NO152972B - Analogifremgangsmaate for fremstilling av 2-(1-fenylbenzimidazolyl)-acetohydroksamsyre med terapeutisk aktivitet - Google Patents

Analogifremgangsmaate for fremstilling av 2-(1-fenylbenzimidazolyl)-acetohydroksamsyre med terapeutisk aktivitet Download PDF

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Publication number
NO152972B
NO152972B NO803337A NO803337A NO152972B NO 152972 B NO152972 B NO 152972B NO 803337 A NO803337 A NO 803337A NO 803337 A NO803337 A NO 803337A NO 152972 B NO152972 B NO 152972B
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preparation
acid
acetoh
therapeutic activity
analogy procedure
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NO803337A
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English (en)
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NO152972C (no
NO803337L (no
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Louis Lafon
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Lafon Labor
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Publication of NO803337L publication Critical patent/NO803337L/no
Application filed by Lafon Labor filed Critical Lafon Labor
Publication of NO152972B publication Critical patent/NO152972B/no
Publication of NO152972C publication Critical patent/NO152972C/no

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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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
    • 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
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/64—Acyl halides
    • C07C57/72—Acyl halides containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
    • C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
    • 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
    • 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/56—Radicals substituted by sulfur atoms

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Neurosurgery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Neurology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biomedical Technology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Description

Foreliggende oppfinnelse angår fremstilling av 2-(l-fenyl-benzimidazolyl)-acetohydroksamsyre som har terapeutisk an-vendelse, særlig som reagent med virkning på sentralnervesystemet .
Enkelte hydroksamsyrer er allerede beskrevet, og enkelte av disse har vist seg inaktive terapeutisk, særlig 4-a-naftyloksy-3- hydroksybutyrohydroksamsyre (se eks. 5 [sammenlignings-eksempel] i US patent 3.819.702), andre har vist seg å ha virkning på sentralnervesystemet, særlig 4-fenylsulfinyl-butyrohydroksamsyre, 4-(p-fluorfenylsulfinyl)-butyrohydroksam-syre, 3-(p-fluorfenylsulfinyl)-propionhydroksamsyre, og 4- (p-klorfenylsulfinyl)-butyrohydroksamsyre (se eks. 12
til 15 i fransk patentsøknad 27483 [1975]) og syrene p-benz-hydrylsulfinylacetohydroksamsyre, 3-benzhydrylsulfinylpropion-hydroksamsyre og 4-benzhydrylsulfinylbutyrohydroksamsyre (se eks. 1, 6 og 9 i britisk søknad 40419 [1975]).
Ifølge foreliggende oppfinnelse fremstilles 2-(1-fenylbenz-imidazolyl)-acetohydroksamsyre med terapeutisk aktivitet og med formelen: og denne fremgangsmåten er kjennetegnet ved at man omsetter 2-(1-fenylbenzimidazolyl)-etylacetat med formelen:
med hydroksylamin.
Omsetningen foretas i oppløsning eller suspensjon i pyridin eller lavere alkanol (C^-C^) som metanol, etanol, propanol eller isopropanol. .Terapeutiske preparater inneholder forbindelse (I) sammen med en fysiologisk eksipiens.
Følgende eksempel illustrerer oppfinnelsen.
Eksempel
Fremstilling av 2-( 1- fenylbenzimidalzolyl)- acetohydroksamsyre
1) Fremstilling av 2-( 1- fenylbenzimidazolyl)- etylacetat
( utgangsforbindeIse)
Ved 20°C omrøres en oppløsning av 11,75 g (0,064 mol) orto-aminodifenylamin i 90 ml etanol, og 12,5 g (0,064 mol) etyl-karboksiminoetylacetathydroklorid tilsettes. Etter 2 timer
i kontakt filtreres det dannede ammoniumklorid fra, og man inndamper filtratet i vakuum. Inndampningsresten oppløses i eter, vaskes med vann, tørkes, eteren avdampes, resten krystalliseres fra petroleter, filtreres og krystalliseres fra diisopropyleter. Man får 16 g (98%) av den angitte ester som smelter ved 84°C.
2. Fremstilling av tittelproduktet
Man fremstiller en oppløsning av hydroksylamin ut fra 3,5 g
(0,05 mol) hydroksylamlnhydroklorid i 50 ml vannfri metanol og 2,3 g (0,1 g-atom) natrium i 50 ml vannfri metanol.
Man filtrerer det dannede natriumklorid fra og tilsetter til filtratet 14 g (0,05 mol) 2-(1-fenylbenzimidazolyl)-etylacetat, og blandingen hensettes over natten. Det inndampes i vakuum til tørrhet, og man opptar inndampningsresten i vann, nøytraliserer med 3N HCl, filtrerer, vasker med vann og tørker. Ved omkrystallisasjon fra metanol får man det ønskede tittelprodukt, smp. 212-215°C (dekomp.), utbytte 68%.
Nedenfor sammenfattes resultater fra forsøk som er gjort med den ifølge oppfinnelsen fremstilte forbindelse. Forbindelsen ble administrert som en suspensjon i en gummioppløsning (gummi arabikum) ad intraperitoneal vei, i en mengde på
20 ml pr. kg for mus.
A_-_Toksisitet
Hos mus er LD-0 over 1024 mg/kg.
B_-_Virkning_gå_sentralnervesysteme^ .
2-(1-fenylbenzimidazolyl)-acetohydroksamsyre i doser på
128 mg/kg motvirker hypertermi som skyldes reserpin. I doser på 512 mg/kg reduseres den motoriske aktivitet hos mus.
Generelt viser de samlede farmakologiske og kliniske forsøk at forbindelsen fremstilt ifølge oppfinnelsen er en forbindelse som innvirker på sentralnervesystemet som et psykotropt middel og mer spesielt som et beroligende, anti-depressivt psykostimulerende eller anxiolytisk middel.

