NO860285L - Fremgangsmaate ved fremstilling av imidazolderivater. - Google Patents
Fremgangsmaate ved fremstilling av imidazolderivater.Info
- Publication number
- NO860285L NO860285L NO860285A NO860285A NO860285L NO 860285 L NO860285 L NO 860285L NO 860285 A NO860285 A NO 860285A NO 860285 A NO860285 A NO 860285A NO 860285 L NO860285 L NO 860285L
- Authority
- NO
- Norway
- Prior art keywords
- group
- formula
- imidazole
- denotes
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 58
- 238000002360 preparation method Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 106
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
- 239000001257 hydrogen Substances 0.000 claims abstract description 43
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 50
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 45
- -1 oxy compound Chemical class 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 29
- 239000003153 chemical reaction reagent Substances 0.000 claims description 28
- 238000009833 condensation Methods 0.000 claims description 25
- 230000005494 condensation Effects 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 24
- 125000002883 imidazolyl group Chemical group 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052727 yttrium Inorganic materials 0.000 claims description 14
- 238000005804 alkylation reaction Methods 0.000 claims description 13
- 239000012442 inert solvent Substances 0.000 claims description 13
- 230000029936 alkylation Effects 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 238000010511 deprotection reaction Methods 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- 238000012360 testing method Methods 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims description 9
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 150000002825 nitriles Chemical class 0.000 claims description 8
- 230000009467 reduction Effects 0.000 claims description 8
- 238000006722 reduction reaction Methods 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 230000018044 dehydration Effects 0.000 claims description 7
- 238000006297 dehydration reaction Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 6
- 150000001409 amidines Chemical class 0.000 claims description 6
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 238000006254 arylation reaction Methods 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 150000002460 imidazoles Chemical class 0.000 claims description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- GWEBNTZNQUIGRG-UHFFFAOYSA-N 5-(1,1-diphenylpentan-2-yl)-1h-imidazole Chemical compound C=1N=CNC=1C(CCC)C(C=1C=CC=CC=1)C1=CC=CC=C1 GWEBNTZNQUIGRG-UHFFFAOYSA-N 0.000 claims description 4
- CGWCKWISXYESMC-UHFFFAOYSA-N 5-(2,2-diphenylethyl)-1h-imidazole Chemical compound C=1N=CNC=1CC(C=1C=CC=CC=1)C1=CC=CC=C1 CGWCKWISXYESMC-UHFFFAOYSA-N 0.000 claims description 4
- UCJKAZHIPMERPB-UHFFFAOYSA-N 5-(2-methoxy-1,1-diphenylpentan-2-yl)-1h-imidazole Chemical compound C=1N=CNC=1C(OC)(CCC)C(C=1C=CC=CC=1)C1=CC=CC=C1 UCJKAZHIPMERPB-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 150000004705 aldimines Chemical class 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004122 cyclic group Chemical class 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 150000002081 enamines Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 238000006138 lithiation reaction Methods 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 238000006477 desulfuration reaction Methods 0.000 claims description 2
- 230000023556 desulfurization Effects 0.000 claims description 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 230000026030 halogenation Effects 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
- 150000002527 isonitriles Chemical class 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 238000006481 deamination reaction Methods 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- GLDOAMWVDAZGLH-UHFFFAOYSA-N azane;guanidine Chemical compound N.NC(N)=N GLDOAMWVDAZGLH-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 230000009615 deamination Effects 0.000 claims 1
- 238000006735 epoxidation reaction Methods 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 150000003555 thioacetals Chemical class 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 7
- 229940124597 therapeutic agent Drugs 0.000 abstract description 3
- 230000002082 anti-convulsion Effects 0.000 abstract description 2
- 230000000903 blocking effect Effects 0.000 abstract description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- 230000000694 effects Effects 0.000 description 43
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 33
- 239000000047 product Substances 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 229960002896 clonidine Drugs 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 24
