NO139503B - REAGENTS FOR DETERMINATION OF A TOTAL BILIRUBINE CONTENT IN SULFANILIC ACID BASED LIQUIDS - Google Patents
REAGENTS FOR DETERMINATION OF A TOTAL BILIRUBINE CONTENT IN SULFANILIC ACID BASED LIQUIDS Download PDFInfo
- Publication number
- NO139503B NO139503B NO74740089A NO740089A NO139503B NO 139503 B NO139503 B NO 139503B NO 74740089 A NO74740089 A NO 74740089A NO 740089 A NO740089 A NO 740089A NO 139503 B NO139503 B NO 139503B
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- Prior art keywords
- bilirubin
- reagent
- determination
- serum
- content
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- 239000003153 chemical reaction reagent Substances 0.000 title claims description 22
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 title claims description 16
- 229950000244 sulfanilic acid Drugs 0.000 title claims description 14
- 239000007788 liquid Substances 0.000 title 1
- 238000008050 Total Bilirubin Reagent Methods 0.000 claims description 4
- 229940023964 caffeine and sodium benzoate Drugs 0.000 claims description 4
- JWBPVFVNISJVEM-UHFFFAOYSA-M sodium caffeine benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1.CN1C(=O)N(C)C(=O)C2=C1N=CN2C JWBPVFVNISJVEM-UHFFFAOYSA-M 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 210000001124 body fluid Anatomy 0.000 claims description 2
- 239000010839 body fluid Substances 0.000 claims description 2
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 44
- 239000000243 solution Substances 0.000 description 19
- 210000002966 serum Anatomy 0.000 description 17
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
- 235000010288 sodium nitrite Nutrition 0.000 description 7
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 4
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 229960001948 caffeine Drugs 0.000 description 3
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 3
- 235000010234 sodium benzoate Nutrition 0.000 description 3
- 239000004299 sodium benzoate Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 210000000941 bile Anatomy 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- -1 hydroxylamine compound Chemical class 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000008789 Direct Bilirubin Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/72—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving blood pigments, e.g. haemoglobin, bilirubin or other porphyrins; involving occult blood
- G01N33/728—Bilirubin; including biliverdin
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Bilirubin er et farvestoff i blodet som kan- tilbakeføres Bilirubin is a dye in the blood that can be returned
på den naturlige.spaltning av blodlegemér. Den utskilles over, leveren og gallen. Mens små mengder av bilirubin i serum er helt: on the natural breakdown of blood cells. It is excreted in the liver and bile. While small amounts of bilirubin in serum are completely:
normalt, .indikerer større verdier en forstyrrelse av utsondrings-systemet i leveren og gallen. En i lengre tid kjent metode for bestemmelse av bilirubin . i serum er koblingen av denne substans til diazotert sulfanilsyre. Man skiller herved mellom bilirubin som med en gang kan kobles (= direkte bilirubin), og bilirubin som først må frigis ved hjelp av en akselerator for å kunne tre inn i koblingsreaksjonsn (= indirekte bilirubin). For de "fleste diagnostiske tilfeller er det imidlertid tilstrekkelig å bestemme den totale bilirubin. Man bestemmer altså sammen direkte og indirekte bilirubin, idet man utfører.bestemmelsen i nærvær av en akselerator. En kjent, ofte -anvendt akselerator er en oppløsning av koffein og natriumbenzoat. De hittil vanlige bilirubinbestemmelser har den ulempe at ferdige oppløsninger av diazotert sulfanilsyre bare er holdbare en kort tid. Man må derfor hver gang påny før bestemmelsen, preparere den såkalte diazonløsning; enten ved at man tilsetter en oppløsning av natriumnitritt til en surgjort oppløsning av sulfanilsyre og.lar det således dannede "diazoreagens" innvirke på blandingen av akselerator bg.serum, eller ved at mån først fremstiller i.under-søkelsesrøret en liten mengde av diazoreagenset ved blanding av tilsvarende små mengder av sulfanilsyre og natriumnitrittoppløsning og derefter tilsetter serum og akséierator. I hvert av dissé tilfeller er det nødvendig med minst ett særlig arbeidstrinn (pipettering) for fremstilling av diazoreagenset. normally, larger values indicate a disturbance of the excretory system in the liver and bile. A long-known method for determining bilirubin. in serum, the link of this substance is to diazotized sulphanilic acid. In this way, a distinction is made between bilirubin, which can be linked immediately (= direct bilirubin), and bilirubin that must first be released with the help of an accelerator in order to enter the coupling reaction (= indirect bilirubin). For most diagnostic cases, however, it is sufficient to determine the total bilirubin. Direct and indirect bilirubin are therefore determined together, as the determination is carried out in the presence of an accelerator. A well-known, often-used accelerator is a solution of caffeine and sodium benzoate The hitherto common bilirubin determinations have the disadvantage that ready-made solutions of diazotized sulphanilic acid are only stable for a short time. One must therefore prepare the so-called diazone solution each time before the determination, either by adding a solution of sodium nitrite to an acidified solution of sulphanilic acid and.allowing the "diazo reagent" thus formed to act on the mixture of accelerator and serum, or by first preparing a small amount of the diazo reagent in the test tube by mixing correspondingly small amounts of sulphanilic acid and sodium nitrite solution and then adding serum and accelerator In each of these cases, at least one special ar is required pickling step (pipetting) for the preparation of the diazo reagent.
