CN101547602B - 四氧取代丁烷桥修饰的ndga衍生物,它们的合成方法和药学用途 - Google Patents
四氧取代丁烷桥修饰的ndga衍生物,它们的合成方法和药学用途 Download PDFInfo
- Publication number
- CN101547602B CN101547602B CN200780044510.7A CN200780044510A CN101547602B CN 101547602 B CN101547602 B CN 101547602B CN 200780044510 A CN200780044510 A CN 200780044510A CN 101547602 B CN101547602 B CN 101547602B
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- China
- Prior art keywords
- acid
- compound
- ndga
- butane
- bis
- 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.)
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- RMBXNEIPKBSTAP-UHFFFAOYSA-N C(CCc(cc1)cc(OCCN2CCCCC2)c1OCCN1CCCCC1)Cc(cc1OCCN2CCCCC2)ccc1OCCN1CCCCC1 Chemical compound C(CCc(cc1)cc(OCCN2CCCCC2)c1OCCN1CCCCC1)Cc(cc1OCCN2CCCCC2)ccc1OCCN1CCCCC1 RMBXNEIPKBSTAP-UHFFFAOYSA-N 0.000 description 1
- PJTBQVJOQYFDMJ-QGZVFWFLSA-N COc(ccc(CC[C@H](Cc(cc1)cc(OC)c1OC)CO)c1)c1OC Chemical compound COc(ccc(CC[C@H](Cc(cc1)cc(OC)c1OC)CO)c1)c1OC PJTBQVJOQYFDMJ-QGZVFWFLSA-N 0.000 description 1
- GMYCFOWTCMWAGK-PSWAGMNNSA-N C[C@H](Cc(cc1)cc(OC(CN(C)C)=O)c1OC(CN(C)C)=O)[C@@H](C)Cc(cc1)cc(OC(CN(C)C)=O)c1OC(CN(C)C)=O Chemical compound C[C@H](Cc(cc1)cc(OC(CN(C)C)=O)c1OC(CN(C)C)=O)[C@@H](C)Cc(cc1)cc(OC(CN(C)C)=O)c1OC(CN(C)C)=O GMYCFOWTCMWAGK-PSWAGMNNSA-N 0.000 description 1
- PLGOVVDLHPLNJT-CRAIPNDOSA-N C[C@H](Cc(cc1)cc(OC)c1OC)[C@H](Cc(cc1)cc(OC)c1OC)CF Chemical compound C[C@H](Cc(cc1)cc(OC)c1OC)[C@H](Cc(cc1)cc(OC)c1OC)CF PLGOVVDLHPLNJT-CRAIPNDOSA-N 0.000 description 1
- ORQFDHFZSMXRLM-IYBDPMFKSA-N C[C@H](Cc(cc1OC)ccc1OC)[C@@H](C)Cc(cc1)cc(OC)c1OC Chemical compound C[C@H](Cc(cc1OC)ccc1OC)[C@@H](C)Cc(cc1)cc(OC)c1OC ORQFDHFZSMXRLM-IYBDPMFKSA-N 0.000 description 1
- JMYXNUMGPRHHBC-UHFFFAOYSA-N Oc1ccc(CCCCc(cc2)cc(O)c2O)cc1O Chemical compound Oc1ccc(CCCCc(cc2)cc(O)c2O)cc1O JMYXNUMGPRHHBC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/20—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/33—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/367—Halogenated derivatives polycyclic non-condensed, containing only six-membered aromatic rings as cyclic parts, e.g. halogenated poly-hydroxyphenylalkanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
- C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/26—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups
- C07C47/27—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/26—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups
- C07C47/273—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Diabetes (AREA)
- Virology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82778306P | 2006-10-02 | 2006-10-02 | |
| US60/827,783 | 2006-10-02 | ||
| PCT/US2007/080231 WO2008042921A2 (en) | 2006-10-02 | 2007-10-02 | Tetra-o-substituted butane-bridge modified ndga derivatives, their synthesis and pharmaceutical use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101547602A CN101547602A (zh) | 2009-09-30 |
| CN101547602B true CN101547602B (zh) | 2014-01-22 |
Family
ID=39269174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200780044510.7A Active CN101547602B (zh) | 2006-10-02 | 2007-10-02 | 四氧取代丁烷桥修饰的ndga衍生物,它们的合成方法和药学用途 |
Country Status (6)
| Country | Link |
|---|---|
| US (4) | US8232277B2 (enExample) |
| EP (1) | EP2076125B1 (enExample) |
| JP (1) | JP5362572B2 (enExample) |
| CN (1) | CN101547602B (enExample) |
| ES (1) | ES2449237T3 (enExample) |
| WO (1) | WO2008042921A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010011117A2 (ko) * | 2008-07-25 | 2010-01-28 | 국립암센터 | Ndga를 포함하는 트란스글루타미나제 억제용 조성물 |
