FI79302C - Foerfarande foer framstaellning av farmakologiskt aktiva trifenylimidazolyloxialkansyror och derivat daerav. - Google Patents
Foerfarande foer framstaellning av farmakologiskt aktiva trifenylimidazolyloxialkansyror och derivat daerav. Download PDFInfo
- Publication number
- FI79302C FI79302C FI832730A FI832730A FI79302C FI 79302 C FI79302 C FI 79302C FI 832730 A FI832730 A FI 832730A FI 832730 A FI832730 A FI 832730A FI 79302 C FI79302 C FI 79302C
- Authority
- FI
- Finland
- Prior art keywords
- yloxy
- acid
- formula
- alkali metal
- preparation
- Prior art date
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- 239000002253 acid Substances 0.000 title claims abstract description 31
- 150000007513 acids Chemical class 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims description 40
- RNIPJYFZGXJSDD-UHFFFAOYSA-N 2,4,5-triphenyl-1h-imidazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 RNIPJYFZGXJSDD-UHFFFAOYSA-N 0.000 title 1
- -1 1,4,5-triphenylimidazol-2-yloxy Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229910052783 alkali metal Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 150000001340 alkali metals Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- AICIYIDUYNFPRY-UHFFFAOYSA-N 1,3-dihydro-2H-imidazol-2-one Chemical compound O=C1NC=CN1 AICIYIDUYNFPRY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000000956 alloy Substances 0.000 claims 1
- 229910045601 alloy Inorganic materials 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 230000003143 atherosclerotic effect Effects 0.000 abstract description 2
- 201000010099 disease Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 230000002757 inflammatory effect Effects 0.000 abstract description 2
- 230000009424 thromboembolic effect Effects 0.000 abstract description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- 239000000203 mixture Substances 0.000 description 20
- 239000007858 starting material Substances 0.000 description 20
- 159000000000 sodium salts Chemical class 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 17
- 229960002446 octanoic acid Drugs 0.000 description 17
- 238000004440 column chromatography Methods 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- 239000000725 suspension Substances 0.000 description 14
- 239000002480 mineral oil Substances 0.000 description 13
- 235000010446 mineral oil Nutrition 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 11
- 229910000105 potassium hydride Inorganic materials 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- IZIJRYNUYQXBPG-UHFFFAOYSA-N methyl 8-bromooctanoate Chemical compound COC(=O)CCCCCCCBr IZIJRYNUYQXBPG-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 6
- RVTZDVRBBLITAE-UHFFFAOYSA-N 3,4,5-triphenyl-1h-imidazol-2-one Chemical compound C=1C=CC=CC=1N1C(O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 RVTZDVRBBLITAE-UHFFFAOYSA-N 0.000 description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 230000002785 anti-thrombosis Effects 0.000 description 5
