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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- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
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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
- ZBQCPWMIGVSOGB-UHFFFAOYSA-N non-7-enoic acid Chemical compound CC=CCCCCCC(O)=O ZBQCPWMIGVSOGB-UHFFFAOYSA-N 0.000 description 1
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- 230000003000 nontoxic effect Effects 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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- 235000008390 olive oil Nutrition 0.000 description 1
- 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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- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 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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- 238000003822 preparative gas chromatography Methods 0.000 description 1
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- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 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
- 230000005855 radiation Effects 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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- 125000001544 thienyl group Chemical group 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 | 1990-04-04 | ||
| JP9089590 | 1990-04-04 | ||
| JP90895/1990 | 1990-04-04 | ||
| JP22164690 | 1990-08-22 | ||
| JP221646/1990 | 1990-08-22 | ||
| JP221646 | 1990-08-22 | ||
| JP2931091 | 1991-01-29 | ||
| JP29310/1991 | 1991-01-29 | ||
| JP29310 | 1992-04-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR910018027A KR910018027A (ko) | 1991-11-30 |
| KR970005172B1 true KR970005172B1 (ko) | 1997-04-14 |
Family
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Family Applications (1)
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|---|---|---|---|
| KR1019910005502A Expired - Lifetime KR970005172B1 (ko) | 1990-04-04 | 1991-04-04 | 15-케토프로스타글란딘 화합물을 이용한 백내장의 치료 |
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|---|---|
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| 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) | TW249226B (enExample) |
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| TW205508B (enExample) * | 1990-08-02 | 1993-05-11 | Kabushikaisha Ueno Seiyaku Oyo Kenkyujo | |
| 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 |
| US5352708A (en) * | 1992-09-21 | 1994-10-04 | Allergan, Inc. | Non-acidic cyclopentane heptanoic acid, 2-cycloalkyl or arylalkyl 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 |
| DE69434617D1 (de) * | 1993-11-19 | 2006-04-06 | Univ Sydney | Verfahren zur prophylaxe oder kontrolle des katarakts |
| SE9403160D0 (sv) * | 1994-09-21 | 1994-09-21 | Pharmacia Ab | Method and means for prevention and treatment of secondary cataract |
| CN102126998B (zh) * | 1996-06-10 | 2013-06-12 | 苏坎波公司 | 内皮素拮抗剂 |
| DE69809268T2 (de) * | 1997-09-09 | 2003-08-28 | The Procter & Gamble Co., Cincinnati | Aromatische c16-c20-substituierte tetrahydro-prostaglandine und ihre verwendung als prostaglandin f agonisten |
| BR9811774A (pt) * | 1997-09-09 | 2000-08-29 | Procter & Gamble | Tetraidroprostaglandinas aromáticas substituìdas por c16-c20 úteis como agonistas fp |
| DE69839767D1 (de) * | 1997-11-28 | 2008-09-04 | Sucampo Ag | Verwendung von 15-keto-prostaglandin-e verbindungen als endothelin antagonisten |
| ATE281432T1 (de) | 1999-03-05 | 2004-11-15 | Univ Duke | C-16 ungesätigte fp-selektive prostaglandin analoge |
| 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 |
| EP1272194A2 (en) * | 2000-03-16 | 2003-01-08 | Sucampo AG | Composition for use in treatment of ocular hypertension and glaucoma |
| WO2001070233A2 (en) | 2000-03-24 | 2001-09-27 | Sucampo Ag | Apoptosis inhibiting composition comprising a 15-keto-prostaglandin or derivative thereof |
| 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 |
| US20020013294A1 (en) * | 2000-03-31 | 2002-01-31 | Delong Mitchell Anthony | Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives |
| US20020037914A1 (en) | 2000-03-31 | 2002-03-28 | Delong Mitchell Anthony | Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins |
| CN1241570C (zh) | 2000-04-06 | 2006-02-15 | 苏坎波公司 | 胆汁分泌促进组合物 |
| TWI302100B (en) | 2001-05-02 | 2008-10-21 | Sucampo Ag | Composition for treating drug-induced constipation |
| JP2004521960A (ja) * | 2001-08-23 | 2004-07-22 | スキャンポ・アーゲー | 高眼圧症および緑内障の処置のための方法および組成物 |
| WO2003030912A1 (en) | 2001-08-31 | 2003-04-17 | Sucampo Ag | Prostaglandin analogs as chloride channel opener |