>••-: '1 I 1 tysk'voffentiiggjørelsesskrift 2.016.555 beskrives / anvendelse av en hydroksylaminforbindelse ved bilirubinundersøkelse. >••-: '1 In 1 German publication publication 2,016,555 the use of a hydroxylamine compound in bilirubin examination is described.
Det fremheves at tilsetning av hydroksylaminsaltet stabiliserer farven på det azobilirubin som dannes ved innvirkning av reagens-oppløsningen, og forhindrer dessuten reaksjon, med ubundet . .bilirubin efter tilsetning av alkali. Det er der. således tale om .en spesiell metode for bestemmelse av det bundne bilirubin, hvor det som reagensoppløsning anvendes en oppløsning med vanlig : sammensetning bestående av koffein, natriumbenzoat, sulfanilsyre og en nitrittoppløsning. , Det er nå overraskende funnet at man kan innspare minst " én pipettering hvis man blander en akselerator i form av e_n_opp-løsning av koffein og natriumbenzoat, med sulfanilsyren og over-fører denne holdbare blanding ved tilsetning av en dråpe av natriumnitritt-oppløsning i et bruksferdig farvereagens for bestemmelse av det totale bilirubininnhold. Til dette reagens må man bare tilsette det serum som skal undersøkes for å bevirke koblingen av den i serumet tilstedeværende bilirubin til det tilsvarende azofarvestoff. Farveintensiteten av prøven represen-terer et mål for bilirubinspeilet i serumet. It is emphasized that the addition of the hydroxylamine salt stabilizes the color of the azobilirubin that is formed when exposed to the reagent solution, and also prevents reaction with unbound . .bilirubin after addition of alkali. It is there. thus it is a special method for determining the bound bilirubin, where a solution with the usual composition consisting of caffeine, sodium benzoate, sulphanilic acid and a nitrite solution is used as the reagent solution. , It has now surprisingly been found that one can save at least one pipetting if one mixes an accelerator in the form of a solution of caffeine and sodium benzoate with the sulphanilic acid and transfers this stable mixture by adding a drop of sodium nitrite solution in a ready-to-use color reagent for determining the total bilirubin content. To this reagent one only needs to add the serum to be examined in order to cause the coupling of the bilirubin present in the serum to the corresponding azo dye. The color intensity of the sample represents a measure of the bilirubin level in the serum.
I henhold til oppfinnelsen tilveiebringes et reagens for bestemmelse av det totale bilirubininnhold i kroppsvæsker på basis av sulfanilsyre. Reagenset karakteriseres ved at det foruten sulfanilsyren inneholder den for gjennomføring av bestemmelsen nødvendige tilsetning av koffein og natriumbenzoat som i og for seg kjente akseleratorer i sur, vandig oppløsning. According to the invention, a reagent is provided for determining the total bilirubin content in body fluids based on sulphanilic acid. The reagent is characterized by the fact that, in addition to sulphanilic acid, it contains the addition of caffeine and sodium benzoate, which are known in and of themselves as accelerators in an acidic, aqueous solution, necessary for carrying out the determination.
At denne blandingen er vellykket, er desto mer overraskende da blandingen akseleråtor/natriumnitritt ved tilsetning av sulfanilsyre ikke fører til dannelse av et koblingsdyktig bilirubiri-reagens. Reagenset kan eventuelt inneholde et stabiliseringsmiddel, som i og for seg kjent, f.eks. trietanolamin. That this mixture is successful is all the more surprising as the accelerator/sodium nitrite mixture does not lead to the formation of a coupling-capable bilirubiri reagent when sulphanilic acid is added. The reagent may optionally contain a stabilizer, which is known per se, e.g. triethanolamine.
