KR970005172B1 - 15-케토프로스타글란딘 화합물을 이용한 백내장의 치료 - Google Patents
15-케토프로스타글란딘 화합물을 이용한 백내장의 치료 Download PDFInfo
- Publication number
- KR970005172B1 KR970005172B1 KR1019910005502A KR910005502A KR970005172B1 KR 970005172 B1 KR970005172 B1 KR 970005172B1 KR 1019910005502 A KR1019910005502 A KR 1019910005502A KR 910005502 A KR910005502 A KR 910005502A KR 970005172 B1 KR970005172 B1 KR 970005172B1
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- South Korea
- Prior art keywords
- compound
- keto
- alkyl
- dihydro
- difluoro
- Prior art date
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- Expired - Lifetime
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- 150000001875 compounds Chemical class 0.000 claims description 225
- 239000000203 mixture Substances 0.000 claims description 101
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
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- 235000010409 propane-1,2-diol alginate Nutrition 0.000 description 6
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- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 5
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- YCJZWBZJSYLMPB-UHFFFAOYSA-N n-(2-chloropyrimidin-4-yl)-2,5-dimethyl-1-phenylimidazole-4-carboxamide Chemical compound CC=1N(C=2C=CC=CC=2)C(C)=NC=1C(=O)NC1=CC=NC(Cl)=N1 YCJZWBZJSYLMPB-UHFFFAOYSA-N 0.000 description 1
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
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- 229940054534 ophthalmic solution Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- WKMKTIVRRLOHAJ-UHFFFAOYSA-N oxygen(2-);thallium(1+) Chemical compound [O-2].[Tl+].[Tl+] WKMKTIVRRLOHAJ-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
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- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
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- RRUYLMFSYDCRIZ-ADMXILSSSA-N propan-2-yl (z)-9-[(1r,2r,3r)-3-hydroxy-5-oxo-2-(3-oxodecyl)cyclopentyl]non-7-enoate Chemical compound CCCCCCCC(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCCCC(=O)OC(C)C RRUYLMFSYDCRIZ-ADMXILSSSA-N 0.000 description 1
- NFUUAVFPTHMLHW-VOQKXKRBSA-N propan-2-yl (z)-9-[(1r,2r,3r,5s)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]non-7-enoate Chemical compound CCCCCCCC(=O)CC[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCCCC(=O)OC(C)C NFUUAVFPTHMLHW-VOQKXKRBSA-N 0.000 description 1
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical compound CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- NPRDHMWYZHSAHR-UHFFFAOYSA-N pyridine;trioxochromium Chemical compound O=[Cr](=O)=O.C1=CC=NC=C1.C1=CC=NC=C1 NPRDHMWYZHSAHR-UHFFFAOYSA-N 0.000 description 1
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- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 201000008525 senile cataract Diseases 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
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- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
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- 125000005490 tosylate group Chemical group 0.000 description 1
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
- A61K31/5575—Eicosanoids, e.g. leukotrienes or prostaglandins having a cyclopentane, e.g. prostaglandin E2, prostaglandin F2-alpha
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP90895/1990 | 1990-04-04 | ||
| JP90895 | 1990-04-04 | ||
| JP9089590 | 1990-04-04 | ||
| JP221646/1990 | 1990-08-22 | ||
| JP22164690 | 1990-08-22 | ||
| JP221646 | 1990-08-22 | ||
| JP2931091 | 1991-01-29 | ||
| JP29310/1991 | 1991-01-29 | ||
