JP4987715B2 - 上皮関連状態のための局所用組成物及び方法 - Google Patents
上皮関連状態のための局所用組成物及び方法 Download PDFInfo
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- JP4987715B2 JP4987715B2 JP2007527776A JP2007527776A JP4987715B2 JP 4987715 B2 JP4987715 B2 JP 4987715B2 JP 2007527776 A JP2007527776 A JP 2007527776A JP 2007527776 A JP2007527776 A JP 2007527776A JP 4987715 B2 JP4987715 B2 JP 4987715B2
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- acid
- polyisoprenyl
- protein inhibitor
- inhibitor compound
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Description
本出願は、2004年6月12日に出願された米国仮出願第60/579,093号の優先権の利益を主張する。本出願はまた、2005年2月14日に出願された米国仮特許出願第60/652,921号の優先権の利益を主張する。米国仮特許出願第60/579,093号及び米国仮特許出願第60/652,921号の開示全体が、参照により本明細書に援用される。
R1は、炭素数1〜3のアルキルであり、
R2は、−COX(ここで、Xは、−OH、−OCH3、−NH2、−NHR4、−N(R4)2又はハロゲンである)であり、
R3は、炭素数10〜25の直鎖又は分枝鎖アルキル、炭素数10〜25の直鎖又は分枝鎖アルケニル(ポリ不飽和アルケニルを包含する)であり、
R4は、炭素数が少なくとも1〜約25のアルキルである)
により表される特許文献1に記載される化合物及びそれらの誘導体、並びにそれらのこれらの化合物の薬学的に許容可能な塩及びエステルが挙げられる。
W−Y−Q−Z (II)
又は下記式(III):
W−Y−Z (III)
(式中、Wは、ファルネシル基、ゲラニルゲラニル基、置換ファルネシル基又は置換ゲラニルゲラニル基であり、
Yは、
である)
から選択される化合物を包含する。C1...Cnは、炭素数1〜6を表すこと、及び2つ又はそれ以上の炭素が存在する場合、それらは共有結合により直鎖で結合されることが理解されよう。共有結合は、単結合、二重結合又は三重結合であり得る。3つ又はそれ以上の炭素が存在する場合、結合はすべて、同じタイプである必要はない。例えば、C1は、単結合によりC2に結合されてもよく、C2は、二重結合によりC3に結合されてもよい。二重又は三重結合が存在する場合、T1’...Tn’の2つ又はそれ以上が脱離される。T1’...Tn’及びT1”...Tn”はそれぞれ独立して、H、Fl、Br、−NHCOCH3、−NH2、ペプチド(好ましくはアミド結合によりCnに連結され、好ましくは10個又はそれ未満のアミノ酸を有する)、アルケン基(好ましくはアミド結合によりCnに連結され、好ましくは20個又はそれ未満の炭素を有する)、ポリエチレングリコール基(好ましくはアミド結合によりCnに連結される)、飽和脂肪酸(好ましくはアミド結合によりCnに連結され、好ましくは20個又はそれ未満の炭素を有する)、又は不飽和脂肪酸(好ましくはアミド結合を介してCnに連結され、好ましくは20個又はそれ未満の炭素を有する)、単糖(好ましくは炭素又は酸素を介してCnに連結される)、又は二糖(好ましくは炭素又は酸素を介してCnに連結される)であり、Zは、−COOH或いはそれらの塩又はエステル(例えば、メチル、エチル又はプロピルエステル)である。−COOH、−PO3又は−SO3のエステルは、それらが細胞によりより容易に取り込まれるため、遊離酸よりも好ましい。多くの細胞は、場合によっては好ましい遊離酸を再生することができるエステラーゼを有する。
