SE442865B - Farmaceutiskt aktiva 2-substituerade-5-hydroxi-1h-imidazol-4-karboxamidderivat - Google Patents
Farmaceutiskt aktiva 2-substituerade-5-hydroxi-1h-imidazol-4-karboxamidderivatInfo
- Publication number
- SE442865B SE442865B SE7809373A SE7809373A SE442865B SE 442865 B SE442865 B SE 442865B SE 7809373 A SE7809373 A SE 7809373A SE 7809373 A SE7809373 A SE 7809373A SE 442865 B SE442865 B SE 442865B
- Authority
- SE
- Sweden
- Prior art keywords
- group
- imidazole
- hydroxy
- carboxamide
- dec
- Prior art date
Links
- -1 2-SUBSTITUTED-5-HYDROXY-1H-IMIDAZOLE-4-CARBOXAMIDE Chemical class 0.000 title claims description 31
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical group [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 3
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 18
- GFQBSQXXHYLABK-UHFFFAOYSA-N 2-aminopropanediamide Chemical group NC(=O)C(N)C(N)=O GFQBSQXXHYLABK-UHFFFAOYSA-N 0.000 description 16
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 238000010992 reflux Methods 0.000 description 13
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 238000000921 elemental analysis Methods 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 150000002463 imidates Chemical class 0.000 description 11
- 239000013078 crystal Substances 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000003308 immunostimulating effect Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 230000001093 anti-cancer Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002905 orthoesters Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 1
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QNCSFBSIWVBTHE-UHFFFAOYSA-N 1-oxidopyridin-1-ium-4-carbonitrile Chemical compound [O-][N+]1=CC=C(C#N)C=C1 QNCSFBSIWVBTHE-UHFFFAOYSA-N 0.000 description 1
- ZBNZAJFNDPPMDT-UHFFFAOYSA-N 1h-imidazole-5-carboxamide Chemical compound NC(=O)C1=CNC=N1 ZBNZAJFNDPPMDT-UHFFFAOYSA-N 0.000 description 1
- MZJLVGGJMYBESS-UHFFFAOYSA-N 2-(2-fluorophenyl)-4-hydroxy-1h-imidazole-5-carboxamide Chemical compound N1C(O)=C(C(=O)N)N=C1C1=CC=CC=C1F MZJLVGGJMYBESS-UHFFFAOYSA-N 0.000 description 1
- IMXPVTPDGBSUGN-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-hydroxy-1h-imidazole-5-carboxamide Chemical compound N1C(O)=C(C(=O)N)N=C1C1=CC=CC(Cl)=C1 IMXPVTPDGBSUGN-UHFFFAOYSA-N 0.000 description 1
- GNADMXHOOKCGRO-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-hydroxy-1h-imidazole-5-carboxamide Chemical compound N1C(O)=C(C(=O)N)N=C1C1=CC=CC(F)=C1 GNADMXHOOKCGRO-UHFFFAOYSA-N 0.000 description 1
- XTYMGZYAWAGQQD-UHFFFAOYSA-N 2-(4-carbamoylphenyl)-4-hydroxy-1h-imidazole-5-carboxamide Chemical compound N1C(O)=C(C(=O)N)N=C1C1=CC=C(C(N)=O)C=C1 XTYMGZYAWAGQQD-UHFFFAOYSA-N 0.000 description 1
- HLLFQIXYEUVSMG-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-hydroxy-1h-imidazole-5-carboxamide Chemical compound N1C(O)=C(C(=O)N)N=C1C1=CC=C(Cl)C=C1 HLLFQIXYEUVSMG-UHFFFAOYSA-N 0.000 description 1
- FYDQRJFHULGPOQ-UHFFFAOYSA-N 2-benzyl-4-hydroxy-1h-imidazole-5-carboxamide Chemical compound N1C(O)=C(C(=O)N)N=C1CC1=CC=CC=C1 FYDQRJFHULGPOQ-UHFFFAOYSA-N 0.000 description 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
- XUGMCLCIVMIHQR-UHFFFAOYSA-N 2-cycloheptyl-4-hydroxy-1h-imidazole-5-carboxamide Chemical compound N1C(O)=C(C(=O)N)N=C1C1CCCCCC1 XUGMCLCIVMIHQR-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- FFBYSINTBOQQMB-UHFFFAOYSA-N 2-tert-butyl-4-hydroxy-1h-imidazole-5-carboxamide Chemical compound CC(C)(C)C1=NC(C(N)=O)=C(O)N1 FFBYSINTBOQQMB-UHFFFAOYSA-N 0.000 description 1
