CA2637392A1 - Imidazopyridine derivatives inhibiting protein kinase activity, method for the preparation thereof and pharmaceutical composition containing same - Google Patents

Info

Publication number

CA2637392A1

CA2637392A1 CA002637392A CA2637392A CA2637392A1 CA 2637392 A1 CA2637392 A1 CA 2637392A1 CA 002637392 A CA002637392 A CA 002637392A CA 2637392 A CA2637392 A CA 2637392A CA 2637392 A1 CA2637392 A1 CA 2637392A1

Authority

CA

Canada

Prior art keywords

imidazo

pyridine

phenyl

carboxylic acid

amide

Prior art date

2006-01-23

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

• 230000000694 effects Effects 0.000 title claims abstract description 26
• 102000001253 Protein Kinase Human genes 0.000 title claims abstract description 20
• 108060006633 protein kinase Proteins 0.000 title claims abstract description 20
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
• 238000000034 method Methods 0.000 title claims description 39
• 230000002401 inhibitory effect Effects 0.000 title claims description 19
• 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title abstract 2
• 238000002360 preparation method Methods 0.000 title description 46
• 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims abstract description 20
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 12
• 108091008611 Protein Kinase B Proteins 0.000 claims abstract description 11
• 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 claims abstract description 10
• 201000011510 cancer Diseases 0.000 claims abstract description 9
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 9
• 102000003989 Aurora kinases Human genes 0.000 claims abstract description 7
• 108090000433 Aurora kinases Proteins 0.000 claims abstract description 7
• 108010007457 Extracellular Signal-Regulated MAP Kinases Proteins 0.000 claims abstract description 7
• 102000007665 Extracellular Signal-Regulated MAP Kinases Human genes 0.000 claims abstract description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 6
• 206010061218 Inflammation Diseases 0.000 claims abstract description 5
• 230000004054 inflammatory process Effects 0.000 claims abstract description 5
• 206010012289 Dementia Diseases 0.000 claims abstract description 4
• 201000010099 disease Diseases 0.000 claims abstract description 4
• 208000008589 Obesity Diseases 0.000 claims abstract description 3
• 235000020824 obesity Nutrition 0.000 claims abstract description 3
• 102000005765 Proto-Oncogene Proteins c-akt Human genes 0.000 claims abstract 2
• -1 C1-6alkyloxy Chemical group 0.000 claims description 310
• 239000002253 acid Substances 0.000 claims description 254
• 150000001875 compounds Chemical class 0.000 claims description 245
• 150000001408 amides Chemical group 0.000 claims description 149
• 239000000203 mixture Substances 0.000 claims description 106
• DIEZPEIBLRSBCS-UHFFFAOYSA-N 2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=C(F)C=C1 DIEZPEIBLRSBCS-UHFFFAOYSA-N 0.000 claims description 94
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 90
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
• 239000002904 solvent Substances 0.000 claims description 43
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
• 229910001868 water Inorganic materials 0.000 claims description 39
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 38
• FEQIQCKIKLJLFO-UHFFFAOYSA-N 2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C=1C=CSC=1 FEQIQCKIKLJLFO-UHFFFAOYSA-N 0.000 claims description 36
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 34
• 229910052736 halogen Inorganic materials 0.000 claims description 34
• 150000002367 halogens Chemical group 0.000 claims description 34
