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ES256264A1 - Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof - Google Patents

Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof

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Publication number
ES256264A1
ES256264A1 ES0256264A ES256264A ES256264A1 ES 256264 A1 ES256264 A1 ES 256264A1 ES 0256264 A ES0256264 A ES 0256264A ES 256264 A ES256264 A ES 256264A ES 256264 A1 ES256264 A1 ES 256264A1
Authority
ES
Spain
Prior art keywords
alkyl
alkoxy
phenyl ring
compounds
benzyl
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
ES0256264A
Other languages
Spanish (es)
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
Application filed by Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Publication of ES256264A1 publication Critical patent/ES256264A1/en
Expired legal-status Critical Current

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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
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
    • C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
    • C07C217/20—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
    • 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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • 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
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen 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
    • C07D333/06—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)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Furan Compounds (AREA)

Abstract

The invention comprises quaternary amino compounds containing a cation of the formula R.W.CH2CH2.N+XY.CH2.L, wherein R is a phenyl ring, substituted in the m- or p-positions by a halogen, alkyl, alkoxy, hydroxy, formyl, acetyl, alkoxycarbonyl, amino, acetamido, cyano or nitro substituent when L is a phenyl ring optionally bearing a halogen, alkyl, alkoxy, cyano or nitro substituent or a thienyl or furyl ring optionally bearing a 5-halo or 5-nitro substituent or R is a phenyl ring optionally substituted in the o-position by a halogen, alkyl, alkoxy, hydroxy, formyl, acetyl, alkoxy-carbonyl, amino, acetamido, cyano or nitro substituent when L is a phenyl ring substituted in the m- or p-position by a halogen, alkyl, alkoxy cyano or nitro substituent W is a straight saturated chain containing 1-3 nonadjacent oxygen atoms and 0-16 carbon atoms and X and Y are each an alkyl or alkyl group or NXY forms a pyrrolidino, piperidino or morpholino ring, the terms "alkyl", "alkoxy" and "alkoxycarbonyl" denoting groups of 1-4 carbon atoms with the exception of compounds containing a N-5-p-chlorophenoxy-3-oxapentyl-N-p-chlorobenzyl-N, N-dimethylammonium, N - p - t - butylphenoxyethoxyethyl-N-benzyl-N,N-dimethylammonium, N - benzyl-N-5-p-methylphenoxy-3-oxapentyl-N,N-dimethylammonium, N - benzyl - N,N-diethyl - N-2-m-methoxyphenoxyethylammonium or N - benzyl - N, N - diethyl - N - 2 - m butoxyethylammonium cation. It comprises also a process for preparing these compounds by reacting the corresponding tertiary amine with a reactive ester of the hydroxy derivative of the group it is desired to introduce, e.g. with an alkylating agent. Alternatively a secondary amine may be treated with two equivalents of an alkylating agent or with an a ,o -disubstituted butane, pentane or 3-oxapentane (to form the pyrrolidine, piperidine or morpholine groups). Similarly the products may also be made by internal quaternisation of a tertiary amine R.W.CH2CH2.N(XYZ). CH2L wherein XY is a tetramethylene pentamethylene or 3-oxapentamethylene chain bearing a terminal ester group Z. When R is a phenyl ring bearing an amino substituent it is necessary to protect the amine group with an acyl, alkoxycarbonyl or hydrocarbonsulphonyl group which is subsequently removed by hydrolysis of the quaternary compound. Salts of the products are made by conventional processes of salt - formation, double decomposition and anion exchange. Secondary and tertiary amines, corresponding to the above quaternary compounds, are prepared by standard methods. p-2-Bromoethoxyacetophenone is made by the action of ethylene dibromide on p-hydroxyacetophenone Phenoxy alkyl halides of the formula R2-C6H4.W.CH2CH2Z, wherein R2 is Br, CH3, CH3O or NO2 and Z is Br or Cl are described. 1-o-Bromobenzyloxy-2-chloroethane is made by reacting o-bromobenzyl bromide with ethylene glycol and chlorinating the resulting 1-o-bromobenzyloxy-2-hydroxyethane. Pharmaceutical preparations for the treatment of nematode infestations comprise the above quaternary compounds (including the compounds specifically excluded from the product claims), suitably in the form of salts with borofluoride, perchlorate, laurylsulphate, dodecylsulphonate, p-toluenesulphonate, p-chlorobenzenesulphonate, p-bromobenzenesulphonate, p-acylaminobenzenesulphonate, acylaminocarboxylate, diphenylsulphonate, naphthalene mono- and di-sulphonate, naphthoate, dihydroxydiarylmethane dicarboxylate, piperazine-1,4-bis-carbodithioate, diaminostilbenedisulphonate, phenate or trichlorophenate anions, and a pharmaceutical carrier. The preparations may suitably take the form of tablets, granules, capsules, cachets, suspensions, emulsions or a draft or drench in water or a syrup.
ES0256264A 1959-03-13 1960-03-04 Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof Expired ES256264A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB8878/59A GB924961A (en) 1959-03-13 1959-03-13 Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof
GB887959 1959-03-13
GB3955859 1959-11-20
GB3955959 1959-11-20

