FI68619C - Foerfarande foer framstaellning av antiinflammatoriska 1-substituerade 4,5-diaryl-2-(substituerad tio)-imidazolderivat ochderas motsvarande sulfoner - Google Patents
Foerfarande foer framstaellning av antiinflammatoriska 1-substituerade 4,5-diaryl-2-(substituerad tio)-imidazolderivat ochderas motsvarande sulfoner Download PDFInfo
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- FI68619C FI68619C FI780429A FI780429A FI68619C FI 68619 C FI68619 C FI 68619C FI 780429 A FI780429 A FI 780429A FI 780429 A FI780429 A FI 780429A FI 68619 C FI68619 C FI 68619C
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- Prior art keywords
- phenyl
- formula
- och
- compound
- solvent
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 62
- 239000000203 mixture Substances 0.000 claims description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 23
- 238000010992 reflux Methods 0.000 claims description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 16
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 13
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- -1 2-tetrahydropyranyl Chemical group 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000003457 sulfones Chemical class 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims description 4
- 125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 3
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 3
- 229910006080 SO2X Inorganic materials 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 3
- 235000015320 potassium carbonate Nutrition 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- ZVKAMDSUUSMZES-NZQWGLPYSA-N OS II Natural products CC(=O)N[C@H]1[C@H](OC[C@@H](O)[C@@H](O)[C@@H](O)CO)O[C@H](CO)[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H]1O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O ZVKAMDSUUSMZES-NZQWGLPYSA-N 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 31
- 239000000047 product Substances 0.000 description 22
- 238000004458 analytical method Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 10
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 10
- XVLMMLFVASDPEI-UHFFFAOYSA-N 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylsulfanyl)-1h-imidazole Chemical compound N1C(SC(F)(F)C(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 XVLMMLFVASDPEI-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 210000002683 foot Anatomy 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 206010003246 arthritis Diseases 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 239000012259 ether extract Substances 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 7
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- GLYOPNLBKCBTMI-UHFFFAOYSA-N [2-chloro-2-(1-chloro-2-phenylethoxy)ethyl]benzene Chemical compound C=1C=CC=CC=1CC(Cl)OC(Cl)CC1=CC=CC=C1 GLYOPNLBKCBTMI-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 244000028419 Styrax benzoin Species 0.000 description 5
- 235000000126 Styrax benzoin Nutrition 0.000 description 5
- 235000008411 Sumatra benzointree Nutrition 0.000 description 5
- 229960002130 benzoin Drugs 0.000 description 5
- 235000019382 gum benzoic Nutrition 0.000 description 5
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 210000000548 hind-foot Anatomy 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- SMPOWYNHWWUUOU-UHFFFAOYSA-N 1-(benzenesulfonyl)-4,5-bis(4-fluorophenyl)imidazole Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC(F)=CC=2)N(S(=O)(=O)C=2C=CC=CC=2)C=N1 SMPOWYNHWWUUOU-UHFFFAOYSA-N 0.000 description 2
