SU1041033A3 - Способ получени производных аминопропанола или их солей - Google Patents

Способ получени производных аминопропанола или их солей Download PDF

Info

Publication number: SU1041033A3
Authority: SU; USSR - Soviet Union
Prior art keywords: propoxy; hydroxy; phenoxymethylpiperidino; indole; hydrogen
Prior art date: 1976-11-12

Application number

SU772541695A

Other languages

English (en)

Russian (ru)

Inventor

Кампе Вольфганг

Фрибе Вальтер-Гунар

Видеманн Фритц

Шпонер Гисберт

Барч Вольфганг

Дитманн Карл

Original Assignee

Берингер Маннхайм Гмбх (Фирма)

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-11-12

Filing date

1977-11-11

Publication date

1983-09-07

1977-11-11 Application filed by Берингер Маннхайм Гмбх (Фирма) filed Critical Берингер Маннхайм Гмбх (Фирма)

1983-09-07 Application granted granted Critical

1983-09-07 Publication of SU1041033A3 publication Critical patent/SU1041033A3/ru

Links

150000003839 salts Chemical class 0.000 title claims abstract description 6
MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 title claims abstract 3
238000004519 manufacturing process Methods 0.000 title claims 2
125000000217 alkyl group Chemical group 0.000 claims abstract 9
125000003545 alkoxy group Chemical group 0.000 claims abstract 7
125000004414 alkyl thio group Chemical group 0.000 claims abstract 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 3
125000001589 carboacyl group Chemical group 0.000 claims abstract 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 3
125000003435 aroyl group Chemical group 0.000 claims abstract 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 28
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims 3
150000002431 hydrogen Chemical class 0.000 claims 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
150000002825 nitriles Chemical class 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
125000005429 oxyalkyl group Chemical group 0.000 claims 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
-1 benzyloxy, benzyloxycarbonyl Chemical group 0.000 abstract description 60
BREBKAKBNYXIOP-UHFFFAOYSA-N 4-(phenoxymethyl)piperidine Chemical compound C1CNCCC1COC1=CC=CC=C1 BREBKAKBNYXIOP-UHFFFAOYSA-N 0.000 abstract description 12
CTWQPSSVUYPWOM-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-1h-indole Chemical compound C=1C=CC=2NC=CC=2C=1OCC1CO1 CTWQPSSVUYPWOM-UHFFFAOYSA-N 0.000 abstract description 4
125000001475 halogen functional group Chemical group 0.000 abstract 2
208000001953 Hypotension Diseases 0.000 abstract 1
125000004423 acyloxy group Chemical group 0.000 abstract 1
102000012740 beta Adrenergic Receptors Human genes 0.000 abstract 1
108010079452 beta Adrenergic Receptors Proteins 0.000 abstract 1
208000021822 hypotensive Diseases 0.000 abstract 1
230000001077 hypotensive effect Effects 0.000 abstract 1
239000003112 inhibitor Substances 0.000 abstract 1
229940124549 vasodilator Drugs 0.000 abstract 1
239000003071 vasodilator agent Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 20
239000013078 crystal Substances 0.000 description 17
235000019439 ethyl acetate Nutrition 0.000 description 17
239000000203 mixture Substances 0.000 description 16
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
229960004592 isopropanol Drugs 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 9
