KR870005985A - 구아니디노벤조 에스테르유도체 및 그의 제조방법 - Google Patents
구아니디노벤조 에스테르유도체 및 그의 제조방법 Download PDFInfo
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- KR870005985A KR870005985A KR860011333A KR860011333A KR870005985A KR 870005985 A KR870005985 A KR 870005985A KR 860011333 A KR860011333 A KR 860011333A KR 860011333 A KR860011333 A KR 860011333A KR 870005985 A KR870005985 A KR 870005985A
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- pharmacologically acceptable
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- 150000002148 esters Chemical class 0.000 title claims abstract 10
- 238000002360 preparation method Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- 206010033645 Pancreatitis Diseases 0.000 claims abstract 2
- 208000007536 Thrombosis Diseases 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 16
- -1 4- (2-hydroxyethylthio) phenyl Chemical group 0.000 claims 5
- 241001465754 Metazoa Species 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- PXPIXLVXGYQMFM-UHFFFAOYSA-N phenyl 4-(diaminomethylideneamino)benzoate Chemical compound C1=CC(N=C(N)N)=CC=C1C(=O)OC1=CC=CC=C1 PXPIXLVXGYQMFM-UHFFFAOYSA-N 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- FCEQRBOTYXIORK-UHFFFAOYSA-N 2-(diaminomethylideneamino)benzoic acid Chemical compound NC(=N)NC1=CC=CC=C1C(O)=O FCEQRBOTYXIORK-UHFFFAOYSA-N 0.000 claims 1
- 208000000668 Chronic Pancreatitis Diseases 0.000 claims 1
- KBAOCNGKFWTEFO-UHFFFAOYSA-N N(C(=N)N)C1=C(C(=O)O)C=CC=C1.[P] Chemical compound N(C(=N)N)C1=C(C(=O)O)C=CC=C1.[P] KBAOCNGKFWTEFO-UHFFFAOYSA-N 0.000 claims 1
- 206010033647 Pancreatitis acute Diseases 0.000 claims 1
- 206010033649 Pancreatitis chronic Diseases 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 201000003229 acute pancreatitis Diseases 0.000 claims 1
- 230000000740 bleeding effect Effects 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108010088842 Fibrinolysin Proteins 0.000 abstract 1
- 108090000190 Thrombin Proteins 0.000 abstract 1
- 108090000631 Trypsin Proteins 0.000 abstract 1
- 102000004142 Trypsin Human genes 0.000 abstract 1
- 229940088598 enzyme Drugs 0.000 abstract 1
- 208000031169 hemorrhagic disease Diseases 0.000 abstract 1
- 229940012957 plasmin Drugs 0.000 abstract 1
- 229960004072 thrombin Drugs 0.000 abstract 1
- 229960001322 trypsin Drugs 0.000 abstract 1
- 239000012588 trypsin Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
- 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
-
- 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
-
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/16—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/44—Two oxygen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (20)
- 일반식을 갖는 것을 특징으로 하는 구아니디노벤조에스테르 유도체 및 이의 약리적으로 허용할 수 있는염.상기식에서 X는 식인기, 여기에서 Y는 식:m이 정수 2 또는 3인 -(CH2)m-,또는 식:-OR 인기,여기에서 R은 수소원자 또는 저급알킬기,를 나타내며 n은 정수 1 내지 5를 나타낸다.
- 제1항에 있어서, X는 식:인기를 나타내는 것을 특징으로 하는 구아니디노벤조에스테르유도체 및 이의 약리적으로 허용할 수 있는 염.상기 식에서 Y는 식: m이 정수 2 또는 3인 -(CH2)m-
- 제1항에 있어서, X는 R이 수소원자 또는 저급알킬기인 식:-OR 인기를 나타내는 것을 특징으로 하는 구아니디노벤조에스테르유도체 및 이의 약리적으로 허용할수 있는 염.
- 제1항에 있어서, X는 식:인기를 나타내는 것을 특징으로 하는 구아니디노벤조에스테르유도체 및 이의 약리적으로 허용할 수 있는 염.상기 식에서 Y는 식: m이 정수 또는 3인 -(CH2)m-인 기이다.
- 제1항에 있어서, n는 2 내지 5인 것을 특징으로 하는 구아니디노벤조에스테르유도체 및 이의 약리적으로 허용할 수 있는 염.
- 제1항에 있어서, n은 2 내지 5를 나타내며, X는 식:의 기를 나타내는 것을 특징으로 하는 구아니디노벤조에스테르유도체 및 이의 약리적으로 허용할 수 있는 염.상기 식에서 Y는 식: m이 정수 또는 3인 -(CH2)m-인 기이다.
- 제1항에 있어서, n은 정수 2를 나타내는 것을 특징으로 하는 구아니디노벤조에스테르유도체 및 이의 약리적으로 허용할 수 있는 염.
- 제1항에 있어서, n은 정수2 를 나타내며 X는 식:의 기를 나타내는 것을 특징으로 하는 구아니디노벤조에스테르유도체 및 이의 약리적으로 허용할 수 있는 염.상기 식에서 Y는 식:m이 정수 또는 3인 -(CH2)m-인 기이다.
