NO311024B1 - Imidazolderivater med affinitet for <alfa> 2- reseptoraktivitet, preparat inneholdende det, samt anvendelse avderivatet - Google Patents
Imidazolderivater med affinitet for <alfa> 2- reseptoraktivitet, preparat inneholdende det, samt anvendelse avderivatet Download PDFInfo
- Publication number
- NO311024B1 NO311024B1 NO19981496A NO981496A NO311024B1 NO 311024 B1 NO311024 B1 NO 311024B1 NO 19981496 A NO19981496 A NO 19981496A NO 981496 A NO981496 A NO 981496A NO 311024 B1 NO311024 B1 NO 311024B1
- Authority
- NO
- Norway
- Prior art keywords
- hydrogen
- alkyl
- imidazole
- hydroxy
- nmr
- Prior art date
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- 150000002460 imidazoles Chemical class 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract description 4
- 230000000694 effects Effects 0.000 title description 3
- 102000005962 receptors Human genes 0.000 title description 3
- 108020003175 receptors Proteins 0.000 title description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 80
- 239000001257 hydrogen Substances 0.000 claims abstract description 80
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 27
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- 150000002367 halogens Chemical class 0.000 claims abstract description 17
- -1 C3-C7-cycloalkyl Chemical group 0.000 claims abstract description 15
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 11
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 10
- 208000002193 Pain Diseases 0.000 claims abstract description 10
- 230000036506 anxiety Effects 0.000 claims abstract description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 9
- 150000002148 esters Chemical class 0.000 claims abstract description 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 6
- 206010012735 Diarrhoea Diseases 0.000 claims abstract description 6
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 6
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 6
- 208000023178 Musculoskeletal disease Diseases 0.000 claims abstract description 6
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 6
- 208000025966 Neurological disease Diseases 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 208000010877 cognitive disease Diseases 0.000 claims abstract description 6
- 206010027599 migraine Diseases 0.000 claims abstract description 6
- 230000000926 neurological effect Effects 0.000 claims abstract description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 6
- 208000000094 Chronic Pain Diseases 0.000 claims abstract description 5
- 208000005298 acute pain Diseases 0.000 claims abstract description 5
- 230000001684 chronic effect Effects 0.000 claims abstract description 5
- 201000009240 nasopharyngitis Diseases 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 150000003573 thiols Chemical class 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 206010020772 Hypertension Diseases 0.000 claims abstract description 4
