DD262428A1 - Verfahren zur herstellung neuer 4-pyridonderivate und deren physiologisch vertraeglicher salze und ester - Google Patents
Verfahren zur herstellung neuer 4-pyridonderivate und deren physiologisch vertraeglicher salze und ester Download PDFInfo
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- DD262428A1 DD262428A1 DD87304673A DD30467387A DD262428A1 DD 262428 A1 DD262428 A1 DD 262428A1 DD 87304673 A DD87304673 A DD 87304673A DD 30467387 A DD30467387 A DD 30467387A DD 262428 A1 DD262428 A1 DD 262428A1
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- DD
- German Democratic Republic
- Prior art keywords
- formula
- compounds
- general formula
- hydrogen
- ind
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 24
- 150000003839 salts Chemical class 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- MPOYBFYHRQBZPM-UHFFFAOYSA-N 3h-pyridin-4-one Chemical class O=C1CC=NC=C1 MPOYBFYHRQBZPM-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- -1 methylamino, 4-fluorophenyl Chemical group 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- VQFAIAKCILWQPZ-UHFFFAOYSA-N bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims abstract description 8
- 125000006239 protecting group Chemical group 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000003776 cleavage reaction Methods 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
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- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 3
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- 229910052796 boron Inorganic materials 0.000 claims description 2
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- 229940052810 complex b Drugs 0.000 claims description 2
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- 229960004236 pefloxacin Drugs 0.000 description 6
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
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- 241001465754 Metazoa Species 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- OKVJWADVFPXWQD-UHFFFAOYSA-N difluoroborinic acid Chemical compound OB(F)F OKVJWADVFPXWQD-UHFFFAOYSA-N 0.000 description 4
- IDYZIJYBMGIQMJ-UHFFFAOYSA-N enoxacin Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 IDYZIJYBMGIQMJ-UHFFFAOYSA-N 0.000 description 4
- 229960002549 enoxacin Drugs 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
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- 230000002829 reductive effect Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical class N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- 241000588697 Enterobacter cloacae Species 0.000 description 3
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- 241000588772 Morganella morganii Species 0.000 description 3
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- 241000589517 Pseudomonas aeruginosa Species 0.000 description 3
- 241000607715 Serratia marcescens Species 0.000 description 3
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- HNHBNEMSYQAAIM-UHFFFAOYSA-N 7-(2,5-diazabicyclo[2.2.1]heptan-2-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(N3C4CC(NC4)C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1F HNHBNEMSYQAAIM-UHFFFAOYSA-N 0.000 description 2
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- YTSWVGNFUCBHNG-UHFFFAOYSA-N 7-(5-benzyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(N3C4CC(N(C4)CC=4C=CC=CC=4)C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1F YTSWVGNFUCBHNG-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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- OGMCNLQGJGWEPU-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC=CC=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1 OGMCNLQGJGWEPU-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
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- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical class C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