- 239000003146 anticoagulant agent Substances 0.000 description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- AURRKGGYZZOUHD-UHFFFAOYSA-N 11-(1,4,5-triphenylimidazol-2-yl)oxyundecanoic acid Chemical compound C=1C=CC=CC=1N1C(OCCCCCCCCCCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 AURRKGGYZZOUHD-UHFFFAOYSA-N 0.000 description 4
- ANNAWUMOXMGCJH-UHFFFAOYSA-N 5-(1,4,5-triphenylimidazol-2-yl)oxypentanoic acid Chemical compound C=1C=CC=CC=1N1C(OCCCCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ANNAWUMOXMGCJH-UHFFFAOYSA-N 0.000 description 4
- JJNUVQIGQRFZAC-UHFFFAOYSA-N 8-(1,4,5-triphenylimidazol-2-yl)oxyoctanoic acid Chemical compound C=1C=CC=CC=1N1C(OCCCCCCCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JJNUVQIGQRFZAC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- KYFDWGXIJFYPRS-UHFFFAOYSA-N 4-(1,4,5-triphenylimidazol-2-yl)oxybutanoic acid Chemical compound C=1C=CC=CC=1N1C(OCCCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 KYFDWGXIJFYPRS-UHFFFAOYSA-N 0.000 description 3
- TUVHAQBFXQPBJV-UHFFFAOYSA-N 6-(1,4,5-triphenylimidazol-2-yl)oxyhexanoic acid Chemical compound C=1C=CC=CC=1N1C(OCCCCCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 TUVHAQBFXQPBJV-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- UIPUKNMMAHKQSR-UHFFFAOYSA-N methyl 8-(1,4,5-triphenylimidazol-2-yl)oxyoctanoate Chemical compound C=1C=CC=CC=1N1C(OCCCCCCCC(=O)OC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 UIPUKNMMAHKQSR-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- QNEGRLRRTFXNNT-UHFFFAOYSA-N 10-(1,4,5-triphenylimidazol-2-yl)oxydecanoic acid Chemical compound C=1C=CC=CC=1N1C(OCCCCCCCCCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 QNEGRLRRTFXNNT-UHFFFAOYSA-N 0.000 description 2
- WJCDRCCRRWVSCN-UHFFFAOYSA-N 2-(1,4,5-triphenylimidazol-2-yl)oxyacetic acid Chemical compound C=1C=CC=CC=1N1C(OCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 WJCDRCCRRWVSCN-UHFFFAOYSA-N 0.000 description 2
- IPLKGJHGWCVSOG-UHFFFAOYSA-N 4-chlorobutanoic acid Chemical compound OC(=O)CCCCl IPLKGJHGWCVSOG-UHFFFAOYSA-N 0.000 description 2
- OBSXDBAFNHKZPX-UHFFFAOYSA-N 8-[1-(4-methoxyphenyl)-4,5-diphenylimidazol-2-yl]oxyoctanoic acid Chemical compound C1=CC(OC)=CC=C1N1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1OCCCCCCCC(O)=O OBSXDBAFNHKZPX-UHFFFAOYSA-N 0.000 description 2
- CGZRSRPJNXHYIH-UHFFFAOYSA-N 8-[4,5-bis(4-methoxyphenyl)-1-phenylimidazol-2-yl]oxyoctanoic acid Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N(C=2C=CC=CC=2)C(OCCCCCCCC(O)=O)=N1 CGZRSRPJNXHYIH-UHFFFAOYSA-N 0.000 description 2
- MXRVFFABSUMFPM-UHFFFAOYSA-N 9-(1,4,5-triphenylimidazol-2-yl)oxynonanoic acid Chemical compound C=1C=CC=CC=1N1C(OCCCCCCCCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MXRVFFABSUMFPM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000000879 anti-atherosclerotic effect Effects 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZZPLHDDZCSZACK-UHFFFAOYSA-N ethyl 6-(1,4,5-triphenylimidazol-2-yl)oxyhexanoate Chemical compound C=1C=CC=CC=1N1C(OCCCCCC(=O)OCC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ZZPLHDDZCSZACK-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 150000003254 radicals Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- PGVRSPIEZYGOAD-UHFFFAOYSA-N 10-bromodecanoic acid Chemical compound OC(=O)CCCCCCCCCBr PGVRSPIEZYGOAD-UHFFFAOYSA-N 0.000 description 1