| JP29310 | 1991-01-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR910018027A KR910018027A (ko) | 1991-11-30 |
| KR970005172B1 true KR970005172B1 (ko) | 1997-04-14 |
Family
ID=27286510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019910005502A Expired - Lifetime KR970005172B1 (ko) | 1990-04-04 | 1991-04-04 | 15-케토프로스타글란딘 화합물을 이용한 백내장의 치료 |
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|---|---|
| US (2) | US5212324A (enExample) |
| EP (1) | EP0453127B1 (enExample) |
| KR (1) | KR970005172B1 (enExample) |
| AT (1) | ATE169219T1 (enExample) |
| AU (1) | AU644148B2 (enExample) |
| CA (1) | CA2039420C (enExample) |
| DE (1) | DE69129921T2 (enExample) |
| DK (1) | DK0453127T3 (enExample) |
| ES (1) | ES2119762T3 (enExample) |
| GR (1) | GR3027666T3 (enExample) |
| TW (2) | TW224942B (enExample) |
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| TW205508B (enExample) * | 1990-08-02 | 1993-05-11 | Kabushikaisha Ueno Seiyaku Oyo Kenkyujo | |
| US5352708A (en) * | 1992-09-21 | 1994-10-04 | Allergan, Inc. | Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents |
| US5688819A (en) * | 1992-09-21 | 1997-11-18 | Allergan | Cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl derivatives as therapeutic agents |
| US5972991A (en) | 1992-09-21 | 1999-10-26 | Allergan | Cyclopentane heptan(ene) oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
| US5328933A (en) * | 1992-10-28 | 1994-07-12 | Allergan, Inc. | Cyclopentane heptenylnitro and heptanylnitro-2-aliphatic or aryl aliphatic derivatives and homologues |
| SE9303627D0 (sv) * | 1993-11-03 | 1993-11-03 | Kabi Pharmacia Ab | Method and means for prevention of cataract |
| EP0735895B1 (en) * | 1993-11-19 | 2006-01-18 | The University Of Sydney | A method for preventing or controlling cataract |
| SE9403160D0 (sv) * | 1994-09-21 | 1994-09-21 | Pharmacia Ab | Method and means for prevention and treatment of secondary cataract |
| ES2182088T3 (es) | 1996-06-10 | 2003-03-01 | Sucampo Ag | Antagonista de la endotelina. |
| IL134839A0 (en) * | 1997-09-09 | 2001-05-20 | Procter & Gamble | Aromatic c16-c20-substituted tetrahydro prostaglandins useful as fp agonists |
| DK1012137T3 (da) * | 1997-09-09 | 2003-03-10 | Procter & Gamble | Aromatiske C-16-C-20-substituerede tetrahydro-prostaglandiner og deres anvendelse som prostaglandin FP-agonister |
| ATE401894T1 (de) * | 1997-11-28 | 2008-08-15 | Sucampo Ag | Verwendung von 15-keto-prostaglandin-e verbindungen als endothelin antagonisten |
| WO2000051980A1 (en) | 1999-03-05 | 2000-09-08 | The Procter & Gamble Company | C16 unsaturated fp-selective prostaglandins analogs |
| TWI225398B (en) * | 1999-07-14 | 2004-12-21 | R Tech Ueno Ltd | Composition for treatment of external secretion disorders |
| US6458836B1 (en) | 2000-03-16 | 2002-10-01 | Sucampo, A.G. | Treatment of ocular hypertension and glaucoma |
| HUP0300391A3 (en) * | 2000-03-16 | 2008-05-28 | Sucampo Ag | Use of prostaglandin related compounds for preparation of composition for use in treatment of ocular hypertension and glaucoma |
| JP2003527430A (ja) | 2000-03-24 | 2003-09-16 | スカンポ・アクチェンゲゼルシャフト | １５−ケトプロスタグランジンまたはその誘導体を含むアポトーシス抑制剤 |
| US20020013294A1 (en) | 2000-03-31 | 2002-01-31 | Delong Mitchell Anthony | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
| US20020146439A1 (en) * | 2000-03-31 | 2002-10-10 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using oximyl and hydroxylamino prostaglandins |
| US20020172693A1 (en) | 2000-03-31 | 2002-11-21 | Delong Michell Anthony | Compositions and methods for treating hair loss using non-naturally occurring prostaglandins |
