KR850003715A - 5-아실-2(1h)-피리디논의 알콕시이미노 에테르 유도체의 제조방법 - Google Patents
5-아실-2(1h)-피리디논의 알콕시이미노 에테르 유도체의 제조방법 Download PDFInfo
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- KR850003715A KR850003715A KR1019840006867A KR840006867A KR850003715A KR 850003715 A KR850003715 A KR 850003715A KR 1019840006867 A KR1019840006867 A KR 1019840006867A KR 840006867 A KR840006867 A KR 840006867A KR 850003715 A KR850003715 A KR 850003715A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- hydrogen
- lower alkyl
- ethyl
- pyridinone
- Prior art date
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- 238000000034 method Methods 0.000 title claims 17
- -1 alkoxyimino ether derivative Chemical class 0.000 title claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000005262 alkoxyamine group Chemical group 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000002541 furyl group Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical class 0.000 claims 1
- 125000001544 thienyl group Chemical class 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
-
- 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
-
- 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
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (17)
- 일반식(Ⅱ)의 5-아실-2(1H)-피리디논(Ⅱ)과 일반식 R1ONH2(R1은 후술한다)의 알콕시아민을 염기의 존재하에 반응시킴을 특징으로 하여, 일반식(I)의 알콕시이미노 에테르 및 약제학적으로 무독한 그의 염을 제조하는 방법.상기식에서, R1은 C1-10알킬이고, R3는 H, 저급알킬, -C≡N,NHx,CONH2및 COOR(R은 수소 또는 저급알킬이다)이며, R4는 수소 또는 저급알킬이고, R5는 C1-10알킬, 페닐, x-치환된 페닐, 피리딜, 티에닐, 푸릴, 피롤일 및 OR(여기서, R은 수소 또는 저급알킬이며, x는 저급알킬, 저급알콕시, 저급알킬티오, 저급알킬술폰, 저급알킬술폭시드, 할로겐, 니트로, 저급알카노일, 알콕시카르보닐, 카르복시, 시아노, NH2, CONH2, COOR(R은 전술한 바와 같다), 아미디노, 이미다졸-2-일 및 CF3이다)이며, R6는 수소 또는 R5이다.
- 제1항에 있어서, 알콕시아민이 산부가염의 형태인 방법.
- 제1항에 있어서, 반응이 염기로서 피리딘을 사용하여 수행되는 방법.
- 제1항에 있어서, R3가 시아노인 방법.
- 제1항에 있어서, R3가 수소인 방법.
- 제1항에 있어서, R1이 메틸인 방법.
- 제1항에 있어서, R5가 메틸인 방법.
- 제1항에 있어서, R5가 에틸인 방법.
- 제1항에 있어서, R5가 프로필인 방법.
- 제1항에 있어서, R6가 부틸인 방법.
- 제1항에 있어서, R5가 펜틸인 방법.
- 제1항에 있어서, R6가 메틸인 방법.
- 제1항에 있어서, R6가 에틸인 방법.
- 제1항에 있어서, R4가 수소이고, R1이 메틸이고, R5가 메틸이며 R6가 메틸인 방법.
- 제1항에 있어서, R4가 수소이고, R1이 메틸이고, R5가 메틸이며 R6가 에틸인 방법.
- 제1항에 있어서, R4가 수소이고, R1이 메틸이고, R5가 프로필이며 R6가 메틸인 방법.
- 제1항에 있어서, R4가 수소이고, R1이 메틸이고, R5가 프로필이며 R6가 에틸인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54839883A | 1983-11-03 | 1983-11-03 | |
| US548398 | 1983-11-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850003715A true KR850003715A (ko) | 1985-06-26 |
| KR900005012B1 KR900005012B1 (ko) | 1990-07-16 |
Family
ID=24188699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840006867A KR900005012B1 (ko) | 1983-11-03 | 1984-11-02 | 5-아실-2(1h)-피리디논의 알콕시이미노 에테르 유도체 및 이의 제조방법 |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0140375B1 (ko) |
| JP (1) | JPS60120862A (ko) |
| KR (1) | KR900005012B1 (ko) |
| AR (1) | AR240556A1 (ko) |
| AT (1) | ATE80874T1 (ko) |
| AU (1) | AU572214B2 (ko) |
| CA (1) | CA1291138C (ko) |
| DE (1) | DE3485933T2 (ko) |
| DK (1) | DK524384A (ko) |
| ES (1) | ES537295A0 (ko) |
| GR (1) | GR80819B (ko) |
| HU (1) | HU193464B (ko) |
| IL (1) | IL73362A (ko) |
| NO (1) | NO164538C (ko) |
| NZ (1) | NZ210036A (ko) |
| PH (2) | PH21171A (ko) |
| PT (1) | PT79444B (ko) |
| ZA (1) | ZA848428B (ko) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3190800A (en) * | 1961-09-29 | 1965-06-22 | Atlas Chem Ind | Method of producing depressant effect |