- 230000002829 reductive effect Effects 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 241000699670 Mus sp. Species 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 15
- 230000005764 inhibitory process Effects 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 239000000284 extract Substances 0.000 description 10
- 102000005962 receptors Human genes 0.000 description 10
- 108020003175 receptors Proteins 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 235000011054 acetic acid Nutrition 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 230000000295 complement effect Effects 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 230000009466 transformation Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 230000001773 anti-convulsant effect Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000556 agonist Substances 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 125000002524 organometallic group Chemical group 0.000 description 5
- 239000011343 solid material Substances 0.000 description 5
- 230000000638 stimulation Effects 0.000 description 5
- ZSTKHSQDNIGFLM-UHFFFAOYSA-N 5-methoxy-N,N-dimethyltryptamine Chemical compound COC1=CC=C2NC=C(CCN(C)C)C2=C1 ZSTKHSQDNIGFLM-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000003042 antagnostic effect Effects 0.000 description 4
- 210000003169 central nervous system Anatomy 0.000 description 4
- 230000001684 chronic effect Effects 0.000 description 4
- 231100000673 dose–response relationship Toxicity 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000013067 intermediate product Substances 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 125000001979 organolithium group Chemical class 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 230000002295 serotoninergic effect Effects 0.000 description 4
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 3
- MTOGRKZPJQVAMC-UHFFFAOYSA-N 4-(2,2-diphenylethyl)-5-methyl-1-tritylimidazole Chemical compound N1=CN(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C(C)=C1CC(C=1C=CC=CC=1)C1=CC=CC=C1 MTOGRKZPJQVAMC-UHFFFAOYSA-N 0.000 description 3
- JXVUYNVJEVJRIB-UHFFFAOYSA-N 5-(1,1-diphenylpent-1-en-2-yl)-1h-imidazole Chemical compound C=1N=CNC=1C(CCC)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JXVUYNVJEVJRIB-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000000670 adrenergic alpha-2 receptor antagonist Substances 0.000 description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 3
- 239000001961 anticonvulsive agent Substances 0.000 description 3
- 239000000935 antidepressant agent Substances 0.000 description 3
- 229940005513 antidepressants Drugs 0.000 description 3
- 229960003965 antiepileptics Drugs 0.000 description 3
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 3
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 3
- 229940125388 beta agonist Drugs 0.000 description 3
- 230000027455 binding Effects 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
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Classifications
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- C07C47/00—Compounds having —CHO groups
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Reproductive Health (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU85747A LU85747A1 (fr) | 1985-01-28 | 1985-01-28 | Derives d'imidazole leur preparation et utilisation ainsi que les compositions pharmaceutiques contenant des derives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO860285L true NO860285L (no) | 1986-07-29 |
Family
ID=19730397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO860285A NO860285L (no) | 1985-01-28 | 1986-01-27 | Fremgangsmaate ved fremstilling av imidazolderivater. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4738979A (de) |
| EP (1) | EP0194984B1 (de) |
| JP (1) | JPS61176571A (de) |
| KR (1) | KR890001972B1 (de) |
| AT (1) | ATE51618T1 (de) |
| AU (1) | AU597239B2 (de) |
| CA (1) | CA1273942C (de) |
| DE (1) | DE3670081D1 (de) |
| DK (1) | DK39286A (de) |
| ES (3) | ES8802141A1 (de) |
| FI (1) | FI860369A7 (de) |
| GR (1) | GR860223B (de) |
| IE (1) | IE860222L (de) |
| IL (1) | IL77717A (de) |
| LU (1) | LU85747A1 (de) |
| NO (1) | NO860285L (de) |
| PT (1) | PT81910B (de) |
| ZA (1) | ZA86596B (de) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU85747A1 (fr) * | 1985-01-28 | 1986-08-04 | Continental Pharma | Derives d'imidazole leur preparation et utilisation ainsi que les compositions pharmaceutiques contenant des derives |
| US4882343A (en) * | 1987-08-28 | 1989-11-21 | G. D. Searle & Co. | Biarylalkylimidazole derivatives as anti-depressants |
| GB2210875B (en) * | 1987-10-09 | 1991-05-29 | Farmos Oy | Aromatase inhibiting 4(5)-imidazoles |
| DE68917897D1 (de) * | 1988-12-15 | 1994-10-06 | Texaco Development Corp | Verfahren zur Herstellung von Imidazolen. |
| CA1321751C (en) * | 1989-02-21 | 1993-08-31 | Eugene C. Crichlow | Mechanism mediating ruminal stasis in ruminal lactic acidosis |