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 28
• 125000003118 aryl group Chemical group 0.000 claims description 28
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
• FXLXAUUIWODDSG-UHFFFAOYSA-N 2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=CS1 FXLXAUUIWODDSG-UHFFFAOYSA-N 0.000 claims description 26
• JSRJCOJTWVQZSD-UHFFFAOYSA-N 2-(furan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=CO1 JSRJCOJTWVQZSD-UHFFFAOYSA-N 0.000 claims description 25
• RPHWPBRVXJHHLL-UHFFFAOYSA-N 2-(furan-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C=1C=COC=1 RPHWPBRVXJHHLL-UHFFFAOYSA-N 0.000 claims description 25
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 24
• ZXISZMDLMKPPRD-UHFFFAOYSA-N 2-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=CC=C1 ZXISZMDLMKPPRD-UHFFFAOYSA-N 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 16
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
• 125000001072 heteroaryl group Chemical group 0.000 claims description 16
• 150000003839 salts Chemical class 0.000 claims description 16
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 15
• CHXNAASGPJTHBO-UHFFFAOYSA-N 2-(4-chlorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=C(Cl)C=C1 CHXNAASGPJTHBO-UHFFFAOYSA-N 0.000 claims description 15
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
• 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
• 239000003960 organic solvent Substances 0.000 claims description 12
• 108090000623 proteins and genes Proteins 0.000 claims description 12
• 239000011593 sulfur Substances 0.000 claims description 12
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
• 108010055717 JNK Mitogen-Activated Protein Kinases Proteins 0.000 claims description 10
• 102000043136 MAP kinase family Human genes 0.000 claims description 10
• 108091054455 MAP kinase family Proteins 0.000 claims description 10
• ABDMQSFNJPYOLA-UHFFFAOYSA-N NS(=O)(=O)[N+]([O-])=O Chemical group NS(=O)(=O)[N+]([O-])=O ABDMQSFNJPYOLA-UHFFFAOYSA-N 0.000 claims description 10
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 10
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 10
• 239000012453 solvate Substances 0.000 claims description 10
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 102000004169 proteins and genes Human genes 0.000 claims description 9
• 235000011121 sodium hydroxide Nutrition 0.000 claims description 9
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 8
• 108091000080 Phosphotransferase Proteins 0.000 claims description 8
• 239000004480 active ingredient Substances 0.000 claims description 8
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
• 238000010438 heat treatment Methods 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims description 8
• 102000020233 phosphotransferase Human genes 0.000 claims description 8
• 239000012286 potassium permanganate Substances 0.000 claims description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 7
• 238000010992 reflux Methods 0.000 claims description 7
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
• 102000053067 Pyruvate Dehydrogenase Acetyl-Transferring Kinase Human genes 0.000 claims description 6
• 102000016549 Vascular Endothelial Growth Factor Receptor-2 Human genes 0.000 claims description 6
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 6
• 101710159466 [Pyruvate dehydrogenase (acetyl-transferring)] kinase, mitochondrial Proteins 0.000 claims description 6
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 239000007822 coupling agent Substances 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000002757 morpholinyl group Chemical group 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• 150000007524 organic acids Chemical class 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 6
