JP2017217500A - 抗酸化物質を含む皮膚充填剤組成物 - Google Patents
抗酸化物質を含む皮膚充填剤組成物 Download PDFInfo
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- JP2017217500A JP2017217500A JP2017157047A JP2017157047A JP2017217500A JP 2017217500 A JP2017217500 A JP 2017217500A JP 2017157047 A JP2017157047 A JP 2017157047A JP 2017157047 A JP2017157047 A JP 2017157047A JP 2017217500 A JP2017217500 A JP 2017217500A
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Abstract
【解決手段】ヒアルロン酸と、前記ヒアルロン酸に共有結合されたビタミンC誘導体とを含み、結合度が約3モル%〜約40モル%である、注入可能な皮膚充填剤。
【選択図】なし
Description
本出願は、2011年6月3日出願の米国仮特許出願第61/493,309号に対する優先権およびその利益を主張するものであり、この全開示は、この参照により本明細書に組み込まれる。
1つの実施形態において、組成物は、非架橋結合グリコサミノグリカン重合体を含み、ここでその非架橋結合グリコサミノグリカン重合体は本明細書中に開示されるように皮膚状態を改善するのに十分な量で存在する。この実施形態の態様において、組成物は、非架橋結合グリコサミノグリカンを含み、ここでその非架橋結合グリコサミノグリカンは、例えば、約2mg/g、約3mg/g、約4mg/g、約5mg/g、約6mg/g、約7mg/g、約8mg/g、約9mg/g、約10mg/g、約11mg/g、約12mg/g、約13mg/g、約13.5mg/g、約14mg/g、約15mg/g、約16mg/g、約17mg/g、約18mg/g、約19mg/g、約20mg/g、約40mg/g、または約60mg/gの濃度で存在する。この実施形態の他の態様において、組成物は、非架橋結合グリコサミノグリカンを含み、ここでその非架橋結合グリコサミノグリカンは、例えば、少なくとも1mg/g、少なくとも2mg/g、少なくとも3mg/g、少なくとも4mg/g、少なくとも5mg/g、少なくとも10mg/g、少なくとも15mg/g、少なくとも20mg/g、少なくとも25mg/g、少なくとも35mg/g、または少なくとも40mg/gの濃度で存在する。この実施形態のさらに他の態様において、組成物は、非架橋結合グリコサミノグリカンを含み、ここでその非架橋結合グリコサミノグリカンは、例えば、最大1mg/g、最大2mg/g、最大3mg/g、最大4mg/g、最大5mg/g、最大10mg/g、最大15mg/g、最大20mg/g、または最大25mg/gの濃度で存在する。この実施形態のさらに他の態様において、組成物は、非架橋結合グリコサミノグリカンを含み、ここでその非架橋結合グリコサミノグリカンは、例えば、約1mg/g〜約60mg/g、約10mg/g〜約40mg/g、約7.5mg/g〜約19.5mg/g、約8.5mg/g〜約18.5mg/g、約9.5mg/g〜約17.5mg/g、約10.5mg/g〜約16.5mg/g、約11.5mg/g〜約15.5mg/g、または約12.5mg/g〜約14.5mg/gの濃度で存在する。
**仮定:
・AsAは一定の速度で放出される。
・AsAの有効な濃度は0.05mMであり、そして2日間超、有効性を維持する。2.13*2/(0.05*30)=2.8(ヶ月)
実施例
