NO323312B1 - 2-(1H-indol-3yl)-2-okso-acetamider, sammensetninger inneholdende disse og deres anvendelse - Google Patents

Info

Publication number

NO323312B1

NO323312B1 NO20022976A NO20022976A NO323312B1 NO 323312 B1 NO323312 B1 NO 323312B1 NO 20022976 A NO20022976 A NO 20022976A NO 20022976 A NO20022976 A NO 20022976A NO 323312 B1 NO323312 B1 NO 323312B1

Authority

NO

Norway

Prior art keywords

oxo

indol

acetamide

chlorobenzyl

methyl

Prior art date

1999-12-23

Links

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• AWMLDBKLOPNOAR-UHFFFAOYSA-N 2-(1h-indol-3-yl)-2-oxoacetamide Chemical class C1=CC=C2C(C(=O)C(=O)N)=CNC2=C1 AWMLDBKLOPNOAR-UHFFFAOYSA-N 0.000 title abstract description 4
• 239000000203 mixture Substances 0.000 title description 10
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 11
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
• 239000001301 oxygen Substances 0.000 claims abstract description 5
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
• 125000004434 sulfur atom Chemical group 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 57
• -1 hydroxy, methoxy, benzyloxy Chemical group 0.000 claims description 57
• 239000000460 chlorine Substances 0.000 claims description 31
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 10
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 125000005336 allyloxy group Chemical group 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
• 229910052794 bromium Inorganic materials 0.000 claims description 7
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 239000011737 fluorine Substances 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 150000003839 salts Chemical class 0.000 claims description 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 2
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
• 229940079593 drug Drugs 0.000 claims description 2
• 239000003814 drug Substances 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 150000002367 halogens Chemical class 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 229910052705 radium Inorganic materials 0.000 claims description 2
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
• 230000000259 anti-tumor effect Effects 0.000 abstract description 6
• 210000001072 colon Anatomy 0.000 abstract description 4
• 208000029742 colonic neoplasm Diseases 0.000 abstract description 4
• 208000037841 lung tumor Diseases 0.000 abstract description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
• 239000003921 oil Substances 0.000 description 53
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
• 239000000243 solution Substances 0.000 description 25
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• 238000006243 chemical reaction Methods 0.000 description 19
• 238000005160 1H NMR spectroscopy Methods 0.000 description 18
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
• 238000000921 elemental analysis Methods 0.000 description 18
• 238000001914 filtration Methods 0.000 description 14
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
• 238000000034 method Methods 0.000 description 11
• 239000007787 solid Substances 0.000 description 11
• 239000002904 solvent Substances 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 8
• 238000002360 preparation method Methods 0.000 description 8
• 239000011541 reaction mixture Substances 0.000 description 8
• 229910000104 sodium hydride Inorganic materials 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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
• 239000012312 sodium hydride Substances 0.000 description 6
• 230000000694 effects Effects 0.000 description 5
• 239000003480 eluent Substances 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• USNYBYHFYRBYOM-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-2-oxoacetyl chloride Chemical compound C12=CC=CC=C2C(C(=O)C(=O)Cl)=CN1CC1=CC=C(Cl)C=C1 USNYBYHFYRBYOM-UHFFFAOYSA-N 0.000 description 4
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
• 239000005695 Ammonium acetate Substances 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
• 235000019257 ammonium acetate Nutrition 0.000 description 4
• 229940043376 ammonium acetate Drugs 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 238000007398 colorimetric assay Methods 0.000 description 4
