GB1098569A - Hexahydro-11bh-benzo[a]quinolizine derivatives and preparation thereof - Google Patents

Hexahydro-11bh-benzo[a]quinolizine derivatives and preparation thereof

Info

Publication number
GB1098569A
GB1098569A GB5661766A GB5661766A GB1098569A GB 1098569 A GB1098569 A GB 1098569A GB 5661766 A GB5661766 A GB 5661766A GB 5661766 A GB5661766 A GB 5661766A GB 1098569 A GB1098569 A GB 1098569A
Authority
GB
United Kingdom
Prior art keywords
ester
general formula
acid
substituted
reacting
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
GB5661766A
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.)
Merck KGaA
Original Assignee
E Merck 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 E Merck AG filed Critical E Merck AG
Publication of GB1098569A publication Critical patent/GB1098569A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems
    • 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
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
    • C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Novel quinolizines of the general formula <FORM:1098569/C2/1> wherein R1 and R2 are H C1-C4 alkyl groups and in which the benzene rings may be substituted with 1 or more F, Cl, Br, C1-C4 alkyl and/or C1-C3 alkoxy or methylene-dioxy substituents and their acid addition and quaternary ammonium salts are prepared by reacting a dihydroisoquinoline of the general formula <FORM:1098569/C2/2> which may be substituted as above defined, or a salt of such a compound, with methylvinylketone, a Mannich base of acetone or a quaternary salt of such a Mannich base, or by subjecting an ester of general formula <FORM:1098569/C2/3> wherein R3 is H or COOR and R is C1-C4 alkyl1 and in which the benzene rings may be substituted as above to intra-molecular condensation in the presence of an inert solvent and a cyclizing agent and hydrolysing and decarboxylating the resulting keto ester. The dihydroisoquinolines of the second formula above are prepared by reacting a compound of the general formula (C6H5)2CR1CHR2NH2, where the phenyl groups may be substituted as above defined, but an H atom is present in at least one of the ortho-positions, with formic acid and ring closing the N-formyl derivative using a cyclizing agent. Esters of the third formula above may be prepared by reacting the above 2,2-diarylethylamines with malonic acid esters, or malonic acid hemiester acid chlorides, cyclizing the semi-ester amide formed, catalytically hydrogenating the 1,2-double linkage of the resulting 1 - carboxylic ester - 4 - aryl-3,4-dihydroisoquinoline and alkylating the resulting secondary amino ester with an acrylic acid or a beta-halopropionic acid ester at the nitrogen atom. Pharmaceutical compositions comprise as active ingredient a compound of the first general formula above and a conventional excipient. The compositions may be in the form of oily or aqueous solutions or suspensions or emulsion for parenteral application, tablets or dragees for enteral application and ointments or creams for topical application. Adjuvants such as preserving, stabilizing or wetting agents or salts may also be present.
GB5661766A 1966-01-07 1966-12-19 Hexahydro-11bh-benzo[a]quinolizine derivatives and preparation thereof Expired GB1098569A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEM0067937 1966-01-07

Publications (1)

Publication Number Publication Date
GB1098569A true GB1098569A (en) 1968-01-10

Family

ID=7312393

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5661766A Expired GB1098569A (en) 1966-01-07 1966-12-19 Hexahydro-11bh-benzo[a]quinolizine derivatives and preparation thereof

Country Status (9)

Country Link
BE (1) BE692193A (en)
CH (1) CH484140A (en)
DE (1) DE1595977A1 (en)
DK (1) DK119164B (en)
ES (1) ES335330A1 (en)
GB (1) GB1098569A (en)
IL (1) IL27024A (en)
NL (1) NL6617790A (en)
SE (1) SE335536B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4421917A (en) * 1982-07-16 1983-12-20 Mcneilab, Inc. Derivatives of 2-ureido-7-phenylhexahydrobenzo[a]quinolizines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4421917A (en) * 1982-07-16 1983-12-20 Mcneilab, Inc. Derivatives of 2-ureido-7-phenylhexahydrobenzo[a]quinolizines

Also Published As

Publication number Publication date
DE1595977A1 (en) 1970-03-12
ES335330A1 (en) 1968-04-01
SE335536B (en) 1971-06-01
BE692193A (en) 1967-07-04
DK119164B (en) 1970-11-23
NL6617790A (en) 1967-07-10
CH484140A (en) 1970-01-15
IL27024A (en) 1970-07-19

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