FI57113C - Foerfarande foer framstaellning av nya gona-4,9(10)-diener med progestagen verkan - Google Patents
Foerfarande foer framstaellning av nya gona-4,9(10)-diener med progestagen verkan Download PDFInfo
- Publication number
- FI57113C FI57113C FI771865A FI771865A FI57113C FI 57113 C FI57113 C FI 57113C FI 771865 A FI771865 A FI 771865A FI 771865 A FI771865 A FI 771865A FI 57113 C FI57113 C FI 57113C
- Authority
- FI
- Finland
- Prior art keywords
- gona
- water
- diene
- general formula
- hydroxy
- Prior art date
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 230000000757 progestagenic effect Effects 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 150000001993 dienes Chemical class 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000007530 organic bases Chemical group 0.000 claims description 2
- 125000000466 oxiranyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 6
- 230000003389 potentiating effect Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 229960004400 levonorgestrel Drugs 0.000 description 3
- 239000012434 nucleophilic reagent Substances 0.000 description 3
- 239000000583 progesterone congener Substances 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- WWYNJERNGUHSAO-XUDSTZEESA-N (+)-Norgestrel Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 WWYNJERNGUHSAO-XUDSTZEESA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ONKUMRGIYFNPJW-KIEAKMPYSA-N ethynodiol diacetate Chemical compound C1C[C@]2(C)[C@@](C#C)(OC(C)=O)CC[C@H]2[C@@H]2CCC3=C[C@@H](OC(=O)C)CC[C@@H]3[C@H]21 ONKUMRGIYFNPJW-KIEAKMPYSA-N 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 2
- VBNLSJXBGNWBCU-BIVWLKFRSA-N (8S,13R,14R)-16-ethyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC(=O)C=C2CC[C@@H]([C@H]3[C@@H](CC(C3)CC)CC3)C3=C21 VBNLSJXBGNWBCU-BIVWLKFRSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 208000017701 Endocrine disease Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 210000004696 endometrium Anatomy 0.000 description 1
- 125000003500 enol ether group Chemical group 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- 229960000218 etynodiol Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0044—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 with an estrane or gonane skeleton, including 18-substituted derivatives and derivatives where position 17-beta is substituted by a carbon atom not directly bonded to another carbon atom and not being part of an amide group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD7600193348A DD132497A1 (de) | 1976-06-14 | 1976-06-14 | Verfahren zur herstellung von neuen gona-4,9(10)-dienen |
| DD19334876 | 1976-06-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI771865A7 FI771865A7 (cs) | 1977-12-15 |
| FI57113B FI57113B (fi) | 1980-02-29 |
| FI57113C true FI57113C (fi) | 1980-06-10 |
Family
ID=5504816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI771865A FI57113C (fi) | 1976-06-14 | 1977-06-14 | Foerfarande foer framstaellning av nya gona-4,9(10)-diener med progestagen verkan |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4248790A (cs) |
| JP (1) | JPS5312849A (cs) |
| BE (1) | BE855617A (cs) |
| BR (1) | BR7703832A (cs) |
| CH (1) | CH635594A5 (cs) |
| DE (1) | DE2718872A1 (cs) |
| DK (1) | DK259477A (cs) |
| ES (1) | ES461987A3 (cs) |
| FI (1) | FI57113C (cs) |
| FR (1) | FR2393008A1 (cs) |
| GB (1) | GB1524917A (cs) |
| HU (1) | HU177333B (cs) |
| IT (1) | IT1116654B (cs) |
| MX (1) | MX4685E (cs) |
| NL (1) | NL187167C (cs) |
| NO (2) | NO145244C (cs) |
| SE (1) | SE426833B (cs) |
| YU (1) | YU39804B (cs) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6322598A (ja) * | 1986-07-14 | 1988-01-30 | Mitsubishi Chem Ind Ltd | ゴナトリエン誘導体およびその製造法 |
| HU201091B (en) | 1985-12-26 | 1990-09-28 | Mitsubishi Chem Ind | Process for producing gonatriene derivatives and pharmaceutical compositions comprising same |
| JPS6372627A (ja) * | 1986-09-17 | 1988-04-02 | Mitsubishi Kasei Corp | 子宮内膜症治療薬 |
| JPH0780335B2 (ja) * | 1989-11-20 | 1995-08-30 | 富士通株式会社 | リボンカセット |
| DK0654267T3 (da) * | 1993-11-19 | 2002-05-13 | Jenapharm Gmbh | Carcinostatisk middel til hormonterapi indeholdende dienogest som aktiv komponent |
| ATE167190T1 (de) * | 1995-12-22 | 1998-06-15 | Jenapharm Gmbh | Neue 17alpha-cyanomethylestra-4,9-dien-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische zusammensetzungen |
