KR840007877A - 퀴놀온 카복실 산 및 이들의 화합물을 함유하는 항 박테리아제의 제조방법 - Google Patents
퀴놀온 카복실 산 및 이들의 화합물을 함유하는 항 박테리아제의 제조방법 Download PDFInfo
- Publication number
- KR840007877A KR840007877A KR1019840000933A KR840000933A KR840007877A KR 840007877 A KR840007877 A KR 840007877A KR 1019840000933 A KR1019840000933 A KR 1019840000933A KR 840000933 A KR840000933 A KR 840000933A KR 840007877 A KR840007877 A KR 840007877A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- carbon atoms
- optionally
- substituted
- carboxylic acid
- 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.)
- Granted
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
Claims (3)
- (a) 일반식(Ⅱ)의 화합물을 일반식(Ⅲ)의 화합물과 반응시키거나, (b) 일반식(Ⅱ)의 화합물을 일반식(Ⅳ)의 이소시아네이트와 반응시키거나 또는, (c) 일반식(Ⅱ)의 화합물을 일반식(Ⅴ)의 무수물과 반응시키는 것을 특징으로 하여, 일반식(Ⅰ)의 퀴놀은 카복실산을 제조하는 방법.상기식에서, R1은 라디칼 CO-R6, CN, SO2-R7또는 S-R8이고, R6은 수소, 경우에 따라 치환된 1 내지 6 탄소원자를 갖는 직쇄 또는 측쇄 알킬, 경우에 따라 치환된 6 또는 10탄소원자를 갖는 아릴, 경우에 따라 치환된 아릴 위치에 6 탄소원자를 갖고 알킬 위치에 1 내지 3 탄소원자를 갖는 아르알킬, 경우에 따는 치환된 1 내지 6 탄소원자를 갖는 알콕시 또는 알킬티오, 경우에 따라 치환된 6 탄소원자를 갖는 아릴옥시, 경우에 따라 치환된 벤질옥시, 아미노, 경우에 따라 치환된 알킬 라디칼 속에 1 내지 6탄소원자를 갖는 알킬아미노 또는 디 알킬아미노, 또는 경우에 따라 치환된 페닐 아미노이고, R7은 경우에 따라 치환된 1 내지 5탄소원자를 갖는 직쇄 또는 측쇄 알킬, 페닐 또는 메틸페닐이며, R8은 메톡시카보닐, 트리클로로메틸, 트리플루오로메틸 또는 디 클로로플루오로 메틸이고, R2,R3,R4및 R5는 같거나 또는 다르고 수소, 메틸, 에틸, n-또는 i-프로필이고, X는 수소, 바람직하게는 불소 또는 염소와 같은 할로겐, 또는 질소이다. Y는 바람직하게는 염소, 불소 또는 브롬과 같은 할로겐, 메톡시, 에톡시, 펜옥시, 4-니트로펜옥시 또는 2,3,5-트리클로로펜옥시 또는 알킬카보닐옥시와 같은 이탈 그룹이고, R'는 경우에 따라 치환된 알킬 또는 페닐이며, A는 경우에 따라 치환된 2 또는 3 탄소원자를 갖는 알킬렌 사슬이고 또는 아릴렌 라디칼이다.
- 제1항의 일반식(Ⅰ)의 퀴놀은 카복실 산을, 불활성, 비독성, 약제학적으로 적절한 부형제와 혼합하는 것을 특징으로 하여 항 박테리아성 약제를 제조하는 방법.
