JP5607127B2 - 水素結合ヒドロゲル - Google Patents
水素結合ヒドロゲル Download PDFInfo
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- JP5607127B2 JP5607127B2 JP2012230447A JP2012230447A JP5607127B2 JP 5607127 B2 JP5607127 B2 JP 5607127B2 JP 2012230447 A JP2012230447 A JP 2012230447A JP 2012230447 A JP2012230447 A JP 2012230447A JP 5607127 B2 JP5607127 B2 JP 5607127B2
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Classifications
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- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6903—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being semi-solid, e.g. an ointment, a gel, a hydrogel or a solidifying gel
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- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
- C08L101/14—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity the macromolecular compounds being water soluble or water swellable, e.g. aqueous gels
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- Materials For Medical Uses (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Colloid Chemistry (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Description
以下を含むヒドロゲル:
(a)少なくとも2個の4H単位が共有結合している親水性ポリマーからなる、前記ヒドロゲルの総重量に対して0.3〜50.0重量%の水ゲル化剤であって、前記4H単位が、一般式(1)又は(2)を有している水ゲル化剤
(b)50.0〜99.7重量%の水。
4H単位が、X1...X4及びY1...Y4という4個のドナー又はアクセプタを含むように、式(1)及び(2)においては、n=4であることが好ましい。4H単位は、自己相補的(すなわち、2個の水素結合単位X1...X4及びY1...Y4が、ドナー及びアクセプタについて同等の配列を有する)であってもよく、非自己相補的(すなわち、2個の水素結合単位X1...X4及びY1...Y4が、ドナー及びアクセプタについて2つの異なる配列を有する)であってもよい。4H単位は、2個の連続したドナーの後に2個の連続したアクセプタを含んでいることが好ましい。すなわち、X1及びX2がドナーで、X3及びX4がアクセプタであることが好ましい。かかるドナー及びアクセプタは、O、S、及びN原子であることが好ましい。4H単位は、参照により本明細書に組み込まれる米国特許第6320018号明細書にて、詳しく開示されている。
(a)水素;
(b)C1〜C20アルキル;
(c)C6〜C12アリール;
(d)C7〜C12アルカリル;
(e)C7〜C12アルキルアリール;
(f)式(5)を有するポリエステル基
(g)式(6)に記載の1〜4個のウレイド基で置換されたC1〜C10アルキル基
R5−NH−C(O)−NH−
(6)
(式中、R5は、水素及びC1〜C6直鎖又は分岐アルキルからなる群から選択される。);
(h)式(7)を有するポリエーテル基
前記4H単位は、R1、R2及び/又はR3を介して(R1、R2又はR3が直接結合を表すように)、(a)〜(h)に記載の側鎖を独立して表している他のR基と共にポリマー骨格に結合している。
本発明の水ゲル化剤は、親水性ポリマーのポリマー骨格に共有結合している4H単位を、2〜50個含んでいることが好ましく、3〜50個含んでいることがより好ましく、4〜30個含んでいることがさらに好ましく、6〜20個含んでいることが最も好ましい。
(a)式(8)に記載のモノマー
(i)OH;
