AU708006B2 - New crystal modification of CDCH, a process for its preparation and pharmaceutical formulations comprising this modification - Google Patents
New crystal modification of CDCH, a process for its preparation and pharmaceutical formulations comprising this modification Download PDFInfo
- Publication number
- AU708006B2 AU708006B2 AU74216/96A AU7421696A AU708006B2 AU 708006 B2 AU708006 B2 AU 708006B2 AU 74216/96 A AU74216/96 A AU 74216/96A AU 7421696 A AU7421696 A AU 7421696A AU 708006 B2 AU708006 B2 AU 708006B2
- Authority
- AU
- Australia
- Prior art keywords
- cdch
- monohydrate
- preparation
- modification
- anhydrous
- 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.)
- Expired
Links
- 239000013078 crystal Substances 0.000 title claims description 30
- 238000002360 preparation method Methods 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 13
- 238000012986 modification Methods 0.000 title claims description 12
- 230000004048 modification Effects 0.000 title claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- 230000008569 process Effects 0.000 title claims description 10
- 102100034741 Cyclin-dependent kinase 20 Human genes 0.000 title claims 4
- 101500014379 Lymnaea stagnalis Ovulation hormone Proteins 0.000 title claims 4
- 150000004682 monohydrates Chemical class 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 8
- 230000000844 anti-bacterial effect Effects 0.000 claims description 3
- 241000894006 Bacteria Species 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- 238000002156 mixing Methods 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 238000001413 far-infrared spectroscopy Methods 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001757 thermogravimetry curve Methods 0.000 description 5
- 238000001237 Raman spectrum Methods 0.000 description 4
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001069 Raman spectroscopy Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000007864 suspending Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940032049 enterococcus faecalis Drugs 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- IDIIJJHBXUESQI-DFIJPDEKSA-N moxifloxacin hydrochloride Chemical compound Cl.COC1=C(N2C[C@H]3NCCC[C@H]3C2)C(F)=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 IDIIJJHBXUESQI-DFIJPDEKSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000010996 solid-state NMR spectroscopy Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19546249 | 1995-12-12 | ||
| DE19546249A DE19546249A1 (de) | 1995-12-12 | 1995-12-12 | Neue Kristallmodifikation des 1-Cyclopropyl-7-([S,S]-2,8-diazabicyclo[4,3,0]non-8-yl)-6-fluor-1,4-dihydro-8-methoxy-4-oxo-3-chinolincarbonsäure Hydrochlorid (CDCH), Verfahren zu dessen Herstellung und diese enthaltende pharmazeutische Zubereitungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7421696A AU7421696A (en) | 1997-06-19 |
| AU708006B2 true AU708006B2 (en) | 1999-07-29 |
Family
ID=7779831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU74216/96A Expired AU708006B2 (en) | 1995-12-12 | 1996-12-06 | New crystal modification of CDCH, a process for its preparation and pharmaceutical formulations comprising this modification |
Country Status (42)
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1895233A (zh) * | 1997-09-25 | 2007-01-17 | 拜尔公司 | 控释活性化合物的药物制剂 |
