NO874780L - Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrrolo-benzimidazol-derivater. - Google Patents
Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrrolo-benzimidazol-derivater.Info
- Publication number
- NO874780L NO874780L NO874780A NO874780A NO874780L NO 874780 L NO874780 L NO 874780L NO 874780 A NO874780 A NO 874780A NO 874780 A NO874780 A NO 874780A NO 874780 L NO874780 L NO 874780L
- Authority
- NO
- Norway
- Prior art keywords
- dimethyl
- group
- pyrrolo
- dihydro
- benzimidazol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- BKOVMXWXILSWCU-UHFFFAOYSA-N pyrrolo[3,2-e]benzimidazole Chemical class C1=CC2=NC=CC2=C2N=CN=C21 BKOVMXWXILSWCU-UHFFFAOYSA-N 0.000 title claims description 3
- 230000001225 therapeutic effect Effects 0.000 title 1
- -1 aminophenyl group Chemical group 0.000 claims description 222
- 150000001875 compounds Chemical class 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- MYTGJCXFDULENS-UHFFFAOYSA-N 5-ethyl-7,7-dimethyl-2-pyridin-4-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=NC=C1 MYTGJCXFDULENS-UHFFFAOYSA-N 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 230000010933 acylation Effects 0.000 claims description 5
- 238000005917 acylation reaction Methods 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 235000005985 organic acids Nutrition 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 238000005661 deetherification reaction Methods 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 150000003248 quinolines Chemical class 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 238000002844 melting Methods 0.000 description 222
- 230000008018 melting Effects 0.000 description 222
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 164
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
- 229910001868 water Inorganic materials 0.000 description 76
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 49
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 43
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 229960000583 acetic acid Drugs 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000012362 glacial acetic acid Substances 0.000 description 20
- 229910052739 hydrogen Inorganic materials 0.000 description 20
- 239000001257 hydrogen Substances 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
- 239000007868 Raney catalyst Substances 0.000 description 12
- 229910000564 Raney nickel Inorganic materials 0.000 description 12
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000005605 benzo group Chemical group 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- XTKWIKUPRBPXBE-UHFFFAOYSA-N 5,6-diamino-1-ethyl-3,3-dimethylindol-2-one Chemical compound NC1=C(N)C=C2N(CC)C(=O)C(C)(C)C2=C1 XTKWIKUPRBPXBE-UHFFFAOYSA-N 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- CDBTVKDGZGEGEY-UHFFFAOYSA-N 5,6-diamino-1-ethyl-3,3-dimethylindol-2-one;dihydrochloride Chemical compound Cl.Cl.NC1=C(N)C=C2N(CC)C(=O)C(C)(C)C2=C1 CDBTVKDGZGEGEY-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 229940093915 gynecological organic acid Drugs 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- RLXNFNLXONWHJZ-UHFFFAOYSA-N 5-ethyl-2-(2-methoxy-4-methylsulfanylphenyl)-7,7-dimethyl-1H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=C(SC)C=C1OC RLXNFNLXONWHJZ-UHFFFAOYSA-N 0.000 description 3
- KJLGETIVHDHEML-UHFFFAOYSA-N 5-ethyl-7,7-dimethyl-2-(4-methylsulfanylphenyl)-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=C(SC)C=C1 KJLGETIVHDHEML-UHFFFAOYSA-N 0.000 description 3
- IRDXDAWEYIPLJT-UHFFFAOYSA-N 7,7-dimethyl-2-(4-methylsulfanylphenyl)-5-propyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=C(SC)C=C1 IRDXDAWEYIPLJT-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- GQZBTQCSVMYMBH-UHFFFAOYSA-N 2-(4-aminophenyl)-5-ethyl-7,7-dimethyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=C(N)C=C1 GQZBTQCSVMYMBH-UHFFFAOYSA-N 0.000 description 2
- GGMRTDZPPGFMPB-UHFFFAOYSA-N 2-phenyl-n-(1,3,3-trimethyl-6-nitro-2-oxoindol-5-yl)prop-2-enamide Chemical compound [O-][N+](=O)C=1C=C2N(C)C(=O)C(C)(C)C2=CC=1NC(=O)C(=C)C1=CC=CC=C1 GGMRTDZPPGFMPB-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- YPRCKKHHMOZUMZ-UHFFFAOYSA-N 5-(2-methoxyethyl)-2-(4-methoxyphenyl)-7,7-dimethyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=C(OC)C=C1 YPRCKKHHMOZUMZ-UHFFFAOYSA-N 0.000 description 2
- JRRYHWVZPKFVIK-UHFFFAOYSA-N 5-(2-methoxyethyl)-7,7-dimethyl-2-pyridin-3-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=CN=C1 JRRYHWVZPKFVIK-UHFFFAOYSA-N 0.000 description 2
- LUEOVMBMFVUKOT-UHFFFAOYSA-N 5-amino-1,3,3-trimethyl-6-nitroindol-2-one Chemical compound NC1=C([N+]([O-])=O)C=C2N(C)C(=O)C(C)(C)C2=C1 LUEOVMBMFVUKOT-UHFFFAOYSA-N 0.000 description 2
- ZTLFEJSBWUFVFY-UHFFFAOYSA-N 5-amino-1-ethyl-3,3-dimethyl-6-nitroindol-2-one Chemical compound NC1=C([N+]([O-])=O)C=C2N(CC)C(=O)C(C)(C)C2=C1 ZTLFEJSBWUFVFY-UHFFFAOYSA-N 0.000 description 2
- DIEITLQKPJZWIH-UHFFFAOYSA-N 5-ethyl-2-(4-methoxyphenyl)-7,7-dimethyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=C(OC)C=C1 DIEITLQKPJZWIH-UHFFFAOYSA-N 0.000 description 2
- IJHAAEXLUUASAT-UHFFFAOYSA-N 5-ethyl-2-(furan-2-yl)-7,7-dimethyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical group N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=CO1 IJHAAEXLUUASAT-UHFFFAOYSA-N 0.000 description 2
- BFTKZPQSNCADBB-UHFFFAOYSA-N 5-ethyl-7,7-dimethyl-2-(4-methyl-1,3-oxazol-5-yl)-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C=1OC=NC=1C BFTKZPQSNCADBB-UHFFFAOYSA-N 0.000 description 2
- HXEXZNSKKSBTJR-UHFFFAOYSA-N 5h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C=1C2=NC=NC2=CC2=CC(=O)NC2=1 HXEXZNSKKSBTJR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BHRHUZMEAXFXBV-UHFFFAOYSA-N N-(1-ethyl-3,3-dimethyl-6-nitro-2-oxoindol-5-yl)-2-thiophen-2-ylacetamide Chemical compound [O-][N+](=O)C=1C=C2N(CC)C(=O)C(C)(C)C2=CC=1NC(=O)CC1=CC=CS1 BHRHUZMEAXFXBV-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000002785 anti-thrombosis Effects 0.000 description 2
- WOXQTRUXNFNMDU-UHFFFAOYSA-N benzimidazol-5-one Chemical compound O=C1C=CC2=NC=NC2=C1 WOXQTRUXNFNMDU-UHFFFAOYSA-N 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229950005499 carbon tetrachloride Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- BNTRVUUJBGBGLZ-UHFFFAOYSA-N hydron;pyridine-4-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=NC=C1 BNTRVUUJBGBGLZ-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 2
- HPMLYJGINHZAQD-UHFFFAOYSA-N n-(1,3,3-trimethyl-2-oxoindol-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2N(C)C(=O)C(C)(C)C2=C1 HPMLYJGINHZAQD-UHFFFAOYSA-N 0.000 description 2
- ONANFVRERAJCQS-UHFFFAOYSA-N n-(1,3,3-trimethyl-6-nitro-2-oxoindol-5-yl)pyridine-4-carboxamide Chemical compound [O-][N+](=O)C=1C=C2N(C)C(=O)C(C)(C)C2=CC=1NC(=O)C1=CC=NC=C1 ONANFVRERAJCQS-UHFFFAOYSA-N 0.000 description 2
- PHOQDQVKFPOSGM-UHFFFAOYSA-N n-(1-butyl-3,3-dimethyl-6-nitro-2-oxoindol-5-yl)-2-thiophen-2-ylacetamide Chemical compound [O-][N+](=O)C=1C=C2N(CCCC)C(=O)C(C)(C)C2=CC=1NC(=O)CC1=CC=CS1 PHOQDQVKFPOSGM-UHFFFAOYSA-N 0.000 description 2
- MNHXHIQKCPRVEU-UHFFFAOYSA-N n-(1-butyl-3,3-dimethyl-6-nitro-2-oxoindol-5-yl)-2-thiophen-3-ylacetamide Chemical compound [O-][N+](=O)C=1C=C2N(CCCC)C(=O)C(C)(C)C2=CC=1NC(=O)CC=1C=CSC=1 MNHXHIQKCPRVEU-UHFFFAOYSA-N 0.000 description 2
