KR920000312B1 - N-글리코실화 카복스아미드 유도체의 제조방법 - Google Patents
N-글리코실화 카복스아미드 유도체의 제조방법 Download PDFInfo
- Publication number
- KR920000312B1 KR920000312B1 KR1019830001562A KR830001562A KR920000312B1 KR 920000312 B1 KR920000312 B1 KR 920000312B1 KR 1019830001562 A KR1019830001562 A KR 1019830001562A KR 830001562 A KR830001562 A KR 830001562A KR 920000312 B1 KR920000312 B1 KR 920000312B1
- Authority
- KR
- South Korea
- Prior art keywords
- radical
- octadecyl
- glucopyranosyl
- carbon atoms
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
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- 150000002772 monosaccharides Chemical class 0.000 claims description 7
- 150000002016 disaccharides Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229920001542 oligosaccharide Polymers 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
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- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 9
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
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- 229910052757 nitrogen Inorganic materials 0.000 description 8
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 8
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
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- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 7
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
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- 230000003204 osmotic effect Effects 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
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- 229940049954 penicillin Drugs 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 235000010413 sodium alginate Nutrition 0.000 description 1
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- 230000002588 toxic effect Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DUAJIKVIRGATIW-UHFFFAOYSA-N trinitrogen(.) Chemical group [N]=[N+]=[N-] DUAJIKVIRGATIW-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- 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
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/12—Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Immunology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Hydrogenated Pyridines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3213650.1 | 1982-04-14 | ||
| DE3213650.1 | 1982-04-14 | ||
| DE19823213650 DE3213650A1 (de) | 1982-04-14 | 1982-04-14 | N-glycosylierte carbonsaeureamid-derivate, verfahren zu ihrer herstellung sowie ihre verwendung zur beeinflussung der koerpereigenen abwehr |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840004761A KR840004761A (ko) | 1984-10-24 |
| KR920000312B1 true KR920000312B1 (ko) | 1992-01-11 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830001562A Expired KR920000312B1 (ko) | 1982-04-14 | 1983-04-14 | N-글리코실화 카복스아미드 유도체의 제조방법 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4683222A (https=) |
| EP (1) | EP0091645B1 (https=) |
| JP (1) | JPS58188891A (https=) |
| KR (1) | KR920000312B1 (https=) |
| AT (1) | ATE25525T1 (https=) |
| AU (1) | AU561016B2 (https=) |
| CA (1) | CA1230594A (https=) |
| DE (2) | DE3213650A1 (https=) |
| DK (1) | DK162883A (https=) |
| ES (1) | ES8402313A1 (https=) |
| FI (1) | FI75172C (https=) |
| GR (1) | GR78512B (https=) |
| HU (1) | HU194262B (https=) |
| IE (1) | IE55112B1 (https=) |
| IL (1) | IL68350A (https=) |
| NO (1) | NO157145C (https=) |
| PH (1) | PH25527A (https=) |
| PT (1) | PT76502B (https=) |
