DE1920150C2 - 3-(l-Methyl-5-nitro-2-imidazolyl-methylenamino)-2-oxazolidone - Google Patents

3-(l-Methyl-5-nitro-2-imidazolyl-methylenamino)-2-oxazolidone

Info

Publication number
DE1920150C2
DE1920150C2 DE1920150A DE1920150A DE1920150C2 DE 1920150 C2 DE1920150 C2 DE 1920150C2 DE 1920150 A DE1920150 A DE 1920150A DE 1920150 A DE1920150 A DE 1920150A DE 1920150 C2 DE1920150 C2 DE 1920150C2
Authority
DE
Germany
Prior art keywords
nitro
methyl
imidazolyl
oxazolidone
methylenamino
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
DE1920150A
Other languages
English (en)
Other versions
DE1920150A1 (de
Inventor
Hans-Joachim Dr.agr. 1000 Berlin Keßler
Clemens Dr.Rer.Nat. Rufer
Eberhard Dr.rer.nat. Schröder
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.)
Bayer Pharma AG
Original Assignee
Schering 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
Application filed by Schering AG filed Critical Schering AG
Priority to DE1920150A priority Critical patent/DE1920150C2/de
Priority to CS2057A priority patent/CS178401B2/cs
Priority to ES378236A priority patent/ES378236A1/es
Priority to CH511470A priority patent/CH529163A/de
Priority to DK178770AA priority patent/DK123242B/da
Priority to NO01431/70A priority patent/NO126321B/no
Priority to FR707013768A priority patent/FR2042338B1/fr
Priority to SE05228/70A priority patent/SE364961B/xx
Priority to US00029236A priority patent/US3752809A/en
Priority to AT351370A priority patent/AT295518B/de
Priority to BE749101D priority patent/BE749101A/xx
Priority to GB1852170A priority patent/GB1312054A/en
Priority to JP45032905A priority patent/JPS5030074B1/ja
Priority to FI701069A priority patent/FI52862C/fi
Priority to CA080420A priority patent/CA919671A/en
Priority to NL7005633A priority patent/NL7005633A/xx
Publication of DE1920150A1 publication Critical patent/DE1920150A1/de
Priority to US00352310A priority patent/US3839567A/en
Application granted granted Critical
Publication of DE1920150C2 publication Critical patent/DE1920150C2/de
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
    • C07D295/12—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 or doubly bound nitrogen atoms
    • C07D295/125—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/91—Nitro radicals
    • C07D233/92—Nitro radicals attached in position 4 or 5
    • C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/34—Compounds containing oxirane rings with hydrocarbon radicals, substituted by sulphur, selenium or tellurium atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Treatment Of Fiber Materials (AREA)

