GB977788A - Emetine derivatives and their preparation - Google Patents

Emetine derivatives and their preparation

Info

Publication number
GB977788A
GB977788A GB2038760A GB2038760A GB977788A GB 977788 A GB977788 A GB 977788A GB 2038760 A GB2038760 A GB 2038760A GB 2038760 A GB2038760 A GB 2038760A GB 977788 A GB977788 A GB 977788A
Authority
GB
United Kingdom
Prior art keywords
reduction
hydroxyalkyl
alkyl
emetine
group
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
GB2038760A
Inventor
Alexander Crawford Ritchie
Keith Desmond Eric Whiting
Dennis Edward Clark
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 GB2038760A priority Critical patent/GB977788A/en
Priority to DK345262A priority patent/DK107940C/en
Priority to BE604728A priority patent/BE604728A/en
Priority to CH661861A priority patent/CH416637A/en
Priority to BR12988261A priority patent/BR6129882D0/en
Priority to DE19611445833 priority patent/DE1445833A1/en
Priority to DE19611445058 priority patent/DE1445058A1/en
Priority to SE606561A priority patent/SE307357B/xx
Publication of GB977788A publication Critical patent/GB977788A/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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention comprises N-substituted derivatives of 1-emetine having the general formula <FORM:0977788/C1/1> (wherein R represents an unsubstituted alkyl, hydroxyalkyl, or esterified hydroxyalkyl group, the N-alkyl portion of which contains 2 to 7 carbon atoms) their non-toxic acid addition salts, particularly the mono- and di-hydrochlorides, hydrobromides, hydroiodides, sulphates, nitrates, citrates and tartrates, also addition complexes with bismuth halides also processes for their preparation (a) by N-alkylating l-emetine to introduce an N-alkyl, N-hydroxyalkyl or N-(esterified hydroxyalkyl) group at the 21-position; (b) by reacting a compound of the general formula <FORM:0977788/C1/2> (wherein R11 is an alkyl or hydroxyalkyl group of from 1 to 7 carbon atoms) in one or more stages with reagents serving to reduce a ketonic carbonyl group to a methylene group. The principal methods for process (a) are (i) reaction of l-emetine with a functional derivative of an acid R1COOH (R1 is alkyl), and then reduction of the carbonyl group of the resulting amide, e.g. with complex metal hydrides; (ii) reaction of l-emetine with a vinyl ketone CH2:CHCOR11 (R11 being alkyl of from one to four atoms), followed by reduction of the carbonyl group in the resulting N-oxoalkyl compound, e.g. with hydrazine and alkali, or by conversion to the ethylene thioketal or benzylmercaptol derivative followed by reduction with a Raney metal, or, if a hydroxyalkyl compound is required by reduction of the carbonyl group with a complex metal hydride. The methods for process (b) involve direct reduction with hydrazine and alkali, or reduction of the thioketal derivative e.g. with a Raney metal. The compounds of second general formula above are themselves prepared by reduction of compounds of the formula <FORM:0977788/C1/3> R11 is alkyl, hydroxyalkyl or oxoalkyl with a metal/ammonia or metal/amine reducing system followed by isomerization of the 3b -acetyl compound obtained. Any methoxyl groups that are converted to hydroxyl during the processes are remethylated, e.g. using a phenyl trimethylammonium salt. The invention is illustrated by 11 detailed examples. Specifications 960,181 and 960,182 also are referred to.
GB2038760A 1960-06-09 1960-06-09 Emetine derivatives and their preparation Expired GB977788A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
GB2038760A GB977788A (en) 1960-06-09 1960-06-09 Emetine derivatives and their preparation
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
BR12988261A BR6129882D0 (en) 1960-06-09 1961-06-08 PROCESS FOR PREPARATION OF L-EMETINE DERIVATIVES
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

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2038760A GB977788A (en) 1960-06-09 1960-06-09 Emetine derivatives and their preparation

Publications (1)

Publication Number Publication Date
GB977788A true GB977788A (en) 1964-12-16

Family

ID=10145113

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2038760A Expired GB977788A (en) 1960-06-09 1960-06-09 Emetine derivatives and their preparation

Country Status (1)

Country Link
GB (1) GB977788A (en)

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