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 9
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
239000000706 filtrate Substances 0.000 description 5
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
239000005711 Benzoic acid Substances 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
235000010233 benzoic acid Nutrition 0.000 description 4
239000012964 benzotriazole Substances 0.000 description 4
239000003610 charcoal Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 3
KIBXUXDCTYYPQG-UHFFFAOYSA-N 2-benzylindazol-4-ol Chemical compound C1=C2C(O)=CC=CC2=NN1CC1=CC=CC=C1 KIBXUXDCTYYPQG-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000021736 acetylation Effects 0.000 description 3
238000006640 acetylation reaction Methods 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
229940073608 benzyl chloride Drugs 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000007327 hydrogenolysis reaction Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229910052759 nickel Inorganic materials 0.000 description 3
239000002243 precursor Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
LRJIACGZPACLFS-UHFFFAOYSA-N 2-benzyl-7-methyl-4-(oxiran-2-ylmethoxy)indazole Chemical compound C12=CN(CC=3C=CC=CC=3)N=C2C(C)=CC=C1OCC1CO1 LRJIACGZPACLFS-UHFFFAOYSA-N 0.000 description 2
BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-metylindole Natural products C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 2
CCZZNPBXUZCPEZ-UHFFFAOYSA-N 4-[(2-methoxyphenoxy)methyl]piperidine Chemical compound COC1=CC=CC=C1OCC1CCNCC1 CCZZNPBXUZCPEZ-UHFFFAOYSA-N 0.000 description 2
IGXCLKXDHNOUIB-UHFFFAOYSA-N 4-[(3-methylphenoxy)methyl]piperidine Chemical compound CC1=CC=CC(OCC2CCNCC2)=C1 IGXCLKXDHNOUIB-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
YMEGIDOLDLRACF-UHFFFAOYSA-N [4-(oxiran-2-ylmethoxy)-2h-indazol-3-yl]methyl acetate Chemical compound C=12C(COC(=O)C)=NNC2=CC=CC=1OCC1CO1 YMEGIDOLDLRACF-UHFFFAOYSA-N 0.000 description 2
150000001242 acetic acid derivatives Chemical class 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
238000007098 aminolysis reaction Methods 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
238000005574 benzylation reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000000034 method Methods 0.000 description 2
230000009935 nitrosation Effects 0.000 description 2
238000007034 nitrosation reaction Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
BSUZDWHFIHRVGS-UHFFFAOYSA-N (1-acetyl-4-hydroxyindazol-3-yl)methyl acetate Chemical compound C1=CC(O)=C2C(COC(=O)C)=NN(C(C)=O)C2=C1 BSUZDWHFIHRVGS-UHFFFAOYSA-N 0.000 description 1
BJMLLSSSTGHJJE-UHFFFAOYSA-N (4-methylbenzoyl) 4-methylbenzoate Chemical compound C1=CC(C)=CC=C1C(=O)OC(=O)C1=CC=C(C)C=C1 BJMLLSSSTGHJJE-UHFFFAOYSA-N 0.000 description 1
RVDRWZKPARNFLI-UHFFFAOYSA-N 1,3-dimethyl-2-nitro-4-phenylmethoxybenzene Chemical compound CC1=C([N+]([O-])=O)C(C)=CC=C1OCC1=CC=CC=C1 RVDRWZKPARNFLI-UHFFFAOYSA-N 0.000 description 1
CORAVBWSIRXYHF-UHFFFAOYSA-N 1-benzyl-4-nitroindazole Chemical compound N1=CC=2C([N+](=O)[O-])=CC=CC=2N1CC1=CC=CC=C1 CORAVBWSIRXYHF-UHFFFAOYSA-N 0.000 description 1
BKTILQSMSXKUMS-UHFFFAOYSA-N 1-benzyl-7-methyl-4-phenylmethoxyindazole Chemical compound C1=2C=NN(CC=3C=CC=CC=3)C=2C(C)=CC=C1OCC1=CC=CC=C1 BKTILQSMSXKUMS-UHFFFAOYSA-N 0.000 description 1
