SE456992B - Foerfarande foer framstaellning av 2-(1-fenyl-bensimidazolyl)-acetohydroxamsyra - Google Patents

Foerfarande foer framstaellning av 2-(1-fenyl-bensimidazolyl)-acetohydroxamsyra

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Publication number
SE456992B
SE456992B SE8302173A SE8302173A SE456992B SE 456992 B SE456992 B SE 456992B SE 8302173 A SE8302173 A SE 8302173A SE 8302173 A SE8302173 A SE 8302173A SE 456992 B SE456992 B SE 456992B
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SE
Sweden
Prior art keywords
phenyl
benzimidazolyl
preparation
acetoh
procedure
Prior art date
Application number
SE8302173A
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English (en)
Other versions
SE8302173L (sv
SE8302173D0 (sv
Inventor
L Lafon
Original Assignee
Lafon Labor
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Filing date
Publication date
Application filed by Lafon Labor filed Critical Lafon Labor
Publication of SE8302173L publication Critical patent/SE8302173L/sv
Publication of SE8302173D0 publication Critical patent/SE8302173D0/sv
Publication of SE456992B publication Critical patent/SE456992B/sv

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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)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Description

456 992 2 genom att 2-(l-fenylbensimidazolyl)-etylacetat med formeln: O ff””N >--CH2 -cf (II) N oczns c6H5 bringas att reagera med hydroxylamin.
Etylacetatet med formeln II bringas att reagera med hydroxylamin i lösning eller i suspension i pyridin eller en lâgalkanol med l-3 kolatomer, såsom metanol, etanol, propanol och isopropanol.
En terapeutisk komposition kan förutom en fysio- logiskt godtagbar konstituent innehålla minst en före- ning med formel I.
Andra fördelar och egenskaper hos uppfinningen belyses av följande framställningsexempel, vilket inte är avsett att begränsa uppfinningen.
EXEMPEL 2-(1-fenyl-bensimidazolyl)~acetohydroxamsyr§ N o >icnz - c% (I) N \m¶on Kodnummer: CRL 40 490 1) Etyl-2-(1-fenyl-bensimidazolyl)-acetat Man omrör vid 20°C en lösning av 11,75 g (0,064 mol) ortoaminodifenylamin i 90 ml etanol och tillsätter 12,5 g (0,064 mol) etylkarboxiimino-acetathydroklorid.
V. 456 992 3 Efter 2 h avfiltreras bildad ammoniumklorid och filtra- tet indunstas i vakuum. Man tar upp återstoden i eter, tvättar med vatten, torkar, förângar etern, kristalli- serar återstoden ur petroleumeter, centrifugerar och omkristalliserar ur diisopropyleter. Man erhåller 16 g (ubyte 89%) av den angivna estern, som smälter vid 84°C. 2) CRL 40 490 Man framställer en lösning av hydroxylamin med 3,5 g (0,05 mol) hydroxylaminhydroklorid i S0 ml vat- tenfri metanol och 2,3 g (0,1 gramatomer) natrium i 50 ml vattenfri metanol. Man avfiltrerar bildad natriumklorid och sätter till filtratet 14 g (0,0S ml) etyl-2-(1-fenylbensimidazolyl)-acetat och låter bland- ningen stå över natten. Man indunstar den erhållna blandningen till torrhet i vakuum, tar upp återstoden i vatten, neutralisera: med 3 N HCl, centrifugerar, tvättar med vatten och torkar. Efter omkristallisation ur metanol erhaller man CRL 40 490.
Smp: 212-2l5°C (sönderdelning). Utbyte; 68%.
Nedan sammanfattas resultaten från de försök, som har genomförts med produkten med formeln I, vilken produkt administreras (om ej annat anges) suspenderad i en gummilösning (gummi arabicum) pá intraperitoneal väg med en volym på 20 ml/kg till möss.
A ' ÉQEÉEÉÉÉÉ DL-0 för möss överstiger 1024 mg/kg.
B - lnrszlsaanzê_ssatrëlë_nsrrsrsssæsz CRL 40 490 i en dos på 128 mg/kg motverkar reser- pinhypotermi. I dosen 512 mg/kg minskar CRL 40 490 rörelseaktiviteten hos möss.
De farmakologiska och kliniska försöken visar att produkten med formeln I är en substans, som verkar på det centrala nervsystemet som ett psykotropt och särskilt som ett sedativt, anti-depressivt, psyko- stimulerande eller ångestdämpande medel.

