LU84827A1 - PHARMACEUTICAL COMPOSITIONS CONTAINING AT LEAST ONE POLYFLUORINATED ALCOHOL - Google Patents
PHARMACEUTICAL COMPOSITIONS CONTAINING AT LEAST ONE POLYFLUORINATED ALCOHOL Download PDFInfo
- Publication number
- LU84827A1 LU84827A1 LU84827A LU84827A LU84827A1 LU 84827 A1 LU84827 A1 LU 84827A1 LU 84827 A LU84827 A LU 84827A LU 84827 A LU84827 A LU 84827A LU 84827 A1 LU84827 A1 LU 84827A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- composition according
- formula
- component
- parts
- polyfluorinated
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 23
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 17
- 235000012000 cholesterol Nutrition 0.000 claims description 9
- KUGBQWBWWNPMIT-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluoropentan-1-ol Chemical compound CC(F)(F)C(F)(F)C(F)(F)C(O)(F)F KUGBQWBWWNPMIT-UHFFFAOYSA-N 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 239000008159 sesame oil Substances 0.000 claims description 5
- 235000011803 sesame oil Nutrition 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 230000002485 urinary effect Effects 0.000 claims 2
- 230000000118 anti-neoplastic effect Effects 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 241001465754 Metazoa Species 0.000 description 7
- GUAMVMSOIYAUSK-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-hexadecafluorononan-1-ol Chemical compound CC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(O)(F)F GUAMVMSOIYAUSK-UHFFFAOYSA-N 0.000 description 5
- 230000001925 catabolic effect Effects 0.000 description 5
- BYKNGMLDSIEFFG-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoroheptan-1-ol Chemical compound OCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)F BYKNGMLDSIEFFG-UHFFFAOYSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 206010070863 Toxicity to various agents Diseases 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 230000001195 anabolic effect Effects 0.000 description 2
- 230000007665 chronic toxicity Effects 0.000 description 2
- 231100000160 chronic toxicity Toxicity 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 231100000456 subacute toxicity Toxicity 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000207961 Sesamum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 231100000915 pathological change Toxicity 0.000 description 1
- 230000036285 pathological change Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/38—Halogenated alcohols containing only fluorine as halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
La présente invention concerne des compositions pharmaceutiques pos sédant une activité antinioplastique et contenant, à titre d'ingrédients actifs, (a) au moins un alcool polyfluorl de formule I : CHV(Cr2>n-CH20H (I) 5 dans laquelle n est un nombre égal à 3, 5, T ou 9 et facultativement (h) du cholestérol.The present invention relates to pharmaceutical compositions pos sedating an antinioplastic activity and containing, as active ingredients, (a) at least one polyfluorl alcohol of formula I: CHV (Cr2> n-CH20H (I) 5 in which n is a number equal to 3, 5, T or 9 and optionally (h) cholesterol.
**
De préférence, les compositions selon l'invention contiennent au moins , deux alcools polyfluorés de formule (i) et du cholestérol. Il est meme plusPreferably, the compositions according to the invention contain at least two polyfluorinated alcohols of formula (i) and cholesterol. It is even more
10 avantageux à'employer une composition contenant (a) trois alcools polyfluorés de formule (i) et en plus (h) le cholestérol. Les proportions relatives des trois alcools polyfluorés dans les compositions préférées selon l'invention peuvent varier entre de larges limites, par exemple de 12 parties de dodé-cafluoroheptanol(composé I dans lequel n = 5) + 1 partie d'octafluoropentanol ; 15 ( composé I dans lequel n = 3) + 1 partie d'hexadêcafluorononanol (composé IIt is advantageous to use a composition containing (a) three polyfluorinated alcohols of formula (i) and in addition (h) cholesterol. The relative proportions of the three polyfluorinated alcohols in the preferred compositions according to the invention can vary between wide limits, for example of 12 parts of dodé-cafluoroheptanol (compound I in which n = 5) + 1 part of octafluoropentanol; 15 (compound I in which n = 3) + 1 part of hexadecafluorononanol (compound I
I dans lequel n = T), à 1 partie de dodécafluoroheptanol + 12 parties d'octafluoro- | pentanol + 1 partie d'hexadêcafluorononanol, jusqu’à 1 partie de dodécafluoro- i heptanol + 1 partie d'octafluoropentanol +12 parties d'hexadêcafluorononanol J Les proportions relatives entre les composants (a) et (h) peuvent 20 varier entre 10:1 et 1:10.I in which n = T), to 1 part of dodecafluoroheptanol + 12 parts of octafluoro- | pentanol + 1 part of hexadecafluorononanol, up to 1 part of dodecafluoro- i heptanol + 1 part of octafluoropentanol +12 parts of hexadecafluorononanol J The relative proportions between components (a) and (h) can vary between 10: 1 and 1:10.
