KR930000051B1 - 안구의 저혈압 치료제 - Google Patents
안구의 저혈압 치료제 Download PDFInfo
- Publication number
- KR930000051B1 KR930000051B1 KR1019880012030A KR880012030A KR930000051B1 KR 930000051 B1 KR930000051 B1 KR 930000051B1 KR 1019880012030 A KR1019880012030 A KR 1019880012030A KR 880012030 A KR880012030 A KR 880012030A KR 930000051 B1 KR930000051 B1 KR 930000051B1
- Authority
- KR
- South Korea
- Prior art keywords
- dihydro
- keto
- ethyl
- prostaglandin
- pge
- 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 - Lifetime
Links
- 208000007950 Ocular Hypotension Diseases 0.000 title claims description 14
- -1 hydroxy, hydroxy Chemical group 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 14
- 208000001953 Hypotension Diseases 0.000 claims description 12
- 150000000258 13,14-dihydro-15-keto-prostaglandin D2 derivatives Chemical class 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 229940124597 therapeutic agent Drugs 0.000 claims description 8
- 230000036543 hypotension Effects 0.000 claims description 7
- 208000010412 Glaucoma Diseases 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- TVHAZVBUYQMHBC-SNHXEXRGSA-N unoprostone Chemical compound CCCCCCCC(=O)CC[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O TVHAZVBUYQMHBC-SNHXEXRGSA-N 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
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- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- VKTIONYPMSCHQI-XAGFEHLVSA-N 13,14-dihydro-15-keto-PGF2alpha Chemical compound CCCCCC(=O)CC[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O VKTIONYPMSCHQI-XAGFEHLVSA-N 0.000 claims 2
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- 230000035479 physiological effects, processes and functions Effects 0.000 claims 1
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- 238000003822 preparative gas chromatography Methods 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
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- 125000004432 carbon atom Chemical group C* 0.000 description 10
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
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- 238000007254 oxidation reaction Methods 0.000 description 7
- CUJMXIQZWPZMNQ-XYYGWQPLSA-N 13,14-dihydro-15-oxo-prostaglandin E2 Chemical compound CCCCCC(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O CUJMXIQZWPZMNQ-XYYGWQPLSA-N 0.000 description 6
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
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- 125000001424 substituent group Chemical group 0.000 description 6
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
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- 208000021822 hypotensive Diseases 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
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- 238000011200 topical administration Methods 0.000 description 5
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- 239000004215 Carbon black (E152) Substances 0.000 description 4
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- 239000007900 aqueous suspension Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 210000004087 cornea Anatomy 0.000 description 4
- 210000003608 fece Anatomy 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 238000002690 local anesthesia Methods 0.000 description 4
- 239000002207 metabolite Substances 0.000 description 4
- PRGUDWLMFLCODA-UHFFFAOYSA-N oxybuprocaine hydrochloride Chemical compound [Cl-].CCCCOC1=CC(C(=O)OCC[NH+](CC)CC)=CC=C1N PRGUDWLMFLCODA-UHFFFAOYSA-N 0.000 description 4
- 230000001766 physiological effect Effects 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000009530 blood pressure measurement Methods 0.000 description 3
- 210000000795 conjunctiva Anatomy 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 238000010537 deprotonation reaction Methods 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- VSRXYLYXIXYEST-KZTWKYQFSA-N 13,14-dihydro-15-ketoprostaglandin D2 Chemical compound CCCCCC(=O)CC[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O VSRXYLYXIXYEST-KZTWKYQFSA-N 0.000 description 2
- CDUVSQMTLOYKTR-ZHALLVOQSA-N 13,14-dihydro-15-oxoprostaglandin E1 Chemical compound CCCCCC(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O CDUVSQMTLOYKTR-ZHALLVOQSA-N 0.000 description 2
- FMKLAIBZMCURLI-BFVRRIQPSA-N 15-Keto-13,14-dihydroprostaglandin A2 Chemical compound CCCCCC(=O)CC[C@H]1C=CC(=O)[C@@H]1C\C=C/CCCC(O)=O FMKLAIBZMCURLI-BFVRRIQPSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
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- CVMKPYXSQWWZFH-UHFFFAOYSA-N 1-dimethoxyphosphorylnonan-2-one Chemical compound CCCCCCCC(=O)CP(=O)(OC)OC CVMKPYXSQWWZFH-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Ophthalmology & Optometry (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Materials For Medical Uses (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP235890/87 | 1987-09-18 | ||
| JP235890 | 1987-09-18 | ||
| JP23589087 | 1987-09-18 | ||
| JP334037/87 | 1987-12-29 | ||
| JP33403787 | 1987-12-29 | ||
| JP334037 | 1987-12-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR890004707A KR890004707A (ko) | 1989-05-09 |
| KR930000051B1 true KR930000051B1 (ko) | 1993-01-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019880012030A Expired - Lifetime KR930000051B1 (ko) | 1987-09-18 | 1988-09-16 | 안구의 저혈압 치료제 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5001153A (enExample) |
