DE69827516T2 - Azabenzimidazol-verbindungen zur modulation der serin/threonin protein-kinase funktion - Google Patents
Azabenzimidazol-verbindungen zur modulation der serin/threonin protein-kinase funktion Download PDFInfo
- Publication number
- DE69827516T2 DE69827516T2 DE69827516T DE69827516T DE69827516T2 DE 69827516 T2 DE69827516 T2 DE 69827516T2 DE 69827516 T DE69827516 T DE 69827516T DE 69827516 T DE69827516 T DE 69827516T DE 69827516 T2 DE69827516 T2 DE 69827516T2
- Authority
- DE
- Germany
- Prior art keywords
- pyridine
- imidazo
- group
- alkyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 title claims description 173
- 108060006633 protein kinase Proteins 0.000 title description 96
- 102000001253 Protein Kinase Human genes 0.000 title description 94
- MTCFGRXMJLQNBG-UHFFFAOYSA-N serine Chemical compound OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 title description 10
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 title description 3
- 239000004473 Threonine Substances 0.000 title description 3
- 241001522306 Serinus serinus Species 0.000 title 1
- 238000000034 method Methods 0.000 claims description 114
- 230000006870 function Effects 0.000 claims description 47
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 101710199605 Endoribonuclease Proteins 0.000 claims description 34
- 206010028980 Neoplasm Diseases 0.000 claims description 34
- 101710113029 Serine/threonine-protein kinase Proteins 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 31
- -1 Azabenzimidazole compound Chemical class 0.000 claims description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
- 239000003814 drug Substances 0.000 claims description 30
- 150000002148 esters Chemical class 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 208000035475 disorder Diseases 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 18
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 230000003993 interaction Effects 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 201000011510 cancer Diseases 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 108091000080 Phosphotransferase Proteins 0.000 claims description 15
- 150000007942 carboxylates Chemical group 0.000 claims description 15
- 102000020233 phosphotransferase Human genes 0.000 claims description 15
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 238000003786 synthesis reaction Methods 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 239000000376 reactant Substances 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 230000019491 signal transduction Effects 0.000 claims description 11
- 239000003226 mitogen Substances 0.000 claims description 9
- 230000001105 regulatory effect Effects 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 5
- 230000004075 alteration Effects 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- BZZXQZOBAUXLHZ-UHFFFAOYSA-N (c-methylsulfanylcarbonimidoyl)azanium;sulfate Chemical compound CSC(N)=N.CSC(N)=N.OS(O)(=O)=O BZZXQZOBAUXLHZ-UHFFFAOYSA-N 0.000 claims description 4
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 201000001441 melanoma Diseases 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- WERABQRUGJIMKQ-UHFFFAOYSA-N 6-chloro-3-nitropyridin-2-amine Chemical compound NC1=NC(Cl)=CC=C1[N+]([O-])=O WERABQRUGJIMKQ-UHFFFAOYSA-N 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- 206010009944 Colon cancer Diseases 0.000 claims description 3
- 201000008808 Fibrosarcoma Diseases 0.000 claims description 3
- 208000032612 Glial tumor Diseases 0.000 claims description 3
- 206010018338 Glioma Diseases 0.000 claims description 3
- 206010033128 Ovarian cancer Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 208000029742 colonic neoplasm Diseases 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- RMAHPRNLQIRHIJ-UHFFFAOYSA-N methyl carbamimidate Chemical compound COC(N)=N RMAHPRNLQIRHIJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- 206010016654 Fibrosis Diseases 0.000 claims description 2
- 208000007766 Kaposi sarcoma Diseases 0.000 claims description 2
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 3
- 102100030011 Endoribonuclease Human genes 0.000 claims 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 230000001028 anti-proliverative effect Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 230000037361 pathway Effects 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 133
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 58
- 108090000623 proteins and genes Proteins 0.000 description 33
- 102100030013 Endoribonuclease Human genes 0.000 description 32
- 230000000694 effects Effects 0.000 description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 238000012360 testing method Methods 0.000 description 26
- 230000002159 abnormal effect Effects 0.000 description 25
- 102000004169 proteins and genes Human genes 0.000 description 25
- 108091054455 MAP kinase family Proteins 0.000 description 24
- 102000043136 MAP kinase family Human genes 0.000 description 24
- 229940079593 drug Drugs 0.000 description 20
- 230000008859 change Effects 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 230000026731 phosphorylation Effects 0.000 description 18
- 238000006366 phosphorylation reaction Methods 0.000 description 18
- 102000004232 Mitogen-Activated Protein Kinase Kinases Human genes 0.000 description 17
- 108090000744 Mitogen-Activated Protein Kinase Kinases Proteins 0.000 description 17
- 230000004663 cell proliferation Effects 0.000 description 17
- 239000000758 substrate Substances 0.000 description 17
- 239000002609 medium Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 102000005962 receptors Human genes 0.000 description 15
- 108020003175 receptors Proteins 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 239000001963 growth medium Substances 0.000 description 14
- 230000003197 catalytic effect Effects 0.000 description 13
- 239000006166 lysate Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 210000001519 tissue Anatomy 0.000 description 11
- 102000001291 MAP Kinase Kinase Kinase Human genes 0.000 description 10
- 108060006687 MAP kinase kinase kinase Proteins 0.000 description 10
- 201000010099 disease Diseases 0.000 description 10
- 230000012010 growth Effects 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- 239000000872 buffer Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 230000001413 cellular effect Effects 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 8
- 239000010452 phosphate Substances 0.000 description 8
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 210000004204 blood vessel Anatomy 0.000 description 7
- 230000003834 intracellular effect Effects 0.000 description 7
- 230000002062 proliferating effect Effects 0.000 description 7
- 230000035755 proliferation Effects 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 7
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 7
- 239000013598 vector Substances 0.000 description 7
- 102000001301 EGF receptor Human genes 0.000 description 6
- 108060006698 EGF receptor Proteins 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000006180 TBST buffer Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000011550 stock solution Substances 0.000 description 6
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002965 ELISA Methods 0.000 description 5
- 241000282412 Homo Species 0.000 description 5
- 102100033479 RAF proto-oncogene serine/threonine-protein kinase Human genes 0.000 description 5
- 101710141955 RAF proto-oncogene serine/threonine-protein kinase Proteins 0.000 description 5
- 150000001413 amino acids Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 230000004071 biological effect Effects 0.000 description 5
- 208000035269 cancer or benign tumor Diseases 0.000 description 5
- 230000010261 cell growth Effects 0.000 description 5
- 210000000170 cell membrane Anatomy 0.000 description 5
- 230000003176 fibrotic effect Effects 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 239000002953 phosphate buffered saline Substances 0.000 description 5
- 229940002612 prodrug Drugs 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- MSMVDUXXGHXHMO-UHFFFAOYSA-N 6-phenoxy-1H-imidazo[4,5-b]pyridine Chemical compound C=1N=C2NC=NC2=CC=1OC1=CC=CC=C1 MSMVDUXXGHXHMO-UHFFFAOYSA-N 0.000 description 4
- GJOKLMLGDMONLW-UHFFFAOYSA-N 6-phenylsulfanylpyridine-2,3-diamine Chemical compound N1=C(N)C(N)=CC=C1SC1=CC=CC=C1 GJOKLMLGDMONLW-UHFFFAOYSA-N 0.000 description 4
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 206010027476 Metastases Diseases 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000001594 aberrant effect Effects 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000033228 biological regulation Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 208000019425 cirrhosis of liver Diseases 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 230000014509 gene expression Effects 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 230000003211 malignant effect Effects 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 238000012544 monitoring process Methods 0.000 description 4
- 108020004707 nucleic acids Proteins 0.000 description 4
- 102000039446 nucleic acids Human genes 0.000 description 4
