DK146336B - Analogifremgangsmaade til fremstilling af syreadditionssalte af svovlholdige diarylforbindelser - Google Patents

Analogifremgangsmaade til fremstilling af syreadditionssalte af svovlholdige diarylforbindelser Download PDF

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DK146336B
DK146336B DK437075A DK437075A DK146336B DK 146336 B DK146336 B DK 146336B DK 437075 A DK437075 A DK 437075A DK 437075 A DK437075 A DK 437075A DK 146336 B DK146336 B DK 146336B
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preparation
addition salts
sulful
acid addition
compounds
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DK437075A
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DK146336C (da
DK437075A (da
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Victor Lafon
Louis Lafon
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Lafon Labor
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Priority claimed from FR7502307A external-priority patent/FR2258846A1/fr
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Priority to DK31780A priority Critical patent/DK31780A/da
Priority to DK31680A priority patent/DK152206C/da
Priority to DK31580A priority patent/DK159966C/da
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    • 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
    • A61K31/12—Ketones
    • A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
    • A61K31/125—Camphor; Nuclear substituted derivatives thereof
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/255—Esters, e.g. nitroglycerine, selenocyanates of sulfoxy acids or sulfur analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
    • 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
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/22—Radicals substituted by oxygen atoms
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205—Radicals derived from carbonic acid