- XQLFGTCGUBPEQU-UHFFFAOYSA-N n-(1-ethyl-3,3-dimethyl-2-oxoindol-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2N(CC)C(=O)C(C)(C)C2=C1 XQLFGTCGUBPEQU-UHFFFAOYSA-N 0.000 description 2
- MUSGGRBWOBTFDM-UHFFFAOYSA-N n-(1-ethyl-3,3-dimethyl-6-nitro-2-oxoindol-5-yl)-2-thiophen-3-ylacetamide Chemical compound [O-][N+](=O)C=1C=C2N(CC)C(=O)C(C)(C)C2=CC=1NC(=O)CC=1C=CSC=1 MUSGGRBWOBTFDM-UHFFFAOYSA-N 0.000 description 2
- WANVWWNIVMVTTM-UHFFFAOYSA-N n-(3,3-dimethyl-2-oxo-1h-indol-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2NC(=O)C(C)(C)C2=C1 WANVWWNIVMVTTM-UHFFFAOYSA-N 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 230000009090 positive inotropic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- CJVXTSNZRBONJH-UHFFFAOYSA-N 1,3,3-trimethyl-5-(methylamino)-6-nitroindol-2-one Chemical compound C1=C([N+]([O-])=O)C(NC)=CC2=C1N(C)C(=O)C2(C)C CJVXTSNZRBONJH-UHFFFAOYSA-N 0.000 description 1
- BCQLKOHITIMFRI-UHFFFAOYSA-N 1,3,3-trimethyl-6-(methylamino)-5-nitroindol-2-one Chemical compound C1=C([N+]([O-])=O)C(NC)=CC2=C1C(C)(C)C(=O)N2C BCQLKOHITIMFRI-UHFFFAOYSA-N 0.000 description 1
- DFYDCCLRYRKXPE-UHFFFAOYSA-N 1,5,7,7-tetramethyl-2-pyridin-3-ylpyrrolo[2,3-f]benzimidazol-6-one Chemical compound N1=CC(=CC=C1)C1=NC2=C(N1C)C=C1C(=C2)N(C(C1(C)C)=O)C DFYDCCLRYRKXPE-UHFFFAOYSA-N 0.000 description 1
- OHXLISJFEWDBFP-UHFFFAOYSA-N 1,5,7,7-tetramethyl-2-pyridin-4-ylpyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(C)C(=O)C(C)(C)C3=CC=2N(C)C=1C1=CC=NC=C1 OHXLISJFEWDBFP-UHFFFAOYSA-N 0.000 description 1
- CZFQQWVFWKGYLK-UHFFFAOYSA-N 1,5,7-trimethyl-2-pyridin-2-yl-7h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound CN1C=2C=C3C(C)C(=O)N(C)C3=CC=2N=C1C1=CC=CC=N1 CZFQQWVFWKGYLK-UHFFFAOYSA-N 0.000 description 1
- HIJGSCXBOWBDMT-UHFFFAOYSA-N 1,5,7-trimethyl-2-pyridin-3-yl-7h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound CN1C=2C=C3C(C)C(=O)N(C)C3=CC=2N=C1C1=CC=CN=C1 HIJGSCXBOWBDMT-UHFFFAOYSA-N 0.000 description 1
- FBNSNUQEZKDBPJ-UHFFFAOYSA-N 1,5,7-trimethyl-2-pyridin-4-yl-7h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound CN1C=2C=C3C(C)C(=O)N(C)C3=CC=2N=C1C1=CC=NC=C1 FBNSNUQEZKDBPJ-UHFFFAOYSA-N 0.000 description 1
- KMZFGZKAUWCHRQ-UHFFFAOYSA-N 1,5-dimethyl-2-pyridin-2-yl-7h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(C)C(=O)CC3=CC=2N(C)C=1C1=CC=CC=N1 KMZFGZKAUWCHRQ-UHFFFAOYSA-N 0.000 description 1
- IPAYDGAPEAVKHK-UHFFFAOYSA-N 1,5-dimethyl-2-pyridin-3-yl-7h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(C)C(=O)CC3=CC=2N(C)C=1C1=CC=CN=C1 IPAYDGAPEAVKHK-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 description 1
- GNLNICJZIINYQB-UHFFFAOYSA-N 2-(2,6-dichloropyridin-4-yl)-5-ethyl-7,7-dimethyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC(Cl)=NC(Cl)=C1 GNLNICJZIINYQB-UHFFFAOYSA-N 0.000 description 1
- VGUUPUPDIJMXGB-UHFFFAOYSA-N 2-(2-chloro-6-methoxyquinolin-4-yl)-5-ethyl-7,7-dimethyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C(OC)C=C2C(C=3NC=4C=C5C(C)(C)C(=O)N(C5=CC=4N=3)CC)=CC(Cl)=NC2=C1 VGUUPUPDIJMXGB-UHFFFAOYSA-N 0.000 description 1
- BMGQAHXHFAECTA-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-ethyl-7,7-dimethyl-1H-pyrrolo[2,3-f]benzimidazol-6-one hydrochloride Chemical compound Cl.N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=CC=C1Cl BMGQAHXHFAECTA-UHFFFAOYSA-N 0.000 description 1
- HTAPHXDFPBLLCE-UHFFFAOYSA-N 2-(4-amino-3,5-dibromophenyl)-5-ethyl-7,7-dimethyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC(Br)=C(N)C(Br)=C1 HTAPHXDFPBLLCE-UHFFFAOYSA-N 0.000 description 1
- UVNVJAIMCIGJHI-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-1,5,7,7-tetramethylpyrrolo[2,3-f]benzimidazol-6-one Chemical compound OC1=CC=C(C=C1)C1=NC2=C(N1C)C=C1C(=C2)N(C(C1(C)C)=O)C UVNVJAIMCIGJHI-UHFFFAOYSA-N 0.000 description 1
- OXILGFMYMGCROS-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-3,5,7,7-tetramethylpyrrolo[3,2-f]benzimidazol-6-one Chemical compound OC1=CC=C(C=C1)C=1N(C2=C(N1)C=C1C(=C2)N(C(C1(C)C)=O)C)C OXILGFMYMGCROS-UHFFFAOYSA-N 0.000 description 1
- CIISJCPOVGLCKU-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-3,5,7-trimethyl-7H-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound OC1=CC=C(C=C1)C=1N(C2=C(N1)C=C1C(=C2)N(C(C1C)=O)C)C CIISJCPOVGLCKU-UHFFFAOYSA-N 0.000 description 1
- YOCFDBNSZSVHEP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-3,5-dimethyl-7H-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C(=NC2=C1C=C1C(=C2)CC(N1C)=O)C1=CC=C(C=C1)O YOCFDBNSZSVHEP-UHFFFAOYSA-N 0.000 description 1
- NAZBOMLLDHXOME-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-5,7,7-trimethyl-1H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound OC1=CC=C(C=C1)C=1NC2=C(N1)C=C1C(=C2)N(C(C1(C)C)=O)C NAZBOMLLDHXOME-UHFFFAOYSA-N 0.000 description 1
- DKBUNFVDCIXKPP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-5-(2-methoxyethyl)-1,7,7-trimethylpyrrolo[2,3-f]benzimidazol-6-one Chemical compound COCCN1C(=O)C(C)(C)c2cc3n(C)c(nc3cc12)-c1ccc(O)cc1 DKBUNFVDCIXKPP-UHFFFAOYSA-N 0.000 description 1
- TWCOHCOHOJDACO-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-5-(2-methoxyethyl)-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound COCCN1C(CC=2C1=CC1=C(N=C(N1)C1=CC=C(C=C1)O)C=2)=O TWCOHCOHOJDACO-UHFFFAOYSA-N 0.000 description 1
- PJOYMIRQWWAULP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-5-(2-methoxyethyl)-1,7-dimethyl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound COCCN1C(=O)C(C)c2cc3n(C)c(nc3cc12)-c1ccc(O)cc1 PJOYMIRQWWAULP-UHFFFAOYSA-N 0.000 description 1
- YRRIXBWHSYTQFT-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-5-(2-methoxyethyl)-1-methyl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound COCCN1C(CC=2C1=CC1=C(N(C(=N1)C1=CC=C(C=C1)O)C)C=2)=O YRRIXBWHSYTQFT-UHFFFAOYSA-N 0.000 description 1
- IBLFQOJXCZWFHX-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-5-(2-methoxyethyl)-3,7-dimethyl-7H-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound COCCN1C(=O)C(C)c2cc3nc(-c4ccc(O)cc4)n(C)c3cc12 IBLFQOJXCZWFHX-UHFFFAOYSA-N 0.000 description 1
- PQFQGYKFECDTTO-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-5-(2-methoxyethyl)-3-methyl-7H-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound OC1=CC=C(C=C1)C=1N(C2=C(N=1)C=C1C(=C2)N(C(C1)=O)CCOC)C PQFQGYKFECDTTO-UHFFFAOYSA-N 0.000 description 1
- WDYJVBKEGVDVTB-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-5-(2-methoxyethyl)-7,7-dimethyl-1H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound CC1(C(N(C2=CC3=C(N=C(N3)C3=CC=C(C=C3)O)C=C21)CCOC)=O)C WDYJVBKEGVDVTB-UHFFFAOYSA-N 0.000 description 1
- CTIYOULOCOSAKH-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-5-(2-methoxyethyl)-7-methyl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound COCCN1C(C(C=2C1=CC1=C(N=C(N1)C1=CC=C(C=C1)O)C=2)C)=O CTIYOULOCOSAKH-UHFFFAOYSA-N 0.000 description 1
- PJHUTZWWTJDZFY-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-5-methyl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound CN1C(CC=2C1=CC1=C(N=C(N1)C1=CC=C(C=C1)O)C2)=O PJHUTZWWTJDZFY-UHFFFAOYSA-N 0.000 description 1
- LAVXELNYVZXDIC-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1,5,7-trimethyl-7h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=CC(OC)=CC=C1C(N(C1=C2)C)=NC1=CC1=C2C(C)C(=O)N1C LAVXELNYVZXDIC-UHFFFAOYSA-N 0.000 description 1
