JP2005220138A - 1,2−ジアミノシクロヘキサン−白金(ii)−錯体の製造方法 - Google Patents
1,2−ジアミノシクロヘキサン−白金(ii)−錯体の製造方法 Download PDFInfo
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- JP2005220138A JP2005220138A JP2005031078A JP2005031078A JP2005220138A JP 2005220138 A JP2005220138 A JP 2005220138A JP 2005031078 A JP2005031078 A JP 2005031078A JP 2005031078 A JP2005031078 A JP 2005031078A JP 2005220138 A JP2005220138 A JP 2005220138A
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- diaminocyclohexane
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- 238000004519 manufacturing process Methods 0.000 title claims description 5
- SGLJYTWMWIAGEU-UHFFFAOYSA-N cyclohexane-1,2-diamine;platinum(2+) Chemical compound [Pt+2].NC1CCCCC1N SGLJYTWMWIAGEU-UHFFFAOYSA-N 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims abstract description 13
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 claims abstract description 9
- UGQDIOUBRRLHMW-UHFFFAOYSA-N cyclohexane-1,1-diamine;platinum(2+) Chemical compound [Pt+2].NC1(N)CCCCC1 UGQDIOUBRRLHMW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 102100028735 Dachshund homolog 1 Human genes 0.000 claims abstract description 4
- 101000915055 Homo sapiens Dachshund homolog 1 Proteins 0.000 claims abstract description 4
- 230000002950 deficient Effects 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000000047 product Substances 0.000 claims description 13
- 239000002244 precipitate Substances 0.000 claims description 8
- 229960001756 oxaliplatin Drugs 0.000 claims description 5
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- VBIXEXWLHSRNKB-UHFFFAOYSA-N ammonium oxalate Chemical compound [NH4+].[NH4+].[O-]C(=O)C([O-])=O VBIXEXWLHSRNKB-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 2
- 230000001580 bacterial effect Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 229910021642 ultra pure water Inorganic materials 0.000 claims description 2
- 239000012498 ultrapure water Substances 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 150000003891 oxalate salts Chemical group 0.000 claims 1
- 238000000746 purification Methods 0.000 abstract description 4
- 239000013543 active substance Substances 0.000 abstract 1
- 239000013049 sediment Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical class N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229960004316 cisplatin Drugs 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- MSMNVXKYCPHLLN-UHFFFAOYSA-N azane;oxalic acid;hydrate Chemical compound N.N.O.OC(=O)C(O)=O MSMNVXKYCPHLLN-UHFFFAOYSA-N 0.000 description 1
- 238000002288 cocrystallisation Methods 0.000 description 1
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 1
- -1 diaqua compound Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
Abstract
【解決手段】K2PtX2と1,2−ジアミノシクロヘキサン(DACH)との反応により次の式の化合物にし、(2)と銀塩AgnAとの反応により次の式の化合物にし、かつ生じたAgX沈殿物を除去し、(3)とジカルボキシラートとの反応により次の式の化合物にし、生成物(1)を単離する工程を有する、ジアミノシクロヘキサン−白金(II)−ジカルボキシラートの製造方法において、工程Cにおいて銀塩を不足量で使用することを特徴とする方法
