RU2006134014A - Региоспецифический синтез производных 42-эфира рапамицина - Google Patents
Региоспецифический синтез производных 42-эфира рапамицина Download PDFInfo
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- RU2006134014A RU2006134014A RU2006134014/04A RU2006134014A RU2006134014A RU 2006134014 A RU2006134014 A RU 2006134014A RU 2006134014/04 A RU2006134014/04 A RU 2006134014/04A RU 2006134014 A RU2006134014 A RU 2006134014A RU 2006134014 A RU2006134014 A RU 2006134014A
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- Prior art keywords
- vinyl
- rapamycin
- lipase
- ether
- group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems
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- 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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/436—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having oxygen as a ring hetero atom, e.g. rapamycin
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
- C12N9/18—Carboxylic ester hydrolases (3.1.1)
- C12N9/20—Triglyceride splitting, e.g. by means of lipase
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/188—Heterocyclic compound containing in the condensed system at least one hetero ring having nitrogen atoms and oxygen atoms as the only ring heteroatoms
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Wood Science & Technology (AREA)
- Immunology (AREA)
- Zoology (AREA)
- Genetics & Genomics (AREA)
- General Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Transplantation (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Enzymes And Modification Thereof (AREA)
Claims (18)
1. Способ региоспецифического получения производных 42-эфира рапамицина с формулой (I)
где R является линейным или циклическим, алифатическим или ароматическим, насыщенным или ненасыщенным углеводородом, который по выбору содержит гидроксил, галоген и/или серу, вышеуказанный способ, включающий ацилирование 42-гидроксирапамицина с ацильным донором в присутствии липазы.
2. Способ, по п.1, используемая липаза представляет собой микробную липазу, полученную из таких микроорганизмов, как Aspergillus niger, Candida antarctica, Candida rugosa, Mucor miehei, Pseudomonas cepacia, Pseudomonas fluorescens, Rhizopus delemar.
3. Способ, по п.2, в котором используют липазу типа В, полученную из Candida antarctica (липаза NOVOZYM 435) или Pseudemonas cepacia (липаза PS-C "Amano" II).
4. Способ, по любому из пп.1-3, в котором ацильным донором является виниловый эфир, изопропениловый эфир или ангидрид.
5. Способ по п.4, в котором виниловый эфир имеет формулу СН2=СН-O-COR1, где R1 выбирается из группы, состоящей из алкила C1-C6, алкенила С2-С6, арила C6-C14, бензила, замещенных по выбору группой, независимо выбранной из гидроксила, галогена и SH.
6. Способ по п.5, в котором виниловый эфир выбирается из группы, состоящей из винилацетата, винилпропионата, винилхлорацетата, винилкротоната, винилбензоата и винилдеканоата.
7. Способ по п.4, в котором виниловым эфиром является изопропилиден защищенный винил 3-гидрокси-2-(гидроксиметил)-2-метилпропионат.
8. Способ по п.4, в котором изопропениловый эфир имеет формулу СН2=С(СН3)-OCOR2, где R2 выбирается из группы, состоящей из алкила C1-C6, алкенила С2-С6, арила С6-С14, бензила, замещенных по выбору группой, независимо выбранной из гидроксила, галогена и SH.
9. Способ по п.8, где изопропениловым эфиром является изопропенилацетат.
10. Способ по п.4, в котором ангидридом является алкановый ангидрид С1-С8 с прямой или разветвленной цепью, замещенный по выбору группой независимо выбранной из галогена или гидроксила.
11. Способ по любому из пп.1-3 или 5-10, в которых реакция происходит в органическом растворителе, выбранном из группы растворителей, состоящей из толуола, трет-бутилметилового эфира (ТБМЭ), этилового эфира, тетрагидрофурана (ТГФ), MeCN, CH2Cl2, CHCl3, гексана, диоксана или их смеси.
12. Способ по п.11, в котором реакцию проводят в диапазоне температур 20-75°С.
13. Региоспецифическое приготовление 42-эфира рапамицина с изопропилиденкеталь защищенной 3-гидрокси-2-(гидроксиметил)-2-метилпропионовой кислотой, предшественником CCI-779.
14. Состав, включающий региоспецифические 42-производные рапамицина, полученные в соответствии со способом любого из пп.1-12.
15. Состав, включающий получение региоспецифических 42-производных рапамицина в соответствии с п.13.
16. Состав, в соответствии с п.14 или 15, кроме того, включающий физиологически совместимый носитель.
17. Продукт, включающий состав в соответствии с любым из пп.14-16 и упаковку для вышеуказанной композиции.
