DE3050999C2 - Medicines containing 2-isopropylamino-4-hydroxypyrimidine - Google Patents

Medicines containing 2-isopropylamino-4-hydroxypyrimidine

Info

Publication number
DE3050999C2
DE3050999C2 DE3050999A DE3050999A DE3050999C2 DE 3050999 C2 DE3050999 C2 DE 3050999C2 DE 3050999 A DE3050999 A DE 3050999A DE 3050999 A DE3050999 A DE 3050999A DE 3050999 C2 DE3050999 C2 DE 3050999C2
Authority
DE
Germany
Prior art keywords
isopropylamino
hydroxypyrimidine
medicaments
contain
effect
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DE3050999A
Other languages
German (de)
Other versions
DE3050999A1 (en
Inventor
André Paris Esanu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
D'etudes De Produits Chimiques Sa Paris Fr Ste
Original Assignee
D'etudes De Produits Chimiques Sa Paris Fr Ste
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Application filed by D'etudes De Produits Chimiques Sa Paris Fr Ste filed Critical D'etudes De Produits Chimiques Sa Paris Fr Ste
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

Beispiel
2-Isopropylamino-4-hydroxypyrimidinexample
2-isopropylamino-4-hydroxypyrimidine

Das Ausgangs-Methylthiouracil wird dadurch erhalten, daß man Methyljodid mit Thiouracil in Gegenwart von Natriummethanolat umsetzt. Das so erhaltene Methylthiouracil (20 g; 0,14 Mol) wird zusammen mit 200 ml trockenem Toluol und 200 ml Isopropylamin in einen 1-1-Druckreaktor gebracht. Die Reaktion wird 24 h bei 110 bis 120°C unter Druck durchgeführt. Das resultierende Gemisch wird zur Trockene eingedampft, mit Aceton und Diäthyläther (50/50) behandelt, filtriert, mit Wasser gewaschen und in Isopropylacetat umkristallisiert. Auf diese Weise werden 17 g eines weißen kristallinen Produkts (Ausbeute 84%) mit einem Schmelzpunkt von 14O0C erhalten. Die Analyse des Produkts zeigt eine gute Übereinstimmung mit der Formel C7HnN3O. Es wird auch das Hydrochlorid dieser Verbindung (Schmelzpunkt 233 bis 234° C (Tottoli)) hergestellt, das gleichfalls ein weißes kristallines Produkt ist. Die entsprechenden Werte des UV-Spektrums sind wie folgt:The starting methylthiouracil is obtained by reacting methyl iodide with thiouracil in the presence of sodium methoxide. The methylthiouracil thus obtained (20 g; 0.14 mol) is placed in a 1-1 pressure reactor together with 200 ml of dry toluene and 200 ml of isopropylamine. The reaction is carried out under pressure at 110 to 120 ° C. for 24 hours. The resulting mixture is evaporated to dryness, treated with acetone and diethyl ether (50/50), filtered, washed with water and recrystallized from isopropyl acetate. In this manner, 17 g of a white crystalline product (yield 84%) with a melting point of 14O 0 C was obtained. Analysis of the product shows good agreement with the formula C 7 H n N 3 O. The hydrochloride of this compound (melting point 233 to 234 ° C. (Tottoli)) is also prepared, which is also a white crystalline product. The corresponding values of the UV spectrum are as follows:

In Wasser (für das Hydrochlorid)In water (for the hydrochloride)

In Methanol (für die Base)In methanol (for the base)

266266 nmnm r-1%
£lcmr-1%
£ lcm = 210= 210 217217 nmnm r-1%
£lcmr-1%
£ lcm = 740= 740 290290 nmnm

Xmax: = 293 nm
Xmax\ = 222 nm X max : = 293 nm
X max = 222 nm

E\'L = 510 E[L = 730 E \ 'L = 510 E [L = 730

Die Base ist ein weißes kristallines Produkt (Molekulargewicht 153,18), das in Wasser unlöslich, jedoch in Chloroform löslich ist.The base is a white crystalline product (molecular weight 153.18) which is insoluble in water but in Chloroform is soluble.

