PL81365B1 - 4-(2-hydroxy-3-amino propoxy)-indole derivatives[us3696120a] - Google Patents
4-(2-hydroxy-3-amino propoxy)-indole derivatives[us3696120a] Download PDFInfo
- Publication number
- PL81365B1 PL81365B1 PL1970142487A PL14248770A PL81365B1 PL 81365 B1 PL81365 B1 PL 81365B1 PL 1970142487 A PL1970142487 A PL 1970142487A PL 14248770 A PL14248770 A PL 14248770A PL 81365 B1 PL81365 B1 PL 81365B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- compounds
- methyl
- hydroxy
- ethyl ester
- Prior art date
Links
- 229940054051 antipsychotic indole derivative Drugs 0.000 title claims abstract description 6
- CKNUDCBHUGWSEL-UHFFFAOYSA-N 1-amino-3-(1h-indol-4-yloxy)propan-2-ol Chemical class NCC(O)COC1=CC=CC2=C1C=CN2 CKNUDCBHUGWSEL-UHFFFAOYSA-N 0.000 title 1
- 150000002475 indoles Chemical class 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 107
- -1 alkyl radical Chemical class 0.000 claims description 67
- 238000000034 method Methods 0.000 claims description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 239000003054 catalyst Substances 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 28
- 125000004494 ethyl ester group Chemical group 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 20
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 9
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 9
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- ZIBZWXSKLNGAMQ-UHFFFAOYSA-N 1-[(2,3-dimethyl-1H-indol-4-yl)oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC=1NC2=CC=CC(=C2C1C)OCC(CNC(C)C)O ZIBZWXSKLNGAMQ-UHFFFAOYSA-N 0.000 claims description 4
- AJWIXHIEDSHFQF-UHFFFAOYSA-N ethyl 4-[2-hydroxy-3-(pentan-3-ylamino)propoxy]-3-methyl-1H-indole-2-carboxylate Chemical compound C(C)OC(=O)C=1NC2=CC=CC(=C2C1C)OCC(CNC(CC)CC)O AJWIXHIEDSHFQF-UHFFFAOYSA-N 0.000 claims description 4
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000002466 imines Chemical class 0.000 claims description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- ANRYNMHEXSKMAJ-UHFFFAOYSA-N C(C)OC(=O)C=1NC2=CC=CC(=C2C1C)OCC(CNC1CC1)O Chemical compound C(C)OC(=O)C=1NC2=CC=CC(=C2C1C)OCC(CNC1CC1)O ANRYNMHEXSKMAJ-UHFFFAOYSA-N 0.000 claims 1
- XMMQQCNXXIYFFK-UHFFFAOYSA-N CCOC(C(NC1=CC=C2)=C(C)C1=C2OCC(CNC(C)(C)C)O)=O Chemical compound CCOC(C(NC1=CC=C2)=C(C)C1=C2OCC(CNC(C)(C)C)O)=O XMMQQCNXXIYFFK-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- QIWNOVRXWQPVIY-UHFFFAOYSA-N propylbenzene Chemical compound [CH2]CCC1=CC=CC=C1 QIWNOVRXWQPVIY-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 229910052763 palladium Inorganic materials 0.000 description 16
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 235000002906 tartaric acid Nutrition 0.000 description 8
- 239000011975 tartaric acid Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- YZPMQHFEXAJCIY-UHFFFAOYSA-N (4-phenylmethoxy-1h-indol-2-yl)methanol Chemical compound C1=CC=C2NC(CO)=CC2=C1OCC1=CC=CC=C1 YZPMQHFEXAJCIY-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000005902 aminomethylation reaction Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- GUKLAUJRBOSKNR-UHFFFAOYSA-N 2,3-dimethyl-1h-indol-4-ol Chemical compound C1=CC(O)=C2C(C)=C(C)NC2=C1 GUKLAUJRBOSKNR-UHFFFAOYSA-N 0.000 description 4
