AR004706A1 - Un compuesto derivado de benzoxazina y pirido-oxazina utiles como antimicrobianos, composicion farmaceutica que lo contienen, un metodo para preparar dichos compuestos e intermediarios utiles para dicho metodo. - Google Patents
Un compuesto derivado de benzoxazina y pirido-oxazina utiles como antimicrobianos, composicion farmaceutica que lo contienen, un metodo para preparar dichos compuestos e intermediarios utiles para dicho metodo.Info
- Publication number
- AR004706A1 AR004706A1 ARP960105075A ARP960105075A AR004706A1 AR 004706 A1 AR004706 A1 AR 004706A1 AR P960105075 A ARP960105075 A AR P960105075A AR P960105075 A ARP960105075 A AR P960105075A AR 004706 A1 AR004706 A1 AR 004706A1
- Authority
- AR
- Argentina
- Prior art keywords
- co2h
- alkyl
- useful
- hydroxy
- halogen
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 4
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 239000004599 antimicrobial Substances 0.000 title 1
- -1 hydroxy, amino, nitro, sulfonylamino Chemical group 0.000 abstract 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 abstract 1
- SHASOVNNKCSWPT-UHFFFAOYSA-N 2h-pyrido[2,3-e]oxazine Chemical compound C1=CN=C2C=CNOC2=C1 SHASOVNNKCSWPT-UHFFFAOYSA-N 0.000 abstract 1
- 101100439663 Arabidopsis thaliana CHR7 gene Proteins 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000002148 esters Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000000651 prodrug Chemical group 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
-
- 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
-
- 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
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
Abstract
Un compuesto derivado de benzoxazina y pirido-oxazina que está seleccionado entre los de la fórmula (I), en el cual la porción Q es una porción fenilofusionada o una porción piridilo fusionada; Z1 es H, halógeno, alquilo C1-C6, fenilo,hidroxi,amin o, nitro, sulfonilamino o trifluorometilo; Z2 es H ó unhalógeno; X es H u oxígeno: A es alquilo C1-C6,alquilarilo C1-C6, ó alquilheterociclilo, donde arilo es bifenilo, naftilo o fenilo; y heterocicliloes un grupo heterocíclico de 5a 6 m iembros saturado o insaturado que contiene de 1 a 4 átomos de H, un átomo de oxígeno o un átomo de azufre; donde dichoarilo o grupo heterocíclico es optativamente sustituido con alquilo (C1-C6), bencido, oxibencilo, fenoxi, hidroxi,alcoxi, halóg eno, dihalógeno,nitro,amino,carboxilo, carbo (C1-C4)alcoxi o metilsulfonilamino; n es un entero 0-3; Y es una porción seleccionada entre: (a)NHR1R2; N+R1R2R3; (b)(II); (c) CO2H, CHO;(d) CH(R6)CO2H, CH(R6)CO2CH3 CH=CHR7, CH=C(CO2H)2;(e) una porció n de la fórmula (III); (f) 5-tetrazolilo; donde R1, R2 y R3 son, independientemenete,H, alquilo C1-C6, o t-butoxicarbonilo; R4 y R5 son, independientemente, t- butoxicarbonilo ó H ó R4 y R5 pueden estar unidos para formarun anillo deimida zolina, imidazolilo o pirimidina; R6 es H, hidroxi o cloro; R7es CO2H ó C(O)NH(CH2)pOH, donde p es un entero de 1 a 4: y las sales farmacéuticamenteaceptables, ésteres y formas profármacos de los mismos, composición farmacéuticaque lo contienen, un método para preparar dichos compuestos eintermediarios útiles para dicho método.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/553,188 US5696117A (en) | 1995-11-07 | 1995-11-07 | Benzoxazine antimicrobial agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR004706A1 true AR004706A1 (es) | 1999-03-10 |