- QZMWWWCATUYUEB-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1,5-dimethyl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound CN1C(=NC2=C1C=C1C(=C2)N(C(C1)=O)C)C1=CC=C(C=C1)OC QZMWWWCATUYUEB-UHFFFAOYSA-N 0.000 description 1
- NNXDCKPOGGOZDW-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3,5-dimethyl-7h-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound C1=CC(OC)=CC=C1C(N(C1=C2)C)=NC1=CC1=C2N(C)C(=O)C1 NNXDCKPOGGOZDW-UHFFFAOYSA-N 0.000 description 1
- JTZQLEXCRGUKSS-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5,7,7-trimethyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=CC(OC)=CC=C1C(NC1=C2)=NC1=CC1=C2C(C)(C)C(=O)N1C JTZQLEXCRGUKSS-UHFFFAOYSA-N 0.000 description 1
- AUEPMOPPIZPQSE-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5,7-dimethyl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=CC(OC)=CC=C1C(NC1=C2)=NC1=CC1=C2C(C)C(=O)N1C AUEPMOPPIZPQSE-UHFFFAOYSA-N 0.000 description 1
- FJXAUMGCAKEEEW-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-methyl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=CC(OC)=CC=C1C(NC1=C2)=NC1=CC1=C2CC(=O)N1C FJXAUMGCAKEEEW-UHFFFAOYSA-N 0.000 description 1
- XHUUTQQIKOFTLE-UHFFFAOYSA-N 2-(4-methoxyphenyl)-7,7-dimethyl-5-pentyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCCCC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=C(OC)C=C1 XHUUTQQIKOFTLE-UHFFFAOYSA-N 0.000 description 1
- HIYMVJOXQFLOSR-UHFFFAOYSA-N 2-(4-methoxyphenyl)-7,7-dimethyl-5-propan-2-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=CC(OC)=CC=C1C(NC1=C2)=NC1=CC1=C2C(C)(C)C(=O)N1C(C)C HIYMVJOXQFLOSR-UHFFFAOYSA-N 0.000 description 1
- WWCJTVDXZUIFNF-UHFFFAOYSA-N 2-(furan-3-yl)-5-(2-methoxyethyl)-7,7-dimethyl-1H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)(C)C3=CC=2NC=1C=1C=COC=1 WWCJTVDXZUIFNF-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- RTWGUAOCCYXKFE-UHFFFAOYSA-N 2-benzyl-5,7,7-trimethyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(C)C(=O)C(C)(C)C3=CC=2NC=1CC1=CC=CC=C1 RTWGUAOCCYXKFE-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- YTRMTPPVNRALON-UHFFFAOYSA-N 2-phenyl-4-quinolinecarboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1 YTRMTPPVNRALON-UHFFFAOYSA-N 0.000 description 1
- SAADHTGAYJGHJD-UHFFFAOYSA-N 2-phenyl-n-(1,3,3-trimethyl-6-nitro-2-oxoindol-5-yl)acetamide Chemical compound [O-][N+](=O)C=1C=C2N(C)C(=O)C(C)(C)C2=CC=1NC(=O)CC1=CC=CC=C1 SAADHTGAYJGHJD-UHFFFAOYSA-N 0.000 description 1
- BPMVWRKZYYJRHW-UHFFFAOYSA-N 3,5,7,7-tetramethyl-2-pyridin-2-ylpyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(C)C(=O)C(C)(C)C3=CC=2N=C1C1=CC=CC=N1 BPMVWRKZYYJRHW-UHFFFAOYSA-N 0.000 description 1
- USWJIWVDUPDBEI-UHFFFAOYSA-N 3,5,7,7-tetramethyl-2-pyridin-3-ylpyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(C)C(=O)C(C)(C)C3=CC=2N=C1C1=CC=CN=C1 USWJIWVDUPDBEI-UHFFFAOYSA-N 0.000 description 1
- XRUSWUPNRLPGJK-UHFFFAOYSA-N 3,5,7,7-tetramethyl-2-pyridin-4-ylpyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(C)C(=O)C(C)(C)C3=CC=2N=C1C1=CC=NC=C1 XRUSWUPNRLPGJK-UHFFFAOYSA-N 0.000 description 1
- XTHIPJYGZHMZGZ-UHFFFAOYSA-N 3,5-dimethyl-2-pyridin-3-yl-7h-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(C)C(=O)CC3=CC=2N=C1C1=CC=CN=C1 XTHIPJYGZHMZGZ-UHFFFAOYSA-N 0.000 description 1
- HOASQMPPYNKSDB-UHFFFAOYSA-N 3,5-dimethyl-2-pyridin-4-yl-7h-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(C)C(=O)CC3=CC=2N=C1C1=CC=NC=C1 HOASQMPPYNKSDB-UHFFFAOYSA-N 0.000 description 1
- NHHLMQNXFUCWGE-UHFFFAOYSA-N 3-amino-1-nitro-3H-indol-2-one Chemical class C1=CC=C2C(N)C(=O)N([N+]([O-])=O)C2=C1 NHHLMQNXFUCWGE-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- IKOUOYTVSULRQG-UHFFFAOYSA-N 3-phenyl-n-(1,3,3-trimethyl-6-nitro-2-oxoindol-5-yl)propanamide Chemical compound [O-][N+](=O)C=1C=C2N(C)C(=O)C(C)(C)C2=CC=1NC(=O)CCC1=CC=CC=C1 IKOUOYTVSULRQG-UHFFFAOYSA-N 0.000 description 1
- WSXGQYDHJZKQQB-UHFFFAOYSA-N 3-pyridin-4-ylpropanoic acid Chemical compound OC(=O)CCC1=CC=NC=C1 WSXGQYDHJZKQQB-UHFFFAOYSA-N 0.000 description 1
- WGNUNYPERJMVRM-UHFFFAOYSA-N 3-pyridylacetic acid Chemical compound OC(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-N 0.000 description 1
- KJUCKWGCMSXNMM-UHFFFAOYSA-N 4-(5-ethyl-7,7-dimethyl-6-oxo-1h-pyrrolo[2,3-f]benzimidazol-2-yl)benzonitrile Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=C(C#N)C=C1 KJUCKWGCMSXNMM-UHFFFAOYSA-N 0.000 description 1
- XIYPBQCSUQJYHA-UHFFFAOYSA-N 4-methoxy-n-(1,3,3-trimethyl-6-nitro-2-oxoindol-5-yl)benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC(C(C(=O)N2C)(C)C)=C2C=C1[N+]([O-])=O XIYPBQCSUQJYHA-UHFFFAOYSA-N 0.000 description 1
- VDIDAFWGKAHVBY-UHFFFAOYSA-N 4-methoxy-n-[1-(2-methoxyethyl)-3,3-dimethyl-6-nitro-2-oxoindol-5-yl]benzamide Chemical compound [O-][N+](=O)C=1C=C2N(CCOC)C(=O)C(C)(C)C2=CC=1NC(=O)C1=CC=C(OC)C=C1 VDIDAFWGKAHVBY-UHFFFAOYSA-N 0.000 description 1
- HUTNXAYRNHOZHL-UHFFFAOYSA-N 4-methyl-3h-1,3-oxazol-2-one Chemical compound CC1=COC(=O)N1 HUTNXAYRNHOZHL-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- BIRIVPOTERXIOW-UHFFFAOYSA-N 4-oxo-7-(trifluoromethyl)-1h-quinoline-3-carboxylic acid Chemical compound FC(F)(F)C1=CC=C2C(=O)C(C(=O)O)=CNC2=C1 BIRIVPOTERXIOW-UHFFFAOYSA-N 0.000 description 1
- KRRYJIQEDPVZQK-UHFFFAOYSA-N 5,7,7-trimethyl-2-(2-phenylethenyl)-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(C)C(=O)C(C)(C)C3=CC=2NC=1C=CC1=CC=CC=C1 KRRYJIQEDPVZQK-UHFFFAOYSA-N 0.000 description 1
- KIXPKBYRLIXWKA-UHFFFAOYSA-N 5,7,7-trimethyl-2-(2-phenylethyl)-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N1C=2C=C3N(C)C(=O)C(C)(C)C3=CC=2N=C1CCC1=CC=CC=C1 KIXPKBYRLIXWKA-UHFFFAOYSA-N 0.000 description 1
- ROQCIARGYQPYDB-UHFFFAOYSA-N 5,7,7-trimethyl-2-pyridin-2-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(C)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=CC=N1 ROQCIARGYQPYDB-UHFFFAOYSA-N 0.000 description 1
- ZJPLZLWESAEIDB-UHFFFAOYSA-N 5,7,7-trimethyl-2-pyridin-3-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(C)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=CN=C1 ZJPLZLWESAEIDB-UHFFFAOYSA-N 0.000 description 1
- JWPIRNZNWQJMLA-UHFFFAOYSA-N 5,7,7-trimethyl-2-pyridin-4-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(C)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=NC=C1 JWPIRNZNWQJMLA-UHFFFAOYSA-N 0.000 description 1
- KAUYSJBBYSDHEH-UHFFFAOYSA-N 5,7,7-trimethyl-2-thiophen-2-yl-1H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound S1C(=CC=C1)C=1NC2=C(N=1)C=C1C(=C2)N(C(C1(C)C)=O)C KAUYSJBBYSDHEH-UHFFFAOYSA-N 0.000 description 1
- QPSSFMKJCNAXEH-UHFFFAOYSA-N 5,7-dimethyl-2-pyridin-2-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N1C=2C=C3C(C)C(=O)N(C)C3=CC=2N=C1C1=CC=CC=N1 QPSSFMKJCNAXEH-UHFFFAOYSA-N 0.000 description 1
- GAFCALDSBZKICJ-UHFFFAOYSA-N 5,7-dimethyl-2-pyridin-3-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N1C=2C=C3C(C)C(=O)N(C)C3=CC=2N=C1C1=CC=CN=C1 GAFCALDSBZKICJ-UHFFFAOYSA-N 0.000 description 1
- NSTQJTIZPJCVDA-UHFFFAOYSA-N 5,7-dimethyl-2-pyridin-4-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N1C=2C=C3C(C)C(=O)N(C)C3=CC=2N=C1C1=CC=NC=C1 NSTQJTIZPJCVDA-UHFFFAOYSA-N 0.000 description 1
- PVMBATGAYRHMHC-UHFFFAOYSA-N 5-(2-hydroxyethyl)-1,7,7-trimethyl-2-pyridin-2-ylpyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C2=CC=3N(CCO)C(=O)C(C)(C)C=3C=C2N(C)C=1C1=CC=CC=N1 PVMBATGAYRHMHC-UHFFFAOYSA-N 0.000 description 1