- IETGSAMCULXTOG-UHFFFAOYSA-N 3-(methylamino)pyridine-2-carboxylic acid Chemical compound CNC1=CC=CN=C1C(O)=O IETGSAMCULXTOG-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- IJFQCOBGFVCTPD-UHFFFAOYSA-N 3-methylimino-4H-pyridine-4-carboxylic acid Chemical compound CN=C1C=NC=CC1C(=O)O IJFQCOBGFVCTPD-UHFFFAOYSA-N 0.000 description 1
- RUSAWEHOGCWOPG-UHFFFAOYSA-N 3-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=CC(C#N)=C1 RUSAWEHOGCWOPG-UHFFFAOYSA-N 0.000 description 1
- YVLRHIMNXOWHQU-UHFFFAOYSA-N 4-hydroxy-2-(2-nitrophenyl)-1h-imidazole-5-carboxamide Chemical compound N1C(O)=C(C(=O)N)N=C1C1=CC=CC=C1[N+]([O-])=O YVLRHIMNXOWHQU-UHFFFAOYSA-N 0.000 description 1
- RWABBLDTJMANCX-UHFFFAOYSA-N 4-hydroxy-2-(3-nitrophenyl)-1h-imidazole-5-carboxamide Chemical compound N1C(O)=C(C(=O)N)N=C1C1=CC=CC([N+]([O-])=O)=C1 RWABBLDTJMANCX-UHFFFAOYSA-N 0.000 description 1
- OUZBFKYPDVFZBH-UHFFFAOYSA-N 4-hydroxy-2-(4-nitrophenyl)-1h-imidazole-5-carboxamide Chemical compound N1C(O)=C(C(=O)N)N=C1C1=CC=C([N+]([O-])=O)C=C1 OUZBFKYPDVFZBH-UHFFFAOYSA-N 0.000 description 1
- DAZPQOYRUKVDFY-UHFFFAOYSA-N 4-hydroxy-2-[(2-methoxyphenyl)methyl]-1h-imidazole-5-carboxamide Chemical compound COC1=CC=CC=C1CC1=NC(C(N)=O)=C(O)N1 DAZPQOYRUKVDFY-UHFFFAOYSA-N 0.000 description 1
- CFTWNQIGFUYEEE-UHFFFAOYSA-N 4-hydroxy-2-[(3-methoxyphenyl)methyl]-1h-imidazole-5-carboxamide Chemical compound COC1=CC=CC(CC=2NC(O)=C(C(N)=O)N=2)=C1 CFTWNQIGFUYEEE-UHFFFAOYSA-N 0.000 description 1
- QAFUKXKIRCOMJD-UHFFFAOYSA-N 4-hydroxy-2-phenyl-1h-imidazole-5-carboxamide Chemical compound N1C(O)=C(C(=O)N)N=C1C1=CC=CC=C1 QAFUKXKIRCOMJD-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- UEWSIIBPZOBMBL-UHFFFAOYSA-N 5-hydroxyimidazole-4-carboxamide Chemical compound NC(=O)C1=C([O-])[NH2+]C=N1 UEWSIIBPZOBMBL-UHFFFAOYSA-N 0.000 description 1
- HLOAUTGENTUURB-UHFFFAOYSA-N 6-methylimino-5-nitrocyclohexa-2,4-diene-1-carboxylic acid Chemical compound CN=C1C(C=CC=C1[N+](=O)[O-])C(=O)O HLOAUTGENTUURB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000027932 Collagen disease Diseases 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- 208000006268 Sarcoma 180 Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
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- IVTWTKYSRBJJBW-UHFFFAOYSA-N [4-(5-carbamoyl-4-hydroxy-1h-imidazol-2-yl)phenyl] benzoate Chemical compound N1C(O)=C(C(=O)N)N=C1C(C=C1)=CC=C1OC(=O)C1=CC=CC=C1 IVTWTKYSRBJJBW-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
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- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
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- 210000000601 blood cell Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
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- 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
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- HXDVBUOHJZMCDP-UHFFFAOYSA-N ethyl 2-imino-2-phenylacetate;hydrochloride Chemical compound Cl.CCOC(=O)C(=N)C1=CC=CC=C1 HXDVBUOHJZMCDP-UHFFFAOYSA-N 0.000 description 1
- HSHJBSIHSQDZIU-UHFFFAOYSA-N ethyl 3-(5-carbamoyl-4-hydroxy-1h-imidazol-2-yl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C=2NC(O)=C(C(N)=O)N=2)=C1 HSHJBSIHSQDZIU-UHFFFAOYSA-N 0.000 description 1
- MODZVIMSNXSQIH-UHFFFAOYSA-N ethyl benzenecarboximidate;hydron;chloride Chemical compound Cl.CCOC(=N)C1=CC=CC=C1 MODZVIMSNXSQIH-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