18. Фармацевтический комплект, включающий единицу региоспецифического 42-производного рапамицина, полученного в соответствии с любым из пп.1-12 в форме одноразовой дозированной формы.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56192604P | 2004-04-14 | 2004-04-14 | |
| US60/561,926 | 2004-04-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2006134014A true RU2006134014A (ru) | 2008-05-20 |
| RU2387657C2 RU2387657C2 (ru) | 2010-04-27 |
Family
ID=34965235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2006134014/04A RU2387657C2 (ru) | 2004-04-14 | 2005-04-12 | Региоспецифический синтез производных 42-эфира рапамицина |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7268144B2 (ru) |
| EP (1) | EP1737869A1 (ru) |
| JP (1) | JP4224115B2 (ru) |
| KR (1) | KR20070015544A (ru) |
| CN (1) | CN1942476A (ru) |
| AR (1) | AR049019A1 (ru) |
| AU (1) | AU2005238431A1 (ru) |
| BR (1) | BRPI0509852A (ru) |
| CA (1) | CA2562952A1 (ru) |
| CL (1) | CL2008000507A1 (ru) |
| CR (1) | CR8646A (ru) |
| EC (1) | ECSP066927A (ru) |
| GT (1) | GT200500085A (ru) |
| IL (1) | IL178315A0 (ru) |
| MX (1) | MXPA06011881A (ru) |
| NO (1) | NO20065090L (ru) |
| PA (1) | PA8629901A1 (ru) |
| PE (1) | PE20060253A1 (ru) |
| RU (1) | RU2387657C2 (ru) |
| SG (1) | SG152234A1 (ru) |
| TW (1) | TW200536542A (ru) |
| UA (1) | UA87492C2 (ru) |
| WO (1) | WO2005105811A1 (ru) |
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|---|---|---|---|---|
| RU2344821C2 (ru) | 2002-07-30 | 2009-01-27 | Уайт | Парентеральные композиции, содержащие гидроксиэфиры рапамицина |
| DE602005010228D1 (de) * | 2004-04-14 | 2008-11-20 | Wyeth Corp | Verfahren zur herstellung von rapamycin-42-estern und fk-506-32-estern mit dicarbonsäure, vorstufen für rapamycinkonjugate und antikörper |
| AU2005238493A1 (en) * | 2004-04-27 | 2005-11-10 | Wyeth | Labeling of rapamycin using rapamycin-specific methylases |
| TW200616633A (en) * | 2004-08-10 | 2006-06-01 | Wyeth Corp | CCI-779 derivatives and methods of making same |
| WO2006086172A1 (en) * | 2005-02-09 | 2006-08-17 | Wyeth | Cci-779 polymorph and use thereof |
| US7538119B2 (en) * | 2005-11-04 | 2009-05-26 | Wyeth | 41-Methoxy isotope labeled rapamycin 42-ester |
| JP2009518648A (ja) * | 2005-12-07 | 2009-05-07 | ワイス | 結晶性ラパマイシンを調製するための方法およびを示差走査熱量測定使用してラパマイシン化合物の結晶化度を測定するための方法 |
| AU2006322029A1 (en) * | 2005-12-07 | 2007-06-14 | Wyeth | Process for the preparation of purified crystalline CCI-779 |
| BRPI0619578A2 (pt) * | 2005-12-07 | 2011-10-04 | Wyeth Corp | processo para preparar um 42-éster de rapamicina, composto, método para isolar o boronato do 42-éster de rapamicina bruto a partir do licor mãe, método para purificação de um boronato do 42-éster de rapamicina, e, boronato de cci-779 |
| EP1993610A2 (en) * | 2006-03-07 | 2008-11-26 | Wyeth | Process for preparing water-soluble polyethylene glycol conjugates of macrolide immunosuppressants |
| US9700704B2 (en) | 2006-11-20 | 2017-07-11 | Lutonix, Inc. | Drug releasing coatings for balloon catheters |
| US20080276935A1 (en) | 2006-11-20 | 2008-11-13 | Lixiao Wang | Treatment of asthma and chronic obstructive pulmonary disease with anti-proliferate and anti-inflammatory drugs |
| US8414910B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US9737640B2 (en) | 2006-11-20 | 2017-08-22 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US8998846B2 (en) | 2006-11-20 | 2015-04-07 | Lutonix, Inc. | Drug releasing coatings for balloon catheters |
| US8414526B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Medical device rapid drug releasing coatings comprising oils, fatty acids, and/or lipids |
| US8425459B2 (en) | 2006-11-20 | 2013-04-23 | Lutonix, Inc. | Medical device rapid drug releasing coatings comprising a therapeutic agent and a contrast agent |
