JP2005513492A - 光学活性支持体材料、それらの調製方法及びそれらの使用 - Google Patents
光学活性支持体材料、それらの調製方法及びそれらの使用 Download PDFInfo
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- JP2005513492A JP2005513492A JP2003556165A JP2003556165A JP2005513492A JP 2005513492 A JP2005513492 A JP 2005513492A JP 2003556165 A JP2003556165 A JP 2003556165A JP 2003556165 A JP2003556165 A JP 2003556165A JP 2005513492 A JP2005513492 A JP 2005513492A
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- APPHRAMBJODYPA-UHFFFAOYSA-B tris(1-oxo-2,4,5-trioxa-1lambda5-arsa-3-stannabicyclo[1.1.1]pentan-3-yl) arsorate Chemical compound [Sn+4].[Sn+4].[Sn+4].[O-][As]([O-])([O-])=O.[O-][As]([O-])([O-])=O.[O-][As]([O-])([O-])=O.[O-][As]([O-])([O-])=O APPHRAMBJODYPA-UHFFFAOYSA-B 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
PS-(OZ)n (I)
(式中、
PSは少なくとも6オシド単位を有する多糖又はオリゴ糖を表し、
nは12から30000まで変化し、
夫々のOZ基は互いに独立にOH、-O-C(O)-NH-R又は-O-C(O)-R(式中、Rはおそらく特に硫黄、窒素、酸素、リン、塩素、フッ素、臭素、ヨウ素及びケイ素を含む群から選ばれた少なくとも1個のヘテロ原子により置換された、1〜40個の炭素原子を有するアルキル基、アリール基、アルカリール基又はアラルキル基を表す)を表し得る)
を有する。
−室温で、又は加熱により、常圧又は真空下の、固体支持体及び多糖又はオリゴ糖の前記エステル誘導体及び/又はカルバメート誘導体の溶液からつくられた、懸濁液の蒸発、又は
−固体支持体及び多糖又はオリゴ糖の前記エステル誘導体及び/又はカルバメート誘導体の溶液からつくられた懸濁液への、式(I)の化合物の非溶媒の穏やかな添加及び濾過による単離
で行ない得る。
式(I)の化合物をプロトン性又は非プロトン性の極性有機溶媒に溶解し、
得られた溶液に、本発明の固体支持体を添加し、得られた懸濁液を完全に均一にし、
溶媒を常圧及び/又は真空下で、室温から約100℃までの範囲の温度で蒸発させ、又は一般式Iの誘導体の非溶媒を先の工程で得られた懸濁液に穏やかに添加し、
得られた光学活性支持体を室温で、又は常圧もしくは真空下で加熱することにより乾燥させることを含む連続工程を有する上記第一の実施態様の光学活性支持体の調製方法に関する。
[実施例1]
微結晶性セルロース(100の平均重合度n)2.5g、ピリジン75ml及びヘプタン38mlを反応器に入れる。撹拌し、還流下で加熱して共沸連行によりセルロースの脱水を可能にする。3,5-ジメチルフェニルイソシアネート8.15g及びジメチルアミノピリジン0.05gを添加し、その媒体を24時間にわたって還流下に保つ。その溶液を冷却し、それをメタノール100mlに注入する。沈殿をメタノール300mlで洗浄し、次いでそれを真空下で50℃で乾燥させる(乾燥重量=CDMPC6.5g)。
b/ ポリアミド/CDMPC CSPの調製
メルク社により表示32 121 232のもとに販売される、ポリアミド支持体を15〜40μmで篩分ける。次いで上記工程a/で調製された、CDMPC0.45gをテトラヒドロフラン(THF)40mlに溶解する。
溶離流量1ml/分、
検出波長254nm、
溶離移動相変動(結果の表を参照のこと)、
注入されたラセミ体混合物の量:1μg、
25μlの注入ループ、
注入溶媒エタノール。