- FEXSVCTUDASSOQ-UHFFFAOYSA-N 10-chlorodecanoic acid Chemical compound OC(=O)CCCCCCCCCCl FEXSVCTUDASSOQ-UHFFFAOYSA-N 0.000 description 1
- SIWQADQLOLPSIF-UHFFFAOYSA-N 10-iododecanoic acid Chemical compound OC(=O)CCCCCCCCCI SIWQADQLOLPSIF-UHFFFAOYSA-N 0.000 description 1
- IUDGNRWYNOEIKF-UHFFFAOYSA-N 11-bromo-undecanoic acid Chemical compound OC(=O)CCCCCCCCCCBr IUDGNRWYNOEIKF-UHFFFAOYSA-N 0.000 description 1
- GVZXFVFTBUYBJD-UHFFFAOYSA-N 11-chloroundecanoic acid Chemical compound OC(=O)CCCCCCCCCCCl GVZXFVFTBUYBJD-UHFFFAOYSA-N 0.000 description 1
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- MKXBETPREJCAPH-UHFFFAOYSA-N 3-(1,4,5-triphenylimidazol-2-yl)oxypropanoic acid Chemical compound C=1C=CC=CC=1N1C(OCCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MKXBETPREJCAPH-UHFFFAOYSA-N 0.000 description 1
- KMRNTNDWADEIIX-UHFFFAOYSA-N 3-Iodopropanoic acid Chemical compound OC(=O)CCI KMRNTNDWADEIIX-UHFFFAOYSA-N 0.000 description 1
- DHXNZYCXMFBMHE-UHFFFAOYSA-N 3-bromopropanoic acid Chemical compound OC(=O)CCBr DHXNZYCXMFBMHE-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- BWLPBGHFKALLAI-UHFFFAOYSA-N 4,5-bis(4-chlorophenyl)-3-phenyl-1h-imidazol-2-one Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)N(C=2C=CC=CC=2)C(=O)N1 BWLPBGHFKALLAI-UHFFFAOYSA-N 0.000 description 1
- MWMLOSZQVXIKRU-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-3-phenyl-1h-imidazol-2-one Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)N(C=2C=CC=CC=2)C(=O)N1 MWMLOSZQVXIKRU-UHFFFAOYSA-N 0.000 description 1
- XILQGXZARXHSEI-UHFFFAOYSA-N 4-bromopentanoic acid Chemical compound CC(Br)CCC(O)=O XILQGXZARXHSEI-UHFFFAOYSA-N 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- RBFGSILNBZJPFI-UHFFFAOYSA-N 5-iodopentanoic acid Chemical compound OC(=O)CCCCI RBFGSILNBZJPFI-UHFFFAOYSA-N 0.000 description 1
- NVRVNSHHLPQGCU-UHFFFAOYSA-N 6-bromohexanoic acid Chemical compound OC(=O)CCCCCBr NVRVNSHHLPQGCU-UHFFFAOYSA-N 0.000 description 1
- XWWKSLXUVZVGSP-UHFFFAOYSA-N 6-chlorohexanoic acid Chemical compound OC(=O)CCCCCCl XWWKSLXUVZVGSP-UHFFFAOYSA-N 0.000 description 1
- STHOLCAXALUYCX-UHFFFAOYSA-N 6-iodohexanoic acid Chemical compound OC(=O)CCCCCI STHOLCAXALUYCX-UHFFFAOYSA-N 0.000 description 1
- UYTMGZMVSJPEPM-UHFFFAOYSA-N 8-[1,4,5-tris(4-chlorophenyl)imidazol-2-yl]oxyoctanoic acid Chemical compound C=1C=C(Cl)C=CC=1N1C(OCCCCCCCC(=O)O)=NC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 UYTMGZMVSJPEPM-UHFFFAOYSA-N 0.000 description 1
- RBDSMGXISWEQEC-UHFFFAOYSA-N 8-[1-(3,4-dimethoxyphenyl)-4,5-diphenylimidazol-2-yl]oxyoctanoic acid Chemical compound C1=C(OC)C(OC)=CC=C1N1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1OCCCCCCCC(O)=O RBDSMGXISWEQEC-UHFFFAOYSA-N 0.000 description 1
- XZVXJCUCOCOYON-UHFFFAOYSA-N 8-[1-(4-methylphenyl)-4,5-diphenylimidazol-2-yl]oxyoctanoic acid Chemical compound C1=CC(C)=CC=C1N1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N=C1OCCCCCCCC(O)=O XZVXJCUCOCOYON-UHFFFAOYSA-N 0.000 description 1
