NO157701B - Analogifremgangsmte for fremstilling av terapeutisk aktive 15,16-methylen-17alfa-pregna-4,6-dien-21-carboxylsyresalter. - Google Patents
Analogifremgangsmte for fremstilling av terapeutisk aktive 15,16-methylen-17alfa-pregna-4,6-dien-21-carboxylsyresalter. Download PDFInfo
- Publication number
- NO157701B NO157701B NO842887A NO842887A NO157701B NO 157701 B NO157701 B NO 157701B NO 842887 A NO842887 A NO 842887A NO 842887 A NO842887 A NO 842887A NO 157701 B NO157701 B NO 157701B
- Authority
- NO
- Norway
- Prior art keywords
- pregna
- methylene
- carboxylic acid
- diene
- acid salts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- BBKXKEBYSQYKKY-WLQQXYQASA-N 3-[(1R,2S,6R,7R,10S,11R)-7,11-dimethyl-6-pentacyclo[8.8.0.02,7.03,5.011,16]octadeca-15,17-dienyl]propanoic acid Chemical class C1CC[C@]2(C)[C@H]3CC[C@](C)([C@@H](C4CC44)CCC(O)=O)[C@@H]4[C@@H]3C=CC2=C1 BBKXKEBYSQYKKY-WLQQXYQASA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 3
- 230000001864 anti-aldosterone effect Effects 0.000 abstract description 2
- 230000002280 anti-androgenic effect Effects 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000000757 progestagenic effect Effects 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- -1 alkali metal salts Chemical class 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- JTZQCHFUGHIPDF-RYVBEKKQSA-M potassium canrenoate Chemical compound [K+].O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)CCC([O-])=O)[C@@H]4[C@@H]3C=CC2=C1 JTZQCHFUGHIPDF-RYVBEKKQSA-M 0.000 description 3
- 229960000206 potassium canrenoate Drugs 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000002170 aldosterone antagonist Substances 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 206010048962 Brain oedema Diseases 0.000 description 1
- VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010020571 Hyperaldosteronism Diseases 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- WAHQVRCNDCHDIB-QZYSPNBYSA-N [(3s,8r,9s,10r,13s,14s,17r)-17-acetyl-17-acetyloxy-6,10,13-trimethyl-1,2,3,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-yl] 3-cyclopentylpropanoate Chemical compound O([C@@H]1C=C2C(C)=C[C@H]3[C@@H]4CC[C@]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)(OC(=O)C)C(C)=O)C(=O)CCC1CCCC1 WAHQVRCNDCHDIB-QZYSPNBYSA-N 0.000 description 1
- 229960002478 aldosterone Drugs 0.000 description 1
- 230000001838 anti-progestagenic effect Effects 0.000 description 1
- 239000000051 antiandrogen Substances 0.000 description 1
- 208000006752 brain edema Diseases 0.000 description 1
- 230000007882 cirrhosis Effects 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 238000001816 cooling 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
- 229960003654 desoxycortone Drugs 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000472 traumatic effect Effects 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
- C07J53/008—3 membered carbocyclic rings in position 15/16
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Reinforced Plastic Materials (AREA)
- Saccharide Compounds (AREA)
Description
Oppfinnelsen angår en analogifiremgangsmåte for fremstilling av terapeutisk aktive 15,16-methylen-17a-pregna-4,6-dien-21-carboxylsyresalter med den generelle formel:
hvor
1 2
R og R hver for seg er hydrogen eller sammen er en
ytterligere CC-binding eller en methylengruppe, og M er et alkalimetall,
og methylengruppen i 15,16-stillingen står i a- eller stilling.
De nye forbindelser med den generelle formel I er alkalimetallsalter av den 3-substituerte propionsyre. Som alkalimetallsalter kommer kalium-, natrium- eller lithium-salter, fortrinnsvis kaliumsalter, på tale.