微結晶性セルロース(100の平均重合度n)2.5g、ピリジン75ml及びヘプタン38mlを反応器に入れる。撹拌し、還流下で加熱して共沸連行によりセルロースの脱水を可能にする。3,5-ジクロロフェニルイソシアネート10.42g及びジメチルアミノピリジン0.05gを添加し、その媒体を24時間にわたって還流下に保つ。その溶液を冷却し、それをメタノール100mlに注入する。沈殿をメタノール300mlで洗浄し、次いでそれを真空下で50℃で乾燥させる。
b/ ポリアミド/CDCPC CSPの調製
メルク社により表示32 121 232のもとに販売される、ポリアミド支持体を15〜40μmで篩分ける。次いで上記工程a/で調製された、CDCPCの0.45gをテトラヒドロフラン(THF)40mlに溶解する。
溶離流量1ml/分、
検出波長254nm、
溶離移動相変動(結果の表を参照のこと)、
注入されたラセミ体混合物の量:1μg、
25μlの注入ループ、
注入溶媒エタノール。
溶離流量1ml/分、
検出波長254nm、
溶離移動相変動(結果の表を参照のこと)、
注入されたラセミ体混合物の量:1μg、
25μlの注入ループ、
注入溶媒エタノール。
溶離流量1ml/分、
検出波長254nm、
溶離移動相:ヘプタン/イソプロパノール95/5。
[実施例5]
溶離流量1ml/分、
検出波長254nm、
溶離移動相:ヘプタン/イソプロパノール90/10。
[実施例7]
a/ 混合アミローストリス-2,3,6-(3,5-ジメチルフェニルカルバメート及び4-ビニルベンゾエート)の調製
アミロース(平均重合度100)2.5g、ピリジン75ml及びヘプタン38mlを反応器に入れる。アミロースを共沸連行により脱水する。懸濁された媒体を冷却し、次いで3,5-ジメチルフェニルイソシアネート6g及び4-ビニルベンゾイルクロリド3gを連続して添加する。1時間撹拌した後、ジメチルアミノピリジン0.05gを添加し、その媒体を24時間にわたって還流下に保つ。得られた溶液を冷却し、次いでそれをメタノール100mlに注入する。得られた固体を濾過し、それをメタノール300mlで洗浄し、次いでそれを50℃で一定重量まで乾燥させる。混合アミロース誘導体トリス-2,3,6-(3,5-ジメチルフェニルカルバメート及び4-ビニルベンゾエート)7.15gを得る。
ゼオライト(フルカから、表示9606)5gを還流下でトルエン50ml中で共沸連行により脱水する。γ-メルカプトプロピルトリメトキシシラン3gを一度に添加し、その反応懸濁液を72時間にわたって還流下に保つ。懸濁液を濾過し、固体をトルエン2 x 50mlで洗浄する。60℃で真空下で乾燥させた後、メルカプトプロピルゼオライト誘導体6.25gを得る。
ケイ酸マグネシウム(表示288705、スペルコ社からのフロリシル吸収剤)5gをトルエン50ml中で還流下で共沸連行により脱水する。
a/ トリス-2,3,6-(3,5-ジメチルフェニルカルバメート及び4-ビニルベンゾエート)混合アミロースの調製
アミロース(平均重合度100)2.5g、ピリジン75ml及びヘプタン38mlを反応器に入れる。アミロースを共沸連行により脱水する。懸濁中の媒体を冷却し、次いで3,5-ジメチルフェニルイソシアネート6g及び4-ビニルベンゾイルクロリド3gを連続して添加する。1時間撹拌した後、ジメチルアミノピリジン0.05gを添加し、その媒体を24時間にわたって還流下に保つ。得られた溶液を冷却し、次いでそれをメタノール100mlに注入する。得られた固体を濾過し、それをメタノール300mlで洗浄し、次いでそれを50℃で一定重量まで乾燥させる。トリス-2,3,6-(3,5-ジメチルフェニルカルバメート及び4-ビニルベンゾエート)混合アミロース誘導体7.15gを得る。
ゼオライト(フルカから、表示9606)5gを還流下でトルエン50ml中で共沸連行により脱水する。γ-メルカプトプロピルトリメトキシシラン3gを一度に添加し、その反応懸濁液を72時間にわたって還流下に保つ。懸濁液を濾過し、固体をトルエン2 x 50mlで洗浄する。60℃で真空下で乾燥させた後、メルカプトプロピルゼオライト誘導体6.25gを得る。
Claims (21)
- 多糖又はオリゴ糖の一種以上のエステル誘導体、及び/又は一種以上のカルバメート誘導体、及び/又は一種以上の混合エステル及びカルバメート誘導体、並びに有機源及び/又は無機源の固体支持体からなる光学活性支持体であって、前記固体支持体はシリカゲル、アルミナ、マグネシア、二酸化チタン、ガラス、カオリン、ケイ酸塩、酸化クロム、酸化ホウ素、ジルコニア、クレー、ポリビニルアルコール、カーボン、ポリアミド、ポリスチレン、ポリアクリレート及びポリアクリルアミドを含む群から選ばれることができない前記光学活性支持体。
