SE435180B - HYDROXIDE DERIVATIVES OF 2-ISOPROPYLAMINO-PYRIMIDINE AND SETS FOR PREPARING THEREOF - Google Patents

HYDROXIDE DERIVATIVES OF 2-ISOPROPYLAMINO-PYRIMIDINE AND SETS FOR PREPARING THEREOF

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Publication number
SE435180B
SE435180B SE8001812A SE8001812A SE435180B SE 435180 B SE435180 B SE 435180B SE 8001812 A SE8001812 A SE 8001812A SE 8001812 A SE8001812 A SE 8001812A SE 435180 B SE435180 B SE 435180B
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SE
Sweden
Prior art keywords
pyrimidine
hydrogen atom
isopropylamino
derivatives
preparing
Prior art date
Application number
SE8001812A
Other languages
Swedish (sv)
Other versions
SE8001812L (en
Inventor
A Esanu
Original Assignee
Soc D Etudes Prod Chimique
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Application filed by Soc D Etudes Prod Chimique filed Critical Soc D Etudes Prod Chimique
Publication of SE8001812L publication Critical patent/SE8001812L/en
Publication of SE435180B publication Critical patent/SE435180B/en

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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

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  • 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

, aee1s12-o 2 110_120°C. Den erhållna blandningen indunstas till torrhet, behandlas med aceton och dietyleter (50/50), filtreras, tvät- tas med vatten och omkristalliseras i isopropylacetat. Man erhåller sålunda 17 g (84-procentigt utbyte) av en vit kristal- lin produkt med en smältpunkt av 140°C, vars analys visar god överensstämmelse med formeln C?H11N50. Hydrokloriden av denna förening framställes också, smäitpunkt 255_254°c (mnttnli), som också är en vit kristallin produkt. Data för U.V.-spektrum: I vatten (för hydrokloriden) I metanol (för basen) amax = 266 nn Elfm = 210V nmax = 295 nn Eïfm = 510 1° 10 amax : 217 Dm Elšm = 740 ñmax : 222 nm Elšm = 730 fimax : 290 nm Basen är en vit kristallin produkt (molekylvikt 155,18), olöslig i vatten men löslig i kloroform._ Exempel 2: 5-hydroxi-2-isopropylamíno-pyrimidin Förfarandet enligt exempel 1 upprepades men 5-hydroxi-2- -tiometyl-pyrimidin användes. Utbyte 85 %. Reaktionstempera- turen var 105°C, smältpunkt 161°C (Tottoli). U.V.~spektrum Å vatten 60/metanol 40: Hmax = 541 nn E1fm = 205 amax ; 241 nn Elfm = 1210 Exempel 5: 4.6-dihydroxi-2-isopropylamino-pyrimidin Förfarandet enligt exempel 1 upprepades men 4,6-dihydro- -2-tiometyl-pyrimidin användes. Utbyte 67 %. Reaktionstempe- raturen 11000. Smältpunkt 215_220°C under sönderfall (Tottoli) för hydrokloriden med formeln C7H11N5O3,HCl. Detta är en vit kristallin produkt, olöslig i vatten vid rumstemperatur. , aee1s12-o 2 110_120 ° C. The resulting mixture is evaporated to dryness, treated with acetone and diethyl ether (50/50), filtered, washed with water and recrystallized from isopropyl acetate. 17 g (84% yield) of a white crystalline product with a melting point of 140 DEG C. are thus obtained, the analysis of which shows good agreement with the formula C1H11N50. The hydrochloride of this compound is also prepared, m.p. 255 DEG-254 DEG C. (mint), which is also a white crystalline product. Data for UV spectrum: In water (for the hydrochloride) In methanol (for the base) amax = 266 nn Elfm = 210V nmax = 295 nn Eïfm = 510 1 ° 10 amax: 217 Dm Elšm = 740 ñmax: 222 nm Elšm = 730 fi max : 290 nm The base is a white crystalline product (molecular weight 155,18), insoluble in water but soluble in chloroform. Example 2: 5-hydroxy-2-isopropylaminopyrimidine The procedure of Example 1 was repeated but 5-hydroxy-2- thiomethyl-pyrimidine was used. Yield 85%. The reaction temperature was 105 ° C, melting point 161 ° C (Tottoli). U.V. ~ spectrum Å water 60 / methanol 40: Hmax = 541 nn E1fm = 205 amax; 241 nn Elfm = 1210 Example 5: 4,6-Dihydroxy-2-isopropylamino-pyrimidine The procedure of Example 1 was repeated but 4,6-dihydro--2-thiomethyl-pyrimidine was used. Yield 67%. Reaction temperature 11000. Melting point 215-220 ° C during decomposition (Tottoli) of the hydrochloride of the formula C7H11N5O3, HCl. This is a white crystalline product, insoluble in water at room temperature.

