KR930012034A - 급성 췌장염 치료용 브래디키닌-길항제 - Google Patents
급성 췌장염 치료용 브래디키닌-길항제 Download PDFInfo
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- KR930012034A KR930012034A KR1019920024742A KR920024742A KR930012034A KR 930012034 A KR930012034 A KR 930012034A KR 1019920024742 A KR1019920024742 A KR 1019920024742A KR 920024742 A KR920024742 A KR 920024742A KR 930012034 A KR930012034 A KR 930012034A
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- 206010033645 Pancreatitis Diseases 0.000 title claims abstract 5
- 206010033647 Pancreatitis acute Diseases 0.000 title claims abstract 5
- 201000003229 acute pancreatitis Diseases 0.000 title claims abstract 5
- 239000003152 bradykinin antagonist Substances 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 8
- ODKSFYDXXFIFQN-SCSAIBSYSA-N D-arginine Chemical compound OC(=O)[C@H](N)CCCNC(N)=N ODKSFYDXXFIFQN-SCSAIBSYSA-N 0.000 claims abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 7
- 239000001257 hydrogen Substances 0.000 claims abstract 7
- FXHCFPUEIDRTMR-UHFFFAOYSA-N hydron;1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid;chloride Chemical compound Cl.C1=CC=C2CNC(C(=O)O)CC2=C1 FXHCFPUEIDRTMR-UHFFFAOYSA-N 0.000 claims abstract 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 7
- -1 mercapto, hydroxyphenyl Chemical group 0.000 claims abstract 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 6
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 claims abstract 5
- LEIKGVHQTKHOLM-IUCAKERBSA-N Pro-Pro-Gly Chemical compound OC(=O)CNC(=O)[C@@H]1CCCN1C(=O)[C@H]1NCCC1 LEIKGVHQTKHOLM-IUCAKERBSA-N 0.000 claims abstract 5
- 108010087846 prolyl-prolyl-glycine Proteins 0.000 claims abstract 5
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims abstract 3
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 4
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract 1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/043—Kallidins; Bradykinins; Related peptides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/08—Peptides having 5 to 11 amino acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/18—Kallidins; Bradykinins; Related peptides
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- Life Sciences & Earth Sciences (AREA)
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- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
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- Proteomics, Peptides & Aminoacids (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Gastroenterology & Hepatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Diabetes (AREA)
- Biochemistry (AREA)
- Hematology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
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Abstract
본 발명은 급성 췌장염을 치료하기 위한 하기 서열식(1) 브래디키닌-길항제 및 이의 생리학적으로 허용되는 염, 이를 함유하는 약제 및 적절한 약제학적 조성물을 제조하기 위한 이의 용도에 관한 것이다:
R1-A-B-C-E-F-C-J-K-R2(1)
상기식에서, R1은 수소; 머캅토, 하이드록시페닐 또는 (4-벤조일)펜옥시에 의해 치환될 수 있는 C1-4-알카노일; 또는 (4-벤조일)벤조일-Lys이고, A는 D-Arg; D-Lys; 또는 직접 결합이며, B는 NO2또는 톨루올-4-설포닐에 의해 치환될 수 있는 Arg; 또는 톨루올-4-설포닐 또는 CO-NH-C6H5에 의해 치환될 수 있고 Lys; 또는 직접 결합이고, C는 Hyp-Pro-Gly; Pro-Hyp-Gly; Pro-Pro-Gly; 또는 데하이드로 Pro-Hyp-Gly이며, E는 Thi; Phe; Leu; 또는 Cha이고, F는 Ser; 또는 Cys이며, G는 C1-C4-알콕시에 의해 치환된 D-Tic, D-Phe 또는 D-Hyp이고, J는 Tic; Aoc; 또는 Oic이며, K는 Arg; Ahx; 또는 직접 결합이고, R2는 하이드록시; 또는 아미노이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- 약제학적으로 허용되는 비이콜중에, 약리학적 활성량의 서열식(1)의 펩타이드 또는 이의 생리학적으로 허용되는 염을 함유함을 특징으로 하는, 급성 췌장염 치료용 약제학적 조성물.R1-A-B-C-E-F-G-J-K-R2(1)상기식에서, R1은 수소 머캅토, 하이드록시페닐 또는 (4-벤조일) 펜옥시에 의해 치환될 수 있는 C1-4-알카노일; 또는 (4-벤조일) 벤조일-Lys이고, A는 D-Arg; D-Lys; 또는 직접 결합이며, B는 NO2또는 톨루올-4-설포닐에 의해 치환될 수 있는 Arg; 또는 톨루올-4-설포닐 또는 CO-NH-C6H5에 의해 치환될 수 있는 Lys;또는 직접 결합이고, C는 Hyp-Pro-Gly; Pro-Hyp-Gly; Pro-Pro-Gly; 또는 데하이드로 Pro-Hyp-Gly이며, E는 Thi; Phe; Leu; 또는 Cha이고, F는 Ser; 또는 Cys이며, G는 C1-C4-알콕시에 의해 치환된 D-Tic, D-Phe 또는 D-Hyp이고, J는 Ti이 Aoc; 또는 Oic이며, K는 Arg; Ahx; 또는 직접 결합이고, R2는 하이드록시; 또는 아미노이다.
