HUP0302755A2 - Eljárás kamptotecin-analóg vegyületek előállítására - Google Patents
Eljárás kamptotecin-analóg vegyületek előállításáraInfo
- Publication number
- HUP0302755A2 HUP0302755A2 HU0302755A HUP0302755A HUP0302755A2 HU P0302755 A2 HUP0302755 A2 HU P0302755A2 HU 0302755 A HU0302755 A HU 0302755A HU P0302755 A HUP0302755 A HU P0302755A HU P0302755 A2 HUP0302755 A2 HU P0302755A2
- Authority
- HU
- Hungary
- Prior art keywords
- compound
- general formula
- formula
- converted
- camptothecin
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 9
- 238000000034 method Methods 0.000 title abstract 4
- 230000002194 synthesizing effect Effects 0.000 title 1
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 abstract 3
- HHCZNCHGYNRIBP-UHFFFAOYSA-N 1-(2-amino-5-hydroxyphenyl)propan-1-one Chemical compound CCC(=O)C1=CC(O)=CC=C1N HHCZNCHGYNRIBP-UHFFFAOYSA-N 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
- 238000000844 transformation Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/20—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C07C205/21—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C205/22—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring having one nitro groups bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
-
- 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)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A találmány tárgya eljárás kamptotecin-analógok szintéziséhezhasználható (e) képletű 2'-amino-5'-hidroxi-propiofenon előállítására,amelynek során az (a) képletű vegyületet (b) általános képletűvegyületté alakítják, a (b) általános képletű vegyületet (c) általánosképletű vegyületté alakítják, a (c) általános képletű vegyületet (d)általános képletű vegyületté alakítják, és a (d) általános képletűvegyületet az (e) képletű 2'-amino-5'-hidroxi-propiofenonná alakítják- a képletekben R katalitikus redukcióval lehasítható védőcsoportotjelent. A találmány tárgya továbbá eljárás kamptotecin-analógokszintéziséhez használható (h) képletű triciklusos keton előállításárajavított módszerrel. Az (e) és (h) képletű vegyületek reagáltatásávalés szükség szerinti utólagos átalakításokkal a kamptotecin-analógokigen jó hatásfokkal állíthatók elő. Ó
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2001045430 | 2001-02-21 | ||
JP2001309322 | 2001-10-05 | ||
PCT/JP2002/001538 WO2002066416A1 (en) | 2001-02-21 | 2002-02-21 | Method of synthesizing camptothecin-relating compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
HUP0302755A2 true HUP0302755A2 (hu) | 2003-12-29 |
HUP0302755A3 HUP0302755A3 (en) | 2008-03-28 |
Family
ID=26609837
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU0302755A HUP0302755A3 (en) | 2001-02-21 | 2002-02-21 | Method of synthesizing camptothecin-relating compounds |
Country Status (23)
Country | Link |
---|---|
US (2) | US7126000B2 (hu) |
EP (1) | EP1378505B1 (hu) |
JP (2) | JP4210119B2 (hu) |
KR (2) | KR100858972B1 (hu) |
CN (1) | CN100408550C (hu) |
AR (2) | AR035684A1 (hu) |
AU (1) | AU2002237527B2 (hu) |
BG (2) | BG108031A (hu) |
BR (1) | BR0207470A (hu) |
CA (2) | CA2683768C (hu) |
CZ (1) | CZ20032470A3 (hu) |
EE (1) | EE05361B1 (hu) |
HU (1) | HUP0302755A3 (hu) |
IL (2) | IL156949A0 (hu) |
MX (1) | MXPA03007528A (hu) |
NO (2) | NO328628B1 (hu) |
NZ (2) | NZ527615A (hu) |
PL (2) | PL217238B1 (hu) |
RO (2) | RO125158A2 (hu) |
RU (1) | RU2308447C2 (hu) |
SK (2) | SK288149B6 (hu) |
TW (1) | TWI245768B (hu) |
WO (1) | WO2002066416A1 (hu) |