- 150000007523 nucleic acids Chemical class 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000001488 sodium phosphate Substances 0.000 description 4
- 229910000162 sodium phosphate Inorganic materials 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 4
- 239000011534 wash buffer Substances 0.000 description 4
- 230000029663 wound healing Effects 0.000 description 4
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 4
- ZKKBWNOSVZIFNJ-UHFFFAOYSA-N 2-amino-3,7-dihydropurin-6-one;diphosphono hydrogen phosphate Chemical compound O=C1NC(N)=NC2=C1NC=N2.OP(O)(=O)OP(O)(=O)OP(O)(O)=O ZKKBWNOSVZIFNJ-UHFFFAOYSA-N 0.000 description 3
- XHGUJNXOPXCSLA-UHFFFAOYSA-N 3-nitro-6-phenylsulfanylpyridin-2-amine Chemical compound C1=C([N+]([O-])=O)C(N)=NC(SC=2C=CC=CC=2)=C1 XHGUJNXOPXCSLA-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 102000045595 Phosphoprotein Phosphatases Human genes 0.000 description 3
- 108700019535 Phosphoprotein Phosphatases Proteins 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 241000256251 Spodoptera frugiperda Species 0.000 description 3
- 229920004890 Triton X-100 Polymers 0.000 description 3
- 239000013504 Triton X-100 Substances 0.000 description 3
- 230000033115 angiogenesis Effects 0.000 description 3
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000030833 cell death Effects 0.000 description 3
- 230000024245 cell differentiation Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 230000001086 cytosolic effect Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 230000004069 differentiation Effects 0.000 description 3
- 239000003102 growth factor Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 230000002934 lysing effect Effects 0.000 description 3
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 3
- 229940031826 phenolate Drugs 0.000 description 3
- 229940080469 phosphocellulose Drugs 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 230000014616 translation Effects 0.000 description 3
- 210000004881 tumor cell Anatomy 0.000 description 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 3
- 230000004862 vasculogenesis Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- SWYXLKSBTAOWOT-UHFFFAOYSA-N 6-phenylsulfanyl-1H-imidazo[4,5-b]pyridine Chemical compound C=1N=C2NC=NC2=CC=1SC1=CC=CC=C1 SWYXLKSBTAOWOT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 0 CC(*c1c(*)c(*)c(**)nc1C)=O Chemical compound CC(*c1c(*)c(*)c(**)nc1C)=O 0.000 description 2
- 101800003838 Epidermal growth factor Proteins 0.000 description 2
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 2
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 2
- 102100033067 Growth factor receptor-bound protein 2 Human genes 0.000 description 2
- 102000016285 Guanine Nucleotide Exchange Factors Human genes 0.000 description 2
- 108010067218 Guanine Nucleotide Exchange Factors Proteins 0.000 description 2
- 101000871017 Homo sapiens Growth factor receptor-bound protein 2 Proteins 0.000 description 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 102100033237 Pro-epidermal growth factor Human genes 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 239000012083 RIPA buffer Substances 0.000 description 2
- 102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 description 2
- 108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 238000001042 affinity chromatography Methods 0.000 description 2
- 150000001345 alkine derivatives Chemical group 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 230000000692 anti-sense effect Effects 0.000 description 2
- 230000006907 apoptotic process Effects 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 230000022131 cell cycle Effects 0.000 description 2
- 230000003915 cell function Effects 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000010367 cloning Methods 0.000 description 2
- 239000002299 complementary DNA Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 239000012149 elution buffer Substances 0.000 description 2
- 229940116977 epidermal growth factor Drugs 0.000 description 2
- 238000011067 equilibration Methods 0.000 description 2
- 239000006167 equilibration buffer Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 210000002744 extracellular matrix Anatomy 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000004153 glucose metabolism Effects 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 238000003018 immunoassay Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 201000005296 lung carcinoma Diseases 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 210000003584 mesangial cell Anatomy 0.000 description 2
- 230000009401 metastasis Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- GDZILRLVFHLOMA-UHFFFAOYSA-N methyl n-(6-phenylsulfanyl-1h-imidazo[4,5-b]pyridin-2-yl)carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC=C1 GDZILRLVFHLOMA-UHFFFAOYSA-N 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 230000002297 mitogenic effect Effects 0.000 description 2
- 230000004118 muscle contraction Effects 0.000 description 2
- 230000035772 mutation Effects 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000002773 nucleotide Substances 0.000 description 2
- 125000003729 nucleotide group Chemical group 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 238000003566 phosphorylation assay Methods 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 238000001243 protein synthesis Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 208000037803 restenosis Diseases 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000013207 serial dilution Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000000527 sonication Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000012089 stop solution Substances 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 1
- XVGQHRKNXSUPEF-UHFFFAOYSA-N 2-(trifluoromethyl)benzenethiol Chemical compound FC(F)(F)C1=CC=CC=C1S XVGQHRKNXSUPEF-UHFFFAOYSA-N 0.000 description 1
- ZOQOPXVJANRGJZ-UHFFFAOYSA-N 2-(trifluoromethyl)phenol Chemical compound OC1=CC=CC=C1C(F)(F)F ZOQOPXVJANRGJZ-UHFFFAOYSA-N 0.000 description 1
- DSCJETUEDFKYGN-UHFFFAOYSA-N 2-Methoxybenzenethiol Chemical compound COC1=CC=CC=C1S DSCJETUEDFKYGN-UHFFFAOYSA-N 0.000 description 1
- VRACOPWGUKNVMP-UHFFFAOYSA-N 2-[(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-6-yl)amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CN=C(NC(=O)N2)C2=C1 VRACOPWGUKNVMP-UHFFFAOYSA-N 0.000 description 1
- LXNVXVIFFJFIAH-UHFFFAOYSA-N 2-[(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-6-yl)oxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CN=C(NC(=O)N2)C2=C1 LXNVXVIFFJFIAH-UHFFFAOYSA-N 0.000 description 1
- BEIOXCWZCVRLJL-UHFFFAOYSA-N 2-[(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-6-yl)sulfanyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1SC1=CN=C(NC(=O)N2)C2=C1 BEIOXCWZCVRLJL-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
- AUCPBDMASFBHQR-UHFFFAOYSA-N 2-[[2-(ethoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]amino]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=CC=C1C(O)=O AUCPBDMASFBHQR-UHFFFAOYSA-N 0.000 description 1
- HTQDZQQDPLKNKF-UHFFFAOYSA-N 2-[[2-(ethoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]oxy]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=CC=C1C(O)=O HTQDZQQDPLKNKF-UHFFFAOYSA-N 0.000 description 1
- ALTORJUGDMYIBI-UHFFFAOYSA-N 2-[[2-(ethoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]sulfanyl]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1SC1=CC=CC=C1C(O)=O ALTORJUGDMYIBI-UHFFFAOYSA-N 0.000 description 1
- KEJRPDSYRYQLSS-UHFFFAOYSA-N 2-[[2-(methoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]amino]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC=C1C(O)=O KEJRPDSYRYQLSS-UHFFFAOYSA-N 0.000 description 1
- JDEHKUCFWSGRDM-UHFFFAOYSA-N 2-[[2-(methoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]oxy]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC=C1C(O)=O JDEHKUCFWSGRDM-UHFFFAOYSA-N 0.000 description 1
- DQRBJFMMSDGYJB-UHFFFAOYSA-N 2-[[2-(methoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]sulfanyl]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC=C1C(O)=O DQRBJFMMSDGYJB-UHFFFAOYSA-N 0.000 description 1
- JWDLEVZYUTZUBA-UHFFFAOYSA-N 2-amino-3,7-dihydropurin-6-one;phosphono dihydrogen phosphate Chemical compound OP(O)(=O)OP(O)(O)=O.O=C1NC(N)=NC2=C1NC=N2 JWDLEVZYUTZUBA-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- PWOBDMNCYMQTCE-UHFFFAOYSA-N 2-chlorobenzenethiol Chemical compound SC1=CC=CC=C1Cl PWOBDMNCYMQTCE-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 1
- WJTZZPVVTSDNJJ-UHFFFAOYSA-N 2-fluorobenzenethiol Chemical compound FC1=CC=CC=C1S WJTZZPVVTSDNJJ-UHFFFAOYSA-N 0.000 description 1
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- JKIFPWHZEZQCQA-UHFFFAOYSA-N 2-nitrobenzenethiol Chemical compound [O-][N+](=O)C1=CC=CC=C1S JKIFPWHZEZQCQA-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- RYCSNJCJOVQGBC-UHFFFAOYSA-N 3-(1-cyclopropyl-2h-pyridin-4-yl)-1h-quinolin-2-one Chemical class O=C1NC2=CC=CC=C2C=C1C(C=C1)=CCN1C1CC1 RYCSNJCJOVQGBC-UHFFFAOYSA-N 0.000 description 1
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
- SCURCOWZQJIUGR-UHFFFAOYSA-N 3-(trifluoromethyl)benzenethiol Chemical compound FC(F)(F)C1=CC=CC(S)=C1 SCURCOWZQJIUGR-UHFFFAOYSA-N 0.000 description 1
- UGEJOEBBMPOJMT-UHFFFAOYSA-N 3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1 UGEJOEBBMPOJMT-UHFFFAOYSA-N 0.000 description 1