| US20020037914A1 (en) * | 2000-03-31 | 2002-03-28 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
| MXPA02009915A (es) * | 2000-04-06 | 2003-03-27 | Sucampo Ag | Composicion promotora de secrecion de bilis. |
| TWI302100B (en) | 2001-05-02 | 2008-10-21 | Sucampo Ag | Composition for treating drug-induced constipation |
| KR20040029012A (ko) * | 2001-08-23 | 2004-04-03 | 수캄포 아게 | 안내압항진 및 녹내장 치료용 방법 및 조성물 |
| CA2458471C (en) | 2001-08-31 | 2012-07-31 | Sucampo Ag | Prostaglandin analogs as chloride channel opener |
| US8580851B2 (en) * | 2002-08-21 | 2013-11-12 | Sucampo Ag | Ophthalmic solution |
| WO2005018646A1 (ja) | 2003-08-21 | 2005-03-03 | Sucampo Ag | 眼科用組成物 |
| WO2004037268A1 (en) * | 2002-10-23 | 2004-05-06 | Sucampo Ag | Prostaglandin compounds for the treatment of obesity |
| JP4889219B2 (ja) | 2002-12-27 | 2012-03-07 | スキャンポ・アーゲー | 腹部不快感の処置のためのプロスタグランジン誘導体 |
| US8337891B2 (en) * | 2003-07-03 | 2012-12-25 | Sucampo Ag | Enteric coated composition comprising prostaglandin analogs as chloride channel opener |
| TWI348386B (en) * | 2003-08-12 | 2011-09-11 | R Tech Ueno Ltd | Composition and method for promoting hair growth |
| SE0303179D0 (sv) * | 2003-11-26 | 2003-11-26 | Astrazeneca Ab | Novel compounds |
| US7321057B2 (en) * | 2004-08-02 | 2008-01-22 | R-Tech Ueno, Ltd. | Method for manufacturing prostaglandin analogue |
| CA2595898C (en) | 2005-01-27 | 2015-04-28 | Sucampo Ag | Method and composition for treating central nervous system disorders |
| DK1853271T3 (da) | 2005-03-04 | 2011-01-24 | Sucampo Ag | Fremgangsmåde og præparat til behandling af perifere vaskulære sygdomme |
| US7851504B2 (en) | 2005-03-16 | 2010-12-14 | Allergan, Inc. | Enhanced bimatoprost ophthalmic solution |
| US9241918B2 (en) | 2005-03-16 | 2016-01-26 | Allergan, Inc. | Enhanced bimatoprost ophthalmic solution |
| US20060281818A1 (en) | 2005-03-21 | 2006-12-14 | Sucampo Ag, North Carolina State University | Method for treating mucosal disorders |
| JP5711442B2 (ja) * | 2005-04-12 | 2015-04-30 | スキャンポ・アーゲーＳｕｃａｍｐｏ ＡＧ | 胃腸障害の処置のためのプロスタグランジン化合物およびプロトンポンプ阻害剤の併用 |
| CN104971056A (zh) | 2006-01-24 | 2015-10-14 | 株式会社·R-技术上野 | 软明胶胶囊制剂 |
| KR20140147142A (ko) | 2006-01-24 | 2014-12-29 | 가부시키가이샤 아루떼꾸 우에노 | 바이-사이클릭 화합물을 함유하는 약학적 조성물 및 바이-사이클릭 화합물의 안정화 방법 |
| JPWO2007105691A1 (ja) | 2006-03-13 | 2009-07-30 | 株式会社アールテック・ウエノ | 水性組成物 |
| US8871752B2 (en) | 2008-02-19 | 2014-10-28 | Sucampo Ag | Method for modulating stem cell growth |
| US8722739B2 (en) * | 2008-10-29 | 2014-05-13 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| US8623918B2 (en) * | 2008-10-29 | 2014-01-07 | Novaer Holdings, Inc. | Amino acid salts of prostaglandins |
| US8609729B2 (en) * | 2009-04-15 | 2013-12-17 | Sucampo Ag | Method for treating macular degeneration |
| US8569279B2 (en) * | 2009-05-27 | 2013-10-29 | Sucampo Ag | Method for modulating claudin mediated functions |
| US9084815B2 (en) * | 2009-09-16 | 2015-07-21 | Sucampo Ag | Method for treating damage induced by an anti-tumor agent, treating mucositis and treating tumor |
| US9522153B2 (en) | 2009-12-22 | 2016-12-20 | Allergan, Inc. | Compositions and methods for lowering intraocular pressure |
| JP2014510022A (ja) | 2011-04-07 | 2014-04-24 | スキャンポ・アーゲー | 眼精疲労の処置方法 |
| JP6193230B2 (ja) | 2011-08-05 | 2017-09-06 | スキャンポ・アーゲーＳｕｃａｍｐｏ ＡＧ | 統合失調症の処置方法 |
| AR092821A1 (es) | 2012-04-20 | 2015-05-06 | Sucampo Ag | Conjugado de derivado de acido graso-polimero |
| US20150057351A1 (en) | 2013-08-22 | 2015-02-26 | Sucampo Ag | Method for treating neuropathic pain |