Family
ID=24208465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP960105075A AR004706A1 (es) | 1995-11-07 | 1996-11-06 | Un compuesto derivado de benzoxazina y pirido-oxazina utiles como antimicrobianos, composicion farmaceutica que lo contienen, un metodo para preparar dichos compuestos e intermediarios utiles para dicho metodo. |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US5696117A (es) |
| EP (1) | EP0869949B1 (es) |
| JP (1) | JP2000500134A (es) |
| KR (1) | KR100503910B1 (es) |
| AR (1) | AR004706A1 (es) |
| AT (1) | ATE229944T1 (es) |
| AU (1) | AU720743B2 (es) |
| BR (1) | BR9611400A (es) |
| CZ (1) | CZ137998A3 (es) |
| DE (1) | DE69625515T2 (es) |
| DK (1) | DK0869949T3 (es) |
| ES (1) | ES2188795T3 (es) |
| HU (1) | HUP9901184A3 (es) |
| IL (1) | IL124337A (es) |
| MX (1) | MX9803650A (es) |
| MY (1) | MY128650A (es) |
| NO (1) | NO311026B1 (es) |
| NZ (1) | NZ321251A (es) |
| PL (1) | PL189987B1 (es) |
| RU (1) | RU2191179C2 (es) |
| SK (2) | SK285388B6 (es) |
| TW (1) | TW536537B (es) |
| WO (1) | WO1997017333A1 (es) |
| ZA (1) | ZA969326B (es) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6265401B1 (en) * | 1997-10-27 | 2001-07-24 | Reddy-Cheminor, Inc. | Bicyclic compounds and their use in medicine, process for their preparation and pharmaceutical compositions containing them |
| RU2247722C2 (ru) | 1997-10-27 | 2005-03-10 | Др. Редди`З Лабораториз Лимитед | Производные арилкарбоновых кислот, способы их получения, фармацевтическая композиция на их основе, способы лечения и предупреждения различных заболеваний, промежуточные соединения и способы их получения |
| WO1999052861A1 (de) * | 1998-04-09 | 1999-10-21 | Institut für Diagnostikforschung GmbH an der Freien Universität Berlin | Neue benzylguanidinderivate für die therapie, in-vivo- und in-vitro-diagnostik |
| US6667299B1 (en) * | 2000-03-16 | 2003-12-23 | Hollis-Eden Pharmaceuticals, Inc. | Pharmaceutical compositions and treatment methods |
| WO2001012600A1 (en) * | 1999-08-12 | 2001-02-22 | Cor Therapeutics, Inc. | INHIBITORS OF FACTOR Xa |
| US6908908B2 (en) | 2000-05-12 | 2005-06-21 | Ortho-Mcneil Pharmaceutical, Inc. | Biologically active 4H-benzo [1,4] oxazin-3-ones |
| US6555536B2 (en) | 2000-05-12 | 2003-04-29 | Ortho-Mcneil Pharmaceutical, Inc. | Biologically active 4H-benzo [1,4]oxazin-3-ones |
| WO2001087860A2 (en) * | 2000-05-12 | 2001-11-22 | Ortho-Mcneil Pharmaceutical, Inc. | Novel benzoxazinones as peroxisome proliferator activated receptor gamma modulators and method of treatment |
| EP1280783A2 (en) * | 2000-05-12 | 2003-02-05 | Ortho-McNeil Pharmaceutical, Inc. | Methods of treatment using benzoxazinones as peroxisome proliferator activated receptor gamma modulators |
| EP1554572B1 (en) | 2001-07-25 | 2009-10-14 | Raptor Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
| WO2005021518A1 (ja) * | 2003-09-01 | 2005-03-10 | Ono Pharmaceutical Co., Ltd. | 縮環化合物およびその用途 |
