GB942548A - - Google Patents
Info
- Publication number
- GB942548A GB942548A GB1016660A GB1016660A GB942548A GB 942548 A GB942548 A GB 942548A GB 1016660 A GB1016660 A GB 1016660A GB 1016660 A GB1016660 A GB 1016660A GB 942548 A GB942548 A GB 942548A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- reacting
- indole
- reducing
- hydrogen atom
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 150000004820 halides Chemical class 0.000 abstract 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 3
- -1 indole magnesium halide Chemical class 0.000 abstract 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 150000001540 azides Chemical class 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- OCDGBSUVYYVKQZ-UHFFFAOYSA-N gramine Chemical compound C1=CC=C2C(CN(C)C)=CNC2=C1 OCDGBSUVYYVKQZ-UHFFFAOYSA-N 0.000 abstract 2
- GOERTRUXQHDLHC-UHFFFAOYSA-N gramine Natural products COC1=CC=C2NC=C(CN(C)C)C2=C1 GOERTRUXQHDLHC-UHFFFAOYSA-N 0.000 abstract 2
- 150000002475 indoles Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000004971 nitroalkyl group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- HCGYMSSYSAKGPK-UHFFFAOYSA-N 2-nitro-1h-indole Chemical class C1=CC=C2NC([N+](=O)[O-])=CC2=C1 HCGYMSSYSAKGPK-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
-
- 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
-
- 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
-
- 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
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7167759A CH373381A (de) | 1959-07-13 | 1959-07-13 | Verfahren zur Herstellung neuer basischer Indol-Derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB942548A true GB942548A (enrdf_load_stackoverflow) | 1963-11-27 |
Family
ID=4531186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1016660A Expired GB942548A (enrdf_load_stackoverflow) | 1959-07-13 | 1960-03-22 |
Country Status (3)
| Country | Link |
|---|---|
| CH (4) | CH373381A (enrdf_load_stackoverflow) |
| ES (1) | ES257146A1 (enrdf_load_stackoverflow) |
| GB (1) | GB942548A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7125906B2 (en) | 2002-04-03 | 2006-10-24 | Astrazeneca Ab | Indole derivatives having anti-angiogenetic activity |
| WO2022000091A1 (en) | 2020-06-30 | 2022-01-06 | Field Trip Psychedelics Inc. | Tryptamine prodrugs |
| US11591353B2 (en) | 2020-02-04 | 2023-02-28 | Mindset Pharma Inc. | Psilocin derivatives as serotonergic psychedelic agents for the treatment of CNS disorders |
| US11746087B1 (en) | 2022-03-18 | 2023-09-05 | Enveric Biosciences Canada Inc. | C4-carboxylic acid-substituted tryptamine derivatives and methods of using |
| EP4229036A4 (en) * | 2020-10-13 | 2024-09-04 | Caamtech, Inc. | TRYPTAMINE DERIVATIVES AND THEIR THERAPEUTIC USES |
| WO2025049510A1 (en) * | 2023-08-29 | 2025-03-06 | Caamtech, Inc. | 4-hydroxy-n-ethyltryptamine |
| EP4337666A4 (en) * | 2021-05-10 | 2025-03-26 | London Pharmaceuticals and Research Corporation | Psilocybin and psilocin conjugates for treatment of mental illnesses |
-
1959
- 1959-07-13 CH CH7167759A patent/CH373381A/de unknown
- 1959-08-21 CH CH724364A patent/CH380131A/de unknown
- 1959-08-21 CH CH724264A patent/CH380130A/de unknown
-
1960
- 1960-02-24 CH CH204960A patent/CH383379A/de unknown
- 1960-03-22 GB GB1016660A patent/GB942548A/en not_active Expired
- 1960-04-06 ES ES0257146A patent/ES257146A1/es not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7125906B2 (en) | 2002-04-03 | 2006-10-24 | Astrazeneca Ab | Indole derivatives having anti-angiogenetic activity |
| US11591353B2 (en) | 2020-02-04 | 2023-02-28 | Mindset Pharma Inc. | Psilocin derivatives as serotonergic psychedelic agents for the treatment of CNS disorders |
| US12054505B2 (en) | 2020-02-04 | 2024-08-06 | Mindset Pharma Inc. | Psilocin derivatives as serotonergic psychedelic agents for the treatment of CNS disorders |
| US12378266B2 (en) | 2020-02-04 | 2025-08-05 | Mindset Pharma Inc. | Psilocin derivatives as serotonergic psychedelic agents for the treatment of CNS disorders |
| WO2022000091A1 (en) | 2020-06-30 | 2022-01-06 | Field Trip Psychedelics Inc. | Tryptamine prodrugs |
| EP4229036A4 (en) * | 2020-10-13 | 2024-09-04 | Caamtech, Inc. | TRYPTAMINE DERIVATIVES AND THEIR THERAPEUTIC USES |
| EP4337666A4 (en) * | 2021-05-10 | 2025-03-26 | London Pharmaceuticals and Research Corporation | Psilocybin and psilocin conjugates for treatment of mental illnesses |
| US11746087B1 (en) | 2022-03-18 | 2023-09-05 | Enveric Biosciences Canada Inc. | C4-carboxylic acid-substituted tryptamine derivatives and methods of using |
| US12065404B2 (en) | 2022-03-18 | 2024-08-20 | Enveric Biosciences Canada Inc. | C4-carboxylic acid-substituted tryptamine derivatives and methods of using |
| US12077498B2 (en) | 2022-03-18 | 2024-09-03 | Enveric Biosciences Canada Inc. | C4-carboxylic acid-substituted tryptamine derivatives and methods of using |
| WO2025049510A1 (en) * | 2023-08-29 | 2025-03-06 | Caamtech, Inc. | 4-hydroxy-n-ethyltryptamine |
Also Published As
| Publication number | Publication date |
|---|---|
| CH383379A (de) | 1964-10-31 |
| CH380130A (de) | 1964-07-31 |
| CH380131A (de) | 1964-07-31 |
| ES257146A1 (es) | 1960-12-01 |
| CH373381A (de) | 1963-11-30 |
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