Toxizitättoxicity

Die akute Toxizität (mg/kg) von 2-Isopropylamino-4-hydroxypyrimidin wurde bei der Maus intraperitoneal und per os bestimmt. Die erhaltenen Werte sind in der folgenden Tabelle zusammengestellt:The acute toxicity (mg / kg) of 2-isopropylamino-4-hydroxypyrimidine was determined intraperitoneally in the mouse and determined per os. The values obtained are summarized in the following table:

VerabreichungswegRoute of administration

2-Isopropylamino-4-hydroxypyrimidin 2-isopropylamino-4-hydroxypyrimidine

2-IsopropyIamino-2-isopropylamino-

pyrimidin-ortho-pyrimidine-ortho-

phosphatphosphate

(DE 27 07 095)(DE 27 07 095)

Intraperitoneal Per osIntraperitoneal per os

1530 28301530 2830

Pharmakologiepharmacology

Die pharmakologische Aktivität von 2-Isopropy!amino-4-hydroxypyrimidin wurde durch die folgenden Ver gleichsversuche über die Regenerierung des Ischiasnervs von männlichen ausgewachsenen Ratten (Wistar) ermittelt.The pharmacological activity of 2-isopropylamino-4-hydroxypyrimidine was determined by the following Ver Similar experiments on the regeneration of the sciatic nerve in male adult rats (Wistar) determined.

Eine Läsion des Ischiasnervs von Ratten wurde dadurch bewirkt, daß 20 min lang eine Thennosonde von -20° C an den Nerv angelegt wurde. Sodann wurden die Ratten intraperitoneal mit dem Vergleichsprodukt oder mit 2-Isopropylamino-4-hydroxypyrimidin während einer vorbestimmten Dauer behandelt Danach wurden die Ratten getötet, und der Ischiasnerv wurde herausgetrennt. Dieser wurde mit einer Reihe von 70 dünnen parallelen Platindrähten (Abstand 1 mm) in Kontakt gebracht. Ein elektrisches Signal, das stromaufwärts der Läsionsstelle ausgesandt wurde, wurde mittels der Platindrähte erfaßt: der entferntere Draht, an dem das Signal empfangen werden kann, ergibt die regenerierte Länge.A rat sciatic nerve lesion was caused by a thennoprobe of -20 ° C was applied to the nerve. The rats were then given the comparative product intraperitoneally or treated with 2-isopropylamino-4-hydroxypyrimidine for a predetermined period Rats were killed and the sciatic nerve was excised. This one was made with a series of 70 thin parallels Platinum wires (distance 1 mm) brought into contact. An electrical signal that is upstream of the lesion site was detected by means of the platinum wires: the more distant wire on which the signal was received can be, gives the regenerated length.

Für jede Testzusammensetzung und jede Behandlungsdauer wurde eine Gruppe von 8 Ratten verwendet.A group of 8 rats was used for each test composition and treatment period.

Zwei Mittel wurden intraperitoneal getestet: die Verbindung des Beispiels und als Vergleichssubstanz 2-Isopropylaminopyrimidin-orthophosphat (DE 27 07 095). Die Kontrolltiere erhielten überhaupt keine Behandlung. Fünf Gruppen mit je 8 Tieren wurden für jede Dauer (7,11,14,17 und 21 Tage) sowohl für die Kontrollprobe als auch für die Verbindung des Beispiels oder die Vergleichsverbindung verwendet.Two agents were tested intraperitoneally: the compound of the example and, as a comparison substance, 2-isopropylaminopyrimidine orthophosphate (DE 27 07 095). The control animals received no treatment at all. Five groups of 8 animals each were given for each duration (7, 11, 14, 17 and 21 days) for both the control sample as well as used for the connection of the example or the comparison connection.

Die erhaltenen Versuchsergebnisse sind in der folgenden Tabelle zusammen mit den für die Kontrolltiere erhaltenen Werten zusammengestellt. Die Länge der regenerierten Nerven ist in mm in den entsprechenden Spalten der Tage angegeben. Es handelt sich um einen Mittelwert der Längen, die bei allen Tieren jeder Gruppe gemessen wurden. Wenn kein Wert angegeben ist (17 und 21 Tage), dann bedeutet dies, daß die Regenerierungslänge über die Länge der genommenen Probe hinausging. The test results obtained are in the following table together with those for the control animals values obtained. The length of the regenerated nerves is in mm in the corresponding Columns of days given. It is an average of the lengths found in all animals in each group were measured. If no value is given (17 and 21 days) it means that the regeneration length exceeded the length of the sample taken.