- 제1항의 일반식(Ⅰ)의 퀴놀은 카복실산을 박테리아 감염된 인간 또는 동물에게 투여하는 것을 특징으로 하여 박테리아성 질병을 퇴치하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019870002771A KR870000894B1 (ko) | 1983-02-25 | 1987-03-26 | 퀴놀론 카복실산의 제조방법 |
| KR1019870002770A KR870000893B1 (ko) | 1983-02-25 | 1987-03-26 | 퀴놀론 카복실산의 제조방법 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3306771.6 | 1983-02-25 | ||
| DE19833306771 DE3306771A1 (de) | 1983-02-25 | 1983-02-25 | Chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019870002771A Division KR870000894B1 (ko) | 1983-02-25 | 1987-03-26 | 퀴놀론 카복실산의 제조방법 |
| KR1019870002770A Division KR870000893B1 (ko) | 1983-02-25 | 1987-03-26 | 퀴놀론 카복실산의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840007877A true KR840007877A (ko) | 1984-12-11 |
| KR870000892B1 KR870000892B1 (ko) | 1987-05-02 |
Family
ID=6191896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840000933A Expired KR870000892B1 (ko) | 1983-02-25 | 1984-02-25 | 퀴놀론카복실산의 제조방법 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4559341A (ko) |
| EP (1) | EP0117473B1 (ko) |
| JP (1) | JPS59163369A (ko) |
| KR (1) | KR870000892B1 (ko) |
| AT (1) | ATE25245T1 (ko) |
| AU (1) | AU563748B2 (ko) |
| CA (1) | CA1246574A (ko) |
| DE (2) | DE3306771A1 (ko) |
| DK (1) | DK103384A (ko) |
| ES (1) | ES530046A0 (ko) |
| FI (1) | FI79702C (ko) |
| GR (1) | GR79989B (ko) |
| HU (1) | HU192399B (ko) |
| IL (1) | IL71037A (ko) |
| NO (1) | NO840558L (ko) |
| NZ (1) | NZ207239A (ko) |
| PH (2) | PH23256A (ko) |
| PT (1) | PT78113B (ko) |
| ZA (1) | ZA841373B (ko) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3306771A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3306772A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinolonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3308909A1 (de) * | 1983-03-12 | 1984-09-13 | Bayer Ag, 5090 Leverkusen | Bakterizide mittel auf chinoloncarbonsaeure-basis |
| DE3318145A1 (de) * | 1983-05-18 | 1984-11-22 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-6,8-difluor-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| IT1196051B (it) * | 1984-03-16 | 1988-11-10 | Schiena Ricerche | Composti ad attivita' antibatterica |
| DE3420770A1 (de) * | 1984-06-04 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-(3-oxo-1-piperazinyl)-3-chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3508816A1 (de) * | 1985-01-10 | 1986-07-10 | Bayer Ag, 5090 Leverkusen | 6,7-disubstituierte 1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphtyridin-3-carbonsaeuren |
| DE3509546A1 (de) * | 1985-03-16 | 1986-09-25 | Bayer Ag, 5090 Leverkusen | 7-amino-1-(subst.cyclopropyl)-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| US4686221A (en) * | 1985-10-01 | 1987-08-11 | Kanebo, Ltd. | Quinolinecarboxylic acid compounds and antimicrobial agent containing the same |
| DE3537761A1 (de) * | 1985-10-24 | 1987-04-30 | Bayer Ag | Infusionsloesungen der 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7- (1-piperazinyl)-chinolin-3-carbonsaeure |
| AU594983B2 (en) * | 1985-10-29 | 1990-03-22 | Dainippon Pharmaceutical Co. Ltd. | Novel quinoline derivatives and processes for preparation thereof |
| EP0224121A3 (en) * | 1985-11-19 | 1987-11-11 | ROTTAPHARM S.p.A. | 7-[4-amino-piperazinyl]- or 7-[4-chloro-piperazinyl]quinolinone derivatives, a process for the preparation thereof and pharmaceutical compositions containing them |
| DE3542002A1 (de) * | 1985-11-28 | 1987-06-04 | Bayer Ag | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7- (1-piperazinyl)-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3601566A1 (de) * | 1986-01-21 | 1987-07-23 | Bayer Ag | Pharmazeutische zubereitungen von ciprofloxacin |