Claims (1)

  1. Analogifremgangsmåte for fremstilling av 2-(1-fenylbenzimidazolyl)-acetohydroksamsyre med terapeutisk aktivitet med formelen:
    karakterisert ved at man omsetter 2-(1-fenylbenzimidazolyl)-etylacetat med formelen:
    med hydroksylamin.
NO803337A 1976-03-23 1980-11-06 Analogifremgangsmaate for fremstilling av 2-(1-fenylbenzimidazolyl)-acetohydroksamsyre med terapeutisk aktivitet. NO152972C (no)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB11710/76A GB1574822A (en) 1976-03-23 1976-03-23 Acetohydroxamic acid derivatives and pharmaceutical compositions thereof
GB629877 1977-02-15

Publications (3)

Publication Number Publication Date
NO803337L NO803337L (no) 1977-09-26
NO152972B true NO152972B (no) 1985-09-16
NO152972C NO152972C (no) 1985-12-27

Family

ID=26240593

Family Applications (4)

Application Number Title Priority Date Filing Date
NO771006A NO144420C (no) 1976-03-23 1977-03-22 Analogifremgangsmaate for fremstilling av terapeutisk virksomme hydroksansyrer
NO803337A NO152972C (no) 1976-03-23 1980-11-06 Analogifremgangsmaate for fremstilling av 2-(1-fenylbenzimidazolyl)-acetohydroksamsyre med terapeutisk aktivitet.
NO803336A NO146431C (no) 1976-03-23 1980-11-06 Analogifremgangsmaate for fremstilling av nye terapeutisk virksomme arylsulfinylacetohydroksamsyrer
NO803338A NO145881C (no) 1976-03-23 1980-11-06 Analogifremgangsmaate for fremstilling av nye terapeutisk virksomme acetohydroksamsyrer

Family Applications Before (1)

Application Number Title Priority Date Filing Date
NO771006A NO144420C (no) 1976-03-23 1977-03-22 Analogifremgangsmaate for fremstilling av terapeutisk virksomme hydroksansyrer

Family Applications After (2)

Application Number Title Priority Date Filing Date
NO803336A NO146431C (no) 1976-03-23 1980-11-06 Analogifremgangsmaate for fremstilling av nye terapeutisk virksomme arylsulfinylacetohydroksamsyrer
NO803338A NO145881C (no) 1976-03-23 1980-11-06 Analogifremgangsmaate for fremstilling av nye terapeutisk virksomme acetohydroksamsyrer

Country Status (25)

