NO791707L - Fremgangsmaate ved fremstilling av nye imidazolderivater - Google Patents
Fremgangsmaate ved fremstilling av nye imidazolderivaterInfo
- Publication number
- NO791707L NO791707L NO791707A NO791707A NO791707L NO 791707 L NO791707 L NO 791707L NO 791707 A NO791707 A NO 791707A NO 791707 A NO791707 A NO 791707A NO 791707 L NO791707 L NO 791707L
- Authority
- NO
- Norway
- Prior art keywords
- imidazole
- bis
- methoxyphenyl
- residue
- general formula
- Prior art date
Links
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title claims abstract description 19
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 6
- 150000002460 imidazoles Chemical class 0.000 claims abstract description 33
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- 150000007513 acids Chemical class 0.000 claims abstract 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- -1 4-dimethylaminophenyl residue Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 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 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- BUXHLLFKSLFFIS-UHFFFAOYSA-N 2-[(4,5-dithiophen-2-yl-1h-imidazol-2-yl)sulfanyl]ethanol Chemical compound C=1C=CSC=1C=1NC(SCCO)=NC=1C1=CC=CS1 BUXHLLFKSLFFIS-UHFFFAOYSA-N 0.000 claims description 4
- 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
- FBTNERVLZODKEZ-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfinyl]ethanol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S(=O)CCO)=N1 FBTNERVLZODKEZ-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 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 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-butanediol Substances OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 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
- CLORITHERGEEGK-UHFFFAOYSA-N 2-(2,2-dimethoxyethylsulfinyl)-4,5-bis(4-methoxyphenyl)-1h-imidazole Chemical compound N1C(S(=O)CC(OC)OC)=NC(C=2C=CC(OC)=CC=2)=C1C1=CC=C(OC)C=C1 CLORITHERGEEGK-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- OXSRPBUYYQACSP-UHFFFAOYSA-N 2-[(4,5-dipyridin-2-yl-1h-imidazol-2-yl)sulfinyl]ethanol Chemical compound N1C(S(=O)CCO)=NC(C=2N=CC=CC=2)=C1C1=CC=CC=N1 OXSRPBUYYQACSP-UHFFFAOYSA-N 0.000 claims description 2
- TWEBZYAMLAYUSX-UHFFFAOYSA-N 2-[(4,5-dipyridin-2-yl-1h-imidazol-2-yl)sulfonyl]ethanol Chemical compound N1C(S(=O)(=O)CCO)=NC(C=2N=CC=CC=2)=C1C1=CC=CC=N1 TWEBZYAMLAYUSX-UHFFFAOYSA-N 0.000 claims description 2
- WJZZKVVBHCOPGQ-UHFFFAOYSA-N 2-[(4,5-dithiophen-2-yl-1h-imidazol-2-yl)sulfinyl]ethanol Chemical compound C=1C=CSC=1C=1NC(S(=O)CCO)=NC=1C1=CC=CS1 WJZZKVVBHCOPGQ-UHFFFAOYSA-N 0.000 claims description 2
- FCOCWTQBKIUBSS-UHFFFAOYSA-N 2-[(4,5-dithiophen-2-yl-1h-imidazol-2-yl)sulfonyl]ethanol Chemical compound C=1C=CSC=1C=1NC(S(=O)(=O)CCO)=NC=1C1=CC=CS1 FCOCWTQBKIUBSS-UHFFFAOYSA-N 0.000 claims description 2
- ULIGPRQYPVGWAY-UHFFFAOYSA-N 2-[[4,5-bis(4-chlorophenyl)-1h-imidazol-2-yl]sulfinyl]ethanol Chemical compound N1C(S(=O)CCO)=NC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 ULIGPRQYPVGWAY-UHFFFAOYSA-N 0.000 claims description 2
- NHGLZUXMCRFRMT-UHFFFAOYSA-N 2-[[4,5-bis(4-chlorophenyl)-1h-imidazol-2-yl]sulfonyl]ethanol Chemical compound N1C(S(=O)(=O)CCO)=NC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 NHGLZUXMCRFRMT-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- YBMNMHBQDQGPCT-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfinyl]-2-methylpropan-1-ol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S(=O)C(C)(C)CO)=N1 YBMNMHBQDQGPCT-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- BCTIQOWCSDPGCG-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfonyl]ethanol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S(=O)(=O)CCO)=N1 BCTIQOWCSDPGCG-UHFFFAOYSA-N 0.000 claims description 2
- LWVXZPJROPYWIH-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfonyl]propan-1-ol Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S(=O)(=O)C(C)CO)=N1 LWVXZPJROPYWIH-UHFFFAOYSA-N 0.000 claims description 2