マウス耳モデルにおいて浮腫を低減させることに関して、本発明のAFC組成物の影響を評価するために、皮膚炎症の確立モデルを使用した(非特許文献11、非特許文献12、非特許文献13、及び非特許文献14を参照)。
浮腫を誘導することが知られている化合物であるTPAに関する用量応答範囲を確定した。TPAは、浮腫(耳隆起(ear swelling:耳介腫張))の増大をもたらし、6時間で最大に達する。
ポリイソプレニル−タンパク質阻害剤化合物であるAFC5mg〜32mgをアセトン20μlと混合して、本発明のAFC組成物を作成した。各濃度の本発明のAFC組成物のそれぞれ10μlが右耳の内部耳表面へ塗布され、且つ10μlが外部耳表面へ塗布されるように、各濃度を、マイクロピペッターを活用して、6匹のマウスそれぞれの右耳へ塗布した。本発明のAFC化合物を、ピペットチップを用いて均一に広げた。各対側耳は、同じ様式でアセトンのみで処置した。続いて、マウスをマウスのケージへ戻した。5.5時間後に、マウスを屠殺して、6mmパンチを各耳から採取して、秤量した。浮腫応答は、未処置(アセトン、賦形剤のみ)耳を上回る処置耳の重量の増大パーセントとして表した。
TPA誘導性浮腫に対する本発明の組成物の影響を評価するために、アセトン20μl中のTPA 2μgを、マイクロピペッターを活用して、6匹のマウスのそれぞれの両耳上へ塗布した。マウスをマウスのケージへ戻した。15分後、アセトン10μl中の増大する濃度のAFCを、上述するように右耳の内部及び外部表面へ塗布した。アセトン賦形剤20μlを同様に、内部陰性対照として各マウスの左耳へ塗布した。処置後、マウスをマウスのケージへ5.5時間戻した。マウスを頚椎脱臼により屠殺した。耳を即座にその根元で取り出して、直径6mmのパンチ生検材料を各耳の中心から採取した。上述のように耳パンチを浮腫測定に関して化学天秤上で秤量した。様々な濃度のAFCの、TPA誘導性浮腫を阻害する能力は、TPAにより誘導される耳パンチ重量の増大に関して、AFC処置耳とアセトン(賦形剤)のみで処置した耳との間での重量の差を確定することにより評価した。
A.TPAは、マウスにおいて好中球浸潤を誘導する。
TPAのような急性接触刺激薬はまた、好中球の皮膚浸潤を誘導し得る。これは、1)最大好中球応答は最大浮腫応答に対して遅延され、2)刺激薬によっては好中球浸潤とは無関係に浮腫を誘導し、3)既知の抗炎症剤の幾つかは一方を低減させるが、他方は低減させないため、浮腫の低減とは無関係であり得るか、又は無関係でない場合がある(非特許文献15を参照)。本発明者等は、局所的に塗布されたAFCが、TPAによりもたらされる急性局所的刺激に応答して好中球浸潤に影響を及ぼすかどうかを確定しようと努めた。
同様に、本発明のAFC組成物を使用して、皮膚好中球浸潤の低減における有効性を評価した(浮腫と好中球浸潤との間の関連性、及びこれらの可変要素に対する既知の抗炎症剤の影響に関する議論に関して、非特許文献15を参照)。
好中球浸潤がMPO分析により測定される場合、AFCが用量依存性様式で好中球浸潤を低減させるように作用することが、結果により示された。AFCが好中球浸潤アッセイで試験された場合、AFCは、それ自体で炎症活性を有さないことがわかった。AFCは、MPO活性において80%を上回るTPA誘導性増大の阻害をもたらし、0.065mg/20μlのED50を有することがデータにより示されている(図4)。
この組織学的分析は、急性接触刺激に応答する皮膚好中球浸潤を抑制する際のAFCの有効性を実証した。図5で観察されるように、TPA単独処置耳における好中球の存在が、処置の24時間後に明らかに観察された。TPAへ暴露しなかった耳では、本質的に好中球は観察されなかった。TPAで前処置した後、賦形剤又はAFCで処置した耳では、好中球の数は、賦形剤+TPA処置耳は、TPA単独で処置した耳と匹敵していた。好中級の実質的な低減は、AFC処置耳で観察することができる。