Families Citing this family (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CZ299329B6 (cs) * | 2003-08-26 | 2008-06-18 | Pliva-Lachema A.S. | Zpusob výroby 7-ethyl-10-[ 4-(1-piperidino)-1-piperidino]karbonyloxykamptothecinu |
CZ299593B6 (cs) * | 2003-12-16 | 2008-09-10 | Pliva-Lachema A. S. | Zpusob výroby 7-ethyl-10-hydroxykamptothecinu |
WO2006016203A1 (en) * | 2004-08-09 | 2006-02-16 | Shilpa Medicare Limited | An improved process for the preparation of irinotecan hydrochloride trihydrate |
ES2391775T3 (es) * | 2004-11-05 | 2012-11-29 | Samyang Biopharmaceuticals Corporation | Formulación farmacéutica para aumentar la solubilidad de compuestos de 10-hidroxicamptotecina en disolventes polares no acuosos |
PL1846412T3 (pl) * | 2005-02-07 | 2010-03-31 | Fermion Oy | Sposób wytwarzania 7-etylo-10-hydroksykamptotecyny |
PL1928883T3 (pl) * | 2005-02-08 | 2014-03-31 | Fermion Oy | Sposób otrzymywania chlorowodorku irynotekanu |
US7662964B2 (en) | 2005-02-08 | 2010-02-16 | Fermion Oy | Process for producing [1,4′] bipiperidinyl-1′-carbonyl chloride or hydrochloride thereof |
US8112154B2 (en) * | 2005-04-13 | 2012-02-07 | The Cleveland Clinic Foundation | Systems and methods for neuromodulation using pre-recorded waveforms |
TWI375678B (en) * | 2005-06-09 | 2012-11-01 | Yakult Honsha Kk | A method of preparation of a tricyclic ketone |
EP1910269B1 (en) * | 2005-08-03 | 2013-09-18 | Avra Laboratories PVT. Ltd. | Method of synthesizing key intermediates for the production of camptothecin derivatives |
EP1803725A1 (en) * | 2005-12-13 | 2007-07-04 | W.C. Heraeus GmbH | Methods for preparing irinotecan |
US9220889B2 (en) | 2008-02-11 | 2015-12-29 | Intelect Medical, Inc. | Directional electrode devices with locating features |
CN101824038B (zh) * | 2009-03-06 | 2013-08-21 | 复旦大学 | 喜树碱及其类似物的制备方法 |
JP5734295B2 (ja) | 2009-08-27 | 2015-06-17 | ザ クリーブランド クリニック ファウンデーション | 組織活性の部位を推定するためのシステムおよび方法 |
JP5599094B2 (ja) * | 2010-05-20 | 2014-10-01 | 国立大学法人 千葉大学 | ニトリル化合物の製造方法 |
CA2802708A1 (en) | 2010-06-14 | 2011-12-22 | Boston Scientific Neuromodulation Corporation | Programming interface for spinal cord neuromodulation |
US9925382B2 (en) | 2011-08-09 | 2018-03-27 | Boston Scientific Neuromodulation Corporation | Systems and methods for stimulation-related volume analysis, creation, and sharing |
AU2013308906B2 (en) | 2012-08-28 | 2016-07-21 | Boston Scientific Neuromodulation Corporation | Point-and-click programming for deep brain stimulation using real-time monopolar review trendlines |
WO2014070290A2 (en) | 2012-11-01 | 2014-05-08 | Boston Scientific Neuromodulation Corporation | Systems and methods for voa model generation and use |
US8722886B1 (en) * | 2012-11-13 | 2014-05-13 | Bionumerik Pharmaceuticals, Inc. | Methods for the total chemical synthesis of enantiomerically-pure 7-(2′-trimethylsilyl)ethyl camptothecin |
US9959388B2 (en) | 2014-07-24 | 2018-05-01 | Boston Scientific Neuromodulation Corporation | Systems, devices, and methods for providing electrical stimulation therapy feedback |
US10272247B2 (en) | 2014-07-30 | 2019-04-30 | Boston Scientific Neuromodulation Corporation | Systems and methods for stimulation-related volume analysis, creation, and sharing with integrated surgical planning and stimulation programming |
US10265528B2 (en) | 2014-07-30 | 2019-04-23 | Boston Scientific Neuromodulation Corporation | Systems and methods for electrical stimulation-related patient population volume analysis and use |
US9974959B2 (en) | 2014-10-07 | 2018-05-22 | Boston Scientific Neuromodulation Corporation | Systems, devices, and methods for electrical stimulation using feedback to adjust stimulation parameters |
