KR840008023A - 크로몬-및 티오크로몬-치환된 1,4- 디하이드로피리딘유도체의 제조방법 - Google Patents
크로몬-및 티오크로몬-치환된 1,4- 디하이드로피리딘유도체의 제조방법 Download PDFInfo
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- KR840008023A KR840008023A KR1019840001522A KR840001522A KR840008023A KR 840008023 A KR840008023 A KR 840008023A KR 1019840001522 A KR1019840001522 A KR 1019840001522A KR 840001522 A KR840001522 A KR 840001522A KR 840008023 A KR840008023 A KR 840008023A
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- South Korea
- Prior art keywords
- alkyl
- formula
- mono
- halogen
- poly
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 9
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 title claims 2
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- -1 benzylidene compound Chemical class 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 150000002081 enamines Chemical class 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000005122 aminoalkylamino group Chemical group 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (5)
- A) 일반식(Ⅱ)의 알데하이드와 일반식(Ⅲ)의 엔아민 및 일반식(Ⅳ)의 케톤을, 적절하게는 불활성 유기용매의 존재하에 20내지 150℃에서 반응시키거나; B) 일반식(Ⅱ)의 알데하이드와 일반식(Ⅴ)의 케톤 및 일반식(Ⅵ)의 에아민을, 적절하게는 불활성 유기용매의 존재하에 20내 150℃지에서 반응시키거나; C) 일반식(Ⅶ)의 일리덴 화합물과 일반식(Ⅵ)의 엔아민을, 적절하게는 불활성 유기 용매 존재하에 20내지 150℃에서 반응시키거나; D) 일반식(Ⅷ)의 벤질리덴 화합물과 일반식(Ⅲ)의 엔아민을, 적절하게는 불활성 유기 용매의 존재하에 20°내지 150℃에서 반응시킴을 특징으로 하여, 일반식(I)의 디하이드로피리딘 및 그의 약제학적으로 무독한 염을 제조하는 방법.상기식에서, R1은 수소, 탄소수 1내지 10의 직쇄, 사이클릭 또는 측쇄 지방족 탄화수소 라디칼, 카복실산 알킬에스테르(여기에서 알킬라디칼은 C1내지 C10임)이거나, 할로겐, C1내지 C10의 알킬, C1내지 C10의 알콕시, C1내지 C10의 알킬티오, C1내지 C10의 알킬 설피닐, 시아노, 하이드록실, 니트로, C1내지 C5의 모노-또는 폴리-플루오로알킬 C1내지 C5의 모노-또는 폴리-플루오로알킬시, C1내지 C5의 모노-또는 폴리-플루오로알킬티오, 아미노, C1내지 C5의 모노알킬아미노, 및 각알킬라디칼이 C1내지 C5인 디알킬아미노로 이루어진 그룹중에서 선택된 1내지 5개의 동일하거나 다른 치환기로 임의 치환될 수 있는 방향족 또는 헤테로 방향족라디칼이고; R2는 1내지 3개의 할로겐 원자 또는 수소이며; R4는 C1내지 C10의 알콕시, C1내지 C10의 알킬티오, C1내지 C10의 알킬설피닐, 각알킬라디칼이 C1내지 C6인 트리알킬실릴, 할로겐, 시아노, 하이드록실, 아미노, C1내지 C6의 알킬아미노, 각알킬라디칼이 C1내지 C6인 디알킬아미노, 모풀리닐, 피페리딜, 피페라지닐, 니트로, 니트레이트, 아릴 또는 헤테로아릴 (여기에서 아릴 또는 헤테로아릴라디칼은 할로겐, C1내지 C6의 알킬, C1내지 C6의 알콕시, C1내지 C6의 알킬티오, C1내지 C6의 알킬설피닐, C1내지 C6의 알킬설포닐, 하이드록실, 시아노, 니트로, 아미노, C1내지 C6의 알킬아미노, 각 알킬라디칼 C1이내 C6지 인디알킬아미노, C1내지 C6의 모노-또는 폴리-플루오로알킬 및 C1내지 C6의 모노-또는 폴리-플루오로알콕시의 그룹중에서 선택된 1내지 3개의 동일하거나 다른치 환기로임의 치환될수 있다)로 임의 치환된 탄소수 1내지 20의 포화 또는 불포화된 직쇄, 측쇄 또는 사이클릭 탄화수소라디칼이고 R5및 R7은 동일하거나 다를 수 있으며, 수소이거나, 임의로 O,CO,NH,N-(C1내지 C8) 알킬, S 및 SO2의 그룹중에서 선택된 1 또는 2개의 동일하거나 다른 헤테로 쇄원을 함유하며, 할로겐, 니트로, 시아노, 아지도, 하이드록실, 아릴, 헤테로아릴, 아미노 또는 각 알킬기가 C1내지 C6인 모노알킬아미노 또는 디알킬아미노로 임의 치환된 탄소수 1내지 10의 포화 또는 불포화된 직쇄, 측쇄 또는 사이클릭 지방족 알킬라디칼이며; R6는 수소이거나, C1내지 C10의 알콕시, 할로겐 또는 모폴리노로 임의 치환된 탄소수 1내지 20의 직쇄 또는 측쇄 알킬라디칼이고; R8은 수소, 니트로, 시아노, 할로겐, C1내지 C4의 알킬, C1내지 C4의 모노-또는 폴리-플루오로알킬 또는 하이드록시카보닐이며; A는 직접 결합을 나타내거나, O 또는 S로 임의 차단될 수 있는 C1내지 C20의 알킬렌쇄 또는 C2내지 C20의 알케닐렌쇄이고; X는 O 또는 S이며; Y는 직접 결합을 나타내거나, O,S,-NH-또는 -N-(C1내지 C8) 알킬이다.