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Description

i 146336
Den foreliggende opfindelse angår en analogifremgangsmåde til fremstilling af hidtil ukendte syreadditionssalte af svovlholdige diarylforbindelser, hvilke salte har den almene formel 2 01—\ / 3°n \ ' (?Η2>ιο β u>
\=/ S(CH2)2NH2(CH2)20H
hvori n er 0, 1 eller 2, og Alk er CHiCH^) eller C(CH3)2.
Disse syreadditionssalte har en nyttig hypolipidæmisk virkning.
Fra tysk offentliggørelsesskrift nr. 2 355 115 kendes beslægtede diarylforbindelser med nyttig hypolipidæmisk virkning.
Denne nyttige virkning er imidlertid ikke så udpræget som virkningen af forbindelserne fremstillet ifølge opfindelsen.
Fremgangsmåden ifølge opfindelsen er ejendommelig ved, at man omsætter en svovlholdig diarylcarboxylsyre med den almene formel
Cl_ / V so„ / V 0-Alk-C00H (II) \=/ \=/ hvori n og Alk har de ovenfor angivne betydninger, med forbindelsen 6,17-dithia-3,20-diaza-l,22-docosandiol, som har formlen HO(CH2)2NH(CH2)2S-(CH2)λ0-S(CH2)2NH(CH2)20H (III) 2 148336
En opløsning af den udvalgte forbindelse med formel II i varm ethanol udhældes i en varm opløsning af den halve molære mængde af forbindelsen med formel III i ethanol. Efter omrøring eller henstand afdampes opløsningsmidlet til opnåelse af saltet med formel I.
Fremstillingen af forbindelsen (III) er beskrevet i FR patentskrift nr. 2258846.
De omhandlede forbindelser kan formuleres til terapeutiske midler i kombination med en fysiologisk acceptabel excipiens.
Fremgangsmåden ifølge opfindelsen illustreres nærmere ved de følgende eksempler.
EKSEMPEL_1
Di-p-(g-chlorphenylthio)-phenoxy-isobutyratet af 6,17-dithia-5»20-diaza-1^22-docosandiol CCH2)10£S-(CB2)2-»H2-(CB2)2-0H]2, 2CU-^^-S-^^-0-C-C00 Kode nr. CRL 40.240.
I en vann opløsning af 3,8 g (0,01 mol) 6,17-dithia-3,20-diaza- 1,22-docosandiol i 25 ml vandfri ethanol udhældes en varm opløsning af 6,45 g (0,02 mol) p-(p-chlorphenylthio)-phenoxy-isosmørsyre i 25 ml vandfri ethanol. Man omrører i 2 timer ved omgivelsestemperaturen, hvorpå man afdamper opløsningsmidlet under reduceret tryk. Efter at have udvasket remanensen med acetonitril opnår man 8,4 g af et svagt beigefarvet pulver, der er uopløseligt i vand, men opløseligt i alkohol.
Smp. (Kofler) = 75 °C.
Udbytte = 82 %.
3 146336 EKSEMPEL_2_
Pi—p-(p-chlorphen.ylsulf onyl)-phenoxy-isobutyratet af 6,17-dithia- 5,20-diaza-1,22-docosandiol ® . _ /=\ /-\ Γ3 Θ
(CH2) s~cCH?>2-KH2-(cn2)2-0H/2 , 2G1-^ jj- SO^ ^-O-C-COO
Kode nr. CR1 40.241.
I en varm opløsning af 5,54 g (0,0095 mol) 6,17-dithia-5,20-diaza- 1,22-docosandiol i 25 ml vandfrit ethanol udhældes en varm opløsning af 6,6 g (0,0186 mol) p-.(p-chlorphenylsulfonyl)-phenoxy-iso-smørsyre i 25 ml vandfri ethanol. Man omrører i 2 timer ved omgivelsestemperaturen, hvorpå man afdamper opløsningsmidlet under reduceret tryk. Efter udvaskning med acetonitril opnår man 9,9 g af et svagt rosa pulver, der er uopløseligt i vand, men opløseligt i varm alkohol.
Smp. (Kofler) = 157° 0.
Udbytte =98 EKSEMPEL-3
Di-(-)-2-[ p-(p-chl or phenyl sulf onyl)-phenoxy] -propionatet af 6^,17-MjMa^^O-diaza-l^gg-dicosandiol ® _ r\ JT\ i"3 0
(CH2)lc/S'(CH2)2"NH2“(CH2)2"0-i » 2C1*\ / S02\ Vo-CH-COO
Kode nr. CR1 40.249.
I en varm opløsning af 2,84 g (0,0075 mol) 6,17-dithia-5,20-diaza- 4 1-46336 1,22-docosandiol i 20 ml vandfri ethanol udhaeldes en varm opløsning af 5,10 g (0,0150 mol) (-)-2-[p-(p-chlorphenylsulfo-nyl)-phenoxy]-propionsyre i 20 ml vandfri ethanol. Efter henstand i 15 minutter afdamper man opløsningsmidlet under reduceret tryk, og den krystallinske remanens udvaskes derpå med acetonitril, hvorved man opnår 7,8 g af et hvidt pulver, der er uopløseligt i vand og alkohol.
Smp.: (Kofler) = 149-150 °C Udbytte = 98,3 %.
EKSEMPEL_4 dithia-3,20-diaza-l,22-docosandiol CCK2)10 L s-(CH2)2-liH2-(cH2)2-0H' ]2, 2C1--^"^-SO-^ ^—O-j-COO®
Kode nr. CR1 40.242.