- NFUMICZSYFJBCV-UHFFFAOYSA-N 1-(oxan-2-yl)-4,5-diphenyl-2-(trifluoromethylsulfanyl)imidazole Chemical compound C1CCCOC1N1C(SC(F)(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 NFUMICZSYFJBCV-UHFFFAOYSA-N 0.000 description 2
- ORDFEFKKYKLUNW-UHFFFAOYSA-N 1-(oxan-2-yl)-4,5-diphenylimidazole Chemical compound O1CCCCC1N1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1 ORDFEFKKYKLUNW-UHFFFAOYSA-N 0.000 description 2
- XUOAKFNMJMYKBY-UHFFFAOYSA-N 4,5-bis(4-fluorophenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)-1h-imidazole Chemical compound N1C(S(=O)(=O)C(F)(F)C(F)F)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 XUOAKFNMJMYKBY-UHFFFAOYSA-N 0.000 description 2
- TVTOLIQBOMHYGM-UHFFFAOYSA-N 4,5-diphenyl-1-(phenylmethoxymethyl)-2-(1,1,2,2-tetrafluoroethylsulfanyl)imidazole Chemical compound C=1C=CC=CC=1COCN1C(SC(F)(F)C(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 TVTOLIQBOMHYGM-UHFFFAOYSA-N 0.000 description 2
- DEEUWJDZFZVYNP-UHFFFAOYSA-N 4,5-diphenyl-1-(phenylmethoxymethyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole Chemical compound C=1C=CC=CC=1COCN1C(S(=O)(=O)C(F)(F)C(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 DEEUWJDZFZVYNP-UHFFFAOYSA-N 0.000 description 2
- ZZTPKLVEMYFHIF-UHFFFAOYSA-N 4,5-diphenyl-1-(phenylmethoxymethyl)imidazole Chemical compound C=1C=CC=CC=1COCN1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ZZTPKLVEMYFHIF-UHFFFAOYSA-N 0.000 description 2
- CPHGOBGXZQKCKI-UHFFFAOYSA-N 4,5-diphenyl-1h-imidazole Chemical compound N1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CPHGOBGXZQKCKI-UHFFFAOYSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
- 208000009386 Experimental Arthritis Diseases 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000002456 anti-arthritic effect Effects 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- WJANVLMIWXWROB-UHFFFAOYSA-N ethyl 4,5-bis(4-fluorophenyl)-2-(1,1,2,2-tetrafluoroethylsulfanyl)imidazole-1-carboxylate Chemical compound CCOC(=O)N1C(SC(F)(F)C(F)F)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 WJANVLMIWXWROB-UHFFFAOYSA-N 0.000 description 2
- NLFHWENMPYXYEL-UHFFFAOYSA-N ethyl 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylsulfanyl)imidazole-1-carboxylate Chemical compound CCOC(=O)N1C(SC(F)(F)C(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 NLFHWENMPYXYEL-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229960001680 ibuprofen Drugs 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- POXAIQSXNOEQGM-UHFFFAOYSA-N propan-2-ylthiourea Chemical compound CC(C)NC(N)=S POXAIQSXNOEQGM-UHFFFAOYSA-N 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- OJOAMQCGGMHOPO-UHFFFAOYSA-N 1-(benzenesulfonyl)-4,5-bis(4-fluorophenyl)-2-(trifluoromethylsulfanyl)imidazole Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC(F)=CC=2)N(S(=O)(=O)C=2C=CC=CC=2)C(SC(F)(F)F)=N1 OJOAMQCGGMHOPO-UHFFFAOYSA-N 0.000 description 1
- MCRDRLRVYIFIRU-UHFFFAOYSA-N 1-(benzenesulfonyl)-4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylsulfanyl)imidazole Chemical compound C=1C=CC=CC=1S(=O)(=O)N1C(SC(F)(F)C(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MCRDRLRVYIFIRU-UHFFFAOYSA-N 0.000 description 1