- 제1항에 있어서, 동물량의 반응물을 사용함을 특징으로 하는 방법.
- 제1항에 있어서, 방법 A)에서의 일반식(Ⅲ) 또는 (Ⅳ) 화합물, 방법 B)에서의 일반식 (Ⅴ) 또는 (Ⅵ) 화합물, 방법 C)에서의 일반식(Ⅵ) 화합물 및 방법 D)에서의 일반식(Ⅲ) 화합물을 3몰까지의 양으로 사용함을 특징으로 하는 방법.
- 제1항에 있어서, 30내지 120℃의 온도에서 반응을 수행함을 특징으로 하는 방법.
- 제1항에 있어서, 사용된 용매의 비점에서 반응을 수행함을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3311005.0 | 1983-03-25 | ||
| DE19833311005 DE3311005A1 (de) | 1983-03-25 | 1983-03-25 | Chromon- und thiochromonsubstituierte 1,4-dihydropyridinderivate, mehrere verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| DEP3311005.0 | 1983-03-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840008023A true KR840008023A (ko) | 1984-12-12 |
| KR910007973B1 KR910007973B1 (ko) | 1991-10-05 |
Family
ID=6194712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840001522A KR910007973B1 (ko) | 1983-03-25 | 1984-03-24 | 크로몬-및 티오크로몬-치환된 1,4-디하이드로피리딘 유도체의 제조방법 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4540789A (ko) |
| EP (1) | EP0123112B1 (ko) |
| JP (1) | JPS59176281A (ko) |
| KR (1) | KR910007973B1 (ko) |
| AT (1) | ATE37367T1 (ko) |
| AU (1) | AU558035B2 (ko) |
| CA (1) | CA1236460A (ko) |
| DE (2) | DE3311005A1 (ko) |
| DK (1) | DK163733B (ko) |
| ES (4) | ES8607290A1 (ko) |
| FI (1) | FI82463C (ko) |
| HU (1) | HU191302B (ko) |
| NO (1) | NO840951L (ko) |
| ZA (1) | ZA842165B (ko) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8412208D0 (en) * | 1984-05-12 | 1984-06-20 | Pfizer Ltd | Quinolone inotropic agents |
| IT1190405B (it) * | 1985-10-22 | 1988-02-16 | Recordati Chem Pharm | Derivati del flavone |
| DE3601397A1 (de) * | 1986-01-18 | 1987-07-23 | Bayer Ag | Substituierte 1,4-dihydropyridin-3-carbonsaeurepiperazide, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| IN164232B (ko) * | 1986-04-11 | 1989-02-04 | Hoechst India | |
| DE3712369A1 (de) * | 1987-04-11 | 1988-10-27 | Bayer Ag | Substituierte 5-nitro-1,4-dihydropyridine, verfahren zur herstellung und ihre verwendung |
| US5045551A (en) * | 1989-09-19 | 1991-09-03 | Allergan, Inc. | Acetylenes disubstituted with a heteroaromatic group and a 2-substituted chromanyl, thiochromanyl or 1,2,3,4-tetrahydroquinolinyl group having retinoid-like activity |
| DE4011105A1 (de) * | 1990-04-06 | 1991-10-10 | Bayer Ag | Neue 4-chinolyl-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| US5204472A (en) * | 1990-04-06 | 1993-04-20 | Bayer Aktiengesellschaft | Quinoline and isoquinoline intermediates |
| JPH0413679A (ja) * | 1990-05-07 | 1992-01-17 | Wakunaga Pharmaceut Co Ltd | 新規ジヒドロピリジン誘導体 |
| DE4321030A1 (de) * | 1993-06-24 | 1995-01-05 | Bayer Ag | 4-bicyclisch substituierte Dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimittel |
| DE102005034267A1 (de) * | 2005-07-22 | 2007-01-25 | Bayer Healthcare Ag | 4-Chromenonyl-1,4-dihydropyridine und ihre Verwendung |
| DE102005034264A1 (de) | 2005-07-22 | 2007-02-01 | Bayer Healthcare Ag | 4-Chromenonyl-1,4-dihydropyridincarbonitrile und ihre Verwendung |