- YSWRBWMHNQDRAA-UHFFFAOYSA-N 8-[4,5-bis(4-chlorophenyl)-1-phenylimidazol-2-yl]oxyoctanoic acid Chemical compound C=1C=CC=CC=1N1C(OCCCCCCCC(=O)O)=NC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 YSWRBWMHNQDRAA-UHFFFAOYSA-N 0.000 description 1
- DQGUQAPNUXMJQK-UHFFFAOYSA-N 8-[4,5-bis(4-fluorophenyl)-1-phenylimidazol-2-yl]oxyoctanoic acid Chemical compound C=1C=CC=CC=1N1C(OCCCCCCCC(=O)O)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 DQGUQAPNUXMJQK-UHFFFAOYSA-N 0.000 description 1
- SCTRLHIAVHHIEJ-UHFFFAOYSA-N 8-chlorooctanoic acid Chemical compound OC(=O)CCCCCCCCl SCTRLHIAVHHIEJ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XBDGQDFYRTXBTR-UHFFFAOYSA-N C(C)OC(CCCCCCCCCCOC=1N(C(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)=O Chemical compound C(C)OC(CCCCCCCCCCOC=1N(C(=C(N1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)=O XBDGQDFYRTXBTR-UHFFFAOYSA-N 0.000 description 1
- RGTRSHIDNFUSIQ-UHFFFAOYSA-N COC(C(CCCCCC)OC=1N(C(=C(N1)C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC)C1=CC=CC=C1)=O Chemical compound COC(C(CCCCCC)OC=1N(C(=C(N1)C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC)C1=CC=CC=C1)=O RGTRSHIDNFUSIQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- IQNMLTVFFQLACD-UHFFFAOYSA-M [Na+].C1(=CC=CC=C1)N1C(=NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)OC(CC(=O)[O-])CCCCC Chemical compound [Na+].C1(=CC=CC=C1)N1C(=NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)OC(CC(=O)[O-])CCCCC IQNMLTVFFQLACD-UHFFFAOYSA-M 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RVGRNEMSIRZFLX-UHFFFAOYSA-N benzyl 8-(1,4,5-triphenylimidazol-2-yl)oxyoctanoate Chemical compound C=1C=CC=CC=1COC(=O)CCCCCCCOC(N1C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 RVGRNEMSIRZFLX-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- BQLBBMUNEPMXIP-UHFFFAOYSA-N ethyl 4-(1,4,5-triphenylimidazol-2-yl)oxybutanoate Chemical compound C=1C=CC=CC=1N1C(OCCCC(=O)OCC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 BQLBBMUNEPMXIP-UHFFFAOYSA-N 0.000 description 1
- OPXNFHAILOHHFO-UHFFFAOYSA-N ethyl 4-chlorobutanoate Chemical compound CCOC(=O)CCCCl OPXNFHAILOHHFO-UHFFFAOYSA-N 0.000 description 1
- AIEAQDBEOIZCCK-UHFFFAOYSA-N ethyl 5-(1,4,5-triphenylimidazol-2-yl)oxypentanoate Chemical compound C=1C=CC=CC=1N1C(OCCCCC(=O)OCC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 AIEAQDBEOIZCCK-UHFFFAOYSA-N 0.000 description 1
- AFRWBGJRWRHQOV-UHFFFAOYSA-N ethyl 5-bromopentanoate Chemical compound CCOC(=O)CCCCBr AFRWBGJRWRHQOV-UHFFFAOYSA-N 0.000 description 1
- DXBULVYHTICWKT-UHFFFAOYSA-N ethyl 6-bromohexanoate Chemical compound CCOC(=O)CCCCCBr DXBULVYHTICWKT-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- BEOWOPXJMFBLOS-UHFFFAOYSA-N hexyl 8-(1,4,5-triphenylimidazol-2-yl)oxyoctanoate Chemical compound C=1C=CC=CC=1N1C(OCCCCCCCC(=O)OCCCCCC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 BEOWOPXJMFBLOS-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- HFNPVFKUZYCDIB-UHFFFAOYSA-N methyl 11-bromoundecanoate Chemical compound COC(=O)CCCCCCCCCCBr HFNPVFKUZYCDIB-UHFFFAOYSA-N 0.000 description 1
- VRCNQQIUZHGXFE-UHFFFAOYSA-N methyl 4-(1,4,5-triphenylimidazol-2-yl)oxybutanoate Chemical compound C=1C=CC=CC=1N1C(OCCCC(=O)OC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 VRCNQQIUZHGXFE-UHFFFAOYSA-N 0.000 description 1