- YLDAWJZLIJLULE-UHFFFAOYSA-N 2-(hydroxymethyl)-3-methyl-1h-indol-4-ol Chemical compound C1=CC(O)=C2C(C)=C(CO)NC2=C1 YLDAWJZLIJLULE-UHFFFAOYSA-N 0.000 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 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
- WUCPCORZZJWVHG-UHFFFAOYSA-N 4-bromo-2-propylthiophene Chemical compound CCCC1=CC(Br)=CS1 WUCPCORZZJWVHG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MDVSNUBLGQABAR-UHFFFAOYSA-N 1-[[2-(hydroxymethyl)-3-methyl-1H-indol-4-yl]oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound OC(COC1=C2C(=C(NC2=CC=C1)CO)C)CNC(C)C MDVSNUBLGQABAR-UHFFFAOYSA-N 0.000 description 2
- GBVHBAQGRMFKIJ-UHFFFAOYSA-N 2-(hydroxymethyl)-1h-indol-4-ol Chemical compound C1=CC=C2NC(CO)=CC2=C1O GBVHBAQGRMFKIJ-UHFFFAOYSA-N 0.000 description 2
- LSGNIYBPNQLMTO-UHFFFAOYSA-N 2-methylindole-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C)(C(O)=O)C=C21 LSGNIYBPNQLMTO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000006683 Mannich reaction Methods 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- OZQXZSIVKVCSDF-UHFFFAOYSA-N ethyl 3-methyl-1h-indole-2-carboxylate Chemical compound C1=CC=C2C(C)=C(C(=O)OCC)NC2=C1 OZQXZSIVKVCSDF-UHFFFAOYSA-N 0.000 description 2
- NLACEZDIDFTMBA-UHFFFAOYSA-N ethyl 4-hydroxy-3-methyl-1h-indole-2-carboxylate Chemical compound C1=CC(O)=C2C(C)=C(C(=O)OCC)NC2=C1 NLACEZDIDFTMBA-UHFFFAOYSA-N 0.000 description 2
- HIQPISGKBJHKIN-UHFFFAOYSA-N ethyl 4-phenylmethoxy-1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=CC2=C1OCC1=CC=CC=C1 HIQPISGKBJHKIN-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- AXPRURZTNUHICG-UHFFFAOYSA-N methyl 4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-methyl-1H-indole-2-carboxylate Chemical compound COC(=O)C=1NC2=CC=CC(=C2C1C)OCC(CNC(C)C)O AXPRURZTNUHICG-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- BYNYWOCKJMPYRJ-UHFFFAOYSA-N (3-methyl-1h-indol-2-yl)methanol Chemical compound C1=CC=C2C(C)=C(CO)NC2=C1 BYNYWOCKJMPYRJ-UHFFFAOYSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- ZRZHWRGNHGOPTB-UHFFFAOYSA-N 1-[[2-(hydroxymethyl)-1H-indol-4-yl]oxy]-4-phenyl-3-(propan-2-ylamino)butan-2-ol Chemical compound C(C1=CC=CC=C1)C(C(COC1=C2C=C(NC2=CC=C1)CO)O)NC(C)C ZRZHWRGNHGOPTB-UHFFFAOYSA-N 0.000 description 1
- XEEANGGQJOWRTG-UHFFFAOYSA-N 1h-indol-2-ylmethanol Chemical compound C1=CC=C2NC(CO)=CC2=C1 XEEANGGQJOWRTG-UHFFFAOYSA-N 0.000 description 1
- PTWSSXBAMVQSJP-UHFFFAOYSA-N 2,3-dimethyl-4-(oxiran-2-ylmethoxy)-1h-indole Chemical compound C=12C(C)=C(C)NC2=CC=CC=1OCC1CO1 PTWSSXBAMVQSJP-UHFFFAOYSA-N 0.000 description 1
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 1
- QGWACZFSCSTOCG-UHFFFAOYSA-N 2-methyl-4-phenylmethoxy-1h-indole Chemical compound C1=CC=C2NC(C)=CC2=C1OCC1=CC=CC=C1 QGWACZFSCSTOCG-UHFFFAOYSA-N 0.000 description 1