De nye forbindelser med den generelle formel I har den egenskap at de opphever, hhv. snur, virkningen av aldosteron eller desoxycorticosteron på natrium- og kaliumsaltutskillelse. De nye forbindelser er lett vannoppløselige som det kjente kaliumcanrenoat, men de er overlegne over kaliumcanrenoat med hensyn til antialdosteronvirkning og har en nedsatt anti-androgen og gestagen bivirkning. Antialdosteronvirkningen ble målt i forsøksmodellen til Hollmann (Naunyn-Schmiede-
bergs Arch. Exp. Path. Pharmak. 247 (1964), s. 419).
I den følgende tabell er de relative verdier av anti-aldosteronvirkningsstyrken (med kaliumcanrenoat = 1) sammen-stilt med forbindelsene fremstilt ifølge oppfinnelsen, A, B
og C.
A 17(3-hydroxy-15(3,16(3-methylen-3-oxo-17oc-pregna-l, 4 , 6-trien-21-carboxylsyre-kaliumsalt,
B la,2a;150,160-dlmethylen-170-hydroxy-3-oxo-17a-pregna-4,6-dien-21-carboxylsyre-kaliumsalt og
C 17f3-hydroxy-15a, 16a-methylen-3-oxo-17a-pregna-4, 6-dien-21-carboxylsyre-kaliumsalt.
De nye forbindelser er egnet til behandling av sykdomstilstander til hvilke er knyttet en primær eller sekundær hyperaldosteronisme. Til disse sykdomstilstander som kan behandles med de nye forbindelser, hører f.eks. levercirrhose med ascites og ødemer, alvorlig hjerteinsuffisiens, nefrotisk syndrom, traumatisk hjerneødem osv.
Virkestoffene administreres fortrinnsvis intravenøst i vandig oppløsning. Doseringen av virkestoffene kan variere fra tilfelle til tilfelle og avhenger av typen og alvorlig-heten av sykdommen. I alminnelighet vil virkestoffmengden til mennesker utgjøre ca. 50 til 600 mg pr. dag.
Den vandige oppløsning av virkestoffet kan oppbevares
i ampuller som inneholder 50 til 200 mg virkestoff.
Analogifremgangsmåten ifølge oppfinnelsen er kjenne-tegnet ved at man på i og for seg kjent vis lar alkali innvirke på et 21,17-carbolacton med den generelle formel:
12
hvor R og R er som ovenfor angitt.
Carbolactonet oppvarmes til 50 til 100°C med alkalihydroxyd i en lavere alkohol, som f.eks. methanol, ethanol, isopropanol, propanol eller butanol. Som alkalihydroxyd kommer natrium-, kalium- eller lithiumhydroxyd på tale.
De som utgangsmateriale benyttede 21,17-carbolactoner med den generelle formel II er kjent, f.eks. fra DE-OS 27 22 706.
Eksempel 1
Til en oppløsning av 3,0 g 153,16f}-methylen-3-oxo-17a-pregna-1,4,6-trien-21,17-carbolacton i 45 ml 2-propanol til-settes 9 ml av en 1 N kaliumhydroxydoppløsning i methanol,
og det kokes i 30 minutter under tilbakeløp. Efter avkjøling helles reaksjonsblandingen i 45 ml iskald diethylether, bunnfallet frafiltreres og eftervaskes med diethylether.
Det erholdte bunnfall blir så utrørt i eddiksyreester, avsuget og tørret i vakuum. Man får 2,6 g 17&-hydroxy-153,163-methylen-3-oxo-17a-pregna-l,4,6-trien-21-carboxylsyre-kalium-salt.
IR (KBr): 3410, 1650, 1600, 1580, 1400 cm"<1.>
Eksempel 2
Under de i eksempel 1 beskrevne betingelser får man av 300 mg la,2a;150,160-dimethylen-3-oxo-17a-pregna-4,6-dien-21, 17-carbolacton 180 mg la, 2a;150, 160-dimeth<y>len-170-hydroxy-3-oxo-17a-pregna-4,6-dien-21-carboxylsyre-kaliumsalt med smp. 183-186°C.
