GB1014348A - Antidepressant compositions comprising phenoxyalkylamines - Google Patents

Antidepressant compositions comprising phenoxyalkylamines

Info

Publication number
GB1014348A
GB1014348A GB46923/63A GB4692363A GB1014348A GB 1014348 A GB1014348 A GB 1014348A GB 46923/63 A GB46923/63 A GB 46923/63A GB 4692363 A GB4692363 A GB 4692363A GB 1014348 A GB1014348 A GB 1014348A
Authority
GB
United Kingdom
Prior art keywords
give
radical
preparation
methyl radical
hydrogen
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
GB46923/63A
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 GB1014348A publication Critical patent/GB1014348A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrrole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Phenoxyalkylamines of the general formula <FORM:1014348/C2/1> wherein R and R1 are each a hydrogen, chlorine or bromine atom, a trifluoromethyl radical or a C1- 4 alkyl or alkoxy group, X is a divalent alkylene group having the formula <FORM:1014348/C2/2> R2 is a hydrogen atom or a methyl radical and R3 is a methyl radical, or R2, R3 and the nitrogen atom together form a pyrrolidine or piperidine ring, may be prepared by condensing the appropriate phenol (as its sodium salt) with an aminoalkyl halide to give the product directly or, alternatively, the phenol may be condensed with an a -haloalkanoamide to give the corresponding a -phenoxyamide which may then be reduced to the amine, e.g. with LiAlH4. The products may be converted to acid addition salts. The Specification also discloses the preparation of N,N - dimethyl - a - bromo - propionamide by reacting a -bromopropionyl bromide with dimethylamine; the preparation of 2-(2,6-dichlorophenoxy) - N,N,1 - trimethylethylamine by reacting 2,6-dichlorophenol with chloroacetone to give 2,6-dichlorophenoxyacetone which is reacted with dimethylamine and formic acid to give the required product; and the preparation of N-monomethyl-2-(2,6-dichlorophenoxy) - propylamine by heating the corresponding N,N-dimethyl compound with cyanogen bromide and hydrolysing the product.ALSO:Pharmaceutical compositions in unit dosage form comprise a carrier and phenoxyalkylamine (or an acid addition salt thereof) of the general formula <FORM:1014348/A5-A6/1> wherein R and R1 are each a hydrogen, chlorine or bromine atom a trifluoromethyl radical or a C1-4 alkyl or alkoxy radical, X is a divalent alkylene group having the formula <FORM:1014348/A5-A6/2> or <FORM:1014348/A5-A6/3> R2 is a hydrogen atom or a methyl radical and R3 is a methyl radical or R2, R3 and the nitrogen atom together form a pyrrolidine or peperidine ring. The compositions-which have anti-depressant activity-may be in conventional forms for oral or parenteral administration, e.g. a tablet, powder, capsules, troche, lozenge, or injectable preparation.
GB46923/63A 1962-12-24 1963-11-27 Antidepressant compositions comprising phenoxyalkylamines Expired GB1014348A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US246672A US3205136A (en) 1962-12-24 1962-12-24 Antidepressant phenyloxyalkylamines

Publications (1)

Publication Number Publication Date
GB1014348A true GB1014348A (en) 1965-12-22

Family

ID=22931695

Family Applications (1)

Application Number Title Priority Date Filing Date
GB46923/63A Expired GB1014348A (en) 1962-12-24 1963-11-27 Antidepressant compositions comprising phenoxyalkylamines

Country Status (4)

Country Link
US (1) US3205136A (en)
BE (1) BE640617A (en)
FR (1) FR3075M (en)
GB (1) GB1014348A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003011210A2 (en) * 2001-07-31 2003-02-13 Astrazeneca Ab Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase
US6887871B2 (en) 2000-02-23 2005-05-03 Astrazeneca Ab Use of phenylheteroakylamine derivatives
US6900243B2 (en) 2000-02-23 2005-05-31 Astrazeneca Ab Phenylheteroalkylamine derivatives
US6953797B2 (en) 2000-02-23 2005-10-11 Astrazeneca Ab Use of phenylheteroalkylamine derivatives

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3515741A (en) * 1964-04-20 1970-06-02 Boehringer Sohn Ingelheim 1-cyanophenoxy-2-amino-alkanes
GB1161915A (en) * 1966-06-03 1969-08-20 Ciba Ltd Pharmaceutical Preparations comprising Sulphur-Containing Amino-Compounds for the Treatment of Depressive Conditions
BE761623A (en) * 1970-04-15 1971-06-16 Recordati Chem Pharm NEW THERAPEUTICALLY ACTIVE PHENOXYETHYLAMINES SUBSTITUTES AND PROCESS FOR THEIR PREPARATION
GB1374366A (en) * 1972-07-21 1974-11-20 Science Union & Cie Propanol derivatives and a process for their preparation
DE2524363A1 (en) * 1975-06-02 1976-12-16 Boehringer Sohn Ingelheim NEW PHARMACEUTICAL PRODUCTS
IE47716B1 (en) * 1977-08-05 1984-05-30 Kabi Ab Geminally disubstituted indene derivatives
HU184392B (en) * 1981-03-04 1984-08-28 Gyogyszerkutato Intezet Process for producing new alkylene-diamine derivatives
ZA855101B (en) * 1984-07-13 1986-05-28 Merrell Dow Pharma Fluoroallylaine derivatives
US4795758A (en) * 1986-02-10 1989-01-03 Societe A Responsabilite Limitee: Institut De Recherches Chimiques Et Biologiques Appliquees (I.R.C.E.B.A.) 5-[2-(pyrrolidin-1-yl)ethoxy]-p-cymene derivatives, the process for the preparation of the said derivatives and drugs in which the said derivatives are present
AR004691A1 (en) 1995-10-27 1999-03-10 Astrazeneca Ab NEW DERIVATIVES OF [3-ALCOXI-PENOXI -) - ETIL] -DIALKYLAMINE, A PHARMACEUTICAL COMPOSITION THAT INCLUDES THEM, THEIR USE AS LOCAL ANESTHETICS AND A PROCEDURE FOR THEIR PREPARATION

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB765849A (en) * 1953-09-21 1957-01-16 Univ Leeds Improvements in or relating to new aminoalkyl phenyl ethers
CH380746A (en) * 1958-11-06 1964-08-15 Ciba Geigy Process for the preparation of new secondary amines
US3077472A (en) * 1961-03-21 1963-02-12 Univ Kansas Res Foundation 3-[4-(aminoalkoxy)-phenyl]-4-(4-oxyphenyl)-alkanes and alkenes

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6887871B2 (en) 2000-02-23 2005-05-03 Astrazeneca Ab Use of phenylheteroakylamine derivatives
US6900243B2 (en) 2000-02-23 2005-05-31 Astrazeneca Ab Phenylheteroalkylamine derivatives
US6953797B2 (en) 2000-02-23 2005-10-11 Astrazeneca Ab Use of phenylheteroalkylamine derivatives
WO2003011210A2 (en) * 2001-07-31 2003-02-13 Astrazeneca Ab Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase
US7223794B2 (en) 2001-07-31 2007-05-29 Astrazeneca Ab Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase
WO2003011210A3 (en) * 2001-07-31 2007-10-25 Astrazeneca Ab Arylheteroalkylamine derivatives and their use as inhibitors of nitric oxide synthase

Also Published As

Publication number Publication date
BE640617A (en) 1964-05-29
US3205136A (en) 1965-09-07
FR3075M (en) 1965-01-18

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