GUTJGRXTAAMNBO-UHFFFAOYSA-N 1-benzylindazol-4-amine Chemical compound N1=CC=2C(N)=CC=CC=2N1CC1=CC=CC=C1 GUTJGRXTAAMNBO-UHFFFAOYSA-N 0.000 description 1
HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
DVOYFAQCMNHJBW-UHFFFAOYSA-N 1h-indazole;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2C=NNC2=C1 DVOYFAQCMNHJBW-UHFFFAOYSA-N 0.000 description 1
ARYFLJOBGQNBLX-UHFFFAOYSA-N 1h-indol-2-ylmethyl 2,2-dimethylpropanoate Chemical compound C1=CC=C2NC(COC(=O)C(C)(C)C)=CC2=C1 ARYFLJOBGQNBLX-UHFFFAOYSA-N 0.000 description 1
DGBNUTJYQXQLSV-UHFFFAOYSA-N 1h-triazol-1-ium;chloride Chemical compound Cl.C1=CNN=N1 DGBNUTJYQXQLSV-UHFFFAOYSA-N 0.000 description 1
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
PBXYRJKKBWMVSG-UHFFFAOYSA-N 2,4-dimethyl-3-nitrophenol Chemical compound CC1=CC=C(O)C(C)=C1[N+]([O-])=O PBXYRJKKBWMVSG-UHFFFAOYSA-N 0.000 description 1
SHRJPIBSGVMGNL-UHFFFAOYSA-N 2-(3-bromopropoxy)-1h-indole Chemical compound C1=CC=C2NC(OCCCBr)=CC2=C1 SHRJPIBSGVMGNL-UHFFFAOYSA-N 0.000 description 1
LWKAAJKRJOLVQR-UHFFFAOYSA-N 2-benzyl-7-methyl-4-phenylmethoxyindazole Chemical compound C12=CN(CC=3C=CC=CC=3)N=C2C(C)=CC=C1OCC1=CC=CC=C1 LWKAAJKRJOLVQR-UHFFFAOYSA-N 0.000 description 1
VCMUBTODJYIRJM-UHFFFAOYSA-N 2-benzyl-7-methylindazol-4-ol Chemical compound N1=C2C(C)=CC=C(O)C2=CN1CC1=CC=CC=C1 VCMUBTODJYIRJM-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
PBSZHNXXFIYDBU-UHFFFAOYSA-N 2-methyl-1-nitro-3-phenylmethoxybenzene Chemical compound C1=CC=C([N+]([O-])=O)C(C)=C1OCC1=CC=CC=C1 PBSZHNXXFIYDBU-UHFFFAOYSA-N 0.000 description 1
HLDVKIKLLBOOPW-UHFFFAOYSA-N 2-methyl-1h-indol-3-ol Chemical compound C1=CC=C2C(O)=C(C)NC2=C1 HLDVKIKLLBOOPW-UHFFFAOYSA-N 0.000 description 1
WQAFOHJDMDYCPB-UHFFFAOYSA-N 3-(2-benzylindazol-4-yl)oxypropan-1-ol Chemical compound C1=C2C(OCCCO)=CC=CC2=NN1CC1=CC=CC=C1 WQAFOHJDMDYCPB-UHFFFAOYSA-N 0.000 description 1
RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
CSJRQRBMUOOMFH-UHFFFAOYSA-N 3-butyl-2h-indazole Chemical compound C1=CC=C2C(CCCC)=NNC2=C1 CSJRQRBMUOOMFH-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
GGHVECOXMJTFAC-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-1h-indazole Chemical compound C=1C=CC=2NN=CC=2C=1OCC1CO1 GGHVECOXMJTFAC-UHFFFAOYSA-N 0.000 description 1
PPFALTLMNHVYKA-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=C1OCC1CO1 PPFALTLMNHVYKA-UHFFFAOYSA-N 0.000 description 1
YEDQERJRGLCJKY-UHFFFAOYSA-N 4-[(2-chlorophenoxy)methyl]piperidine Chemical compound ClC1=CC=CC=C1OCC1CCNCC1 YEDQERJRGLCJKY-UHFFFAOYSA-N 0.000 description 1
PVLZQVJPOZTGMJ-UHFFFAOYSA-N 4-[(2-methylphenoxy)methyl]piperidine Chemical compound CC1=CC=CC=C1OCC1CCNCC1 PVLZQVJPOZTGMJ-UHFFFAOYSA-N 0.000 description 1
FXSNZTZVVUCCPE-UHFFFAOYSA-N 4-[(2-phenylmethoxyphenoxy)methyl]piperidine Chemical compound C1CNCCC1COC1=CC=CC=C1OCC1=CC=CC=C1 FXSNZTZVVUCCPE-UHFFFAOYSA-N 0.000 description 1
JRKWHWMRJYOIEA-UHFFFAOYSA-N 4-[(3-chlorophenoxy)methyl]piperidine Chemical compound ClC1=CC=CC(OCC2CCNCC2)=C1 JRKWHWMRJYOIEA-UHFFFAOYSA-N 0.000 description 1
KWLNQJLKIFFYNF-UHFFFAOYSA-N 4-[(4-chlorophenoxy)methyl]piperidine Chemical compound C1=CC(Cl)=CC=C1OCC1CCNCC1 KWLNQJLKIFFYNF-UHFFFAOYSA-N 0.000 description 1
WBTVZVUYPVQEIF-UHFFFAOYSA-N 4-nitro-1h-indazole Chemical compound [O-][N+](=O)C1=CC=CC2=C1C=NN2 WBTVZVUYPVQEIF-UHFFFAOYSA-N 0.000 description 1
