KR20050071549A - 10,11-디히드로-10-히드록시-5Ｈ-디벤즈[ｂ,ｆ]아제핀-5-카르복스아미드의 두가지 거울상이성질체 및 이들의 신규한결정형의 거울상이성질체선택적 제조 방법 - Google Patents
10,11-디히드로-10-히드록시-5Ｈ-디벤즈[ｂ,ｆ]아제핀-5-카르복스아미드의 두가지 거울상이성질체 및 이들의 신규한결정형의 거울상이성질체선택적 제조 방법 Download PDFInfo
- Publication number
- KR20050071549A KR20050071549A KR1020057005920A KR20057005920A KR20050071549A KR 20050071549 A KR20050071549 A KR 20050071549A KR 1020057005920 A KR1020057005920 A KR 1020057005920A KR 20057005920 A KR20057005920 A KR 20057005920A KR 20050071549 A KR20050071549 A KR 20050071549A
- Authority
- KR
- South Korea
- Prior art keywords
- azepine
- hydroxy
- dibenz
- dihydro
- carboxamide
- 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.)
- Withdrawn
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- 239000013078 crystal Substances 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims description 16
- BMPDWHIDQYTSHX-UHFFFAOYSA-N licarbazepine Chemical compound C1C(O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 BMPDWHIDQYTSHX-UHFFFAOYSA-N 0.000 title abstract description 6
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 title abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
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- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
- 206010015037 epilepsy Diseases 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
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- 239000000155 melt Substances 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 2
- NPKCAMZGRRHFTJ-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepin-5-ol Chemical compound OC1CC2=CC=CC=C2NC2=CC=CC=C12 NPKCAMZGRRHFTJ-UHFFFAOYSA-N 0.000 claims 1
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- 239000003054 catalyst Substances 0.000 abstract description 5
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- UVGSRARLWOYTNE-UHFFFAOYSA-N OC1=C2C=CC=CC2=NC2=CCCCC2=C1 Chemical class OC1=C2C=CC=CC2=NC2=CCCCC2=C1 UVGSRARLWOYTNE-UHFFFAOYSA-N 0.000 abstract description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- -1 —O—CH 2 —O— Chemical group 0.000 description 19
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- CTRLABGOLIVAIY-UHFFFAOYSA-N oxcarbazepine Chemical compound C1C(=O)C2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 CTRLABGOLIVAIY-UHFFFAOYSA-N 0.000 description 8
- 230000005855 radiation Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- 238000010521 absorption reaction Methods 0.000 description 6
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
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- 238000004566 IR spectroscopy Methods 0.000 description 4
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- 239000002608 ionic liquid Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- AJUXDFHPVZQOGF-UHFFFAOYSA-N n,n-dimethyl-1-naphthylamine Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1 AJUXDFHPVZQOGF-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 208000027232 peripheral nervous system disease Diseases 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
- C07D223/24—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0223224.7 | 2002-10-07 | ||
| GBGB0223224.7A GB0223224D0 (en) | 2002-10-07 | 2002-10-07 | Organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050071549A true KR20050071549A (ko) | 2005-07-07 |
Family
ID=9945425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020057005920A Withdrawn KR20050071549A (ko) | 2002-10-07 | 2003-10-06 | 10,11-디히드로-10-히드록시-5Ｈ-디벤즈[ｂ,ｆ]아제핀-5-카르복스아미드의 두가지 거울상이성질체 및 이들의 신규한결정형의 거울상이성질체선택적 제조 방법 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US20060142566A1 (https=) |
| EP (1) | EP1551808A1 (https=) |
| JP (1) | JP2006504710A (https=) |
