IL123721A - History of imidazole with affinities for alpha 2 receptors, methods for their preparation and pharmaceutical preparations containing them - Google Patents
History of imidazole with affinities for alpha 2 receptors, methods for their preparation and pharmaceutical preparations containing themInfo
- Publication number
- IL123721A IL123721A IL12372196A IL12372196A IL123721A IL 123721 A IL123721 A IL 123721A IL 12372196 A IL12372196 A IL 12372196A IL 12372196 A IL12372196 A IL 12372196A IL 123721 A IL123721 A IL 123721A
- Authority
- IL
- Israel
- Prior art keywords
- hydrogen
- alkyl
- derivative
- hydroxy
- derivative according
- Prior art date
Links
- 150000002460 imidazoles Chemical class 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title description 6
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 4
- 239000008194 pharmaceutical composition Substances 0.000 title description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
- 239000001257 hydrogen Substances 0.000 claims abstract description 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- -1 C3-C7-cycloalkyl Chemical group 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 125000003277 amino group Chemical group 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 150000001721 carbon Chemical group 0.000 claims abstract description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 208000019901 Anxiety disease Diseases 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 8
- 230000036506 anxiety Effects 0.000 claims description 8
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 7
- 206010012335 Dependence Diseases 0.000 claims description 5
- 206010012735 Diarrhoea Diseases 0.000 claims description 5
- 208000010412 Glaucoma Diseases 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 208000019695 Migraine disease Diseases 0.000 claims description 5
- 208000023178 Musculoskeletal disease Diseases 0.000 claims description 5
- 208000012902 Nervous system disease Diseases 0.000 claims description 5
- 208000025966 Neurological disease Diseases 0.000 claims description 5
- 208000010877 cognitive disease Diseases 0.000 claims description 5
- 208000028867 ischemia Diseases 0.000 claims description 5
- 206010027599 migraine Diseases 0.000 claims description 5
- 230000000926 neurological effect Effects 0.000 claims description 5
- 208000020016 psychiatric disease Diseases 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 208000000094 Chronic Pain Diseases 0.000 claims description 4
- 208000005298 acute pain Diseases 0.000 claims description 4
- 229940124534 adjunct to anesthesia Drugs 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 201000009240 nasopharyngitis Diseases 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract description 3
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 7
- 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
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003396 thiol group Chemical class [H]S* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- 238000005481 NMR spectroscopy Methods 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- 239000000047 product Substances 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 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 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
- 239000000908 ammonium hydroxide Substances 0.000 description 9
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 8
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 8
