NO325617B1 - Anvendelse av 7-(2-oksa-5,8-diazabicyklo[4.3.0]non-8-yl)-kinolonkarboksylsyre og naftyridonkarboksylsyrederivater for fremstilling av legemidler for behandling av helicobacter pylori infeksjoner og dermed forbundede gastroduodenale sykdommer, diastereomerrene og enantiomerrene forbindelser, anvendelse derav samt legemiddel inneholdende disse. - Google Patents
Anvendelse av 7-(2-oksa-5,8-diazabicyklo[4.3.0]non-8-yl)-kinolonkarboksylsyre og naftyridonkarboksylsyrederivater for fremstilling av legemidler for behandling av helicobacter pylori infeksjoner og dermed forbundede gastroduodenale sykdommer, diastereomerrene og enantiomerrene forbindelser, anvendelse derav samt legemiddel inneholdende disse. Download PDFInfo
- Publication number
- NO325617B1 NO325617B1 NO19992903A NO992903A NO325617B1 NO 325617 B1 NO325617 B1 NO 325617B1 NO 19992903 A NO19992903 A NO 19992903A NO 992903 A NO992903 A NO 992903A NO 325617 B1 NO325617 B1 NO 325617B1
- Authority
- NO
- Norway
- Prior art keywords
- stands
- oxa
- diazabicyclo
- oxo
- methyl
- Prior art date
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- -1 naphthyridone carboxylic acid derivatives Chemical class 0.000 title claims abstract description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 16
- 206010019375 Helicobacter infections Diseases 0.000 title claims abstract description 13
- 238000011282 treatment Methods 0.000 title claims description 27
- 239000003814 drug Substances 0.000 title claims description 16
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- HBOHUPRFLRTLDQ-UHFFFAOYSA-N 7-(3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b][1,4]oxazin-6-yl)-2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1C2NCCOC2CN1C1=CC=C2C=C(C(=O)O)C(=O)NC2=C1 HBOHUPRFLRTLDQ-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 18
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
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- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- 229940077716 histamine h2 receptor antagonists for peptic ulcer and gord Drugs 0.000 description 1
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N hydroxylamine hydrochloride Substances Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
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- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
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- ZEKZLJVOYLTDKK-UHFFFAOYSA-N lomefloxacin Chemical compound FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNC(C)C1 ZEKZLJVOYLTDKK-UHFFFAOYSA-N 0.000 description 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
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- SGXXNSQHWDMGGP-IZZDOVSWSA-N nizatidine Chemical compound [O-][N+](=O)\C=C(/NC)NCCSCC1=CSC(CN(C)C)=N1 SGXXNSQHWDMGGP-IZZDOVSWSA-N 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
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- WVPSKSLAZQPAKQ-CDMJZVDBSA-N trovafloxacin Chemical compound C([C@H]1[C@@H]([C@H]1C1)N)N1C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=NC=1N2C1=CC=C(F)C=C1F WVPSKSLAZQPAKQ-CDMJZVDBSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5383—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines having two or more nitrogen atoms in the same ring, e.g. oxadiazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19652239A DE19652239A1 (de) | 1996-12-16 | 1996-12-16 | Verwendung von 7-(2-Oxa-5,8-diazabicyclo[4.3.0]non-8-yl)-chinolon- und -naphthyridoncarbonsäure-Derivaten zur Therapie von Helicobacter-pylori-Infektionen und den damit assoziierten gastroduodenalen Erkrankungen |
