CH532041A - Verfahren zur Herstellung neuer Indolderivate - Google Patents
Verfahren zur Herstellung neuer IndolderivateInfo
- Publication number
- CH532041A CH532041A CH1087972A CH1087972A CH532041A CH 532041 A CH532041 A CH 532041A CH 1087972 A CH1087972 A CH 1087972A CH 1087972 A CH1087972 A CH 1087972A CH 532041 A CH532041 A CH 532041A
- Authority
- CH
- Switzerland
- Prior art keywords
- compounds
- formula
- prepn
- indolyl
- amino ethers
- Prior art date
Links
- MSEWZDUFOHBRKK-UHFFFAOYSA-N o-(1h-indol-4-yl)hydroxylamine Chemical class NOC1=CC=CC2=C1C=CN2 MSEWZDUFOHBRKK-UHFFFAOYSA-N 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 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 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229940054051 antipsychotic indole derivative Drugs 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 150000002475 indoles Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000002876 beta blocker Substances 0.000 abstract 1
- 229940030611 beta-adrenergic blocking agent Drugs 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- -1 diethyl ether Chemical compound 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YKGJUSKLOHNPIM-UHFFFAOYSA-N 1-(1H-indol-4-yloxy)-4-phenyl-3-(propan-2-ylamino)butan-2-ol Chemical compound C(C1=CC=CC=C1)C(C(COC1=C2C=CNC2=CC=C1)O)NC(C)C YKGJUSKLOHNPIM-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BYGRDLSPZRUONE-UHFFFAOYSA-N C(C(=O)O)(=O)O.C1(=CC=CC=C1)CCCNCC(COC1=C2C=CNC2=CC=C1)OC(C(C)(C)C)=O Chemical compound C(C(=O)O)(=O)O.C1(=CC=CC=C1)CCCNCC(COC1=C2C=CNC2=CC=C1)OC(C(C)(C)C)=O BYGRDLSPZRUONE-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- DJAVTUKKYQWOAP-UHFFFAOYSA-N [1-(1H-indol-4-yloxy)-4-phenyl-3-(propan-2-ylamino)butan-2-yl] 2,2-dimethylpropanoate Chemical compound C(C1=CC=CC=C1)C(C(COC1=C2C=CNC2=CC=C1)OC(C(C)(C)C)=O)NC(C)C DJAVTUKKYQWOAP-UHFFFAOYSA-N 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000012928 buffer substance Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000001834 epinephrinelike Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1087972A CH532041A (de) | 1970-03-24 | 1970-03-24 | Verfahren zur Herstellung neuer Indolderivate |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH437970A CH532040A (de) | 1970-03-24 | 1970-03-24 | Verfahren zur Herstellung neuer Indolderivate |
| CH1087972A CH532041A (de) | 1970-03-24 | 1970-03-24 | Verfahren zur Herstellung neuer Indolderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH532041A true CH532041A (de) | 1972-12-31 |
Family
ID=4275012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1087972A CH532041A (de) | 1970-03-24 | 1970-03-24 | Verfahren zur Herstellung neuer Indolderivate |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5442979B1 (enExample) |
| CH (1) | CH532041A (enExample) |
| ES (2) | ES389422A1 (enExample) |
| HU (1) | HU164315B (enExample) |
| IE (1) | IE35285B1 (enExample) |
| IL (1) | IL36456A (enExample) |
| PL (1) | PL83145B1 (enExample) |
| SU (1) | SU378006A3 (enExample) |
| ZA (1) | ZA711917B (enExample) |
-
1970
- 1970-03-24 CH CH1087972A patent/CH532041A/de not_active IP Right Cessation
-
1971
- 1971-03-22 PL PL14707071A patent/PL83145B1/pl unknown
- 1971-03-22 HU HUSA2180A patent/HU164315B/hu unknown
- 1971-03-22 IE IE359/71A patent/IE35285B1/xx unknown
- 1971-03-22 ES ES389422A patent/ES389422A1/es not_active Expired
- 1971-03-22 IL IL36456A patent/IL36456A/xx unknown
- 1971-03-23 JP JP1681971A patent/JPS5442979B1/ja active Pending
- 1971-03-24 ZA ZA711917A patent/ZA711917B/xx unknown
- 1971-03-24 SU SU1636301A patent/SU378006A3/ru active
-
1973
- 1973-07-16 ES ES416951A patent/ES416951A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL36456A (en) | 1974-03-14 |
| PL83145B1 (enExample) | 1975-12-31 |
| IL36456A0 (en) | 1971-05-26 |
| ZA711917B (en) | 1972-10-25 |
| HU164315B (enExample) | 1974-01-28 |
| ES389422A1 (es) | 1974-12-16 |
| ES416951A1 (es) | 1976-05-01 |
| SU378006A3 (enExample) | 1973-04-17 |
| IE35285B1 (en) | 1976-01-07 |
| JPS5442979B1 (enExample) | 1979-12-17 |
| IE35285L (en) | 1971-09-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |