DE69112989T2 - Aminocoumaranderivate, ihre Herstellung und Verwendung. - Google Patents

Aminocoumaranderivate, ihre Herstellung und Verwendung.

Info

Publication number
DE69112989T2
DE69112989T2 DE69112989T DE69112989T DE69112989T2 DE 69112989 T2 DE69112989 T2 DE 69112989T2 DE 69112989 T DE69112989 T DE 69112989T DE 69112989 T DE69112989 T DE 69112989T DE 69112989 T2 DE69112989 T2 DE 69112989T2
Authority
DE
Germany
Prior art keywords
amino
dihydrobenzofuran
tetramethyl
group
yield
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 - Fee Related
Application number
DE69112989T
Other languages
German (de)
English (en)
Other versions
DE69112989D1 (de
Inventor
Tetsuya Aono
Takayuki Doi
Shigenori Ohkawa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Takeda Pharmaceutical Co Ltd
Original Assignee
Takeda Chemical Industries Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd
Publication of DE69112989D1 publication Critical patent/DE69112989D1/de
Application granted granted Critical
Publication of DE69112989T2 publication Critical patent/DE69112989T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/80—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (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)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Cardiology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Pyrane Compounds (AREA)
  • Cephalosporin Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyrrole Compounds (AREA)
  • Saccharide Compounds (AREA)
DE69112989T 1990-11-01 1991-10-29 Aminocoumaranderivate, ihre Herstellung und Verwendung. Expired - Fee Related DE69112989T2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP29865090 1990-11-01
JP24566791 1991-09-25

Publications (2)

Publication Number Publication Date
DE69112989D1 DE69112989D1 (de) 1995-10-19
DE69112989T2 true DE69112989T2 (de) 1996-02-15

Family

ID=26537343

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69112989T Expired - Fee Related DE69112989T2 (de) 1990-11-01 1991-10-29 Aminocoumaranderivate, ihre Herstellung und Verwendung.

Country Status (13)

Country Link
US (4) US5376681A (enExample)
EP (1) EP0483772B1 (enExample)
JP (1) JP2672423B2 (enExample)
KR (1) KR100202463B1 (enExample)
AT (1) ATE127797T1 (enExample)
CA (1) CA2054619C (enExample)
DE (1) DE69112989T2 (enExample)
DK (1) DK0483772T3 (enExample)
ES (1) ES2077138T3 (enExample)
GR (1) GR3017981T3 (enExample)
HU (2) HUT60258A (enExample)
IE (1) IE68675B1 (enExample)
TW (1) TW199152B (enExample)

Families Citing this family (40)

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HUT68721A (en) * 1990-12-28 1995-07-28 Teijin Ltd Benzofuran and benzizoxazole derivatives, pharmaceutical composition containing said compounds as active agent and process for preparing them
FI944655L (fi) * 1992-04-06 1994-10-05 Merrell Dow Pharma Uudet 2,3-dihydro-2,2,4,6,7-penta-alkyyli-5-bentsofuranolit
US5721233A (en) * 1992-04-06 1998-02-24 Merrell Pharmaceuticals Inc. Derivatives of 2,3-dihydro benzofuranols
JP3198395B2 (ja) 1992-05-28 2001-08-13 武田薬品工業株式会社 アミノクマラン誘導体
TW334433B (en) * 1992-12-09 1998-06-21 Takeda Pharm Industry Co Ltd Crystalline salt of (S)-(+)-5-amino-2,4,6,7-tetramethyl-2-(4-phenylpiperidinomethyl)-2,3-dihydrobenzo(b)furan dihydrochloride their production and use
EP0640609A1 (en) * 1993-08-24 1995-03-01 Ono Pharmaceutical Co., Ltd. Fused phenol derivatives having inhibitory activity on TXA2 synthetase, and 5-lipoxygenase and scavenging activity on oxygen species
DE59401926D1 (de) * 1993-11-11 1997-04-10 Basf Ag P-Hydroxyanilinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schadpilzen oder Schädlingen
ATE163639T1 (de) * 1993-11-11 1998-03-15 Basf Ag P-hydroxyanilinderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen oder schädlingen
DE69426871T2 (de) * 1993-12-08 2001-06-21 Alcon Laboratories, Inc. Verbindungen die sowohl starke calcium-antagonistische und antioxydatieve aktivitaet haben und deren verwendung als zellschuetzende mittel.
US6017953A (en) * 1993-12-28 2000-01-25 Allergan Sales, Inc. Thromboxane ligands
US6743808B1 (en) 1994-06-08 2004-06-01 H. Lundbeck A/S 4-aryl-1-(indanmethyl, dihydrobenzofuranmethyl or dihydrobenzothiophenemethyl) tetrahydropyridines or piperazines
IL114026A (en) 1994-06-08 1999-06-20 Lundbeck & Co As H 4-aryl-1-(indanmethyl dihydrobenzofuranmethyl or dihydrobenzo thiophenemethyl) piperidines tetrahydropyridines or piperazines and pharmaceutical compositions containing them
CA2215105A1 (en) * 1995-03-10 1996-09-19 Hoechst Marion Roussel, Inc. Novel process for preparing 2,3-dihydro-benzofuranol derivatives
HUP9903557A2 (en) * 1996-08-29 2002-08-28 Takeda Chemical Industries Ltd Cyclic ether compounds, producing and useing them
ZA9711376B (en) 1996-12-20 1998-07-21 Lundbeck & Co As H Indole or dihydroindole derivatives
CA2291026A1 (en) 1997-06-05 1998-12-10 Takeda Chemical Industries, Ltd. Heterocyclic compounds, their production and use
AU746158B2 (en) * 1997-11-12 2002-04-18 Darwin Discovery Limited Hydroxamic and carboxylic acid derivatives having MMP and TNF inhibitory activity
AU753360B2 (en) 1998-07-31 2002-10-17 Nippon Soda Co., Ltd. Phenylazole compounds, process for producing the same and drugs for hyperlipemia
US6479536B1 (en) 1998-12-04 2002-11-12 Takeda Chemical Industries, Ltd. Benzofuran derivatives, process for the preparation of the same and uses thereof
SE9902267D0 (sv) * 1999-06-16 1999-06-16 Astra Ab New compounds
DE19935692A1 (de) * 1999-07-29 2001-02-01 Merck Patent Gmbh Nitrierung in einem statischen Mikromischer
EP1211253B1 (en) * 1999-08-20 2004-10-13 Takeda Chemical Industries, Ltd. Tricyclic dihydrobenzofuran derivatives, process for the preparation thereof and agents
JP4721494B2 (ja) * 1999-08-20 2011-07-13 武田薬品工業株式会社 三環性ジヒドロフラン誘導体、その製造法及び剤
EP1125905A1 (en) * 2000-02-16 2001-08-22 Pepscan Systems B.V. Segment synthesis
EP1197755A1 (en) * 2000-10-11 2002-04-17 Pepscan Systems B.V. Identification of protein binding sites
WO2002053551A1 (en) * 2000-12-28 2002-07-11 Takeda Chemical Industries, Ltd. Process for preparing optically active 2,3-dihydro- benzofuran compounds
DE10115408A1 (de) * 2001-03-29 2002-10-02 Bayer Ag Benzofuran-Derivate
ATE406357T1 (de) 2001-07-13 2008-09-15 Takeda Pharmaceutical Verfahren zur herstellung von benzofuranderivaten
EP1452868A2 (en) 2003-02-27 2004-09-01 Pepscan Systems B.V. Method for selecting a candidate drug compound
ES2320995T3 (es) * 2003-04-14 2009-06-01 Nippon Soda Co., Ltd. Derivado de diamina, procedimiento de produccion y farmaco antioxidante.
WO2005000829A1 (ja) * 2003-06-26 2005-01-06 Takeda Pharmaceutical Company Limited カンナビノイド受容体調節剤
US7553837B2 (en) * 2003-08-01 2009-06-30 Nippon Soda Co., Ltd. Phenylazole compounds production process and antioxidants
US7485711B2 (en) * 2005-08-12 2009-02-03 Mayo Foundation For Medical Education And Research CYP19A1 polymorphisms
US20100172909A1 (en) * 2005-10-24 2010-07-08 Masahiro Nishibori Cerebral edema suppressant
JP3882090B1 (ja) * 2006-05-19 2007-02-14 国立大学法人 岡山大学 脳血管攣縮抑制剤
DE102007018833A1 (de) 2007-04-20 2008-10-23 Febit Holding Gmbh Verbesserte molekularbiologische Prozessanlage
DE102006062089A1 (de) 2006-12-29 2008-07-03 Febit Holding Gmbh Verbesserte molekularbiologische Prozessanlage
ES2487616T3 (es) 2009-03-10 2014-08-22 Takeda Pharmaceutical Company Limited Derivados de benzofurano
JP2009215301A (ja) * 2009-04-27 2009-09-24 Morinaga Milk Ind Co Ltd プロテアーゼ阻害剤
US8563705B2 (en) 2010-05-12 2013-10-22 Mayo Foundation For Medical Education And Research Ribonucleic acid binding motif protein 20 sequence variants