(ii)1〜6個のヒドロキシ基で置換されていてもよいC1〜C12直鎖又は分岐アルコキシ;
(iii)式−N(R10)2に記載のアミドであって、式中、R10は、水素、又は1〜6個のヒドロキシ基で置換されていてもよいC1〜C6直鎖又は分岐アルキルであってもよい;
(iv)式−[N(R10)3]+X−に記載のアンモニウム塩であって、式中、R10は、(iii)で定義した通りであり、Xは、ハロゲン原子である;及び、
(v)式(9)に記載の基
(b)C1〜C12直鎖又は分岐アルキルビニルエーテル;
(c)ビニルアルコール;
(d)アルカリ土類金属カチオン又はアルカリ金属カチオンを有するC2〜C12α−アルケニレンω−スルホン酸;
(e)式(10)に記載のC7〜C12ビニルアリールスルホン酸
(f)CH2=CH−R11であって、式中、R11は、ピロリル、イミダゾリル、ピラゾリル、ピリジニル、ピラジニル、ピリミジニル、ピロリジル、インドリル、インドリジニル、インダゾリル、プリニル、キノリジニル、キノリニル、イソキノリニル、フタリジニル、ナフチピリジニル、キノキサリニル、キナゾリニル、シンノリニル、プテリジニル、ピロリドニル、ピロリニル、ピロリジニル、イミダゾリジニル、イミダゾリニル、ピラゾリジニル、ピラゾリニル、ピペリジル、ピペラジニル、インドリニル、イソインドリニル、モルホリニル、イソオキサゾリル、フラザニル、及びイソチアゾリルからなる群から選択される;
(g)CH2=CH−O−C(O)R12であって、式中、R12は、C1〜C6直鎖又は分岐アルキルからなる群から選択される;
(h)CH2=CH−CH2OR13であって、式中、R13は、水素及びC1〜C6直鎖又は分岐アルキルからなる群から選択される;及び、
(i)式(11)に記載のN−ビニルラクタム。
Z−[(CH2CH2O)r−H]s
(12)
式中、Zはコア分子を表し、rは4〜50の範囲内であり、sは2〜30の範囲内であり、より好ましくは、sは2〜15の範囲内であり、最も好ましくは、sは3〜12の範囲内である。
(a)ポリオキシアルキレン構造及びOH末端基を有するポリエーテルジオール;
(b)OH末端基を有するポリエステル及びコポリエステル;
(c)OH末端基を有するポリカーボネート及びコポリカーボネート;
(d)OH末端基を有するポリオルソエステル;
(e)(水素化)ポリオレフィンジオール;及び
(f)ポリウレタン;及び
(g)これらの好ましいポリマー(a)〜(e)の組合せを主成分とするポリマー及びコポリマー。
本発明のある実施形態において、水ゲル化剤は生分解性部分を含んでおり、そうした生分解性部分は、一重結合(例えば、エステル結合)又は結合(linkages)であるかもしれず、又は複数の生分解性結合(biodegradable bonds)を有する領域(例えば、ポリエステル又はオリゴエステル)であるかもしれない。前記生分解性部分は、親水性ポリマーの4H単位を含まない部分の内部、4H単位そのものの中、及び/又は親水性ポリマーと4H単位との間の結合部分(attachments)中に生じる場合がある。生分解性結合又は結合の例としては、共有エステル結合、チオエステル結合、オルソエステル結合、チオオルソエステル結合、ウレタン結合、チオウレタン結合、又はアミド結合などがあるが、エステル結合が好ましい。
以下の実施例により、本発明の好ましい実施形態についてさらに説明する。特に記載のない場合、化学品はAldrich社より入手している。
1,6−ヘキシルジイソシアネート(650g)及びメチルイソシトシン(又は2−アミノ−4−ヒドロキシ−6−メチル−ピリミジン、65.1g)を、容量2リットルのフラスコ内で懸濁した。混合液を、アルゴン雰囲気下、100℃にて一晩攪拌した。室温まで冷却した後、攪拌を続けながら、1リットルのペンタンを懸濁液に添加した。生成物を濾過し、ペンタンで数回洗浄して、真空乾燥を行った。白色粉末を得た。1H−NMR(400MHz、CDCl3):δ13.1(1H)、11.8(1H)、10.1(1H)、5.8(1H)、3.3(4H)、2.1(3H)、1.6(4H)、1.4(4H)。FT−IR(ニート):ν(cm−1)。2935、2281、1698、1668、1582、1524、1256。
2−アミノ−4−ヒドロキシ−5−(2−ヒドロキシエチル)−6−メチル−ピリミジン(12グラム)を、IPDI(150mL)中に懸濁し、アルゴン雰囲気下、90℃にて一晩攪拌した。透明な溶液となった。かかる溶液を冷却し、ヘキサン中で沈殿させた。固形物を濾過し、別のヘキサン中で攪拌した後、濾過、ヘキサンでの洗浄、及び残渣の乾燥により、生成物を単離した。収率:98%。1H−NMR(400MHz、CDCl3):δ13.1(1H)、11.9(1H)、10.2(1H)、4.8〜4.5(1H)、4.2(2H)、4.0〜3.2(3H)、3.1〜2.9(3H)、2.7(2H)、2.3(3H)、1.9〜1.6(4H)、1.4〜0.8(26H)。FT−IR(ニート):ν(cm−1)。2954、2254、1690、1664、1637、1590、1532、1461、1364、1307、1257、1034、791。MALDI−TOF−MS、[M+]=614、[M+Na+]=636。