Description

H2N-N
CH2-R
(Π)
O3N
CH3
Morpholinogruppe bedeutet, sowie deren physiologisch verträglichen Salze.
Die neuen Verbindungen können hergestellt werden, indem man 1-Methyl-5-nitro-2-imidazolyl-aldehyd mit einem 3-Amino-oxazolidon der allgemeinen Formel Il
10
in der R eine Dialkylaminogruppe mit 1—5 Kohlenstoffatomen in jedem geradkettigen Alkylrest oder eine Morpholinogruppe bedeutet sowie deren physiologisch verträglichen Salze.
2. S-il-Meihyl-S-nitro^-imidazolyl-methylenamino)-5-morpholinomethyl-2-oxazolidon-HydrochIo-
3. Verfahren zur Herstellung der Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß man l-Methyl-5-nitro-2-imidazo!ylaldehyd mit einem 3-Amino-oxazolidon der allgemeinen Formel II
25
worin R die oben angegebene Bedeutung hat, in an sich bekannter Weise kondensiert und die so erhaltene Verbindung anschließend gewünschtenfalls in ein physiologisch verträgliches Salz überführt
4. Arzneimittel, bestehend aus einer oder mehreren Verbindungen gemäß Anspruch 1 und üblichen Hilfs- und Trägsrstoffen.
30
35
40
Gegenstand der Erfindung sind neue 3-(l-Methyl-5-nitro-2-imidazolyl-methylenamino)-2-oxazolidone der allgemeinen Formel I *5
■ τ-CHj—R
CH = N-N O (D
in der R eine Dialkylaminogruppe mit I - 5 Kohlenstoff atomen in jedem geradkettigen Alkylrest oder eine
CH1-R
(Π)
worin R die oben angegebene Bedeutung hat, in an sich bekannter Weise kondensiert und die so erhaltene Verbindung anschließend gegebenenfalls in ein physiologisch verträgliches Salz überführt
Die Kondensation von l-Methyl-5-nitro-2-imidazolyl-aldehyd mit einem substituierten 3-Amino-oxazolidon kann beispielsweise in Wasser oder niederen Alkoholen bei Raumtemperatur oder erhöhter Temperatur durchgeführt werden. In Anwesenheit von Säuren verläuft die Reaktion schneller und mit höherer Ausbeute, in diesem Fall werden die entsprechenden Salze erhalten.
Das physiologisch verträgliche Salz einer Verbindung der allgemeinen Formel I kann mittels üblicher Arbeitsweisen isoliert werden. Als Säuren für diese Salzbildung kommen z. B. in Frage: Salzsäure. Schwefelsäure. Essigsäure, Milchsäure. Bernsteinsäure, Weinsäure.
Die erfindungsgemäßen 3-(l-Methyl-5-nitro-2-imidazolyl-methylenamino)-2-oxazolidone der allgemeinen Formel I zeigen gute antimikrobielle Wirkungen, insbesondere gegen Trichomonas vaginalis. Die Tabelle zeigt lite überlegene Wirkung der neuen Substanzen an Hand der Verbindungen A-C gegen Trichomonas vaginalis im Vergleich zu Metronidazol. Die Versuche wurden als Reihenverdünnungstests in flüssigen Medien (Analytical Microbiology. F. Kananagh. Edit.. Academic Press. New York and London 1963) ausgeführt und die minimalen Hemmkonzentrationen (MHK) ermittelt.
Die Toxizität der neuen Verbindungen ist gering. Toxizitäts-Langzeitstudien der aus den Verbindungen A-C ausgewählten Verbindung C[3-(l-Methyl-5-nitro-Z-imidazolyl-methylenaminoJ-S-morpholinomethvl^- oxazolidon-Hydrochlorid] stellen im Gegensatz zu dem bei einer Dosis von 100 mg/kg bereits unverträglichen Metronidazol die Eignung der r'findungsgemäßen Verbindungen zur Behandlung vom Trichomonas-vagin->lis-Infektionen unter Beweis.
Die neuen ^'erbindungen können in den pharmazeutisch üblichen Applikationsformen, wie Pillen, Dragees, Kapseln. Säften. Lösungen verabfolgt werden.
Verbindung
MHK
Trichomonas
vaginalis
y/ml
ED50
(Maus, p. o.) (T. vaginalis)
rng/k* LD*,
(Maus, p. o)
g/kg
Therapeut.
Quotient
LD50
ED50
14-Wochen-Toxizität
3 rf, 3 <j> Beagle-Hunde
100 mg/kg/p ο/täglich
Metronidazol 1,60
(Vergleichssubstanz)
4,56
0,659 schwere neurotoxische
Symptome (3 Tiere
mußten bereits
zwischen 45. und 68.
Behandlungstag
getötet werden)
Fortsetzung Verbindung
MHK
Trichomonas
vaginaJis
y/ml
ED50
(Maus, p. o.) (T. vaginal is)
mg/kg LD50
(Maus, p. o.)
g/kg
Therapeut
Quotient
LD50
ED50
14-Wochen-Toxizität
3 4, 3 £ Beagle-Hunde
100 mg/kg/p. o./täglich
3-(l-Methyl-5-nitro-2-imidazolyl-methylenamino)-5-di-n-propylaminomethyl-2-oxazolidon (Beispiel 4)
imidazolyl-methylenamino)-5-di-n-butyI-aminomethyl-2-oxazolidon (Beispiel 3)
3-(l-Mcthyl-5-iiitro-2-
nnidazuiyl-fflcibyicn-
amino)-5-morphoIino-
methyl-2-oxazolidon-
Hydrochlorid
(Beispiel 2)
0,05
0,20
1,60
1,67
3,20
>4 3,2
2,4
3,5 1,095 ohne toxische
Symptome
Beispiel 1
mg 5-Nitro-1-mßthyl-2-imidazolyl-aldehyd und mg S-Amino-S-diäthylaminomethyl^-oxazolidon werden in 4 ml Äthanol mit 4 mI 12,5 t. methanolischer Salzsäure eine Stunde gekocht NjcK Abkühlen wird mit wenig Isopropylalkohol und Äther vers tzt Absaugen und Umkristallisation aus Isopropylalkohol-Methanol ergibt 310 mg 3-(5-Nitro-l-methyl-2-imidazolyl-methylenamino)-5-diäthylaminomethyl-2-oxazolidon als Hydrochlorid vom Schmelzpunkt 233 - 234°C.
Beispiel 2
mg 5-Nitro-l-methyl-2-imidazolyI-aldehyd und mg S-Amino-S-morphoIinomethyl^-oxazolidon werden in 6 ml Äthanol mit 2 ml 11,8 η methanolischer Salzsäure 4 Stunden gekocht. Kühlen und Absaugen ergeben 553 mg 3-(5-Nitro-l-methyl-2-imidazolyl-methylenamino)-5-morpholinomethyl-2-oxazolidon als Hydrochlorid vom Schmelzpunkt 214 -215°C
Beispiel 3
155 mg 5-Nitro-l-methyl-2-imidazolylaldehyd und 242 mg 3-Amino-5-dibutylaminomethyl-2-oxazolidon werden in 3 ml Äthanol mit 0,096 ml 12,5 η methanolischer Salzsäure vier Stunden gekocht Kühlen und Absaugen ergeben 53 mg 3-(l-Methyl-5-nitro-2-imid-
azolylmethylenamino)-5-dibutylaminomethyI-2-oxazolidon vom Schmelzpunkt 136"C
Beispiel 4
155 mg S-Nitro-l-methyl^-imidazolylaidehyd und 215 mg S-Amino-S-di-n-propylaminomethyl^-oxazolidon werden in 1,5 ml Wasser und 1.25 ml 2 η Salzsäure oei Raumtemperatur gerührt Danach wird mit 1 η KOH alkalisch gemacht und abgesaugt Man erhält 193,6 mg
♦5 (55% der theoretischen Ausbeute). 3-(l-Methyl-5-nitro-2-imidazolyl-methylen-amino)-5-di-n-propylarninomethyl-2-oxazolidon vom Schmelzpunkt 169—1700C (aus Methanol-lsopropanol).