- 208000028867 ischemia Diseases 0.000 claims abstract description 4
- 150000001721 carbon Chemical group 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical group C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 10
- 206010002091 Anaesthesia Diseases 0.000 claims description 6
- 230000037005 anaesthesia Effects 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- ABBXOJTZYKLTBP-UHFFFAOYSA-N 5-(2,3-dihydro-1h-inden-1-yl)-1h-imidazole Chemical compound C1CC2=CC=CC=C2C1C1=CNC=N1 ABBXOJTZYKLTBP-UHFFFAOYSA-N 0.000 claims description 4
- HEDLYDWGJOTEQS-UHFFFAOYSA-N 5-(5-chloro-1,2,3,4-tetrahydronaphthalen-1-yl)-1h-imidazole Chemical compound C1CCC=2C(Cl)=CC=CC=2C1C1=CNC=N1 HEDLYDWGJOTEQS-UHFFFAOYSA-N 0.000 claims description 4
- 238000001949 anaesthesia Methods 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 3
- XXQLSAWUSXSJTK-UHFFFAOYSA-N 5-(4-methyl-2,3-dihydro-1h-inden-1-yl)-1h-imidazole Chemical compound C1CC=2C(C)=CC=CC=2C1C1=CNC=N1 XXQLSAWUSXSJTK-UHFFFAOYSA-N 0.000 claims description 2
- JXODZIKMPVKXSX-UHFFFAOYSA-N 5-(6-methyl-2,3-dihydro-1h-inden-1-yl)-1h-imidazole Chemical compound C12=CC(C)=CC=C2CCC1C1=CNC=N1 JXODZIKMPVKXSX-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 101100495911 Arabidopsis thaliana CHR10 gene Proteins 0.000 abstract 1
- 206010012335 Dependence Diseases 0.000 abstract 1
- 229940124534 adjunct to anesthesia Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
- 238000005481 NMR spectroscopy Methods 0.000 description 92
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 69
- 150000003840 hydrochlorides Chemical class 0.000 description 54
- 239000000243 solution Substances 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- 239000000203 mixture Substances 0.000 description 51
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000000047 product Substances 0.000 description 31
- 238000000034 method Methods 0.000 description 29
- 239000011541 reaction mixture Substances 0.000 description 27
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 239000012043 crude product Substances 0.000 description 24
- 229910052938 sodium sulfate Inorganic materials 0.000 description 21
- 235000011152 sodium sulphate Nutrition 0.000 description 21
- 238000003818 flash chromatography Methods 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 14
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 13
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000908 ammonium hydroxide Substances 0.000 description 12
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000003480 eluent Substances 0.000 description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- 238000007363 ring formation reaction Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 6
- 229940098779 methanesulfonic acid Drugs 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- QONDAZCJAPQGRX-UHFFFAOYSA-N 3-benzylimidazole-4-carbaldehyde Chemical compound O=CC1=CN=CN1CC1=CC=CC=C1 QONDAZCJAPQGRX-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