- BDQIVAQFXQLHBI-UHFFFAOYSA-N methyl 8-[1,4,5-tris(4-chlorophenyl)imidazol-2-yl]oxyoctanoate Chemical compound C=1C=C(Cl)C=CC=1N1C(OCCCCCCCC(=O)OC)=NC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 BDQIVAQFXQLHBI-UHFFFAOYSA-N 0.000 description 1
- ZVVQRFVYBAQHOA-UHFFFAOYSA-N methyl 8-[1-(2-fluorophenyl)-4,5-diphenylimidazol-2-yl]oxyoctanoate Chemical compound C=1C=CC=C(F)C=1N1C(OCCCCCCCC(=O)OC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ZVVQRFVYBAQHOA-UHFFFAOYSA-N 0.000 description 1
- NLPWRXLJEKJTGN-UHFFFAOYSA-N methyl 8-[1-(4-chlorophenyl)-4,5-diphenylimidazol-2-yl]oxyoctanoate Chemical compound C=1C=C(Cl)C=CC=1N1C(OCCCCCCCC(=O)OC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 NLPWRXLJEKJTGN-UHFFFAOYSA-N 0.000 description 1
- BIHGSQNEABQNAL-UHFFFAOYSA-N methyl 8-[1-(4-methoxyphenyl)-4,5-diphenylimidazol-2-yl]oxyoctanoate Chemical compound C=1C=C(OC)C=CC=1N1C(OCCCCCCCC(=O)OC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 BIHGSQNEABQNAL-UHFFFAOYSA-N 0.000 description 1
- QNECGIBZUGWXCD-UHFFFAOYSA-N methyl 8-[1-(4-methylphenyl)-4,5-diphenylimidazol-2-yl]oxyoctanoate Chemical compound C=1C=C(C)C=CC=1N1C(OCCCCCCCC(=O)OC)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 QNECGIBZUGWXCD-UHFFFAOYSA-N 0.000 description 1
- KGZLQQZQGLBONN-UHFFFAOYSA-N methyl 8-[4,5-bis(4-chlorophenyl)-1-phenylimidazol-2-yl]oxyoctanoate Chemical compound C=1C=CC=CC=1N1C(OCCCCCCCC(=O)OC)=NC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 KGZLQQZQGLBONN-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012430 organic reaction media Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 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
- C07D233/70—One oxygen atom
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3228271 | 1982-07-29 | ||
| DE3228271A DE3228271A1 (de) | 1982-07-29 | 1982-07-29 | Triphenylimidazolyloxyalkansaeuren und ihre derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI832730A0 FI832730A0 (fi) | 1983-07-28 |
| FI832730L FI832730L (fi) | 1984-01-30 |
| FI79302B FI79302B (fi) | 1989-08-31 |
| FI79302C true FI79302C (fi) | 1989-12-11 |
Family
ID=6169571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI832730A FI79302C (fi) | 1982-07-29 | 1983-07-28 | Foerfarande foer framstaellning av farmakologiskt aktiva trifenylimidazolyloxialkansyror och derivat daerav. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4460598A (en, 2012) |
| EP (1) | EP0104342B1 (en, 2012) |
| JP (1) | JPS5951269A (en, 2012) |
| AT (1) | ATE25246T1 (en, 2012) |
| DE (2) | DE3228271A1 (en, 2012) |
| DK (1) | DK158723C (en, 2012) |
| ES (1) | ES524512A0 (en, 2012) |
| FI (1) | FI79302C (en, 2012) |
| GR (1) | GR78654B (en, 2012) |
| IE (1) | IE55485B1 (en, 2012) |
| NO (1) | NO160579C (en, 2012) |
| PT (1) | PT77125B (en, 2012) |
| ZA (1) | ZA834648B (en, 2012) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3323870A1 (de) * | 1983-07-02 | 1985-01-03 | A. Nattermann & Cie GmbH, 5000 Köln | Neue imidazol-2-ylthioalkansaeuren und ihre derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| US4598149A (en) * | 1984-03-02 | 1986-07-01 | Merck & Co., Inc. | 3-amino-2-hydroxypropyl of pyrimidin-4-one useful as antihypertensive, cardioprotective, antiarrythmic, and antianginal agents |
