NO155804B - Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin. - Google Patents
Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin. Download PDFInfo
- Publication number
- NO155804B NO155804B NO810485A NO810485A NO155804B NO 155804 B NO155804 B NO 155804B NO 810485 A NO810485 A NO 810485A NO 810485 A NO810485 A NO 810485A NO 155804 B NO155804 B NO 155804B
- Authority
- NO
- Norway
- Prior art keywords
- melting point
- ethyl
- alkyl
- irimycin
- preparation
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 230000001225 therapeutic effect Effects 0.000 title description 3
- RMCNETIHECSPMZ-UHFFFAOYSA-N piperidine-3,4,5-triol Chemical class OC1CNCC(O)C1O RMCNETIHECSPMZ-UHFFFAOYSA-N 0.000 title description 2
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
- 229960001214 clofibrate Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000000502 dialysis Methods 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
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000005429 filling process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 229950006238 nadide Drugs 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940127017 oral antidiabetic Drugs 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000013573 potato product Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Polymers & Plastics (AREA)
- Endocrinology (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Food Science & Technology (AREA)
- Emergency Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fodder In General (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Supply Devices, Intensifiers, Converters, And Telemotors (AREA)
- Rolls And Other Rotary Bodies (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803007078 DE3007078A1 (de) | 1980-02-26 | 1980-02-26 | Neue derivate von 3,4,5-trihydroxypiperidin, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel sowie in der tierernaehrung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO810485L NO810485L (no) | 1981-08-27 |
| NO155804B true NO155804B (no) | 1987-02-23 |
Family
ID=6095540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO810485A NO155804B (no) | 1980-02-26 | 1981-02-12 | Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4407809A (es) |
| EP (1) | EP0034784B1 (es) |
| JP (3) | JPS56133267A (es) |
| AT (1) | ATE8623T1 (es) |
| AU (1) | AU538463B2 (es) |
| CA (1) | CA1160634A (es) |
| DE (2) | DE3007078A1 (es) |
| DK (1) | DK153545C (es) |
| ES (1) | ES499782A0 (es) |
| FI (1) | FI75807C (es) |
| GR (1) | GR73691B (es) |
| HU (1) | HU183346B (es) |
| IE (1) | IE51317B1 (es) |
| IL (1) | IL62198A (es) |
| NO (1) | NO155804B (es) |
| PT (1) | PT72507B (es) |
| SU (1) | SU1014471A3 (es) |
| ZA (1) | ZA811252B (es) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3737523A1 (de) * | 1987-11-05 | 1989-05-18 | Bayer Ag | Verwendung von substituierten hydroxypiperidinen als antivirale mittel |
| GB8827701D0 (en) * | 1987-12-09 | 1988-12-29 | Nippon Shinyaku Co Ltd | Thrombolytic &c compositions |
| US5192772A (en) * | 1987-12-09 | 1993-03-09 | Nippon Shinyaku Co. Ltd. | Therapeutic agents |
| US4985445A (en) * | 1988-02-12 | 1991-01-15 | Meiji Seika Kaisha, Ltd. | Cancer cell metastasis inhibitors and novel compounds |
| KR920703056A (ko) * | 1989-09-07 | 1992-12-17 | 아만 히데아키 | 항 바이러스제 |
| US5252587A (en) * | 1990-04-27 | 1993-10-12 | Merrell Dow Pharmaceuticals, Inc. | N-derivatives of 1-deoxy nojirimycin |
| US5536732A (en) * | 1990-04-27 | 1996-07-16 | Merrell Pharmaceuticals Inc. | N-derivatives of 1-deoxy nojirimycin |
| US5258518A (en) * | 1992-04-01 | 1993-11-02 | G. D. Searle & Co. | 2-substituted tertiary carbinol derivatives of deoxynojirimycin |
| JP4564108B2 (ja) * | 1996-07-15 | 2010-10-20 | ジェンザイム コーポレーション | デオキシノジリマイシン誘導体及び該誘導体のグルコシルセラミダーゼ阻害剤としての用途 |
| GB0100889D0 (en) * | 2001-01-12 | 2001-02-21 | Oxford Glycosciences Uk Ltd | Compounds |
| ES2393331T3 (es) * | 2002-07-17 | 2012-12-20 | Actelion Pharmaceuticals Ltd. | Derivados de piperidintriol como inhibidores de la glucosiliceramida sintasa |
| AU2003248960B2 (en) | 2002-07-17 | 2009-06-25 | Idorsia Pharmaceuticals Ltd | Piperidinetriol derivatives as inhibitors of glycosylceramidsynthase |
