NO845278L - Substituerte imidazoler. - Google Patents
Substituerte imidazoler.Info
- Publication number
- NO845278L NO845278L NO845278A NO845278A NO845278L NO 845278 L NO845278 L NO 845278L NO 845278 A NO845278 A NO 845278A NO 845278 A NO845278 A NO 845278A NO 845278 L NO845278 L NO 845278L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- compound
- residue
- phenyl
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 117
- 150000003839 salts Chemical class 0.000 claims description 54
- -1 1-[-(3-methoxy-phenyl)-ethyl]-2-methyl-imidazole Chemical compound 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- CILDGVODBJAMGO-UHFFFAOYSA-N 2-methyl-1-(1-phenylethyl)imidazole Chemical compound C1=CN=C(C)N1C(C)C1=CC=CC=C1 CILDGVODBJAMGO-UHFFFAOYSA-N 0.000 claims description 8
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 3
- GHRIIVLOPKZOSX-UHFFFAOYSA-N 1-[1-(2,3-dimethoxyphenyl)ethyl]-2-methylimidazole Chemical compound COC1=CC=CC(C(C)N2C(=NC=C2)C)=C1OC GHRIIVLOPKZOSX-UHFFFAOYSA-N 0.000 claims description 2
- BQKOTSFOFCIBBI-UHFFFAOYSA-N 1-[1-(2,3-dimethylphenyl)ethyl]-2-methylimidazole Chemical compound C1=CN=C(C)N1C(C)C1=CC=CC(C)=C1C BQKOTSFOFCIBBI-UHFFFAOYSA-N 0.000 claims description 2
- MBVSJGYRZOVPLT-UHFFFAOYSA-N 1-[1-(2,6-dimethoxyphenyl)ethyl]-2-methylimidazole Chemical compound COC1=CC=CC(OC)=C1C(C)N1C(C)=NC=C1 MBVSJGYRZOVPLT-UHFFFAOYSA-N 0.000 claims description 2
- ZMPUEZSKKQYTIH-UHFFFAOYSA-N 1-[1-(2,6-dimethylphenyl)ethyl]-2-methylimidazole Chemical compound C1=CN=C(C)N1C(C)C1=C(C)C=CC=C1C ZMPUEZSKKQYTIH-UHFFFAOYSA-N 0.000 claims description 2
- PDCKEFKFQGVGRN-UHFFFAOYSA-N 1-[1-(2-ethylphenyl)ethyl]-2-methylimidazole Chemical compound CCC1=CC=CC=C1C(C)N1C(C)=NC=C1 PDCKEFKFQGVGRN-UHFFFAOYSA-N 0.000 claims description 2
- XEMAHKDYQSYSJZ-UHFFFAOYSA-N 1-[1-(2-methoxyphenyl)ethyl]-2-methylimidazole Chemical compound COC1=CC=CC=C1C(C)N1C(C)=NC=C1 XEMAHKDYQSYSJZ-UHFFFAOYSA-N 0.000 claims description 2
- VYZUVHXMYUUWCL-UHFFFAOYSA-N 2-methyl-1-(1-phenylpropyl)imidazole Chemical compound C1=CN=C(C)N1C(CC)C1=CC=CC=C1 VYZUVHXMYUUWCL-UHFFFAOYSA-N 0.000 claims description 2
- VUSYGDCECFZYRZ-UHFFFAOYSA-N 2-methyl-1-[1-(2,4,6-trimethylphenyl)ethyl]imidazole Chemical compound C1=CN=C(C)N1C(C)C1=C(C)C=C(C)C=C1C VUSYGDCECFZYRZ-UHFFFAOYSA-N 0.000 claims description 2
- JULVGTZEGOFPSR-UHFFFAOYSA-N 2-methyl-1-[1-(2-methylphenyl)ethyl]imidazole Chemical compound C1=CN=C(C)N1C(C)C1=CC=CC=C1C JULVGTZEGOFPSR-UHFFFAOYSA-N 0.000 claims description 2
- AKAJCYZGUXNBJC-UHFFFAOYSA-N 2-methyl-1-[1-(3-methylphenyl)ethyl]imidazole Chemical compound C1=CN=C(C)N1C(C)C1=CC=CC(C)=C1 AKAJCYZGUXNBJC-UHFFFAOYSA-N 0.000 claims description 2
- QUDYEMXSFYTKNP-UHFFFAOYSA-N 2-methyl-1-[1-(4-methylphenyl)ethyl]imidazole Chemical compound C1=CN=C(C)N1C(C)C1=CC=C(C)C=C1 QUDYEMXSFYTKNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- ZIBMBPFYMHCCEY-UHFFFAOYSA-N 1-[1-(4-methoxyphenyl)ethyl]-2-methylimidazole Chemical compound C1=CC(OC)=CC=C1C(C)N1C(C)=NC=C1 ZIBMBPFYMHCCEY-UHFFFAOYSA-N 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 65
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