Toxicitet ben akuta toxiciteten (mg/kg)píör föreningarna enligt upp- finningen bestämdes på möss i.p. och per os, och värdena anges 1 följande tabell; sea1s12-o Förening “\~ Ex. 1 Ex. 2 Ex. 5 Administrerings:“\»-\\ sätt “*~ i.p. 200 240 260 per os 205 555 285 Farmakologi Den farmakologiska aktiviteten hos föreningen enligt upp- finningen har undersökts med följande jämförande experiment, som utförts med avseende på regenereringen av höftnerven på fullvuxna hanràttor (Wistar).Toxicity to bone The acute toxicity (mg / kg) of the compounds of the invention was determined in mice i.p. and per os, and the values are given in the following table; sea1s12-o Association “\ ~ Ex. 1 Ex. 2 Ex. Administration: “\» - \\ way “* ~ i.p. 200 240 260 per os 205 555 285 Pharmacology The pharmacological activity of the compound according to the invention has been investigated by the following comparative experiments, which have been carried out with respect to the regeneration of the hip nerve in adult male rats (Wistar).

En skada orsakas på ràttornas höftnerv genom applicering av en termosond vid -2000 under 20 min. på nerven. Råttorna behandlas därefter i.p. med referensprodukten eller med före- ningarna enligt uppfinningen under en förutbestämd tid. I slutet av behandlingen dödas råttorna, höftnerverna separeras och placeras i kontakt med en serie av 70 tunna parallella pla- tinatràdar (intervall 1 mm) och en elektrisk signal, anbringad uppströms om punkten för økadan, sökes på platinatrådarna.An injury is caused to the hip nerve of the rats by applying a thermal probe at -2000 for 20 min. on the nerve. The rats are then treated i.p. with the reference product or with the compounds of the invention for a predetermined time. At the end of the treatment, the rats are killed, the hip nerves are separated and placed in contact with a series of 70 thin parallel platinum wires (range 1 mm) and an electrical signal, applied upstream of the point of the eccentricity, is sought on the platinum wires.

Den bortersta tråden, där signalen kan uppsamlas, ger den rege- nererade längden.The farthest wire, where the signal can be collected, gives the regenerated length.

För varje undersökt komposition och varje behandlingstid användes en grupp om 8 råttor.For each composition tested and each treatment time, a group of 8 rats was used.

För jämförelsens skull har följande föreningar undersökts i.p.: förening enligt exempel 1, förening enligt exempel 2, förening enligt exempel 5, alla vid den i.p. dosen av 10 mg/kg och som referens en blandning av vitaminerna B1 (500 mg/kg), (500 må/kg) och B12 (5 mg/kg), som är känd inom tekniken för att vara den mest effektiva kompositionen inom detta område.For the sake of comparison, the following compounds have been tested i.p .: compound of Example 1, compound of Example 2, compound of Example 5, all at the i.p. dose of 10 mg / kg and as a reference a mixture of vitamins B1 (500 mg / kg), (500 mg / kg) and B12 (5 mg / kg), which is known in the art to be the most effective composition in this area.

Kontroller fick ingen behandling alls. Fem grupper om 8 djur användes för varje tidsperiod (7, 11, 14, 17 och 21 dagar) både för kontroller och för föreningar 1, 2, 5 och referens- blandningen.Controls received no treatment at all. Five groups of 8 animals were used for each time period (7, 11, 14, 17 and 21 days) both for controls and for compounds 1, 2, 5 and the reference mixture.

Resultaten av detta försök återges i följande tabell till- sammans med de siffror, som erhölls för kontrolldjuren. Längden av regenererade nerver anges i mm i de respektive dagkolumnerna såsom ett medelvärde för de längder, som uppmättes för alla :øe1s12-o 4 djur i varje grupp. När inga siffror förekommer (17 och 21 dagar) betyder detta att den regenererade längden överskred längden av det uttagna provet.The results of this experiment are given in the following table together with the figures obtained for the control animals. The length of regenerated nerves is given in mm in the respective day columns as an average of the lengths measured for all: øe1s12-o 4 animals in each group. When no numbers appear (17 and 21 days), this means that the regenerated length exceeded the length of the sample taken.