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- GWFALVUXAGYMHR-UHFFFAOYSA-N 4-(bromomethyl)-5-methyl-1,3-dioxol-2-one Chemical compound CC=1OC(=O)OC=1CBr GWFALVUXAGYMHR-UHFFFAOYSA-N 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- DHKXYRLLOOJYTH-UHFFFAOYSA-N 6-fluoro-1-(4-fluorophenyl)-4-oxo-7-[5-(2-oxopropyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]quinoline-3-carboxylic acid Chemical compound CC(=O)CN1CC2CC1CN2C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=CC=1N2C1=CC=C(F)C=C1 DHKXYRLLOOJYTH-UHFFFAOYSA-N 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
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- UXAWXZDXVOYLII-UHFFFAOYSA-N tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C1C2N(C(=O)OC(C)(C)C)CC1NC2 UXAWXZDXVOYLII-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07D211/86—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3622509 | 1986-07-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD262428A1 true DD262428A1 (de) | 1988-11-30 |
Family
ID=6304401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD87304673A DD262428A1 (de) | 1986-07-04 | 1987-07-06 | Verfahren zur herstellung neuer 4-pyridonderivate und deren physiologisch vertraeglicher salze und ester |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5045549A (cs) |
| EP (1) | EP0251308B1 (cs) |
| JP (1) | JPH07103123B2 (cs) |
| KR (1) | KR880001595A (cs) |
| AR (1) | AR245450A1 (cs) |
| AT (1) | ATE58538T1 (cs) |
| AU (1) | AU608515B2 (cs) |
| CS (1) | CS277415B6 (cs) |
| DD (1) | DD262428A1 (cs) |
| DE (1) | DE3766299D1 (cs) |
| DK (1) | DK342187A (cs) |
| ES (1) | ES2018667B3 (cs) |
| FI (1) | FI88506C (cs) |
| GR (1) | GR3001097T3 (cs) |
| HU (1) | HU197907B (cs) |
| IL (1) | IL83049A (cs) |
| MY (1) | MY101261A (cs) |
| NO (1) | NO166130C (cs) |
| NZ (1) | NZ220950A (cs) |
| PH (1) | PH24239A (cs) |
| PT (1) | PT85257B (cs) |
| SU (1) | SU1551248A3 (cs) |
| YU (1) | YU45039B (cs) |
| ZA (1) | ZA874849B (cs) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IN166416B (cs) * | 1985-09-18 | 1990-05-05 | Pfizer | |
| SI8810667A8 (en) * | 1987-04-08 | 1996-04-30 | Chinoin Gyogyszer Es Vegyeszet | Anhydride of quinoline carboxylic acid of boron acid and process for their production. |
| JPH02131453A (ja) * | 1988-04-15 | 1990-05-21 | Asahi Glass Co Ltd | ２―クロロ―４，５―ジフルオロベンゾイルアクリル酸誘導体 |
| JPH072679B2 (ja) * | 1988-04-15 | 1995-01-18 | 旭硝子株式会社 | ２―クロロ―４，５―ジフルオロ安息香酸誘導体 |
| WO1989012055A1 (en) * | 1988-06-08 | 1989-12-14 | Kyorin Pharmaceutical Co., Ltd. | Antitumor agent |
| JPH02298946A (ja) * | 1989-05-15 | 1990-12-11 | Johoku Seihan Center:Kk | 製版・版下作製材および製版・版下作製における貼付方法 |
| EP0449445A3 (en) * | 1990-03-27 | 1993-08-25 | Pfizer Inc. | Preparation of beta-ketoesters useful in preparing quinolone antibiotics |
| KR100204987B1 (ko) | 1990-04-18 | 1999-06-15 | 제이코버스 코넬리스 레이서 | 항미생물성 퀴놀로닐 락탐 |
| FR2692577B1 (fr) * | 1992-05-26 | 1996-02-02 | Bouchara Sa | Nouvelles quinolones fluorees, leur procede de preparation et les compositions pharmaceutiques en renfermant. |
| TW252107B (cs) * | 1993-08-27 | 1995-07-21 | Hokuriku Pharmacetical Co Ltd | |
| ES2092963B1 (es) * | 1995-04-12 | 1997-12-16 | Sint Quimica Sa | Procedimiento para la preparacion del acido 1-ciclopropil-6-fluoro-1, 4-dihidro-7-(1s,4s)-5-metil-2,5-diazabiciclo(2.2.1) hept-2-il)-4-oxo-3-quinolincarboxilico y sus sales. |
| SE0003795D0 (sv) | 2000-10-20 | 2000-10-20 | Astrazeneca Ab | Pharmaceutically useful compounds |
| WO2011031745A1 (en) | 2009-09-09 | 2011-03-17 | Achaogen, Inc. | Antibacterial fluoroquinolone analogs |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1175836A (en) * | 1977-09-20 | 1984-10-09 | Marcel Pesson | Production of 1,4-dihydroquinoline-3-carboxylic acid derivatives |
| DE2808070A1 (de) * | 1978-02-24 | 1979-08-30 | Bayer Ag | Verfahren zur herstellung von 4-pyridon-3-carbonsaeuren und/oder deren derivaten |