400.6mgのLMW HAをシリンジ中の1802mgの1重量%NaOH中で約30分間水和した。800.7mgのAA2G、続いて713.7mgのBDDE、および1416.8mgの10%NaOHをバイアル中に入れた。上記溶液(pH12超)を50℃の水浴中で約20分間反応させ、その後上記水和HAに添加した。その添加後、その混合物を2つのシリンジ間を行ったり来たりさせることにより約20回混合した。その混合ペーストをバイアル中に入れ、そして50℃の水浴中に約2.5時間入れた。223.5mgの12M HClを9.05gのPBS(pH7.4)に添加した。約2.5時間後、HA‐AA2Gゲルが形成された。そのゲルを切断して断片にし、そしてHCl‐PBS溶液をそれに添加した。そのゲルを中和させ、そして環状振騰器上で一晩膨潤させた。そのゲルを、約60μmスクリーンをとおしてふるいにかけ、そして2つのシリンジ間を行ったり来たりさせることにより約20回混合した。そのゲルを15,000MWCO RC透析バッグ中に入れ、PBS緩衝液(pH7.4)中で透析した。その透析を、PBS緩衝液を頻繁に交換しながら約185時間続けた。その透析後、そのゲルをシリンジ中に入れ、そして4℃の冷蔵庫内で貯蔵した。
実施例1中に示されるようなゲルの重量を透析直前、および透析後に決定した。そのゲルが透析後に約1g/mLであったと仮定した。透析を、1LのPBS中で8時間超あたりに顕著なAA2Gが出てこなくなった点で止めた。そのAA2GをUV/Vis分光光度計(Nanodrop 2000C、ThermoScientific)を用いて260nmで計測した。AA2Gの較正曲線を2%HA中の様々な濃度のAA2Gを用いて計算した(260nmでの吸収=1.4838[AA2G(mM)])。
透析後のHAの重量:HAの出発重量×(透析前の実際の重量/理論的重量)
透析後のAA2Gのmmol:式(260nmでの吸収=1.4838[AA2G(mM)])中に透析後の260nmでの吸収を入れた。
AA2Gでの結合:(AA2G(mmol)/HA(mmol))×100%
実施例1中に示されるようなゲル中のAA2G結合度は14.7モル%である。
振動平行プレートレオメータ(Anton Paar, Physica MCR 301)を実施例1中で得られたゲルの特性を計測するために使用した。使用されたプレートの直径は25mmであった。そのプレート間のギャップを1mmに設定した。各計測について、一定の歪みでの周波数掃引をはじめに、その後、固定周波数での歪み掃引を行った。G’(貯蔵弾性率)を1%の歪みでの歪み掃引曲線から得た。そのゲルについてのその値は1450Paである。
本手順は実施例1中に示されるものと類似した。結合度は架橋剤対HAおよびAA2Gモル率を調整することにより改変される。ゲル特性を実施例3中に示されるように計測した。詳細は以下のとおりである。
400.8mgのLMW HAをシリンジ中の1752.1mgの1%NaOH中で約30分間水和した。800.3mgのAA2G、続いて354.1mgのBDDE、および1402.0mgの10%NaOHをバイアル中に入れた。上記溶液(pH12超)を50℃の水浴中で約20分間反応させ、その後上記水和HAに添加した。その添加後、その混合物を2つのシリンジ間を行ったり来たりさせることにより約20回混合した。その混合ペーストをバイアル中に入れ、そして50℃の水浴中に約2.5時間入れた。140.9mgの12M HClを9.0053gのPBS(pH7.4)に添加した。約2.5時間後、HA‐AA2Gゲルが形成された。そのゲルを切断して断片にし、HCl‐PBS溶液をそれに添加した。そのゲルを中和させ、そして環状振騰器上で一晩膨潤させた。そのゲルを、約60μmスクリーンをとおしてふるいにかけ、そして2つのシリンジ間を行ったり来たりさせることにより約20回混合した。そのゲルを15,000MWCO RC透析バッグ中に入れ、PBS緩衝液(pH7.4)中で透析した。その透析を、PBS緩衝液を頻繁に交換しながら約164.5時間続けた。その透析後、そのゲルをシリンジ中に入れ、そして4℃の冷蔵庫内で貯蔵した。結合度は13%である。ゲル貯蔵弾性率(G’)は、803Paである。