| KR (1) | KR20050071549A (https=) |
| CN (2) | CN101062932A (https=) |
| AR (1) | AR041544A1 (https=) |
| AU (1) | AU2003276055B2 (https=) |
| BR (1) | BR0315113A (https=) |
| CA (1) | CA2501237A1 (https=) |
| EC (1) | ECSP055738A (https=) |
| GB (1) | GB0223224D0 (https=) |
| HK (1) | HK1079790A1 (https=) |
| MX (1) | MXPA05003737A (https=) |
| NO (1) | NO20052244L (https=) |
| PE (1) | PE20040686A1 (https=) |
| PL (1) | PL376379A1 (https=) |
| RU (1) | RU2005114350A (https=) |
| TW (1) | TW200413324A (https=) |
| WO (1) | WO2004031155A1 (https=) |
| ZA (1) | ZA200502561B (https=) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0303615D0 (en) * | 2003-02-17 | 2003-03-19 | Novartis Ag | Use of organic compounds |
| GB0425320D0 (en) | 2004-11-17 | 2004-12-22 | Johnson Matthey Plc | Diamines |
| US20060252745A1 (en) | 2005-05-06 | 2006-11-09 | Almeida Jose L D | Methods of preparing pharmaceutical compositions comprising eslicarbazepine acetate and methods of use |
| GB0515690D0 (en) | 2005-07-29 | 2005-09-07 | Portela & Ca Sa | Asymmetric catalytic reduction |
| GB2437078A (en) * | 2006-04-11 | 2007-10-17 | Portela & Ca Sa | 10-Acyloxy-5H-dibenzo[b,f]azepine-5-carboxamides & their asymmetric hydrogenation to the chiral 10,11-dihydro derivatives |
| JP5172124B2 (ja) * | 2006-09-29 | 2013-03-27 | 関東化学株式会社 | ２位に置換基を有する光学活性キヌクリジノール類の製造方法 |
| GB0700773D0 (en) | 2007-01-15 | 2007-02-21 | Portela & Ca Sa | Drug therapies |
| WO2011045648A2 (en) * | 2009-10-12 | 2011-04-21 | Matrix Laboratories Limited | Process for preparing (s)-(-)-10-acetoxy-10,11-dihydro-5h-dibenz[b,f]azepine-5-carboxamide and its esters thereof |
| EP2383261B1 (en) | 2010-04-23 | 2013-09-04 | Euticals GmbH | Process for the asymmetric hydrogenation of ketones |
| CN102250005B (zh) * | 2010-05-19 | 2015-04-08 | 浙江九洲药物科技有限公司 | 艾利西平的制备方法 |
| WO2012120356A2 (en) | 2011-03-08 | 2012-09-13 | Jubilant Life Sciences Limited | Process for the preparation of (s)-(+)-or (r)-(-)-10 hydroxy dihydrodibenz[b,f]azepines by enantioselective reduction of 10, 11-dihydro-10-oxo-5h-dibenz[b,f]azepines and polymorphs thereof |
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| US9399634B2 (en) | 2012-05-07 | 2016-07-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of depression |
| WO2013167985A1 (en) * | 2012-05-07 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of neurological disorders |
| WO2013168021A1 (en) | 2012-05-07 | 2013-11-14 | Mahesh Kandula | Compositions and methods for treatment of neuromuscular disorders and neurodegenerative disorders |
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| WO2013167997A2 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of metabolic syndrome |
| US9321775B2 (en) | 2012-05-10 | 2016-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of moderate to severe pain |
| WO2013168012A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of respiratory disorders |
| US9273061B2 (en) | 2012-05-10 | 2016-03-01 | Cellix Bio Private Limited | Compositions and methods for the treatment of chronic pain |
| WO2013168000A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of severe pain |
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| IN2015DN02296A (https=) | 2012-09-26 | 2015-08-21 | Ranbaxy Lab Ltd | |
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| CN103483257A (zh) * | 2013-09-06 | 2014-01-01 | 江苏同禾药业有限公司 | 一种亚氨基芪的合成方法 |
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| ES2799309T3 (es) | 2014-09-29 | 2020-12-16 | Cellix Bio Private Ltd | Compuestos y composiciones para el tratamiento de esclerosis múltiple |
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| WO2016088132A1 (en) | 2014-12-01 | 2016-06-09 | Cellix Bio Private Limited | Compositions and methods for the treatment of multiple sclerosis |