| DE19751948A1 (de) | 1997-11-24 | 1999-05-27 | Bayer Ag | Verfahren zur Herstellung von 8-Methoxy-Chinoloncarbonsäuren |
| US6509327B1 (en) | 1998-09-30 | 2003-01-21 | Alcon Manufacturing, Ltd. | Compositions and methods for treating otic, ophthalmic and nasal infections |
| US6716830B2 (en) | 1998-09-30 | 2004-04-06 | Alcon, Inc. | Ophthalmic antibiotic compositions containing moxifloxacin |
| US6395746B1 (en) | 1998-09-30 | 2002-05-28 | Alcon Manufacturing, Ltd. | Methods of treating ophthalmic, otic and nasal infections and attendant inflammation |
| DK1128831T3 (da) | 1998-11-10 | 2005-01-17 | Bayer Healthcare Ag | Farmaceutisk moxifloxacinpræparat |
| DE19854357A1 (de) * | 1998-11-25 | 2000-05-31 | Bayer Ag | Semi-Hydrochlorid von 8-Cyan-1-cyclopropyl-7-(1S,6S-2,8-diazabicyclo/4.3.0/ -nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsäure |
| DE19854356A1 (de) * | 1998-11-25 | 2000-05-31 | Bayer Ag | Kristallmodifikation A von 8-Cyan-1-cyclopropyl-7-(1S,6S-2,8-diazabicyclo-/4.3.0/nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsäure |
| DE19854355A1 (de) * | 1998-11-25 | 2000-05-31 | Bayer Ag | Kristallmodifikation B von 8-Cyan-1-cyclopropyl-7-(1S, 6S-2,8-diazabicyclo-/4.3.O/nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsäure |
| DE19908449A1 (de) * | 1999-02-26 | 2000-08-31 | Bayer Ag | Kristallmodifikation C von 8-Cyan-1-cyclopropyl-7-(1S,6S-2,8-diazabicylo-[4.3.0]nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chino/incarbonsäure |
| EP1562942A1 (en) * | 2002-10-31 | 2005-08-17 | Ranbaxy Laboratories, Ltd. | Amorphous moxifloxacin hydrochloride |
| EP2113505A1 (en) | 2003-04-09 | 2009-11-04 | Dr. Reddy's Laboratories, Ltd. | A crystalline form III of anhydrous moxifloxacin hydrochloride and processes for the preparation thereof |
| EP1651630A1 (en) * | 2003-08-05 | 2006-05-03 | Matrix Laboratories Ltd | An improved process for the preparation of moxifloxacin hydrochloride |
| WO2005054240A1 (en) * | 2003-11-20 | 2005-06-16 | Chemi Spa | Polymorphs of 1-cyclopropyl-7-([s,s]-2,8-diazadicyclo[4.3.0]non-8-yl)-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid hydrochloride and methods for the preparation thereof |
| ITMI20032259A1 (it) | 2003-11-20 | 2005-05-21 | Chemi Spa | Nuovo polimorfo dell'acido 1-ciclopropil-7-(s,s-2,8-diazabciclo-4.3.0-non-8-il)-6-fluoro-1,4-diidro-8-metossi-4-oxo-chinolin carbossilico cloridrato e metodi per la sua preparazione |
| US7491725B2 (en) | 2004-02-06 | 2009-02-17 | Bristol-Myers Squibb Company | Process for preparing 2-aminothiazole-5-aromatic carboxamides as kinase inhibitors |
| DE102004015981A1 (de) * | 2004-04-01 | 2005-10-20 | Bayer Healthcare Ag | Neue kirstalline Form von 8-Cyan-1-cyclopropyl-7-(1S,6S-2,8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsäure |
| DE102004063347A1 (de) * | 2004-12-23 | 2006-07-13 | Stada Arzneimittel Ag | Gebrauchsfertige Gemcitabinlösungen und Gemcitabinlösungskonzentrate |
| WO2007033515A1 (fr) * | 2005-09-21 | 2007-03-29 | Shenzhen Tys R & D Co., Ltd. | Formulation orale contenant de la moxifloxacine et son procédé de préparation |
| GB0612422D0 (en) * | 2006-06-23 | 2006-08-02 | Generics Uk Ltd | Novel hydrate form |
| CN101484411A (zh) | 2006-06-27 | 2009-07-15 | 桑多斯股份公司 | 盐的新制备方法 |
