GB1004077A - Pharmaceutical compositions containing dibenzoquinolizines - Google Patents

Pharmaceutical compositions containing dibenzoquinolizines

Info

Publication number
GB1004077A
GB1004077A GB3430463A GB3430463A GB1004077A GB 1004077 A GB1004077 A GB 1004077A GB 3430463 A GB3430463 A GB 3430463A GB 3430463 A GB3430463 A GB 3430463A GB 1004077 A GB1004077 A GB 1004077A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
methoxy
dibenzo
ethoxy
hydroxy
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
GB3430463A
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.)
Smith Kline and French Laboratories Ltd
Original Assignee
Smith Kline and French Laboratories 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 Smith Kline and French Laboratories Ltd filed Critical Smith Kline and French Laboratories Ltd
Publication of GB1004077A publication Critical patent/GB1004077A/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
    • 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
    • C07D217/02—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
    • C07D217/06—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 with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
    • 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
    • C07D217/18—Aralkyl radicals
    • C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

5,6,13,13a - Tetrahydro - 8H - dibenzo-(a,g) - quinolizines of the general formula <FORM:1004077/C2/1> where R1 and R2 represent hydrogen, hydroxy, methoxy, ethoxy or, when taken together, methylenedioxy; R3 and R5 represent hydrogen ar methoxy; R4 represents hydrogen, hydroxy, methoxy, or ethoxy; and R6 and R7 represent hydrogen or methyl; may be prepared by condensing the appropriately substituted phenylacetic acid and phenethylamine to give the N-substituted phenethylamide which is ring-closed by heating in the presence of phosphorus oxychloride to the 3,4-dihydroisoquinoline. Reduction of the latter with hydrogen and platinum oxide catalyst gives the corresponding 1,2,3,4-tetrahydroisoquinoline. Reaction of the latter with a 37% formaldehyde solution gives the final 5,6,13,13a - tetrahydro - 8H - dibenzo-(a.g) quinolizine of the above formula.ALSO:A pharmaceutical composition having tranquillising, antidepressant and antiemetic activity comprises a pharmaceutical carrier and a 5, 6, 13, 13a-tetrahydro-8-dibenzo-(a,g)-quinolizine or a non-toxic pharmaceutically acceptable addition salt thereof, said dibenzo-(a,g)-quinolizine having the formula <FORM:1004077/A5-A6/1> in which R1 and R2 are hydrogen, hydroxy, methoxy, ethoxy or, when taken together, methylenedioxy; R3 and R5 are hydrogen or methoxy; R4 is hydrogen, hydroxy, methoxy, or ethoxy; and R6 and R7 are hydrogen or methyl. The pharmaceutically active compound may be in the racemic, d, or l forms. The compositions may contain from 5 mg. to 150 mg. per dosage unit. The carrier may be solid or liquid and may contain a time-delay material. The composition may be tabletted, placed in a gelatine capsule, troche, or lozenge, or suspended in a liquid water-soluble salts of the active medicament may be dissolved in water or saline solution such that 1 cc of solution contains 10-50 mg of active medicament. The solution may be incorporated in ampoules.
GB3430463A 1962-09-21 1963-08-29 Pharmaceutical compositions containing dibenzoquinolizines Expired GB1004077A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US22535862A 1962-09-21 1962-09-21

Publications (1)

Publication Number Publication Date
GB1004077A true GB1004077A (en) 1965-09-08

Family

ID=22844557

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3430463A Expired GB1004077A (en) 1962-09-21 1963-08-29 Pharmaceutical compositions containing dibenzoquinolizines

Country Status (1)

Country Link
GB (1) GB1004077A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0028959A1 (en) * 1979-11-13 1981-05-20 U.R.P.H.A. 5,8,13,13a-Tetrahydro-6H-dibenzo(a,g)quinolizine derivatives, process for their preparation and pharmaceutical compositions containing them
FR2537583A1 (en) * 1982-12-14 1984-06-15 Urpha LEVOGYRANT ENANTIOMERS OF TETRAHYDRO-5, 6, 13, 13A-8H-DIBENZO (A, G-) QUINOLIZINE DERIVATIVES, METHODS OF OBTAINING THEM, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AND USE THEREOF
US6030978A (en) * 1998-04-24 2000-02-29 Hanwha Corporation Antifungal formulation comprising protoberberine derivatives and salts thereof

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0028959A1 (en) * 1979-11-13 1981-05-20 U.R.P.H.A. 5,8,13,13a-Tetrahydro-6H-dibenzo(a,g)quinolizine derivatives, process for their preparation and pharmaceutical compositions containing them
FR2469413A1 (en) * 1979-11-13 1981-05-22 Urpha 6H-DIBENZO (A, G) 5,8,13,13A-TETRAHYDROQUINOLIZINE DERIVATIVES, PROCESS FOR OBTAINING AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
FR2537583A1 (en) * 1982-12-14 1984-06-15 Urpha LEVOGYRANT ENANTIOMERS OF TETRAHYDRO-5, 6, 13, 13A-8H-DIBENZO (A, G-) QUINOLIZINE DERIVATIVES, METHODS OF OBTAINING THEM, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AND USE THEREOF
WO1984002342A1 (en) * 1982-12-14 1984-06-21 Urpha LAEVOGYROUS ENANTIOMERS OF TETRAHYDRO-5,6,13,13a-8H-DIBENZO ADa,g BD-QUINOLIZINE DERIVATIVES
EP0112252A1 (en) * 1982-12-14 1984-06-27 U.R.P.H.A. Levorotatory enantiomers of derivatives of tetrahydro-5,6,13,13a-8H-dibenzo(a,g)quinolizine, process for their preparation, phamaceutical composition containing them, and their application
US4645772A (en) * 1982-12-14 1987-02-24 Urpha Levorotatory enantiomers of derivatives of 5,6,13,13a-tetrahydro-8H-dibenzo [A,G]quinolizine, preparative process, pharmaceutical compositions containing them and application
US6030978A (en) * 1998-04-24 2000-02-29 Hanwha Corporation Antifungal formulation comprising protoberberine derivatives and salts thereof

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