• 229940124530 sulfonamide Drugs 0.000 claims description 6
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
• 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 5
• 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 5
• FKEVBALJZQKULE-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=C(F)C=C1F FKEVBALJZQKULE-UHFFFAOYSA-N 0.000 claims description 4
• 102000003903 Cyclin-dependent kinases Human genes 0.000 claims description 4
• 108090000266 Cyclin-dependent kinases Proteins 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
• 239000003054 catalyst Substances 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 4
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 239000007800 oxidant agent Substances 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 102000005962 receptors Human genes 0.000 claims description 4
• 108020003175 receptors Proteins 0.000 claims description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims description 4
• 235000011149 sulphuric acid Nutrition 0.000 claims description 4
• UOPKVHCDEOWBAC-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[2-[4-(ethylsulfonylamino)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C=CC(Cl)=CC=1)N2 UOPKVHCDEOWBAC-UHFFFAOYSA-N 0.000 claims description 3
• 229910006124 SOCl2 Inorganic materials 0.000 claims description 3
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
• 238000001816 cooling Methods 0.000 claims description 3
• 125000004188 dichlorophenyl group Chemical group 0.000 claims description 3
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 3
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 3
• 229940073584 methylene chloride Drugs 0.000 claims description 3
• PQCORBHAPGUMBJ-UHFFFAOYSA-N n-[2-[4-(ethylsulfonylamino)phenyl]ethyl]-2-thiophen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1SC=CC=1)N2 PQCORBHAPGUMBJ-UHFFFAOYSA-N 0.000 claims description 3
• 125000003944 tolyl group Chemical group 0.000 claims description 3
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
• FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 2
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 2
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 2
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
• ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims description 2
• VKSFGYPSXMVOKE-UHFFFAOYSA-N 2-(furan-3-yl)-n-[2-[4-(methanesulfonamido)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1=COC=C1)N2 VKSFGYPSXMVOKE-UHFFFAOYSA-N 0.000 claims description 2
• BMFDCOAWYIWFJJ-UHFFFAOYSA-N 2-cyclopropyl-n-[2-[4-(methanesulfonamido)phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C1CC1)N2 BMFDCOAWYIWFJJ-UHFFFAOYSA-N 0.000 claims description 2
• QAJJXHRQPLATMK-UHFFFAOYSA-N 4,5-dichloro-1h-imidazole Chemical compound ClC=1N=CNC=1Cl QAJJXHRQPLATMK-UHFFFAOYSA-N 0.000 claims description 2
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 2
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
• 229910018162 SeO2 Inorganic materials 0.000 claims description 2
• 239000012317 TBTU Substances 0.000 claims description 2
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
• ZIHQUWYJSTVYAT-UHFFFAOYSA-N [NH-][N+]([O-])=O Chemical group [NH-][N+]([O-])=O ZIHQUWYJSTVYAT-UHFFFAOYSA-N 0.000 claims description 2
• CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 claims description 2
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
• 125000004212 difluorophenyl group Chemical group 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
• JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 claims description 2
• 125000002541 furyl group Chemical group 0.000 claims description 2
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
• 125000001041 indolyl group Chemical group 0.000 claims description 2
• JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical group C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 2
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical group C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
• 235000017550 sodium carbonate Nutrition 0.000 claims description 2
• 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
• YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 2
• 125000001544 thienyl group Chemical group 0.000 claims description 2
• 229930192474 thiophene Chemical group 0.000 claims description 2
• YTHVZLQCXJKFCN-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethylamino]phenyl]-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound C1=CC(NCCN(C)C)=CC=C1C1=NC2=C(C(O)=O)C=CN=C2N1 YTHVZLQCXJKFCN-UHFFFAOYSA-N 0.000 claims 18
• ODJBWKPAXQTWRT-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound C1CN(C)CCN1C1=CC=C(C=2NC3=NC=CC(=C3N=2)C(O)=O)C=C1 ODJBWKPAXQTWRT-UHFFFAOYSA-N 0.000 claims 10
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
• OKIGKGXBKIDQCW-UHFFFAOYSA-N 2-(4-pyrrolidin-1-ylphenyl)-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C(C=C1)=CC=C1N1CCCC1 OKIGKGXBKIDQCW-UHFFFAOYSA-N 0.000 claims 7
• YYLGFKSVCZCPPV-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=CC(F)=C1 YYLGFKSVCZCPPV-UHFFFAOYSA-N 0.000 claims 6
• KYQHPBHCANAVMX-UHFFFAOYSA-N 2-(4-piperidin-1-ylphenyl)-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N1(CCCCC1)C1=CC=C(C=C1)C1=NC=2C(=NC=CC=2C(=O)O)N1 KYQHPBHCANAVMX-UHFFFAOYSA-N 0.000 claims 6
• MADDGOYCVBBCPW-UHFFFAOYSA-N 2-[4-(2-morpholin-4-ylethylamino)phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C(C=C1)=CC=C1NCCN1CCOCC1 MADDGOYCVBBCPW-UHFFFAOYSA-N 0.000 claims 6
• OWFKJWOVBUONMG-UHFFFAOYSA-N 2-pyridin-3-yl-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N1=CC(=CC=C1)C1=NC=2C(=NC=CC=2C(=O)O)N1 OWFKJWOVBUONMG-UHFFFAOYSA-N 0.000 claims 6
• VZWQWIABGPXJSY-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=C(Cl)C=C1Cl VZWQWIABGPXJSY-UHFFFAOYSA-N 0.000 claims 5
• RTGHKIIZLAVHKB-UHFFFAOYSA-N 2-cyclopropyl-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N1C=2C(C(=O)O)=CC=NC=2N=C1C1CC1 RTGHKIIZLAVHKB-UHFFFAOYSA-N 0.000 claims 5
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
• HQGXXVORJDZFLH-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)ethyl-methylamino]phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound CN(CCN(C1=CC=C(C=C1)C1=NC=2C(=NC=CC=2C(=O)O)N1)C)C HQGXXVORJDZFLH-UHFFFAOYSA-N 0.000 claims 4
• KBDULIPYGZKXLV-UHFFFAOYSA-N 2-pyridin-2-yl-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N1=C(C=CC=C1)C1=NC=2C(=NC=CC=2C(=O)O)N1 KBDULIPYGZKXLV-UHFFFAOYSA-N 0.000 claims 4
• MUFRLVBIHPTHDD-UHFFFAOYSA-N 2-(4-morpholin-4-ylphenyl)-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C(C=C1)=CC=C1N1CCOCC1 MUFRLVBIHPTHDD-UHFFFAOYSA-N 0.000 claims 3
• AYILHZSYWQDSNE-UHFFFAOYSA-N 2-[4-[3-(diethylamino)pyrrolidin-1-yl]phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound C1C(N(CC)CC)CCN1C1=CC=C(C=2NC3=NC=CC(=C3N=2)C(O)=O)C=C1 AYILHZSYWQDSNE-UHFFFAOYSA-N 0.000 claims 3
• DYRZJCJXPVFJNV-UHFFFAOYSA-N 2-pyridin-4-yl-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N1=CC=C(C=C1)C1=NC=2C(=NC=CC=2C(=O)O)N1 DYRZJCJXPVFJNV-UHFFFAOYSA-N 0.000 claims 3
• OPOGWUQXARTHMP-UHFFFAOYSA-N 6-bromo-2-phenyl-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=CC=C1)C(=O)O OPOGWUQXARTHMP-UHFFFAOYSA-N 0.000 claims 3