400.3mgのLMW HAをシリンジ中の3002.0mgの1%NaOH中で約30分間水和した。800.5mgのAA2G、続いて264.3mgのBDDE、および1100.0mgの10%NaOHをバイアル中に入れた。上記溶液(pH12超)を50℃の水浴中で約20分間反応させ、その後上記水和HAに添加した。その添加後、その混合物を2つのシリンジ間を行ったり来たりさせることにより約20回混合した。その混合ペーストをバイアル中に入れ、そして50℃の水浴中に約2.5時間入れた。104.2mgの12M HClを8.5128gのPBS(pH7.4)に添加した。約2.5時間後、HA‐AA2Gゲルが形成され、そしてHCl‐PBS溶液をそれに添加した。そのゲルを中和させ、そして環状振騰器上で週末にかけて(約55時間)膨潤させた。そのゲルを、約60μmスクリーンをとおしてふるいにかけ、そして2つのシリンジ間を行ったり来たりさせることにより約20回混合した。そのゲルを15,000MWCO RC透析バッグ中に入れ、PBS緩衝液(pH7.4)中で透析した。その透析を、PBS緩衝液を頻繁に交換しながら約114時間続けた。その透析後、そのゲルをシリンジ中に入れ、そして4℃の冷蔵庫内で貯蔵した。結合度およびゲル流体力学的特性を実施例2および3中に示されるような手順で計測する。結合度は5.3%である。ゲル貯蔵弾性率は約300Paである。
200.4mgのLMW HAをシリンジ中の2000mgの1%NaOH中で約30分間水和した。400mgのAA2G、続いて312.7mgのstar‐PEGエポキシド、および1026.5mgの10%NaOHをバイアル中に入れた。上記溶液を50℃の水浴中で約20分間反応させ、その後上記水和HAに添加した。その添加後、その混合物を2つのシリンジ間を行ったり来たりさせることにより約20回混合した。その混合ペーストをバイアル中に入れ、そして50℃の水浴中に約2.5時間入れた。187.4mgの12M HClを3.034gのPBS(pH7.4)に添加した。約2.5時間後、HA‐AA2Gゲルが形成され、そしてHCl‐PBS溶液をそれに添加した。そのゲルを中和させ、そして環状振騰器上で週末にかけて(約68時間)膨潤させた。そのゲルを、約60μmスクリーンをとおしてふるいにかけ、そして2つのシリンジ間を行ったり来たりさせることにより約20回混合した。そのゲルを15,000MWCO RC透析バッグ中に入れ、PBS緩衝液(pH7.4)中で透析した。その透析を、PBS緩衝液を頻繁に交換しながら約95時間続けた。その透析後、そのゲルをシリンジ中に入れ、そして4℃の冷蔵庫内で貯蔵した。結合度およびゲル流体力学的特性は実施例2および3中に示されるような手順で計測される。結合度は29.4%である。ゲル貯蔵弾性率は約235Paである。
200.3mgのLMW HAをシリンジ中の2000mgの1%NaOH中で約30分間水和した。400.2mgのAA2G、続いて313.4mgのstar‐PEGエポキシド、および1022.6mgの10%NaOHをバイアル中に入れた。上記溶液を上記水和HAに添加した。その添加後、その混合物を2つのシリンジ間を行ったり来たりさせることにより約20回混合した。その混合ペーストをバイアル中に入れ、そして50℃の水浴中に約2.5時間入れた。196.5mgの12M HClを3.016gのPBS(pH7.4)に添加した。約2.5時間後、HA‐AA2Gゲルが形成され、そして上記HCl‐PBS溶液をそれに添加した。そのゲルを中和させ、そして環状振騰器上で一晩(約24時間)膨潤させた。そのゲルを、約60μmスクリーンをとおしてふるいにかけ、そして2つのシリンジ間を行ったり来たりさせることにより約20回混合した。そのゲルを15,000MWCO RC透析バッグ中に入れ、PBS緩衝液(pH7.4)中で透析した。その透析を、PBS緩衝液を頻繁に交換しながら約98.5時間続けた。その透析後、そのゲルをシリンジ中に入れ、そして4℃の冷蔵庫内で貯蔵した。結合度およびゲル流体力学的特性を実施例2および3中に示されるような手順で計測する。結合度は27.8%である。ゲル貯蔵弾性率は約363Paである。