- BJOMANWEPTZALW-UHFFFAOYSA-N 3-propoxy-1H-indole-2-carboxylic acid Chemical compound CCCOc1c([nH]c2ccccc12)C(O)=O BJOMANWEPTZALW-UHFFFAOYSA-N 0.000 description 1
- RLEYZYROXADSIU-UHFFFAOYSA-N 4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-methyl-1H-indole-2-carboxylic acid Chemical compound OC(COC1=C2C(=C(NC2=CC=C1)C(=O)O)C)CNC(C)C RLEYZYROXADSIU-UHFFFAOYSA-N 0.000 description 1
- WLTUAEIHGDPQQT-UHFFFAOYSA-N 4-hydroxy-3-methyl-1h-indole-2-carboxylic acid Chemical compound C1=CC(O)=C2C(C)=C(C(O)=O)NC2=C1 WLTUAEIHGDPQQT-UHFFFAOYSA-N 0.000 description 1
- GSXFWBDVTDHJFZ-UHFFFAOYSA-N 4-phenylmethoxy-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1OCC1=CC=CC=C1 GSXFWBDVTDHJFZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000020446 Cardiac disease Diseases 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- MDPUIQKXQCOEKH-UHFFFAOYSA-N N,N-dimethyl-1-(4-phenylmethoxy-1H-indol-2-yl)methanamine Chemical compound C(C1=CC=CC=C1)OC1=C2C=C(NC2=CC=C1)CN(C)C MDPUIQKXQCOEKH-UHFFFAOYSA-N 0.000 description 1
- SFCTUUHIYYPOAD-UHFFFAOYSA-N N,N-dimethyl-4-phenylmethoxy-1H-indole-2-carboxamide Chemical compound CN(C(=O)C=1NC2=CC=CC(=C2C1)OCC1=CC=CC=C1)C SFCTUUHIYYPOAD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010040844 Skin exfoliation Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- VMWZRHGIAVCFNS-UHFFFAOYSA-J aluminum;lithium;tetrahydroxide Chemical compound [Li+].[OH-].[OH-].[OH-].[OH-].[Al+3] VMWZRHGIAVCFNS-UHFFFAOYSA-J 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-M cyclohexylsulfamate Chemical compound [O-]S(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-M 0.000 description 1
- 230000009615 deamination Effects 0.000 description 1
- 238000006481 deamination reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000035618 desquamation Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- QSJJWHZIFNMGDY-UHFFFAOYSA-N ethyl 3-methyl-4-phenylmethoxy-1h-indole-2-carboxylate Chemical compound C=12C(C)=C(C(=O)OCC)NC2=CC=CC=1OCC1=CC=CC=C1 QSJJWHZIFNMGDY-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- JPELCBSZNYYDPE-UHFFFAOYSA-N formaldehyde;lithium Chemical compound [Li].O=C JPELCBSZNYYDPE-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000009884 interesterification Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940049920 malate Drugs 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
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- USBAUXJPPHVCTF-UHFFFAOYSA-N n-benzylcyclopropanamine Chemical compound C=1C=CC=CC=1CNC1CC1 USBAUXJPPHVCTF-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1191869A CH514586A (de) | 1969-08-05 | 1969-08-05 | Verfahren zur Herstellung neuer Indolverbindungen |
| CH1586569 | 1969-10-24 | ||
| CH1586669 | 1969-10-24 | ||
| CH438370A CH525884A (de) | 1970-03-24 | 1970-03-24 | Verfahren zur Herstellung neuer Indolderivate |
| CH953670 | 1970-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL81365B1 true PL81365B1 (en) | 1975-08-30 |
Family