- FLPWXPDTPDPKDS-UHFFFAOYSA-N 2-[[4,5-bis(4-methylphenyl)-1h-imidazol-2-yl]sulfinyl]ethanol Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC(C)=CC=2)NC(S(=O)CCO)=N1 FLPWXPDTPDPKDS-UHFFFAOYSA-N 0.000 claims description 2
- RCVVLHNEMQCSGL-UHFFFAOYSA-N 2-[[4,5-bis(4-methylphenyl)-1h-imidazol-2-yl]sulfonyl]ethanol Chemical compound C1=CC(C)=CC=C1C1=C(C=2C=CC(C)=CC=2)NC(S(=O)(=O)CCO)=N1 RCVVLHNEMQCSGL-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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004277 1,3-dioxalan-2-yl group Chemical group [H]C1([H])OC([H])(*)OC1([H])[H] 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
- 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 1
- MLXDUYUQINCFFV-UHFFFAOYSA-N 2-acetyloxyacetic acid Chemical compound CC(=O)OCC(O)=O MLXDUYUQINCFFV-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 3
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 101
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 229910052938 sodium sulfate Inorganic materials 0.000 description 26
- 235000011152 sodium sulphate Nutrition 0.000 description 26
- 235000019439 ethyl acetate Nutrition 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000005457 ice water Substances 0.000 description 19
- 229910052786 argon Inorganic materials 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- NZKLDYYRLVFZCE-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-1,3-dihydroimidazole-2-thione Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S)=N1 NZKLDYYRLVFZCE-UHFFFAOYSA-N 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
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- 238000001953 recrystallisation Methods 0.000 description 8
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
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- 238000002474 experimental method Methods 0.000 description 5
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 5
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 210000000548 hind-foot Anatomy 0.000 description 4
- 230000003902 lesion Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 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 description 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 description 3
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
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- 230000002401 inhibitory effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 235000019359 magnesium stearate 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
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
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- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 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)
- Epoxy Resins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
|---|---|
| NO791707L true NO791707L (no) | 1979-11-27 |
Family
ID=6040343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO791707A NO791707L (no) | 1978-05-24 | 1979-05-23 | Fremgangsmaate ved fremstilling av nye imidazolderivater |
Country Status (24)
| Country | Link |
|---|---|
| US (3) | US4269847A (fr) |
| EP (1) | EP0005545B1 (fr) |
| JP (1) | JPS54154766A (fr) |
| AT (1) | ATE15662T1 (fr) |
| AU (1) | AU4737979A (fr) |
| BG (1) | BG32268A3 (fr) |
| CA (1) | CA1177836A (fr) |
| DD (1) | DD143770A5 (fr) |
| DE (2) | DE2823197A1 (fr) |
| DK (1) | DK208979A (fr) |
| EG (1) | EG14365A (fr) |
| ES (1) | ES480809A1 (fr) |
| FI (1) | FI791639A (fr) |
| FR (1) | FR2426682A1 (fr) |
| GB (1) | GB2023600B (fr) |
| GR (1) | GR72243B (fr) |
| IE (1) | IE48416B1 (fr) |
| IL (1) | IL57384A0 (fr) |
| NO (1) | NO791707L (fr) |
| NZ (1) | NZ190529A (fr) |
| PL (1) | PL215774A1 (fr) |
| PT (1) | PT69618A (fr) |
| RO (1) | RO77293A (fr) |
| ZA (1) | ZA792522B (fr) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2963572D1 (en) * | 1978-04-11 | 1982-10-21 | Ciba Geigy Ag | Mercapto-imidazole derivatives, their preparation, mercapto-imidazole derivatives for the treatment of inflammatory diseases and their pharmaceutical compositions |