| GB0313678D0 (en) * | 2003-06-13 | 2003-07-16 | Oxford Glycosciences Uk Ltd | Novel compounds |
| GB0313677D0 (en) * | 2003-06-13 | 2003-07-16 | Oxford Glycosciences Uk Ltd | Novel compound |
| EP2023927B1 (en) * | 2006-05-24 | 2015-02-25 | United Therapeutics Corporation | Deoxynojirimycin and d-arabinitol analogs and methods of using |
| US9040488B2 (en) * | 2008-09-02 | 2015-05-26 | Baruch S. Blumberg Institute | Imino sugar derivatives demonstrate potent antiviral activity and reduced toxicity |
| IN2014MN02539A (es) * | 2012-06-06 | 2015-07-24 | Unither Virology Llc | |
| RU2702133C2 (ru) * | 2013-09-16 | 2019-10-04 | ЭМЕРГЕНТ ВИРОЛОДЖИ ЭлЭлСи | Производные дезоксинойиримицина и способы их применения |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1555654A (en) * | 1977-06-25 | 1979-11-14 | Exxon Research Engineering Co | Agricultural burner apparatus |
| NO154918C (no) * | 1977-08-27 | 1987-01-14 | Bayer Ag | Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin. |
| GB2020278B (en) * | 1978-05-03 | 1983-02-23 | Nippon Shinyaku Co Ltd | Moranoline dervitives |
| DE2839309A1 (de) * | 1978-09-09 | 1980-03-27 | Bayer Ag | 3,4,5-trihydroxypiperidin-derivate |
| JPS5683409A (en) * | 1979-12-13 | 1981-07-08 | Nippon Shinyaku Co Ltd | Plant growth regulator |
| DE3322006A1 (de) * | 1983-06-18 | 1984-12-20 | Robert Bosch Gmbh, 7000 Stuttgart | Vorrichtung zur steuerung eines induktiven stellgliedes, insbesondere eines vergasers |
-
1980
- 1980-02-26 DE DE19803007078 patent/DE3007078A1/de not_active Withdrawn
-
1981
- 1981-02-05 US US06/231,695 patent/US4407809A/en not_active Expired - Lifetime
- 1981-02-12 NO NO810485A patent/NO155804B/no unknown
- 1981-02-14 AT AT81101056T patent/ATE8623T1/de not_active IP Right Cessation
- 1981-02-14 EP EP81101056A patent/EP0034784B1/de not_active Expired
- 1981-02-14 DE DE8181101056T patent/DE3164944D1/de not_active Expired
- 1981-02-16 PT PT72507A patent/PT72507B/pt not_active IP Right Cessation
- 1981-02-20 AU AU67480/81A patent/AU538463B2/en not_active Ceased
- 1981-02-23 IL IL62198A patent/IL62198A/xx not_active IP Right Cessation
- 1981-02-23 SU SU813246202A patent/SU1014471A3/ru active
- 1981-02-24 GR GR64232A patent/GR73691B/el unknown
- 1981-02-24 FI FI810559A patent/FI75807C/fi not_active IP Right Cessation
- 1981-02-24 CA CA000371582A patent/CA1160634A/en not_active Expired
- 1981-02-25 ES ES499782A patent/ES499782A0/es active Granted
- 1981-02-25 ZA ZA00811252A patent/ZA811252B/xx unknown
- 1981-02-25 IE IE391/81A patent/IE51317B1/en not_active IP Right Cessation
- 1981-02-25 DK DK084181A patent/DK153545C/da not_active IP Right Cessation
- 1981-02-25 JP JP2556881A patent/JPS56133267A/ja active Granted
- 1981-02-26 HU HU81468A patent/HU183346B/hu not_active IP Right Cessation
-
1984
- 1984-12-21 JP JP59268709A patent/JPS60166663A/ja active Pending
- 1984-12-21 JP JP59268708A patent/JPS60166616A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IL62198A (en) | 1985-03-31 |
| ZA811252B (en) | 1982-03-31 |
| DE3164944D1 (en) | 1984-08-30 |
| IL62198A0 (en) | 1981-03-31 |
| CA1160634A (en) | 1984-01-17 |
| ATE8623T1 (de) | 1984-08-15 |
| DK153545C (da) | 1988-12-05 |
| DK153545B (da) | 1988-07-25 |
| PT72507B (en) | 1982-02-05 |
| DK84181A (da) | 1981-08-27 |
| JPS60166616A (ja) | 1985-08-29 |
| ES8201549A1 (es) | 1981-12-16 |
| IE810391L (en) | 1981-08-26 |
| NO810485L (no) | 1981-08-27 |
| SU1014471A3 (ru) | 1983-04-23 |
| GR73691B (es) | 1984-04-03 |
| EP0034784B1 (de) | 1984-07-25 |
| FI75807C (fi) | 1988-08-08 |
| IE51317B1 (en) | 1986-12-10 |
| JPS60166663A (ja) | 1985-08-29 |
| FI75807B (fi) | 1988-04-29 |
| JPS6152147B2 (es) | 1986-11-12 |
| AU6748081A (en) | 1981-09-03 |
| FI810559L (fi) | 1981-08-27 |
| JPS56133267A (en) | 1981-10-19 |
| HU183346B (en) | 1984-04-28 |
| JPH0342243B2 (es) | 1991-06-26 |
| AU538463B2 (en) | 1984-08-16 |
| DE3007078A1 (de) | 1981-09-10 |
| US4407809A (en) | 1983-10-04 |
| PT72507A (en) | 1981-03-01 |
| EP0034784A1 (de) | 1981-09-02 |
| ES499782A0 (es) | 1981-12-16 |
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