CA2495511A1 - Use of and some novel imidazopyridines - Google Patents

Info

Publication number

CA2495511A1

CA2495511A1 CA002495511A CA2495511A CA2495511A1 CA 2495511 A1 CA2495511 A1 CA 2495511A1 CA 002495511 A CA002495511 A CA 002495511A CA 2495511 A CA2495511 A CA 2495511A CA 2495511 A1 CA2495511 A1 CA 2495511A1

Authority

CA

Canada

Prior art keywords

imidazo

bromo

pyridin

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000005232 imidazopyridines Chemical class 0.000 title description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 364
• 150000003839 salts Chemical class 0.000 claims abstract description 57
• 238000000034 method Methods 0.000 claims abstract description 52
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 35
• 201000010099 disease Diseases 0.000 claims abstract description 34
• 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 19
• 239000003814 drug Substances 0.000 claims abstract description 17
• 230000000694 effects Effects 0.000 claims abstract description 14
• 230000008569 process Effects 0.000 claims abstract description 12
• 238000011321 prophylaxis Methods 0.000 claims abstract description 12
• 230000005764 inhibitory process Effects 0.000 claims abstract description 11
• 238000002360 preparation method Methods 0.000 claims abstract description 11
• 238000004519 manufacturing process Methods 0.000 claims abstract description 10
• 230000009286 beneficial effect Effects 0.000 claims abstract description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 150
• 125000000217 alkyl group Chemical group 0.000 claims description 147
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 125
• -1 methoxyphenyl Chemical group 0.000 claims description 99
• 125000001072 heteroaryl group Chemical group 0.000 claims description 83
• 229910052736 halogen Inorganic materials 0.000 claims description 82
• 125000005842 heteroatom Chemical group 0.000 claims description 82
• 229910052760 oxygen Inorganic materials 0.000 claims description 77
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 77
• 150000002367 halogens Chemical class 0.000 claims description 70
• 229910052757 nitrogen Inorganic materials 0.000 claims description 68
• 229910052717 sulfur Inorganic materials 0.000 claims description 54
• 125000003545 alkoxy group Chemical group 0.000 claims description 47
• 229920006395 saturated elastomer Polymers 0.000 claims description 41
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
• 238000006243 chemical reaction Methods 0.000 claims description 33
• 150000001412 amines Chemical class 0.000 claims description 32
• 125000001041 indolyl group Chemical group 0.000 claims description 29
• 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
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
• 125000001424 substituent group Chemical group 0.000 claims description 22
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 18
• 125000004076 pyridyl group Chemical group 0.000 claims description 18
• 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
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 14
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 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
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 125000001589 carboacyl group Chemical group 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
• 208000006673 asthma Diseases 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 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
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
• 239000004593 Epoxy Substances 0.000 claims description 5
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
• 229910019213 POCl3 Inorganic materials 0.000 claims description 4
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
• 201000010105 allergic rhinitis Diseases 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=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
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-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
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 3
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
• MEKQYJWMCICGAG-SRVKJERBSA-N (1S,2S)-2-[2-[4-(6-bromo-1H-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethylamino]cyclohexan-1-ol 6-bromo-2-[4-[2-(4-pyrazin-2-ylpiperazin-1-yl)ethoxy]phenyl]-1H-imidazo[4,5-b]pyridine Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCN[C@@H]1[C@H](CCCC1)O)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)OCCN1CCN(CC1)C1=NC=CN=C1 MEKQYJWMCICGAG-SRVKJERBSA-N 0.000 claims description 2
• 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 2
• YZHBSLHIRAFDFN-UHFFFAOYSA-N 3-[[4-(6-chloro-7-methoxy-1h-imidazo[4,5-b]pyridin-2-yl)anilino]methyl]benzonitrile Chemical compound N1C=2C(OC)=C(Cl)C=NC=2N=C1C(C=C1)=CC=C1NCC1=CC=CC(C#N)=C1 YZHBSLHIRAFDFN-UHFFFAOYSA-N 0.000 claims description 2
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 2
• 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 2
• FOXIBDPJZKCGLH-GOSISDBHSA-N 5-(6-chloro-7-methyl-1h-imidazo[4,5-b]pyridin-2-yl)-2-(2-morpholin-4-ylethoxy)-n-[[(2r)-pyrrolidin-2-yl]methyl]aniline Chemical compound N=1C=2C(C)=C(Cl)C=NC=2NC=1C(C=C1NC[C@@H]2NCCC2)=CC=C1OCCN1CCOCC1 FOXIBDPJZKCGLH-GOSISDBHSA-N 0.000 claims description 2
• 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 2
• BUZYLPBAQPTBJM-UHFFFAOYSA-N 6-chloro-n-(1-methylsulfonylpyrrolidin-3-yl)-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-amine Chemical compound C1N(S(=O)(=O)C)CCC1NC1=C(Cl)C=NC2=C1NC(C=1C=CC(OCCN3CCOCC3)=CC=1)=N2 BUZYLPBAQPTBJM-UHFFFAOYSA-N 0.000 claims description 2
• SJZGYUZAVWGQHY-UHFFFAOYSA-N BrC=1C(=C2C(=NC1)N=C(N2)C2=CC=C(C=C2)NS(=O)(=O)C=2N=CN(C2)C)C.BrC=2C(=C1C(=NC2)N=C(N1)C1=CC=C(C=C1)NS(=O)(=O)C1=CC=C(C=C1)OCCC#N)C Chemical compound BrC=1C(=C2C(=NC1)N=C(N2)C2=CC=C(C=C2)NS(=O)(=O)C=2N=CN(C2)C)C.BrC=2C(=C1C(=NC2)N=C(N1)C1=CC=C(C=C1)NS(=O)(=O)C1=CC=C(C=C1)OCCC#N)C SJZGYUZAVWGQHY-UHFFFAOYSA-N 0.000 claims description 2
• LSQYOOPAWMHNNC-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)NCC2=CC(=CC=C2)OC.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)NCC1=C(C=CC=C1)OC Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)NCC2=CC(=CC=C2)OC.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)NCC1=C(C=CC=C1)OC LSQYOOPAWMHNNC-UHFFFAOYSA-N 0.000 claims description 2
• VQCUYKCYCAOSPT-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)NCC2=CC=C(C=C2)Cl.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)NCC1=C(C=CC=C1)Cl Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)NCC2=CC=C(C=C2)Cl.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)NCC1=C(C=CC=C1)Cl VQCUYKCYCAOSPT-UHFFFAOYSA-N 0.000 claims description 2
• ZEMUHYLWEODVSC-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)NCC2=CN=CN2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)NCC=1NC=CN1 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)NCC2=CN=CN2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)NCC=1NC=CN1 ZEMUHYLWEODVSC-UHFFFAOYSA-N 0.000 claims description 2
• ZPLUOYFPJKSYIS-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCN(CCOC)CCOC)C=C2.C(C)(=O)N2CCN(CC2)CCOC2=CC=C(C=C2)C2=NC=1C(=NC=C(C1)Br)N2 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCN(CCOC)CCOC)C=C2.C(C)(=O)N2CCN(CC2)CCOC2=CC=C(C=C2)C2=NC=1C(=NC=C(C1)Br)N2 ZPLUOYFPJKSYIS-UHFFFAOYSA-N 0.000 claims description 2
• XESZNJJUBOMVMD-UHFFFAOYSA-N C(C1=CC=CC=C1)NC1=NC=C(C=C1)C1=NC=2C(=NC=C(C2)Br)N1.BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)NCC=2C=C(N(C2)C)C(=O)OC Chemical compound C(C1=CC=CC=C1)NC1=NC=C(C=C1)C1=NC=2C(=NC=C(C2)Br)N1.BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)NCC=2C=C(N(C2)C)C(=O)OC XESZNJJUBOMVMD-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• NMWYWGOOOCHTRL-UHFFFAOYSA-N ClC=1C(=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)OCCN2CCCCC2)OC.ClC=2C(=C1C(=NC2)N=C(N1)C1=CC=C(C=C1)NS(=O)(=O)C1=CC=C(C=C1)C#N)OC Chemical compound ClC=1C(=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)OCCN2CCCCC2)OC.ClC=2C(=C1C(=NC2)N=C(N1)C1=CC=C(C=C1)NS(=O)(=O)C1=CC=C(C=C1)C#N)OC NMWYWGOOOCHTRL-UHFFFAOYSA-N 0.000 claims description 2
• OXCHCDKFBODTNK-UHFFFAOYSA-N ClC=1C(=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)OCCN2CCOCC2)N2CCCC2.ClC=2C(=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)OCCN1CCOCC1)NCCN1CCOCC1 Chemical compound ClC=1C(=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)OCCN2CCOCC2)N2CCCC2.ClC=2C(=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)OCCN1CCOCC1)NCCN1CCOCC1 OXCHCDKFBODTNK-UHFFFAOYSA-N 0.000 claims description 2
• VPZONHBYECNKPC-UHFFFAOYSA-N N-[2-[4-(6-bromo-1H-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]cyclopentanamine 6-bromo-2-[4-[2-(2-pyridin-3-ylpiperidin-1-yl)ethoxy]phenyl]-1H-imidazo[4,5-b]pyridine Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCNC1CCCC1)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)OCCN1C(CCCC1)C=1C=NC=CC1 VPZONHBYECNKPC-UHFFFAOYSA-N 0.000 claims description 2
• NXSZQWXQTAQARO-UHFFFAOYSA-N N1(CCOCC1)CCOC1=CC=C(C=C1)C1=NC=2C(=NC=C(C2C#N)C#N)N1.ClC=1C(=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)OCCN2CCOCC2)C2=CSC=C2 Chemical compound N1(CCOCC1)CCOC1=CC=C(C=C1)C1=NC=2C(=NC=C(C2C#N)C#N)N1.ClC=1C(=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)OCCN2CCOCC2)C2=CSC=C2 NXSZQWXQTAQARO-UHFFFAOYSA-N 0.000 claims description 2
• GUTYSUNIKJNUTN-UHFFFAOYSA-N ethyl 4-[[3-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-2-hydroxypropyl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NCC(O)COC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 GUTYSUNIKJNUTN-UHFFFAOYSA-N 0.000 claims description 2
• YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 2
• 150000002780 morpholines Chemical class 0.000 claims description 2
• HRXCKAKMQBABME-UHFFFAOYSA-N n-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]-2-methoxyethanamine Chemical compound C1=CC(OCCNCCOC)=CC=C1C1=NC2=CC(Br)=CN=C2N1 HRXCKAKMQBABME-UHFFFAOYSA-N 0.000 claims description 2
• WPNNHTYXMIDNBU-UHFFFAOYSA-N n-[4-(6-bromo-7-methyl-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]-3-cyanobenzenesulfonamide Chemical compound N1C=2C(C)=C(Br)C=NC=2N=C1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=CC(C#N)=C1 WPNNHTYXMIDNBU-UHFFFAOYSA-N 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims 12
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 9
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 8
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
• 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 1
• 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 1
• 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 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
• BWZKPNWQLWMTLE-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-[(4-chlorophenyl)methylamino]propan-2-ol Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCC(O)CNCC1=CC=C(Cl)C=C1 BWZKPNWQLWMTLE-UHFFFAOYSA-N 0.000 claims 1
• OWCINWSBIDNAND-UHFFFAOYSA-N 1-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-3-[4-(2-hydroxyethyl)piperazin-1-yl]propan-2-ol Chemical compound C1CN(CCO)CCN1CC(O)COC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 OWCINWSBIDNAND-UHFFFAOYSA-N 0.000 claims 1
• XTDBHCCLBHTPBF-UHFFFAOYSA-N 2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-n-(furan-2-ylmethyl)ethanamine;2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-n-(oxolan-2-ylmethyl)ethanamine Chemical compound N1C2=CC(Br)=CN=C2N=C1C(C=C1)=CC=C1OCCNCC1CCCO1.N1C2=CC(Br)=CN=C2N=C1C(C=C1)=CC=C1OCCNCC1=CC=CO1 XTDBHCCLBHTPBF-UHFFFAOYSA-N 0.000 claims 1