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US3686188A (en) * 1970-06-30 1972-08-22 Ciba Geigy Corp N-benzofurylmethyl-arylalkyleneimines
CA1337429C (en) * 1983-12-05 1995-10-24 Guy Rosalia Eugene Van Lommen Derivatives of 2,2'-iminobisethanol
CA1297877C (en) * 1983-12-22 1992-03-24 Daniel Lednicer Benzofurancarboxamides useful as antiemetic or antipsychotic agents
US4888353A (en) * 1986-02-28 1989-12-19 Erbamont, Inc. Carboxamides useful as antiemetic or antipsychotic agents
US5087638A (en) * 1984-06-20 1992-02-11 Merck Frosst Canada, Inc. Benzofuran derivatives
CA1281325C (en) * 1984-06-20 1991-03-12 Patrice C. Belanger Benzofuran derivatives
JPS6133183A (ja) * 1984-07-25 1986-02-17 Mitsubishi Chem Ind Ltd ２，３−ジヒドロ−７−アミノベンゾフランの製造法
US4772730A (en) * 1985-04-19 1988-09-20 Fmc Corporation Tetrafluoro-2,3-dihydrobenzofurans
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US4772459A (en) * 1986-09-09 1988-09-20 Erbamont, Inc. Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein
EP0273647B1 (en) * 1986-12-27 1992-03-11 Takeda Chemical Industries, Ltd. Coumaran derivatives, their production and use
US4873255A (en) * 1987-02-04 1989-10-10 Sankyo Company Limited Thiazolidinone derivatives, their preparation and their use
GB8704572D0 (en) * 1987-02-26 1987-04-01 Lundbeck & Co As H Organic compounds
JP2855341B2 (ja) * 1988-06-10 1999-02-10 武田薬品工業株式会社 新規２―置換クマラン誘導体
JP2855340B2 (ja) * 1988-06-10 1999-02-10 武田薬品工業株式会社 ２―置換クマラン誘導体

Also Published As

Publication number Publication date
US5770772A (en) 1998-06-23
EP0483772A1 (en) 1992-05-06
IE68675B1 (en) 1996-07-10
KR920009815A (ko) 1992-06-25
HUT60258A (en) 1992-08-28
TW199152B (enExample) 1993-02-01
ES2077138T3 (es) 1995-11-16
DE69112989D1 (de) 1995-10-19
HU211480A9 (en) 1995-11-28
CA2054619C (en) 2003-06-10
ATE127797T1 (de) 1995-09-15
EP0483772B1 (en) 1995-09-13
CA2054619A1 (en) 1992-05-02
JPH05140142A (ja) 1993-06-08
HU913436D0 (en) 1992-01-28
US5594154A (en) 1997-01-14
KR100202463B1 (ko) 1999-06-15
JP2672423B2 (ja) 1997-11-05
GR3017981T3 (en) 1996-02-29
US5376681A (en) 1994-12-27
IE913724A1 (en) 1992-05-22
DK0483772T3 (da) 1996-01-22
US5478844A (en) 1995-12-26

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