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
QSWWZRWKIMIEJK-UHFFFAOYSA-N 5-(3-chloropropoxy)-1h-indole Chemical compound ClCCCOC1=CC=C2NC=CC2=C1 QSWWZRWKIMIEJK-UHFFFAOYSA-N 0.000 description 1
QEXOXABEHNRXRP-UHFFFAOYSA-N 5-(oxiran-2-ylmethoxy)-1h-indole Chemical compound C=1C=C2NC=CC2=CC=1OCC1CO1 QEXOXABEHNRXRP-UHFFFAOYSA-N 0.000 description 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
SKVHQYVHEVLNKR-UHFFFAOYSA-N 6-(3-chloropropoxy)-1h-indole Chemical compound ClCCCOC1=CC=C2C=CNC2=C1 SKVHQYVHEVLNKR-UHFFFAOYSA-N 0.000 description 1
ONYNOPPOVKYGRS-UHFFFAOYSA-N 6-methylindole Natural products CC1=CC=C2C=CNC2=C1 ONYNOPPOVKYGRS-UHFFFAOYSA-N 0.000 description 1
UTAZKQRKYUPPHU-UHFFFAOYSA-N 7-methyl-4-phenylmethoxy-1h-indazole Chemical compound C1=2C=NNC=2C(C)=CC=C1OCC1=CC=CC=C1 UTAZKQRKYUPPHU-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
USQOVYLRWBOSQC-HNNXBMFYSA-N CCCCCCNC(=O)Oc1cccc(c1)-c1ccc(cc1F)[C@H](C)C(O)=O Chemical compound CCCCCCNC(=O)Oc1cccc(c1)-c1ccc(cc1F)[C@H](C)C(O)=O USQOVYLRWBOSQC-HNNXBMFYSA-N 0.000 description 1
DRYZOOWDKZSLAP-UHFFFAOYSA-N CCCOC1=CC2=C(N1)C=C(C=C2)C(=O)OC Chemical compound CCCOC1=CC2=C(N1)C=C(C=C2)C(=O)OC DRYZOOWDKZSLAP-UHFFFAOYSA-N 0.000 description 1
QZGRLEMHXRGWCJ-UHFFFAOYSA-N CCCOC1=NC2=C(N1)C=CC=C2N3CCC(CC3)COC4=CC=CC=C4 Chemical compound CCCOC1=NC2=C(N1)C=CC=C2N3CCC(CC3)COC4=CC=CC=C4 QZGRLEMHXRGWCJ-UHFFFAOYSA-N 0.000 description 1
KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical group CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
QRMHDGWGLNLHMN-UHFFFAOYSA-N Methyl methoxyacetate Chemical compound COCC(=O)OC QRMHDGWGLNLHMN-UHFFFAOYSA-N 0.000 description 1
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
VERDEAUBKSHANT-UHFFFAOYSA-N N1C(=CC2=CC=CC=C12)C1=CC=CC=C1C(=O)OOCCC Chemical compound N1C(=CC2=CC=CC=C12)C1=CC=CC=C1C(=O)OOCCC VERDEAUBKSHANT-UHFFFAOYSA-N 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
VCDNGAOUMLSXDW-UHFFFAOYSA-N [4-(oxiran-2-ylmethoxy)-1h-indol-2-yl]methyl 2,2-dimethylpropanoate Chemical compound C1=CC=C2NC(COC(=O)C(C)(C)C)=CC2=C1OCC1CO1 VCDNGAOUMLSXDW-UHFFFAOYSA-N 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
MQTYQCAVOMQEFJ-UHFFFAOYSA-N benzene;trihydrochloride Chemical compound Cl.Cl.Cl.C1=CC=CC=C1 MQTYQCAVOMQEFJ-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
OTGAHJPFNKQGAE-UHFFFAOYSA-N cresatin Chemical compound CC(=O)OC1=CC=CC(C)=C1 OTGAHJPFNKQGAE-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
DDNRNCSGIYDEMC-UHFFFAOYSA-N ethanol;formic acid Chemical compound CCO.OC=O DDNRNCSGIYDEMC-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
SVEIFRZAHBWLFT-UHFFFAOYSA-N methyl 4-(oxiran-2-ylmethoxy)-1h-indole-6-carboxylate Chemical compound C=12C=CNC2=CC(C(=O)OC)=CC=1OCC1CO1 SVEIFRZAHBWLFT-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
BFEAKHXJJMDHKD-UHFFFAOYSA-N n,n-dimethyl-4-(oxiran-2-ylmethoxy)-1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N(C)C)=CC2=C1OCC1CO1 BFEAKHXJJMDHKD-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SU772541695A 1976-11-12 1977-11-11 Способ получени производных аминопропанола или их солей SU1041033A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19762651574 DE2651574A1 (de)	1976-11-12	1976-11-12	Ein neues aminopropanol-derivat und verfahren zu dessen herstellung