• FVUZWLYBAFHLJZ-UHFFFAOYSA-N 2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-n-[(3-chlorophenyl)methyl]ethanamine Chemical compound ClC1=CC=CC(CNCCOC=2C=CC(=CC=2)C=2NC3=CC(Br)=CN=C3N=2)=C1 FVUZWLYBAFHLJZ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• LWJOMKRAKUJILB-UHFFFAOYSA-N 4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)-n-[(3-methylimidazol-4-yl)methyl]aniline Chemical compound CN1C=NC=C1CNC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 LWJOMKRAKUJILB-UHFFFAOYSA-N 0.000 claims 1
• CZMUQNQZFQWIBE-UHFFFAOYSA-N 4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)-n-[(4-bromothiophen-2-yl)methyl]aniline;4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)-n-(1h-imidazol-5-ylmethyl)aniline Chemical compound N1C2=CC(Br)=CN=C2N=C1C(C=C1)=CC=C1NCC1=CN=CN1.BrC1=CSC(CNC=2C=CC(=CC=2)C=2NC3=CC(Br)=CN=C3N=2)=C1 CZMUQNQZFQWIBE-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 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
• UGOXLKIBIFCXAM-UHFFFAOYSA-N 4-[2-[4-[6-chloro-7-(4-methylphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]morpholine;6-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-n-(1-phenylethyl)-1h-imidazo[4,5-b]pyridin-7-amine Chemical compound C1=CC(C)=CC=C1C1=C(Cl)C=NC2=C1NC(C=1C=CC(OCCN3CCOCC3)=CC=1)=N2.C=1C=CC=CC=1C(C)NC(C=1N2)=C(Cl)C=NC=1N=C2C(C=C1)=CC=C1OCCN1CCOCC1 UGOXLKIBIFCXAM-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
• CMRPWNIRAMEQHN-SFVHDIHTSA-N 6-[4-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]piperazin-1-yl]pyridine-3-carbonitrile;(2s)-1-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]pyrrolidine-2-carboxamide Chemical compound NC(=O)[C@@H]1CCCN1CCOC1=CC=C(C=2NC3=CC(Br)=CN=C3N=2)C=C1.N1C2=CC(Br)=CN=C2N=C1C(C=C1)=CC=C1OCCN(CC1)CCN1C1=CC=C(C#N)C=N1 CMRPWNIRAMEQHN-SFVHDIHTSA-N 0.000 claims 1
• XGKWTAJSMRYNMF-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;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=CC(Br)=CN=C3N=2)C=CC=1OCC(O)CNC1=NC=CS1.C=1C=C(C=2NC3=CC(Br)=CN=C3N=2)C=CC=1OCC(O)CN(CC1)CCN1C1=CC=C(C#N)C=N1 XGKWTAJSMRYNMF-UHFFFAOYSA-N 0.000 claims 1
• YPYZUHTWDNOADA-UHFFFAOYSA-N 6-bromo-2-[4-[2-[4-(2-methoxyethyl)piperazin-1-yl]ethoxy]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C1CN(CCOC)CCN1CCOC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 YPYZUHTWDNOADA-UHFFFAOYSA-N 0.000 claims 1
• YYBPTEBQLHBZRW-UHFFFAOYSA-N 6-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-n-(4-morpholin-4-ylphenyl)-1h-imidazo[4,5-b]pyridin-7-amine Chemical compound ClC1=CN=C2N=C(C=3C=CC(OCCN4CCOCC4)=CC=3)NC2=C1NC(C=C1)=CC=C1N1CCOCC1 YYBPTEBQLHBZRW-UHFFFAOYSA-N 0.000 claims 1
• SJMIFQGACFOHIW-UHFFFAOYSA-N 6-chloro-2-[4-(2-morpholin-4-ylethylamino)phenyl]-n-phenyl-1h-imidazo[4,5-b]pyridin-7-amine;n-[4-(6,7-dichloro-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(C=2NC3=C(Cl)C(Cl)=CN=C3N=2)C=C1.ClC1=CN=C2N=C(C=3C=CC(NCCN4CCOCC4)=CC=3)NC2=C1NC1=CC=CC=C1 SJMIFQGACFOHIW-UHFFFAOYSA-N 0.000 claims 1
• MTGYZTJPUSEPNV-UHFFFAOYSA-N BrC=1C(=C2C(=NC1)N=C(N2)C2=CC=C(C=C2)NS(=O)(=O)C2=CC=C(C=C2)OC)C.BrC=2C(=C1C(=NC2)N=C(N1)C1=CC=C(C=C1)NS(=O)(=O)C=1C=CC=C2C=CC=NC12)C Chemical compound BrC=1C(=C2C(=NC1)N=C(N2)C2=CC=C(C=C2)NS(=O)(=O)C2=CC=C(C=C2)OC)C.BrC=2C(=C1C(=NC2)N=C(N1)C1=CC=C(C=C1)NS(=O)(=O)C=1C=CC=C2C=CC=NC12)C MTGYZTJPUSEPNV-UHFFFAOYSA-N 0.000 claims 1
• PSPLFABSDLTRMS-UHFFFAOYSA-N BrC=1C(=C2C(=NC1)N=C(N2)C2=CC=C(N)C=C2)C.BrC=2C(=C1C(=NC2)N=C(N1)C1=CC=C(C=C1)[N+](=O)[O-])C.BrC=1C(=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)OCCN2CCCCC2)C Chemical compound BrC=1C(=C2C(=NC1)N=C(N2)C2=CC=C(N)C=C2)C.BrC=2C(=C1C(=NC2)N=C(N1)C1=CC=C(C=C1)[N+](=O)[O-])C.BrC=1C(=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)OCCN2CCCCC2)C PSPLFABSDLTRMS-UHFFFAOYSA-N 0.000 claims 1
• DSCVTYBHZLGDRC-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)NCC2=CC=C(C=C2)OC.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)NCC=1C=C(C#N)C=CC1 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)NCC2=CC=C(C=C2)OC.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)NCC=1C=C(C#N)C=CC1 DSCVTYBHZLGDRC-UHFFFAOYSA-N 0.000 claims 1
• OKTYKKMWGKNOKB-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCC(CN1CC(CCC1)C(=O)N)O)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCC(CN2CCC(CC2)C(=O)N)O)C=C1 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCC(CN1CC(CCC1)C(=O)N)O)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCC(CN2CCC(CC2)C(=O)N)O)C=C1 OKTYKKMWGKNOKB-UHFFFAOYSA-N 0.000 claims 1
• YFYQKLIIRHWTGH-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCC(CN1CC(CCC1)O)O)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCC(CNCCCN2C(CCC2)=O)O)C=C1 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCC(CN1CC(CCC1)O)O)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCC(CNCCCN2C(CCC2)=O)O)C=C1 YFYQKLIIRHWTGH-UHFFFAOYSA-N 0.000 claims 1
• QBORUKJFSDMBKW-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCC(CN1CCC(CC1)(O)C1=CC=CC=C1)O)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCC(CN2C(CCCC2)C=2C=NC=CC2)O)C=C1 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCC(CN1CCC(CC1)(O)C1=CC=CC=C1)O)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCC(CN2C(CCCC2)C=2C=NC=CC2)O)C=C1 QBORUKJFSDMBKW-UHFFFAOYSA-N 0.000 claims 1
• JQCHSPCWQAXZPN-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCC(CNC1CC1)O)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCC(CN2CCN(CC2)CCOC)O)C=C1 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCC(CNC1CC1)O)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCC(CN2CCN(CC2)CCOC)O)C=C1 JQCHSPCWQAXZPN-UHFFFAOYSA-N 0.000 claims 1
• UGBBJKYLHDQEFY-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCC(CNCC1=C(C=CC=C1)OC)O)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCC(CN2CCN(CC2)C2=NC=CN=C2)O)C=C1 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCC(CNCC1=C(C=CC=C1)OC)O)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCC(CN2CCN(CC2)C2=NC=CN=C2)O)C=C1 UGBBJKYLHDQEFY-UHFFFAOYSA-N 0.000 claims 1
• YRUMUZDWPREKFI-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCN1CC(CCC1)C(=O)N)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCCNCCC=2N=CNC2)C=C1 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCN1CC(CCC1)C(=O)N)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCCNCCC=2N=CNC2)C=C1 YRUMUZDWPREKFI-UHFFFAOYSA-N 0.000 claims 1
• UCADVMLKXHSLFJ-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCN1CCC(CC1)C(=O)N)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCCNC=2SC=CN2)C=C1 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCN1CCC(CC1)C(=O)N)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCCNC=2SC=CN2)C=C1 UCADVMLKXHSLFJ-UHFFFAOYSA-N 0.000 claims 1
• ZIBWWOOMJRGVPI-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCN1CCN(CC1)C1=C(C#N)C=CC=C1)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCCNC2=NNC=N2)C=C1 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCN1CCN(CC1)C1=C(C#N)C=CC=C1)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCCNC2=NNC=N2)C=C1 ZIBWWOOMJRGVPI-UHFFFAOYSA-N 0.000 claims 1
• QUPRPCBAYCKYEK-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCN1CCN(CC1)CCO)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)OCCN1CCC(CC1)C1=C(C=CC=C1)OC Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCN1CCN(CC1)CCO)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)OCCN1CCC(CC1)C1=C(C=CC=C1)OC QUPRPCBAYCKYEK-UHFFFAOYSA-N 0.000 claims 1
• FPKLCXSOOMMCOW-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCNCC1=CC=C(C=C1)Cl)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCCNCC2=CC(=CC=C2)OC)C=C1 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCNCC1=CC=C(C=C1)Cl)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCCNCC2=CC(=CC=C2)OC)C=C1 FPKLCXSOOMMCOW-UHFFFAOYSA-N 0.000 claims 1
• IUSXZAVLAJRXHX-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCNCC1=CC=C(C=C1)OC)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCCNCCCN2C=NC=C2)C=C1 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCNCC1=CC=C(C=C1)OC)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCCNCCCN2C=NC=C2)C=C1 IUSXZAVLAJRXHX-UHFFFAOYSA-N 0.000 claims 1
• ZICQDOVVPQGDEC-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCNCC=1SC=CC1)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCCNCC2=CC=NC=C2)C=C1 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCNCC=1SC=CC1)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCCNCC2=CC=NC=C2)C=C1 ZICQDOVVPQGDEC-UHFFFAOYSA-N 0.000 claims 1
• UIKIOXUSLJQBMT-UHFFFAOYSA-N C(C1=CC=CC=C1)N(C)CCOC1=CC=C(C=C1)C1=NC=2C(=NC=C(C2)Br)N1.BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCN(CCN(C)C)CC)C=C2 Chemical compound C(C1=CC=CC=C1)N(C)CCOC1=CC=C(C=C1)C1=NC=2C(=NC=C(C2)Br)N1.BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCN(CCN(C)C)CC)C=C2 UIKIOXUSLJQBMT-UHFFFAOYSA-N 0.000 claims 1
• HUGARKPRRBTXRP-UHFFFAOYSA-N ClC=1C(=C2C(=NC1)N=C(N2)C2=CC=C(C=C2)OCCN2CCOCC2)N2C=CC=C2.ClC=2C(=C1C(=NC2)N=C(N1)C1=CC=C(C=C1)OCCN1CCOCC1)N Chemical compound ClC=1C(=C2C(=NC1)N=C(N2)C2=CC=C(C=C2)OCCN2CCOCC2)N2C=CC=C2.ClC=2C(=C1C(=NC2)N=C(N1)C1=CC=C(C=C1)OCCN1CCOCC1)N HUGARKPRRBTXRP-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• CZZALBNDDHGBTK-UHFFFAOYSA-N ClC=1C(=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)NCCN2CCOCC2)Cl.NC2=CC=C(C=C2)C2=NC=1C(=NC=C(C1NC1=CC=CC=C1)Cl)N2 Chemical compound ClC=1C(=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)NCCN2CCOCC2)Cl.NC2=CC=C(C=C2)C2=NC=1C(=NC=C(C1NC1=CC=CC=C1)Cl)N2 CZZALBNDDHGBTK-UHFFFAOYSA-N 0.000 claims 1
• BYJONXOFNTVHNT-UHFFFAOYSA-N ClC=1C(=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)OCCN2CCOCC2)C=2C=C(C=CC2)NC(C)=O.ClC=2C(=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)OCCN1CCOCC1)C1=CC(=CC=C1)OC Chemical compound ClC=1C(=C2C(=NC1)NC(=N2)C2=CC=C(C=C2)OCCN2CCOCC2)C=2C=C(C=CC2)NC(C)=O.ClC=2C(=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)OCCN1CCOCC1)C1=CC(=CC=C1)OC BYJONXOFNTVHNT-UHFFFAOYSA-N 0.000 claims 1
• VMCDUWCFGJWEPI-UHFFFAOYSA-N ClC=1C(=C2C(=NC1)NC(=N2)C=2C=CC(=C(C2)N)N2CCOCC2)Cl.ClC=2C(=C1C(=NC2)N=C(N1)C1=CC=C(C=C1)N1CCOCC1)Cl Chemical compound ClC=1C(=C2C(=NC1)NC(=N2)C=2C=CC(=C(C2)N)N2CCOCC2)Cl.ClC=2C(=C1C(=NC2)N=C(N1)C1=CC=C(C=C1)N1CCOCC1)Cl VMCDUWCFGJWEPI-UHFFFAOYSA-N 0.000 claims 1
• JNXLGHBJPNHBNQ-UTONKHPSSA-N ClC=1C(=C2C(=NC1)NC(=N2)C=2C=CC(=C(C2)O)NC[C@@H]2NCCC2)C.NC2=C(C=C(C=C2)C2=NC=1C(=NC=C(C1C)Cl)N2)O Chemical compound ClC=1C(=C2C(=NC1)NC(=N2)C=2C=CC(=C(C2)O)NC[C@@H]2NCCC2)C.NC2=C(C=C(C=C2)C2=NC=1C(=NC=C(C1C)Cl)N2)O JNXLGHBJPNHBNQ-UTONKHPSSA-N 0.000 claims 1
• XQZCGVDIXGWWMB-UHFFFAOYSA-N N(C1=CC=CC=C1)C1=C2C(=NC=C1C#N)NC(=N2)C2=CC=C(C=C2)OCCN(C)CCOC.ClC2=C1C(=NC=C2C#N)NC(=N1)C1=CC=C(C=C1)OCCN1CCOCC1 Chemical compound N(C1=CC=CC=C1)C1=C2C(=NC=C1C#N)NC(=N2)C2=CC=C(C=C2)OCCN(C)CCOC.ClC2=C1C(=NC=C2C#N)NC(=N1)C1=CC=C(C=C1)OCCN1CCOCC1 XQZCGVDIXGWWMB-UHFFFAOYSA-N 0.000 claims 1
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• VVHSEWBARKYCSD-UHFFFAOYSA-N n-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]-1-phenylethanamine Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCCNC(C)C1=CC=CC=C1 VVHSEWBARKYCSD-UHFFFAOYSA-N 0.000 claims 1
• UVZJGXVXLUPJHO-UHFFFAOYSA-N n-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]-2-morpholin-4-ylethanamine;2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-n-[(2-methoxyphenyl)methyl]ethanamine Chemical compound N1C2=CC(Br)=CN=C2N=C1C(C=C1)=CC=C1OCCNCCN1CCOCC1.COC1=CC=CC=C1CNCCOC1=CC=C(C=2NC3=CC(Br)=CN=C3N=2)C=C1 UVZJGXVXLUPJHO-UHFFFAOYSA-N 0.000 claims 1