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- 238000006467 substitution reaction Methods 0.000 description 4
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- BLQNOZHGIDFFAS-UHFFFAOYSA-N 1-(3-benzylimidazol-4-yl)ethanone Chemical compound CC(=O)C1=CN=CN1CC1=CC=CC=C1 BLQNOZHGIDFFAS-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 238000003747 Grignard reaction Methods 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- XQBBUKOBDKYVEH-UHFFFAOYSA-N 1-(1h-imidazol-5-ylmethyl)-6-methoxy-2,3-dihydro-1h-indene-5-carbaldehyde Chemical compound C1CC=2C=C(C=O)C(OC)=CC=2C1CC1=CNC=N1 XQBBUKOBDKYVEH-UHFFFAOYSA-N 0.000 description 2
- KJOLQJSKPGLFEU-UHFFFAOYSA-N 2-(3-benzylimidazol-4-yl)-4-phenylbutan-2-ol Chemical compound C=1N=CN(CC=2C=CC=CC=2)C=1C(O)(C)CCC1=CC=CC=C1 KJOLQJSKPGLFEU-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- OYKZVKWXOWICFI-UHFFFAOYSA-N 3-(1h-imidazol-1-ium-4-ylmethyl)-2,3-dihydro-1h-inden-5-ol;chloride Chemical compound Cl.C12=CC(O)=CC=C2CCC1CC1=CN=CN1 OYKZVKWXOWICFI-UHFFFAOYSA-N 0.000 description 2
- DKMJTMGANVYTDU-UHFFFAOYSA-N 3-(1h-imidazol-5-yl)-5-(2-methylpropyl)-2,3-dihydro-1h-inden-1-ol Chemical compound C12=CC(CC(C)C)=CC=C2C(O)CC1C1=CNC=N1 DKMJTMGANVYTDU-UHFFFAOYSA-N 0.000 description 2
- NOEANSSBIYXYCA-UHFFFAOYSA-N 3-(1h-imidazol-5-yl)-5-methoxy-6,7-dimethyl-2,3-dihydro-1h-inden-1-ol Chemical compound C1C(O)C=2C(C)=C(C)C(OC)=CC=2C1C1=CNC=N1 NOEANSSBIYXYCA-UHFFFAOYSA-N 0.000 description 2
- HMBWEFQRLYYKGK-UHFFFAOYSA-N 3-(1h-imidazol-5-yl)-5-methoxy-6,7-dimethyl-2,3-dihydroinden-1-one Chemical compound C1C(=O)C=2C(C)=C(C)C(OC)=CC=2C1C1=CNC=N1 HMBWEFQRLYYKGK-UHFFFAOYSA-N 0.000 description 2
- JJKKPNBICLHKCB-UHFFFAOYSA-N 3-(1h-imidazol-5-ylmethyl)-6-methoxy-2,3-dihydro-1h-indene-5-carbaldehyde Chemical compound C1=2C=C(C=O)C(OC)=CC=2CCC1CC1=CNC=N1 JJKKPNBICLHKCB-UHFFFAOYSA-N 0.000 description 2
- BYMJOQWPXDYBLF-UHFFFAOYSA-N 3-(3-benzylimidazol-4-yl)-1-[4-(2-methylpropyl)phenyl]prop-2-en-1-one Chemical compound C1=CC(CC(C)C)=CC=C1C(=O)C=CC1=CN=CN1CC1=CC=CC=C1 BYMJOQWPXDYBLF-UHFFFAOYSA-N 0.000 description 2
- SSYSWTZOXJUOTK-UHFFFAOYSA-N 3-(3-benzylimidazol-4-yl)-5-(2-methylpropyl)-2,3-dihydroinden-1-one Chemical compound C12=CC(CC(C)C)=CC=C2C(=O)CC1C1=CN=CN1CC1=CC=CC=C1 SSYSWTZOXJUOTK-UHFFFAOYSA-N 0.000 description 2
- MFADXYVDOSAINE-UHFFFAOYSA-N 3-(3-benzylimidazol-4-yl)-5-methoxy-6,7-dimethyl-2,3-dihydroinden-1-one Chemical compound C1C(=O)C=2C(C)=C(C)C(OC)=CC=2C1C1=CN=CN1CC1=CC=CC=C1 MFADXYVDOSAINE-UHFFFAOYSA-N 0.000 description 2
- GQNQOBBLCVTMRM-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-1-(1h-imidazol-5-yl)propan-1-ol Chemical compound C1=CC(C(C)(C)C)=CC=C1CCC(O)C1=CNC=N1 GQNQOBBLCVTMRM-UHFFFAOYSA-N 0.000 description 2