• RNJXYMFLEOXNBQ-UHFFFAOYSA-N 2-(1-oxothiophen-3-yl)-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C=1C=CS(=O)C=1 RNJXYMFLEOXNBQ-UHFFFAOYSA-N 0.000 claims 2
• USLKSBWEDVVGFB-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-(4-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(C(=O)NC=3C(=CC=NC=3)C)C=CN=C2N1 USLKSBWEDVVGFB-UHFFFAOYSA-N 0.000 claims 2
• KCOHGYMERVIMPD-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-(6-methoxypyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(C(=O)NC=3C=NC(OC)=CC=3)C=CN=C2N1 KCOHGYMERVIMPD-UHFFFAOYSA-N 0.000 claims 2
• MEUCXTWWHIWTFZ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-(6-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(C(=O)NC=3C=NC(C)=CC=3)C=CN=C2N1 MEUCXTWWHIWTFZ-UHFFFAOYSA-N 0.000 claims 2
• FIKYJRZIEBMIRV-UHFFFAOYSA-N 2-[4-(2-piperidin-1-ylethylamino)phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C(C=C1)=CC=C1NCCN1CCCCC1 FIKYJRZIEBMIRV-UHFFFAOYSA-N 0.000 claims 2
• MNDJLWLXNHDEIL-UHFFFAOYSA-N 2-[4-(3-pyrrolidin-1-ylpropylamino)phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N1(CCCC1)CCCNC1=CC=C(C=C1)C1=NC=2C(=NC=CC=2C(=O)O)N1 MNDJLWLXNHDEIL-UHFFFAOYSA-N 0.000 claims 2
• WLKFYKGSAFDUMK-UHFFFAOYSA-N 2-[4-[3-(dimethylamino)propylamino]phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound C1=CC(NCCCN(C)C)=CC=C1C1=NC2=C(C(O)=O)C=CN=C2N1 WLKFYKGSAFDUMK-UHFFFAOYSA-N 0.000 claims 2
• HVZFEGGFYDPCRX-UHFFFAOYSA-N 2-[4-[4-(dimethylamino)butylamino]phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound CN(CCCCNC1=CC=C(C=C1)C1=NC=2C(=NC=CC=2C(=O)O)N1)C HVZFEGGFYDPCRX-UHFFFAOYSA-N 0.000 claims 2
• VNGVFHUEAOFUFL-UHFFFAOYSA-N 6-bromo-2-(3-fluorophenyl)-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=CC=C1)F)C(=O)O VNGVFHUEAOFUFL-UHFFFAOYSA-N 0.000 claims 2
• MQBDNSDYRHAIFK-UHFFFAOYSA-N n-(4-ethoxypyridin-3-yl)-2-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(OC)=CC=1)N2 MQBDNSDYRHAIFK-UHFFFAOYSA-N 0.000 claims 2
• CWHPXAXQZKXBTI-UHFFFAOYSA-N n-(6-methoxy-4-methylpyridin-3-yl)-2-(4-methoxyphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(C(=O)NC=3C(=CC(OC)=NC=3)C)C=CN=C2N1 CWHPXAXQZKXBTI-UHFFFAOYSA-N 0.000 claims 2
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
• RESOGTFBLIUXKJ-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-n-[2-[4-[[2-(dimethylamino)acetyl]amino]phenyl]ethyl]-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(NC(=O)CN(C)C)=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C(=CC(Cl)=CC=1)Cl)N2 RESOGTFBLIUXKJ-UHFFFAOYSA-N 0.000 claims 1
• SNFMPYNCDDDXMP-UHFFFAOYSA-N 2-(3-chlorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C1=CC=CC(Cl)=C1 SNFMPYNCDDDXMP-UHFFFAOYSA-N 0.000 claims 1
• BJCUCIYPKOQESA-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-(4-ethoxypyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=C(Cl)C=CC=1)N2 BJCUCIYPKOQESA-UHFFFAOYSA-N 0.000 claims 1
• BJYUDQWXCKOMFI-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-(4-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=C(Cl)C=CC=1)N2 BJYUDQWXCKOMFI-UHFFFAOYSA-N 0.000 claims 1
• NUTSBBKBRGDWBN-UHFFFAOYSA-N 2-(3-chlorophenyl)-n-(6-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(C)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=C(Cl)C=CC=1)N2 NUTSBBKBRGDWBN-UHFFFAOYSA-N 0.000 claims 1
• 125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
• CNSQWZVWEBCADO-UHFFFAOYSA-N 2-(3-methoxyphenyl)-n-(4-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound COC1=CC=CC(C=2NC3=NC=CC(=C3N=2)C(=O)NC=2C(=CC=NC=2)C)=C1 CNSQWZVWEBCADO-UHFFFAOYSA-N 0.000 claims 1
• JYADFVHDJMJOFK-UHFFFAOYSA-N 2-(3-methoxyphenyl)-n-(6-methoxypyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound COC1=CC=CC(C=2NC3=NC=CC(=C3N=2)C(=O)NC=2C=NC(OC)=CC=2)=C1 JYADFVHDJMJOFK-UHFFFAOYSA-N 0.000 claims 1
