GB969077A - Novel tertiary amines and a process for the manufacture thereof - Google Patents

Novel tertiary amines and a process for the manufacture thereof

Info

Publication number
GB969077A
GB969077A GB14803/62A GB1480362A GB969077A GB 969077 A GB969077 A GB 969077A GB 14803/62 A GB14803/62 A GB 14803/62A GB 1480362 A GB1480362 A GB 1480362A GB 969077 A GB969077 A GB 969077A
Authority
GB
United Kingdom
Prior art keywords
compound
hydrogenated
optically active
racemic
compounds
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
GB14803/62A
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 GB969077A publication Critical patent/GB969077A/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
    • C07D217/04—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 hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • 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
    • C07D217/10—Quaternary compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention comprises compounds of the general formula: <FORM:0969077/C1/1> (wherein X is an ethylene or methyl-substituted ethylene group and S stands for one or two chlorine, bromine or fluorine atoms or a p-nitro group) in their racemic and optically active forms, medicinally acceptable acid addition salts thereof, their preparation by quaternising an isoquinoline of the general formula: <FORM:0969077/C1/2> (wherein S1 stands for one or two chlorine, bromine or fluorine atoms and the broken lines denote optional substituents) with a methylating agent, converting the resulting quaternary salt to the corresponding quaternary ammonium hydroxide, subjecting the latter to a Hofmann degradation to produce an olefinic compound of the formula: <FORM:0969077/C1/3> hydrogenating this compound at the olefinic bond, nitrating the hydrogenated compound when it contains an unsubstituted phenyl group and, if desired, converting the hydrogenated or hydrogenated and nitrated compound as the case may be to an acid addition salt, and pharmaceutical preparations containing a compound of the invention in association with a carrier. The optically active compounds may be prepared by using an optically active starting material or by using a racemic starting material and separating the optical antipodes after the hydrogenation step. 1-(2-Vinyl-4, 5-dimethoxyphenyl) -1- dimethylamino -3- (4-chlorophenyl)- propane is characterized as the methiodide and D-camphorsulphonate. (-) and (+) 1-[(3, 4-Dichlorophenyl)-ethyl]-2-methyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinoline are prepared from the racemic compound. The compounds of the invention possess analgesic, spasmolytic, antitussive and bloodpressure lowering properties and may be administered enterally or parenterally in the form of pharmaceutical preparations (e.g. tablets, dragees, suppositories, capsules, solutions, suspensions or emulsions) containing them, with or without other (unspecified) therapeutically valuable substances, in association with a carrier. Specification 862,052 is referred to.
GB14803/62A 1961-04-21 1962-04-17 Novel tertiary amines and a process for the manufacture thereof Expired GB969077A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH471261A CH410007A (en) 1961-04-21 1961-04-21 Process for the preparation of tertiary amines

Publications (1)

Publication Number Publication Date
GB969077A true GB969077A (en) 1964-09-09

Family

ID=4281191

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14803/62A Expired GB969077A (en) 1961-04-21 1962-04-17 Novel tertiary amines and a process for the manufacture thereof

Country Status (5)

Country Link
BE (1) BE616393A (en)
CH (1) CH410007A (en)
ES (1) ES276647A1 (en)
FR (1) FR1824M (en)
GB (1) GB969077A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001009101A1 (en) * 1999-07-29 2001-02-08 EGIS Gyógyszergyár Rt. Isoquinoline derivatives, pharmaceutical compositions containing the same, and a process for the preparation of the active substance

Also Published As

Publication number Publication date
ES276647A1 (en) 1962-10-16
BE616393A (en) 1962-10-15
FR1824M (en) 1963-05-20
CH410007A (en) 1966-03-31

Similar Documents

Publication Publication Date Title
FI77018B (en) ANALOGIFICATION OF THE ANTIDEPRESSIVE ACTIVATED (-) - ENANTIERS OF N-METHYL-N- [3- (2-METHYLPHENOXY) -3-PHENYLPROPYL / AMINE IN THE PHARMACEUTICAL FORM OF THE PRODUCT &#34;SALT.
DE1543374C3 (en) 3,4 Dihydroxyphenylalkanolamines and their acid addition salts, processes for their production and pharmaceutical preparations
Zirkle et al. 2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions
DE1668055B2 (en) BASIC SUBSTITUTED CYCLOPENTYLPHENOLETHERS, THEIR SALT WITH PHYSIOLOGICALLY COMPATIBLE ACIDS AND PROCESS FOR THEIR PRODUCTION
US3536713A (en) N-(hydroxy-cyclohexyl)-aminobenzylamines and the salts thereof
EP0374756A2 (en) Nitrogen-containing cyclic compounds
DE2143204B2 (en) N-fluoroalkyl-phenylisopropylamine derivatives and their salts, processes for their preparation and pharmaceuticals based on them
DE3010752A1 (en) SUBSTITUTED AETHANOLAMINE
CH616146A5 (en)
US3980655A (en) Basically substituted 1,4-dihydro-2H-isoquinoline derivatives and process for preparing them
SK280776B6 (en) Benzomorphanes, method of their preparation, pharmaceutical agents containing them, and their use
DE2115926B2 (en) 1- (4-HYDROXY-3-DIMETHYLAMINOSULFAMIDOPHENYL) -2-AMINOETHANE DERIVATIVES, THE PROCESS FOR THEIR PREPARATION AND AGENTS CONTAINING THESE
US3138639A (en) Tertiary amines and a process for producing same
GB969077A (en) Novel tertiary amines and a process for the manufacture thereof
US3225098A (en) N-substituted phenylalkylamines
Miller et al. Optically active catecholimidazolines: a study of steric interactions at. alpha.-adrenoreceptors
Maciąg et al. Evaluation of some aroxyethylamine derivatives for hypotensive properties and their affinities for adrenergic receptors
US3127405A (en) I-phenylalkyl
AT230870B (en) Process for the preparation of tertiary amines and their salt-like derivatives
US2600301A (en) N-substituted-beta halo-ethyl amines
US3600380A (en) Certain 1-aralkyl-3-azetidinol compounds
CA1209586A (en) Naphthalenecarboxamides, their production and use
Henze et al. Synthesis of 5-Disubstituted Aminomethyl-5-phenethylhydantoins1
US3188349A (en) N-secondary-alkyl-2-(3-hydroxyphenyl)-2-ethyl-alkylamines
Lourie et al. The Syntheses and Hypotensive Activities of Some Substituted 1, 4-Diazabicyclo [4.4. 0] decanes