GB1235002A - Improvements in or relating to oxazoloisoquinoline derivatives - Google Patents

Improvements in or relating to oxazoloisoquinoline derivatives

Info

Publication number
GB1235002A
GB1235002A GB38266/68A GB3826668A GB1235002A GB 1235002 A GB1235002 A GB 1235002A GB 38266/68 A GB38266/68 A GB 38266/68A GB 3826668 A GB3826668 A GB 3826668A GB 1235002 A GB1235002 A GB 1235002A
Authority
GB
United Kingdom
Prior art keywords
general formula
acid addition
addition salt
phenyl
tetrahydroisoquinoline
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
GB38266/68A
Inventor
William Joseph Houlihan
Robert Everett Manning
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.)
Sandoz AG
Original Assignee
Sandoz 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 Sandoz AG filed Critical Sandoz AG
Publication of GB1235002A publication Critical patent/GB1235002A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
    • C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Abstract

1,235,002. 1 - Phenyl - 3 - imino - 1,5,6,10btetrahydro - 3H - oxazolo[4,3-a]isoquinolines. SANDOZ Ltd. 9 Aug., 1968 [25 Aug., 1967; 21 May, 1968], No. 38266/68. Heading C2C. Novel 1 - phenyl - 3 - imino - 1,5,6,10b - tetrahydro - 3H - oxazolo[4,3-a]isoquinolines of the general formula wherein R, R 1 , R 2 and R 3 are each a hydrogen, fluorine or chlorine atom or a trifluoromethyl group, R 4 and R 5 are each a hydrogen, fluorine or chlorine atom or a straight chain C 1-4 alkyl group and R 6 is a hydrogen atom or a straight chain C 1-4 alkyl group, with the provisos (i) that no more than three of R, R 1 , R 2 , R 3 , R 4 and R 5 are other than a hydrogen atom and. (ii) R, R 1 , R 2 and R 3 are such that there is never a trifluoromethyl group on each of two adjacent carbon atoms, the compounds being in free base or acid addition salt form when R 6 is a hydrogen atom and in acid addition salt form when R 6 is an alkyl group, are prepared as follows: (a) obtaining a hydrochloride by reaction of a 1-(α- hydroxybenzyl) - 1,2,3,4 - tetrahydroisoquinoline-2-carboxamide of the general formula with thionyl chloride; (b) obtaining a mixed salt of a compound of the first general formula above wherein R 6 is a hydrogen atom by reaction of an α-phenyl-1,2,3,4-tetrahydroisoquinoline-1-methanol of the general formula with cyanogen bromide and lithium, sodium, potassium or calcium acetate in the presence of an inert organic solvent; (c) obtaining an acid addition salt of a compound of the first general formula above wherein R 6 is a straight chain C 1-4 alkyl group by reaction of an α-phenyl- 1, 2, 3,4-tetrahydroisoquinoline-1-methanol of the general formula wherein R<SP>1</SP> 6 is a straight chain C 1-4 alkyl group, with cyanogen bromide and the acetate of lithium, sodium, potassium or calcium, and reaction of the resulting 1-(α-hydroxybenzyl)- 1,2,3,4 - tetrahydroisoquinoline - 2 - carbonitrile of the general formula with an acid; (d) obtaining a compound of the first general formula above wherein R 6 is a hydrogen atom or an acid addition salt thereof by basifying an acid addition salt of the general formula wherein A is a chlorine or bromine atom or an acetate group, and, when an acid addition salt is required, reacting the resulting compound of the first general formula above wherein R 6 is a hydrogen atom with an acid; and (e) obtaining an acid addition salt of a compound of the first general formula above wherein R 6 is a straight chain C 1-4 alkyl group by basifying and then acidifying the corresponding hydrochloride salt. Pharmaceutical compositions having antidepressant and anorexic activity comprise, as active ingredient, a 1-phenyl-3-imino-1,5,6,10btetrahydro - 3H - oxazolo[4,3-a]isoquinoline of the first general formula above or a pharmaceutically acceptable acid addition salt thereof, the compound being in the form of a said acid addition salt unless R 6 is a hydrogen atom, in association with a pharmaceutically acceptable carrier or diluent, and may be administered orally or parenterally. 1 - (α - Hydroxybenzyl) - 1,2,3,4 - tetrahydroisoquinoline-2-carboxamides of the second general formula above are prepared by treatment of an α - phenyl - 1,2,3,4 - tetrahydroisoquinoline- 1-methanol of the general formula under acidic conditions with an alkali metal isocyanate in an inert organic solvent. α - Phenyl - 1,2,3,4 - tetrahydroisoquinoline- 1 -methanols of the general formula immediately above are prepared (a) by cyclization of an N- phenethyl - 2 - phenyl - acetamide of the general formula with phosphorus pentoxide in an inert solvent at 75-150‹ C., treatment of the resulting 1 - benzyl - 3,4 - dihydroisoquinoline of the general formula with air or oxygen and reduction of the obtained 1 - benzoyl - 3,4 - dihydroisoquinoline of the general formula at 20-50‹ C. in an inert solvent with hydrogen in the presence of a platinum catalyst; or (b) by reaction of a 1-cyano-2-benzoyl-1,2-dihydroisoquinoline with a lithium compound and a benzaldehyde derivative, followed by catalytic hydrogenation.
GB38266/68A 1967-08-25 1968-08-09 Improvements in or relating to oxazoloisoquinoline derivatives Expired GB1235002A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US66321867A 1967-08-25 1967-08-25
US73095768A 1968-05-21 1968-05-21

Publications (1)

Publication Number Publication Date
GB1235002A true GB1235002A (en) 1971-06-09

Family

ID=27098701

Family Applications (1)

Application Number Title Priority Date Filing Date
GB38266/68A Expired GB1235002A (en) 1967-08-25 1968-08-09 Improvements in or relating to oxazoloisoquinoline derivatives

Country Status (8)

Country Link
JP (1) JPS4826019B1 (en)
BE (1) BE719921A (en)
CH (2) CH498144A (en)
DE (1) DE1795189A1 (en)
ES (3) ES357503A1 (en)
FR (2) FR1587682A (en)
GB (1) GB1235002A (en)
SE (1) SE333144B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51147818A (en) * 1975-06-11 1976-12-18 Aisin Seiki Co Ltd Seat slide adjusting device
DE102007006795B3 (en) * 2007-02-12 2008-04-03 Takraf Gmbh Dust-free bulk material transfer device e.g. for ship loader, has annular seal provided between transfer chute and rotational cute

Also Published As

Publication number Publication date
ES357503A1 (en) 1970-03-16
FR1587682A (en) 1970-03-27
JPS4826019B1 (en) 1973-08-03
BE719921A (en) 1969-02-24
ES389793A1 (en) 1974-03-01
CH498145A (en) 1970-10-31
SE333144B (en) 1971-03-08
FR8101M (en) 1970-07-27
CH498144A (en) 1970-10-31
DE1795189A1 (en) 1972-01-05
ES373529A1 (en) 1972-06-01

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