400.3mgのHMW HAをシリンジ中の2501.3mgの4重量%NaOH中で約30分間水和した。1200mgのAA2G、続いて304.7mgのBDDE、および1178.6mgの16重量%NaOHをバイアル中に入れた。上記溶液(pH12超)を50℃の水浴中で約20分間反応させ、そして20ccのシリンジに移し、その後上記水和HAに添加した。その添加後、その混合物を2つのシリンジ間を行ったり来たりさせることにより約20回混合した。その混合ペーストを20ccのバイアル中に入れ、そして50℃の水浴中に約2.5時間入れた。約2.5時間後、HA‐AA2Gゲルが形成された。その後、226.6mgの12M HClを8492.2mgの10倍PBS(pH7.4)に添加し、HCl‐PBS溶液を得、そのHCl‐PBS溶液を、上記ゲルを中和させ、膨潤させるために添加した。そのゲルを環状振騰器上で48時間にわたり、中和させ、そして膨潤させた。そのゲルを、約60μmスクリーンをとおしてふるいにかけ、そして2つのシリンジ間を行ったり来たりさせることにより約20回混合した。そのゲルを20,000MWCO CE透析バッグ中に入れ、PBS緩衝液(pH7.4)中で透析した。その透析を、PBS緩衝液を頻繁に交換しながら約114時間続けた。その透析後、そのゲルをシリンジ中に入れ、そして4℃の冷蔵庫内で貯蔵した。結合度およびゲル流体力学的特性を実施例2および3中に示されるような手順で計測する。結合度は5.3%である。ゲル貯蔵弾性率は約300Paである。
398.2mgのLMW HAをシリンジ中の1753.24mgの1重量%NaOH中で約40分間水和した。BDDE(311.7mg)を膨潤したHAに添加し、そしてHAをさらなる80分間、膨潤させ続けた。膨潤したHA/BDDE混合物を50℃で20分間予め反応させた。
801.9mgのビタゲンを1459.7mgの10重量%NaOH中で別に溶解し、そしてBDDEと予め反応させたHAと混合した。その混合物を50℃でさらなる2.5時間、反応させ続けた。約2.5時間後、HA‐ビタゲンゲルが形成された。その後、195mgの12M HClを9004.0mgの10倍PBS(pH7.4)に添加し、HCl‐PBS溶液を得、そしてそのHCl‐PBS溶液を、上記ゲルを中和させ、そして膨潤させるために添加した。そのゲルを環状振騰器上で48時間にわたり、中和させ、そして膨潤させた。そのゲルを、約60μmスクリーンをとおしてふるいにかけ、そして2つのシリンジ間を行ったり来たりさせることにより約20分間混合した。そのゲルを20,000MWCO CE透析バッグ中に入れ、PBS緩衝液(pH7.4)中で透析した。その透析を、PBS緩衝液を頻繁に交換しながら約120時間続けた。その透析後、そのゲルをシリンジ中に入れ、そして4℃の冷蔵庫内で貯蔵した。そのゲルの流体力学的特性を実施例3中に示されるような手順で計測した。結合度は物質収支により約15モル%と計算される。ゲル貯蔵弾性率は約365Paである。
200.3mgのHMW HAを60ccのシリンジ中の10mLの水中で水和した。500mgのビタゲンを0.5mLの水中に溶解し、そして溶液をpH4.8まで中和した。197.7mgのEDCおよび149mgのNHSを6mLの水中で別に溶解した。上記溶液(溶液およびEDC/NHS溶液)を23.5mLの水を含有する別の60ccシリンジに添加する。その2つのシリンジを、2つのシリンジ間を行ったり来たりさせることにより20回混合する。その混合物を1つのシリンジ中で貯蔵し、そして37℃浴中に4時間浸した。最後に、その溶液を、顕著なビタゲンが観察されなくなるまで、PBS緩衝液(pH7.4)に対して透析した。結合度を、示される実施例3と類似の方法により決定した。結合度は約10モル%である。
200.4mgのLMW HAをシリンジ中の1000mgのMES 5.2緩衝液中で約30分間水和する。292mgのAA2Pをバイアル中に入れ、続いて300mgのstar‐PEGアミンを添加する。上記溶液を室温で一晩反応させる。そのゲルをPBS緩衝液で水和し、PBS緩衝液に対して透析し、未反応のAA2Pを除去した。最終的なゲルを実施例2および3中に示されるように特徴付け、結合度およびゲル流体力学的特性を決定した。結合度は約20モル%である。貯蔵弾性率(G’)は約500Paである。
上記実施例中に示されるゲルのいずれにも、透析後、好適な量の遊離HAゲルが、ゲルの粘着性および/または注入可能性を改善改変するよう、そのゲルに添加され得る。例えば、均一な粘弾性ゲル(「遊離」HAゲル)を得るために、遊離HA繊維をリン酸緩衝液中で膨潤させる。(例えば、約1w/w%〜約5w/w%の遊離HAを有する組成物を得るために)この非架橋結合ゲルは透析ステップ前に、実施例1中で得られたHA/BDDE架橋結合ゲルに添加される。生じるゲルをその後、処理済み滅菌シリンジ中に満たし、そして滅菌のために十分な温度および圧で少なくとも約1分間オートクレーブにかける。オートクレーブ後、最終的なHA‐AA2G製品を包装し、そして皮膚充填剤として使用するために医師に配布する。