- VLFFTKCFMDZYCR-UHFFFAOYSA-N 5-(2-hydroxyethyl)-1,7,7-trimethyl-2-pyridin-3-ylpyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C2=CC=3N(CCO)C(=O)C(C)(C)C=3C=C2N(C)C=1C1=CC=CN=C1 VLFFTKCFMDZYCR-UHFFFAOYSA-N 0.000 description 1
- AJXAYJFDDXUFQX-UHFFFAOYSA-N 5-(2-hydroxyethyl)-1,7-dimethyl-2-pyridin-2-yl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound CN1C=2C=C3C(C)C(=O)N(CCO)C3=CC=2N=C1C1=CC=CC=N1 AJXAYJFDDXUFQX-UHFFFAOYSA-N 0.000 description 1
- KMNMVSLJIUVPRS-UHFFFAOYSA-N 5-(2-hydroxyethyl)-1,7-dimethyl-2-pyridin-3-yl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound CN1C=2C=C3C(C)C(=O)N(CCO)C3=CC=2N=C1C1=CC=CN=C1 KMNMVSLJIUVPRS-UHFFFAOYSA-N 0.000 description 1
- ZSQVBBACEBMGJR-UHFFFAOYSA-N 5-(2-hydroxyethyl)-1,7-dimethyl-2-pyridin-4-yl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound CN1C=2C=C3C(C)C(=O)N(CCO)C3=CC=2N=C1C1=CC=NC=C1 ZSQVBBACEBMGJR-UHFFFAOYSA-N 0.000 description 1
- ILBXAWVSAVIZEX-UHFFFAOYSA-N 5-(2-hydroxyethyl)-1-methyl-2-pyridin-2-yl-7h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C2=CC=3N(CCO)C(=O)CC=3C=C2N(C)C=1C1=CC=CC=N1 ILBXAWVSAVIZEX-UHFFFAOYSA-N 0.000 description 1
- FUXUVXFOYCPKAZ-UHFFFAOYSA-N 5-(2-hydroxyethyl)-1-methyl-2-pyridin-3-yl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C2=CC=3N(CCO)C(=O)CC=3C=C2N(C)C=1C1=CC=CN=C1 FUXUVXFOYCPKAZ-UHFFFAOYSA-N 0.000 description 1
- POOHKKVHQSHPPD-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-1,7,7-trimethylpyrrolo[2,3-f]benzimidazol-6-one Chemical compound Cn1c(nc2cc3N(CCO)C(=O)C(C)(C)c3cc12)-c1ccc(O)cc1 POOHKKVHQSHPPD-UHFFFAOYSA-N 0.000 description 1
- WHVNBMDLLBMLJP-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound OCCN1C(=O)Cc2cc3[nH]c(nc3cc12)-c1ccc(O)cc1 WHVNBMDLLBMLJP-UHFFFAOYSA-N 0.000 description 1
- IZQZKVPVYIEHKZ-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-1-methyl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound OCCN1C(CC=2C1=CC1=C(N(C(=N1)C1=CC=C(C=C1)O)C)C=2)=O IZQZKVPVYIEHKZ-UHFFFAOYSA-N 0.000 description 1
- UTNGNLJBQPKVNY-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-3,7,7-trimethylpyrrolo[3,2-f]benzimidazol-6-one Chemical compound Cn1c(nc2cc3c(cc12)N(CCO)C(=O)C3(C)C)-c1ccc(O)cc1 UTNGNLJBQPKVNY-UHFFFAOYSA-N 0.000 description 1
- IWACTLLKPBUHFO-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-3,7-dimethyl-7H-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound CC1C(=O)N(CCO)c2cc3n(C)c(nc3cc12)-c1ccc(O)cc1 IWACTLLKPBUHFO-UHFFFAOYSA-N 0.000 description 1
- DSEBWKRLXMCQEC-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-(4-hydroxyphenyl)-7,7-dimethyl-1H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound CC1(C(N(C2=CC3=C(N=C(N3)C3=CC=C(C=C3)O)C=C21)CCO)=O)C DSEBWKRLXMCQEC-UHFFFAOYSA-N 0.000 description 1
- RNNUKSDPWKWTKP-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-1,7,7-trimethylpyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=CC(OC)=CC=C1C(N(C1=C2)C)=NC1=CC1=C2C(C)(C)C(=O)N1CCO RNNUKSDPWKWTKP-UHFFFAOYSA-N 0.000 description 1
- NPOSMSQTOUDRLI-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound OCCN1C(CC=2C1=CC1=C(N=C(N1)C1=CC=C(C=C1)OC)C=2)=O NPOSMSQTOUDRLI-UHFFFAOYSA-N 0.000 description 1
- SGCDSPZJIZBKRQ-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-1-methyl-7h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=CC(OC)=CC=C1C(N(C1=C2)C)=NC1=CC1=C2CC(=O)N1CCO SGCDSPZJIZBKRQ-UHFFFAOYSA-N 0.000 description 1
- HEHYFOJDNGWEOK-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-3,7,7-trimethylpyrrolo[3,2-f]benzimidazol-6-one Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC(C(C(=O)N3CCO)(C)C)=C3C=C2N1C HEHYFOJDNGWEOK-UHFFFAOYSA-N 0.000 description 1
- UBOZFAKXFILSCG-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-3,7-dimethyl-7H-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound C1=CC(OC)=CC=C1C(N(C1=C2)C)=NC1=CC1=C2N(CCO)C(=O)C1C UBOZFAKXFILSCG-UHFFFAOYSA-N 0.000 description 1
- DHWHQIRPUVWURR-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-7,7-dimethyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=CC(OC)=CC=C1C(NC1=C2)=NC1=CC1=C2C(C)(C)C(=O)N1CCO DHWHQIRPUVWURR-UHFFFAOYSA-N 0.000 description 1
- GRJVDWCKFOFROO-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-(4-methoxyphenyl)-7-methyl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=CC(OC)=CC=C1C(NC1=C2)=NC1=CC1=C2C(C)C(=O)N1CCO GRJVDWCKFOFROO-UHFFFAOYSA-N 0.000 description 1
- WQBPQYFCPGJSRY-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-pyridin-3-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCO)C(=O)CC3=CC=2NC=1C1=CC=CN=C1 WQBPQYFCPGJSRY-UHFFFAOYSA-N 0.000 description 1
- JKJWIXCJQOHGBL-UHFFFAOYSA-N 5-(2-hydroxyethyl)-2-pyridin-4-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound OCCN1C(CC=2C1=CC1=C(N=C(N1)C1=CC=NC=C1)C=2)=O JKJWIXCJQOHGBL-UHFFFAOYSA-N 0.000 description 1
- IPLLDIVMMNVPFS-UHFFFAOYSA-N 5-(2-hydroxyethyl)-3,7,7-trimethyl-2-pyridin-2-ylpyrrolo[3,2-f]benzimidazol-6-one Chemical compound N=1C2=CC(C(C(=O)N3CCO)(C)C)=C3C=C2N(C)C=1C1=CC=CC=N1 IPLLDIVMMNVPFS-UHFFFAOYSA-N 0.000 description 1
- PRTOLBGOYDZXOG-UHFFFAOYSA-N 5-(2-hydroxyethyl)-3,7,7-trimethyl-2-pyridin-4-ylpyrrolo[3,2-f]benzimidazol-6-one Chemical compound N=1C2=CC(C(C(=O)N3CCO)(C)C)=C3C=C2N(C)C=1C1=CC=NC=C1 PRTOLBGOYDZXOG-UHFFFAOYSA-N 0.000 description 1
- SXBANFKEFZGSCT-UHFFFAOYSA-N 5-(2-hydroxyethyl)-3,7-dimethyl-2-pyridin-3-yl-7H-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound N=1C=2C=C3C(C)C(=O)N(CCO)C3=CC=2N(C)C=1C1=CC=CN=C1 SXBANFKEFZGSCT-UHFFFAOYSA-N 0.000 description 1
- SDXUPXYTHSCYPG-UHFFFAOYSA-N 5-(2-hydroxyethyl)-3,7-dimethyl-2-pyridin-4-yl-7H-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound N=1C=2C=C3C(C)C(=O)N(CCO)C3=CC=2N(C)C=1C1=CC=NC=C1 SDXUPXYTHSCYPG-UHFFFAOYSA-N 0.000 description 1
- ZLPWRNCUZQOWPP-UHFFFAOYSA-N 5-(2-hydroxyethyl)-3-methyl-2-pyridin-2-yl-7H-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound OCCN1C(CC=2C1=CC1=C(N=C(N1C)C1=NC=CC=C1)C=2)=O ZLPWRNCUZQOWPP-UHFFFAOYSA-N 0.000 description 1
- QOZHJHPLHMUYGB-UHFFFAOYSA-N 5-(2-hydroxyethyl)-7,7-dimethyl-2-pyridin-2-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N1C=2C=C3C(C)(C)C(=O)N(CCO)C3=CC=2N=C1C1=CC=CC=N1 QOZHJHPLHMUYGB-UHFFFAOYSA-N 0.000 description 1
- YYPOAMRGUGKUBC-UHFFFAOYSA-N 5-(2-hydroxyethyl)-7,7-dimethyl-2-pyridin-3-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N1C=2C=C3C(C)(C)C(=O)N(CCO)C3=CC=2N=C1C1=CC=CN=C1 YYPOAMRGUGKUBC-UHFFFAOYSA-N 0.000 description 1
- VBNUAWCLLYTLTK-UHFFFAOYSA-N 5-(2-hydroxyethyl)-7,7-dimethyl-2-pyridin-4-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N1C=2C=C3C(C)(C)C(=O)N(CCO)C3=CC=2N=C1C1=CC=NC=C1 VBNUAWCLLYTLTK-UHFFFAOYSA-N 0.000 description 1
- NDUHYTARQAXWOY-UHFFFAOYSA-N 5-(2-hydroxyethyl)-7-methyl-2-pyridin-2-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N1C=2C=C3C(C)C(=O)N(CCO)C3=CC=2N=C1C1=CC=CC=N1 NDUHYTARQAXWOY-UHFFFAOYSA-N 0.000 description 1
- XQSPRHRKLBLENZ-UHFFFAOYSA-N 5-(2-hydroxyethyl)-7-methyl-2-pyridin-3-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N1C=2C=C3C(C)C(=O)N(CCO)C3=CC=2N=C1C1=CC=CN=C1 XQSPRHRKLBLENZ-UHFFFAOYSA-N 0.000 description 1
- JQYMADJWEUTCDT-UHFFFAOYSA-N 5-(2-hydroxyethyl)-7-methyl-2-pyridin-4-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N1C=2C=C3C(C)C(=O)N(CCO)C3=CC=2N=C1C1=CC=NC=C1 JQYMADJWEUTCDT-UHFFFAOYSA-N 0.000 description 1
- QFTGXKDKWAOUIK-UHFFFAOYSA-N 5-(2-methoxyethyl)-1,7,7-trimethyl-2-pyridin-3-ylpyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)(C)C3=CC=2N(C)C=1C1=CC=CN=C1 QFTGXKDKWAOUIK-UHFFFAOYSA-N 0.000 description 1
