LT4460B - Imidazolo dariniai, giminingi alfa2 receptoriams - Google Patents
Imidazolo dariniai, giminingi alfa2 receptoriams Download PDFInfo
- Publication number
- LT4460B LT4460B LT98-057A LT98057A LT4460B LT 4460 B LT4460 B LT 4460B LT 98057 A LT98057 A LT 98057A LT 4460 B LT4460 B LT 4460B
- Authority
- LT
- Lithuania
- Prior art keywords
- hydrogen
- derivative according
- alkyl
- nmr
- imidazole
- Prior art date
Links
- 150000002460 imidazoles Chemical class 0.000 title claims abstract description 7
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract description 3
- 230000000694 effects Effects 0.000 title description 2
- 102000005962 receptors Human genes 0.000 title description 2
- 108020003175 receptors Proteins 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 62
- 239000001257 hydrogen Substances 0.000 claims abstract description 62
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 39
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 17
- -1 C3-C7-cycloalkyl Chemical group 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000002367 halogens Chemical class 0.000 claims abstract description 14
- 208000002193 Pain Diseases 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 8
- 206010012735 Diarrhoea Diseases 0.000 claims abstract description 7
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 7
- 206010020772 Hypertension Diseases 0.000 claims abstract description 7
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 7
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 7
- 208000025966 Neurological disease Diseases 0.000 claims abstract description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
- 208000010877 cognitive disease Diseases 0.000 claims abstract description 7
- 208000028867 ischemia Diseases 0.000 claims abstract description 7
- 206010027599 migraine Diseases 0.000 claims abstract description 7
- 230000000926 neurological effect Effects 0.000 claims abstract description 7
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 7
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
- 208000000094 Chronic Pain Diseases 0.000 claims abstract description 6
- 208000005298 acute pain Diseases 0.000 claims abstract description 6
- 230000001684 chronic effect Effects 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 150000003573 thiols Chemical class 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 150000001721 carbon Chemical group 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 6
- 208000021642 Muscular disease Diseases 0.000 claims description 5
- 230000003387 muscular Effects 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000003444 anaesthetic effect Effects 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 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 description 3
- 241001465754 Metazoa Species 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 206010016275 Fear Diseases 0.000 claims 3
- 150000001356 alkyl thiols Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000009429 distress Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- YIAPLDFPUUJILH-UHFFFAOYSA-N indan-1-ol Chemical group C1=CC=C2C(O)CCC2=C1 YIAPLDFPUUJILH-UHFFFAOYSA-N 0.000 claims 1
- 238000002483 medication Methods 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 7
- 208000019901 Anxiety disease Diseases 0.000 abstract description 6
- 230000036506 anxiety Effects 0.000 abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 6
- 206010012335 Dependence Diseases 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 101100495911 Arabidopsis thaliana CHR10 gene Proteins 0.000 abstract 1
- 208000023178 Musculoskeletal disease Diseases 0.000 abstract 1
- 229940124534 adjunct to anesthesia Drugs 0.000 abstract 1
- 201000009240 nasopharyngitis Diseases 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- 238000005481 NMR spectroscopy Methods 0.000 description 92
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 150000003840 hydrochlorides Chemical class 0.000 description 53
- 239000000243 solution Substances 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
- 239000000047 product Substances 0.000 description 35
- 239000011541 reaction mixture Substances 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 238000000034 method Methods 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
- 229910052938 sodium sulfate Inorganic materials 0.000 description 21
- 235000011152 sodium sulphate Nutrition 0.000 description 21
- 239000012043 crude product Substances 0.000 description 19
- 238000003818 flash chromatography Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 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
- 239000000908 ammonium hydroxide Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 11
- 239000003480 eluent Substances 0.000 description 10
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 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
- 230000015572 biosynthetic process Effects 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
- 125000006239 protecting group Chemical group 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 125000003287 1H-imidazol-4-ylmethyl group Chemical group [H]N1C([H])=NC(C([H])([H])[*])=C1[H] 0.000 description 5
- 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 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 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
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- QONDAZCJAPQGRX-UHFFFAOYSA-N 3-benzylimidazole-4-carbaldehyde Chemical compound O=CC1=CN=CN1CC1=CC=CC=C1 QONDAZCJAPQGRX-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
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 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 3
- 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 description 3
- XEXPATNGWGSUHA-UHFFFAOYSA-N 6-(hydroxymethyl)-3-(1h-imidazol-5-ylmethyl)-2,3-dihydro-1h-inden-5-ol Chemical compound C1=2C=C(O)C(CO)=CC=2CCC1CC1=CNC=N1 XEXPATNGWGSUHA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 238000003747 Grignard reaction Methods 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- 230000008484 agonism Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000002585 base Substances 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
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 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
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
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- 230000001423 neocortical effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000725 suspension Substances 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
