SE431455B - SET TO MAKE AMINOIMIDAZOISOKINOLIN DERIVATIVES - Google Patents

SET TO MAKE AMINOIMIDAZOISOKINOLIN DERIVATIVES

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Publication number
SE431455B
SE431455B SE8000253A SE8000253A SE431455B SE 431455 B SE431455 B SE 431455B SE 8000253 A SE8000253 A SE 8000253A SE 8000253 A SE8000253 A SE 8000253A SE 431455 B SE431455 B SE 431455B
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Sweden
Prior art keywords
carbon atoms
atoms containing
derivatives
acid addition
general formula
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SE8000253A
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Swedish (sv)
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SE8000253L (en
Inventor
K Takacs
L Szekeres
K Harsanyi
G Papp
A Neszmelyi
E Benedek
Original Assignee
Chinoin Gyogyszer Es Vegyeszet
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Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet
Publication of SE8000253L publication Critical patent/SE8000253L/en
Publication of SE431455B publication Critical patent/SE431455B/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
    • H01J23/00—Details of transit-time tubes of the types covered by group H01J25/00
    • H01J23/02—Electrodes; Magnetic control means; Screens
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
    • H01J25/00—Transit-time tubes, e.g. klystrons, travelling-wave tubes, magnetrons
    • H01J25/34—Travelling-wave tubes; Tubes in which a travelling wave is simulated at spaced gaps

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Microwave Tubes (AREA)

Description

10 15 20 25 30 35 40 aooozsz-8 2 i vilken A och D har ovan angivna betydelser, upphettas i ett lösningsmedel eller i smälta vid en temperatur över 10000, varpå den erhållna föreningen med formeln II eventuellt omvandlas till ett syraadditionssalt därav eller basen med den allmänna formeln I eventuellt frigöres ur ett salt därav. 10 15 20 25 30 35 40 aooozsz-8 2 in which A and D have the meanings given above, are heated in a solvent or in a melt at a temperature above 10000, whereupon the obtained compound with formula II is optionally converted to an acid addition salt thereof or the base with the general formula I is optionally liberated from a salt thereof.

Som lösningsmedel användes xylen eller 1, 2, 3, 4-tetrahydronaftalen.The solvent used is xylene or 1,2,3,4-tetrahydronaphthalene.

Reaktionen sker vid en temperatur över 10000. I VêttGH1ÖSHlH9 HV fllkflllm9tö11~ hydroxid âstadkommes reaktionen genom kokning. Föreningarna med den allmänna formeln II kan framställas genom Bischler-Napieralsky-reaktionen genom att man cykliserar de motsvarande N-(2-fenyletyl)-1,2,4-oxadiazolon-5,3yl acetamidderi- vaten.The reaction takes place at a temperature above 10000. I VêttGH1ÖSHlH9 HV fl lk fl llm9tö11 ~ hydroxide, the reaction is effected by boiling. The associations with the general Formula II can be prepared by the Bischler-Napieralsky reaction by cyclize the corresponding N- (2-phenylethyl) -1,2,4-oxadiazolone-5,3yl acetamide vaten.