- 固体支持体が特にポリ(置換スチレン)、ポリオレフィン、ポリビニルエーテル、ポリアルキルビニルケトン、ポリアルキン、ポリイソシアネート、ポリイソニトリル、ポリオキシラン、ポリチイラン、ポリアジリジン、ポリエステル、ポリチオエステル、ポリウレタン、ポリ尿素、ポリスルホンアミド、フェノール/ホルムアルデヒド樹脂、ポリアセナフチレン、ポリ(アクリルアミド-アクリル酸)、ポリ-(2-アクリルアミド-ジアリルジメチルアンモニウムクロリド)、ポリ-(2-アクリルアミド-2-メチル-1-プロパンスルホン酸)、ポリ-(2-アクリルアミド-2-メチル-1-プロパンスルホン酸-アクリロニトリル)、ポリ(2-アクリルアミド-2-メチル-1-プロパンスルホン酸-スチレン)、ポリ(アクリル酸)、ポリ(アクリル酸-アクリルアミド)、ポリ(アクリル酸-マレイン酸)、グラフトされ、架橋されたポリ(アクリル酸)ポリ(エチレンオキサイド)、網状ポリアクリル酸-相互網状ポリシロキサン、ポリアクリロニトリル、ポリ(アクリロニトリル-ブタジエン)、ポリ(アクリロニトリル-ブタジエン-アクリル酸)、ポリ(アクリロニトリル-ブタジエン-スチレン)、ポリ(アクリロニトリル-メタクリロニトリル)、ポリ(アクリロニトリル-メチルアクリレート)、ポリ(アクリロニトリル-塩化ビニリデン-メチルメタクリレート)、ポリ(アリルアミン)、ポリ(アミド-イミド)、ポリアニリン、ポリ(アスパラギン酸)、ポリ(無水アゼライン酸)、ポリアジリジン、ポリ(ベンジルメタクリレート)、ポリ(ビスフェノールAカーボネート)、ポリ(ビスフェノールA-エピクロロヒドリン)、ポリ(4-ブロモスチレン)、ポリ(1-ブテン)、ポリ(tert-ブチルアクリレート-エチルアクリレート-メタクリル酸)、ポリ(1,4-ブチレンアジペート)、ポリ(1,4-ヘキサフルオロ-プロピレン)、ポリ(ビニルメチルケトン)、ポリ(1-ビニルナフタレン)、ポリ(ビニルフェニルケトン)、ポリ(4-ビニルピリジン-スチレン-ジビニルベンゼン)、ポリビニルピロリドン、ポリビニルピロリドン-スチレン-ジビニルベンゼン、ポリビニルトルエン、ポリアミド6、ポリアミド6D、ポリアミド6DF、ポリ(ビニルアルコール-ジビニル-エチレン尿素)、(2-ブロモエチル)-ポリスチレン、〔2-(6,6’-ジエトキシヘキサノイルアミノ)エチル〕-ポリスチレン、〔2-(スクシニルアミノ)エチル〕-ポリスチレン、2-〔4(ヒドロキシメチル)フェノキシアセトアミド〕-エチル-ポリスチレン、(アミノメチル)-ポリスチレン、(アミノエチル)-ポリスチレン、ポリ〔(4-マレイドブチルアミドメチル)-スチレン-ジビニルベンゼン〕、ポリ〔(2,3-ジヒドロキシ 1-プロピル チオメチルチオメチル)スチレン-ジビニル〕ベンゼン、ポリ(N-アクリロイル-2-アミノ-2-ヒドロキシル-1,3-プロパンジオール)、ポリアクリロイルモルホリン、ポリアクリロイルトリヒドロキシメチルアクリルアミド及びポリジメチルアクリルアミド、多糖、例えば、セルロース、アガロース、デキストラン、キトサン又はそれらの誘導体、例えば、セルロースアセテート又はセルローストリアセテート、架橋多糖、例えば、2官能性薬剤、例えば、エピクロロヒドリン、エチレングリコール-ジグリシジルエーテル、ジビニルスルホン又は2,3-ジブロモプロパノールで架橋された、セルロース、アガロース、デキストラン、シクロデキストリン、キトサン、澱粉、又はそれらの誘導体だけでなく、サッカリド部分を有するコポリマー、例えば、ポリアクリルアミド/アガロース又はアリルデキストラン/アガロースを含む群から選ばれた有機ポリマーであることを特徴とする、請求項1記載の光学活性支持体。
- 固体支持体が有機源及び無機源の両方であり、有機系複合材料及び無機系複合材料の全ての既存の型、例えば、シリカ/デキストラン複合材料又はヒドロキシアパタイト/アガロース複合材料から選ばれることを特徴とする、請求項1記載の光学活性支持体。
- 固体支持体がケイ酸マグネシウム、ゼオライト、ケイソウ土、リン酸塩、例えば、カルシウム、ジルコニウム、チタン、ハフニウム、ゲルマニウム、スズ又は鉛のリン酸塩、ヒ酸塩、例えば、チタン、ジルコニウム又はスズのヒ酸塩、セラミック、例えば、二酸化チタン/酸化マグネシウム、アルミナ/シリカ及びジルコニア/シリカセラミック、アパタイト、例えば、フルオロアパタイト又はヒドロキシアパタイト及びカーボン、酸化マグネシウム、酸化クロムを含む群から選ばれることを特徴とする、請求項1記載の光学活性支持体。