- FDUMLSBFNVTMCB-UHFFFAOYSA-N 1-(oxolan-2-yl)-4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylsulfanyl)imidazole Chemical compound C1CCOC1N1C(SC(F)(F)C(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 FDUMLSBFNVTMCB-UHFFFAOYSA-N 0.000 description 1
- DETHAVCKPCXRMD-UHFFFAOYSA-N 1-[4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylsulfanyl)imidazol-1-yl]ethanone Chemical compound CC(=O)N1C(SC(F)(F)C(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 DETHAVCKPCXRMD-UHFFFAOYSA-N 0.000 description 1
- FGYADSCZTQOAFK-UHFFFAOYSA-N 1-methylbenzimidazole Chemical compound C1=CC=C2N(C)C=NC2=C1 FGYADSCZTQOAFK-UHFFFAOYSA-N 0.000 description 1
- IOHCXXVLWAKZJN-UHFFFAOYSA-N 2-(1,1,2-trifluoroethylsulfanyl)-1h-imidazole Chemical class FCC(F)(F)SC1=NC=CN1 IOHCXXVLWAKZJN-UHFFFAOYSA-N 0.000 description 1
- ZVAKZVDJIUFFFP-UHFFFAOYSA-N 2-chlorooxolane Chemical compound ClC1CCCO1 ZVAKZVDJIUFFFP-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- CDNHLXOFELOEOL-UHFFFAOYSA-N 3-methyl-1h-benzimidazole-2-thione Chemical compound C1=CC=C2N(C)C(S)=NC2=C1 CDNHLXOFELOEOL-UHFFFAOYSA-N 0.000 description 1
- JPXCIPNJJMSYDI-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-methylsulfanyl-1h-imidazole Chemical class N1C(SC)=NC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 JPXCIPNJJMSYDI-UHFFFAOYSA-N 0.000 description 1
- YSHHCGKYKAFBRC-UHFFFAOYSA-N 4,5-bis(4-fluorophenyl)-1-methyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazole Chemical compound N1=C(S(=O)(=O)C(F)(F)C(F)F)N(C)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 YSHHCGKYKAFBRC-UHFFFAOYSA-N 0.000 description 1
- WQFDOANAJYBPJZ-UHFFFAOYSA-N 4,5-bis(4-fluorophenyl)-1-propan-2-yl-2-(1,1,2,2-tetrafluoroethylsulfanyl)imidazole Chemical compound CC(C)N1C(SC(F)(F)C(F)F)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 WQFDOANAJYBPJZ-UHFFFAOYSA-N 0.000 description 1
- MIZORTJPUUOUSA-UHFFFAOYSA-N 4,5-bis(4-fluorophenyl)-1h-imidazole Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC(F)=CC=2)NC=N1 MIZORTJPUUOUSA-UHFFFAOYSA-N 0.000 description 1
- OOIBHJONYFZSOW-UHFFFAOYSA-N 4,5-bis(4-fluorophenyl)-2-(trifluoromethylsulfanyl)-1h-imidazole Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CC(F)=CC=2)NC(SC(F)(F)F)=N1 OOIBHJONYFZSOW-UHFFFAOYSA-N 0.000 description 1
- XJXSIQHSQFQXPU-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-2-methylsulfanyl-1h-imidazole Chemical class C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC)=N1 XJXSIQHSQFQXPU-UHFFFAOYSA-N 0.000 description 1
- JNWDXTYJQCVTJE-UHFFFAOYSA-N 4,5-diphenyl-1-(phenylmethoxymethyl)-2-(trifluoromethylsulfanyl)imidazole Chemical compound C=1C=CC=CC=1COCN1C(SC(F)(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JNWDXTYJQCVTJE-UHFFFAOYSA-N 0.000 description 1
- HRKFATZEMKPDKK-UHFFFAOYSA-N 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylsulfonyl)-1h-imidazole Chemical compound N1C(S(=O)(=O)C(F)(F)C(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 HRKFATZEMKPDKK-UHFFFAOYSA-N 0.000 description 1
