GB981192A - Improvements in or relating to 4 hydroxytryptamine esters - Google Patents

Improvements in or relating to 4 hydroxytryptamine esters

Info

Publication number
GB981192A
GB981192A GB872261A GB872261A GB981192A GB 981192 A GB981192 A GB 981192A GB 872261 A GB872261 A GB 872261A GB 872261 A GB872261 A GB 872261A GB 981192 A GB981192 A GB 981192A
Authority
GB
United Kingdom
Prior art keywords
methyl
diethylaminoethyl
acid
benzyloxyindole
general formula
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
Application number
GB872261A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
WESTMINSTER BANK Ltd
Original Assignee
WESTMINSTER BANK Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from CH356360A external-priority patent/CH386422A/en
Application filed by WESTMINSTER BANK Ltd filed Critical WESTMINSTER BANK Ltd
Publication of GB981192A publication Critical patent/GB981192A/en
Expired legal-status Critical Current

Links

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0981192/C2/1> and their acid addition salts in which either each of R1 and R2 represents a C1-4 alkyl group with the proviso that R1 and R2 need not be dissimila or R1 and R2 together represent a tetra-or penta-methylene chain, R3 represents a C1-4-alkyl group, a C2-4 alkenyl group or an aralkyl group containing up to 10 carbon atoms inclusive and R4 represents the radical of an organic carboxylic acid containing up to 10 carbon atoms inclusive or sulphuric acid and the preparation thereof by esterifying an appropriate 4-hydroxytryptamine with an acid anhydride (R4)2O or acid halide R4-halogen or (when R3 represents an alkenyl group) reacting a compound of the general formula <FORM:0981192/C2/2> (wherein R is an organic carboxylic acid residue which is not split off under the reaction conditions) with an appropriate alkenyl halide. 1 - Methyl - 3 - (21 - diethylaminoethyl) - 4 - hydroxyindol is prepared by condensing 3-(21-diethylaminoethyl) - 4 - benzyloxyindole with methyl iodide and hydrogenolysing the 1-methyl - 3 - (21 - diethylaminoethyl) - 4 - benzyloxyindole so formed. Similarly were prepared 1 - methyl - 3 - (21 - piperidinoethyl) - 4 - benzyloxyan -4-hydroxy-indoles. Pharmaceutical compositions comprise the tryptamine esters of the invention together with an inert carrier. The compounds show central sympathetic nerve system stimulant action and some show serotonin antagonistic properties.
GB872261A 1960-03-30 1961-03-09 Improvements in or relating to 4 hydroxytryptamine esters Expired GB981192A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH356360A CH386422A (en) 1960-03-30 1960-03-30 Process for the production of new esters of the indole series

Publications (1)

Publication Number Publication Date
GB981192A true GB981192A (en) 1965-01-20

Family

ID=4258692

Family Applications (1)

Application Number Title Priority Date Filing Date
GB872261A Expired GB981192A (en) 1960-03-30 1961-03-09 Improvements in or relating to 4 hydroxytryptamine esters

Country Status (2)

Country Link
ES (1) ES266125A1 (en)
GB (1) GB981192A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0776977A1 (en) * 1995-12-06 1997-06-04 L'oreal Process for the preparation of indol compounds
US8710093B2 (en) 2002-12-20 2014-04-29 BASF SE Ludwigshafen Synthesis of amines and intermediates for the synthesis thereof
WO2021179091A1 (en) * 2020-03-12 2021-09-16 Bright Minds Biosciences Inc. 3-(2-(aminoethyl)-indol-4-ol derivatives, methods of preparation thereof, and the use as 5-ht2 receptor modulators
US11518743B2 (en) 2020-06-12 2022-12-06 Beckley Psytech Limited Pharmaceutical composition comprising 5-methoxy-N,N-dimethyltryptamine
US11591353B2 (en) 2020-02-04 2023-02-28 Mindset Pharma Inc. Psilocin derivatives as serotonergic psychedelic agents for the treatment of CNS disorders
US11724985B2 (en) 2020-05-19 2023-08-15 Cybin Irl Limited Deuterated tryptamine derivatives and methods of use
US11746087B1 (en) 2022-03-18 2023-09-05 Enveric Biosciences Canada Inc. C4-carboxylic acid-substituted tryptamine derivatives and methods of using
US11773063B1 (en) 2022-08-19 2023-10-03 Beckley Psytech Limited Pharmaceutically acceptable salts and compositions thereof

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2742162A1 (en) * 1995-12-06 1997-06-13 Oreal PROCESS FOR THE PREPARATION OF INDOLIC COMPOUNDS
US5717108A (en) * 1995-12-06 1998-02-10 L'oreal Process for the preparation of indole compounds
EP0776977A1 (en) * 1995-12-06 1997-06-04 L'oreal Process for the preparation of indol compounds
US8710093B2 (en) 2002-12-20 2014-04-29 BASF SE Ludwigshafen Synthesis of amines and intermediates for the synthesis thereof
US8822702B2 (en) 2002-12-20 2014-09-02 Basf Se Synthesis of amines and intermediates for the synthesis thereof
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
WO2021179091A1 (en) * 2020-03-12 2021-09-16 Bright Minds Biosciences Inc. 3-(2-(aminoethyl)-indol-4-ol derivatives, methods of preparation thereof, and the use as 5-ht2 receptor modulators
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
US11746088B2 (en) 2020-05-19 2023-09-05 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
US12110272B2 (en) 2020-05-19 2024-10-08 Cybin Irl Limited Deuterated tryptamine derivatives and methods of use
US11603353B2 (en) 2020-06-12 2023-03-14 Beckley Psytech Limited Composition comprising a benzoate salt of 5-methoxy-N,N-dimethyltryptamine
US11680044B2 (en) 2020-06-12 2023-06-20 Beckley Psytech Limited Pharmaceutical composition comprising 5-methoxy-n,n-dimethyltryptamine
US11518742B2 (en) 2020-06-12 2022-12-06 Beckley Psytech Limited Composition comprising a benzoate salt of 5-methoxy-N,N-dimethyltryptamine
US11518743B2 (en) 2020-06-12 2022-12-06 Beckley Psytech Limited Pharmaceutical composition comprising 5-methoxy-N,N-dimethyltryptamine
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
US11773063B1 (en) 2022-08-19 2023-10-03 Beckley Psytech Limited Pharmaceutically acceptable salts and compositions thereof

Also Published As

Publication number Publication date
ES266125A1 (en) 1961-11-01

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