【選択図】なし
Description
1. 高い純度、特に低いAg含有量;
2. 欧州薬局方(European Pharmacopoeia, 4th edition, 2002, supplement 4.4)の要求を満たすか又は上回る;
3. 最終生成物の精製のために再結晶する必要がない;
4. 高い収率で得られる;
5. 腸管外適用のための作用物質の特別な適性。
B K2PtX2と1,2−ジアミノシクロヘキサン(DACH)との反応により次の式の化合物にする
もちろん、K2PlI4から直接行う(工程Bから出発する)ことも可能である。更に、K2PtCl4をDACHと直接反応させることも可能である。しかしながら、このヨージドは、Ag沈殿物の可溶性が低いために、最終生成物の純度について有利な展望が開ける。
C 銀反応からの反応混合物を濾過の前に10℃より低く冷却する。それにより沈殿物は可能な限り完全に除去され、かつこの生成物は銀をわずかに含有する。
中間体:異性体/エナンチオマー純粋なジアミノシクロヘキサン、適当な酒石酸塩を用いた結晶化及び/又は蒸留により精製。
テトラクロロ白金酸カリウム(K2[PtCl4])と、ヨウ化カリウム(KI)及び1,2−ジアミノシクロヘキサンとの反応、その際、まず式(2)のジヨージド−化合物(X=I)が得られる。
実施例1
K2[PtCl4](59.60g)を水(439ml)に溶かした。ヨウ化カリウム(168.0g)を水(147ml)に溶かした。両方の溶液を合わせ、30分撹拌した。
Claims (12)
- 次の工程:
B K2PtX2と1,2−ジアミノシクロヘキサン(DACH)との反応により次の式の化合物にする工程、
D (3)とジカルボキシラートとの反応により次の式の化合物にする工程、
その際、R1及びR2は一緒になってジカルボキシラト基を形成し、XはCl又はIを表し、Aは鉱酸の1〜2価のアニオンを表し、nは1又は2を表す、ジアミノシクロヘキサン−白金(II)−ジカルボキシラートの製造方法において、工程Cにおいて銀塩を不足量で使用することを特徴とする、ジアミノシクロヘキサン−白金(II)−ジカルボキシラートの製造方法。 - XはIを表し、ジカルボキシラートはオキサラートである、請求項1記載の方法。
- オキサリプラチンの製造のために、次の工程:
A K2PtCl4をKIと反応させてK2PtI4にする工程を有する、請求項2記載の方法。 - 工程Cにおいて、沈殿物の除去の前に、この混合物を1〜10℃に冷却することを特徴とする、請求項1から3までのいずれか1項記載の方法。
- 工程Dにおいてシュウ酸アンモニウムを使用することを特徴とする、請求項1から4までのいずれか1項記載の方法。
- 工程Dの後で得られた溶液を、
E 活性炭で連続して2回精製しかつ濾過することを特徴とする、請求項1から5までのいずれか1項記載の方法。 - 工程D又はEの後に得られた溶液を、生成物1g当たり10mlより少なくなるまで濃縮することを特徴とする、請求項1から6までのいずれか1項記載の方法。
- 制限されたバクテリア含有量を有する、精製された、エンドトキシンの少ない水(EP 4もしくはUSP 27による「純水」)中で実施することを特徴とする、請求項1から7までのいずれか1項記載の方法。
- 水がEP(欧州薬局方、第4版、2002)による「超純水」である、請求項8記載の方法。
- 工程E)により得られた溶液を滅菌濾過し、次いで濃縮し、
F 固形物成分を濾過し、乾燥することを特徴とする、請求項6記載の方法。 - 工程F)の後に、
G 生成物を請求項8又は9記載の水で、引き続き薬理学的に許容性の低沸点溶剤を用いて洗浄することを特徴とする、請求項1から10までのいずれか1項記載の方法。 - 溶剤が、アセトン又はメタノールである、請求項11記載の方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004005906A DE102004005906B3 (de) | 2004-02-05 | 2004-02-05 | Verfahren zur Herstellung von 1,2-Diaminocylohexan-Platin(II)-Komplexen |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005220138A true JP2005220138A (ja) | 2005-08-18 |
JP3997232B2 JP3997232B2 (ja) | 2007-10-24 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2005031078A Expired - Fee Related JP3997232B2 (ja) | 2004-02-05 | 2005-02-07 | 1,2−ジアミノシクロヘキサン−白金(ii)−錯体の製造方法 |
Country Status (17)
Country | Link |
---|---|
US (1) | US7309796B2 (ja) |
EP (1) | EP1561754B1 (ja) |
JP (1) | JP3997232B2 (ja) |
CN (2) | CN1680411A (ja) |
AR (1) | AR047519A1 (ja) |
AT (1) | ATE356136T1 (ja) |
AU (1) | AU2005200417C1 (ja) |
BR (1) | BRPI0500307A (ja) |
CA (1) | CA2492254C (ja) |
CY (1) | CY1106579T1 (ja) |
DE (2) | DE102004005906B3 (ja) |
DK (1) | DK1561754T3 (ja) |
ES (1) | ES2281031T3 (ja) |
MX (1) | MXPA05001428A (ja) |
PL (1) | PL1561754T3 (ja) |
PT (1) | PT1561754E (ja) |
SI (1) | SI1561754T1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009525273A (ja) * | 2006-01-30 | 2009-07-09 | プラットコー テクノロジーズ (プロプライエタリー) リミテッド | 白金(ii)錯体の調製 |
