FI80707B - Foerfarande foer framstaellning av terapeutiskt anvaendbara homonojirimycinglykosider. - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara homonojirimycinglykosider. Download PDFInfo
- Publication number
- FI80707B FI80707B FI854944A FI854944A FI80707B FI 80707 B FI80707 B FI 80707B FI 854944 A FI854944 A FI 854944A FI 854944 A FI854944 A FI 854944A FI 80707 B FI80707 B FI 80707B
- Authority
- FI
- Finland
- Prior art keywords
- glycero
- guloheptitol
- dideoxy
- imino
- glucopyranosyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Luminescent Compositions (AREA)
Claims (11)
1. Förfarande för framställning av en terapeutiskt användbar förening med formeln (a)
5 HO-il M- NH H v X HO 4-1 CH2-OR
10 OH väri R är en glykosyl- eller en acylerad glykosylradikal, vilken innehäller 1-3 hexos- eller pentosenheter och bindningen tili glykosylradikalen sker i 1-ställningen, och av dess farmaceutiskt godtagbara syraadditionssalter, 15 kännetecknat därav, att en förening med formeln (b) CBZ BnO —η | )-N H f& BnO ^ CH20H OBn väri Bn är bensyl och DBZ är bensyloxikarbonyl, bringas 25 att reagera med en glykosylbromid eller -klorid, vars hydroxigrupp skyddats med bensylgrupp eller alkanoylgrupp som innehäller upp till 6 kolatomer, varefter man vid behov hydrerar katalytiskt eller förtvälar för att avlägs-na bensyl- eller esterskyddsgrupperna. 30 2. Förfarande enligt patentkravet 1 för framställ ning av en förening med formeln (a) HO-il H / \/ (a) 35 A/H s/\ 7 HO 4-T CH2-OR OH 24 8 0 7 0 7 väri R är glukosyl, galaktosyl, fukosyl, ribosyl, cello-biosyl, maltotriosyl, cellotriosyl, arabinosyl eller xy-losyl, kännetecknat därav, att en förening med formeIn (b)
5 CBZ BnO-1 | )-N H /λΧ BnO -f CH20H
10 OBn väri Bn är bensyl och CBZ är bensyloxikarbonyl, bringas att reagera med en glykosylbromid eller -klorid, väri glykosylen är den samma som den ovan definierade gruppen 15 R, vilkens hydroxigrupper skyddats med bensylgrupper eller alkanoylgrupper som innehäller upp tili 6 kolatomer, var-efter man vid behov hydrerar katalytiskt eller förtvälar för att avlägsna bensyl- eller esterskyddsgrupperna.
3. Förfarande enligt patentkravet 1 för framställ-20 ning av en förening med formeln (a) H0—iL —NH H , x 25 3/vX HO 4-f CH2-OR OH väri R är glukosyl, L-fukosyl eller cellobiosyl, kännetecknat därav, att en förening med form-30 eln (b) CBZ BnO-1 | )-N H (b) L OBn Y
35 NZA BnO \ CH20H OBn 25 80707 väri Bn är bensyl och CBZ är bensyloxikarbonyl, bringas att reagera med en glykosylbromid eller -klorid, vari glykosylen är den sanuna som ovan definierade gruppen R, vilkens hydroxigrupper skyddats med bensylgrupper eller 5 alkanoylgrupper som innehäller upp till 6 kolatomer, var-efter man vid behov hydrerar katalytiskt eller förtvälar för att avlägsna bensyl- eller esterskyddsgrupperna.
