GB912714A - Improvements in or relating to phosphorus-containing indole derivatives - Google Patents
Improvements in or relating to phosphorus-containing indole derivativesInfo
- Publication number
- GB912714A GB912714A GB28884/59A GB2888459A GB912714A GB 912714 A GB912714 A GB 912714A GB 28884/59 A GB28884/59 A GB 28884/59A GB 2888459 A GB2888459 A GB 2888459A GB 912714 A GB912714 A GB 912714A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compounds
- alkyl
- nitrogen atom
- addition salts
- 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 150000002475 indoles Chemical class 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000003386 piperidinyl group Chemical group 0.000 abstract 2
- OHHYMKDBKJPILO-UHFFFAOYSA-N 3-[2-(diethylamino)ethyl]-1h-indol-4-ol Chemical compound C1=CC(O)=C2C(CCN(CC)CC)=CNC2=C1 OHHYMKDBKJPILO-UHFFFAOYSA-N 0.000 abstract 1
- NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical class OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 abstract 1
- HDFFVHSMHLDSLO-UHFFFAOYSA-N Dibenzyl phosphate Chemical class C=1C=CC=CC=1COP(=O)(O)OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-N 0.000 abstract 1
- SMVXYBYTGKEHCS-UHFFFAOYSA-N [benzyl(chloro)phosphoryl]methylbenzene Chemical compound C=1C=CC=CC=1CP(=O)(Cl)CC1=CC=CC=C1 SMVXYBYTGKEHCS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000026731 phosphorylation Effects 0.000 abstract 1
- 238000006366 phosphorylation reaction Methods 0.000 abstract 1
- SPCIYGNTAMCTRO-UHFFFAOYSA-N psilocin Chemical compound C1=CC(O)=C2C(CCN(C)C)=CNC2=C1 SPCIYGNTAMCTRO-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
- C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Compounds of formula I <FORM:0912714/IV (b)/1> wherein R11 and R21 are C1-4 alkyl or together with the adjacent nitrogen atom form a piperidine ring are prepared by esterifying a salt of an inorganic base with a 4-hydroxyindole derivative of formula <FORM:0912714/IV (b)/2> dissolved in an inert organic solvent, by a method known to effect phosphorylation of a phenolic hydroxy group, e.g. by treatment with dibenzylphosphoryl chloride followed by hydrogenation. The invention also comprises those compounds of formula I and their acid addition salts wherein R11 and R21 are C1-4 alkyl or together with the adjacent nitrogen atom form a piperidine ring, with the proviso that R1 and R2 together must contain at least 3 carbon atoms, and also comprises the dibenzylphosphoric acid esters of 4-hydroxydimethyltryptamine, 4-hydroxydiethyltryptamine and of 4-hydroxy-3-(21-piperidinoethyl)-indole. The compounds of formula I and their acid addition salts are used in pharmaceutical compositions for oral and parenteral administration, the drugs having psychomimetic properties. Specification 912,715 is referred to.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6387558A CH370409A (en) | 1958-09-12 | 1958-09-12 | Process for the production of new, phosphorus-containing indole derivatives |
| CH6842459A CH375359A (en) | 1959-01-16 | 1959-01-16 | Process for the production of new, phosphorus-containing indole derivatives |
| CH7074259 | 1959-03-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB912714A true GB912714A (en) | 1962-12-12 |
Family
ID=27178509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28884/59A Expired GB912714A (en) | 1958-09-12 | 1959-08-24 | Improvements in or relating to phosphorus-containing indole derivatives |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE582353A (en) |
| DE (1) | DE1211645B (en) |
| ES (1) | ES251430A1 (en) |
| FR (1) | FR1311106A (en) |
| GB (1) | GB912714A (en) |
| LU (1) | LU37646A1 (en) |
| NL (2) | NL243249A (en) |
| OA (1) | OA01253A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019073379A1 (en) * | 2017-10-09 | 2019-04-18 | Compass Pathways Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US11564935B2 (en) | 2019-04-17 | 2023-01-31 | Compass Pathfinder Limited | Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin |
| US11724985B2 (en) | 2020-05-19 | 2023-08-15 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
-
0
- NL NL121067D patent/NL121067C/xx active
- LU LU37646D patent/LU37646A1/xx unknown