• NXYQAVZJAUFUIP-UHFFFAOYSA-N 2-(3-methoxyphenyl)-n-(6-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound COC1=CC=CC(C=2NC3=NC=CC(=C3N=2)C(=O)NC=2C=NC(C)=CC=2)=C1 NXYQAVZJAUFUIP-UHFFFAOYSA-N 0.000 claims 1
• HEDUISLYKUXQCT-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(4-ethoxypyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCOC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(Cl)=CC=1)N2 HEDUISLYKUXQCT-UHFFFAOYSA-N 0.000 claims 1
• WYZSUVDLXPUOMS-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(4-ethylsulfanylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CCSC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(Cl)=CC=1)N2 WYZSUVDLXPUOMS-UHFFFAOYSA-N 0.000 claims 1
• HZPRBVFHGGHKBK-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(4-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=NC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(Cl)=CC=1)N2 HZPRBVFHGGHKBK-UHFFFAOYSA-N 0.000 claims 1
• LFILIIYOVZWXQP-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(6-methylpyridin-3-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=NC(C)=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(Cl)=CC=1)N2 LFILIIYOVZWXQP-UHFFFAOYSA-N 0.000 claims 1
• MMBLOGUQTXFDRH-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(1h-indol-5-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=C4C=CNC4=CC=3)C=CN=C2N1 MMBLOGUQTXFDRH-UHFFFAOYSA-N 0.000 claims 1
• PNRQKQIJBSGBSQ-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(2,4,4-trimethylpentan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N=1C=2C(C(=O)NC(C)(C)CC(C)(C)C)=CC=NC=2NC=1C1=CC=C(F)C=C1 PNRQKQIJBSGBSQ-UHFFFAOYSA-N 0.000 claims 1
• ZSUVKQIGZLYKBT-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(2-methylbutan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N=1C=2C(C(=O)NC(C)(C)CC)=CC=NC=2NC=1C1=CC=C(F)C=C1 ZSUVKQIGZLYKBT-UHFFFAOYSA-N 0.000 claims 1
• OWSWOLJBRUIBRZ-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(2-methylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 OWSWOLJBRUIBRZ-UHFFFAOYSA-N 0.000 claims 1
• MYYXECYPOSWJRO-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(3,3,5-trimethylcyclohexyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1C(C)(C)CC(C)CC1NC(=O)C1=CC=NC2=C1N=C(C=1C=CC(F)=CC=1)N2 MYYXECYPOSWJRO-UHFFFAOYSA-N 0.000 claims 1
• LMWBLUOSHRWDFY-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-(5-methylhexan-2-yl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound N=1C=2C(C(=O)NC(C)CCC(C)C)=CC=NC=2NC=1C1=CC=C(F)C=C1 LMWBLUOSHRWDFY-UHFFFAOYSA-N 0.000 claims 1
• NSOAUQXIPCRWHD-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-naphthalen-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=C4C=CC=CC4=CC=3)C=CN=C2N1 NSOAUQXIPCRWHD-UHFFFAOYSA-N 0.000 claims 1
• QAGFQPQTMMVBOB-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-phenyl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=CC=CC=3)C=CN=C2N1 QAGFQPQTMMVBOB-UHFFFAOYSA-N 0.000 claims 1
• HUBLLQRDAVHKSE-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-phenyl-n-propan-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=CC=CC=1N(C(C)C)C(=O)C(C=1N=2)=CC=NC=1NC=2C1=CC=C(F)C=C1 HUBLLQRDAVHKSE-UHFFFAOYSA-N 0.000 claims 1
• OPKDMPYKGNOJNL-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-piperidin-4-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC3CCNCC3)C=CN=C2N1 OPKDMPYKGNOJNL-UHFFFAOYSA-N 0.000 claims 1
• ZNOJAIYGZRZNHV-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-pyridin-2-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3N=CC=CC=3)C=CN=C2N1 ZNOJAIYGZRZNHV-UHFFFAOYSA-N 0.000 claims 1