| PCT/EP1997/006781 WO1998026779A1 (de) | 1996-12-16 | 1997-12-04 | Verwendung von 7-(2-oxa-5,8-diazabicyclo[4.3.0]non-8-yl)-chinoloncarbonsäure- und -naphthyridoncarbonsäure-derivaten zur therapie von helicobacter-pylori-infektionen und den damit assoziierten gastroduodenalen erkrankungen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO992903L NO992903L (no) | 1999-06-14 |
| NO992903D0 NO992903D0 (no) | 1999-06-14 |
| NO325617B1 true NO325617B1 (no) | 2008-06-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19992903A NO325617B1 (no) | 1996-12-16 | 1999-06-14 | Anvendelse av 7-(2-oksa-5,8-diazabicyklo[4.3.0]non-8-yl)-kinolonkarboksylsyre og naftyridonkarboksylsyrederivater for fremstilling av legemidler for behandling av helicobacter pylori infeksjoner og dermed forbundede gastroduodenale sykdommer, diastereomerrene og enantiomerrene forbindelser, anvendelse derav samt legemiddel inneholdende disse. |
Country Status (28)
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| US (2) | US6133260A (ko) |
| EP (1) | EP0946176B1 (ko) |
| JP (3) | JP3463939B2 (ko) |
| KR (1) | KR100536153B1 (ko) |
| CN (1) | CN100335054C (ko) |
| AT (1) | ATE214929T1 (ko) |
| AU (1) | AU717751B2 (ko) |
| BG (1) | BG64615B1 (ko) |
| BR (1) | BR9714032A (ko) |
| CA (1) | CA2274894C (ko) |
| CZ (2) | CZ297364B6 (ko) |
| DE (2) | DE19652239A1 (ko) |
| DK (1) | DK0946176T3 (ko) |
| EA (1) | EA002477B1 (ko) |
| EE (1) | EE04090B1 (ko) |
| ES (1) | ES2175519T3 (ko) |
| HK (1) | HK1025517A1 (ko) |
| HU (1) | HU226523B1 (ko) |
| IL (1) | IL130311A (ko) |
| NO (1) | NO325617B1 (ko) |
| NZ (2) | NZ336228A (ko) |
| PL (1) | PL191193B1 (ko) |
| PT (1) | PT946176E (ko) |
| RS (1) | RS49684B (ko) |
| SK (2) | SK283223B6 (ko) |
| TR (1) | TR199901754T2 (ko) |
| UA (1) | UA57055C2 (ko) |
| WO (1) | WO1998026779A1 (ko) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19633805A1 (de) * | 1996-02-23 | 1997-08-28 | Bayer Ag | Gegenenenfalls substituierte 8-Cyan-l-cyclopropyl-7-(2,8-diazabicyclo-[4.3.0]-nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsäuren und ihre Derivate |
| ES2203254T3 (es) * | 1998-11-18 | 2004-04-01 | Asahi Glass Company Ltd. | Derivados de acido aminoacrilico y procedimiento de produccion correspondiente. |
| DE19917617A1 (de) * | 1999-04-19 | 2000-10-26 | Bayer Ag | -(-)Enantiomeres des 2-[2-(1-Chlor-cyclopropyl)-3-(2-chlorphenyl) 2-hydroxy-propyl]-2,4-dihydro-[1,2,4]-triazol-3-thions |
| US6858625B1 (en) * | 1999-07-01 | 2005-02-22 | Wakunaga Pharmaceutical Co., Ltd. | Quinolinecarboxylic acid derivative or salts thereof |
| JP4803935B2 (ja) * | 1999-10-08 | 2011-10-26 | アフィニアム・ファーマシューティカルズ・インコーポレイテッド | Ｆａｂｉ阻害剤 |
| EP1560584B1 (en) * | 2001-04-06 | 2009-01-14 | Affinium Pharmaceuticals, Inc. | Fab i inhibitors |
| DK1575951T3 (da) * | 2002-12-06 | 2014-09-15 | Debiopharm Int Sa | Heterocykliske forbindelser, fremgangsmåder til fremstilling deraf og deres anvendelse i terapi |
| JP4880448B2 (ja) | 2003-03-17 | 2012-02-22 | アフィナム ファーマシューティカルズ，インコーポレーテッド | 複数の抗生物質を含む組成物、及びそれを用いる方法 |