En reagensoppløsning ifølge oppfinnelsen kan f.eks. fremstilles av 0,1-0,3 mol koffein, 0,005-0,02 mol sulfanilsyre, 0,3-0,6 mol natriumbenzoat og eventuelt 0,1-0,3 mol av en fortrinns-vis organisk base, f.eks. trietanolamin, som stabiliseringsmiddel. Disse stoffer bringes i de angitte mengder ved tilsetning av vann til et volum på 1 liter og surgjøres med en mineralsyre, f.eks. en halogenhydrogensyre, fosforsyre eller salpetersyre til en betydelig sur reaksjon...Den tilsatte nitritt-oppløsning kan foreligge i 1-9 molar konsentrasjon. A reagent solution according to the invention can e.g. is prepared from 0.1-0.3 mol caffeine, 0.005-0.02 mol sulfanilic acid, 0.3-0.6 mol sodium benzoate and optionally 0.1-0.3 mol of a preferably organic base, e.g. . triethanolamine, as stabilizer. These substances are brought in the indicated amounts by adding water to a volume of 1 liter and acidified with a mineral acid, e.g. a hydrohalic acid, phosphoric acid or nitric acid to a significantly acidic reaction...The added nitrite solution can be present in 1-9 molar concentration.
Reagenset ifølge oppfinnelsen for bestemmelse av bilirubin har den fordel at man ved siden av pipetteringen av serum bare trenger The reagent according to the invention for the determination of bilirubin has the advantage that, in addition to the pipetting of serum, only
en avmålt mengde av reagenset, da nitritt-oppløsningen kan til-. settes fra en dråpeflaske. De herved mulige forskjeller i dråpe-størrelsen har bare en neglisjerbar innvirkning på resultatet. Anvendelse av reagenset betyr derfor en vesentlig tids-besparelse bg en usedvanlig stor økning av nøyaktigheten. ,"\ - Presisjonen er her tre ganger .større enn ved de hittil vanlige , bestemmelsesmetoder. Dette kommer til uttrykk ved den.relative standardavvikelse (variasjonskoeffisient) på ± 0,60%.for frem-gangsmåten ifølge oppfinnelsen, mens \ deri ved den vanlige fremgangs-måte utgjør ± 2,0% tii ± 3,0%. 1 v'\ a measured amount of the reagent, as the nitrite solution can add-. put from a dropper bottle. The resulting possible differences in the droplet size only have a negligible effect on the result. Use of the reagent therefore means a significant time saving and an exceptionally large increase in accuracy. "\ - The precision here is three times greater than with the previously common determination methods. This is expressed by the relative standard deviation (coefficient of variation) of ± 0.60% for the method according to the invention, while normal procedure amounts to ± 2.0% tii ± 3.0%. 1 v'\
Dessuten er det mulig å ha reagenset allerede i avmålt mengde i en flaske eller kolbe, så at brukeren bare må tilsette en dråpe av nitritt-oppløsningen, og innpipettere serum som skal undersøkes. Anvendelsen av dette reagens i analyseautomater betyr likeledes en vesentlig forenkling av innretningen for bestemmelse av bilirubin. Kålibreringskurven forløper rettlinjet inntil over. In addition, it is possible to have the reagent already in a measured amount in a bottle or flask, so that the user only has to add a drop of the nitrite solution, and pipet in the serum to be examined. The use of this reagent in automatic analyzers also means a significant simplification of the device for determining bilirubin. The calibration curve runs in a straight line up to the top.
20 mg bilirubin pr. 100 ml serum. 20 mg bilirubin per 100 ml of serum.
Eksempel Example
For å fremstille bilirubinreagenset ifølge oppfinnelsen - - tilsetter man 0,25 mol saltsyre til 0,2 mol koffein, 0,014 mol sulfanilsyre, 0,42 mol natriumbenzoat og 0,175 mol trietanolamin som oppløses i vann til 1 liter. I tillegg tilbereder man en 8,7-molar natriumnitritt-oppløsning. To prepare the bilirubin reagent according to the invention - - 0.25 mol hydrochloric acid is added to 0.2 mol caffeine, 0.014 mol sulphanilic acid, 0.42 mol sodium benzoate and 0.175 mol triethanolamine which is dissolved in water to 1 litre. In addition, an 8.7-molar sodium nitrite solution is prepared.
Gjennomføringen av analysen forløper som følger: The analysis proceeds as follows:
2,0 ml bilirubinreagens blandes med 1 dråpe (0,05 ml) natriumnitritt-oppløsning og tilsettes nøyaktig 0,2 ml serum. Mix 2.0 ml of bilirubin reagent with 1 drop (0.05 ml) of sodium nitrite solution and add exactly 0.2 ml of serum.
