DK164478B - Anvendelse af 9alpha,11beta-dichlor-16alpha-methyl-21-oxycarbonyldicyclohexylmethyloxypregna-1,4-dien-3,20-dion til fremstilling af et farmaceutisk praeparat til behandling af betaendelsestilstande i retcum eller colon - Google Patents
Anvendelse af 9alpha,11beta-dichlor-16alpha-methyl-21-oxycarbonyldicyclohexylmethyloxypregna-1,4-dien-3,20-dion til fremstilling af et farmaceutisk praeparat til behandling af betaendelsestilstande i retcum eller colon Download PDFInfo
- Publication number
- DK164478B DK164478B DK146785A DK146785A DK164478B DK 164478 B DK164478 B DK 164478B DK 146785 A DK146785 A DK 146785A DK 146785 A DK146785 A DK 146785A DK 164478 B DK164478 B DK 164478B
- Authority
- DK
- Denmark
- Prior art keywords
- preparation
- methyl
- 9alpha
- 11beta
- diene
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 9ALPHA, 11BETA-DICHLOR-16ALPHA-METHYL-21-OXYCARBONYLDICYCLOHEXYLMETHYLOXYPREGNA-1,4-DIENE-3,20-DION Chemical class 0.000 title claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 210000001072 colon Anatomy 0.000 claims abstract description 7
- 210000000664 rectum Anatomy 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 239000007903 gelatin capsule Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000000932 sedative agent Substances 0.000 claims 1
- 230000001624 sedative effect Effects 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 2
- QIEPWCSVQYUPIY-LEKSSAKUSA-N Delta(1)-progesterone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 QIEPWCSVQYUPIY-LEKSSAKUSA-N 0.000 abstract 1
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 229940126062 Compound A Drugs 0.000 description 11
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 11
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 208000025865 Ulcer Diseases 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 210000004100 adrenal gland Anatomy 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 210000001541 thymus gland Anatomy 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229960003957 dexamethasone Drugs 0.000 description 2
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229960005205 prednisolone Drugs 0.000 description 2
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 2
- 206010036784 proctocolitis Diseases 0.000 description 2
- 208000011231 Crohn disease Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010048768 Dermatosis Diseases 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000011554 guinea pig model Methods 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940068917 polyethylene glycols Drugs 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
- i -
DK 164478 B
Opfindelsen angår anvendelsen af 9alpha,llbeta-dichlor-16 alpha-methyl-21-oxycarbonyldicyclohexylmethyloxypregna-l,4--dien-3,20-dion (forbindelse A) til fremstilling af et farmaceutisk præparat til oral indgift og til behandling af 5 betændelsestilstande i rectum eller colon.
Forbindelse A er beskrevet som kemisk forbindelse i fransk patentskrift nr. 2.462.443. I dette patentskrift er der ligeledes for denne forbindelse nævnt en betændelseshæmmen-10 de virkning in loco. Det angives ligeledes i dette patent-skrift, at forbindelse A er uvirksom ad oral vej, og at adskillelsen mellem den betændelseshæmmende virkning in loco og aktiviteten ad generel vej, navnlig ad oral vej, gør forbindelsen særlig interessant til anvendelse i aerosol.
15 I angivne terapeutiske anvendelser i det nævnte franske patentskrift nr. 2.462.443 er således astma, ødem, dermatose, pruritis, forskellige former for eksem og solskoldning.
20 Det har nu vist sig, at forbindelsen A har en meget interessant virkning over for betændelsessygdomme i colon og rectum og navnlig i tilfælde af hemorragisk rectocolitis og Crohn's sygdom.
25 Den foreliggende opfindelse angår således anvendelse af forbindelsen A til fremstilling af et farmaceutisk præparat til peroral indgift, som er i stand til i kraft af dets indhold af tilsætningsstof at tillade virkningen af denne aktive bestanddel i colon eller rectum. Disse præparater 30 kan navnlig foreligge i følgende orale former: uoversukre- de eller oversukrede tabletter, gelatinekapsler, granulat, kapsler til henfald i tarmen.
Det ser ud til, at indgift ad oral vej tillader den aktive 35 bestanddel at passere størstedelen af fordøjelseskanalen uden omdannelse og således at nå colon eller rectum for på - 2 -
DK 164478 B
dette sted at udøve den ønskede virkning.
Den aktive bestanddel kan inkorporeres deri sammen med i farmaceutiske præparater normalt benyttede tilsætningsstof-5 fer såsom talkum, lactose, stivelse og derivater deraf, po-lyvinylpyrrolidon, silicagel, polyethylenglykoler, dicalci-umfosfat, tricalciumfosfat, polymere af acrylsyre, polymere af methacrylsyre og methacrylat, gelatine, magnesiumstea-rat, vandige eller ikke-vandige bærestoffer, fedtstoffer af 10 animalsk, vegetabilsk eller syntetisk oprindelse, paraffinderivater, glykoler og diverse fugte-, dispergerings- eller emulgeringsmidler samt konserveringsmidler.
