SK282433B6 - Spôsob prípravy častíc S(+)-ibuprofénu - Google Patents

Spôsob prípravy častíc S(+)-ibuprofénu Download PDF

Info

Publication number: SK282433B6
Authority: SK; Slovakia
Prior art keywords: ibuprofen; crystalline; added; molten; dissolving agent
Prior art date: 1994-01-28

Application number

SK964-96A

Other languages

English (en)

Slovak (sk)

Other versions

SK96496A3 (en

Inventor

Torsten Mller

Gerhard Hantich

Ernst Hesse

Original Assignee

Gebro Pharma Gmbh

Priority date (The priority date 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 date listed.)

1994-01-28

Filing date

1995-01-26

Publication date

2002-02-05

1995-01-26 Application filed by Gebro Pharma Gmbh filed Critical Gebro Pharma Gmbh

1997-01-08 Publication of SK96496A3 publication Critical patent/SK96496A3/sk

2002-02-05 Publication of SK282433B6 publication Critical patent/SK282433B6/sk

Links

HEFNNWSXXWATRW-JTQLQIEISA-N dexibuprofen Chemical compound CC(C)CC1=CC=C([C@H](C)C(O)=O)C=C1 HEFNNWSXXWATRW-JTQLQIEISA-N 0.000 title claims abstract description 62
239000002245 particle Substances 0.000 title claims abstract description 21
238000004519 manufacturing process Methods 0.000 title abstract description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
238000002360 preparation method Methods 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 39
230000008569 process Effects 0.000 claims description 24
239000003795 chemical substances by application Substances 0.000 claims description 13
239000000155 melt Substances 0.000 claims description 7
238000002844 melting Methods 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
230000008018 melting Effects 0.000 claims description 5
238000003756 stirring Methods 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 3
238000001035 drying Methods 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 3
239000007884 disintegrant Substances 0.000 claims description 2
238000002347 injection Methods 0.000 claims 1
239000007924 injection Substances 0.000 claims 1
239000003826 tablet Substances 0.000 abstract description 25
239000000203 mixture Substances 0.000 abstract description 9
238000007907 direct compression Methods 0.000 abstract description 4
239000004615 ingredient Substances 0.000 abstract description 4
238000010791 quenching Methods 0.000 abstract description 4
230000000171 quenching effect Effects 0.000 abstract description 2
239000007950 delayed release tablet Substances 0.000 abstract 1
239000000047 product Substances 0.000 description 17
239000013543 active substance Substances 0.000 description 16
239000004480 active ingredient Substances 0.000 description 12
239000002775 capsule Substances 0.000 description 9
239000013078 crystal Substances 0.000 description 8
238000004090 dissolution Methods 0.000 description 6
239000000654 additive Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 4
CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 4
230000002035 prolonged effect Effects 0.000 description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
230000002776 aggregation Effects 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
239000011575 calcium Substances 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229960001680 ibuprofen Drugs 0.000 description 3
239000000463 material Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000008363 phosphate buffer Substances 0.000 description 3
229910001220 stainless steel Inorganic materials 0.000 description 3
239000010935 stainless steel Substances 0.000 description 3
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
238000005054 agglomeration Methods 0.000 description 2
230000008901 benefit Effects 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
238000007906 compression Methods 0.000 description 2
230000006835 compression Effects 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000008298 dragée Substances 0.000 description 2
230000007613 environmental effect Effects 0.000 description 2
238000011049 filling Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
238000013467 fragmentation Methods 0.000 description 2
238000006062 fragmentation reaction Methods 0.000 description 2
239000008187 granular material Substances 0.000 description 2
229960003893 phenacetin Drugs 0.000 description 2
238000012545 processing Methods 0.000 description 2
238000007873 sieving Methods 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
229920002785 Croscarmellose sodium Polymers 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
235000019484 Rapeseed oil Nutrition 0.000 description 1
230000009471 action Effects 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000011246 composite particle Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000007948 fast release tablet Substances 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
238000009472 formulation Methods 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
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
-1 hydroxypropyl Chemical group 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
HEFNNWSXXWATRW-SNVBAGLBSA-N levibuprofen Chemical compound CC(C)CC1=CC=C([C@@H](C)C(O)=O)C=C1 HEFNNWSXXWATRW-SNVBAGLBSA-N 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000010309 melting process Methods 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
239000003566 sealing material Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003892 spreading Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1682—Processes
- A61K9/1688—Processes resulting in pure drug agglomerate optionally containing up to 5% of excipient
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin

Landscapes

Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyurethanes Or Polyureas (AREA)

SK964-96A 1994-01-28 1995-01-26 Spôsob prípravy častíc S(+)-ibuprofénu SK282433B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
AT0015894A AT401871B (de)	1994-01-28	1994-01-28	Verfahren zur herstellung von s(+)-ibuprofen- partikeln mit verbesserten fliesseigenschaften und deren verwendung zur arzneimittelherstellung
PCT/AT1995/000014 WO1995020382A1 (de)	1994-01-28	1995-01-26	Verfahren zur herstellung von s(+)-ibuprofen-partikeln

Publications (2)

Publication Number	Publication Date
SK96496A3 SK96496A3 (en)	1997-01-08
SK282433B6 true SK282433B6 (sk)	2002-02-05

Family

ID=3483086

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK964-96A SK282433B6 (sk)	1994-01-28	1995-01-26	Spôsob prípravy častíc S(+)-ibuprofénu

Country Status (20)

Country	Link
US (1)	US5869101A (cs)
EP (1)	EP0741565B1 (cs)
JP (1)	JP2840132B2 (cs)
AT (2)	AT401871B (cs)
AU (1)	AU689531B2 (cs)
CA (1)	CA2181810C (cs)
CZ (1)	CZ287998B6 (cs)
DE (1)	DE59508198D1 (cs)
DK (1)	DK0741565T3 (cs)
ES (1)	ES2146744T3 (cs)
FI (1)	FI112030B (cs)
GR (1)	GR3033841T3 (cs)
HU (1)	HU217798B (cs)
NO (1)	NO313982B1 (cs)
NZ (1)	NZ278551A (cs)
PL (1)	PL179095B1 (cs)
PT (1)	PT741565E (cs)
SI (1)	SI9520030A (cs)
SK (1)	SK282433B6 (cs)
WO (1)	WO1995020382A1 (cs)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TWI225402B (en)	1996-03-13	2004-12-21	Biochemie Gmbh	Auxiliary-free agglomerates
GB9613470D0 (en) *	1996-06-27	1996-08-28	Ciba Geigy Ag	Small solid oral dosage form
IT1301966B1 (it)	1998-07-30	2000-07-20	Zambon Spa	Composizioni farmaceutiche ad attivita' analgesica
MXPA01009808A (es) †	1999-04-01	2002-04-24	Dsm Nv	Aglomerados por cristalizacion.
US8124124B2 (en) *	1999-12-09	2012-02-28	Reckitt Benckiser Healthcare (Uk) Limited	Compressed tablet formulation comprising non-steroidal anti-inflammatory drugs and methods
KR100700721B1 (ko) *	2000-09-08	2007-03-27	지상철	안정성 및 용출율이 향상된 ｓ(+)-이부프로펜의 정제
GB0113839D0 (en) *	2001-06-07	2001-08-01	Boots Co Plc	Therapeutic agents
US6984403B2 (en) *	2003-12-04	2006-01-10	Pfizer Inc.	Azithromycin dosage forms with reduced side effects
WO2005053652A1 (en)	2003-12-04	2005-06-16	Pfizer Products Inc.	Multiparticulate crystalline drug compositions containing a poloxamer and a glyceride
WO2005053639A2 (en) *	2003-12-04	2005-06-16	Pfizer Products Inc.	Controlled release multiparticulates formed with dissolution enhancers
MXPA06005913A (es) *	2003-12-04	2006-06-27	Pfizer Prod Inc	Formas de dosificacion de multiparticulas de azitromicina por procedimientos basados en liquidos.
KR100844628B1 (ko) *	2003-12-04	2008-07-07	화이자 프로덕츠 인크.	제약상 다입자의 제조 방법
EP1701702A1 (en) *	2003-12-04	2006-09-20	Pfizer Products Inc.	Spray-congeal process using an extruder for preparing multiparticulate azithromycin compositions containing preferably a poloxamer and a glyceride
CA2547597A1 (en) *	2003-12-04	2005-06-16	Pfizer Products Inc.	Multiparticulate compositions with improved stability
ES2600577T3 (es) *	2003-12-04	2017-02-09	Bend Research, Inc.	Procedimiento de pulverización-solidificación que usa un extrusor para preparar composiciones en multipartículas de fármacos cristalinos
CZ297830B6 (cs) *	2005-08-30	2007-04-11	I.Q.A., A. S.	Zpusob výroby jemne krystalické smesi obsahující nesteroidní protizánetlivé lécivo, jemne krystalická smes pripravitelná tímto zpusobem a pevný farmaceutický prostredek tuto smes obsahující
CN105963259A (zh) *	2016-05-25	2016-09-28	山东理工大学	一种采用常压过滤制备布洛芬微球的方法
CN109956860B (zh) *	2019-03-08	2022-03-01	天津大学	一种布洛芬球形晶体的制备方法
CN110041191A (zh) *	2019-04-30	2019-07-23	湖南九典宏阳制药有限公司	一种培比洛芬的纯化方法