• DYEDOXXZFLAMCF-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=NC=CC=3)C=CN=C2N1 DYEDOXXZFLAMCF-UHFFFAOYSA-N 0.000 claims 1
• BVQXBIYLJQDDNR-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-pyridin-4-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=CN=CC=3)C=CN=C2N1 BVQXBIYLJQDDNR-UHFFFAOYSA-N 0.000 claims 1
• CLCZTFQKXCHQGG-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-quinolin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=C4C=CC=CC4=NC=3)C=CN=C2N1 CLCZTFQKXCHQGG-UHFFFAOYSA-N 0.000 claims 1
• IHOYHHJZSFKVHH-UHFFFAOYSA-N 2-(4-fluorophenyl)-n-quinolin-6-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC=3C=C4C=CC=NC4=CC=3)C=CN=C2N1 IHOYHHJZSFKVHH-UHFFFAOYSA-N 0.000 claims 1
• KHPNUIAWAQGPJW-UHFFFAOYSA-N 2-(4-morpholin-4-ylphenyl)-n-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC(=CC=3)N3CCOCC3)=NC=2C=1C(=O)NC1=CC=CN=C1 KHPNUIAWAQGPJW-UHFFFAOYSA-N 0.000 claims 1
• NPOWZLUWBWSCRY-UHFFFAOYSA-N 2-(4-piperidin-1-ylphenyl)-n-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC(=CC=3)N3CCCCC3)=NC=2C=1C(=O)NC1=CC=CN=C1 NPOWZLUWBWSCRY-UHFFFAOYSA-N 0.000 claims 1
• YANQLUHXIURGSC-UHFFFAOYSA-N 2-[2-[2-[[2-(2,4-dichlorophenyl)-1h-imidazo[4,5-b]pyridine-7-carbonyl]amino]ethyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC=C1CCNC(=O)C1=CC=NC2=C1N=C(C=1C(=CC(Cl)=CC=1)Cl)N2 YANQLUHXIURGSC-UHFFFAOYSA-N 0.000 claims 1
• AUWDQLMIROWQBQ-UHFFFAOYSA-N 2-[3-[2-[(2-phenyl-1h-imidazo[4,5-b]pyridine-7-carbonyl)amino]ethyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C=CC=CC=2)=C1 AUWDQLMIROWQBQ-UHFFFAOYSA-N 0.000 claims 1
• BEGFBKZRIWCJJK-UHFFFAOYSA-N 2-[3-[2-[[2-(2,4-dichlorophenyl)-1h-imidazo[4,5-b]pyridine-7-carbonyl]amino]ethyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(CCNC(=O)C=2C=3N=C(NC=3N=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1 BEGFBKZRIWCJJK-UHFFFAOYSA-N 0.000 claims 1
• VUZDOEHITRVKIW-UHFFFAOYSA-N 2-[4-(2-piperazin-1-ylethylamino)phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C(C=C1)=CC=C1NCCN1CCNCC1 VUZDOEHITRVKIW-UHFFFAOYSA-N 0.000 claims 1
• VDNHHYXGZIFLMB-UHFFFAOYSA-N 2-[4-(2-pyrrolidin-1-ylethylamino)phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N=1C=2C(C(=O)O)=CC=NC=2NC=1C(C=C1)=CC=C1NCCN1CCCC1 VDNHHYXGZIFLMB-UHFFFAOYSA-N 0.000 claims 1
• CPCWXHMBIYZORT-UHFFFAOYSA-N 2-[4-(3-morpholin-4-ylpropylamino)phenyl]-1H-imidazo[4,5-b]pyridine-7-carboxylic acid Chemical compound N1(CCOCC1)CCCNC1=CC=C(C=C1)C1=NC=2C(=NC=CC=2C(=O)O)N1 CPCWXHMBIYZORT-UHFFFAOYSA-N 0.000 claims 1
• XAWXRXNZBKUQHS-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)phenyl]-n-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1CN(C)CCN1C1=CC=C(C=2NC3=NC=CC(=C3N=2)C(=O)NC=2C=NC=CC=2)C=C1 XAWXRXNZBKUQHS-UHFFFAOYSA-N 0.000 claims 1
• KYDFTLLBJAJVRL-UHFFFAOYSA-N 2-[4-(diethylamino)phenyl]-n-pyridin-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(N(CC)CC)=CC=C1C1=NC2=C(C(=O)NC=3C=NC=CC=3)C=CN=C2N1 KYDFTLLBJAJVRL-UHFFFAOYSA-N 0.000 claims 1
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• WGYZRXIWOLISCB-UHFFFAOYSA-N n-cyclohexyl-2-(4-fluorophenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(=O)NC3CCCCC3)C=CN=C2N1 WGYZRXIWOLISCB-UHFFFAOYSA-N 0.000 claims 1
• OCNKAAKYDHRMQV-UHFFFAOYSA-N n-cyclohexyl-2-(4-morpholin-4-ylphenyl)-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C=3C=CC(=CC=3)N3CCOCC3)=NC=2C=1C(=O)NC1CCCCC1 OCNKAAKYDHRMQV-UHFFFAOYSA-N 0.000 claims 1
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• NMYRPXBRICOTPO-UHFFFAOYSA-N n-pyridin-3-yl-2-thiophen-3-yl-1h-imidazo[4,5-b]pyridine-7-carboxamide Chemical compound C=1C=NC=2NC(C3=CSC=C3)=NC=2C=1C(=O)NC1=CC=CN=C1 NMYRPXBRICOTPO-UHFFFAOYSA-N 0.000 claims 1
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