- 固体支持体が1μmから10mmまでの直径を有する粒子及び1Åから4000Åまでの開口部直径を有する細孔の形態であることを特徴とする、請求項1から4のいずれか1項記載の光学活性支持体。
- 多糖又はオリゴ糖の一種以上のエステル誘導体及び/又は一種以上のカルバメート誘導体及び/又は一種以上の混合エステル及びカルバメート誘導体が下記の一般式:
PS-(OZ)n
(式中、
PSは少なくとも6オシド単位を有する多糖又はオリゴ糖を表し、
nは12から30000まで変化し、
夫々のOZ基は互いに独立にOH、-O-C(O)-NH-R又は-O-C(O)-R(式中、Rはおそらく特に硫黄、窒素、酸素、リン、塩素、フッ素、臭素、ヨウ素及びケイ素を含む群から選ばれた少なくとも1個のヘテロ原子により置換された、1〜40個の炭素原子を有するアリール基、アルカリール基又はアラルキル基だけでなく、共役系の基、例えば、ビニル及びアリルオキシフェニルを表す)を表し得る)
を有することを特徴とする、請求項1から5のいずれか1項記載の光学活性支持体。 - Rがフェニル、トリル、3,5-ジメチルフェニル、4-クロロフェニル、3,5-ジクロロフェニル及び4-tert-ブチルフェニルを含む群から選ばれることを特徴とする、請求項6記載の支持体。
- 多糖又はオリゴ糖の一種以上のエステル誘導体及び/又は一種以上のカルバメート誘導体及び/又は一種以上の混合エステル及びカルバメート誘導体が特に20〜10000の平均重合度を有する、セルロース、アミロース、澱粉、キトサン、並びにα、β及びγ-シクロデキストリンを含む群から選ばれた多糖又はオリゴ糖の誘導体であることを特徴とする、請求項1から7のいずれか1項記載の支持体。
- 多糖又はオリゴ糖の一種以上のエステル誘導体及び/又は一種以上のカルバメート誘導体及び/又は一種以上の混合エステル及びカルバメート誘導体が合計質量の2〜70%に相当することを特徴とする、請求項1から8のいずれか1項記載の支持体。
- 多糖又はオリゴ糖の一種以上のエステル誘導体及び/又は一種以上のカルバメート誘導体及び/又は一種以上の混合エステル及びカルバメート誘導体が有機源及び/又は無機源の支持体に共有結合により結合されず、かつ互いに化学的に結合されないことを特徴とする、請求項1から9のいずれか1項記載の光学活性支持体。
- 固体支持体が更に酸化クロム、酸化ホウ素、ケイ酸アルミニウム、クレー、カーボン、ポリアミド又はポリビニルアルコールであってもよいことを特徴とする、請求項10記載の光学活性支持体。
- 多糖又はオリゴ糖の一種以上のエステル誘導体及び/又は一種以上のカルバメート誘導体及び/又は一種以上の混合エステル及びカルバメート誘導体が有機源及び/又は無機源の支持体に化学共有結合により結合され、固体支持体がおそらく既に2官能性薬剤で化学的に変性されていることを特徴とする、請求項1から9のいずれか1項記載の光学活性支持体。
- 固体支持体が更にクレー、カーボン、ポリアミド又はポリビニルアルコールであってもよいことを特徴とする、請求項12記載の光学活性支持体。
- 多糖又はオリゴ糖の一種以上のエステル誘導体及び/又は一種以上のカルバメート誘導体及び/又は一種以上の混合エステル及びカルバメート誘導体が有機源及び/又は無機源の支持体に共有結合により結合されず、かつ互いに化学的に結合されることを特徴とする、請求項1から9のいずれか1項記載の光学活性支持体。
- 固体支持体が更にケイ酸アルミニウム、酸化クロム、酸化ホウ素又はポリアミドであってもよいことを特徴とする、請求項14記載の光学活性支持体。
- 多糖又はオリゴ糖の一種以上のエステル誘導体及び/又は一種以上のカルバメート誘導体及び/又は一種以上の混合エステル及びカルバメート誘導体が有機源及び/又は無機源の支持体に化学共有結合により結合され、かつ互いに化学的に結合されることを特徴とする、請求項1から9のいずれか1項記載の光学活性支持体。
- 固体支持体が更にケイ酸アルミニウム、酸化クロム又は酸化ホウ素であってもよいことを特徴とする、請求項16記載の光学活性支持体。
- 式(I)の多糖又はオリゴ糖の一種以上のエステル誘導体及び/又は一種以上のカルバメート誘導体及び/又は一種以上の混合エステル及びカルバメート誘導体をプロトン性又は非プロトン性の極性有機溶媒に溶解し、
