CA1177836A - 4,5-bisphenyl-2-sulphur containing imidazole compounds - Google Patents
4,5-bisphenyl-2-sulphur containing imidazole compoundsInfo
- Publication number
- CA1177836A CA1177836A CA000328095A CA328095A CA1177836A CA 1177836 A CA1177836 A CA 1177836A CA 000328095 A CA000328095 A CA 000328095A CA 328095 A CA328095 A CA 328095A CA 1177836 A CA1177836 A CA 1177836A
- Authority
- CA
- Canada
- Prior art keywords
- bis
- methoxyphenyl
- radical
- imidazole
- produced
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000002460 imidazoles Chemical class 0.000 title claims description 32
- 239000005864 Sulphur Substances 0.000 title 1
- -1 alkyl radicals Chemical class 0.000 claims abstract description 114
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 83
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000000524 functional group Chemical group 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 123
- 230000008569 process Effects 0.000 claims description 123
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 105
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 71
- 239000000126 substance Substances 0.000 claims description 69
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 68
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 63
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 43
- 229910052786 argon Inorganic materials 0.000 claims description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 26
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 16
- 239000011734 sodium Substances 0.000 claims description 16
- 229910052708 sodium Inorganic materials 0.000 claims description 16
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- LKJOIMMFMMZDIE-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfanyl]ethanol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SCCO)=N1 LKJOIMMFMMZDIE-UHFFFAOYSA-N 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
- 229960000583 acetic acid Drugs 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 6
- 239000012312 sodium hydride Substances 0.000 claims description 6
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001117 sulphuric acid Substances 0.000 claims description 5
- 235000011149 sulphuric acid Nutrition 0.000 claims description 5
- OWBGGOHIBJRGQL-UHFFFAOYSA-N 2-[[4,5-bis(4-fluorophenyl)-1h-imidazol-2-yl]sulfanyl]ethanol Chemical compound N1C(SCCO)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 OWBGGOHIBJRGQL-UHFFFAOYSA-N 0.000 claims description 4
- NSKBCBZIXJYLMA-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfanyl]-2-methylpropan-1-ol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC(C)(C)CO)=N1 NSKBCBZIXJYLMA-UHFFFAOYSA-N 0.000 claims description 4
- LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- 235000011054 acetic acid Nutrition 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 4
- 150000002596 lactones Chemical class 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- LFJJGHGXHXXDFT-UHFFFAOYSA-N 3-bromooxolan-2-one Chemical compound BrC1CCOC1=O LFJJGHGXHXXDFT-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 229940071870 hydroiodic acid Drugs 0.000 claims description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims description 3
- 235000011007 phosphoric acid Nutrition 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- HZDNNJABYXNPPV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) acetate Chemical compound CC(=O)OCC(Cl)=O HZDNNJABYXNPPV-UHFFFAOYSA-N 0.000 claims description 2
- HVLALTSPOCWDHT-UHFFFAOYSA-N 1-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfanyl]-2-methylpropan-2-ol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SCC(C)(C)O)=N1 HVLALTSPOCWDHT-UHFFFAOYSA-N 0.000 claims description 2