TPA塗布前及び後での様々な時間におけるAFC処置の有効性は、好中球浸潤の尺度としてMPOを用いて評価した。この実施例では、6匹のマウスの両耳を1μg/20μl用量のアセトン中のTPAで処置した。続いて、右耳を、TPA塗布前及び後での様々な時間で、1mg/20μlの本発明のAFC化合物で処置した一方で、同時に対側耳をアセトンで処置した。
好中球MPO活性のTPA誘導に対するAFCの影響を、AFCと異なるメカニズムにより炎症を阻害する通常使用される異なる種類の抗炎症薬を代表する2つの他の作用物質と比較した。これらは、ステロイドであるデキサメタゾン、及び非ステロイド抗炎症薬であるインドメタゾン(これは、シクロオキシゲナーゼを標的とする)を包含した。したがって、このモデルにおけるAFCの作用を、デキサメタゾン及びインドメタゾンの作用と比較した。これらの作用物質をそれぞれ、AFCを試験するのに使用されるものと同じプロトコルを使用して試験した。
ステロイド系及び非ステロイド系抗炎症剤の両方の有効性をアッセイするためのマウス耳モデルにおいて、接触刺激薬として日常的に使用される別の標準的な作用物質であるアラキドン酸(「AA」)は、多数のリポキシゲナーゼ及びシクロオキシゲナーゼ産物に関する代謝前駆体である。その作用機序、したがってそれが活性化するシグナル伝達経路は、局所的に塗布されたTPAにより活性化されるものと異なる。AAは、塗布の1時間後にピークに達するTPAよりも迅速に浮腫を生じる。AAに応答して最小の組織学的に観察可能な好中球浸潤が見られるが、MPOの増大が検出され得る。このモデルにおけるシクロオキシゲナーゼ活性化炎症に対する有効性は、TPA活性化炎症に対する有効性よりも、あまりヒト炎症性疾患に対する有効性の予測とならないことが経験的に示されている。
この実施例では、マウスの両耳を、1μg/20μl用量のアセトン中のTPAで処置した。1時間後に、右耳を1mg/20μlの本発明のAFC組成物で処置して、左耳をアセトン単独で処置した。Nikon D70デジタルカメラを使用して、23時間後に写真を撮った。本発明者等は、TPA誘導性紅斑に対する本発明のAFC組成物の影響を観察した(図10)。
刺激薬を、20%SDS溶液0.2ml及びWebrilパッドを伴うHill−Top Chamberパッチを使用して、ヒトの上背の中央に塗布した。AFCは、水性配合物中140mMの濃度で、パッチ帯域1a及び1bへ予め塗布した(図11)。パッチ1a及び2aは2時間後に取り外したのに対して、パッチ1b及び2bは、2時間半後に取り外した。高レベルの炎症はパッチ部位2a及び2bで明白であった。部位1aは、正常な皮膚を示したのに対して、1bは軽い応答を示した。これらの結果は、本発明の組成物が、ヒト皮膚が刺激薬に暴露される場合に炎症を低減又は防止することができることを示す。
確立された慢性炎症に対する本発明の組成物の有効性は、非特許文献17の技法の変法を使用してアッセイされる。各マウスの両耳を、上記のように、0、2、4、7及び9日目の午前中の一連の5回塗布でアセトン中のTPAで処置する。処置耳に、AFC及びアセトンを含有する本発明の組成物を、7、8及び9日目に6時間空けて塗布されるように、一連の3回の対となる塗布で施した。耳のパンチを、浮腫アッセイ及び好中球の浸潤用に、上記のように、耳のパンチを10日目の午後に採取して、浮腫アッセイ及び好中球の浸潤のために調製した。総顆粒球浸潤は、MPO活性を測定することによりアッセイされる。マクロファージ浸潤は、MOMA−2抗体を使用して免疫細胞学的に確定される。炎症性浮腫顆粒化浸潤及びマクロファージ浸潤を低減させることが知られているヒドロコルチゾンを陽性対照として使用する。アセトン中のAFCが、マウスにおいて慢性浮腫及び好中球数を低減させることが結果により示されるであろう。