• LMOQIZILLDCHJP-UHFFFAOYSA-N n-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]-n-methyl-2-phenylethanamine;6-bromo-2-[4-[2-(4-pyridin-2-ylpiperazin-1-yl)ethoxy]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C=1C=C(C=2NC3=CC(Br)=CN=C3N=2)C=CC=1OCCN(C)CCC1=CC=CC=C1.N1C2=CC(Br)=CN=C2N=C1C(C=C1)=CC=C1OCCN(CC1)CCN1C1=CC=CC=N1 LMOQIZILLDCHJP-UHFFFAOYSA-N 0.000 claims 1
• RRDNFJDKDYTHKC-UHFFFAOYSA-N n-[4-(6-bromo-7-methyl-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]-4-cyanobenzenesulfonamide Chemical compound N1C=2C(C)=C(Br)C=NC=2N=C1C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(C#N)C=C1 RRDNFJDKDYTHKC-UHFFFAOYSA-N 0.000 claims 1
• KZWKCKYROXFVQK-UHFFFAOYSA-N n-benzyl-2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethanamine Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCNCC1=CC=CC=C1 KZWKCKYROXFVQK-UHFFFAOYSA-N 0.000 claims 1
• FUCYQQLCDVEALL-UHFFFAOYSA-N n-benzyl-4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)aniline;4-[[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)anilino]methyl]benzonitrile Chemical compound N1C2=CC(Br)=CN=C2N=C1C(C=C1)=CC=C1NCC1=CC=CC=C1.N1C2=CC(Br)=CN=C2N=C1C(C=C1)=CC=C1NCC1=CC=C(C#N)C=C1 FUCYQQLCDVEALL-UHFFFAOYSA-N 0.000 claims 1
• SSIFZJALHGDESM-UHFFFAOYSA-N n-benzyl-6-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-amine;6-chloro-n-cyclopentyl-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-amine Chemical compound ClC1=CN=C2N=C(C=3C=CC(OCCN4CCOCC4)=CC=3)NC2=C1NC1CCCC1.ClC1=CN=C2N=C(C=3C=CC(OCCN4CCOCC4)=CC=3)NC2=C1NCC1=CC=CC=C1 SSIFZJALHGDESM-UHFFFAOYSA-N 0.000 claims 1
• XIOZFJDWXCPTFO-UHFFFAOYSA-N n-benzyl-6-chloro-n-methyl-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-amine;6-chloro-n-methyl-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-amine Chemical compound N1C=2C(NC)=C(Cl)C=NC=2N=C1C(C=C1)=CC=C1OCCN1CCOCC1.ClC=1C=NC=2N=C(C=3C=CC(OCCN4CCOCC4)=CC=3)NC=2C=1N(C)CC1=CC=CC=C1 XIOZFJDWXCPTFO-UHFFFAOYSA-N 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 64
• 238000002560 therapeutic procedure Methods 0.000 abstract description 3
• 238000000668 atmospheric pressure chemical ionisation mass spectrometry Methods 0.000 description 297
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 182
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 130
• 229910052739 hydrogen Inorganic materials 0.000 description 127
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 114
• 238000005160 1H NMR spectroscopy Methods 0.000 description 90
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 72
• 239000000047 product Substances 0.000 description 72
• 238000005481 NMR spectroscopy Methods 0.000 description 65
• 235000019439 ethyl acetate Nutrition 0.000 description 62
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 59
• 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 description 53
• VXPIILRXXPFCHD-UHFFFAOYSA-N 6-bromo-2-[4-(2-chloroethoxy)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(OCCCl)=CC=C1C1=NC2=CC(Br)=CN=C2N1 VXPIILRXXPFCHD-UHFFFAOYSA-N 0.000 description 53
• 239000011541 reaction mixture Substances 0.000 description 50
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
• 239000000243 solution Substances 0.000 description 39
• YRGMYJUKFJPNPD-UHFFFAOYSA-N 5-bromopyridine-2,3-diamine Chemical compound NC1=CC(Br)=CN=C1N YRGMYJUKFJPNPD-UHFFFAOYSA-N 0.000 description 38
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
• DIQBTWWFJFOKCC-UHFFFAOYSA-N 6-bromo-2-[4-(oxiran-2-ylmethoxy)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCC1CO1 DIQBTWWFJFOKCC-UHFFFAOYSA-N 0.000 description 36
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
• 239000002904 solvent Substances 0.000 description 28
• ATOQENUJNICCNS-UHFFFAOYSA-N 4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=NC2=CC(Br)=CN=C2N1 ATOQENUJNICCNS-UHFFFAOYSA-N 0.000 description 27
• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 27
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
• 239000012074 organic phase Substances 0.000 description 25
• 239000000843 powder Substances 0.000 description 25
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
• 229910052799 carbon Inorganic materials 0.000 description 23
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 21
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 21
• 239000007787 solid Substances 0.000 description 21
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 20
• 239000012267 brine Substances 0.000 description 19
• 238000001704 evaporation Methods 0.000 description 19
• 230000008020 evaporation Effects 0.000 description 19
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
• 239000008346 aqueous phase Substances 0.000 description 16
• 239000000460 chlorine Substances 0.000 description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
• 238000001914 filtration Methods 0.000 description 15
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 15
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
• 238000004440 column chromatography Methods 0.000 description 13
• 206010039083 rhinitis Diseases 0.000 description 13
• GOVJRSTWOQZULF-UHFFFAOYSA-N 4,5-dichloropyridine-2,3-diamine Chemical compound NC1=NC=C(Cl)C(Cl)=C1N GOVJRSTWOQZULF-UHFFFAOYSA-N 0.000 description 12
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
• 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 description 11
• 239000000377 silicon dioxide Substances 0.000 description 11
• 208000030507 AIDS Diseases 0.000 description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 10
• 238000000746 purification Methods 0.000 description 10
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 239000013078 crystal Substances 0.000 description 9
• 239000002244 precipitate Substances 0.000 description 9
• ZWULFIBGPXWGFG-UHFFFAOYSA-N 2-methyl-1h-imidazole-5-carbaldehyde Chemical compound CC1=NC=C(C=O)N1 ZWULFIBGPXWGFG-UHFFFAOYSA-N 0.000 description 8
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 8
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 8
• 230000002829 reductive effect Effects 0.000 description 8
• DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 7
• OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 7
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
• 208000010668 atopic eczema Diseases 0.000 description 7
• 239000003054 catalyst Substances 0.000 description 7
• KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 7
• 239000000741 silica gel Substances 0.000 description 7
• 229910002027 silica gel Inorganic materials 0.000 description 7
• LHDLDVJLRBQBFT-UHFFFAOYSA-N 4-(6-bromo-1H-imidazo[4,5-b]pyridin-2-yl)phenol Chemical compound C1=CC(O)=CC=C1C1=NC2=CC(Br)=CN=C2N1 LHDLDVJLRBQBFT-UHFFFAOYSA-N 0.000 description 6
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• 239000001828 Gelatine Substances 0.000 description 6
• YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
• 239000007868 Raney catalyst Substances 0.000 description 6
• 229910000564 Raney nickel Inorganic materials 0.000 description 6
• 210000001744 T-lymphocyte Anatomy 0.000 description 6
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 6
• 238000007792 addition Methods 0.000 description 6
• 230000000172 allergic effect Effects 0.000 description 6
• 239000013058 crude material Substances 0.000 description 6
• 239000012043 crude product Substances 0.000 description 6
• 239000003480 eluent Substances 0.000 description 6
• 229920000159 gelatin Polymers 0.000 description 6
• 235000019322 gelatine Nutrition 0.000 description 6
• 239000000543 intermediate Substances 0.000 description 6
• 230000001404 mediated effect Effects 0.000 description 6
• 238000001953 recrystallisation Methods 0.000 description 6
• 210000001519 tissue Anatomy 0.000 description 6
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
• 230000004913 activation Effects 0.000 description 5
• 238000003556 assay Methods 0.000 description 5
• 125000001246 bromo group Chemical group Br* 0.000 description 5
• 230000005587 bubbling Effects 0.000 description 5
• 239000002775 capsule Substances 0.000 description 5
• 238000007429 general method Methods 0.000 description 5
• 238000004128 high performance liquid chromatography Methods 0.000 description 5
• 239000003112 inhibitor Substances 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 5
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 239000012312 sodium hydride Substances 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• 239000000758 substrate Substances 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
• PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 4
• MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 4
• WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 4
• DORCKMVRRGNWSY-UHFFFAOYSA-N 4-(6-chloro-7-methoxy-1h-imidazo[4,5-b]pyridin-2-yl)aniline Chemical compound N=1C=2C(OC)=C(Cl)C=NC=2NC=1C1=CC=C(N)C=C1 DORCKMVRRGNWSY-UHFFFAOYSA-N 0.000 description 4
• RWYBUQRPDSEALC-UHFFFAOYSA-N 5-(6-chloro-7-methyl-1h-imidazo[4,5-b]pyridin-2-yl)-2-nitrophenol Chemical compound N=1C=2C(C)=C(Cl)C=NC=2NC=1C1=CC=C([N+]([O-])=O)C(O)=C1 RWYBUQRPDSEALC-UHFFFAOYSA-N 0.000 description 4
• RSWAKJOKUAKTLU-UHFFFAOYSA-N 5-chloro-4-methylpyridine-2,3-diamine Chemical compound CC1=C(Cl)C=NC(N)=C1N RSWAKJOKUAKTLU-UHFFFAOYSA-N 0.000 description 4
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
• 206010020751 Hypersensitivity Diseases 0.000 description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
• 239000002253 acid Substances 0.000 description 4
• 229910021529 ammonia Inorganic materials 0.000 description 4
• 230000001363 autoimmune Effects 0.000 description 4
• 239000002585 base Substances 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• 230000003197 catalytic effect Effects 0.000 description 4
• 239000003153 chemical reaction reagent Substances 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 4
• 238000001035 drying Methods 0.000 description 4
• 238000003818 flash chromatography Methods 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• 230000003463 hyperproliferative effect Effects 0.000 description 4
• 230000002757 inflammatory effect Effects 0.000 description 4
• 229910052740 iodine Inorganic materials 0.000 description 4
• LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
• RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 4
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
• 239000003921 oil Substances 0.000 description 4
• 235000019198 oils Nutrition 0.000 description 4
• 210000000056 organ Anatomy 0.000 description 4
• ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
• 230000002265 prevention Effects 0.000 description 4
• 230000002062 proliferating effect Effects 0.000 description 4
• 239000002002 slurry Substances 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• 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 description 3
• 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 description 3
• HGZJJKZPPMFIBU-UHFFFAOYSA-N 3-formylbenzonitrile Chemical compound O=CC1=CC=CC(C#N)=C1 HGZJJKZPPMFIBU-UHFFFAOYSA-N 0.000 description 3
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 3
• NBJHDLKSWUDGJG-UHFFFAOYSA-N 4-(2-chloroethyl)morpholin-4-ium;chloride Chemical compound Cl.ClCCN1CCOCC1 NBJHDLKSWUDGJG-UHFFFAOYSA-N 0.000 description 3
• WCLJTEXCGGSJJN-UHFFFAOYSA-N 4-(2-piperidin-1-ylethoxy)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCCN1CCCCC1 WCLJTEXCGGSJJN-UHFFFAOYSA-N 0.000 description 3
