WO2007026766A1 - 1,3-ジヨードヒダントイン化合物およびその製造方法 - Google Patents
1,3-ジヨードヒダントイン化合物およびその製造方法 Download PDFInfo
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- WO2007026766A1 WO2007026766A1 PCT/JP2006/317113 JP2006317113W WO2007026766A1 WO 2007026766 A1 WO2007026766 A1 WO 2007026766A1 JP 2006317113 W JP2006317113 W JP 2006317113W WO 2007026766 A1 WO2007026766 A1 WO 2007026766A1
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- compound
- dih
- wet body
- jodohydantoin
- present
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
- C07D233/82—Halogen atoms
Definitions
- the present invention relates to a 1,3-Jodohydantoin compound and a method for producing the same. Specifically, the present invention relates to improvements for improving the long-term stability of the compounds. Background art
- 1,3-Jodohydantoin compounds (hereinafter also simply referred to as “DIH compounds”) are used as photosensitizers such as photographs, or as iodizing agents or oxidizing agents in the production process of pharmaceuticals, agricultural chemicals, chemicals, etc. Widely used.
- DIH compound for example, a method of reacting iodine monochloride with a hydantoin compound in an aqueous solution in the presence of a base has been disclosed (for example, JP 2002-30072 and J. Org. Chem., 30 (1965) 1101 ⁇ : see L 104).
- a technique has the advantage that it is simple and highly efficient, and that post-treatment such as purification and waste liquid treatment is easy.
- Japanese Patent Laid-Open No. 2002-30072 describes, as a method for purifying a DIH compound from a reaction system, that "the collected crystals are collected by filtration and the obtained crystals are dried under reduced pressure". It has been done.
- the DIH compound produced by the method described in the above-mentioned literature is usually stored until it is used for the above-mentioned use.
- a powerful storage method for example, a method of storing in a dark place under reduced pressure under a nitrogen atmosphere is disclosed (for example, J. Labelled Compd. Radiopharm., 44—12 (2001) 815 — See 830). Disclosure of the invention
- the above document does not describe a DIH compound that is easy to handle and has excellent storage stability.
- the DIH compound is produced by the production method described in the above document, it is described in the above document.
- the DIH compound is stored by the general storage method as described above, it has been found by the present inventors that the DIH compound has a problem that the purity tends to be lowered. The strong decrease in purity is caused by the decomposition of DIH compounds and This is thought to be due to liberation as a simple substance (I). When I liberates like this,
- the present invention suppresses the liberation of I during the production and storage of DIH compounds.
- the purpose is to do.
- DIH compounds are unstable even at room temperature in a wet state containing liquid components such as water and organic solvents to some extent, and this is the cause of I release as described above.
- the present inventors based on the above knowledge, prevent decomposition of DIH compound and accompanying release of I by controlling the drying means during production of DIH compound and the temperature condition during storage.
- the present invention provides a step of preparing a wet body containing a 1,3-Jodohydantoin compound, and (1) contacting the wet body with a heated gas to dry the wet body Or (2) a step of freeze-drying the wet body, and a method for producing a 1,3-Jodohydantoin compound.
- the present invention is a method for storing a 1,3-Jodohydantoin compound, comprising a step of storing the 1,3-Jodohydantoin compound under a temperature condition of 15 ° C or lower.
- the present invention relates to 1,3-Jodohydantoy, wherein the free I content is 1% by mass or less.
- the first of the present invention relates to a method for producing a DIH compound. Specifically, first, DIH compound Prepare a wet body containing objects. Then, (1) the wet body is dried by contacting the wet body with a heated gas, or (2) the wet body is freeze-dried.
- the DIH compound is unstable in a wet state containing a certain amount of liquid components, and this causes I release as described above. And maybe
- the first step in the first production method of the present invention that is, the step of preparing a wet body containing a DIH compound will be described.
- DIH compound means the following chemical formula (I):
- R 1 and R 2 are each independently a hydrogen atom or a C to C alkyl group
- the method for obtaining a wet body containing a DIH compound is not particularly limited.
- the wet body containing the DIH compound may be synthesized according to a known method (for example, the method described in JP-A-2002-30072) or by purchasing a commercially available product. May be used.