Vid jämförande försök, vid vilka föreningen enligt uppfinningen HE-36:3-Ben- zylamino-5,6-dihydro-8,9-dimetoxi-imidazo/5,1-a/isokinolin-hydroklorid (jämför exempel 4c), jämföres i synnerhet beträffande antiarytmiverkan på hjärtat med den för detta ändamål för sin goda verkan välkända föreningen Chinidin, erhölls följande resultat: LD5Ui.v. pâ råttor Antiarytmiverkan Förmak Kammaren relativ terapeutisk relativ terapeutisk aktivitet index aktivitet index HE-36 17 mg/kg 8,66 90,00 ' 2,80 32,9 Chinidin 46 mg/kg 1,00 17,7 1,00 20,0 Antiarytmiaktiviteten bestämdes på grundval av den verkan som utövades på för- maks- och kammarmuskelns elektriskt-fibrillära tröskel. Undersökningarna genomför- des pâ kattor som hade en kroppsvikt av 2,2 - 3,5 kg och som narkotiserats med kloralos-uretan i en dos om 50/300 mg/kg i.v. Den elektriskt fibrillära tröskeln (den lägsta strömintensiteten som erfordras för förmaks- och kammarfibrillofladder) genomfördes enligt de metoder som beskrives i litteraturen: Szekeres, Mëhes och Papp: Brit. J. Pharmacol. 17. 167, 1961: och Szekeres och Papp: Experimental car- diac arrhytmias and antiarrhytmic drugs. Akadëmiai Kiadö, Budapest, 1971.In comparative experiments, in which the compound of the invention HE-36: 3-Ben- zylamino-5,6-dihydro-8,9-dimethoxy-imidazo [5,1-a] isoquinoline hydrochloride (compare Example 4c), is compared in particular with respect to antiarrhythmic action on the heart with the compound well known for this purpose for its good effect, Chinidine, was obtained following results: LD5Ui.v. in rats Antiarrhythmic effect Atrium Chamber relatively therapeutic relatively therapeutic activity index activity index HE-36 17 mg / kg 8.66 90.00 '2.80 32.9 Quinidine 46 mg / kg 1.00 17.7 1.00 20.0 Antiarrhythmic activity was determined on the basis of the effect exerted on the the electrical-fibrillar threshold of the maxillary and ventricular muscle. The surveys are were found in cats with a body weight of 2.2 - 3.5 kg and which were anesthetized with chloralose urethane at a dose of 50/300 mg / kg i.v. The electrically fibrillar threshold (the lowest current intensity required for atrial and ventricular fibrillation flutter) was performed according to the methods described in the literature: Szekeres, Mëhes and Papp: Brit. J. Pharmacol. 17. 167, 1961: and Szekeres and Papp: Experimental car- diac arrhythmias and antiarrhythmic drugs. Akadëmiai Kiadö, Budapest, 1971.

Bröstkorgen öppnades på försöksdjuren och under undersökningarna tillämpades genomgående konstgjord andning. De genom den i perikardium gjorda lilla öppningen genomförda stimulerande elektroderna fästes i det högra förmaket vid auricula res- pektive fastsyddes vid den främre ytan i hjärtkammaren. Man tillämpade rätvink- liga slag genom elektrisk ström med en varaktighet av 1 msek och med en frekvens av 20 Hz under en period av 4 sek. Impulsernas intensitet stegrades till dess att fibrillo-fladder uppträdde och detta bestämdes med EKG delvis efter det plötsliga blodtrycksfallet och genom omedelbar iakttagelse av hjärtat.The chest was opened on the experimental animals and applied during the examinations continuous artificial respiration. They through the small opening made in the pericardium performed stimulating electrodes are attached to the right atrium at the auricular residual respectively was attached to the anterior surface of the ventricle. Right-angled stroke by electric current with a duration of 1 msec and with a frequency of 20 Hz for a period of 4 sec. The intensity of the impulses increased until fibrillo flutter appeared and this was determined by ECG partly after the sudden the drop in blood pressure and by immediate observation of the heart.

Under sådana betingelser visar antagandet av den elektriskt-fibrillära tröskeln C71 10 20 25 30 35 40 8000253-8 3 den antifibriiiära aktiviteten och antiarytmiaktiviteten.Under such conditions, the assumption of the electro-fibrillar threshold shows C71 10 20 25 30 35 40 8000253-8 3 the antifibrillary activity and the antiarrhythmic activity.

