PL84268B1 - - Google Patents

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Publication number
PL84268B1
PL84268B1 PL1971174913A PL17491371A PL84268B1 PL 84268 B1 PL84268 B1 PL 84268B1 PL 1971174913 A PL1971174913 A PL 1971174913A PL 17491371 A PL17491371 A PL 17491371A PL 84268 B1 PL84268 B1 PL 84268B1
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PL
Poland
Prior art keywords
group
hydroxy
hydrogen
phenyl
lower alkyl
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Application number
PL1971174913A
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English (en)
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Publication of PL84268B1 publication Critical patent/PL84268B1/pl

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/007—Pulmonary tract; Aromatherapy
    • A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
    • A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/56—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
    • C07C215/58—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • C07C215/62—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups with hydroxy groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain the chain having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • 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
    • C07C217/48—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 unsaturated and containing rings
    • 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
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/64—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
    • C07C217/66—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain
    • C07C217/72—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms with singly-bound oxygen atoms and six-membered aromatic rings bound to the same carbon atom of the carbon chain linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Emergency Medicine (AREA)
  • Otolaryngology (AREA)
  • Pulmonology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Przedmiotem wynalazku jest sposób wytwarzania nowych l-hydroksyfenylo-l-hydroksy-2- (3-airylo-3- -hydroksypropylo)-aminoetanów w postaci racematu ewentualnie diastereomerycznych enancjomerów, czystyich, optycanie czynnych izomerów oraz ich 5 soli addycyjnych z kfwa Nowym zwiazkom odpowiada wzór ogólny 1, w którym Rt oznacza wodór lub nizsza grupe alkilowa lub alkoksylowa, R2 oznacza wodór, grupe metylowa hub etylowa, R8 oznacza wodór lmb giru/pe metylowa, i0 R4 oznacza wodór lub nizsza grupe alkilowa, R5 oznacza wodór lub grupe hydroksylowa i A oznacza ewentualnie podstawiona chlorowcem, nizsza grupe alkilowa, nizsza grupe alkoksylowa i/lub hydroksy¬ lowa grupe fenylowa lub skondensowana grupe dwu- 15 cykliczna, w której nie zwiazany bezposrednio z lan¬ cuchem alifatycznym pierscien jest izocykliczny lub heterocykliczny, nasycony lub aromatyczny, przy czym do grup dwucyklicznych tego rodzaju zaliczaja sie, np. grupa naftylowa, 3,4-metylenodwuoksyfeny- 20 Iowa i benzodioksanylowa.Wedlug wynalazku nowe zwiazki wytwarza sie przez redukcje zwiazku o wzorze ogólnym 2, w któ¬ rym wszystkie symbole maja wyzej podane znacze¬ nie. Reakcje prowadzi sie przez katalityczne uwodór- 25 nienie w obecnosci niklu, platyny lub palladu, jako katalizatora lub przez redukcje kompleksowymi wo¬ dorkami, w szczególnosci borowodorkiem sodowym.Otrzymany produkt ewentualnie rozdziela sie na op¬ tycznie czynne postacie lub ewentualnie w diastereo- 30 2 meryczne enancjomery i/lub przeprowadza sie w sole addycyjne z kwasami. Produkty wyjsciowe wytwa¬ rza sie znanymi do wytwarzania takich zwiazków metodami.Zwiazki, otrzymywane sposobem wedlug wynalaz¬ ku, wykazuja wlasciwosci terapeutyczne. Stanowia one substancje czynna leków stosowanych w cho¬ robach serca i krazeniowych. Srodki te stosuje sie w postaci znanych preparatów galenowych, zawie¬ rajacych znane srodki pomocnicze i nosniki, np. w postaci tabletek, drazetek, kapsulek, aerozoli, kropli i roztworów injekcyjnych. Pojedyncza dawka wy¬ nosi okolo 0,1—20 mg. Nastepujace pmzyiklaidy wyja¬ sniaja blizej wynalazek, nie ograniczajac jego zakre¬ su. Wydajnosc kazdorazowo podana jest w % wydaj¬ nosci teoretycznej.Przyklad I. Erytro-*l-(4-hydroksyfenylo)-l-hy- droksy-2-metylo-2-[(3-fenylo-3-hydroksy)-propylo]- -aminoetan. 