| FR5428M (ko) * | 1966-03-28 | 1967-10-02 | ||
| HU177578B (en) * | 1976-08-27 | 1981-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing new 0-/3-amino-2-hydroxy-propyl/-amidoxime derivatives |
| US4220648A (en) * | 1979-01-22 | 1980-09-02 | The Upjohn Company | Antidiabetic 1,2-dihydro-2-oxo-6-neopentyl-nicotinic acids |
| US4313951A (en) * | 1979-11-26 | 1982-02-02 | Sterling Drug Inc. | 3-Substituted-6-(lower-alkyl)-5-(pyridinyl)-2(1H)-pyridinones, their cardiotonic use and intermediates therefor |
| DE3005069A1 (de) * | 1980-02-11 | 1981-08-20 | Cassella Ag, 6000 Frankfurt | Pyridonderivate, ihre herstellung und ihre verwendung |
| US4305948A (en) * | 1980-12-22 | 1981-12-15 | Sterling Drug Inc. | N-Hydroxy-1,2-dihydro-2-oxo-5-(pyridinyl)-nicotinimidamide and their cardiotonic use |
| US4524149A (en) * | 1982-03-15 | 1985-06-18 | Sterling Drug Inc. | 5-Alkanoyl-6-alkyl-2(1H)-pyridinones, their preparation and their cardiotonic use |
-
1984
- 1984-10-29 ZA ZA848428A patent/ZA848428B/xx unknown
- 1984-10-30 IL IL73362A patent/IL73362A/xx unknown
- 1984-10-30 AU AU34831/84A patent/AU572214B2/en not_active Ceased
- 1984-10-30 NZ NZ210036A patent/NZ210036A/en unknown
- 1984-10-30 AT AT84113085T patent/ATE80874T1/de not_active IP Right Cessation
- 1984-10-30 EP EP84113085A patent/EP0140375B1/en not_active Expired - Lifetime
- 1984-10-30 DE DE8484113085T patent/DE3485933T2/de not_active Expired - Fee Related
- 1984-10-31 ES ES537295A patent/ES537295A0/es active Granted
- 1984-10-31 AR AR29844884A patent/AR240556A1/es active
- 1984-11-01 CA CA000466802A patent/CA1291138C/en not_active Expired - Lifetime
- 1984-11-01 JP JP59229066A patent/JPS60120862A/ja active Granted
- 1984-11-01 GR GR80819A patent/GR80819B/el unknown
- 1984-11-02 PT PT79444A patent/PT79444B/pt not_active IP Right Cessation
- 1984-11-02 HU HU844080A patent/HU193464B/hu not_active IP Right Cessation
- 1984-11-02 PH PH31400A patent/PH21171A/en unknown
- 1984-11-02 PH PH31401A patent/PH22188A/en unknown
- 1984-11-02 NO NO844359A patent/NO164538C/no unknown
- 1984-11-02 DK DK524384A patent/DK524384A/da not_active Application Discontinuation
- 1984-11-02 KR KR1019840006867A patent/KR900005012B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PT79444B (en) | 1986-09-15 |
| EP0140375A3 (en) | 1988-06-22 |
| HU193464B (en) | 1987-10-28 |
| HUT35646A (en) | 1985-07-29 |
| JPS60120862A (ja) | 1985-06-28 |
| PH21171A (en) | 1987-08-07 |
| JPH0477745B2 (ko) | 1992-12-09 |
| NO164538B (no) | 1990-07-09 |
| AU572214B2 (en) | 1988-05-05 |
| AU3483184A (en) | 1985-05-09 |
| ES8507116A1 (es) | 1985-08-16 |
| IL73362A0 (en) | 1985-01-31 |
| ATE80874T1 (de) | 1992-10-15 |
| NO844359L (no) | 1985-05-06 |
| GR80819B (en) | 1985-03-04 |
| ES537295A0 (es) | 1985-08-16 |
| NO164538C (no) | 1990-10-17 |
| IL73362A (en) | 1989-03-31 |
| NZ210036A (en) | 1987-08-31 |
| ZA848428B (en) | 1985-06-26 |
| DK524384D0 (da) | 1984-11-02 |
| AR240556A1 (es) | 1990-05-31 |
| CA1291138C (en) | 1991-10-22 |
| PT79444A (en) | 1984-12-01 |
| DE3485933T2 (de) | 1993-02-11 |
| DE3485933D1 (de) | 1992-10-29 |
| KR900005012B1 (ko) | 1990-07-16 |
| DK524384A (da) | 1985-05-04 |
| EP0140375A2 (en) | 1985-05-08 |
| PH22188A (en) | 1988-06-28 |
| EP0140375B1 (en) | 1992-09-23 |
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