GB992731A - Aminoalkyl-indolyl-benzyl alcohols - Google Patents

Aminoalkyl-indolyl-benzyl alcohols

Info

Publication number
GB992731A
GB992731A GB3698262A GB3698262A GB992731A GB 992731 A GB992731 A GB 992731A GB 3698262 A GB3698262 A GB 3698262A GB 3698262 A GB3698262 A GB 3698262A GB 992731 A GB992731 A GB 992731A
Authority
GB
United Kingdom
Prior art keywords
alkyl
methyl
hydrogen
benzoyl
hydrolysis
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
GB3698262A
Inventor
Robert Cornelis Roozemond
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.)
Koninklijke Pharmaceutische Fabrieken NV
Original Assignee
Koninklijke Pharmaceutische Fabrieken NV
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
Application filed by Koninklijke Pharmaceutische Fabrieken NV filed Critical Koninklijke Pharmaceutische Fabrieken NV
Priority to GB3698262A priority Critical patent/GB992731A/en
Publication of GB992731A publication Critical patent/GB992731A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0992731/C2/1> where R1 is hydrogen, halogen or alkoxy, R2 is hydrogen or alkyl, R3 is hydrogen, alkyl or aralkyl, R4 is hydrogen, halogen, alkoxy, alkyl or trifluoromethyl, A is C2-6 alkylene, and B is alkylamino, dialkylamino, or a saturated mononuclear 5- or 6-membered heterocyclic group attached via nitrogen, "alkyl" and "alkoxy" having up to 6C; and non-toxic acid addition salts thereof; and their production by reacting appropriately substituted reactants as follows: (i) an indolyl phenyl ketone with a compound BAMgX (where X is halogen) followed by hydrolysis; (ii) an indolyl aminoalkyl ketone with a phenyllithium or phenylmagnesium halide, followed by hydrolysis; and (iii) an indol-2-yllithium with an aminoalkyl phenyl ketone, followed by hydrolysis. The preparation of the starting compounds is described, and in particular: 2-benzoylindole and its o-, m- and p-methyl and p-chloro-derivatives; 1-methyl-2-benzoylindole and its o-, m- and p-methyl and p-chloro and p-methoxy-derivatives; and 2-benzoyl-3-methylindole and 2-benzoyl-3-ethylindole are prepared from phenylethium or a substituted phenyllithium and the appropriate indole-2-carboxylic acid; 2-benzoyl-3-methylindole is obtained from N,N-dumethylbenzamide, skatole and POCl3; and 1-methylindol-2 - yl 2 - dimethylaminoethyl ketone hydrochloride is obtained from 1-methyl-2-acetylindole, dimethylamine hydrochloride and paraformaldehyde. The compounds of the invention possess sedative activity, and may be used with pharmacologically acceptable carriers, e.g. as tablets, pills, capsules, suspensions, emulsions, syrups or elixirs for oral administration, or as a suspension or emulsion in sterile water or an organic liquid.
GB3698262A 1962-09-28 1962-09-28 Aminoalkyl-indolyl-benzyl alcohols Expired GB992731A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3698262A GB992731A (en) 1962-09-28 1962-09-28 Aminoalkyl-indolyl-benzyl alcohols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3698262A GB992731A (en) 1962-09-28 1962-09-28 Aminoalkyl-indolyl-benzyl alcohols

Publications (1)

Publication Number Publication Date
GB992731A true GB992731A (en) 1965-05-19

Family

ID=10392756

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3698262A Expired GB992731A (en) 1962-09-28 1962-09-28 Aminoalkyl-indolyl-benzyl alcohols

Country Status (1)

Country Link
GB (1) GB992731A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7446118B2 (en) 2005-11-30 2008-11-04 Roche Palo Alto Llc 3-amino-1-arylpropyl indoles and aza-substituted indoles and uses thereof
US7598399B2 (en) 2005-11-30 2009-10-06 Roche Palo Alto Llc Methods for synthesis of 3-amino-1-arylpropyl indoles
US7638517B2 (en) 2005-11-30 2009-12-29 Roche Palo Alto Llc 3-Amino-1-arylpropyl azaindoles and uses thereof
US7863305B2 (en) 2004-06-01 2011-01-04 Roche Palo Alto Llc 3-amino-1-arylpropyl indoles as monoamine reuptake inhibitors

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7863305B2 (en) 2004-06-01 2011-01-04 Roche Palo Alto Llc 3-amino-1-arylpropyl indoles as monoamine reuptake inhibitors
US7446118B2 (en) 2005-11-30 2008-11-04 Roche Palo Alto Llc 3-amino-1-arylpropyl indoles and aza-substituted indoles and uses thereof
US7598399B2 (en) 2005-11-30 2009-10-06 Roche Palo Alto Llc Methods for synthesis of 3-amino-1-arylpropyl indoles
US7638517B2 (en) 2005-11-30 2009-12-29 Roche Palo Alto Llc 3-Amino-1-arylpropyl azaindoles and uses thereof
US7803830B2 (en) 2005-11-30 2010-09-28 Roche Palo Alto Llc 3-amino-1-arylpropyl indoles and AZA-substituted indoles and uses thereof

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