IR (KBr): 3420, 1645, 1575, 1400 cm"<1>.
Eksempel 3
Under de i eksempel 1 beskrevne betingelser får man av
1 g 150,160-methylen-3-oxo-17a-pregna-4,6-dien-21,17-carbolacton 620 mg 170-hydroxy-150,160-methylen-3-oxo-17a-pregna-4,6-dien-21-carboxylsyre-kaliumsalt.
IR (KBr): 3410, 1650, 1580, 1400 cm"<1.>
Eksempel 4
Under de i eksempel 1 beskrevne betingelser får man av 500 mg 15a,16a-methylen-3-oxo-17a-pregna-l,4,6-trien-21,17-carbolacton 325 mg 170-hydroxy-15a-16a-methylen-3-oxo-17a-pregna-1,4,6-trien-21-carboxylsyre-kaliumsalt.
UV: e283 = 2240°-
Eksempel 5
Under de i eksempel 1 beskrevne betingelser får man av 377 mg la,2a;15a,16a-dimethylen-3-oxo-17a-pregna-4,6-dien-21,17-carbolacton 280 mg la,2a;15a,16a-dimethylen-170-hydroxy-3-oxo-17a-pregna-4,6-dien-21-carboxylsyre-kaliumsalt med smp. 281-284°C.
UV: £283 = 17900.
Eksempel 6
Under de i eksempel 1 beskrevne betingelser får man av 350 mg 15a,16a-methylen-3-oxo-17a-pregna-4,6-dien-21,17-carbolacton 180 mg 170-hydroxy-15a,16a-methylen-3-oxo-17a-pregna-4,6-dien-21-carboxylsyre-kaliumsalt med smp. 278-283°C. UV: <£>283 = 2430°-
Claims (1)
- Analogifremgangsmåte for fremstilling av terapeutisk aktive 15,16-methylen-17a-pregna-4,6-dien-21-carboxylsyre-salter med den generelle formel:hvor 1 ?R og R' hver for seg er hydrogen eller sammen er en ytterligere CC-binding eller en methylengruppe, og M er et alkalimetall,og methylengruppen i 15,16-stillingen står i a- eller 3-stilling, karakterisert ved at man på i og for seg kjent vis lar alkali innvirke på et 21,17-carbolacton med den generelle formel: 1 2hvor R og R er som ovenfor angitt.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3326013A DE3326013A1 (de) | 1983-07-15 | 1983-07-15 | 15,16-methylen-17(alpha)-pregna-4,6-dien-21-carbonsaeuresalze, diese enthaltende pharmazeutische praeparate sowie verfahren zu deren herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO842887L NO842887L (no) | 1985-01-16 |
| NO157701B true NO157701B (no) | 1988-01-25 |
| NO157701C NO157701C (no) | 1988-05-04 |
Family
ID=6204355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO842887A NO157701C (no) | 1983-07-15 | 1984-07-13 | Analogifremgangsmaate for fremstilling av terapeutisk aktive 15,16-methylen-17alfa-pregna-4,6-dien-21-carboxylsyresalter. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4542024A (no) |
| EP (1) | EP0131899B1 (no) |
| JP (1) | JPS6038397A (no) |
| AT (1) | ATE31066T1 (no) |
| AU (1) | AU572863B2 (no) |
| CA (1) | CA1212102A (no) |
| CS (1) | CS244691B2 (no) |
| DD (1) | DD216469A5 (no) |
| DE (2) | DE3326013A1 (no) |
| DK (1) | DK325584A (no) |
| ES (1) | ES534214A0 (no) |
| FI (1) | FI842742A (no) |
| GR (1) | GR81526B (no) |
| HU (1) | HU189422B (no) |
| NO (1) | NO157701C (no) |
| ZA (1) | ZA845443B (no) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4102244A1 (de) * | 1991-01-24 | 1992-07-30 | Schering Ag | 14,16ss-ethano-15ss, 16(pfeil hoch)1(pfeil hoch)-cyclo-14ss-estra-1,3,5(10)-triene |