- 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 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- ZQEXIXXJFSQPNA-UHFFFAOYSA-N 1h-imidazole-5-carbaldehyde Chemical compound O=CC1=CNC=N1 ZQEXIXXJFSQPNA-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
- 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
- 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
- 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
- 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
- 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 description 2
- 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 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
- 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
- LYPWHPZUHOVYBB-UHFFFAOYSA-N 5-[(6-methoxy-2,3-dihydro-1h-inden-1-yl)methyl]-1h-imidazole;hydrochloride Chemical compound Cl.C12=CC(OC)=CC=C2CCC1CC1=CNC=N1 LYPWHPZUHOVYBB-UHFFFAOYSA-N 0.000 description 2
- 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
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- HRLIOXLXPOHXTA-NSHDSACASA-N dexmedetomidine Chemical compound C1([C@@H](C)C=2C(=C(C)C=CC=2)C)=CN=C[N]1 HRLIOXLXPOHXTA-NSHDSACASA-N 0.000 description 2
- 229960004253 dexmedetomidine Drugs 0.000 description 2
- GRTGGSXWHGKRSB-UHFFFAOYSA-N dichloromethyl methyl ether Chemical compound COC(Cl)Cl GRTGGSXWHGKRSB-UHFFFAOYSA-N 0.000 description 2
- MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
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- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
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- 238000006467 substitution reaction Methods 0.000 description 2
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- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- GSAZPQZZGMCQHA-UHFFFAOYSA-N 1,3-dibromo-8-(1h-imidazol-5-ylmethyl)-5,6,7,8-tetrahydronaphthalen-2-ol Chemical compound C12=C(Br)C(O)=C(Br)C=C2CCCC1CC1=CNC=N1 GSAZPQZZGMCQHA-UHFFFAOYSA-N 0.000 description 1
- UHKAJLSKXBADFT-UHFFFAOYSA-N 1,3-indandione Chemical group C1=CC=C2C(=O)CC(=O)C2=C1 UHKAJLSKXBADFT-UHFFFAOYSA-N 0.000 description 1
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000006519 Mcmurry reaction Methods 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
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- 229930006000 Sucrose Natural products 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
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- 108020004101 alpha-2 Adrenergic Receptor Proteins 0.000 description 1
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- 239000002643 anesthesia adjuvant Substances 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
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- 150000001649 bromium compounds Chemical class 0.000 description 1
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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- YRRWNBMOJMMXQY-UHFFFAOYSA-N n,n-dimethylimidazole-1-sulfonamide Chemical compound CN(C)S(=O)(=O)N1C=CN=C1 YRRWNBMOJMMXQY-UHFFFAOYSA-N 0.000 description 1
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- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
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- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
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- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 108090000623 proteins and genes Proteins 0.000 description 1
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- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
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Classifications
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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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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-
- 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)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Anesthesiology (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Otolaryngology (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9520150.5A GB9520150D0 (en) | 1995-10-03 | 1995-10-03 | New imidazole derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LT98057A LT98057A (en) | 1998-09-25 |
| LT4460B true LT4460B (lt) | 1999-02-25 |
Family
ID=10781676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LT98-057A LT4460B (lt) | 1995-10-03 | 1998-04-22 | Imidazolo dariniai, giminingi alfa2 receptoriams |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US6313311B1 (ru) |
| EP (1) | EP0888309B1 (ru) |
| JP (1) | JP4129891B2 (ru) |
| KR (1) | KR19990064013A (ru) |
| CN (1) | CN1068592C (ru) |
| AT (1) | ATE234819T1 (ru) |
| AU (1) | AU708002B2 (ru) |
| BG (1) | BG63916B1 (ru) |
| CA (1) | CA2231535C (ru) |
| CZ (1) | CZ291576B6 (ru) |
| DE (1) | DE69626862T2 (ru) |
| DK (1) | DK0888309T3 (ru) |
| EE (1) | EE04436B1 (ru) |
| ES (1) | ES2195013T3 (ru) |
| GB (1) | GB9520150D0 (ru) |
| HK (1) | HK1014951A1 (ru) |
| HU (1) | HU224197B1 (ru) |
| IL (1) | IL123721A (ru) |
| LT (1) | LT4460B (ru) |
| LV (1) | LV12108B (ru) |
| NO (1) | NO311024B1 (ru) |
| NZ (1) | NZ319169A (ru) |
| PL (1) | PL189110B1 (ru) |
| PT (1) | PT888309E (ru) |
| RO (1) | RO120409B1 (ru) |
| RU (1) | RU2188194C2 (ru) |
| SI (1) | SI9620111B (ru) |
| SK (1) | SK283542B6 (ru) |
| UA (1) | UA49847C2 (ru) |
| WO (1) | WO1997012874A1 (ru) |
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| DE102004035322A1 (de) * | 2004-07-21 | 2006-02-16 | Universität des Saarlandes | Selektive Hemmstoffe humaner Corticoidsynthasen |
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| JP5341084B2 (ja) | 2007-08-03 | 2013-11-13 | エフ．ホフマン−ラ ロシュ アーゲー | Ｔａａｒ１リガンドとしてのピリジンカルボキシアミド及びベンズアミド誘導体 |
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| MY178667A (en) | 2012-09-14 | 2020-10-20 | Hoffmann La Roche | Pyrazole carboxamide derivatives as taar modulators for use in the treatment of several disorders, such as depression, diabetes and parkinson's disease |
| MX361761B (es) | 2012-09-17 | 2018-12-17 | Hoffmann La Roche | Derivados de triazol carboxamida. |
| WO2015165085A1 (en) | 2014-04-30 | 2015-11-05 | F.Hoffmann-La Roche Ag | Morpholin-pyridine derivatives |
| CN106470994B (zh) | 2014-08-27 | 2019-09-24 | 豪夫迈·罗氏有限公司 | 用于治疗cns疾病的取代的吡嗪并[2,1-a]异喹啉衍生物 |
| BR112017000160A2 (pt) | 2014-08-27 | 2017-10-31 | Hoffmann La Roche | derivados de azetidina substituidos como ligantes de taar |
| RU2731095C2 (ru) | 2016-03-17 | 2020-08-28 | Ф. Хоффманн-Ля Рош Аг | Производное 5-этил-4-метил-пиразол-3-карбоксамида, обладающее активностью агониста taar |
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