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4086346A (en) *	1974-04-06	1978-04-25	Bayer Aktiengesellschaft	Preparation of melt-sprayed spherical phenacetin granules
JPS52111533A (en) *	1976-03-12	1977-09-19	Kanebo Ltd	Preparation of fine powder of ibuprophene
US4476248A (en) *	1983-02-28	1984-10-09	The Upjohn Company	Crystallization of ibuprofen
US4609675A (en) *	1984-08-17	1986-09-02	The Upjohn Company	Stable, high dose, high bulk density ibuprofen granulations for tablet and capsule manufacturing
ES2055685T3 (es) *	1986-11-14	1994-09-01	Puetter Medice Chem Pharm	Procedimiento para la obtencion de un medicamento que contiene ibuprofen.
GB8716975D0 (en) *	1987-07-17	1987-08-26	Boots Co Plc	Therapeutic agents
US5198568A (en) *	1988-04-07	1993-03-30	Sepracor, Inc.	Compounds useful in enzymatic resolution systems and their preparation
DE3833446A1 (de) *	1988-10-01	1990-04-05	Hoechst Ag	Verfahren zur herstellung von arzneimittelwirkstoff-partikeln mit verbesserten fliess-, lager- und formulierungseigenschaften sowie arzneimittel, die diese arzneimittelwirkstoff-partikeln enthalten
DE3833448A1 (de) *	1988-10-01	1990-04-12	Hoechst Ag	Verfahren zur gewinnung von ibuprofen fuer die direkttablettierung
AU624421B2 (en) *	1988-10-05	1992-06-11	Pharmacia & Upjohn Company	Finely divided solid crystalline powders via precipitation into an anti-solvent
JPH082781B2 (ja) *	1988-10-18	1996-01-17	嘉明川島	中空顆粒状医薬及びその製法
US5104656A (en) *	1989-06-16	1992-04-14	Seth Pyare L	Percutaneous treatment with a high potency non-steroidal anti-inflammatory agent
EP0558621B1 (en) *	1990-11-19	1995-03-08	Albemarle Corporation	Process for improving flow characteristics of crystalline ibuprofen
DE4122591C1 (en) *	1991-07-08	1993-02-18	Roland 8012 Ottobrunn De Bodmeier	Producing microcapsules of water insoluble polymer and active agent - includes dissolving or dispersing active agent in aq. polymer contg. gellable assistants
US5191114A (en) *	1991-10-09	1993-03-02	Sage Pharmaceuticals, Inc.	Process for enhancing the flow characteristics of ibuprofen
DE4140179C2 (de) *	1991-12-05	1995-12-21	Alfatec Pharma Gmbh	Akutform für ein Ibuprofen enthaltendes Arzneimittel