- the following method can be used as a method for preparing a wet body containing a DIH compound by itself.
- the following preparation method is merely an example, and even if a “wet body containing DIH compound” prepared by a method other than the following form is used, of course, Good.
- the DIH compound (chemical formula (1)) is a hydantoin compound (chemicals) in the presence of a base in an aqueous solution, for example, as shown in chemical reaction formula 1 below. It is produced by reacting iodine monochloride with formula ( ⁇ )).
- R 1 and IT have the same definitions as above.
- R 1 and R 2 have the same definitions as above.
- R 1 and R 2 are a hydrogen atom or a C to C alkyl group as described above.
- R 1 and R 2 may be the same or different. Considering the yield of the synthesis reaction and the ease of handling, R 1 and R 2 are preferably the same.
- the alkyl group may be linear, branched or cyclic.
- the alkyl group has 1 to 6 carbon atoms, preferably 1 to 2 carbon atoms, and more preferably 1 carbon atom.
- Specific examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sbutyl group, tbutyl group, pentyl group, isopentyl group, neopentyl group, and hexyl group. Is mentioned.
- Alkyl groups other than these may be used. Among these, from the viewpoint of being inexpensive and easy to obtain from an industrial viewpoint, both R 1 and R 2 are cation groups. Preferably there is.
- the method for obtaining the hydantoin compound ( ⁇ ) is not particularly limited!
- the hydantoin compound synthesized according to a known method may be used, or a hydantoin compound commercially available may be purchased.
- Iodine monochloride is a compound represented by the chemical formula "IC1", and since it contains iodine having an acid number +1, it is highly reactive, and as an iodinating agent for many synthetic reactions. Used.
- the method for obtaining iodine monochloride (IC1) is not particularly limited, and it may be synthesized according to a known method, or purchased by purchasing commercially available iodine monochloride. Good.
- An example of a method for synthesizing iodine monochloride by itself is a method of distilling after liquefaction by passing chlorine over iodine.
- silicon monochloride synthesized by other methods may be used.
- the reaction between the hydantoin compound and iodine monochloride is carried out in the presence of a base.
- This base functions as a catalyst in a reaction system containing a hydantoin compound and iodine monochloride.
- the specific form of the base is not particularly limited, and a base generally used in such a synthesis reaction can be similarly used.
- bases include, for example, alkali metal Z alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, and the like. And carbonates. Only one of these bases may be used alone, or two or more of these bases may be used in combination.
- the above reaction is performed in an aqueous solution, but a solvent other than water may be included.
- a solvent other than water may be included.
- amide solvents and ester solvents may be included.
- the mixing ratio of each component in the above reaction is not particularly limited, and conventionally known knowledge (particularly, the above-mentioned JP-A-2002-30072) can be appropriately referred to.
- the reaction system When the above reaction is completed, components other than the DIH compound are removed from the reaction system. This gives a solution of the DIH compound. Subsequently, most of the solvent contained in the solution is removed. Thereby, a “wet body containing a DIH compound” can be prepared. However, the step of removing the solvent may be performed before removing components other than the DIH compound.
- the method for removing components other than the DIH compound from the reaction system is not particularly limited, and examples thereof include methods of filtration, recrystallization and extraction, and combinations thereof. Other techniques may be used.
- the "wet body containing a DIH compound" prepared in this step is composed of a DIH compound, a solvent, and, in some cases, a small amount of impurities, and the content of the solvent in the wet body is particularly high. Not limited.
- the content of the solvent is about 8 to 30% by mass with respect to the total amount of the wet body.
- the content of the solvent in the wet body may be large, but if the content of the solvent is too large, it takes a long time for drying, which may increase the production cost.
- the wet body containing a DIH compound obtained above, (1) the wet body is dried by contacting the wet body with a heated gas. Or (2) freeze-drying the wet body.
- the wet body containing the DIH compound prepared above is contacted with a heated gas to dry the wet body. That is, in the method (1), so-called “fluidized drying” is adopted.
- an industrially common drying method has been adopted as a method of drying a wet body containing a DIH compound.