| 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 |
| DE3504677A1 (de) * | 1985-02-12 | 1986-08-14 | A. Nattermann & Cie GmbH, 5000 Köln | Neue imidazol-2-yloxyalkansaeuren und ihre derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| DE3504680A1 (de) * | 1985-02-12 | 1986-08-14 | A. Nattermann & Cie GmbH, 5000 Köln | Neue ether des 2-hydroxyimidazols, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| DE3504679A1 (de) * | 1985-02-12 | 1986-08-14 | A. Nattermann & Cie GmbH, 5000 Köln | Amide der 2-imidazolyloxyalkansaeuren, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| JPH0680057B2 (ja) * | 1986-04-28 | 1994-10-12 | 保土谷化学工業株式会社 | トリフエニルイミダゾ−ル及びその二量体 |
| NO890522L (no) * | 1988-02-25 | 1989-08-28 | Bayer Ag | Substituerte imidazolinoner og imidazolinthioner. |
| US4900744A (en) * | 1988-09-14 | 1990-02-13 | E. I. Du Pont De Nemours And Company | Antihypercholesterolemic 4,5-diaryl-2-substituted thioimidazoles |
| US5166214A (en) * | 1988-12-05 | 1992-11-24 | Du Pont Merck Pharmaceutical Company | Use of imidazoles for the treatment of atherosclerosis |
| CA2014537A1 (en) * | 1989-04-26 | 1990-10-26 | Yoshio Hayashi | 4-imidazoline derivatives |
| US4994482A (en) * | 1989-07-31 | 1991-02-19 | Bristol-Myers Squibb Company | Arylpyrazol derivatives as anti-platelet agents, compositions and use |
| US5019572A (en) * | 1990-02-07 | 1991-05-28 | Merck & Co., Inc. | Imidazole compounds and their use as transglutaminase inhibitors |
| US5262540A (en) * | 1989-12-20 | 1993-11-16 | Bristol-Myers Squibb Company | [2(4,5-diaryl-2 oxazoyl substituted phenoxy alkanoic acid and esters |
| US5152988A (en) * | 1990-02-07 | 1992-10-06 | Merck & Co., Inc. | Imidazole compounds in compositions and methods in thrombolytic therapy |
| US5011851A (en) * | 1990-02-13 | 1991-04-30 | Bristol-Myers Squibb Co. | Imidazole carboxylic acids and esters and inhibition of blood platelet aggregation therewith |
| EP0442448A3 (en) | 1990-02-13 | 1992-08-12 | Bristol-Myers Squibb Company | Heterocyclic carboxylic acids and esters |
| GB9019838D0 (en) * | 1990-09-11 | 1990-10-24 | Smith Kline French Lab | Compounds |
| US5428041A (en) * | 1991-05-31 | 1995-06-27 | The Du Pont Merck Pharmaceutical Company | Antihypercholesterolemic bis-trifluoromethyl-substituted imidazolines and derivatives thereof |
| 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 |
| US5187188A (en) * | 1992-04-03 | 1993-02-16 | Bristol-Myers Squibb Company | Oxazole carboxylic acid derivatives |
| US5254576A (en) * | 1992-04-03 | 1993-10-19 | Bristol-Myers Squibb Company | Diphenyl-heterocyclic-oxazole as platelet aggregation inhibitors |
| US5348969A (en) * | 1992-04-03 | 1994-09-20 | Bristol-Myers Squibb Company | Diphenyloxazolyl-oxazoles as platelet aggregation inhibitors |
| US5310748A (en) * | 1992-05-11 | 1994-05-10 | The Du Pont Merck Pharmaceutical Company | Imidazoles for the treatment of atherosclerosis |