実施例12の手順に従う、ただし、透析ステップ後、かつ遊離HAゲル添加前に、リドカインクロル水和物(リドカインHCl)をその混合物に添加する。粉末形態のリドカインHClははじめにWFI中で可溶化され、そして0.2μmフィルターをとおしてろ過され得る。希釈NaOH溶液をわずかに塩基性のpH(例えば、約7.5〜約8のpH)に到達させるためにその粘着性HA‐AA2Gゲルに添加する。上記リドカインHCl溶液をその後、そのわずかに塩基性のゲルに添加し、最終的に所望される濃度、例えば、約0.3w/w%に到達させる。HA‐AA2G/リドカイン混合物の結果としてのpHは、そのとき、約7であり、そしてHA濃度は約24mg/mLである。適切なブレンダー機構を備えた標準の反応器中で、適切な均一性を得るために機械的混合を行う。
レチノイン酸(トレチノインとしても知られる)、アダパレンス(adapalence)(、およびアルファ‐リポ酸等の、添加物はカルボキシル官能基(‐COOH)を含有する。これらの添加物はEDC化学反応を用いたエステル化によりHAヒドロゲルに結合される。本発明の1つの実施形態に従う結合についての実施例は、以下のように説明される。
200mgのHMW HAを60ccシリンジ中の10mLのMES緩衝液(pH4.8)中で水和する。別のシリンジ中で、200mgのレチノイン酸を5mLの水‐アセトン混合物(水/アセトン体積率1:3)中に溶解する。上記2つのシリンジをシリンジ接続器により約20回混合する。その後、197.7mgのEDCおよび149mgのNHSを別のシリンジ中の6mLの水中で別に溶解する。EDCおよびNHSを含有するシリンジをHAおよびレチノイン酸を含有するシリンジと繋げ、2つのシリンジ間を行ったり来たりさせることにより反応物を少なくとも20回混合する。その混合物を1つのシリンジ中で貯蔵し、そして37℃浴中に4時間浸す。そのゲルをイソプロパノールに対して透析し、未結合のレチノイン酸を除去し、そしてその後、無菌条件下でPBS緩衝液に対して透析する。そのゲルを滅菌シリンジ中に包装し、そして4℃で貯蔵する。
レチノール(トレチノインとしても知られる)、カタラーゼ、ジメチルアミノエタノール、およびg‐トコフェロール等の添加物はヒドロキシル官能基(‐OH)を含有する。これらの添加物はEDC化学反応を用いたエステル化によりHAヒドロゲルに結合される。結合についての典型的な実施例は、以下のように説明される。
200mgのHMW HAを60ccのシリンジ中の10mLの2‐(N‐モルホリノ)エタンスルホン酸(MES)緩衝液(pH4.8)中で水和する。別のシリンジ中で、200mgのレチノール酸を5mLの水‐アセトン混合物(水/アセトン体積率1:3)中に溶解する。上記2つのシリンジをシリンジ接続器により約20回混合する。その後、197.7mgのEDCおよび149mgのNHSを別のシリンジ中の6mLの水中で別に溶解する。EDCおよびNHSを含有するシリンジをHAおよびレチノールを含有するシリンジに繋げ、2つのシリンジ間を行ったり来たりさせることにより反応物を少なくとも20回混合する。その混合物を1つのシリンジ中で貯蔵し、そして37℃浴中に4時間浸す。そのゲルをイソプロパノールに対して透析し、未結合のレチノールを除去し、そしてその後、無菌(aspect)条件下でPBS緩衝液に対して透析する。そのゲルを滅菌シリンジ中に包装し、そして4℃で貯蔵する。
これは2つのステップのプロセスである。ステップ1:HAヒドロゲル、例えば、ジュビダームまたはレスチラン(restylane)をEDC/NHSで処理し、HAのカルボキシル基を活性化する。ステップ2:活性化されたHAヒドロゲルを、ヒドロキシル基を含有する添加物で処理する。ヒドロキシル基を含有する添加物はレチノール、カタラーゼ、ジメチルアミノエタノール、およびg‐トコフェロールヒドロキシル官能基(‐OH)である。架橋結合されたHAゲルへの添加物の結合についての典型的な実施例は、以下のとおりである。