Föreningarna I och salter därav kan användas inom farmacin i form av prepa- rat innehåiiande den verksamma bestándsdeien i biandning med ogiftiga, inerta. farmaceutiskt användbara, organiska e11er oorganiska bärare. Preparaten beredes i fast form (exempeivis tabietter, fiimbeiagda tabietter, dragéer, enterosoivent- dragëer, piiier, kapsiar) e11er i vätskeform, exempeivis i form av suspensioner, iösningar e11er emuisioner. Som bärare kan man använda exempeivis taik. stärkeise, geiatin, vatten, poiyaikyiengiykoi etc. Preparaten kan iikaiedes innehàiia andra hjäipmedei, såsom vätmedei, emuigatorer, dispergatorer, sådana saiter som buffert- substanser som förändrar det osmotiska trycket och underiättar preparatets upp- iösning och/e11er andra farmaceutiskt aktiva substanser.The compounds I and salts thereof can be used in pharmacy in the form of preparations rat containing the active constituent in admixture with non-toxic, inert. pharmaceutically usable organic or inorganic carriers. The preparations are prepared in solid form (e.g. tablets, fibrous tablets, dragéer, enterosoivent- dragëer, piiier, kapsiar) e11er in liquid form, for example in the form of suspensions, solutions e11er emuitions. As a carrier, you can use, for example, taik. starch, geiatin, water, poiyaikyiengiykoi etc. The preparations may iikaiedes contain other auxiliaries, such as wetting agents, emuctors, dispersants, such as buffers. substances that alter the osmotic pressure and facilitate the uptake of the preparation solution and / or other pharmaceutically active substances.

Bâflflßllf 0,5 g 3-/6,7~dimetoxi-3,4-dihydro-1-isokinoiyi/-metyi-4-etyi- ÅÄ2-1,2,4-oxa- diazoion-5-on smäites på ett oijebad vid en temperatur av 15000 och smältan hölis därefter i ytteriigare 5 minuter vid nämnda temperatur. Sedan reaktionsbiandningen kaiinat tiiisattes 20 m1 vatten. Man erhöii på detta sätt 0,45 g 3-ety1amino-5,6- dihydro-8,9-dimetoxi-imidazo[§,1~§7isokino1in-monohydrat med en smäitpunkt av 128-130°C (efter omkristaiiisation i 50 3-ig etanoi).Bâfl fl ßllf 0.5 g of 3- [6,7-dimethoxy-3,4-dihydro-1-isoquinyl] -methyl-4-ethyl-α diazoion-5-one is forged on an oil bath at a temperature of 15,000 and the melt is healed then for another 5 minutes at said temperature. Then the reaction mixture The kaiinate was added 20 ml of water. There was thus obtained 0.45 g of 3-ethylamino-5,6- dihydro-8,9-dimethoxy-imidazo [§, 1 ~ §7isoquinoline monohydrate with a melting point of 128-130 ° C (after recrystallization from 50 3 g of ethanol).

Anaiysz C15H19N302.H20 teoretiskt funnet 61,83 % 62,11 % 7,26 2 7,23 % 14,39 2 14,56 % *íï.>i<flPffl_š= 2 g 3-/6,7-dimetoxi-3,4-dihydro-1-isokinoiyi/-metyi-4-bensy1- ħ2-1,2,4-oxa- diazoiin-5-on smäites på ett metaiibad. Efter avkyining omkristaiiiserades produk- ten i bensen och man erhö11 1,2 g 3-bensyiamino-5,6-dihydro-8,9-dimetoxi-imidazo/ [É,11§7-isokinoiin med en smäitpunkt av 135°C.Anaiysz C15H19N302.H20 theoretically found 61.83% 62.11% 7.26 2 7.23% 14.39 2 14.56% * íï.> i <fl Pf fl_ š = 2 g of 3- [6,7-dimethoxy-3,4-dihydro-1-isoquinyl] -methyl-4-benzyl- [2,2-1,2,4-oxa- diazoiin-5-one is forged on a metai bath. After cooling, the product was recrystallized. 1,2 g of 3-benzylamino-5,6-dihydro-8,9-dimethoxy-imidazo. [,, 11§7-isoquinoline with a melting point of 135 ° C.

Analys: C2ÜH21N302 teoretiskt funnet 71.62 % 71,52 % 6,31 % 5,98 % 12.53 ä 12,42 % I Produktens NMR-spektrum uppträdde protonen i stäiiningen 1 - 6,85 ppm.Analysis: C 21 H 21 N 3 O 2 theoretically found 71.62% 71.52% 6.31% 5.98% 12.53 to 12.42% In the NMR spectrum of the product, the proton appeared in the position 1 - 6.85 ppm.