• 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 description 3
• RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 3
• SRAQFLSCIKIOES-UHFFFAOYSA-N 5-chloro-4-methoxypyridine-2,3-diamine Chemical compound COC1=C(Cl)C=NC(N)=C1N SRAQFLSCIKIOES-UHFFFAOYSA-N 0.000 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• 201000010717 Bruton-type agammaglobulinemia Diseases 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
• 201000004624 Dermatitis Diseases 0.000 description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
• 229930195725 Mannitol Natural products 0.000 description 3
• 241000699670 Mus sp. Species 0.000 description 3
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• 208000016349 X-linked agammaglobulinemia Diseases 0.000 description 3
• 230000001154 acute effect Effects 0.000 description 3
• 229910052786 argon Inorganic materials 0.000 description 3
• 239000012131 assay buffer Substances 0.000 description 3
• 238000009835 boiling Methods 0.000 description 3
• 125000004803 chlorobenzyl group Chemical group 0.000 description 3
• 238000004587 chromatography analysis Methods 0.000 description 3
• 238000005859 coupling reaction Methods 0.000 description 3
• 239000012458 free base Substances 0.000 description 3
• 239000001257 hydrogen Substances 0.000 description 3
• 208000015181 infectious disease Diseases 0.000 description 3
• NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 3
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
• 210000004072 lung Anatomy 0.000 description 3
• 239000000594 mannitol Substances 0.000 description 3
• 235000010355 mannitol Nutrition 0.000 description 3
• 239000000463 material Substances 0.000 description 3
• QNUQDDPNECMPAT-UHFFFAOYSA-N methyl 4-(2-morpholin-4-ylethoxy)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OCCN1CCOCC1 QNUQDDPNECMPAT-UHFFFAOYSA-N 0.000 description 3
• RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 3
• 229910017604 nitric acid Inorganic materials 0.000 description 3
• BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 3
• 239000003960 organic solvent Substances 0.000 description 3
• 239000012071 phase Substances 0.000 description 3
• 238000002953 preparative HPLC Methods 0.000 description 3
• 108090000765 processed proteins & peptides Proteins 0.000 description 3
• 125000006239 protecting group Chemical group 0.000 description 3
• TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 3
• 230000035484 reaction time Effects 0.000 description 3
• 230000009467 reduction Effects 0.000 description 3
• 238000004007 reversed phase HPLC Methods 0.000 description 3
• 230000011664 signaling Effects 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• 235000000346 sugar Nutrition 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
• 239000011701 zinc Substances 0.000 description 3
• PXJACNDVRNAFHD-UHFFFAOYSA-N (2-methoxyphenyl)methanamine Chemical compound COC1=CC=CC=C1CN PXJACNDVRNAFHD-UHFFFAOYSA-N 0.000 description 2
• VLJNHYLEOZPXFW-SCSAIBSYSA-N (2r)-pyrrolidine-2-carboxamide Chemical compound NC(=O)[C@H]1CCCN1 VLJNHYLEOZPXFW-SCSAIBSYSA-N 0.000 description 2
• SUZZEFBECOIRIY-BXXIVHCWSA-N (2s)-2-amino-3-methylbutan-1-ol Chemical compound CC(C)[C@H](N)CO.CC(C)[C@H](N)CO SUZZEFBECOIRIY-BXXIVHCWSA-N 0.000 description 2
• BJFPYGGTDAYECS-UHFFFAOYSA-N (3-chlorophenyl)methanamine Chemical compound NCC1=CC=CC(Cl)=C1 BJFPYGGTDAYECS-UHFFFAOYSA-N 0.000 description 2
• GRRIMVWABNHKBX-UHFFFAOYSA-N (3-methoxyphenyl)methanamine Chemical compound COC1=CC=CC(CN)=C1 GRRIMVWABNHKBX-UHFFFAOYSA-N 0.000 description 2
• YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 2
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
• GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• BMEMBBFDTYHTLH-UHFFFAOYSA-N 1-(2-methoxyethyl)piperazine Chemical compound COCCN1CCNCC1 BMEMBBFDTYHTLH-UHFFFAOYSA-N 0.000 description 2
• HJORCZCMNWLHMB-UHFFFAOYSA-N 1-(3-aminopropyl)pyrrolidin-2-one Chemical compound NCCCN1CCCC1=O HJORCZCMNWLHMB-UHFFFAOYSA-N 0.000 description 2
• PZIBVWUXWNYTNL-UHFFFAOYSA-N 1-(3-methoxyphenyl)piperazine Chemical compound COC1=CC=CC(N2CCNCC2)=C1 PZIBVWUXWNYTNL-UHFFFAOYSA-N 0.000 description 2
• IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 2
• HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
• WAKUKXKZEXFXJP-UHFFFAOYSA-N 1-ethylpiperidin-3-amine Chemical compound CCN1CCCC(N)C1 WAKUKXKZEXFXJP-UHFFFAOYSA-N 0.000 description 2
• BKMMTJMQCTUHRP-UHFFFAOYSA-O 1-hydroxypropan-2-ylazanium Chemical compound CC([NH3+])CO BKMMTJMQCTUHRP-UHFFFAOYSA-O 0.000 description 2
• PKDPUENCROCRCH-UHFFFAOYSA-N 1-piperazin-1-ylethanone Chemical compound CC(=O)N1CCNCC1 PKDPUENCROCRCH-UHFFFAOYSA-N 0.000 description 2
• ZQEXIXXJFSQPNA-UHFFFAOYSA-N 1h-imidazole-5-carbaldehyde Chemical compound O=CC1=CNC=N1 ZQEXIXXJFSQPNA-UHFFFAOYSA-N 0.000 description 2
• 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 description 2
• ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 2
• FRICBZWJFIRJOB-UHFFFAOYSA-N 2-piperazin-1-ylbenzonitrile Chemical compound N#CC1=CC=CC=C1N1CCNCC1 FRICBZWJFIRJOB-UHFFFAOYSA-N 0.000 description 2
• WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 2
• HCGFLVDMFDHYJD-UHFFFAOYSA-N 2-piperazin-1-ylpyrazine Chemical compound C1CNCCN1C1=CN=CC=N1 HCGFLVDMFDHYJD-UHFFFAOYSA-N 0.000 description 2
• UNIJBMUBHBAUET-UHFFFAOYSA-N 3-(methylamino)propanenitrile Chemical compound CNCCC#N UNIJBMUBHBAUET-UHFFFAOYSA-N 0.000 description 2
• RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 2
• KYVDKOZOAOAFDC-UHFFFAOYSA-N 4,5-dichloro-3-nitropyridin-2-amine Chemical group NC1=NC=C(Cl)C(Cl)=C1[N+]([O-])=O KYVDKOZOAOAFDC-UHFFFAOYSA-N 0.000 description 2
• VCDGTEZSUNFOKA-UHFFFAOYSA-N 4-(2-hydroxyethoxy)benzaldehyde Chemical compound OCCOC1=CC=C(C=O)C=C1 VCDGTEZSUNFOKA-UHFFFAOYSA-N 0.000 description 2
• BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 2
• AMDKFMKXNZPPPV-UHFFFAOYSA-N 4-(methylamino)cyclohexane-1-carbonitrile Chemical compound CNC1CCC(C#N)CC1 AMDKFMKXNZPPPV-UHFFFAOYSA-N 0.000 description 2
• DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 description 2
• VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 2
• WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 2
• DBMFYTQPPBBKHI-UHFFFAOYSA-N 4-cyanobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(C#N)C=C1 DBMFYTQPPBBKHI-UHFFFAOYSA-N 0.000 description 2
• BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 2
• SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 2
• KQKFQBTWXOGINC-UHFFFAOYSA-N 4-phenylpiperidin-4-ol Chemical compound C=1C=CC=CC=1C1(O)CCNCC1 KQKFQBTWXOGINC-UHFFFAOYSA-N 0.000 description 2
• WDANSDASCKBVKH-UHFFFAOYSA-N 4-propan-2-yloxybenzaldehyde Chemical compound CC(C)OC1=CC=C(C=O)C=C1 WDANSDASCKBVKH-UHFFFAOYSA-N 0.000 description 2
• ZRCMCGQDIYNWDX-UHFFFAOYSA-N 5-chloropyridine-2,3-diamine Chemical compound NC1=CC(Cl)=CN=C1N ZRCMCGQDIYNWDX-UHFFFAOYSA-N 0.000 description 2
• NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 2
• AITFREYTVOPXOT-UHFFFAOYSA-N 5-methylpyridine-2,3-diamine Chemical compound CC1=CN=C(N)C(N)=C1 AITFREYTVOPXOT-UHFFFAOYSA-N 0.000 description 2
• XUKLJCAVGFQNHY-UHFFFAOYSA-N 6-bromo-2-[4-(3-chloropropoxy)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(OCCCCl)=CC=C1C1=NC2=CC(Br)=CN=C2N1 XUKLJCAVGFQNHY-UHFFFAOYSA-N 0.000 description 2
• ZYNPMKJQFWNFMI-UHFFFAOYSA-N 6-piperazin-1-ylpyridine-3-carbonitrile Chemical compound N1=CC(C#N)=CC=C1N1CCNCC1 ZYNPMKJQFWNFMI-UHFFFAOYSA-N 0.000 description 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
• 206010067484 Adverse reaction Diseases 0.000 description 2
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• 239000005711 Benzoic acid Substances 0.000 description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
• 206010014950 Eosinophilia Diseases 0.000 description 2
• 102000005720 Glutathione transferase Human genes 0.000 description 2
• 108010070675 Glutathione transferase Proteins 0.000 description 2
• 229910004373 HOAc Inorganic materials 0.000 description 2
• 101700012268 Holin Proteins 0.000 description 2
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
• 241001465754 Metazoa Species 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
• 241000336691 Notolopas brasiliensis Species 0.000 description 2
• 241000721454 Pemphigus Species 0.000 description 2
• 239000002202 Polyethylene glycol Substances 0.000 description 2
• 102000001253 Protein Kinase Human genes 0.000 description 2
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 2
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• 229920002472 Starch Polymers 0.000 description 2
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
• 229930006000 Sucrose Natural products 0.000 description 2
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
• 239000007983 Tris buffer Substances 0.000 description 2
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
• 230000006838 adverse reaction Effects 0.000 description 2
• 239000000443 aerosol Substances 0.000 description 2
• 208000030961 allergic reaction Diseases 0.000 description 2
• MTXSIJUGVMTTMU-UHFFFAOYSA-N anabasine Chemical compound N1CCCCC1C1=CC=CN=C1 MTXSIJUGVMTTMU-UHFFFAOYSA-N 0.000 description 2
• 235000010233 benzoic acid Nutrition 0.000 description 2
• WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
• 229910052794 bromium Inorganic materials 0.000 description 2
• 230000001684 chronic effect Effects 0.000 description 2
• 230000008878 coupling Effects 0.000 description 2
• 238000010168 coupling process Methods 0.000 description 2
• WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 2
• SGJSQQLUMMGQOS-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#C[C]1CCCCC1 SGJSQQLUMMGQOS-UHFFFAOYSA-N 0.000 description 2
• NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 2
• 230000001086 cytosolic effect Effects 0.000 description 2
• 238000010511 deprotection reaction Methods 0.000 description 2
• 238000013461 design Methods 0.000 description 2
• 230000004069 differentiation Effects 0.000 description 2
• 239000002270 dispersing agent Substances 0.000 description 2
• 239000002552 dosage form Substances 0.000 description 2
• 229940079593 drug Drugs 0.000 description 2
• 229940112141 dry powder inhaler Drugs 0.000 description 2
• GQQQULCEHJQUJT-UHFFFAOYSA-N ethyl 4-aminopiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(N)CC1 GQQQULCEHJQUJT-UHFFFAOYSA-N 0.000 description 2
• 238000004108 freeze drying Methods 0.000 description 2
• 125000000524 functional group Chemical group 0.000 description 2
• HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
• 210000001035 gastrointestinal tract Anatomy 0.000 description 2
• RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
• 239000008187 granular material Substances 0.000 description 2
• 210000003958 hematopoietic stem cell Anatomy 0.000 description 2
• 239000005457 ice water Substances 0.000 description 2
• RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
• 239000008101 lactose Substances 0.000 description 2
• HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
• 206010025135 lupus erythematosus Diseases 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
• 125000002757 morpholinyl group Chemical group 0.000 description 2
• FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 2
• 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 description 2
• NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 2
• SASNBVQSOZSTPD-UHFFFAOYSA-N n-methylphenethylamine Chemical compound CNCCC1=CC=CC=C1 SASNBVQSOZSTPD-UHFFFAOYSA-N 0.000 description 2
