ES2339213T1 - Hidrocloruro de lercanidipino amorfo. - Google Patents
Hidrocloruro de lercanidipino amorfo. Download PDFInfo
- Publication number
- ES2339213T1 ES2339213T1 ES06723128T ES06723128T ES2339213T1 ES 2339213 T1 ES2339213 T1 ES 2339213T1 ES 06723128 T ES06723128 T ES 06723128T ES 06723128 T ES06723128 T ES 06723128T ES 2339213 T1 ES2339213 T1 ES 2339213T1
- Authority
- ES
- Spain
- Prior art keywords
- lercanidipine hydrochloride
- pharmaceutical composition
- ester
- amorphous
- organic solvent
- 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.)
- Granted
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title 1
- WMFYOYKPJLRMJI-UHFFFAOYSA-N Lercanidipine hydrochloride Chemical compound Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)(C)CN(C)CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 WMFYOYKPJLRMJI-UHFFFAOYSA-N 0.000 claims abstract 12
- 229960002162 lercanidipine hydrochloride Drugs 0.000 claims abstract 12
- 238000000034 method Methods 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 150000002148 esters Chemical class 0.000 claims 5
- 239000003960 organic solvent Substances 0.000 claims 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 125000005456 glyceride group Chemical group 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000000194 fatty acid Substances 0.000 claims 2
- 229930195729 fatty acid Natural products 0.000 claims 2
- 150000004665 fatty acids Chemical class 0.000 claims 2
- -1 fatty acyl esters Chemical class 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- 239000002244 precipitate Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 150000005846 sugar alcohols Polymers 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 239000007884 disintegrant Substances 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 239000008157 edible vegetable oil Substances 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 150000002190 fatty acyls Chemical group 0.000 claims 1
- 235000003599 food sweetener Nutrition 0.000 claims 1
- 239000007903 gelatin capsule Substances 0.000 claims 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims 1
- 229960003943 hypromellose Drugs 0.000 claims 1
- 238000009413 insulation Methods 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 239000000314 lubricant Substances 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000004014 plasticizer Substances 0.000 claims 1
- 229920005862 polyol Polymers 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 claims 1
- 229920001451 polypropylene glycol Polymers 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000003755 preservative agent Substances 0.000 claims 1
- 230000002335 preservative effect Effects 0.000 claims 1
- 239000003586 protic polar solvent Substances 0.000 claims 1
- 238000000935 solvent evaporation Methods 0.000 claims 1
- 239000000375 suspending agent Substances 0.000 claims 1
- 239000003765 sweetening agent Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4422—1,4-Dihydropyridines, e.g. nifedipine, nicardipine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
- C07B63/04—Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicinal Preparation (AREA)
Abstract
Hidrocloruro de lercanidipino amorfo que presenta una pureza de por lo menos el 95%.
Claims (20)
1. Hidrocloruro de lercanidipino amorfo que
presenta una pureza de por lo menos el 95%.
2. Hidrocloruro de lercanidipino amorfo según la
reivindicación 1, que presenta una pureza de por lo menos el
99%.
3. Hidrocloruro de lercanidipino amorfo según la
reivindicación 1, que presenta una pureza de por lo menos el
99,5%.
4. Hidrocloruro de lercanidipino amorfo según
cualquiera de las reivindicaciones 1 a 3, que carece sustancialmente
de hidrocloruro de lercanidipino cristalino.
5. Hidrocloruro de lercanidipino amorfo según
cualquiera de las reivindicaciones 1 a 4, que se ha micronizado
hasta un tamaño de partícula de D (90%) < 15 \mum.
6. Procedimiento para la preparación de
hidrocloruro de lercanidipino amorfo, comprendiendo el
procedimiento
- (a)
- la disolución del hidrocloruro de lercanidipino cristalino en un disolvente orgánico; y
- (b)
- el aislamiento del hidrocloruro de lercanidipino amorfo mediante
- (i)
- la adición de la disolución a agua para formar un precipitado y la recogida del precipitado, o
- (ii)
- la retirada por evaporación del disolvente orgánico.
7. Procedimiento según la reivindicación 6, en
el que el disolvente orgánico es un disolvente polar prótico o
aprótico o una mezcla de los mismos.
8. Procedimiento según la reivindicación 6, en
el que el disolvente orgánico es un alcohol, una cetona, un
disolvente clorado o una amida.
9. Procedimiento según la reivindicación 6, en
el que el disolvente orgánico es metanol o diclorometano.
10. Procedimiento según la reivindicación 6, en
el que el disolvente orgánico es acetona, dimetilformamida o una
mezcla de metanol y etanol.