| ES2402420T3 (es) | 2003-09-29 | 2013-05-03 | Daiichi Sankyo Company, Limited | Derivado del ácido 8-cianoquinolonacarboxílico |
| CN1244582C (zh) * | 2004-04-21 | 2006-03-08 | 中国医学科学院医药生物技术研究所 | 喹诺酮羧酸类化合物及其制备方法和医药用途 |
| US7759362B2 (en) | 2004-04-21 | 2010-07-20 | Institut Of Medicinal Biotechnology Chinese Academy Of Medical Sciences | Quinolonecarboxylic acid compounds, preparation methods and pharmaceutical uses thereof |
| WO2007053131A2 (en) | 2004-06-04 | 2007-05-10 | Affinium Pharmaceuticals, Inc. | Acrylamide derivatives as antibiotic agents |
| US20090156578A1 (en) * | 2005-12-05 | 2009-06-18 | PAULS Henry | 3-Heterocyclylacrylamide Compounds as Fab I Inhibitors and Antibacterial Agents |
| CA2658506C (en) | 2006-07-20 | 2016-01-26 | Affinium Pharmaceuticals, Inc. | Acrylamide derivatives as fab 1 inhibitors |
| US8263613B2 (en) * | 2007-02-16 | 2012-09-11 | Affinium Pharmaceuticals, Inc. | Salts, prodrugs and polymorphs of fab I inhibitors |
| AU2010266120B2 (en) * | 2009-07-02 | 2014-02-06 | Curofin Pharma Gmbh | Compositions comprising finafloxacin and methods for treating ophthalmic, otic, or nasal infections |
| RU2449805C1 (ru) | 2011-01-27 | 2012-05-10 | Общество С Ограниченной Ответственностью "Гармония" | Пептидная фармацевтическая композиция, средство на ее основе для лечения гастродуоденальных заболеваний, вызываемых helicobacter pylori, и способ его использования |
| KR101720885B1 (ko) | 2012-06-19 | 2017-03-28 | 데비오팜 인터네셔날 에스 에이 | (e)-n-메틸-n-((3-메틸벤조푸란-2-일)메틸)-3-(7-옥소-5,6,7,8-테트라히드로-1,8-나프티리딘-3-일)아크릴아미드의전구약물 유도체 |
| US9504691B2 (en) * | 2012-12-06 | 2016-11-29 | Alcon Research, Ltd. | Finafloxacin suspension compositions |
| US20150045739A1 (en) | 2013-08-12 | 2015-02-12 | Novartis Ag | Method for treating otic infections after tympanostomy tube placement |
| DE102014115951A1 (de) | 2014-11-03 | 2016-05-04 | Merlion Pharmaceuticals Pte Ltd. | Zusammensetzungen, die Finafloxacin und Tris enthalten |
| DE102015100068A1 (de) | 2015-01-06 | 2016-07-07 | Merlion Pharmaceuticals Pte Ltd. | Finafloxacin zur verwendung bei der behandlung von harnwegsinfektionen |
| LT3419628T (lt) | 2016-02-26 | 2021-01-25 | Debiopharm International Sa | Medikamentas diabetinėms pėdų infekcijoms gydyti |
| CN107987074B (zh) * | 2017-10-27 | 2020-12-29 | 浙江美诺华药物化学有限公司 | 一种普拉沙星的合成方法 |
| CN111989314B (zh) | 2018-04-25 | 2024-04-30 | 拜耳动物保健有限责任公司 | 喹诺酮甲酸酯水解的方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4822801A (en) * | 1984-07-20 | 1989-04-18 | Warner-Lambert Company | 4-oxo-1,4-dihydroquinoline-3-carboxylic acid derivative as antibacterial agents |
| JPS62205060A (ja) * | 1986-03-04 | 1987-09-09 | Kyorin Pharmaceut Co Ltd | ８位置換キノロンカルボン酸誘導体 |
| DE3702393A1 (de) * | 1987-01-28 | 1988-08-11 | Bayer Ag | 8-cyano-1-cyclopropyl-1,4-dihydro-4-oxo- 3-chinolincarbonsaeuren, verfahren zu ihrer herstellung und diese enthaltende antibakterielle mittel |
| US5563138A (en) * | 1987-04-16 | 1996-10-08 | Otsuka Pharmaceutical Company, Limited | Benzoheterocyclic compounds |
| US4889857A (en) * | 1987-10-12 | 1989-12-26 | Yoshitomi Pharmaceutical Industries, Ltd. | Quinolonecarboxylic acid compounds and pharmaceutical use thereof |
| WO1989005643A1 (en) * | 1987-12-18 | 1989-06-29 | Pfizer Inc. | Heterocyclic-substituted quinoline-carboxylic acids |