La composition selon l'invention peut en outre contenir des véhicules | lipophiles tels que l'huile de sésame ou une substance analogue. Tous les com- | posants des compositions pharmaceutiques selon l'invention sont bien connus et | j disponibles dans le commerce.The composition according to the invention may also contain vehicles | lipophiles such as sesame oil or the like. All the com | pharmaceutical compositions according to the invention are well known and | j commercially available.
' 25 nés exemples suivants, dans lesquels toutes les proportions sont en poids, servent à illustrer l'invention sans aucunement en limiter la portée.The following 25 examples, in which all the proportions are by weight, serve to illustrate the invention without in any way limiting its scope.
EXEMPLE 1EXAMPLE 1
Dans 150 g d'huile de sésame, or. dissout 3 g d'octafluoropentanol, 5 g de dodécafluoroheptanol eu 7,3 g d?riexadécafluc-rononanol. On ajoute è la solution 2,5 g de cholestérol tout en chauffant pendant une brève durée à 35~ ko°c.In 150 g of sesame oil, gold. dissolves 3 g of octafluoropentanol, 5 g of dodecafluoroheptanol or 7.3 g of riexadecafluc-rononanol. 2.5 g of cholesterol are added to the solution while heating for a short time at 35 ~ ko ° c.
EXE·?LE 2 A 100 g d'huile ce sésame» en ajoute 2,3 g de dodécafluoroheptanol, 2,5 g d'hexadêcafluorononanol et 5 g d'octafluoropentanol ainsi que t g de t ! ' · i I 2 cholestérol, en agitant jusqu'à dissolution complète.EXE ·? LE 2 To 100 g of oil this sesame "add 2.3 g of dodecafluoroheptanol, 2.5 g of hexadecafluorononanol and 5 g of octafluoropentanol as well as t g of t! '· I I 2 cholesterol, shaking until completely dissolved.
EXEMPLE 3 A 17¾ g d'huile de sésame, on ajoute les composants suivants tout en agitant jusqu'à dissolution complète : dodécafluoroheptanol (I, n = 5) 12g hexadécafluorononanol (l,n=7) i g octafluoropentanol (i, n = 3) Itg - cholestérol 6 g IOn répartit la solution ainsi obtenue en fioles d'une contenance de 10 ο 3 0,2 cm , en fioles d'une contenance de 0,3 cm et en fioles d'une contenance 3 de 0,5 cm . On stérilise les fioles par chauffage.EXAMPLE 3 To 17¾ g of sesame oil, the following components are added while stirring until complete dissolution: dodecafluoroheptanol (I, n = 5) 12g hexadecafluorononanol (l, n = 7) ig octafluoropentanol (i, n = 3 ) Itg - cholesterol 6 g IOn distribute the solution thus obtained in vials with a capacity of 10 ο 3 0.2 cm, in vials with a capacity of 0.3 cm and in vials with a capacity 3 of 0.5 cm. The vials are sterilized by heating.
EXEMPLEEXAMPLE
On prépare la composition de la même façon que dans l'exemple 1 en ] ^ ajoutant 2 g d'eicosafluorundécanol (I, n = 9).The composition is prepared in the same way as in Example 1 by] ^ adding 2 g of eicosafluorundecanol (I, n = 9).
j EXEMPLE 5 ; On procède comme dans l'exemple 1 mais en remplaçant l'hexadécafluo-j EXAMPLE 5; The procedure is as in Example 1 but by replacing the hexadecafluo-
IIII
rononanol par une quantité égale d'octafluoropentanol.rononanol with an equal amount of octafluoropentanol.
20 EXEMPLE 6 ji On procède comme dans l'exemple S mais on n'ajoute pas de cholestérol.EXAMPLE 6 The procedure is as in Example S, but no cholesterol is added.
! On a étudié la composition selon l’exemple 3 pour déterminer la toxi- î cité aigue, la toxicité subaiguë et la toxicité chronique.! The composition according to Example 3 was studied to determine the acute toxicity, the subacute toxicity and the chronic toxicity.