| ES2303768B1 (es) * | 2006-09-08 | 2009-06-05 | Quimica Sintetica, S.A. | Nueva forma cristalina de moxifloxacino clorhidrato. |
| JP2010509305A (ja) * | 2006-11-13 | 2010-03-25 | シプラ・リミテッド | モキシフロキサシン塩酸塩の合成方法 |
| EP1992626A1 (en) * | 2007-05-10 | 2008-11-19 | Sandoz AG | Process for the preparation of moxifloxacin hydrochloride |
| EP2083010A1 (en) * | 2008-01-08 | 2009-07-29 | Chemo Ibérica, S.A. | Polymorphic Forms of Moxifloxacin hydrochloride and processes for preparation thereof |
| EP2154137A1 (en) | 2008-08-04 | 2010-02-17 | Chemo Ibérica, S.A. | Crystalline form of moxifloxacin base |
| EP2349220B1 (en) | 2008-10-09 | 2012-07-25 | Abdi Ibrahim Ilac Sanayi ve Ticaret Anonim Sirketi | Using of organic solvents in wet granulation of moxifloxacin |
| WO2010052726A1 (en) * | 2008-11-06 | 2010-05-14 | Hetero Research Foundation | Novel polymorph of moxifloxacin hydrochloride |
| ES2467105T5 (es) | 2008-12-08 | 2017-12-05 | Ratiopharm Gmbh | Moxifloxacino compactado |
| WO2010131054A1 (en) | 2009-05-15 | 2010-11-18 | Bradford Pharma Limited | Redox drug derivatives |
| WO2011121596A2 (en) * | 2010-04-01 | 2011-10-06 | Neuland Laboratories Ltd. | Crystal modification of moxifloxacin hydrochloride |
| BRPI1106900A2 (pt) | 2011-12-26 | 2013-11-05 | Ems Sa | Composição farmacêutica sólida compreendendo antibótico da familia das quinolonas e processo de sua obtenção |
| FR2992218B1 (fr) | 2012-06-22 | 2015-01-23 | Rivopharm Sa | Composition pharmaceutique de chlorhydrate de moxifloxacine et procede de preparation |
| CN102924449B (zh) * | 2012-10-30 | 2015-08-12 | 重庆福安药业集团庆余堂制药有限公司 | 盐酸莫西沙星h晶型及其制备方法和药物组合物 |
| EP2928892B1 (en) | 2012-12-04 | 2018-03-21 | Mankind Pharma Ltd. | An improved process for the preparation of moxifloxacin hydrochloride |
| RU2561037C2 (ru) * | 2013-02-07 | 2015-08-20 | Открытое акционерное общество "Химико-фармацевтический комбинат "АКРИХИН" (ОАО "АКРИХИН") | Антибактериальная фармацевтическая композиция и способ ее получения |
| AU2014239965A1 (en) | 2013-03-15 | 2015-09-24 | Melinta Subsidiary Corp. | Methods of treating infections in overweight and obese patients using antibiotics |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3601567A1 (de) * | 1986-01-21 | 1987-07-23 | Bayer Ag | 7-(azabicycloalkyl)-chinoloncarbonsaeure- und -naphthyridon-carbonsaeure-derivate |
| DK164287A (da) * | 1986-03-31 | 1987-10-01 | Sankyo Co | Quinolin-3-carboxylsyrederivater og fremgangsmaade til fremstilling deraf og deres anvendelse |
| AU609974B2 (en) * | 1988-05-18 | 1991-05-09 | Warner-Lambert Company | Improved process for the preparation of 5-amino-7- (substituted amino)-quinoline-3-carboxylic acids |
| DE3910663A1 (de) * | 1989-04-03 | 1990-10-04 | Bayer Ag | 5-alkylchinoloncarbonsaeuren |
| RO108347B1 (ro) * | 1989-10-30 | 1994-04-28 | Bellon Labor Sa Roger | DERIVATI DE BENZO-(b)-NAFTIRIDIN-1,8 SI PROCEDEU DE PREPARARE A ACESTORA |
| TW209865B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-01-10 | 1993-07-21 | Bayer Ag | |
| CA2128601C (en) * | 1992-01-31 | 2003-07-15 | Hiroyuki Nagano | Quinolone carboxylic acid derivatives in crystalline hydrate form |
| DE4234078A1 (de) * | 1992-10-09 | 1994-04-14 | Bayer Ag | Chinoloncarbonsäuren |