| DE3705621C2 (de) * | 1986-02-25 | 1997-01-09 | Otsuka Pharma Co Ltd | Heterocyclisch substituierte Chinoloncarbonsäurederivate |
| HU196987B (en) * | 1986-10-15 | 1989-02-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing quinoline-carboxylic acid derivatives |
| US4851418A (en) * | 1987-08-21 | 1989-07-25 | Warner-Lambert Company | Naphthyridine antibacterial agents containing an α-amino acid in the side chain of the 7-substituent |
| SI8712447A8 (en) * | 1987-12-31 | 1995-12-31 | Krka Tovarna Zdravil | Process for preparing 1-substituted 6-fluoro-4-oxo-7-(1-piperazinyl) -1,4-dihydroquinoline-3-carboxylic acid and new intermediate used in this process |
| DE3902079A1 (de) * | 1988-04-15 | 1989-10-26 | Bayer Ag | I.m. injektionsformen von gyrase-inhibitoren |
| US5262417A (en) * | 1988-12-06 | 1993-11-16 | The Upjohn Company | Antibacterial quinolone compounds |
| FR2676445B1 (fr) * | 1991-05-16 | 1995-02-03 | Esteve Labor Dr | Derives de pyridone amino acide azetidinyl substitues, leur preparation et leur application en tant que medicaments. |
| FR2694751B1 (fr) * | 1992-08-14 | 1994-11-25 | Bouchara Sa | Nouveaux dérivés sulfonamides, leurs procédés de préparation et les compositions en renfermant. |
| CA2114981A1 (en) | 1993-02-09 | 1994-08-10 | Kazumi Ogata | Quinolonecarboxylic acid derivatives |
| US5395936A (en) * | 1993-06-04 | 1995-03-07 | Manzo; Ruben H. | 7-(4-[4-aminophenyl)sulphonyl]-1-piperazinyl fluorquinolonic derivatives and synthesis |
| US7842693B2 (en) * | 2002-06-12 | 2010-11-30 | Chemocentryx, Inc. | Substituted piperazines |
| US7589199B2 (en) | 2002-06-12 | 2009-09-15 | Chemocentryx, Inc. | Substituted piperazines |
| EP1531822B1 (en) | 2002-06-12 | 2009-08-05 | ChemoCentryx Inc | 1-aryl-4-substituted piperazine derivatives for use as ccr1 antagonists for the treatment of inflammation and immune disorders |
| US20050256130A1 (en) * | 2002-06-12 | 2005-11-17 | Chemocentryx, Inc. | Substituted piperazines |
| US7435831B2 (en) * | 2004-03-03 | 2008-10-14 | Chemocentryx, Inc. | Bicyclic and bridged nitrogen heterocycles |
| AU2005219438B2 (en) * | 2004-03-03 | 2011-02-17 | Chemocentryx, Inc. | Bicyclic and bridged nitrogen heterocycles |
| US8143398B1 (en) * | 2010-02-19 | 2012-03-27 | University Of South Florida | Activity of new N-acylated ciprofloxacin derivatives against faculative intracellular bacteria |
| US9670179B1 (en) * | 2013-03-14 | 2017-06-06 | University Of South Florida | Antibiotic compositions and methods of use |
| EP2957561A1 (en) | 2014-06-18 | 2015-12-23 | Université Paris 6 Pierre et Marie Curie UPMC | Novel fluoroquinolones and use thereof to treat bacterial infections |
| CN104230889A (zh) * | 2014-08-29 | 2014-12-24 | 南京大学 | 环丙沙星衍生物及其制备方法与用途 |
| US11529309B2 (en) * | 2016-04-29 | 2022-12-20 | University Of Houston System | Compositions, methods and kits for treating a contact lens |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3149104A (en) * | 1961-01-03 | 1964-09-15 | Sterling Drug Inc | 4-hydroxy-7-styryl-1, 8-naphthyridine-3-carboxylic acids and esters |
| JPS5750783B2 (ko) * | 1974-02-07 | 1982-10-28 | ||
| SE444566B (sv) * | 1977-09-20 | 1986-04-21 | Bellon Labor Sa Roger | 7-dialkylamin-6-halogen-4-oxo-1,4-dihydrokinolin-3-karboxylsyra, forfarande for framstellning derav och farmaceutiskt preparat derav |
| JPS5466686A (en) * | 1977-09-20 | 1979-05-29 | Dainippon Pharmaceut Co Ltd | Quinoline-3-carboxylic acid derivative, its preparation, and pharmaceutical composition containig the same |