Claims (10)

  1. 456 992PATENTKRAV
  2. Analogiförfarande för framställning av terapeu-
  3. tiskt verksam 2-(1-fenylbensímidazolyl)-acetohydroxam-
  4. syra med formeln
  5. 5N o
  6. 1/
  7. \>:c1¶2 - c/ (I)
  8. 1:1 \NHoH
  9. C H
  10. 10 6 5
    k ä n n e t e c k n a t därav, att 2-(l-feny1bens-
    imidazolyl)-etylacetat med formeln
    15
    N O
    /
    >-~CH2 - c< (II)
    § OCZHS
    20
    Cefls
    bringas att reagera med hydroxylamin.
    25
    \!
SE8302173A 1976-03-23 1983-04-19 Foerfarande foer framstaellning av 2-(1-fenyl-bensimidazolyl)-acetohydroxamsyra SE456992B (sv)

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
SE8302173L SE8302173L (sv) 1983-04-19
SE8302173D0 SE8302173D0 (sv) 1983-04-19
SE456992B true SE456992B (sv) 1988-11-21

Family

ID=26240593

Family Applications (4)

Application Number Title Priority Date Filing Date
SE7703263A SE432420B (sv) 1976-03-23 1977-03-22 Forfarande for framstellning av terapeutiskt verksamma hydroxamsyror
SE8302173A SE456992B (sv) 1976-03-23 1983-04-19 Foerfarande foer framstaellning av 2-(1-fenyl-bensimidazolyl)-acetohydroxamsyra
SE8302171A SE452155B (sv) 1976-03-23 1983-04-19 Analogiforfarande for framstellning av terapeutiskt verksamma arylsulfinylacetohydroxamsyraderivat
SE8302172A SE458605B (sv) 1976-03-23 1983-04-19 Foerfarande foer framstaellning av acetohydroxamsyror

Family Applications Before (1)

Application Number Title Priority Date Filing Date
SE7703263A SE432420B (sv) 1976-03-23 1977-03-22 Forfarande for framstellning av terapeutiskt verksamma hydroxamsyror

Family Applications After (2)

Application Number Title Priority Date Filing Date
SE8302171A SE452155B (sv) 1976-03-23 1983-04-19 Analogiforfarande for framstellning av terapeutiskt verksamma arylsulfinylacetohydroxamsyraderivat
SE8302172A SE458605B (sv) 1976-03-23 1983-04-19 Foerfarande foer framstaellning av acetohydroxamsyror

Country Status (25)

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

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AT356078B (de) 1980-04-10
CA1130301A (en) 1982-08-24
US4209523A (en) 1980-06-24
FR2453148A1 (fr) 1980-10-31
FR2453158B1 (sv) 1982-08-06
NO803338L (no) 1977-09-26
US4151300A (en) 1979-04-24
ATA840078A (de) 1980-11-15
DE2711451A1 (de) 1977-10-06
DK126677A (da) 1977-09-24
NO152972B (no) 1985-09-16
FR2453133A1 (fr) 1980-10-31
SE8302171L (sv) 1983-04-19
NO771006L (no) 1977-09-26
FR2345430B1 (sv) 1982-07-23
FI62821C (fi) 1983-03-10
FI62821B (fi) 1982-11-30
FR2453158A1 (fr) 1980-10-31
NO803336L (no) 1977-09-26
JPS52144601A (en) 1977-12-02
NO146431B (no) 1982-06-21
ATA839878A (de) 1980-09-15
SE8302171D0 (sv) 1983-04-19
JPS628424B2 (sv) 1987-02-23
DK171197B1 (da) 1996-07-22
SE8302172L (sv) 1983-04-19
US4152458A (en) 1979-05-01
AT362793B (de) 1981-06-10
SE8302173L (sv) 1983-04-19
FR2345430A1 (fr) 1977-10-21
NL188801C (nl) 1992-10-01
IE44721L (en) 1977-09-23
IL51705A0 (en) 1977-05-31
NO145881B (no) 1982-03-08
SE8302172D0 (sv) 1983-04-19
DE2711451C2 (sv) 1990-05-10
US4122186A (en) 1978-10-24
LU76989A1 (sv) 1977-07-18
AU516473B2 (en) 1981-06-04
AU2334477A (en) 1978-09-21
AT374191B (de) 1984-03-26
PT66300B (pt) 1978-08-10
FI770859A (sv) 1977-09-24
SU689617A3 (ru) 1979-09-30
GB1574822A (en) 1980-09-10
ES457105A1 (es) 1978-10-16
SE432420B (sv) 1984-04-02
AT358556B (de) 1980-09-25
NO144420C (no) 1981-08-26
ATA501480A (de) 1983-08-15
US4183951A (en) 1980-01-15
SE7703263L (sv) 1977-09-24
CA1120928A (en) 1982-03-30
SE458605B (sv) 1989-04-17
NO803337L (no) 1977-09-26
NO145881C (no) 1982-06-16
ATA193077A (de) 1979-09-15
IL51705A (en) 1982-09-30
SE452155B (sv) 1987-11-16
NO152972C (no) 1985-12-27
US4225617A (en) 1980-09-30
PT66300A (fr) 1977-04-01
BE852738A (fr) 1977-09-22
SE8302173D0 (sv) 1983-04-19
AT361932B (de) 1981-04-10
NZ183616A (en) 1979-03-28
FR2453148B1 (sv) 1983-12-02
US4209524A (en) 1980-06-24
CH620894A5 (sv) 1980-12-31
FR2453133B1 (sv) 1984-04-06
DD129645A5 (de) 1978-02-01
ATA839978A (de) 1980-02-15
CS200511B2 (en) 1980-09-15
PH16271A (en) 1983-08-25
NL7703168A (nl) 1977-09-27
NO144420B (no) 1981-05-18
IE44721B1 (en) 1982-03-10
NO146431C (no) 1982-09-29

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