- DPGCTXQRUWDQNA-UHFFFAOYSA-N 3-[1-(1h-imidazol-5-yl)propyl]-2,3-dihydro-1h-inden-5-ol Chemical compound C1CC2=CC=C(O)C=C2C1C(CC)C1=CNC=N1 DPGCTXQRUWDQNA-UHFFFAOYSA-N 0.000 description 2
- JUVLKUBXUALSMA-UHFFFAOYSA-N 5-(1-methyl-2,3-dihydroinden-1-yl)-1h-imidazole Chemical compound C1CC2=CC=CC=C2C1(C)C1=CNC=N1 JUVLKUBXUALSMA-UHFFFAOYSA-N 0.000 description 2
- NJZVTLVQUICYRE-UHFFFAOYSA-N 5-(6-methoxy-4,5-dimethyl-2,3-dihydro-1h-inden-1-yl)-1h-imidazole Chemical compound C1CC=2C(C)=C(C)C(OC)=CC=2C1C1=CNC=N1 NJZVTLVQUICYRE-UHFFFAOYSA-N 0.000 description 2
- PLIPPAVFBJYEPZ-UHFFFAOYSA-N 5-(6-tert-butyl-2,3-dihydro-1h-inden-1-yl)-1h-imidazole Chemical compound C12=CC(C(C)(C)C)=CC=C2CCC1C1=CNC=N1 PLIPPAVFBJYEPZ-UHFFFAOYSA-N 0.000 description 2
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- DCPDKKDLGGMCDM-UHFFFAOYSA-N 5-[(6-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]-1h-imidazole Chemical compound C1CCC2=CC(OC)=CC=C2C1CC1=CNC=N1 DCPDKKDLGGMCDM-UHFFFAOYSA-N 0.000 description 2
- GDCKWMLPTVCZGU-UHFFFAOYSA-N 5-[(6-methoxy-2,3-dihydro-1h-inden-1-yl)methyl]-1h-imidazole Chemical compound C12=CC(OC)=CC=C2CCC1CC1=CNC=N1 GDCKWMLPTVCZGU-UHFFFAOYSA-N 0.000 description 2
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- FUSLZONREWHZRR-UHFFFAOYSA-N 5-[1-(6-methoxy-2,3-dihydro-1h-inden-1-yl)propyl]-1h-imidazole Chemical compound C1CC2=CC=C(OC)C=C2C1C(CC)C1=CNC=N1 FUSLZONREWHZRR-UHFFFAOYSA-N 0.000 description 2
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- OVLZWLQHLLVLAS-UHFFFAOYSA-N 6-hydroxy-1-(1h-imidazol-5-ylmethyl)-2,3-dihydro-1h-indene-5-carbaldehyde Chemical compound C1CC=2C=C(C=O)C(O)=CC=2C1CC1=CNC=N1 OVLZWLQHLLVLAS-UHFFFAOYSA-N 0.000 description 2
- JFFOKYWPLPKADR-UHFFFAOYSA-N 6-hydroxy-3-(1h-imidazol-5-ylmethyl)-2,3-dihydro-1h-indene-5-carbaldehyde Chemical compound C1=2C=C(C=O)C(O)=CC=2CCC1CC1=CNC=N1 JFFOKYWPLPKADR-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Physical Education & Sports Medicine (AREA)
- Anesthesiology (AREA)
- Communicable Diseases (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Otolaryngology (AREA)
- Virology (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9520150.5A GB9520150D0 (en) | 1995-10-03 | 1995-10-03 | New imidazole derivatives |
PCT/FI1996/000518 WO1997012874A1 (en) | 1995-10-03 | 1996-10-02 | Imidazole derivatives having affinity for alpha2 receptors activity |
Publications (3)
Publication Number | Publication Date |
---|---|
NO981496D0 NO981496D0 (no) | 1998-04-02 |
NO981496L NO981496L (no) | 1998-04-02 |
NO311024B1 true NO311024B1 (no) | 2001-10-01 |
Family
ID=10781676
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19981496A NO311024B1 (no) | 1995-10-03 | 1998-04-02 | Imidazolderivater med affinitet for <alfa> 2- reseptoraktivitet, preparat inneholdende det, samt anvendelse avderivatet |
Country Status (30)
Country | Link |
---|---|
US (2) | US6313311B1 (lt) |
EP (1) | EP0888309B1 (lt) |
JP (1) | JP4129891B2 (lt) |
KR (1) | KR19990064013A (lt) |
CN (1) | CN1068592C (lt) |