| 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 |
| 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 |
| 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 |
| 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 |
| KR20010014288A (ko) * | 1997-06-30 | 2001-02-26 | 오르토-맥네일 파마슈티칼, 인코퍼레이티드 | 염증성 질환의 치료에 유용한 2-치환된 이미다졸 |
| 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 (fr) * | 2006-08-24 | 2008-03-05 | Merckle Gmbh | Derivés d'imidazole ayant une activité anti-inflammatoire |
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 |
| NL6614808A (fr) * | 1965-10-21 | 1967-04-24 | ||
| 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 (fr) * | 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 |
| SE428686B (sv) * | 1975-08-11 | 1983-07-18 | Du Pont | Forfarande for framstellning av antiinflammatoriskt aktiva imidazoler |
| 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 |
| 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 |
| 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 |
| LU77703A1 (de) * | 1977-07-07 | 1979-03-26 | Ciba Geigy Ag | Verfahren zur herstellung von bicyclischen thia-diaza-verbindungen |
| DE2963572D1 (en) * | 1978-04-11 | 1982-10-21 | Ciba Geigy Ag | Mercapto-imidazole derivatives, their preparation, mercapto-imidazole derivatives for the treatment of inflammatory diseases and their pharmaceutical compositions |
-
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 AT AT79101509T patent/ATE15662T1/de not_active IP Right Cessation
- 1979-05-17 EP EP79101509A patent/EP0005545B1/fr not_active Expired
- 1979-05-17 DE DE7979101509T patent/DE2967513D1/de not_active Expired
- 1979-05-21 BG BG7943677A patent/BG32268A3/xx unknown
- 1979-05-21 FR FR7912876A patent/FR2426682A1/fr not_active Withdrawn
- 1979-05-22 DK DK208979A patent/DK208979A/da not_active Application Discontinuation
- 1979-05-22 US US06/041,367 patent/US4269847A/en not_active Expired - Lifetime
- 1979-05-22 PL PL21577479A patent/PL215774A1/xx unknown
- 1979-05-22 ES ES480809A patent/ES480809A1/es not_active Expired
- 1979-05-22 GR GR59147A patent/GR72243B/el unknown
- 1979-05-22 DD DD79213065A patent/DD143770A5/de unknown
- 1979-05-23 JP JP6277479A patent/JPS54154766A/ja active Granted
- 1979-05-23 NZ NZ190529A patent/NZ190529A/xx unknown
- 1979-05-23 GB GB7917874A patent/GB2023600B/en not_active Expired
- 1979-05-23 IL IL57384A patent/IL57384A0/xx unknown
- 1979-05-23 CA CA000328095A patent/CA1177836A/fr not_active Expired
- 1979-05-23 EG EG311/79A patent/EG14365A/xx active
- 1979-05-23 NO NO791707A patent/NO791707L/no unknown
- 1979-05-23 FI FI791639A patent/FI791639A/fi not_active Application Discontinuation
- 1979-05-23 ZA ZA792522A patent/ZA792522B/xx unknown
- 1979-05-24 AU AU47379/79A patent/AU4737979A/en not_active Abandoned
- 1979-05-24 RO RO7997627A patent/RO77293A/fr unknown
- 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 |
|---|---|
| EP0005545A2 (fr) | 1979-11-28 |
| AU4737979A (en) | 1979-11-29 |
| JPH0336834B2 (fr) | 1991-06-03 |
| ZA792522B (en) | 1980-06-25 |
| EP0005545A3 (en) | 1980-01-09 |
| DK208979A (da) | 1979-11-25 |
| ATE15662T1 (de) | 1985-10-15 |
| IL57384A0 (en) | 1979-09-30 |
| CA1177836A (fr) | 1984-11-13 |
| PT69618A (de) | 1979-06-01 |
| EP0005545B1 (fr) | 1985-09-18 |
| JPS54154766A (en) | 1979-12-06 |
| IE791000L (en) | 1979-11-24 |
| GB2023600A (en) | 1980-01-03 |
| NZ190529A (en) | 1982-02-23 |
| FI791639A (fi) | 1979-11-25 |
| DE2967513D1 (en) | 1985-10-24 |
| PL215774A1 (fr) | 1980-02-25 |
| US4355039A (en) | 1982-10-19 |
| IE48416B1 (en) | 1985-01-09 |
| US4440776A (en) | 1984-04-03 |
| GR72243B (fr) | 1983-10-04 |
| US4269847A (en) | 1981-05-26 |
| RO77293A (fr) | 1981-08-17 |
| BG32268A3 (en) | 1982-06-15 |
| DE2823197A1 (de) | 1979-11-29 |
| DD143770A5 (de) | 1980-09-10 |
| FR2426682A1 (fr) | 1979-12-21 |
| ES480809A1 (es) | 1979-12-01 |
| GB2023600B (en) | 1982-11-03 |
| EG14365A (en) | 1984-03-31 |
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