DK175504B1 - Farmaceutisk præparat indeholdende 3alfa-hydroxy-5beta-pregnan-20-on og fremstilling deraf - Google Patents
Farmaceutisk præparat indeholdende 3alfa-hydroxy-5beta-pregnan-20-on og fremstilling deraf Download PDFInfo
- Publication number
- DK175504B1 DK175504B1 DK198700621A DK62187A DK175504B1 DK 175504 B1 DK175504 B1 DK 175504B1 DK 198700621 A DK198700621 A DK 198700621A DK 62187 A DK62187 A DK 62187A DK 175504 B1 DK175504 B1 DK 175504B1
- Authority
- DK
- Denmark
- Prior art keywords
- oil
- pregnanolone
- amount
- water
- final preparation
- Prior art date
Links
- AURFZBICLPNKBZ-YZRLXODZSA-N 3alpha-hydroxy-5beta-pregnan-20-one Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 AURFZBICLPNKBZ-YZRLXODZSA-N 0.000 title claims abstract description 33
- AURFZBICLPNKBZ-UHFFFAOYSA-N Pregnanolone Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(=O)C)C1(C)CC2 AURFZBICLPNKBZ-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims description 29
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- 229950007402 eltanolone Drugs 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 239000007764 o/w emulsion Substances 0.000 claims abstract description 14
- 238000001990 intravenous administration Methods 0.000 claims abstract description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000008215 water for injection Substances 0.000 claims description 11
- 229940099371 diacetylated monoglycerides Drugs 0.000 claims description 10
- 239000008344 egg yolk phospholipid Substances 0.000 claims description 8
- 229940068998 egg yolk phospholipid Drugs 0.000 claims description 8
- 239000003549 soybean oil Substances 0.000 claims description 8
- 235000012424 soybean oil Nutrition 0.000 claims description 8
- WLNARFZDISHUGS-MIXBDBMTSA-N cholesteryl hemisuccinate Chemical compound C1C=C2C[C@@H](OC(=O)CCC(O)=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 WLNARFZDISHUGS-MIXBDBMTSA-N 0.000 claims description 6
- 239000003921 oil Substances 0.000 claims description 5
- 235000012343 cottonseed oil Nutrition 0.000 claims description 4
- 239000002385 cottonseed oil Substances 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- 235000019198 oils Nutrition 0.000 claims description 4
- 235000010469 Glycine max Nutrition 0.000 claims description 3
- 235000019485 Safflower oil Nutrition 0.000 claims description 3
- 235000021324 borage oil Nutrition 0.000 claims description 3
- 239000003240 coconut oil Substances 0.000 claims description 3
- 235000019864 coconut oil Nutrition 0.000 claims description 3
- 150000004668 long chain fatty acids Chemical class 0.000 claims description 3
- 150000004667 medium chain fatty acids Chemical class 0.000 claims description 3
- 235000005713 safflower oil Nutrition 0.000 claims description 3
- 239000003813 safflower oil Substances 0.000 claims description 3
- -1 glyceride lipid Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 150000003904 phospholipids Chemical class 0.000 claims description 2
- 206010002091 Anaesthesia Diseases 0.000 claims 2
- 230000037005 anaesthesia Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- 230000007717 exclusion Effects 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 125000005456 glyceride group Chemical group 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000839 emulsion Substances 0.000 description 11
- 150000003431 steroids Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 8
- 230000003444 anaesthetic effect Effects 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000003193 general anesthetic agent Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229940124326 anaesthetic agent Drugs 0.000 description 2
- 229940035674 anesthetics Drugs 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- USPYDUPOCUYHQL-NHRYOTLXSA-N (8r,9s,10s,13s,14s,17s)-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC21 USPYDUPOCUYHQL-NHRYOTLXSA-N 0.000 description 1
- DUHUCHOQIDJXAT-OLVMNOGESA-N 3-hydroxy-(3-α,5-α)-Pregnane-11,20-dione Chemical compound C([C@@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1=O DUHUCHOQIDJXAT-OLVMNOGESA-N 0.000 description 1
- AURFZBICLPNKBZ-GRWISUQFSA-N 3beta-hydroxy-5beta-pregnan-20-one Chemical compound C([C@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)C)[C@@]2(C)CC1 AURFZBICLPNKBZ-GRWISUQFSA-N 0.000 description 1
