BRPI0409166B1 - Processo para preparação de ferutinina a partir de plantas do gênero ferula e uso de p-pivaloilóxi-ferutina - Google Patents
Processo para preparação de ferutinina a partir de plantas do gênero ferula e uso de p-pivaloilóxi-ferutina Download PDFInfo
- Publication number
- BRPI0409166B1 BRPI0409166B1 BRPI0409166-3A BRPI0409166A BRPI0409166B1 BR PI0409166 B1 BRPI0409166 B1 BR PI0409166B1 BR PI0409166 A BRPI0409166 A BR PI0409166A BR PI0409166 B1 BRPI0409166 B1 BR PI0409166B1
- Authority
- BR
- Brazil
- Prior art keywords
- ferutinin
- ferula
- formula
- esters
- process according
- Prior art date
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- CYSHNJQMYORNJI-UHFFFAOYSA-N p-hydroxybenzoate of jaeschkeanadiol Natural products C12C(C(C)C)(O)CCC2(C)CC=C(C)CC1OC(=O)C1=CC=C(O)C=C1 CYSHNJQMYORNJI-UHFFFAOYSA-N 0.000 title claims abstract description 32
- CYSHNJQMYORNJI-YUVXSKOASA-N [(3r,3as,4s,8ar)-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] 4-hydroxybenzoate Chemical compound O([C@H]1CC(C)=CC[C@@]2(C)CC[C@@]([C@H]12)(O)C(C)C)C(=O)C1=CC=C(O)C=C1 CYSHNJQMYORNJI-YUVXSKOASA-N 0.000 title claims abstract description 30
- 241000510609 Ferula Species 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 14
- DVPFKQLUSCPERE-UHFFFAOYSA-N Ferutinin Natural products CC(C)C1(O)CCC2(C)CCC(=CC(OC(=O)c3ccc(O)cc3)C12)C DVPFKQLUSCPERE-UHFFFAOYSA-N 0.000 title claims description 30
- 238000002360 preparation method Methods 0.000 title claims description 6
- UUXOUABMYCIFOZ-UHFFFAOYSA-N ferutin Natural products COc1ccc(cc1O)C(=O)OC2C=C(C)CCC3(C)CCC(O)(C(C)C)C23 UUXOUABMYCIFOZ-UHFFFAOYSA-N 0.000 title 1
- 239000002537 cosmetic Substances 0.000 claims abstract description 6
- 241000554103 Ferula hermonis Species 0.000 claims description 11
- -1 daucane esters Chemical class 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 241000533992 Ferula communis Species 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- 229930015303 daucane Natural products 0.000 claims description 6
- HDPCDSVIGNIWKD-UHFFFAOYSA-N 4-(2,2-dimethylpropanoyloxy)benzoic acid Chemical compound CC(C)(C)C(=O)OC1=CC=C(C(O)=O)C=C1 HDPCDSVIGNIWKD-UHFFFAOYSA-N 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000001569 carbon dioxide Substances 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
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- 239000000243 solution Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 210000003491 skin Anatomy 0.000 description 14
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- 239000003208 petroleum Substances 0.000 description 10
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- 238000006243 chemical reaction Methods 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
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- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 4
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
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- 239000008213 purified water Substances 0.000 description 4
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- QYYMDNHUJFIDDQ-UHFFFAOYSA-N 5-chloro-2-methyl-1,2-thiazol-3-one;2-methyl-1,2-thiazol-3-one Chemical compound CN1SC=CC1=O.CN1SC(Cl)=CC1=O QYYMDNHUJFIDDQ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 2
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 2
- 239000002148 ERα-agonist Substances 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/23—Apiaceae or Umbelliferae (Carrot family), e.g. dill, chervil, coriander or cumin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/86—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/30—Azulenes; Hydrogenated azulenes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
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- Dermatology (AREA)
- Birds (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000661A ITMI20030661A1 (it) | 2003-04-04 | 2003-04-04 | Processo per la preparazione della ferutinina da piante del genere ferula |
| ITMI2003A000661 | 2003-04-04 | ||
| PCT/EP2004/003055 WO2004087179A1 (en) | 2003-04-04 | 2004-03-23 | A process for the preparation of ferutinine from ferula genus plants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BRPI0409166A BRPI0409166A (pt) | 2006-04-11 |
| BRPI0409166B1 true BRPI0409166B1 (pt) | 2015-09-01 |
Family
ID=33105046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0409166-3A BRPI0409166B1 (pt) | 2003-04-04 | 2004-03-23 | Processo para preparação de ferutinina a partir de plantas do gênero ferula e uso de p-pivaloilóxi-ferutina |
Country Status (19)
| Country | Link |
|---|---|
| US (4) | US7371886B2 (enExample) |
| EP (1) | EP1615651B1 (enExample) |
| JP (2) | JP4648305B2 (enExample) |
| KR (2) | KR101169893B1 (enExample) |
| CN (2) | CN101371818A (enExample) |
| AT (1) | ATE517631T1 (enExample) |