- HEFZDUMNYRCJDB-UHFFFAOYSA-N 5-(2-methoxyethyl)-1,7,7-trimethyl-2-pyridin-4-ylpyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)(C)C3=CC=2N(C)C=1C1=CC=NC=C1 HEFZDUMNYRCJDB-UHFFFAOYSA-N 0.000 description 1
- KNNPYKLDHSXVQN-UHFFFAOYSA-N 5-(2-methoxyethyl)-1,7-dimethyl-2-pyridin-2-yl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)C3=CC=2N(C)C=1C1=CC=CC=N1 KNNPYKLDHSXVQN-UHFFFAOYSA-N 0.000 description 1
- GFGPZGQQEOOWHE-UHFFFAOYSA-N 5-(2-methoxyethyl)-1,7-dimethyl-2-pyridin-3-yl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)C3=CC=2N(C)C=1C1=CC=CN=C1 GFGPZGQQEOOWHE-UHFFFAOYSA-N 0.000 description 1
- KBUVIFOXRQVOAG-UHFFFAOYSA-N 5-(2-methoxyethyl)-1,7-dimethyl-2-pyridin-4-yl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)C3=CC=2N(C)C=1C1=CC=NC=C1 KBUVIFOXRQVOAG-UHFFFAOYSA-N 0.000 description 1
- ZZEJWCCCVZXYJS-UHFFFAOYSA-N 5-(2-methoxyethyl)-2-(4-methoxyphenyl)-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)CC3=CC=2NC=1C1=CC=C(OC)C=C1 ZZEJWCCCVZXYJS-UHFFFAOYSA-N 0.000 description 1
- GNFFZRNDIZMLRK-UHFFFAOYSA-N 5-(2-methoxyethyl)-2-(4-methoxyphenyl)-1,7-dimethyl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)C3=CC=2N(C)C=1C1=CC=C(OC)C=C1 GNFFZRNDIZMLRK-UHFFFAOYSA-N 0.000 description 1
- NLZGWEBWDZFUEX-UHFFFAOYSA-N 5-(2-methoxyethyl)-2-(4-methoxyphenyl)-3,7,7-trimethylpyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(CCOC)C(=O)C(C)(C)C3=CC=2N=C1C1=CC=C(OC)C=C1 NLZGWEBWDZFUEX-UHFFFAOYSA-N 0.000 description 1
- GMCQXRXBIZCWRV-UHFFFAOYSA-N 5-(2-methoxyethyl)-2-(4-methoxyphenyl)-3-methyl-7h-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(CCOC)C(=O)CC3=CC=2N=C1C1=CC=C(OC)C=C1 GMCQXRXBIZCWRV-UHFFFAOYSA-N 0.000 description 1
- FCMMPWLUFIMNSL-UHFFFAOYSA-N 5-(2-methoxyethyl)-2-pyridin-2-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)CC3=CC=2NC=1C1=CC=CC=N1 FCMMPWLUFIMNSL-UHFFFAOYSA-N 0.000 description 1
- MFMHMKGYFAZNFH-UHFFFAOYSA-N 5-(2-methoxyethyl)-3,7-dimethyl-2-pyridin-2-yl-7H-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(CCOC)C(=O)C(C)C3=CC=2N=C1C1=CC=CC=N1 MFMHMKGYFAZNFH-UHFFFAOYSA-N 0.000 description 1
- KPYFNCYVOBIAAX-UHFFFAOYSA-N 5-(2-methoxyethyl)-3,7-dimethyl-2-pyridin-4-yl-7H-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(CCOC)C(=O)C(C)C3=CC=2N=C1C1=CC=NC=C1 KPYFNCYVOBIAAX-UHFFFAOYSA-N 0.000 description 1
- PBTKNQBFZXWGOK-UHFFFAOYSA-N 5-(2-methoxyethyl)-3-methyl-2-pyridin-3-yl-7h-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(CCOC)C(=O)CC3=CC=2N=C1C1=CC=CN=C1 PBTKNQBFZXWGOK-UHFFFAOYSA-N 0.000 description 1
- QUDOIEZYVTTYKP-UHFFFAOYSA-N 5-(2-methoxyethyl)-7,7-dimethyl-2-(5-methylfuran-3-yl)-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)(C)C3=CC=2NC=1C1=COC(C)=C1 QUDOIEZYVTTYKP-UHFFFAOYSA-N 0.000 description 1
- BWDJYMUXELVGBJ-UHFFFAOYSA-N 5-(2-methoxyethyl)-7,7-dimethyl-2-pyridin-2-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=CC=N1 BWDJYMUXELVGBJ-UHFFFAOYSA-N 0.000 description 1
- ADWUHUYXDAAAPU-UHFFFAOYSA-N 5-(2-methoxyethyl)-7,7-dimethyl-2-pyridin-4-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=NC=C1 ADWUHUYXDAAAPU-UHFFFAOYSA-N 0.000 description 1
- AUYDFJPSTMKAIK-UHFFFAOYSA-N 5-(2-methoxyethyl)-7,7-dimethyl-2-thiophen-3-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)(C)C3=CC=2NC=1C=1C=CSC=1 AUYDFJPSTMKAIK-UHFFFAOYSA-N 0.000 description 1
- UQBULGZFSJPIJV-UHFFFAOYSA-N 5-(2-methoxyethyl)-7-methyl-2-pyridin-2-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)C3=CC=2NC=1C1=CC=CC=N1 UQBULGZFSJPIJV-UHFFFAOYSA-N 0.000 description 1
- CTFOGRIZRXKLJS-UHFFFAOYSA-N 5-(2-methoxyethyl)-7-methyl-2-pyridin-3-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)C3=CC=2NC=1C1=CC=CN=C1 CTFOGRIZRXKLJS-UHFFFAOYSA-N 0.000 description 1
- YWEBUEOVDJJWBH-UHFFFAOYSA-N 5-(2-methoxyethyl)-7-methyl-2-pyridin-4-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCOC)C(=O)C(C)C3=CC=2NC=1C1=CC=NC=C1 YWEBUEOVDJJWBH-UHFFFAOYSA-N 0.000 description 1
- WKEIVQDLRKJMAT-UHFFFAOYSA-N 5-amino-1-benzyl-3,3-dimethyl-6-nitroindol-2-one Chemical compound C12=CC([N+]([O-])=O)=C(N)C=C2C(C)(C)C(=O)N1CC1=CC=CC=C1 WKEIVQDLRKJMAT-UHFFFAOYSA-N 0.000 description 1
- ICBJQAQVPUEHDE-UHFFFAOYSA-N 5-amino-1-butyl-3,3-dimethyl-6-nitroindol-2-one Chemical compound NC1=C([N+]([O-])=O)C=C2N(CCCC)C(=O)C(C)(C)C2=C1 ICBJQAQVPUEHDE-UHFFFAOYSA-N 0.000 description 1
- GSMBWZOCXWPNTQ-UHFFFAOYSA-N 5-amino-1-ethyl-3-methyl-6-nitro-3h-indol-2-one Chemical compound NC1=C([N+]([O-])=O)C=C2N(CC)C(=O)C(C)C2=C1 GSMBWZOCXWPNTQ-UHFFFAOYSA-N 0.000 description 1
- VUTOTLVYHUHMIP-UHFFFAOYSA-N 5-amino-1-methyl-6-nitro-3h-indol-2-one Chemical compound NC1=C([N+]([O-])=O)C=C2N(C)C(=O)CC2=C1 VUTOTLVYHUHMIP-UHFFFAOYSA-N 0.000 description 1
- SGWIEDLGSVLJAA-UHFFFAOYSA-N 5-amino-3,3-dimethyl-6-nitro-1-pentylindol-2-one Chemical compound NC1=C([N+]([O-])=O)C=C2N(CCCCC)C(=O)C(C)(C)C2=C1 SGWIEDLGSVLJAA-UHFFFAOYSA-N 0.000 description 1
- UAXOQLGZLOVTKH-UHFFFAOYSA-N 5-amino-3,3-dimethyl-6-nitro-1-propan-2-ylindol-2-one Chemical compound NC1=C([N+]([O-])=O)C=C2N(C(C)C)C(=O)C(C)(C)C2=C1 UAXOQLGZLOVTKH-UHFFFAOYSA-N 0.000 description 1
- QIZGCBUEKSQKQS-UHFFFAOYSA-N 5-amino-3,3-dimethyl-6-nitro-1-propylindol-2-one Chemical compound NC1=C([N+]([O-])=O)C=C2N(CCC)C(=O)C(C)(C)C2=C1 QIZGCBUEKSQKQS-UHFFFAOYSA-N 0.000 description 1
- MQTJCHVLUVJNDL-UHFFFAOYSA-N 5-benzyl-2-(4-methoxyphenyl)-7,7-dimethyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=CC(OC)=CC=C1C(NC1=C2)=NC1=CC1=C2C(C)(C)C(=O)N1CC1=CC=CC=C1 MQTJCHVLUVJNDL-UHFFFAOYSA-N 0.000 description 1
- BXMYEZWUYCDMEU-UHFFFAOYSA-N 5-benzyl-7,7-dimethyl-2-pyridin-2-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C12=CC=3N=C(C=4N=CC=CC=4)NC=3C=C2C(C)(C)C(=O)N1CC1=CC=CC=C1 BXMYEZWUYCDMEU-UHFFFAOYSA-N 0.000 description 1
- SHPDYWSPXZHGCY-UHFFFAOYSA-N 5-benzyl-7,7-dimethyl-2-pyridin-3-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C12=CC=3N=C(C=4C=NC=CC=4)NC=3C=C2C(C)(C)C(=O)N1CC1=CC=CC=C1 SHPDYWSPXZHGCY-UHFFFAOYSA-N 0.000 description 1
- RDPZWPIGGOZJMR-UHFFFAOYSA-N 5-benzyl-7,7-dimethyl-2-pyridin-4-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C12=CC=3N=C(C=4C=CN=CC=4)NC=3C=C2C(C)(C)C(=O)N1CC1=CC=CC=C1 RDPZWPIGGOZJMR-UHFFFAOYSA-N 0.000 description 1
- SCRPTFVDUYTGGD-UHFFFAOYSA-N 5-butyl-2-(4-methoxyphenyl)-7,7-dimethyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCCC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=C(OC)C=C1 SCRPTFVDUYTGGD-UHFFFAOYSA-N 0.000 description 1
- QBZMIZYTEPMUPF-UHFFFAOYSA-N 5-butyl-7,7-dimethyl-2-(thiophen-2-ylmethyl)-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCCC)C(=O)C(C)(C)C3=CC=2NC=1CC1=CC=CS1 QBZMIZYTEPMUPF-UHFFFAOYSA-N 0.000 description 1
- HVACZENXIOSULD-UHFFFAOYSA-N 5-butyl-7,7-dimethyl-2-(thiophen-3-ylmethyl)-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCCC)C(=O)C(C)(C)C3=CC=2NC=1CC=1C=CSC=1 HVACZENXIOSULD-UHFFFAOYSA-N 0.000 description 1
- ZZQMSMGFIQQPJB-UHFFFAOYSA-N 5-butyl-7,7-dimethyl-2-pyridin-3-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCCC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=CN=C1 ZZQMSMGFIQQPJB-UHFFFAOYSA-N 0.000 description 1
- CTGVVBDBKCZDSI-UHFFFAOYSA-N 5-ethyl-1,7-dimethyl-2-pyridin-2-yl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)C3=CC=2N(C)C=1C1=CC=CC=N1 CTGVVBDBKCZDSI-UHFFFAOYSA-N 0.000 description 1