ID=27509196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970142487A PL81365B1 (en) | 1969-08-05 | 1970-08-03 | 4-(2-hydroxy-3-amino propoxy)-indole derivatives[us3696120a] |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3696120A (en, 2012) |
| JP (1) | JPS5022555B1 (en, 2012) |
| BE (1) | BE754360A (en, 2012) |
| DE (1) | DE2038482A1 (en, 2012) |
| FR (1) | FR2068461B1 (en, 2012) |
| GB (1) | GB1318050A (en, 2012) |
| PL (1) | PL81365B1 (en, 2012) |
| SE (1) | SE369522B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4152446A (en) * | 1974-11-16 | 1979-05-01 | Boehringer Mannheim Gmbh | Aminopropanol compounds and compositions for the treatment of cardiac and circulatory diseases |
| US4076829A (en) * | 1974-11-16 | 1978-02-28 | Boehringer Mannheim Gmbh | Aminopropanol compounds and compositions for the treatment of cardiac and circulatory diseases |
| DE2508251C2 (de) * | 1975-02-26 | 1983-12-29 | Boehringer Mannheim Gmbh, 6800 Mannheim | Derivate des Indols, Verfahren zu deren Herstellung sowie diese enthaltende Arzneimittel |
| US4340541A (en) * | 1975-08-15 | 1982-07-20 | Sandoz Ltd. | 4-(2-Benzoyloxy-3-tert.-butylaminopropoxy-2-methyl indole |
| US4235919A (en) * | 1977-07-21 | 1980-11-25 | Sandoz Ltd. | 1-(Indol-4-yloxy)-3-(2-substituted amino)-2-propanols and pharmaceutical use thereof |
| JPS54156272U (en, 2012) * | 1978-04-24 | 1979-10-30 | ||
| JPS5746200Y2 (en, 2012) * | 1978-06-26 | 1982-10-12 | ||
| DE3068678D1 (en) * | 1979-08-10 | 1984-08-30 | Sandoz Ag | 3-aminopropoxyaryl derivatives, their preparation and pharmaceutical compositions containing them |
| DE3115993A1 (de) * | 1981-04-13 | 1982-11-11 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue indol-derivate, verfahren zu ihrer herstellung und pharmazeutische praeparate, die diese verbindungen enthalten |
| HU195972B (en) * | 1985-07-01 | 1988-08-29 | Richter Gedeon Vegyeszet | Process for producing new diamino-androstane derivatives and pharmaceutical compositions containing them |
| US5013761A (en) * | 1988-06-03 | 1991-05-07 | Eli Lilly And Company | Serotonin antagonists |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1129072A (en) * | 1966-02-01 | 1968-10-02 | Ici Ltd | Benzofuran and indole derivatives |
| US3471515A (en) * | 1965-02-01 | 1969-10-07 | Sandoz Ag | (2-hydroxy-3-substituted aminopropoxy)indoles |
| FR353F (en, 2012) * | 1968-06-07 | 1972-01-07 | ||
| DE1948507C2 (de) * | 1969-09-25 | 1982-10-21 | Sandoz-Patent-GmbH, 7850 Lörrach | 4-(2-Hydroxy-3-aminopropoxy)-indolderivate, ihre Salze, Verfahren zu ihrer Herstellung und Heilmittel |
-
0
- BE BE754360D patent/BE754360A/xx unknown
-
1970
- 1970-07-20 GB GB3509970A patent/GB1318050A/en not_active Expired
- 1970-07-28 US US58985A patent/US3696120A/en not_active Expired - Lifetime
- 1970-08-03 SE SE10622/70A patent/SE369522B/xx unknown
- 1970-08-03 DE DE19702038482 patent/DE2038482A1/de not_active Ceased
- 1970-08-03 PL PL1970142487A patent/PL81365B1/pl unknown
- 1970-08-04 JP JP45068283A patent/JPS5022555B1/ja active Pending