Exempei 3: _ 10 mi Xyien sattes ti11 1,5 g 3-/6,7~dimetoxi-3,4-dihydro-1-isokino1y1/-mety1- 4-bensy1- ZX 2-1,2.4-oxadiazoiin-5-on och biandningen kokades under återfiöde i två timmar. Vid avkyining erhö11s 1,1 g 3-bensyiamino-5,6-dihydr-8,9-dimetoxi-imi- dazo[§Å11§]-isokinoiin i kristaiiiserad form. Produkten visade sig vara identisk med den eniigt exempei 2.Example 3: _ 10 ml of Xylene were added to 1.5 g of 3- [6,7-dimethoxy-3,4-dihydro-1-isoquinyl] -methyl- 4-Benzyl-ZX 2-1,2,4-oxadiazolin-5-one and the mixture were boiled under reflux in two hours. On cooling, 1.1 g of 3-benzylamino-5,6-dihydr-8,9-dimethoxy-imi- dazo [§Å11§] -isokinoiin in crystallized form. The product turned out to be identical with the only example 2.

Claims (2)

10 15 20 8030253-8 'i10 15 20 8030253-8 'i 1. Sätt att framställa nya aminoimidazoisokinolinderivat med den allmänna formeln i -v/wíï , ' L A/ k» _/ _ \ ç_.nHD I Hc- n och syraadditionssalter därav, i vilken formel A representerar en 1 - 4 kolatomer innehållande alkoxigrupp och D representerar en 1 - 4 kolatomer innehållande al- kylgrupp eller en i alkyldelen 1 - 4 kolatomer innehållande fenyl-alkylgrupp, k ä n n e t e c k n a t 1 av att föreningar med den allmänna formeln k//ï/ 1 11 ' l 'n Mflvsfrfl :Fb _ c _ 1: - I) i. J, l'.\o,.b §_O där A och D har ovan angivna betydelser, upphettas vid en temperatur över 100°C i ett lösningsmedel eller i en smälta, varpå den så erhållna föreningen I even- tuellt omvandlas till syraadditionssalter eller baserna med den allmänna formeln I frigöres ur sina salter. IA process for the preparation of novel aminoimidazoisoquinoline derivatives of the general formula i -v / wíï, 'LA / k D represents a 1-4 carbon atoms containing alkyl group or one in the alkyl moiety 1-4 carbon atoms containing phenyl-alkyl group, characterized in that compounds of the general formula k // ï / 1 11 'l' n M fl vsfr fl: Fb _ c _ 1: - I) i. J, l '. \ o, .b §_O where A and D have the meanings given above, heated at a temperature above 100 ° C in a solvent or in a melt, whereupon the so obtained compound I is optionally converted to acid addition salts or the bases of general formula I are liberated from their salts. IN 2. Sätt enligt krav 1, k ä n n e t e c k n a t medel använder xylen eller 1,2,3,4-tetrahydronaftalen. av att man som lösnings- Bä/Gen QÛ-01-07 âíïüüßläï ß ~l :AMJULN D R A G Uppfinningen hänför sig tiii ett förfarande för framstäiining av nya aminoimidazoisokinoiinderivat med den aiimänna formein f. _\ /ßx A/QÛ K \ç__nun Hc.. N och syraadditionssaiter därav, i viiken formei A representerar en 1 - 4 kol- atomer innehâiiande aikoxigrupp och D representerar en 1 - 4 koïatomer inne- hâïiande alkyigrupp e11er en i a1ky1de1en 1 - 4 koïatomer innehâiiande fenyi- aikyïgrupp. Vid detta förfarande upphettas en förening med den aiimänna formein A\\.//\ /,\\ 1 1 II AIX :v l/ÄJH HC _ c _ 1: ~ I» f; ß \,, e. (i där A och D har ovan angivna betydelser, vid en temperatur över 100°C i ett ïös- ningsmedei e11er i en smäita, varpå den så erhåiina föreningen med den ovan defi- 8000253-8 níerade formeln I eventueHt omvandïas till ett syraaddítíonssalt eHer en bas med' den aHmänna formeïn I frigöres ur något av sina saïter. Föreningarna som faTler under den aïïmänna formeln I har värdefuH anti- arytmíverkan och påverkar hjärtkammar- och förmaksmuskeïns fibríflära tröskel.2. A method according to claim 1, characterized in that the agent uses xylene or 1,2,3,4-tetrahydronaphthalene. BACKGROUND OF THE INVENTION This invention relates to a process for the preparation of novel aminoimidazoisoquinoin derivatives having the same form of fc. N and acid addition sites thereof, in which form A represents a 1-4 carbon atoms containing alkoxy group and D represents a 1-4 carbon atoms containing alkyl group or a 1-4 carbon atoms containing phenylalkyl group. In this process, a compound of the general form A \\ .// \ /, \\ 1 1 II AIX: v l / ÄJH HC _ c _ 1: ~ I »f; (in which A and D have the meanings given above, at a temperature above 100 ° C in a solvent medium or in a melt, then the compound thus obtained of the above-defined formula I may be converted to an acid addition salt or a base of the general form I is liberated from any of its sites.
SE8000253A 1972-06-30 1980-01-11 SET TO MAKE AMINOIMIDAZOISOKINOLIN DERIVATIVES SE431455B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HUCI1248A HU167240B (en) 1972-06-30 1972-06-30