- MCPVJXGDJLZYEG-UHFFFAOYSA-N 5-phenyl-2-(1,1,2,2-tetrafluoroethylsulfanyl)-1H-imidazole Chemical compound C1(=CC=CC=C1)C=1N=C(NC=1)SC(C(F)F)(F)F MCPVJXGDJLZYEG-UHFFFAOYSA-N 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- OMOIOXXXSGBLPX-UHFFFAOYSA-N [4,5-bis(4-fluorophenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)imidazol-1-yl]methyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCN1C(S(=O)(=O)C(F)(F)C(F)F)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 OMOIOXXXSGBLPX-UHFFFAOYSA-N 0.000 description 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 210000004404 adrenal cortex Anatomy 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- ZQDOJKBVJFGNCQ-UHFFFAOYSA-N benzyl 4,5-diphenyl-2-(1,1,2,2-tetrafluoroethylsulfanyl)imidazole-1-carboxylate Chemical compound C=1C=CC=CC=1COC(=O)N1C(SC(F)(F)C(F)F)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ZQDOJKBVJFGNCQ-UHFFFAOYSA-N 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- RDISTZICXURGDY-UHFFFAOYSA-N ethyl 4-(4-fluorophenyl)-5-phenyl-2-(1,1,2,2-tetrafluoroethylsulfanyl)imidazole-1-carboxylate Chemical compound CCOC(=O)N1C(SC(F)(F)C(F)F)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=CC=C1 RDISTZICXURGDY-UHFFFAOYSA-N 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BYTZSXLPLBPFBR-UHFFFAOYSA-N hexane methylcyclohexane Chemical compound CCCCCC.CC1CCCCC1 BYTZSXLPLBPFBR-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 229940117615 mineral oil 5 mg/ml Drugs 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- OFHCXWMZXQBQMH-UHFFFAOYSA-N trifluoro(trifluoromethylsulfanyl)methane Chemical compound FC(F)(F)SC(F)(F)F OFHCXWMZXQBQMH-UHFFFAOYSA-N 0.000 description 1
- CGMFFOXAQVRUAZ-UHFFFAOYSA-N trifluoro-(trifluoromethyldisulfanyl)methane Chemical compound FC(F)(F)SSC(F)(F)F CGMFFOXAQVRUAZ-UHFFFAOYSA-N 0.000 description 1
- RQYLOOVORNJDQX-UHFFFAOYSA-N trifluoromethyl thiohypochlorite Chemical compound FC(F)(F)SCl RQYLOOVORNJDQX-UHFFFAOYSA-N 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
- C07D233/84—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]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76721977A | 1977-02-09 | 1977-02-09 | |
| US76721977 | 1977-02-09 | ||
| US05/865,831 US4182769A (en) | 1977-02-09 | 1978-01-05 | Anti-inflammatory 1-substituted-4,5-diaryl-2-(substituted-thio) imidazoles and their corresponding sulfoxides and sulfones |
| US86583178 | 1978-01-05 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI780429A7 FI780429A7 (fi) | 1978-08-10 |
| FI68619B FI68619B (fi) | 1985-06-28 |
| FI68619C true FI68619C (fi) | 1985-10-10 |
Family
ID=27117878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI780429A FI68619C (fi) | 1977-02-09 | 1978-02-09 | Foerfarande foer framstaellning av antiinflammatoriska 1-substituerade 4,5-diaryl-2-(substituerad tio)-imidazolderivat ochderas motsvarande sulfoner |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4182769A (de) |
| JP (1) | JPS53130665A (de) |
| AR (1) | AR221590A1 (de) |
| AT (1) | AT363076B (de) |
| AU (1) | AU524360B2 (de) |
| CA (1) | CA1107286A (de) |
| CH (1) | CH643834A5 (de) |
| DE (1) | DE2805166A1 (de) |
| DK (1) | DK16878A (de) |
| ES (1) | ES466793A1 (de) |
| FI (1) | FI68619C (de) |
| FR (1) | FR2380264A1 (de) |
| GB (1) | GB1587373A (de) |
| GR (1) | GR64157B (de) |
| HU (1) | HU181868B (de) |
| IE (1) | IE46454B1 (de) |
| IL (1) | IL53996A (de) |
| IT (1) | IT1092439B (de) |
| LU (1) | LU79028A1 (de) |
| MX (1) | MX5934E (de) |
| NL (1) | NL7801454A (de) |
| NO (1) | NO149813C (de) |
| NZ (1) | NZ186411A (de) |
| PT (1) | PT67625B (de) |
| SE (1) | SE7801466L (de) |
| SU (1) | SU867301A3 (de) |
