NO812265L - Fremgangsmaate ved fremstilling av nye imidazolderivater - Google Patents
Fremgangsmaate ved fremstilling av nye imidazolderivater Download PDFInfo
- Publication number
- NO812265L NO812265L NO812265A NO812265A NO812265L NO 812265 L NO812265 L NO 812265L NO 812265 A NO812265 A NO 812265A NO 812265 A NO812265 A NO 812265A NO 812265 L NO812265 L NO 812265L
- Authority
- NO
- Norway
- Prior art keywords
- imidazole
- bis
- methoxyphenyl
- residue
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 12
- 150000002460 imidazoles Chemical class 0.000 claims abstract description 21
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 5
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims abstract 3
- 150000007513 acids Chemical class 0.000 claims abstract 3
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 125000002541 furyl group Chemical group 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- -1 hydroxy- Chemical class 0.000 claims description 49
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 13
- USGVCCDFZGKEAM-UHFFFAOYSA-N 2-(2-fluorophenyl)sulfanyl-4,5-bis(4-methoxyphenyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC=2C(=CC=CC=2)F)=N1 USGVCCDFZGKEAM-UHFFFAOYSA-N 0.000 claims description 4
- PMSRSEWSFQOTNC-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-2-thiophen-2-ylsulfanyl-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC=2SC=CC=2)=N1 PMSRSEWSFQOTNC-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- UMBASFFXUMUKHM-UHFFFAOYSA-N 1-benzyl-4,5-bis(4-methoxyphenyl)-2-(4-methylphenyl)sulfonylimidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N(CC=2C=CC=CC=2)C(S(=O)(=O)C=2C=CC(C)=CC=2)=N1 UMBASFFXUMUKHM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- CAMCMFXJVDUERU-UHFFFAOYSA-N 2-(2-fluorophenyl)sulfonyl-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)C=2C(=CC=CC=2)F)=N1 CAMCMFXJVDUERU-UHFFFAOYSA-N 0.000 claims description 2
- BOHQVTKZPPPCEK-UHFFFAOYSA-N 2-(benzenesulfinyl)-4,5-bis(4-methoxyphenyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S(=O)C=2C=CC=CC=2)=N1 BOHQVTKZPPPCEK-UHFFFAOYSA-N 0.000 claims description 2
- PCRSXQSMLBBZMV-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfinyl]-1,3-thiazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S(=O)C=2SC=CN=2)=N1 PCRSXQSMLBBZMV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- RVDHDNKRMPDTSL-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-2-(2-methoxyphenyl)sulfonyl-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S(=O)(=O)C=2C(=CC=CC=2)OC)=N1 RVDHDNKRMPDTSL-UHFFFAOYSA-N 0.000 claims description 2
- NJNXYZFFVIJBRY-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-2-(4-methoxyphenyl)sulfonyl-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(S(=O)(=O)C=2C=CC(OC)=CC=2)=N1 NJNXYZFFVIJBRY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000003277 amino group Chemical group 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
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 125000004423 acyloxy group Chemical group 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 334
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 282
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 276
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 165
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 162
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 157
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 128
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 103
- 229910052938 sodium sulfate Inorganic materials 0.000 description 100
- 235000011152 sodium sulphate Nutrition 0.000 description 100
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 96
- 239000000203 mixture Substances 0.000 description 96