- MHCPIAJWYAOKAZ-UHFFFAOYSA-N 3-[(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-6-yl)amino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC=2C=C3NC(=O)NC3=NC=2)=C1 MHCPIAJWYAOKAZ-UHFFFAOYSA-N 0.000 description 1
- OWJWZTZMVHSBHX-UHFFFAOYSA-N 3-[(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-6-yl)oxy]benzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=C3NC(=O)NC3=NC=2)=C1 OWJWZTZMVHSBHX-UHFFFAOYSA-N 0.000 description 1
- SAKWCOZLYHYTRZ-UHFFFAOYSA-N 3-[(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-6-yl)sulfanyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(SC=2C=C3NC(=O)NC3=NC=2)=C1 SAKWCOZLYHYTRZ-UHFFFAOYSA-N 0.000 description 1
- PUBLQAYQAOLYDU-UHFFFAOYSA-N 3-[[2-(ethoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]amino]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=CC(C(O)=O)=C1 PUBLQAYQAOLYDU-UHFFFAOYSA-N 0.000 description 1
- MGIOZSGPBLNMEI-UHFFFAOYSA-N 3-[[2-(ethoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]oxy]benzoic acid Chemical compound C1=C2NC(NC(=O)OCC)=NC2=NC=C1OC1=CC=CC(C(O)=O)=C1 MGIOZSGPBLNMEI-UHFFFAOYSA-N 0.000 description 1
- ZNCCJQDHOBKJJI-UHFFFAOYSA-N 3-[[2-(ethoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]sulfanyl]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1SC1=CC=CC(C(O)=O)=C1 ZNCCJQDHOBKJJI-UHFFFAOYSA-N 0.000 description 1
- HCDBHHKSQZISNR-UHFFFAOYSA-N 3-[[2-(methoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]amino]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC(C(O)=O)=C1 HCDBHHKSQZISNR-UHFFFAOYSA-N 0.000 description 1
- YLJCJDYCJGQHOD-UHFFFAOYSA-N 3-[[2-(methoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]oxy]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC(C(O)=O)=C1 YLJCJDYCJGQHOD-UHFFFAOYSA-N 0.000 description 1
- BJOIEHPRYLAOTH-UHFFFAOYSA-N 3-[[2-(methoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]sulfanyl]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC(C(O)=O)=C1 BJOIEHPRYLAOTH-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- CQJDYPZUDYXHLM-UHFFFAOYSA-N 3-chlorobenzenethiol Chemical compound SC1=CC=CC(Cl)=C1 CQJDYPZUDYXHLM-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 1
- ZDEUGINAVLMAET-UHFFFAOYSA-N 3-fluorobenzenethiol Chemical compound FC1=CC=CC(S)=C1 ZDEUGINAVLMAET-UHFFFAOYSA-N 0.000 description 1
- SJTBRFHBXDZMPS-UHFFFAOYSA-N 3-fluorophenol Chemical compound OC1=CC=CC(F)=C1 SJTBRFHBXDZMPS-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- QMVAZEHZOPDGHA-UHFFFAOYSA-N 3-methoxybenzenethiol Chemical compound COC1=CC=CC(S)=C1 QMVAZEHZOPDGHA-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- HBCSOCHVMJKLLO-UHFFFAOYSA-N 3-nitrobenzenethiol Chemical compound [O-][N+](=O)C1=CC=CC(S)=C1 HBCSOCHVMJKLLO-UHFFFAOYSA-N 0.000 description 1
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 description 1
- RSFDFESMVAIVKO-UHFFFAOYSA-N 3-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=CC(S)=C1 RSFDFESMVAIVKO-UHFFFAOYSA-N 0.000 description 1
- WCMLRSZJUIKVCW-UHFFFAOYSA-N 4-(trifluoromethyl)benzenethiol Chemical compound FC(F)(F)C1=CC=C(S)C=C1 WCMLRSZJUIKVCW-UHFFFAOYSA-N 0.000 description 1
- BAYGVMXZJBFEMB-UHFFFAOYSA-N 4-(trifluoromethyl)phenol Chemical compound OC1=CC=C(C(F)(F)F)C=C1 BAYGVMXZJBFEMB-UHFFFAOYSA-N 0.000 description 1
- OKIHXNKYYGUVTE-UHFFFAOYSA-N 4-Fluorothiophenol Chemical compound FC1=CC=C(S)C=C1 OKIHXNKYYGUVTE-UHFFFAOYSA-N 0.000 description 1
- CMJQGCFPKAYVDH-UHFFFAOYSA-N 4-[(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-6-yl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=CN=C(NC(=O)N2)C2=C1 CMJQGCFPKAYVDH-UHFFFAOYSA-N 0.000 description 1
- BZAQKTCIWZWDQC-UHFFFAOYSA-N 4-[(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-6-yl)oxy]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CN=C(NC(=O)N2)C2=C1 BZAQKTCIWZWDQC-UHFFFAOYSA-N 0.000 description 1
- ZMVSXJADQVFHPR-UHFFFAOYSA-N 4-[(2-oxo-1,3-dihydroimidazo[4,5-b]pyridin-6-yl)sulfanyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1SC1=CN=C(NC(=O)N2)C2=C1 ZMVSXJADQVFHPR-UHFFFAOYSA-N 0.000 description 1
- KTDQEWQSNDITOT-UHFFFAOYSA-N 4-[[2-(ethoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]amino]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=C(C(O)=O)C=C1 KTDQEWQSNDITOT-UHFFFAOYSA-N 0.000 description 1
- MKQKOMJTRSQZAB-UHFFFAOYSA-N 4-[[2-(ethoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]oxy]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=C(C(O)=O)C=C1 MKQKOMJTRSQZAB-UHFFFAOYSA-N 0.000 description 1
- FXKWZOUMKACBME-UHFFFAOYSA-N 4-[[2-(ethoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]sulfanyl]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1SC1=CC=C(C(O)=O)C=C1 FXKWZOUMKACBME-UHFFFAOYSA-N 0.000 description 1
- SWJWJDPCTANTIK-UHFFFAOYSA-N 4-[[2-(methoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]amino]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=C(C(O)=O)C=C1 SWJWJDPCTANTIK-UHFFFAOYSA-N 0.000 description 1
- DXYOSVDHCYUPNN-UHFFFAOYSA-N 4-[[2-(methoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]oxy]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=C(C(O)=O)C=C1 DXYOSVDHCYUPNN-UHFFFAOYSA-N 0.000 description 1
- HYCQJGXAJGDGSQ-UHFFFAOYSA-N 4-[[2-(methoxycarbonylamino)-1h-imidazo[4,5-b]pyridin-6-yl]sulfanyl]benzoic acid Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=C(C(O)=O)C=C1 HYCQJGXAJGDGSQ-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- NIFAOMSJMGEFTQ-UHFFFAOYSA-N 4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1 NIFAOMSJMGEFTQ-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- AXBVSRMHOPMXBA-UHFFFAOYSA-N 4-nitrothiophenol Chemical compound [O-][N+](=O)C1=CC=C(S)C=C1 AXBVSRMHOPMXBA-UHFFFAOYSA-N 0.000 description 1
- LMJXSOYPAOSIPZ-UHFFFAOYSA-N 4-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=C(S)C=C1 LMJXSOYPAOSIPZ-UHFFFAOYSA-N 0.000 description 1
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 1
- BCLFYSGTMUEFJU-UHFFFAOYSA-N 6-(2-chloroanilino)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CC=CC=C1NC1=CN=C(NC(=O)N2)C2=C1 BCLFYSGTMUEFJU-UHFFFAOYSA-N 0.000 description 1
- VIHHWQIHQVMSIO-UHFFFAOYSA-N 6-(2-chlorophenoxy)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CC=CC=C1OC1=CN=C(NC(=O)N2)C2=C1 VIHHWQIHQVMSIO-UHFFFAOYSA-N 0.000 description 1
- FMQIIYGGGDCOAO-UHFFFAOYSA-N 6-(2-chlorophenyl)sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CC=CC=C1SC1=CN=C(NC(=O)N2)C2=C1 FMQIIYGGGDCOAO-UHFFFAOYSA-N 0.000 description 1
- UYYWSCANCYITQI-UHFFFAOYSA-N 6-(2-fluoroanilino)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=CC=C1NC1=CN=C(NC(=O)N2)C2=C1 UYYWSCANCYITQI-UHFFFAOYSA-N 0.000 description 1
- MVAQXTUMAZDEOX-UHFFFAOYSA-N 6-(2-fluorophenoxy)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=CC=C1OC1=CN=C(NC(=O)N2)C2=C1 MVAQXTUMAZDEOX-UHFFFAOYSA-N 0.000 description 1
- HFBFLQANDAGXDA-UHFFFAOYSA-N 6-(2-fluorophenyl)sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=CC=C1SC1=CN=C(NC(=O)N2)C2=C1 HFBFLQANDAGXDA-UHFFFAOYSA-N 0.000 description 1
- NCIFCGLYQSAODX-UHFFFAOYSA-N 6-(2-methoxyanilino)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound COC1=CC=CC=C1NC1=CN=C(NC(=O)N2)C2=C1 NCIFCGLYQSAODX-UHFFFAOYSA-N 0.000 description 1
- VWVSLADBEZLDCW-UHFFFAOYSA-N 6-(2-methoxyphenoxy)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound COC1=CC=CC=C1OC1=CN=C(NC(=O)N2)C2=C1 VWVSLADBEZLDCW-UHFFFAOYSA-N 0.000 description 1
- HIHDEMAORREJOU-UHFFFAOYSA-N 6-(2-methoxyphenyl)sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound COC1=CC=CC=C1SC1=CN=C(NC(=O)N2)C2=C1 HIHDEMAORREJOU-UHFFFAOYSA-N 0.000 description 1
- JADLOEGQFIRCSC-UHFFFAOYSA-N 6-(2-methylanilino)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound CC1=CC=CC=C1NC1=CN=C(NC(=O)N2)C2=C1 JADLOEGQFIRCSC-UHFFFAOYSA-N 0.000 description 1
- BMTCSPPAEHTLKI-UHFFFAOYSA-N 6-(2-methylphenoxy)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound CC1=CC=CC=C1OC1=CN=C(NC(=O)N2)C2=C1 BMTCSPPAEHTLKI-UHFFFAOYSA-N 0.000 description 1
- MAMDOKAXXDGYOU-UHFFFAOYSA-N 6-(2-methylphenyl)sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound CC1=CC=CC=C1SC1=CN=C(NC(=O)N2)C2=C1 MAMDOKAXXDGYOU-UHFFFAOYSA-N 0.000 description 1
- CNYKNPREOZEOQR-UHFFFAOYSA-N 6-(2-nitroanilino)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CN=C(NC(=O)N2)C2=C1 CNYKNPREOZEOQR-UHFFFAOYSA-N 0.000 description 1
- CGXQACFHEXFREX-UHFFFAOYSA-N 6-(2-nitrophenoxy)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1=CN=C(NC(=O)N2)C2=C1 CGXQACFHEXFREX-UHFFFAOYSA-N 0.000 description 1
- DPXBBPWDFRQCIV-UHFFFAOYSA-N 6-(3-chloroanilino)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CC=CC(NC=2C=C3NC(=O)NC3=NC=2)=C1 DPXBBPWDFRQCIV-UHFFFAOYSA-N 0.000 description 1
- KXVXPISBZBPBJE-UHFFFAOYSA-N 6-(3-chlorophenoxy)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CC=CC(OC=2C=C3NC(=O)NC3=NC=2)=C1 KXVXPISBZBPBJE-UHFFFAOYSA-N 0.000 description 1
- XYDYFROPWZCXHE-UHFFFAOYSA-N 6-(3-chlorophenyl)sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CC=CC(SC=2C=C3NC(=O)NC3=NC=2)=C1 XYDYFROPWZCXHE-UHFFFAOYSA-N 0.000 description 1
- RORAGQRKBRCNJQ-UHFFFAOYSA-N 6-(3-fluoroanilino)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=CC(NC=2C=C3NC(=O)NC3=NC=2)=C1 RORAGQRKBRCNJQ-UHFFFAOYSA-N 0.000 description 1