1994
- 1994-01-28 AT AT0015894A patent/AT401871B/de not_active IP Right Cessation
1995
- 1995-01-26 PT PT95906207T patent/PT741565E/pt unknown
- 1995-01-26 CZ CZ19962131A patent/CZ287998B6/cs not_active IP Right Cessation
- 1995-01-26 JP JP7519783A patent/JP2840132B2/ja not_active Expired - Fee Related
- 1995-01-26 CA CA002181810A patent/CA2181810C/en not_active Expired - Fee Related
- 1995-01-26 DK DK95906207T patent/DK0741565T3/da active
- 1995-01-26 EP EP95906207A patent/EP0741565B1/de not_active Expired - Lifetime
- 1995-01-26 WO PCT/AT1995/000014 patent/WO1995020382A1/de not_active Ceased
- 1995-01-26 AU AU14499/95A patent/AU689531B2/en not_active Ceased
- 1995-01-26 SI SI9520030A patent/SI9520030A/sl not_active IP Right Cessation
- 1995-01-26 HU HU9602013A patent/HU217798B/hu unknown
- 1995-01-26 SK SK964-96A patent/SK282433B6/sk not_active IP Right Cessation
- 1995-01-26 AT AT95906207T patent/ATE191848T1/de active
- 1995-01-26 ES ES95906207T patent/ES2146744T3/es not_active Expired - Lifetime
- 1995-01-26 DE DE59508198T patent/DE59508198D1/de not_active Expired - Lifetime
- 1995-01-26 US US08/682,515 patent/US5869101A/en not_active Expired - Lifetime
- 1995-01-26 PL PL95315655A patent/PL179095B1/pl unknown
- 1995-01-26 NZ NZ278551A patent/NZ278551A/en not_active IP Right Cessation
1996
- 1996-07-15 NO NO19962966A patent/NO313982B1/no not_active IP Right Cessation
- 1996-07-16 FI FI962866A patent/FI112030B/fi not_active IP Right Cessation
2000
- 2000-06-30 GR GR20000401542T patent/GR3033841T3/el unknown

Also Published As

Publication number	Publication date
JP2840132B2 (ja)	1998-12-24
FI962866A0 (fi)	1996-07-16
NO962966D0 (no)	1996-07-15
DK0741565T3 (da)	2000-09-04
SK96496A3 (en)	1997-01-08
DE59508198D1 (de)	2000-05-25
NO313982B1 (no)	2003-01-13
CZ287998B6 (cs)	2001-03-14
AT401871B (de)	1996-12-27
JPH09503522A (ja)	1997-04-08
FI112030B (fi)	2003-10-31
AU689531B2 (en)	1998-04-02
EP0741565A1 (de)	1996-11-13
NZ278551A (en)	1997-10-24
US5869101A (en)	1999-02-09
GR3033841T3 (en)	2000-10-31
ATE191848T1 (de)	2000-05-15
AU1449995A (en)	1995-08-15
HU9602013D0 (en)	1996-09-30
WO1995020382A1 (de)	1995-08-03
FI962866L (fi)	1996-07-16
CZ213196A3 (en)	1996-10-16
PL315655A1 (en)	1996-11-25
CA2181810C (en)	2000-10-24
HU217798B (hu)	2000-04-28
NO962966L (no)	1996-07-15
SI9520030A (en)	1996-12-31
EP0741565B1 (de)	2000-04-19
ATA15894A (de)	1996-05-15
PT741565E (pt)	2000-09-29
PL179095B1 (pl)	2000-07-31
HUT74853A (en)	1997-02-28
ES2146744T3 (es)	2000-08-16

Legal Events

Date	Code	Title	Description
2012-10-02	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20120126

Publication	Publication Date	Title
SK282433B6 (sk)	2002-02-05	Spôsob prípravy častíc S(+)-ibuprofénu
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