GB982071A - Process for the production of emetine and related compounds - Google Patents

Process for the production of emetine and related compounds

Info

Publication number
GB982071A
GB982071A GB9913/61A GB991361A GB982071A GB 982071 A GB982071 A GB 982071A GB 9913/61 A GB9913/61 A GB 9913/61A GB 991361 A GB991361 A GB 991361A GB 982071 A GB982071 A GB 982071A
Authority
GB
United Kingdom
Prior art keywords
metal
alkali
reduction
preparation
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
GB9913/61A
Inventor
Dennis Edward Clark
Alexander Crawford Ritchie
Thomas Walker
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.)
Glaxo Group Ltd
Original Assignee
Glaxo Group 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 Glaxo Group Ltd filed Critical Glaxo Group Ltd
Priority to GB9913/61A priority Critical patent/GB982071A/en
Priority to DK345262A priority patent/DK107940C/en
Priority to BE604728A priority patent/BE604728A/en
Priority to CH661861A priority patent/CH416637A/en
Priority to DE19611445833 priority patent/DE1445833A1/en
Priority to DE19611445058 priority patent/DE1445058A1/en
Priority to SE606561A priority patent/SE307357B/xx
Priority to BE615033A priority patent/BE615033A/en
Priority to SE2955/62A priority patent/SE304271B/xx
Priority to CH321862A priority patent/CH422797A/en
Publication of GB982071A publication Critical patent/GB982071A/en
Expired legal-status Critical Current

Links

Classifications

    • 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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention comprises the preparation of compounds of the general formula <FORM:0982071/C2/1> (wherein R represents a hydrocarbon group and wherein one or more substituents, especially alkoxy or methylenedioxy groups, may be present in the 31, 41, 51, 61, 71 81, 8, 9, 10 and/or 11 positions) by oxidation of corresponding compounds in which the nitrogen atom of the isoquinoline nucleus carries a substituent of the formula <FORM:0982071/C2/2> (wherein R1 represents a hydrocarbon group) by means of an alkali metal alkoxide and a ketone stable in the presence of alkali, and the combination of this process with the preparation of the starting materials by reduction of a compound of the general formula <FORM:0982071/C2/3> (optionally substituted as before) by means of a metal/ammonia or metal/amine reducing system to a compound of the general formula <FORM:0982071/C2/4> which, after isomerization at the 3-position under strong enolizing conditions, is reduced with a metal/acid reducing system or with hydrazine and alkali or by conversion to a thioketal and reduction of this with hydrazine and alkali or with a Raney metal, preferably in the presence of hydrogen. (Under suitable conditions, isomerization and the second reduction can be effected simultaneously). When the starting material contains methoxy groups (e.g. in the preparation of emetine or isoemetine), these may undergo hydrolysis during the oxidation process, in which event the resulting hydroxy groups may be re-methylated. Specification 977,788 is referred to.
GB9913/61A 1960-06-09 1961-03-17 Process for the production of emetine and related compounds Expired GB982071A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
GB9913/61A GB982071A (en) 1961-03-17 1961-03-17 Process for the production of emetine and related compounds
DK345262A DK107940C (en) 1960-06-09 1961-06-01 Process for the preparation of an emetine derivative or acid addition salts thereof.
BE604728A BE604728A (en) 1960-06-09 1961-06-07 New derivatives of emtine and their preparation.
CH661861A CH416637A (en) 1960-06-09 1961-06-07 Process for the preparation of derivatives of 1-emetine
DE19611445833 DE1445833A1 (en) 1960-06-09 1961-06-09 Process for the preparation of N-substituted 1-emetine derivatives
DE19611445058 DE1445058A1 (en) 1960-06-09 1961-06-09 Process for the preparation of N-substituted derivatives of 1-emitin
SE606561A SE307357B (en) 1960-06-09 1961-06-09
BE615033A BE615033A (en) 1961-03-17 1962-03-13 Improvements in the production of emetine and analogs
SE2955/62A SE304271B (en) 1961-03-17 1962-03-16
CH321862A CH422797A (en) 1961-03-17 1962-03-16 Process for the preparation of emetine and its analogues

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB9913/61A GB982071A (en) 1961-03-17 1961-03-17 Process for the production of emetine and related compounds

Publications (1)

Publication Number Publication Date
GB982071A true GB982071A (en) 1965-02-03

Family

ID=9881096

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9913/61A Expired GB982071A (en) 1960-06-09 1961-03-17 Process for the production of emetine and related compounds

Country Status (4)

Country Link
BE (1) BE615033A (en)
CH (1) CH422797A (en)
GB (1) GB982071A (en)
SE (1) SE304271B (en)

Also Published As

Publication number Publication date
CH422797A (en) 1966-10-31
BE615033A (en) 1962-09-13
SE304271B (en) 1968-09-23

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