| YU (1) | YU28978A (de) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2823197A1 (de) * | 1978-05-24 | 1979-11-29 | Schering Ag | Neue imidazolderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| CY1344A (en) * | 1978-08-10 | 1987-01-16 | Ciba Geigy Ag | Substituted anthranilic acid amides,process for their preparation,and pharmaceutical compositions containing them |
| US4308277A (en) * | 1978-08-10 | 1981-12-29 | Ciba-Geigy Corporation | 2,4,5-Trisubstituted imidazolines and pharmaceutical compositions containing same |
| US4199592A (en) * | 1978-08-29 | 1980-04-22 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-2-nitroimidazoles |
| DK337779A (da) * | 1978-10-02 | 1980-04-03 | Du Pont | Fremgangsmaade til fremstilling af antiinflammatoriske 2-substituerede 1h-phenantro (9,10)-imidazoler |
| DE2856909A1 (de) * | 1978-12-28 | 1980-07-17 | Schering Ag | Neue imidazolderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| IT1110282B (it) * | 1979-02-19 | 1985-12-23 | Acraf | Tio-indazoli basici |
| 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 |
| US4438117A (en) | 1980-09-03 | 1984-03-20 | E. I. Du Pont De Nemours And Company | 2-Substituted thio-4,5-diarylpyrimidines |
| US4355041A (en) * | 1982-01-04 | 1982-10-19 | E. I. Du Pont De Nemours And Company | 4,5-Bis-(4-fluorophenyl)-1-(4-nitrobenzyl)-2-[((1,1,2,2-tetrafluoroethyl)sulfonyl]-1H-imidazole, composition and use |
| US4503065A (en) * | 1982-08-03 | 1985-03-05 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl 1-2-halo imidazoles |
| ZA826501B (en) * | 1982-09-06 | 1984-04-25 | Du Pont | Anti-hypertensive imidazole derivative |
| DE3504678A1 (de) * | 1985-02-12 | 1986-08-14 | A. Nattermann & Cie GmbH, 5000 Köln | Neue imidazolyl-oxyalkansaeuren und -thioalkansaeuren, ihre derivate und verfahren zu ihrer herstellung |
| DE3508665A1 (de) * | 1985-03-12 | 1986-09-18 | Hoechst Ag, 6230 Frankfurt | Heterocyclische sulfide und ihre anwendung als immunmodulatoren |
| US4686231A (en) * | 1985-12-12 | 1987-08-11 | Smithkline Beckman Corporation | Inhibition of 5-lipoxygenase products |
| US4780470A (en) * | 1986-08-19 | 1988-10-25 | Smithkline Beckman Corporation | Inhibition of interleukin-1 by monocytes and/or macrophages |
| US5300519A (en) * | 1988-07-06 | 1994-04-05 | The University Of Sheffield | Immunosuppressive agents |
| US5098707A (en) * | 1989-07-31 | 1992-03-24 | Merck & Co., Inc. | Imidazole compounds and their use as transglutaminase inhibitors |
| US5030644A (en) * | 1989-07-31 | 1991-07-09 | Merck & Co., Inc. | Imidazole compounds and their use as transglutaminase inhibitors |
| JPH03145473A (ja) * | 1989-10-27 | 1991-06-20 | Hisamitsu Pharmaceut Co Inc | 新規なイミダゾール酢酸誘導体 |
| GB9005966D0 (en) * | 1990-03-16 | 1990-05-09 | May & Baker Ltd | New compositions of matter |
| DE4010797A1 (de) * | 1990-04-04 | 1991-10-10 | Hoechst Ag | Substituierte azole, verfahren zu deren herstellung, diese enthaltende mittel und deren verwendung |
| WO1999003837A1 (en) * | 1997-06-30 | 1999-01-28 | Ortho-Mcneil Pharmaceutical, Inc. | 2-substituted imidazoles useful in the treatment of inflammatory diseases |
| FR2823747B1 (fr) * | 2001-04-24 | 2003-05-23 | Oreal | Nouveaux composes de la famille des 3-alkyl-(4,5 diphenyl- imidazol-1-yl) et leur utilisation comme anti-inflammatoires |
| US10023567B2 (en) | 2014-07-18 | 2018-07-17 | Ohio University | Imidazole and thiazole compositions for modifying biological signaling |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL26729A (en) * | 1965-10-21 | 1970-10-30 | Geigy Ag J R | 2-mercaptoimidazole derivatives and process for their preparation |