- PTPGYUVZLXUIBQ-UHFFFAOYSA-N 6-(3-fluorophenoxy)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=CC(OC=2C=C3NC(=O)NC3=NC=2)=C1 PTPGYUVZLXUIBQ-UHFFFAOYSA-N 0.000 description 1
- LLAYVGDVYSFLOA-UHFFFAOYSA-N 6-(3-fluorophenyl)sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound FC1=CC=CC(SC=2C=C3NC(=O)NC3=NC=2)=C1 LLAYVGDVYSFLOA-UHFFFAOYSA-N 0.000 description 1
- RXODFABAQNQROV-UHFFFAOYSA-N 6-(3-methoxyanilino)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound COC1=CC=CC(NC=2C=C3NC(=O)NC3=NC=2)=C1 RXODFABAQNQROV-UHFFFAOYSA-N 0.000 description 1
- ZRSXBGYTEDPJKO-UHFFFAOYSA-N 6-(3-methoxyphenoxy)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound COC1=CC=CC(OC=2C=C3NC(=O)NC3=NC=2)=C1 ZRSXBGYTEDPJKO-UHFFFAOYSA-N 0.000 description 1
- NHKMZQBPZYFEGC-UHFFFAOYSA-N 6-(3-methoxyphenyl)sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound COC1=CC=CC(SC=2C=C3NC(=O)NC3=NC=2)=C1 NHKMZQBPZYFEGC-UHFFFAOYSA-N 0.000 description 1
- HFXRMMFDKXGLIB-UHFFFAOYSA-N 6-(3-methylanilino)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound CC1=CC=CC(NC=2C=C3NC(=O)NC3=NC=2)=C1 HFXRMMFDKXGLIB-UHFFFAOYSA-N 0.000 description 1
- UYSKHPCFOKFRCQ-UHFFFAOYSA-N 6-(3-methylphenoxy)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound CC1=CC=CC(OC=2C=C3NC(=O)NC3=NC=2)=C1 UYSKHPCFOKFRCQ-UHFFFAOYSA-N 0.000 description 1
- OAFZMFXQZKSHBP-UHFFFAOYSA-N 6-(3-methylphenyl)sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound CC1=CC=CC(SC=2C=C3NC(=O)NC3=NC=2)=C1 OAFZMFXQZKSHBP-UHFFFAOYSA-N 0.000 description 1
- MNYSNSLTWRYODG-UHFFFAOYSA-N 6-(3-nitroanilino)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound [O-][N+](=O)C1=CC=CC(NC=2C=C3NC(=O)NC3=NC=2)=C1 MNYSNSLTWRYODG-UHFFFAOYSA-N 0.000 description 1
- PAFRWPYCKWNSNU-UHFFFAOYSA-N 6-(3-nitrophenoxy)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound [O-][N+](=O)C1=CC=CC(OC=2C=C3NC(=O)NC3=NC=2)=C1 PAFRWPYCKWNSNU-UHFFFAOYSA-N 0.000 description 1
- UPGODGAQGSUMEQ-UHFFFAOYSA-N 6-(3-nitrophenyl)sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound [O-][N+](=O)C1=CC=CC(SC=2C=C3NC(=O)NC3=NC=2)=C1 UPGODGAQGSUMEQ-UHFFFAOYSA-N 0.000 description 1
- WMRRMCSFEJZBLE-UHFFFAOYSA-N 6-(4-chloroanilino)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC(Cl)=CC=C1NC1=CN=C(NC(=O)N2)C2=C1 WMRRMCSFEJZBLE-UHFFFAOYSA-N 0.000 description 1
- TWKVYABQAUIKPN-UHFFFAOYSA-N 6-(4-chlorophenoxy)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC(Cl)=CC=C1OC1=CN=C(NC(=O)N2)C2=C1 TWKVYABQAUIKPN-UHFFFAOYSA-N 0.000 description 1
- LSZXJUFWKNCMOI-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC(Cl)=CC=C1SC1=CN=C(NC(=O)N2)C2=C1 LSZXJUFWKNCMOI-UHFFFAOYSA-N 0.000 description 1
- IONRPAUXLLDSPV-UHFFFAOYSA-N 6-(4-fluoroanilino)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC(F)=CC=C1NC1=CN=C(NC(=O)N2)C2=C1 IONRPAUXLLDSPV-UHFFFAOYSA-N 0.000 description 1
- VWJUSSVNTRLAKF-UHFFFAOYSA-N 6-(4-fluorophenoxy)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC(F)=CC=C1OC1=CN=C(NC(=O)N2)C2=C1 VWJUSSVNTRLAKF-UHFFFAOYSA-N 0.000 description 1
- KYMFMQFKGVGBGB-UHFFFAOYSA-N 6-(4-fluorophenyl)sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC(F)=CC=C1SC1=CN=C(NC(=O)N2)C2=C1 KYMFMQFKGVGBGB-UHFFFAOYSA-N 0.000 description 1
- FIHGZFCAFNFENF-UHFFFAOYSA-N 6-(4-methoxyanilino)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC(OC)=CC=C1NC1=CN=C(NC(=O)N2)C2=C1 FIHGZFCAFNFENF-UHFFFAOYSA-N 0.000 description 1
- IVRRBGOPFUXEGZ-UHFFFAOYSA-N 6-(4-methoxyphenoxy)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC(OC)=CC=C1OC1=CN=C(NC(=O)N2)C2=C1 IVRRBGOPFUXEGZ-UHFFFAOYSA-N 0.000 description 1
- YMZAZPRTVVHZSK-UHFFFAOYSA-N 6-(4-methoxyphenyl)sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC(OC)=CC=C1SC1=CN=C(NC(=O)N2)C2=C1 YMZAZPRTVVHZSK-UHFFFAOYSA-N 0.000 description 1
- IKCJIIPHDPQPJH-UHFFFAOYSA-N 6-(4-methylanilino)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC(C)=CC=C1NC1=CN=C(NC(=O)N2)C2=C1 IKCJIIPHDPQPJH-UHFFFAOYSA-N 0.000 description 1
- DSLPHUQEJQIUOE-UHFFFAOYSA-N 6-(4-methylphenoxy)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC(C)=CC=C1OC1=CN=C(NC(=O)N2)C2=C1 DSLPHUQEJQIUOE-UHFFFAOYSA-N 0.000 description 1
- KANKWZFQWTXGHH-UHFFFAOYSA-N 6-(4-methylphenyl)sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC(C)=CC=C1SC1=CN=C(NC(=O)N2)C2=C1 KANKWZFQWTXGHH-UHFFFAOYSA-N 0.000 description 1
- RIJJOTFXGCYQKL-UHFFFAOYSA-N 6-(4-nitroanilino)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=CN=C(NC(=O)N2)C2=C1 RIJJOTFXGCYQKL-UHFFFAOYSA-N 0.000 description 1
- RBLYLFXNSFOOEM-UHFFFAOYSA-N 6-(4-nitrophenoxy)-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CN=C(NC(=O)N2)C2=C1 RBLYLFXNSFOOEM-UHFFFAOYSA-N 0.000 description 1
- BCEYYHZDNCHCFJ-UHFFFAOYSA-N 6-(4-nitrophenyl)sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1SC1=CN=C(NC(=O)N2)C2=C1 BCEYYHZDNCHCFJ-UHFFFAOYSA-N 0.000 description 1
- JHERKWILCBCFLG-UHFFFAOYSA-N 6-[2-(trifluoromethyl)anilino]-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound FC(F)(F)C1=CC=CC=C1NC1=CN=C(NC(=O)N2)C2=C1 JHERKWILCBCFLG-UHFFFAOYSA-N 0.000 description 1
- SUMTZEAZFUYABK-UHFFFAOYSA-N 6-[2-(trifluoromethyl)phenoxy]-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound FC(F)(F)C1=CC=CC=C1OC1=CN=C(NC(=O)N2)C2=C1 SUMTZEAZFUYABK-UHFFFAOYSA-N 0.000 description 1
- WIUVIWUJQCOUGC-UHFFFAOYSA-N 6-[2-(trifluoromethyl)phenyl]sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound FC(F)(F)C1=CC=CC=C1SC1=CN=C(NC(=O)N2)C2=C1 WIUVIWUJQCOUGC-UHFFFAOYSA-N 0.000 description 1
- DMPLINVHRCSRLI-UHFFFAOYSA-N 6-[3-(trifluoromethyl)anilino]-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound FC(F)(F)C1=CC=CC(NC=2C=C3NC(=O)NC3=NC=2)=C1 DMPLINVHRCSRLI-UHFFFAOYSA-N 0.000 description 1
- NGFNAAVNYFLOHR-UHFFFAOYSA-N 6-[3-(trifluoromethyl)phenoxy]-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound FC(F)(F)C1=CC=CC(OC=2C=C3NC(=O)NC3=NC=2)=C1 NGFNAAVNYFLOHR-UHFFFAOYSA-N 0.000 description 1
- QBOURYCAAVLXOY-UHFFFAOYSA-N 6-[3-(trifluoromethyl)phenyl]sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound FC(F)(F)C1=CC=CC(SC=2C=C3NC(=O)NC3=NC=2)=C1 QBOURYCAAVLXOY-UHFFFAOYSA-N 0.000 description 1
- BUIXZEQBRBXSED-UHFFFAOYSA-N 6-[4-(trifluoromethyl)anilino]-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=CN=C(NC(=O)N2)C2=C1 BUIXZEQBRBXSED-UHFFFAOYSA-N 0.000 description 1
- KGLFHZHBIJYHIE-UHFFFAOYSA-N 6-[4-(trifluoromethyl)phenoxy]-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1=CN=C(NC(=O)N2)C2=C1 KGLFHZHBIJYHIE-UHFFFAOYSA-N 0.000 description 1
- DHZMKHOFVMMRNA-UHFFFAOYSA-N 6-[4-(trifluoromethyl)phenyl]sulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1SC1=CN=C(NC(=O)N2)C2=C1 DHZMKHOFVMMRNA-UHFFFAOYSA-N 0.000 description 1
- WRMLYRNFAYQZLE-UHFFFAOYSA-N 6-anilino-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C=1N=C2NC(=O)NC2=CC=1NC1=CC=CC=C1 WRMLYRNFAYQZLE-UHFFFAOYSA-N 0.000 description 1
- PLMXCKPTUPPSCJ-UHFFFAOYSA-N 6-phenoxy-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C=1N=C2NC(=O)NC2=CC=1OC1=CC=CC=C1 PLMXCKPTUPPSCJ-UHFFFAOYSA-N 0.000 description 1
- NSPKDLXLANEZRE-UHFFFAOYSA-N 6-phenylsulfanyl-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical compound C=1N=C2NC(=O)NC2=CC=1SC1=CC=CC=C1 NSPKDLXLANEZRE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 108700028369 Alleles Proteins 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OGBVRMYSNSKIEF-UHFFFAOYSA-N Benzylphosphonic acid Chemical class OP(O)(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-N 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 description 1
- 206010012689 Diabetic retinopathy Diseases 0.000 description 1
- 108700022174 Drosophila Son of Sevenless Proteins 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- 238000012286 ELISA Assay Methods 0.000 description 1
- 241000206602 Eukaryota Species 0.000 description 1
- 241000975394 Evechinus chloroticus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 208000022461 Glomerular disease Diseases 0.000 description 1
- 206010018364 Glomerulonephritis 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
- 241000238631 Hexapoda Species 0.000 description 1
- 241001272567 Hominoidea Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 108020004711 Nucleic Acid Probes Proteins 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 208000022873 Ocular disease Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 101150062264 Raf gene Proteins 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 102100036407 Thioredoxin Human genes 0.000 description 1
- 208000034841 Thrombotic Microangiopathies Diseases 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 description 1
- OJQHCVNTVNFPHH-UHFFFAOYSA-N [O-][N+](=O)C1=CC=CC=C1SC1=CN=C(NC(=O)N2)C2=C1 Chemical compound [O-][N+](=O)C1=CC=CC=C1SC1=CN=C(NC(=O)N2)C2=C1 OJQHCVNTVNFPHH-UHFFFAOYSA-N 0.000 description 1
- CDXSJGDDABYYJV-UHFFFAOYSA-N acetic acid;ethanol Chemical compound CCO.CC(O)=O CDXSJGDDABYYJV-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 108091005764 adaptor proteins Proteins 0.000 description 1
- 102000035181 adaptor proteins Human genes 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000002009 alkene group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 230000002491 angiogenic effect Effects 0.000 description 1
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 description 1
- 238000003782 apoptosis assay Methods 0.000 description 1