Claims (1)

Patentansprüche:
1. 3-(l -Methyl-i-nitro-^-iniidazolyl-methylenamino)-2-oxazolidone der allgemeinen Formel I
-N
O2N
-InJ-CH=N-N O
I Y
CH,
DE1920150A 1969-04-17 1969-04-17 3-(l-Methyl-5-nitro-2-imidazolyl-methylenamino)-2-oxazolidone Expired DE1920150C2 (de)

Priority Applications (17)

Application Number Priority Date Filing Date Title
DE1920150A DE1920150C2 (de) 1969-04-17 1969-04-17 3-(l-Methyl-5-nitro-2-imidazolyl-methylenamino)-2-oxazolidone
CS2057A CS178401B2 (de) 1969-04-17 1970-03-27
ES378236A ES378236A1 (es) 1969-04-17 1970-04-03 Procedimiento para la preparacion de nuevas 3 - (5-nitro-2-imidazolilmetilenamino)-2-oxazolidinonas.
CH511470A CH529163A (de) 1969-04-17 1970-04-07 Verfahren zur Herstellung von neuen 3-(5-Nitro-2-imidazolylmethylenamino)-2-oxazolidinonen
DK178770AA DK123242B (da) 1969-04-17 1970-04-09 Analogifremgangsmåde til fremstilling af 3-(5-nitro-2-imidazolylmetylenamino)-2-oksazolidinoner eller salte deraf.
FR707013768A FR2042338B1 (de) 1969-04-17 1970-04-16
SE05228/70A SE364961B (de) 1969-04-17 1970-04-16
US00029236A US3752809A (en) 1969-04-17 1970-04-16 3-(5-nitro-2-imidazolyl-methylenamino)-2-oxazolidinones
NO01431/70A NO126321B (de) 1969-04-17 1970-04-16
BE749101D BE749101A (fr) 1969-04-17 1970-04-17 3-(5-nitro-2-imidazolyl-methyleneamino)-2-oxazolidinones et leur procede de preparation
GB1852170A GB1312054A (en) 1969-04-17 1970-04-17 3-5,-nitro-2,-imidazolyl-methyleneamino-2-oxazolidinones
JP45032905A JPS5030074B1 (de) 1969-04-17 1970-04-17
FI701069A FI52862C (fi) 1969-04-17 1970-04-17 Menetelmä uusien mikrobinvastaisten 3-(5-nitro-2-imidatsolyyli-metylee ni-amino)-2-oksatsolidinonien valmistamiseksi.
CA080420A CA919671A (en) 1969-04-17 1970-04-17 3-(5-nitro-2-imidazolyl-methylenamino)-2-oxazolidinone
AT351370A AT295518B (de) 1969-04-17 1970-04-17 Verfahren zur Herstellung neuer 3-(5-Nitro-2-imidazolyl-methylenamino)-2-oxazolidinonderivate und ihrer Salze
NL7005633A NL7005633A (de) 1969-04-17 1970-04-17
US00352310A US3839567A (en) 1969-04-17 1973-04-18 Pharmaceutical compositions comprising 3-(5-nitro-2-imidazolyl-methylen-amino)-2-oxazolidinones and their use in trichomoniasia