Publications (2)

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SE8000253L SE8000253L (en) 1980-01-11
SE431455B true SE431455B (en) 1984-02-06

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ID=10994443

Family Applications (6)

Application Number Title Priority Date Filing Date
SE8002538A SE7308998L (en) 1972-06-30 1973-06-26 METHODS OF PREPARING NEW AMINOIMIDAZOISOCHINOIN DERIVATIVES AND SALTS THEREOF
SE7610169A SE410189B (en) 1972-06-30 1976-09-14 METHOD OF PRODUCING 3-AMINO-IMIDAZO (5.1-A) ISOKINOLINE DERIVATIVES
SE7610171A SE410190B (en) 1972-06-30 1976-09-14 METHOD OF PREPARING AMINOPYRAZOLO (5.1-A) ISOKINOLIN DERIVATIVES
SE7610170A SE425314B (en) 1972-06-30 1976-09-14 SET TO PREPARE 2-AMINO-PYRAZOLO / 5, 1-A / ISOQINOLINE DERIVATIVES
SE8000253A SE431455B (en) 1972-06-30 1980-01-11 SET TO MAKE AMINOIMIDAZOISOKINOLIN DERIVATIVES
SE8002538A SE420968B (en) 1972-06-30 1980-04-02 PROVIDED TO COMPENSATE THE HARMFUL INCREASE OF THE CATHODE DRUM DURING THE STARTING PERIOD OF A WALKING WAGON

Family Applications Before (4)

Application Number Title Priority Date Filing Date
SE8002538A SE7308998L (en) 1972-06-30 1973-06-26 METHODS OF PREPARING NEW AMINOIMIDAZOISOCHINOIN DERIVATIVES AND SALTS THEREOF
SE7610169A SE410189B (en) 1972-06-30 1976-09-14 METHOD OF PRODUCING 3-AMINO-IMIDAZO (5.1-A) ISOKINOLINE DERIVATIVES
SE7610171A SE410190B (en) 1972-06-30 1976-09-14 METHOD OF PREPARING AMINOPYRAZOLO (5.1-A) ISOKINOLIN DERIVATIVES
SE7610170A SE425314B (en) 1972-06-30 1976-09-14 SET TO PREPARE 2-AMINO-PYRAZOLO / 5, 1-A / ISOQINOLINE DERIVATIVES

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Application Number Title Priority Date Filing Date
SE8002538A SE420968B (en) 1972-06-30 1980-04-02 PROVIDED TO COMPENSATE THE HARMFUL INCREASE OF THE CATHODE DRUM DURING THE STARTING PERIOD OF A WALKING WAGON