4,79 g 4-benzyloksy-a-N-benzylo-N-(3- -fenylo-3-hydroksy)-propyloamino-propiofenonu uwodarnia sie w 100 ml metanolu, w obecnosci ni¬ klu Raney'a jako katalizatora, w normalnych wa¬ runkach do erytro-l-(4-hydroksyfenylo)-l-hydroksy- -2-metylo-2-[(3-fenylo-3-hydroksy)-propylo] -amino- etanu, o temperaturze topnienia 186°C (z izopropano- lu).Przyklad II. l-(3,5-dwuhydroksyfenylo)-l-hy- droksy-2- [(3-fenylo-3-hydroksy-l,l-dwumetylo)-pro¬ pylo]-amiinoetan. Przez reakcje 3,5^wiufbenzytloksy- -w-bromocefofenonu z (3-fenylo-3-hydroksy-l,l-dwu-84 268 3 4 metylo)-propyloamina otrzymuje sie z 7(1% wydajno¬ scia chlorowodorek (3,5-dwubenzyloksy)-co-N-(3-fe- nylo-3-hydroksy-1,1- dwumetylo)-propyloainino-ace- tofenomi (temperatura topnienia 120°C). Aminoketon piizepiio/waidzia sie w zasade i w meltamodu uwoldorniia wobec ixikl,u. Raney'a do l-(3,5-dwuhydroksyfenylo)- -l-hydroksy-2-[(3-fenylio-3-hydroksy-l,l-dwumety- lo)-propylo]-aminoetanu. Po dodaniu kwasu benzo¬ esowego wyodrebnia sie z acetonitrylu diastereome- ryczny benzoesan, o temperaturze topnienia 19,9°C i 142°C (wodzian).Przyklad III. l-(4-hydroksyfe:nylo)-l-Gydro- ksy-2-[(3-fenylo^3-hydroksy)-propylo] -aminoetan. 23,3 g (0,05 mola) 4-benzyloksy-a-N-benzylo-N-(3-fe- nylo-3-hydroksy) -propyloamino-aoetofenonu zadaje sie w mieszaninie 125 ml metanolu i wody 10 ml 17,6% roztworem eterowym kwasu solnego i uwo¬ dornia w temperaturze 60°C i 5 atn, w obecnosci pal¬ ladu na weglu jako katalizatora, az do pobrania 0,1 mola wodoru. Utworzony chlorowodorek 4-hydro- ksyfenylo-co-N- (3-fenylo-3-hydroksy)-propyloamino- -aoetofenonu (temperatura topnienia: 188°C, z wo¬ dy) uwodornia sie w obecnosci platyny jako. katali¬ zatora do 1-(4-hydroksyfenylo)-1-hydroksy-2-[(3-fe- nylo-3-hydroksy)-propylo]-aminoetanu. Rozdzielenie na diastereomery zachodzi przez zasajde. Diastereo- meryczne zwiazki topnieja w temperaturze 112 wzglednie 158°C.Odpowiednio do podanych przykladów otrzymuje sie nastepujace zwiazki: siarczan l-(4-hydroksysenylo)-l-hydroksy-2-[(3^£eny- lo-3-metoksy)-propylo]-aminoetanu, temperatura top¬ nienia: 205°C, benzoesan 1 - (3-hydroksyfenylo)-1-hydroksy-2- [(3-fe- nylo-3-hydroksy)-propylo] -aminoetanu, temperatura ^o^nienia: 128°C, chlorowodorek 1^ (4-hydroksyfenylo) -l-hydroksy-2- -[(3-fenylo-3-hydroksy-l,l-dwumetyloXpiropylo]-ami¬ noetanu, temperatura topnienia: 212°C, chlorowodorek treo-1-(4-hydroksyfenylo)-1-hydro- ksy-2-metylo^2- [(3-fenylo-3-hydroksy)-propylo]-ami¬ noetanu, temperatura topnienia: 160°C, X-(4-^diroksy-3-naetoksyfenylo)-l-hydroksy-2-[(3- -fenylo-3-hydroksy)-propylo]-aminoetan, postac X: zasada, temperatura topnienia: 162°C, siarczan: tem¬ peratura topnienia 163°C, postac Y:zasada, tempera¬ tura topmjienda 133°C, ohlorofwotioirek: temperatura topnienia 125°C. l-(3,5-d)wfunydiiiok&^^ E(3-fenylo- -3-hydroksy)-propylo] ^aminoetan, postac X: tempe- rajtura topnienia: 187°C, postac Y: ternperaituira top- nienlia: 102°C. benzoesan 1-(3,5-dwuhydroksyfenylo)-1 -hydroksy-2- -[(S-fenylcHS-hydroksy-ljl-dwumetylo^-propylo]- -aminoetanu, postac X: temperatura topnienia: 199°C, postac Y: temperatura topnienia: 142°C (wodzian), chlorowodorek l-(3,5-dwuhydroiks3rfenylo)-l-hodro- ksy-2- [(3-a-naftylo-3-hydroksy-1,1 -dwumetylo)-pro- pyilolHaimliinoetaniU', positac X: leniperaitura topnienia: 235°C, postac Y: temperatura topnienia: 149°C, benzoesan 1-(4-hydroksy-2-metylofenylo)-1-hydro- ksy-2- [i(3-o^me1y,Jjofenyao/-3-hydirioikBy)-propylo]- -aminoetanu, temperatura topnienia: 164°C, l-(4-hydroksy-2-metylofenylo)-l-hydroksy-2-[(3-p- -metoksyfenylo-3-hydroksy) -propylo]-amiinoetan, temperatura topnienia: 161°C, l-(4-hydroksy-2-metylofenylo)-l-hyiciroksy-2-[(3-p- -hydroksy-m-chloirofenylo-3-hydroksy)-propylo] - -aminoetan, postac X: temperatura topnienia: 161°C (chlorowodorek), postac Y: temperatura topnienia: 81CC (benzoesan), 1- (4-hydroksy-3-butoksyfenylo)-1-hydroksy-2-[3- -m,p-dwuetpksyfenyk-3-hydroksy) -propylo]-amino¬ etan^ zasiada: temperatura topnienia: 108°C, benzoesan: i^mperatura topnienia: 128°C, chlorowo¬ dorek: temperatura topnienia: 125°C, siarczan: tem¬ peratura topnienia: 172°C, benzoesan 1- (4-hydroksy-3-butoksyfenylo) -1-hydro- ksy-2-[(S-mjP-dwubutoksj^enylo-^-hydiioksy)-pro¬ pylo]-aminoetanu, temperatura topnienia: 101°C. PL PL PL PL PL PL