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 84
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 84
- 235000017557 sodium bicarbonate Nutrition 0.000 description 64
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 64
- 238000002844 melting Methods 0.000 description 63
- 230000008018 melting Effects 0.000 description 63
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 54
- 239000000741 silica gel Substances 0.000 description 54
- 229910002027 silica gel Inorganic materials 0.000 description 54
- 235000019439 ethyl acetate Nutrition 0.000 description 53
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- 239000006260 foam Substances 0.000 description 43
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
- 238000003756 stirring Methods 0.000 description 40
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 32
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 28
- 238000001953 recrystallisation Methods 0.000 description 26
- 239000000047 product Substances 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 229910052786 argon Inorganic materials 0.000 description 16
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 15
- 239000012312 sodium hydride Substances 0.000 description 15
- 229910000104 sodium hydride Inorganic materials 0.000 description 15
- 239000005457 ice water Substances 0.000 description 14
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 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 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 239000012300 argon atmosphere Substances 0.000 description 7
- 239000012954 diazonium Substances 0.000 description 7
- 150000001989 diazonium salts Chemical class 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 7
- 235000010288 sodium nitrite Nutrition 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- JHGPPHBZIZQSRU-UHFFFAOYSA-N 1-benzyl-4,5-bis(4-methoxyphenyl)imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N(CC=2C=CC=CC=2)C=N1 JHGPPHBZIZQSRU-UHFFFAOYSA-N 0.000 description 4
- TZGFQIXRVUHDLE-UHFFFAOYSA-N 1-chloro-2-nitro-4-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1Cl TZGFQIXRVUHDLE-UHFFFAOYSA-N 0.000 description 4
- PJINSVZDDIRODC-UHFFFAOYSA-N 2-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfanyl]pyridine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC=2N=CC=CC=2)=N1 PJINSVZDDIRODC-UHFFFAOYSA-N 0.000 description 4
- YIJUBZDDOUUKDA-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC=N1 YIJUBZDDOUUKDA-UHFFFAOYSA-N 0.000 description 4
- UEGKKYRWJFRTOO-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-2-[4-(trifluoromethyl)phenyl]sulfanyl-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC=2C=CC(=CC=2)C(F)(F)F)=N1 UEGKKYRWJFRTOO-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- VKEJDZGOQIQFKW-UHFFFAOYSA-N 1-(methoxymethyl)-4,5-bis(4-methoxyphenyl)imidazole Chemical compound COCN1C=NC(C=2C=CC(OC)=CC=2)=C1C1=CC=C(OC)C=C1 VKEJDZGOQIQFKW-UHFFFAOYSA-N 0.000 description 3
- AHPTWLVCTNZQCX-UHFFFAOYSA-N 2-(4-fluorophenyl)sulfanyl-4,5-bis(4-methoxyphenyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC=2C=CC(F)=CC=2)=N1 AHPTWLVCTNZQCX-UHFFFAOYSA-N 0.000 description 3
- DYDPDDOTOAULRA-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-2-thiophen-2-ylsulfanyl-1h-imidazole Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)NC(SC=2SC=CC=2)=N1 DYDPDDOTOAULRA-UHFFFAOYSA-N 0.000 description 3
- BKCYPFPBTODILR-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-1-(oxan-2-yl)imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N(C2OCCCC2)C=N1 BKCYPFPBTODILR-UHFFFAOYSA-N 0.000 description 3
- IGENVQBTQQROKE-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-1-methylimidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N(C)C=N1 IGENVQBTQQROKE-UHFFFAOYSA-N 0.000 description 3