4. Förfarande enligt patentkravet 1 för framställ-ning av 2,6-imino-2,6-dideoxi-7-0-(β-D-glukopyranosyl)-D-10 glycero-L-guloheptitol, kännetecknat därav, att 2,6-dideoxi-2,6-{[(fenylmetoxi)karbonyl]imino}- 1,3,4,5-tetrakis-0-( fenylmetyl )-D-glycero-L-guloheptitol bringas att reagera med 2,3,4,6-tetra-0-(fenylmetyl)a-D-glukopyranosylbromid och sedan hydreras katalytiskt. 15 5. Förfarande enligt patentkravet 1 för framställ- ning av 2,6-imino-2,6-dideoxi-7-0-(β-D-glukopyranosyl)-D-glycero-L-guloheptitol, kännetec knat därav, att 2,6-dideoxi-2,6 — {[(fenylmetoxi)karbonyl]imino}- 1,3,4, 5-tetrakis-O- ( fenylmetyl)-D-glycero-L-guloheptitol 20 bringas att reagera med 2,3,4,6-tetraacetyl-a-D-glukopyra- nosylbromid och sedan med natriummetoxid i metanol och sedan hydreras katalytiskt.
6. Förfarande enligt patentkravet 1 för framställ-ning av 2,6-imino-2,6-dideoxi-7-0-(6-deoxi-3~D-gaalktopy- 25 ranosyl)-D-glycero-L-guloheptitol, känneteck nat därav, att 2,6-dideoxi-2,6-{[(fenylmetoxi)karbo-nyl]imino}-l,3,4,5-tetrakis-0-(fenylmetyl)-D-glycero-L-guloheptitol bringas att reagera med 2,3,4-triacetyl-6-deoxi-a-D-galaktopyranosylklorid och sedan med natrium-30 metoxid i metanol och sedan hydreras katalytiskt.
7. Förfarande enligt patentkravet 1 för framställ-ning av 2,6-imino-2,6-dideoxi-7-0-(6-deoxi-p-L-galaktopy-ranosyl)-D-glycero-L-guloheptitol, kännetecknat därav, att 2,6-dideoxi-2,6-{[(fenylmetoxi)karbo- 35 nyl]irnino}-!,3,4,5-tetrakis-0-(fenylmetyl)-D-glycero-L- 26 80707 guloheptitol bringas att reagera med 2,3,4-triacetyl-6-deoxi-a-L-galaktopyranosylklorid och sedan med natrium-metoxid i metanol och sedan hydreras katalytiskt.
8. Förfarande enligt patentkravet 1 för framställ-5 ning av 0-p-D-glukopyranosyl-( 1 >4)-0-p-D-glukopyranosyl-(1 >7)-2,6-dideox±-2,6-imino-D-glycero-L-guloheptitol, kännetecknat därav, att 2,6-dideoxi-2,6-{[(fe-nylmetoxi) karbonyl ] imino} -1,3,4,5-tetrakis-O- (f enylmetyl) -D-glycero-L-guloheptitol bringas att reagera med 4-0-10 (2,3,4,6-tetra-O-acetyl-p-D-glukopyranosyl-a-D-glukopyra- nosylbromidtriacetat och sedan med natriummetoxid i metanol och sedan hydreras katalytiskt.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68312784 | 1984-12-18 | ||
| US06/683,127 US4634765A (en) | 1984-12-18 | 1984-12-18 | Homodisaccharide hypoglycemic agents |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI854944A0 FI854944A0 (fi) | 1985-12-13 |
| FI854944A FI854944A (fi) | 1986-06-19 |
| FI80707B true FI80707B (fi) | 1990-03-30 |
| FI80707C FI80707C (sv) | 1990-07-10 |
Family
ID=24742682
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI854944A FI80707C (sv) | 1984-12-18 | 1985-12-13 | Förfarande för framställning av terapeutiskt användbara homonojirimyci nglykosider |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4634765A (sv) |
| EP (1) | EP0186103B1 (sv) |
| JP (1) | JPS61158994A (sv) |
| KR (1) | KR900005607B1 (sv) |
| CN (1) | CN1016784B (sv) |
| AT (1) | ATE62249T1 (sv) |
| AU (1) | AU574246B2 (sv) |
| CA (1) | CA1240989A (sv) |
| DE (1) | DE3582420D1 (sv) |