| PT770332E (pt) | 1995-10-16 | 2001-11-30 | Nestle Sa | Sobremesa de camadas multiplas bem como processo e dispositivo para a sua preparacao |
| ITMI20010821A1 (it) * | 2001-04-17 | 2002-10-17 | Gienne Pharma S P A | Impiego di composti derivati dallo spirolattone per inibire l'azione pro-fibrigenetica delle cellule stellate epatiche e delle cellule musco |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2264189C3 (de) * | 1972-12-29 | 1979-05-31 | Merck & Co., Inc., Rahway, N.J. (V.St.A.) | 3'-(3-Oxo-17beta-hydroxy-6,7-methylen-androst-4en-bzw.-l,4-dien-17 a-yl) -propionsäureverbindungen, Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Mittel |
| DE2744255A1 (de) * | 1976-10-05 | 1978-04-06 | Ciba Geigy Ag | Verfahren zur herstellung neuer steroidverbindungen mit 19-staendiger sauerstoffunktion |
| DE2922500A1 (de) * | 1979-05-31 | 1980-12-04 | Schering Ag | 6 beta .7 beta |
| 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 |
-
1983
- 1983-07-15 DE DE3326013A patent/DE3326013A1/de not_active Withdrawn
-
1984
- 1984-07-03 DK DK325584A patent/DK325584A/da not_active Application Discontinuation
- 1984-07-09 FI FI842742A patent/FI842742A/fi not_active Application Discontinuation
- 1984-07-11 JP JP59142526A patent/JPS6038397A/ja active Pending
- 1984-07-11 AT AT84108122T patent/ATE31066T1/de not_active IP Right Cessation
- 1984-07-11 ES ES534214A patent/ES534214A0/es active Granted
- 1984-07-11 DE DE8484108122T patent/DE3467760D1/de not_active Expired
- 1984-07-11 EP EP84108122A patent/EP0131899B1/de not_active Expired
- 1984-07-11 DD DD84265163A patent/DD216469A5/de unknown
- 1984-07-12 AU AU30514/84A patent/AU572863B2/en not_active Ceased
- 1984-07-13 CA CA000458866A patent/CA1212102A/en not_active Expired
- 1984-07-13 US US06/630,552 patent/US4542024A/en not_active Expired - Fee Related
- 1984-07-13 NO NO842887A patent/NO157701C/no unknown
- 1984-07-13 ZA ZA845443A patent/ZA845443B/xx unknown
- 1984-07-13 HU HU842750A patent/HU189422B/hu unknown
- 1984-07-13 GR GR75298A patent/GR81526B/el unknown
- 1984-07-16 CS CS845490A patent/CS244691B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU572863B2 (en) | 1988-05-19 |
| GR81526B (no) | 1984-12-11 |
| CS244691B2 (en) | 1986-08-14 |
| ES8503690A1 (es) | 1985-04-01 |
| JPS6038397A (ja) | 1985-02-27 |
| US4542024A (en) | 1985-09-17 |
| ZA845443B (en) | 1985-03-27 |
| EP0131899B1 (de) | 1987-11-25 |
| ATE31066T1 (de) | 1987-12-15 |
| ES534214A0 (es) | 1985-04-01 |
| FI842742A (fi) | 1985-01-16 |
| DD216469A5 (de) | 1984-12-12 |
| NO157701C (no) | 1988-05-04 |
| AU3051484A (en) | 1985-01-17 |
| HU189422B (en) | 1986-07-28 |
| FI842742A0 (fi) | 1984-07-09 |
| DE3467760D1 (en) | 1988-01-07 |
| DK325584D0 (da) | 1984-07-03 |
| EP0131899A2 (de) | 1985-01-23 |
| CA1212102A (en) | 1986-09-30 |
| DE3326013A1 (de) | 1985-01-24 |
| DK325584A (da) | 1985-01-16 |
| NO842887L (no) | 1985-01-16 |
| HUT34514A (en) | 1985-03-28 |
| EP0131899A3 (en) | 1985-08-21 |
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