| ZA (1) | ZA832580B (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3213650A1 (de) * | 1982-04-14 | 1983-10-27 | Bayer Ag, 5090 Leverkusen | N-glycosylierte carbonsaeureamid-derivate, verfahren zu ihrer herstellung sowie ihre verwendung zur beeinflussung der koerpereigenen abwehr |
| DE3339694A1 (de) * | 1983-11-03 | 1985-05-15 | Bayer Ag, 5090 Leverkusen | Verwendung n-glycosilierter carbonsaeureamid-derivate als wachstumsfoerderer in der tierernaehrung |
| DE3403495A1 (de) * | 1983-11-23 | 1985-05-30 | Bayer Ag, 5090 Leverkusen | Phosphorylierte glycosylamide, -harnstoffe, -carbamate und -thiocarbamate, verfahren zu ihrer herstellung sowie ihre verwendung |
| DE3344257A1 (de) * | 1983-12-07 | 1985-06-13 | Bayer Ag, 5090 Leverkusen | Substituierte o-acyl-glycosylamide, verfahren zu iherer herstellung sowie ihre verwendung |
| DE3346623A1 (de) * | 1983-12-14 | 1985-07-04 | Bayer Ag, 5090 Leverkusen | N-glycosylierte harnstoffe, carbamate und thiocarbamate, verfahren zu ihrer herstellung sowie ihre verwendung |
| DE3347522A1 (de) * | 1983-12-30 | 1985-07-11 | Troponwerke GmbH & Co KG, 5000 Köln | N-glycosylierte carbonsaeureamid-derivate als mittel bei der bekaempfung von erkrankungen des rheumatischen formenkreises |
| DE3410238A1 (de) * | 1984-03-21 | 1985-10-03 | Bayer Ag, 5090 Leverkusen | Glycolipid-aehnliche substanzen in liposomenform |
| DE3508025A1 (de) * | 1985-03-07 | 1986-09-11 | Bayer Ag, 5090 Leverkusen | Substituierte o-sulfonyl-glycosylamide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE3521994A1 (de) * | 1985-06-20 | 1987-01-02 | Bayer Ag | N-(2-aminoacylamido-2-desoxy-hexosyl)-amide-, -carbamate und -harnstoffe, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| DE3604681A1 (de) * | 1986-02-14 | 1987-08-20 | Bayer Ag | Neue n-glycosylamidderivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE3812681A1 (de) * | 1988-04-16 | 1989-11-02 | Bayer Ag | Substituierte n-glycosylamide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US5476924A (en) * | 1989-01-27 | 1995-12-19 | Duke University | Protecting group for acetals and methods of using the same in the activation of saccharides |
| FR2676739B1 (fr) * | 1991-05-22 | 1996-10-11 | Stepan Europe | N-alkyl, n-acetylosylamines, leur procede de preparation et leurs utilisations notamment en tant qu'agents tensioactifs ou agents de solubilisation pour l'isolement de proteines membranaires. |
| US5362480A (en) * | 1991-12-31 | 1994-11-08 | Lever Brothers Company, Division Of Conopco, Inc. | Oral hygiene compositions containing amino sugars as antiplaque agents |
| US5455232A (en) * | 1992-02-04 | 1995-10-03 | Piljac; Goran | Pharmaceutical preparation based on rhamnolipid |
| FR2709061B1 (fr) * | 1993-08-17 | 1996-07-19 | Ladislas Robert | Utilisation d'oligosaccharides dans la prévention et le traitement du vieillissement des tissus. |
| DE4329094A1 (de) * | 1993-08-30 | 1995-03-02 | Bayer Ag | (Glycosylamid)-uronsäure-derivate |
| US5905071A (en) * | 1993-08-30 | 1999-05-18 | Bayer Aktiengesellschaft | Glycosylamides of 2-aminoacylamino-2-deoxy sugars |
| AU7613694A (en) * | 1993-08-30 | 1995-03-22 | Bayer Aktiengesellschaft | Glycosyl amides of 6-amino-6-deoxy sugars |
| AU4371996A (en) * | 1994-12-16 | 1996-07-03 | Alcon Laboratories, Inc. | Ophthalmic formulations of substituted glycosides |
| US6290971B1 (en) * | 1995-06-15 | 2001-09-18 | Aventis Pasteur Limited | Adjuvant compositions comprising a mineral salt and another immunostimulating compound |
| US5872111A (en) * | 1997-05-19 | 1999-02-16 | Lever Brothers Company, Division Of Conopco, Inc. | Compositions comprising glycosylamide surfactants |
| US6670330B1 (en) | 2000-05-01 | 2003-12-30 | Theodore J. Lampidis | Cancer chemotherapy with 2-deoxy-D-glucose |