| US9206111B1 (en) | 2014-12-17 | 2015-12-08 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological diseases |
| SG11201705524SA (en) | 2015-01-06 | 2017-08-30 | Cellix Bio Private Ltd | Compositions and methods for the treatment of inflammation and pain |
| EP3064490A1 (en) | 2015-03-06 | 2016-09-07 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Improved process for the preparation of eslicarbazepine and eslicarbazepine acetate |
| CN107033079B (zh) * | 2016-10-17 | 2020-07-28 | 扬子江药业集团北京海燕药业有限公司 | 醋酸艾司利卡西平的制备方法 |
| CN112679433B (zh) * | 2019-10-18 | 2024-05-24 | 浙江九洲药业股份有限公司 | 一种艾利西平的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT101732B (pt) * | 1995-06-30 | 1997-12-31 | Portela & Ca Sa | Novas di-hidrodibenzo<b,f>azepinas substituidas processo para a sua preparacao composicoes farmaceuticas que as contem e utilizacao dos novos compostos na preparacao de composicoes farmaceuticas empregues em doencas do sistema nervoso |
| JP2003502296A (ja) * | 1999-06-15 | 2003-01-21 | ロディア・シミ | スルホニルアミド及びカルボキサミド並びに不斉触媒作用におけるそれらの使用 |
| ES2211373T1 (es) * | 2001-02-12 | 2004-07-16 | Teva Pharmaceutical Industries Ltd. | Nuevas formas cristalinas de oxcarbazepina y procedimientos para su preparacion. |
-
2002
- 2002-10-07 GB GBGB0223224.7A patent/GB0223224D0/en not_active Ceased
-
2003
- 2003-10-06 CA CA002501237A patent/CA2501237A1/en not_active Abandoned
- 2003-10-06 KR KR1020057005920A patent/KR20050071549A/ko not_active Withdrawn
- 2003-10-06 AU AU2003276055A patent/AU2003276055B2/en not_active Expired - Fee Related
- 2003-10-06 BR BR0315113-1A patent/BR0315113A/pt not_active IP Right Cessation
- 2003-10-06 EP EP03798930A patent/EP1551808A1/en not_active Withdrawn
- 2003-10-06 HK HK05112208.8A patent/HK1079790A1/zh unknown
- 2003-10-06 US US10/530,617 patent/US20060142566A1/en not_active Abandoned
- 2003-10-06 CN CNA2007101126346A patent/CN101062932A/zh active Pending
- 2003-10-06 PL PL03376379A patent/PL376379A1/xx unknown
- 2003-10-06 RU RU2005114350/04A patent/RU2005114350A/ru not_active Application Discontinuation
- 2003-10-06 MX MXPA05003737A patent/MXPA05003737A/es not_active Application Discontinuation
- 2003-10-06 JP JP2004540788A patent/JP2006504710A/ja active Pending
- 2003-10-06 WO PCT/EP2003/011034 patent/WO2004031155A1/en not_active Ceased
- 2003-10-06 CN CNA2003801013117A patent/CN1703404A/zh active Pending
- 2003-10-07 PE PE2003001022A patent/PE20040686A1/es not_active Application Discontinuation
- 2003-10-07 AR ARP030103648A patent/AR041544A1/es not_active Application Discontinuation
- 2003-10-07 TW TW092127799A patent/TW200413324A/zh unknown
-
2005
- 2005-03-30 ZA ZA200502561A patent/ZA200502561B/en unknown
- 2005-04-06 EC EC2005005738A patent/ECSP055738A/es unknown
- 2005-05-06 NO NO20052244A patent/NO20052244L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PL376379A1 (en) | 2005-12-27 |
| BR0315113A (pt) | 2005-08-23 |
| AU2003276055A1 (en) | 2004-04-23 |
| RU2005114350A (ru) | 2006-01-20 |
| ECSP055738A (es) | 2005-07-06 |
| CN101062932A (zh) | 2007-10-31 |
| AU2003276055B2 (en) | 2008-01-03 |
| NO20052244L (no) | 2005-07-07 |
| AR041544A1 (es) | 2005-05-18 |
| WO2004031155A1 (en) | 2004-04-15 |
| TW200413324A (en) | 2004-08-01 |
| GB0223224D0 (en) | 2002-11-13 |
| ZA200502561B (en) | 2006-02-22 |
| EP1551808A1 (en) | 2005-07-13 |
| NO20052244D0 (no) | 2005-05-06 |
| PE20040686A1 (es) | 2004-10-29 |
| CN1703404A (zh) | 2005-11-30 |
| MXPA05003737A (es) | 2005-06-17 |
| JP2006504710A (ja) | 2006-02-09 |
| CA2501237A1 (en) | 2004-04-15 |
| HK1079790A1 (zh) | 2006-04-13 |
| US20060142566A1 (en) | 2006-06-29 |
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