メチルイソシトシン(5.2g)をイソホロンジイソシアネート(IPDI、50mL)に添加した後、アルゴン雰囲気下、90℃にて3日間攪拌した。結果として得られた透明な溶液を、ヘプタン中で沈殿させた。白色の粘性物質を回収し、150mLのヘプタン中で加熱して、氷上で冷却し、濾過した。白色の残渣について同じ手順をもう1回繰り返し、白色粉末を得た。1H−NMR(400MHz、CDCl3):δ13.1(1H)、12.0(1H)、10.1(1H)、5.9(1H)、4.1〜3.1(3H)、2.1(3H)、2.0〜0.9(15H)。FT−IR(ニート):ν(cm−1)2954、2255、1696、1662、1582、1524、1247。
UPy1(実施例1、79g)をクロロホルム(1.5L)に懸濁し、その後、ヒドロキシエチルメタクリレート(HEMA、64mL)及び15滴のジブチル錫ジラウレートを添加した。混合液を、オイルバス温度90℃にて4時間攪拌し、その後、冷却して濾過した。濾過物を濃縮して過剰のジエチルエーテル中に滴下した。白色沈殿物を濾過により回収し、ジエチルエーテルで洗浄した。真空乾燥を行ったところ、4H単位を含有するメタクリレートからなる白色固形生成物(90g)を得た。1H−NMR(400MHz、CDCl3):δ13.1(1H)、11.8(1H)、10.1(1H)、6.1(1H)、5.8(1H)、5.6(1H)、5.0(1H)、4.3(4H)、3.3〜3.2(4H)、2.1(3H)、1.9(3H)、1.7〜1.2(8H)。FT−IR(ニート):n3301、2932、1720、1699、1685、1665、1582、1525、1258。
チコリから得たイヌリン(1.8g、DP:10〜14)に対し、70℃で12時間の真空乾燥を行った。乾燥させたイヌリンを無水NMP(10mL)に溶解させ、70℃に加熱した結果、黄色味を帯びたやや濁りのある溶液を得た。この溶液にUPy1(0.98g)を添加し、反応混合液を70℃で12時間攪拌し、続いて水(60mL)を添加したところ、ヒドロゲルが形成された。結果として得られたヒドロゲルを、その後、水(10mL)で6回すすいだ。
5重量%の乳酸を含む水に高分子量のキトサンを溶解させ、全濃度5重量%のキトサンを含む溶液を得た。全キトサン濃度が1重量%に達するまで、この溶液をDMSOで希釈した。この溶液にUPy1(キトサン中の反復単位数と比較して、0.3等量)を添加した後、混合液をボルテックスしてテフロン(登録商標)製の型に流し入れ、続いて75℃で1時間硬化させたところ、透明なゲル化された系(gelled system)を得た。DMSOを除去するため、及び透明で剛性のキトサンヒドロゲルを得るため、これらのゲルをエタノールで5回抽出した。
6merのグリセロールを主成分とする8つのヒドロキシ開始側(initiator sides)を備えた開始剤を用いた酸化エチレンのイオン重合により、総分子量が10kDaの8星型ポリ(エチレングリコール)を得た。このPEG−星形(1.0g)を80℃で12時間真空乾燥させた後、クロロホルム(50mL)に溶解させ、続いてUPy3(278mg)及び2滴のジブチル錫ジラウレートを添加した。反応混合液を80℃に加熱し、8時間攪拌した後、水を4滴添加した。反応混合液を冷却し、濾過してジエチルエーテル中で沈殿させ、白色沈殿物を得た。1H−NMR(400MHz、CDCl3):δ13.1、11.8、10.1、5.8、5.0〜4.6、4.2、3.8〜2.8、2.2、1.9〜1.5、1.4〜0.8。
実施例8D用に例示する一般的な手順:テレケリックヒドロキシ末端PEG−6000(10.20g)を、三つ口フラスコ内において真空中で120分間、120℃に加熱し(実施例8c及び実施例8Gでは、この乾燥ステップの前に2回目のテレケリックポリマーを添加する)、その後、80℃に冷却した。UPy2(1.25g)及び2滴のジブチル錫ジラウレートを溶解させたトルエン(40mL)をポリマー融液に添加し、アルゴン下、80℃にて、溶液を一晩攪拌した。反応混合液を40mLのTHFで希釈し、ジエチルエーテル中に沈殿させた。物質は白色(半結晶状)で、弾性及び頑強性がある。1H−NMR(300MHz、CDCl3/CD3OD):δ4.1、3.6、2.8、2.2、1.8〜1.4、1.2〜0.8。
Claims (11)
- 以下を含むヒドロゲル:
(a)少なくとも2個の4H単位が共有結合している親水性ポリマーからなる、前記ヒドロゲルの総重量に対して0.3〜50.0重量%の水ゲル化剤であって、前記4H単位が、一般式(3)又は式(4)、及びその互変異性体を有し
(i)水素;
(ii)C1〜C20アルキル;
(iii)C6〜C12アリール;