• 230000007935 neutral effect Effects 0.000 description 2
• BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 description 2
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
• 238000010534 nucleophilic substitution reaction Methods 0.000 description 2
• VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 2
• 230000000414 obstructive effect Effects 0.000 description 2
• YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 2
• 239000000546 pharmaceutical excipient Substances 0.000 description 2
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
• 230000026731 phosphorylation Effects 0.000 description 2
• 238000006366 phosphorylation reaction Methods 0.000 description 2
• PRAYXGYYVXRDDW-UHFFFAOYSA-N piperidin-2-ylmethanol Chemical compound OCC1CCCCN1 PRAYXGYYVXRDDW-UHFFFAOYSA-N 0.000 description 2
• BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 description 2
• HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 2
• XBXHCBLBYQEYTI-UHFFFAOYSA-N piperidin-4-ylmethanol Chemical compound OCC1CCNCC1 XBXHCBLBYQEYTI-UHFFFAOYSA-N 0.000 description 2
• 229920001223 polyethylene glycol Polymers 0.000 description 2
• 108060006633 protein kinase Proteins 0.000 description 2
• 125000003373 pyrazinyl group Chemical group 0.000 description 2
• HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 2
• ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical class NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 2
• GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical compound C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 description 2
• ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 2
• NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 2
• JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 2
• 230000001105 regulatory effect Effects 0.000 description 2
• 208000023504 respiratory system disease Diseases 0.000 description 2
• 230000004044 response Effects 0.000 description 2
• 230000002441 reversible effect Effects 0.000 description 2
• SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 210000003491 skin Anatomy 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
• 239000008107 starch Substances 0.000 description 2
• 235000019698 starch Nutrition 0.000 description 2
• 239000007858 starting material Substances 0.000 description 2
• 229960004793 sucrose Drugs 0.000 description 2
• 239000006188 syrup Substances 0.000 description 2
• 235000020357 syrup Nutrition 0.000 description 2
• 230000009885 systemic effect Effects 0.000 description 2
• PAYVKFGFVBUQPP-OAHLLOKOSA-N tert-butyl (2r)-2-[[4-(6-chloro-7-methyl-1h-imidazo[4,5-b]pyridin-2-yl)-2-hydroxyanilino]methyl]pyrrolidine-1-carboxylate Chemical compound N=1C=2C(C)=C(Cl)C=NC=2NC=1C(C=C1O)=CC=C1NC[C@H]1CCCN1C(=O)OC(C)(C)C PAYVKFGFVBUQPP-OAHLLOKOSA-N 0.000 description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 238000012360 testing method Methods 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
• APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
• 238000005406 washing Methods 0.000 description 2
• HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
• GFQZSGGPNZDNBC-UHFFFAOYSA-N (1-methylbenzimidazol-2-yl)methanamine Chemical compound C1=CC=C2N(C)C(CN)=NC2=C1 GFQZSGGPNZDNBC-UHFFFAOYSA-N 0.000 description 1
• RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 1
• LKKCSUHCVGCGFA-RIHPBJNCSA-N (1r,2s)-2-aminocyclohexan-1-ol;hydrochloride Chemical compound Cl.N[C@H]1CCCC[C@H]1O LKKCSUHCVGCGFA-RIHPBJNCSA-N 0.000 description 1
• LKKCSUHCVGCGFA-GEMLJDPKSA-N (1s,2s)-2-aminocyclohexan-1-ol;hydrochloride Chemical compound Cl.N[C@H]1CCCC[C@@H]1O LKKCSUHCVGCGFA-GEMLJDPKSA-N 0.000 description 1
• KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 1
• YDCBPRUBLDZYBI-UHFFFAOYSA-N (2-ethyl-1h-imidazol-5-yl)methanamine Chemical compound CCC1=NC=C(CN)N1 YDCBPRUBLDZYBI-UHFFFAOYSA-N 0.000 description 1
• DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-N 0.000 description 1
• KLPIBROKEWCCIL-INIZCTEOSA-N (2s)-1-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]pyrrolidine-2-carboxamide Chemical compound NC(=O)[C@@H]1CCCN1CCOC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 KLPIBROKEWCCIL-INIZCTEOSA-N 0.000 description 1
• IBTSWKLSEOGJGJ-UHFFFAOYSA-N (3-acetamidophenyl)boronic acid Chemical compound CC(=O)NC1=CC=CC(B(O)O)=C1 IBTSWKLSEOGJGJ-UHFFFAOYSA-N 0.000 description 1
• OJZQOQNSUZLSMV-UHFFFAOYSA-N (3-aminophenyl)methanol Chemical compound NC1=CC=CC(CO)=C1 OJZQOQNSUZLSMV-UHFFFAOYSA-N 0.000 description 1
• NLLGFYPSWCMUIV-UHFFFAOYSA-N (3-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1 NLLGFYPSWCMUIV-UHFFFAOYSA-N 0.000 description 1
• VBIGYQPQZQSQDU-UHFFFAOYSA-N (3-methoxyphenyl)methanamine 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.COC=1C=C(CN)C=CC1 VBIGYQPQZQSQDU-UHFFFAOYSA-N 0.000 description 1
• MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
• BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• BATOPAZDIZEVQF-MQQKCMAXSA-N (E,E)-2,4-hexadienal Chemical compound C\C=C\C=C\C=O BATOPAZDIZEVQF-MQQKCMAXSA-N 0.000 description 1
• IJXJGQCXFSSHNL-QMMMGPOBSA-N (R)-(-)-2-Phenylglycinol Chemical compound OC[C@H](N)C1=CC=CC=C1 IJXJGQCXFSSHNL-QMMMGPOBSA-N 0.000 description 1
• UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
• ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
• MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
• ZGTFNNUASMWGTM-UHFFFAOYSA-N 1,3-thiazole-2-carbaldehyde Chemical compound O=CC1=NC=CS1 ZGTFNNUASMWGTM-UHFFFAOYSA-N 0.000 description 1
• QDVBKXJMLILLLB-UHFFFAOYSA-N 1,4'-bipiperidine Chemical compound C1CCCCN1C1CCNCC1 QDVBKXJMLILLLB-UHFFFAOYSA-N 0.000 description 1
• APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
• VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 1
• ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 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 description 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 description 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 description 1
• QBJSSOBNVYDCDQ-UHFFFAOYSA-N 1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(N)(=O)=O)=C1 QBJSSOBNVYDCDQ-UHFFFAOYSA-N 0.000 description 1
• KXUGUWTUFUWYRS-UHFFFAOYSA-N 1-methylimidazole-4-sulfonyl chloride Chemical compound CN1C=NC(S(Cl)(=O)=O)=C1 KXUGUWTUFUWYRS-UHFFFAOYSA-N 0.000 description 1
• UDYSDVVJHGYAHB-UHFFFAOYSA-N 1-methylsulfonylpyrrolidin-3-amine Chemical compound CS(=O)(=O)N1CCC(N)C1 UDYSDVVJHGYAHB-UHFFFAOYSA-N 0.000 description 1
• ZGIBIGDAAQIUKA-UHFFFAOYSA-N 1-oxidopyridin-1-ium-3-amine Chemical compound NC1=CC=C[N+]([O-])=C1 ZGIBIGDAAQIUKA-UHFFFAOYSA-N 0.000 description 1
• RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
• ICFGFAUMBISMLR-UHFFFAOYSA-N 1h-pyrazole-5-carbaldehyde Chemical compound O=CC=1C=CNN=1 ICFGFAUMBISMLR-UHFFFAOYSA-N 0.000 description 1
• GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 1
• VKJCJJYNVIYVQR-UHFFFAOYSA-N 2-(3-bromopropyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCBr)C(=O)C2=C1 VKJCJJYNVIYVQR-UHFFFAOYSA-N 0.000 description 1
• SRXFXCKTIGELTI-UHFFFAOYSA-N 2-(4-chlorophenyl)ethanamine Chemical compound NCCC1=CC=C(Cl)C=C1 SRXFXCKTIGELTI-UHFFFAOYSA-N 0.000 description 1
• XNIOWJUQPMKCIJ-UHFFFAOYSA-N 2-(benzylamino)ethanol Chemical compound OCCNCC1=CC=CC=C1 XNIOWJUQPMKCIJ-UHFFFAOYSA-N 0.000 description 1
• KMNXYBHVYDCCNC-UHFFFAOYSA-N 2-(diethylamino)-1,3-thiazole-5-carbaldehyde Chemical compound CCN(CC)C1=NC=C(C=O)S1 KMNXYBHVYDCCNC-UHFFFAOYSA-N 0.000 description 1
• IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 1
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
• JUZIXSBTKXXVQT-UHFFFAOYSA-N 2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-n-(furan-2-ylmethyl)ethanamine Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCNCC1=CC=CO1 JUZIXSBTKXXVQT-UHFFFAOYSA-N 0.000 description 1
• SZSSWDKWOVCHHZ-UHFFFAOYSA-N 2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-n-(pyridin-3-ylmethyl)ethanamine Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCNCC1=CC=CN=C1 SZSSWDKWOVCHHZ-UHFFFAOYSA-N 0.000 description 1
• GKCWGAIZPUIRGE-UHFFFAOYSA-N 2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-n-(thiophen-2-ylmethyl)ethanamine Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCNCC1=CC=CS1 GKCWGAIZPUIRGE-UHFFFAOYSA-N 0.000 description 1
• SSSWSGMNSFNRFZ-UHFFFAOYSA-N 2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-n-[(4-chlorophenyl)methyl]ethanamine Chemical compound C1=CC(Cl)=CC=C1CNCCOC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 SSSWSGMNSFNRFZ-UHFFFAOYSA-N 0.000 description 1
• GUGYHMCGSUBYSF-UHFFFAOYSA-N 2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-n-[(4-methoxyphenyl)methyl]ethanamine Chemical compound C1=CC(OC)=CC=C1CNCCOC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 GUGYHMCGSUBYSF-UHFFFAOYSA-N 0.000 description 1
• VKEUSVOCTJLZND-UHFFFAOYSA-N 2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1C1=NC2=CC(Br)=CN=C2N1 VKEUSVOCTJLZND-UHFFFAOYSA-N 0.000 description 1
• BPEIAZCXFMZYDG-UHFFFAOYSA-N 2-[4-(6-chloro-7-methoxy-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethanol Chemical compound N=1C=2C(OC)=C(Cl)C=NC=2NC=1C1=CC=C(OCCO)C=C1 BPEIAZCXFMZYDG-UHFFFAOYSA-N 0.000 description 1
• RGTLWAFHMDMKCU-UHFFFAOYSA-N 2-[4-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1CCOC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 RGTLWAFHMDMKCU-UHFFFAOYSA-N 0.000 description 1
• QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
• FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
• FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 1
• IBZKBSXREAQDTO-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)ethanamine Chemical compound COCCNCCOC IBZKBSXREAQDTO-UHFFFAOYSA-N 0.000 description 1
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
• 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
• SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 1
• MOLKLIYWXFEEJM-UHFFFAOYSA-N 2h-triazole-4-carbaldehyde Chemical compound O=CC1=CNN=N1 MOLKLIYWXFEEJM-UHFFFAOYSA-N 0.000 description 1
• HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
• BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
• CETXOEGRUBXUAL-UHFFFAOYSA-N 3-(hydroxymethyl)furan-2-carbaldehyde Chemical compound OCC=1C=COC=1C=O CETXOEGRUBXUAL-UHFFFAOYSA-N 0.000 description 1
• YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
• 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 description 1
• WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
• SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
• SRWILAKSARHZPR-UHFFFAOYSA-N 3-chlorobenzaldehyde Chemical compound ClC1=CC=CC(C=O)=C1 SRWILAKSARHZPR-UHFFFAOYSA-N 0.000 description 1
• BHNRGBRMCNHNQD-UHFFFAOYSA-N 3-cyanobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC(C#N)=C1 BHNRGBRMCNHNQD-UHFFFAOYSA-N 0.000 description 1
• AMKPQMFZCBTTAT-UHFFFAOYSA-N 3-ethylaniline Chemical compound CCC1=CC=CC(N)=C1 AMKPQMFZCBTTAT-UHFFFAOYSA-N 0.000 description 1
• PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 1
• AZVSIHIBYRHSLB-UHFFFAOYSA-N 3-furaldehyde Chemical compound O=CC=1C=COC=1 AZVSIHIBYRHSLB-UHFFFAOYSA-N 0.000 description 1
• AUBBVPIQUDFRQI-UHFFFAOYSA-N 3-hydroxy-4-nitrobenzaldehyde Chemical compound OC1=CC(C=O)=CC=C1[N+]([O-])=O AUBBVPIQUDFRQI-UHFFFAOYSA-N 0.000 description 1
• KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 description 1
• JSHLOPGSDZTEGQ-UHFFFAOYSA-N 3-methoxy-4-phenylmethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC=C1OCC1=CC=CC=C1 JSHLOPGSDZTEGQ-UHFFFAOYSA-N 0.000 description 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 description 1
