DE1445665A1 - Verfahren zur Herstellung neuer pharmazeutisch wirksamer Verbindungen - Google Patents

Verfahren zur Herstellung neuer pharmazeutisch wirksamer Verbindungen

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Publication number
DE1445665A1
DE1445665A1 DE19631445665 DE1445665A DE1445665A1 DE 1445665 A1 DE1445665 A1 DE 1445665A1 DE 19631445665 DE19631445665 DE 19631445665 DE 1445665 A DE1445665 A DE 1445665A DE 1445665 A1 DE1445665 A1 DE 1445665A1
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Germany
Prior art keywords
preparation
morpholino
compounds
parts
salts
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Pending
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DE19631445665
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English (en)
Inventor
Helmut Beschke
Schuler Dr Wilhelm
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Evonik Operations GmbH
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Degussa GmbH
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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
    • C07D213/60—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 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • 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
    • C07D213/60—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 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • 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
    • C07D213/60—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 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C07D213/71—Sulfur atoms to which a second hetero atom is attached
    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

DEUTSCHE GOLD-I:MD SILBEK-SCIiJSJDEANSTALT VOKMALS HOESSLER Frankfurt aiii Main, tfeissfraueastrasse 9
Verfaiiren zur Herste Llung neuer pncirinazeutxscn wirksamer Ver-Dindungen
Ό-'.e Erfindung Detrii'ft ein Verfahren zur Herstellung neuer Veri>inoii eier allgemeinen Formel
κ.
:__.. s - Ch., - Gu2 - η w Ό
(Ο«
worin H ein Wasserstoff- «der üalogenatoai und n die .',ca: eil J ccler " bedeutet und deren 5a!üe,
Üi.o lierstellun^, der eri'indungs{;eiii:issen Vert>xjiduji;',en uer ciii^ Füi'HieJ I erfolgt in an sich beicamitei· iieise tlurcii Oxydation einer Verulndun^ der «dlgemoinen i'orniel T, in der ii die oben angegebene Bedeutung nut und η die Zatil ο bedeutet oder deren Salze, mit Wassers toffpero d, Kaliunfperinanganat, i'eressigsüure oder Salpetersäure« Die ernalteilen Basen Können gegebenenfalls ΐιιΐΐ einer Suure in ein Salz übergeführt werden«
Die Ausgangsstoffe Können nach dein Verfahren der Patentanmeldung D J8 ^99 gewonnen werden.
Die erfiiidungsgemässen Verbindungen sind anaigetiscn wirtcsain. ™
in der folgenden Tabelle wird die anaigetische Wirkung und die To. izität der Verfahrensprodukte bei verscniedenen AppÜKationen mit dem beKannten Ifandelspriiparat iforaiuidopyrinmethansulfonat-Natriuiii (N-Methyl-l-Pneiiyl-2, i-dimetiiyl-3-oxo-pyrazolin-( ;)-yl-( I) -aininomethansulf onsaures Natrium) verglichen.
BAD ORIGINAL 809810/1306
Unterlagen (Art7S1Abs.2Nr.l Satz3d*eÄnderuno8ae8-v,4,9.19' '.
Mäuseschwanz-Test nach Th 2 s üb cut ein Haffner 4 ; intraperi-
; toneal		 . Th
I		 7,4 LD 50 ■ ;?;,20 Maus (ingy'kg) intrapei
toneal
Sub oral ,1 ED 50
mg/kg		 ,1 ED 50
mg/kg		 6 9,5 oral : •;'.i50 sub-
cu tan
stanz ED 50
in g/kg		 1 ,6 1 Th ,5 . 5 • 1,8 6,9 - 9
1 4 1000 ,8 ! 1/00 4,9 ": 2-. 30 8 2200
A 3000 ,'}■ 181 5 ,1 226 - ;>050 i4oo 5200 1140
B : 750 6 ,9\ 156 6 1;-". 11,7 ■■460 2100 i;io -
C 507 5 211 5 111 9,4 4650 900 I3OO
i
D j		 371 9. 250 5 0 ' 235 5,7 2250 980 2210
/10 ;* G, 90 12 18 3 8,5
I		 313O I050
F : 484 2, δ 147 6 148 1 - I26O
G ■::90 6, ι - 12, 9 - I77O -
H 535 6, 15'^ 1 109 - 730
I 339 273 8, 218 1220 1985
J ioi6 173 9, 182 239O 1260
K - 7, I23O
.Ίΐ - therapeutische Breite
Norarnidopyrinmethansulf onat-Natrium (2-Morpholino-äthyl)- |j3-chlorp\ ridyl-( 2) Z -sulfoxyd-KCl (2-Morpholino-äthyl)- £5-chlorpyridyl-( 2) J -sulfo ,yd-IICl (2-Morpholino-äthyl)- [j6-chlorpyridyl-( Z) j -sulfo yd-HCl ( 2-Morpholino-äthyl )-pyridyl-( 2) -sulfo yd-IICl (2-Morpholino-äthyl)- £6-brompyridyl-( 2) J -sulfo -yd-tICl (2-Morpholino-äthyl)- [j3-chlorpyridyl-( 2)1 -sulfon-HCl ( 2-Morpholino-äthyl)- f5-chlorpyridyl-( 2)J. -sulf on-TICl (2-Morpholino-äthyl)- Co"-chlorpyridyl-( 2) ~_ -sulfon-HCl (2-Morpholino-äthyl)-pyridyl-(2)-sulfon-HCl (2-Morpholino-äthyl)- I 6-brompyridyl-(2)J —sulfon—HCl
809810/1306
-j-
BAD ORiGiNAL
GOPY