Den benyttede dosis varierer i afhængighed af den behandle-15 de patient og den pågældende lidelse. Den kan ligge mellem 1 og 100 mg pr. dag og specielt mellem 5 og 50 mg og navnlig mellem 20 og 50 mg pr. dag.
Eksempel 20
Man fremstiller gelatinekapsler efter følgende recept:
Forbindelse A .................................. 10 mg - Tilsætningsstof til dannelse af en kapsel på ... 120 mg 25
Forbindelse A .................................. 25 mg - Tilsætningsstof til dannelse af en kapsel på ... 150 mg
Det farmaceutiske præparat kan især foreligge i form af 30 tablet eller gelatinekapsel.
Især foreligger det farmaceutiske præparat ifølge opfindelsen i form af tabletter.
35 - 3 -
DK 164478 B
Farmakologisk undersøgelse af 9alpha,llbeta-dichlor--16alpha-methyl-21-oxycarbonyldicyclohexylmethyloxy-pregna-1,4-dien-3,20-dion (forbindelse A)
Hanrotter af stammen Sprague-Dawley (200-250 g)sensibilise-5 res ved kutan påføring af en alkoholisk opløsning af dini-trochlorbenzen (DNCB) på 2,5%. Efter at man har udvalgt de dyr, som på den syvende dag udviser en positiv hypersensi-bilitetsreaktion, udfører man prøven som følger: 10 Man indgiver daglig i tre på hinanden følgende dage ad in-trarektal vej 2 ml 2,5%'s opløsning af DNCB i en blanding af acetone og vaselineolie. På samme tid indgiver man ad oral vej de forbindelser, som skal undersøges. » 15 Disse dyr aflives 24 timer efter den sidste behandling, og graden af alvorlighed af de ulcerøse læsioner vurderes.
Efter at man har vurderet de eventuelle systemiske virkninger af forbindelserne, fjerner man ligeledes thymus og binyrerne.
20 (Denne prøve er en modifikation af metoden ifølge A.A. Norris, Action of anti-colitic drugs on a guinea-pigmodel of immune colitis. Agents and Actions, 12_ 1/2, 239-242 (1982).) 25
Man får følgende resultater;
Dosis mg/kg Vægt af Vægt af forbin- % rotter thymus binyrer delse med ulcus i mg i mg 30
Kontrol 0 420 -24 40 -0,2 DNCB 72 349 ^44 45 -1,6 DNCB + forbindelse A 20 28 377 -24 42 ^0,2 DNCB + forbindelse A 50 14 345 -17 41 -1,5 35 DNCB + dexamethason 0,1 72 117 -6 30-1,7 DNCB + prednisolon 50 100 109 -11 31 -2,7
DK 164478 B
- 4 -
Konklusion
Disse resultater viser, at forbindelse A har klar aktivitet i denne model for immun rectocolitis uden systemisk effekt. Derimod viser dexamethason og prednisolon sig at være inak-5 tive mod ulcerøse læsioner fremkaldt af DNCB, men de har en systemisk aktivitet, således som nedgangen i vægten af thymus og binyrer viser.
10 15
Claims (3)
1. Anvendelse af 9alpha,llbeta-dichlor-16alpha-methyl-21--oxycarbonyldicyclohexylmethyloxypregna-1,4-dien-3,20-dion 5 til fremstilling af et farmaceutisk præparat til oral indgift og til behandling af beteendel sestil stande i rectum eller colon.
