GB926493A - Novel iú¾ú´quinoline derivatives and a process for the manufacture thereof - Google Patents

Novel iú¾ú´quinoline derivatives and a process for the manufacture thereof

Info

Publication number
GB926493A
GB926493A GB11483/61A GB1148361A GB926493A GB 926493 A GB926493 A GB 926493A GB 11483/61 A GB11483/61 A GB 11483/61A GB 1148361 A GB1148361 A GB 1148361A GB 926493 A GB926493 A GB 926493A
Authority
GB
United Kingdom
Prior art keywords
acid
homoveratrylamide
methyl
derivatives
methyl derivatives
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
GB11483/61A
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 GB926493A publication Critical patent/GB926493A/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
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring

Landscapes

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

Abstract

The invention comprises substituted tetrahydroisoquinolines of the general formula <FORM:0926493/IV(a)/1> (wherein R1 is a hydrogen atom or an alkyl group, n is 1 or 2 and S stands for 6- or 7-methoxy, 6,7-dimethoxy or 6,7-methylenedioxy substitution), their N-methyl derivatives, addition salts of the N-methyl derivatives with inorganic and organic acids, a process for the preparation of the substituted tetrahydroisoquinolines by cyclizing the appropriately substituted phenalkanoic acid phenethylamide in the presence of a cyclizing agent and reducing the resulting 3,4-dihydroisoquinoline derivative with an alkali metal aluminium hydride or borohydride (and, optionally, resolving the racemic product), followed by N-methylation (and, optionally, salt formation) in the case of the N-methyl derivatives, and pharmaceutical compositions containing an N-methyl derivative or acid addition salt thereof in association with a pharmaceutical carrier. 4-Nitrodihydrocinnamic acid homoveratrylamide, homopiperonylamide and 3-methoxyphenethylamide, g -(4-nitrophenyl)-butyric acid homoveratrylamide, 3- nitrodihydrocinnamic acid homoveratrylamide and 1-methyl-2-(4-nitrophenyl)- propionic acid homoveratrylamide are prepared by condensing the parent acid and amine, and are cyclized to the corresponding 3,4-dihydroisoquinoline derivatives. The N-methyl derivatives and their acid addition salts exhibit analgesic, spasmolytic and antitussive activity and may be administered enterally or parenterally in the form of pharmaceutical compositions (e.g. tablets, dragees, suppositories, capsules, solutions, emulsions or suspensions) containing them in association with a carrier, with or without other (unspecified) therapeutically useful substances.
GB11483/61A 1960-04-01 1961-03-29 Novel iú¾ú´quinoline derivatives and a process for the manufacture thereof Expired GB926493A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH366460 1960-04-01
CH924860 1960-08-15

Publications (1)

Publication Number Publication Date
GB926493A true GB926493A (en) 1963-05-22

Family

ID=25693560

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11483/61A Expired GB926493A (en) 1960-04-01 1961-03-29 Novel iú¾ú´quinoline derivatives and a process for the manufacture thereof

Country Status (3)

Country Link
BE (1) BE601828A (en)
FR (1) FR1032M (en)
GB (1) GB926493A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3378561A (en) * 1965-03-18 1968-04-16 Bristol Myers Co 1-beta-arylthioethyltetrahydro-isoquinolines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3378561A (en) * 1965-03-18 1968-04-16 Bristol Myers Co 1-beta-arylthioethyltetrahydro-isoquinolines

Also Published As

Publication number Publication date
BE601828A (en) 1961-07-27
FR1032M (en) 1962-01-02

Similar Documents

Publication Publication Date Title
IE43506L (en) Isoquinolines
US3534053A (en) Quinuclidine derivatives
Yamato et al. Synthesis of 6, 7-dihydrox-1, 2, 3, 4-tetrahydroisoquinoline derivatives
US3733330A (en) Benzomorphan derivatives
US3389141A (en) 1-beta-aryloxyethyltetrahydro-isoquinolines
US2885401A (en) Process for making morphinan dertva-
US3483206A (en) N-isoquinolylalkanoyl-n-arylamines
GB926493A (en) Novel iú¾ú´quinoline derivatives and a process for the manufacture thereof
US2619484A (en) Y-dihydro - sh-dibenz
GB964143A (en) Substituted quinolines
US3647802A (en) 2-amino-4-aryl-3 4-dihydroquinolines
US2655498A (en) N-benzhydbyl-n alkyl-substituted
US3437662A (en) Polyhydroisoquinoline antiviral agents
US3238212A (en) 1-substituted-1-phenyl(or substituted phenyl)-2-[2-methyl-6, 7-substituted-1, 2, 3, 4-tetrahydroisoquinolinyl-(1)] ethanes
US3067203A (en) Tetrahybroisqquinoline derivatives
US3870721A (en) 4-alkanoylamino isoquinoline diones and 3-alkanoyloxy-4-alkanoylamino isoquinolones
Jacobson et al. Paradoxical effects of N-cyanoalkyl substituents upon the activities of several classes of opioids
US4194044A (en) Process for preparing 3-phenoxy morphinans
US3311633A (en) Behydro-emehnes
US3476755A (en) 8,13-diazasteroids
EP0051190A2 (en) N-(amino(or hydroxy) phenethyl)-1,2,3,4-tetrahydroisoquinolines, precursors thereof, and methods of preparation
US3578668A (en) 1-aminoalkylamino-benzo(b) quinolizines
Govindachari et al. Synthesis of quinolizine derivatives
US3497501A (en) Heterocyclic amino esters of 2-phenylacrylic acid
US3903093A (en) 2-({62 -Alkyl thioethyl)-6,7-benzomorphans