1010

2020th

Verbindung und Dosis intraperitonealConnection and dose intraperitoneally

Versuchsdauer (Tage) 7 11 14Test duration (days) 7 11 14

1717th

2121

2525th

KontrollversucheControl attempts 5,15.1 10,210.2 12,812.8 Verbindung des Beispiels
10 mg/kgConnection of the example
10 mg / kg 6,66.6 14,114.1 26,326.3 2-lsopropylaminopyrimidin-orthophosphat
(DE 27 07 095)
145 mg/kg (entsprechend 87 mg/kg freie Base)2-isopropylaminopyrimidine orthophosphate
(DE 27 07 095)
145 mg / kg (corresponding to 87 mg / kg free base) 6,76.7 16,216.2 22,722.7

17,817.8

22,422.4

Die erfindungsgemäß verwendete Verbindung zeigt überraschenderweise eine günstigere Relation von wirksamer zu letaler Dosis als die Vergleichsverbindung bei größerer Regenerierungslänge nach 14 Tagen.The compound used according to the invention surprisingly shows a more favorable ratio of more effective a lethal dose than the comparison compound with a longer regeneration length after 14 days.

Darreichung - DosiologiePresentation - Dosiology

2-Isopropylamino-4-hydroxypyrimidin kann in jeder beliebigen therapeutisch annehmbaren Form, beispielsweise in Tabletten oder in Gelatinekapseln, die 5 mg Wirkstoff pro Dosiseinheit zusammen mit einem Streckmittel enthalten, verabreicht werden. Für injizierbare Zubereitungen kann das Produkt in Ampullen dosiert werden, die mindestens 1 mg Wirkstoff in Form des Hydrochlorids, gelöst in Wasser, enthalten. In der Humanmedizin erfordert die orale Verabreichung 20 mg bis 1 g pro Tag, während injizierbare Zubereitungen in Dosen zwischen 1 mg und 50 mg pro Tag verabreicht werden können.2-Isopropylamino-4-hydroxypyrimidine can be in any therapeutically acceptable form, for example in tablets or in gelatin capsules containing 5 mg of active ingredient per dose unit together with an excipient contain, are administered. For injectable preparations, the product can be dosed in ampoules that contain at least 1 mg of active ingredient in the form of the hydrochloride dissolved in water. In human medicine Oral administration requires 20 mg to 1 g per day while injectable preparations are in doses between 1 mg and 50 mg per day can be administered.

Nachstehend wird ein Beispiel für eine Tablettenform angegeben:An example of a tablet shape is given below:

2-Isopropylamlno-4-hydΓoxypyrlmldln2-Isopropylamine-4-hydoxy-oxypyrlmldln 5 mg5 mg LactoseLactose 70 mg70 mg TalkTalk 20 mg20 mg MagnesiumstearatMagnesium stearate 5 mg5 mg

100 mg100 mg

3030th

3535

4040

4545

5050

5555

6060

Claims (1)