US8068647B2 (en) | 2005-06-14 | 2011-11-29 | General Electric Company | Method and apparatus for real-time motion correction for ultrasound spatial compound imaging |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2547275A1 (en) | 2003-11-25 | 2005-06-09 | Platco Technologies (Proprietary) Limited | Platinum(ii) complexes, preparation and use |
TW200617014A (en) * | 2004-07-12 | 2006-06-01 | Sicor Inc | Cis-diiodo-(trans-l-1,2-cyclohexanediamine) platinum (Ⅱ) complex and processes for preparing high purity oxaliplatin |
ES2327346T3 (es) * | 2004-09-01 | 2009-10-28 | Platco Technologies (Proprietary) Limited | Preparacion de complejos de platino (ii). |
US20090076139A1 (en) * | 2007-09-19 | 2009-03-19 | Protia, Llc | Deuterium-enriched oxalplatin |
AR072238A1 (es) * | 2009-01-13 | 2010-08-18 | Eriochem Sa | Proceso para preparar derivados antineoplasicos neutros de platino (ii) grado farmaceutico con bajo contenido de plata |
EP2208731B1 (en) | 2009-06-26 | 2012-08-15 | Umicore AG & Co. KG | Process for preparation of 1,2-diamino-cyclohexane-platinum(II) complexes |
CN101891771B (zh) * | 2010-07-30 | 2012-12-12 | 重庆泰濠制药有限公司 | 一种制备奥沙利铂的方法 |
CN103232494A (zh) * | 2012-05-22 | 2013-08-07 | 湖北一半天制药有限公司 | 奥沙利铂的制备方法 |
CA3110611A1 (en) | 2018-09-01 | 2020-03-05 | Beijing Showby Pharmaceutical Co., Ltd. | Phosphate of platinum compound and preparation method therefor |
CN111569868A (zh) * | 2020-06-10 | 2020-08-25 | 上海济平新能源科技有限公司 | 一种载于碳上的催化剂的制作方法 |
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JPS6041077B2 (ja) | 1976-09-06 | 1985-09-13 | 喜徳 喜谷 | 1,2‐ジアミノシクロヘキサン異性体のシス白金(2)錯体 |
US4206208A (en) * | 1977-08-29 | 1980-06-03 | The United States Of America As Represented By The Department Of Health, Education And Welfare | Use of 4-carboxy-phthalato(1,2-diaminocyclohexane)-platinum(II) and alkali metal salts thereof with cyclophosphamide and 5-fluorouracil in alleviating L1210 murine leukemia |
US4206226A (en) | 1977-08-29 | 1980-06-03 | The United States Of America As Represented By The Department Of Health, Education And Welfare | Use of 4-carboxy-phthalato-(1,2-diaminocyclohexane)-platinum(II) and alkali metal salts thereof in alleviating L1210 murine leukemia |
GR75598B (ja) * | 1980-04-29 | 1984-08-01 | Sanofi Sa | |
US4665210A (en) * | 1984-12-17 | 1987-05-12 | American Cyanamid Company | Platinum complexes of aliphatic tricarboxylic acids |
DE3575144D1 (de) | 1984-12-17 | 1990-02-08 | American Cyanamid Co | Platinkomplexe von aliphatischen tricarbonsaeuren. |
EP0376076A1 (en) * | 1988-12-27 | 1990-07-04 | Ss Pharmaceutical Co., Ltd. | Novel platinum complex |
JPH0776230B2 (ja) * | 1992-01-13 | 1995-08-16 | 田中貴金属工業株式会社 | 白金化合物の製造方法 |
JPH06287021A (ja) * | 1992-04-22 | 1994-10-11 | Tanaka Kikinzoku Kogyo Kk | 光学活性な白金錯化合物の光学的分割方法 |
JP2673331B2 (ja) * | 1993-01-12 | 1997-11-05 | 田中貴金属工業 株式会社 | 光学的に高純度なシス―オキザラート(トランス―1―1,2―シクロヘキサンジアミン)白金(▲ii▼) |
