DE60315674T2 - Neue imidazopyridine und ihre verwendung - Google Patents

Info

Publication number

DE60315674T2

DE60315674T2 DE60315674T DE60315674T DE60315674T2 DE 60315674 T2 DE60315674 T2 DE 60315674T2 DE 60315674 T DE60315674 T DE 60315674T DE 60315674 T DE60315674 T DE 60315674T DE 60315674 T2 DE60315674 T2 DE 60315674T2

Authority

DE

Germany

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.)

Expired - Fee Related

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• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 361
• 150000003839 salts Chemical class 0.000 claims abstract description 57
• 201000010099 disease Diseases 0.000 claims abstract description 35
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 35
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 20
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 20
• 238000000034 method Methods 0.000 claims abstract description 19
• 239000003814 drug Substances 0.000 claims abstract description 18
• 238000011282 treatment Methods 0.000 claims abstract description 16
• 230000000694 effects Effects 0.000 claims abstract description 14
• 230000008569 process Effects 0.000 claims abstract description 11
• 238000002360 preparation method Methods 0.000 claims abstract description 10
• 238000011321 prophylaxis Methods 0.000 claims abstract description 10
• 238000004519 manufacturing process Methods 0.000 claims abstract description 9
• 230000005764 inhibitory process Effects 0.000 claims abstract description 8
• -1 6-Bromo-3 H -imidazo [4,5-b] pyridin-2-yl Chemical group 0.000 claims description 351
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 167
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 126
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 121
• 150000001412 amines Chemical class 0.000 claims description 97
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 89
• 125000000217 alkyl group Chemical group 0.000 claims description 84
• 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
• 229910052760 oxygen Inorganic materials 0.000 claims description 55
• 125000001072 heteroaryl group Chemical group 0.000 claims description 53
• 125000005842 heteroatom Chemical group 0.000 claims description 53
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
• 229910052757 nitrogen Inorganic materials 0.000 claims description 48
• 229910052717 sulfur Inorganic materials 0.000 claims description 48
• 229910052736 halogen Inorganic materials 0.000 claims description 45
• 150000002367 halogens Chemical group 0.000 claims description 45
• 229910052799 carbon Inorganic materials 0.000 claims description 38
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims description 33
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 32
• 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 29
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• 229920006395 saturated elastomer Polymers 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 28
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 27
• 125000001041 indolyl group Chemical group 0.000 claims description 20
• 208000006673 asthma Diseases 0.000 claims description 19
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 18
• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 15
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 claims description 15
• 239000000460 chlorine Substances 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 14
• 125000004076 pyridyl group Chemical group 0.000 claims description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 125000000335 thiazolyl group Chemical group 0.000 claims description 11
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
• 210000003630 histaminocyte Anatomy 0.000 claims description 9
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 8
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 8
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 125000001425 triazolyl group Chemical group 0.000 claims description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 claims description 7
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 7
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 6
• ULLOAXQMXSOFLT-UHFFFAOYSA-N 2-amino-5-(6-chloro-7-methyl-1h-imidazo[4,5-b]pyridin-2-yl)phenol Chemical compound N=1C=2C(C)=C(Cl)C=NC=2NC=1C1=CC=C(N)C(O)=C1 ULLOAXQMXSOFLT-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
• 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
• 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 6
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 6
• 125000003386 piperidinyl 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
• GRRIMVWABNHKBX-UHFFFAOYSA-N (3-methoxyphenyl)methanamine Chemical compound COC1=CC=CC(CN)=C1 GRRIMVWABNHKBX-UHFFFAOYSA-N 0.000 claims description 5
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 5
• 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 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 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
• 125000001589 carboacyl group Chemical group 0.000 claims description 5
• 229940079593 drug Drugs 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
• YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 5
• PXJACNDVRNAFHD-UHFFFAOYSA-N (2-methoxyphenyl)methanamine Chemical compound COC1=CC=CC=C1CN PXJACNDVRNAFHD-UHFFFAOYSA-N 0.000 claims description 4