| BRPI0414487A (pt) * | 2003-09-17 | 2006-11-14 | Ono Pharmaceutical Co | composto de ácido carboxìlico e composições medicinais contendo os mesmos como o ingrediente ativo |
| US20050266575A1 (en) * | 2004-05-27 | 2005-12-01 | Mayo Kevin H | Pharmacophores for nociceptin, methods of obtaining and using in screening for nociceptin mimics |
| GB0423405D0 (en) * | 2004-10-21 | 2004-11-24 | Novartis Ag | Organic compounds |
| WO2006082495A1 (en) * | 2005-02-02 | 2006-08-10 | Ranbaxy Laboratories Limited | Peroxisome proliferator activated receptor modulators |
| CN101287411B (zh) | 2005-04-28 | 2013-03-06 | 普罗秋斯生物医学公司 | 药物信息系统及其用途 |
| EP1953154A4 (en) * | 2005-11-24 | 2013-11-20 | Eisai R&D Man Co Ltd | CINNAMIDE COMPOUNDS OF MORPHOLINE TYPE |
| WO2007086504A1 (ja) * | 2006-01-27 | 2007-08-02 | Japan Tobacco Inc. | カルボン酸化合物及びその用途 |
| US20070197512A1 (en) * | 2006-01-27 | 2007-08-23 | Japan Tobacco Inc. | Carboxylic Acid Compounds and Use Thereof |
| TWI385161B (zh) | 2006-02-02 | 2013-02-11 | Mitsubishi Tanabe Pharma Corp | 含氮雜雙環化合物 |
| JP5099814B2 (ja) * | 2006-02-02 | 2012-12-19 | 田辺三菱製薬株式会社 | 含窒素複素二環式化合物 |
| EP2279662A3 (en) * | 2006-03-10 | 2011-04-13 | Yuuzou Tsuchida | 5,7,4'-trihydroxy-3',5'-dimethoxyflavone as an antibacterial agent |
| EP2063905B1 (en) | 2006-09-18 | 2014-07-30 | Raptor Pharmaceutical Inc | Treatment of liver disorders by administration of receptor-associated protein (rap)-conjugates |
| TWI410410B (zh) * | 2007-08-10 | 2013-10-01 | Ono Pharmaceutical Co | Phenylacetic acid compounds |
| HUE059078T2 (hu) | 2009-02-20 | 2022-10-28 | Enhanx Biopharm Inc | Glutation-alapú hatóanyagszállító rendszer |
| BRPI1015525A2 (pt) * | 2009-04-14 | 2015-09-01 | Nissan Chemical Ind Ltd | Derivados de haloalquilsulfonanilida, seus usos, seus intermediários e seu método de uso, bem como agroquímico e herbicida |
| KR101909711B1 (ko) | 2009-05-06 | 2018-12-19 | 라보라토리 스킨 케어, 인크. | 활성제-칼슘 포스페이트 입자 복합체를 포함하는 피부 전달 조성물 및 이들을 이용하는 방법 |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
| US8669363B2 (en) | 2011-03-24 | 2014-03-11 | Southern Methodist University | Quinoxaline compounds and derivatives |
| US9493452B2 (en) | 2011-03-24 | 2016-11-15 | Southern Methodist University | Compounds and derivatives of 2H-pyrido (3,2-b)(1, 4) oxazin 3)4H)-ones as raf kinase and LRRK2 inhibitors |
| US9309208B2 (en) | 2012-03-23 | 2016-04-12 | Southern Methodist University | Methods of making and using thioxothiazolidine and rhodanine derivatives as HIV-1 and JSP-1 inhibitors |
| GB2533925A (en) * | 2014-12-31 | 2016-07-13 | Univ Bath | Antimicrobial compounds, compositions and methods |
| EP3871667A4 (en) * | 2018-10-23 | 2022-08-17 | Japan Science and Technology Agency | PPAR DELTA ACTIVATOR |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3635956A (en) * | 1968-03-01 | 1972-01-18 | Squibb & Sons Inc | Benzothiazines related compounds derivatives and salts thereof |
| US3725403A (en) * | 1970-10-20 | 1973-04-03 | Squibb & Sons Inc | Benzothiazine derivatives |
| JPS5547006B2 (es) * | 1973-04-04 | 1980-11-27 | ||
