GB1036271A - New tertiary aryloxyalkylaminoalkylamines and their manufacture - Google Patents

New tertiary aryloxyalkylaminoalkylamines and their manufacture

Info

Publication number
GB1036271A
GB1036271A GB4139661A GB4139661A GB1036271A GB 1036271 A GB1036271 A GB 1036271A GB 4139661 A GB4139661 A GB 4139661A GB 4139661 A GB4139661 A GB 4139661A GB 1036271 A GB1036271 A GB 1036271A
Authority
GB
United Kingdom
Prior art keywords
group
reaction
formula
groups
reduction
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
GB4139661A
Inventor
Elzina Geertr Proosdij-Hartzem
Geertruida Cornelia Va Leeuwen
Antony Marie Akkerman
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.)
Nederlandsche Combinatie voor Chemische Industrie NV
Original Assignee
Nederlandsche Combinatie voor Chemische Industrie NV
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 Nederlandsche Combinatie voor Chemische Industrie NV filed Critical Nederlandsche Combinatie voor Chemische Industrie NV
Priority to GB4139661A priority Critical patent/GB1036271A/en
Priority to US212456A priority patent/US3239520A/en
Priority to DE19621470119 priority patent/DE1470119A1/en
Priority to CH1344762A priority patent/CH421103A/en
Priority to CH1344862A priority patent/CH451148A/en
Priority to DEN22367A priority patent/DE1283841B/en
Priority to BR144752/62A priority patent/BR6244752D0/en
Priority to BR144753/62A priority patent/BR6244753D0/en
Priority to DK497162AA priority patent/DK105205C/en
Priority to FR924587A priority patent/FR2468M/en
Publication of GB1036271A publication Critical patent/GB1036271A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
    • C07D241/18—Oxygen or sulfur atoms

Landscapes

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

Abstract

The invention comprises compounds of formula Ar-O-X-NR1-Y-NR2R3 wherein Ar is a pyridyl or pyrazyl radical optionally substituted by one or more C1- 4 alkyl groups, or a phenyl group optionally substituted by a methylenedioxy group, one or two C1- 4 alkyl groups or halogen atoms of which at most one is in an ortho-position with respect to the aminoalkylaminoalkoxy group, or one or more C1- 4 alkoxy, nitro or trifluoromethyl groups, X and Y are C2- 4 alkylene groups, R1 is a hydroge atom or a C1- 4 alkyl group and R2 and R3 are C1- 4 alkyl groups which may be linked directly or through an oxygen or sulphur atom, and addition salts thereof, and their preparation by (a) reaction of an amine with an aryloxyalkanoyl halide to form an amide of formula Ar-O-X1-CONR1-Y-NR2R3 wherein X1 is an alkylene group having one carbon atom less than X, and reducing the carbonyl group, (b) reaction of an aryl halide with the alkali metal salt of a tertiary-aminoalkylamino alkylamino alkanol, (c) reduction of a compound of formula Ar-O-X1-CONR1-Y1-CONR2R2 wherein X1 and Y1 are alkylene groups, each having one carbon atom less than X and Y respectively, (d) reaction of an aryloxyalkyl halide with an aminoalkylamine, (e) reaction of an aryloxyacetone with an aminoethylamine, followed by reduction of the azomethine product of formula Ar-O-CH2-C(CH3) = N-CH2CH2NR2R3 or (f) N-alkylation to reduce the group R1 by acylation and reduction. The compounds of the invention have anti-tussive activity.
GB4139661A 1961-11-20 1961-11-20 New tertiary aryloxyalkylaminoalkylamines and their manufacture Expired GB1036271A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
GB4139661A GB1036271A (en) 1961-11-20 1961-11-20 New tertiary aryloxyalkylaminoalkylamines and their manufacture
US212456A US3239520A (en) 1961-11-20 1962-07-25 N-(monocarbocyclic aryloxy-lower alkyl)-n' (diloweralkyl, or heterocyclic)-lower alkylene diamines
DE19621470119 DE1470119A1 (en) 1961-11-20 1962-11-16 Process for the preparation of substituted phenoxyalkylaminoalkyl tertiary amines and their acidic addition salts
CH1344762A CH421103A (en) 1961-11-20 1962-11-16 Process for the preparation of new tertiary alkyl amines
CH1344862A CH451148A (en) 1961-11-20 1962-11-16 Process for the preparation of new tertiary amines
DEN22367A DE1283841B (en) 1961-11-20 1962-11-16 Basically substituted ethers of ethanolamine
BR144752/62A BR6244752D0 (en) 1961-11-20 1962-11-19 PROCESS FOR PREPARING NEW REPLACED FERROXI-LAQUIL-AMINO-ALKYL-SUBSTITUTED AMINES AND THEIR SALTS
BR144753/62A BR6244753D0 (en) 1961-11-20 1962-11-19 PROCESS TO PREPARE NEW HETERO-ARYLOXYALKYL-AMINO-ALKYLIC TYPICAL TYPICAL AMINES AND THEIR SALTS
DK497162AA DK105205C (en) 1961-11-20 1962-11-19 Process for the preparation of pyridyl or pyrazyloxyalkylaminoalkylamines or acid addition salts thereof.
FR924587A FR2468M (en) 1961-11-20 1963-02-13 New cough suppressants.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4139661A GB1036271A (en) 1961-11-20 1961-11-20 New tertiary aryloxyalkylaminoalkylamines and their manufacture

Publications (1)

Publication Number Publication Date
GB1036271A true GB1036271A (en) 1966-07-20

Family

ID=10419503

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4139661A Expired GB1036271A (en) 1961-11-20 1961-11-20 New tertiary aryloxyalkylaminoalkylamines and their manufacture

Country Status (1)

Country Link
GB (1) GB1036271A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5780642A (en) * 1993-06-22 1998-07-14 Knoll Aktiengesellschaft Imidazole derivatives as therapeutic agents

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5780642A (en) * 1993-06-22 1998-07-14 Knoll Aktiengesellschaft Imidazole derivatives as therapeutic agents

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