DD242410C4 - Verfahren zur herstellung von 7 alpha-substituirten 3-oxo-17 alpha-pregn-4-en -21.17-carbolactonen - Google Patents
Verfahren zur herstellung von 7 alpha-substituirten 3-oxo-17 alpha-pregn-4-en -21.17-carbolactonen Download PDFInfo
- Publication number
- DD242410C4 DD242410C4 DD84285918A DD28591884A DD242410C4 DD 242410 C4 DD242410 C4 DD 242410C4 DD 84285918 A DD84285918 A DD 84285918A DD 28591884 A DD28591884 A DD 28591884A DD 242410 C4 DD242410 C4 DD 242410C4
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- oxo
- carbolactone
- methylene
- pregn
- ene
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 8
- 239000002170 aldosterone antagonist Substances 0.000 abstract description 3
- 125000004423 acyloxy group Chemical group 0.000 abstract description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract description 2
- 230000002124 endocrine Effects 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
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- -1 alkyl radical Chemical class 0.000 description 75
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 238000002844 melting Methods 0.000 description 50
- 230000008018 melting Effects 0.000 description 50
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- 238000006243 chemical reaction Methods 0.000 description 21
- AVGAIPMGSIOHFZ-UHFFFAOYSA-N dichloromethane;2-propan-2-yloxypropane Chemical compound ClCCl.CC(C)OC(C)C AVGAIPMGSIOHFZ-UHFFFAOYSA-N 0.000 description 20
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- 238000004587 chromatography analysis Methods 0.000 description 6
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- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 6
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- 239000007787 solid Substances 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 5
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- 239000004280 Sodium formate Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- CUUJBILPCIHYMU-KZQZKKBSSA-N [Si](C)(C)(C(C)(C)C)OC[C@@]12CCC[C@H]1[C@@H]1[C@@H](CC3=CC[C@H]4[C@@H]([C@]3(C)[C@H]1CC2)C4)C(C)O Chemical compound [Si](C)(C)(C(C)(C)C)OC[C@@]12CCC[C@H]1[C@@H]1[C@@H](CC3=CC[C@H]4[C@@H]([C@]3(C)[C@H]1CC2)C4)C(C)O CUUJBILPCIHYMU-KZQZKKBSSA-N 0.000 description 1
- PNZVFASWDSMJER-UHFFFAOYSA-N acetic acid;lead Chemical compound [Pb].CC(O)=O PNZVFASWDSMJER-UHFFFAOYSA-N 0.000 description 1
- LVAMVZXECCXUGI-UHFFFAOYSA-N acetic acid;thallium Chemical compound [Tl].CC(O)=O LVAMVZXECCXUGI-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 102000001307 androgen receptors Human genes 0.000 description 1
- 108010080146 androgen receptors Proteins 0.000 description 1
- 230000001548 androgenic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004281 calcium formate Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical group [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 230000007882 cirrhosis Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 229960003654 desoxycortone Drugs 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- HBFXVTVOSLPOEY-UHFFFAOYSA-N ethoxyethane;2-propan-2-yloxypropane Chemical compound CCOCC.CC(C)OC(C)C HBFXVTVOSLPOEY-UHFFFAOYSA-N 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 230000003152 gestagenic effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
- 229910001641 magnesium iodide Inorganic materials 0.000 description 1
- LWLPYZUDBNFNAH-UHFFFAOYSA-M magnesium;butane;bromide Chemical compound [Mg+2].[Br-].CCC[CH2-] LWLPYZUDBNFNAH-UHFFFAOYSA-M 0.000 description 1
- UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229960000990 monobenzone Drugs 0.000 description 1
- 239000004311 natamycin Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical class C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 208000013846 primary aldosteronism Diseases 0.000 description 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- RNXMWPUTWQJQSU-TVXKTTBDSA-N s-[(7r,8s,9s,10r,13r,14s,17r)-17-ethyl-10,13-dimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-7-yl] ethanethioate Chemical compound C([C@H]1SC(C)=O)C2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@H](CC)[C@@]1(C)CC2 RNXMWPUTWQJQSU-TVXKTTBDSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
- C07J53/005—3 membered carbocyclic rings in position 12
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/003—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring the S atom directly linked to a ring carbon atom of the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
- C07J53/008—3 membered carbocyclic rings in position 15/16
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3330084A DE3330084A1 (de) | 1983-08-17 | 1983-08-17 | 7(alpha)-alkoxycarbonyl-3-oxo-17(alpha)-pregn-4-en-21,17-carbolactone und deren 21-carbonsaeuresalze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| DE19833330086 DE3330086A1 (de) | 1983-08-17 | 1983-08-17 | 7(alpha)-mercapto- und 7(alpha)-alkylthio-3-oxo-17(alpha)-pregn-4-en-21,17-carbolactone, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate |
| DE19833330085 DE3330085A1 (de) | 1983-08-17 | 1983-08-17 | 7(alpha)-(1-oxoalkyl)-3-oxo-17(alpha)-pregn-4-en-21,17-carbolactone und deren 21-carbonsaeuresalze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DD242410A5 DD242410A5 (de) | 1987-01-28 |
| DD242410C4 true DD242410C4 (de) | 1987-11-11 |
Family
ID=27191224
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84285918A DD242410C4 (de) | 1983-08-17 | 1984-08-15 | Verfahren zur herstellung von 7 alpha-substituirten 3-oxo-17 alpha-pregn-4-en -21.17-carbolactonen |
| DD84266308A DD253626A5 (de) | 1983-08-17 | 1984-08-15 | Verfahren zur herstellung von 7 delta-substituierten-3-oxo-17delta-pregn-4-en-21.17-carbolactonen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84266308A DD253626A5 (de) | 1983-08-17 | 1984-08-15 | Verfahren zur herstellung von 7 delta-substituierten-3-oxo-17delta-pregn-4-en-21.17-carbolactonen |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4559331A (da) |
| EP (2) | EP0134529B1 (da) |
| AT (1) | ATE51233T1 (da) |
| AU (1) | AU578034B2 (da) |
| DD (2) | DD242410C4 (da) |
| DE (1) | DE3481707D1 (da) |
| DK (1) | DK395584A (da) |
| ES (1) | ES535187A0 (da) |
| FI (1) | FI843208A7 (da) |
| GR (1) | GR80115B (da) |
| HU (1) | HU193694B (da) |
| IL (1) | IL72709A (da) |
| NO (1) | NO843277L (da) |
| PT (1) | PT79091B (da) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3414508A1 (de) * | 1984-04-13 | 1985-10-24 | Schering AG, 1000 Berlin und 4709 Bergkamen | Mehrfach tritiierte steroid-20.17-spirolactone und ihre verwendung als tracersubstanzen |
| US4670551A (en) * | 1984-06-21 | 1987-06-02 | Ciba-Geigy Corporation | Epoxy steroids |
| US5506222A (en) * | 1991-09-25 | 1996-04-09 | Laboratorios Beta S.A. | Method and composition for treating increased androgenic activity |
| ITMI20040367A1 (it) * | 2004-03-01 | 2004-06-01 | Ind Chimica Srl | Processo per la preparazione di drospirenone |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3013012A (en) * | 1960-12-22 | 1961-12-12 | Searle & Co | Alkanoylthio-17alpha-carboxyethyl-17beta-hydroxyandrosten-3-one lactones |