- TUXWKBSMCQEOCY-UHFFFAOYSA-N 5-ethyl-1,7-dimethyl-2-pyridin-3-yl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)C3=CC=2N(C)C=1C1=CC=CN=C1 TUXWKBSMCQEOCY-UHFFFAOYSA-N 0.000 description 1
- ZEOIREZOVTVMJS-UHFFFAOYSA-N 5-ethyl-1-methyl-2-pyridin-2-yl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)CC3=CC=2N(C)C=1C1=CC=CC=N1 ZEOIREZOVTVMJS-UHFFFAOYSA-N 0.000 description 1
- RJAHKEQEHSVDNO-UHFFFAOYSA-N 5-ethyl-1-methyl-2-pyridin-3-yl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)CC3=CC=2N(C)C=1C1=CC=CN=C1 RJAHKEQEHSVDNO-UHFFFAOYSA-N 0.000 description 1
- HQGYOPGKHZTTQU-UHFFFAOYSA-N 5-ethyl-2,7,7-trimethyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C1=C2N(CC)C(=O)C(C)(C)C2=CC2=C1N=C(C)N2 HQGYOPGKHZTTQU-UHFFFAOYSA-N 0.000 description 1
- ZEAHYGAVHYXDEM-UHFFFAOYSA-N 5-ethyl-2-(4-hydroxyphenyl)-1,7,7-trimethylpyrrolo[2,3-f]benzimidazol-6-one Chemical compound CCN1C(=O)C(C)(C)c2cc3n(C)c(nc3cc12)-c1ccc(O)cc1 ZEAHYGAVHYXDEM-UHFFFAOYSA-N 0.000 description 1
- UAAGZKSVDUAECG-UHFFFAOYSA-N 5-ethyl-2-(4-hydroxyphenyl)-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C(C)N1C(CC=2C1=CC1=C(N=C(N1)C1=CC=C(C=C1)O)C=2)=O UAAGZKSVDUAECG-UHFFFAOYSA-N 0.000 description 1
- FKFMXGKMCBDBCO-UHFFFAOYSA-N 5-ethyl-2-(4-hydroxyphenyl)-1,7-dimethyl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound CCN1C(=O)C(C)c2cc3n(C)c(nc3cc12)-c1ccc(O)cc1 FKFMXGKMCBDBCO-UHFFFAOYSA-N 0.000 description 1
- YTILRTVCJZVCMZ-UHFFFAOYSA-N 5-ethyl-2-(4-hydroxyphenyl)-3,7,7-trimethylpyrrolo[3,2-f]benzimidazol-6-one Chemical compound C(C)N1C(C(C=2C1=CC1=C(N=C(N1C)C1=CC=C(C=C1)O)C=2)(C)C)=O YTILRTVCJZVCMZ-UHFFFAOYSA-N 0.000 description 1
- HSTPJFJFKGLPEK-UHFFFAOYSA-N 5-ethyl-2-(4-hydroxyphenyl)-3,7-dimethyl-7H-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound C(C)N1C(C(C=2C1=CC1=C(N=C(N1C)C1=CC=C(C=C1)O)C=2)C)=O HSTPJFJFKGLPEK-UHFFFAOYSA-N 0.000 description 1
- AVNAFAKAKLMCNH-UHFFFAOYSA-N 5-ethyl-2-(4-hydroxyphenyl)-7,7-dimethyl-1H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C(C)N1C(C(C=2C1=CC1=C(N=C(N1)C1=CC=C(C=C1)O)C=2)(C)C)=O AVNAFAKAKLMCNH-UHFFFAOYSA-N 0.000 description 1
- GXXHOECDDJNUNL-UHFFFAOYSA-N 5-ethyl-2-(4-hydroxyphenyl)-7-methyl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C(C)N1C(C(C=2C1=CC1=C(N=C(N1)C1=CC=C(C=C1)O)C=2)C)=O GXXHOECDDJNUNL-UHFFFAOYSA-N 0.000 description 1
- RBCRDENRNWLKKX-UHFFFAOYSA-N 5-ethyl-2-(4-methoxyphenyl)-1,7,7-trimethylpyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2N(C)C=1C1=CC=C(OC)C=C1 RBCRDENRNWLKKX-UHFFFAOYSA-N 0.000 description 1
- QPUOIMYARSZZOX-UHFFFAOYSA-N 5-ethyl-2-(4-methoxyphenyl)-1,7-dimethyl-7H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)C3=CC=2N(C)C=1C1=CC=C(OC)C=C1 QPUOIMYARSZZOX-UHFFFAOYSA-N 0.000 description 1
- BEZSRYAQDUCIHJ-UHFFFAOYSA-N 5-ethyl-2-(4-methoxyphenyl)-1-methyl-7h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)CC3=CC=2N(C)C=1C1=CC=C(OC)C=C1 BEZSRYAQDUCIHJ-UHFFFAOYSA-N 0.000 description 1
- USONSNYJPNYCLS-UHFFFAOYSA-N 5-ethyl-2-(4-methoxyphenyl)-3,7,7-trimethylpyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2N=C1C1=CC=C(OC)C=C1 USONSNYJPNYCLS-UHFFFAOYSA-N 0.000 description 1
- GOLHYCKACSWOBH-UHFFFAOYSA-N 5-ethyl-2-(4-methoxyphenyl)-7-methyl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound C(C)N1C(C(C=2C1=CC1=C(N=C(N1)C1=CC=C(C=C1)OC)C=2)C)=O GOLHYCKACSWOBH-UHFFFAOYSA-N 0.000 description 1
- FZLLAOIDMAJIRY-UHFFFAOYSA-N 5-ethyl-2-pyridin-3-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)CC3=CC=2NC=1C1=CC=CN=C1 FZLLAOIDMAJIRY-UHFFFAOYSA-N 0.000 description 1
- HNOACCNXGZIPKD-UHFFFAOYSA-N 5-ethyl-2-pyridin-4-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)CC3=CC=2NC=1C1=CC=NC=C1 HNOACCNXGZIPKD-UHFFFAOYSA-N 0.000 description 1
- QHHSEERZSKMPEG-UHFFFAOYSA-N 5-ethyl-3,7,7-trimethyl-2-pyridin-3-ylpyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2N=C1C1=CC=CN=C1 QHHSEERZSKMPEG-UHFFFAOYSA-N 0.000 description 1
- GAXYXCLYEOGSPJ-UHFFFAOYSA-N 5-ethyl-3,7,7-trimethyl-2-pyridin-4-ylpyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2N=C1C1=CC=NC=C1 GAXYXCLYEOGSPJ-UHFFFAOYSA-N 0.000 description 1
- UPPJMAKYUVYPDV-UHFFFAOYSA-N 5-ethyl-3-methyl-2-pyridin-2-yl-7H-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(CC)C(=O)CC3=CC=2N=C1C1=CC=CC=N1 UPPJMAKYUVYPDV-UHFFFAOYSA-N 0.000 description 1
- JTAYYMAGUTWGGJ-UHFFFAOYSA-N 5-ethyl-3-methyl-2-pyridin-3-yl-7h-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(CC)C(=O)CC3=CC=2N=C1C1=CC=CN=C1 JTAYYMAGUTWGGJ-UHFFFAOYSA-N 0.000 description 1
- DEMDQCPAIXDZRF-UHFFFAOYSA-N 5-ethyl-3-methyl-2-pyridin-4-yl-7h-pyrrolo[3,2-f]benzimidazol-6-one Chemical compound CN1C=2C=C3N(CC)C(=O)CC3=CC=2N=C1C1=CC=NC=C1 DEMDQCPAIXDZRF-UHFFFAOYSA-N 0.000 description 1
- QXBBYZNPRNXGPA-UHFFFAOYSA-N 5-ethyl-7,7-dimethyl-1H-pyrrolo[2,3-f]benzimidazol-6-one hydrochloride Chemical compound Cl.C(C)N1C(C(C=2C1=CC1=C(N=CN1)C2)(C)C)=O QXBBYZNPRNXGPA-UHFFFAOYSA-N 0.000 description 1
- KBNFRUMCXSNNAB-UHFFFAOYSA-N 5-ethyl-7,7-dimethyl-2-(1H-pyrrol-2-yl)-1H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C(C)N1C(C(C=2C1=CC1=C(N=C(N1)C=1NC=CC=1)C=2)(C)C)=O KBNFRUMCXSNNAB-UHFFFAOYSA-N 0.000 description 1
- KGKLATVRHXOKLE-UHFFFAOYSA-N 5-ethyl-7,7-dimethyl-2-(2-morpholin-4-ylpyridin-3-yl)-1H-pyrrolo[2,3-f]benzimidazol-6-one hydrochloride Chemical compound Cl.N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=CN=C1N1CCOCC1 KGKLATVRHXOKLE-UHFFFAOYSA-N 0.000 description 1
- RLMWJXNHODVUFL-UHFFFAOYSA-N 5-ethyl-7,7-dimethyl-2-(2-pyridin-4-ylethyl)-1H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound C(C)N1C(C(C=2C1=CC1=C(N=C(N1)CCC1=CC=NC=C1)C=2)(C)C)=O RLMWJXNHODVUFL-UHFFFAOYSA-N 0.000 description 1
- IEXQUGIIRJGVAT-UHFFFAOYSA-N 5-ethyl-7,7-dimethyl-2-(4-methylsulfinylphenyl)-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=C(S(C)=O)C=C1 IEXQUGIIRJGVAT-UHFFFAOYSA-N 0.000 description 1
- LNUDSXWFRHAZHX-UHFFFAOYSA-N 5-ethyl-7,7-dimethyl-2-(4-methylsulfonylphenyl)-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=C(S(C)(=O)=O)C=C1 LNUDSXWFRHAZHX-UHFFFAOYSA-N 0.000 description 1
- UIZFEBKXZXYDJK-UHFFFAOYSA-N 5-ethyl-7,7-dimethyl-2-(pyridin-3-ylmethyl)-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1CC1=CC=CN=C1 UIZFEBKXZXYDJK-UHFFFAOYSA-N 0.000 description 1
- CCHAGZZOTNZKFA-UHFFFAOYSA-N 5-ethyl-7,7-dimethyl-2-(thiophen-2-ylmethyl)-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1CC1=CC=CS1 CCHAGZZOTNZKFA-UHFFFAOYSA-N 0.000 description 1
- PVLDVADLALNQNF-UHFFFAOYSA-N 5-ethyl-7,7-dimethyl-2-pyrazin-2-yl-1H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CN=CC=N1 PVLDVADLALNQNF-UHFFFAOYSA-N 0.000 description 1
- AQRAIGPRWCJCIW-UHFFFAOYSA-N 5-ethyl-7,7-dimethyl-2-pyridazin-4-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=NN=C1 AQRAIGPRWCJCIW-UHFFFAOYSA-N 0.000 description 1
- OTSUUIYCNKJRBK-UHFFFAOYSA-N 5-ethyl-7,7-dimethyl-2-pyridin-2-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=CC=N1 OTSUUIYCNKJRBK-UHFFFAOYSA-N 0.000 description 1
- BRUMNRGDPHZVPO-UHFFFAOYSA-N 5-ethyl-7,7-dimethyl-2-pyridin-3-yl-1H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=CN=C1 BRUMNRGDPHZVPO-UHFFFAOYSA-N 0.000 description 1
- KORLXLXNLXKMSM-UHFFFAOYSA-N 5-ethyl-7-methyl-2-pyridin-2-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)C3=CC=2NC=1C1=CC=CC=N1 KORLXLXNLXKMSM-UHFFFAOYSA-N 0.000 description 1
- VRENMDAOLDETLA-UHFFFAOYSA-N 5-ethyl-7-methyl-2-pyridin-3-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)C3=CC=2NC=1C1=CC=CN=C1 VRENMDAOLDETLA-UHFFFAOYSA-N 0.000 description 1