- NL NL243249D patent/NL243249A/xx unknown
- BE BE582353D patent/BE582353A/xx unknown
-
1959
- 1959-08-13 ES ES0251430A patent/ES251430A1/en not_active Expired
- 1959-08-24 GB GB28884/59A patent/GB912714A/en not_active Expired
- 1959-09-08 DE DES64818A patent/DE1211645B/en active Pending
- 1959-09-10 FR FR804443A patent/FR1311106A/en not_active Expired
-
1964
- 1964-12-31 OA OA51500A patent/OA01253A/en unknown
Cited By (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11180517B2 (en) | 2017-10-09 | 2021-11-23 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| IL273883B1 (en) * | 2017-10-09 | 2024-05-01 | Compass Pathfinder Ltd | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| WO2019073379A1 (en) * | 2017-10-09 | 2019-04-18 | Compass Pathways Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US10519175B2 (en) | 2017-10-09 | 2019-12-31 | Compass Pathways Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| DE202018006384U1 (en) | 2017-10-09 | 2020-03-19 | Compass Pathways Limited | Production of psilocybin, various polymorphic forms, intermediates, formulations and their use |
| GB2571696B (en) * | 2017-10-09 | 2020-05-27 | Compass Pathways Ltd | Large scale method for the preparation of Psilocybin and formulations of Psilocybin so produced |
| CN111491919A (en) * | 2017-10-09 | 2020-08-04 | 指南针路径有限公司 | Preparation of siloxibin, different polymorphic forms, intermediates, formulations and uses thereof |
| JP2020536960A (en) * | 2017-10-09 | 2020-12-17 | コンパス パスファインダー リミテッド | Preparation of psilocybin, different polymorphs, intermediates, formulations and their use |
| US10947257B2 (en) | 2017-10-09 | 2021-03-16 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US10954259B1 (en) | 2017-10-09 | 2021-03-23 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| GB2588506A (en) * | 2017-10-09 | 2021-04-28 | Compass Pathfinder Ltd | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US11149044B2 (en) | 2017-10-09 | 2021-10-19 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| GB2572023A (en) * | 2017-10-09 | 2019-09-18 | Compass Pathways Ltd | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| GB2571696A (en) * | 2017-10-09 | 2019-09-11 | Compass Pathways Ltd | Preparation of Psilocybin, different polymorphic forms, intermediates, formulations and their use |
| GB2588506B (en) * | 2017-10-09 | 2022-07-06 | Compass Pathfinder Ltd | Psilocybin polymorphic form A, formulations and use in medicine |
| US11505564B2 (en) | 2017-10-09 | 2022-11-22 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US11939346B2 (en) | 2017-10-09 | 2024-03-26 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| JP2023024755A (en) * | 2017-10-09 | 2023-02-16 | コンパス パスファインダー リミテッド | Preparation of psilocybin, different polymorphic forms, intermediates and formulations, and their use |
| US11629159B2 (en) | 2017-10-09 | 2023-04-18 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US11851451B2 (en) | 2017-10-09 | 2023-12-26 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US11447510B2 (en) | 2017-10-09 | 2022-09-20 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US11738035B2 (en) | 2019-04-17 | 2023-08-29 | Compass Pathfinder Limited | Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin |
| US11564935B2 (en) | 2019-04-17 | 2023-01-31 | Compass Pathfinder Limited | Method for treating anxiety disorders, headache disorders, and eating disorders with psilocybin |
| US11834410B2 (en) | 2020-05-19 | 2023-12-05 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
| US11724985B2 (en) | 2020-05-19 | 2023-08-15 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
| US11958807B2 (en) | 2020-05-19 | 2024-04-16 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
| US11746088B2 (en) | 2020-05-19 | 2023-09-05 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
Also Published As
| Publication number | Publication date |
|---|---|
| ES251430A1 (en) | 1960-04-01 |
| NL243249A (en) | |
| FR1311106A (en) | 1962-12-07 |
| OA01253A (en) | 1969-01-25 |
| LU37646A1 (en) | |
| NL121067C (en) | |
| DE1211645B (en) | 1966-03-03 |
| BE582353A (en) |
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