- the present inventors have found that, depending on these methods, a part of the wet body containing the DIH compound is decomposed and I is liberated. Specifically, 2
- the heat-labile DIH compound is decomposed when the wet body is exposed to a high temperature condition for several hours, ie, for several hours. Therefore, according to the production method of the present application, the liberation of I during the production of the DIH compound is minimized.
- fluid drying is not particularly limited, and conventionally known knowledge can be appropriately referred to in the field of compound synthesis. Examples of preferred forms in fluid drying are shown below. However, it is not limited only to the following forms.
- heated gas means a gas having a temperature at which the wet body can be dried by contact with the wet body containing a DIH compound.
- the heated gas is preferably a gas that does not react with the DIH compound.
- Specific examples of the composition of the heated gas include nitrogen gas, argon gas, helium gas, air gas, and a mixed gas thereof, but the composition of the heated gas is not limited to these.
- air gas is preferably used as the heating gas.
- the temperature of the heated gas at the time of contact with the wet body is not particularly limited, and can be determined by comprehensively considering physical properties of the DIH compound to be produced and general knowledge on fluid drying.
- the temperature of the heated gas is preferably 20 to 200 ° C, more preferably 40 to 170 ° C, and still more preferably 90 to 130 ° C. If the temperature of the heated gas is too low, the amount of heat is insufficient, and as a result, drying may take a long time, or it may not be possible to dry to the desired liquid content. On the other hand, if the temperature of the heated gas is too high, the DIH compound may be altered (decomposed or melted) by overheating.
- the flow rate of the heated gas when contacting the wet body is preferably 0.1 to: LO. Om / low, more preferably 0.3 to 5 Om / low, more preferably 0.5 to 3. OmZ seconds. If the flow rate of the heated gas is too small, the heated gas cannot sufficiently contact the entire wet body. As a result, the drying may take a long time or may not be dried to a desired liquid content. On the other hand, if the flow rate of the heated gas is too large, the wet body may be scattered excessively, making it difficult to collect.
- freeze-drying it can be suppressed to a minimum. It is estimated that the mechanism by which freeze-drying is used to solve the conventional problems is the same as in the case of fluidized drying.
- the method (1) and the method (2) are the same.
- Freeze-drying is also referred to as freeze-drying, in which a wet body is rapidly frozen at a temperature below the freezing point, and the solvent is sublimated by sublimation to a vapor pressure below the solvent of the frozen material to be removed. In this method, the wet body is dried.
- lyophilization is not particularly limited, and conventionally known knowledge can be appropriately referred to in the field of compound synthesis. Examples of preferred forms in lyophilization are shown below. However, it is not limited only to the following forms.
- the wet body containing the DIH compound is rapidly cooled to a predetermined temperature. As a result, the wet body is frozen.
- the temperature reached by rapid cooling is not limited, but the wet body is preferably cooled to 196 to 0 ° C, more preferably 100 to 20 ° C.
- the frozen material is depressurized, and the pressure condition at this time is not particularly limited, and may be depressurized to a level necessary for removing the solvent contained in the wet body. For example, 10-15
- the wet body is dried by the method of (2), a solvent is further added to the "wet body containing DIH compound" prepared above to prepare a slurry wet body, and the obtained slurry
- the wet body may be lyophilized by the method described above. According to such a form, the sublimation of the whole wet slurry is more likely to sublime due to freezing of the entire wet slurry in comparison with the case where the wet body prepared above is simply lyophilized as it is. can get.
- the solvent added to the wet body when preparing the slurry-like wet body is not particularly limited.
- a solvent that does not react with the DIH compound and easily sublimes in the subsequent lyophilization examples include water, ethyl acetate, n-butyl acetate, N, N-dimethylformamide and the like. Of these, it is preferable to add more water from the viewpoint of being inexpensive and suitable for lyophilization that is easy to handle.
- the addition amount of the solvent when adding the solvent to the wet body is not particularly limited, but the total content of the solvent with respect to the total amount of the slurry-like wet body is preferably 30 to 70 mass%, more preferably 50. What is necessary is just to add the solvent of the quantity used as -60 mass%.