- 제1항에 있어서, R1이 수소; 머캅토 또는 (4-벤조일)펜옥시에 의해 치환될 수 있는 아세틸; 또는 (4-벤조일)벤조일-Lys이고, A가 D-Arg; 또는 직접 결합이며, B가 톨루올-4-설포닐에 의해 치환될 수 있는 Arg; 또는 직접 결합이고, C가 Pro-Hyp-Gly; Pro-Pro-Gly; 또는 데하이드로 Pro-Hyp-Gly이며, E가 Thi; Phe; 또는 Leu이고, F가 Ser; 또는 Cys이며, G가 D-Tic; D-Phe; D-HypE(트렌스메틸); 또는 D-HypE(트렌스프로필)이고, J가 Tic; Aoc; 또는 Oic이며, K가 Arg이고, R2가 하이드록시인 서열식(1)의 펩타이드 또는 이의 생리학적으로 허용되는 염을 사용하는 조성물.
- 제1항 또는 3항에 있어서, R1이 수소; 또는 (4-벤조일)벤조일-Lys이고, A가 D-Arg이며, B가 Arg이고; C가 Pro-Hyp-Gly; 또는 Pro-Pro-Cly이며, E가 Thi; Phe; 또는 Leu이고, F가 Ser이며, G가 D-Tic: 또는 D-HypE(트렌스프로필)이고, J가 Oic이며, K가 Arg이고, Y가 하이드록시인 서열식(1)의 펩타이드 또는 이의 생리학적으로 허용되는 염을 사용하는 조성물.
- 제1항 내지 3항중 어느 한 항에 있어서, H-D-Arg-Arg-Pro-Hyp-Gly-Thi-Ser-D-Tic-Oic-Arg-OH(서열동정번호: 1), H-D-Arg-Arg-Pro-Pro-Gly-Thi-Ser-D-Tic-Oic-Arg-OH(서열동정번호: 2), H-D-Arg-Arg-Pro-Hyp-Gly-Phe-Ser-D-Tic-Oic-Arg-OH(서열동정번호: 3), H-(4-벤조일)벤조일)LyS-D-Arg-Arg-Pro-Hyp-Gly-Thi-Ser-D-Tic-Oic-Arg-OH(서열동정번호: 4), H-D-Arg-Arg-Pro-Hyp-Gly-Leu-Ser-D-Tic-Oic-Arg-OH(서열동정번호: 5), H-D-Arg-Arg-Pro-Hyp-Gly-Phe-Ser-D-HypE(트렌스프로필)-Oic-Arg-OH(서열동정번호: 6), 또는 이의 생리학적으로 허용되는 염을 사용하는 조성물.
- 급성 췌장염을 치료하기 위한 서열식(1)의 펩타이드 또는 이의 생리학적으로 허용되는 염의 용도.R1-A-B-C-E-F-G-J-K-R2(1)상기식에서, R1은 수소;머캅토, 하이드록시페닐 또는 (4-벤조일)펜옥시에 의해 치환될 수 있는 C1-C4-알카노일; 또는 (4-벤조일)벤조일-Lys이고, A는 D-Arg; D-Lys; 또는 직접 결합이며, B는 NO2또는 톨루올-4-설포닐에 의해 치환될 수 있는 Arg; 또는 톨루올-4-설포닐 또는 CO-NH-C6H5에 의해 치환될 수 있는 Lys;또는 직접 결합이고, C는 Hyp-Pro-Gly; Pro-Hyp-Cly; Pro-PrO-Gly;또는 데하이드로 Pro-Hyp-Gly이며, E는 Thi; Phe; Leu; 또는 Cha이고, F는 Ser; 또는 Cys이며, C는 C1-C4-알콕시에 의해 치환된 D-Tic, D-Phe 또는 D-Hyp이고, J는 Tic; Aoc; 또는 Oic이며, K는 Arg; Ahx; 또는 직접 결합이고, R2는 하이드록시; 또는 아미노이다.