- 239000000155 melt Substances 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000002904 solvent Substances 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 26
- 239000013543 active substance 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000002585 base Substances 0.000 description 18
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 17
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
- 235000019341 magnesium sulphate Nutrition 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 230000002378 acidificating effect Effects 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 14
- 229910052736 halogen Inorganic materials 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 150000002367 halogens Chemical class 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 11
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000000825 pharmaceutical preparation Substances 0.000 description 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 229910052744 lithium Inorganic materials 0.000 description 7
- 239000000052 vinegar Substances 0.000 description 7
- 235000021419 vinegar Nutrition 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 5
- 230000001476 alcoholic effect Effects 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 235000011852 gelatine desserts Nutrition 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- 235000012222 talc Nutrition 0.000 description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- 102000010909 Monoamine Oxidase Human genes 0.000 description 4
- 108010062431 Monoamine oxidase Proteins 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- DNHQUGRUHBFDFT-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)ethanol Chemical compound CC(O)C1=CC=C(C)C=C1C DNHQUGRUHBFDFT-UHFFFAOYSA-N 0.000 description 3
- ZLKAKOOPZYTDOD-UHFFFAOYSA-N 2-methyl-1-(1-phenylethyl)imidazole;hydrochloride Chemical compound Cl.C1=CN=C(C)N1C(C)C1=CC=CC=C1 ZLKAKOOPZYTDOD-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 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
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- PPLYZPAMMOECNS-UHFFFAOYSA-N n'-(1-phenylethyl)ethane-1,2-diamine Chemical compound NCCNC(C)C1=CC=CC=C1 PPLYZPAMMOECNS-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 229920001592 potato starch Polymers 0.000 description 3
- 230000000069 prophylactic effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
- XABRUGLLZWCSPM-UHFFFAOYSA-N 1-(2,6-dimethoxyphenyl)ethanol Chemical compound COC1=CC=CC(OC)=C1C(C)O XABRUGLLZWCSPM-UHFFFAOYSA-N 0.000 description 2
- JESIHYIJKKUWIS-UHFFFAOYSA-N 1-(4-Methylphenyl)ethanol Chemical compound CC(O)C1=CC=C(C)C=C1 JESIHYIJKKUWIS-UHFFFAOYSA-N 0.000 description 2
- CRJFHXYELTYDSG-UHFFFAOYSA-N 1-(4-nitrophenyl)ethanol Chemical compound CC(O)C1=CC=C([N+]([O-])=O)C=C1 CRJFHXYELTYDSG-UHFFFAOYSA-N 0.000 description 2
- HBIXOIOMBMDWQG-UHFFFAOYSA-N 2,2-dimethoxy-n-(1-phenylethyl)ethanamine Chemical compound COC(OC)CNC(C)C1=CC=CC=C1 HBIXOIOMBMDWQG-UHFFFAOYSA-N 0.000 description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- XALRZLLUQUXZMB-UHFFFAOYSA-N 2-(2-methylimidazol-1-yl)-2-phenylethanol;hydrochloride Chemical compound Cl.CC1=NC=CN1C(CO)C1=CC=CC=C1 XALRZLLUQUXZMB-UHFFFAOYSA-N 0.000 description 2
