 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
• 201000010105 allergic rhinitis Diseases 0.000 claims description 5
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 5
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 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 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
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
• 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 3
• DXRKECQKPDRDGO-UHFFFAOYSA-N 1-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCOC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 DXRKECQKPDRDGO-UHFFFAOYSA-N 0.000 claims description 3
• ZISQRLGGGPCFCX-UHFFFAOYSA-N 1-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]pyrrolidin-3-ol Chemical compound C1C(O)CCN1CCOC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 ZISQRLGGGPCFCX-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• FBGXXORWXFHNAC-UHFFFAOYSA-N 1-[3-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethylamino]propyl]pyrrolidin-2-one Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCNCCCN1CCCC1=O FBGXXORWXFHNAC-UHFFFAOYSA-N 0.000 claims description 3
• 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
• YJVVVSGGIJNPQZ-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-(diethylamino)propan-2-ol Chemical compound C1=CC(OCC(O)CN(CC)CC)=CC=C1C1=NC2=CC(Br)=CN=C2N1 YJVVVSGGIJNPQZ-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
• ZNMGJLKHJVHQKU-UHFFFAOYSA-N 1-[4-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCOC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 ZNMGJLKHJVHQKU-UHFFFAOYSA-N 0.000 claims description 3
• CZONLRTYELSYPW-UHFFFAOYSA-N 1-n-[6-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-yl]-4-n,4-n-diethylbenzene-1,4-diamine Chemical compound C1=CC(N(CC)CC)=CC=C1NC1=C(Cl)C=NC2=C1NC(C=1C=CC(OCCN3CCOCC3)=CC=1)=N2 CZONLRTYELSYPW-UHFFFAOYSA-N 0.000 claims description 3
• FZARSSDDUKIBLJ-UHFFFAOYSA-N 2-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethylamino]propan-1-ol Chemical compound C1=CC(OCCNC(CO)C)=CC=C1C1=NC2=CC(Br)=CN=C2N1 FZARSSDDUKIBLJ-UHFFFAOYSA-N 0.000 claims description 3
• FUDBLECKQUEVQP-UHFFFAOYSA-N 2-[[6-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-yl]amino]ethanol Chemical compound N1C=2C(NCCO)=C(Cl)C=NC=2N=C1C(C=C1)=CC=C1OCCN1CCOCC1 FUDBLECKQUEVQP-UHFFFAOYSA-N 0.000 claims description 3
• VTKQKSGLBXMDCD-UHFFFAOYSA-N 2-[[6-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-yl]amino]phenol Chemical compound OC1=CC=CC=C1NC1=C(Cl)C=NC2=C1NC(C=1C=CC(OCCN3CCOCC3)=CC=1)=N2 VTKQKSGLBXMDCD-UHFFFAOYSA-N 0.000 claims description 3
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
• YQBKRVPVCLINJJ-UHFFFAOYSA-N 3-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl-methylamino]propanenitrile Chemical compound C1=CC(OCCN(C)CCC#N)=CC=C1C1=NC2=CC(Br)=CN=C2N1 YQBKRVPVCLINJJ-UHFFFAOYSA-N 0.000 claims description 3
• OHJVBZCLUWFMAS-UHFFFAOYSA-N 3-[[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)anilino]methyl]benzonitrile Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1NCC1=CC=CC(C#N)=C1 OHJVBZCLUWFMAS-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
• XRVSYXLGKUEKAW-UHFFFAOYSA-N 4-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl-methylamino]cyclohexane-1-carbonitrile Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCCN(C)C1CCC(C#N)CC1 XRVSYXLGKUEKAW-UHFFFAOYSA-N 0.000 claims description 3
• WQZOKDIZFQILKX-UHFFFAOYSA-N 4-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethylamino]cyclohexan-1-ol Chemical compound C1CC(O)CCC1NCCOC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 WQZOKDIZFQILKX-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
• JJDVDAYTHAFKKJ-UHFFFAOYSA-N 4-[2-[4-(6-chloro-7-phenoxy-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]morpholine Chemical compound ClC1=CN=C2N=C(C=3C=CC(OCCN4CCOCC4)=CC=3)NC2=C1OC1=CC=CC=C1 JJDVDAYTHAFKKJ-UHFFFAOYSA-N 0.000 claims description 3
• KNIOJIRSCQWGGB-UHFFFAOYSA-N 4-[2-[4-(6-chloro-7-pyrrol-1-yl-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]morpholine Chemical compound ClC1=CN=C2N=C(C=3C=CC(OCCN4CCOCC4)=CC=3)NC2=C1N1C=CC=C1 KNIOJIRSCQWGGB-UHFFFAOYSA-N 0.000 claims description 3
• VJPLYMWICGUWAX-UHFFFAOYSA-N 4-[2-[4-(7-benzylsulfanyl-6-chloro-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]morpholine Chemical compound ClC1=CN=C2N=C(C=3C=CC(OCCN4CCOCC4)=CC=3)NC2=C1SCC1=CC=CC=C1 VJPLYMWICGUWAX-UHFFFAOYSA-N 0.000 claims description 3
• WHOGMXGOVZDSCZ-UHFFFAOYSA-N 4-[2-[4-[6-chloro-7-(2,3-dihydroindol-1-yl)-1h-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]morpholine Chemical compound N1C2=C(N3C4=CC=CC=C4CC3)C(Cl)=CN=C2N=C1C(C=C1)=CC=C1OCCN1CCOCC1 WHOGMXGOVZDSCZ-UHFFFAOYSA-N 0.000 claims description 3
• MEVPMQHLJLPVST-UHFFFAOYSA-N 4-[2-[4-[6-chloro-7-(2-pyrrolidin-1-ylethoxy)-1h-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]morpholine Chemical compound ClC1=CN=C2N=C(C=3C=CC(OCCN4CCOCC4)=CC=3)NC2=C1OCCN1CCCC1 MEVPMQHLJLPVST-UHFFFAOYSA-N 0.000 claims description 3
• IVGYDLUYWIQCGC-UHFFFAOYSA-N 4-[2-[4-[6-chloro-7-(3-methoxyphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]morpholine Chemical compound COC1=CC=CC(C=2C=3N=C(NC=3N=CC=2Cl)C=2C=CC(OCCN3CCOCC3)=CC=2)=C1 IVGYDLUYWIQCGC-UHFFFAOYSA-N 0.000 claims description 3
• MKDIXOUTQXWDIJ-UHFFFAOYSA-N 4-[6-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-yl]morpholine Chemical compound ClC1=CN=C2N=C(C=3C=CC(OCCN4CCOCC4)=CC=3)NC2=C1N1CCOCC1 MKDIXOUTQXWDIJ-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
• VZHNIBIDHAGTHT-GFCCVEGCSA-N 5-(6-chloro-7-methyl-1h-imidazo[4,5-b]pyridin-2-yl)-2-[[(2r)-pyrrolidin-2-yl]methylamino]phenol Chemical compound N=1C=2C(C)=C(Cl)C=NC=2NC=1C(C=C1O)=CC=C1NC[C@H]1CCCN1 VZHNIBIDHAGTHT-GFCCVEGCSA-N 0.000 claims description 3
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