| US3707475A (en) * | 1970-11-16 | 1972-12-26 | Pfizer | Antiinflammatory imidazoles |
| US3929807A (en) * | 1971-05-10 | 1975-12-30 | Ciba Geigy Corp | 2-Substituted-4(5)-(aryl)-5(4)-(2,3 or -4-pyridyl)-imidazoles |
| JPS5343958B2 (de) * | 1972-07-29 | 1978-11-24 |
-
1978
- 1978-01-05 US US05/865,831 patent/US4182769A/en not_active Expired - Lifetime
- 1978-01-13 DK DK16878A patent/DK16878A/da not_active Application Discontinuation
- 1978-02-06 PT PT67625A patent/PT67625B/pt unknown
- 1978-02-07 CA CA296,605A patent/CA1107286A/en not_active Expired
- 1978-02-07 IT IT20079/78A patent/IT1092439B/it active
- 1978-02-08 NZ NZ186411A patent/NZ186411A/xx unknown
- 1978-02-08 LU LU79028A patent/LU79028A1/xx unknown
- 1978-02-08 SU SU782574555A patent/SU867301A3/ru active
- 1978-02-08 FR FR7803517A patent/FR2380264A1/fr not_active Withdrawn
- 1978-02-08 AT AT0087078A patent/AT363076B/de not_active IP Right Cessation
- 1978-02-08 YU YU00289/78A patent/YU28978A/xx unknown
- 1978-02-08 AU AU33097/78A patent/AU524360B2/en not_active Expired
- 1978-02-08 MX MX786830U patent/MX5934E/es unknown
- 1978-02-08 NO NO780432A patent/NO149813C/no unknown
- 1978-02-08 DE DE19782805166 patent/DE2805166A1/de not_active Withdrawn
- 1978-02-08 IE IE280/78A patent/IE46454B1/en unknown
- 1978-02-08 IL IL53996A patent/IL53996A/xx unknown
- 1978-02-08 ES ES466793A patent/ES466793A1/es not_active Expired
- 1978-02-08 GB GB5097/78A patent/GB1587373A/en not_active Expired
- 1978-02-08 NL NL7801454A patent/NL7801454A/xx not_active Application Discontinuation
- 1978-02-08 SE SE7801466A patent/SE7801466L/xx unknown
- 1978-02-09 FI FI780429A patent/FI68619C/fi not_active IP Right Cessation
- 1978-02-09 GR GR55397A patent/GR64157B/el unknown
- 1978-02-09 CH CH147578A patent/CH643834A5/de not_active IP Right Cessation
- 1978-02-09 HU HU78DU280A patent/HU181868B/hu unknown
- 1978-02-09 JP JP1304778A patent/JPS53130665A/ja active Pending
- 1978-02-09 AR AR271047A patent/AR221590A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| SU867301A3 (ru) | 1981-09-23 |
| IL53996A (en) | 1982-04-30 |
| AT363076B (de) | 1981-07-10 |
| PT67625B (en) | 1979-07-17 |
| MX5934E (es) | 1984-08-30 |
| NO149813B (no) | 1984-03-19 |
| ES466793A1 (es) | 1979-08-01 |
| NO780432L (no) | 1978-08-10 |
| JPS53130665A (en) | 1978-11-14 |
| IT1092439B (it) | 1985-07-12 |
| US4182769A (en) | 1980-01-08 |
| IE46454B1 (en) | 1983-06-15 |
| AR221590A1 (es) | 1981-02-27 |
| IT7820079A0 (it) | 1978-02-07 |
| FI780429A7 (fi) | 1978-08-10 |
| ATA87078A (de) | 1980-12-15 |
| AU3309778A (en) | 1979-08-16 |
| NZ186411A (en) | 1981-03-16 |
| NL7801454A (nl) | 1978-08-11 |
| LU79028A1 (fr) | 1979-05-25 |
| IE780280L (en) | 1978-08-09 |
| GR64157B (en) | 1980-02-05 |
| AU524360B2 (en) | 1982-09-16 |
| SE7801466L (sv) | 1978-08-10 |
| CH643834A5 (de) | 1984-06-29 |
| NO149813C (no) | 1984-06-27 |
| IL53996A0 (en) | 1978-04-30 |
| YU28978A (en) | 1983-01-21 |
| GB1587373A (en) | 1981-04-01 |
| DK16878A (da) | 1978-08-10 |
| DE2805166A1 (de) | 1978-08-10 |
| FR2380264A1 (fr) | 1978-09-08 |
| FI68619B (fi) | 1985-06-28 |
| PT67625A (en) | 1978-03-01 |
| HU181868B (en) | 1983-11-28 |
| CA1107286A (en) | 1981-08-18 |
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| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: E.I. DU PONT DE NEMOURS AND COMPANY |