EP3209666B1 (en) * | 2014-10-22 | 2019-08-21 | Vivacitas Oncology Inc. | Methods and systems for camptothecin analog synthesis |
US10780283B2 (en) | 2015-05-26 | 2020-09-22 | Boston Scientific Neuromodulation Corporation | Systems and methods for analyzing electrical stimulation and selecting or manipulating volumes of activation |
US9956419B2 (en) | 2015-05-26 | 2018-05-01 | Boston Scientific Neuromodulation Corporation | Systems and methods for analyzing electrical stimulation and selecting or manipulating volumes of activation |
US10441800B2 (en) | 2015-06-29 | 2019-10-15 | Boston Scientific Neuromodulation Corporation | Systems and methods for selecting stimulation parameters by targeting and steering |
WO2017003946A1 (en) | 2015-06-29 | 2017-01-05 | Boston Scientific Neuromodulation Corporation | Systems and methods for selecting stimulation parameters based on stimulation target region, effects, or side effects |
WO2017062378A1 (en) | 2015-10-09 | 2017-04-13 | Boston Scientific Neuromodulation Corporation | System and methods for clinical effects mapping for directional stimulations leads |
US10716942B2 (en) | 2016-04-25 | 2020-07-21 | Boston Scientific Neuromodulation Corporation | System and methods for directional steering of electrical stimulation |
CN109416937A (zh) | 2016-06-24 | 2019-03-01 | 波士顿科学神经调制公司 | 用于临床效果的视觉分析的系统和方法 |
US10350404B2 (en) | 2016-09-02 | 2019-07-16 | Boston Scientific Neuromodulation Corporation | Systems and methods for visualizing and directing stimulation of neural elements |
US10780282B2 (en) | 2016-09-20 | 2020-09-22 | Boston Scientific Neuromodulation Corporation | Systems and methods for steering electrical stimulation of patient tissue and determining stimulation parameters |
AU2017341910B2 (en) | 2016-10-14 | 2020-05-14 | Boston Scientific Neuromodulation Corporation | Systems and methods for closed-loop determination of stimulation parameter settings for an electrical simulation system |
AU2017391436B2 (en) | 2017-01-03 | 2020-06-18 | Boston Scientific Neuromodulation Corporation | Systems and methods for selecting MRI-compatible stimulation parameters |
US10589104B2 (en) | 2017-01-10 | 2020-03-17 | Boston Scientific Neuromodulation Corporation | Systems and methods for creating stimulation programs based on user-defined areas or volumes |
US10625082B2 (en) | 2017-03-15 | 2020-04-21 | Boston Scientific Neuromodulation Corporation | Visualization of deep brain stimulation efficacy |
WO2018187090A1 (en) | 2017-04-03 | 2018-10-11 | Boston Scientific Neuromodulation Corporation | Systems and methods for estimating a volume of activation using a compressed database of threshold values |
EP3651849B1 (en) | 2017-07-14 | 2023-05-31 | Boston Scientific Neuromodulation Corporation | Estimating clinical effects of electrical stimulation |
EP3634569A1 (en) | 2017-08-15 | 2020-04-15 | Boston Scientific Neuromodulation Corporation | Systems and methods for controlling electrical stimulation using multiple stimulation fields |
EP3784331B1 (en) | 2018-04-27 | 2023-01-18 | Boston Scientific Neuromodulation Corporation | Multi-mode electrical stimulation systems and methods of making and using |
WO2019210214A1 (en) | 2018-04-27 | 2019-10-31 | Boston Scientific Neuromodulation Corporation | Systems for visualizing and programming electrical stimulation |
US11434196B2 (en) * | 2019-01-15 | 2022-09-06 | Laurus Labs Limited | Process for preparation of 2-Amino-5-hydroxy propiophenone |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5391745A (en) * | 1992-07-23 | 1995-02-21 | Sloan-Kettering Institute For Cancer Research | Methods of preparation of camptothecin analogs |
