KR20060005333A - 특정의 신규한 이미다조피리딘 및 그의 용도 - Google Patents
특정의 신규한 이미다조피리딘 및 그의 용도 Download PDFInfo
- 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
- 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- Withdrawn
Links
- 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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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4162—1,2-Diazoles condensed with heterocyclic ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0202462-8 | 2002-08-14 | ||
| SE0202462A SE0202462D0 (sv) | 2002-08-14 | 2002-08-14 | Novel use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20060005333A true KR20060005333A (ko) | 2006-01-17 |
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Family Applications (1)
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| EP (1) | EP1539759B1 (enExample) |
| JP (1) | JP2006503010A (enExample) |
| KR (1) | KR20060005333A (enExample) |
| CN (1) | CN100358893C (enExample) |
| AT (1) | ATE370138T1 (enExample) |
| AU (1) | AU2003251272A1 (enExample) |
| BR (1) | BR0313461A (enExample) |
| CA (1) | CA2495511A1 (enExample) |
| DE (1) | DE60315674T2 (enExample) |
| ES (1) | ES2290538T3 (enExample) |
| IL (1) | IL166413A0 (enExample) |
| MX (1) | MXPA05001581A (enExample) |
| NO (1) | NO20051265L (enExample) |
| NZ (1) | NZ538156A (enExample) |
| SE (1) | SE0202462D0 (enExample) |
| WO (1) | WO2004016611A1 (enExample) |
| ZA (1) | ZA200500887B (enExample) |
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| MXPA06011021A (es) * | 2004-03-25 | 2007-04-13 | Johnson & Johnson | Compuestos de imidazol. |
| US7714130B2 (en) | 2004-06-17 | 2010-05-11 | Wyeth | Processes for preparing gonadotropin releasing hormone receptor antagonists |
| CN101006078A (zh) | 2004-06-17 | 2007-07-25 | 惠氏公司 | 促性腺素释放激素受体拮抗剂 |
| US7799778B1 (en) * | 2005-01-12 | 2010-09-21 | Alcon, Inc. | 5-substituted 2-aminopyridine analogs for treating allergic and inflammatory diseases |
| KR20060087386A (ko) | 2005-01-28 | 2006-08-02 | 주식회사 대웅제약 | 신규 벤조이미다졸 유도체 및 이를 함유하는 약제학적조성물 |
| US7538113B2 (en) | 2005-02-18 | 2009-05-26 | Wyeth | 4-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7582634B2 (en) | 2005-02-18 | 2009-09-01 | Wyeth | 7-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7534796B2 (en) | 2005-02-18 | 2009-05-19 | Wyeth | Imidazo[4,5-b]pyridine antagonists of gonadotropin releasing hormone receptor |
| US7531542B2 (en) | 2005-05-18 | 2009-05-12 | Wyeth | Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor |
| US7582636B2 (en) | 2005-05-26 | 2009-09-01 | Wyeth | Piperazinylimidazopyridine and piperazinyltriazolopyridine antagonists of Gonadotropin Releasing Hormone receptor |
| EP1910358A2 (en) * | 2005-07-14 | 2008-04-16 | Astellas Pharma Inc. | Heterocyclic janus kinase 3 inhibitors |
| CN101208339B (zh) | 2005-08-01 | 2010-12-29 | 霍夫曼-拉罗奇有限公司 | 杂环苄基氨基衍生物，它们的制备以及作为药剂的应用 |
| BRPI0503681A (pt) | 2005-08-19 | 2007-04-10 | Fundacao Oswaldo Cruz | compostos azóis usados como agentes tuberculostáticos e leishmanicidas, composições farmacêuticas contendo os mesmos, uso das respectivas composições farmacêuticas no tratamento ou inibição de doenças, bem como método de tratamento ou inibição de doenças |
| AR057525A1 (es) * | 2005-10-03 | 2007-12-05 | Astrazeneca Ab | Compuestos inhibidores selectivos de gsk3 y un proceso para su preparacion |