Aus der Tabelle geht hervor, dass die Verfahrensprodukte oral 3-7, parenteral sogar 4-19 mal analgetisch wirksamer als das 'Vergleichsprodukt sind. Dasselbe gilt für die therapeutische Breite (LD 50/ ED 50) j die bei oraler und intraperitonealer Aj^plikation mindestens das Doppelte und ma imal sogar das Sechsfache des Wertes der Vergleichssubstanz ist«, Damit ist die Überlegenheit der Verfahrensprodukte sowohl in der anaigetischen Wirkung als auch in der Verträglichkeit gegenüber dem Handelsprodukt Noramidopyrinrnethansulf onat-Natriurn eindeutig bewiesen,
Methodik:
1. Analgetische Wirkung
Die analgetische Wirkung wurde im Mäuseschwanztest nach Haffner (Deutsche Medizinische Wochenschrift j5jj, /31, 1929) geprüft. Ermittelt wurde die Dosis in mg/kg, die bei $0 ^o der eingesetzten Tiere eine analgetische Wirkung hervorrief (ED 50)* Die Substanzen wurden oral, subcutan und intraporitoneal zugeführt«
2. Toxikologische Prüfung
Die To. izitätsprüfung wurde an der Maus in mehreren Verabreichungsformen (oral, subcutan, inrraperitoneal) durch Bestimmung der akuten To izität (LD 50 in mg/kg) nach Miller und Tainter (Proc.Soc.Exper. Biol.and Med.,57, 26l, 1944) durchgeführt. Beobachtungszeit: 24 Stunden.
3. Therapeutische Breite
Die therapeutische Breite ist das Verhältnis von toxischer zu wirKsamer Dosis und wird dux'ch den Faktor LD 50/ED 50 ausgedrückt. Je grosser dieser FaKtor, desto grosser· ist auch der Abstand der wirksamen Dosis zur to ischen Dosis, d.h. desto besser ist die Verträglichkeit der Verbindung.
809810/1306 C0PY
ORIGINAL INSPECTED
Beispiel 1
48 Teile 2-(Morpholinoäthylmercapto)—pyridin werden in 250 Teilen Methanol gelöst und mit methanol!scher Salzsäure bis pH = 4 angesäuert. Nun wird auf 500C angeheizt und unter Rühren werden 23 Teile 35/oige Wasserstoffperoxydlösung zugegeben. Ans chi ie s send wird 5 Stunden am Rückfluss gekocht, danach im Vakuum eingedampft und aus Äthanol umkristallisiert. Es werden 42 Teile des Monohydrochlorids vom 2-(Morpholinoäthyl)-pyridyl-(2)-sulfoxyd erhalten. Der Schmelzpunkt liegt bei 186°C.
Beispiel 2
20 Teile 2-(Morpholinoäthylmercapto)-3-chlorpyridin werden in 200 Teilen Methanol gelöst, mit Salzsäure bis auf pH = 4 angesäuert und auf 50°C erwärmt. Dann werden 8 Teile 35$iges Wasserstoffperoxyd zugegeben und 5 Stunden am Rückfluss gekocht. Nach Eindampfen im Vakuum wird aus Methanol umkristallisiert. Es werden 19>5 Teile des Hydrochloride vom 2-(Morpholinoäthyl)—3-chlorpyridyl-(2)—sulfoxyd erhalten. Der Schmelzpunkt liegt bei 2020C (Zersetzung).
Beispiel 3
50 Teile 2-(Morph"olinoäthylmercapto)-3-chlorpyridin werden in 450 Teilen Eisessig gelöst und auf 4o°C angeheizt. Dann werden 55 Teile Kaliumpermanganat, gelöst in 500 Teilen Wasser, portionsweise zugesetzt. Dabei steigt die Temperatur auf 650C an. Es wird 1 Stunde nachgerührt und anschliessend vom gebildeten Braunstein abgesaugt unter Zuhilfenahme von Kieselgur als Filterhilfe. Das Filtrat wird mit wenig Ameisensäure zur Zerstörung von eventuell noch vorhandenem Permanganat versetzt, alkalisch gemacht und mit Benzol extrahiert. Die eingedampfte Benzollösung ergibt 35 Teile kristalliner Base des 2-(Morpholinoäthy3)-3-chlorpyridyl-( 2)-sulfone, aus dem in Methanol das Hydrochlorid mit einem Schmelzpunkt von 219°C gefällt wird.
Beispiel 4
Verfährt man wie in Beispiel 2 unter Verwendung von 2-(Morpholino- äthylmercapto)-6-chlorpyridin, so wird das Hydrochlorid des entsprechenden Sulfoxyds erhalten, welches bei 193°C schmilzt.
- 5 809810/1306 qBl6lNAUNSPECTED
I ~f ~T W \J
Beispiel 5
Wird unter Verwendung von 2-(Morpholinoäthylmercapto)-6-chlorpyridin wie in Beispiel 3 verfahren, so erhält man das entsprechende Sulfon, dessen Hydrochlorid bei 211°C schmilzt.
Beispiel 6
Verfährt man, wie in Beispiel 2 beschrieben, mit 2-(2-Morpholinoäthylmercapto)-5-chlorpyridin, so erhält man das entsprechende SuIfoxyd, dessen Hydrochlorid bei 216 - 218°C schmilztβ
Beispiel J
Verfährt man, Wie in Beispiel 3 beschrieben, mit 2-(Morpholinoäthylmercapto)-5-chlorpyridin, so erhält man das entsprechende Sulfon, dessen Hydrochlorid bei 237 - 2*fO°C schmilzt,,
Beispiel 8
Verfährt man, wie in Beispiel 3» unter Verwendung von 2-(2-Morpholino-
äthylmercapto)-6-brompyridin, so erhält man das entsprechende Sulfon,
dessen Hydrochlorid bei 207 - 210°C schmilzt»
Beispiel Q
Verfährt man, wie in Beispiel 3» unter Verwendung von 2-(2-Morpholinoäthylmercapto)—pyridin, so erhält man das entsprechende Sulfon, dessen Hydrochlorid bei 222 - 225°C schmilzt.
Beispiel 10
Verfährt man, wie in Beispiel 2. unter Verwendung von 2-(2-Morpholino-
äthylmercapto)-6-broBipyridin, so erhält man das entsprechende SuIfoxyd,
dessen Hydrochlorid bei 200 - 2O2°C schmilzt.
809810/1308