JPH07101956A (ja) * | 1993-10-05 | 1995-04-18 | Tanabe Seiyaku Co Ltd | ヒドロキシカンプトテシン化合物の製法 |
KR960029336A (ko) * | 1995-01-09 | 1996-08-17 | 김충환 | 캄토테신 유도체, 그의 제조 방법 및 이를 함유하는 항암제 |
JPH08225482A (ja) * | 1995-02-22 | 1996-09-03 | Dai Ichi Seiyaku Co Ltd | テトラロン関連化合物及びその製法 |
TW438775B (en) | 1995-04-07 | 2001-06-07 | Pharmacia & Upjohn Co Llc | Novel intermediates and process for the manufacture of camptothecin derivatives (CPT-11) and related compounds |
CZ133898A3 (cs) | 1995-11-02 | 1998-08-12 | Glaxo Wellcome Inc. | Způsob výroby derivátů camptothecinu |
SG104284A1 (en) * | 1996-10-30 | 2004-06-21 | Tanabe Seiyaku Co | S type 2-substituted hydroxy-2-indolidinylbutyric ester compounds and process for preparation thereof |
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2002
- 2002-02-20 AR ARP020100579A patent/AR035684A1/es active IP Right Grant
- 2002-02-20 TW TW091102967A patent/TWI245768B/zh not_active IP Right Cessation
- 2002-02-21 KR KR1020037010841A patent/KR100858972B1/ko active IP Right Grant
- 2002-02-21 PL PL399009A patent/PL217238B1/pl unknown
- 2002-02-21 WO PCT/JP2002/001538 patent/WO2002066416A1/ja active IP Right Grant
- 2002-02-21 CA CA2683768A patent/CA2683768C/en not_active Expired - Fee Related
- 2002-02-21 HU HU0302755A patent/HUP0302755A3/hu unknown
- 2002-02-21 CA CA2437702A patent/CA2437702C/en not_active Expired - Fee Related
- 2002-02-21 EP EP02703874.4A patent/EP1378505B1/en not_active Expired - Lifetime
- 2002-02-21 EE EEP200300373A patent/EE05361B1/xx not_active IP Right Cessation
- 2002-02-21 PL PL363440A patent/PL218065B1/pl unknown
- 2002-02-21 KR KR1020077030609A patent/KR100864692B1/ko active IP Right Grant
- 2002-02-21 CN CNB028053230A patent/CN100408550C/zh not_active Expired - Fee Related
- 2002-02-21 RO ROA200900165A patent/RO125158A2/ro unknown
- 2002-02-21 RU RU2003128530/04A patent/RU2308447C2/ru not_active IP Right Cessation
- 2002-02-21 SK SK5001-2011A patent/SK288149B6/sk not_active IP Right Cessation
- 2002-02-21 US US10/467,987 patent/US7126000B2/en not_active Expired - Lifetime
- 2002-02-21 SK SK1147-2003A patent/SK288073B6/sk not_active IP Right Cessation
- 2002-02-21 MX MXPA03007528A patent/MXPA03007528A/es active IP Right Grant
- 2002-02-21 CZ CZ20032470A patent/CZ20032470A3/cs unknown
- 2002-02-21 RO ROA200300695A patent/RO122639B9/ro unknown
- 2002-02-21 NZ NZ52761502A patent/NZ527615A/xx not_active IP Right Cessation
- 2002-02-21 IL IL15694902A patent/IL156949A0/xx unknown
- 2002-02-21 JP JP2002565934A patent/JP4210119B2/ja not_active Expired - Fee Related
- 2002-02-21 BR BRPI0207470-2A patent/BR0207470A/pt not_active IP Right Cessation
- 2002-02-21 AU AU2002237527A patent/AU2002237527B2/en not_active Ceased
-
2003
- 2003-07-15 IL IL156949A patent/IL156949A/en not_active IP Right Cessation
- 2003-07-25 BG BG108031A patent/BG108031A/bg active Pending
- 2003-08-13 NO NO20033579A patent/NO328628B1/no not_active IP Right Cessation
- 2003-08-14 NZ NZ534374A patent/NZ534374A/xx not_active IP Right Cessation
-
2006
- 2006-09-08 US US11/517,621 patent/US7378555B2/en not_active Expired - Lifetime
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2008
- 2008-03-28 JP JP2008085358A patent/JP4805967B2/ja not_active Expired - Lifetime
-
2009
- 2009-11-24 NO NO20093402A patent/NO331656B1/no not_active IP Right Cessation
-
2011
- 2011-08-11 AR ARP110102927A patent/AR082663A2/es not_active Application Discontinuation
-
2013
- 2013-04-23 BG BG10111453A patent/BG111453A/en unknown
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