| GB2248058B (en) * | 1990-09-21 | 1994-09-14 | Orion Yhtymae Oy | Aromatase inhibiting 4(5)-imidazoles |
| AU627559B2 (en) * | 1989-03-30 | 1992-08-27 | Farmos-Yhtyma Oy | Novel aromatase inhibiting 4(5)-imidazoles |
| GB2229719B (en) * | 1989-03-30 | 1992-04-29 | Farmos Oy | Novel aromatase inhibiting 4(5)-imidazoles |
| GB2244431A (en) * | 1990-05-31 | 1991-12-04 | Farmos Oy | Treatment of age related memory impairment and other cognitive disorders |
| GB9012469D0 (en) * | 1990-06-05 | 1990-07-25 | Glaxo Group Ltd | Medicaments |
| FR2732017B1 (fr) * | 1995-03-21 | 2000-09-22 | Inst Nat Sante Rech Med | Nouveaux derives de l'imidazole antagonistes et/ou agonistes du recepteur h3 de l'histamine, leur preparation et leurs applications therapeutiques |
| US6841684B2 (en) | 1997-12-04 | 2005-01-11 | Allergan, Inc. | Imidiazoles having reduced side effects |
| US6329369B1 (en) | 1997-12-04 | 2001-12-11 | Allergan Sales, Inc. | Methods of treating pain and other conditions |
| PT1036065E (pt) * | 1997-12-04 | 2004-09-30 | Allergan Inc | Derivados de imidazol substituidos com actividade do tipo agonista nos receptores alfa 2b ou 2b/2c adrenergicos |
| CA2521656A1 (en) * | 2003-04-10 | 2004-10-21 | Orion Corporation | Treatment of epilepsy |
| US20080146523A1 (en) * | 2006-12-18 | 2008-06-19 | Guido Galley | Imidazole derivatives |
| US11827606B2 (en) | 2015-11-18 | 2023-11-28 | Spirify Pharma Inc. | Phenyl cyclohexanone derivatives and methods of making and using them |
| US11111210B2 (en) | 2015-11-18 | 2021-09-07 | Spirify Pharma Inc. | Phenyl cyclohexanone derivatives and methods of making and using them |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2069481B (en) * | 1980-02-13 | 1983-07-27 | Farmos Oy | Substituted imidazole derivatives |
| US4281141A (en) * | 1980-05-30 | 1981-07-28 | Eli Lilly And Company | 3-(Imidazol-4-yl)-2-phenylpropanenitriles |
| CA1238640A (en) * | 1984-06-18 | 1988-06-28 | Kenneth S. Hirsch | 4(5)-substituted imidazoles |
| US4605661A (en) * | 1984-06-18 | 1986-08-12 | Eli Lilly And Company | Aromastase inhibiting α,α-diarylimidazole-4(5)-propionitriles, α,α-diarylimidazole-4(5)-propionamides, and 4(5)-(2,2-diarylethyl)imidazoles |
| LU85747A1 (fr) * | 1985-01-28 | 1986-08-04 | Continental Pharma | Derives d'imidazole leur preparation et utilisation ainsi que les compositions pharmaceutiques contenant des derives |
-
1985
- 1985-01-28 LU LU85747A patent/LU85747A1/fr unknown
-
1986
- 1986-01-24 AU AU52696/86A patent/AU597239B2/en not_active Ceased
- 1986-01-27 IL IL77717A patent/IL77717A/xx unknown
- 1986-01-27 US US06/823,157 patent/US4738979A/en not_active Expired - Fee Related
- 1986-01-27 ES ES551274A patent/ES8802141A1/es not_active Expired
- 1986-01-27 CA CA500447A patent/CA1273942C/en not_active Expired
- 1986-01-27 KR KR1019860000517A patent/KR890001972B1/ko not_active Expired
- 1986-01-27 FI FI860369A patent/FI860369A7/fi not_active Application Discontinuation
- 1986-01-27 DK DK39286A patent/DK39286A/da not_active Application Discontinuation
- 1986-01-27 DE DE8686870010T patent/DE3670081D1/de not_active Expired - Fee Related
- 1986-01-27 AT AT86870010T patent/ATE51618T1/de not_active IP Right Cessation
- 1986-01-27 PT PT81910A patent/PT81910B/pt unknown
- 1986-01-27 EP EP86870010A patent/EP0194984B1/de not_active Expired - Lifetime
- 1986-01-27 IE IE860222A patent/IE860222L/xx unknown
- 1986-01-27 NO NO860285A patent/NO860285L/no unknown
- 1986-01-27 JP JP61015570A patent/JPS61176571A/ja active Pending
- 1986-01-27 GR GR860223A patent/GR860223B/el unknown
- 1986-01-27 ZA ZA86596A patent/ZA86596B/xx unknown
-
1987
- 1987-08-13 ES ES557663A patent/ES8900137A1/es not_active Expired
- 1987-08-13 ES ES557664A patent/ES8801216A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61176571A (ja) | 1986-08-08 |
| ES8900137A1 (es) | 1989-01-16 |
| ES551274A0 (es) | 1988-04-01 |
| FI860369L (fi) | 1986-07-29 |
| FI860369A7 (fi) | 1986-07-29 |
| PT81910A (en) | 1986-02-01 |
| DK39286D0 (da) | 1986-01-27 |
| US4738979A (en) | 1988-04-19 |
| DE3670081D1 (de) | 1990-05-10 |
| DK39286A (da) | 1986-07-29 |
| ATE51618T1 (de) | 1990-04-15 |
| ES557663A0 (es) | 1989-01-16 |
| AU597239B2 (en) | 1990-05-31 |
| EP0194984A1 (de) | 1986-09-17 |
| ES557664A0 (es) | 1987-12-16 |
| FI860369A0 (fi) | 1986-01-27 |
| GR860223B (en) | 1986-04-24 |
| AU5269686A (en) | 1986-07-31 |
| ES8802141A1 (es) | 1988-04-01 |
| EP0194984B1 (de) | 1990-04-04 |
| CA1273942A (en) | 1990-09-11 |
| LU85747A1 (fr) | 1986-08-04 |
| KR860005794A (ko) | 1986-08-13 |
| ZA86596B (en) | 1986-09-24 |
| IE860222L (en) | 1986-07-28 |
| PT81910B (en) | 1987-05-13 |
| ES8801216A1 (es) | 1987-12-16 |
| KR890001972B1 (ko) | 1989-06-05 |
| IL77717A (en) | 1990-07-12 |
| CA1273942C (en) | 1990-09-11 |
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