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US (7) US4122186A (no)
JP (1) JPS52144601A (no)
AT (5) AT356078B (no)
AU (1) AU516473B2 (no)
BE (1) BE852738A (no)
CA (2) CA1120928A (no)
CH (1) CH620894A5 (no)
CS (1) CS200511B2 (no)
DD (1) DD129645A5 (no)
DE (1) DE2711451A1 (no)
DK (1) DK171197B1 (no)
ES (1) ES457105A1 (no)
FI (1) FI62821C (no)
FR (4) FR2345430A1 (no)
GB (1) GB1574822A (no)
IE (1) IE44721B1 (no)
IL (1) IL51705A (no)
LU (1) LU76989A1 (no)
NL (1) NL188801C (no)
NO (4) NO144420C (no)
NZ (1) NZ183616A (no)
PH (1) PH16271A (no)
PT (1) PT66300B (no)
SE (4) SE432420B (no)
SU (1) SU689617A3 (no)

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WO2008094592A1 (en) * 2007-02-01 2008-08-07 Panthera Biopharna, Llc Hydroxamic acid derivatives of aniline useful as therapeutic agents for treating anthrax poisoning
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CN101982459A (zh) * 2010-10-21 2011-03-02 山东华尔康生物技术有限公司 乙酰氧肟酸的制备工艺
GB201509663D0 (en) * 2015-06-03 2015-07-15 Johnson Matthey Plc Benzo(h)quinoline ligands and complexes thereof
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CS200511B2 (en) 1980-09-15
FR2453133B1 (no) 1984-04-06
ES457105A1 (es) 1978-10-16
SE8302172D0 (sv) 1983-04-19
AT374191B (de) 1984-03-26
US4151300A (en) 1979-04-24
IL51705A0 (en) 1977-05-31
US4183951A (en) 1980-01-15
SE8302172L (sv) 1983-04-19
NL188801C (nl) 1992-10-01
IL51705A (en) 1982-09-30
JPS628424B2 (no) 1987-02-23
ATA840078A (de) 1980-11-15
AT356078B (de) 1980-04-10
FI770859A (no) 1977-09-24
FI62821C (fi) 1983-03-10
CA1120928A (en) 1982-03-30
NO145881B (no) 1982-03-08
SE452155B (sv) 1987-11-16
NO771006L (no) 1977-09-26
SU689617A3 (ru) 1979-09-30
AT362793B (de) 1981-06-10
ATA839878A (de) 1980-09-15
SE432420B (sv) 1984-04-02
NO144420B (no) 1981-05-18
US4122186A (en) 1978-10-24
US4209523A (en) 1980-06-24
AT361932B (de) 1981-04-10
IE44721L (en) 1977-09-23
DE2711451C2 (no) 1990-05-10
DD129645A5 (de) 1978-02-01
FR2345430A1 (fr) 1977-10-21
NZ183616A (en) 1979-03-28
US4152458A (en) 1979-05-01
FR2453133A1 (fr) 1980-10-31
ATA839978A (de) 1980-02-15
SE8302173L (sv) 1983-04-19
NO145881C (no) 1982-06-16
DK171197B1 (da) 1996-07-22
CA1130301A (en) 1982-08-24
SE8302171D0 (sv) 1983-04-19
US4225617A (en) 1980-09-30
NO146431B (no) 1982-06-21
LU76989A1 (no) 1977-07-18
SE8302173D0 (sv) 1983-04-19
NO144420C (no) 1981-08-26
SE458605B (sv) 1989-04-17
PT66300B (pt) 1978-08-10
AU2334477A (en) 1978-09-21
IE44721B1 (en) 1982-03-10
SE7703263L (sv) 1977-09-24
NO152972C (no) 1985-12-27
JPS52144601A (en) 1977-12-02
FR2345430B1 (no) 1982-07-23
SE456992B (sv) 1988-11-21
BE852738A (fr) 1977-09-22
ATA193077A (de) 1979-09-15
SE8302171L (sv) 1983-04-19
FR2453158A1 (fr) 1980-10-31
PH16271A (en) 1983-08-25
AU516473B2 (en) 1981-06-04
FI62821B (fi) 1982-11-30
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FR2453148B1 (no) 1983-12-02
US4209524A (en) 1980-06-24
PT66300A (fr) 1977-04-01
CH620894A5 (no) 1980-12-31
GB1574822A (en) 1980-09-10
FR2453148A1 (fr) 1980-10-31
FR2453158B1 (no) 1982-08-06
NO146431C (no) 1982-09-29
DE2711451A1 (de) 1977-10-06
NO803337L (no) 1977-09-26
DK126677A (da) 1977-09-24
AT358556B (de) 1980-09-25
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NO803338L (no) 1977-09-26
NO803336L (no) 1977-09-26

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