| US8414525B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US8414909B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| TW200845960A (en) * | 2007-04-05 | 2008-12-01 | Wyeth Corp | Wortmannin-rapalog conjugate and uses thereof |
| US20090253733A1 (en) * | 2008-04-02 | 2009-10-08 | Biointeractions, Ltd. | Rapamycin carbonate esters |
| US20110098241A1 (en) * | 2008-04-14 | 2011-04-28 | Poniard Pharmaceuticals, Inc. | Rapamycin analogs as anti-cancer agents |
| WO2010024898A2 (en) | 2008-08-29 | 2010-03-04 | Lutonix, Inc. | Methods and apparatuses for coating balloon catheters |
| CN101676291B (zh) * | 2008-09-18 | 2012-05-09 | 上海海和药物研究开发有限公司 | 一类雷帕霉素碳酸酯类似物、其药物组合物及其制备方法和用途 |
| CA2937492C (en) | 2008-11-11 | 2019-08-13 | The Board Of Regents Of The University Of Texas System | Inhibition of mammalian target of rapamycin |
| IT1394309B1 (it) * | 2009-05-22 | 2012-06-06 | Poli Ind Chimica Spa | Nuovo approccio chimico-enzimatico alla sintesi del pimecrolimus |
| US9283211B1 (en) | 2009-11-11 | 2016-03-15 | Rapamycin Holdings, Llc | Oral rapamycin preparation and use for stomatitis |
| US9051336B2 (en) * | 2011-04-01 | 2015-06-09 | Sandoz | Regioselective acylation of rapamycin at the C-42 position |
| US10751450B2 (en) | 2012-06-08 | 2020-08-25 | Biotronik Ag | Rapamycin 40-O-cyclic hydrocarbon esters, compositions and methods |
| SG11201405777YA (en) * | 2012-06-08 | 2014-10-30 | Biotronik Ag | Rapamycin 40-o-cyclic hydrocarbon esters, compositions and methods |
| WO2014160328A1 (en) | 2013-03-13 | 2014-10-02 | The Board Of Regents Of The University Of Texas System | Mtor inhibitors for prevention of intestinal polyp growth |
| CN108864149B (zh) | 2013-03-15 | 2022-04-05 | 生物传感器国际集团有限公司 | 雷帕霉素衍生物的纯化 |
| ES2900426T3 (es) | 2013-12-31 | 2022-03-16 | Rapamycin Holdings Llc | Preparaciones orales y uso de nanopartículas de rapamicina |
| US9700544B2 (en) | 2013-12-31 | 2017-07-11 | Neal K Vail | Oral rapamycin nanoparticle preparations |
| WO2018152286A1 (en) | 2017-02-17 | 2018-08-23 | Trevena, Inc. | 7-membered aza-heterocyclic containing delta-opioid receptor modulating compounds, methods of using and making the same |
| EP3848065B1 (en) | 2017-05-15 | 2023-07-26 | C. R. Bard, Inc. | Medical device with drug-eluting coating and intermediate layer |
| AU2018370237A1 (en) * | 2017-11-20 | 2020-06-04 | Icahn School Of Medicine At Mount Sinai | Inhibiting trained immunity with a therapeutic nanobilogic composition |
| US11541152B2 (en) | 2018-11-14 | 2023-01-03 | Lutonix, Inc. | Medical device with drug-eluting coating on modified device surface |
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| EP4308105A1 (en) | 2021-03-19 | 2024-01-24 | Trained Therapeutix Discovery, Inc. | Compounds for regulating trained immunity, and their methods of use |
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| ZA737247B (en) | 1972-09-29 | 1975-04-30 | Ayerst Mckenna & Harrison | Rapamycin and process of preparation |
| US4316885A (en) | 1980-08-25 | 1982-02-23 | Ayerst, Mckenna And Harrison, Inc. | Acyl derivatives of rapamycin |
| US4650803A (en) | 1985-12-06 | 1987-03-17 | University Of Kansas | Prodrugs of rapamycin |
| US5210030A (en) * | 1990-06-25 | 1993-05-11 | Merck & Co., Inc. | Process for selectively acylating immunomycin |
| PT98990A (pt) * | 1990-09-19 | 1992-08-31 | American Home Prod | Processo para a preparacao de esteres de acidos carboxilicos de rapamicina |
| US5233036A (en) | 1990-10-16 | 1993-08-03 | American Home Products Corporation | Rapamycin alkoxyesters |
| US5100883A (en) | 1991-04-08 | 1992-03-31 | American Home Products Corporation | Fluorinated esters of rapamycin |
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| US5118677A (en) | 1991-05-20 | 1992-06-02 | American Home Products Corporation | Amide esters of rapamycin |
| US5260300A (en) | 1992-11-19 | 1993-11-09 | American Home Products Corporation | Rapamycin carbonate esters as immuno-suppressant agents |