- 230000005775 apoptotic pathway Effects 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000013592 cell lysate Substances 0.000 description 1
- 230000006037 cell lysis Effects 0.000 description 1
- 230000036755 cellular response Effects 0.000 description 1
- 230000004715 cellular signal transduction Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000007882 cirrhosis Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 210000004246 corpus luteum Anatomy 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 208000033679 diabetic kidney disease Diseases 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 230000013020 embryo development Effects 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- JTPGTFBZMYKQLC-UHFFFAOYSA-N ethyl N-[6-(4-methylphenyl)sulfanyl-1H-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C(C)OC(=O)NC1=NC=2C(=NC=C(C=2)SC2=CC=C(C=C2)C)N1 JTPGTFBZMYKQLC-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- BWQXKLDQKVDDSL-UHFFFAOYSA-N ethyl n-(6-anilino-1h-imidazo[4,5-b]pyridin-2-yl)carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=CC=C1 BWQXKLDQKVDDSL-UHFFFAOYSA-N 0.000 description 1
- SLXMOEYNWMXISJ-UHFFFAOYSA-N ethyl n-(6-phenoxy-1h-imidazo[4,5-b]pyridin-2-yl)carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=CC=C1 SLXMOEYNWMXISJ-UHFFFAOYSA-N 0.000 description 1
- UDULKYNJASPYFM-UHFFFAOYSA-N ethyl n-(6-phenylsulfanyl-1h-imidazo[4,5-b]pyridin-2-yl)carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1SC1=CC=CC=C1 UDULKYNJASPYFM-UHFFFAOYSA-N 0.000 description 1
- CMPJKVORAOOCDN-UHFFFAOYSA-N ethyl n-[6-(2-chloroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=CC=C1Cl CMPJKVORAOOCDN-UHFFFAOYSA-N 0.000 description 1
- NETAKSJDYQHGOX-UHFFFAOYSA-N ethyl n-[6-(2-chlorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=CC=C1Cl NETAKSJDYQHGOX-UHFFFAOYSA-N 0.000 description 1
- DGEZYOJUXDKAGL-UHFFFAOYSA-N ethyl n-[6-(2-chlorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1SC1=CC=CC=C1Cl DGEZYOJUXDKAGL-UHFFFAOYSA-N 0.000 description 1
- ZKFGQYDICZXTTH-UHFFFAOYSA-N ethyl n-[6-(2-fluoroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=CC=C1F ZKFGQYDICZXTTH-UHFFFAOYSA-N 0.000 description 1
- JFNOJKXQIGBIIC-UHFFFAOYSA-N ethyl n-[6-(2-fluorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=CC=C1F JFNOJKXQIGBIIC-UHFFFAOYSA-N 0.000 description 1
- HWMPZJXZVUYRFW-UHFFFAOYSA-N ethyl n-[6-(2-fluorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1SC1=CC=CC=C1F HWMPZJXZVUYRFW-UHFFFAOYSA-N 0.000 description 1
- RGBPQRMFYUXYEA-UHFFFAOYSA-N ethyl n-[6-(2-methoxyanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=CC=C1OC RGBPQRMFYUXYEA-UHFFFAOYSA-N 0.000 description 1
- FQSMIJYVBGFFBF-UHFFFAOYSA-N ethyl n-[6-(2-methoxyphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=CC=C1OC FQSMIJYVBGFFBF-UHFFFAOYSA-N 0.000 description 1
- KOIYVNLDHMGGEK-UHFFFAOYSA-N ethyl n-[6-(2-methylanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=CC=C1C KOIYVNLDHMGGEK-UHFFFAOYSA-N 0.000 description 1
- YFKYMTYTANTRIV-UHFFFAOYSA-N ethyl n-[6-(2-methylphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=CC=C1C YFKYMTYTANTRIV-UHFFFAOYSA-N 0.000 description 1
- XVIZASNPIIXYFS-UHFFFAOYSA-N ethyl n-[6-(2-methylphenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OCC)=NC2=NC=C1SC1=CC=CC=C1C XVIZASNPIIXYFS-UHFFFAOYSA-N 0.000 description 1
- UAPIBXWJMAEOQK-UHFFFAOYSA-N ethyl n-[6-(2-nitroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OCC)=NC2=NC=C1NC1=CC=CC=C1[N+]([O-])=O UAPIBXWJMAEOQK-UHFFFAOYSA-N 0.000 description 1
- UNAIIPOTUBJZFB-UHFFFAOYSA-N ethyl n-[6-(2-nitrophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=CC=C1[N+]([O-])=O UNAIIPOTUBJZFB-UHFFFAOYSA-N 0.000 description 1
- WSLKTTNBQNIELC-UHFFFAOYSA-N ethyl n-[6-(2-nitrophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1SC1=CC=CC=C1[N+]([O-])=O WSLKTTNBQNIELC-UHFFFAOYSA-N 0.000 description 1
- YXKHTXMDNZETTG-UHFFFAOYSA-N ethyl n-[6-(3-chloroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=CC(Cl)=C1 YXKHTXMDNZETTG-UHFFFAOYSA-N 0.000 description 1
- KOJLBAQXILWHDE-UHFFFAOYSA-N ethyl n-[6-(3-chlorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=CC(Cl)=C1 KOJLBAQXILWHDE-UHFFFAOYSA-N 0.000 description 1
- PJRPZLKFGSVYBW-UHFFFAOYSA-N ethyl n-[6-(3-chlorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OCC)=NC2=NC=C1SC1=CC=CC(Cl)=C1 PJRPZLKFGSVYBW-UHFFFAOYSA-N 0.000 description 1
- UKTFDABUUJRXFR-UHFFFAOYSA-N ethyl n-[6-(3-fluoroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=CC(F)=C1 UKTFDABUUJRXFR-UHFFFAOYSA-N 0.000 description 1
- SPBQLGLLPWQCPN-UHFFFAOYSA-N ethyl n-[6-(3-fluorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=CC(F)=C1 SPBQLGLLPWQCPN-UHFFFAOYSA-N 0.000 description 1
- YVFADCCNIZYYTB-UHFFFAOYSA-N ethyl n-[6-(3-fluorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OCC)=NC2=NC=C1SC1=CC=CC(F)=C1 YVFADCCNIZYYTB-UHFFFAOYSA-N 0.000 description 1
- MHTQHYOMDMXAJE-UHFFFAOYSA-N ethyl n-[6-(3-methoxyanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=CC(OC)=C1 MHTQHYOMDMXAJE-UHFFFAOYSA-N 0.000 description 1
- LDFXIOMQYOIDLI-UHFFFAOYSA-N ethyl n-[6-(3-methoxyphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=CC(OC)=C1 LDFXIOMQYOIDLI-UHFFFAOYSA-N 0.000 description 1
- ZYJMUAZJNSUWFK-UHFFFAOYSA-N ethyl n-[6-(3-methoxyphenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OCC)=NC2=NC=C1SC1=CC=CC(OC)=C1 ZYJMUAZJNSUWFK-UHFFFAOYSA-N 0.000 description 1
- LDBCPOGRWYBFOO-UHFFFAOYSA-N ethyl n-[6-(3-methylanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=CC(C)=C1 LDBCPOGRWYBFOO-UHFFFAOYSA-N 0.000 description 1
- ZJZAXCGBRGFRGZ-UHFFFAOYSA-N ethyl n-[6-(3-methylphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=CC(C)=C1 ZJZAXCGBRGFRGZ-UHFFFAOYSA-N 0.000 description 1
- MLOQRPFZBLQCBT-UHFFFAOYSA-N ethyl n-[6-(3-methylphenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1SC1=CC=CC(C)=C1 MLOQRPFZBLQCBT-UHFFFAOYSA-N 0.000 description 1
- FXERICCUVLXJHQ-UHFFFAOYSA-N ethyl n-[6-(3-nitroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=CC([N+]([O-])=O)=C1 FXERICCUVLXJHQ-UHFFFAOYSA-N 0.000 description 1
- URHXFJWKKOLTNT-UHFFFAOYSA-N ethyl n-[6-(3-nitrophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OCC)=NC2=NC=C1OC1=CC=CC([N+]([O-])=O)=C1 URHXFJWKKOLTNT-UHFFFAOYSA-N 0.000 description 1
- WEINZALJCNBCST-UHFFFAOYSA-N ethyl n-[6-(3-nitrophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1SC1=CC=CC([N+]([O-])=O)=C1 WEINZALJCNBCST-UHFFFAOYSA-N 0.000 description 1
- NGIOBQDUUFDIHO-UHFFFAOYSA-N ethyl n-[6-(4-chloroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=C(Cl)C=C1 NGIOBQDUUFDIHO-UHFFFAOYSA-N 0.000 description 1
- AWBQAVWWSWDLSJ-UHFFFAOYSA-N ethyl n-[6-(4-chlorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=C(Cl)C=C1 AWBQAVWWSWDLSJ-UHFFFAOYSA-N 0.000 description 1
- ASMHGXYDGLONOQ-UHFFFAOYSA-N ethyl n-[6-(4-chlorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1SC1=CC=C(Cl)C=C1 ASMHGXYDGLONOQ-UHFFFAOYSA-N 0.000 description 1
- XZMJKGJEBDFIBE-UHFFFAOYSA-N ethyl n-[6-(4-fluoroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=C(F)C=C1 XZMJKGJEBDFIBE-UHFFFAOYSA-N 0.000 description 1
- VIUQHTNPTZKYSC-UHFFFAOYSA-N ethyl n-[6-(4-fluorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=C(F)C=C1 VIUQHTNPTZKYSC-UHFFFAOYSA-N 0.000 description 1
- CGIANNMJUVFOOC-UHFFFAOYSA-N ethyl n-[6-(4-fluorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1SC1=CC=C(F)C=C1 CGIANNMJUVFOOC-UHFFFAOYSA-N 0.000 description 1
- CNACYSZWISYFSH-UHFFFAOYSA-N ethyl n-[6-(4-methoxyanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=C(OC)C=C1 CNACYSZWISYFSH-UHFFFAOYSA-N 0.000 description 1
- BQXQWWAWZNLWHN-UHFFFAOYSA-N ethyl n-[6-(4-methoxyphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=C(OC)C=C1 BQXQWWAWZNLWHN-UHFFFAOYSA-N 0.000 description 1
- GBIJZQXIFIOLFR-UHFFFAOYSA-N ethyl n-[6-(4-methoxyphenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1SC1=CC=C(OC)C=C1 GBIJZQXIFIOLFR-UHFFFAOYSA-N 0.000 description 1
- DMPFGDHRUDFPAB-UHFFFAOYSA-N ethyl n-[6-(4-methylphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=C(C)C=C1 DMPFGDHRUDFPAB-UHFFFAOYSA-N 0.000 description 1
- IQGOJCUGYJOJLD-UHFFFAOYSA-N ethyl n-[6-(4-nitroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=C([N+]([O-])=O)C=C1 IQGOJCUGYJOJLD-UHFFFAOYSA-N 0.000 description 1
- PQVLZNYXJDNGDA-UHFFFAOYSA-N ethyl n-[6-(4-nitrophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=C([N+]([O-])=O)C=C1 PQVLZNYXJDNGDA-UHFFFAOYSA-N 0.000 description 1
- GLLBNVHWEPGYNT-UHFFFAOYSA-N ethyl n-[6-(4-nitrophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1SC1=CC=C([N+]([O-])=O)C=C1 GLLBNVHWEPGYNT-UHFFFAOYSA-N 0.000 description 1
- RPOKTDNFJGXHIU-UHFFFAOYSA-N ethyl n-[6-[2-(trifluoromethyl)anilino]-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=CC=C1C(F)(F)F RPOKTDNFJGXHIU-UHFFFAOYSA-N 0.000 description 1
- ZIIGXAWBUQGLFX-UHFFFAOYSA-N ethyl n-[6-[2-(trifluoromethyl)phenoxy]-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=CC=C1C(F)(F)F ZIIGXAWBUQGLFX-UHFFFAOYSA-N 0.000 description 1
- KRCYMJYAVLFVCJ-UHFFFAOYSA-N ethyl n-[6-[2-(trifluoromethyl)phenyl]sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OCC)=NC2=NC=C1SC1=CC=CC=C1C(F)(F)F KRCYMJYAVLFVCJ-UHFFFAOYSA-N 0.000 description 1
- XVIZOQPBWCVCAR-UHFFFAOYSA-N ethyl n-[6-[3-(trifluoromethyl)anilino]-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OCC)=NC2=NC=C1NC1=CC=CC(C(F)(F)F)=C1 XVIZOQPBWCVCAR-UHFFFAOYSA-N 0.000 description 1