| FR2588868B1 (fr) * | 1985-10-21 | 1988-11-10 | Negma Laboratoires | Acyl-7 benzoxazinones et leurs derives, procede pour les obtenir et compositions pharmaceutiques les contenant |
| EP0233728A1 (en) * | 1986-02-11 | 1987-08-26 | Takeda Chemical Industries, Ltd. | 1,4-Benzoxazine derivatives their production and use |
| DE3705621C2 (de) * | 1986-02-25 | 1997-01-09 | Otsuka Pharma Co Ltd | Heterocyclisch substituierte Chinoloncarbonsäurederivate |
| EP0489733A1 (en) * | 1989-04-26 | 1992-06-17 | The Upjohn Company | Antibacterial pyrido(1,2,3-de)-1,4-benzoxazinone agents |
| FI96313C (fi) * | 1990-11-28 | 1996-06-10 | Daiichi Seiyaku Co | Menetelmä terapeuttisesti käyttökelpoisten ja optisesti aktiivisten 10-(3-amino-4,4-dialkyyli-1-pyrrolidinyyli)-9-fluori-2,3-dihydro-3(S)-metyyli-7-okso-7H-pyrido/1,2,3-de//1,4/bentsoksatsiini-6-karboksyylihappojen valmistamiseksi |
| DE4304806A1 (de) * | 1993-02-17 | 1994-08-18 | Kali Chemie Pharma Gmbh | 5-Phenyl-pyrrolo-1,4-benzoxazin- und -thiazin-Derivate sowie Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| FR2714381B1 (fr) * | 1993-12-29 | 1996-02-02 | Pharmascience Lab | Dérivés de la benzoxazine, leurs procédés d'obtention et leur utilisation en tant que médicaments . |
-
1995
- 1995-11-07 US US08/553,188 patent/US5696117A/en not_active Expired - Lifetime
-
1996
- 1996-10-17 NZ NZ321251A patent/NZ321251A/en unknown
- 1996-10-17 CZ CZ981379A patent/CZ137998A3/cs unknown
- 1996-10-17 ES ES96936648T patent/ES2188795T3/es not_active Expired - Lifetime
- 1996-10-17 AT AT96936648T patent/ATE229944T1/de not_active IP Right Cessation
- 1996-10-17 BR BR9611400-2A patent/BR9611400A/pt not_active IP Right Cessation
- 1996-10-17 PL PL96326704A patent/PL189987B1/pl not_active IP Right Cessation
- 1996-10-17 JP JP9518188A patent/JP2000500134A/ja not_active Ceased
- 1996-10-17 RU RU98110572/04A patent/RU2191179C2/ru not_active IP Right Cessation
- 1996-10-17 HU HU9901184A patent/HUP9901184A3/hu unknown
- 1996-10-17 EP EP96936648A patent/EP0869949B1/en not_active Expired - Lifetime
- 1996-10-17 SK SK1033-2002A patent/SK285388B6/sk not_active IP Right Cessation
- 1996-10-17 DK DK96936648T patent/DK0869949T3/da active
- 1996-10-17 IL IL12433796A patent/IL124337A/en not_active IP Right Cessation
- 1996-10-17 SK SK597-98A patent/SK283888B6/sk not_active IP Right Cessation
- 1996-10-17 WO PCT/US1996/016669 patent/WO1997017333A1/en not_active Ceased
- 1996-10-17 AU AU74519/96A patent/AU720743B2/en not_active Ceased
- 1996-10-17 KR KR10-1998-0703405A patent/KR100503910B1/ko not_active Expired - Fee Related
- 1996-10-17 DE DE69625515T patent/DE69625515T2/de not_active Expired - Fee Related
- 1996-11-06 AR ARP960105075A patent/AR004706A1/es active IP Right Grant
- 1996-11-06 ZA ZA9609326A patent/ZA969326B/xx unknown
- 1996-11-07 MY MYPI96004648A patent/MY128650A/en unknown
- 1996-11-25 TW TW085114485A patent/TW536537B/zh not_active IP Right Cessation
-
1997
- 1997-07-23 US US08/899,235 patent/US5854242A/en not_active Expired - Lifetime
-
1998
- 1998-05-06 NO NO19982071A patent/NO311026B1/no not_active IP Right Cessation
- 1998-05-07 MX MX9803650A patent/MX9803650A/es not_active IP Right Cessation
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