JP2006503010A5 - - Google Patents
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- JP2006503010A5 JP2006503010A5 JP2004529004A JP2004529004A JP2006503010A5 JP 2006503010 A5 JP2006503010 A5 JP 2006503010A5 JP 2004529004 A JP2004529004 A JP 2004529004A JP 2004529004 A JP2004529004 A JP 2004529004A JP 2006503010 A5 JP2006503010 A5 JP 2006503010A5
- Authority
- JP
- Japan
- Prior art keywords
- imidazo
- pyridin
- bromo
- phenyl
- phenoxy
- Prior art date
- 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.)
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- -1 methoxyphenyl Chemical group 0.000 claims description 99
- 125000000217 alkyl group Chemical group 0.000 claims description 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
- 125000001072 heteroaryl group Chemical group 0.000 claims description 51
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 46
- 125000005842 heteroatom Chemical group 0.000 claims description 46
- 229910052760 oxygen Inorganic materials 0.000 claims description 46
- 229910052717 sulfur Inorganic materials 0.000 claims description 46
- 150000002367 halogens Chemical class 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 19
- 125000001041 indolyl group Chemical group 0.000 claims description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 239000004593 Epoxy Substances 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 26
- 150000001412 amines Chemical class 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
- 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 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- XOFXOXYZRJFXAA-UHFFFAOYSA-N 1-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(=CC=2)C=2NC3=NC=C(Br)C=C3N=2)CCC1(O)C1=CC=CC=C1 XOFXOXYZRJFXAA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- UUJHKACVKQWFNA-UHFFFAOYSA-N 1-[3-[[3-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-2-hydroxypropyl]amino]propyl]pyrrolidin-2-one Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CNCCCN1CCCC1=O UUJHKACVKQWFNA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- ZVWDFMPWYLNSBM-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-(pyridin-3-ylmethylamino)propan-2-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CNCC1=CC=CN=C1 ZVWDFMPWYLNSBM-UHFFFAOYSA-N 0.000 claims 1
- JMQGGIWFJJIZNK-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-(pyridin-4-ylmethylamino)propan-2-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CNCC1=CC=NC=C1 JMQGGIWFJJIZNK-UHFFFAOYSA-N 0.000 claims 1
- GLRMASZSUMHSJM-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-[(1-ethylpiperidin-3-yl)amino]propan-2-ol Chemical compound C1N(CC)CCCC1NCC(O)COC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 GLRMASZSUMHSJM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- IYQWHRBFNVYLHV-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-[2-hydroxyethyl(methyl)amino]propan-2-ol Chemical compound C1=CC(OCC(O)CN(CCO)C)=CC=C1C1=NC2=CC(Br)=CN=C2N1 IYQWHRBFNVYLHV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- OTXXKRHRGXTAKE-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-[methyl(2-phenylethyl)amino]propan-2-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN(C)CCC1=CC=CC=C1 OTXXKRHRGXTAKE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003287 1H-imidazol-4-ylmethyl group Chemical group [H]N1C([H])=NC(C([H])([H])[*])=C1[H] 0.000 claims 1
- 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 1
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 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 1
- 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 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 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 1
- 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 1