| US20100093872A1 (en) * | 2008-10-15 | 2010-04-15 | Erimos Pharmaceuticals Llc | Stable aqueous formulations of water insoluble or poorly soluble drugs |
| WO2012145749A1 (en) | 2011-04-22 | 2012-10-26 | Napo Pharmaceuticals, Inc. | Pharmacologically optimized multimodal drug delivery system for nordihydroguiaretic acid (ndga) |
| US9084779B2 (en) * | 2011-05-31 | 2015-07-21 | The Johns Hopkins University | Conjugates of nitroimidazoles and their use as chemotherapeutic agents |
| US9834575B2 (en) | 2013-02-26 | 2017-12-05 | Triact Therapeutics, Inc. | Cancer therapy |
| KR20160104612A (ko) | 2013-07-26 | 2016-09-05 | 업데이트 파마 인코포레이트 | 비산트렌의 치료 효과 개선용 조성물 |
| WO2022159326A1 (en) | 2021-01-19 | 2022-07-28 | Erimos Pharmaceuticals, Llc | Terameprocol and nordihydroguaiaretic acid (ndga) derivatives as coronavirus anti-viral agents |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4708964A (en) * | 1984-02-09 | 1987-11-24 | Chemex Pharmaceuticals | Lipoxygenase inhibitors |
| EP0289506A4 (en) * | 1986-11-19 | 1990-12-12 | Chemex Pharmaceuticals, Inc. | Lipoxygenase inhibitors |
| EP0290442A4 (en) * | 1986-11-19 | 1990-07-03 | Chemex Pharmaceuticals Inc | MEDICINAL PREPARATIONS AND MIXTURES THEREOF, ORGANIC COMPOSITIONS AND METAL SALTS. |
| US6579880B2 (en) * | 2000-06-06 | 2003-06-17 | Ortho-Mcneil Pharmaceutical, Inc. | Isoxazoles and oxadiazoles as anti-inflammatory inhibitors of IL-8 |
| AU2003237379A1 (en) * | 2002-06-10 | 2003-12-22 | Oklahoma Medical Research Foundation | A method for using tethered bis(polyhydroxyphenyls) and o-alkyl derivatives thereof in treating inflammatory conditions of the central nervous system |
| ES2536177T3 (es) * | 2005-01-27 | 2015-05-21 | Erimos Pharmaceuticals Llc | Formulaciones para la inyección de butanos catecólicos, incluyendo compuestos de NDGA, en animales |
| US7741357B1 (en) * | 2006-04-17 | 2010-06-22 | Johns Hopkins University | Heterocyclic and carbonate derivatives of NDGA and their use as new anti-HIV and anti-cancer agents |
-
2007
- 2007-10-02 CN CN200780044510.7A patent/CN101547602B/zh active Active
- 2007-10-02 EP EP07853744.6A patent/EP2076125B1/en not_active Not-in-force
- 2007-10-02 WO PCT/US2007/080231 patent/WO2008042921A2/en not_active Ceased
- 2007-10-02 US US12/443,926 patent/US8232277B2/en active Active - Reinstated
- 2007-10-02 ES ES07853744.6T patent/ES2449237T3/es active Active
- 2007-10-02 JP JP2009531568A patent/JP5362572B2/ja not_active Expired - Fee Related
-
2012
- 2012-07-30 US US13/561,517 patent/US8691845B2/en active Active - Reinstated
-
2014
- 2014-04-07 US US14/246,741 patent/US9481660B2/en active Active - Reinstated
-
2016
- 2016-10-31 US US15/339,822 patent/US20170044121A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US9481660B2 (en) | 2016-11-01 |
| ES2449237T3 (es) | 2014-03-18 |
| EP2076125A4 (en) | 2011-05-04 |
| US20090306070A1 (en) | 2009-12-10 |
| EP2076125A2 (en) | 2009-07-08 |
| HK1136159A1 (en) | 2010-06-25 |
| US8232277B2 (en) | 2012-07-31 |
| US20130053378A1 (en) | 2013-02-28 |
| JP5362572B2 (ja) | 2013-12-11 |
| JP2010505869A (ja) | 2010-02-25 |
| EP2076125B1 (en) | 2013-12-04 |
| US20140221384A1 (en) | 2014-08-07 |
| WO2008042921A3 (en) | 2008-06-05 |
| WO2008042921A2 (en) | 2008-04-10 |
| CN101547602A (zh) | 2009-09-30 |
| US20170044121A1 (en) | 2017-02-16 |
| US8691845B2 (en) | 2014-04-08 |
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