Claims (2)

1. Zastrzezenia patentowe i ; 1. Sposób wytWiarzania nowych 1-hydroksyfenylo- «1-hydroksy-2-(3-arylo-3-hydroksypropylo)-amino- etanów o wzorze ogólnym 1, w którym Rt oznacza wodór lub. nizsza grupe alkilowa lub alkoksylowa, R2 oznacza wodór, grupe metylowa lub etylowa, R3 oznacza wodór lub grupe metylowa, R4 oznacza wo¬ dór luJb nizsza grupe aiMlowa, R5 oznacza wodór lub grupe hydroksylowa i A oznacza grupe fenylowa ewentualnie podstawiona chlorowcem, nizsza grupa alkilowa, nizsza grupa alkoksylowa i/lub hydjroiksy- lowa albo skondensowana dwucykliczna grupe, w której pierscien nie zwiazany bezposrednio z ali¬ fatycznym lancuchem jest izocykliczny lub heterocy-. kliczny, nasycony lub aromatyczny, w postaci rape- maitu ewenrtoalnie diiasiter^eomer^cz^ eaancjiGime-, rów, czystych, optycznie czynnych izomerów, zna¬ mienny tym, ze zwiazek o wzorze ogólnym 2, w któ¬ rym Rt—R5 i A maja wyzej podane znaczenie, redu¬ kuje sie i otrzymany zwiazek w postaci diasteLreome- rycznych enancjomerów lub czystych izomerów op¬ tycznie czynnych ewentualnie rozdziela sie i otrzy¬ mana zasade ewentualnie przeprowadza w sól ad¬ dycyjna z kwasem lub z otrzymanej soli uwalnia sie zasade.
2. Sposób wedlug zastrz. 1, znamienny tym, ze jako produkt wyjsciowy stosuje sie zwiazek o wzorze ogólnym 2a, w którym Rt—R4 maja znaczenie poda¬ ne W zastrz. 1 i At oznacza grupe fenylowa lub pod¬ stawiona, w szczególnosci chlorowcem, nizsza grupe alkilowa ,nizsza grupe alkoksylowa i/lub grupa hy¬ droksylowa, grupe fenylowa. 15 20 25 30 35 40 43 5084-268 R- R. HO £ CH0H-CHR2-NH-C(R3)-CH-CH0RrA wzdR 1 R5 x^\ HO C0-CHR2-NH-C(fyjCH2-CH0RrA WZdR 2 R. HO 1^yC0-CHR-NH-C(R3)2-CH2-CH0RrA WZdR 2o PL PL PL PL PL PL
PL1971174913A 1970-02-25 1971-02-24 PL84268B1 (pl)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19702008654 DE2008654A1 (de) 1970-02-25 1970-02-25 Ammoathanoldenvate

