DE1231702B - Process for the production of new ethers - Google Patents

Process for the production of new ethers

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Publication number
DE1231702B
DE1231702B DEH52256A DEH0052256A DE1231702B DE 1231702 B DE1231702 B DE 1231702B DE H52256 A DEH52256 A DE H52256A DE H0052256 A DEH0052256 A DE H0052256A DE 1231702 B DE1231702 B DE 1231702B
Authority
DE
Germany
Prior art keywords
production
dimethyl
pyridylmethoxy
formula
reaction
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.)
Pending
Application number
DEH52256A
Other languages
German (de)
Inventor
Dr Gustav Erlemann
Dr Waldemar Guex
Dr Otto Schnider
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
Priority claimed from US273271A external-priority patent/US3230228A/en
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of DE1231702B publication Critical patent/DE1231702B/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/673—Vitamin B group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Pyridine Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Int. Cl.:Int. Cl .:

C07dC07d

Deutschem.: 12 ρ-1/01German: 12 ρ-1/01

Nummer: 1 231 702Number: 1 231 702

Aktenzeichen: H 52256IV d/12 ρFile number: H 52256IV d / 12 ρ

Anmeldetag: 4. April 1964 Filing date: April 4, 1964

Auslegetag: 5. Januar 1967Opened on: January 5, 1967

Die vorliegende Erfindung bezieht sich auf ein Verfahren zur Herstellung von neuen Äthern der allgemeinen FormelThe present invention relates to a process for the production of new ethers of the general formula

(i)(i)

worin X ein Sauerstoff- oder Schwefelatom und R den jS-Pyridylmethyl- oder den Cetylrest darstellt.wherein X is an oxygen or sulfur atom and R is the jS-pyridylmethyl or the cetyl radical.

Das erfindungsgemäße Verfahren ist dadurch gekennzeichnet, daß man racemisches oder optisch aktives «-Hydroxy-zS^-dimethyl-y-butyrolacton mit einem Amin der allgemeinen FormelThe inventive method is characterized in that one racemic or optical active «-hydroxy-zS ^ -dimethyl-y-butyrolactone with an amine of the general formula

H2N-CH2-CH2-CH2-X-R (II)H 2 N-CH 2 -CH 2 -CH 2 -XR (II)

worin die Symbole X und R die obige Bedeutung haben, umsetzt.wherein the symbols X and R have the above meaning.

«-Hydroxy-jS^-dimethyl-y-butyrolacton ist eine bekannte Substanz, und zwar sind sowohl die racemische Form als auch die optisch aktiven Formen dieses Lactons bekannt.«-Hydroxy-jS ^ -dimethyl-y-butyrolactone is a well-known one Substance, both the racemic form and the optically active forms are this Known lactons.

Die Amine der obigen Formel II können in einfacher Weise dadurch hergestellt werden, daß man den entsprechenden Alkohol bzw. das entsprechende Thiol mit Acrylnitril umsetzt und hierauf die Cyangruppe des so erhaltenen Umsetzungsproduktes hydriert. So kann beispielsweise das 3-(^-Pyridylmethoxy)-propylamin dadurch hergestellt werden, daß man ß-(Hydroxymethyl)-pyridin mit Acrylnitril umsetzt und das erhaltene 3-(^-Pyridylmethoxy)-propionitril hydriert.The amines of the above formula II can be prepared in a simple manner by reacts the corresponding alcohol or the corresponding thiol with acrylonitrile and then the cyano group of the reaction product thus obtained is hydrogenated. For example, 3 - (^ - pyridylmethoxy) propylamine be prepared by ß- (hydroxymethyl) pyridine with acrylonitrile and the 3 - (^ - pyridylmethoxy) propionitrile obtained is hydrogenated.