| EP (2) | EP0308135B1 (enExample) |
| JP (2) | JPH02108A (enExample) |
| KR (1) | KR930000051B1 (enExample) |
| AT (2) | ATE108330T1 (enExample) |
| CA (1) | CA1328075C (enExample) |
| DE (2) | DE3850676T2 (enExample) |
| ES (1) | ES2052735T3 (enExample) |
| GB (1) | GB2209939B (enExample) |
| GR (1) | GR3006319T3 (enExample) |
| NZ (1) | NZ226197A (enExample) |
Families Citing this family (112)
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|---|---|---|---|---|
| CA1322749C (en) * | 1987-01-28 | 1993-10-05 | Ryuzo Ueno | Prostaglandins of the d series, and tranquilizers and soporifics containing the same |
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| EP1300150A3 (en) * | 1988-09-06 | 2003-05-14 | Pharmacia Aktiebolag | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
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| US5321128A (en) * | 1988-09-06 | 1994-06-14 | Kabi Pharmacia Ab | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
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| ATE121624T1 (de) * | 1989-08-09 | 1995-05-15 | Ueno Seiyaku Oyo Kenkyujo Kk | Verwendung von prostansäurederivaten zur herstellung von arzneimitteln zur verbesserung der ausscheidung von nichtprotein in die därme. |
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| TW249226B (enExample) * | 1990-04-04 | 1995-06-11 | Aderk Ueno Kk | |
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| DK2498783T3 (en) | 2009-11-09 | 2018-12-10 | Allergan Inc | COMPOSITIONS AND PROCEDURES FOR STIMULATING HAIR GROWTH |
| US9149484B2 (en) | 2009-11-09 | 2015-10-06 | Allergan, Inc. | Compositions and methods for stimulating hair growth |
| BR112013002584A2 (pt) | 2010-08-02 | 2016-06-07 | Pharma Patent Holding Inc | composição, processo de kit para aperfeiçoamento de cabelo |
| US8859616B2 (en) | 2011-01-21 | 2014-10-14 | Allergan, Inc. | Compounds and methods for enhancing hair growth |
| EP2671586B1 (en) | 2011-02-04 | 2018-05-30 | Kowa Co., Ltd. | Drug therapy for preventing or treating glaucoma |
| 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 |
| UA124698C2 (uk) | 2014-10-20 | 2021-11-03 | Сентіс Фарма Прайвет Лімітед | Офтальмологічний розчин |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1476661A (en) * | 1974-05-13 | 1977-06-16 | American Cyanamid Co | Prostaglandins |
| US4599353A (en) * | 1982-05-03 | 1986-07-08 | The Trustees Of Columbia University In The City Of New York | Use of eicosanoids and their derivatives for treatment of ocular hypertension and glaucoma |
| ES2053458T3 (es) * | 1986-03-13 | 1994-08-01 | Univ Columbia | Utilizacion de prostaglandinas a, b y c y derivados de las mismas, para el tratamiento de la hipertension ocular y glaucoma. |
| US4824857A (en) * | 1986-05-16 | 1989-04-25 | Yasumasa Goh | Use of prostaglandin D2 -active substances |
| 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. |
| JPS6453101A (en) * | 1987-05-25 | 1989-03-01 | Kurashiki Boseki Kk | Equal tilt angle interference type film thickness gauge |
| 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 |
-
1988
- 1988-09-08 DE DE3850676T patent/DE3850676T2/de not_active Expired - Lifetime
- 1988-09-08 AT AT91108317T patent/ATE108330T1/de not_active IP Right Cessation
- 1988-09-08 AT AT88308299T patent/ATE82499T1/de not_active IP Right Cessation
- 1988-09-08 DE DE8888308299T patent/DE3876050T2/de not_active Expired - Lifetime
- 1988-09-08 GB GB8821104A patent/GB2209939B/en not_active Expired - Lifetime
- 1988-09-08 ES ES88308299T patent/ES2052735T3/es not_active Expired - Lifetime
- 1988-09-08 EP EP88308299A patent/EP0308135B1/en not_active Expired - Lifetime
- 1988-09-08 EP EP91108317A patent/EP0455264B1/en not_active Expired - Lifetime
- 1988-09-13 CA CA000577220A patent/CA1328075C/en not_active Expired - Lifetime
- 1988-09-14 JP JP63230469A patent/JPH02108A/ja active Granted
- 1988-09-15 NZ NZ226197A patent/NZ226197A/en unknown
- 1988-09-16 KR KR1019880012030A patent/KR930000051B1/ko not_active Expired - Lifetime
- 1988-09-19 US US07/246,059 patent/US5001153A/en not_active Expired - Lifetime
-
1992
- 1992-11-24 GR GR920402682T patent/GR3006319T3/el unknown
-
1993
- 1993-02-12 JP JP5024099A patent/JP2592204B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GR3006319T3 (enExample) | 1993-06-21 |
| GB2209939B (en) | 1992-01-02 |
| JPH0571567B2 (enExample) | 1993-10-07 |
| DE3876050D1 (de) | 1992-12-24 |
| CA1328075C (en) | 1994-03-29 |
| ES2052735T3 (es) | 1994-07-16 |
| DE3876050T2 (de) | 1993-03-25 |
| AU2231388A (en) | 1989-03-23 |
| GB2209939A (en) | 1989-06-01 |
| US5001153A (en) | 1991-03-19 |
| EP0455264B1 (en) | 1994-07-13 |
| GB8821104D0 (en) | 1988-10-05 |
| NZ226197A (en) | 1992-02-25 |
| EP0455264A3 (en) | 1991-11-27 |
| EP0455264A2 (en) | 1991-11-06 |
| JPH02108A (ja) | 1990-01-05 |
| DE3850676T2 (de) | 1994-11-03 |
| JPH0680571A (ja) | 1994-03-22 |
| KR890004707A (ko) | 1989-05-09 |
| DE3850676D1 (de) | 1994-08-18 |
| EP0308135A2 (en) | 1989-03-22 |
| JP2592204B2 (ja) | 1997-03-19 |
| ATE108330T1 (de) | 1994-07-15 |
| EP0308135A3 (en) | 1989-06-14 |
| ATE82499T1 (de) | 1992-12-15 |
| EP0308135B1 (en) | 1992-11-19 |
| AU600168B2 (en) | 1990-08-02 |
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