| US8580851B2 (en) * | 2002-08-21 | 2013-11-12 | Sucampo Ag | Ophthalmic solution |
| JP4705782B2 (ja) * | 2002-10-23 | 2011-06-22 | スキャンポ・アーゲー | 肥満の処置のためのプロスタグランジン化合物 |
| 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 |
| EP1641462B1 (en) * | 2003-07-03 | 2010-11-24 | Sucampo AG | Enteric coated composition comprising prostaglandin analogs as chloride channel opener |
| TWI495471B (zh) * | 2003-08-12 | 2015-08-11 | R Tech Ueno Ltd | 促進毛髮生長之組成物及方法 |
| EP1661573B1 (en) | 2003-08-21 | 2013-09-25 | Sucampo AG | Ophtalmic composition comprising unoprostone ispopropyl ester and a viscosity agent |
| SE0303179D0 (sv) * | 2003-11-26 | 2003-11-26 | Astrazeneca Ab | Novel compounds |
| JP4690814B2 (ja) * | 2004-08-02 | 2011-06-01 | 株式会社アールテック・ウエノ | プロスタグランジン誘導体の製造法 |
| NZ556710A (en) | 2005-01-27 | 2010-08-27 | Sucampo Ag | Method and composition for treating central nervous system disorders |
| NZ561414A (en) | 2005-03-04 | 2010-10-29 | Sucampo Ag | Method and composition for treating peripheral vascular diseases |
| 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 |
| EP1871380B1 (en) * | 2005-04-12 | 2011-10-19 | Sucampo AG | Combined use of prostaglandin compound and proton pump inhibitor for the treatment of gastrointestinal disorders |
| EP2682130A1 (en) | 2006-01-24 | 2014-01-08 | R-Tech Ueno, Ltd. | Pharmaceutical composition comprising a bi-cyclic compound and method for stabilizing the bi-cyclic compound |
| NZ570191A (en) * | 2006-01-24 | 2010-09-30 | R Tech Ueno Ltd | Soft-gelatin capsule formulation comprising a keto-prostaglandin compound |
| CN104224704A (zh) | 2006-03-13 | 2014-12-24 | 株式会社·R-技术上野 | 水性组合物 |
| 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 |
| EP2694077A4 (en) | 2011-04-07 | 2015-01-21 | Sucampo Ag | METHOD FOR TREATING ASTHENOPY |
| CN107903173A (zh) | 2011-08-05 | 2018-04-13 | 苏坎波公司 | 治疗精神分裂症的方法 |
| 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 |
| WO2016203317A1 (en) | 2015-06-19 | 2016-12-22 | Sucampo Ag | Pharmaceutical compositions comprising fatty acid derivative |
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|---|---|---|---|---|
| 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 |
| CA1323364C (en) * | 1987-01-28 | 1993-10-19 | Ryuzo Ueno | Prostaglandins e and anti ulcer agents containing same |
| CA1322749C (en) * | 1987-01-28 | 1993-10-05 | Ryuzo Ueno | Prostaglandins of the d series, and tranquilizers and soporifics containing the 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. |
| DE3850676T2 (de) * | 1987-09-18 | 1994-11-03 | Ueno Seiyaku Oyo Kenkyujo Kk | Hypotensive okulare Mittel. |
| DE3873007T2 (de) * | 1987-10-02 | 1992-12-03 | Ueno Seiyaku Oyo Kenkyujo Kk | Kathartica. |
| 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 |
| 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 |
| AU619543B2 (en) * | 1988-05-11 | 1992-01-30 | Sucampo Ag | Use of 15-ketoprostaglandin e or f compounds for uterine contraction |
| 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 |
| ATE162074T1 (de) * | 1988-10-01 | 1998-01-15 | R Tech Ueno Ltd | Oculare hypotensive mittel |
| TW205508B (enExample) * | 1990-08-02 | 1993-05-11 | Kabushikaisha Ueno Seiyaku Oyo Kenkyujo |
-
1991
- 1991-03-28 TW TW081106617A patent/TW249226B/zh not_active IP Right Cessation
- 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
- 1991-04-03 ES ES91302925T patent/ES2119762T3/es not_active Expired - Lifetime
- 1991-04-03 DE DE69129921T patent/DE69129921T2/de not_active Expired - Lifetime
- 1991-04-03 DK DK91302925T patent/DK0453127T3/da active
- 1991-04-03 US US07/680,187 patent/US5212324A/en not_active Expired - Lifetime
- 1991-04-03 AT AT91302925T patent/ATE169219T1/de not_active IP Right Cessation
- 1991-04-03 EP EP91302925A patent/EP0453127B1/en not_active Expired - Lifetime
- 1991-04-03 AU AU74047/91A patent/AU644148B2/en not_active Expired
- 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 |
|---|---|
| EP0453127A3 (en) | 1992-12-09 |
| US5212324A (en) | 1993-05-18 |
| EP0453127A2 (en) | 1991-10-23 |
| GR3027666T3 (en) | 1998-11-30 |
| TW224942B (enExample) | 1994-06-11 |
| KR910018027A (ko) | 1991-11-30 |
| US5686487A (en) | 1997-11-11 |
| EP0453127B1 (en) | 1998-08-05 |
| CA2039420C (en) | 1996-12-10 |
| CA2039420A1 (en) | 1991-10-05 |
| ATE169219T1 (de) | 1998-08-15 |
| AU644148B2 (en) | 1993-12-02 |
| DE69129921T2 (de) | 1999-01-14 |
| DE69129921D1 (de) | 1998-09-10 |
| TW249226B (enExample) | 1995-06-11 |
| AU7404791A (en) | 1991-10-10 |
| ES2119762T3 (es) | 1998-10-16 |
| DK0453127T3 (da) | 1998-10-26 |
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