Patentanspruch:Claim: Arzneimittel, enthaltend 2-Isopropylamino-4-hydroxyp)'rimidin neben üblichen Hilfs- und/oder Zusatzstoffen. Medicaments containing 2-isopropylamino-4-hydroxyp) 'rimidine in addition to customary auxiliaries and / or additives. Die Erfindung betrifft Arzneimittel, die 2-Isopropylamino-4-hydroxypyrimidin enthalten.The invention relates to medicaments which contain 2-isopropylamino-4-hydroxypyrimidine. In der DE-OS 21 09 880 sind fungizide 2-Alkylamino-4-hydroxypyiimidine beschrieben, wobei als 2-Alkylaminorest auch der Isopropylaminorest genannt ist. Eine Wirkung dieser Verbindung als Arzneimittel ist nicht erwähnt.In DE-OS 21 09 880 fungicidal 2-alkylamino-4-hydroxypyiimidines are described, with the 2-alkylamino radical the isopropylamino radical is also called. This compound has no effect as a medicinal product mentioned. In der DE-AS 22 49 425 ist das 2-Isopropylaminopyrimidindichloracetat und in der DE-AS 27 07 095 das 2-Isopropylaminopyrimidin-orthophosphat offenbart. Für beide Verbindungen wird eine Wirkung auf die Regenerierung von Nervenfasern beschrieben.In DE-AS 22 49 425 the 2-isopropylaminopyrimidinedichloroacetate and in DE-AS 27 07 095 that 2-isopropylaminopyrimidine orthophosphate is disclosed. For both compounds there will be an effect on regeneration described by nerve fibers. Gegenstand der Erfindung sind Arzneimittel, die 2-Isopropylamino-4-hydroxypyrimidin neben üblichen Hilfs- und/oder Zusatzstoffen enthalten.The invention relates to medicaments which contain 2-isopropylamino-4-hydroxypyrimidine in addition to the usual Contain auxiliaries and / or additives. Der erfindungsgemäß verwendete Wirkstoff kann hergestellt werden, indem man 2-Methylthio-4-hydroxypyrimidin in an sich bekannter Weise mit Isopropylamin in einem nicht-polaren Lösungsmittel bei 100 bis 120° C und unter Druck umsetzt.The active ingredient used in the present invention can be prepared by adding 2-methylthio-4-hydroxypyrimidine in a manner known per se with isopropylamine in a non-polar solvent at 100 to 120.degree and converts it under pressure. Die erfiiidungsgemäßen Arzneimittel sind insbesondere wegen ihrer Wirkungen auf dem Gebiete der Nervenregenerierung und zur Behandlung von Muskeldystrophien von Interesse. Sie zeigen eine überraschend bessere Wirkung als die aus den DE-AS 22 49 425 und 27 07 095 bekannten Verbindungen.The medicaments according to the invention are particularly important because of their effects in the field of nerve regeneration and for the treatment of muscular dystrophies of interest. They show a surprisingly better one Effect than the compounds known from DE-AS 22 49 425 and 27 07 095.
DE3050999A 1979-03-10 1980-03-10 Medicines containing 2-isopropylamino-4-hydroxypyrimidine Expired DE3050999C2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB7908494 1979-03-10
GB7914987 1979-04-30

Publications (2)

Publication Number Publication Date
DE3050999A1 DE3050999A1 (en) 1985-08-14
DE3050999C2 true DE3050999C2 (en) 1986-08-14

Family

ID=26270867

Family Applications (3)

Application Number Title Priority Date Filing Date
DE3050999A Expired DE3050999C2 (en) 1979-03-10 1980-03-10 Medicines containing 2-isopropylamino-4-hydroxypyrimidine
DE3009071A Expired DE3009071C2 (en) 1979-03-10 1980-03-10 2-isopropylamino-hydroxypyrimidine compounds, processes for their preparation and pharmaceuticals containing these compounds
DE19803016752 Granted DE3016752A1 (en) 1979-03-10 1980-04-30 METHOD FOR PRODUCING 2-ISOPROPYLAMINOPYRIMIDINE HYDROXY DERIVATIVES

Family Applications After (2)

Application Number Title Priority Date Filing Date
DE3009071A Expired DE3009071C2 (en) 1979-03-10 1980-03-10 2-isopropylamino-hydroxypyrimidine compounds, processes for their preparation and pharmaceuticals containing these compounds
DE19803016752 Granted DE3016752A1 (en) 1979-03-10 1980-04-30 METHOD FOR PRODUCING 2-ISOPROPYLAMINOPYRIMIDINE HYDROXY DERIVATIVES

Country Status (24)

