KR900011789A - 새로운 헤파린 유도체 및 그 제조방법 - Google Patents
새로운 헤파린 유도체 및 그 제조방법 Download PDFInfo
- Publication number
- KR900011789A KR900011789A KR1019900000266A KR900000266A KR900011789A KR 900011789 A KR900011789 A KR 900011789A KR 1019900000266 A KR1019900000266 A KR 1019900000266A KR 900000266 A KR900000266 A KR 900000266A KR 900011789 A KR900011789 A KR 900011789A
- Authority
- KR
- South Korea
- Prior art keywords
- reaction mixture
- alkaline earth
- optionally
- alkali metal
- earth metal
- Prior art date
Links
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical class OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 title claims 8
- 239000002628 heparin derivative Substances 0.000 title claims 5
- 238000002360 preparation method Methods 0.000 title claims 2
- 239000011541 reaction mixture Substances 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- 229910052783 alkali metal Inorganic materials 0.000 claims 6
- 150000001340 alkali metals Chemical class 0.000 claims 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 6
- 239000007864 aqueous solution Substances 0.000 claims 5
- 235000019441 ethanol Nutrition 0.000 claims 5
- 230000007935 neutral effect Effects 0.000 claims 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 4
- 239000002585 base Substances 0.000 claims 4
- 239000003638 chemical reducing agent Substances 0.000 claims 4
- 238000000502 dialysis Methods 0.000 claims 4
- 238000005342 ion exchange Methods 0.000 claims 4
- 229910052700 potassium Inorganic materials 0.000 claims 4
- 239000011591 potassium Substances 0.000 claims 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- -1 alkaline earth metal salt Chemical class 0.000 claims 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims 3
- 230000003197 catalytic effect Effects 0.000 claims 3
- 238000001914 filtration Methods 0.000 claims 3
- 238000004108 freeze drying Methods 0.000 claims 3
- 229960002897 heparin Drugs 0.000 claims 3
- 229920000669 heparin Polymers 0.000 claims 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 229910052788 barium Inorganic materials 0.000 claims 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 2
- 229910052791 calcium Inorganic materials 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- 239000011777 magnesium Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 206010029148 Nephrolithiasis Diseases 0.000 claims 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003055 low molecular weight heparin Substances 0.000 claims 1
- 229940127215 low-molecular weight heparin Drugs 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 1
- 235000019341 magnesium sulphate Nutrition 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 1
- 235000011152 sodium sulphate Nutrition 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0075—Heparin; Heparan sulfate; Derivatives thereof, e.g. heparosan; Purification or extraction methods thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
- Materials For Medical Uses (AREA)
- Pyridine Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- 약 101.3 ppm에서 특성 시그널이 존재하며 특히 102와 92사이의 영역에서 시판용 헤파린과는 다른13C-NMR 스펙트럼을 나타내며, 546nm에서의 비선광도는 수용액중에 약 15°-약 40°사이이고, 황함량은 약 6%-약 9%이며, 황산염/카르복실 비는 약 1.20 - 약 1.70이고, 유리아미노기의 함량은 약 0.4%- 약 2.1%인 것을 특징으로 하는 새로운 헤파린 유도체.
- 시판용 또는 정제된 또는 저분자량에 헤파린을 함유하는 수용액을 임의 선택적으로 약 1N농도 이하의 알카리금속 또는 알칼리토금속염 및 촉매적량의 환원제 존재하에 약 0.01N-약 1N의 알칼리금속 또는 알칼리토금속염기로 약 75℃ 와 반응 혼합물의 끓는 점 사이의 온도에서 약 0.5- 약 24시간 동안 처리하고, 필요시이 반응혼합물을 이온교환 컬럼을 통한 여과 또는 투석 등에 의해 정재한 다음, 약 중성 pH에서 C1-C3알콜을 약 2-4부피 가하거나 동결건조하여 침전시킴으로써 수정된 구조를 가지는 생성물을 분리해내는 단계를 포함하는, 제1항의 새로운 헤파린 유도체의 제조방법.
- 시판용 또는 정재된 또는 저분자량에 헤파린을 함유하는 수용액을 임의 선택적으로 약 1N이하의 알칼리금속 또는 알칼리토금속염 및 촉매 적량의 환원제 존재하에 약 0.01- 약 1N의 알칼리금속 또는 알칼리토금속 염기로 약 40℃- 약 70℃ 온도에서 약 0.5- 약 24시간동안 처리한 다음 이 반응 혼합물을 이온교환컬럼의 통과 또는 투석에 의한 정제를 거친다음 약 중성 pH에서 C1-C3알콜을 약 2- 약4부피 가하거나 동결건조하여 침전시킴으로써 중간 반응 화합물을 분리해낸 다음, 이 중간 반응 혼합물의 수용액을 약 75℃-반응혼합물의 끓는점 사이의 온도에서 약 0.5-약 24시간동안 항온 시킨후, 필요시 이 반응 혼합물을 이온 교환 컬럼을 통한 여과 또는 투석등에 의해 정제한 다음, 약 중성 pH에서 C1-C3알콜을 약 2-4 부피 가하거나 동결건조하여 침전시킴으로써 목적하는 생성물을 분리해내는 단계를 포함하는 제1항의 새로운 헤파린 유도체의 제조방법.