• REGFWZVTTFGQOJ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine Chemical compound NC1=NCCS1 REGFWZVTTFGQOJ-UHFFFAOYSA-N 0.000 description 1
• YYGOSKGTMMGUEV-UHFFFAOYSA-N 4-(2-cyanoethoxy)benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(OCCC#N)C=C1 YYGOSKGTMMGUEV-UHFFFAOYSA-N 0.000 description 1
• SRAVSVBVHDLLPO-UHFFFAOYSA-N 4-(2-methoxyphenyl)piperidine Chemical compound COC1=CC=CC=C1C1CCNCC1 SRAVSVBVHDLLPO-UHFFFAOYSA-N 0.000 description 1
• CSNHQUYGQIHHLS-UHFFFAOYSA-N 4-(2-morpholin-4-ylethoxy)-3-nitrobenzoic acid Chemical compound [O-][N+](=O)C1=CC(C(=O)O)=CC=C1OCCN1CCOCC1 CSNHQUYGQIHHLS-UHFFFAOYSA-N 0.000 description 1
• MTTBXKVGISPBNJ-UHFFFAOYSA-N 4-(2-morpholin-4-ylethoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OCCN1CCOCC1 MTTBXKVGISPBNJ-UHFFFAOYSA-N 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
• AZTNWFDTMYSJHW-UHFFFAOYSA-N 4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)-n-(1,3-thiazol-2-ylmethyl)aniline Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1NCC1=NC=CS1 AZTNWFDTMYSJHW-UHFFFAOYSA-N 0.000 description 1
• WSYLDMIAEBMLEJ-UHFFFAOYSA-N 4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)-n-(1h-pyrazol-5-ylmethyl)aniline Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1NCC=1C=CNN=1 WSYLDMIAEBMLEJ-UHFFFAOYSA-N 0.000 description 1
• YGHRVUOQDCXNJU-UHFFFAOYSA-N 4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)-n-[(4-methoxyphenyl)methyl]aniline Chemical compound C1=CC(OC)=CC=C1CNC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 YGHRVUOQDCXNJU-UHFFFAOYSA-N 0.000 description 1
• BFJMFHQXPVAQOQ-UHFFFAOYSA-N 4-(6-chloro-7-methyl-1H-imidazo[4,5-b]pyridin-2-yl)-2-nitrophenol Chemical compound N=1C=2C(C)=C(Cl)C=NC=2NC=1C1=CC=C(O)C([N+]([O-])=O)=C1 BFJMFHQXPVAQOQ-UHFFFAOYSA-N 0.000 description 1
• HGDRXADJVGVGBC-UHFFFAOYSA-N 4-(dimethylamino)-2-methoxybenzaldehyde Chemical compound COC1=CC(N(C)C)=CC=C1C=O HGDRXADJVGVGBC-UHFFFAOYSA-N 0.000 description 1
• BEVJZBLKTKOLNS-UHFFFAOYSA-N 4-(hydroxymethoxy)benzaldehyde Chemical compound OCOC1=CC=C(C=O)C=C1 BEVJZBLKTKOLNS-UHFFFAOYSA-N 0.000 description 1
• SKLUWKYNZNXSLX-UHFFFAOYSA-N 4-Acetamidobenzaldehyde Chemical compound CC(=O)NC1=CC=C(C=O)C=C1 SKLUWKYNZNXSLX-UHFFFAOYSA-N 0.000 description 1
• BUCQKDJJDPGCLD-UHFFFAOYSA-N 4-[(5-chlorothiadiazol-4-yl)methoxy]benzaldehyde Chemical compound S1N=NC(COC=2C=CC(C=O)=CC=2)=C1Cl BUCQKDJJDPGCLD-UHFFFAOYSA-N 0.000 description 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 group 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 description 1
• GBHNAHRCTNGIMC-UHFFFAOYSA-N 4-[2-[4-[6-chloro-7-(4-methylphenyl)-1h-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]morpholine Chemical compound C1=CC(C)=CC=C1C1=C(Cl)C=NC2=C1N=C(C=1C=CC(OCCN3CCOCC3)=CC=1)N2 GBHNAHRCTNGIMC-UHFFFAOYSA-N 0.000 description 1
• ZYOHTXKOHWSJMZ-UHFFFAOYSA-N 4-[3-(dimethylamino)propoxy]benzaldehyde Chemical compound CN(C)CCCOC1=CC=C(C=O)C=C1 ZYOHTXKOHWSJMZ-UHFFFAOYSA-N 0.000 description 1
• YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 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 description 1
• XYWIPYBIIRTJMM-IBGZPJMESA-N 4-[[(2S)-2-[4-[5-chloro-2-[4-(trifluoromethyl)triazol-1-yl]phenyl]-5-methoxy-2-oxopyridin-1-yl]butanoyl]amino]-2-fluorobenzamide Chemical compound CC[C@H](N1C=C(OC)C(=CC1=O)C1=C(C=CC(Cl)=C1)N1C=C(N=N1)C(F)(F)F)C(=O)NC1=CC(F)=C(C=C1)C(N)=O XYWIPYBIIRTJMM-IBGZPJMESA-N 0.000 description 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 description 1
• KJQKPYPZLHTLLO-UHFFFAOYSA-N 4-[[[2-hydroxy-3-[4-(6-methyl-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]propyl]amino]methyl]phenol Chemical compound N=1C2=CC(C)=CN=C2NC=1C(C=C1)=CC=C1OCC(O)CNCC1=CC=C(O)C=C1 KJQKPYPZLHTLLO-UHFFFAOYSA-N 0.000 description 1
• KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
• RKTQEVMZBCBOSB-UHFFFAOYSA-N 4-aminocyclohexan-1-ol;hydron;chloride Chemical compound Cl.NC1CCC(O)CC1 RKTQEVMZBCBOSB-UHFFFAOYSA-N 0.000 description 1
• UWGFONONBAIDAF-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carbaldehyde Chemical compound BrC=1C=NNC=1C=O UWGFONONBAIDAF-UHFFFAOYSA-N 0.000 description 1
• PDONIKHDXYHTLS-UHFFFAOYSA-N 4-bromothiophene-2-carbaldehyde Chemical compound BrC1=CSC(C=O)=C1 PDONIKHDXYHTLS-UHFFFAOYSA-N 0.000 description 1
• ARIREUPIXAKDAY-UHFFFAOYSA-N 4-butylbenzaldehyde Chemical compound CCCCC1=CC=C(C=O)C=C1 ARIREUPIXAKDAY-UHFFFAOYSA-N 0.000 description 1
• AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
• BOJWTAQWPVBIPG-UHFFFAOYSA-N 4-fluoro-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C([N+]([O-])=O)=C1 BOJWTAQWPVBIPG-UHFFFAOYSA-N 0.000 description 1
• YTHJCZRFJGXPTL-UHFFFAOYSA-N 4-hydroxy-3-nitrobenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1[N+]([O-])=O YTHJCZRFJGXPTL-UHFFFAOYSA-N 0.000 description 1
• DTJVECUKADWGMO-UHFFFAOYSA-N 4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1 DTJVECUKADWGMO-UHFFFAOYSA-N 0.000 description 1
• XJEVFFNOMKXBLU-UHFFFAOYSA-N 4-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(N)C=C1 XJEVFFNOMKXBLU-UHFFFAOYSA-N 0.000 description 1
• PSVPUHBSBYJSMQ-UHFFFAOYSA-N 4-methylsulfonylbenzaldehyde Chemical compound CS(=O)(=O)C1=CC=C(C=O)C=C1 PSVPUHBSBYJSMQ-UHFFFAOYSA-N 0.000 description 1
• PHNDZBFLOPIMSM-UHFFFAOYSA-N 4-morpholin-4-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCOCC1 PHNDZBFLOPIMSM-UHFFFAOYSA-N 0.000 description 1
• XVAJKPNTGSKZSQ-UHFFFAOYSA-N 4-morpholinobenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1CCOCC1 XVAJKPNTGSKZSQ-UHFFFAOYSA-N 0.000 description 1
• QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
• OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
• ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
• RTSOJVJDKNKNFU-UHFFFAOYSA-N 5-(4-nitrophenyl)furan-2-carbaldehyde Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC=C(C=O)O1 RTSOJVJDKNKNFU-UHFFFAOYSA-N 0.000 description 1
• HOCSBVMMCCWNFT-UHFFFAOYSA-N 5-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)-n-[(3-methoxyphenyl)methyl]pyridin-2-amine Chemical compound COC1=CC=CC(CNC=2N=CC(=CC=2)C=2NC3=NC=C(Br)C=C3N=2)=C1 HOCSBVMMCCWNFT-UHFFFAOYSA-N 0.000 description 1
• IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
• QOOCOFOGYRQPPN-UHFFFAOYSA-N 5-bromo-3-nitropyridin-2-amine Chemical compound NC1=NC=C(Br)C=C1[N+]([O-])=O QOOCOFOGYRQPPN-UHFFFAOYSA-N 0.000 description 1
• IIBUKQZJUPSIQA-UHFFFAOYSA-N 5-bromopyridine-2,3-diamine;2-methyl-1h-imidazole-5-carbaldehyde Chemical compound CC1=NC(C=O)=CN1.NC1=CC(Br)=CN=C1N IIBUKQZJUPSIQA-UHFFFAOYSA-N 0.000 description 1
• FXVNVJFNMIOKOL-UHFFFAOYSA-N 5-chloro-4-methoxypyridin-2-amine Chemical compound COC1=CC(N)=NC=C1Cl FXVNVJFNMIOKOL-UHFFFAOYSA-N 0.000 description 1
• LLWKTQALVZANCU-UHFFFAOYSA-N 5-chloro-4-methyl-3-nitropyridin-2-amine Chemical compound CC1=C(Cl)C=NC(N)=C1[N+]([O-])=O LLWKTQALVZANCU-UHFFFAOYSA-N 0.000 description 1
• KMWCSNCNHSEXIF-UHFFFAOYSA-N 5-methyl-1h-imidazole-4-carbaldehyde Chemical compound CC=1N=CNC=1C=O KMWCSNCNHSEXIF-UHFFFAOYSA-N 0.000 description 1
• CHTSWZNXEKOLPM-UHFFFAOYSA-N 5-nitrothiophene-2-carbaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)S1 CHTSWZNXEKOLPM-UHFFFAOYSA-N 0.000 description 1
• OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 1
• CWPORJHTLXOHOQ-UHFFFAOYSA-N 6,7-dichloro-2-(4-nitrophenyl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NC2=C(Cl)C(Cl)=CN=C2N1 CWPORJHTLXOHOQ-UHFFFAOYSA-N 0.000 description 1
• KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
• UAWMVMPAYRWUFX-UHFFFAOYSA-N 6-Chloronicotinic acid Chemical compound OC(=O)C1=CC=C(Cl)N=C1 UAWMVMPAYRWUFX-UHFFFAOYSA-N 0.000 description 1
• KXXNSRRQEABRTD-UHFFFAOYSA-N 6-bromo-2-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(OC)=CC=C1C1=NC2=NC=C(Br)C=C2N1 KXXNSRRQEABRTD-UHFFFAOYSA-N 0.000 description 1
• HNIRXAAMHVGEQT-UHFFFAOYSA-N 6-bromo-2-(4-methylphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(C)=CC=C1C1=NC2=CC(Br)=CN=C2N1 HNIRXAAMHVGEQT-UHFFFAOYSA-N 0.000 description 1
• MHFSRMPSKPLZSA-UHFFFAOYSA-N 6-bromo-2-(4-nitrophenyl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NC2=CC(Br)=CN=C2N1 MHFSRMPSKPLZSA-UHFFFAOYSA-N 0.000 description 1
• VOEWMVOTAKGUHD-UHFFFAOYSA-N 6-bromo-2-(6-chloropyridin-3-yl)-1h-imidazo[4,5-b]pyridine Chemical compound C1=NC(Cl)=CC=C1C1=NC2=CC(Br)=CN=C2N1 VOEWMVOTAKGUHD-UHFFFAOYSA-N 0.000 description 1
• FVVYARDSFYOHSX-UHFFFAOYSA-N 6-bromo-2-[4-(2-piperidin-1-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCN1CCCCC1 FVVYARDSFYOHSX-UHFFFAOYSA-N 0.000 description 1
• JFKBMRRXYUCKDV-UHFFFAOYSA-N 6-bromo-2-[4-(3-piperidin-1-ylpropoxy)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCCN1CCCCC1 JFKBMRRXYUCKDV-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• HSGIAQPAZMREJF-UHFFFAOYSA-N 6-bromo-2-[4-(bromomethyl)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(CBr)=CC=C1C1=NC2=CC(Br)=CN=C2N1 HSGIAQPAZMREJF-UHFFFAOYSA-N 0.000 description 1
• UBJUDMRXEXDDCK-UHFFFAOYSA-N 6-bromo-2-[5-(4-nitrophenyl)furan-2-yl]-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)O1 UBJUDMRXEXDDCK-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• AFBVNOQYJUVZGR-UHFFFAOYSA-N 6-chloro-2-(4-fluoro-3-nitrophenyl)-7-methyl-1h-imidazo[4,5-b]pyridine Chemical compound N=1C=2C(C)=C(Cl)C=NC=2NC=1C1=CC=C(F)C([N+]([O-])=O)=C1 AFBVNOQYJUVZGR-UHFFFAOYSA-N 0.000 description 1
• FXHQROHRCLWIOU-UHFFFAOYSA-N 6-chloro-2-(4-nitrophenyl)-n-phenyl-1h-imidazo[4,5-b]pyridin-7-amine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(NC1=NC=C2Cl)=NC1=C2NC1=CC=CC=C1 FXHQROHRCLWIOU-UHFFFAOYSA-N 0.000 description 1
• INIKPKBUENGBCJ-UHFFFAOYSA-N 6-chloro-2-[4-(2-chloroethoxy)phenyl]-7-methoxy-1h-imidazo[4,5-b]pyridine Chemical compound N=1C=2C(OC)=C(Cl)C=NC=2NC=1C1=CC=C(OCCCl)C=C1 INIKPKBUENGBCJ-UHFFFAOYSA-N 0.000 description 1
• MJUAYHZFPGUPAX-UHFFFAOYSA-N 6-chloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-n-(1-phenylethyl)-1h-imidazo[4,5-b]pyridin-7-amine Chemical compound C=1C=CC=CC=1C(C)NC(C=1N=2)=C(Cl)C=NC=1NC=2C(C=C1)=CC=C1OCCN1CCOCC1 MJUAYHZFPGUPAX-UHFFFAOYSA-N 0.000 description 1
• NQNBFKJDZAZRAS-UHFFFAOYSA-N 6-chloro-6-hydroxycyclohexa-2,4-diene-1-carbaldehyde Chemical compound OC1(Cl)C=CC=CC1C=O NQNBFKJDZAZRAS-UHFFFAOYSA-N 0.000 description 1
• UNFRFBOIYMMWAB-UHFFFAOYSA-N 6-chloro-7-methoxy-2-(4-nitrophenyl)-1h-imidazo[4,5-b]pyridine Chemical compound N=1C=2C(OC)=C(Cl)C=NC=2NC=1C1=CC=C([N+]([O-])=O)C=C1 UNFRFBOIYMMWAB-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• 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 description 1
• XFWJEVAKZHLUAG-UHFFFAOYSA-N 6-chloro-n-cyclopentyl-2-[4-(2-morpholin-4-ylethoxy)phenyl]-1h-imidazo[4,5-b]pyridin-7-amine Chemical compound ClC1=CN=C2N=C(C=3C=CC(OCCN4CCOCC4)=CC=3)NC2=C1NC1CCCC1 XFWJEVAKZHLUAG-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• KTUFZHVVJBHGKZ-UHFFFAOYSA-N 7-methyl-1h-indole-3-carbaldehyde Chemical compound CC1=CC=CC2=C1NC=C2C=O KTUFZHVVJBHGKZ-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 1
• 244000215068 Acacia senegal Species 0.000 description 1
• 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
• 208000035939 Alveolitis allergic Diseases 0.000 description 1
• 229920000945 Amylopectin Polymers 0.000 description 1
• 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
• 102000009515 Arachidonate 15-Lipoxygenase Human genes 0.000 description 1
• 108010048907 Arachidonate 15-lipoxygenase Proteins 0.000 description 1
• 240000005528 Arctium lappa Species 0.000 description 1