| US5362718A (en) * | 1994-04-18 | 1994-11-08 | American Home Products Corporation | Rapamycin hydroxyesters |
| US5780462A (en) | 1995-12-27 | 1998-07-14 | American Home Products Corporation | Water soluble rapamycin esters |
| TWI256395B (en) * | 1999-09-29 | 2006-06-11 | Wyeth Corp | Regioselective synthesis of rapamycin derivatives |
| US6277983B1 (en) | 2000-09-27 | 2001-08-21 | American Home Products Corporation | Regioselective synthesis of rapamycin derivatives |
| EP1319008B1 (en) | 2000-09-19 | 2008-10-15 | Wyeth | Water soluble rapamycin esters |
| RU2344821C2 (ru) | 2002-07-30 | 2009-01-27 | Уайт | Парентеральные композиции, содержащие гидроксиэфиры рапамицина |
| JP4227649B2 (ja) | 2003-08-07 | 2009-02-18 | ワイス | Ｃｃｉ−７７９の位置選択的合成 |
| AU2004270154A1 (en) | 2003-09-03 | 2005-03-17 | Wyeth | Amorphous rapamycin 42-ester with 3-hydroxy-2-(hydroxymethyl)-2-methylpropionic acid and its pharmaceutical compositions containing the same |
| KR20060130162A (ko) | 2004-01-08 | 2006-12-18 | 와이어쓰 | Ｃｃｉ-779 의 경구 투여용, 직접 압축식 약학적 조성물 |
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2005
- 2005-04-12 MX MXPA06011881A patent/MXPA06011881A/es active IP Right Grant
- 2005-04-12 CN CNA2005800112769A patent/CN1942476A/zh active Pending
- 2005-04-12 SG SG200902515-6A patent/SG152234A1/en unknown
- 2005-04-12 RU RU2006134014/04A patent/RU2387657C2/ru not_active IP Right Cessation
- 2005-04-12 JP JP2007508442A patent/JP4224115B2/ja not_active Expired - Fee Related
- 2005-04-12 WO PCT/US2005/012266 patent/WO2005105811A1/en active Application Filing
- 2005-04-12 US US11/103,799 patent/US7268144B2/en not_active Expired - Fee Related
- 2005-04-12 KR KR1020067021378A patent/KR20070015544A/ko not_active Application Discontinuation
- 2005-04-12 BR BRPI0509852-1A patent/BRPI0509852A/pt not_active IP Right Cessation
- 2005-04-12 AU AU2005238431A patent/AU2005238431A1/en not_active Abandoned
- 2005-04-12 CA CA002562952A patent/CA2562952A1/en not_active Abandoned
- 2005-04-12 EP EP05733853A patent/EP1737869A1/en not_active Withdrawn
- 2005-04-13 PA PA20058629901A patent/PA8629901A1/es unknown
- 2005-04-13 TW TW094111640A patent/TW200536542A/zh unknown
- 2005-04-13 PE PE2005000409A patent/PE20060253A1/es not_active Application Discontinuation
- 2005-04-13 GT GT200500085A patent/GT200500085A/es unknown
- 2005-04-13 AR ARP050101447A patent/AR049019A1/es unknown
- 2005-12-04 UA UAA200610949A patent/UA87492C2/ru unknown
-
2006
- 2006-09-21 CR CR8646A patent/CR8646A/es not_active Application Discontinuation
- 2006-09-26 IL IL178315A patent/IL178315A0/en unknown
- 2006-10-16 EC EC2006006927A patent/ECSP066927A/es unknown
- 2006-11-03 NO NO20065090A patent/NO20065090L/no not_active Application Discontinuation
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2008
- 2008-02-19 CL CL200800507A patent/CL2008000507A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR049019A1 (es) | 2006-06-21 |
| NO20065090L (no) | 2006-11-13 |
| CN1942476A (zh) | 2007-04-04 |
| TW200536542A (en) | 2005-11-16 |
| BRPI0509852A (pt) | 2007-10-23 |
| US20050234234A1 (en) | 2005-10-20 |
| CL2008000507A1 (es) | 2008-07-04 |
| US7268144B2 (en) | 2007-09-11 |
| JP2007532134A (ja) | 2007-11-15 |
| ECSP066927A (es) | 2006-12-20 |
| CR8646A (es) | 2007-08-28 |
| WO2005105811A1 (en) | 2005-11-10 |
| GT200500085A (es) | 2005-11-03 |
| MXPA06011881A (es) | 2006-12-14 |
| RU2387657C2 (ru) | 2010-04-27 |
| PE20060253A1 (es) | 2006-03-30 |
| PA8629901A1 (es) | 2006-06-02 |
| JP4224115B2 (ja) | 2009-02-12 |
| SG152234A1 (en) | 2009-05-29 |
| IL178315A0 (en) | 2007-02-11 |
| KR20070015544A (ko) | 2007-02-05 |
| CA2562952A1 (en) | 2005-11-10 |
| EP1737869A1 (en) | 2007-01-03 |
| UA87492C2 (en) | 2009-07-27 |
| AU2005238431A1 (en) | 2005-11-10 |
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