- the second of the present invention is a DIH compound with a reduced free I content. At this time, the present invention
- the content of free I in the second DIH compound is preferably 1% by mass or less, and more
- the content is preferably 0.8% by mass or less, more preferably 0.4% by mass or less, and particularly preferably 0.2% by mass or less. As mentioned above, free I can cause various problems.
- the technical scope of the first production method of the present invention is that such an amount of free I
- DIH compound containing 2 is produced. In some cases, DIH compounds containing amounts of free I outside this range may be produced. Also,
- the technical scope of the DIH compound of the present invention is not limited to the form produced by the first production method of the present invention, and may be produced by another production method. .
- the content of free I in the manufactured DIH compound is not limited to the form produced by the first production method of the present invention, and may be produced by another production method.
- the second DIH compound of the present invention has a low water content in addition to the free I content.
- the water content in the second DIH compound of the invention is preferably 6% by mass or less, more preferably 5% by mass or less, further preferably 3% by mass or less, and particularly preferably 1% by mass. It is as follows. Therefore, when the wet body containing the DIH compound is fluidized (1) or freeze-dried (2) in the first production method of the present invention, the water content in the obtained DIH compound is within the above range. It is preferable to control the drying conditions so as to obtain a value.
- the use of the second DIH compound of the present invention is not particularly limited.
- a photosensitizing agent such as a photograph, or an iodinating agent or an oxidizing agent in a manufacturing process of pharmaceuticals, agricultural chemicals, chemicals and the like. Can be adopted.
- a third aspect of the present invention is a method for storing a DIH compound, comprising a step of storing the DIH compound under a temperature condition of 15 ° C or lower.
- the DIH compound used in the third storage method of the present invention is not particularly limited, and a conventionally known DIH compound is used. However, the decomposition of DIH compounds and the resulting release of I
- the DI H compound produced by the first production method of the present invention or the DIH compound provided by the second of the present invention is preferably used. Since specific forms of these DIH compounds are as described above, detailed description thereof is omitted here.
- the DIH compound is stored under a temperature condition of 15 ° C or lower, preferably 10 ° C or lower, more preferably 5 ° C or lower.
- the specific form other than being stored under the above temperature condition is not particularly limited, and conventionally known knowledge about the storage of the compound can be appropriately referred to.
- the DIH compound kept in one place, but also forms such as “transport” that move through various places until it is used for a predetermined use. It can be included in the concept of “storage”.
- the humidity condition for storing the DIH compound is not particularly limited. In general, it is preferably stored under a low humidity condition. Specifically, the relative humidity (RH) of the atmosphere at the storage location is preferably 50% or less, more preferably 30% or less.
- the DIH compound is usually stored in a state filled in a predetermined container, but the specific form of the container is not particularly limited, and the compound storage field Conventionally known storage containers can be used as appropriate.
- the constituent material of the storage container include industrially used resin, and specific examples thereof include polyethylene, polypropylene, polystyrene, polyester, polyvinyl chloride, polyvinyl chloride and polyvinylidene.
- the shape of the storage container is not particularly limited, and examples thereof include a bag shape, a box shape, and a drum shape.
- the storage container has a sealing function. From such a point of view, it is preferable that a polysalt-vinylidene Z-polyethylene composite material or a highly noble polymer is used as a constituent material of the storage container. A resin-lined metal container can also be used as a storage container. However, in a powerful form, a very small amount of I
- the temperature condition does not have to be within the above-mentioned range over the entire storage period, but it is temporarily placed in a temperature condition of about room temperature due to movement or the like. Except for this period, the temperature condition may be within the above range for a period of about 100%.
- the third storage method of the present invention may be combined with the first production method of the present invention.
- the DIH compound is stored using the third storage method of the present invention
- the DIH compound is manufactured by the first manufacturing method of the present invention, It is convenient to store DIH compounds by the storage method described in 3.
- the wet body prepared above is charged into a fluidized dryer, and the wet body is dried by contacting air at 110 ° C as a heated gas at a flow rate of 1 mZ seconds for 30 minutes. Five,
- a pale yellow crystalline powder of 5 dimethyl-1,3 joadhydantoin was obtained with a purity of 98% or more.