- LEQLESVTPBMHAB-UHFFFAOYSA-N ethyl n-[6-[3-(trifluoromethyl)phenoxy]-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=CC(C(F)(F)F)=C1 LEQLESVTPBMHAB-UHFFFAOYSA-N 0.000 description 1
- WADFDMUXBMRCPS-UHFFFAOYSA-N ethyl n-[6-[3-(trifluoromethyl)phenyl]sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OCC)=NC2=NC=C1SC1=CC=CC(C(F)(F)F)=C1 WADFDMUXBMRCPS-UHFFFAOYSA-N 0.000 description 1
- JTOBZWNFBIQPNZ-UHFFFAOYSA-N ethyl n-[6-[4-(trifluoromethyl)anilino]-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1NC1=CC=C(C(F)(F)F)C=C1 JTOBZWNFBIQPNZ-UHFFFAOYSA-N 0.000 description 1
- HCKXQCAHQSURIK-UHFFFAOYSA-N ethyl n-[6-[4-(trifluoromethyl)phenoxy]-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OCC)=NC2=CC=1OC1=CC=C(C(F)(F)F)C=C1 HCKXQCAHQSURIK-UHFFFAOYSA-N 0.000 description 1
- IHEDSANMRNYSLW-UHFFFAOYSA-N ethyl n-[6-[4-(trifluoromethyl)phenyl]sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OCC)=NC2=NC=C1SC1=CC=C(C(F)(F)F)C=C1 IHEDSANMRNYSLW-UHFFFAOYSA-N 0.000 description 1
- 210000003527 eukaryotic cell Anatomy 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 108020001507 fusion proteins Proteins 0.000 description 1
- 102000037865 fusion proteins Human genes 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 208000037841 lung tumor Diseases 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- BLVGTOKCEIAUDA-UHFFFAOYSA-N methyl n-[6-(2-chloroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC=C1Cl BLVGTOKCEIAUDA-UHFFFAOYSA-N 0.000 description 1
- ULGHSKKANLFGMO-UHFFFAOYSA-N methyl n-[6-(2-chlorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC=C1Cl ULGHSKKANLFGMO-UHFFFAOYSA-N 0.000 description 1
- DXHRHXQVGBSZEM-UHFFFAOYSA-N methyl n-[6-(2-chlorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC=C1Cl DXHRHXQVGBSZEM-UHFFFAOYSA-N 0.000 description 1
- GTFTTWFGAUGHEC-UHFFFAOYSA-N methyl n-[6-(2-fluoroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC=C1F GTFTTWFGAUGHEC-UHFFFAOYSA-N 0.000 description 1
- JVKZNYHUWAXLIH-UHFFFAOYSA-N methyl n-[6-(2-fluorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC=C1F JVKZNYHUWAXLIH-UHFFFAOYSA-N 0.000 description 1
- QDRVDJCMQMVSHZ-UHFFFAOYSA-N methyl n-[6-(2-fluorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC=C1F QDRVDJCMQMVSHZ-UHFFFAOYSA-N 0.000 description 1
- YYXJQLOOPZZUOP-UHFFFAOYSA-N methyl n-[6-(2-methoxyanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC=C1OC YYXJQLOOPZZUOP-UHFFFAOYSA-N 0.000 description 1
- JLKYYEQFCFSAHE-UHFFFAOYSA-N methyl n-[6-(2-methoxyphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC=C1OC JLKYYEQFCFSAHE-UHFFFAOYSA-N 0.000 description 1
- BBUFWKOHEXBJHX-UHFFFAOYSA-N methyl n-[6-(2-methoxyphenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC=C1OC BBUFWKOHEXBJHX-UHFFFAOYSA-N 0.000 description 1
- QAGUHLKOQASYRM-UHFFFAOYSA-N methyl n-[6-(2-methylanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC=C1C QAGUHLKOQASYRM-UHFFFAOYSA-N 0.000 description 1
- CGEYSZLFQLBOQJ-UHFFFAOYSA-N methyl n-[6-(2-methylphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC=C1C CGEYSZLFQLBOQJ-UHFFFAOYSA-N 0.000 description 1
- MVDFKSUNQKEZDG-UHFFFAOYSA-N methyl n-[6-(2-methylphenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OC)=NC2=NC=C1SC1=CC=CC=C1C MVDFKSUNQKEZDG-UHFFFAOYSA-N 0.000 description 1
- QHAPGOHBRDXDJH-UHFFFAOYSA-N methyl n-[6-(2-nitroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC=C1[N+]([O-])=O QHAPGOHBRDXDJH-UHFFFAOYSA-N 0.000 description 1
- UHPOXMGLKCSMEI-UHFFFAOYSA-N methyl n-[6-(2-nitrophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC=C1[N+]([O-])=O UHPOXMGLKCSMEI-UHFFFAOYSA-N 0.000 description 1
- AHQYHAIUJWDGCW-UHFFFAOYSA-N methyl n-[6-(2-nitrophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC=C1[N+]([O-])=O AHQYHAIUJWDGCW-UHFFFAOYSA-N 0.000 description 1
- LEFCCEOVCXOZFW-UHFFFAOYSA-N methyl n-[6-(3-chloroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC(Cl)=C1 LEFCCEOVCXOZFW-UHFFFAOYSA-N 0.000 description 1
- KPKLDOVGEZXDGY-UHFFFAOYSA-N methyl n-[6-(3-chlorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC(Cl)=C1 KPKLDOVGEZXDGY-UHFFFAOYSA-N 0.000 description 1
- XGCVHDXETITBKK-UHFFFAOYSA-N methyl n-[6-(3-chlorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC(Cl)=C1 XGCVHDXETITBKK-UHFFFAOYSA-N 0.000 description 1
- UJGVWDDHQMIEHG-UHFFFAOYSA-N methyl n-[6-(3-fluoroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC(F)=C1 UJGVWDDHQMIEHG-UHFFFAOYSA-N 0.000 description 1
- LTEJAPLVONTXLX-UHFFFAOYSA-N methyl n-[6-(3-fluorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC(F)=C1 LTEJAPLVONTXLX-UHFFFAOYSA-N 0.000 description 1
- XXFGWVGPJHLUAA-UHFFFAOYSA-N methyl n-[6-(3-fluorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC(F)=C1 XXFGWVGPJHLUAA-UHFFFAOYSA-N 0.000 description 1
- MIRJINYQCNZPPH-UHFFFAOYSA-N methyl n-[6-(3-methoxyanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC(OC)=C1 MIRJINYQCNZPPH-UHFFFAOYSA-N 0.000 description 1
- PCJKQZZRZGJKFN-UHFFFAOYSA-N methyl n-[6-(3-methoxyphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC(OC)=C1 PCJKQZZRZGJKFN-UHFFFAOYSA-N 0.000 description 1
- XEJDQGSVVYABQK-UHFFFAOYSA-N methyl n-[6-(3-methoxyphenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC(OC)=C1 XEJDQGSVVYABQK-UHFFFAOYSA-N 0.000 description 1
- UDDIDNHSMUCTEE-UHFFFAOYSA-N methyl n-[6-(3-methylanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC(C)=C1 UDDIDNHSMUCTEE-UHFFFAOYSA-N 0.000 description 1
- GJGRCSBQWUGOSD-UHFFFAOYSA-N methyl n-[6-(3-methylphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC(C)=C1 GJGRCSBQWUGOSD-UHFFFAOYSA-N 0.000 description 1
- MHOKSXDPQKGZGI-UHFFFAOYSA-N methyl n-[6-(3-methylphenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC(C)=C1 MHOKSXDPQKGZGI-UHFFFAOYSA-N 0.000 description 1
- JHAAYIJXKUZKBR-UHFFFAOYSA-N methyl n-[6-(3-nitroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC([N+]([O-])=O)=C1 JHAAYIJXKUZKBR-UHFFFAOYSA-N 0.000 description 1
- NCRPWNBUYGEHHP-UHFFFAOYSA-N methyl n-[6-(3-nitrophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC([N+]([O-])=O)=C1 NCRPWNBUYGEHHP-UHFFFAOYSA-N 0.000 description 1
- PWFAVHFFLZRGQN-UHFFFAOYSA-N methyl n-[6-(3-nitrophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=CC([N+]([O-])=O)=C1 PWFAVHFFLZRGQN-UHFFFAOYSA-N 0.000 description 1
- YPVOGSUISPYBCN-UHFFFAOYSA-N methyl n-[6-(4-chloroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=C(Cl)C=C1 YPVOGSUISPYBCN-UHFFFAOYSA-N 0.000 description 1
- CZWTULUSEUKILH-UHFFFAOYSA-N methyl n-[6-(4-chlorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=C(Cl)C=C1 CZWTULUSEUKILH-UHFFFAOYSA-N 0.000 description 1
- OYSANANHGSOVFE-UHFFFAOYSA-N methyl n-[6-(4-chlorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=C(Cl)C=C1 OYSANANHGSOVFE-UHFFFAOYSA-N 0.000 description 1
- SFFIYVRUXFJDCB-UHFFFAOYSA-N methyl n-[6-(4-fluoroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OC)=NC2=NC=C1NC1=CC=C(F)C=C1 SFFIYVRUXFJDCB-UHFFFAOYSA-N 0.000 description 1
- NKYAZOVOFPQQNT-UHFFFAOYSA-N methyl n-[6-(4-fluorophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=C(F)C=C1 NKYAZOVOFPQQNT-UHFFFAOYSA-N 0.000 description 1
- ABWQLPCUFRXYKV-UHFFFAOYSA-N methyl n-[6-(4-fluorophenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=C(F)C=C1 ABWQLPCUFRXYKV-UHFFFAOYSA-N 0.000 description 1
- WSCBVHOTTPJEAE-UHFFFAOYSA-N methyl n-[6-(4-methoxyanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=C(OC)C=C1 WSCBVHOTTPJEAE-UHFFFAOYSA-N 0.000 description 1
- UYPXRHKDZQBFIZ-UHFFFAOYSA-N methyl n-[6-(4-methoxyphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=C(OC)C=C1 UYPXRHKDZQBFIZ-UHFFFAOYSA-N 0.000 description 1
- RUWOPKQVIPYRBV-UHFFFAOYSA-N methyl n-[6-(4-methoxyphenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=C(OC)C=C1 RUWOPKQVIPYRBV-UHFFFAOYSA-N 0.000 description 1
- GZPMAWXTIOHRIV-UHFFFAOYSA-N methyl n-[6-(4-methylanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=C(C)C=C1 GZPMAWXTIOHRIV-UHFFFAOYSA-N 0.000 description 1
- YASXIBIDERFXIA-UHFFFAOYSA-N methyl n-[6-(4-methylphenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=C(C)C=C1 YASXIBIDERFXIA-UHFFFAOYSA-N 0.000 description 1
- CPDIUUMCRDJJCT-UHFFFAOYSA-N methyl n-[6-(4-methylphenyl)sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1SC1=CC=C(C)C=C1 CPDIUUMCRDJJCT-UHFFFAOYSA-N 0.000 description 1
- WWEUMGJVCHMHGM-UHFFFAOYSA-N methyl n-[6-(4-nitroanilino)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=C([N+]([O-])=O)C=C1 WWEUMGJVCHMHGM-UHFFFAOYSA-N 0.000 description 1
- XOVPOVYOAPDAHL-UHFFFAOYSA-N methyl n-[6-(4-nitrophenoxy)-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=C([N+]([O-])=O)C=C1 XOVPOVYOAPDAHL-UHFFFAOYSA-N 0.000 description 1
- OWJLMTLGUWZTAH-UHFFFAOYSA-N methyl n-[6-[2-(trifluoromethyl)anilino]-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=CC=C1C(F)(F)F OWJLMTLGUWZTAH-UHFFFAOYSA-N 0.000 description 1
- IYCICJSDXRUOJR-UHFFFAOYSA-N methyl n-[6-[2-(trifluoromethyl)phenoxy]-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC=C1C(F)(F)F IYCICJSDXRUOJR-UHFFFAOYSA-N 0.000 description 1
- LBSVCLACLYZXEK-UHFFFAOYSA-N methyl n-[6-[2-(trifluoromethyl)phenyl]sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OC)=NC2=NC=C1SC1=CC=CC=C1C(F)(F)F LBSVCLACLYZXEK-UHFFFAOYSA-N 0.000 description 1