AT (1) | ATE234819T1 (lt) |
AU (1) | AU708002B2 (lt) |
BG (1) | BG63916B1 (lt) |
CA (1) | CA2231535C (lt) |
CZ (1) | CZ291576B6 (lt) |
DE (1) | DE69626862T2 (lt) |
DK (1) | DK0888309T3 (lt) |
EE (1) | EE04436B1 (lt) |
ES (1) | ES2195013T3 (lt) |
GB (1) | GB9520150D0 (lt) |
HK (1) | HK1014951A1 (lt) |
HU (1) | HU224197B1 (lt) |
IL (1) | IL123721A (lt) |
LT (1) | LT4460B (lt) |
LV (1) | LV12108B (lt) |
NO (1) | NO311024B1 (lt) |
NZ (1) | NZ319169A (lt) |
PL (1) | PL189110B1 (lt) |
PT (1) | PT888309E (lt) |
RO (1) | RO120409B1 (lt) |
RU (1) | RU2188194C2 (lt) |
SI (1) | SI9620111B (lt) |
SK (1) | SK283542B6 (lt) |
UA (1) | UA49847C2 (lt) |
WO (1) | WO1997012874A1 (lt) |
Families Citing this family (52)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA981080B (en) * | 1997-02-11 | 1998-08-12 | Warner Lambert Co | Bicyclic inhibitors of protein farnesyl transferase |
US6329369B1 (en) | 1997-12-04 | 2001-12-11 | Allergan Sales, Inc. | Methods of treating pain and other conditions |
AU2002254265B2 (en) * | 1997-12-04 | 2008-05-15 | Allergan, Inc. | Imidiazole derivatives and their use as agonists selective at alpha 2B or 2B/2C adrenergic receptors |
US6841684B2 (en) * | 1997-12-04 | 2005-01-11 | Allergan, Inc. | Imidiazoles having reduced side effects |
EP1036065B1 (en) * | 1997-12-04 | 2004-05-12 | Allergan, Inc. | Substituted imidazole derivatives having agonist-like activity at alpha 2b or 2b/2c adrenergic receptors |
EP1117399B1 (en) * | 1998-09-28 | 2005-02-09 | Orion Corporation | Use of 3-(1h-imidazol-4-ylmethyl)-indan-5-ol in the manufacture of a medicament for intraspinal, intrathecal or epidural administration |
TWI283669B (en) * | 1999-06-10 | 2007-07-11 | Allergan Inc | Compounds and method of treatment having agonist-like activity selective at alpha 2B or 2B/2C adrenergic receptors |
WO2001000192A2 (en) * | 1999-06-25 | 2001-01-04 | Orion Corporation | Method of administering an imidazole derivative to obtain analgesia |
AU778522B2 (en) * | 1999-10-29 | 2004-12-09 | Orion Corporation | Treatment or prevention of hypotension and shock |
US6388090B2 (en) | 2000-01-14 | 2002-05-14 | Orion Corporation | Imidazole derivatives |
FI20000073A0 (fi) * | 2000-01-14 | 2000-01-14 | Orion Yhtymae Oy | Uusia imidatsolijohdannaisia |
JP2003532712A (ja) * | 2000-05-08 | 2003-11-05 | オリオン コーポレーション | α2アドレナリン作用活性を有する新規な多環式インダニルイミダゾール |
TW200930291A (en) | 2002-04-29 | 2009-07-16 | Bayer Cropscience Ag | Pesticidal heterocycles |
FR2839719B1 (fr) * | 2002-05-16 | 2004-08-06 | Pf Medicament | Nouveaux composes imidazoliques, leur procede de preparation et leur utilisation a titre de medicaments |
FI20022159A0 (fi) * | 2002-12-05 | 2002-12-05 | Orion Corp | Uusia farmaseuttisia yhdisteitä |
DE102004035322A1 (de) * | 2004-07-21 | 2006-02-16 | Universität des Saarlandes | Selektive Hemmstoffe humaner Corticoidsynthasen |