i : 25 Toxicité aisuë : L'injection sous-cutanée de doses supérieures a 0,5 cm à des u 1 1 ' souris pesant 30 g provoque, comme unique svmpucme, le sommeil après lequel les ; animaux se réveillent au bout de quelques heures sans aucune manifestation î anormale. Le même phénomène apparaît chez les rats avec des doses supérieures ; v N < — «* + t~. r __ | c. I 5^· CiL "pOXL· 1 Ü'J g * ; —i , Toxicité subaiguë : L'administration par voie sous-cutanée à raison de 0,3 cm-3 j, par jour pendant une période de 5 jours au cours d'une semaine, durant trois ;' _ semaines consécutives à ces souris pesant 30 g ne provoque aucun svmptîne toxi- , W * * i, aient. été sacrifiés.i: 25 Easy toxicity: The subcutaneous injection of doses greater than 0.5 cm in u 1 1 'mouse weighing 30 g causes, as the only swmpucme, sleep after which; animals wake up after a few hours without any abnormal manifestation. The same phenomenon occurs in rats with higher doses; v N <- "* + t ~. r __ | vs. I 5 ^ · CiL "pOXL · 1 Ü'J g *; —i, Subacute toxicity: Subcutaneous administration at a rate of 0.3 cm-3 d, per day for a period of 5 days during one week, for three; ' _ consecutive weeks, these mice weighing 30 g do not cause any toxic symptoms, W * * i, have been sacrificed.
! 35 1' Toxicité chronique : On soumet des souris pesant 30 g à ces injections sous- * » i I 3 ! cutanées de 0,2 cnf* par jour, trois fois par semaine pendant trois mois con sécutifs. Les animaux ne manifestent aucune réaction anormale par rapport aux témoins et on ne constate aucun changement pathologique chez les animaux après qu'ils aient été sacrifiés.! Chronic toxicity: Mice weighing 30 g are subjected to these sub-injections. 0.2 cnf * skin daily, three times a week for three consecutive months. The animals did not show any abnormal reaction compared to the controls and there was no pathological change in the animals after they were sacrificed.
OO
5 On obtient des résultats identiques en administrant 0,¾ cnr pour 100 g à des rats. On ne constate aucun phénomène toxique quand on administre la composition aux souris et aux rats par voie orale à l'aide d'un cathéter à O n raison de 0,2 cnr par jour ou 0,¾ cnr pour 100 g par jour dans le cadre de traitemenlB prolongés. On ne constate egalement aucun symptôme toxique lors-10 quîon ajoute 1 % de cette composition à l'alimentation de certains animaux hien que quelques animaux manifestent une certaine réluctance à manger les aliments contenant cet additif.5 Identical results are obtained by administering ¾ cnr per 100 g to rats. No toxic phenomenon is observed when the composition is administered to mice and rats orally using an O n catheter at the rate of 0.2 cnr per day or 0, ¾ cnr per 100 g per day in the extended treatment framework. There are also no toxic symptoms when adding 1% of this composition to the diet of some animals, although some animals show a certain reluctance to eat foods containing this additive.
En se basant sur ce qui précède, on démontre que les composés selon l'invention sont pratiquement exempts de toxicité.Based on the above, it is demonstrated that the compounds according to the invention are practically free from toxicity.
115 Pharmacologie : Le concept de la dualité anabolique/catabolique et les définitions apparentées, dont il sera question ci-après, sont largement illustrés également du point de vue expérimental, aussi bien chez les animaux que chez l'homme par E. Revici, Research in physiopathology, Van Kostrand, édit.115 Pharmacology: The concept of anabolic / catabolic duality and related definitions, which will be discussed below, are also widely illustrated from an experimental point of view, both in animals and in humans by E. Revici, Research in physiopathology, Van Kostrand, ed.
j Princeton, 1961. Cependant l'originalité de l'invention ne dépend pas de l'exacti- 120 tude des théories étudiées dans ce traité. Les compositions selon l'invention et en particulier la composition objet de l'exemple 3, a une influence très favorable sur les lésions développant ainsi un effet catabolique. Cette influence est clairement montrée par la guérison des blessures et des brûlures. Bans le cas du cancer expérimental, on a constaté une différence très nette-de com-25 portement selon le caractère anabolique ou catabolique des tumeurs. En fait, jj * dans le premier cas, les compositions selon l'invention retardent seulement la Îsort des animaux mais ces mêmes compositions exercent un effet bénéfique important sur les tumeurs de caractère catabolique, avec nécrose et accumulation ce i, fluide et de cellules dans la pycnose.j Princeton, 1961. However, the originality of the invention does not depend on the exactitude of the theories studied in this treatise. The compositions according to the invention and in particular the composition object of Example 3, has a very favorable influence on the lesions thus developing a catabolic effect. This influence is clearly shown by the healing of wounds and burns. In the case of experimental cancer, there was a very clear difference in behavior depending on the anabolic or catabolic nature of the tumors. In fact, in the first case, the compositions according to the invention only delay the release of animals, but these same compositions exert a significant beneficial effect on tumors of catabolic character, with necrosis and accumulation of this fluid and cells in pycnosis.