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 claims description 4
• GLUWOZCDSYAXCB-UHFFFAOYSA-N 6-bromo-2-[4-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethoxy]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=CC=C1N1CCN(CCOC=2C=CC(=CC=2)C=2NC3=NC=C(Br)C=C3N=2)CC1 GLUWOZCDSYAXCB-UHFFFAOYSA-N 0.000 claims description 4
• FZTGUNDGNSUAEM-UHFFFAOYSA-N 6-bromo-7-methyl-2-(4-nitrophenyl)-1h-imidazo[4,5-b]pyridine Chemical compound N1C=2C(C)=C(Br)C=NC=2N=C1C1=CC=C([N+]([O-])=O)C=C1 FZTGUNDGNSUAEM-UHFFFAOYSA-N 0.000 claims description 4
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
• SASNBVQSOZSTPD-UHFFFAOYSA-N n-methylphenethylamine Chemical compound CNCCC1=CC=CC=C1 SASNBVQSOZSTPD-UHFFFAOYSA-N 0.000 claims description 4
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 4
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
• HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 claims description 4
• TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 claims description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000001113 thiadiazolyl group Chemical group 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
• UVFOQCOVJMTDHO-UHFFFAOYSA-N 1-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]piperidin-3-ol Chemical compound C1C(O)CCCN1CCOC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 UVFOQCOVJMTDHO-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
• 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 3
• XRRXYCPDSISAKX-UHFFFAOYSA-N 1-[3-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-2-hydroxypropyl]piperidin-3-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN1CCCC(O)C1 XRRXYCPDSISAKX-UHFFFAOYSA-N 0.000 claims description 3
• CREAJNYSPKVFRR-UHFFFAOYSA-N 1-[3-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-2-hydroxypropyl]piperidin-4-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN1CCC(O)CC1 CREAJNYSPKVFRR-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
• YYBGWSSXRSEVEK-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-(1-hydroxypropan-2-ylamino)propan-2-ol Chemical compound C1=CC(OCC(O)CNC(CO)C)=CC=C1C1=NC2=CC(Br)=CN=C2N1 YYBGWSSXRSEVEK-UHFFFAOYSA-N 0.000 claims description 3
• PRHMLBRBXTXRCQ-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-(2-hydroxypropylamino)propan-2-ol Chemical compound C1=CC(OCC(O)CNCC(O)C)=CC=C1C1=NC2=CC(Br)=CN=C2N1 PRHMLBRBXTXRCQ-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• CQJZCNHAEFJZQN-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-(4-hydroxypiperazin-1-yl)propan-2-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN1CCN(O)CC1 CQJZCNHAEFJZQN-UHFFFAOYSA-N 0.000 claims description 3
• LWMVGOUQVKBUJY-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-(4-pyrazin-2-ylpiperazin-1-yl)propan-2-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN(CC1)CCN1C1=CN=CC=N1 LWMVGOUQVKBUJY-UHFFFAOYSA-N 0.000 claims description 3
• GGSSNJUKJOAUPB-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-(4-pyridin-2-ylpiperazin-1-yl)propan-2-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN(CC1)CCN1C1=CC=CC=N1 GGSSNJUKJOAUPB-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
• SEIDDLKXHXRNFT-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-[2-(hydroxymethyl)piperidin-1-yl]propan-2-ol Chemical compound OCC1CCCCN1CC(O)COC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 SEIDDLKXHXRNFT-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
• ATFBAZBERICHMA-UHFFFAOYSA-N 1-[benzyl(methyl)amino]-3-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]propan-2-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN(C)CC1=CC=CC=C1 ATFBAZBERICHMA-UHFFFAOYSA-N 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
• KEUWLKYTGAIQPK-UHFFFAOYSA-N 2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridine-6,7-dicarbonitrile Chemical compound N=1C2=C(C#N)C(C#N)=CN=C2NC=1C(C=C1)=CC=C1OCCN1CCOCC1 KEUWLKYTGAIQPK-UHFFFAOYSA-N 0.000 claims description 3
• SJMCFPBDLIPYIT-UHFFFAOYSA-N 2-[4-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]piperazin-1-yl]benzonitrile Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCN(CC1)CCN1C1=CC=CC=C1C#N SJMCFPBDLIPYIT-UHFFFAOYSA-N 0.000 claims description 3
• OXFUYIAWQXPBCA-UHFFFAOYSA-N 2-[4-[3-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-2-hydroxypropyl]piperazin-1-yl]benzonitrile Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN(CC1)CCN1C1=CC=CC=C1C#N OXFUYIAWQXPBCA-UHFFFAOYSA-N 0.000 claims description 3
• IUNXRUVRQUDTPL-UHFFFAOYSA-N 2-[[3-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-2-hydroxypropyl]amino]-3-methylbutan-1-ol Chemical compound C1=CC(OCC(O)CNC(CO)C(C)C)=CC=C1C1=NC2=CC(Br)=CN=C2N1 IUNXRUVRQUDTPL-UHFFFAOYSA-N 0.000 claims description 3
• FUIYBQFBGDTJSR-UHFFFAOYSA-N 3-[[3-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-2-hydroxypropyl]-methylamino]propanenitrile Chemical compound C1=CC(OCC(O)CN(CCC#N)C)=CC=C1C1=NC2=CC(Br)=CN=C2N1 FUIYBQFBGDTJSR-UHFFFAOYSA-N 0.000 claims description 3
• PYXORGTWETYHTI-UHFFFAOYSA-N 4-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)-2-nitrophenoxy]ethyl]morpholine Chemical compound [O-][N+](=O)C1=CC(C=2NC3=NC=C(Br)C=C3N=2)=CC=C1OCCN1CCOCC1 PYXORGTWETYHTI-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
• 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
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