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- 150000003840 hydrochlorides Chemical class 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
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- 239000011630 iodine Substances 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
- 238000002955 isolation Methods 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 150000007522 mineralic acids Chemical class 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
- 230000003472 neutralizing effect Effects 0.000 description 1
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- WOZBDBXOUNJZIO-UHFFFAOYSA-N phenyl 3-(5-carbamoyl-4-hydroxy-1h-imidazol-2-yl)benzoate Chemical compound N1C(O)=C(C(=O)N)N=C1C1=CC=CC(C(=O)OC=2C=CC=CC=2)=C1 WOZBDBXOUNJZIO-UHFFFAOYSA-N 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
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- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003826 tablet Substances 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BQFPCTXLBRVFJL-UHFFFAOYSA-N triethoxymethylbenzene Chemical compound CCOC(OCC)(OCC)C1=CC=CC=C1 BQFPCTXLBRVFJL-UHFFFAOYSA-N 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10764177A JPS5441874A (en) | 1977-09-06 | 1977-09-06 | Novel 2-substituted imidazole derivative |
| JP12499277A JPS5459273A (en) | 1977-10-17 | 1977-10-17 | Novel 2-arylimidazole derivative |
| JP12499577A JPS5459284A (en) | 1977-10-17 | 1977-10-17 | Novel 2-pyridylimidazole derivative |
| JP2890078A JPS54122272A (en) | 1978-03-13 | 1978-03-13 | Novel 2-substituted phenylimidazole derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7809373L SE7809373L (sv) | 1979-03-07 |
| SE442865B true SE442865B (sv) | 1986-02-03 |
Family
ID=27458967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7809373A SE442865B (sv) | 1977-09-06 | 1978-09-06 | Farmaceutiskt aktiva 2-substituerade-5-hydroxi-1h-imidazol-4-karboxamidderivat |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4218457A (de) |
| AT (1) | AT367412B (de) |
| AU (1) | AU507066B1 (de) |
| BE (1) | BE870236A (de) |
| CA (1) | CA1110623A (de) |
| CH (1) | CH636862A5 (de) |
| DE (1) | DE2838892A1 (de) |
| DK (1) | DK392578A (de) |
| FR (1) | FR2401916A1 (de) |
| GB (1) | GB2004544B (de) |
| HU (1) | HU184188B (de) |
| IT (1) | IT1160633B (de) |
| NL (1) | NL7809075A (de) |
| SE (1) | SE442865B (de) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU530916B2 (en) * | 1979-08-08 | 1983-08-04 | Sumitomo Chemical Company, Limited | 4-carbamoyl imidazolium-5-olate derivatives |
| CA1151651A (en) * | 1979-08-08 | 1983-08-09 | Takao Kiyohara | Antitumor and immunosuppressive 4-carbamoyl imidazolium-5-olate derivatives, pharmaceutical composition and production thereof |
| US4464531A (en) * | 1981-04-20 | 1984-08-07 | Sumitomo Chemical Company, Limited | 4-Carbamoylimidazolium-5-olate derivatives |
| US4503235A (en) * | 1983-03-11 | 1985-03-05 | Warner-Lambert Company | Process for producing 4-carbamoyl-1H-imidazolium-5-olate |
| JPS60193997A (ja) * | 1984-03-14 | 1985-10-02 | Sumitomo Chem Co Ltd | 新規シアノイミダゾ−ルリボヌクレオシド誘導体およびその製造法 |
| CA2613458A1 (en) * | 2005-07-12 | 2007-01-18 | Acadia Pharmaceuticals Inc. | Compounds with activity at retinoic acid receptors |
| JP5153773B2 (ja) * | 2006-07-07 | 2013-02-27 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | フェニル置換ヘテロアリール誘導体及び抗癌剤としてのその使用 |
| JPWO2008136428A1 (ja) | 2007-04-27 | 2010-07-29 | 武田薬品工業株式会社 | 含窒素５員複素環化合物 |