上述するマウス耳モデルを、免疫ベースの炎症モデルにおける抗炎症剤の影響をアッセイするために変更させる(非特許文献18及び非特許文献19を参照)。このモデルでは、アセトン中1〜3%のジニトロフルオロベンゼン(「DNFB」)の感作用量を、Back他による方法(非特許文献20及び非特許文献2を参照)の変法に従って、マウスの剃毛した腹部へ局所的に塗布して、免疫応答を誘発する。5日目に、各耳に対して0.5〜1%のDNFB 40μlでマウスを免疫刺激する。免疫刺激の30分前又は免疫刺激の15分後に、本発明のAFC化合物を一方の耳へ塗布して、賦形剤を他方の耳へ塗布する。耳は、5時間後に浮腫又は好中球浸潤に関してアッセイする。デキサメタゾンを陽性対照として使用する。5日後、接触刺激をもたらすのに不十分なDNFBの用量で耳を局所的に免疫刺激する。同時に、細胞浸潤試験を開始する。最初は、マクロファージよりも好中球が多い。48〜72時間までに、マクロファージは、優勢な集団となる。炎症応答は観察されない。したがって、本発明のAFC組成物は、浮腫及び好中球浸潤の両方を低減させるのに有効である。
Claims (47)
- 被験体の炎症を処置するための局所用組成物であって、
下記式(1)で表される、少なくとも1種のポリイソプレニル−タンパク質阻害剤化合物:
R1は、炭素数1〜3のアルキルであり、
R2は、−COX(ここで、Xは、−OH、−OCH3、−NH2、−NHR4、−N(R4)2又はハロゲンである)であり、
R3は、炭素数10〜25の直鎖又は分枝鎖アルキル、又は炭素数10〜25の直鎖又は分枝鎖アルケニルであり、
R4は、炭素数1〜25のアルキルである]、又はそれらの薬学的に許容可能な塩又はエステル;及び
キャリアからなり、
前記局所用組成物は、粉末、ヒドロゲル、オイル、クリーム、軟膏、ゲル、ローション、シャンプー、乳液、クレンザー、保湿剤、スプレー、包帯、絆創膏又は皮膚パッチの形態であり、
前記局所用組成物は、局所的に塗布された場合、炎症を抑えるのに効果のある量の少なくとも1種のポリイソプレニル−タンパク質阻害剤化合物を供給するように処方されている、
ことを特徴とする組成物。 - ポリイソプレニル−タンパク質阻害剤化合物が、N−アセチル−S−ゲラニルシステイン、N−アセチル−S−ファルネシルシステイン(AFC)又はN−アセチル−S−ゲラニルゲラニルシステイン(AGGC)である、請求項1に記載の組成物。
- R1がメチルである、請求項1に記載の組成物。
- R2がCOOHである、請求項1に記載の組成物。
- R3がファルネシルである、請求項1に記載の組成物。
- R 1 がメチルであり、Xが−OHであり、及びR 3 がファルネシルである、請求項1に記載の組成物。
- R 1 がメチルであり、Xが−OCH 3 であり、及びR 3 がファルネシルである、請求項1に記載の組成物。
- Xが−OHであり、薬学的に許容可能な塩が、アルカリ金属塩、アルカリ土類金属塩、アンモニウム塩及び置換アンモニウム塩から成る群から選択される、請求項1記載の組成物。
- 被験体の炎症を処置するための局所用組成物であって、
S−ファルネシルシステイン、N−アセチル−S−ゲラニルシステイン、N−アセチル−S−ファルネシルシステイン(AFC)、N−アセチル−S−ゲラニルゲラニルシステイン(AGGC)、S−ファルネシル−2−メルカプトエタンスルホン酸、S−ファルネシルチオ酢酸、S−ファルネシルメルカプトコハク酸、S−ファルネシルチオトリアゾール、S−ファルネシルチオサリチル酸(FTS)、S−ファルネシルチオコハク酸、2−クロロ−5−ファルネシルアミノ安息香酸、2−ファルネシル−チオニコチン酸(FTN)、5−フルオロ−FTS、5−クロロ−FTS、4−クロロ−FTS、S−ファルネシル−メチルチオサリチル酸及びそれらの薬学的に許容可能な塩及びエステルから成る群から選択される、少なくとも1種のポリイソプレニル−タンパク質阻害剤化合物;及び
キャリアからなり、
前記局所用組成物は、粉末、ヒドロゲル、オイル、クリーム、軟膏、ゲル、ローション、シャンプー、乳液、クレンザー、保湿剤、スプレー、包帯、絆創膏又は皮膚パッチの形態であり、
前記局所用組成物は、局所的に塗布された場合、炎症を抑えるのに効果のある量の少なくとも1種のポリイソプレニル−タンパク質阻害剤化合物を供給するように処方されている、
ことを特徴とする組成物。 - 被験体の炎症を処置するための局所用組成物であって、
N−アセチル−S−ファルネシルシステイン(AFC)、及び
キャリアからなり、