- 시판용 또는 정제된 또는 저분자량의 헤파린을 함유하는 수용액을 임의 선택적으로 약 1N이하의 알칼리금속또는 알칼리토금속염 및 촉매 적량의 환원제 존재하에, 약 0.01N- 약 1N의 알칼리금속 또는 알칼리토금속 염기로 약 40℃- 약 70℃온도에서 약 0.5- 약 24시간 동안 처리한 다음, 이 반응혼합물을 중성 pH로 조절하고, 약 75℃-반응혼합물의 끓는 점 사이의 온도에서 약 0.5-24시간동안 항온시킨후, 필요시 이 반응혼합물을 이온교환 컬럼을 통한 여과 또는 투석에 의해 정제시킨 다음, 약 중성 pH에서 C1-C3알콜을 약 2-4부피 가하거나 동결 건조하여 침전시킴으로써 목적하는 생성물을 분리해내는 단계를 포함하는, 제1항의 새로운 헤파린 유도체의 제조방법.
- 제2항 또는 제3항 또는 제4항에 있어서, 염기는 수산화나트륨, 칼륨 및 바륨중에서 선택되고 염은 초산나트륨, 칼륨, 바륨, 칼슘 및 마그네슘, 염화나트륨, 칼륨, 칼슘 및 마그네슘 및 황산나트륨, 칼륨 및 마그네슘중에서 선택되며, 환원제는 수소화붕소나트륨이고 목적하는 생성물 2,5부피의 에틸알콜에 의해 침전되는 것을 특징으로 하는 제조방법.
- 신장결석증 치료용 약제로서의 제1항의 새로운 헤파린유도체의 사용.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3328A/89 | 1989-01-30 | ||
| IT8903328A IT1234826B (it) | 1989-01-30 | 1989-01-30 | Derivati eparinici e procedimento per la loro preparazione |
| IT3328A89 | 1989-01-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR900011789A true KR900011789A (ko) | 1990-08-02 |
| KR0161667B1 KR0161667B1 (ko) | 1998-11-16 |
Family
ID=11105069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019900000266A KR0161667B1 (ko) | 1989-01-30 | 1990-01-11 | 헤파린 유도체 및 그 제조방법과 그를 함유하는 의약품 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5104860A (ko) |
| EP (1) | EP0380943B1 (ko) |
| JP (1) | JPH0678369B2 (ko) |
| KR (1) | KR0161667B1 (ko) |
| AT (1) | ATE111107T1 (ko) |
| AU (1) | AU610034B2 (ko) |
| CA (1) | CA2007616C (ko) |
| DE (1) | DE69012154T2 (ko) |
| DK (1) | DK0380943T3 (ko) |
| ES (1) | ES2058609T3 (ko) |
| FI (1) | FI96425C (ko) |
| IE (1) | IE66563B1 (ko) |
| IL (1) | IL92912A (ko) |
| IT (1) | IT1234826B (ko) |
| NO (1) | NO301719B1 (ko) |
| NZ (1) | NZ232115A (ko) |
| PT (1) | PT92991B (ko) |
| ZA (1) | ZA90263B (ko) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1234826B (it) * | 1989-01-30 | 1992-05-29 | Alfa Wassermann Spa | Derivati eparinici e procedimento per la loro preparazione |
| US5250519A (en) * | 1991-03-29 | 1993-10-05 | Glycomed Incorporated | Non-anticoagulant heparin derivatives |
| IT1254216B (it) * | 1992-02-25 | 1995-09-14 | Opocrin Spa | Derivati polisaccaridici di eparina, eparan solfato, loro frazioni e frammenti, procedimento per la loro preparazione e composizioni farmaceutiche che li contengono |
| IT1260137B (it) * | 1992-04-17 | 1996-03-28 | Alfa Wassermann Spa | Glicosaminoglicani semisintetici a struttura eparinica od eparanica modificati nella posizione 2 dell'acido alfa-l-iduronico-2-0-solfato |
| IT1260136B (it) * | 1992-04-17 | 1996-03-28 | Alfa Wassermann Spa | Glicosaminoglicani semisintetici contenenti acido alfa-l-galatturonicosostituito con radicali nucleofili in posizione 3 |
| US5668118A (en) * | 1992-07-24 | 1997-09-16 | Cavalier Pharmaceuticals | Method of synthesis of 2-O-desulfated Heparin and use thereof for inhibition of elastase and Cathepspin G |
| US5296471A (en) * | 1992-12-22 | 1994-03-22 | Glycomed Incorporated | Method for controlling o-desulfation of heparin and compositions produced thereby |
| US5696100A (en) * | 1992-12-22 | 1997-12-09 | Glycomed Incorporated | Method for controlling O-desulfation of heparin and compositions produced thereby |
| US5336620A (en) * | 1993-01-27 | 1994-08-09 | American Home Products Corporation | Process for the production of an anticoagulant composition |