Publications (1)

Publication Number	Publication Date
SU1041033A3 true SU1041033A3 (ru)	1983-09-07

Family

ID=5992970

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU772541695A SU1041033A3 (ru)	1976-11-12	1977-11-11	Способ получени производных аминопропанола или их солей

Country Status (4)

Country	Link
BE (1)	BE860701A (fr)
DE (1)	DE2651574A1 (fr)
SU (1)	SU1041033A3 (fr)
ZA (1)	ZA776647B (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2737630A1 (de) *	1977-08-20	1979-03-01	Boehringer Mannheim Gmbh	Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2905877A1 (de)	1979-02-16	1980-08-28	Boehringer Mannheim Gmbh	Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3068678D1 (en) *	1979-08-10	1984-08-30	Sandoz Ag	3-aminopropoxyaryl derivatives, their preparation and pharmaceutical compositions containing them
DE3721260A1 (de) *	1987-06-27	1989-01-12	Beiersdorf Ag	Neue indolylpropanole, verfahren zu ihrer herstellung und ihre verwendung sowie die verbindungen enthaltende zubereitungen
ZA9610741B (en)	1995-12-22	1997-06-24	Warner Lambert Co	4-Substituted piperidine analogs and their use as subtype selective nmda receptor antagonists
ZA9610738B (en)	1995-12-22	1997-06-24	Warner Lambert Co	Subtype selective nmda receptor ligands and the use thereof
ZA9610745B (en) *	1995-12-22	1997-06-24	Warner Lambert Co	4-Subsituted piperidine analogs and their use as subtype selective nmda receptor antagonists
ZA9610736B (en)	1995-12-22	1997-06-27	Warner Lambert Co	2-Substituted piperidine analogs and their use as subtypeselective nmda receptor antagonists
CN110974975B (zh) *	2019-12-12	2023-10-20	成都百利多特生物药业有限责任公司	一种快速释放的抗体药物偶联物

1976
- 1976-11-12 DE DE19762651574 patent/DE2651574A1/de not_active Withdrawn
1977
- 1977-11-07 ZA ZA00776647A patent/ZA776647B/xx unknown
- 1977-11-10 BE BE182523A patent/BE860701A/fr not_active IP Right Cessation
- 1977-11-11 SU SU772541695A patent/SU1041033A3/ru active

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
1. Неакцептованна за вка DE 2619164, кл. С 07 D 231/56, опублик. 1975. *

Also Published As

Publication number	Publication date
ZA776647B (en)	1978-09-27
BE860701A (fr)	1978-05-10
DE2651574A1 (de)	1978-05-18

Publication	Publication Date	Title
US4243807A (en)	1981-01-06	4-Phenoxymethyl-piperidines
US4029801A (en)	1977-06-14	Pharmaceutical compositions and methods of treating hypertension
US4584383A (en)	1986-04-22	Substituted 2-mercapto-imidazoles and their preparation
NO118710B (fr)	1970-02-02
NO162176B (no)	1989-08-14	Middel for bekjempelse av plantesykdommer og anvendelse derav.
CS228106B2 (en)	1984-05-14	Production of novel derivatives of 3-/4-phenoxymethylpiperidino/-propanol
NO126734B (fr)	1973-03-19
FI62052B (fi)	1982-07-30	Foerfarande foer framstaellning av farmakologiskt vaerdefulla 4-aminofenyletanolaminer med saerskilt beta 2-mimetisk och/eller alfa 1-blockerande verkan
US4404384A (en)	1983-09-13	O-[3-(4-Substituted-piperazin-1-yl)-2-hydroxypropyl]-hydroxylamines
US4073911A (en)	1978-02-14	Indolylalkylpiperidines
NO125911B (fr)	1972-11-27
US4569933A (en)	1986-02-11	Antihypertensive substituted derivatives of 2,5-diamino 1,4-diazole
US4046767A (en)	1977-09-06	Piperidino compounds
JPS6019305B2 (ja)	1985-05-15	ジヒドロベンゾフラン誘導体
DE2737630C2 (fr)	1987-11-05
US3992389A (en)	1976-11-16	Heterocyclic compounds
NO164899B (no)	1990-08-20	Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazolylindolforbindelser.
US4853408A (en)	1989-08-01	4-phenylpropyl-indoles having antiarythmic activity
US4242347A (en)	1980-12-30	Hypotensive indolylalkylpiperidyl guanidines and isoureas
US4147786A (en)	1979-04-03	1-Indolylalkyl-3-or 4-trimethyleneurido-piperidines
NO138250B (no)	1978-04-24	Analogifremgangsmaate for fremstilling av farmakologisk aktive benzylaminer
JPS628117B2 (fr)	1987-02-20
US4927968A (en)	1990-05-22	Chemical intermediates and process
NO158940B (no)	1988-08-08	Analogifremgangsmaate for fremstilling av nye, terapeutiskvirksomme indolderivater.
JPS624263A (ja)	1987-01-10	ヒドロキシアルコキシ―４―フェニルプロピルインドールの新規な誘導体及びその塩、それらの製造方法並びに不整脈防止剤