• 201000001320 Atherosclerosis Diseases 0.000 description 1
• 201000008283 Atrophic Rhinitis Diseases 0.000 description 1
• 108091008875 B cell receptors Proteins 0.000 description 1
• 102100035634 B-cell linker protein Human genes 0.000 description 1
• 101710083670 B-cell linker protein Proteins 0.000 description 1
• 208000009137 Behcet syndrome Diseases 0.000 description 1
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
• JIIPAQGMTNSKPD-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC(=C(C=C2)OCCN2CCOCC2)[N+](=O)[O-].ClC=2C=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)OCCN1CCCCC1 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC(=C(C=C2)OCCN2CCOCC2)[N+](=O)[O-].ClC=2C=C1C(=NC2)NC(=N1)C1=CC=C(C=C1)OCCN1CCCCC1 JIIPAQGMTNSKPD-UHFFFAOYSA-N 0.000 description 1
• OCLMFIRXERQIML-UHFFFAOYSA-N C(C1=CC=CC=C1)N(C1=C2C(=NC=C1Cl)N=C(N2)C2=CC=C(C=C2)OCCN2CCOCC2)C.ClC=2C(=C1C(=NC2)N=C(N1)C1=CC=C(C=C1)OCCN1CCOCC1)NCCO Chemical compound C(C1=CC=CC=C1)N(C1=C2C(=NC=C1Cl)N=C(N2)C2=CC=C(C=C2)OCCN2CCOCC2)C.ClC=2C(=C1C(=NC2)N=C(N1)C1=CC=C(C=C1)OCCN1CCOCC1)NCCO OCLMFIRXERQIML-UHFFFAOYSA-N 0.000 description 1
• 101150041968 CDC13 gene Proteins 0.000 description 1
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
• UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 208000015943 Coeliac disease Diseases 0.000 description 1
• 206010009900 Colitis ulcerative Diseases 0.000 description 1
• 206010010744 Conjunctivitis allergic Diseases 0.000 description 1
• 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• 208000011231 Crohn disease Diseases 0.000 description 1
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• QWIZNVHXZXRPDR-UHFFFAOYSA-N D-melezitose Natural products O1C(CO)C(O)C(O)C(O)C1OC1C(O)C(CO)OC1(CO)OC1OC(CO)C(O)C(O)C1O QWIZNVHXZXRPDR-UHFFFAOYSA-N 0.000 description 1
• 206010012442 Dermatitis contact Diseases 0.000 description 1
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 1
• 101100456896 Drosophila melanogaster metl gene Proteins 0.000 description 1
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
• 239000004150 EU approved colour Substances 0.000 description 1
• 206010014989 Epidermolysis bullosa Diseases 0.000 description 1
• 206010015150 Erythema Diseases 0.000 description 1
• DNPIGRLFVYOBRA-UHFFFAOYSA-N FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.C(C)N1CC(CCC1)N Chemical compound FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.C(C)N1CC(CCC1)N DNPIGRLFVYOBRA-UHFFFAOYSA-N 0.000 description 1
• GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
• 208000027445 Farmer Lung Diseases 0.000 description 1
• 206010016228 Fasciitis Diseases 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
• 208000005577 Gastroenteritis Diseases 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• 108010024636 Glutathione Proteins 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 239000007995 HEPES buffer Substances 0.000 description 1
• 208000030836 Hashimoto thyroiditis Diseases 0.000 description 1
• 241000238631 Hexapoda Species 0.000 description 1
• 101001047640 Homo sapiens Linker for activation of T-cells family member 1 Proteins 0.000 description 1
• 101001090688 Homo sapiens Lymphocyte cytosolic protein 2 Proteins 0.000 description 1
• 101000702132 Homo sapiens Protein spinster homolog 1 Proteins 0.000 description 1
• 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
• 101000914514 Homo sapiens T-cell-specific surface glycoprotein CD28 Proteins 0.000 description 1
• MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
• 201000003838 Idiopathic interstitial pneumonia Diseases 0.000 description 1
• 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 1
• 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
• 208000009388 Job Syndrome Diseases 0.000 description 1
• ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
• VLJNHYLEOZPXFW-BYPYZUCNSA-N L-prolinamide Chemical compound NC(=O)[C@@H]1CCCN1 VLJNHYLEOZPXFW-BYPYZUCNSA-N 0.000 description 1
• 241000222722 Leishmania <genus> Species 0.000 description 1
• 206010024227 Lepromatous leprosy Diseases 0.000 description 1
• 102100024032 Linker for activation of T-cells family member 1 Human genes 0.000 description 1
• 241001490312 Lithops pseudotruncatella Species 0.000 description 1
• 102100034709 Lymphocyte cytosolic protein 2 Human genes 0.000 description 1
• 108091054455 MAP kinase family Proteins 0.000 description 1
• 102000043136 MAP kinase family Human genes 0.000 description 1
• 208000019695 Migraine disease Diseases 0.000 description 1
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
• AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
• FEYNFHSRETUBEM-UHFFFAOYSA-N N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide Chemical compound COc1ccc(cc1)N1N=C(C)C(C(=O)Nc2cccc(c2)C(C)(F)F)C1=O FEYNFHSRETUBEM-UHFFFAOYSA-N 0.000 description 1
• 238000012565 NMR experiment Methods 0.000 description 1
• 206010028735 Nasal congestion Diseases 0.000 description 1
• 206010029164 Nephrotic syndrome Diseases 0.000 description 1
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
• IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
• 239000005642 Oleic acid Substances 0.000 description 1
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
• NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
• 241000042032 Petrocephalus catostoma Species 0.000 description 1
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 1
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 1
• 206010036774 Proctitis Diseases 0.000 description 1
• ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
• 201000004681 Psoriasis Diseases 0.000 description 1
• 201000001263 Psoriatic Arthritis Diseases 0.000 description 1
• 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
• MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
• 208000033464 Reiter syndrome Diseases 0.000 description 1
• 206010039088 Rhinitis atrophic Diseases 0.000 description 1
• 208000036284 Rhinitis seasonal Diseases 0.000 description 1
• 102000014400 SH2 domains Human genes 0.000 description 1
• 108050003452 SH2 domains Proteins 0.000 description 1
• 102000000395 SH3 domains Human genes 0.000 description 1
• 108050008861 SH3 domains Proteins 0.000 description 1
• 101710184528 Scaffolding protein Proteins 0.000 description 1
• 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
• 208000009359 Sezary Syndrome Diseases 0.000 description 1
• 208000021388 Sezary disease Diseases 0.000 description 1
• 208000021386 Sjogren Syndrome Diseases 0.000 description 1
• 201000009594 Systemic Scleroderma Diseases 0.000 description 1
• 206010042953 Systemic sclerosis Diseases 0.000 description 1
• 230000006044 T cell activation Effects 0.000 description 1
• 108091008874 T cell receptors Proteins 0.000 description 1
• 102000016266 T-Cell Antigen Receptors Human genes 0.000 description 1
• 102100027213 T-cell-specific surface glycoprotein CD28 Human genes 0.000 description 1
• 102000040945 Transcription factor Human genes 0.000 description 1
• 108091023040 Transcription factor Proteins 0.000 description 1
• HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
• MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
• 201000006704 Ulcerative Colitis Diseases 0.000 description 1
• 208000024780 Urticaria Diseases 0.000 description 1
• 206010046851 Uveitis Diseases 0.000 description 1
• 206010047112 Vasculitides Diseases 0.000 description 1
• 206010047115 Vasculitis Diseases 0.000 description 1
• 101001038499 Yarrowia lipolytica (strain CLIB 122 / E 150) Lysine acetyltransferase Proteins 0.000 description 1
• LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
• 239000000205 acacia gum Substances 0.000 description 1
• 235000010489 acacia gum Nutrition 0.000 description 1
• SLORFTKXKGVINN-UHFFFAOYSA-N acetic acid;2,2,2-trifluoroacetic acid Chemical compound CC(O)=O.OC(=O)C(F)(F)F.OC(=O)C(F)(F)F SLORFTKXKGVINN-UHFFFAOYSA-N 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 239000004480 active ingredient Substances 0.000 description 1
• 238000001042 affinity chromatography Methods 0.000 description 1
• 201000009961 allergic asthma Diseases 0.000 description 1
• 208000002205 allergic conjunctivitis Diseases 0.000 description 1
• 230000007815 allergy Effects 0.000 description 1
• 208000004631 alopecia areata Diseases 0.000 description 1
• HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• 235000019270 ammonium chloride Nutrition 0.000 description 1
• UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
• 239000000538 analytical sample Substances 0.000 description 1
• 239000003146 anticoagulant agent Substances 0.000 description 1
• 229940127219 anticoagulant drug Drugs 0.000 description 1
• 239000012300 argon atmosphere Substances 0.000 description 1
• 150000001491 aromatic compounds Chemical class 0.000 description 1
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
• 125000004429 atom Chemical group 0.000 description 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
• 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 1
• 210000003719 b-lymphocyte Anatomy 0.000 description 1
• 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
• WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 1
• UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
• 239000003833 bile salt Substances 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• JFIOVJDNOJYLKP-UHFFFAOYSA-N bithionol Chemical compound OC1=C(Cl)C=C(Cl)C=C1SC1=CC(Cl)=CC(Cl)=C1O JFIOVJDNOJYLKP-UHFFFAOYSA-N 0.000 description 1
• 230000036772 blood pressure Effects 0.000 description 1
• 210000000988 bone and bone Anatomy 0.000 description 1
• 210000001185 bone marrow Anatomy 0.000 description 1
• 206010006451 bronchitis Diseases 0.000 description 1
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
• 235000013539 calcium stearate Nutrition 0.000 description 1
• 239000008116 calcium stearate Substances 0.000 description 1
• 230000003185 calcium uptake Effects 0.000 description 1
• 125000002837 carbocyclic group Chemical group 0.000 description 1
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
• 239000000496 cardiotonic agent Substances 0.000 description 1
• 230000003177 cardiotonic effect Effects 0.000 description 1
• 239000002327 cardiovascular agent Substances 0.000 description 1
• 229940125692 cardiovascular agent Drugs 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
• 210000004027 cell Anatomy 0.000 description 1
• 230000011712 cell development Effects 0.000 description 1
• 230000024245 cell differentiation Effects 0.000 description 1
• 230000003915 cell function Effects 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 239000003610 charcoal Substances 0.000 description 1
• DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 1
• 239000003638 chemical reducing agent Substances 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 229940068911 chloride hexahydrate Drugs 0.000 description 1
• VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
• 208000017760 chronic graft versus host disease Diseases 0.000 description 1
• 201000009151 chronic rhinitis Diseases 0.000 description 1
• 208000027157 chronic rhinosinusitis Diseases 0.000 description 1
• 238000010549 co-Evaporation Methods 0.000 description 1
• 208000010247 contact dermatitis Diseases 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 210000004087 cornea Anatomy 0.000 description 1
• 239000006184 cosolvent Substances 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
• 230000003226 decolorizating effect Effects 0.000 description 1
