GB999093A - Manufacture of 3,4-dihydroisoquinoline compounds - Google Patents

Manufacture of 3,4-dihydroisoquinoline compounds

Info

Publication number
GB999093A
GB999093A GB977560A GB977560A GB999093A GB 999093 A GB999093 A GB 999093A GB 977560 A GB977560 A GB 977560A GB 977560 A GB977560 A GB 977560A GB 999093 A GB999093 A GB 999093A
Authority
GB
United Kingdom
Prior art keywords
methylpsychotrine
dehydro
isoemetine
alkali
treating
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
GB977560A
Inventor
Norman Whittaker
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation 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
Application filed by Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB977560A priority Critical patent/GB999093A/en
Priority to CH312661A priority patent/CH409958A/en
Priority to DE19611445183 priority patent/DE1445183A1/en
Priority to DK114061A priority patent/DK107025C/en
Priority to BE601459A priority patent/BE601459A/en
Priority to BR12774861A priority patent/BR6127748D0/en
Priority to SE2903/61A priority patent/SE318567B/xx
Publication of GB999093A publication Critical patent/GB999093A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
    • C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems
    • C07D455/08—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems having an isoquinolyl-1, a substituted isoquinolyl-1 or an alkylenedioxyisoquinolyl-1 radical linked through only one carbon atom, attached in position 2, e.g. emetine

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

3,4-Dihydroisoquinolines of the general formula <FORM:0999093/C2/1> are prepared by treating the corresponding 1,2,3,4 - tetrahydroisoquinoline with an N-halogenating agent and subsequently heating with alkali; (R represents a hydrogen atom or an alkyl or indifferently substituted alkyl group, and the benzenoid ring may be substituted by one or more alkoxy groups or by an alkylenedioxy group). The process may be used for the conversion of isoemetine or 2-dehydro-isoemetine into emetine or 2-dehydroemetine, respectively, by treating with an N-halogenating agent, e.g. a hypochlorite or N-chloroamide, subsequently heating with an alkali and then reducing the O-methylpsychotrine or 2-dehydro-O-methylpsychotrine produced. Detailed examples illustrate the preparation of 3,4-dihydro-6,7-dimethoxyisoquinoline, its 1-methyl derivative, 3,4-dihydroisoquinoline, (+)-O-methylpsychotrine dihydrogen oxalate, and racemic 2 - dehydro - O - methyl - psychotrine. Specifications 798,847, 999,095 and 999,096 are referred to.
GB977560A 1960-03-18 1960-03-18 Manufacture of 3,4-dihydroisoquinoline compounds Expired GB999093A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
GB977560A GB999093A (en) 1960-03-18 1960-03-18 Manufacture of 3,4-dihydroisoquinoline compounds
CH312661A CH409958A (en) 1960-03-18 1961-03-15 Process for the preparation of 3,4-dihydroisoquinolines
DE19611445183 DE1445183A1 (en) 1960-03-18 1961-03-17 Manufacture of organic chemical compounds
DK114061A DK107025C (en) 1960-03-18 1961-03-17 Process for the preparation of 3,4-dihydroisoquinoline derivatives.
BE601459A BE601459A (en) 1960-03-18 1961-03-17 Preparation of 3,4-dihydro-isoquinolines.
BR12774861A BR6127748D0 (en) 1960-03-18 1961-03-17 PROCESS FOR THE PREPARATION OF 3.4 DIHIDROISOQUINOLINAS
SE2903/61A SE318567B (en) 1960-03-18 1961-03-18

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB977560A GB999093A (en) 1960-03-18 1960-03-18 Manufacture of 3,4-dihydroisoquinoline compounds

Publications (1)

Publication Number Publication Date
GB999093A true GB999093A (en) 1965-07-21

Family

ID=9878531

Family Applications (1)

Application Number Title Priority Date Filing Date
GB977560A Expired GB999093A (en) 1960-03-18 1960-03-18 Manufacture of 3,4-dihydroisoquinoline compounds

Country Status (2)

Country Link
BR (1) BR6127748D0 (en)
GB (1) GB999093A (en)

Also Published As

Publication number Publication date
BR6127748D0 (en) 1973-06-07

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