Die Umsetzung des Butyrolactons mit dem Amin der Formel II wird zweckmäßigerweise in Abwesenheit eines Lösungsmittels durchgeführt. Diese Reaktion ist exotherm und setzt sofort beim Vermischen des Butyrolactons mit dem Amin ein. Vorzugsweise Verfahren zur Herstellung von neuen ÄthernThe reaction of the butyrolactone with the amine of the formula II is expediently carried out in the absence carried out a solvent. This reaction is exothermic and starts immediately when the Butyrolactones with the amine. Preferably method for the production of new ethers

Anmelder:Applicant:

F. Hoffmann-La Roche & Co. Aktiengesellschaft, Basel (Schweiz)F. Hoffmann-La Roche & Co. Aktiengesellschaft, Basel (Switzerland)

Vertreter:Representative:

G. Schmitt, Rechtsanwalt,
Lörrach (Bad.), Friedrichstr. 3G. Schmitt, lawyer,
Loerrach (Bad.), Friedrichstr. 3

Als Erfinder benannt:
Dr. Gustav Erlemann, Riehen;
Dr. Waldemar Guex, Bottmingen;
Dr. Otto Schnider, Basel (Schweiz)Named as inventor:
Dr. Gustav Erlemann, Riehen;
Dr. Waldemar Guex, Bottmingen;
Dr. Otto Schnider, Basel (Switzerland)

Beanspruchte Priorität:Claimed priority:

V. St. v. Amerika vom 16. April 1963 (273 271)V. St. v. America April 16, 1963 (273 271)

werden äquimolare Mengen der Reaktionskomponenten verwendet. Es empfiehlt sich, das Reaktionsgemisch nach Abklingen der Wärmeentwicklung noch einige Stunden bei oder wenig über Raumtemperatur stehenzulassen.equimolar amounts of the reaction components are used. It is advisable to start the reaction mixture after the evolution of heat has subsided let stand for a few more hours at or a little above room temperature.

Als Ausgangsmaterialien der Formel II eignen sich besonders solche Amine, in denen X ein Sauerstoffatom bedeutet. Man erhält hierdurch entsprechende Verbindungen der Formel I, in denen X Sauerstoff ist, nämlich N-(«,y-Dihydroxy-/3,^-dimethyl-butyryl)-3-(/3-pyridylmethoxy)-propylamin der FormelParticularly suitable starting materials of the formula II are those amines in which X is an oxygen atom means. This gives corresponding compounds of the formula I in which X is oxygen is, namely N - («, y-dihydroxy- / 3, ^ - dimethyl-butyryl) -3 - (/ 3-pyridylmethoxy) -propylamine the formula

CH3 CH 3

HO —CH2-C-CHOH-CO-NH-CH2-CH2-CH2-O-CH2-HO —CH 2 -C-CHOH-CO-NH-CH 2 -CH 2 -CH 2 -O-CH 2 -

CH3 Ν>CH 3 Ν >

(in)(in)

bzw. N-(«,y-Dihydroxy-/3,/^dimethyl-butyryl)-3-cetyloxy-propylamin. or N - («, y-dihydroxy- / 3, / ^ dimethyl-butyryl) -3-cetyloxypropylamine.

Die Verbindungen der Formel I sind in den üblichen organischen Lösungsmitteln, beispielsweise in Äthylalkohol, Äthylacetat und Aceton leicht löslich. Der /3-Pyridylmethyläther ist auch in Wasser löslich.The compounds of formula I are in the usual organic solvents, for example in ethyl alcohol, Easily soluble in ethyl acetate and acetone. The / 3-pyridyl methyl ether is also soluble in water.

Die Verbindungen der Formel I, und zwar besonders das N-(«,y-Dihydroxy-/3,/^dimethyl-butyryl)-3-cetyloxy-propylamin, können für die Herstellung von kosmetischen Präparaten, beispielsweise von Haarwässern, Haarölen und von Präparaten für die Hautpflege verwendet werden.
Die neuen Verbindungen der Formel I, und zwar besonders das N-(oc,y-Dihydroxy-/3,/?-dimethyl-butyryl)-3-(/3-pyridylmethoxy)-propylamin, das neben seiner Pantothensäurewirkung auch eine die BlutzirkulationThe compounds of the formula I, especially the N - («, y-dihydroxy- / 3, / ^ dimethyl-butyryl) -3-cetyloxy-propylamine, can be used for the production of cosmetic preparations, for example of hair lotions, hair oils and of Preparations used for skin care.
The new compounds of the formula I, specifically N- (oc, y-dihydroxy- / 3, /? - dimethyl-butyryl) -3 - (/ 3-pyridylmethoxy) propylamine, which in addition to its pantothenic acid effect also stimulates blood circulation

609 750/397609 750/397

fördernde Wirksamkeit aufweist, können auch zur Herstellung von pharmazeutischen Präparaten verwendet werden.Has promoting effectiveness, can also be used for the production of pharmaceutical preparations will.