11. Procedimiento según cualquiera de las
reivindicaciones 6 a 10, en el que la etapa (a) se realiza a una
temperatura comprendida entre 30ºC y 50ºC.
12. Procedimiento según cualquiera de las
reivindicaciones 6 a 11, en el que el agua de la etapa (i) se
encuentra a una temperatura comprendida entre 1ºC y 20ºC. y la
disolución permanece a dicha temperatura durante un período
comprendido entre 4 y 24 horas para permitir que se complete la
precipitación.
13. Procedimiento según cualquiera de las
reivindicaciones 6 a 11, en el que la evaporación del disolvente se
realiza al vacío a una temperatura comprendida entre 20ºC y
40ºC.
14. Composición farmacéutica que comprende
hidrocloruro de lercanidipino amorfo según cualquiera de las
reivindicaciones 1 a 5 o hidrocloruro de lercanidipino amorfo
preparado mediante un método según cualquiera de las
reivindicaciones 6 a 13 y un diluyente, vehículo y/o excipiente
farmacéuticamente aceptables.
15. Composición farmacéutica según la
reivindicación 14, comprendiendo la composición por lo menos un
componente seleccionado de entre un diluyente, un saborizante, un
edulcorante, un conservante, un tinte, un aglutinante, un agente de
suspensión, un agente para aumentar la viscosidad, un agente
dispersante, un colorante, un desintegrante, un lubricante, un
antioxidante, un plastificante, y un aceite comestible, todos ellos
farmacéuticamente acepta-
bles.
bles.
16. Composición farmacéutica según la
reivindicación 14, adaptándose la composición para una liberación
modificada y comprendiendo por lo menos una sustancia cerosa.
17. Composición farmacéutica según la
reivindicación 16, en la que la sustancia cerosa es un éster de
acilo graso con polialcohol o una mezcla de ésteres de acilo graso
con polialcohol.
18. Composición farmacéutica según la
reivindicación 17, en la que el o cada éster de acilo graso con
polialcohol es un éster de polietilenglicol, un éster de
polipropilenglicol o un glicérido de un ácido graso.
\newpage
19. Composición farmacéutica según la
reivindicación 16, en la que la sustancia cerosa es un glicérido
poliglicolizado que comprende un éster de un ácido graso y un éster
de polietilenglicol, presentando el glicérido poliglicolizado un
punto de fusión comprendido entre 33ºC y 64ºC y un valor del
equilibrio hidrófilo - lipófilo (HLB) comprendido entre 1 y 14.
20. Composición farmacéutica según cualquiera de
las reivindicaciones 14 a 20, adaptándose la composición para una
liberación modificada, siendo en forma de dosis unitaria y
encontrándose contenida en una cápsula de gelatina, hipromelosa o
pululano.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65683605P | 2005-02-25 | 2005-02-25 | |
| US656836P | 2005-02-25 | ||
| PCT/EP2006/001782 WO2006089787A1 (en) | 2005-02-25 | 2006-02-24 | Amorphous lercanidipine hydrochloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES2339213T1 true ES2339213T1 (es) | 2010-05-18 |
| ES2339213T3 ES2339213T3 (es) | 2020-05-28 |
Family
ID=36585434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES06723128T Expired - Lifetime ES2339213T3 (es) | 2005-02-25 | 2006-02-24 | Clorhidrato de lercanidipino amorfo |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US7820701B2 (es) |
| EP (1) | EP1856051B1 (es) |
| JP (1) | JP2008531515A (es) |
| KR (1) | KR20070105979A (es) |
| CN (1) | CN101124204A (es) |
| AR (1) | AR052918A1 (es) |
| AU (1) | AU2006218026B9 (es) |
| BR (1) | BRPI0608138A2 (es) |
| CA (1) | CA2598016A1 (es) |
| CY (1) | CY1122429T1 (es) |
| DK (1) | DK1856051T3 (es) |