- OPOPQHQVTAOUHQ-UHFFFAOYSA-N 5-ethyl-7-methyl-2-pyridin-4-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)C3=CC=2NC=1C1=CC=NC=C1 OPOPQHQVTAOUHQ-UHFFFAOYSA-N 0.000 description 1
- YKYMKQPRWLIZBF-UHFFFAOYSA-N 5-methyl-2-pyridin-3-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(C)C(=O)CC3=CC=2NC=1C1=CC=CN=C1 YKYMKQPRWLIZBF-UHFFFAOYSA-N 0.000 description 1
- WARHAEMSSNFGNR-UHFFFAOYSA-N 5-methyl-2-pyridin-4-yl-1,7-dihydropyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(C)C(=O)CC3=CC=2NC=1C1=CC=NC=C1 WARHAEMSSNFGNR-UHFFFAOYSA-N 0.000 description 1
- ATQXNYQCZFMIKY-UHFFFAOYSA-N 6-methoxy-2-oxo-1h-quinoline-4-carboxylic acid Chemical compound N1C(=O)C=C(C(O)=O)C2=CC(OC)=CC=C21 ATQXNYQCZFMIKY-UHFFFAOYSA-N 0.000 description 1
- RZOKQIPOABEQAM-UHFFFAOYSA-N 6-methylpyridine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C=N1 RZOKQIPOABEQAM-UHFFFAOYSA-N 0.000 description 1
- RHRFJUKDHMVOIR-UHFFFAOYSA-N 7,7-dimethyl-2-(4-methylsulfonylphenyl)-5-pentyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCCCC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=C(S(C)(=O)=O)C=C1 RHRFJUKDHMVOIR-UHFFFAOYSA-N 0.000 description 1
- FMUPEROLOCBKDL-UHFFFAOYSA-N 7,7-dimethyl-2-(5-methylfuran-3-yl)-5-pentyl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCCCC)C(=O)C(C)(C)C3=CC=2NC=1C1=COC(C)=C1 FMUPEROLOCBKDL-UHFFFAOYSA-N 0.000 description 1
- RKNBYPNFNFQXAW-UHFFFAOYSA-N 7,7-dimethyl-5-pentyl-2-thiophen-2-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCCCC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=CS1 RKNBYPNFNFQXAW-UHFFFAOYSA-N 0.000 description 1
- CYVDNBDFGMEFHY-UHFFFAOYSA-N 7,7-dimethyl-5-pentyl-2-thiophen-3-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCCCC)C(=O)C(C)(C)C3=CC=2NC=1C=1C=CSC=1 CYVDNBDFGMEFHY-UHFFFAOYSA-N 0.000 description 1
- MDMPCDFKGICDFP-UHFFFAOYSA-N 7,7-dimethyl-5-propyl-2-pyrazin-2-yl-1H-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound CC1(C(N(C2=CC3=C(N=C(N3)C3=NC=CN=C3)C=C21)CCC)=O)C MDMPCDFKGICDFP-UHFFFAOYSA-N 0.000 description 1
- VRACKAUKGFFROF-UHFFFAOYSA-N 7,7-dimethyl-5-propyl-2-pyridin-3-yl-1h-pyrrolo[2,3-f]benzimidazol-6-one Chemical compound N=1C=2C=C3N(CCC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=CN=C1 VRACKAUKGFFROF-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- VLBKASGXQFZRAP-UHFFFAOYSA-N C(C)N1C(C(C=2C1=CC1=C(N=C(N1)C1=CC=CC=C1)C2)(C)C)=O Chemical compound C(C)N1C(C(C=2C1=CC1=C(N=C(N1)C1=CC=CC=C1)C2)(C)C)=O VLBKASGXQFZRAP-UHFFFAOYSA-N 0.000 description 1
- LCRSUEAQXRWAPV-UHFFFAOYSA-N C(C)N1C(C(C=2C1=CC1=C(N=C(N1C)C1=NC=CC=C1)C2)C)=O Chemical compound C(C)N1C(C(C=2C1=CC1=C(N=C(N1C)C1=NC=CC=C1)C2)C)=O LCRSUEAQXRWAPV-UHFFFAOYSA-N 0.000 description 1
- YIEFDCRXNVNCOW-UHFFFAOYSA-N CC1(C2=CC3=C(C=C2N(C1=O)CCO)N(C(=N3)C4=CN=CC=C4)C)C Chemical compound CC1(C2=CC3=C(C=C2N(C1=O)CCO)N(C(=N3)C4=CN=CC=C4)C)C YIEFDCRXNVNCOW-UHFFFAOYSA-N 0.000 description 1
- PPBRCHJQWSGIGA-UHFFFAOYSA-N CC1C2=CC3=C(C=C2N(C1=O)CCOC)N(C(=N3)C4=CN=CC=C4)C Chemical compound CC1C2=CC3=C(C=C2N(C1=O)CCOC)N(C(=N3)C4=CN=CC=C4)C PPBRCHJQWSGIGA-UHFFFAOYSA-N 0.000 description 1
- FLQMGAKXRFQKGM-UHFFFAOYSA-N CCN1C(=O)CC2=CC3=C(C=C21)N=C(N3)C4=CC=CC=N4 Chemical compound CCN1C(=O)CC2=CC3=C(C=C21)N=C(N3)C4=CC=CC=N4 FLQMGAKXRFQKGM-UHFFFAOYSA-N 0.000 description 1
- QMLYJRQEMSDUJD-UHFFFAOYSA-N COCCN1C(C(C=2C1=CC1=C(N(C(=N1)C1=CC=C(C=C1)OC)C)C2)(C)C)=O Chemical compound COCCN1C(C(C=2C1=CC1=C(N(C(=N1)C1=CC=C(C=C1)OC)C)C2)(C)C)=O QMLYJRQEMSDUJD-UHFFFAOYSA-N 0.000 description 1
- LWXPUDNZJRTOFM-UHFFFAOYSA-N COCCN1C(C(C=2C1=CC1=C(N(C(=N1)C1=NC=CC=C1)C)C2)(C)C)=O Chemical compound COCCN1C(C(C=2C1=CC1=C(N(C(=N1)C1=NC=CC=C1)C)C2)(C)C)=O LWXPUDNZJRTOFM-UHFFFAOYSA-N 0.000 description 1
- ZTPKVELQXQDINT-UHFFFAOYSA-N COCCN1C(CC=2C1=CC1=C(N=C(N1)C=1C=NC=CC1)C2)=O Chemical compound COCCN1C(CC=2C1=CC1=C(N=C(N1)C=1C=NC=CC1)C2)=O ZTPKVELQXQDINT-UHFFFAOYSA-N 0.000 description 1
- 206010007556 Cardiac failure acute Diseases 0.000 description 1
- 206010007558 Cardiac failure chronic Diseases 0.000 description 1
- AXJQKDIXPTWSNM-UHFFFAOYSA-N Cl.C(C)N1C(C(C=2C1=CC1=C(N=C(N1)C1=NC=NC=C1)C2)(C)C)=O Chemical compound Cl.C(C)N1C(C(C=2C1=CC1=C(N=C(N1)C1=NC=NC=C1)C2)(C)C)=O AXJQKDIXPTWSNM-UHFFFAOYSA-N 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- SIOGZPWQFXQJGL-UHFFFAOYSA-N N-(1-ethyl-3,3-dimethyl-6-nitro-2-oxoindol-5-yl)acetamide Chemical compound C(C)(=O)NC=1C=C2C(C(N(C2=CC=1[N+](=O)[O-])CC)=O)(C)C SIOGZPWQFXQJGL-UHFFFAOYSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QLYVBDSXJDVDKB-UHFFFAOYSA-N OC1=CC=C(C=C1)C=1N(C2=C(N1)C=C1C(=C2)N(C(C1(C)C)=O)CCOC)C Chemical compound OC1=CC=C(C=C1)C=1N(C2=C(N1)C=C1C(=C2)N(C(C1(C)C)=O)CCOC)C QLYVBDSXJDVDKB-UHFFFAOYSA-N 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000001435 Thromboembolism Diseases 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 210000000702 aorta abdominal Anatomy 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 210000005242 cardiac chamber Anatomy 0.000 description 1
- 230000003177 cardiotonic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229950007593 homonicotinic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- XVDFTPMOHNLNCB-UHFFFAOYSA-N methyl hypoiodite Chemical compound COI XVDFTPMOHNLNCB-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- UMXSFTCPZHSJLE-UHFFFAOYSA-N n-(1-benzyl-3,3-dimethyl-2-oxoindol-5-yl)acetamide Chemical compound O=C1C(C)(C)C2=CC(NC(=O)C)=CC=C2N1CC1=CC=CC=C1 UMXSFTCPZHSJLE-UHFFFAOYSA-N 0.000 description 1
- LWGWXFBFYSULBE-UHFFFAOYSA-N n-(1-butyl-3,3-dimethyl-2-oxoindol-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2N(CCCC)C(=O)C(C)(C)C2=C1 LWGWXFBFYSULBE-UHFFFAOYSA-N 0.000 description 1
- CEYWMYMQPLDKKL-UHFFFAOYSA-N n-(1-ethyl-3,3-dimethyl-6-nitro-2-oxoindol-5-yl)-4-methoxybenzamide Chemical compound [O-][N+](=O)C=1C=C2N(CC)C(=O)C(C)(C)C2=CC=1NC(=O)C1=CC=C(OC)C=C1 CEYWMYMQPLDKKL-UHFFFAOYSA-N 0.000 description 1
- SHUXSVDTHUEEOL-UHFFFAOYSA-N n-(1-ethyl-3-methyl-2-oxo-3h-indol-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2N(CC)C(=O)C(C)C2=C1 SHUXSVDTHUEEOL-UHFFFAOYSA-N 0.000 description 1
- PHWPSQGJFXTDEM-UHFFFAOYSA-N n-(1-methyl-2-oxo-3h-indol-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2N(C)C(=O)CC2=C1 PHWPSQGJFXTDEM-UHFFFAOYSA-N 0.000 description 1
- FYQGDGSHNVXCOH-UHFFFAOYSA-N n-(3,3-dimethyl-2-oxo-1-propan-2-ylindol-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2N(C(C)C)C(=O)C(C)(C)C2=C1 FYQGDGSHNVXCOH-UHFFFAOYSA-N 0.000 description 1
- NNSYKXCUQRNDCE-UHFFFAOYSA-N n-(3,3-dimethyl-2-oxo-1-propylindol-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2N(CCC)C(=O)C(C)(C)C2=C1 NNSYKXCUQRNDCE-UHFFFAOYSA-N 0.000 description 1
- UBGUIHKHPFPOLN-UHFFFAOYSA-N n-(6-amino-1-ethyl-3,3-dimethyl-2-oxoindol-5-yl)-4-cyanobenzamide Chemical compound NC=1C=C2N(CC)C(=O)C(C)(C)C2=CC=1NC(=O)C1=CC=C(C#N)C=C1 UBGUIHKHPFPOLN-UHFFFAOYSA-N 0.000 description 1
- NAHPPFKKGIUXEX-UHFFFAOYSA-N n-[1-(2-methoxyethyl)-3,3-dimethyl-2-oxoindol-5-yl]acetamide Chemical compound CC(=O)NC1=CC=C2N(CCOC)C(=O)C(C)(C)C2=C1 NAHPPFKKGIUXEX-UHFFFAOYSA-N 0.000 description 1
- OWLDUCMLQPXFNO-UHFFFAOYSA-N n-[1-(2-methoxyethyl)-3,3-dimethyl-6-nitro-2-oxoindol-5-yl]pyridine-2-carboxamide Chemical compound [O-][N+](=O)C=1C=C2N(CCOC)C(=O)C(C)(C)C2=CC=1NC(=O)C1=CC=CC=N1 OWLDUCMLQPXFNO-UHFFFAOYSA-N 0.000 description 1