H 3QH 3Q
!; Etude clinique : Egalement dans le traitement de natients affectés de tumeurs h - ” ‘ | * cataboliques, la composition selon l'invention administrée par injection intra- I ^ ·* 3 s I musculaire à une 'dose de 2 a 3 cet développent une action nettement favorable [’ en éliminant ou en recuisant, la souffrance pensant plusieurs heures.!; Clinical study: Also in the treatment of patients affected by h - ”‘ tumors | * catabolic, the composition according to the invention administered by intra-I ^ · * 3 s I muscular injection at a dose of 2 to 3 which develop a clearly favorable action [’by eliminating or annealing, suffering thinking for several hours.
t! j I 1t! j I 1
Claims (8)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2155382 | 1982-05-28 | ||
| IT8221553A IT8221553A0 (en) | 1982-05-28 | 1982-05-28 | PHARMACEUTICAL COMPOSITIONS ANTINEOPLASTIC ADAPTIVITY. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU84827A1 true LU84827A1 (en) | 1983-11-17 |
Family
ID=11183507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU84827A LU84827A1 (en) | 1982-05-28 | 1983-05-27 | PHARMACEUTICAL COMPOSITIONS CONTAINING AT LEAST ONE POLYFLUORINATED ALCOHOL |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS591414A (en) |
| AU (2) | AU552557B2 (en) |
| BE (1) | BE896838A (en) |
| CH (1) | CH653890A5 (en) |
| DE (1) | DE3319304A1 (en) |
| FR (1) | FR2527439A1 (en) |
| GB (1) | GB2121280B (en) |
| IE (1) | IE55137B1 (en) |
| IL (1) | IL68796A0 (en) |
| IN (1) | IN157042B (en) |
| IT (1) | IT8221553A0 (en) |
| LU (1) | LU84827A1 (en) |
| NL (1) | NL8301899A (en) |
| NZ (1) | NZ204393A (en) |
| SE (1) | SE8302976L (en) |
| ZA (1) | ZA833871B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3836971C1 (en) * | 1988-10-31 | 1990-05-17 | Weck, Wolfgang, Dr.Med., 6990 Bad Mergentheim, De |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3219004C1 (en) * | 1982-05-19 | 1984-03-01 | Philippine Dr. 8000 München Hartmann | Pharmaceutical compositions for the treatment of tumours |
-
1982
- 1982-05-28 IT IT8221553A patent/IT8221553A0/en unknown
-
1983
- 1983-05-20 CH CH2772/83A patent/CH653890A5/en not_active IP Right Cessation
- 1983-05-26 GB GB08314540A patent/GB2121280B/en not_active Expired
- 1983-05-26 JP JP58093889A patent/JPS591414A/en active Pending
- 1983-05-26 AU AU15000/83A patent/AU552557B2/en not_active Expired - Fee Related
- 1983-05-26 BE BE2/60100A patent/BE896838A/en not_active IP Right Cessation
- 1983-05-26 IL IL68796A patent/IL68796A0/en unknown
- 1983-05-26 SE SE8302976A patent/SE8302976L/en not_active Application Discontinuation
- 1983-05-27 IN IN673/CAL/83A patent/IN157042B/en unknown
- 1983-05-27 IE IE1259/83A patent/IE55137B1/en unknown
- 1983-05-27 LU LU84827A patent/LU84827A1/en unknown
- 1983-05-27 ZA ZA833871A patent/ZA833871B/en unknown
- 1983-05-27 DE DE19833319304 patent/DE3319304A1/en not_active Ceased
- 1983-05-27 FR FR8308776A patent/FR2527439A1/en not_active Withdrawn
- 1983-05-27 NL NL8301899A patent/NL8301899A/en not_active Application Discontinuation
- 1983-05-27 NZ NZ204393A patent/NZ204393A/en unknown
-
1988
- 1988-05-04 AU AU15570/88A patent/AU1557088A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU1557088A (en) | 1988-11-10 |
| NL8301899A (en) | 1983-12-16 |
| ZA833871B (en) | 1984-07-25 |
| IN157042B (en) | 1986-01-04 |
| IE55137B1 (en) | 1990-06-06 |
| BE896838A (en) | 1983-09-16 |
| GB8314540D0 (en) | 1983-06-29 |
| FR2527439A1 (en) | 1983-12-02 |
| GB2121280B (en) | 1985-08-29 |
| SE8302976D0 (en) | 1983-05-26 |
| SE8302976L (en) | 1983-11-29 |
| GB2121280A (en) | 1983-12-21 |
| IE831259L (en) | 1983-11-28 |
| AU552557B2 (en) | 1986-06-05 |
| IT8221553A0 (en) | 1982-05-28 |
| JPS591414A (en) | 1984-01-06 |
| IL68796A0 (en) | 1983-09-30 |
| DE3319304A1 (en) | 1983-12-01 |
| CH653890A5 (en) | 1986-01-31 |
| NZ204393A (en) | 1986-03-14 |
| AU1500083A (en) | 1983-12-01 |
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