前記局所用組成物は、粉末、ヒドロゲル、オイル、クリーム、軟膏、ゲル、ローション、シャンプー、乳液、クレンザー、保湿剤、スプレー、包帯、絆創膏又は皮膚パッチの形態であり、
前記局所用組成物は、局所的に塗布された場合、炎症を抑えるのに効果のある量の少なくとも1種のポリイソプレニル−タンパク質阻害剤化合物を供給するように処方されている、
ことを特徴とする組成物。 - 第2活性成分をさらに含む、請求項1、9又は10に記載の組成物。
- 第2活性成分が、保護剤、皮膚軟化薬、収斂剤、刺激薬、角質溶解剤、日焼け防止剤、日焼け剤、抗生物質、抗真菌剤、抗ウイルス剤、抗原虫剤、抗挫瘡剤、麻酔剤、ステロイド系抗炎症剤、非ステロイド系抗炎症剤、かゆみ止め剤、酸化防止剤、化学療法剤、抗ヒスタミン剤、ビタミン、ホルモン、ふけ防止剤、しわ防止剤、抗皮膚萎縮剤、硬化剤、クレンジング剤、腐食剤及び低顔料着色剤から成る群から選択される少なくとも1種の成分である、請求項11に記載の組成物。
- 保護剤が、吸着剤、粘滑剤及び乾燥剤から成る群から選択される、請求項12に記載の組成物。
- 刺激薬が発赤薬である、請求項12に記載の組成物。
- レチオノイド、α−ヒドロキシ酸、β−ヒドロキシ酸、抗生物質、抗真菌剤、日焼け防止剤、ステロイド系抗炎症剤、酸化チタン、酸化亜鉛、過酸化ベンゾイル、フルオロウラシル、レゾルシノール、サリチル酸、及びそれらの混合物から成る群から選択される薬剤をさらに含む、請求項1、9又は10に記載の組成物。
- レチノイドが、ビタミンA、レチノール、レチナール、レチニルパルミチン酸、レチノイン酸、トレチノインもしくはイソ−トレチノイン又はそれらの混合物のうち少なくとも1つである、請求項15に記載の組成物。
- 薬剤がα−ヒドロキシ酸である、請求項15に記載の組成物。
- α−ヒドロキシ酸が、グリコール酸、乳酸、酒石酸、リンゴ酸もしくはクエン酸又はそれらの混合物のうち少なくとも1つである、請求項17に記載の組成物。
- 薬剤がβ−ヒドロキシ酸である、請求項15に記載の組成物。
- 薬剤が抗生物質である、請求項15に記載の組成物。
- 薬剤が抗真菌剤である、請求項15に記載の組成物。
- 薬剤が日焼け止め剤である、請求項15に記載の組成物。
- 薬剤がステロイド系抗炎症剤である、請求項15に記載の組成物。
- 薬剤が、二酸化チタン、酸化亜鉛、過酸化ベンゾイル、フルオロウラシル、レゾルシノール、もしくはサリチル酸又はそれらの混合物である、請求項15に記載の組成物。
- 少なくとも1種のポリイソプレニル−タンパク質阻害剤化合物がAFCである、請求項15〜24のいずれかに記載の組成物。
- 請求項1、9又は10に記載の被験体の炎症を処置するための局所用組成物の製造方法であって、
少なくとも1種のポリイソプレニル−タンパク質阻害剤化合物又はその薬学的に許容可能な塩又はエステル並びにキャリアを混合して、粉末、ヒドロゲル、オイル、クリーム、軟膏、ゲル、ローション、シャンプー、乳液、クレンザー、保湿剤、スプレー、包帯、絆創膏又は皮膚パッチを形成し、
前記局所用組成物は、局所的に塗布された場合、炎症を抑えるのに効果のある量の少なくとも1種のポリイソプレニル−タンパク質阻害剤化合物を供給するように処方されている、
ことを特徴とする方法。 - キャリアが薬学的に許容可能なキャリアである、請求項1、9又は10に記載の組成物。
- 薬学的に許容可能なキャリアが遅延放出キャリアである、請求項27記載の組成物。
- 遅延放出キャリアが、リポソーム、マイクロスポンジ、ミクロスフェア、及びマイクロカプセルから成る群から選択されるキャリアである、請求項28に記載の組成物。
- 少なくとも1種のポリイソプレニル−タンパク質阻害剤化合物が、N−アセチル−S−ファルネシルシステインである、請求項26に記載の方法。
- 少なくとも1種のポリイソプレニル−タンパク質阻害剤化合物が、N−アセチル−S−ゲラニルゲラニルシステインである、請求項26に記載の方法。