| DK (1) | DK587085A (sv) |
| ES (1) | ES8706164A1 (sv) |
| FI (1) | FI80707C (sv) |
| GR (1) | GR853032B (sv) |
| HU (1) | HU194263B (sv) |
| IE (1) | IE58186B1 (sv) |
| NO (1) | NO162387B (sv) |
| NZ (1) | NZ214570A (sv) |
| PH (1) | PH23660A (sv) |
| PT (1) | PT81689B (sv) |
| ZA (1) | ZA859573B (sv) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2181729B (en) * | 1985-10-12 | 1990-04-04 | Nippon Shinyaku Co Ltd | Glucosylmoranoline derivatives and production thereof |
| JPS62242692A (ja) * | 1986-04-15 | 1987-10-23 | Nippon Shinyaku Co Ltd | モラノリン誘導体の製造法 |
| EP0345104B1 (en) * | 1988-06-02 | 1995-11-02 | Merrell Dow Pharmaceuticals Inc. | Novel Alpha-glucosidase inhibitors |
| EP0344383A1 (en) * | 1988-06-02 | 1989-12-06 | Merrell Dow Pharmaceuticals Inc. | Novel alpha-Glucosidase inhibitors |
| US4880917A (en) * | 1988-07-01 | 1989-11-14 | Merrell Dow Pharmaceuticals Inc. | Process for hydrolyzing 2,6-dideoxy-2,6-iminoheptononitrile derivatives using trifluoroacetic acid and dinitrogen tetroxide |
| US4908439A (en) * | 1988-09-16 | 1990-03-13 | Merrell Dow Pharmaceuticals Inc. | Synthesis of intermediate useful in the preparation of nojirimycin and related compounds |
| US5227479A (en) * | 1989-12-20 | 1993-07-13 | Merrell Dow Pharmaceuticals Inc. | Process for the preparation of nojirimycin and related compounds |
| US5504078A (en) * | 1990-06-08 | 1996-04-02 | Merrell Dow Pharmaceuticals Inc. | α-glucosidase inhibitors |
| EP1598054B1 (en) * | 1997-04-15 | 2011-03-16 | Csir | Non-therapeutic methods of suppressing appetite |
| GB2396815B (en) * | 1999-10-27 | 2004-09-08 | Phytopharm Plc | A composition comprising a pregnenone derivative and an NSAID |
| KR100446483B1 (ko) | 2000-03-31 | 2004-09-01 | 미시간 스테이트 유니버시티 | 옥심 또는 이민으로부터 1,5-디데옥시-1,5-이미노 헥시톨제조방법 |
| GB2363985B (en) | 2000-06-30 | 2004-09-29 | Phytopharm Plc | Extracts,compounds & pharmaceutical compositions having anti-diabetic activity and their use |
| US7262318B2 (en) * | 2004-03-10 | 2007-08-28 | Pfizer, Inc. | Substituted heteroaryl- and phenylsulfamoyl compounds |
| US20050288340A1 (en) * | 2004-06-29 | 2005-12-29 | Pfizer Inc | Substituted heteroaryl- and phenylsulfamoyl compounds |
| EP1819681B1 (en) * | 2004-11-23 | 2009-08-12 | Warner-Lambert Company LLC | 7-(2h-pyrazol-3-yl)-3,5-dihydroxy-heptanoic acid derivatives as hmg co-a reductase inhibitors for the treatment of lipidemia |
| CN101228173A (zh) * | 2005-06-08 | 2008-07-23 | 阿米库斯治疗学公司 | 三氟甲磺酸酯化的化合物的稳定化 |
| DK2027137T3 (en) * | 2005-06-08 | 2015-05-18 | Amicus Therapeutics Inc | Imino and aminosugar PURIFICATION |
| WO2006133447A1 (en) * | 2005-06-08 | 2006-12-14 | Amicus Therapeutics, Inc. | Crystalline sugar compositions and method of making |
| US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| ATE547394T1 (de) | 2006-12-01 | 2012-03-15 | Bristol Myers Squibb Co | N-((3-benzyl)-2,2-(bis-phenyl)-propan-1- aminderivate als cetp-hemmer für die behandlung von atherosklerose und herz-kreislauf- erkrankungen |