得られた溶液に、おそらく2官能性薬剤で前もって化学的に変性された、固体支持体を添加し、得られた懸濁液を完全に均一にし、
溶媒を常圧及び/又は真空下で、室温から約100℃までの範囲の温度で蒸発させ、又は一般式Iの誘導体の非溶媒を先の工程で得られた懸濁液に穏やかに添加し、
得られた鏡像体選択的クロマトグラフィー支持体を室温で、又は常圧もしくは真空下で加熱することにより乾燥させることからなる連続工程を含む、請求項1から17のいずれか1項記載の光学活性支持体の調製方法であって、該方法は、乾燥工程の前又は後に、固体支持体と多糖又はオリゴ糖の誘導体の間に共有結合を生じ、かつ/又は多糖又はオリゴ糖の誘導体を一緒に架橋することからなる追加の工程を含むことが更に可能である前記調製方法。 - 有機分子、無機分子又は有機-無機分子を含む群から選ばれた少なくとも2種の成分の混合物から、これらの成分のうちの一種の少なくとも一部を取り出すため、又は前記成分をクロマトグラフィー技術により分離するための、請求項1から17のいずれか1項記載の光学活性支持体又は請求項18記載の方法により調製された光学活性支持体の使用。
- 有機分子、無機分子又は有機-無機分子を含む群から選ばれた、少なくとも2種の鏡像体の混合物から、これらの成分のうちの一種の少なくとも一部を取り出して、その混合物を鏡像体の一種について濃縮し、こうして濃縮された別の鏡像体、即ち、初期の混合物の旋光能より大きい旋光能を有する鏡像体を得るための、請求項1から17のいずれか1項記載の光学活性支持体又は請求項18記載の方法により調製された光学活性支持体の使用。
- 鏡像体をクロマトグラフィー技術により分離するための、請求項1から17のいずれか1項記載の光学活性支持体又は請求項18記載の方法により調製された光学活性支持体の使用。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0116933A FR2834227A1 (fr) | 2001-12-27 | 2001-12-27 | Materiaux supports optiquement actifs, leur procede de preparation et leurs utilisations |
PCT/FR2002/004391 WO2003055594A2 (fr) | 2001-12-27 | 2002-12-17 | Materiaux supports optiquement actifs, leur procede de prepartion et leurs utilisations |
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EP (1) | EP1458475A2 (ja) |
JP (1) | JP2005513492A (ja) |
KR (1) | KR20040078656A (ja) |
CN (1) | CN1617762A (ja) |
AU (1) | AU2002364659B2 (ja) |
FR (1) | FR2834227A1 (ja) |
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WO2010148191A2 (en) * | 2009-06-17 | 2010-12-23 | Board Of Regents, The University Of Texas System | Compositions and methods for cyclofructans as separation agents |
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US9592540B2 (en) | 2011-02-02 | 2017-03-14 | Bio-Rad Laboratories, Inc. | Apatite surface neutralization with alkali solutions |
CN102205770B (zh) * | 2011-03-16 | 2013-09-25 | 北京培宏望志科技有限公司 | 将平面图片中的影像做成立体实物的方法 |