| DE3267485D1 (en) * | 1981-02-18 | 1986-01-02 | Nippon Shinyaku Co Ltd | Substituted carboxylic acid derivatives |
| US4499091A (en) * | 1982-03-31 | 1985-02-12 | Sterling Drug Inc. | 1-Amino (or substituted amino)-1,4-dihydro-4-oxo-6-fluoro-7-heterylquinoline-3-carboxylic acids and their use as antibacterial agents |
| EP0090424B1 (en) * | 1982-03-31 | 1986-05-28 | Sterling Drug Inc. | New quinolone compounds and preparation thereof |
| US4730000A (en) * | 1984-04-09 | 1988-03-08 | Abbott Laboratories | Quinoline antibacterial compounds |
| JPS6056959A (ja) * | 1983-07-18 | 1985-04-02 | アボツト ラボラトリ−ズ | キノリン抗菌性化合物 |
| NZ208470A (en) * | 1983-07-18 | 1988-06-30 | Abbott Lab | 6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid derivatives and antibacterial compositions containing such |
| US4571396A (en) * | 1984-04-16 | 1986-02-18 | Warner-Lambert Company | Antibacterial agents |
| EP0181521A1 (en) * | 1984-10-19 | 1986-05-21 | Otsuka Pharmaceutical Co., Ltd. | Antimicrobial 1-substituted Phenyl-4-oxoquinoline-3-carboxylic acid compounds |
| US4578473A (en) * | 1985-04-15 | 1986-03-25 | Warner-Lambert Company | Process for quinoline-3-carboxylic acid antibacterial agents |
| IN166416B (cs) * | 1985-09-18 | 1990-05-05 | Pfizer | |
| DE3601567A1 (de) * | 1986-01-21 | 1987-07-23 | Bayer Ag | 7-(azabicycloalkyl)-chinoloncarbonsaeure- und -naphthyridon-carbonsaeure-derivate |
| US4962108A (en) * | 1987-07-31 | 1990-10-09 | Warner-Lambert Company | Antibacterial quinoline compounds |
| US4923879A (en) * | 1987-07-31 | 1990-05-08 | Warner-Lambert Company | 1,8-Naphthyridines and their use as antibacterial agents |
| US4962112A (en) * | 1987-08-04 | 1990-10-09 | Abbott Laboratories | 7-(2-methyl-4-aminopyrrolidinyl)naphthryidine and quinoline compounds |
| US4780468A (en) * | 1987-08-07 | 1988-10-25 | Warner-Lambert Company | 8-trifluoromethyl quinolones as antibacterial agents |
| 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 |
| WO1989005643A1 (en) * | 1987-12-18 | 1989-06-29 | Pfizer Inc. | Heterocyclic-substituted quinoline-carboxylic acids |
| US4920120A (en) * | 1988-01-25 | 1990-04-24 | Warner-Lambert Company | Antibacterial agents |
-
1987
- 1987-07-01 DE DE8787109461T patent/DE3766299D1/de not_active Expired - Lifetime
- 1987-07-01 ES ES87109461T patent/ES2018667B3/es not_active Expired - Lifetime
- 1987-07-01 EP EP87109461A patent/EP0251308B1/de not_active Expired - Lifetime
- 1987-07-01 FI FI872897A patent/FI88506C/fi not_active IP Right Cessation
- 1987-07-01 IL IL83049A patent/IL83049A/xx not_active IP Right Cessation
- 1987-07-01 AT AT87109461T patent/ATE58538T1/de not_active IP Right Cessation
- 1987-07-02 YU YU1246/87A patent/YU45039B/xx unknown
- 1987-07-02 NO NO872778A patent/NO166130C/no unknown
- 1987-07-03 MY MYPI87000937A patent/MY101261A/en unknown
- 1987-07-03 SU SU874203001A patent/SU1551248A3/ru active
- 1987-07-03 JP JP62165560A patent/JPH07103123B2/ja not_active Expired - Lifetime
- 1987-07-03 PH PH35494A patent/PH24239A/en unknown
- 1987-07-03 AU AU75080/87A patent/AU608515B2/en not_active Ceased
- 1987-07-03 CS CS875055A patent/CS277415B6/cs unknown
- 1987-07-03 HU HU873023A patent/HU197907B/hu not_active IP Right Cessation
- 1987-07-03 ZA ZA874849A patent/ZA874849B/xx unknown
- 1987-07-03 DK DK342187A patent/DK342187A/da not_active Application Discontinuation
- 1987-07-03 PT PT85257A patent/PT85257B/pt not_active IP Right Cessation
- 1987-07-03 NZ NZ220950A patent/NZ220950A/xx unknown
- 1987-07-03 AR AR87308059A patent/AR245450A1/es active
- 1987-07-04 KR KR1019870007133A patent/KR880001595A/ko not_active Ceased
- 1987-07-06 DD DD87304673A patent/DD262428A1/de not_active IP Right Cessation
- 1987-07-06 US US07/070,351 patent/US5045549A/en not_active Expired - Fee Related
-
1990
- 1990-11-23 GR GR90400603T patent/GR3001097T3/el unknown
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