I en varm opløsning af 3,8 g (0,01 mol) 6,17-dithia-3,20-diaza- 1,22-docosandiol i 25 ml ethanol udhældes en varm opløsning af 6,77 g (0,02 mol) 4-{4-chlorphenylsulfinyl)-phenoxyisosmørsyre i 25 ml ethanol. Man omrører i 30 minutter ved omgivelsestemperaturen, hvorpå opløsningsmidlet afdampes under reduceret tryk. Efter at have optaget remanensen i diisopropylether opnås 10,4 g af et hvidt vanduopløseligt pulver, der er opløseligt i alkohol.
Smp.: (Kofler); Cirka 85 °C Udbytte: = 98,5 % 146336 5 EKSEMPEL_5
Di(g-chlorphenylthio) -phenoxy-isoljutyratet af 6,17-clithia-3,20-diaza-1?22-docosandiol © ' /=\ /=\ f‘3 © (CH2\oCS~'CH2>2~KV(CH2>2"OHV2' C1—^ //~S~\
Kode nr. CRL -40.247.
I en varm opløsning af 2,84 g (0,0075 mol) 6,17-dithia-3,20-diaza- 1,22-docosandiol i 20 ml vandfri ethanol udhældes en varm opløsning af 4,62 g (0,015 mol) (-)-2-[4-chlorphenylthio]-phenoxypro-pionsyre i 20 ml vandfri ethanol. Efter henstand i 15 minutter afdamper man opløsningsmidlet under reduceret tryk. Remanensen omkrystalliseres fra acetonitril under dannelse af 7,2 g af et hvidt vanduopløseligt pulver, der er opløseligt i alkohol.
Smp. (Kofler) = Cirka 70 °C Udbytte = 96,5 %.
Biologiske undersøgelser
Forbindelserne fremstillet ifølge opfindelsen har en u-ventet nyttig hypolipidæmisk virkning i sammenligning med de nært beslægtede diarylforbindelser, der kendes fra det ovennævnte tyske offentliggørelseskrift nr. 2 355 115.
Denne overraskende virkningforbedring i forhold til den kendte teknik er eftervist ved nedenstående sammenligningsforsøg imellem forbindelser fremstillet ifølge opfindelsen og forbindelser kendt fra det nævnte tyske offentliggørelsesskrift. Der er foretaget sammenligner af lipid-varia-tion og cholesterol-variation imellem forbindelserne fremstillet ifølge eksemplerne 1-5 og fem nært beslægtede kendte forbindelser.
Forbindelserne, der skulle afprøves, blev indgivet til schweiziske rotter, der hver vejede 200 g (10 rotter pr. gruppe), ved 146336 6 oral intubation i en gummi arabicum-suspension (3%) 16 og 24 timer efter iværksættelse af faste. Kontroldyrene modtog kun bærestoffet» der blev udtaget blodprøver fra retro orbital sinus, og disse blodprøver blev anbragt i tørre glas og centrifugeret 24 timer efter den første intubation. Den totale mængde serum-cholesterol blev doseret colorimetrisk ifølge metoden beskrevet af Watson, D. Clin. Chim. Acta 5, side 637-643 (1960), og den totale mængde serum-lipider blev bestemt med sulfophosphorvanillin ifølge Chabrol et al., Presse Med.
Vol. 45, side 1713-1714 (1937).
De opnåede resultater fremgår af den efterfølgende tabel.
Doseringen er 100 mg/kg. Lipid- og cholesterol-variationerne er angivet i procent beregnet på kontroldyrene.
TABEL
Forbindelse Dosis Lipid Cholesterol _variation_variation
Eksempel 1 100 -30 -25
Sml. A 100 -21 -25
Eksempel 2 100 -33 -27
Sml. B 100 -12 -12
Eksempel 3 100 -32 -28
Sml. C 100 -7 -10
Eksempel 4 100 -31 -25
Sml. D 100 -20 -23
Eksempel 5 100 -30 -27
Sml. E. 100 -8 -8
Sammenligningsforbindelser: A: 4-(4-chlorphenylthio)-phenoxyisosmørsyre.
B: 4-(4-chlorphenylsulfonyl)-phenoxyisosmørsyre.
C: (—)—2—[4—(4-chlorphenylsulfonyl)-phenoxy]-propionsyre.
D: 4-(4-chlorphenylsulfonyl)-phenoxyisosmørsyre.
E: (-)-2- [4-chlorphenylthio)-phenoxy]-propionsyre.
Saltene fremstillet ifølge opfindelsen er mere aktive som lipidre-ducerende midler end de tilsvarende syrer.
DK437075A 1974-09-30 1975-09-29 Analogifremgangsmaade til fremstilling af syreadditionssalte af svovlholdige diarylforbindelser DK146336C (da)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DK31780A DK31780A (da) 1974-09-30 1980-01-25 Analogifremgangsmaade til fremstilling af oxygenholdige diarylforbindelser og syreadditionssalte heraf
DK31680A DK152206C (da) 1974-09-30 1980-01-25 Analogifremgangsmaade til fremstilling af svovl- og/eller oxygenholdige diarylforbindelser eller syreadditionssalte heraf
DK31580A DK159966C (da) 1974-09-30 1980-01-25 Analogifremgangsmaade til fremstilling af oxygenholdige diarylforbindelser