| AR055669A1 (es) * | 2005-10-03 | 2007-08-29 | Astrazeneca Ab | Derivados de 3h - imidazo[4, 5 -b]piridina como inhibidores selectivos de gsk3, metodos e internediarios para su preparacion, composiciones farmaceuticas que los contienen y su uso para la elaboracion de un medicamento para el tratamiento de enfermedades neurodegenerativas y mentales. |
| EP1954287B2 (en) † | 2005-10-31 | 2016-02-24 | Merck Sharp & Dohme Corp. | Cetp inhibitors |
| US8088761B2 (en) | 2005-12-22 | 2012-01-03 | Cancer Research Technology Limited | Enzyme inhibitors |
| CA2637392A1 (en) * | 2006-01-23 | 2007-07-26 | Crystalgenomics, Inc. | Imidazopyridine derivatives inhibiting protein kinase activity, method for the preparation thereof and pharmaceutical composition containing same |
| ITMI20061581A1 (it) * | 2006-08-04 | 2008-02-05 | Univ Bari | Ligandi del recettore beta-3 adrenergico e loro uso in terapia |
| US8153792B2 (en) * | 2007-02-13 | 2012-04-10 | Ab Science | Process for the synthesis of 2-aminothiazole compounds as kinase inhibitors |
| WO2008121063A1 (en) * | 2007-03-30 | 2008-10-09 | Astrazeneca Ab | New imidazo[ 4,5-b]pyridine-7-carboxamides 704 |
| WO2008121064A1 (en) * | 2007-03-30 | 2008-10-09 | Astrazeneca Ab | New imidazo[4,5-b]pyridine-6-halo-7-aryl/heteroaryl compounds 705 |
| WO2009001021A1 (en) * | 2007-06-26 | 2008-12-31 | Chroma Therapeutics Ltd. | Imidazopyridine derivatives useful as enzyme inhibitors for the treatment of cell proliferative and autoimmune diseases |
| CN102264745B (zh) * | 2008-11-10 | 2015-07-22 | 财团法人卫生研究院 | 作为酪胺酸激酶抑制剂的稠合双环及多环嘧啶化合物 |
| TWI461425B (zh) * | 2009-02-19 | 2014-11-21 | Janssen Pharmaceuticals Inc | 作為伽瑪分泌酶調節劑之新穎經取代的苯并唑、苯并咪唑、唑并吡啶及咪唑并吡啶衍生物類 |
| AU2011308256B2 (en) * | 2010-09-28 | 2015-08-20 | Daewoong Pharmaceutical Co., Ltd. | Novel method of preparing benzoimidazole derivatives |
| WO2013116291A1 (en) * | 2012-01-30 | 2013-08-08 | Cephalon, Inc. | Imidazo [4, 5 - b] pyridine derivatives as alk and jak modulators for the treatment of proliferative disorders |
| WO2013153539A1 (en) | 2012-04-13 | 2013-10-17 | Glenmark Pharmaceuticals S.A. | Tricyclic compounds as tec kinase inhibitors |
| CN103724331A (zh) * | 2012-10-11 | 2014-04-16 | 韩冰 | 一类治疗脑性瘫痪的化合物及其用途 |
| CN103800328A (zh) * | 2012-11-07 | 2014-05-21 | 韩冰 | 一类治疗神经退行性疾病的化合物及其用途 |
| GB201302927D0 (en) | 2013-02-20 | 2013-04-03 | Cancer Therapeutics Crc Pty Ltd | Compounds |
| WO2014175370A1 (ja) * | 2013-04-25 | 2014-10-30 | 塩野義製薬株式会社 | ピロリジン誘導体およびそれらを含有する医薬組成物 |
| MX392373B (es) | 2013-10-25 | 2025-03-24 | Pharmacyclics Llc | Uso de ibrutinib en el tratamiento de enfermedad injerto contra huesped cronica |
| WO2016034673A1 (en) | 2014-09-03 | 2016-03-10 | Ctxt Pty Ltd | Tetrahydroisoquinoline derived prmt5-inhibitors |
| US10005792B2 (en) | 2014-09-03 | 2018-06-26 | Ctxt Pty. Ltd. | Aminoindane-, aminotetrahydronaphthalene- and aminobenzocyclobutane-derived PRMT5-inhibitors |
| GB201415573D0 (en) | 2014-09-03 | 2014-10-15 | Cancer Therapeutics Crc Pty Ltd | Compounds |
| BR112017016428B1 (pt) | 2015-02-02 | 2023-10-24 | Kancera Ab | Composto ou sal farmaceuticamente aceitável, composição farmacêutica, e, uso de um composto ou sal farmaceuticamente aceitável |
| CN108135904A (zh) | 2015-08-31 | 2018-06-08 | 药品循环有限责任公司 | 用于治疗多发性骨髓瘤的btk抑制剂组合 |
| GB201604031D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
| GB201604022D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