- FTACQLGWOYVDMM-UHFFFAOYSA-N methyl n-[6-[3-(trifluoromethyl)anilino]-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OC)=NC2=NC=C1NC1=CC=CC(C(F)(F)F)=C1 FTACQLGWOYVDMM-UHFFFAOYSA-N 0.000 description 1
- PGLGGDDQKJQMSU-UHFFFAOYSA-N methyl n-[6-[3-(trifluoromethyl)phenoxy]-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=CC(C(F)(F)F)=C1 PGLGGDDQKJQMSU-UHFFFAOYSA-N 0.000 description 1
- CXZNPFRNZIIIET-UHFFFAOYSA-N methyl n-[6-[3-(trifluoromethyl)phenyl]sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OC)=NC2=NC=C1SC1=CC=CC(C(F)(F)F)=C1 CXZNPFRNZIIIET-UHFFFAOYSA-N 0.000 description 1
- DBFDTTYFRUYTSD-UHFFFAOYSA-N methyl n-[6-[4-(trifluoromethyl)anilino]-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1NC1=CC=C(C(F)(F)F)C=C1 DBFDTTYFRUYTSD-UHFFFAOYSA-N 0.000 description 1
- VGEZGJFDNATKTL-UHFFFAOYSA-N methyl n-[6-[4-(trifluoromethyl)phenoxy]-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C=1N=C2NC(NC(=O)OC)=NC2=CC=1OC1=CC=C(C(F)(F)F)C=C1 VGEZGJFDNATKTL-UHFFFAOYSA-N 0.000 description 1
- RAHISYKDQUPPFI-UHFFFAOYSA-N methyl n-[6-[4-(trifluoromethyl)phenyl]sulfanyl-1h-imidazo[4,5-b]pyridin-2-yl]carbamate Chemical compound C1=C2NC(NC(=O)OC)=NC2=NC=C1SC1=CC=C(C(F)(F)F)C=C1 RAHISYKDQUPPFI-UHFFFAOYSA-N 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 238000000520 microinjection Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 230000017095 negative regulation of cell growth Effects 0.000 description 1
- 201000009925 nephrosclerosis Diseases 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 239000002853 nucleic acid probe Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 231100000590 oncogenic Toxicity 0.000 description 1
- 230000002246 oncogenic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000008723 osmotic stress Effects 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000005522 programmed cell death Effects 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 208000023958 prostate neoplasm Diseases 0.000 description 1
- 239000003909 protein kinase inhibitor Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 108060008226 thioredoxin Proteins 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 102000027257 transmembrane receptors Human genes 0.000 description 1
- 108091008578 transmembrane receptors Proteins 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
- 230000005748 tumor development Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 108010002164 tyrosine receptor Proteins 0.000 description 1
- 150000003668 tyrosines Chemical class 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
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6014597P | 1997-09-26 | 1997-09-26 | |
| US60145P | 1997-09-26 | ||
| PCT/US1998/019973 WO1999016438A1 (en) | 1997-09-26 | 1998-09-23 | Azabenzimidazole-based compounds for modulating serine/threonine protein kinase function |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69827516D1 DE69827516D1 (de) | 2004-12-16 |
| DE69827516T2 true DE69827516T2 (de) | 2005-12-01 |
Family
ID=22027657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69827516T Expired - Fee Related DE69827516T2 (de) | 1997-09-26 | 1998-09-23 | Azabenzimidazol-verbindungen zur modulation der serin/threonin protein-kinase funktion |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US6093728A (enExample) |
| EP (1) | EP1017384B1 (enExample) |
| JP (1) | JP2001517699A (enExample) |
| KR (1) | KR100547929B1 (enExample) |
| CN (1) | CN1167420C (enExample) |
| AR (1) | AR017266A1 (enExample) |
| AT (1) | ATE281834T1 (enExample) |
| AU (1) | AU748849B2 (enExample) |
| BG (1) | BG64784B1 (enExample) |
| BR (1) | BR9812682A (enExample) |
| CA (1) | CA2305370C (enExample) |
| DE (1) | DE69827516T2 (enExample) |
| DK (1) | DK1017384T3 (enExample) |
| ES (1) | ES2230719T3 (enExample) |
| HU (1) | HUP0004024A3 (enExample) |
| IL (4) | IL135109A0 (enExample) |
| NO (1) | NO325663B1 (enExample) |
| NZ (2) | NZ503432A (enExample) |
| PL (1) | PL191618B1 (enExample) |
| PT (1) | PT1017384E (enExample) |
| RU (1) | RU2230553C2 (enExample) |
| SK (1) | SK285357B6 (enExample) |
| TR (1) | TR200001546T2 (enExample) |
| TW (1) | TW581815B (enExample) |
| UA (1) | UA72448C2 (enExample) |
| WO (1) | WO1999016438A1 (enExample) |
| ZA (1) | ZA988797B (enExample) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060142236A1 (en) * | 1994-05-31 | 2006-06-29 | Isis Pharmaceuticals, Inc. | Antisense oligonucleotide modulation of raf gene expression |
| US6919366B2 (en) * | 1998-05-22 | 2005-07-19 | Avanir Pharmaceuticals | Benzimidazole derivatives as modulators of IgE |
| US6911462B2 (en) * | 1998-05-22 | 2005-06-28 | Avanir Pharmaceuticals | Benzimidazole compounds for regulating IgE |
| US6384049B1 (en) * | 2000-05-25 | 2002-05-07 | The Procter & Gamble Company | Cancer treatment |
| ES2291455T3 (es) * | 2001-03-12 | 2008-03-01 | Avanir Pharmaceuticals | Compuestos de bencimidazol para modular ige e inhibir la proliferacion celular. |
| TW200304820A (en) * | 2002-03-25 | 2003-10-16 | Avanir Pharmaceuticals | Use of benzimidazole analogs in the treatment of cell proliferation |
| TWI276631B (en) * | 2002-09-12 | 2007-03-21 | Avanir Pharmaceuticals | Phenyl-aza-benzimidazole compounds for modulating IgE and inhibiting cellular proliferation |
| AU2003270426A1 (en) | 2002-09-12 | 2004-04-30 | Avanir Pharmaceuticals | PHENYL-INDOLE COMPOUNDS FOR MODULATING IgE AND INHIBITING CELLULAR PROLIFERATION |
| US20050256179A1 (en) * | 2003-08-08 | 2005-11-17 | Sircar Jagadish C | Selective pharmacologic inhibition of protein trafficking and related methods of treating human diseases |
| GB0423554D0 (en) | 2004-10-22 | 2004-11-24 | Cancer Rec Tech Ltd | Therapeutic compounds |
| EP1962892A4 (en) | 2005-11-22 | 2011-10-12 | Univ South Florida | INHIBITION OF CELL PROLIFERATION |
| JP2009534457A (ja) | 2006-04-26 | 2009-09-24 | キャンサー・リサーチ・テクノロジー・リミテッド | がん治療用化合物としてのイミダゾ［４，５−ｂ］ピリジン−２−オンおよびオキサゾロ［４，５−ｂ］ピリジン−２−オン化合物およびその類似体 |
| EP2457913B1 (en) * | 2006-10-19 | 2017-04-19 | Signal Pharmaceuticals, LLC | Heteroaryl compounds, compositions thereof, and methods of treatment therewith |
| EP2839839B1 (en) * | 2007-02-28 | 2018-01-17 | Yeda Research And Development Company Limited | Nuclear targeting sequences |
| AR066845A1 (es) | 2007-06-05 | 2009-09-16 | Takeda Pharmaceutical | Derivados de triazolopiridina e imidazopiridina una composicion farmaceutica que los comprende y su uso en la preparacion de un medicamento para el tratamiento del cancer |
| EP2181987B9 (en) | 2007-08-23 | 2014-09-03 | Takeda Pharmaceutical Company Limited | 2-Carbonylaminobenzothiazoles and their use for the prophylaxis and treatment of cancer |
| EP2184285B1 (en) * | 2007-08-29 | 2015-11-04 | Takeda Pharmaceutical Company Limited | Heterocyclic compound and use thereof |
| BRPI0821227A2 (pt) | 2007-12-19 | 2015-06-16 | Cancer Rec Tech Ltd | Composto, composição farmacêutica, método para preparar a mesma, uso de um composto, método para tratar uma doença ou distúrbio, para inibir função de raf e para inibir proliferação celular, inibir progressão do ciclo celular, promover apoptose, ou uma combinação de um ou mais dos mesmos |
| GB0807609D0 (en) | 2008-04-25 | 2008-06-04 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| US20100184851A1 (en) * | 2008-08-29 | 2010-07-22 | University Of South Florida | Inhibition of cell proliferation |
| US8110578B2 (en) | 2008-10-27 | 2012-02-07 | Signal Pharmaceuticals, Llc | Pyrazino[2,3-b]pyrazine mTOR kinase inhibitors for oncology indications and diseases associated with the mTOR/PI3K/Akt pathway |
| WO2010064611A1 (ja) | 2008-12-01 | 2010-06-10 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| JO3101B1 (ar) | 2008-12-02 | 2017-09-20 | Takeda Pharmaceuticals Co | مشتقات بنزوثيازول كعوامل مضادة للسرطان |
| JP2012197231A (ja) * | 2009-08-06 | 2012-10-18 | Oncotherapy Science Ltd | Ｔｔｋ阻害作用を有するピリジンおよびピリミジン誘導体 |
| JP2013508456A (ja) | 2009-10-26 | 2013-03-07 | シグナル ファーマシューティカルズ， エルエルシー | ヘテロアリール化合物の合成方法および精製方法 |
| EP2531502B1 (en) | 2010-02-01 | 2014-04-02 | Cancer Research Technology Limited | 1-(5-tert-butyl-2-phenyl-2h-pyrazol-3-yl)-3-[2-fluoro-4-(1-methyl-2-oxo-2,3-dihydro-1h-imidazo[4,5-b]pyridin-7-yloxy)-phenyl]-urea and related compounds and their use in therapy |
| SG10201912850WA (en) | 2011-10-19 | 2020-02-27 | Signal Pharm Llc | Treatment Of Cancer With TOR Kinase Inhibitors |
| ES2694413T3 (es) | 2011-12-02 | 2018-12-20 | Signal Pharmaceuticals, Llc | Composiciones farmacéuticas de 7-(6-(2-hidroxipropan-2-il)piridin-3-il)-1-((trans)-4-metoxiciclohexil)-3,4-dihidropirazino [2,3-b]pirazin-2(1H)-ona, una forma sólida de la misma y métodos para su uso |
| CA2864905A1 (en) | 2012-02-24 | 2013-08-29 | Signal Pharmaceuticals, Llc | Methods for treating non- small cell lung cancer using tor kinase inhibitor combination therapy |
| AU2013203714B2 (en) | 2012-10-18 | 2015-12-03 | Signal Pharmaceuticals, Llc | Inhibition of phosphorylation of PRAS40, GSK3-beta or P70S6K1 as a marker for TOR kinase inhibitory activity |
| EP2945636B1 (en) | 2013-01-16 | 2017-06-28 | Signal Pharmaceuticals, LLC | Substituted pyrrolopyrimidine compounds, compositions thereof, and methods of treatment therewith |
| US9650376B2 (en) | 2013-03-15 | 2017-05-16 | Knopp Biosciences Llc | Imidazo(4,5-B) pyridin-2-yl amides as KV7 channel activators |