- 239000003480 eluent Substances 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- QONDAZCJAPQGRX-UHFFFAOYSA-N 3-benzylimidazole-4-carbaldehyde Chemical compound O=CC1=CN=CN1CC1=CC=CC=C1 QONDAZCJAPQGRX-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000008484 agonism Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 230000001423 neocortical effect Effects 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 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 3
- 238000010626 work up procedure Methods 0.000 description 3
- 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
- DPHNJPUOMLRELT-UHFFFAOYSA-N 2,3-dihydro-1h-inden-4-ol Chemical compound OC1=CC=CC2=C1CCC2 DPHNJPUOMLRELT-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
- 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
- WOVCHPLIEOXTHP-UHFFFAOYSA-N 5-[(5-methoxy-2,3-dihydro-1h-inden-1-yl)methyl]-1h-imidazole Chemical compound C1CC2=CC(OC)=CC=C2C1CC1=CNC=N1 WOVCHPLIEOXTHP-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
- 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
- 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
- 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
- 108060003345 Adrenergic Receptor Proteins 0.000 description 2
- 102000017910 Adrenergic receptor Human genes 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 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
- 239000002552 dosage form Substances 0.000 description 2
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- 210000001177 vas deferen Anatomy 0.000 description 2
- 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 1
- BUMMJRQZIJBYDM-UHFFFAOYSA-N 1-(3-benzylimidazol-4-yl)-3-(4-tert-butylphenyl)prop-2-en-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1C=CC(=O)C1=CN=CN1CC1=CC=CC=C1 BUMMJRQZIJBYDM-UHFFFAOYSA-N 0.000 description 1
- QMGCDGOYTMKLIQ-UHFFFAOYSA-N 1-(3-benzylimidazol-4-yl)propan-1-one Chemical compound CCC(=O)C1=CN=CN1CC1=CC=CC=C1 QMGCDGOYTMKLIQ-UHFFFAOYSA-N 0.000 description 1
- RFJHPPQPQWYNPA-UHFFFAOYSA-N 1-benzyl-5-(2,3-dihydroinden-1-ylidenemethyl)imidazole Chemical compound C1=NC=C(C=C2C3=CC=CC=C3CC2)N1CC1=CC=CC=C1 RFJHPPQPQWYNPA-UHFFFAOYSA-N 0.000 description 1
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- WWSJZGAPAVMETJ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethoxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OCC WWSJZGAPAVMETJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- DZSQSLQSMKNVBV-UHFFFAOYSA-N 4-nemd Chemical class C=1C=CC2=CC=CC=C2C=1C(C)C1=CN=CN1 DZSQSLQSMKNVBV-UHFFFAOYSA-N 0.000 description 1
- OTXINXDGSUFPNU-UHFFFAOYSA-N 4-tert-butylbenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C=C1 OTXINXDGSUFPNU-UHFFFAOYSA-N 0.000 description 1
- VFXTUXUMIJBKKH-UHFFFAOYSA-N 5-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-1h-imidazole Chemical compound C1CCC2=CC=CC=C2C1CC1=CNC=N1 VFXTUXUMIJBKKH-UHFFFAOYSA-N 0.000 description 1
- MYWZHULNDAGTQR-UHFFFAOYSA-N 5-(4-methyl-2,3-dihydro-1h-inden-1-yl)-1h-imidazole;hydrochloride Chemical compound Cl.C1CC=2C(C)=CC=CC=2C1C1=CNC=N1 MYWZHULNDAGTQR-UHFFFAOYSA-N 0.000 description 1
- XIXCWQZCYYNJEE-UHFFFAOYSA-N 5-(6-tert-butyl-4-methyl-2,3-dihydro-1h-inden-1-yl)-1h-imidazole Chemical compound C1CC=2C(C)=CC(C(C)(C)C)=CC=2C1C1=CNC=N1 XIXCWQZCYYNJEE-UHFFFAOYSA-N 0.000 description 1
- KXBOHUGIOAHDMK-UHFFFAOYSA-N 5-[(4-methoxy-2,3-dihydro-1h-inden-1-yl)methyl]-1h-imidazole Chemical compound C1CC=2C(OC)=CC=CC=2C1CC1=CNC=N1 KXBOHUGIOAHDMK-UHFFFAOYSA-N 0.000 description 1