2. Anvendelse ifølge krav 1, kendetegnet ved, 10 at præparatet fremstilles i form af tabletter eller gelatinekapsler .
3. Anvendelse ifølge krav 1-2, kendetegnet ved, at præparatet fremstilles i form af tabletter. 15 20
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8405222 | 1984-04-03 | ||
| FR8405222A FR2561919B1 (fr) | 1984-04-03 | 1984-04-03 | Composition pharmaceutique constituee d'une part, a titre de principe actif, par la 9a,11b-dichloro 16a-methyl 21-oxycarbonyldicyclohexyl methyloxy pregna-1,4-diene 3,20-dione et d'autre part, par un excipient pharmaceutique inerte apte a permettre l'action du produit dans le rectum ou le colon |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| DK146785D0 DK146785D0 (da) | 1985-04-01 |
| DK146785A DK146785A (da) | 1985-10-04 |
| DK164478B true DK164478B (da) | 1992-07-06 |
| DK164478C DK164478C (da) | 1992-11-23 |
Family
ID=9302777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK146785A DK164478C (da) | 1984-04-03 | 1985-04-01 | Anvendelse af 9alpha,11beta-dichlor-16alpha-methyl-21-oxycarbonyldicyclohexylmethyloxypregna-1,4-dien-3,20-dion til fremstilling af et farmaceutisk praeparat til behandling af betaendelsestilstande i retcum eller colon |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4614736A (da) |
| EP (1) | EP0161144B1 (da) |
| JP (1) | JPS60224615A (da) |
| AT (1) | ATE41604T1 (da) |
| AU (1) | AU571073B2 (da) |
| CA (1) | CA1226817A (da) |
| DE (1) | DE3568944D1 (da) |
| DK (1) | DK164478C (da) |
| FR (1) | FR2561919B1 (da) |
| GR (1) | GR850815B (da) |
| HU (1) | HU196122B (da) |
| IL (1) | IL74642A (da) |
| MA (1) | MA20388A1 (da) |
| OA (1) | OA07978A (da) |
| PT (1) | PT80214B (da) |
| ZA (1) | ZA851927B (da) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8909559D0 (en) * | 1989-04-26 | 1989-06-14 | Smith Kline French Lab | Pharmaceutical compositions |
| US5578576A (en) * | 1994-09-02 | 1996-11-26 | Dalhousie University | Method and composition for treating intestinal wounds or ulcers |
| US20050059583A1 (en) | 2003-09-15 | 2005-03-17 | Allergan, Inc. | Methods of providing therapeutic effects using cyclosporin components |
| US7151085B2 (en) * | 2004-11-15 | 2006-12-19 | Allergan, Inc. | Therapeutic methods using cyclosporine components |
| US7135455B2 (en) * | 2004-11-15 | 2006-11-14 | Allergan, Inc | Methods for the therapeutic use of cyclosporine components |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2462443A1 (fr) * | 1979-07-26 | 1981-02-13 | Roussel Uclaf | Nouveau derive halogene de la serie du 16a-methyl pregnane, son procede de preparation et son application comme medicament |
| FR2471186A1 (fr) * | 1979-12-10 | 1981-06-19 | Roussel Uclaf | Nouveaux comprimes a delitescence colique, ainsi que leur procede de preparation |
| FR2533928A1 (fr) * | 1982-10-05 | 1984-04-06 | Roussel Uclaf | Nouveaux derives dichlores de la serie du 16a-methyl pregnane, leur procede de preparation et leur application comme medicaments |
-
1984
- 1984-04-03 FR FR8405222A patent/FR2561919B1/fr not_active Expired
-
1985
- 1985-03-14 ZA ZA851927A patent/ZA851927B/xx unknown
- 1985-03-19 IL IL74642A patent/IL74642A/xx unknown
- 1985-03-26 MA MA20612A patent/MA20388A1/fr unknown
- 1985-03-28 DE DE8585400612T patent/DE3568944D1/de not_active Expired
- 1985-03-28 AT AT85400612T patent/ATE41604T1/de not_active IP Right Cessation
- 1985-03-28 EP EP85400612A patent/EP0161144B1/fr not_active Expired
- 1985-04-01 GR GR850815A patent/GR850815B/el unknown
- 1985-04-01 JP JP60066731A patent/JPS60224615A/ja active Pending
- 1985-04-01 DK DK146785A patent/DK164478C/da not_active IP Right Cessation
- 1985-04-01 US US06/718,175 patent/US4614736A/en not_active Expired - Fee Related
- 1985-04-02 PT PT80214A patent/PT80214B/pt not_active IP Right Cessation
- 1985-04-02 CA CA000478163A patent/CA1226817A/fr not_active Expired
- 1985-04-02 HU HU851257A patent/HU196122B/hu not_active IP Right Cessation
- 1985-04-03 AU AU40800/85A patent/AU571073B2/en not_active Ceased
- 1985-04-03 OA OA58554A patent/OA07978A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK146785A (da) | 1985-10-04 |
| HU196122B (en) | 1988-10-28 |
| PT80214B (en) | 1987-02-17 |
| CA1226817A (fr) | 1987-09-15 |
| AU4080085A (en) | 1985-10-10 |
| GR850815B (da) | 1985-07-23 |
| DK146785D0 (da) | 1985-04-01 |
| IL74642A0 (en) | 1985-06-30 |
| OA07978A (fr) | 1987-01-31 |
| FR2561919A1 (fr) | 1985-10-04 |
| EP0161144B1 (fr) | 1989-03-22 |
| ZA851927B (en) | 1986-04-30 |
| AU571073B2 (en) | 1988-03-31 |
| JPS60224615A (ja) | 1985-11-09 |
| FR2561919B1 (fr) | 1986-12-19 |
| US4614736A (en) | 1986-09-30 |
| DE3568944D1 (en) | 1989-04-27 |
| ATE41604T1 (de) | 1989-04-15 |
| IL74642A (en) | 1988-09-30 |
| DK164478C (da) | 1992-11-23 |
| MA20388A1 (fr) | 1985-10-01 |
| EP0161144A1 (fr) | 1985-11-13 |
| PT80214A (en) | 1985-05-01 |
| HUT44436A (en) | 1988-03-28 |
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