| EA (1) | EA014383B1 (es) |
| ES (1) | ES2339213T3 (es) |
| HR (1) | HRP20192302T1 (es) |
| HU (1) | HUE046910T2 (es) |
| IL (1) | IL184349A0 (es) |
| LT (1) | LT1856051T (es) |
| ME (1) | ME03659B (es) |
| MX (1) | MX2007010093A (es) |
| MY (1) | MY142129A (es) |
| NO (1) | NO344559B1 (es) |
| NZ (1) | NZ556667A (es) |
| PE (1) | PE20061014A1 (es) |
| PL (1) | PL1856051T3 (es) |
| PT (1) | PT1856051T (es) |
| RS (1) | RS59654B1 (es) |
| SI (1) | SI1856051T1 (es) |
| TW (1) | TW200640861A (es) |
| UA (1) | UA90130C2 (es) |
| UY (1) | UY29401A1 (es) |
| WO (1) | WO2006089787A1 (es) |
| ZA (1) | ZA200708127B (es) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1532248B1 (en) * | 2002-07-26 | 2009-04-01 | Novartis Vaccines and Diagnostics, Inc. | Modified small interfering rna molecules and methods of use |
| AR052918A1 (es) | 2005-02-25 | 2007-04-11 | Recordati Ireland Ltd | Clorhidrato de lercanidipina amorfo |
| WO2007031865A2 (en) | 2005-09-16 | 2007-03-22 | Glenmark Pharmaceuticals Limited | Polymorphic form of lercanidipine hydrochloride and process for the preparation thereof |
| PT2046745E (pt) * | 2006-08-04 | 2014-01-15 | Recordati Ireland Ltd | Processo para preparação de cloridrato de lercanidipina amorfo |
| WO2008068777A2 (en) * | 2006-12-06 | 2008-06-12 | Torrent Pharmaceuticals Limited | Stable lercanidipine formulation |
| CN101868442A (zh) * | 2007-03-05 | 2010-10-20 | 阿克塔维什集团Ptc公司 | 盐酸乐卡地平多晶型物和1,1,n-三甲基-n-(3,3-二苯基丙基)-2-氨基乙酰醋酸乙酯的改进制法 |
| JP5637568B2 (ja) * | 2009-05-12 | 2014-12-10 | コーセプト セラピューティクス， インコーポレイテッド | 固体形態および調製のためのプロセス |
| DE102010005124A1 (de) * | 2010-01-19 | 2012-03-01 | Stada Arzneimittel Ag | Feste pharmazeutische Zusammensetzung umfassend Lercanidipin |
| EP2444394A1 (en) | 2010-10-21 | 2012-04-25 | Alembic Pharmaceuticals Limited | Process for the preparation of amorphous form of lercanidipine HCI |
| CN102558032B (zh) * | 2011-12-16 | 2014-02-26 | 华润赛科药业有限责任公司 | 一种无定形盐酸乐卡地平及其制备方法 |
| CN102531999B (zh) * | 2011-12-16 | 2014-02-26 | 华润赛科药业有限责任公司 | 无定形盐酸乐卡地平及其制备方法 |
| CN102600146B (zh) * | 2012-04-11 | 2014-10-08 | 兆科药业（合肥）有限公司 | 一种盐酸乐卡地平和氯沙坦钾复方制剂及其制备方法 |
| US9951009B2 (en) * | 2013-08-29 | 2018-04-24 | Cadila Healthcare Limited | Polymorphic form of pyrrole derivative and intermediate thereof |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8403866D0 (en) | 1984-02-14 | 1984-03-21 | Recordati Chem Pharm | Diphenylalkylaminoalkyl esters |
| US5696139A (en) | 1995-05-12 | 1997-12-09 | Recordati S.A., Chemical And Pharmaceutical Company | Use of S-enantiomers of 1,4-dihydropyridine derivatives for treating heart failure |
| US5912351A (en) | 1995-05-12 | 1999-06-15 | Recordati, S.A. Chemical And Pharmaceutical Company | Anhydrous 1,4-Dihydropyridines and salts thereof |
| IT1274480B (it) | 1995-05-12 | 1997-07-17 | Recordati Chem Pharm | Procedimento migliorato per la preparazione della lercanidipina cloridrato |
| US20030069285A1 (en) | 2001-08-06 | 2003-04-10 | Recordati Ireland Limited | Novel solvate and crystalline forms of lercanidipine hydrochloride |
| ITMI20011727A1 (it) | 2001-08-06 | 2003-02-06 | Recordati Ind Chimica E Farma | Solvati della lercanidipina cloridrato e nuove forme cristalline della lercanidipina cloridrato ottenute da essi |
| US6852737B2 (en) | 2001-08-06 | 2005-02-08 | Recordati Ireland Limited | Crude and crystalline forms of lercanidipine hydrochloride |
| ITMI20011726A1 (it) | 2001-08-06 | 2003-02-06 | Recordati Ind Chimica E Farma | Forme polimorfe della lercanidipina cloridrato |
