GB1019571A - Preparation of 2-dehydroemetine derivatives - Google Patents

Preparation of 2-dehydroemetine derivatives

Info

Publication number
GB1019571A
GB1019571A GB3157161A GB3157161A GB1019571A GB 1019571 A GB1019571 A GB 1019571A GB 3157161 A GB3157161 A GB 3157161A GB 3157161 A GB3157161 A GB 3157161A GB 1019571 A GB1019571 A GB 1019571A
Authority
GB
United Kingdom
Prior art keywords
group
metal
aliphatic
araliphatic
substituents
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
GB3157161A
Inventor
Alexander Crawford Ritchie
Dennis Edward Clark
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 GB3157161A priority Critical patent/GB1019571A/en
Priority to DK369362A priority patent/DK111620B/en
Priority to CH1273366A priority patent/CH449015A/en
Priority to CH1027562A priority patent/CH447177A/en
Priority to DE19621445807 priority patent/DE1445807A1/en
Publication of GB1019571A publication Critical patent/GB1019571A/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
    • 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)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the formula <FORM:1019571/C2/1> and their acid addition salts, wherein R1 is an aliphatic, araliphatic or aromatic hydrocarbon group, R1 is an aliphatic, araliphatic or aromatic hydrocarbon group which may have hydroxy or acyloxy substituents and R3 is hydrogen or an acyl group, and wherein the benzene rings optionally bear one or more aliphatic, araliphatic or aromatic hydrocarbon or ether (including methylenedioxy) groups as substituents; and the process for the production of the corresponding derivatives having a group R1.CH2- in place of R1.CH(OR3)- in the 3-position by reducing compounds of the above formula wherein R3 is an acyl group by means of a metal/ammonia or metal/primary amine reducing system, e.g. lithium or calcium in liquid ammonia. The compounds of Formula II are prepared by reducing a corresponding ketone (having a group R1CO in the 3-position and in which R1 may also bear oxo substituents) with a reagent serving to reduce an oxo group to a hydroxyl group, e.g. a metal hydride reducing agent such as an alkali or alkaline earth metal borohydride or aluminium hydride, and acylating the product, e.g. by reaction with an acid anhydride such as acetic anhydride. When the starting material contains a group R2CO.CH2-CH2- as the substituent R1 in the 21-position (R2 being an aliphatic or araliphatic hydrocarbon group, e.g. CH3), reduction converts this to the corresponding 3-hydroxy radical and, on esterification to the 3-acyloxy radical, which remain unreduced by the subsequent metal/ammonia or metal/primary amine reaction. The resulting product containing a 21-(3-hydroxyalkyl)-side chain may be oxidized to the corresponding 3-oxo-alkyl derivative and the side chain may then be removed by oxidation and treatment with hydrazine or a base, or in one step by Oppenhauer oxidation with an alkali-metal alkoxide and a ketone. Preferably the ring system contains methoxy substituents in the 61, 71, 9 and 10 positions giving products of the emetine series. In examples 3-acetyl - 1,4,6,7 - tetrahydro - 9,10 - dimethoxy - 2 - [11,21,31,41 - tetrahydro - 61,71 - dimethoxy - 21 - (311 - oxobutyl isoquinol - 11 - yl] - methyl - 11b[H]-benzo-[a]-quinolizine is reduced with sodium borohydride to give the corresponding 3 - a - hydroxyethyl - 21 - (311 - hydroxybutyl) - compound, treated with acetic anhydride to form the diacetate, reduced with lithium aluminium hydride in liquid ammonia to give N-(3-hydroxybutyl) dehydroemetine and treated with potassium t.-butoxide and benzophenone to give dehydroemetine (hydrogen chloride); similarly the reduction is also effected with sodium and calcium in liquid ammonia in place of lithium.
GB3157161A 1961-09-01 1961-09-01 Preparation of 2-dehydroemetine derivatives Expired GB1019571A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
GB3157161A GB1019571A (en) 1961-09-01 1961-09-01 Preparation of 2-dehydroemetine derivatives
DK369362A DK111620B (en) 1961-09-01 1962-08-23 Process for the preparation of benzoquinolizine compounds.
CH1273366A CH449015A (en) 1961-09-01 1962-08-29 Process for making new esters
CH1027562A CH447177A (en) 1961-09-01 1962-08-29 Process for the preparation of 2-dehydroemetine derivatives
DE19621445807 DE1445807A1 (en) 1961-09-01 1962-08-31 Process for the preparation of 2-dehydroemetine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3157161A GB1019571A (en) 1961-09-01 1961-09-01 Preparation of 2-dehydroemetine derivatives

Publications (1)

Publication Number Publication Date
GB1019571A true GB1019571A (en) 1966-02-09

Family

ID=10325115

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3157161A Expired GB1019571A (en) 1961-09-01 1961-09-01 Preparation of 2-dehydroemetine derivatives

Country Status (4)

Country Link
CH (2) CH447177A (en)
DE (1) DE1445807A1 (en)
DK (1) DK111620B (en)
GB (1) GB1019571A (en)

Also Published As

Publication number Publication date
DK111620B (en) 1968-09-23
CH449015A (en) 1967-12-31
CH447177A (en) 1967-11-30
DE1445807A1 (en) 1969-12-11

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