RO91871B - Process for preparing 1,4-dihydro-4-oxonaphtiridine derivatives - Google Patents
Process for preparing 1,4-dihydro-4-oxonaphtiridine derivativesInfo
- Publication number
- RO91871B RO91871B RO118517A RO11851785A RO91871B RO 91871 B RO91871 B RO 91871B RO 118517 A RO118517 A RO 118517A RO 11851785 A RO11851785 A RO 11851785A RO 91871 B RO91871 B RO 91871B
- Authority
- RO
- Romania
- Prior art keywords
- lower alkoxy
- alkoxy
- dihydro
- alkyl
- derivatives
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 7
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- NQUIRWXTTAMWIU-UHFFFAOYSA-N 1h-1,8-naphthyridin-4-one Chemical class C1=CC=C2C(O)=CC=NC2=N1 NQUIRWXTTAMWIU-UHFFFAOYSA-N 0.000 abstract 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 125000006244 carboxylic acid protecting group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 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
- C07D213/60—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
- C07D213/61—Halogen atoms or nitro radicals
-
- 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
-
- 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
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Inventia se refera la un procedeu pentru prepararea unor derivati de 1,4-dihidro-4-oxonaftiridina cu formula generala I : sau o sare a acesteia în care R reprezinta o grupa fenol, eventual substituita cu atomul de halogen, hidroxi, alchil, alcoxi inferior, clano, acilamino sau trihalogen alchil si R1 reprezinta o amina ciclica aleasa dintre 1-pirolidinil, piperidini, 1-piperazinil, sau morfolil eventual substituita cu hidroxialchil, hidroxil, alchenil, acil, alcilamino, diaschilamino, acilamino, alcoxicarbonil si N-acid-N-alchilamino. Procedeul consta în tratarea unui compus cu formula generala II : în care Ra reprezinta hidrogen sau o grupa de protectie carboxilic cu compusi cu formula III : în care R1 are semnificatiile de mai sus, în mediul de cloroform sau dimetilsufoxid în prezenta trietilaminei sau al unui exces din compusul cu formula III ca agent de legare a acidului la temperaturi de 30..70 degree C, urmata de tratare cu acid clorhidric, acid bromhidric sau hidrixid de sodiu la temperaturi de 40..125 degree C.The invention relates to a process for the preparation of 1,4-dihydro-4-oxonaphthyridine derivatives of the general formula I: or a salt thereof wherein R represents a phenol group optionally substituted with a halogen atom, hydroxy, alkyl, alkoxy lower alkyl, haloalkyl, lower alkyl, lower alkoxy, lower alkyl, lower alkoxy, lower alkoxy, lower alkoxy, lower alkoxy, lower alkoxy, -N-alkylamino. The process consists in treating a compound of general formula II: wherein Ra represents hydrogen or a carboxylic acid protecting group with compounds of formula III: wherein R1 has the above meaning in chloroform or dimethylsulfoxide in the presence of triethylamine or an excess of the compound of formula III as an acid-binding agent at temperatures of 30-70 ° C, followed by treatment with hydrochloric acid, hydrobromic acid or sodium hydride at temperatures of 40 to 125 ° C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59084963A JPS60228479A (en) | 1984-04-26 | 1984-04-26 | 1,4-dihydro-4-oxonaphthyridine derivatives and salts thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RO91871A RO91871A (en) | 1987-07-30 |
