NZ538156A - Use of and some novel imidazopyridines - Google Patents

Info

Publication number

NZ538156A

NZ538156A NZ538156A NZ53815603A NZ538156A NZ 538156 A NZ538156 A NZ 538156A NZ 538156 A NZ538156 A NZ 538156A NZ 53815603 A NZ53815603 A NZ 53815603A NZ 538156 A NZ538156 A NZ 538156A

Authority

NZ

New Zealand

Prior art keywords

imidazo

pyridin

bromo

phenyl

phenoxy

Prior art date

2002-08-14

Links

• Espacenet
• Global Dossier
• Discuss

• 150000005232 imidazopyridines Chemical class 0.000 title description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 447
• 150000001875 compounds Chemical class 0.000 claims abstract description 372
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 160
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 101
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 95
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 91
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 78
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 76
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 66
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 55
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
• 125000001041 indolyl group Chemical group 0.000 claims abstract description 38
• 201000010099 disease Diseases 0.000 claims abstract description 37
• 238000011282 treatment Methods 0.000 claims abstract description 22
• 239000003814 drug Substances 0.000 claims abstract description 20
• 230000000694 effects Effects 0.000 claims abstract description 17
• 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 15
• 230000005764 inhibitory process Effects 0.000 claims abstract description 14
• 238000004519 manufacturing process Methods 0.000 claims abstract description 13
• 230000009286 beneficial effect Effects 0.000 claims abstract description 10
• 125000005843 halogen group Chemical group 0.000 claims abstract 16
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 311
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 286
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 259
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 143
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 138
• 150000001412 amines Chemical class 0.000 claims description 105
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 95
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 95
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 83
• 229910052801 chlorine Inorganic materials 0.000 claims description 79
• 150000002367 halogens Chemical class 0.000 claims description 75
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 64
• 150000003839 salts Chemical class 0.000 claims description 62
• 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 60
• -1 N-[4-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)phenyl]-N-(lH-imidazol-5-ylmethyl)amine 3-( {[4-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)phenyl]amino) methyl)benzonitrile Chemical compound 0.000 claims description 60
• 229910052739 hydrogen Inorganic materials 0.000 claims description 56
• 238000000034 method Methods 0.000 claims description 52
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
• 229920006395 saturated elastomer Polymers 0.000 claims description 45
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 44
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 35
• 238000006243 chemical reaction Methods 0.000 claims description 32
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 29
• 125000000623 heterocyclic group Chemical group 0.000 claims description 29
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 28
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 27
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
• 125000001424 substituent group Chemical group 0.000 claims description 26
• 108091000080 Phosphotransferase Proteins 0.000 claims description 22
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 22
• 102000020233 phosphotransferase Human genes 0.000 claims description 22
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 21
• 125000004076 pyridyl group Chemical group 0.000 claims description 21
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 19
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 17
• 125000000335 thiazolyl group Chemical group 0.000 claims description 17
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 16
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
• 238000011321 prophylaxis Methods 0.000 claims description 14
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 230000008569 process Effects 0.000 claims description 12
• 125000001425 triazolyl group Chemical group 0.000 claims description 12
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 11
• 125000003386 piperidinyl group Chemical group 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 11
• 125000001589 carboacyl group Chemical group 0.000 claims description 10
• QISLSNOTFIIUEE-UHFFFAOYSA-N 5H-1,2-thiazol-2-amine Chemical compound NN1SCC=C1 QISLSNOTFIIUEE-UHFFFAOYSA-N 0.000 claims description 9
• 210000003630 histaminocyte Anatomy 0.000 claims description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 8
• 208000006673 asthma Diseases 0.000 claims description 8
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
• 239000002671 adjuvant Substances 0.000 claims description 7
• 210000003651 basophil Anatomy 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 5
• 239000004593 Epoxy Substances 0.000 claims description 5
• 229910052786 argon Inorganic materials 0.000 claims description 5
• YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 5
• YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 5
• 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 claims description 4
• DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 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