| AR105029A1 (es) | 2015-06-19 | 2017-08-30 | Sucampo Ag | Composición farmacéutica que comprende derivado de ácido graso |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3505386A (en) * | 1965-12-29 | 1970-04-07 | Upjohn Co | Compounds related to prostaglandins |
| US3974195A (en) * | 1974-10-02 | 1976-08-10 | The Upjohn Company | 2A,2B-Dihomo-15-alkyl-PGF2.sub.α analogs |
| EP0153858A3 (en) * | 1984-02-29 | 1985-12-11 | The Upjohn Company | The therapeutic use of prostaglandins |
| CA1322749C (en) * | 1987-01-28 | 1993-10-05 | Ryuzo Ueno | Prostaglandins of the d series, and tranquilizers and soporifics containing the same |
| CA1323364C (en) * | 1987-01-28 | 1993-10-19 | Ryuzo Ueno | Prostaglandins e and anti ulcer agents containing same |
| CA1324129C (en) * | 1987-04-30 | 1993-11-09 | Ryuzo Ueno | Prostaglandins of the f series |
| DE3869471D1 (de) * | 1987-05-15 | 1992-04-30 | Ueno Seiyaku Oyo Kenkyujo Kk | Fiebersteigende zusammensetzung. |
| GB2209939B (en) * | 1987-09-18 | 1992-01-02 | R Tech Ueno Ltd | The use of 13,14-dihydro-15-keto-prostaglandins as ocular hypotensive agents |
| EP0310305B1 (en) * | 1987-10-02 | 1992-07-22 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Cathartics |
| JP2597629B2 (ja) * | 1988-02-26 | 1997-04-09 | 株式会社 上野製薬応用研究所 | １３，１４−ジヒドロ−１５−ケトプロスタグランジン類の安定化 |
| AU619543B2 (en) * | 1988-05-11 | 1992-01-30 | Sucampo Ag | Use of 15-ketoprostaglandin e or f compounds for uterine contraction |
| JP2597649B2 (ja) * | 1988-05-11 | 1997-04-09 | 株式会社上野製薬応用研究所 | 気管・気管支拡張剤 |
| DE68906193T2 (de) * | 1988-05-23 | 1993-08-05 | Ueno Seiyaku Oyo Kenkyujo Kk | Hypersphyxia verursachende zusammensetzung. |
| AU604156B2 (en) * | 1988-09-14 | 1990-12-06 | R-Tech Ueno, Ltd. | Prostaglandins of the F series |
| ATE111736T1 (de) * | 1988-10-01 | 1994-10-15 | R Tech Ueno Ltd | Okulare hypotensive mittel. |
| TW205508B (enExample) * | 1990-08-02 | 1993-05-11 | Kabushikaisha Ueno Seiyaku Oyo Kenkyujo |
-
1991
- 1991-03-28 TW TW080102419A patent/TW224942B/zh not_active IP Right Cessation
- 1991-03-28 CA CA002039420A patent/CA2039420C/en not_active Expired - Lifetime
- 1991-03-28 TW TW081106617A patent/TW249226B/zh not_active IP Right Cessation
- 1991-04-03 US US07/680,187 patent/US5212324A/en not_active Expired - Lifetime
- 1991-04-03 ES ES91302925T patent/ES2119762T3/es not_active Expired - Lifetime
- 1991-04-03 DE DE69129921T patent/DE69129921T2/de not_active Expired - Lifetime
- 1991-04-03 AU AU74047/91A patent/AU644148B2/en not_active Expired
- 1991-04-03 EP EP91302925A patent/EP0453127B1/en not_active Expired - Lifetime
- 1991-04-03 AT AT91302925T patent/ATE169219T1/de not_active IP Right Cessation
- 1991-04-03 DK DK91302925T patent/DK0453127T3/da active
- 1991-04-04 KR KR1019910005502A patent/KR970005172B1/ko not_active Expired - Lifetime
-
1994
- 1994-09-06 US US08/300,541 patent/US5686487A/en not_active Expired - Lifetime
-
1998
- 1998-08-19 GR GR980400874T patent/GR3027666T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0453127A2 (en) | 1991-10-23 |
| DK0453127T3 (da) | 1998-10-26 |
| AU7404791A (en) | 1991-10-10 |
| EP0453127A3 (en) | 1992-12-09 |
| GR3027666T3 (en) | 1998-11-30 |
| CA2039420A1 (en) | 1991-10-05 |
| TW249226B (enExample) | 1995-06-11 |
| CA2039420C (en) | 1996-12-10 |
| TW224942B (enExample) | 1994-06-11 |
| US5212324A (en) | 1993-05-18 |
| KR910018027A (ko) | 1991-11-30 |
| ATE169219T1 (de) | 1998-08-15 |
| DE69129921D1 (de) | 1998-09-10 |
| DE69129921T2 (de) | 1999-01-14 |
| ES2119762T3 (es) | 1998-10-16 |
| US5686487A (en) | 1997-11-11 |
| EP0453127B1 (en) | 1998-08-05 |
| AU644148B2 (en) | 1993-12-02 |
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