GB1024901A - A process for the manufacture of dehydro-emetines and analogues thereof - Google Patents

A process for the manufacture of dehydro-emetines and analogues thereof

Info

Publication number
GB1024901A
GB1024901A GB11168/63A GB1116863A GB1024901A GB 1024901 A GB1024901 A GB 1024901A GB 11168/63 A GB11168/63 A GB 11168/63A GB 1116863 A GB1116863 A GB 1116863A GB 1024901 A GB1024901 A GB 1024901A
Authority
GB
United Kingdom
Prior art keywords
alkyl
quinolizine
dimethoxy
benzo
tetrahydro
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
GB11168/63A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1024901A publication Critical patent/GB1024901A/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
    • 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)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises (-)-dehydroemtines and alkyl analogues thereof of the formula <FORM:1024901/C2/1> where R represents an alkyl group of not more than 4 carbon atoms, and the preparation thereof by condensing a (-)-2-alkoxycarbonylmethyl - 3 - alkyl - 9,10 - dimethoxy - 1,4,6,7-tetrahydro - 116H - benzo[a]quinolizine, where the alkoxy group has up to 4 carbon atoms or the corresponding 2-carboxymethyl compound with homoveratrylamine; cyclizing the (-)-homoveretrylamide of 2-carboxymethyl-3-alkyl - 9,10 - dimethoxy - 1,4,6,7 - tetrahydro-116H - benzo[a]quinolizine so produced, reducing the resulting 2-dehydro-O-methyl-psychotrine or 3-alkyl-analogue thereof and, if desired, separating the (-)-isomer from the resulting mixture. (-)-2-Carboxymethyl - 3 - alkyl - 9,10 - dimethoxy - 1,4,6,7 - tetrahydro - 116H - benzo[a] quinolizine is made by the saponification of the corresponding alkyl ester. Therapeutic compositions with amoebicidal properties for enteral and parenteral application, which may be in the form of tablets, dragees, suppositories, capsules, solutions, suspensions or emulsions, comprise compounds of the above formula and pharmaceutically acceptable salts thereof.
GB11168/63A 1962-03-21 1963-03-21 A process for the manufacture of dehydro-emetines and analogues thereof Expired GB1024901A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH338662A CH419138A (en) 1962-03-21 1962-03-21 Process for the preparation of enantiomeric compounds from the dehydroemetin series

Publications (1)

Publication Number Publication Date
GB1024901A true GB1024901A (en) 1966-04-06

Family

ID=4254829

Family Applications (4)

Application Number Title Priority Date Filing Date
GB11168/63A Expired GB1024901A (en) 1962-03-21 1963-03-21 A process for the manufacture of dehydro-emetines and analogues thereof
GB43798/65A Expired GB1024904A (en) 1962-03-21 1963-03-21 Novel psychotrine derivatives
GB11454/65A Expired GB1024902A (en) 1962-03-21 1963-03-21 A process for the preparation of optically active benzo[a]quinolizine derivatives
GB43797/65A Expired GB1024903A (en) 1962-03-21 1963-03-21 Novel homoveratryl amides

Family Applications After (3)

Application Number Title Priority Date Filing Date
GB43798/65A Expired GB1024904A (en) 1962-03-21 1963-03-21 Novel psychotrine derivatives
GB11454/65A Expired GB1024902A (en) 1962-03-21 1963-03-21 A process for the preparation of optically active benzo[a]quinolizine derivatives
GB43797/65A Expired GB1024903A (en) 1962-03-21 1963-03-21 Novel homoveratryl amides

Country Status (10)

Country Link
BE (1) BE629898A (en)
BR (1) BR6347679D0 (en)
CH (1) CH419138A (en)
CY (1) CY376A (en)
DE (1) DE1445875A1 (en)
DK (2) DK123654B (en)
ES (1) ES286240A1 (en)
GB (4) GB1024901A (en)
MY (1) MY6700083A (en)
OA (1) OA00962A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4686226A (en) * 1985-09-03 1987-08-11 Merck & Co., Inc. Substituted benzo[b]furo- and benzo[b]thieno quinolizines

Also Published As

Publication number Publication date
GB1024902A (en) 1966-04-06
GB1024903A (en) 1966-04-06
CH419138A (en) 1966-08-31
MY6700083A (en) 1967-12-31
DE1545946B2 (en) 1975-06-19
CY376A (en) 1967-03-01
BE629898A (en) 1963-10-21
DK123654B (en) 1972-07-17
DK107613C (en) 1967-06-19
OA00962A (en) 1968-08-07
BR6347679D0 (en) 1973-08-02
DE1545946A1 (en) 1970-04-09
ES286240A1 (en) 1963-11-16
DE1445875A1 (en) 1969-04-10
GB1024904A (en) 1966-04-06

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