- BEIFCNBGIXMWQS-UHFFFAOYSA-N 5-[(5,6-dimethoxy-2,3-dihydro-1h-inden-1-yl)methyl]-1h-imidazole Chemical compound C1=2C=C(OC)C(OC)=CC=2CCC1CC1=CNC=N1 BEIFCNBGIXMWQS-UHFFFAOYSA-N 0.000 description 1
- RJZWTDXXZFIGSL-UHFFFAOYSA-N 5-[(5,6-dimethoxy-3,3-dimethyl-1,2-dihydroinden-1-yl)methyl]-1h-imidazole Chemical compound C1C(C)(C)C=2C=C(OC)C(OC)=CC=2C1CC1=CNC=N1 RJZWTDXXZFIGSL-UHFFFAOYSA-N 0.000 description 1
- BTSUGOMCHWKSLQ-UHFFFAOYSA-N 5-[(5-tert-butyl-2,3-dihydro-1h-inden-1-yl)methyl]-1h-imidazole Chemical compound C1CC2=CC(C(C)(C)C)=CC=C2C1CC1=CNC=N1 BTSUGOMCHWKSLQ-UHFFFAOYSA-N 0.000 description 1
- KEKSWATUMHUCTR-UHFFFAOYSA-N 5-[(6-fluoro-2,3-dihydro-1h-inden-1-yl)methyl]-1h-imidazole Chemical compound C12=CC(F)=CC=C2CCC1CC1=CNC=N1 KEKSWATUMHUCTR-UHFFFAOYSA-N 0.000 description 1
- IVSMVIOUBJTNGG-UHFFFAOYSA-N 5-[(6-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]-1h-imidazole;hydrochloride Chemical compound Cl.C1CCC2=CC(OC)=CC=C2C1CC1=CNC=N1 IVSMVIOUBJTNGG-UHFFFAOYSA-N 0.000 description 1
- BSRKORSMRSVMEY-UHFFFAOYSA-N 5-[(6-methoxy-3,3-dimethyl-1,2-dihydroinden-1-yl)methyl]-1h-imidazole Chemical compound C=1C(OC)=CC=C(C(C2)(C)C)C=1C2CC1=CNC=N1 BSRKORSMRSVMEY-UHFFFAOYSA-N 0.000 description 1
- GPXTVZSOGLLVDV-UHFFFAOYSA-N 5-[(6-methoxy-4,5-dimethyl-2,3-dihydro-1h-inden-1-yl)methyl]-1h-imidazole Chemical compound C1CC=2C(C)=C(C)C(OC)=CC=2C1CC1=CNC=N1 GPXTVZSOGLLVDV-UHFFFAOYSA-N 0.000 description 1
- YZTLYXFVZUYZNT-UHFFFAOYSA-N 5-[(6-methoxy-4,7-dimethyl-2,3-dihydro-1h-inden-1-yl)methyl]-1h-imidazole Chemical compound C12=C(C)C(OC)=CC(C)=C2CCC1CC1=CNC=N1 YZTLYXFVZUYZNT-UHFFFAOYSA-N 0.000 description 1
- GTLMUGVJBIONCX-UHFFFAOYSA-N 5-[(6-methoxy-5-methyl-2,3-dihydro-1h-inden-1-yl)methyl]-1h-imidazole Chemical compound C1CC=2C=C(C)C(OC)=CC=2C1CC1=CNC=N1 GTLMUGVJBIONCX-UHFFFAOYSA-N 0.000 description 1
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- BXKRBVDCJBLTRO-UHFFFAOYSA-N 5-[(6-tert-butyl-5-methoxy-2,3-dihydro-1h-inden-1-yl)methyl]-1h-imidazole Chemical compound C1=2C=C(C(C)(C)C)C(OC)=CC=2CCC1CC1=CNC=N1 BXKRBVDCJBLTRO-UHFFFAOYSA-N 0.000 description 1
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- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Resins (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (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 (2)
| Publication Number | Publication Date |
|---|---|
| IL123721A0 IL123721A0 (en) | 1998-10-30 |
| IL123721A true IL123721A (en) | 2004-07-25 |
Family
ID=10781676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12372196A IL123721A (en) | 1995-10-03 | 1996-10-02 | History of imidazole with affinities for alpha 2 receptors, methods for their preparation and pharmaceutical preparations containing them |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US6313311B1 (cs) |
| EP (1) | EP0888309B1 (cs) |
| JP (1) | JP4129891B2 (cs) |
| KR (1) | KR19990064013A (cs) |
| CN (1) | CN1068592C (cs) |
| AT (1) | ATE234819T1 (cs) |
| AU (1) | AU708002B2 (cs) |
| BG (1) | BG63916B1 (cs) |
| CA (1) | CA2231535C (cs) |
| CZ (1) | CZ291576B6 (cs) |
| DE (1) | DE69626862T2 (cs) |
| DK (1) | DK0888309T3 (cs) |
| EE (1) | EE04436B1 (cs) |
| ES (1) | ES2195013T3 (cs) |
| GB (1) | GB9520150D0 (cs) |
| HK (1) | HK1014951A1 (cs) |
| HU (1) | HU224197B1 (cs) |
| IL (1) | IL123721A (cs) |
| LT (1) | LT4460B (cs) |
| LV (1) | LV12108B (cs) |
| NO (1) | NO311024B1 (cs) |
| NZ (1) | NZ319169A (cs) |
| PL (1) | PL189110B1 (cs) |
| PT (1) | PT888309E (cs) |
| RO (1) | RO120409B1 (cs) |
| RU (1) | RU2188194C2 (cs) |
| SI (1) | SI9620111B (cs) |