| WO2008110551A1 (en) | 2007-03-12 | 2008-09-18 | Zadec Aps | An anti-diabetic extract of rooibos |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| WO2008151257A2 (en) | 2007-06-04 | 2008-12-11 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| AU2009256157B2 (en) | 2008-06-04 | 2014-12-18 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| EP2321341B1 (en) | 2008-07-16 | 2017-02-22 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| EP2571860A1 (en) | 2010-05-21 | 2013-03-27 | Pfizer Inc | 2-phenyl benzoylamides |
| WO2012027331A1 (en) | 2010-08-27 | 2012-03-01 | Ironwood Pharmaceuticals, Inc. | Compositions and methods for treating or preventing metabolic syndrome and related diseases and disorders |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| CN102462726B (zh) * | 2010-11-04 | 2016-03-09 | 中国医学科学院药物研究所 | 白树总生物碱及多羟基生物碱化合物的提取、分离及用途 |
| WO2012120414A2 (en) | 2011-03-04 | 2012-09-13 | Pfizer Inc. | Edn3-like peptides and uses thereof |
| EP2712362A4 (en) * | 2011-05-13 | 2014-12-24 | Glycom As | MANUFACTURE OF LACTO-N-TETRAOSE |
| MY188344A (en) | 2012-03-09 | 2021-12-01 | Biotropics Malaysia Berhad | Extract formulations of rhodamnia cinerea and uses thereof |
| WO2014151206A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| AU2014235209B2 (en) | 2013-03-15 | 2018-06-14 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists combined with other drugs |
| AU2014255381A1 (en) | 2013-04-17 | 2015-10-08 | Pfizer Inc. | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
| WO2014197720A2 (en) | 2013-06-05 | 2014-12-11 | Synergy Pharmaceuticals, Inc. | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
| MX2017002610A (es) | 2014-08-29 | 2017-10-11 | Tes Pharma S R L | INHIBIDORES DE ACIDO A-AMINO-ß-CARBOXIMUCONICO SEMIALDEHIDO DESCARBOXILASA. |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| CN104530150A (zh) * | 2015-01-14 | 2015-04-22 | 佛山市赛维斯医药科技有限公司 | 含胺基苯和双葡萄糖苷结构化合物、其制备方法和用途 |
| RU2019114228A (ru) | 2016-10-14 | 2020-11-16 | Тес Фарма С.Р.Л. | ИНГИБИТОРЫ ДЕКАРБОКСИЛАЗЫ ПОЛУАЛЬДЕГИДА α-АМИНО-β-КАРБОКСИМУКОНОВОЙ КИСЛОТЫ |
| IT201700078102A1 (it) | 2017-07-11 | 2019-01-11 | Dipharma Francis Srl | Sintesi di un azazucchero e suoi intermedi |
| CN108828121B (zh) * | 2018-06-14 | 2020-06-05 | 华润三九医药股份有限公司 | 一种白树药材中α-高野尻霉素的含量检测方法 |
| AU2019385644A1 (en) | 2018-11-20 | 2021-06-03 | Tes Pharma S.R.L. | Inhibitors of α-Amino-β-carboxymuconic acid semialdehyde decarboxylase |
| JOP20210193A1 (ar) | 2019-01-18 | 2023-01-30 | Astrazeneca Ab | مثبطات pcsk9 وطرق استخدامها |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4065562A (en) * | 1975-12-29 | 1977-12-27 | Nippon Shinyaku Co., Ltd. | Method and composition for reducing blood glucose levels |
| NO154918C (no) * | 1977-08-27 | 1987-01-14 | Bayer Ag | Analogifremgangsmaate til fremstilling av terapeutisk aktive derivater av 3,4,5-trihydroksypiperidin. |
| DE2848117A1 (de) * | 1978-11-06 | 1980-05-14 | Bayer Ag | Derivate des 2-hydroxymethyl-3,4,5- trihydroxy-piperidins, ihre herstellung und verwendung zur beeinflussung des kohlenhydrat- und fettstoffwechsels |