- 1970-08-04 FR FR7028683A patent/FR2068461B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2038482A1 (de) | 1971-02-18 |
| FR2068461B1 (en, 2012) | 1974-01-11 |
| BE754360A (fr) | 1971-02-03 |
| US3696120A (en) | 1972-10-03 |
| JPS5022555B1 (en, 2012) | 1975-07-31 |
| SE369522B (en, 2012) | 1974-09-02 |
| FR2068461A1 (en, 2012) | 1971-08-27 |
| GB1318050A (en) | 1973-05-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI63571C (fi) | Foerfarande foer framstaellning av analgetiskt verkande racemiska eller diastereomera och optiskt aktiva 2-tetrahydrofurfuryl-(1r/s 5r/s 9r/s)-2'-hydroxi-5,9-dimetyl-6,7-bensomorfaner och deras syraadditionssalter | |
| PL81365B1 (en) | 4-(2-hydroxy-3-amino propoxy)-indole derivatives[us3696120a] | |
| HU193536B (en) | Process for the production of new hydroxy-alkane- and alkene-tetrahydrofuran- and tetrahydropyran-derivatives | |
| DE2822227A1 (de) | Spiroaminderivate, verfahren zu ihrer herstellung, diese enthaltende arzneimittel und verwendung derselben | |
| US3705907A (en) | 4-(2-hydroxy)-3-aminopropoxy)-indole derivatives | |
| PL90695B1 (en, 2012) | ||
| US2908691A (en) | Hydroxyphenalkylaminoalkylindoles and ethers corresponding thereto | |
| DE2447756A1 (de) | Verfahren zur herstellung neuer heterocyclischer verbindungen | |
| AU665002B2 (en) | New selective aromatase inhibiting 4(5)-imidazoles | |
| IE50885B1 (en) | 1-phenyl-2-cyclohexene-1-alkylamine derivatives,a process for their preparation and medicaments containing them | |
| PL100799B1 (pl) | Sposob wytwarzania nowych pochodnych aminopropanolu | |
| Chapman et al. | 265. Di-N-substituted 2-halogenoethylamines. Part VI. NN-dialkyl-(or N-alkyl)-2-alkyl (or aryl or arylalkyl) derivatives: synthesis, reactivity, and pharmacology | |
| DE2401374A1 (de) | Tetrahydronaphthyloxyaminderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate | |
| US2355659A (en) | Piperidine derivatives and process for the manufacture of the same | |
| Molina et al. | Fused carbazoles by tandem Aza Wittig/electrocyclic ring closure. Preparation of 6H-pyrido [4, 3-b] carbazole, 11H-pyrido [4, 3-a] carbazole and 11H-pyrido [3, 4-a] carbazole derivatives | |
| EP0074130B1 (en) | New imidazole compounds, process for the preparation thereof and pharmaceutical compositions containing them | |
| PL81987B1 (en, 2012) | ||
| US5182394A (en) | Liquid crystalline diglycidyl compounds | |
| US4252824A (en) | Amino-ethanol derivatives | |
| NZ202857A (en) | Preparation of beta-((2-methylpropoxy)methyl)-n-phenyl-n-(phenylmethyl)-1-pyrrolidineethanamine hydrochloride hydrate | |
| US2694706A (en) | Alkenylamevoalkanoylphenotfflazine | |
| SU841582A3 (ru) | Способ получени аминопроиз-ВОдНыХ АзидОфЕНОлА или иХ СОлЕй | |
| EP0002792A1 (en) | 3-Aminopropoxyaryl derivatives, their preparation and pharmaceutical compositions containing them | |
| US3975539A (en) | Pharmaceutical compositions containing an N,N-bis-(3-phenoxy-2-hydroxy-propyl)-alkylenediamine and method of use | |
| US3068234A (en) | Preparation of 16-oxo-isomorphinan |