| AU (1) | AU2004226853B2 (enExample) |
| BR (1) | BRPI0409166B1 (enExample) |
| CA (2) | CA2521100C (enExample) |
| DK (1) | DK1615651T3 (enExample) |
| ES (1) | ES2367361T3 (enExample) |
| IL (1) | IL171230A (enExample) |
| IT (1) | ITMI20030661A1 (enExample) |
| NO (1) | NO333671B1 (enExample) |
| PL (1) | PL1615651T3 (enExample) |
| PT (1) | PT1615651E (enExample) |
| RU (2) | RU2342153C2 (enExample) |
| SI (1) | SI1615651T1 (enExample) |
| WO (1) | WO2004087179A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20032286A1 (it) * | 2003-11-24 | 2005-05-25 | Indena Spa | Composizioni per il trattamento di dermatiti atopiche di stati allergici cutanei e dell'acne |
| US8536584B2 (en) | 2007-11-14 | 2013-09-17 | Cree, Inc. | High voltage wire bond free LEDS |
| US20100260695A1 (en) * | 2009-04-09 | 2010-10-14 | Mary Kay Inc. | Combination of plant extracts to improve skin tone |
| CA2800383C (en) * | 2010-05-24 | 2019-06-25 | Indena S.P.A. | Tamarind seed polysaccharide for use in the treatment of inflammatory diseases |
| CA2834828A1 (en) | 2011-05-12 | 2012-11-15 | B.R.A.I.N. Biotechnology Research And Information Network Ag | Small molecule inhibitors of trpa1 |
| DE202015004868U1 (de) | 2014-07-11 | 2015-12-23 | Mary Kay Inc. | Topische Hautzusammensetzung und deren Verwendung |
| CN105820146A (zh) * | 2015-01-08 | 2016-08-03 | 辽宁医联新药研究所 | 一种阿魏内酯及其提取纯化的方法 |
| GB2570508A (en) * | 2018-01-30 | 2019-07-31 | Saeed Mohammad Sultan Alaryani Humaid | Preparation for treatment of wounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1604225A (en) * | 1978-05-15 | 1981-12-02 | Skourides A A | Extract of ambelferae for pharmacological use |
| JPH02500362A (ja) * | 1987-05-29 | 1990-02-08 | インスティテュト ヒミイ ラスティテルニハ ベスチェストフ アカデミイ ナウク ウズベクスコイ エスエスエル | エストロゲン効果を有する製剤 |
| RU2090198C1 (ru) * | 1991-03-12 | 1997-09-20 | Иван Иванович Уваров | Способ получения биологически активных веществ, обладающих противогрибковой активностью |
| DE4444238A1 (de) * | 1994-12-13 | 1996-06-20 | Beiersdorf Ag | Kosmetische oder dermatologische Wirkstoffkombinationen aus Zimtsäurederivaten und Flavonglycosiden |
| JP4244093B2 (ja) * | 2000-01-24 | 2009-03-25 | 三省製薬株式会社 | 美白化粧料 |
| CA2417552C (en) * | 2000-06-27 | 2014-05-13 | Qualilife Pharmaceuticals Inc. | Compositions and methods for treating females sexual response |
| US6623768B1 (en) * | 2002-04-16 | 2003-09-23 | Yousry M. A. Naguib | Pharmaceutically active composition extracted from Ferula hermonis and process of its extraction |
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2003
- 2003-04-04 IT IT000661A patent/ITMI20030661A1/it unknown
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2004
- 2004-03-23 KR KR1020117014703A patent/KR101169893B1/ko not_active Expired - Fee Related
- 2004-03-23 ES ES04722572T patent/ES2367361T3/es not_active Expired - Lifetime
- 2004-03-23 RU RU2005130639/15A patent/RU2342153C2/ru not_active IP Right Cessation
- 2004-03-23 AU AU2004226853A patent/AU2004226853B2/en not_active Ceased
- 2004-03-23 WO PCT/EP2004/003055 patent/WO2004087179A1/en not_active Ceased
- 2004-03-23 SI SI200431757T patent/SI1615651T1/sl unknown
- 2004-03-23 PL PL04722572T patent/PL1615651T3/pl unknown
- 2004-03-23 CN CNA2008101489166A patent/CN101371818A/zh active Pending
- 2004-03-23 CN CNB2004800091113A patent/CN100518732C/zh not_active Expired - Fee Related
- 2004-03-23 PT PT04722572T patent/PT1615651E/pt unknown
- 2004-03-23 CA CA2521100A patent/CA2521100C/en not_active Expired - Fee Related
- 2004-03-23 KR KR1020057018336A patent/KR101132526B1/ko not_active Expired - Fee Related
- 2004-03-23 DK DK04722572.7T patent/DK1615651T3/da active
- 2004-03-23 JP JP2006504815A patent/JP4648305B2/ja not_active Expired - Fee Related
- 2004-03-23 CA CA2766702A patent/CA2766702C/en not_active Expired - Fee Related
- 2004-03-23 EP EP04722572A patent/EP1615651B1/en not_active Expired - Lifetime
- 2004-03-23 US US10/551,772 patent/US7371886B2/en not_active Expired - Fee Related
- 2004-03-23 BR BRPI0409166-3A patent/BRPI0409166B1/pt not_active IP Right Cessation
- 2004-03-23 AT AT04722572T patent/ATE517631T1/de active
-
2005
- 2005-10-02 IL IL171230A patent/IL171230A/en not_active IP Right Cessation
- 2005-10-03 NO NO20054545A patent/NO333671B1/no not_active IP Right Cessation
-
2008
- 2008-03-31 US US12/058,776 patent/US20080248139A1/en not_active Abandoned
- 2008-06-03 RU RU2008122295/15A patent/RU2469733C2/ru not_active IP Right Cessation
-
2010
- 2010-05-06 JP JP2010106573A patent/JP5409505B2/ja not_active Expired - Fee Related
- 2010-06-16 US US12/816,671 patent/US8101215B2/en not_active Expired - Fee Related
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2011
- 2011-12-13 US US13/324,339 patent/US8247005B2/en not_active Expired - Fee Related
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