| DE102006026585A1 (de) * | 2006-06-07 | 2007-12-13 | Bayer Healthcare Aktiengesellschaft | Substituierte 4-Aryl-1,4-dihydro-1,6-naphthyridine und ihre Verwendung |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3201406A (en) * | 1963-02-11 | 1965-08-17 | Upjohn Co | Pyridylcoumarins |
| DE3412947A1 (de) * | 1984-04-06 | 1985-10-17 | Bayer Ag, 5090 Leverkusen | Tetrahydothienopyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
-
1983
- 1983-03-25 DE DE19833311005 patent/DE3311005A1/de not_active Withdrawn
-
1984
- 1984-02-29 DK DK145384A patent/DK163733B/da not_active Application Discontinuation
- 1984-03-13 NO NO840951A patent/NO840951L/no unknown
- 1984-03-14 US US06/589,436 patent/US4540789A/en not_active Expired - Lifetime
- 1984-03-16 AT AT84102903T patent/ATE37367T1/de not_active IP Right Cessation
- 1984-03-16 EP EP84102903A patent/EP0123112B1/de not_active Expired
- 1984-03-16 DE DE8484102903T patent/DE3474144D1/de not_active Expired
- 1984-03-20 AU AU25914/84A patent/AU558035B2/en not_active Ceased
- 1984-03-21 ES ES530802A patent/ES8607290A1/es not_active Expired
- 1984-03-22 FI FI841154A patent/FI82463C/fi not_active IP Right Cessation
- 1984-03-23 JP JP59054581A patent/JPS59176281A/ja active Granted
- 1984-03-23 HU HU841178A patent/HU191302B/hu not_active IP Right Cessation
- 1984-03-23 ZA ZA842165A patent/ZA842165B/xx unknown
- 1984-03-23 CA CA000450362A patent/CA1236460A/en not_active Expired
- 1984-03-24 KR KR1019840001522A patent/KR910007973B1/ko not_active IP Right Cessation
-
1986
- 1986-02-20 ES ES552232A patent/ES8705430A1/es not_active Expired
- 1986-02-20 ES ES552231A patent/ES8705429A1/es not_active Expired
- 1986-02-20 ES ES552230A patent/ES8705428A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| HUT34186A (en) | 1985-02-28 |
| CA1236460A (en) | 1988-05-10 |
| DE3474144D1 (en) | 1988-10-27 |
| DE3311005A1 (de) | 1984-09-27 |
| FI82463C (fi) | 1991-03-11 |
| DK145384D0 (da) | 1984-02-29 |
| AU558035B2 (en) | 1987-01-15 |
| EP0123112A2 (de) | 1984-10-31 |
| AU2591484A (en) | 1984-09-27 |
| ES8705429A1 (es) | 1987-05-01 |
| NO840951L (no) | 1984-09-26 |
| ES552230A0 (es) | 1987-05-01 |
| ES530802A0 (es) | 1984-11-01 |
| ZA842165B (en) | 1984-10-31 |
| ES552231A0 (es) | 1987-05-01 |
| EP0123112B1 (de) | 1988-09-21 |
| HU191302B (en) | 1987-02-27 |
| ES8607290A1 (es) | 1986-06-16 |
| ES8705428A1 (es) | 1987-05-01 |
| FI841154A0 (fi) | 1984-03-22 |
| DK163733B (da) | 1992-03-30 |
| ATE37367T1 (de) | 1988-10-15 |
| EP0123112A3 (en) | 1987-07-22 |
| ES552232A0 (es) | 1987-05-01 |
| DK145384A (da) | 1984-09-26 |
| US4540789A (en) | 1985-09-10 |
| JPH0549671B2 (ko) | 1993-07-26 |
| KR910007973B1 (ko) | 1991-10-05 |
| FI82463B (fi) | 1990-11-30 |
| JPS59176281A (ja) | 1984-10-05 |
| ES8705430A1 (es) | 1987-05-01 |
| FI841154A (fi) | 1984-09-26 |
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