- FKWMJKPLHWEZQD-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-2-(4-methylphenyl)sulfanyl-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC=2C=CC(C)=CC=2)=N1 FKWMJKPLHWEZQD-UHFFFAOYSA-N 0.000 description 3
- KYBMJTMKCYEMOM-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-2-phenylsulfanyl-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC=2C=CC=CC=2)=N1 KYBMJTMKCYEMOM-UHFFFAOYSA-N 0.000 description 3
- BEGODYVXAHMFSS-UHFFFAOYSA-N 4-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfanyl]pyridine Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC=2C=CN=CC=2)=N1 BEGODYVXAHMFSS-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 210000000548 hind-foot Anatomy 0.000 description 3
- PGZICZDLRRJWRD-UHFFFAOYSA-N n-[2-[[4,5-bis(4-methoxyphenyl)-1h-imidazol-2-yl]sulfanyl]phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC=2C(=CC=CC=2)NC(C)=O)=N1 PGZICZDLRRJWRD-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- ILZYHMZOLCNNCP-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) thiohypochlorite Chemical compound FC1=C(F)C(F)=C(SCl)C(F)=C1F ILZYHMZOLCNNCP-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- VLGITXIOIKGARU-UHFFFAOYSA-N 1-benzyl-4,5-bis(4-methoxyphenyl)-2-(4-methylphenyl)sulfanylimidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N(CC=2C=CC=CC=2)C(SC=2C=CC(C)=CC=2)=N1 VLGITXIOIKGARU-UHFFFAOYSA-N 0.000 description 2
- ZCVQJAWOHPRBJM-UHFFFAOYSA-N 2-(2,4-difluorophenyl)sulfanyl-4,5-bis(4-methoxyphenyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC=2C(=CC(F)=CC=2)F)=N1 ZCVQJAWOHPRBJM-UHFFFAOYSA-N 0.000 description 2
- JBGIVIMFQSRQLX-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)sulfanyl-4,5-bis(4-methoxyphenyl)-1-(oxan-2-yl)imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N(C2OCCCC2)C(SC=2C=C(Cl)C(Cl)=CC=2)=N1 JBGIVIMFQSRQLX-UHFFFAOYSA-N 0.000 description 2
- SXTMJXICQRLYAA-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)sulfanyl-4,5-bis(4-methoxyphenyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC=2C=C(Cl)C(Cl)=CC=2)=N1 SXTMJXICQRLYAA-UHFFFAOYSA-N 0.000 description 2
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- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803025484 DE3025484A1 (de) | 1980-07-03 | 1980-07-03 | Neue imidazol-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO812265L true NO812265L (no) | 1982-01-04 |
Family
ID=6106465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO812265A NO812265L (no) | 1980-07-03 | 1981-07-02 | Fremgangsmaate ved fremstilling av nye imidazolderivater |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US4402960A (xx) |
| EP (1) | EP0043788B1 (xx) |
| JP (1) | JPS5775973A (xx) |
| AT (1) | ATE16281T1 (xx) |
| AU (1) | AU7249481A (xx) |
| CA (1) | CA1169063A (xx) |
| DD (1) | DD206152A5 (xx) |
| DE (2) | DE3025484A1 (xx) |
| DK (1) | DK293381A (xx) |
| ES (1) | ES8301220A1 (xx) |
| FI (1) | FI812106L (xx) |
| GR (1) | GR78231B (xx) |
| IE (1) | IE52822B1 (xx) |
| IL (1) | IL63190A0 (xx) |
| NO (1) | NO812265L (xx) |
| PT (1) | PT73280B (xx) |
| ZA (1) | ZA814540B (xx) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE3141063A1 (de) * | 1981-10-13 | 1983-04-28 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue imidazol-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| US5300519A (en) * | 1988-07-06 | 1994-04-05 | The University Of Sheffield | Immunosuppressive agents |
| JP2614756B2 (ja) * | 1988-08-10 | 1997-05-28 | 日本ケミファ株式会社 | イミダゾール誘導体およびその製造法ならびにこれを含有する抗潰瘍剤 |
| CA2003283A1 (en) * | 1988-12-05 | 1990-06-05 | C. Anne Higley | Imidazoles for the treatment of atherosclerosis |
| GB8907656D0 (en) * | 1989-04-05 | 1989-05-17 | May & Baker Ltd | New compositions of matter |