- SCMPKZNANUSIEJ-UHFFFAOYSA-N 4-(6-chloro-7-methyl-1h-imidazo[4,5-b]pyridin-2-yl)-1-n-(2-morpholin-4-ylethyl)benzene-1,2-diamine Chemical compound N=1C=2C(C)=C(Cl)C=NC=2NC=1C(C=C1N)=CC=C1NCCN1CCOCC1 SCMPKZNANUSIEJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- WVUAPIBWFHEWMI-UHFFFAOYSA-N 4-[2-[4-(6-chloro-7-pyrrolidin-1-yl-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]morpholine Chemical compound ClC1=CN=C2NC(C=3C=CC(OCCN4CCOCC4)=CC=3)=NC2=C1N1CCCC1 WVUAPIBWFHEWMI-UHFFFAOYSA-N 0.000 claims 1
- WQPNRHACZCAEHS-UHFFFAOYSA-N 4-[2-[4-(7-benzylsulfanyl-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]morpholine 6-chloro-N-methyl-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1H-imidazo[4,5-b]pyridin-7-amine Chemical compound C(C1=CC=CC=C1)SC1=C2C(=NC=C1Cl)N=C(N2)C2=CC=C(C=C2)OCCN2CCOCC2.ClC=2C(=C1C(=NC2)N=C(N1)C1=CC=C(C=C1)OCCN1CCOCC1)NC WQPNRHACZCAEHS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- RSYMBCFJZVPQTO-UHFFFAOYSA-N 4-[4-(6,7-dichloro-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]morpholine Chemical compound N1C2=C(Cl)C(Cl)=CN=C2N=C1C(C=C1)=CC=C1N1CCOCC1 RSYMBCFJZVPQTO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- YVHCOSCTWPGEBH-UHFFFAOYSA-N 4-[[3-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-2-hydroxypropyl]-methylamino]cyclohexane-1-carbonitrile Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN(C)C1CCC(C#N)CC1 YVHCOSCTWPGEBH-UHFFFAOYSA-N 0.000 claims 1
- RUWVZPKTGUZGMK-UHFFFAOYSA-N 4-[[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=C(C#N)C=C1 RUWVZPKTGUZGMK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- RPLRBNKLWIKWBK-UHFFFAOYSA-N 6-[4-[3-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-2-hydroxypropyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CN(CC1)CCN1C1=CC=C(C#N)C=N1 RPLRBNKLWIKWBK-UHFFFAOYSA-N 0.000 claims 1
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|---|---|---|---|---|
| AU2005226729B2 (en) | 2004-03-25 | 2010-01-28 | Janssen Pharmaceutica N.V. | Imidazole compounds |
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| US3985891A (en) | 1973-02-03 | 1976-10-12 | Boehringer Ingelheim Gmbh | 2-Phenyl-imidazo (4,5-b)pyridines and salts thereof |
| DE3037464A1 (de) | 1980-10-03 | 1982-05-19 | Dr. Karl Thomae Gmbh, 7950 Biberach | 6-hydroxy-2-phenyl-imidazo 4,5-b zu pyridine, ihre herstellung und diese sie enthaltende arzneimittel |
| US5296591A (en) * | 1990-12-31 | 1994-03-22 | Fujisawa Pharmaceutical Co., Ltd. | Trifluoromethylketone derivatives, processes for preparation thereof and use thereof |
| JP2004503553A (ja) * | 2000-06-14 | 2004-02-05 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | ６，５−縮合二環式複素環 |
| EP1347982B1 (en) * | 2000-12-12 | 2005-11-16 | Neurogen Corporation | Spiro isobenzofuran-1,4'-piperidin]-3-ones and 3h-spiroisobenzofuran-1,4'-piperidines |
-
2002
- 2002-08-14 SE SE0202462A patent/SE0202462D0/xx unknown
-
2003
- 2003-08-13 KR KR1020057002263A patent/KR20060005333A/ko not_active Withdrawn
- 2003-08-13 EP EP03788216A patent/EP1539759B1/en not_active Expired - Lifetime
- 2003-08-13 NZ NZ538156A patent/NZ538156A/en unknown
- 2003-08-13 CN CNB03823193XA patent/CN100358893C/zh not_active Expired - Fee Related
- 2003-08-13 ES ES03788216T patent/ES2290538T3/es not_active Expired - Lifetime
- 2003-08-13 DE DE60315674T patent/DE60315674T2/de not_active Expired - Fee Related
- 2003-08-13 AU AU2003251272A patent/AU2003251272A1/en not_active Abandoned
- 2003-08-13 MX MXPA05001581A patent/MXPA05001581A/es unknown
- 2003-08-13 CA CA002495511A patent/CA2495511A1/en not_active Abandoned
- 2003-08-13 US US10/524,204 patent/US7410966B2/en not_active Expired - Fee Related
- 2003-08-13 BR BR0313461-0A patent/BR0313461A/pt not_active IP Right Cessation
- 2003-08-13 AT AT03788216T patent/ATE370138T1/de not_active IP Right Cessation
- 2003-08-13 WO PCT/SE2003/001279 patent/WO2004016611A1/en not_active Ceased
- 2003-08-13 JP JP2004529004A patent/JP2006503010A/ja not_active Withdrawn
-
2005
- 2005-01-20 IL IL16641305A patent/IL166413A0/xx unknown
- 2005-01-31 ZA ZA200500887A patent/ZA200500887B/xx unknown
- 2005-03-11 NO NO20051265A patent/NO20051265L/no not_active Application Discontinuation
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