- SXDYWNIUOVOAOP-UHFFFAOYSA-N 2-(2,2-diethoxyethylsulfinyl)-4,5-bis(4-methoxyphenyl)-1h-imidazole Chemical compound N1C(S(=O)CC(OCC)OCC)=NC(C=2C=CC(OC)=CC=2)=C1C1=CC=C(OC)C=C1 SXDYWNIUOVOAOP-UHFFFAOYSA-N 0.000 claims description 2
- WIZMESLZENXELS-UHFFFAOYSA-N 2-[[4,5-bis(4-fluorophenyl)-1h-imidazol-2-yl]sulfonyl]ethanol Chemical compound N1C(S(=O)(=O)CCO)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 WIZMESLZENXELS-UHFFFAOYSA-N 0.000 claims description 2
- LKEPKNMIDXTZLJ-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfanyl]ethyl acetate Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SCCOC(C)=O)=N1 LKEPKNMIDXTZLJ-UHFFFAOYSA-N 0.000 claims description 2
- WJRFDOQPCCQYAT-UHFFFAOYSA-N 2-bromoacetaldehyde;ethene Chemical group C=C.BrCC=O WJRFDOQPCCQYAT-UHFFFAOYSA-N 0.000 claims description 2
- CRZJPEIBPQWDGJ-UHFFFAOYSA-N 2-chloro-1,1-dimethoxyethane Chemical compound COC(CCl)OC CRZJPEIBPQWDGJ-UHFFFAOYSA-N 0.000 claims description 2
- YFSKRSNDBMZROF-UHFFFAOYSA-N 3-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfanyl]prop-2-en-1-ol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC=CCO)=N1 YFSKRSNDBMZROF-UHFFFAOYSA-N 0.000 claims description 2
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 claims description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 claims description 2
- FMVJYQGSRWVMQV-UHFFFAOYSA-N ethyl propiolate Chemical compound CCOC(=O)C#C FMVJYQGSRWVMQV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 claims description 2
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical class C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims 10
- GEAXLHPORCRESC-UHFFFAOYSA-N chlorocyclohexatriene Chemical compound ClC1=CC=C=C[CH]1 GEAXLHPORCRESC-UHFFFAOYSA-N 0.000 claims 7
- PTTVRIGSUJQBPB-UHFFFAOYSA-N fluorocyclohexatriene Chemical compound FC1=CC=C=C[CH]1 PTTVRIGSUJQBPB-UHFFFAOYSA-N 0.000 claims 7
- GPKUICFDWYEPTK-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=CC=C=C[CH]1 GPKUICFDWYEPTK-UHFFFAOYSA-N 0.000 claims 7
- 150000003254 radicals Chemical class 0.000 claims 7
- 239000012300 argon atmosphere Substances 0.000 claims 5
- SRWSLLSPVVKZOJ-UHFFFAOYSA-N 2-(1,3-dioxolan-2-ylmethylsulfanyl)-4,5-bis(4-methoxyphenyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SCC2OCCO2)=N1 SRWSLLSPVVKZOJ-UHFFFAOYSA-N 0.000 claims 3
- YLURJHPLCVFNKZ-UHFFFAOYSA-N 2-(2,2-diethoxyethylsulfanyl)-4,5-bis(4-methoxyphenyl)-1h-imidazole Chemical compound N1C(SCC(OCC)OCC)=NC(C=2C=CC(OC)=CC=2)=C1C1=CC=C(OC)C=C1 YLURJHPLCVFNKZ-UHFFFAOYSA-N 0.000 claims 3
- MOGMNOADWQORRF-UHFFFAOYSA-N 2-(2,2-dimethoxyethylsulfanyl)-4,5-bis(4-methoxyphenyl)-1h-imidazole Chemical compound N1C(SCC(OC)OC)=NC(C=2C=CC(OC)=CC=2)=C1C1=CC=C(OC)C=C1 MOGMNOADWQORRF-UHFFFAOYSA-N 0.000 claims 3
- LRMRMKHHCZNNNW-UHFFFAOYSA-N 2-[[4,5-bis(4-chlorophenyl)-1h-imidazol-2-yl]sulfanyl]ethanol Chemical compound N1C(SCCO)=NC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 LRMRMKHHCZNNNW-UHFFFAOYSA-N 0.000 claims 3
- XDXHXEAAIMZHSP-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfanyl]propan-1-ol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC(C)CO)=N1 XDXHXEAAIMZHSP-UHFFFAOYSA-N 0.000 claims 3
- RTRPCSKTKXJQTD-UHFFFAOYSA-N 2-[[4,5-bis(4-methylphenyl)-1h-imidazol-2-yl]sulfanyl]ethanol Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC(C)=CC=2)NC(SCCO)=N1 RTRPCSKTKXJQTD-UHFFFAOYSA-N 0.000 claims 3
- 239000012458 free base Substances 0.000 claims 3
- MLXDUYUQINCFFV-UHFFFAOYSA-N 2-acetyloxyacetic acid Chemical compound CC(=O)OCC(O)=O MLXDUYUQINCFFV-UHFFFAOYSA-N 0.000 claims 2
- ZYYABLSQHNSPJI-UHFFFAOYSA-N N=1C(C=2C=CC(OC)=CC=2)=C(C=2C=CC(OC)=CC=2)NC=1C1(CC)OC1=S Chemical compound N=1C(C=2C=CC(OC)=CC=2)=C(C=2C=CC(OC)=CC=2)NC=1C1(CC)OC1=S ZYYABLSQHNSPJI-UHFFFAOYSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 2