| RO91871B true RO91871B (en) | 1987-07-31 |
Family
ID=13845280
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RO118517A RO91871B (en) | 1984-04-26 | 1985-04-24 | Process for preparing 1,4-dihydro-4-oxonaphtiridine derivatives |
| RO126286A RO95509B (en) | 1984-04-26 | 1985-04-24 | Process for preparing 1,4-dihydro-4-oxonaphthyridine derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RO126286A RO95509B (en) | 1984-04-26 | 1985-04-24 | Process for preparing 1,4-dihydro-4-oxonaphthyridine derivatives |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS60228479A (en) |
| KR (1) | KR870001693B1 (en) |
| AR (1) | AR241911A1 (en) |
| AT (2) | AT389698B (en) |
| AU (2) | AU565087B2 (en) |
| BE (1) | BE902279A (en) |
| CH (1) | CH673458A5 (en) |
| CS (1) | CS250684B2 (en) |
| DD (1) | DD238795A5 (en) |
| DE (2) | DE3546658C2 (en) |
| DK (1) | DK165877C (en) |
| EG (1) | EG17339A (en) |
| ES (2) | ES8700256A1 (en) |
| FI (1) | FI80453C (en) |
| FR (2) | FR2563521B1 (en) |
| GB (2) | GB2158825B (en) |
| HU (2) | HU194226B (en) |
| ID (1) | ID21142A (en) |
| IL (1) | IL75021A (en) |
| IT (1) | IT1209953B (en) |
| LU (1) | LU85871A1 (en) |
| NL (2) | NL187314C (en) |
| NO (1) | NO162238C (en) |
| NZ (1) | NZ211895A (en) |
| PH (3) | PH22801A (en) |
| PL (1) | PL147392B1 (en) |
| PT (1) | PT80349B (en) |
| RO (2) | RO91871B (en) |
| SE (2) | SE463102B (en) |
| ZA (1) | ZA853102B (en) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6172753A (en) * | 1984-09-18 | 1986-04-14 | Dainippon Pharmaceut Co Ltd | Pyridyl ketone derivative |
| AT392789B (en) * | 1985-01-23 | 1991-06-10 | Toyama Chemical Co Ltd | METHOD FOR PRODUCING 1-SUBSTITUTED ARYL-1,4-DIHYDRO-4-OXONAPHTHYRIDINE DERIVATIVES |
| AU576657B2 (en) * | 1985-01-23 | 1988-09-01 | Toyama Chemical Co. Ltd. | Naphthyridine and pyridine derivatives |
| DE3525108A1 (en) * | 1985-06-07 | 1986-12-11 | Bayer Ag, 5090 Leverkusen | ANTIBACTERIAL EFFECT OF CHINOLON CARBON ACID ESTERS |
| IL79189A (en) * | 1985-06-26 | 1990-07-12 | Daiichi Seiyaku Co | Quinoline and/or naphthyridine-4-oxo-3-carboxylic acid derivatives,process for their preparation and pharmaceutical compositions comprising them |
| IE62600B1 (en) * | 1987-08-04 | 1995-02-22 | Abbott Lab | Naphtyridine antianaerobic compounds |
| US4962112A (en) * | 1987-08-04 | 1990-10-09 | Abbott Laboratories | 7-(2-methyl-4-aminopyrrolidinyl)naphthryidine and quinoline compounds |
| US4859776A (en) * | 1988-03-11 | 1989-08-22 | Abbott Laboratories | (S)-7-(3-aminopyrrolidin-1-yl)-1-(ortho, para-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid and method for its preparation |
| JP2844079B2 (en) * | 1988-05-23 | 1999-01-06 | 塩野義製薬株式会社 | Pyridonecarboxylic acid antibacterial agent |
| DE3934082A1 (en) * | 1989-10-12 | 1991-04-18 | Bayer Ag | CHINOLON CARBONIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS AN ANTIVIRAL AGENT |
| AU1161492A (en) * | 1991-01-14 | 1992-08-17 | Hanmi Pharmaceutical Co., Ltd. | Novel quinolone compounds and processes for preparation thereof |
| FR2692577B1 (en) * | 1992-05-26 | 1996-02-02 | Bouchara Sa | NOVEL FLUORINATED QUINOLONES, THEIR PREPARATION PROCESS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME. |
| KR940014395A (en) * | 1992-12-09 | 1994-07-18 | 강박광 | Novel quinolone derivatives and preparation methods thereof |
| KR0148277B1 (en) * | 1993-01-18 | 1998-11-02 | 채영복 | Novel fluoroquinolone derivatives and process for the preparation thereof |