| SK (1) | SK283542B6 (cs) |
| UA (1) | UA49847C2 (cs) |
| WO (1) | WO1997012874A1 (cs) |
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| ZA981080B (en) * | 1997-02-11 | 1998-08-12 | Warner Lambert Co | Bicyclic inhibitors of protein farnesyl transferase |
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| US6329369B1 (en) | 1997-12-04 | 2001-12-11 | Allergan Sales, Inc. | Methods of treating pain and other conditions |
| RU2235092C2 (ru) * | 1997-12-04 | 2004-08-27 | Оллерган Инк. | Замещенные производные имидазола, способ введения активного соединения и способ лечения на основе этих соединений |
| US6841684B2 (en) * | 1997-12-04 | 2005-01-11 | Allergan, Inc. | Imidiazoles having reduced side effects |
| 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 |
| ATE302757T1 (de) | 2000-05-08 | 2005-09-15 | Orion Corp | Neue polyzyklische indanylimidazole mit alpha2 adrenergik aktivität |
| TW200306783A (en) * | 2002-04-29 | 2003-12-01 | Fmc Corp | 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 |
| US7700592B2 (en) | 2005-08-25 | 2010-04-20 | Schering Corporation | α2C adrenoreceptor agonists |
| RU2008110902A (ru) | 2005-08-25 | 2009-09-27 | Шеринг Корпорейшн (US) | Агонисты адренорецепторов альфа а2с |
| KR20080039982A (ko) | 2005-08-25 | 2008-05-07 | 쉐링 코포레이션 | 작용 선택적 알파2ｃ 아드레날린성 수용체 효능제로서의이미다졸 유도체 |
| RU2440344C2 (ru) * | 2006-01-27 | 2012-01-20 | Ф.Хоффманн-Ля Рош Аг | Применение 2-имидазолов для лечения расстройств цнс |
| AU2007312390B2 (en) | 2006-10-19 | 2013-03-28 | F. Hoffmann-La Roche Ag | Aminomethyl-4-imidazoles |
| JP5064511B2 (ja) | 2006-11-02 | 2012-10-31 | エフ．ホフマン−ラ ロシュ アーゲー | 痕跡アミン関連受容体調節剤としての置換２−イミダゾール |
| KR101134226B1 (ko) | 2006-11-16 | 2012-04-10 | 에프. 호프만-라 로슈 아게 | 치환된 4-이미다졸 |
| WO2008071574A1 (en) | 2006-12-13 | 2008-06-19 | F. Hoffmann-La Roche Ag | Novel 2 -imidazoles as ligands for trace amine associated receptors (taar) |
| US20080146523A1 (en) | 2006-12-18 | 2008-06-19 | Guido Galley | Imidazole derivatives |
| JP5248528B2 (ja) | 2007-02-02 | 2013-07-31 | エフ．ホフマン−ラ ロシュ アーゲー | Ｃｎｓ疾患用のｔａａｒ１リガンドとしての新規２−アミノオキサゾリン |
| CA2678036A1 (en) | 2007-02-13 | 2008-08-21 | Schering Corporation | Functionally selective alpha2c adrenoreceptor agonists |
| US8470863B2 (en) | 2007-02-13 | 2013-06-25 | Merck Sharp & Dohme, Corp. | Derivatives and analogs of chroman as functionally selective ALPHA2C adrenoreceptor agonists |
| JP2010518163A (ja) * | 2007-02-13 | 2010-05-27 | シェーリング コーポレイション | 機能選択性α２Ｃアドレナリン受容体アゴニスト |
| CA2676944C (en) | 2007-02-15 | 2016-01-19 | F. Hoffmann-La Roche Ag | 2-aminooxazolines as taar1 ligands |
| EP2173720A2 (en) | 2007-07-02 | 2010-04-14 | F. Hoffmann-Roche AG | 2-imidazolines having a good affinity to the trace amine associated receptors (taars) |
| BRPI0812833A2 (pt) | 2007-07-03 | 2014-12-09 | Hoffmann La Roche | 4-imidazolinas e seu uso como antidepressivos |
| KR101133862B1 (ko) | 2007-07-27 | 2012-04-06 | 에프. 호프만-라 로슈 아게 | Ｔａａｒ 리간드로서의 2-아제티딘메테인아민 및 2-피롤리딘메테인아민 |
| AU2008285795A1 (en) | 2007-08-03 | 2009-02-12 | F. Hoffmann-La Roche Ag | Pyridinecarboxamide and benzamide derivatives as TAAR1 ligands |
| US8383818B2 (en) | 2008-02-21 | 2013-02-26 | Merck Sharp & Dohme Corp. | Functionally selective alpha2C adrenoreceptor agonists |
| US8242153B2 (en) | 2008-07-24 | 2012-08-14 | Hoffmann-La Roche Inc. | 4,5-dihydro-oxazol-2YL derivatives |
| WO2010042473A1 (en) | 2008-10-07 | 2010-04-15 | Schering Corporation | Biaryl spiroaminooxazoline analogues as alpha2c adrenergic receptor modulators |