| US20030180355A1 (en) | 2001-10-16 | 2003-09-25 | Amedeo Leonardi | Combination therapy for hypertension |
| US20040147566A1 (en) | 2002-10-16 | 2004-07-29 | Amedeo Leonardi | Lisinopril/lercanidipine combination therapy |
| JP4749660B2 (ja) * | 2002-10-16 | 2011-08-17 | 武田薬品工業株式会社 | 安定な固形製剤 |
| US20040198789A1 (en) | 2003-02-28 | 2004-10-07 | Recordati Ireland Limited | Lercanidipine/ARB/diuretic therapeutic combinations |
| TW200613275A (en) | 2004-08-24 | 2006-05-01 | Recordati Ireland Ltd | Lercanidipine salts |
| TW200616681A (en) | 2004-10-05 | 2006-06-01 | Recordati Ireland Ltd | Lercanidipine capsules |
| KR100651212B1 (ko) | 2004-10-27 | 2006-12-01 | 제일약품주식회사 | 무정형 레르카니디핀의 제조방법 |
| AR052918A1 (es) | 2005-02-25 | 2007-04-11 | Recordati Ireland Ltd | Clorhidrato de lercanidipina amorfo |
| WO2007031865A2 (en) | 2005-09-16 | 2007-03-22 | Glenmark Pharmaceuticals Limited | Polymorphic form of lercanidipine hydrochloride and process for the preparation thereof |
| WO2007054969A2 (en) | 2005-09-21 | 2007-05-18 | Torrent Pharmaceuticals Limited | Process for the preparation of lercanidipine and amorphous form of lercanidipine hydrochloride |
| PT2046745E (pt) | 2006-08-04 | 2014-01-15 | Recordati Ireland Ltd | Processo para preparação de cloridrato de lercanidipina amorfo |
-
2006
- 2006-02-22 AR ARP060100641A patent/AR052918A1/es not_active Application Discontinuation
- 2006-02-24 UY UY29401A patent/UY29401A1/es not_active Application Discontinuation
- 2006-02-24 DK DK06723128.2T patent/DK1856051T3/da active
- 2006-02-24 ES ES06723128T patent/ES2339213T3/es not_active Expired - Lifetime
- 2006-02-24 WO PCT/EP2006/001782 patent/WO2006089787A1/en not_active Ceased
- 2006-02-24 KR KR1020077017758A patent/KR20070105979A/ko not_active Ceased
- 2006-02-24 TW TW095106337A patent/TW200640861A/zh unknown
- 2006-02-24 BR BRPI0608138-0A patent/BRPI0608138A2/pt not_active Application Discontinuation
- 2006-02-24 ME MEP-2019-352A patent/ME03659B/me unknown
- 2006-02-24 CA CA002598016A patent/CA2598016A1/en not_active Abandoned
- 2006-02-24 LT LTEP06723128.2T patent/LT1856051T/lt unknown
- 2006-02-24 PE PE2006000224A patent/PE20061014A1/es active IP Right Grant
- 2006-02-24 MY MYPI20060808A patent/MY142129A/en unknown
- 2006-02-24 HR HRP20192302TT patent/HRP20192302T1/hr unknown
- 2006-02-24 HU HUE06723128A patent/HUE046910T2/hu unknown
- 2006-02-24 SI SI200632364T patent/SI1856051T1/sl unknown
- 2006-02-24 RS RS20191591A patent/RS59654B1/sr unknown
- 2006-02-24 AU AU2006218026A patent/AU2006218026B9/en not_active Ceased
- 2006-02-24 PL PL06723128T patent/PL1856051T3/pl unknown
- 2006-02-24 JP JP2007556565A patent/JP2008531515A/ja active Pending
- 2006-02-24 PT PT67231282T patent/PT1856051T/pt unknown
- 2006-02-24 CN CNA2006800054950A patent/CN101124204A/zh active Pending
- 2006-02-24 EP EP06723128.2A patent/EP1856051B1/en not_active Revoked
- 2006-02-24 EA EA200701687A patent/EA014383B1/ru unknown
- 2006-02-24 UA UAA200709786A patent/UA90130C2/ru unknown
- 2006-02-24 MX MX2007010093A patent/MX2007010093A/es not_active Application Discontinuation
- 2006-02-24 NZ NZ556667A patent/NZ556667A/en not_active IP Right Cessation
- 2006-02-27 US US11/364,862 patent/US7820701B2/en active Active
-
2007
- 2007-07-02 IL IL184349A patent/IL184349A0/en active IP Right Grant
- 2007-09-21 ZA ZA200708127A patent/ZA200708127B/xx unknown
- 2007-09-25 NO NO20074874A patent/NO344559B1/no not_active IP Right Cessation
-
2019
- 2019-12-18 CY CY20191101332T patent/CY1122429T1/el unknown
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