| US3509136A (en) * | 1968-07-30 | 1970-04-28 | Searle & Co | 3 - (17beta - hydroxy - 7alpha - (lower alkyl) thio-3-oxoandrost-4-en-17alpha-yl)propionic acid gamma-lactones and congeners |
| GB1368006A (en) * | 1972-08-24 | 1974-09-25 | Searle & Co | 4alpha,7alpha-carbonyl-5-cyano-17-hzydroxy-3-oxo-5beta,17alpha- pregnane-21-carboxylic acid ypsilon-lactone |
| DE2652761C2 (de) * | 1976-11-16 | 1985-11-21 | Schering AG, 1000 Berlin und 4709 Bergkamen | 15,16-Methylen-Spirolactone, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| DE2922500A1 (de) * | 1979-05-31 | 1980-12-04 | Schering Ag | 6 beta .7 beta |
| DE3168754D1 (en) * | 1980-07-09 | 1985-03-21 | Beecham Group Plc | Clonidine derivatives useful in the treatment of diarrhoea |
| DE3111951A1 (de) * | 1981-03-23 | 1982-09-30 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 7(alpha)-alkoxycarbonyl-15ss-methylen-4-androstene, verfahren zu ihrer herstellung und verwendung als arzneimittel |
| JPS5921698A (ja) * | 1982-07-22 | 1984-02-03 | シエ−リング・アクチエンゲゼルシヤフト | １７α−プレグネ−４−エン−３−オキソ−２１−カルボン酸エステル、その製法およびこれを含有する抗アンドロゲン作用を有する医薬 |
| DE3227598A1 (de) * | 1982-07-22 | 1984-01-26 | Schering AG, 1000 Berlin und 4709 Bergkamen | 7(alpha)-acylthio-15.16-methylen-3-oxo-17(alpha)-pregna-1.4-dien-21,17-carbolactone, verfahren zu ihrer herstellung und verwendung als arzneimittel |
| JPS59139400A (ja) * | 1983-01-31 | 1984-08-10 | Shionogi & Co Ltd | 抗アルドステロン活性ステロイド誘導体 |
-
1984
- 1984-07-26 EP EP84108845A patent/EP0134529B1/de not_active Expired - Lifetime
- 1984-07-26 AT AT84108845T patent/ATE51233T1/de not_active IP Right Cessation
- 1984-07-26 DE DE8484108845T patent/DE3481707D1/de not_active Expired - Lifetime
- 1984-08-14 GR GR80115A patent/GR80115B/el unknown
- 1984-08-14 FI FI843208A patent/FI843208A7/fi not_active Application Discontinuation
- 1984-08-15 DD DD84285918A patent/DD242410C4/de unknown
- 1984-08-15 DD DD84266308A patent/DD253626A5/de unknown
- 1984-08-16 ES ES535187A patent/ES535187A0/es active Granted
- 1984-08-16 HU HU843108A patent/HU193694B/hu unknown
- 1984-08-16 NO NO843277A patent/NO843277L/no unknown
- 1984-08-16 AU AU32001/84A patent/AU578034B2/en not_active Ceased
- 1984-08-16 PT PT79091A patent/PT79091B/pt unknown
- 1984-08-17 US US06/641,599 patent/US4559331A/en not_active Expired - Fee Related
- 1984-08-17 IL IL72709A patent/IL72709A/xx unknown
- 1984-08-17 DK DK395584A patent/DK395584A/da not_active Application Discontinuation
-
1988
- 1988-10-17 EP EP88730228A patent/EP0308365A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IL72709A (en) | 1988-08-31 |
| EP0134529B1 (de) | 1990-03-21 |
| ES8504212A1 (es) | 1985-05-01 |
| EP0134529A3 (en) | 1985-08-21 |
| US4559331A (en) | 1985-12-17 |
| AU3200184A (en) | 1985-02-21 |
| DK395584A (da) | 1985-02-18 |
| DD242410A5 (de) | 1987-01-28 |
| PT79091A (de) | 1984-09-01 |
| HUT34995A (en) | 1985-05-28 |
| ES535187A0 (es) | 1985-05-01 |
| FI843208A0 (fi) | 1984-08-14 |
| DE3481707D1 (de) | 1990-04-26 |
| EP0308365A1 (de) | 1989-03-22 |
| GR80115B (en) | 1984-12-14 |
| IL72709A0 (en) | 1984-11-30 |
| FI843208A7 (fi) | 1985-02-18 |
| HU193694B (en) | 1987-11-30 |
| DK395584D0 (da) | 1984-08-17 |
| EP0134529A2 (de) | 1985-03-20 |
| NO843277L (no) | 1985-02-18 |
| DD253626A5 (de) | 1988-01-27 |
| PT79091B (de) | 1986-08-14 |
| ATE51233T1 (de) | 1990-04-15 |
| AU578034B2 (en) | 1988-10-13 |
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