Publications (1)

Publication Number Publication Date
PL84268B1 true PL84268B1 (pl) 1976-03-31

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ID=5763256

Family Applications (3)

Application Number Title Priority Date Filing Date
PL1971174914A PL84395B1 (pl) 1970-02-25 1971-02-24
PL1971146464A PL82843B1 (pl) 1970-02-25 1971-02-24
PL1971174913A PL84268B1 (pl) 1970-02-25 1971-02-24

Family Applications Before (2)

Application Number Title Priority Date Filing Date
PL1971174914A PL84395B1 (pl) 1970-02-25 1971-02-24
PL1971146464A PL82843B1 (pl) 1970-02-25 1971-02-24

Country Status (18)

Country Link
AT (3) AT306707B (pl)
BE (1) BE763408A (pl)
BG (3) BG18856A3 (pl)
CH (4) CH568271A5 (pl)
CS (3) CS166749B2 (pl)
DE (1) DE2008654A1 (pl)
ES (3) ES388561A1 (pl)
FR (1) FR2081541B1 (pl)
GB (1) GB1340407A (pl)
IE (1) IE34970B1 (pl)
IL (1) IL36269A (pl)
NL (1) NL7102432A (pl)
NO (1) NO131983C (pl)
PL (3) PL84395B1 (pl)
RO (3) RO62244A (pl)
SE (1) SE377561B (pl)
SU (2) SU421181A3 (pl)
ZA (1) ZA711204B (pl)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA791403B (en) * 1978-04-10 1980-05-28 Draco Ab Composition of matter
FI70205C (fi) * 1978-05-17 1986-09-15 Degussa Foerfarande foer framstaellning av nya terapeutiskt anvaendbara l-/3-hydroxi-3-fenylpropyl-(2)/-/3-oxo-propyl/aminer
US4853381A (en) * 1984-04-17 1989-08-01 Glaxo Group Limited Ethanolamine compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1250450B (de) * 1962-03-31 1967-09-21 Deutsche Gold- und Silber-Scheideanstalt vormals Roessler, Frankfurt/M Verfahren zur Herstellung von Aminoalkoholen sowie deren Säureadditionssalzen und quartären Ammoniumverbindungen

Also Published As

Publication number Publication date
SU404229A3 (pl) 1973-10-26
IE34970B1 (en) 1975-10-01
AT306706B (de) 1973-04-25
SE377561B (pl) 1975-07-14
CH568269A5 (pl) 1975-10-31
NO131983B (pl) 1975-05-26
FR2081541B1 (pl) 1975-01-17
BG19130A3 (bg) 1975-04-30
BE763408A (fr) 1971-08-24
CH568271A5 (pl) 1975-10-31
BG18855A3 (bg) 1975-03-20
PL84395B1 (pl) 1976-03-31
SU421181A3 (pl) 1974-03-25
SU424349A3 (pl) 1974-04-15
RO60182A (pl) 1976-08-15
CS166748B2 (pl) 1976-03-29
RO62244A (pl) 1977-08-15
BG18856A3 (bg) 1975-03-20
ES396175A1 (es) 1974-04-01
IL36269A (en) 1974-01-14
ES388561A1 (es) 1973-05-16
FR2081541A1 (pl) 1971-12-03
AT306707B (de) 1973-04-25
CH568270A5 (pl) 1975-10-31
IE34970L (en) 1971-08-25
GB1340407A (en) 1973-12-12
IL36269A0 (en) 1971-04-28
CH568268A5 (pl) 1975-10-31
CS166750B2 (pl) 1976-03-29
NL7102432A (pl) 1971-08-27
CS166749B2 (pl) 1976-03-29
PL82843B1 (pl) 1975-10-31
ZA711204B (en) 1972-10-25
AT305250B (de) 1973-02-12
ES396174A1 (es) 1974-04-01
NO131983C (pl) 1975-09-03
RO58559A (pl) 1975-09-15
DE2008654A1 (de) 1971-09-09

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