Blindverdiprøvén for eliminering av egenfarven og en eventuell.uklarhet av serum, er sammensatt av 2,0 ml bilirubinreagens og 0,2 ml serum uten natriumnitrittoppløsning. Den aktuelle prøve blir målt mot blindverdien av serum i fotometer ved Hg 546 i løpet av 3 minutter efter tilsetning av serum. The blank value sample for eliminating the intrinsic color and any turbidity of the serum is composed of 2.0 ml of bilirubin reagent and 0.2 ml of serum without sodium nitrite solution. The relevant sample is measured against the blank value of serum in a photometer at Hg 546 within 3 minutes after the addition of serum.
For å beregne bilirubininnholdet multipliseres den målte ekstinksjon med den eksperimentelt fundne faktor 13,2. To calculate the bilirubin content, the measured extinction is multiplied by the experimentally found factor 13.2.
Resultatet gir bilirubinspeilet i mg/100 ml serum. The result gives the bilirubin level in mg/100 ml of serum.
Beregningseksempel: ekstinksjon = 0,128 Calculation example: extinction = 0.128
0,128 • 13,2 = 1,69 mg/bilirubin/100 ml serum. 0.128 • 13.2 = 1.69 mg/bilirubin/100 ml serum.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2301687A DE2301687A1 (en) | 1973-01-13 | 1973-01-13 | METHOD FOR DETERMINING TOTAL BILIRUBIN IN BODY FLUIDS |
Publications (3)
Publication Number | Publication Date |
---|---|
NO740089L NO740089L (en) | 1974-07-16 |
NO139503B true NO139503B (en) | 1978-12-11 |
NO139503C NO139503C (en) | 1979-03-21 |
Family
ID=5868966
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO740089A NO139503C (en) | 1973-01-13 | 1974-01-11 | REAGENTS FOR DETERMINATION OF A TOTAL BILIRUBINE CONTENT IN SULFANILIC ACID BASED LIQUIDS |
Country Status (11)
Country | Link |
---|---|
AT (1) | AT330366B (en) |
BE (1) | BE809672A (en) |
CH (1) | CH590477A5 (en) |
DE (1) | DE2301687A1 (en) |
ES (1) | ES422249A1 (en) |
FI (1) | FI55912C (en) |
FR (1) | FR2325044A1 (en) |
IT (1) | IT1015804B (en) |
NL (1) | NL7400394A (en) |
NO (1) | NO139503C (en) |
SE (1) | SE414971B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4412005A (en) * | 1979-10-25 | 1983-10-25 | Eastman Kodak Company | Determination of total bilirubin |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3652222A (en) * | 1969-04-07 | 1972-03-28 | American Monitor Corp | Bilirubin assay |
-
1973
- 1973-01-13 DE DE2301687A patent/DE2301687A1/en active Pending
- 1973-12-18 FI FI3897/73A patent/FI55912C/en active
-
1974
- 1974-01-02 AT AT874*BA patent/AT330366B/en not_active IP Right Cessation
- 1974-01-11 NO NO740089A patent/NO139503C/en unknown
- 1974-01-11 SE SE7400396A patent/SE414971B/en unknown
- 1974-01-11 IT IT47661/74A patent/IT1015804B/en active
- 1974-01-11 CH CH38374A patent/CH590477A5/xx not_active IP Right Cessation
- 1974-01-11 BE BE139752A patent/BE809672A/en unknown
- 1974-01-11 NL NL7400394A patent/NL7400394A/xx not_active Application Discontinuation
- 1974-01-11 FR FR7401025A patent/FR2325044A1/en active Granted
- 1974-01-12 ES ES422249A patent/ES422249A1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR2325044A1 (en) | 1977-04-15 |
NO139503C (en) | 1979-03-21 |
CH590477A5 (en) | 1977-08-15 |
ES422249A1 (en) | 1976-04-01 |
SE414971B (en) | 1980-08-25 |
FR2325044B1 (en) | 1978-03-24 |
ATA874A (en) | 1975-09-15 |
IT1015804B (en) | 1977-05-20 |
NL7400394A (en) | 1974-07-16 |
BE809672A (en) | 1974-07-11 |
FI55912B (en) | 1979-06-29 |
NO740089L (en) | 1974-07-16 |
FI55912C (en) | 1979-10-10 |
AT330366B (en) | 1976-06-25 |
DE2301687A1 (en) | 1974-07-18 |
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