- the content of release I was 0.2% by mass or less, and the content of water was 1% by mass or less.
- the used sample was dried at 105 ° C for 2 hours under atmospheric pressure, and the decrease in mass was measured to determine the water content.
- the wet body prepared above was charged into a freeze dryer and cooled to 80 ° C to freeze the wet body. Next, the obtained frozen body was sublimated and dried at 20 ° C. for 22 hours under a reduced pressure of 270 Pa to obtain a light yellow crystalline powder of 5,5 dimethyl-1,3 joadhydantoin.
- the slurry-like wet body prepared above was charged into a freeze dryer and cooled to 80 ° C to freeze the wet body.
- the obtained frozen body was sublimated and dried at 20 ° C for 14 hours under a reduced pressure of 270 Pa to obtain a light yellow crystal powder of 5,5 dimethyl-1,3 joydhydantoin with a purity of 98% or more. It was.
- the content of release I was 0.2% by mass or less, and the content of water was 1% by mass.
- the light yellow crystal powder of 5,5 dimethyl-1,3 joydhydantoin obtained in Examples 1 to 3 above was stored at 5 ° C. in a sealed state in a polyethylene container. As a result, changes in the appearance and free I content of the compound were not observed even after 6 months.
- the wet body prepared as described above was charged into a 1000 L-coal dryer and dried at 40 to 70 ° C under reduced pressure of 2700 to 5300 Pa.
- Each storage container prepared above was filled with 10 kg of the DIH compound prepared in the same manner, and each bag was heat-sealed after filling.
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2006800318215A CN101253156B (zh) | 2005-09-02 | 2006-08-30 | 1,3-二碘乙内酰脲化合物及其制造方法 |
JP2007533295A JP5096150B2 (ja) | 2005-09-02 | 2006-08-30 | 1,3−ジヨードヒダントイン化合物およびその製造方法 |
EP06797085.5A EP1939184B1 (en) | 2005-09-02 | 2006-08-30 | 1,3-diiodohydantoin compound and process for production thereof |
US11/991,285 US7897785B2 (en) | 2005-09-02 | 2006-08-30 | 1,3-Diiodohydantoin compound and production method thereof |
US12/926,899 US8710240B2 (en) | 2005-09-02 | 2010-12-16 | 1,3-diiodohydantoin compound and production method thereof |
US12/926,898 US8722902B2 (en) | 2005-09-02 | 2010-12-16 | 1,3-diiodohydantoin compound and production method thereof |
US12/926,900 US8772506B2 (en) | 2005-09-02 | 2010-12-16 | 1,3-diiodohydantoin compound and production method thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2005255557 | 2005-09-02 | ||
JP2005-255557 | 2005-09-02 |
Related Child Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/991,285 A-371-Of-International US7897785B2 (en) | 2005-09-02 | 2006-08-30 | 1,3-Diiodohydantoin compound and production method thereof |
US12/926,900 Continuation US8772506B2 (en) | 2005-09-02 | 2010-12-16 | 1,3-diiodohydantoin compound and production method thereof |
US12/926,899 Division US8710240B2 (en) | 2005-09-02 | 2010-12-16 | 1,3-diiodohydantoin compound and production method thereof |
US12/926,898 Division US8722902B2 (en) | 2005-09-02 | 2010-12-16 | 1,3-diiodohydantoin compound and production method thereof |
Publications (1)
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WO2007026766A1 true WO2007026766A1 (ja) | 2007-03-08 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/JP2006/317113 WO2007026766A1 (ja) | 2005-09-02 | 2006-08-30 | 1,3-ジヨードヒダントイン化合物およびその製造方法 |
Country Status (5)
Country | Link |
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US (4) | US7897785B2 (ja) |