- IJOZDLAKGSJALH-UHFFFAOYSA-N n-[4-(5-ethyl-7,7-dimethyl-6-oxo-1h-pyrrolo[2,3-f]benzimidazol-2-yl)phenyl]acetamide Chemical compound N=1C=2C=C3N(CC)C(=O)C(C)(C)C3=CC=2NC=1C1=CC=C(NC(C)=O)C=C1 IJOZDLAKGSJALH-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WZRJMTJFQONOQW-UHFFFAOYSA-N n-methyl-n-(1,3,3-trimethyl-2-oxoindol-5-yl)acetamide Chemical compound CC(=O)N(C)C1=CC=C2N(C)C(=O)C(C)(C)C2=C1 WZRJMTJFQONOQW-UHFFFAOYSA-N 0.000 description 1
- VTUHZWPQRALYPH-UHFFFAOYSA-N n-methyl-n-(1,3,3-trimethyl-2-oxoindol-6-yl)acetamide Chemical compound CC(=O)N(C)C1=CC=C2C(C)(C)C(=O)N(C)C2=C1 VTUHZWPQRALYPH-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229960002275 pentobarbital sodium Drugs 0.000 description 1
- 125000002071 phenylalkoxy group Chemical group 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- JUSIWJONLKBPDU-UHFFFAOYSA-N pyridazine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NN=C1 JUSIWJONLKBPDU-UHFFFAOYSA-N 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Natural products OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863639466 DE3639466A1 (de) | 1986-11-18 | 1986-11-18 | Neue pyrrolo-benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO874780D0 NO874780D0 (no) | 1987-11-17 |
| NO874780L true NO874780L (no) | 1988-05-19 |
Family
ID=6314255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO874780A NO874780L (no) | 1986-11-18 | 1987-11-17 | Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrrolo-benzimidazol-derivater. |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0268178A1 (hu) |
| JP (1) | JPS63135385A (hu) |
| KR (1) | KR890003688A (hu) |
| AU (1) | AU8129987A (hu) |
| DD (1) | DD272081A5 (hu) |
| DE (1) | DE3639466A1 (hu) |
| DK (1) | DK602487A (hu) |
| FI (1) | FI875076A (hu) |
| HU (1) | HUT47277A (hu) |
| IE (1) | IE873089L (hu) |
| IL (1) | IL84509A0 (hu) |
| NO (1) | NO874780L (hu) |
| PT (1) | PT86154B (hu) |
| ZA (1) | ZA878590B (hu) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3531678A1 (de) * | 1985-09-05 | 1987-03-12 | Boehringer Mannheim Gmbh | Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3803775A1 (de) * | 1988-02-09 | 1989-08-17 | Boehringer Mannheim Gmbh | Neue substituierte lactame, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
| DE3932953A1 (de) * | 1989-10-03 | 1991-04-11 | Boehringer Mannheim Gmbh | Neue 2-bicyclo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE4027592A1 (de) * | 1990-08-31 | 1992-03-05 | Beiersdorf Ag | Neue pyrrolobenzimidazole, imidazobenzoxazinone und imidazochinolone, verfahren zu ihrer herstellung und ihre verwendung sowie die verbindungen enthaltende zubereitungen |
| EP1598353A1 (en) * | 2004-05-17 | 2005-11-23 | Boehringer Ingelheim International GmbH | Pyrrolobenzimidazolones and their use as antiproliferative agents |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL147842B1 (en) * | 1984-05-12 | 1989-08-31 | Method of obtaining novel pyroisobenzimidazoles | |
| DE3445669A1 (de) * | 1984-12-14 | 1986-06-19 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3501497A1 (de) * | 1985-01-18 | 1986-07-24 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue pyrrolo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel sowie zwischenprodukte |
-
1986
- 1986-11-18 DE DE19863639466 patent/DE3639466A1/de not_active Withdrawn
-
1987
- 1987-11-09 EP EP87116512A patent/EP0268178A1/de not_active Withdrawn
- 1987-11-16 DD DD87309081A patent/DD272081A5/de unknown
- 1987-11-17 IE IE873089A patent/IE873089L/xx unknown
- 1987-11-17 NO NO874780A patent/NO874780L/no unknown
- 1987-11-17 FI FI875076A patent/FI875076A/fi not_active IP Right Cessation
- 1987-11-17 ZA ZA878590A patent/ZA878590B/xx unknown
- 1987-11-17 JP JP62290467A patent/JPS63135385A/ja active Pending
- 1987-11-17 DK DK602487A patent/DK602487A/da not_active Application Discontinuation
- 1987-11-17 HU HU875099A patent/HUT47277A/hu unknown
- 1987-11-17 KR KR870012907A patent/KR890003688A/ko not_active Application Discontinuation
- 1987-11-17 AU AU81299/87A patent/AU8129987A/en not_active Abandoned
- 1987-11-17 IL IL84509A patent/IL84509A0/xx unknown
- 1987-11-17 PT PT86154A patent/PT86154B/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3639466A1 (de) | 1988-05-19 |
| EP0268178A1 (de) | 1988-05-25 |
| NO874780D0 (no) | 1987-11-17 |
| DK602487A (da) | 1988-05-19 |
| FI875076A0 (fi) | 1987-11-17 |
| DD272081A5 (de) | 1989-09-27 |
| IL84509A0 (en) | 1988-04-29 |
| AU8129987A (en) | 1988-05-19 |
| FI875076A (fi) | 1988-05-19 |
| DK602487D0 (da) | 1987-11-17 |
| KR890003688A (ko) | 1989-04-17 |
| JPS63135385A (ja) | 1988-06-07 |
| PT86154A (de) | 1987-12-01 |
| IE873089L (en) | 1988-05-18 |
| ZA878590B (en) | 1989-07-26 |
| PT86154B (pt) | 1990-11-20 |
| HUT47277A (en) | 1989-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0223937B1 (de) | Heterocyclisch substituierte Indole, Zwischenprodukte, Verfahren zu ihrer Herstellung und Arzneimittel | |
| US6451805B1 (en) | Substituted pyrazole derivatives for the treatment of cardiocirculatory diseases | |
| FI81351C (fi) | Foerfarande foer framstaellning av farmakologiskt aktiva 2-pyridylsubstituerade 6,7-dihydro-3h,5h-pyrrolo/ 2,3-f/bentsimidazol-6-oner och -6-tioner. | |
| US4954498A (en) | Tricyclic benzimidazole compounds, pharmaceutical compositions and methods of use | |
| EP0266558A2 (de) | 5-Alkylbenzimidazole, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DK152496B (da) | Analogifremgangsmaade til fremstilling af i 5- eller 6-stilling med en pyridazinonring substituerede benzimidazoler eller deres fysiologisk acceptable syreadditionssalte | |
| NO832356L (no) | Fremgangsmaate for fremstilling av farmakologisk aktive imidazolderivater. | |
| DE3935514A1 (de) | Neue bicyclo-imidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE3614132A1 (de) | 1,3-dihydro-2h-imidazo(4,5-b)chinolin-2-one, verfahren zu deren herstellung und diese verbindungen enthaltende, pharmazeutische mittel | |
| NO874153L (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazo-benzoksazinon-derivater. | |
| EP0189103B1 (de) | Neue Pyrrolo-Benzimidazole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel sowie Zwischenprodukte | |
| AU2006267454A2 (en) | Benzoimidazole compound capable of inhibiting prostaglandin D synthetase | |
| US3993656A (en) | 1,8-Naphthyridine compounds | |
| NO301929B1 (no) | 4-aryl-tiazol- eller -imidazol-derivater | |
| KR20050099525A (ko) | 피롤로트리아진 키나제 억제제의 제조 방법 | |
| EP0181136B1 (en) | Oxindole antiinflammatory agents | |
| US4874756A (en) | Benzodipyrroles, processes for the preparation thereof and pharmaceutical compositions containing them | |
| JPH0471914B2 (hu) | ||
| PT88614B (pt) | Processo para a preparacao de antagonistas do factor activador de plaquetas di-hidropiridinicos | |
| US4835280A (en) | Indoline compounds for synthesis of pharmaceutically active pyrrolobenzimidazoles | |
| CA1287631C (en) | 5-substituted-6-aminopyrimidine derivatives, composition and uses | |
| NO874780L (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrrolo-benzimidazol-derivater. | |
| NO845169L (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive benzimidazol-derivater | |
| EP0306185A1 (en) | Tricyclic fused pyrimidine derivatives their production and use | |
| US4831032A (en) | Cardiotonic benzimidazoles |