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CA (1) CA1014559A (en)
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CH603643A5 (en) * 1976-09-29 1978-08-31 Sandoz Ag
HU176214B (en) * 1977-05-18 1981-01-28 Chinoin Gyogyszer Es Vegyeszet Process for producing new 5,6-dihydro-imidazo-square bracket-5,1-a-square bracket closed-isoquinolin derivatives
CA2372051A1 (en) * 1999-05-19 2000-11-23 The Procter & Gamble Company Imidazo-containing heterocyclic compounds, their compositions and uses
US6552033B1 (en) 2000-05-16 2003-04-22 The Procter & Gamble Co. Imidazo-containing heterocyclic compounds, their compositions and uses
PL2573073T3 (en) * 2011-09-26 2015-04-30 Sanofi Sa Pyrazoloquinolinone derivatives, preparation thereof and therapeutic use thereof

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CH25A (en) * 1888-11-16 1889-04-05 Saurer & Soehne F Machine for threading needles and for tying threads

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SE410189B (en) 1979-10-01
YU36176B (en) 1982-02-25
SE420968B (en) 1981-11-09
CH602730A5 (en) 1978-07-31
JPS5740152B2 (en) 1982-08-25
IN139710B (en) 1976-07-24
PL96818B1 (en) 1978-01-31
IL42613A0 (en) 1973-08-29
SE410190B (en) 1979-10-01
AR209330A1 (en) 1977-04-15
SE7308998L (en) 1980-01-11
PL93702B1 (en) 1977-06-30
YU299579A (en) 1981-06-30
PL97544B1 (en) 1978-03-30
YU36300B (en) 1982-06-18
BE801668A (en) 1973-10-15
GB1438819A (en) 1976-06-09
DE2332860C2 (en) 1982-12-02
AR210066A1 (en) 1977-06-30
PL94059B1 (en) 1977-07-30
SE405603B (en) 1978-12-18
SE7610171L (en) 1976-09-14
JPS4942697A (en) 1974-04-22
SE8002538L (en) 1981-10-03
CA1014559A (en) 1977-07-26
JPS5336480B2 (en) 1978-10-03
SU596170A3 (en) 1978-02-28
YU36177B (en) 1982-02-25
JPS5334799A (en) 1978-03-31
ES416971A1 (en) 1976-02-16
NO138908C (en) 1978-12-06
DE2332860A1 (en) 1974-03-07
CH603647A5 (en) 1978-08-31
NL177750B (en) 1985-06-17
SE7610169L (en) 1976-09-14
PL94046B1 (en) 1977-07-30
SE425314B (en) 1982-09-20
SU584782A3 (en) 1977-12-15
CH602729A5 (en) 1978-07-31
CS179024B1 (en) 1977-10-31
NL177750C (en) 1985-11-18
AR211857A1 (en) 1978-03-31
YU179673A (en) 1981-06-30
SU587863A3 (en) 1978-01-05
FR2190458B1 (en) 1977-04-15
AR208055A1 (en) 1976-11-30
CH603639A5 (en) 1978-08-31
YU299679A (en) 1981-06-30
DK141066B (en) 1980-01-07
FI55199B (en) 1979-02-28
EG11302A (en) 1978-06-30
YU36175B (en) 1982-02-25
SU591148A3 (en) 1978-01-30
NL7309104A (en) 1974-01-02
AT329058B (en) 1976-04-26
PL94060B1 (en) 1977-07-30
SE7610170L (en) 1976-09-14
ATA563773A (en) 1975-07-15
DD108090A1 (en) 1974-09-05
NO138908B (en) 1978-08-28
YU299479A (en) 1981-08-31
AR209331A1 (en) 1977-04-15
CH602731A5 (en) 1978-07-31
FI55199C (en) 1979-06-11
CH610900A5 (en) 1979-05-15
FR2190458A1 (en) 1974-02-01
DK141066C (en) 1980-06-30
IL42613A (en) 1977-05-31
SU584783A3 (en) 1977-12-15
HU167240B (en) 1975-09-27

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