ATE517883T1 (de) | 2005-08-25 | 2011-08-15 | Schering Corp | Imidazolderivate als funktionelle selektive agonisten des alpha2c-adrenorezeptors |
US7700592B2 (en) | 2005-08-25 | 2010-04-20 | Schering Corporation | α2C adrenoreceptor agonists |
JP2009506051A (ja) | 2005-08-25 | 2009-02-12 | シェーリング コーポレイション | α2Cアドレナリン受容体アゴニスト |
EP1981499A1 (en) * | 2006-01-27 | 2008-10-22 | F.Hoffmann-La Roche Ag | Use of 2-imidazoles for the treatment of cns disorders |
ES2381589T3 (es) | 2006-10-19 | 2012-05-29 | F. Hoffmann-La Roche Ag | Aminometil-4-imidazoles |
MX2009004617A (es) | 2006-11-02 | 2009-05-22 | Hoffmann La Roche | 2-imidazoles sustituidos como moduladores de los receptores asociados con trazas de amina. |
CN101535298A (zh) * | 2006-11-16 | 2009-09-16 | 弗·哈夫曼-拉罗切有限公司 | 取代的4-咪唑类化合物 |
KR101189348B1 (ko) | 2006-12-13 | 2012-10-09 | 에프. 호프만-라 로슈 아게 | 미량 아민 결합 수용체(taar)에 대한 리간드로서의 신규한 2-이미다졸 |
US20080146523A1 (en) | 2006-12-18 | 2008-06-19 | Guido Galley | Imidazole derivatives |
ES2510546T3 (es) | 2007-02-02 | 2014-10-21 | F. Hoffmann-La Roche Ag | Nuevas 2-aminooxazolinas como ligandos TAAR1 para trastornos del SNC |
US8017642B2 (en) | 2007-02-13 | 2011-09-13 | Schering Corporation | Functionally selective ALPHA2C adrenoreceptor agonists |
ATE530547T1 (de) | 2007-02-13 | 2011-11-15 | Schering Corp | Derivate und analoge von chroman als funktionell selektive alpha2c-adrenorezeptor-agonisten |
CA2678036A1 (en) | 2007-02-13 | 2008-08-21 | Schering Corporation | Functionally selective alpha2c adrenoreceptor agonists |
ES2525229T3 (es) | 2007-02-15 | 2014-12-19 | F. Hoffmann-La Roche Ag | 2-aminooxazolinas como ligandos de TAAR1 |
CN101687812A (zh) | 2007-07-02 | 2010-03-31 | 弗·哈夫曼-拉罗切有限公司 | 对痕量胺相关受体(taar)具有良好亲和性的2-咪唑啉化合物 |
CN101687811A (zh) | 2007-07-03 | 2010-03-31 | 弗·哈夫曼-拉罗切有限公司 | 4-咪唑啉类及其作为抗抑郁剂的应用 |
WO2009016048A1 (en) | 2007-07-27 | 2009-02-05 | F. Hoffmann-La Roche Ag | 2-azetidinemethaneamines and 2-pyrrolidinemethaneamines as taar-ligands |
CN101784515A (zh) | 2007-08-03 | 2010-07-21 | 弗·哈夫曼-拉罗切有限公司 | 作为taar1配体的吡啶甲酰胺和苯甲酰胺衍生物 |
WO2009105504A2 (en) | 2008-02-21 | 2009-08-27 | Schering Corporation | Functionally selective alpha2c adrenoreceptor agonists |
US8242153B2 (en) | 2008-07-24 | 2012-08-14 | Hoffmann-La Roche Inc. | 4,5-dihydro-oxazol-2YL derivatives |
AR073628A1 (es) | 2008-10-07 | 2010-11-17 | Schering Corp | Analogos de biaril espiroaminooxazolina y espiroaminodiazolina moduladores de receptores adrenergicos alfa2c, composiciones farmaceuticas que los comprenden y uso de los mismos en rinitis alergica,trastornos cardiacos y otras enfermedades |
CA2762107A1 (en) | 2009-05-15 | 2010-11-18 | Recro Pharma, Inc. | Sublingual dexmedetomidine compositions and methods of use thereof |
US8354441B2 (en) | 2009-11-11 | 2013-01-15 | Hoffmann-La Roche Inc. | Oxazoline derivatives |
US9452980B2 (en) | 2009-12-22 | 2016-09-27 | Hoffmann-La Roche Inc. | Substituted benzamides |
US8673950B2 (en) | 2010-11-02 | 2014-03-18 | Hoffmann-Laroche Inc. | Dihydrooxazol-2-amine derivatives |