Publications (1)

Publication Number Publication Date
ES256264A1 true ES256264A1 (en) 1960-08-16

Family

ID=27447685

Family Applications (1)

Application Number Title Priority Date Filing Date
ES0256264A Expired ES256264A1 (en) 1959-03-13 1960-03-04 Quaternary ammonium compounds, the preparation thereof and pharmaceutical compositions thereof

Country Status (10)

Country Link
BE (1) BE588558A (en)
CH (2) CH422758A (en)
DE (1) DE1238485C2 (en)
DK (1) DK104353C (en)
ES (1) ES256264A1 (en)
FR (2) FR1421206A (en)
GB (1) GB924961A (en)
GR (1) GR29331B (en)
LU (1) LU38374A1 (en)
NL (2) NL129619C (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES410734A1 (en) * 1973-01-18 1976-01-01 Rocador Sa Butacaine pamoate
US3956369A (en) * 1973-05-18 1976-05-11 Ozeretskovskaya Natalia Nikola N-β-(2-acetyl-4-chlorophenoxy)-ethyl-N,N-dimethyl-N-benzyl-ammonium-p-chlorobenzene sulphonate, method for preparing same and medicinal preparation based thereon
FR2387213A2 (en) * 1977-04-12 1978-11-10 Nattermann A & Cie Smooth-muscle relaxant quat. ammonium salts - derived from aminoalkoxy-di:phenyl-propiolophenone derivs.
DE2913523A1 (en) 1979-04-04 1980-10-23 Basf Ag SUBSTITUTED ALKYLAMONIUM SALTS, THEIR PRODUCTION AND USE FOR REGULATING PLANT GROWTH
DE3233828A1 (en) * 1982-09-11 1984-03-15 Basf Ag, 6700 Ludwigshafen ARYLOXYALKYLAMINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR CONTROLLING UNWANTED PLANT GROWTH
GB9321811D0 (en) * 1993-10-22 1993-12-15 Smithkline Beecham Plc Pharmaceuticals
GB9321812D0 (en) * 1993-10-22 1993-12-15 Smithkline Beecham Plc Pharmaceuticals
EP0982300A3 (en) * 1998-07-29 2000-03-08 Societe Civile Bioprojet Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications
EP0978512A1 (en) * 1998-07-29 2000-02-09 Societe Civile Bioprojet Non-imidazole aryloxy (or arylthio) alkylamines as histamine H3-receptor antagonists and their therapeutic applications
DE10235312A1 (en) 2002-08-01 2004-02-12 Basf Ag Process for the preparation of aminoalkoxybenzylamines and aminoalkoxybenzonitriles as intermediates
US20130178653A1 (en) * 2010-09-21 2013-07-11 Imperial College Novel precursor of radiolabelled choline analog compounds
US12162851B2 (en) 2020-03-11 2024-12-10 Nocion Therapeutics, Inc. Charged ion channel blockers and methods for use
EP4118070A4 (en) * 2020-03-11 2024-04-10 Nocion Therapeutics, Inc. CHARGED ION CHANNEL BLOCKERS AND METHODS OF USE

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1117600B (en) * 1956-03-29 1961-11-23 Wellcome Found Process for the preparation of quaternary ammonium salts effective against nematodes

Also Published As

Publication number Publication date
NL129619C (en) 1970-08-18
CH436259A (en) 1967-05-31
FR558M (en) 1961-05-29
FR1421206A (en) 1965-12-17
LU38374A1 (en) 1960-09-12
DK104353C (en) 1966-05-09
CH422758A (en) 1966-10-31
NL6909922A (en) 1969-10-27
DE1238485B (en) 1967-04-13
GR29331B (en) 1965-12-29
DE1238485C2 (en) 1967-10-26
GB924961A (en) 1963-05-01
BE588558A (en) 1960-09-12

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