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 4
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• 238000002390 rotary evaporation Methods 0.000 description 4
• 239000000741 silica gel Substances 0.000 description 4
• 229910002027 silica gel Inorganic materials 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• PVHTZECNQVKRJS-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]indole-4-carbaldehyde Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC(C=O)=C2C=C1 PVHTZECNQVKRJS-UHFFFAOYSA-N 0.000 description 3
• JPGCUWZSZNXFQM-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-2-oxo-n-(5-oxo-2h-furan-3-yl)acetamide Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(C(=O)C(=O)NC=2COC(=O)C=2)=C1 JPGCUWZSZNXFQM-UHFFFAOYSA-N 0.000 description 3
• SABBJFPNIAIRGR-UHFFFAOYSA-N 3-amino-2h-furan-5-one Chemical compound NC1=CC(=O)OC1 SABBJFPNIAIRGR-UHFFFAOYSA-N 0.000 description 3
• ZAEATBXDRKDVDD-UHFFFAOYSA-N 3-amino-2h-thiophen-5-one Chemical compound NC1=CC(=O)SC1 ZAEATBXDRKDVDD-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
• 206010009944 Colon cancer Diseases 0.000 description 3
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 3
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
• 239000003513 alkali Substances 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 150000002081 enamines Chemical class 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 229960002949 fluorouracil Drugs 0.000 description 3
• 150000004820 halides Chemical class 0.000 description 3
• LILRHTVWXQWXCQ-UHFFFAOYSA-N methyl 3-(indol-1-ylmethyl)benzoate Chemical compound COC(=O)C1=CC=CC(CN2C3=CC=CC=C3C=C2)=C1 LILRHTVWXQWXCQ-UHFFFAOYSA-N 0.000 description 3
• 239000002480 mineral oil Substances 0.000 description 3
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• 238000012360 testing method Methods 0.000 description 3
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• FUSHTXNJHSYERP-UHFFFAOYSA-N 1-[(2,4,6-trimethylphenyl)methyl]indole Chemical compound CC1=CC(C)=CC(C)=C1CN1C2=CC=CC=C2C=C1 FUSHTXNJHSYERP-UHFFFAOYSA-N 0.000 description 2
• XWHLRMOIAGSFJN-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]indole Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C=C1 XWHLRMOIAGSFJN-UHFFFAOYSA-N 0.000 description 2
• YLCVGDMHLPPFRO-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]indole-4-carboxylic acid Chemical compound C1=CC=2C(C(=O)O)=CC=CC=2N1CC1=CC=C(Cl)C=C1 YLCVGDMHLPPFRO-UHFFFAOYSA-N 0.000 description 2
• NNPAZBSSZIZVEI-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]indole Chemical compound C1=CC(F)=CC=C1CN1C2=CC=CC=C2C=C1 NNPAZBSSZIZVEI-UHFFFAOYSA-N 0.000 description 2
• HKMVVSPWBKYROP-UHFFFAOYSA-N 1-[1-[(4-chlorophenyl)methyl]indol-4-yl]ethanol Chemical compound C1=CC=2C(C(O)C)=CC=CC=2N1CC1=CC=C(Cl)C=C1 HKMVVSPWBKYROP-UHFFFAOYSA-N 0.000 description 2
• VOWUHKQBOIRNJT-UHFFFAOYSA-N 1-octylindole Chemical compound C1=CC=C2N(CCCCCCCC)C=CC2=C1 VOWUHKQBOIRNJT-UHFFFAOYSA-N 0.000 description 2
• QTVIJQZRFMGUOI-UHFFFAOYSA-N 2-[1-[(2,5-difluorophenyl)methyl]indol-3-yl]-2-oxo-n-(5-oxo-2h-furan-3-yl)acetamide Chemical compound FC1=CC=C(F)C(CN2C3=CC=CC=C3C(C(=O)C(=O)NC=3COC(=O)C=3)=C2)=C1 QTVIJQZRFMGUOI-UHFFFAOYSA-N 0.000 description 2
• DMCCIEBOGIXEDK-UHFFFAOYSA-N 2-[1-[(3-nitrophenyl)methyl]indol-3-yl]-2-oxo-n-(5-oxo-2h-furan-3-yl)acetamide Chemical compound [O-][N+](=O)C1=CC=CC(CN2C3=CC=CC=C3C(C(=O)C(=O)NC=3COC(=O)C=3)=C2)=C1 DMCCIEBOGIXEDK-UHFFFAOYSA-N 0.000 description 2
• NMKQCHCMDBAVJH-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]-4-(hydroxymethyl)indol-3-yl]-2-oxo-n-(5-oxo-2h-furan-3-yl)acetamide Chemical compound C1=C(C(=O)C(=O)NC=2COC(=O)C=2)C=2C(CO)=CC=CC=2N1CC1=CC=C(Cl)C=C1 NMKQCHCMDBAVJH-UHFFFAOYSA-N 0.000 description 2
• LXVGFEUOGNYUCY-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]-6-fluoroindol-3-yl]-2-oxo-n-(5-oxo-2h-furan-3-yl)acetamide Chemical compound C12=CC(F)=CC=C2C(C(=O)C(=O)NC=2COC(=O)C=2)=CN1CC1=CC=C(Cl)C=C1 LXVGFEUOGNYUCY-UHFFFAOYSA-N 0.000 description 2
• CPVJOOHQGISVIW-UHFFFAOYSA-N 2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-2-oxo-n-(5-oxo-2h-thiophen-3-yl)acetamide Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(C(=O)C(=O)NC=2CSC(=O)C=2)=C1 CPVJOOHQGISVIW-UHFFFAOYSA-N 0.000 description 2
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