| US5011851A (en) * | 1990-02-13 | 1991-04-30 | Bristol-Myers Squibb Co. | Imidazole carboxylic acids and esters and inhibition of blood platelet aggregation therewith |
| GB9005966D0 (en) * | 1990-03-16 | 1990-05-09 | May & Baker Ltd | New compositions of matter |
| US5441515A (en) * | 1993-04-23 | 1995-08-15 | Advanced Cardiovascular Systems, Inc. | Ratcheting stent |
| CA2295021A1 (en) * | 1997-06-30 | 1999-01-28 | Ortho-Mcneil Pharmaceutical, Inc. | 2-substituted imidazoles useful in the treatment of inflammatory diseases |
| DE19842833B4 (de) | 1998-09-18 | 2005-04-14 | Merckle Gmbh | 2-Arylalkylthio-imidazole, 2-Arylalkenylthio-imidazole und 2-Arylalkinylthio-imidazole als Entzündungs-Hemmstoffe und Hemmstoffe der Cytokin-Freisetzung |
| DE10107683A1 (de) * | 2001-02-19 | 2002-08-29 | Merckle Gmbh Chem Pharm Fabrik | 2-Thio-substituierte Imidazolderivate 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 (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| US4215217A (en) * | 1975-10-29 | 1980-07-29 | Sk&F Lab Co. | Process for preparing 4-substituted imidazole compounds |
| 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 |
| 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 |
| EP0005219B1 (en) * | 1978-04-24 | 1981-07-22 | A/S Dumex (Dumex Ltd.) | Arylimidazoles, their synthesis and pharmaceutical or veterinary preparations containing them |
| DE2823197A1 (de) * | 1978-05-24 | 1979-11-29 | Schering Ag | Neue imidazolderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| 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 |
| US4330552A (en) * | 1980-11-06 | 1982-05-18 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-2-arylthioimidazoles |
-
1980
- 1980-07-03 DE DE19803025484 patent/DE3025484A1/de not_active Withdrawn
-
1981
- 1981-06-26 IL IL63190A patent/IL63190A0/xx unknown
- 1981-06-29 PT PT73280A patent/PT73280B/pt unknown
- 1981-06-30 DE DE8181730061T patent/DE3172757D1/de not_active Expired
- 1981-06-30 EP EP81730061A patent/EP0043788B1/de not_active Expired
- 1981-06-30 AT AT81730061T patent/ATE16281T1/de active
- 1981-07-01 GR GR65403A patent/GR78231B/el unknown
- 1981-07-02 DK DK293381A patent/DK293381A/da not_active Application Discontinuation
- 1981-07-02 AU AU72494/81A patent/AU7249481A/en not_active Abandoned
- 1981-07-02 NO NO812265A patent/NO812265L/no unknown
- 1981-07-02 IE IE1484/81A patent/IE52822B1/en unknown
- 1981-07-02 DD DD81231398A patent/DD206152A5/de unknown
- 1981-07-02 CA CA000380977A patent/CA1169063A/en not_active Expired
- 1981-07-02 US US06/280,163 patent/US4402960A/en not_active Expired - Fee Related
- 1981-07-02 JP JP56102324A patent/JPS5775973A/ja active Granted
- 1981-07-03 ES ES503678A patent/ES8301220A1/es not_active Expired
- 1981-07-03 FI FI812106A patent/FI812106L/fi not_active Application Discontinuation
- 1981-07-03 ZA ZA814540A patent/ZA814540B/xx unknown
-
1983
- 1983-07-22 US US06/516,395 patent/US4528298A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5775973A (en) | 1982-05-12 |
| PT73280B (de) | 1982-07-22 |
| DD206152A5 (de) | 1984-01-18 |
| ES503678A0 (es) | 1982-12-01 |
| IL63190A0 (en) | 1981-09-13 |
| DE3025484A1 (de) | 1982-02-04 |
| IE52822B1 (en) | 1988-03-16 |
| GR78231B (xx) | 1984-09-26 |
| DK293381A (da) | 1982-01-04 |
| US4528298A (en) | 1985-07-09 |
| CA1169063A (en) | 1984-06-12 |
| FI812106L (fi) | 1982-01-04 |
| IE811484L (en) | 1982-01-03 |
| ZA814540B (en) | 1982-07-28 |
| EP0043788A1 (de) | 1982-01-13 |
| ATE16281T1 (de) | 1985-11-15 |
| JPH0254343B2 (xx) | 1990-11-21 |
| ES8301220A1 (es) | 1982-12-01 |
| PT73280A (de) | 1981-07-01 |
| EP0043788B1 (de) | 1985-10-30 |
| DE3172757D1 (en) | 1985-12-05 |
| AU7249481A (en) | 1982-01-07 |
| US4402960A (en) | 1983-09-06 |
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