2gmのジュビダームゲルを200gmのEDCおよび150mgのNHSと室温で混合する。その後、3mLのアセトン‐水混合物中の200mgのレチノールを添加する。上記混合物を37℃で4時間反応させる。そのゲルをイソプロパノールに対して透析し、未結合のレチノールを除去し、そしてその後、無菌条件下でPBS緩衝液に対して透析する。そのゲルを滅菌シリンジ中に包装し、そして4℃で貯蔵する。
官能アミン基を含有する、上皮増殖因子(EGF)、形質転換増殖因子(TGF)、およびペプチド等の、添加物はHAに結合され、有益な皮膚充填剤を形成し得る。これらの添加物はアミド化化学反応によりHAに結合される。結合についての典型的な実施例は、以下のように説明される。
200.3mgのHMW HAを10mLのMES緩衝水(pH5.4)中で水和する。100mgのMES溶液中の20mgのEGFを添加する。上記混合物に、197.7mgのEDCおよび149mgを添加する。生じる反応混合物を37℃で4時間反応させる。反応完了後、そのゲルをイソプロパノールに対してさらに透析し、そしてその後、無菌条件下でPBS緩衝液に対して透析する。そのゲルを滅菌シリンジ中に包装し、4℃で貯蔵する。
[1]
ヒアルロン酸と、
前記ヒアルロン酸に共有結合されたビタミンC誘導体と、
を含み、
結合度が、約3モル%〜約40モル%である、注入可能な皮膚充填剤。
[2]
前記ヒアルロン酸が、Star‐PEGエポキシドと架橋結合される、[1]に記載の皮膚充填剤。
[3]
前記ヒアルロン酸が、Star‐PEGアミンと架橋結合される、[1]に記載の皮膚充填剤。
[4]
前記ヒアルロン酸が、BDDEと架橋結合される、[1]に記載の皮膚充填剤。
[5]
前記結合度が、約3モル%〜約15モル%である、[4]に記載の皮膚充填剤。
[6]
ビタミンC誘導体が、AA2Gである、[1]に記載の皮膚充填剤。
[7]
前記ビタミンC誘導体が、ビタゲンである、[1]に記載の皮膚充填剤。
[8]
前記ビタミンC誘導体が、AA2Pである、[1]に記載の皮膚充填剤。
[9]
ヒトの皮膚に導入されたときに、少なくとも約1ヶ月〜最大約20ヶ月間、前記ヒトにアスコルビン酸を放出する、皮膚欠損の治療に使用される[1]に記載の皮膚充填剤。
[10]
Star PEGアミンと架橋結合され、かつ約3モル%〜約40モル%の結合度を有するヒアルロン酸と、
前記ヒアルロン酸に共有結合されたAA2Pと、
を含み、
前記皮膚充填剤が、ヒトの皮膚に導入されたときに、少なくとも約1ヶ月〜最大約20ヶ月間、前記ヒトにアスコルビン酸を放出する、注入可能な皮膚充填剤。
[11]
皮膚充填剤を作製する方法であって、
ヒアルロン酸を提供するステップと、
架橋剤をビタミンC誘導体と反応させるステップと、
前記反応した架橋剤およびビタミンC誘導体を前記ヒアルロン酸に添加して、共有結合されたビタミンCを含む架橋結合されたヒアルロン酸組成物を形成するステップと、
前記架橋結合されたヒアルロン酸組成物を均質化および中和して、約3モル%〜約40モル%の結合度を有する注入可能なゲルを得るステップと、
を含む、方法。
[12]
前記反応させるステップが、ビタミンC誘導体を架橋剤と予め反応させて、架橋剤によってキャップされたビタミンC誘導体、未反応の架橋剤、および遊離AA2Gを含有する組成物を得ることを含む、[11]に記載の方法。
[13]
前記架橋剤が、BDDEであり、ビタミンC誘導体が、AA2G、ビタゲン、およびSAPである、[12]に記載の方法。
[14]
前記架橋剤が、4‐アームエポキシドであり、ビタミンC誘導体が、AA2G、ビタゲン、およびSAPである、[12]に記載の方法。
[15]
前記架橋剤が、Star‐PEGエポキシドである、[11]に記載の方法。
[16]
前記架橋剤が、Star‐PEGアミンである、[11]に記載の方法。
[17]
ビタミンC誘導体が、AA2Gである、[11]に記載の方法。
[18]
前記ビタミンC誘導体が、ビタゲンである、[11]に記載の方法。
[19]
前記ビタミンC誘導体が、AA2Pである、[11]に記載の方法。
[20]