| GB201604030D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
| GB201604027D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
| GB201604029D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
| GB201604020D0 (en) | 2016-03-09 | 2016-04-20 | Ctxt Pty Ltd | Compounds |
| CN109563092B (zh) * | 2016-07-11 | 2021-09-14 | 坎塞拉有限公司 | 可用作哺乳动物酪氨酸激酶ror1活性的抑制剂的2-苯基咪唑并[4,5-b]吡啶-7-胺衍生物 |
| US11660303B2 (en) | 2016-07-11 | 2023-05-30 | Kancera Ab | 2-phenylimidazo[4,5-b]pyridin-7-amine derivates useful as inhibitors of mammalian tyrosine kinase ROR1 activity |
| WO2018085731A2 (en) | 2016-11-03 | 2018-05-11 | Juno Therapeutics, Inc. | Combination therapy of a t cell therapy and a btk inhibitor |
| EP3787751A1 (en) | 2018-05-03 | 2021-03-10 | Juno Therapeutics, Inc. | Combination therapy of a chimeric antigen receptor (car) t cell therapy and a kinase inhibitor |
| BR112022016400A2 (pt) | 2020-02-18 | 2022-10-25 | Bayer Ag | Compostos inovadores de heteroaril-triazol como pesticidas |
| CN113582988B (zh) * | 2020-04-30 | 2025-09-09 | 正大天晴药业集团股份有限公司 | 吡啶并环类化合物及其医药用途 |
| WO2023220655A1 (en) | 2022-05-11 | 2023-11-16 | Celgene Corporation | Methods to overcome drug resistance by re-sensitizing cancer cells to treatment with a prior therapy via treatment with a t cell therapy |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2001096336A2 (en) * | 2000-06-14 | 2001-12-20 | Warner-Lambert Company | 6,5-fused bicyclic heterocycles |
| AU2002220276A1 (en) * | 2000-12-12 | 2002-06-24 | 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 WO PCT/SE2003/001279 patent/WO2004016611A1/en not_active Ceased
- 2003-08-13 NZ NZ538156A patent/NZ538156A/en unknown
- 2003-08-13 AT AT03788216T patent/ATE370138T1/de not_active IP Right Cessation
- 2003-08-13 BR BR0313461-0A patent/BR0313461A/pt not_active IP Right Cessation
- 2003-08-13 JP JP2004529004A patent/JP2006503010A/ja not_active Withdrawn
- 2003-08-13 AU AU2003251272A patent/AU2003251272A1/en not_active Abandoned
- 2003-08-13 US US10/524,204 patent/US7410966B2/en not_active Expired - Fee Related
- 2003-08-13 ES ES03788216T patent/ES2290538T3/es not_active Expired - Lifetime
- 2003-08-13 CA CA002495511A patent/CA2495511A1/en not_active Abandoned
- 2003-08-13 KR KR1020057002263A patent/KR20060005333A/ko not_active Withdrawn
- 2003-08-13 DE DE60315674T patent/DE60315674T2/de not_active Expired - Fee Related
- 2003-08-13 CN CNB03823193XA patent/CN100358893C/zh not_active Expired - Fee Related
- 2003-08-13 MX MXPA05001581A patent/MXPA05001581A/es unknown
- 2003-08-13 EP EP03788216A patent/EP1539759B1/en not_active Expired - Lifetime
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| ES2290538T3 (es) | 2008-02-16 |
| BR0313461A (pt) | 2005-07-05 |
| DE60315674T2 (de) | 2008-06-19 |
| ZA200500887B (en) | 2006-02-22 |
| US20050261333A1 (en) | 2005-11-24 |
| SE0202462D0 (sv) | 2002-08-14 |
| CA2495511A1 (en) | 2004-02-26 |
| US7410966B2 (en) | 2008-08-12 |
| EP1539759B1 (en) | 2007-08-15 |
| NO20051265L (no) | 2005-05-12 |
| EP1539759A1 (en) | 2005-06-15 |
| ATE370138T1 (de) | 2007-09-15 |
| JP2006503010A (ja) | 2006-01-26 |
| WO2004016611A1 (en) | 2004-02-26 |
| DE60315674D1 (de) | 2007-09-27 |
| AU2003251272A1 (en) | 2004-03-03 |
| MXPA05001581A (es) | 2005-04-25 |
| CN100358893C (zh) | 2008-01-02 |
| CN1684964A (zh) | 2005-10-19 |
| IL166413A0 (en) | 2006-01-15 |
| NZ538156A (en) | 2006-09-29 |
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