GB921978A - Quaternary ammonium compounds, the preparation thereof and the pharmaceutical compositions thereof - Google Patents

Quaternary ammonium compounds, the preparation thereof and the pharmaceutical compositions thereof

Info

Publication number
GB921978A
GB921978A GB8778/59A GB877859A GB921978A GB 921978 A GB921978 A GB 921978A GB 8778/59 A GB8778/59 A GB 8778/59A GB 877859 A GB877859 A GB 877859A GB 921978 A GB921978 A GB 921978A
Authority
GB
United Kingdom
Prior art keywords
methylthio
phenoxyethane
ethyl
methoxy
reacting
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
GB8778/59A
Inventor
Frederick Charles Copp
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation 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
Priority claimed from GB9896/56A external-priority patent/GB824853A/en
Application filed by Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB8778/59A priority Critical patent/GB921978A/en
Priority to FR821113A priority patent/FR84256E/en
Priority to CH1601464A priority patent/CH395126A/en
Priority to CH288660A priority patent/CH388331A/en
Publication of GB921978A publication Critical patent/GB921978A/en
Priority to OA50769A priority patent/OA038E/xx
Priority to MY130/65A priority patent/MY6500130A/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
    • A41—WEARING APPAREL
    • A41D—OUTERWEAR; PROTECTIVE GARMENTS; ACCESSORIES
    • A41D27/00—Details of garments or of their making
    • A41D27/02—Linings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/28—Halogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises quaternary ammonium compounds containing a cation of the general formula <FORM:0921978/IV(a)/1> wherein either R1 is hydrogen or a halogen, methyl, ethyl, methoxy, methylthio, formyl, cyano or nitro substituent and R2 is an iodine, methoxy, nitro, cyano or methylthio substituent or R1 is a fluorine, iodine, ethyl, methoxy, methylthio, formyl or cyano substituent and R2 is hydrogen or a fluorine, chlorine, bromine or methyl substituent, and their preparation by quaternating a corresponding tertiary amine with a reactive ester of the hydroxy derivative containing the group it is desired to introduce; for example, by reacting a suitable N-benzyl-N-methylamino-2-phenoxyethane with a methylating agent, or reacting a 1-dimethylamino-2-phenoxyethane with an appropriate benzylating agent. Alternatively the quaternary compounds may be prepared by reacting a 1-benzylamino-2-phenoxyethane with two mols of a methylating agent. The salt obtained may be converted by double decomposition in solution or on an anion exchange column into the salt of another anion. Starting materials. 1-(N-o-Methoxybenzyl-N-methylamino)-2-phenoxyethane and 1-(N-benzyl-N-methylamino) - 2 - o - (ethyl, fluoro, methoxy, cyano and formyl)-phenoxyethane are made by treating the appropriate N-methyl-benzylamine with a phenoxyethyl bromide. o-Methylthio-benzyl bromide is made by reducing o - methylthio - benzoic acid with lithium aluminium hydride and reacting the resulting o-methylthio-benzyl alcohol with hydrobromic acid. o - Ethyl - phenoxyethyl bromide is made by the action of ethylene dibromide on o-ethyl phenol. Pharmaceutical preparations for the treatment of nematode infestations, especially in animals, comprise the above quaternary compounds of the invention a pharmaceutical carrier. The preparations may suitably take the form of powders or granules for the preparation of a draft or drench in water, capsules, cachets, tablets, suspensions, solutions or emulsions.
GB8778/59A 1956-03-29 1959-03-13 Quaternary ammonium compounds, the preparation thereof and the pharmaceutical compositions thereof Expired GB921978A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB8778/59A GB921978A (en) 1956-03-29 1959-03-13 Quaternary ammonium compounds, the preparation thereof and the pharmaceutical compositions thereof
FR821113A FR84256E (en) 1956-03-29 1960-03-11 Quaternary ammonium compounds and their preparation
CH1601464A CH395126A (en) 1956-05-29 1960-03-12 Process for preparing quaternary ammonium compounds
CH288660A CH388331A (en) 1956-03-29 1960-03-12 Process for preparing quaternary ammonium compounds
OA50769A OA038E (en) 1959-02-13 1964-12-08
MY130/65A MY6500130A (en) 1959-03-13 1965-12-30 Quaternary ammonium compounds the preparation thereof and the pharmaceutical compositions thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9896/56A GB824853A (en) 1956-03-29 1956-03-29 Improvements in and relating to quaternary ammonium compounds and the preparation thereof
GB8778/59A GB921978A (en) 1956-03-29 1959-03-13 Quaternary ammonium compounds, the preparation thereof and the pharmaceutical compositions thereof

Publications (1)

Publication Number Publication Date
GB921978A true GB921978A (en) 1963-03-27

Family

ID=37124676

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8778/59A Expired GB921978A (en) 1956-03-29 1959-03-13 Quaternary ammonium compounds, the preparation thereof and the pharmaceutical compositions thereof

Country Status (2)

Country Link
CH (1) CH388331A (en)
GB (1) GB921978A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2512444A1 (en) * 1981-09-08 1983-03-11 Occidental Chem Co ALKALINE BATHS WITH ELECTROLYTIC ZINC COATING, CONTAINING ALKYLATED HYDROXYLARYLIC COMPOUNDS

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2512444A1 (en) * 1981-09-08 1983-03-11 Occidental Chem Co ALKALINE BATHS WITH ELECTROLYTIC ZINC COATING, CONTAINING ALKYLATED HYDROXYLARYLIC COMPOUNDS

Also Published As

Publication number Publication date
CH388331A (en) 1965-02-28

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