[1]に記載の皮膚充填剤を患者に導入することを含む、皮膚状態を治療する方法。
最後に、本明細書の態様が様々な実施形態について示されているが、当業者は開示される特定の実施例が本明細書中に開示される発明の原理の単に例示であることを容易に理解するであろうことが理解されるべきである。それゆえ、開示される発明は本明細書中に示される特定の方法、プロトコル、および/または試薬等に決して限定されないことが理解されるべきである。よって、本明細書の精神から離れることなく、当業者は多くのおよび様々な改変または変化を作出し得る、あるいは、開示される発明の代替の構成は本明細書中の教示に従ってなされ得る。詳細における変化は付属の請求項中に定義されるような本発明の精神から離れることなく、なされ得る。最後に、本明細書中で使用される用語は特定の実施形態を説明する目的のためのみであり、そして請求項によってのみ定義される本発明の範囲を限定するとは意図されない。さらに、上記説明中に含有される、または付属の図面中に示される全ての事柄は単に例示として、および限定ではないと解釈されるべきであることが意図される。したがって、本発明は示されるおよび説明されるとおりの正確なものに限定されない。
Claims (20)
- ヒアルロン酸と、
前記ヒアルロン酸に共有結合されたビタミンC誘導体と、
を含み、
結合度が、約3モル%〜約40モル%である、注入可能な皮膚充填剤。 - 前記ヒアルロン酸が、Star‐PEGエポキシドと架橋結合される、請求項1に記載の皮膚充填剤。
- 前記ヒアルロン酸が、Star‐PEGアミンと架橋結合される、請求項1に記載の皮膚充填剤。
- 前記ヒアルロン酸が、BDDEと架橋結合される、請求項1に記載の皮膚充填剤。
- 前記結合度が、約3モル%〜約15モル%である、請求項4に記載の皮膚充填剤。
- ビタミンC誘導体が、AA2Gである、請求項1に記載の皮膚充填剤。
- 前記ビタミンC誘導体が、ビタゲンである、請求項1に記載の皮膚充填剤。
- 前記ビタミンC誘導体が、AA2Pである、請求項1に記載の皮膚充填剤。
- ヒトの皮膚に導入されたときに、少なくとも約1ヶ月〜最大約20ヶ月間、前記ヒトにアスコルビン酸を放出する、皮膚欠損の治療に使用される請求項1に記載の皮膚充填剤。
- Star PEGアミンと架橋結合され、かつ約3モル%〜約40モル%の結合度を有するヒアルロン酸と、
前記ヒアルロン酸に共有結合されたAA2Pと、
を含み、
前記皮膚充填剤が、ヒトの皮膚に導入されたときに、少なくとも約1ヶ月〜最大約20ヶ月間、前記ヒトにアスコルビン酸を放出する、注入可能な皮膚充填剤。 - 皮膚充填剤を作製する方法であって、
ヒアルロン酸を提供するステップと、
架橋剤をビタミンC誘導体と反応させるステップと、
前記反応した架橋剤およびビタミンC誘導体を前記ヒアルロン酸に添加して、共有結合されたビタミンCを含む架橋結合されたヒアルロン酸組成物を形成するステップと、
前記架橋結合されたヒアルロン酸組成物を均質化および中和して、約3モル%〜約40モル%の結合度を有する注入可能なゲルを得るステップと、
を含む、方法。 - 前記反応させるステップが、ビタミンC誘導体を架橋剤と予め反応させて、架橋剤によってキャップされたビタミンC誘導体、未反応の架橋剤、および遊離AA2Gを含有する組成物を得ることを含む、請求項11に記載の方法。
- 前記架橋剤が、BDDEであり、ビタミンC誘導体が、AA2G、ビタゲン、およびSAPである、請求項12に記載の方法。
- 前記架橋剤が、4‐アームエポキシドであり、ビタミンC誘導体が、AA2G、ビタゲン、およびSAPである、請求項12に記載の方法。
- 前記架橋剤が、Star‐PEGエポキシドである、請求項11に記載の方法。
- 前記架橋剤が、Star‐PEGアミンである、請求項11に記載の方法。
- ビタミンC誘導体が、AA2Gである、請求項11に記載の方法。
- 前記ビタミンC誘導体が、ビタゲンである、請求項11に記載の方法。
- 前記ビタミンC誘導体が、AA2Pである、請求項11に記載の方法。
- 請求項1に記載の皮膚充填剤を患者に導入することを含む、皮膚状態を治療する方法。
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