- 제1항에 있어서,n은 정수 2 내지 5를 나타내며, X는 m이 정수 2 또는 3인 식; 의기를 나타내는 것을 특징으로 하는 구아니디노벤조에스테르유도체 및 이의 약리적으로 허용할 수 있는 염
- 제1항에 있어서, n은 정수 2 내지 5를 나타내며, X는 식:의 기를 나타내는 것을 특징으로 하는 구아미디노벤조에스테르 및 이의 약리적으로 허용할 수 있는 염.
- 제1항에 있어서, 화합물은 4-(2-히드록시에틸티오) 페닐 4-구아니디노벤조에이트인 것을 특징으로 하는 구아니디노벤조에스테르유도체 또는 이의 약리적으로 허용할 수 있는 염.
- 제1항에 있어서, 화합물은 4-(2-숙신이미도에틸티오)페닐 4-구아니디노벤조에이트인 것을 특징으로 하는 구아니디노벤조에스테르유도체 또는 이의 약리적으로 허용할 수 있는 염.
- 제1항에 있어서, 화합물은 4-(2-에톡시에틸티오)페닐 4-구아니디노벤조에이트인 것을 특징으로 하는 구아니디노벤조에스테르유도체 또는 이의 약리적으로 허용할 수 있는 염.
- 제1항에 있어서, 화합물은 4-(2-에톡시에틸티오)페닐 4-구아니디노벤조에이트인 것을 특징으로 하는 구아니디노벤조에스테르 또는 이의 약리적으로 허용할 수 있는 염.
- 제1항에 있어서, 화합물은 4-[2-(시스-1,2-시클로헥산디카르복시이미도)에틸티오]페닐 4-구아니디노벤조에이트인 것을 특징으로 하는 구아니디노벤조에스테르 또는 이의 약리적으로 허용할 수 있는 염.
- 제1항에 있어서, 화합물은 4-[2-(5,5-디메틸-2,4-디옥소옥사졸리딘-3-일)에틸티오]페닐 4-구아니디노벤조에이트인 것을 특징으로 하는 구아니디노벤조에스테르유도체 또는 이의 약리적으로 허용할 수 있는 염.
- 식 :인 구아니디노벤조산을 일반식:인 화합물로, 상기 식에서 X는 식:인기, 여기에서 Y는 식: m이 정수 2 또는 3인 -(CH2)m-,인기, 또는 식:-OR 인기,여기에서 R은 수소원자 또는 저급알킬기, 를 나타내며, n은 정수 1 내지 5를 나타낸다.에스테르화 시켜 일반식:인 구아니디노벤조에스테르유도체를 형성하며, 상기 식에서, n와 X는 위에 정의한 바와 같다.필요하다면 이렇게 얻은 유도체를 이의 약리적으로 허용할 수 있는 염으로 전환시키는 것을 특징으로 하는 구아니디노벤조에스테르 유도체 또는 이의 약리적으로 허용할 수 있는 염의 제조방법.
- 제1항에서 정의한 약리적으로 효과적인 양의 화합물과 약리적으로 허용할 수있는 담체로 구성되는 것을 특징으로 하는 약학 조성물,
- 제1항에서 정의한 화합물의 투여로 사람 또는 동물의 만성 및 급성 췌장염을 치료하는 것을 특징으로 하는 치료방법.
- 제1항에서 정의한 화합물의 투여로 사람 또는 동물의 출혈병 및 혈전증을 치료하는 것을 특징으로 하는 치료방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60-293268 | 1985-12-27 | ||
| JP60293268A JPH0676373B2 (ja) | 1985-12-27 | 1985-12-27 | グアニジノ安息香酸エステル誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR870005985A true KR870005985A (ko) | 1987-07-08 |
| KR910009980B1 KR910009980B1 (ko) | 1991-12-09 |
Family
ID=17792620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019860011333A KR910009980B1 (ko) | 1985-12-27 | 1986-12-27 | 구아니디노벤조 에스테르유도체 및 그의 제조방법 |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US4801603A (ko) |
| EP (1) | EP0229370B1 (ko) |
| JP (1) | JPH0676373B2 (ko) |
| KR (1) | KR910009980B1 (ko) |
| AT (1) | ATE42279T1 (ko) |
| AU (1) | AU583970B2 (ko) |
| CA (1) | CA1277669C (ko) |
| DE (1) | DE3662883D1 (ko) |
| DK (1) | DK623486A (ko) |
| ES (1) | ES2008670B3 (ko) |
| HU (1) | HU197878B (ko) |
| NZ (1) | NZ218617A (ko) |
| PH (1) | PH25377A (ko) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4808696A (en) * | 1987-06-01 | 1989-02-28 | General Electric Company | Method for making organobis(thioether)s, and products obtained therefrom |
| US5238964A (en) * | 1990-04-05 | 1993-08-24 | Torii & Co., Ltd. | Agent for treatment of cerebrovascular contraction |
| JPH078789B2 (ja) * | 1990-04-05 | 1995-02-01 | 鳥居薬品株式会社 | 脳血管攣縮治療剤 |
| FR2691146B1 (fr) * | 1992-05-15 | 1998-01-02 | Adir | Nouveaux derives d'acides alcenecarboxyliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| WO1997037969A1 (fr) | 1996-04-10 | 1997-10-16 | Ono Pharmaceutical Co., Ltd. | Inhibiteur de tryptase derives de guanidino |
| US5968795A (en) * | 1996-05-15 | 1999-10-19 | Bayer Corporation | Biaryl acetylenes as inhibitors of matrix metalloproteases |
| WO1998005333A1 (en) * | 1996-08-05 | 1998-02-12 | Molecumetics Ltd. | Use of beta-sheet mimetics as protease and kinase inhibitors and as inhibitors of transcription factors |