BeispiellFor example

Zu 39 g d(— )-a-Hydroxy-ß,/^dimethyl-y-butyrolacton wurden unter Rühren 49,8 g 3-(/J-Pyridylmethoxy)-propylamin zugesetzt, worauf die Reaktion sofort unter Selbsterhitzung eintrat. Die Temperatur des Reaktionsgemisches stieg auf etwa 500C an. Nach dem Abklingen der Reaktion wurde das Reaktionsgemisch weitere 30 Minuten auf dieser Temperatur gehalten, worauf es 48 Stunden lang bei Raumtemperatur stehengelassen wurde. Auf diese Weise wurde D(+)-N-(«,y-Dihydroxy-/?,ß-dimethyl-butyryl)-3-(|S-pyridylmethoxy)-propylamin in Form eines farblosen Öls erhalten, das mit Wasser mischbar, in Alkoholen löslich, in Äther jedoch unlöslich ist. [oc]f = +15,2° (c = 3,15 in Wasser).49.8 g of 3 - (/ I-pyridylmethoxy) propylamine were added to 39 g of (-) -a-hydroxy-β, / ^ dimethyl-y-butyrolactone with stirring, whereupon the reaction started immediately with self-heating. The temperature of the reaction mixture rose to about 50 0 C. After the reaction had subsided, the reaction mixture was held at this temperature for an additional 30 minutes, after which it was allowed to stand at room temperature for 48 hours. In this way, D (+) - N - («, y-dihydroxy - / ?, ß-dimethyl-butyryl) -3- (| S-pyridylmethoxy) -propylamine was obtained in the form of a colorless oil which is miscible with water, soluble in alcohols but insoluble in ether. [oc] f = + 15.2 ° (c = 3.15 in water).

Das nach den obigen Angaben als Ausgangsmaterial verwendete 3-(/?-Pyridylmethoxy)-propylamin kann durch katalytische Hydrierung von 3-(/3-Pyridylmethoxy)-propionitril (mit Raney-Nickel) in methanolischem Ammoniak erhalten werden. Siedepunkt = Kp.18 = 163 bis 165° C.The 3 - (/? - pyridylmethoxy) propylamine used as starting material according to the above information can be obtained by catalytic hydrogenation of 3 - (/ 3-pyridylmethoxy) propionitrile (with Raney nickel) in methanolic ammonia. Boiling point = bp 18 = 163 to 165 ° C.

Das 3-(/?-Pyridylmethoxy)-propionitril seinerseits kann durch Umsetzung von /S-(Hydroxy-methyl)-pyridin mit Acrylnitril erhalten werden. Kp.lo = 177 bis 181°C.The 3 - (/? - pyridylmethoxy) propionitrile for its part can be obtained by reacting / S- (hydroxymethyl) pyridine with acrylonitrile. B.p. lo = 177 to 181 ° C.

Beispiel 2Example 2

Zu 6,5 g d(—)-«-Hydroxy-/S,^-dimethyl-y-butyrolacton wurden bei Raumtemperatur unter Rühren 14,35 g - 3-Cetyloxy-propylamin zugesetzt, wobei die Reaktion unmittelbar unter Selbsterhitzung einsetzte und die Temperatur des Reaktionsgemisches auf 540C anstieg. Nach Abklingen der Reaktion wurde das Reaktionsgemisch unter Rühren 2 Stunden lang auf dieser Temperatur gehalten. Hierauf wurde das Gemisch 2 Tage bei Raumtemperatur stehengelassen. Das auf diese Weise in quantitativer Ausbeute erhaltene D(+)-N-(*,y-Dihydroxy-ß,/3-dimethyl-butyryl)-3-cetyloxy-propylamin ist eine farblose, wachsartige Substanz, die in den üblichen Lösungsmitteln, beispielsweise in Alkohol, leicht löslich ist, während sie in Wasser unlöslich ist. [«]?? = +23,5 bis 23,8° (c = 3 in Methanol).14.35 g of 3-cetyloxypropylamine were added to 6.5 g of (-) - «- hydroxy- / S, ^ - dimethyl-y-butyrolactone at room temperature with stirring, the reaction starting immediately with self-heating and the temperature of the reaction mixture rose to 54 ° C. After the reaction had subsided, the reaction mixture was kept at this temperature for 2 hours with stirring. The mixture was then left to stand at room temperature for 2 days. The D (+) - N - (*, y-dihydroxy-ß, / 3-dimethyl-butyryl) -3-cetyloxy-propylamine obtained in this way in quantitative yield is a colorless, waxy substance which, in the usual solvents, for example in alcohol, is readily soluble while it is insoluble in water. [«] ?? = +23.5 to 23.8 ° (c = 3 in methanol).