Country Link
JP (1) JPS55122768A (en)
AR (1) AR222691A1 (en)
AU (1) AU533547B2 (en)
BE (1) BE881752A (en)
CA (1) CA1132561A (en)
CH (1) CH644368A5 (en)
DE (3) DE3050999C2 (en)
EG (1) EG14282A (en)
FI (1) FI66357C (en)
FR (2) FR2451370A1 (en)
GB (1) GB2045756B (en)
HK (1) HK55383A (en)
IE (1) IE49547B1 (en)
IN (1) IN153791B (en)
LU (1) LU82185A1 (en)
MX (1) MX6218E (en)
MY (1) MY8400200A (en)
NL (1) NL184833C (en)
NO (1) NO154054C (en)
NZ (1) NZ192927A (en)
OA (1) OA06484A (en)
PT (1) PT70882A (en)
SE (1) SE435180B (en)
SG (1) SG22683G (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE894517A (en) * 1981-10-16 1983-01-17 Sod Conseils Rech Applic NEW ISOPROPYLAMINO PYRIMIDINE DERIVATIVE, ITS PREPARATION AND THERAPEUTIC COMPOSITION BASED ON ITS COMPOUNDS
US4554276A (en) * 1983-10-03 1985-11-19 Pfizer Inc. 2-Amino-5-hydroxy-4-methylpyrimidine derivatives
US4673677A (en) * 1983-10-03 1987-06-16 Pfizer Inc. Method for treatment of gastrointestinal disorders
US4711888A (en) 1985-07-24 1987-12-08 Pfizer Inc. Hydroxy and alkoxy pyrimidines
WO1989000423A1 (en) * 1987-07-09 1989-01-26 Pfizer Inc. 2-amino-5-hydroxy-4-pyrimidones
US4910204A (en) * 1988-06-28 1990-03-20 Pfizer Inc. 2-amino-5-hydroxy-4-pyrimidones
US5264435A (en) * 1988-12-29 1993-11-23 Mitsui Petrochemical Industries, Ltd. Pyrimidines and their pharmaceutical acceptable salts, and their use as medicines
HU206337B (en) * 1988-12-29 1992-10-28 Mitsui Petrochemical Ind Process for producing pyrimidine derivatives and pharmaceutical compositions
US4940712A (en) * 1989-05-26 1990-07-10 Pfizer Inc. Derivatives of hydroxyprimidines as leukotriene synthesis inhibitors
US5270319A (en) * 1991-09-09 1993-12-14 Warner-Lambert Company 5-hydroxy-2-pyrimidinylmethylene derivatives useful as antiinflammatory agents
US5196431A (en) * 1992-02-24 1993-03-23 Warner-Lambert Company 2-substituted amino-4, 6-di-tertiary-buthyl-5-hydroxy-1, 3-pyrimidines as antiinflammatory agents
US5220025A (en) * 1992-02-24 1993-06-15 Warner-Lambert Company 2-substituted amino-4, 6-di-tertiary-butyl-5-hydroxy-1, 3-pyrimidines as antiinflammatory agents
US9133212B1 (en) * 2005-06-15 2015-09-15 Vanderbilt University Inhibitors of hemeprotein-catalyzed lipid peroxidation

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB741667A (en) * 1952-12-05 1955-12-07 Ici Ltd New pyrimidine derivatives
GB756189A (en) * 1954-02-01 1956-08-29 Ici Ltd New pyrimidine derivatives
ZA711152B (en) * 1970-03-02 1971-11-24 Ici Ltd Manufacture of pyrimidines
GB1525995A (en) * 1976-02-18 1978-09-27 Soc D Etudes Prod Chimique Aminopyrimidine salt

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NICHTS-ERMITTELT

Also Published As

Publication number Publication date
IN153791B (en) 1984-08-18
FR2451370B1 (en) 1983-05-13
GB2045756B (en) 1983-01-26
MY8400200A (en) 1984-12-31
HK55383A (en) 1983-11-25
EG14282A (en) 1983-09-30
DE3016752A1 (en) 1980-12-04
FR2451191A1 (en) 1980-10-10
DE3009071A1 (en) 1980-09-11
AR222691A1 (en) 1981-06-15
BE881752A (en) 1980-05-30
AU533547B2 (en) 1983-12-01
AU5624880A (en) 1980-09-18
MX6218E (en) 1984-12-21
JPS6126996B2 (en) 1986-06-23
GB2045756A (en) 1980-11-05
NL184833C (en) 1989-11-16
DE3009071C2 (en) 1985-11-14
NO800664L (en) 1980-09-11
FI66357C (en) 1984-10-10
SE8001812L (en) 1980-09-11
FI66357B (en) 1984-06-29
CH644368A5 (en) 1984-07-31
DE3050999A1 (en) 1985-08-14
CA1132561A (en) 1982-09-28
NO154054C (en) 1986-07-09
JPS55122768A (en) 1980-09-20
IE800477L (en) 1980-09-10
NL8001289A (en) 1980-09-12
OA06484A (en) 1981-07-31
NZ192927A (en) 1981-07-13
SG22683G (en) 1983-12-16
SE435180B (en) 1984-09-10
LU82185A1 (en) 1980-06-06
FI800566A (en) 1980-09-11
PT70882A (en) 1980-03-01
IE49547B1 (en) 1985-10-30
NL184468B (en) 1989-03-01
NL184833B (en) 1989-06-16
FR2451191B1 (en) 1983-04-29
FR2451370A1 (en) 1980-10-10
NO154054B (en) 1986-04-01
DE3016752C2 (en) 1987-06-25

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