| NZ629411A (en) | 2013-04-17 | 2017-06-30 | Signal Pharm Llc | Treatment of cancer with dihydropyrazino-pyrazines |
| KR102242505B1 (ko) | 2013-04-17 | 2021-04-20 | 시그날 파마소티칼 엘엘씨 | 암 치료용 tor 키나제 억제제 및 시티딘 유사체를 포함하는 병용 요법 |
| ES2944478T3 (es) | 2013-04-17 | 2023-06-21 | Signal Pharm Llc | 1-etil-7-(2-metil-6-(1H-1,2,4-triazol-3-il)piridin-3-il)-3,4-dihidropirazino[2,3-b]pirazin-2(1H)-ona para tratar el glioblastoma multiforme |
| BR112015026257B1 (pt) | 2013-04-17 | 2022-12-20 | Signal Pharmaceuticals, Llc | Uso de um composto dihidropirazino-pirazina e enzalutamida, composição farmacêutica que os compreende, e kit |
| AU2014254057A1 (en) | 2013-04-17 | 2015-11-05 | Signal Pharmaceuticals, Llc | Combination therapy comprising a TOR kinase inhibitor and N-(3-(5-fluoro-2-(4-(2-methoxyethoxy)phenylamino)pyrimidin-4-ylamino)phenyl)acrylamide for treating cancer |
| SG11201508527VA (en) | 2013-04-17 | 2015-11-27 | Signal Pharm Llc | Pharmaceutical formulations, processes, solid forms and methods of use relating to 1-ethyl-7-(2-methyl-6-(1h-1,2,4-triazol-3-yl) pyridin-3-yl) -3,4-dihydropyrazino[2,3-b]pyrazin-2(1h)-one |
| MX368286B (es) | 2013-04-17 | 2019-09-27 | Signal Pharm Llc | Terapia de combinacion que comprende un inhibidor de tor cinasa y un compuesto de quinazolinona 5-sustituida para tratar cancer. |
| JP6401250B2 (ja) | 2013-05-29 | 2018-10-10 | シグナル ファーマシューティカルズ，エルエルシー | ７−（６−（２−ヒドロキシプロパン−２−イル）ピリジン−３−イル）−１−（（ｔｒａｎｓ）−４−メトキシシクロヘキシル）−３，４−ジヒドロピラジノ［２，３−ｂ］ピラジン−２（１Ｈ）−オン、その固体形態の医薬組成物、及びその使用方法 |
| WO2015040609A1 (en) | 2013-09-17 | 2015-03-26 | Yeda Research And Development Co. Ltd. | Erk-derived peptides and uses thereof |
| GB201320732D0 (en) | 2013-11-25 | 2014-01-08 | Cancer Rec Tech Ltd | Methods of chemical synthesis |
| GB201320729D0 (en) | 2013-11-25 | 2014-01-08 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| US9718824B2 (en) | 2014-04-16 | 2017-08-01 | Signal Pharmaceuticals, Llc | Solid forms comprising 7-(6-(2-hydroxypropan-2-yl)pyridin-3-yl)-1-((trans)-4-methoxycyclohexyl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one, and a coformer, compositions and methods of use thereof |
| US9737535B2 (en) | 2014-04-16 | 2017-08-22 | Signal Pharmaceuticals, Llc | Methods for treating cancer using TOR kinase inhibitor combination therapy comprising administering substituted pyrazino[2,3-b]pyrazines |
| NZ714742A (en) | 2014-04-16 | 2017-04-28 | Signal Pharm Llc | Solid forms of 1-ethyl-7-(2-methyl-6-(1h-1,2,4-triazol-3-yl)pyridin-3-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1h)-one, compositions thereof and methods of their use |
| US9512129B2 (en) | 2014-04-16 | 2016-12-06 | Signal Pharmaceuticals, Llc | Solid forms comprising 1-ethyl-7-(2-methyl-6-(1H-1,2,4-triazol-3-yl)pyridin-3-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one and a coformer |
| AU2015289929A1 (en) | 2014-07-14 | 2017-03-02 | Signal Pharmaceuticals, Llc | Methods of treating a cancer using substituted pyrrolopyrimidine compounds, compositions thereof |
| NZ629796A (en) | 2014-07-14 | 2015-12-24 | Signal Pharm Llc | Amorphous form of 4-((4-(cyclopentyloxy)-5-(2-methylbenzo[d]oxazol-6-yl)-7h-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-methoxy-n-methylbenzamide, compositions thereof and methods of their use |
| LT3572405T (lt) | 2014-09-12 | 2023-10-25 | Biohaven Therapeutics Ltd. | Benzoimidazol-1,2-ilo amidai, kaip kv7 kanalų aktyvatoriai |
| EP3641772B1 (en) | 2017-06-22 | 2023-08-02 | Celgene Corporation | Treatment of hepatocellular carcinoma characterized by hepatitis b virus infection |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3590045A (en) * | 1969-09-25 | 1971-06-29 | Smith Kline French Lab | Certain substituted imidazo (4,5-b)pyridines |
| BE788065A (fr) | 1971-08-26 | 1973-02-26 | Degussa | Nouvelles aza-benzimidazoles et procede pour leur preparation |
| SE422799B (sv) | 1975-05-28 | 1982-03-29 | Merck & Co Inc | Analogiforfarande for framstellning av 1,3-dihydroimidazo (4,5-b)pyridin-2-oner |
| ES473201A1 (es) * | 1977-09-26 | 1979-03-16 | Degussa | Procedimiento para la preparacion de 7-azabencimidazoles |
| US5217999A (en) * | 1987-12-24 | 1993-06-08 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Styryl compounds which inhibit EGF receptor protein tyrosine kinase |
| ATE114661T1 (de) * | 1990-04-02 | 1994-12-15 | Pfizer | Benzylphosphonsäure-tyrosinkinaseinhibitoren. |
| US5302606A (en) * | 1990-04-16 | 1994-04-12 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Styryl-substituted pyridyl compounds which inhibit EGF receptor tyrosine kinase |
| AU658646B2 (en) * | 1991-05-10 | 1995-04-27 | Rhone-Poulenc Rorer International (Holdings) Inc. | Bis mono-and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| JPH06503095A (ja) * | 1991-05-29 | 1994-04-07 | ファイザー・インコーポレーテッド | 三環式ポリヒドロキシ系のチロシンキナーゼ阻害薬 |
| GB9300059D0 (en) * | 1992-01-20 | 1993-03-03 | Zeneca Ltd | Quinazoline derivatives |
| EP0654024A1 (en) * | 1992-08-06 | 1995-05-24 | Warner-Lambert Company | 2-thioindoles (selenoindoles) and related disulfides (selenides) which inhibit protein tyrosine kinases and which have antitumor properties |
| US5330992A (en) * | 1992-10-23 | 1994-07-19 | Sterling Winthrop Inc. | 1-cyclopropyl-4-pyridyl-quinolinones |
| GB9226855D0 (en) * | 1992-12-23 | 1993-02-17 | Erba Carlo Spa | Vinylene-azaindole derivatives and process for their preparation |
| US5582995A (en) | 1993-06-11 | 1996-12-10 | The General Hospital Corporation | Methods of screening for compounds which inhibit the direct binding of Ras to Raf |
| CA2166721C (en) * | 1993-07-06 | 1999-07-27 | Allen Jacob Duplantier | Bicyclic tetrahydro pyrazolopyridines |
| US5645982A (en) * | 1993-08-19 | 1997-07-08 | Systemix, Inc. | Method for screening potential therapeutically effective antiviral agents |
| GB9501567D0 (en) * | 1995-01-26 | 1995-03-15 | Pharmacia Spa | Hydrosoluble 3-arylidene-2-oxindole derivatives as tyrosine kinase inhibitors |
| US5880141A (en) * | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
-
1998
- 1998-09-23 ES ES98949464T patent/ES2230719T3/es not_active Expired - Lifetime
- 1998-09-23 WO PCT/US1998/019973 patent/WO1999016438A1/en not_active Ceased
- 1998-09-23 RU RU2000110736/15A patent/RU2230553C2/ru not_active IP Right Cessation
- 1998-09-23 TR TR2000/01546T patent/TR200001546T2/xx unknown
- 1998-09-23 PT PT98949464T patent/PT1017384E/pt unknown
- 1998-09-23 IL IL13510998A patent/IL135109A0/xx not_active IP Right Cessation
- 1998-09-23 SK SK415-2000A patent/SK285357B6/sk unknown
- 1998-09-23 BR BR9812682-2A patent/BR9812682A/pt not_active Application Discontinuation
- 1998-09-23 DE DE69827516T patent/DE69827516T2/de not_active Expired - Fee Related
- 1998-09-23 IL IL15864998A patent/IL158649A0/xx not_active IP Right Cessation
- 1998-09-23 AT AT98949464T patent/ATE281834T1/de not_active IP Right Cessation
- 1998-09-23 HU HU0004024A patent/HUP0004024A3/hu unknown
- 1998-09-23 PL PL339744A patent/PL191618B1/pl not_active IP Right Cessation
- 1998-09-23 DK DK98949464T patent/DK1017384T3/da active
- 1998-09-23 KR KR1020007003192A patent/KR100547929B1/ko not_active Expired - Fee Related
- 1998-09-23 EP EP98949464A patent/EP1017384B1/en not_active Expired - Lifetime
- 1998-09-23 CN CNB988107538A patent/CN1167420C/zh not_active Expired - Fee Related
- 1998-09-23 UA UA2000042349A patent/UA72448C2/uk unknown
- 1998-09-23 CA CA002305370A patent/CA2305370C/en not_active Expired - Fee Related
- 1998-09-23 NZ NZ503432A patent/NZ503432A/xx unknown
- 1998-09-23 US US09/160,212 patent/US6093728A/en not_active Expired - Fee Related
- 1998-09-23 AU AU95781/98A patent/AU748849B2/en not_active Ceased
- 1998-09-23 JP JP2000513574A patent/JP2001517699A/ja not_active Withdrawn
- 1998-09-25 ZA ZA9808797A patent/ZA988797B/xx unknown
- 1998-09-25 TW TW087115979A patent/TW581815B/zh not_active IP Right Cessation
- 1998-09-25 AR ARP980104793A patent/AR017266A1/es unknown
-
2000
- 2000-03-15 IL IL135109A patent/IL135109A/en unknown
- 2000-03-24 NO NO20001555A patent/NO325663B1/no unknown
- 2000-04-19 BG BG104356A patent/BG64784B1/bg unknown
-
2002
- 2002-03-15 NZ NZ517808A patent/NZ517808A/en unknown
- 2002-11-15 US US10/294,802 patent/US6855723B2/en not_active Expired - Fee Related
-
2003
- 2003-10-29 IL IL158649A patent/IL158649A/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69827516T2 (de) | Azabenzimidazol-verbindungen zur modulation der serin/threonin protein-kinase funktion | |
| DE69835612T2 (de) | Methoden zur regulierung der serin/threonin protein kinase funktion mit 5-azaquinoxalinderivaten | |
| US6204267B1 (en) | Methods of modulating serine/thereonine protein kinase function with quinazoline-based compounds | |
| CZ2000990A3 (cs) | Způsob in vitro modulace funkce serin/threonin protein kinázy, způsob in vitro identifikace sloučenin pro tuto modulaci, sloučeniny na bázi azabenzimidazolu,jejich použití, způsob jejich výroby a farmaceutické kompozice | |
| MXPA00002910A (en) | Azabenzimidazole-based compounds for modulating serine/threonine protein kinase function | |
| MXPA00003255A (en) | Methods of modulating serine/threonine protein kinase function with 5-azaquinoxaline-based compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: AETERNA ZENTARIS GMBH, 60314 FRANKFURT, DE |
|
| 8339 | Ceased/non-payment of the annual fee |