| IT1264101B1 (it) * | 1993-03-29 | 1996-09-10 | Alfa Wassermann Spa | Processo per la sintesi di glicosaminoglicani semisintetici a struttura eparinica od eparanica modificati nella posizione 2 |
| IT1264102B1 (it) * | 1993-03-29 | 1996-09-10 | Alfa Wassermann Spa | Processo per la sintesi di glicosaminoglicani semisintetici contenenti acido alfa-l-galatturonico sostituito con radicali |
| US20020055710A1 (en) * | 1998-04-30 | 2002-05-09 | Ronald J. Tuch | Medical device for delivering a therapeutic agent and method of preparation |
| IL129877A (en) * | 1996-11-27 | 2004-08-31 | Aventis Pharm Prod Inc | A pharmaceutical preparation containing a component having an Xa antagonist activity and an antifouling agent |
| US6203536B1 (en) * | 1997-06-17 | 2001-03-20 | Medtronic, Inc. | Medical device for delivering a therapeutic substance and method therefor |
| US6106454A (en) * | 1997-06-17 | 2000-08-22 | Medtronic, Inc. | Medical device for delivering localized radiation |
| US6013099A (en) | 1998-04-29 | 2000-01-11 | Medtronic, Inc. | Medical device for delivering a water-insoluble therapeutic salt or substance |
| US7259152B2 (en) | 2000-06-07 | 2007-08-21 | Alfa Wasserman, Inc. | Methods and compositions using sulodexide for the treatment of diabetic nephropathy |
| AU2007200688B2 (en) * | 2000-09-12 | 2010-02-04 | Massachusetts Institute Of Technology | Methods and products related to low molecular weight heparin |
| CA2422059C (en) * | 2000-09-12 | 2012-05-15 | Massachusetts Institute Of Technology | Methods and products related to low molecular weight heparin |
| EP2402753A1 (en) * | 2002-03-11 | 2012-01-04 | Momenta Pharmaceuticals, Inc. | Analysis of sulfated polysaccharides |
| EP1582531A1 (en) | 2004-03-24 | 2005-10-05 | Aventis Pharma S.A. | Process for oxidizing unfractionated heparins and detecting presence or absence of glycoserine in heparin and heparin products |
| ATE552004T1 (de) | 2005-11-30 | 2012-04-15 | Istituto G Ronzoni | Oral verabreichbare heparinderivate |
| US9139876B1 (en) | 2007-05-03 | 2015-09-22 | Momenta Pharmacueticals, Inc. | Method of analyzing a preparation of a low molecular weight heparin |
| EP2526122B1 (en) * | 2010-01-19 | 2020-06-10 | Momenta Pharmaceuticals, Inc. | Evaluating heparin preparations |
| CN103209997B (zh) * | 2010-09-14 | 2016-03-16 | 国立大学法人宫崎大学 | 高纯度肝素及其制备方法 |
| WO2012115952A1 (en) | 2011-02-21 | 2012-08-30 | Momenta Pharmaceuticals, Inc. | Evaluating heparin preparations |
| CN108498532B (zh) | 2012-05-09 | 2021-07-23 | 坎泰克斯制药股份有限公司 | 骨髓抑制的治疗 |
| US10052346B2 (en) | 2015-02-17 | 2018-08-21 | Cantex Pharmaceuticals, Inc. | Treatment of myelodysplastic syndromes with 2-O and,or 3-O desulfated heparinoids |
| WO2022015794A1 (en) | 2020-07-14 | 2022-01-20 | Optimvia, Llc | Methods for synthesizing non-anticoagulant heparan sulfate |
| WO2021007429A1 (en) | 2019-07-09 | 2021-01-14 | Optimvia Llc | Methods for synthesizing anticoagulant polysaccharides |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5318520B2 (ko) * | 1972-07-05 | 1978-06-15 | ||
| FR2482611B1 (fr) * | 1980-05-14 | 1986-03-07 | Pharmindustrie | Nouveaux polysaccharides sulfates, procedes pour leur preparation et leur utilisation comme medicaments |
| EP0066908B1 (en) * | 1981-05-21 | 1985-08-28 | Akzo N.V. | New anti-thromboticum based on polysacharides, method for its preparation and pharmaceutical compositions |