| AU4272793A (en) * | 1993-04-24 | 1994-11-21 | Korea Research Institute Of Chemical Technology | Novel quinolone carboxylic acid derivatives and process for preparing the same |
| KR950018003A (en) * | 1993-12-09 | 1995-07-22 | 스미스클라인 비참 피엘씨 | Novel quinolone derivatives and methods for their preparation |
| WO1996012704A1 (en) * | 1994-10-20 | 1996-05-02 | Wakunaga Seiyaku Kabushiki Kaisha | Novel pyridonecarboxylate derivative or salt thereof and antibacterial containing the same as active ingredient |
| PT897919E (en) | 1996-04-19 | 2004-11-30 | Wakunaga Pharma Co Ltd | NEW DERIVATIVES OF PYRIDONACARBOXYLIC ACID OR ITS SATISTS AND ANTI-BACTERIAL AGENTS CONTAINING THEM AS AN ACTIVE INGREDIENT |
| CZ154999A3 (en) * | 1996-10-30 | 1999-08-11 | Bayer Aktiengesellschaft | Process for producing naphthyridine compounds and novel intermediates for this production |
| DE19713506A1 (en) | 1997-04-01 | 1998-10-08 | Bayer Ag | Process for the preparation of 2,6-dichloro-5-fluoronicotinonitrile and the chemical compound 3-cyano-2-hydroxy-5-fluoropyrid-6-one monosodium salt and its tautomers |
| RU2270695C2 (en) | 1999-03-17 | 2006-02-27 | Дайити Фармасьютикал Ко., Лтд. | Pharmaceutical composition |
| DE19926400A1 (en) | 1999-06-10 | 2000-12-14 | Bayer Ag | Improved process for the preparation of 2,6-dichloro-5-fluoro-nicotinic acid and coarse and particularly pure 2,6-dichloro-5-fluoro-nicotinic acid |
| AU6868700A (en) | 1999-09-02 | 2001-04-10 | Wakunaga Pharmaceutical Co., Ltd | Quinolinecarboxylic acid derivative or its salt |
| EP1313708A1 (en) * | 2000-08-29 | 2003-05-28 | Chiron Corporation | Quinoline antibacterial compounds and methods of use thereof |
| KR100981351B1 (en) * | 2003-10-29 | 2010-09-10 | 주식회사 엘지생명과학 | Method for preparing 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid |
| CN101792443A (en) * | 2010-03-09 | 2010-08-04 | 北京欧凯纳斯科技有限公司 | Fluoro-carbostyril derivative as well as preparation method and application thereof |
| JOP20190045A1 (en) | 2016-09-14 | 2019-03-14 | Bayer Ag | Amide-1-aryl-naphthridine-3-carboxylic acid amide compounds are substituted at position 7 and used. |
| CN114369092A (en) * | 2021-12-20 | 2022-04-19 | 赤峰万泽药业股份有限公司 | Tosufloxacin tosylate and preparation method thereof |
| CN116606279A (en) * | 2023-03-13 | 2023-08-18 | 广东工业大学 | A kind of fluoroquinolone compound and its preparation method and application |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2125310A1 (en) * | 1971-05-21 | 1972-11-30 | Sterling Drug Inc , New York, NY (V St A) | 1-alkyl-1,4-dihydro-4-oxo-1,8-naphtyridine 3-carboxylic acids antibac |
| AR223983A1 (en) * | 1978-08-25 | 1981-10-15 | Dainippon Pharmaceutical Co | A PROCEDURE FOR PREPARING 6-HALOGEN-4-OXO-7- (1-PIPERAZINYL) -1,8-NAFTIRIDIN-3-CARBOXYLIC ACID DERIVATIVES |
| DE3033157A1 (en) * | 1980-09-03 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | 7-AMINO-1-CYCLOPROPYL-4-OXO-1,4-DIHYDRO-NAPHTHYRIDINE-3-CARBONIC ACIDS, METHOD FOR THE PRODUCTION THEREOF AND THE ANTIBACTERIAL AGENTS CONTAINING THEM |
| US4382937A (en) | 1981-02-27 | 1983-05-10 | Dainippon Pharmaceutical Co., Ltd. | Naphthyridine derivatives and their use as anti-bacterials |
| IE55898B1 (en) * | 1982-09-09 | 1991-02-14 | Warner Lambert Co | Antibacterial agents |
| NZ210847A (en) * | 1984-01-26 | 1988-02-29 | Abbott Lab | Naphthyridine and pyridopyrimidine derivatives and pharmaceutical compositions |