| 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 |
| EP2787970B1 (en) | 2011-12-11 | 2018-04-11 | Recro Pharma, Inc. | Intranasal dexmedetomidine compositions and methods of use thereof |
| MX354815B (es) | 2012-01-12 | 2018-03-22 | Hoffmann La Roche | Derivados heterociclicos como receptores asociados con las aminas traza (taars). |
| PL2895477T3 (pl) | 2012-09-14 | 2018-03-30 | F.Hoffmann-La Roche Ag | Pochodne pirazolokarboksyamidu jako modulatory taar do stosowania w leczeniu kilku zaburzeń, takich jak depresja, cukrzyca i choroba parkinsona |
| ES2605632T3 (es) | 2012-09-17 | 2017-03-15 | F. Hoffmann-La Roche Ag | Derivados triazol carboxamida |
| WO2015165085A1 (en) | 2014-04-30 | 2015-11-05 | F.Hoffmann-La Roche Ag | Morpholin-pyridine derivatives |
| WO2016030306A1 (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 |
| MX2016016488A (es) | 2014-08-27 | 2017-03-30 | Hoffmann La Roche | Derivados de azetidina sustituidos como ligandos de receptores asociados a aminas en trazas (taar). |
| SG11201807516UA (en) | 2016-03-17 | 2018-09-27 | Hoffmann La Roche | 5-ethyl-4-methyl-pyrazole-3-carboxamide derivative having activity as agonist of taar |
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| 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
- 1995-10-03 GB GBGB9520150.5A patent/GB9520150D0/en active Pending
-
1996
- 1996-10-02 CZ CZ19981018A patent/CZ291576B6/cs not_active IP Right Cessation
- 1996-10-02 PL PL96328167A patent/PL189110B1/pl unknown
- 1996-10-02 WO PCT/FI1996/000518 patent/WO1997012874A1/en not_active Application Discontinuation
- 1996-10-02 DE DE69626862T patent/DE69626862T2/de not_active Expired - Lifetime
- 1996-10-02 KR KR1019980702490A patent/KR19990064013A/ko not_active IP Right Cessation
- 1996-10-02 PT PT96932609T patent/PT888309E/pt unknown
- 1996-10-02 HU HU9802927A patent/HU224197B1/hu active IP Right Grant
- 1996-10-02 DK DK96932609T patent/DK0888309T3/da active
- 1996-10-02 ES ES96932609T patent/ES2195013T3/es not_active Expired - Lifetime
- 1996-10-02 NZ NZ319169A patent/NZ319169A/xx not_active IP Right Cessation
- 1996-10-02 JP JP51399497A patent/JP4129891B2/ja not_active Expired - Lifetime
- 1996-10-02 UA UA98031588A patent/UA49847C2/uk unknown
- 1996-10-02 AT AT96932609T patent/ATE234819T1/de active
- 1996-10-02 RO RO98-00825A patent/RO120409B1/ro unknown
- 1996-10-02 SK SK439-98A patent/SK283542B6/sk not_active IP Right Cessation
- 1996-10-02 AU AU71327/96A patent/AU708002B2/en not_active Expired
- 1996-10-02 EP EP96932609A patent/EP0888309B1/en not_active Expired - Lifetime
- 1996-10-02 IL IL12372196A patent/IL123721A/en not_active IP Right Cessation
- 1996-10-02 US US09/051,151 patent/US6313311B1/en not_active Expired - Lifetime
- 1996-10-02 SI SI9620111A patent/SI9620111B/sl unknown
- 1996-10-02 CN CN96197438A patent/CN1068592C/zh not_active Expired - Lifetime
- 1996-10-02 EE EE9800101A patent/EE04436B1/xx unknown
- 1996-10-02 CA CA002231535A patent/CA2231535C/en not_active Expired - Lifetime
- 1996-10-02 RU RU98108027/04A patent/RU2188194C2/ru active
-
1998
- 1998-03-12 BG BG102324A patent/BG63916B1/bg unknown
- 1998-03-31 LV LVP-98-61A patent/LV12108B/en unknown
- 1998-04-02 NO NO19981496A patent/NO311024B1/no not_active IP Right Cessation
- 1998-04-22 LT LT98-057A patent/LT4460B/lt not_active IP Right Cessation
-
1999
- 1999-01-14 HK HK99100180A patent/HK1014951A1/xx not_active IP Right Cessation
-
2001
- 2001-07-16 US US09/904,836 patent/US6479530B2/en not_active Expired - Lifetime
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