| EP1661566A3 (en) * | 1996-08-05 | 2008-04-16 | Myriad Genetics, Inc. | Use of beta-sheet mimetics as protease and kinase inhibitors and as inhibitors of transcription factors |
| US6066673A (en) * | 1998-03-12 | 2000-05-23 | The Procter & Gamble Company | Enzyme inhibitors |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1905813A1 (de) * | 1968-07-04 | 1970-03-05 | Akad Wissenschaften Ddr | 3- oder 4-Guanidobenzoesaeurebenzyl- oder -phenylestern und deren Verwendung als Inhibitoren |
| IL41159A (en) * | 1972-01-12 | 1976-02-29 | Ciba Geigy Ag | Dichloromaleic acid imides,their preparation and their use in the control of plant pathogenic fungi |
| GB1472700A (en) * | 1974-11-01 | 1977-05-04 | Ono Pharmaceutical Co | Guanidinobehzoic acid derivatives and process for preparing the same |
| JPS5470241A (en) * | 1977-11-09 | 1979-06-05 | Ono Pharmaceut Co Ltd | Guanidinobenzoic acid derivative and its preparation |
| GB2044760B (en) * | 1979-03-01 | 1983-03-23 | Ono Pharmaceutical Co | Guanidinobenzoic acid derivatives |
| FR2456731A1 (fr) * | 1979-05-16 | 1980-12-12 | Choay Sa | Nouveaux derives substitues d'ary |
| JPS5634662A (en) * | 1979-08-31 | 1981-04-06 | Ono Pharmaceut Co Ltd | Guanidinobenzoic acid derivative and its preparation |
-
1985
- 1985-12-27 JP JP60293268A patent/JPH0676373B2/ja not_active Expired - Fee Related
-
1986
- 1986-12-12 NZ NZ218617A patent/NZ218617A/xx unknown
- 1986-12-22 EP EP86117885A patent/EP0229370B1/en not_active Expired
- 1986-12-22 ES ES86117885T patent/ES2008670B3/es not_active Expired
- 1986-12-22 DE DE8686117885T patent/DE3662883D1/de not_active Expired
- 1986-12-22 DK DK623486A patent/DK623486A/da not_active Application Discontinuation
- 1986-12-22 AT AT86117885T patent/ATE42279T1/de not_active IP Right Cessation
- 1986-12-23 AU AU66905/86A patent/AU583970B2/en not_active Ceased
- 1986-12-24 US US06/946,458 patent/US4801603A/en not_active Expired - Fee Related
- 1986-12-24 PH PH34668A patent/PH25377A/en unknown
- 1986-12-24 CA CA000526283A patent/CA1277669C/en not_active Expired - Fee Related
- 1986-12-27 HU HU865427A patent/HU197878B/hu not_active IP Right Cessation
- 1986-12-27 KR KR1019860011333A patent/KR910009980B1/ko not_active IP Right Cessation
-
1988
- 1988-07-28 US US07/225,278 patent/US4948808A/en not_active Expired - Lifetime
-
1990
- 1990-03-16 US US07/495,444 patent/US5075335A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR910009980B1 (ko) | 1991-12-09 |
| HUT43809A (en) | 1987-12-28 |
| ATE42279T1 (de) | 1989-05-15 |
| CA1277669C (en) | 1990-12-11 |
| AU6690586A (en) | 1987-07-02 |
| US5075335A (en) | 1991-12-24 |
| ES2008670B3 (es) | 1989-08-01 |
| HU197878B (en) | 1989-06-28 |
| AU583970B2 (en) | 1989-05-11 |
| PH25377A (en) | 1991-06-03 |
| DK623486D0 (da) | 1986-12-22 |
| EP0229370A1 (en) | 1987-07-22 |
| EP0229370B1 (en) | 1989-04-19 |
| JPS62155253A (ja) | 1987-07-10 |
| US4801603A (en) | 1989-01-31 |
| NZ218617A (en) | 1989-02-24 |
| US4948808A (en) | 1990-08-14 |
| DK623486A (da) | 1987-06-28 |
| DE3662883D1 (en) | 1989-05-24 |
| JPH0676373B2 (ja) | 1994-09-28 |
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