| IT1195497B (it) * | 1983-03-08 | 1988-10-19 | Opocrin Spa | Procedimento per la preparazione di frazioni oligosaccaridiche dotate di proprieta' farmacologiche per degradazione chimica di eparina |
| DE3422518A1 (de) * | 1984-06-16 | 1985-12-19 | B. Braun Melsungen Ag, 3508 Melsungen | Heparin-derivate, verfahren zu ihrer herstellung, diese enthaltende arzneimittel und ihre verwendung bei der behandlung von fettstoffwechselstoerungen |
| FR2614026B1 (fr) * | 1987-04-16 | 1992-04-17 | Sanofi Sa | Heparines de bas poids moleculaire, a structure reguliere, leur preparation et leurs applications biologiques |
| IT1234508B (it) * | 1988-06-10 | 1992-05-19 | Alfa Wassermann Spa | Derivati eparinici e procedimento per la loro preparazione |
| IT1234826B (it) * | 1989-01-30 | 1992-05-29 | Alfa Wassermann Spa | Derivati eparinici e procedimento per la loro preparazione |
-
1989
- 1989-01-30 IT IT8903328A patent/IT1234826B/it active
- 1989-12-28 IL IL9291289A patent/IL92912A/en unknown
-
1990
- 1990-01-09 US US07/462,462 patent/US5104860A/en not_active Expired - Fee Related
- 1990-01-11 KR KR1019900000266A patent/KR0161667B1/ko not_active IP Right Cessation
- 1990-01-11 CA CA002007616A patent/CA2007616C/en not_active Expired - Fee Related
- 1990-01-12 DE DE69012154T patent/DE69012154T2/de not_active Expired - Fee Related
- 1990-01-12 ES ES90100593T patent/ES2058609T3/es not_active Expired - Lifetime
- 1990-01-12 AT AT90100593T patent/ATE111107T1/de not_active IP Right Cessation
- 1990-01-12 DK DK90100593.4T patent/DK0380943T3/da active
- 1990-01-12 EP EP90100593A patent/EP0380943B1/en not_active Expired - Lifetime
- 1990-01-15 NZ NZ232115A patent/NZ232115A/en unknown
- 1990-01-15 ZA ZA90263A patent/ZA90263B/xx unknown
- 1990-01-29 JP JP2020343A patent/JPH0678369B2/ja not_active Expired - Fee Related
- 1990-01-29 NO NO900392A patent/NO301719B1/no not_active IP Right Cessation
- 1990-01-29 AU AU48858/90A patent/AU610034B2/en not_active Ceased
- 1990-01-29 IE IE31690A patent/IE66563B1/en not_active IP Right Cessation
- 1990-01-29 FI FI900446A patent/FI96425C/fi not_active IP Right Cessation
- 1990-01-29 PT PT92991A patent/PT92991B/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE69012154D1 (de) | 1994-10-13 |
| FI900446A0 (fi) | 1990-01-29 |
| NO900392D0 (no) | 1990-01-29 |
| IT1234826B (it) | 1992-05-29 |
| IE900316L (en) | 1990-07-30 |
| IL92912A0 (en) | 1990-09-17 |
| JPH0678369B2 (ja) | 1994-10-05 |
| PT92991B (pt) | 1995-12-29 |
| EP0380943A1 (en) | 1990-08-08 |
| PT92991A (pt) | 1990-07-31 |
| CA2007616A1 (en) | 1990-07-30 |
| KR0161667B1 (ko) | 1998-11-16 |
| NZ232115A (en) | 1991-05-28 |
| EP0380943B1 (en) | 1994-09-07 |
| DE69012154T2 (de) | 1995-02-23 |
| CA2007616C (en) | 1996-05-14 |
| JPH02240102A (ja) | 1990-09-25 |
| IL92912A (en) | 1994-06-24 |
| NO301719B1 (no) | 1997-12-01 |
| ZA90263B (en) | 1990-10-31 |
| AU4885890A (en) | 1990-10-25 |
| DK0380943T3 (da) | 1994-12-19 |
| ES2058609T3 (es) | 1994-11-01 |
| IE66563B1 (en) | 1996-01-24 |
| FI96425B (fi) | 1996-03-15 |
| FI96425C (fi) | 1996-06-25 |
| US5104860A (en) | 1992-04-14 |
| IT8903328A0 (it) | 1989-01-30 |
| ATE111107T1 (de) | 1994-09-15 |
| NO900392L (no) | 1990-07-31 |
| AU610034B2 (en) | 1991-05-09 |
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