US9815695B2 (en) | 2012-05-30 | 2017-11-14 | Bio-Rad Laboratories, Inc. | In situ restoration of apatite-based chromatography resins |
US9302203B2 (en) * | 2012-07-20 | 2016-04-05 | Mitsubishi Chemical Corporation | Chromatographic separation material |
CN104755538B (zh) | 2012-08-17 | 2018-08-31 | Cj 第一制糖株式会社 | 用于聚合物共混物的生物基橡胶改性剂 |
CN103105442B (zh) * | 2013-01-18 | 2014-06-18 | 华侨大学 | 凝胶渗透色谱检测高分子嵌段共聚物结构参数的方法 |
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CN105531308B (zh) | 2013-05-30 | 2021-08-10 | Cj 第一制糖株式会社 | 回收物共混物 |
WO2015149029A1 (en) | 2014-03-27 | 2015-10-01 | Metabolix, Inc. | Highly filled polymer systems |
CN103962106B (zh) * | 2014-06-03 | 2016-09-14 | 湖南大学 | 一种壳聚糖/腐植酸修饰的磁性吸附剂去除废水中铅的方法 |
CN105392569B (zh) | 2014-06-23 | 2019-08-20 | 生物辐射实验室股份有限公司 | 磷灰石预处理 |
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CN107923882B (zh) * | 2015-07-31 | 2021-10-15 | 株式会社大赛璐 | 超临界流体色谱法用的固定相 |
CN106582580A (zh) * | 2016-12-22 | 2017-04-26 | 苏州楚博生物技术有限公司 | 层析柱用耐高压亲和层析介质 |
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-
2001
- 2001-12-27 FR FR0116933A patent/FR2834227A1/fr not_active Withdrawn
-
2002
- 2002-12-17 CN CNA028276299A patent/CN1617762A/zh active Pending
- 2002-12-17 EP EP02805798A patent/EP1458475A2/fr not_active Ceased
- 2002-12-17 JP JP2003556165A patent/JP2005513492A/ja active Pending
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- 2004-07-21 NO NO20043125A patent/NO20043125L/no not_active Application Discontinuation
Also Published As
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WO2003055594A2 (fr) | 2003-07-10 |
US20050209100A1 (en) | 2005-09-22 |
US7597804B2 (en) | 2009-10-06 |
EP1458475A2 (fr) | 2004-09-22 |
NO20043125L (no) | 2004-09-27 |
FR2834227A1 (fr) | 2003-07-04 |
AU2002364659B2 (en) | 2008-02-28 |
KR20040078656A (ko) | 2004-09-10 |
AU2002364659A1 (en) | 2003-07-15 |
WO2003055594A3 (fr) | 2003-12-24 |
CN1617762A (zh) | 2005-05-18 |
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