Das als Ausgangsmaterial verwendete 3-Cetyloxypropylamin kann durch katalytische Hydrierung von 3-Cetyloxy-propionitril (mit Raney-Nickel) in Methanol in Gegenwart von Ammoniak erhalten werden. Kp.lo = 210 bis 213°C; F. etwa 300C.The 3-cetyloxypropylamine used as starting material can be obtained by catalytic hydrogenation of 3-cetyloxypropionitrile (with Raney nickel) in methanol in the presence of ammonia. B.p. lo = 210 to 213 ° C; F. about 30 0 C.

Das 3-Cetyloxy-propionitril seinerseits kann durch Umsetzung von Cetylalkohol mit Acrylnitril gewonnen werden; F. = 50 bis 52°C.The 3-cetyloxy-propionitrile in turn can be obtained by reacting cetyl alcohol with acrylonitrile will; F. = 50 to 52 ° C.

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung von neuen Äthern der allgemeinen FormelProcess for the production of new ethers of the general formula CH2(OH — C(CHs)2- CHOH — CONH — (CH2)3— X-RCH 2 (OH - C (CHs) 2 - CHOH - CONH - (CH 2 ) 3 - XR worin X ein Sauerstoff- oder Schwefelatom und R den jS-Pyridylmethyl- oder den Cetylrest darstellt, dadurch gekennzeichnet, daß man racemisch.es oder optisch aktives «-Hydroxy-/δ,/J-dimethyl-y-butyrolacton mit einem Amin der allgemeinen Formelwherein X is an oxygen or sulfur atom and R is the jS-pyridylmethyl or the cetyl radical, characterized in that one racemisch.es or optically active -hydroxy- / δ, / J-dimethyl-y-butyrolactone with an amine of the general formula H2N-CH2-CH2-CH2-X-R (II)H 2 N-CH 2 -CH 2 -CH 2 -XR (II) worin die Symbole X und R die obige Bedeutung haben, umsetzt.wherein the symbols X and R have the above meaning. 609 750/397 12.66 © Bundesdruckerei Berlin609 750/397 12.66 © Bundesdruckerei Berlin
DEH52256A 1963-04-16 1964-04-04 Process for the production of new ethers Pending DE1231702B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US273271A US3230228A (en) 1961-03-30 1963-04-16 Panthenol derivatives and processes for their preparation

Publications (1)

Publication Number Publication Date
DE1231702B true DE1231702B (en) 1967-01-05

Family

ID=23043246

Family Applications (1)

Application Number Title Priority Date Filing Date
DEH52256A Pending DE1231702B (en) 1963-04-16 1964-04-04 Process for the production of new ethers

Country Status (9)

Country Link
BE (1) BE646523A (en)
BR (1) BR6458449D0 (en)
CH (1) CH441309A (en)
DE (1) DE1231702B (en)
DK (1) DK117628B (en)
FR (1) FR3398M (en)
GB (1) GB1042204A (en)
NL (1) NL6404018A (en)
SE (1) SE313806B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0161422A1 (en) * 1984-03-21 1985-11-21 TERUMO KABUSHIKI KAISHA trading as TERUMO CORPORATION Alkanolamine derivatives and platelet aggregation inhibitors containing the same as an active ingredient

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0161422A1 (en) * 1984-03-21 1985-11-21 TERUMO KABUSHIKI KAISHA trading as TERUMO CORPORATION Alkanolamine derivatives and platelet aggregation inhibitors containing the same as an active ingredient
US4619938A (en) * 1984-03-21 1986-10-28 Terumo Kabushiki Kaisha Fatty acid derivatives of aminoalkyl nicotinic acid esters and platelet aggregation inhibitors

Also Published As

Publication number Publication date
NL6404018A (en) 1964-10-19
BR6458449D0 (en) 1973-08-28
DK117628B (en) 1970-05-19
BE646523A (en) 1964-10-14
GB1042204A (en) 1966-09-14
CH441309A (en) 1967-08-15
SE313806B (en) 1969-08-25
FR3398M (en) 1965-06-28

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