| US5364875A (en) * | 1992-05-11 | 1994-11-15 | The Du Pont Merck Pharmaceutical Company | Imidazoles linked to bicyclic heterocyclic groups for the treatment of atherosclerosis |
| US5362879A (en) * | 1993-04-15 | 1994-11-08 | Bristol-Myers Squibb Company | 4-5-diphenyloxazole derivatives as inhibitors of blood platelet aggregation |
| SE527381C3 (sv) * | 2003-04-14 | 2006-03-21 | Linnman Elektronik Ab | Gemensam fältbuss för överföring av data och energi |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3636003A (en) * | 1969-11-17 | 1972-01-18 | Geigy Chem Corp | Substituted 2-mercaptoimidazole derivatives |
| DE2934746A1 (de) * | 1979-08-28 | 1981-03-19 | A. Nattermann & Cie GmbH, 5000 Köln | Oxoimidazolinalkansaeuren, deren salze und ester sowie verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| DE2950478A1 (de) * | 1979-12-14 | 1981-06-19 | A. Nattermann & Cie GmbH, 5000 Köln | 4,5-diaryl-4-imidazolin-2-on-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| DE3042466A1 (de) * | 1980-11-11 | 1982-06-16 | A. Nattermann & Cie GmbH, 5000 Köln | N-substituierte (omega) -(2-oxo-4-imidazolin-l-yl)-alkansaeure-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
-
1982
- 1982-07-29 DE DE3228271A patent/DE3228271A1/de not_active Withdrawn
-
1983
- 1983-06-24 IE IE1483/83A patent/IE55485B1/en not_active IP Right Cessation
- 1983-06-24 ZA ZA834648A patent/ZA834648B/xx unknown
- 1983-06-29 GR GR71796A patent/GR78654B/el unknown
- 1983-07-19 NO NO832630A patent/NO160579C/no unknown
- 1983-07-19 EP EP83107048A patent/EP0104342B1/de not_active Expired
- 1983-07-19 DE DE8383107048T patent/DE3369508D1/de not_active Expired
- 1983-07-19 AT AT83107048T patent/ATE25246T1/de not_active IP Right Cessation
- 1983-07-25 US US06/516,938 patent/US4460598A/en not_active Expired - Fee Related
- 1983-07-28 JP JP58136907A patent/JPS5951269A/ja active Granted
- 1983-07-28 DK DK346783A patent/DK158723C/da not_active IP Right Cessation
- 1983-07-28 PT PT77125A patent/PT77125B/pt not_active IP Right Cessation
- 1983-07-28 ES ES524512A patent/ES524512A0/es active Granted
- 1983-07-28 FI FI832730A patent/FI79302C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI832730A0 (fi) | 1983-07-28 |
| NO160579B (no) | 1989-01-23 |
| FI832730L (fi) | 1984-01-30 |
| PT77125A (en) | 1983-08-01 |
| EP0104342A1 (de) | 1984-04-04 |
| DK346783D0 (da) | 1983-07-28 |
| DK346783A (da) | 1984-01-30 |
| IE831483L (en) | 1983-12-29 |
| DK158723B (da) | 1990-07-09 |
| DK158723C (da) | 1990-12-10 |
| FI79302B (fi) | 1989-08-31 |
| DE3369508D1 (en) | 1987-03-05 |
| JPH0456030B2 (en, 2012) | 1992-09-07 |
| IE55485B1 (en) | 1990-09-26 |
| NO160579C (no) | 1989-05-03 |
| GR78654B (en, 2012) | 1984-09-27 |
| DE3228271A1 (de) | 1984-02-02 |
| ES8404332A1 (es) | 1984-04-16 |
| US4460598A (en) | 1984-07-17 |
| ES524512A0 (es) | 1984-04-16 |
| PT77125B (en) | 1986-01-24 |
| JPS5951269A (ja) | 1984-03-24 |
| EP0104342B1 (de) | 1987-01-28 |
| ATE25246T1 (de) | 1987-02-15 |
| NO832630L (no) | 1984-01-30 |
| ZA834648B (en) | 1984-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: A. NATTERMANN & CIE. G.M.B.H |