| US5888543A (en) * | 1996-07-26 | 1999-03-30 | American Home Products Corporation | Oral contraceptives |
| US6451778B1 (en) | 1996-07-26 | 2002-09-17 | Wyeth | Oral contraceptive |
| US6479475B1 (en) | 1996-07-26 | 2002-11-12 | Wyeth | Oral contraceptive |
| US5858405A (en) * | 1996-07-26 | 1999-01-12 | American Home Products Corporation | Oral contraceptive |
| HUP0501132A2 (en) * | 2005-12-05 | 2007-06-28 | Richter Gedeon Nyrt | 17-alpha-cyanomethyl-17betha-hydroxyestra-4,9-diene-3-one of high purity and process for its production |
| US8617597B2 (en) | 2006-07-06 | 2013-12-31 | Bayer Intellectual Property Gmbh | Pharmaceutical composition containing a tetrahydrofolic acid |
| ES2378604T3 (es) * | 2009-05-22 | 2012-04-16 | HEYL Chemisch-Pharmazeutische Fabrik GmbH und Co. KG | Método para la síntesis de dienogest a partir de 3-metiléter de estrona |
| US20130041166A1 (en) | 2010-04-20 | 2013-02-14 | Lupin Limited | Process for the preparation of dienogest substantially free of impurities |
| CN112724191B (zh) * | 2020-12-30 | 2022-11-15 | 上海汇伦医药股份有限公司 | 一种地诺孕素的精制方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3502699A (en) * | 1962-05-15 | 1970-03-24 | Herchel Smith | Novel delta4,9-3-ketosteroids and method for preparing same |
| DE1214223B (de) * | 1962-11-22 | 1966-04-14 | Roussel Uclaf | Verfahren zur Herstellung von Hydroxy-hydroxymethyl-steroiden |
| US3624110A (en) * | 1964-08-03 | 1971-11-30 | Herchel Smith | 13-ethylgona-4,9-dienes |
| GB1130881A (en) * | 1964-08-06 | 1968-10-16 | Merck & Co Inc | Steroidal-í¸-dien-3-ones and derivatives thereof |
| FR2031807A5 (en) * | 1969-02-07 | 1970-11-20 | Jenapharm Veb | 17a-subst estratrienes |
| US3931154A (en) * | 1973-07-07 | 1976-01-06 | Schering Aktiengesellschaft | Process for the preparation of steroid oxiranes |
| US4029648A (en) * | 1976-01-15 | 1977-06-14 | Veb Jenapharm | Process of making gona-1,3,5(10),9(11)-tetraenes |
-
1977
- 1977-04-28 DE DE19772718872 patent/DE2718872A1/de active Granted
- 1977-06-01 IT IT49669/77A patent/IT1116654B/it active
- 1977-06-09 GB GB24086/77A patent/GB1524917A/en not_active Expired
- 1977-06-13 SE SE7706835A patent/SE426833B/xx unknown
- 1977-06-13 YU YU1465/77A patent/YU39804B/xx unknown
- 1977-06-13 DK DK259477A patent/DK259477A/da not_active Application Discontinuation
- 1977-06-13 CH CH724177A patent/CH635594A5/de not_active IP Right Cessation
- 1977-06-13 NO NO772054A patent/NO145244C/no unknown
- 1977-06-13 BE BE178379A patent/BE855617A/xx not_active IP Right Cessation
- 1977-06-13 NL NLAANVRAGE7706465,A patent/NL187167C/xx not_active IP Right Cessation
- 1977-06-13 FR FR7718009A patent/FR2393008A1/fr active Granted
- 1977-06-13 BR BR7703832A patent/BR7703832A/pt unknown
- 1977-06-14 JP JP7039777A patent/JPS5312849A/ja active Granted
- 1977-06-14 MX MX775803U patent/MX4685E/es unknown
- 1977-06-14 HU HU77JE800A patent/HU177333B/hu unknown
- 1977-06-14 FI FI771865A patent/FI57113C/fi not_active IP Right Cessation
- 1977-08-31 ES ES461987A patent/ES461987A3/es not_active Expired
-
1979
- 1979-02-13 US US06/011,951 patent/US4248790A/en not_active Expired - Lifetime
-
1981
- 1981-05-25 NO NO811764A patent/NO146574C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO145244C (no) | 1982-02-10 |
| NL187167B (nl) | 1991-01-16 |
| JPS616838B2 (cs) | 1986-03-01 |
| NO811764L (no) | 1977-12-15 |
| DE2718872A1 (de) | 1977-12-22 |
| MX4685E (es) | 1982-07-30 |
| US4248790A (en) | 1981-02-03 |
| FR2393008A1 (fr) | 1978-12-29 |
| FI771865A7 (cs) | 1977-12-15 |
| YU39804B (en) | 1985-04-30 |
| SE426833B (sv) | 1983-02-14 |
| BR7703832A (pt) | 1978-04-25 |
| FI57113B (fi) | 1980-02-29 |
| IT1116654B (it) | 1986-02-10 |
| ES461987A3 (es) | 1978-06-01 |
| JPS5312849A (en) | 1978-02-04 |
| DE2718872C2 (cs) | 1987-12-10 |
| NL7706465A (nl) | 1977-12-16 |
| BE855617A (fr) | 1977-12-13 |
| NO145244B (no) | 1981-11-02 |
| YU146577A (en) | 1982-06-30 |
| NL187167C (nl) | 1991-06-17 |
| HU177333B (en) | 1981-09-28 |
| NO772054L (no) | 1977-12-15 |
| FR2393008B1 (cs) | 1982-05-07 |
| NO146574C (no) | 1982-10-27 |
| GB1524917A (en) | 1978-09-13 |
| NO146574B (no) | 1982-07-19 |
| CH635594A5 (de) | 1983-04-15 |
| SE7706835L (sv) | 1978-01-15 |
| DK259477A (da) | 1977-12-15 |
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| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: VEB JENAPHARM |