JP3025602B2 (ja) * | 1993-05-21 | 2000-03-27 | デビオファーム エス.アー. | 光学的に高純度なシス−オキザラート(トランス−l−1,2−シクロヘキサンジアミン)白金(II)錯体の製造方法 |
WO2003004505A1 (en) * | 2001-07-02 | 2003-01-16 | Debiopharm S.A. | Oxaliplatin active substance with a very low content of oxalic acid |
DE10226592B4 (de) * | 2002-06-14 | 2004-07-29 | Faustus Forschungs Cie. Translational Cancer Research Gmbh | Tumorhemmende Platin(II)-oxalato-Komplexe |
TW200617014A (en) * | 2004-07-12 | 2006-06-01 | Sicor Inc | Cis-diiodo-(trans-l-1,2-cyclohexanediamine) platinum (Ⅱ) complex and processes for preparing high purity oxaliplatin |
-
2004
- 2004-02-05 DE DE102004005906A patent/DE102004005906B3/de not_active Expired - Fee Related
-
2005
- 2005-01-11 CA CA2492254A patent/CA2492254C/en not_active Expired - Fee Related
- 2005-01-15 SI SI200530019T patent/SI1561754T1/sl unknown
- 2005-01-15 PT PT05000774T patent/PT1561754E/pt unknown
- 2005-01-15 DE DE502005000428T patent/DE502005000428D1/de active Active
- 2005-01-15 EP EP05000774A patent/EP1561754B1/de active Active
- 2005-01-15 DK DK05000774T patent/DK1561754T3/da active
- 2005-01-15 ES ES05000774T patent/ES2281031T3/es active Active
- 2005-01-15 PL PL05000774T patent/PL1561754T3/pl unknown
- 2005-01-15 AT AT05000774T patent/ATE356136T1/de active
- 2005-01-28 AR ARP050100339A patent/AR047519A1/es active IP Right Grant
- 2005-02-01 AU AU2005200417A patent/AU2005200417C1/en not_active Ceased
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- 2005-02-05 CN CNA2005100083306A patent/CN1680411A/zh active Pending
- 2005-02-05 CN CN2012100261286A patent/CN103214525A/zh active Pending
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8068647B2 (en) | 2005-06-14 | 2011-11-29 | General Electric Company | Method and apparatus for real-time motion correction for ultrasound spatial compound imaging |
JP2009525273A (ja) * | 2006-01-30 | 2009-07-09 | プラットコー テクノロジーズ (プロプライエタリー) リミテッド | 白金(ii)錯体の調製 |
Also Published As
Publication number | Publication date |
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AU2005200417B8 (en) | 2005-08-25 |
CN1680411A (zh) | 2005-10-12 |
ES2281031T3 (es) | 2007-09-16 |
BRPI0500307A (pt) | 2005-11-08 |
DK1561754T3 (da) | 2007-06-11 |
AU2005200417B2 (en) | 2007-07-12 |
AU2005200417C1 (en) | 2008-04-03 |
PT1561754E (pt) | 2007-04-30 |
AU2005200417A1 (en) | 2005-08-25 |
CA2492254A1 (en) | 2005-08-05 |
DE502005000428D1 (de) | 2007-04-19 |
PL1561754T3 (pl) | 2007-07-31 |
JP3997232B2 (ja) | 2007-10-24 |
US7309796B2 (en) | 2007-12-18 |
CA2492254C (en) | 2010-03-16 |
ATE356136T1 (de) | 2007-03-15 |
SI1561754T1 (sl) | 2007-08-31 |
EP1561754B1 (de) | 2007-03-07 |
AR047519A1 (es) | 2006-01-25 |
US20050197389A1 (en) | 2005-09-08 |
EP1561754A1 (de) | 2005-08-10 |
CN103214525A (zh) | 2013-07-24 |
MXPA05001428A (es) | 2005-09-30 |
CY1106579T1 (el) | 2012-01-25 |
DE102004005906B3 (de) | 2005-09-29 |
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