- 제5항에 있어서, R1이 수소; 머캅토 또는 (4-벤조일)펜옥시에 의해 치환될 수 있는 아세틸; 또는 (4-벤조일)벤조일-Lys이고, A가 D-Arg; 또는 직접 결합이며, B가 톨루올-4-설포닐에 의해 치환될 수 있는 Arg; 또는 직접 결합이고, C가 Pro-Hyp-Gly; Pro-Pro-Cly; 또는 데하이드로 Pro-Hyp-Gly이며, E가 Thi; Phe; 또는 Leu이고, F가 Ser; 또는 Cys이며, G가 D-Tic; D-Phe; D-HypE(트랜스메틸); 또는 D-HypE(트랜스프로필)이고, J가 Tic; Aoc; 또는 Oic이며, K가 Arg이고, R2가 하이드록시인 서열식(1)의 펩타이드 또는 이의 생리학적으로 허용되는 염의 용도.
- 제5항 또는 6항에 있어서, R1이 수소; 또는 (4-벤조일) 벤조일-Lys이고, A가 D-Arg이며, B가 Arg이고, C가 Pro-Hyp-Gly; 또는 Pro-Pro-Gly이며, E가 Thi; Phe; 또는 Leu이고, F가 Ser이며, G가 D-Tic; 또는 D-HypE(트랜스프로필)이고, J가 Oic이며, K가 Arg이고, Y가 하이드록시인 서열식(1)의 펩타이드 또는 이의 생리학적으로 허용되는 염의 용도.
- 제5항 또는 제7항중 어느 한 항에 있어서, 급성 췌장염을 치료하기 위한 H-D-Arg-Arg-Pro-Hyp-G1y-Thi-Ser-D-Tic-Oic-Arg-OH(서열동정번호: 1), H-D-Arg-Arg-Pro-Pro-Gly-Thi-Ser-D-Tic-Oic-Arg-OH(서열동정번호: 2), H-D-Arg-Arg-Pro-Hyp-Gly-Phe-Ser-D-Tic-Oic-Arg-OH(서열동정번호: 3), H- (4-벤조일)벤조일)Lys-D-Arg-Arg-Pro-Hyp-Gly-Thi-Ser-D-Tic-Oic-Arg-OH(서열동정번호: 4), H-D-Arg-Arg-Pro-Hyp-Gly-Leu-Ser-D-Tic-Oic-Arg-OH(서열동정번호: 5), H-D-Arg-Arg-Pro-Hyp-Cly-Phe-Ser-D-HypE(트랜스프로필)-Oic-Arg-OH(서열동정번호: 6)을 포함하는 일련의 서열식(1)의 펩타이드 또는 이의 생리학적으로 허용되는 염의 용도.
- 활성 물질을 적합한 부형제, 보조제 및/또는 첨가제를 사용하여 적합한 투여 형태로 전환시킴을 특징으로하여, 제1항 내지 제4항에 따른 약제학적 제제를 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.
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EP91122055.6 | 1991-12-21 | ||
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US (1) | US5670619A (ko) |
EP (1) | EP0548825B1 (ko) |
JP (1) | JP3588472B2 (ko) |
KR (1) | KR930012034A (ko) |
CN (1) | CN1073603A (ko) |
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AU (1) | AU662188B2 (ko) |
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CZ (1) | CZ375692A3 (ko) |
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DK (1) | DK0548825T3 (ko) |
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SI (1) | SI9200406A (ko) |
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US7105172B1 (en) | 1999-11-18 | 2006-09-12 | Bolla John D | Treatment of rosacea |
US20040248809A1 (en) * | 2003-02-07 | 2004-12-09 | Aventis Pharma Deutschland Gmbh | Use of antagonists of the bradykinin B2 receptor for the treatment of osteoarthrosis |
RU2425669C1 (ru) * | 2010-04-13 | 2011-08-10 | Общество С Ограниченной Ответственностью "Гамаветфарм" | Средство для профилактики и лечения острого и хронического панкреатита |
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DE2964956D1 (en) * | 1978-07-18 | 1983-04-07 | Kabi Ab | Bradykinin inhibiting tripeptide derivatives, process for their preparation and pharmaceutical preparations containing them |
US4693993A (en) * | 1985-06-13 | 1987-09-15 | Stewart John M | Bradykinin antagonist peptides |
US4801613A (en) * | 1985-06-13 | 1989-01-31 | Nova Technology Limited Partnership | Bradykinin antagonist peptides |
US4923963A (en) * | 1987-09-02 | 1990-05-08 | Nova Technology Limited Partnership | Bradykinin antagonist peptides |
US5162497A (en) * | 1987-09-24 | 1992-11-10 | The Administrators Of The Tulane Educational Fund | Bradykinin analogs with non-peptide bond |
DE4013270A1 (de) * | 1990-04-26 | 1991-10-31 | Hoechst Ag | Peptide mit bradykinin-antagonistischer wirkung |
IE63490B1 (en) * | 1988-11-24 | 1995-05-03 | Hoechst Ag | Peptides having bradykinin antagonist action |
DE3926822A1 (de) * | 1989-08-14 | 1991-02-21 | Hoechst Ag | Peptide mit bradykinin-antagonistischer wirkung |