Tid (dagar) 7 11 14 17 21 örening och dos i.p.Time (days) 7 11 14 17 21 trout and dose i.p.

I Kontroller 5,1 10,2 12,6 17,8 22,4 Exempel 1 1 6,6 14,1 26,5 _ _ mg/kg _ Exempel 2 6,8 14¿4 26,1 _ _ me/ka ~ Exempel 5 ' 6,7 15,6 26,7 _ _ mg/kg B1, B6, B12 ' 8,8 15,4 15,5 20,4 25,7 500 må/kå, 500 mg/kg och ma/ke Läkemedelsform och daglig dos Dessa derivat kan föreligga i vilken terapeutisk godtag- bar form som helst, t.ex. i form av tabletter eller gelatin- kapslar, som innehåller 5 mg per dosenhet tillsammans med ett utdrygningsmedel. För injicerbar form kan produkten doseras i ampuller, som innehåller minst 1 mg aktiv ingrediens i form av dess hydroklorid, löst i vatten. Den dagliga dosen för människa är vid oral administrering fràn 20 mg till 1 g per dag, under det att injícerbar form kan administreras i doser mellan 1 mg och 50 mg per dag.I Controls 5.1 10.2 12.6 17.8 22.4 Example 1 1 6.6 14.1 26.5 _ _ mg / kg _ Example 2 6.8 14¿4 26.1 _ _ me / Example 5 '6.7 15.6 26.7 _ _ mg / kg B1, B6, B12' 8.8 15.4 15.5 20.4 25.7 500 må / kå, 500 mg / kg and ma / ke Pharmaceutical form and daily dose These derivatives may be in any therapeutically acceptable form, e.g. in the form of tablets or gelatin capsules containing 5 mg per dosage unit together with an excipient. For injectable form, the product may be metered into ampoules containing at least 1 mg of active ingredient in its hydrochloride, dissolved in water. The daily dose for humans is for oral administration from 20 mg to 1 g per day, while injectable form may be administered in doses between 1 mg and 50 mg per day.

Ett exempel på tablettform återges nedan= _ förening enligt något av exemplen -5 mg - laktos 70 mg - talk 20 mg e- magnesiumstearat 2 mg 100 mg'An example of tablet form is given below = compound of any of the examples -5 mg - lactose 70 mg - talc 20 mg e-magnesium stearate 2 mg 100 mg

Claims (2)

1. 8001812-0 Patentkrav 4. 2-isopropylamino-pyrimidin-hydroxiderivat med den allmänna formeln vari var och en av A , A och Aè betecknar en väteatom elharen hydroxigrupp, med det förbehållet att minst en av A4, A5 och A6 inte betecknar en väteatom.A 2-isopropylamino-pyrimidine hydroxide derivative of the general formula wherein each of A, A and Aè represents a hydrogen atom or the hydroxy group, with the proviso that at least one of A4, A5 and A6 does not represent a hydrogen atom. 2. Sätt att framställa 2-isopropylamino-pyrimidin- -hydroxiderivat med den allmänna formeln A . 4 *N I I cH I 5 - A5 NH-cn/ / \cH . A6 N i 3- vari var och en av A4, A5 och A6 betecknar en väteatom elhæren hydroxigrupp, varvid minst en av A4, A5 och A6 inte betecknar en väteatom, k ä n n e t e c k n a t av att man omsätter mot- svarande 2-tiometyl-pyrimidin med isopropylamin i ett icke pdärt lösningsmedel vid 100_120°C under tryck enligt följande schema A A 4 -N H 4 *N CH A5 >_s 0115 + HZN-clï/C 5 -e A5- \ »NH-cn/ 5 \ \ A \ cflš - A N en; 5 . 6 skam e 12-0 Uppfinníngen avser 2-isopropylamino-pyrimídin-hydroxi- derivat med den allmänna formeln ' A4 4 N ca A5 __m1_cn< 5 \ N/ ' CH 5 vari var och en av A4, A5 och A6 betecknar en väteatom anßren hydroxígrupp, med det förbehållet att minst en av A4, A5 och A6 inte betecknar en väteatom. Uppfinningen avser även ett förfarande för framställning av dessa derivat genom omsättning av motsvarande 2-tiometyl-pyrímidin med isopropylamin i ett icke polärt lösningsmedel vid 100-12000 under tryck enligt följande schema: A4 Föreningarna enligt uppfinningen kan användas till regenere- ring av nerver och för behandling av muskeldystrofier. >\ls cnš + H2N___cH/CH3_ A5 />-avH--cH/CH5Ä / \CH5 \ N \cH¿¿ . A6/2. Methods of preparing 2-isopropylamino-pyrimidine hydroxide derivatives of the general formula A. 4 * N I I cH I 5 - A5 NH-cn / / \ cH. A6 N in 3 - wherein each of A4, A5 and A6 represents a hydrogen atom or hydroxy group, at least one of A4, A5 and A6 does not represent a hydrogen atom, characterized in that the corresponding 2-thiomethyl-pyrimidine is reacted with isopropylamine in a non-pert solvent at 100 DEG-120 DEG C. under pressure according to the following scheme AA 4 -NH4 * N CH A5> _s 0115 + HZN-cl1 / C5 -e A5- \ »NH-cn / 5 \ \ A \ c fl š - AN en; 5. The invention relates to 2-isopropylamino-pyrimidine-hydroxy derivatives of the general formula 'A4 4 N ca A5 __m1_cn <5 \ N /' CH 5 wherein each of A4, A5 and A6 represents a hydrogen atom hydroxy group, with the proviso that at least one of A4, A5 and A6 does not represent a hydrogen atom. The invention also relates to a process for the preparation of these derivatives by reacting the corresponding 2-thiomethyl-pyrimidine with isopropylamine in a non-polar solvent at 100-12000 under pressure according to the following scheme: A4 The compounds of the invention can be used for nerve regeneration and for treatment of muscular dystrophies. > \ ls cnš + H2N ___ cH / CH3_ A5 /> - avH - cH / CH5Ä / \ CH5 \ N \ cH¿¿. A6 /
SE8001812A 1979-03-10 1980-03-07 HYDROXIDE DERIVATIVES OF 2-ISOPROPYLAMINO-PYRIMIDINE AND SETS FOR PREPARING THEREOF SE435180B (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
SE8001812L SE8001812L (en) 1980-09-11
SE435180B true SE435180B (en) 1984-09-10