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE1920150A DE1920150C2 (de) 1969-04-17 1969-04-17 3-(l-Methyl-5-nitro-2-imidazolyl-methylenamino)-2-oxazolidone

Publications (2)

Publication Number Publication Date
DE1920150A1 DE1920150A1 (de) 1970-10-22
DE1920150C2 true DE1920150C2 (de) 1983-01-13

Family

ID=5731816

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1920150A Expired DE1920150C2 (de) 1969-04-17 1969-04-17 3-(l-Methyl-5-nitro-2-imidazolyl-methylenamino)-2-oxazolidone

Country Status (16)

Country Link
US (1) US3752809A (de)
JP (1) JPS5030074B1 (de)
AT (1) AT295518B (de)
BE (1) BE749101A (de)
CA (1) CA919671A (de)
CH (1) CH529163A (de)
CS (1) CS178401B2 (de)
DE (1) DE1920150C2 (de)
DK (1) DK123242B (de)
ES (1) ES378236A1 (de)
FI (1) FI52862C (de)
FR (1) FR2042338B1 (de)
GB (1) GB1312054A (de)
NL (1) NL7005633A (de)
NO (1) NO126321B (de)
SE (1) SE364961B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3973019A (en) * 1972-12-21 1976-08-03 Hoechst Aktiengesellschaft Pharmaceutical compositions containing 1,4-bis-(5'-nitroimidazolyl-2'-methylene-imino) piperazine compounds for treating protozoal diseases and methods for treating such diseases
DE2262555A1 (de) * 1972-12-21 1974-06-27 Hoechst Ag 1,4-bis- eckige klammer auf 1'-alkyl5'-nitroimidazolyl-2'-methylen-imino eckige klammer zu -piperazin und verfahren zu ihrer herstellung
DE2335144A1 (de) * 1973-07-07 1975-01-23 Schering Ag Basisch substituierte nitroimidazolmethylenamino-imidazolidinone
DE2629237A1 (de) 1976-06-26 1978-01-05 Schering Ag Mittel zur bekaempfung von erkrankungen im veterinaerbereich

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE624402A (de) *

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NICHTS-ERMITTELT

Also Published As

Publication number Publication date
FR2042338B1 (de) 1973-08-10
CS178401B2 (de) 1977-09-15
CH529163A (de) 1972-10-15
NO126321B (de) 1973-01-22
GB1312054A (en) 1973-04-04
FI52862B (de) 1977-08-31
CA919671A (en) 1973-01-23
FI52862C (fi) 1977-12-12
JPS5030074B1 (de) 1975-09-29
SE364961B (de) 1974-03-11
FR2042338A1 (de) 1971-02-12
DE1920150A1 (de) 1970-10-22
DK123242B (da) 1972-05-29
AT295518B (de) 1972-01-10
NL7005633A (de) 1970-10-20
ES378236A1 (es) 1972-06-01
US3752809A (en) 1973-08-14
BE749101A (fr) 1970-10-19

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