- 150000002118 epoxides Chemical class 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 claims 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-butanediol Substances OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims 1
- IHMQJGSGMXUCMX-UHFFFAOYSA-N 1-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfanyl]propan-2-ol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SCC(C)O)=N1 IHMQJGSGMXUCMX-UHFFFAOYSA-N 0.000 claims 1
- FGWKVHQFLIMCFM-UHFFFAOYSA-N 2-(1,3-dioxolan-2-ylmethylsulfinyl)-4,5-bis(4-methoxyphenyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S(=O)CC2OCCO2)=N1 FGWKVHQFLIMCFM-UHFFFAOYSA-N 0.000 claims 1
- CDOIGVSXFNGTOD-UHFFFAOYSA-N 2-(1,3-dioxolan-2-ylmethylsulfonyl)-4,5-bis(4-methoxyphenyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S(=O)(=O)CC2OCCO2)=N1 CDOIGVSXFNGTOD-UHFFFAOYSA-N 0.000 claims 1
- HSHZEPWRARSAAP-UHFFFAOYSA-N 2-(2,2-dimethoxyethylsulfonyl)-4,5-bis(4-methoxyphenyl)-1h-imidazole Chemical compound N1C(S(=O)(=O)CC(OC)OC)=NC(C=2C=CC(OC)=CC=2)=C1C1=CC=C(OC)C=C1 HSHZEPWRARSAAP-UHFFFAOYSA-N 0.000 claims 1
- ZGULCNWGPGBDQE-UHFFFAOYSA-N 2-(2-methoxyethylsulfanyl)-4,5-bis(4-methoxyphenyl)-1h-imidazole Chemical compound N1C(SCCOC)=NC(C=2C=CC(OC)=CC=2)=C1C1=CC=C(OC)C=C1 ZGULCNWGPGBDQE-UHFFFAOYSA-N 0.000 claims 1
- BXJVRGRBSJAJTI-UHFFFAOYSA-N 2-[4,5-bis(4-methoxyphenyl)-1-methylimidazol-2-yl]sulfanylethanol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N(C)C(SCCO)=N1 BXJVRGRBSJAJTI-UHFFFAOYSA-N 0.000 claims 1
- ZUZZMRBXEUYWAN-UHFFFAOYSA-N 2-[[4,5-bis(4-fluorophenyl)-1h-imidazol-2-yl]sulfinyl]ethanol Chemical compound N1C(S(=O)CCO)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 ZUZZMRBXEUYWAN-UHFFFAOYSA-N 0.000 claims 1
- WZQLUMHOPWGQJD-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfinyl]propan-1-ol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S(=O)C(C)CO)=N1 WZQLUMHOPWGQJD-UHFFFAOYSA-N 0.000 claims 1
- GXQGWEHQTOYFPN-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfonyl]-2-methylpropan-1-ol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S(=O)(=O)C(C)(C)CO)=N1 GXQGWEHQTOYFPN-UHFFFAOYSA-N 0.000 claims 1
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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
- C07D233/84—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Epoxy Resins (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2823197.2 | 1978-05-24 | ||
| DE19782823197 DE2823197A1 (de) | 1978-05-24 | 1978-05-24 | Neue imidazolderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1177836A true CA1177836A (en) | 1984-11-13 |
Family
ID=6040343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000328095A Expired CA1177836A (en) | 1978-05-24 | 1979-05-23 | 4,5-bisphenyl-2-sulphur containing imidazole compounds |
Country Status (24)
| Country | Link |
|---|---|
| US (3) | US4269847A (en, 2012) |
| EP (1) | EP0005545B1 (en, 2012) |
| JP (1) | JPS54154766A (en, 2012) |
| AT (1) | ATE15662T1 (en, 2012) |
| AU (1) | AU4737979A (en, 2012) |
| BG (1) | BG32268A3 (en, 2012) |
| CA (1) | CA1177836A (en, 2012) |
| DD (1) | DD143770A5 (en, 2012) |
| DE (2) | DE2823197A1 (en, 2012) |
| DK (1) | DK208979A (en, 2012) |
| EG (1) | EG14365A (en, 2012) |
| ES (1) | ES480809A1 (en, 2012) |
| FI (1) | FI791639A7 (en, 2012) |
| FR (1) | FR2426682A1 (en, 2012) |
| GB (1) | GB2023600B (en, 2012) |
| GR (1) | GR72243B (en, 2012) |
| IE (1) | IE48416B1 (en, 2012) |
| IL (1) | IL57384A0 (en, 2012) |
| NO (1) | NO791707L (en, 2012) |
| NZ (1) | NZ190529A (en, 2012) |
| PL (1) | PL215774A1 (en, 2012) |
| PT (1) | PT69618A (en, 2012) |
| RO (1) | RO77293A (en, 2012) |