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ID=26270867

Family Applications (1)

Application Number Title Priority Date Filing Date
SE8001812A SE435180B (en) 1979-03-10 1980-03-07 HYDROXIDE DERIVATIVES OF 2-ISOPROPYLAMINO-PYRIMIDINE AND SETS FOR PREPARING THEREOF

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
HU206337B (en) * 1988-12-29 1992-10-28 Mitsui Petrochemical Ind Process for producing pyrimidine derivatives and pharmaceutical compositions
US5264435A (en) * 1988-12-29 1993-11-23 Mitsui Petrochemical Industries, Ltd. Pyrimidines and their pharmaceutical acceptable salts, and their use as medicines
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
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
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
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

Also Published As

Publication number Publication date
IE49547B1 (en) 1985-10-30
BE881752A (en) 1980-05-30
EG14282A (en) 1983-09-30
JPS6126996B2 (en) 1986-06-23
FR2451370A1 (en) 1980-10-10
DE3050999C2 (en) 1986-08-14
FR2451191A1 (en) 1980-10-10
NL184833B (en) 1989-06-16
NL8001289A (en) 1980-09-12
NL184833C (en) 1989-11-16
MY8400200A (en) 1984-12-31
AR222691A1 (en) 1981-06-15
LU82185A1 (en) 1980-06-06
IN153791B (en) 1984-08-18
DE3009071C2 (en) 1985-11-14
AU5624880A (en) 1980-09-18
JPS55122768A (en) 1980-09-20
AU533547B2 (en) 1983-12-01
FI800566A (en) 1980-09-11
NO154054B (en) 1986-04-01
PT70882A (en) 1980-03-01
FI66357B (en) 1984-06-29
OA06484A (en) 1981-07-31
DE3009071A1 (en) 1980-09-11
NZ192927A (en) 1981-07-13
DE3016752A1 (en) 1980-12-04
DE3016752C2 (en) 1987-06-25
MX6218E (en) 1984-12-21
SE8001812L (en) 1980-09-11
FR2451370B1 (en) 1983-05-13
NL184468B (en) 1989-03-01
NO800664L (en) 1980-09-11
NO154054C (en) 1986-07-09
CA1132561A (en) 1982-09-28
IE800477L (en) 1980-09-10
SG22683G (en) 1983-12-16
GB2045756B (en) 1983-01-26
HK55383A (en) 1983-11-25
DE3050999A1 (en) 1985-08-14
FR2451191B1 (en) 1983-04-29
FI66357C (en) 1984-10-10
GB2045756A (en) 1980-11-05
CH644368A5 (en) 1984-07-31

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