(iv)C7〜C12アルカリル;
(v)C7〜C12アルキルアリール;
(vi)式(5)を有するポリエステル基
(式中、R4及びYは、水素及びC1〜C6直鎖又は分岐アルキルからなる群から独立して選択され、nは、1〜6であり、mは、10〜100である。);
(vii)式(6)に記載の1〜4個のウレイド基で置換されたC1〜C10アルキル基
R5−NH−C(O)−NH−
(6)
(式中、R5は、水素及びC1〜C6直鎖又は分岐アルキルからなる群から選択される。);
(viii)式(7)を有するポリエーテル基
(式中、R6、R7及びYは、水素及びC1〜C6直鎖又は分岐アルキルからなる群から独立して選択され、oは、10〜100である。)]、ここで、
前記4H単位が、R 1 及びR 2 を介してポリマー骨格に結合し、R 3 は、(i)〜(viii)からなる群から選択され、あるいは、R 1 及びR 3 を介してポリマー骨格に結合し、R 2 は、(i)〜(viii)からなる群から選択され;
(b)前記ヒドロゲルの総重量に対して50.0〜99.7重量%の水;及び
(c)前記ヒドロゲルの総重量に対して計算して、8重量%未満の他の極性溶媒。 - 2〜50個の4H単位が、親水性ポリマーに共有結合していることを特徴とする請求項1記載のヒドロゲル。
- 水ゲル化剤の数平均分子量が、1200〜1,000,000であることを特徴とする請求項1記載のヒドロゲル。
- 水ゲル化剤が、ブロックコポリマーであり、親水性ポリマーと4H単位が交互になっている、請求項1記載のヒドロゲル。
- 水ゲル化剤の数平均分子量が、1200〜100000であることを特徴とする請求項4記載のヒドロゲル。
- 親水性ポリマーが、ビニルモノマーの(共)重合により得ることができるポリマーから調製され、前記ビニルモノマーが、以下の(a)〜(i)からなる群から選択されることを特徴とする請求項1〜5のいずれか記載のヒドロゲル:
(a)式(8)に記載のモノマー
[式中、R8は、以下の(i)〜(v)からなる群から独立して選択され、R9は、水素又はメチルである:
(i)OH;
(ii)1〜6個のヒドロキシ基で置換されていてもよいC1〜C12直鎖又は分岐アルコキシ;
(iii)式−N(R10)2のアミドであって、式中、R10は、水素、又は1〜6個のヒドロキシ基で置換されていてもよいC1〜C6直鎖又は分岐アルキルであってもよい;
(iv)式−[N(R10)3]+X−に記載のアンモニウム塩であって、式中、R10は、(iii)で定義した通りであり、Xは、ハロゲン原子である;及び、
(v)式(9)に記載の基
(式中、R10は、(iii)で定義した通りであり、pは、1〜50であり、q=2又は3である。)];
(b)C1〜C12直鎖又は分岐アルキルビニルエーテル;
(c)ビニルアルコール;
(d)アルカリ土類金属カチオン又はアルカリ金属カチオンを有するC2〜C12α−アルケニレンω−スルホン酸;
(e)式(10)に記載のC7〜C12ビニルアリールスルホン酸
[式中、R10は、(iii)で定義した通りであり、Mは、アルカリ土類金属又はアルカリ金属カチオンである。];
(f)CH2=CH−R11であって、式中、R11は、ピロリル、イミダゾリル、ピラゾリル、ピリジニル、ピラジニル、ピリミジニル、ピロリジル、インドリル、インドリジニル、インダゾリル、プリニル、キノリジニル、キノリニル、イソキノリニル、フタリジニル、ナフチピリジニル、キノキサリニル、キナゾリニル、シンノリニル、プテリジニル、ピロリドニル、ピロリニル、ピロリジニル、イミダゾリジニル、イミダゾリニル、ピラゾリジニル、ピラゾリニル、ピペリジル、ピペラジニル、インドリニル、イソインドリニル、モルホリニル、イソオキサゾリル、フラザニル、及びイソチアゾリルからなる群から選択される;
(g)CH2=CH−O−C(O)R12であって、式中、R12は、C1〜C6直鎖又は分岐アルキルからなる群から選択される;
(h)CH2=CH−CH2OR13であって、式中、R13は、水素及びC1〜C6直鎖又は分岐アルキルからなる群から選択される;及び、
(i)式(11)に記載のN−ビニルラクタム。
[式中、R13は、(h)で定義した通りであり、rは、2〜6である。] - 親水性ポリマーが、式(12)に記載のOH末端基を有する(酸化)ポリ(エチレン)ポリマーから調製されることを特徴とする請求項1〜6のいずれか記載のヒドロゲル。
Z−[(CH2CH2O)r−H]s
(12)
[式中、Zは、コア分子を表し、rは、4〜50の範囲内であり、sは、2〜30の範囲内である。] - ヒドロゲルが、生物活性若しくは薬学的活性を有する化合物又は生物活性種を含むことを特徴とする請求項1〜9のいずれか記載のヒドロゲル。
- 化粧品用、医薬品用、又は生物医学用組成物における請求項1〜10のいずれか記載のヒドロゲルの使用。
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