Claims (2)

  1. Patentansprüche
    1„ Verfahren zur Herstellung von Verbindungen der allgemeinen Formel I
    ij— S- CH, - CH, - K H © (0)
    in der R ein Wasserstoff- oder Halogenatom und η die Zahlen 1 oder 2 bedeutet und ihren Salzen, dadurch gekennzeichnet, dass man Verbindungen der allgemeinen Formel I, in der R die oben angegebene Bedeutung hat und η die Zahl Null bedeutet oder ihre Salze, in an sich bekannter Weise mit Wasserstoffperoxyd, Kaltumpermanganat, Peressigsäure oder Salpetersäure oxydiert und erwünschtenfalls eine erhaltene Base mit einer Säure in ein Salz umwandelte
    2„ Verbindungen der allgemeinen Formel
    S - CH2 - CH2 - tf H fc> % ''n
    in der R ein Wasserstoff- oder Ralogenatom und η die Zahlen 1 oder 2 bedeutet und ihre Salze»
    Dr.Stm/Pr
    30.7-1968
    Original inspected 809810/1306
    Unterlagen {Art. 7 ί I Aba.
  2. 2 Nr. I Satz 3 des Anderunssoea. v, 4.9. W
DE19631445665 1963-07-11 1963-07-11 Verfahren zur Herstellung neuer pharmazeutisch wirksamer Verbindungen Pending DE1445665A1 (de)

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DED0041963 1963-07-11

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DE1445665A1 true DE1445665A1 (de) 1968-11-28

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Country Status (11)

Country Link
US (1) US3341536A (de)
BE (1) BE650361A (de)
CH (1) CH440274A (de)
DE (1) DE1445665A1 (de)
DK (1) DK108916C (de)
ES (1) ES301922A1 (de)
FI (1) FI43875C (de)
FR (1) FR1451210A (de)
GB (1) GB1054338A (de)
NL (2) NL6407791A (de)
SE (1) SE306086B (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3443968A1 (de) * 1983-12-28 1985-10-31 Degussa Ag, 6000 Frankfurt Neue pyridin-2-ether beziehungsweise pyridin-2-thioether mit einem stickstoffhaltigen cycloaliphatischen ring

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7407384A (de) * 1973-06-08 1974-12-10
US4343805A (en) * 1978-12-16 1982-08-10 John Wyeth & Brother Limited Heterocyclic compounds
GB8708233D0 (en) * 1987-04-07 1987-05-13 Smith Kline French Lab Pharmaceutically active compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3443968A1 (de) * 1983-12-28 1985-10-31 Degussa Ag, 6000 Frankfurt Neue pyridin-2-ether beziehungsweise pyridin-2-thioether mit einem stickstoffhaltigen cycloaliphatischen ring

Also Published As

Publication number Publication date
FI43875B (de) 1971-03-31
CH440274A (de) 1967-07-31
ES301922A1 (es) 1965-01-16
GB1054338A (de)
NL6407791A (de) 1965-01-12
FR1451210A (fr) 1966-01-07
FI43875C (fi) 1971-07-12
US3341536A (en) 1967-09-12
BE650361A (de) 1964-11-03
NL122313C (de)
SE306086B (de) 1968-11-18
DK108916C (da) 1968-02-26

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E77 Valid patent as to the heymanns-index 1977