| DE2808070A1 (de) * | 1978-02-24 | 1979-08-30 | Bayer Ag | Verfahren zur herstellung von 4-pyridon-3-carbonsaeuren und/oder deren derivaten |
| JPS5845426B2 (ja) * | 1978-09-29 | 1983-10-08 | 杏林製薬株式会社 | 置換キノリンカルボン酸誘導体 |
| DE2939783C2 (de) * | 1979-10-01 | 1982-04-29 | UOP Inc., 60016 Des Plaines, Ill. | Verfahren zum Abscheiden von Schwefel- und Stickstoffoxiden aus einem Gasgemisch |
| DE3033157A1 (de) * | 1980-09-03 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3142854A1 (de) * | 1981-10-29 | 1983-05-11 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-piperazino-chinolin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| JPS5762259A (en) * | 1980-09-05 | 1982-04-15 | Kyorin Pharmaceut Co Ltd | Preparation of substituted quinolinecarboxylic acid derivative |
| EP0090424B1 (en) * | 1982-03-31 | 1986-05-28 | Sterling Drug Inc. | New quinolone compounds and preparation thereof |
| DE3306772A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinolonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3306771A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
-
1983
- 1983-02-25 DE DE19833306771 patent/DE3306771A1/de not_active Withdrawn
-
1984
- 1984-02-03 US US06/576,595 patent/US4559341A/en not_active Expired - Fee Related
- 1984-02-08 AU AU24284/84A patent/AU563748B2/en not_active Ceased
- 1984-02-13 EP EP84101442A patent/EP0117473B1/de not_active Expired
- 1984-02-13 AT AT84101442T patent/ATE25245T1/de not_active IP Right Cessation
- 1984-02-13 DE DE8484101442T patent/DE3462255D1/de not_active Expired
- 1984-02-15 NO NO840558A patent/NO840558L/no unknown
- 1984-02-15 PT PT78113A patent/PT78113B/pt not_active IP Right Cessation
- 1984-02-22 NZ NZ207239A patent/NZ207239A/en unknown
- 1984-02-22 JP JP59030468A patent/JPS59163369A/ja active Pending
- 1984-02-22 IL IL71037A patent/IL71037A/xx unknown
- 1984-02-23 CA CA000448124A patent/CA1246574A/en not_active Expired
- 1984-02-23 FI FI840748A patent/FI79702C/fi not_active IP Right Cessation
- 1984-02-23 GR GR73904A patent/GR79989B/el unknown
- 1984-02-24 ES ES530046A patent/ES530046A0/es active Granted
- 1984-02-24 ZA ZA841373A patent/ZA841373B/xx unknown
- 1984-02-24 DK DK103384A patent/DK103384A/da not_active Application Discontinuation
- 1984-02-24 HU HU84750A patent/HU192399B/hu not_active IP Right Cessation
- 1984-02-25 KR KR1019840000933A patent/KR870000892B1/ko not_active Expired
-
1985
- 1985-06-17 PH PH32413A patent/PH23256A/en unknown
- 1985-06-17 PH PH32415A patent/PH23248A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT78113B (en) | 1986-04-30 |
| IL71037A0 (en) | 1984-05-31 |
| AU563748B2 (en) | 1987-07-23 |
| NO840558L (no) | 1984-08-27 |
| AU2428484A (en) | 1984-08-30 |
| PT78113A (en) | 1984-03-01 |
| KR870000892B1 (ko) | 1987-05-02 |
| FI79702B (fi) | 1989-10-31 |
| GR79989B (ko) | 1984-10-31 |
| US4559341A (en) | 1985-12-17 |
| DK103384A (da) | 1984-08-26 |
| CA1246574A (en) | 1988-12-13 |
| DK103384D0 (da) | 1984-02-24 |
| PH23248A (en) | 1989-06-16 |
| ZA841373B (en) | 1984-10-31 |
| FI840748A0 (fi) | 1984-02-23 |
| HU192399B (en) | 1987-06-29 |
| PH23256A (en) | 1989-06-16 |
| ATE25245T1 (de) | 1987-02-15 |
| DE3306771A1 (de) | 1984-08-30 |
| FI79702C (fi) | 1990-02-12 |
| JPS59163369A (ja) | 1984-09-14 |
| IL71037A (en) | 1988-02-29 |
| DE3462255D1 (en) | 1987-03-05 |
| ES8500932A1 (es) | 1984-11-01 |
| NZ207239A (en) | 1986-05-09 |
| ES530046A0 (es) | 1984-11-01 |
| EP0117473B1 (de) | 1987-01-28 |
| EP0117473A1 (de) | 1984-09-05 |
| FI840748L (fi) | 1984-08-26 |
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