| IL74064A (en) * | 1984-01-26 | 1988-09-30 | Abbott Lab | 1,7-disubstituted-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid derivatives and antibacterial compositions containing them |
| AU576657B2 (en) * | 1985-01-23 | 1988-09-01 | Toyama Chemical Co. Ltd. | Naphthyridine and pyridine derivatives |
| DE3525108A1 (en) * | 1985-06-07 | 1986-12-11 | Bayer Ag, 5090 Leverkusen | ANTIBACTERIAL EFFECT OF CHINOLON CARBON ACID ESTERS |
-
1984
- 1984-04-26 JP JP59084963A patent/JPS60228479A/en active Granted
-
1985
- 1985-04-18 DE DE3546658A patent/DE3546658C2/de not_active Expired - Lifetime
- 1985-04-18 DE DE19853514076 patent/DE3514076A1/en active Granted
- 1985-04-23 NL NLAANVRAGE8501172,A patent/NL187314C/en not_active IP Right Cessation
- 1985-04-23 GB GB08510297A patent/GB2158825B/en not_active Expired
- 1985-04-23 PH PH32174A patent/PH22801A/en unknown
- 1985-04-24 PT PT80349A patent/PT80349B/en unknown
- 1985-04-24 NZ NZ211895A patent/NZ211895A/en unknown
- 1985-04-24 DD DD85275518A patent/DD238795A5/en unknown
- 1985-04-24 IL IL7502185A patent/IL75021A/en not_active IP Right Cessation
- 1985-04-24 RO RO118517A patent/RO91871B/en unknown
- 1985-04-24 RO RO126286A patent/RO95509B/en unknown
- 1985-04-24 NO NO851643A patent/NO162238C/en not_active IP Right Cessation
- 1985-04-24 AT AT0122485A patent/AT389698B/en not_active IP Right Cessation
- 1985-04-24 AU AU41650/85A patent/AU565087B2/en not_active Expired
- 1985-04-24 EG EG261/85A patent/EG17339A/en active
- 1985-04-25 HU HU851599A patent/HU194226B/en unknown
- 1985-04-25 HU HU873675A patent/HU197571B/en unknown
- 1985-04-25 FR FR858506327A patent/FR2563521B1/en not_active Expired
- 1985-04-25 ES ES542584A patent/ES8700256A1/en not_active Expired
- 1985-04-25 CS CS853035A patent/CS250684B2/en not_active IP Right Cessation
- 1985-04-25 DK DK185685A patent/DK165877C/en not_active IP Right Cessation
- 1985-04-25 BE BE0/214909A patent/BE902279A/en not_active IP Right Cessation
- 1985-04-25 CH CH1798/85A patent/CH673458A5/de not_active IP Right Cessation
- 1985-04-25 KR KR1019850002822A patent/KR870001693B1/en not_active Expired
- 1985-04-25 AR AR85300190A patent/AR241911A1/en active
- 1985-04-25 ZA ZA853102A patent/ZA853102B/en unknown
- 1985-04-25 ID IDP980525A patent/ID21142A/en unknown
- 1985-04-25 FI FI851637A patent/FI80453C/en not_active IP Right Cessation
- 1985-04-25 SE SE8502017A patent/SE463102B/en not_active IP Right Cessation
- 1985-04-26 LU LU85871A patent/LU85871A1/en unknown
- 1985-04-26 IT IT8548002A patent/IT1209953B/en active
- 1985-04-26 PL PL1985253108A patent/PL147392B1/en unknown
-
1986
- 1986-01-31 ES ES551538A patent/ES8706673A1/en not_active Expired
-
1987
- 1987-07-17 GB GB8716897A patent/GB2191776B/en not_active Expired - Lifetime
- 1987-10-20 PH PH35960A patent/PH25228A/en unknown
- 1987-10-20 PH PH35958A patent/PH25046A/en unknown
- 1987-11-25 AU AU81804/87A patent/AU612993B2/en not_active Expired
-
1988
- 1988-06-30 FR FR888808836A patent/FR2614620B1/en not_active Expired - Lifetime
- 1988-10-31 AT AT0267888A patent/AT390258B/en not_active IP Right Cessation
- 1988-12-20 SE SE8804586A patent/SE501412C2/en not_active IP Right Cessation
-
1991
- 1991-04-15 NL NL9100648A patent/NL9100648A/en not_active Application Discontinuation
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