| JP2010531850A (ja) * | 2007-07-02 | 2010-09-30 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規化合物 |
| CL2008001943A1 (es) | 2007-07-02 | 2009-09-11 | Boehringer Ingelheim Int | Compuestos derivados de fenil-triazol, inhibidores de enzimas de señales especificas que participan del control de la proliferacion celular; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar cancer, infecciones, enfermedades inflamatorias y autoinmunes. |
| MX2011003292A (es) | 2008-09-29 | 2011-04-21 | Boehringer Ingelheim Int | Compuestos antiproliferativos. |
| US9290507B2 (en) | 2010-03-26 | 2016-03-22 | Boehringer Ingelheim International Gmbh | B-RAF kinase inhibitors |
| EP2552907B1 (de) | 2010-03-26 | 2014-10-22 | Boehringer Ingelheim International GmbH | Pyridyltriazole |
| ES2603032T3 (es) | 2010-07-15 | 2017-02-23 | Bayer Intellectual Property Gmbh | Compuestos de 3-piridil-heteroarilcarboxamida como pesticidas |
| US8710055B2 (en) | 2010-12-21 | 2014-04-29 | Boehringer Ingelheim International Gmbh | Triazolylphenyl sulfonamides as serine/threonine kinase inhibitors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1360982A (en) * | 1970-08-27 | 1974-07-24 | Beecham Group Ltd | Derivatives of 1-phenyl-5-aminoimidazole and compositions thereof |
| US3812136A (en) * | 1972-05-05 | 1974-05-21 | Merck & Co Inc | Tri-substituted imidazoles |
| AU502122B2 (en) * | 1976-07-02 | 1979-07-12 | Sumitomo Chemical Company, Limited | 5-0-acylated-imidazole-4-carboxamide derivatives |
| JPS604802B2 (ja) * | 1976-09-07 | 1985-02-06 | 住友化学工業株式会社 | 制癌剤 |
| US4140788A (en) * | 1976-11-10 | 1979-02-20 | Sumitomo Chemical Company, Limited | N-Substituted imidazolecarboxamide derivatives |
-
1978
- 1978-09-01 AU AU39492/78A patent/AU507066B1/en not_active Expired
- 1978-09-05 DK DK392578A patent/DK392578A/da not_active Application Discontinuation
- 1978-09-05 CH CH931278A patent/CH636862A5/de not_active IP Right Cessation
- 1978-09-05 GB GB7835686A patent/GB2004544B/en not_active Expired
- 1978-09-05 IT IT69049/78A patent/IT1160633B/it active
- 1978-09-05 CA CA310,576A patent/CA1110623A/en not_active Expired
- 1978-09-05 FR FR7825487A patent/FR2401916A1/fr active Granted
- 1978-09-05 AT AT0640778A patent/AT367412B/de not_active IP Right Cessation
- 1978-09-05 BE BE6046598A patent/BE870236A/xx not_active IP Right Cessation
- 1978-09-05 HU HU78SU989A patent/HU184188B/hu unknown
- 1978-09-05 NL NL7809075A patent/NL7809075A/xx not_active Application Discontinuation
- 1978-09-06 US US05/940,131 patent/US4218457A/en not_active Expired - Lifetime
- 1978-09-06 DE DE19782838892 patent/DE2838892A1/de not_active Withdrawn
- 1978-09-06 SE SE7809373A patent/SE442865B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU507066B1 (en) | 1980-01-31 |
| GB2004544A (en) | 1979-04-04 |
| AT367412B (de) | 1982-07-12 |
| NL7809075A (nl) | 1979-03-08 |
| SE7809373L (sv) | 1979-03-07 |
| FR2401916B1 (de) | 1982-07-02 |
| CH636862A5 (de) | 1983-06-30 |
| US4218457A (en) | 1980-08-19 |
| DK392578A (da) | 1979-03-07 |
| HU184188B (en) | 1984-07-30 |
| BE870236A (fr) | 1979-03-05 |
| IT7869049A0 (it) | 1978-09-05 |
| IT1160633B (it) | 1987-03-11 |
| CA1110623A (en) | 1981-10-13 |
| GB2004544B (en) | 1982-09-15 |
| ATA640778A (de) | 1981-11-15 |
| FR2401916A1 (fr) | 1979-03-30 |
| DE2838892A1 (de) | 1979-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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