EP (4) | EP2522660B1 (ja) |
JP (3) | JP5096150B2 (ja) |
CN (1) | CN101253156B (ja) |
WO (1) | WO2007026766A1 (ja) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013023475A (ja) * | 2011-07-21 | 2013-02-04 | Toho Earthtech Inc | 1,3−ジヨードヒダントイン類の製造方法 |
WO2014097787A1 (ja) * | 2012-12-19 | 2014-06-26 | 日宝化学株式会社 | ハロヒダントイン化合物の製造方法及びハロヒダントイン化合物 |
WO2014097788A1 (ja) * | 2012-12-19 | 2014-06-26 | 日宝化学株式会社 | ハロヒダントイン化合物の製造方法及び製造装置、再利用システム、ならびにハロヒダントイン化合物 |
WO2014147889A1 (ja) * | 2013-03-19 | 2014-09-25 | 日宝化学株式会社 | ハロヒダントイン化合物の製造方法 |
Families Citing this family (2)
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CN103333115B (zh) * | 2013-07-15 | 2015-01-21 | 河北鑫淘源环保科技有限公司 | 用作化工中间体的溴氯海因的生产方法 |
JP6623090B2 (ja) * | 2016-03-15 | 2019-12-18 | 信越化学工業株式会社 | 高い熱ゲル強度を有するヒドロキシプロピルメチルセルロース及びその製造方法並びにこれを含む食品 |
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JP2002030072A (ja) | 2000-05-10 | 2002-01-29 | Nippon Nohyaku Co Ltd | 1,3−ジヨードヒダントイン類の製造方法 |
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JPH08325192A (ja) * | 1995-05-25 | 1996-12-10 | Bizen Kasei Kk | ドコサヘキサエン酸含有リン脂質の製造方法 |
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EP1301512A2 (en) * | 2000-07-21 | 2003-04-16 | LION Bioscience AG | Bicyclic hydantoin derivatives and combinatorial libraries thereof |
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2006
- 2006-08-30 EP EP12180060.1A patent/EP2522660B1/en active Active
- 2006-08-30 JP JP2007533295A patent/JP5096150B2/ja active Active
- 2006-08-30 EP EP06797085.5A patent/EP1939184B1/en not_active Not-in-force
- 2006-08-30 US US11/991,285 patent/US7897785B2/en not_active Expired - Fee Related
- 2006-08-30 EP EP12180061.9A patent/EP2522661B1/en not_active Not-in-force
- 2006-08-30 EP EP15154215.6A patent/EP2921483A1/en not_active Ceased
- 2006-08-30 CN CN2006800318215A patent/CN101253156B/zh active Active
- 2006-08-30 WO PCT/JP2006/317113 patent/WO2007026766A1/ja active Application Filing
-
2010
- 2010-12-16 US US12/926,899 patent/US8710240B2/en not_active Expired - Fee Related
- 2010-12-16 US US12/926,900 patent/US8772506B2/en not_active Expired - Fee Related
- 2010-12-16 US US12/926,898 patent/US8722902B2/en not_active Expired - Fee Related
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2012
- 2012-08-16 JP JP2012180595A patent/JP5722843B2/ja active Active
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2014
- 2014-12-26 JP JP2014266271A patent/JP2015129123A/ja active Pending
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Also Published As
Publication number | Publication date |
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EP1939184A1 (en) | 2008-07-02 |
US8722902B2 (en) | 2014-05-13 |
US20110087031A1 (en) | 2011-04-14 |
EP1939184B1 (en) | 2013-06-05 |
EP2921483A1 (en) | 2015-09-23 |
CN101253156B (zh) | 2012-07-04 |
JP5722843B2 (ja) | 2015-05-27 |
JPWO2007026766A1 (ja) | 2009-03-12 |
EP2522660B1 (en) | 2014-05-14 |
US20110092714A1 (en) | 2011-04-21 |
EP2522661A1 (en) | 2012-11-14 |
US8710240B2 (en) | 2014-04-29 |
JP2012246305A (ja) | 2012-12-13 |
EP1939184A4 (en) | 2010-07-21 |
US8772506B2 (en) | 2014-07-08 |
US20110144350A1 (en) | 2011-06-16 |
EP2522661B1 (en) | 2015-04-15 |
US7897785B2 (en) | 2011-03-01 |
JP2015129123A (ja) | 2015-07-16 |
EP2522660A1 (en) | 2012-11-14 |
CN101253156A (zh) | 2008-08-27 |
JP5096150B2 (ja) | 2012-12-12 |
US20090259050A1 (en) | 2009-10-15 |
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