| JP2844079B2 (ja) * | 1988-05-23 | 1999-01-06 | 塩野義製薬株式会社 | ピリドンカルボン酸系抗菌剤 |
| DE3906365A1 (de) * | 1988-07-15 | 1990-01-18 | Bayer Ag | 7-(1-pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsaeure-derivate, verfahren sowie substituierte (oxa)diazabicyclooctane und -nonane als zwischenprodukte zu ihrer herstellung, und sie enthaltende antibakterielle mittel und futterzusatzstoffe |
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1996
- 1996-12-16 DE DE19652239A patent/DE19652239A1/de not_active Withdrawn
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1997
- 1997-04-12 UA UA99074093A patent/UA57055C2/uk unknown
- 1997-12-04 AT AT97954354T patent/ATE214929T1/de active
- 1997-12-04 EE EEP199900248A patent/EE04090B1/xx unknown
- 1997-12-04 DE DE59706808T patent/DE59706808D1/de not_active Expired - Lifetime
- 1997-12-04 CA CA002274894A patent/CA2274894C/en not_active Expired - Lifetime
- 1997-12-04 PL PL333928A patent/PL191193B1/pl unknown
- 1997-12-04 HU HU0000450A patent/HU226523B1/hu unknown
- 1997-12-04 EP EP97954354A patent/EP0946176B1/de not_active Expired - Lifetime
- 1997-12-04 BR BR9714032-5A patent/BR9714032A/pt not_active IP Right Cessation
- 1997-12-04 SK SK795-99A patent/SK283223B6/sk not_active IP Right Cessation
- 1997-12-04 CZ CZ20003148A patent/CZ297364B6/cs not_active IP Right Cessation
- 1997-12-04 CZ CZ0216899A patent/CZ297363B6/cs not_active IP Right Cessation
- 1997-12-04 PT PT97954354T patent/PT946176E/pt unknown
- 1997-12-04 IL IL13031197A patent/IL130311A/en not_active IP Right Cessation
- 1997-12-04 KR KR10-1999-7005330A patent/KR100536153B1/ko not_active IP Right Cessation
- 1997-12-04 NZ NZ336228A patent/NZ336228A/xx not_active IP Right Cessation
- 1997-12-04 EA EA199900526A patent/EA002477B1/ru not_active IP Right Cessation
- 1997-12-04 TR TR1999/01754T patent/TR199901754T2/xx unknown
- 1997-12-04 US US09/319,888 patent/US6133260A/en not_active Expired - Lifetime
- 1997-12-04 AU AU58541/98A patent/AU717751B2/en not_active Expired
- 1997-12-04 WO PCT/EP1997/006781 patent/WO1998026779A1/de active IP Right Grant
- 1997-12-04 RS YUP-274/99A patent/RS49684B/sr unknown
- 1997-12-04 ES ES97954354T patent/ES2175519T3/es not_active Expired - Lifetime
- 1997-12-04 DK DK97954354T patent/DK0946176T3/da active
- 1997-12-04 CN CNB971817200A patent/CN100335054C/zh not_active Expired - Lifetime
- 1997-12-04 JP JP52725098A patent/JP3463939B2/ja not_active Expired - Lifetime
- 1997-12-04 SK SK1496-2000A patent/SK283224B6/sk not_active IP Right Cessation
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1999
- 1999-06-08 BG BG103474A patent/BG64615B1/bg unknown
- 1999-06-14 NO NO19992903A patent/NO325617B1/no not_active IP Right Cessation
- 1999-11-08 US US09/436,316 patent/US6432948B1/en not_active Expired - Lifetime
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2000
- 2000-05-25 JP JP2000154543A patent/JP4463380B2/ja not_active Expired - Lifetime
- 2000-08-04 HK HK00104882A patent/HK1025517A1/xx not_active IP Right Cessation
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2009
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| CHAD | Change of the owner's name or address (par. 44 patent law, par. patentforskriften) |
Owner name: BAYER INTELLECTUAL PROPERTY GMBH, DE |
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| MK1K | Patent expired |