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB4238774 1974-09-30
GB4238774A GB1519147A (en) 1974-09-30 1974-09-30 Sulphur and oxygen-containing diaryl compounds
GB158775 1975-01-14
GB158775 1975-01-14
FR7502307A FR2258846A1 (en) 1974-01-25 1975-01-24 Bis((N-hydroxy alkyl)-amino alkyl thio)alkane and derivs - as agents preventing blood platelet aggregation
FR7502307 1975-01-24

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DK437075A DK437075A (da) 1976-03-31
DK146336B true DK146336B (da) 1983-09-12
DK146336C DK146336C (da) 1984-02-20

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CA (1) CA1064504A (da)
CH (1) CH609024A5 (da)
DE (2) DE2543179A1 (da)
DK (1) DK146336C (da)
IE (1) IE42609B1 (da)
NL (1) NL176776C (da)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1571829A (en) 1976-04-06 1980-07-23 Lafon Labor Sulphur-containing diaryl compounds and oxygen-containing diaryl compounds
ES2108855T3 (es) * 1992-07-21 1998-01-01 Ciba Geigy Ag Derivados de acido oxamico como agentes hipocolesteremicos.
CN1250209C (zh) * 1999-11-01 2006-04-12 大正制药株式会社 20－羟基二十碳四烯酸合成酶抑制剂

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* Cited by examiner, † Cited by third party
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DE1935344U (de) 1965-11-09 1966-03-24 Karosserie Migoe Chr H Mittelg Doppelwandung fuer fahrzeugaufbauten, insbesondere fuer kuehl- bzw. thermoswagen od. dgl., bei der der zwischenraum zwischen zwei wandungen durch isolierwerkstoff ausgefuellt ist.
DE1668896C3 (de) 1968-01-11 1974-08-29 Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt Phenoxyalkancarbonsäuren ihre Salze und Ester und Verfahren zur Herstellung dieser Verbindungen
CH511786A (de) * 1968-01-11 1971-08-31 Hoechst Ag Verfahren zur Herstellung von Phenoxyalkancarbonsäuren, deren Salzen und Estern
BE786644A (fr) * 1971-07-23 1973-01-24 Hoechst Ag Derives d'acides phenoxy-4 phenoxy-alcane-carboxyliques leur preparation et les medicaments qui en contiennent
FI55986C (fi) * 1972-05-10 1979-11-12 Ciba Geigy Ag Foer anvaendning som skadedjurs bekaempningsmedel avsedda substituerade fenylderivat
DE2223894C3 (de) * 1972-05-17 1981-07-23 Hoechst Ag, 6000 Frankfurt Herbizide Mittel auf Basis von Phenoxycarbonsäurederivaten
DE2355115A1 (de) * 1972-11-07 1974-05-09 Erba Carlo Spa Substituierte phenoxyalkancarbonsaeuren, funktionelle derivate und salze davon sowie verfahren zu ihrer herstellung

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CH609024A5 (en) 1979-02-15
DE2543179A1 (de) 1976-04-15
DK146336C (da) 1984-02-20
IE42609B1 (en) 1980-09-10
IE42609L (en) 1976-03-30
NL7511452A (nl) 1976-04-01
DE2560602C2 (de) 1986-08-28
DK437075A (da) 1976-03-31
NL176776C (nl) 1985-06-03
NL176776B (nl) 1985-01-02
CA1064504A (en) 1979-10-16

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