• 230000007547 defect Effects 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• 235000013681 dietary sucrose Nutrition 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
• 208000035475 disorder Diseases 0.000 description 1
• 238000006073 displacement reaction Methods 0.000 description 1
• 238000009826 distribution Methods 0.000 description 1
• 239000000428 dust Substances 0.000 description 1
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
• 108010075324 emt protein-tyrosine kinase Proteins 0.000 description 1
• 210000002889 endothelial cell Anatomy 0.000 description 1
• GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
• XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 description 1
• 231100000321 erythema Toxicity 0.000 description 1
• VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 208000022195 farmer lung disease Diseases 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 235000013305 food Nutrition 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
• 238000001640 fractional crystallisation Methods 0.000 description 1
• 230000006870 function Effects 0.000 description 1
• DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 230000002068 genetic effect Effects 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 229960003180 glutathione Drugs 0.000 description 1
• 150000004676 glycans Chemical class 0.000 description 1
• 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
• BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
• 229960001867 guaiacol Drugs 0.000 description 1
• 230000003394 haemopoietic effect Effects 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
• 206010051040 hyper-IgE syndrome Diseases 0.000 description 1
• 230000004047 hyperresponsiveness Effects 0.000 description 1
• 230000001969 hypertrophic effect Effects 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
• 210000002865 immune cell Anatomy 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 229910010272 inorganic material Inorganic materials 0.000 description 1
• 239000011147 inorganic material Substances 0.000 description 1
• 229940030980 inova Drugs 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 239000003456 ion exchange resin Substances 0.000 description 1
• 229920003303 ion-exchange polymer Polymers 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• 230000002427 irreversible effect Effects 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 238000000021 kinase assay Methods 0.000 description 1
• 239000000832 lactitol Substances 0.000 description 1
• VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 description 1
• 235000010448 lactitol Nutrition 0.000 description 1
• 229960003451 lactitol Drugs 0.000 description 1
• 201000010260 leiomyoma Diseases 0.000 description 1
• 201000011486 lichen planus Diseases 0.000 description 1
• 150000002632 lipids Chemical class 0.000 description 1
• 210000004185 liver Anatomy 0.000 description 1
• 230000004807 localization Effects 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
• 239000000845 maltitol Substances 0.000 description 1
• 235000010449 maltitol Nutrition 0.000 description 1
• 229940035436 maltitol Drugs 0.000 description 1
• 229960001855 mannitol Drugs 0.000 description 1
• 238000001819 mass spectrum Methods 0.000 description 1
• 208000008585 mastocytosis Diseases 0.000 description 1
• 210000003519 mature b lymphocyte Anatomy 0.000 description 1
• QWIZNVHXZXRPDR-WSCXOGSTSA-N melezitose Chemical compound O([C@@]1(O[C@@H]([C@H]([C@@H]1O[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O)CO)CO)[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O QWIZNVHXZXRPDR-WSCXOGSTSA-N 0.000 description 1
• 239000012528 membrane Substances 0.000 description 1
• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
• 229910052753 mercury Inorganic materials 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
• CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical group COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 description 1
• 206010027599 migraine Diseases 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 108091006026 monomeric small GTPases Proteins 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• 201000006417 multiple sclerosis Diseases 0.000 description 1
• 206010028417 myasthenia gravis Diseases 0.000 description 1
• 201000005962 mycosis fungoides Diseases 0.000 description 1
• CZGIEJXGCLWRPY-UHFFFAOYSA-N n,1-dimethylpyrrolidin-3-amine Chemical compound CNC1CCN(C)C1 CZGIEJXGCLWRPY-UHFFFAOYSA-N 0.000 description 1
• AVAWMINJNRAQFS-UHFFFAOYSA-N n,n-dimethylpyrrolidin-3-amine Chemical compound CN(C)C1CCNC1 AVAWMINJNRAQFS-UHFFFAOYSA-N 0.000 description 1
• CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
• QUSRVLXZSXFRQC-UHFFFAOYSA-N n-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]-1,3-thiazol-2-amine Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCNC1=NC=CS1 QUSRVLXZSXFRQC-UHFFFAOYSA-N 0.000 description 1
• WYVLUZIBSZJDJH-UHFFFAOYSA-N n-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]-2-(1h-imidazol-5-yl)ethanamine Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCNCCC1=CNC=N1 WYVLUZIBSZJDJH-UHFFFAOYSA-N 0.000 description 1
• YIHTYDCTMYUREO-UHFFFAOYSA-N n-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]-2-(4-chlorophenyl)ethanamine Chemical compound C1=CC(Cl)=CC=C1CCNCCOC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 YIHTYDCTMYUREO-UHFFFAOYSA-N 0.000 description 1
• LMGSTRBDOPUVAD-UHFFFAOYSA-N n-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]-2h-tetrazol-5-amine Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCNC1=NN=NN1 LMGSTRBDOPUVAD-UHFFFAOYSA-N 0.000 description 1
• DMBXOVNEKVFZEK-UHFFFAOYSA-N n-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]-4,5-dihydro-1,3-thiazol-2-amine Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCNC1=NCCS1 DMBXOVNEKVFZEK-UHFFFAOYSA-N 0.000 description 1
• WXINFDSMYUJMLO-UHFFFAOYSA-N n-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]-n-methyl-2-phenylethanamine Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCCN(C)CCC1=CC=CC=C1 WXINFDSMYUJMLO-UHFFFAOYSA-N 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• IIMOILNAFYTXSR-UHFFFAOYSA-N n-[4-(6,7-dichloro-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(C=2NC3=C(Cl)C(Cl)=CN=C3N=2)C=C1 IIMOILNAFYTXSR-UHFFFAOYSA-N 0.000 description 1
• CXONFAMPJGKMFF-UHFFFAOYSA-N n-[4-(6-bromo-7-methyl-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(C=2NC3=C(C)C(Br)=CN=C3N=2)C=C1 CXONFAMPJGKMFF-UHFFFAOYSA-N 0.000 description 1
• LCDSUWMUPJYAPC-UHFFFAOYSA-N n-benzyl-2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-n-methylethanamine Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCCN(C)CC1=CC=CC=C1 LCDSUWMUPJYAPC-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 210000000822 natural killer cell Anatomy 0.000 description 1
• 229910052759 nickel Inorganic materials 0.000 description 1
• 238000006396 nitration reaction Methods 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
• 239000012188 paraffin wax Substances 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000003182 parenteral nutrition solution Substances 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 239000008177 pharmaceutical agent Substances 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
• 150000003904 phospholipids Chemical class 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 1
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 229920005862 polyol Polymers 0.000 description 1
• 150000003077 polyols Chemical class 0.000 description 1
• 229920000137 polyphosphoric acid Polymers 0.000 description 1
• 208000015768 polyposis Diseases 0.000 description 1
• 229920001282 polysaccharide Polymers 0.000 description 1
• 239000005017 polysaccharide Substances 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
• 229920001592 potato starch Polymers 0.000 description 1
• 239000003380 propellant Substances 0.000 description 1
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• 108090000623 proteins and genes Proteins 0.000 description 1
• 208000005069 pulmonary fibrosis Diseases 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
• ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• JUYUYCIJACTHMK-UHFFFAOYSA-N quinoline-8-sulfonyl chloride Chemical compound C1=CN=C2C(S(=O)(=O)Cl)=CC=CC2=C1 JUYUYCIJACTHMK-UHFFFAOYSA-N 0.000 description 1
• MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
• 208000002574 reactive arthritis Diseases 0.000 description 1
• 230000011514 reflex Effects 0.000 description 1
• 230000003252 repetitive effect Effects 0.000 description 1
• 210000002345 respiratory system Anatomy 0.000 description 1
• 206010039073 rheumatoid arthritis Diseases 0.000 description 1
• CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
• 201000000306 sarcoidosis Diseases 0.000 description 1
• 239000012047 saturated solution Substances 0.000 description 1
• 238000012216 screening Methods 0.000 description 1
• XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
• 238000010898 silica gel chromatography Methods 0.000 description 1
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
• 201000009890 sinusitis Diseases 0.000 description 1
• 102000030938 small GTPase Human genes 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
• LDUSJDKDOAZXLC-UHFFFAOYSA-N sodium methanolate 2,2,2-trifluoroacetic acid Chemical compound C[O-].[Na+].FC(C(=O)O)(F)F LDUSJDKDOAZXLC-UHFFFAOYSA-N 0.000 description 1
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 235000010356 sorbitol Nutrition 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 201000005671 spondyloarthropathy Diseases 0.000 description 1
• 108010087686 src-Family Kinases Proteins 0.000 description 1
• 102000009076 src-Family Kinases Human genes 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 239000012258 stirred mixture Substances 0.000 description 1
• 239000012089 stop solution Substances 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 150000005846 sugar alcohols Chemical class 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• 229940124530 sulfonamide Drugs 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 230000002459 sustained effect Effects 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• YDBPZCVWPFMBDH-MRVPVSSYSA-N tert-butyl (2r)-2-formylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H]1C=O YDBPZCVWPFMBDH-MRVPVSSYSA-N 0.000 description 1
• IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
• CWCFCGSAAZGWCE-UHFFFAOYSA-N tert-butyl n-(2-bromoethyl)-n-methylcarbamate Chemical compound BrCCN(C)C(=O)OC(C)(C)C CWCFCGSAAZGWCE-UHFFFAOYSA-N 0.000 description 1
• 239000002562 thickening agent Substances 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
• QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
• 239000004408 titanium dioxide Substances 0.000 description 1
• 235000010215 titanium dioxide Nutrition 0.000 description 1
• DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 1
• 238000002054 transplantation Methods 0.000 description 1
• 229940074410 trehalose Drugs 0.000 description 1
• 201000008827 tuberculosis Diseases 0.000 description 1
• 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
• MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
• 208000001319 vasomotor rhinitis Diseases 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 201000005539 vernal conjunctivitis Diseases 0.000 description 1
• 239000001993 wax Substances 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1