| DE2942365A1 (de) * | 1979-10-19 | 1981-05-14 | Bayer Ag, 5090 Leverkusen | 2-hydroxyalkyl-3,4,5-trihydroxy-(pi)-peridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| GB2064527B (en) * | 1979-12-08 | 1984-05-02 | Nippon Shinyaku Co Ltd | Moranoline derivatives and process for preparation thereof |
| IT1210476B (it) * | 1981-05-28 | 1989-09-14 | Erba Farmitalia | Antracicline. |
-
1984
- 1984-12-18 US US06/683,127 patent/US4634765A/en not_active Expired - Lifetime
-
1985
- 1985-12-05 AU AU50810/85A patent/AU574246B2/en not_active Ceased
- 1985-12-13 ZA ZA859573A patent/ZA859573B/xx unknown
- 1985-12-13 CA CA000497607A patent/CA1240989A/en not_active Expired
- 1985-12-13 FI FI854944A patent/FI80707C/sv not_active IP Right Cessation
- 1985-12-16 NZ NZ214570A patent/NZ214570A/en unknown
- 1985-12-16 HU HU854804A patent/HU194263B/hu not_active IP Right Cessation
- 1985-12-16 PT PT81689A patent/PT81689B/pt not_active IP Right Cessation
- 1985-12-16 IE IE317985A patent/IE58186B1/en not_active IP Right Cessation
- 1985-12-17 NO NO855087A patent/NO162387B/no unknown
- 1985-12-17 CN CN85109548A patent/CN1016784B/zh not_active Expired
- 1985-12-17 GR GR853032A patent/GR853032B/el unknown
- 1985-12-17 DK DK587085A patent/DK587085A/da not_active Application Discontinuation
- 1985-12-17 AT AT85116117T patent/ATE62249T1/de not_active IP Right Cessation
- 1985-12-17 DE DE8585116117T patent/DE3582420D1/de not_active Expired - Fee Related
- 1985-12-17 ES ES550060A patent/ES8706164A1/es not_active Expired
- 1985-12-17 JP JP60282167A patent/JPS61158994A/ja active Granted
- 1985-12-17 EP EP85116117A patent/EP0186103B1/en not_active Expired - Lifetime
- 1985-12-18 KR KR1019850009529A patent/KR900005607B1/ko not_active IP Right Cessation
- 1985-12-18 PH PH33204A patent/PH23660A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR900005607B1 (ko) | 1990-07-31 |
| NO855087L (no) | 1986-06-19 |
| KR860004921A (ko) | 1986-07-16 |
| EP0186103A2 (en) | 1986-07-02 |
| DE3582420D1 (de) | 1991-05-08 |
| NZ214570A (en) | 1988-03-30 |
| DK587085D0 (da) | 1985-12-17 |
| ES550060A0 (es) | 1987-06-01 |
| HU194263B (en) | 1988-01-28 |
| CN85109548A (zh) | 1986-07-09 |
| CN1016784B (zh) | 1992-05-27 |
| CA1240989A (en) | 1988-08-23 |
| HUT40137A (en) | 1986-11-28 |
| FI854944A (fi) | 1986-06-19 |
| FI854944A0 (fi) | 1985-12-13 |
| AU5081085A (en) | 1986-06-26 |
| PH23660A (en) | 1989-09-27 |
| JPH0565519B2 (sv) | 1993-09-17 |
| DK587085A (da) | 1986-06-19 |
| IE853179L (en) | 1986-06-18 |
| US4634765A (en) | 1987-01-06 |
| ATE62249T1 (de) | 1991-04-15 |
| IE58186B1 (en) | 1993-07-28 |
| EP0186103A3 (en) | 1988-02-03 |
| ZA859573B (en) | 1986-08-27 |
| PT81689A (en) | 1986-01-01 |
| JPS61158994A (ja) | 1986-07-18 |
| EP0186103B1 (en) | 1991-04-03 |
| ES8706164A1 (es) | 1987-06-01 |
| FI80707C (sv) | 1990-07-10 |
| AU574246B2 (en) | 1988-06-30 |
| GR853032B (sv) | 1986-04-18 |
| PT81689B (pt) | 1987-11-30 |
| NO162387B (no) | 1989-09-11 |
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