• SGJSQQLUMMGQOS-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#C[C]1CCCCC1 SGJSQQLUMMGQOS-UHFFFAOYSA-N 0.000 claims description 4
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 229940124530 sulfonamide Drugs 0.000 claims description 4
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 4
• PVPTUASRAVWKGX-UHFFFAOYSA-N 1,2-dihydrotriazol-3-amine Chemical compound NN1NNC=C1 PVPTUASRAVWKGX-UHFFFAOYSA-N 0.000 claims description 3
• GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 3
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 3
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 3
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 3
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
• NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims description 3
• 150000002780 morpholines Chemical class 0.000 claims description 3
• BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-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
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 3
• ZTYZEUXZHGOXRT-UHFFFAOYSA-N quinoline-8-sulfonamide Chemical compound C1=CN=C2C(S(=O)(=O)N)=CC=CC2=C1 ZTYZEUXZHGOXRT-UHFFFAOYSA-N 0.000 claims description 3
• YQBKRVPVCLINJJ-UHFFFAOYSA-N 3-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl-methylamino]propanenitrile Chemical compound C1=CC(OCCN(C)CCC#N)=CC=C1C1=NC2=CC(Br)=CN=C2N1 YQBKRVPVCLINJJ-UHFFFAOYSA-N 0.000 claims description 2
• RXXAZAOOQHNXPX-UHFFFAOYSA-N 4-[2-[4-(6-chloro-7-methoxy-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]morpholine Chemical compound N=1C=2C(OC)=C(Cl)C=NC=2NC=1C(C=C1)=CC=C1OCCN1CCOCC1 RXXAZAOOQHNXPX-UHFFFAOYSA-N 0.000 claims description 2
• RSYMBCFJZVPQTO-UHFFFAOYSA-N 4-[4-(6,7-dichloro-1h-imidazo[4,5-b]pyridin-2-yl)phenyl]morpholine Chemical compound N1C2=C(Cl)C(Cl)=CN=C2N=C1C(C=C1)=CC=C1N1CCOCC1 RSYMBCFJZVPQTO-UHFFFAOYSA-N 0.000 claims description 2
• MSZDCGBUFDXUAE-UHFFFAOYSA-N 6-bromo-2-[4-[2-(4-pyrazin-2-ylpiperazin-1-yl)ethoxy]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCN(CC1)CCN1C1=CN=CC=N1 MSZDCGBUFDXUAE-UHFFFAOYSA-N 0.000 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims 2
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 2
• FVSKHRXBFJPNKK-QNFQPYBMSA-N 2,2,3,3,3-pentaprotiopropanenitrile Chemical compound [1H]C([1H])([1H])C([1H])([1H])C#N FVSKHRXBFJPNKK-QNFQPYBMSA-N 0.000 claims 1
• YVPZMBWNDMKAFG-UHFFFAOYSA-N 2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]-n-(oxolan-2-ylmethyl)ethanamine Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1OCCNCC1CCCO1 YVPZMBWNDMKAFG-UHFFFAOYSA-N 0.000 claims 1
• OHJVBZCLUWFMAS-UHFFFAOYSA-N 3-[[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)anilino]methyl]benzonitrile Chemical compound N=1C2=CC(Br)=CN=C2NC=1C(C=C1)=CC=C1NCC1=CC=CC(C#N)=C1 OHJVBZCLUWFMAS-UHFFFAOYSA-N 0.000 claims 1
• XRVSYXLGKUEKAW-UHFFFAOYSA-N 4-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl-methylamino]cyclohexane-1-carbonitrile Chemical compound C=1C=C(C=2NC3=NC=C(Br)C=C3N=2)C=CC=1OCCN(C)C1CCC(C#N)CC1 XRVSYXLGKUEKAW-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
• GRUBFQJKIOHIAU-UHFFFAOYSA-N BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCNC1CN(CCC1)CC)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCCNC(C)C2=CC=CC=C2)C=C1 Chemical compound BrC=1C=C2C(=NC1)NC(=N2)C2=CC=C(OCCNC1CN(CCC1)CC)C=C2.BrC=2C=C1C(=NC2)NC(=N1)C1=CC=C(OCCNC(C)C2=CC=CC=C2)C=C1 GRUBFQJKIOHIAU-UHFFFAOYSA-N 0.000 claims 1
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims 1
• VLJNHYLEOZPXFW-BYPYZUCNSA-N L-prolinamide Chemical compound NC(=O)[C@@H]1CCCN1 VLJNHYLEOZPXFW-BYPYZUCNSA-N 0.000 claims 1
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 1
• 229910052799 carbon Inorganic materials 0.000 claims 1
• 125000004803 chlorobenzyl group Chemical group 0.000 claims 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
• YEWWLHZNWXLVQF-UHFFFAOYSA-N n-[2-[4-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)phenoxy]ethyl]-1-ethylpiperidin-3-amine Chemical compound C1N(CC)CCCC1NCCOC1=CC=C(C=2NC3=NC=C(Br)C=C3N=2)C=C1 YEWWLHZNWXLVQF-UHFFFAOYSA-N 0.000 claims 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 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
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
• 208000010668 atopic eczema Diseases 0.000 abstract description 8
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• 230000001363 autoimmune Effects 0.000 abstract description 5
• 230000002757 inflammatory effect Effects 0.000 abstract description 5
• 230000002062 proliferating effect Effects 0.000 abstract description 5
• 108010075324 emt protein-tyrosine kinase Proteins 0.000 abstract description 2
• 238000000668 atmospheric pressure chemical ionisation mass spectrometry Methods 0.000 description 301
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 130
• 239000000460 chlorine Substances 0.000 description 99
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 98
• 238000005481 NMR spectroscopy Methods 0.000 description 79
• 238000005160 1H NMR spectroscopy Methods 0.000 description 77
• 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
• 235000019439 ethyl acetate Nutrition 0.000 description 62
• 239000000203 mixture Substances 0.000 description 62
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 61
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 61
• 239000011541 reaction mixture Substances 0.000 description 51
• 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 42
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
• 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 37
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 35
• 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
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
• 239000012074 organic phase Substances 0.000 description 26
• 239000000843 powder Substances 0.000 description 25
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