| JP3268098B2 (ja) * | 1992-12-25 | 2002-03-25 | 第一製薬株式会社 | 二環性環状アミン誘導体 |
| ZA946853B (en) * | 1993-09-10 | 1995-04-24 | Daiichi Seiyaku Co | Crystals of antimicrobial compound. |
| EP0676199B1 (en) * | 1994-04-07 | 1998-09-02 | Pfizer Inc. | Use of trovafloxacin or derivatives thereof for the manufacture of a medicament for the treatment of H. pylori infections |
-
1995
- 1995-12-12 DE DE19546249A patent/DE19546249A1/de not_active Withdrawn
-
1996
- 1996-11-22 MA MA24398A patent/MA24342A1/fr unknown
- 1996-11-25 HR HR960558A patent/HRP960558B1/xx not_active IP Right Cessation
- 1996-11-25 RO RO96-02223A patent/RO119782B1/ro unknown
- 1996-11-27 CU CU1996111A patent/CU22774A3/es not_active IP Right Cessation
- 1996-11-29 DE DE59609501T patent/DE59609501D1/de not_active Expired - Lifetime
- 1996-11-29 DK DK96119134T patent/DK0780390T3/da active
- 1996-11-29 PT PT96119134T patent/PT780390E/pt unknown
- 1996-11-29 ES ES96119134T patent/ES2179910T3/es not_active Expired - Lifetime
- 1996-11-29 AT AT96119134T patent/ATE221531T1/de active
- 1996-11-29 SI SI9630468T patent/SI0780390T1/xx unknown
- 1996-11-29 EP EP96119134A patent/EP0780390B1/de not_active Expired - Lifetime
- 1996-12-05 US US08/760,543 patent/US5849752A/en not_active Expired - Lifetime
- 1996-12-05 TR TR96/00970A patent/TR199600970A2/xx unknown
- 1996-12-06 IN IN2723DE1996 patent/IN185805B/en unknown
- 1996-12-06 AU AU74216/96A patent/AU708006B2/en not_active Expired
- 1996-12-06 TW TW085115048A patent/TW411340B/zh not_active IP Right Cessation
- 1996-12-06 YU YU65096A patent/YU49485B/sh unknown
- 1996-12-09 NZ NZ299905A patent/NZ299905A/en not_active IP Right Cessation
- 1996-12-09 AR ARP960105569A patent/AR005009A1/es active IP Right Grant
- 1996-12-09 CA CA002192418A patent/CA2192418C/en not_active Expired - Lifetime
- 1996-12-10 IL IL11979596A patent/IL119795A/en not_active IP Right Cessation
- 1996-12-10 BG BG101043A patent/BG62258B1/bg unknown
- 1996-12-10 ID IDP963684A patent/ID22625A/id unknown
- 1996-12-10 JP JP34450296A patent/JP4104687B2/ja not_active Expired - Lifetime
- 1996-12-10 CO CO96064770A patent/CO4480105A1/es unknown
- 1996-12-10 SG SG1996011612A patent/SG47201A1/en unknown
- 1996-12-10 PL PL96317415A patent/PL184885B1/pl unknown
- 1996-12-11 ZA ZA9610405A patent/ZA9610405B/xx unknown
- 1996-12-11 SK SK1591-96A patent/SK282805B6/sk not_active IP Right Cessation
- 1996-12-11 NO NO19965298A patent/NO306725B1/no not_active IP Right Cessation
- 1996-12-11 BR BR9605968A patent/BR9605968A/pt not_active IP Right Cessation
- 1996-12-11 KR KR1019960064345A patent/KR100525146B1/ko not_active Expired - Lifetime
- 1996-12-11 CZ CZ19963646A patent/CZ288657B6/cs not_active IP Right Cessation
- 1996-12-11 SA SA96170492A patent/SA96170492B1/ar unknown
- 1996-12-11 RU RU96123410/04A patent/RU2162468C2/ru active
- 1996-12-11 EE EE9600201A patent/EE03474B1/xx unknown
- 1996-12-11 MY MYPI96005214A patent/MY117492A/en unknown
- 1996-12-11 UA UA96124628A patent/UA35638C2/uk unknown
- 1996-12-12 SV SV1996000109A patent/SV1996000109A/es active IP Right Grant
- 1996-12-12 HU HU9603428A patent/HU226521B1/hu unknown
- 1996-12-12 CN CN96123220A patent/CN1061348C/zh not_active Expired - Lifetime
-
2002
- 2002-12-05 NL NL300109C patent/NL300109I1/nl unknown
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