US8802673B2 (en) | 2011-03-24 | 2014-08-12 | Hoffmann-La Roche Inc | Heterocyclic amine derivatives |
US9073911B2 (en) * | 2011-06-09 | 2015-07-07 | Hoffmann-La Roche Inc. | Pyrazole derivatives |
US9029370B2 (en) | 2011-06-10 | 2015-05-12 | Hoffmann-La Roche Inc. | Substituted benzamide derivatives |
RU2692245C2 (ru) | 2011-12-11 | 2019-06-24 | Рекро Фарма, Инк. | Интраназальные композиции дексмедетомидина и способы их применения |
CA2856204A1 (en) * | 2012-01-12 | 2013-07-18 | F. Hoffmann-La Roche Ag | Heterocyclic derivatives as trace amine associated receptors (taars) |
KR101706486B1 (ko) | 2012-09-14 | 2017-02-13 | 에프. 호프만-라 로슈 아게 | 우울증, 당뇨병 및 파킨슨병과 같은 몇가지 장애의 치료에 사용하기 위한 taar 조절제로서의 피라졸 카복스아마이드 유도체 |
WO2014041106A1 (en) | 2012-09-17 | 2014-03-20 | F. Hoffmann-La Roche Ag | Triazole carboxamide derivatives |
WO2015165085A1 (en) | 2014-04-30 | 2015-11-05 | F.Hoffmann-La Roche Ag | Morpholin-pyridine derivatives |
CA2953040A1 (en) | 2014-08-27 | 2016-03-03 | F. Hoffmann-La Roche Ag | Substituted pyrazino[2,1-a]isoquinoline derivatives for the treatment of cns disorders |
WO2016030310A1 (en) | 2014-08-27 | 2016-03-03 | F. Hoffmann-La Roche Ag | Substituted azetidine derivatives as taar ligands |
PL3430010T3 (pl) | 2016-03-17 | 2020-11-16 | F. Hoffmann-La Roche Ag | Pochodna 5-etylo-4-metylopirazolo-3-karboksyamidu wykazująca aktywność jako agonista taar |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3636002A (en) * | 1969-12-15 | 1972-01-18 | Janssen Pharmaceutica Nv | 1-(2-halobenzyloxy-1-indanyl)-imidazoles |
ES523609A0 (es) * | 1982-07-05 | 1985-03-01 | Erba Farmitalia | Procedimiento para preparar derivados n-imidazolilicos de compuestos biciclicos. |
US4634705A (en) * | 1984-06-06 | 1987-01-06 | Abbott Laboratories | Adrenergic amidines |
US4659730A (en) * | 1984-06-18 | 1987-04-21 | Eli Lilly And Company | Aromatase inhibiting imidazole derivatives |
GB2167408B (en) * | 1984-11-23 | 1988-05-25 | Farmos Oy | Substituted imidazole derivatives and their preparation and use |
FI81092C (fi) * | 1986-05-15 | 1990-09-10 | Farmos Oy | Foerfarande foer framstaellning av terapeutiskt aktiva 4(5)-(2,3-dihydro-1h-inden-2-yl)-imidazolderivat. |
US4878940A (en) * | 1987-04-02 | 1989-11-07 | Janssen Pharmaceutica N.V. | Herbicidal 1,5-substituted 1H-imidazoles |
IL91542A0 (en) * | 1988-10-06 | 1990-04-29 | Erba Carlo Spa | N-imidazolyl-and n-imidazolyl-methyl derivatives of substituted bicyclic compounds,their preparation and pharmaceutical compositions containing them |
GB9127050D0 (en) * | 1991-12-20 | 1992-02-19 | Orion Yhtymae Oy | Substituted imidazole derivatives and their preparation and use |
GB9425211D0 (en) | 1994-12-14 | 1995-02-15 | Ucb Sa | Substituted 1H-imidazoles |
US6388090B2 (en) * | 2000-01-14 | 2002-05-14 | Orion Corporation | Imidazole derivatives |
-
1995
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