| JP3664401B2 (ja) * | 2003-01-22 | 2005-06-29 | 独立行政法人科学技術振興機構 | N−グリコシド型糖脂質及びこれから成る中空繊維状有機ナノチューブ |
| US20050008699A1 (en) * | 2003-07-11 | 2005-01-13 | Fred Wehling | Effervescent glucosamine composition |
| ME00045B (me) | 2006-01-26 | 2010-10-10 | Zoetis Services Llc | Nove kompozicije glikolipidnog adjuvansa |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2808402A (en) * | 1954-08-19 | 1957-10-01 | Rohm & Haas | Method for preparing nu-sorbitylcarbamates |
| DE1261861B (de) * | 1963-08-22 | 1968-02-29 | Dehydag Gmbh | Verfahren zur Herstellung von Glycaminabkoemmlingen |
| FR2187324B1 (https=) * | 1972-06-14 | 1975-06-20 | Rech Pharmaceut Sc | |
| US4228274A (en) * | 1976-09-28 | 1980-10-14 | Merck & Co., Inc. | 1-Substituted glycopyranosides |
| JPS5649396A (en) * | 1979-09-28 | 1981-05-02 | Dai Ichi Seiyaku Co Ltd | Novel muramyldipeptide derivative |
| DE3213650A1 (de) * | 1982-04-14 | 1983-10-27 | Bayer Ag, 5090 Leverkusen | N-glycosylierte carbonsaeureamid-derivate, verfahren zu ihrer herstellung sowie ihre verwendung zur beeinflussung der koerpereigenen abwehr |
-
1982
- 1982-04-14 DE DE19823213650 patent/DE3213650A1/de not_active Withdrawn
-
1983
- 1983-03-21 AU AU12615/83A patent/AU561016B2/en not_active Ceased
- 1983-03-29 NO NO831163A patent/NO157145C/no unknown
- 1983-04-05 PT PT76502A patent/PT76502B/pt unknown
- 1983-04-06 DE DE8383103325T patent/DE3369851D1/de not_active Expired
- 1983-04-06 EP EP83103325A patent/EP0091645B1/de not_active Expired
- 1983-04-06 AT AT83103325T patent/ATE25525T1/de not_active IP Right Cessation
- 1983-04-08 JP JP58061065A patent/JPS58188891A/ja active Granted
- 1983-04-11 IL IL68350A patent/IL68350A/xx unknown
- 1983-04-12 GR GR71057A patent/GR78512B/el unknown
- 1983-04-12 PH PH28763A patent/PH25527A/en unknown
- 1983-04-12 CA CA000425694A patent/CA1230594A/en not_active Expired
- 1983-04-12 FI FI831230A patent/FI75172C/fi not_active IP Right Cessation
- 1983-04-13 IE IE840/83A patent/IE55112B1/en unknown
- 1983-04-13 ES ES521422A patent/ES8402313A1/es not_active Expired
- 1983-04-13 ZA ZA832580A patent/ZA832580B/xx unknown
- 1983-04-13 DK DK162883A patent/DK162883A/da not_active Application Discontinuation
- 1983-04-14 KR KR1019830001562A patent/KR920000312B1/ko not_active Expired
- 1983-04-14 HU HU831306A patent/HU194262B/hu not_active IP Right Cessation
-
1985
- 1985-04-19 US US06/725,060 patent/US4683222A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA1230594A (en) | 1987-12-22 |
| IE830840L (en) | 1983-10-14 |
| FI831230A0 (fi) | 1983-04-12 |
| DK162883D0 (da) | 1983-04-13 |
| ZA832580B (en) | 1984-01-25 |
| IL68350A0 (en) | 1983-07-31 |
| HU194262B (en) | 1988-01-28 |
| EP0091645A1 (de) | 1983-10-19 |
| PH25527A (en) | 1991-07-24 |
| JPS58188891A (ja) | 1983-11-04 |
| GR78512B (https=) | 1984-09-27 |
| FI75172B (fi) | 1988-01-29 |
| IE55112B1 (en) | 1990-06-06 |
| US4683222A (en) | 1987-07-28 |
| NO157145B (no) | 1987-10-19 |
| NO831163L (no) | 1983-10-17 |
| PT76502A (en) | 1983-05-01 |
| IL68350A (en) | 1988-09-30 |
| ATE25525T1 (de) | 1987-03-15 |
| EP0091645B1 (de) | 1987-02-25 |
| DE3213650A1 (de) | 1983-10-27 |
| ES521422A0 (es) | 1984-01-16 |
| KR840004761A (ko) | 1984-10-24 |
| JPH0140036B2 (https=) | 1989-08-24 |
| ES8402313A1 (es) | 1984-01-16 |
| AU561016B2 (en) | 1987-04-30 |
| FI75172C (fi) | 1988-05-09 |
| FI831230L (fi) | 1983-10-15 |
| PT76502B (en) | 1985-12-10 |
| NO157145C (no) | 1988-01-27 |
| AU1261583A (en) | 1983-10-20 |
| DE3369851D1 (en) | 1987-04-02 |
| DK162883A (da) | 1983-10-15 |
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