WO1991009055A1 (en) * | 1989-12-08 | 1991-06-27 | Boston University | Acylated bradykinin antagonists and uses therefor |
EP0451791A2 (de) * | 1990-04-12 | 1991-10-16 | Hoechst Aktiengesellschaft | Langwirksame Liposomenpräparate von Peptidarzneistoffen und Verfahren zu ihrer Herstellung |
-
1992
- 1992-03-26 TW TW081102310A patent/TW199863B/zh active
- 1992-12-14 BG BG097168A patent/BG97168A/bg unknown
- 1992-12-16 MA MA23033A patent/MA22743A1/fr unknown
- 1992-12-17 PL PL29704492A patent/PL297044A1/xx unknown
- 1992-12-17 AU AU30212/92A patent/AU662188B2/en not_active Ceased
- 1992-12-18 DE DE69219574T patent/DE69219574T2/de not_active Expired - Lifetime
- 1992-12-18 AT AT92121558T patent/ATE152733T1/de active
- 1992-12-18 BR BR9205062A patent/BR9205062A/pt not_active Application Discontinuation
- 1992-12-18 ZA ZA929829A patent/ZA929829B/xx unknown
- 1992-12-18 CA CA002085781A patent/CA2085781C/en not_active Expired - Lifetime
- 1992-12-18 NO NO92924925A patent/NO924925L/no unknown
- 1992-12-18 JP JP33773592A patent/JP3588472B2/ja not_active Expired - Lifetime
- 1992-12-18 FI FI925782A patent/FI925782A/fi unknown
- 1992-12-18 DK DK92121558.8T patent/DK0548825T3/da active
- 1992-12-18 MX MX9207440A patent/MX9207440A/es unknown
- 1992-12-18 IL IL104163A patent/IL104163A0/xx unknown
- 1992-12-18 EP EP92121558A patent/EP0548825B1/en not_active Expired - Lifetime
- 1992-12-18 YU YU108192A patent/YU108192A/sh unknown
- 1992-12-18 ES ES92121558T patent/ES2101017T3/es not_active Expired - Lifetime
- 1992-12-18 CZ CS923756A patent/CZ375692A3/cs unknown
- 1992-12-19 KR KR1019920024742A patent/KR930012034A/ko not_active Application Discontinuation
- 1992-12-21 SI SI19929200406A patent/SI9200406A/sl unknown
- 1992-12-21 CN CN92114564A patent/CN1073603A/zh active Pending
- 1992-12-21 HU HU9204074A patent/HU214056B/hu not_active IP Right Cessation
-
1994
- 1994-04-22 US US08/232,338 patent/US5670619A/en not_active Expired - Lifetime
-
1997
- 1997-07-22 GR GR970401824T patent/GR3024179T3/el unknown
-
1998
- 1998-09-29 CY CY9800034A patent/CY2116B1/xx unknown
Also Published As
Publication number | Publication date |
---|---|
SI9200406A (en) | 1993-06-30 |
CZ375692A3 (en) | 1993-12-15 |
EP0548825A1 (en) | 1993-06-30 |
TW199863B (ko) | 1993-02-11 |
JP3588472B2 (ja) | 2004-11-10 |
PL297044A1 (en) | 1993-09-06 |
HUT63336A (en) | 1993-08-30 |
DK0548825T3 (da) | 1997-11-03 |
CN1073603A (zh) | 1993-06-30 |
HU214056B (en) | 1997-12-29 |
NO924925D0 (no) | 1992-12-18 |
AU662188B2 (en) | 1995-08-24 |
DE69219574D1 (de) | 1997-06-12 |
HU9204074D0 (en) | 1993-04-28 |
YU108192A (sh) | 1995-12-04 |
US5670619A (en) | 1997-09-23 |
MA22743A1 (fr) | 1993-07-01 |
AU3021292A (en) | 1993-06-24 |
FI925782A0 (fi) | 1992-12-18 |
DE69219574T2 (de) | 1997-11-13 |
CY2116B1 (en) | 2002-04-26 |
MX9207440A (es) | 1993-07-01 |
ZA929829B (en) | 1994-02-16 |
FI925782A (fi) | 1993-06-22 |
IL104163A0 (en) | 1993-05-13 |
BR9205062A (pt) | 1993-09-28 |
ES2101017T3 (es) | 1997-07-01 |
EP0548825B1 (en) | 1997-05-07 |
CA2085781A1 (en) | 1993-06-22 |
BG97168A (bg) | 1993-12-24 |
ATE152733T1 (de) | 1997-05-15 |
GR3024179T3 (en) | 1997-10-31 |
NO924925L (no) | 1993-06-22 |
CA2085781C (en) | 2003-09-23 |
JPH05255107A (ja) | 1993-10-05 |
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