| ZA (1) | ZA792522B (en, 2012) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CY1302A (en) * | 1978-04-11 | 1985-12-06 | Ciba Geigy Ag | Mercapto-imidazole derivatives,their preparation,their pharmaceutical compositions and applications |
| DE2856909A1 (de) * | 1978-12-28 | 1980-07-17 | Schering Ag | Neue imidazolderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| DE3025484A1 (de) * | 1980-07-03 | 1982-02-04 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue imidazol-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| US4503065A (en) * | 1982-08-03 | 1985-03-05 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl 1-2-halo imidazoles |
| US4728656A (en) * | 1985-12-12 | 1988-03-01 | Smithkline Beckman Corporation | 2,2-alkyldiylbis(thio)bis(imidazoles) useful for inhibition of the 5-lipoxygenase pathway |
| US4847270A (en) * | 1985-12-12 | 1989-07-11 | Smithkline Beckman Corporation | Inhibition of the 5-lipoxygenase pathway utilizing certain 2,2'-alkyldiyl bis(thio)bis-imidazoles and derivatives |
| JPS6440467A (en) * | 1987-08-04 | 1989-02-10 | Hisamitsu Pharmaceutical Co | Novel substituted diphenylimidazole derivative |
| US4900744A (en) * | 1988-09-14 | 1990-02-13 | E. I. Du Pont De Nemours And Company | Antihypercholesterolemic 4,5-diaryl-2-substituted thioimidazoles |
| GB9005966D0 (en) * | 1990-03-16 | 1990-05-09 | May & Baker Ltd | New compositions of matter |
| US5179117A (en) * | 1991-12-20 | 1993-01-12 | Du Pont Merck Pharmaceutical Company | Antihypercholesterolemic 2-substituted imidazoles |
| ATE193290T1 (de) * | 1992-02-11 | 2000-06-15 | Smithkline Beecham Corp | Coa-it- und paf-inhibitoren |
| US5663053A (en) * | 1992-02-11 | 1997-09-02 | Smithkline Beecham Corporation | Inhibition of inflammatory lipid mediators |
| EP0994858A1 (en) * | 1997-06-30 | 2000-04-26 | Ortho-McNeil Pharmaceutical, Inc. | 2-substituted imidazoles useful in the treatment of inflammatory diseases |
| DE10107683A1 (de) | 2001-02-19 | 2002-08-29 | Merckle Gmbh Chem Pharm Fabrik | 2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie |
| DE10114775A1 (de) * | 2001-03-26 | 2002-10-10 | Gerhard Dannhardt | 2-Mercapto-4,5-diarylimidazolderivate und ihre Verwendung in der Pharmazie |
| DE10238045A1 (de) | 2002-08-20 | 2004-03-04 | Merckle Gmbh Chem.-Pharm. Fabrik | 2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie |
| EP1894925A1 (en) * | 2006-08-24 | 2008-03-05 | Merckle Gmbh | Imidazole compounds having an antiinflammatory effect |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2981739A (en) * | 1958-01-27 | 1961-04-25 | Diamond Alkali Co | Certain alpha-haloaldehyde addition products of ethylenethioureas and process |
| FR1509975A (fr) * | 1965-10-21 | 1968-01-19 | Geigy Ag J R | Dérivés de l'imidazole et leur préparation |
| US3651080A (en) * | 1969-11-07 | 1972-03-21 | Ciba Geigy Corp | Certain substituted 2-alkylmercaptoimidazole derivatives |
| US3636003A (en) * | 1969-11-17 | 1972-01-18 | Geigy Chem Corp | Substituted 2-mercaptoimidazole derivatives |
| US3714179A (en) * | 1970-09-08 | 1973-01-30 | Searle & Co | 1-alkyl-2-furfurylthioimidazoles and congeners |
| JPS5343958B2 (en, 2012) * | 1972-07-29 | 1978-11-24 | ||
| DE2259627A1 (de) * | 1972-12-06 | 1974-06-12 | Hoechst Ag | Imidazolyl-(2)-thio-alkansaeureester und verfahren zu ihrer herstellung |
| US3842097A (en) * | 1973-01-22 | 1974-10-15 | Searle & Co | 2-(phenoxyalkylthio)imidazoles and congeners |
| US4190666A (en) * | 1975-08-11 | 1980-02-26 | E. I. Du Pont De Nemours And Company | Anti-inflammatory 4,5-diarly-2-(substituted-thio)imidazoles and their corresponding sulfoxides and sulfones |
