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
- -1 indole magnesium halide Chemical class 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 3
- 150000002475 indoles Chemical class 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
- 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
- 150000004820 halides Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 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 compound 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
- 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
- 125000005843 halogen group Chemical group 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)
Abstract
942,548. Indoles. SANDOZ Ltd. March 22, 1960 [April 7, 1959; July 13, 1959; Aug. 21, 1959(2); Feb. 24, 1960], No. 10166/60. Addition to 911,946. Heading C2C. The invention comprises indoles of the general formula: and their acid addition salts, wherein R 1 is a hydrogen atom or a C 7-10 aralkyl group, R 2 is a hydrogen atom or a C 1-6 alkyl group or a C 7-10 aralkyl group, each of R 3 and R 4 is a hydrogen atom or a C 1-6 alkyl group and A is a C 1-3 alkylene group with the proviso that R 1 -R 4 may be the same and with the further proviso that A and R 2 together contain at least 2 carbon atoms when R 3 and R 4 each signify an alkyl group and the preparation thereof by introducing, in known manner for such reactions, into the 3-position of an indole of the formula: (wherein R 1 <SP>1</SP> is a C 7-10 aralkyl group) an organic radical containing a nitrogen atom and capable of being converted by a method involving reduction into an amino containing group of the formula: converting the said group into the said amino group by a method involving reduction said reduction being effected under conditions such that the group R 1 <SP>1</SP> is not split off and optionally removing the group R 1 <SP>1</SP> by acid hydrolysis or reduction with hydrogen in the presence of a palladium catalyst or with an alkali metal in liquid ammonia. Compounds of the invention wherein R 2 is a hydrogen atom are prepared by reacting a 1-H-4-OR 1 <SP>1</SP>-indole with an. alkyl magnesium halide to give the indole magnesium halide, reacting this with a compound X 1 -COA-X 2 (wherein X 1 and X 2 each represent the same or different halogen atom) treating the resulting product with an amine, R 3 R 4 NH, and reducing the resulting amino-ketone. The 1- substituted compound may be prepared by reacting the 1-unsubstituted indole thus formed with an alkyl or aralkyl halide in the presence of an alkali condensation agent. Furthermore compounds of the invention are prepared either by reacting an 1-R 2 -4-OR 1 <SP>1</SP>-indole with formaldehyde and a secondary amine, quaternising the gramine so formed, reacting the salt with an alkali metal cyanide to give an indolyl-(3)- acetonitrile. saponifying this to the carboxylic acid converting this to the acid azide or halide, reacting the azide or halide with an amine R 3 R 4 NH and reducing the amide, or (when both R 3 and R 4 are hydrogen atoms) by reducing the nitrile direct to the amine, or (where R 2 R 3 and R 4 are each hydrogen atoms) by reacting an appropriate gramine with a nitroalkane H-ANO 2 in the presence of a proton acceptor and reducing the nitro indole so formed, or by heating a indolyl-(3)-aldehyde in the presence of a condensation agent favouring the splitting off of water with a nitroalkane to give an indole of the formula: (in which 'A' designates the group A less a hydrogen atom) and reducing this to the alkylamino compound. Specifications 744,773, 744,774, 781,390 and 807,876 also are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7167759A CH373381A (en) | 1959-07-13 | 1959-07-13 | Process for the preparation of new basic indole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB942548A true GB942548A (en) | 1963-11-27 |
Family
ID=4531186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1016660A Expired GB942548A (en) | 1959-07-13 | 1960-03-22 |
Country Status (3)
| Country | Link |
|---|---|
| CH (4) | CH373381A (en) |
| ES (1) | ES257146A1 (en) |
| GB (1) | GB942548A (en) |
Cited By (4)
| 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 |
| 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 |
-
1959
- 1959-07-13 CH CH7167759A patent/CH373381A/en unknown
- 1959-08-21 CH CH724364A patent/CH380131A/en unknown
- 1959-08-21 CH CH724264A patent/CH380130A/en unknown
-
1960
- 1960-02-24 CH CH204960A patent/CH383379A/en unknown
- 1960-03-22 GB GB1016660A patent/GB942548A/en not_active Expired
- 1960-04-06 ES ES0257146A patent/ES257146A1/en not_active Expired
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 |
| 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 |
| EP4229036A4 (en) * | 2020-10-13 | 2024-09-04 | Caamtech Inc | Tryptamine derivatives and their therapeutic uses |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES257146A1 (en) | 1960-12-01 |
| CH373381A (en) | 1963-11-30 |
| CH383379A (en) | 1964-10-31 |
| CH380131A (en) | 1964-07-31 |
| CH380130A (en) | 1964-07-31 |
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