- WLHXOSIQSJQAMB-UHFFFAOYSA-N 2-[1-(2-methylimidazol-1-yl)ethyl]phenol Chemical compound C1=CN=C(C)N1C(C)C1=CC=CC=C1O WLHXOSIQSJQAMB-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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- PPQNDCSTOHZQEH-UHFFFAOYSA-N bis(benzotriazol-1-yl) carbonate Chemical compound N1=NC2=CC=CC=C2N1OC(=O)ON1C2=CC=CC=C2N=N1 PPQNDCSTOHZQEH-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- 230000009885 systemic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
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- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
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- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical group CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH698883 | 1983-12-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO845278L true NO845278L (no) | 1985-07-01 |
Family
ID=4318179
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO845278A NO845278L (no) | 1983-12-30 | 1984-12-28 | Substituerte imidazoler. |
Country Status (15)
Country | Link |
---|---|
EP (1) | EP0149976A3 (ja) |
JP (1) | JPS60158176A (ja) |
AU (1) | AU569135B2 (ja) |
CA (1) | CA1233828A (ja) |
DD (1) | DD228249A5 (ja) |
DK (1) | DK614384A (ja) |
ES (6) | ES8800166A1 (ja) |
FI (1) | FI845140L (ja) |
GR (1) | GR82625B (ja) |
HU (1) | HU193916B (ja) |
IL (1) | IL73955A (ja) |
NO (1) | NO845278L (ja) |
NZ (1) | NZ210722A (ja) |
PT (1) | PT79761B (ja) |
ZA (1) | ZA8410105B (ja) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0200947B1 (de) | 1985-04-26 | 1990-09-12 | F. Hoffmann-La Roche Ag | 1,3-Disubstituierte Imidazoliumsalze |
ZA867189B (en) * | 1985-09-23 | 1987-05-27 | Hoechst Ag | Arylmethylazoles and their salts,processes for their preparation,agents which contain these compounds,and their use |
DE3628545A1 (de) * | 1985-09-23 | 1987-04-23 | Hoechst Ag | Arylmethylazole und deren salze, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
US4937250A (en) * | 1988-03-07 | 1990-06-26 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
US4749713A (en) * | 1986-03-07 | 1988-06-07 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
US4978672A (en) * | 1986-03-07 | 1990-12-18 | Ciba-Geigy Corporation | Alpha-heterocyclc substituted tolunitriles |
DE3707151A1 (de) * | 1987-03-06 | 1988-09-15 | Hoechst Ag | 1-(1-aryl-2-hydroxy-ethyl)-imidazole und deren salze, verfahren zu ihrer herstellung, diese verbindungen enthaltende arzneimittel und ihre verwendung |
DE3812483A1 (de) * | 1987-06-27 | 1989-01-05 | Bayer Ag | (azolyl-vinyl)-phenol-alkenylether |
JPH03130266A (ja) * | 1989-07-28 | 1991-06-04 | Hodogaya Chem Co Ltd | 置換フェニルアルキルイミダゾール誘導体 |
DE3931554A1 (de) * | 1989-09-22 | 1991-04-04 | Hoechst Ag | (+)-(2-hydroxy-2-adamantyl)-1-imidazolyl-3- tolyl-methan und dessen salze, verfahren zu dessen herstellung, diese verbindung enthaltende arzneimittel und dessen verwendung |
JP3938651B2 (ja) * | 2000-04-13 | 2007-06-27 | セントラル硝子株式会社 | 光学活性α−メチル−ビス−3、5−(トリフルオロメチル)ベンジルアミンの製造方法 |
DE10032335A1 (de) * | 2000-07-04 | 2002-01-17 | Cognis Deutschland Gmbh | Dimethylbenzol-Derivate |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1487326A (fr) * | 1966-01-18 | 1967-07-07 | Clin Byla Ets | Dérivés imidazoliques et leur préparation |
IE40911B1 (en) * | 1974-04-11 | 1979-09-12 | Schering Ag | Imidazole derivatives and process for their manufacture |
DE2546064A1 (de) * | 1975-10-10 | 1977-04-21 | Schering Ag | Triazolderivate und verfahren zu ihrer herstellung |
DE2862340D1 (en) * | 1978-02-01 | 1983-11-24 | Wellcome Found | Imidazole derivatives and salts thereof, their synthesis, and pharmaceutical formulations thereof |
US4532331A (en) * | 1983-04-12 | 1985-07-30 | Smithkline Beckman Corporation | 1-Benzyl-2-aminomethyl imidazole derivatives |
US4581370A (en) * | 1983-07-12 | 1986-04-08 | Schering A.G. | Antiarrhythmic imidazoliums |
-
1984
- 1984-12-19 EP EP84810643A patent/EP0149976A3/de not_active Ceased
- 1984-12-20 DK DK614384A patent/DK614384A/da not_active Application Discontinuation
- 1984-12-27 IL IL73955A patent/IL73955A/xx unknown
- 1984-12-27 PT PT79761A patent/PT79761B/pt unknown
- 1984-12-27 FI FI845140A patent/FI845140L/fi not_active Application Discontinuation
- 1984-12-28 CA CA000471118A patent/CA1233828A/en not_active Expired
- 1984-12-28 AU AU37235/84A patent/AU569135B2/en not_active Expired - Fee Related
- 1984-12-28 HU HU844868A patent/HU193916B/hu unknown
- 1984-12-28 ZA ZA8410105A patent/ZA8410105B/xx unknown
- 1984-12-28 ES ES539204A patent/ES8800166A1/es not_active Expired
- 1984-12-28 JP JP59275046A patent/JPS60158176A/ja active Pending
- 1984-12-28 DD DD84272059A patent/DD228249A5/de unknown
- 1984-12-28 NO NO845278A patent/NO845278L/no unknown
- 1984-12-31 GR GR82625A patent/GR82625B/el unknown
-
1985
- 1985-01-04 NZ NZ210722A patent/NZ210722A/en unknown
-
1986
- 1986-02-28 ES ES552557A patent/ES8705224A1/es not_active Expired
- 1986-02-28 ES ES552559A patent/ES8705397A1/es not_active Expired
- 1986-02-28 ES ES552556A patent/ES8705395A1/es not_active Expired
- 1986-02-28 ES ES552558A patent/ES8705396A1/es not_active Expired
- 1986-02-28 ES ES552555A patent/ES8705394A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DK614384D0 (da) | 1984-12-20 |
ES552557A0 (es) | 1987-05-01 |
ES552556A0 (es) | 1987-05-01 |
ES8705397A1 (es) | 1987-05-01 |
HU193916B (en) | 1987-12-28 |
ES8705394A1 (es) | 1987-05-01 |
ES8800166A1 (es) | 1987-10-16 |
ES552559A0 (es) | 1987-05-01 |
ES8705395A1 (es) | 1987-05-01 |
ES552558A0 (es) | 1987-05-01 |
PT79761B (en) | 1986-12-10 |
FI845140A0 (fi) | 1984-12-27 |
NZ210722A (en) | 1987-06-30 |
ES539204A0 (es) | 1987-10-16 |
IL73955A (en) | 1988-09-30 |
JPS60158176A (ja) | 1985-08-19 |
FI845140L (fi) | 1985-07-01 |
PT79761A (en) | 1985-01-01 |
AU3723584A (en) | 1985-07-04 |
EP0149976A2 (de) | 1985-07-31 |
IL73955A0 (en) | 1985-03-31 |
CA1233828A (en) | 1988-03-08 |
DK614384A (da) | 1985-07-01 |
ZA8410105B (en) | 1985-08-28 |
AU569135B2 (en) | 1988-01-21 |
ES552555A0 (es) | 1987-05-01 |
HUT36463A (en) | 1985-09-30 |
DD228249A5 (de) | 1985-10-09 |
ES8705224A1 (es) | 1987-05-01 |
ES8705396A1 (es) | 1987-05-01 |
GR82625B (en) | 1985-05-07 |
EP0149976A3 (de) | 1986-12-10 |
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