- USPYDUPOCUYHQL-VEVMSBRDSA-N 5beta-dihydrodeoxycorticosterone Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CC[C@@H]21 USPYDUPOCUYHQL-VEVMSBRDSA-N 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 235000019728 animal nutrition Nutrition 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000007012 clinical effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 239000002960 lipid emulsion Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- NCGLTZSBTFVVAW-KNXRZYMVSA-N minaxolone Chemical compound C1[C@@H](N(C)C)[C@@H]2[C@@]3(C)C[C@H](OCC)[C@@H](O)C[C@@H]3CC[C@H]2[C@@H]2CC[C@H](C(C)=O)[C@]21C NCGLTZSBTFVVAW-KNXRZYMVSA-N 0.000 description 1
- 229960004798 minaxolone Drugs 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- BFQDICGJHAONBN-OOFWROCWSA-M sodium;4-[2-[(5r,8r,9s,10s,13s,14s,17s)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethoxy]-4-oxobutanoate Chemical compound [Na+].C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)COC(=O)CCC([O-])=O)[C@@H]4[C@@H]3CC[C@@H]21 BFQDICGJHAONBN-OOFWROCWSA-M 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Dispersion Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Anesthesiology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Measuring Pulse, Heart Rate, Blood Pressure Or Blood Flow (AREA)
- Ultra Sonic Daignosis Equipment (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8600632A SE8600632D0 (sv) | 1986-02-13 | 1986-02-13 | Novel pharmaceutical composition |
| SE8600632 | 1986-02-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK62187D0 DK62187D0 (da) | 1987-02-06 |
| DK62187A DK62187A (da) | 1987-08-14 |
| DK175504B1 true DK175504B1 (da) | 2004-11-15 |
Family
ID=20363448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK198700621A DK175504B1 (da) | 1986-02-13 | 1987-02-06 | Farmaceutisk præparat indeholdende 3alfa-hydroxy-5beta-pregnan-20-on og fremstilling deraf |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5028600A (enExample) |
| EP (1) | EP0233849B1 (enExample) |
| JP (1) | JPH0788305B2 (enExample) |
| AT (1) | ATE64526T1 (enExample) |
| CA (1) | CA1301651C (enExample) |
| DE (1) | DE3770830D1 (enExample) |
| DK (1) | DK175504B1 (enExample) |
| ES (1) | ES2037742T3 (enExample) |
| FI (1) | FI88676C (enExample) |
| GR (1) | GR3002299T3 (enExample) |
| HK (1) | HK83293A (enExample) |
| NO (1) | NO175040B (enExample) |
| SE (1) | SE8600632D0 (enExample) |
| SG (1) | SG102892G (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9302295D0 (sv) * | 1993-07-02 | 1993-07-02 | Kabi Pharmacia Ab | New pharmaceutical composition |
| US5616330A (en) * | 1994-07-19 | 1997-04-01 | Hemagen/Pfc | Stable oil-in-water emulsions incorporating a taxine (taxol) and method of making same |
| WO1999007381A1 (en) * | 1997-08-11 | 1999-02-18 | Weider Nutrition International, Inc. | Compositions and treatments to reduce side effects of administration of androgenic testosterone precursors |
| JP4198318B2 (ja) | 1998-08-19 | 2008-12-17 | ヤーゴテック アクチェンゲゼルシャフト | プロポフォールの注射可能水性分散物 |
| EP1539104A2 (en) * | 2000-12-29 | 2005-06-15 | The Trustees Of Columbia University In The City Of New York | Use of iv emulsions with different triglyceride composition, particle size and apolipoprotein e for targeted tissue delivery of hydrophobic compounds |
| MXPA04012756A (es) * | 2002-07-02 | 2005-03-23 | Altana Pharma Ag | Suspension acuosa esteril que contiene ciclesonida. |
| PE20050941A1 (es) | 2003-12-16 | 2005-11-08 | Nycomed Gmbh | Suspensiones acuosas de ciclesonida para nebulizacion |
| WO2006030450A2 (en) * | 2004-09-13 | 2006-03-23 | Bharat Serums & Vaccines Ltd. | Stable emulsion compositions for intravenous administration having antimicrobial preservative efficacy |
| WO2012096697A1 (en) * | 2011-01-14 | 2012-07-19 | Simpkins Cuthbert O | Methods and compositions for treating conditions related to lack of blood supply, shock and neuronal injuries |
| US10478505B2 (en) | 2011-09-23 | 2019-11-19 | The Regents Of The University Of California | Edible oils to enhance delivery of orally administered steroids |
| SMT202000008T1 (it) | 2012-01-23 | 2020-03-13 | Sage Therapeutics Inc | Formulazione di steroide neuroattivo comprendente un complesso di allopregnanolone e solfobutil eter beta-ciclodestrina |