| SE428686B (sv) * | 1975-08-11 | 1983-07-18 | Du Pont | Forfarande for framstellning av antiinflammatoriskt aktiva imidazoler |
| US4159338A (en) * | 1977-02-09 | 1979-06-26 | E. I. Du Pont De Nemours And Company | Antiinflammatory-4,5-dicyclic-2-(substituted thio)-imidazoles and their corresponding sulfoxides and sulfones |
| US4182769A (en) * | 1977-02-09 | 1980-01-08 | E. I. Du Pont De Nemours And Company | Anti-inflammatory 1-substituted-4,5-diaryl-2-(substituted-thio) imidazoles and their corresponding sulfoxides and sulfones |
| LU77703A1 (de) * | 1977-07-07 | 1979-03-26 | Ciba Geigy Ag | Verfahren zur herstellung von bicyclischen thia-diaza-verbindungen |
| CY1302A (en) * | 1978-04-11 | 1985-12-06 | Ciba Geigy Ag | Mercapto-imidazole derivatives,their preparation,their pharmaceutical compositions and applications |
-
1978
- 1978-05-24 DE DE19782823197 patent/DE2823197A1/de not_active Withdrawn
-
1979
- 1979-05-16 PT PT69618A patent/PT69618A/pt unknown
- 1979-05-17 DE DE7979101509T patent/DE2967513D1/de not_active Expired
- 1979-05-17 AT AT79101509T patent/ATE15662T1/de not_active IP Right Cessation
- 1979-05-17 EP EP79101509A patent/EP0005545B1/de not_active Expired
- 1979-05-21 BG BG043677A patent/BG32268A3/xx unknown
- 1979-05-21 FR FR7912876A patent/FR2426682A1/fr not_active Withdrawn
- 1979-05-22 DD DD79213065A patent/DD143770A5/de unknown
- 1979-05-22 US US06/041,367 patent/US4269847A/en not_active Expired - Lifetime
- 1979-05-22 GR GR59147A patent/GR72243B/el unknown
- 1979-05-22 PL PL21577479A patent/PL215774A1/xx unknown
- 1979-05-22 ES ES480809A patent/ES480809A1/es not_active Expired
- 1979-05-22 DK DK208979A patent/DK208979A/da not_active Application Discontinuation
- 1979-05-23 ZA ZA792522A patent/ZA792522B/xx unknown
- 1979-05-23 FI FI791639A patent/FI791639A7/fi not_active Application Discontinuation
- 1979-05-23 CA CA000328095A patent/CA1177836A/en not_active Expired
- 1979-05-23 EG EG311/79A patent/EG14365A/xx active
- 1979-05-23 IL IL57384A patent/IL57384A0/xx unknown
- 1979-05-23 NO NO791707A patent/NO791707L/no unknown
- 1979-05-23 GB GB7917874A patent/GB2023600B/en not_active Expired
- 1979-05-23 JP JP6277479A patent/JPS54154766A/ja active Granted
- 1979-05-23 NZ NZ190529A patent/NZ190529A/xx unknown
- 1979-05-24 RO RO7997627A patent/RO77293A/ro unknown
- 1979-05-24 AU AU47379/79A patent/AU4737979A/en not_active Abandoned
- 1979-08-08 IE IE1000/79A patent/IE48416B1/en unknown
-
1980
- 1980-09-24 US US06/190,309 patent/US4355039A/en not_active Expired - Lifetime
-
1982
- 1982-03-24 US US06/361,225 patent/US4440776A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DD143770A5 (de) | 1980-09-10 |
| RO77293A (ro) | 1981-08-17 |
| FR2426682A1 (fr) | 1979-12-21 |
| BG32268A3 (bg) | 1982-06-15 |
| DE2967513D1 (en) | 1985-10-24 |
| IE791000L (en) | 1979-11-24 |
| PT69618A (de) | 1979-06-01 |
| NO791707L (no) | 1979-11-27 |
| GR72243B (en, 2012) | 1983-10-04 |
| US4440776A (en) | 1984-04-03 |
| FI791639A7 (fi) | 1981-01-01 |
| US4355039A (en) | 1982-10-19 |
| JPH0336834B2 (en, 2012) | 1991-06-03 |
| IL57384A0 (en) | 1979-09-30 |
| EP0005545A3 (en) | 1980-01-09 |
| ZA792522B (en) | 1980-06-25 |
| ES480809A1 (es) | 1979-12-01 |
| DK208979A (da) | 1979-11-25 |
| EP0005545B1 (de) | 1985-09-18 |
| EP0005545A2 (de) | 1979-11-28 |
| IE48416B1 (en) | 1985-01-09 |
| GB2023600A (en) | 1980-01-03 |
| AU4737979A (en) | 1979-11-29 |
| PL215774A1 (en, 2012) | 1980-02-25 |
| ATE15662T1 (de) | 1985-10-15 |
| EG14365A (en) | 1984-03-31 |
| GB2023600B (en) | 1982-11-03 |
| JPS54154766A (en) | 1979-12-06 |
| DE2823197A1 (de) | 1979-11-29 |
| US4269847A (en) | 1981-05-26 |
| NZ190529A (en) | 1982-02-23 |
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| MKEX | Expiry |