- 少なくとも1種のポリイソプレニル−タンパク質阻害剤化合物が、S−ファルネシル−2−メルカプトエタンスルホン酸、S−ファルネシルチオ酢酸、S−ファルネシルメルカプトコハク酸、S−ファルネシルチオトリアゾール、S−ファルネシルチオサリチル酸(FTS)、S−ファルネシルチオコハク酸、2−クロロ−5−ファルネシルアミノ安息香酸、2−ファルネシル−チオニコチン酸(FTN)、5−フルオロ−FTS、5−クロロ−FTS、4−クロロ−FTS、S−ファルネシル−メチルチオサリチル酸及びそれらの組み合わせから成る群より選択される、請求項26に記載の方法。
- ポリイソプレニル−タンパク質阻害剤化合物が、組成物中に0.01%〜50重量%存在する、請求項1、9又は10に記載の組成物。
- ポリイソプレニル−タンパク質阻害剤化合物が、組成物中に0.01%〜50重量%存在する、請求項26に記載の方法。
- ポリイソプレニル−タンパク質阻害剤化合物が、組成物中に0.1%〜20重量%存在する、請求項1、9又は10に記載の組成物。
- ポリイソプレニル−タンパク質阻害剤化合物が、組成物中に0.1%〜20重量%存在する、請求項26に記載の方法。
- ポリイソプレニル−タンパク質阻害剤化合物が、組成物中に10重量%未満存在する、請求項1、9又は10に記載の組成物。
- ポリイソプレニル−タンパク質阻害剤化合物が、組成物中に10重量%未満存在する、請求項26に記載の方法。
- ポリイソプレニル−タンパク質阻害剤化合物が、組成物中に5重量%未満存在する、請求項1、9又は10に記載の組成物。
- ポリイソプレニル−タンパク質阻害剤化合物が、組成物中に5重量%未満存在する、請求項26に記載の方法。
- ヒアルロン酸を含む、請求項1、9又は10に記載の組成物。
- グリセリンを含む、請求項1、9又は10に記載の組成物。
- 少なくとも1種の保湿剤を含む、請求項1、9又は10に記載の組成物。
- 保湿剤が、グアニジン、グリコール酸、グリコール酸塩、アロエ、アラントイン、ウラゾール、ポリヒドロキシアルコール、プロピレングリコール、ブチレングリコール、ヘキシレングリコール、ポリエチレングリコール、糖、デンプン、アルコキシル化グルコース、ヒアルロン酸、ラクトアミドモノエタノールアミン、アセトアミドモノエタノールアミン、及びこれらの組み合わせから成る群から選択される、請求項43に記載の組成物。
- 4.0〜7.0のpHを有する、請求項1、9又は10に記載の組成物。
- ポリヒドロキシアルコールが、ソルビトール、グリセロール及びヘキサントリオールから成る群から選択される、請求項44に記載の組成物。
- グリコール酸塩が、アンモニウム塩及び四級アルキルアンモニウム塩から成る群から選択される、請求項44に記載の組成物。
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US60/652,921 | 2005-02-14 | ||
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US20130115320A1 (en) | 2007-03-30 | 2013-05-09 | Dynova Laboratories, Inc. | Therapeutic agent for intranasal administration and method of making and using same |
US9415026B2 (en) * | 2009-11-12 | 2016-08-16 | Signum Biosciences, Inc. | Use of anti-bacterial agents for the treatment of epithelial-related conditions |
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US20150354096A1 (en) | 2012-12-20 | 2015-12-10 | Convatec Technologies Inc. | Processing of chemically modified cellulosic fibres |
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