| WO2014028398A2 (en) | 2012-08-13 | 2014-02-20 | The Regents Of The University Of California | Mitigation of epileptic seizures by combination therapy using benzodiazepines and neurosteroids |
| PL2887944T3 (pl) | 2012-08-21 | 2022-02-21 | Sage Therapeutics, Inc. | Allopregnanolon do leczenia lekoopornego stanu padaczkowego |
| ES2973320T3 (es) | 2012-11-30 | 2024-06-19 | Univ California | Alopregnanolona para tratar, reducir o mitigar los síntomas de la depresión posparto |
| JOP20200195A1 (ar) | 2014-09-08 | 2017-06-16 | Sage Therapeutics Inc | سترويدات وتركيبات نشطة عصبياً، واستخداماتها |
| RU2766155C2 (ru) | 2016-03-08 | 2022-02-08 | Сейдж Терапьютикс, Инк. | Нейроактивные стероиды, их композиции и применения |
| AU2019396217A1 (en) * | 2018-12-10 | 2021-07-08 | Halo Science LLC | Stable formulations of anesthetics and associated dosage forms |
| CA3151334C (en) * | 2019-08-19 | 2024-04-09 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Topical neurosteroid formulations |
| US11969434B1 (en) | 2022-08-29 | 2024-04-30 | Lipocine Inc. | Oral allopregnanolone compositions and methods of use |
| CN114344309B (zh) * | 2021-12-30 | 2024-02-06 | 南京迈诺威医药科技有限公司 | 一种别孕烷醇酮衍生物自乳化制剂及其制备方法 |
| US12186327B2 (en) | 2022-08-29 | 2025-01-07 | Lipocine Inc. | Oral allopregnanolone compositions and methods of use |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1215702B (de) * | 1962-07-03 | 1966-05-05 | Merck Ag E | Verfahren zur Herstellung von 1alpha-Alkylthio-3-keto-androstanen |
| CA895860A (en) * | 1969-11-05 | 1972-03-21 | Kruger Gunther | PROCESS FOR THE PREPARATION OF 3.alpha.-HYDROXY-5.beta.-PREGNAN-20-ONE |
| US3900561A (en) * | 1970-12-17 | 1975-08-19 | Glaxo Lab Ltd | Pharmaceutical compositions |
| US3917830A (en) * | 1970-12-17 | 1975-11-04 | Glaxo Lab Ltd | Steroidal anaesthetic composition for intraveneous injection |
| US4168308A (en) * | 1976-03-12 | 1979-09-18 | Apoteksvarucentralen Vitrum Ab | Composition for enhancing the administration of pharmacologically active agents |
| JPS609726B2 (ja) * | 1980-05-15 | 1985-03-12 | 株式会社 ミドリ十字 | ステロイド製剤 |
| JPS5716818A (en) * | 1981-04-25 | 1982-01-28 | Green Cross Corp:The | Steroid fatty emulsion |
| JPS60258110A (ja) * | 1984-06-05 | 1985-12-20 | Daigo Eiyou Kagaku Kk | 静脈注射可能なプロゲステロン乳化注射液 |
-
1986
- 1986-02-13 SE SE8600632A patent/SE8600632D0/xx unknown
-
1987
- 1987-01-29 EP EP87850029A patent/EP0233849B1/en not_active Expired - Lifetime
- 1987-01-29 DE DE8787850029T patent/DE3770830D1/de not_active Expired - Fee Related
- 1987-01-29 AT AT87850029T patent/ATE64526T1/de not_active IP Right Cessation
- 1987-01-29 ES ES198787850029T patent/ES2037742T3/es not_active Expired - Lifetime
- 1987-02-06 DK DK198700621A patent/DK175504B1/da not_active IP Right Cessation
- 1987-02-12 NO NO870560A patent/NO175040B/no not_active IP Right Cessation
- 1987-02-12 FI FI870589A patent/FI88676C/fi not_active IP Right Cessation
- 1987-02-12 CA CA000529609A patent/CA1301651C/en not_active Expired - Fee Related
- 1987-02-12 JP JP62028395A patent/JPH0788305B2/ja not_active Expired - Fee Related
-
1989
- 1989-02-28 US US07/316,576 patent/US5028600A/en not_active Expired - Lifetime
-
1991
- 1991-07-11 GR GR91400996T patent/GR3002299T3/el unknown
-
1992
- 1992-10-07 SG SG1028/92A patent/SG102892G/en unknown
-
1993
- 1993-08-12 HK HK832/93A patent/HK83293A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GR3002299T3 (en) | 1992-12-30 |
| JPH0788305B2 (ja) | 1995-09-27 |
| SG102892G (en) | 1992-12-04 |
| FI870589L (fi) | 1987-08-14 |
| EP0233849A1 (en) | 1987-08-26 |
| FI870589A0 (fi) | 1987-02-12 |
| SE8600632D0 (sv) | 1986-02-13 |
| NO870560D0 (no) | 1987-02-12 |
| ATE64526T1 (de) | 1991-07-15 |
| US5028600A (en) | 1991-07-02 |
| FI88676C (fi) | 1993-06-28 |
| EP0233849B1 (en) | 1991-06-19 |
| NO175040C (enExample) | 1994-08-24 |
| ES2037742T3 (es) | 1993-07-01 |
| DK62187D0 (da) | 1987-02-06 |
| DK62187A (da) | 1987-08-14 |
| CA1301651C (en) | 1992-05-26 |
| FI88676B (fi) | 1993-03-15 |
| NO175040B (no) | 1994-05-16 |
| DE3770830D1 (de) | 1991-07-25 |
| NO870560L (no) | 1987-08-14 |
| JPS62192322A (ja) | 1987-08-22 |
| HK83293A (en) | 1993-08-20 |
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