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) | NL121067C (en) |
OA (1) | OA01253A (en) |
Cited By (4)
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 |
US12060328B2 (en) | 2022-03-04 | 2024-08-13 | Reset Pharmaceuticals, Inc. | Co-crystals or salts of psilocybin and methods of treatment therewith |
-
0
- NL NL243249D patent/NL243249A/xx unknown
- BE BE582353D patent/BE582353A/xx unknown
- NL NL121067D patent/NL121067C/xx active
- LU LU37646D patent/LU37646A1/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 (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11447510B2 (en) | 2017-10-09 | 2022-09-20 | Compass Pathfinder Limited | 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 |
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 |
US11851451B2 (en) | 2017-10-09 | 2023-12-26 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
US11180517B2 (en) | 2017-10-09 | 2021-11-23 | Compass Pathfinder Limited | 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 |
US11629159B2 (en) | 2017-10-09 | 2023-04-18 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
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 |
WO2019073379A1 (en) * | 2017-10-09 | 2019-04-18 | Compass Pathways 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 |
GB2588506B (en) * | 2017-10-09 | 2022-07-06 | Compass Pathfinder Ltd | Psilocybin polymorphic form A, formulations and use in medicine |
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 |
US11958807B2 (en) | 2020-05-19 | 2024-04-16 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
US11834410B2 (en) | 2020-05-19 | 2023-12-05 | 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 |
US11724985B2 (en) | 2020-05-19 | 2023-08-15 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
US12060328B2 (en) | 2022-03-04 | 2024-08-13 | Reset Pharmaceuticals, Inc. | Co-crystals or salts of psilocybin and methods of treatment therewith |
Also Published As
Publication number | Publication date |
---|---|
DE1211645B (en) | 1966-03-03 |
BE582353A (en) | |
OA01253A (en) | 1969-01-25 |
NL121067C (en) | |
ES251430A1 (en) | 1960-04-01 |
FR1311106A (en) | 1962-12-07 |
NL243249A (en) | |
LU37646A1 (en) |
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