JP2022537849A - Uv及び可視光の吸収剤としての重合性縮合三環式化合物 - Google Patents
Uv及び可視光の吸収剤としての重合性縮合三環式化合物 Download PDFInfo
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- ylidene
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- 125000003118 aryl group Chemical group 0.000 claims description 41
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- TXIBOUCYFJTAOD-UHFFFAOYSA-N 2-(2-cyano-2-thioxanthen-9-ylideneacetyl)oxyethyl 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OCCOC(C(=C1C2=CC=CC=C2SC=2C=CC=CC1=2)C#N)=O TXIBOUCYFJTAOD-UHFFFAOYSA-N 0.000 claims description 2
- DOSSVRGFODSWNA-UHFFFAOYSA-N 2-[(2-cyano-2-xanthen-9-ylideneacetyl)amino]ethyl 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OCCNC(C(=C1C2=CC=CC=C2OC=2C=CC=CC1=2)C#N)=O DOSSVRGFODSWNA-UHFFFAOYSA-N 0.000 claims description 2
- MITUGQXJSFMTLK-UHFFFAOYSA-N 2-[[2-cyano-2-(10-methylacridin-9-ylidene)acetyl]amino]ethyl 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OCCNC(C(=C1C2=CC=CC=C2N(C=2C=CC=CC1=2)C)C#N)=O MITUGQXJSFMTLK-UHFFFAOYSA-N 0.000 claims description 2
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Abstract
Description
本出願は、2020年5月26日出願の米国特許出願第16/883,199号及び2019年6月28日出願の米国特許仮出願第62/867,963号に対する優先権を主張するものであり、その全体が参照により本明細書に組み込まれる。
本発明は、UV及び/又は可視光吸収剤に関する。より具体的には、本発明は、様々な波長のUV及び/又は高エネルギー可視光のような可視光を吸収し、更に物品に組み込まれたときに視覚的に透明である、重合性官能基を有する化合物に関する。したがって、当該化合物は、眼科用デバイスなどの生物医学用デバイスを含むポリマー物品において使用することができる。
反応性混合物に存在し得る親水性モノマーの好適なファミリーの例としては、(メタ)アクリレート、スチレン、ビニルエーテル、(メタ)アクリルアミド、N-ビニルラクタム、N-ビニルアミド、N-ビニルイミド、N-ビニル尿素、O-ビニルカルバメート、O-ビニルカーボネート、他の親水性ビニル化合物、及びこれらの混合物が挙げられる。
本発明での使用に好適なシリコーン含有成分は、1つ又は2つ以上の重合性化合物を含み、各化合物は、独立して、少なくとも1つの重合性基、少なくとも1つのシロキサン基、及び重合性基(複数可)をシロキサン基(複数可)に接続する1つ又は2つ以上の連結基を含む。シリコーン含有成分は、例えば、下記に定義される基などの1~220個のシロキサン反復単位を含有してもよい。シリコーン含有成分はまた、少なくとも1つのフッ素原子も含有し得る。
少なくとも1つのRAは、式Rg-Lの基であり、ここで、Rgは、重合性基であり、Lは、連結基であり、残りのRAは、それぞれ独立して、
(a)Rg-L-、
(b)1つ又は2つ以上のヒドロキシ、アミノ、アミド、オキサ、カルボキシ、アルキルカルボキシ、カルボニル、アルコキシ、アミド、カルバメート、カーボネート、ハロ、フェニル、ベンジル、又はこれらの組み合わせで任意選択的に置換されているC1~C16アルキル、
(c)1つ又は2つ以上のアルキル、ヒドロキシ、アミノ、アミド、オキサ、カルボニル、アルコキシ、アミド、カルバメート、カーボネート、ハロ、フェニル、ベンジル、又はこれらの組み合わせで任意選択的に置換されているC3~C12シクロアルキル、
(d)1つ又は2つ以上のアルキル、ヒドロキシ、アミノ、アミド、オキサ、カルボキシ、アルキルカルボキシ、カルボニル、アルコキシ、アミド、カルバメート、カーボネート、ハロ、フェニル、ベンジル、又はこれらの組み合わせで任意選択的に置換されているC6~C14アリール基、
(e)ハロ、
(f)アルコキシ、環状アルコキシ、又はアリールオキシ、
(g)シロキシ、
(h)ポリエチレンオキシアルキル、ポリプロピレンオキシアルキル、又はポリ(エチレンオキシ-co-プロピレンオキシアルキル)などのアルキレンオキシ-アルキル又はアルコキシ-アルキレンオキシ-アルキル、あるいは
(i)アルキル、アルコキシ、ヒドロキシ、アミノ、オキサ、カルボキシ、アルキルカルボキシ、アルコキシ、アミド、カルバメート、ハロ又はこれらの組み合わせで任意選択的に置換されている1~100個のシロキサン反復単位を含む一価シロキサン鎖であり、
nは、0~500、又は0~200、又は0~100、又は0~20であり、nが0以外であるとき、nが表示値と同等のモードを有する分布であることが理解される。nが2以上であるとき、SiO単位は、同じ又は異なるRA置換基を担持してもよく、異なるRA置換基が存在する場合、n基は、ランダム又はブロック構成であってもよい。
反応性混合物は、少なくとも1つのポリアミドを含んでいてよい。本明細書で使用するとき、「ポリアミド」という用語は、アミド基を含有する反復単位を含むポリマー及びコポリマーを指す。ポリアミドは、環状アミド基、非環状アミド基、及びこれらの組み合わせを含み得、当業者に既知の任意のポリアミドであってもよい。非環状ポリアミドは、ペンダント非環状アミド基を含み、ヒドロキシル基との会合が可能である。環状ポリアミドは、環状アミド基を含み、ヒドロキシル基との会合が可能である。
一般に、架橋モノマー、多官能性マクロマー、及びプレポリマーとも称される1つ又は2つ以上の架橋剤を反応性混合物に添加することが望ましい。架橋剤は、二官能性架橋剤、三官能性架橋剤、四官能性架橋剤、及びこれらの混合物から選択されてもよく、これにはシリコーン含有架橋剤及び非シリコーン含有架橋剤が含まれる。非シリコーン含有架橋剤としては、エチレングリコールジメタクリレート(EGDMA)、テトラエチレングリコールジメタクリレート(TEGDMA)、トリメチロールプロパントリメタクリレート(TMPTMA)、トリアリルシアヌレート(TAC)、グリセロールトリメタクリレート、メタクリルオキシエチルビニルカーボネート(HEMAVc)、アリルメタクリレート、メチレンビスアクリルアミド(MBA)、及びポリエチレングリコールジメタクリレートが挙げられ、ポリエチレングリコールは、最大約5000ダルトンの分子量を有する。架橋剤は、通常の量、例えば、反応性製剤100グラム当たり約0.000415~約0.0156モルで反応性混合物中に用いられる。代替的に、親水性モノマー及び/又はシリコーン含有成分が分子設計により、又は不純物のために多官能性である場合、反応性混合物への架橋剤の添加は、任意選択的である。架橋剤として作用することができ、存在する場合に反応性混合物への追加の架橋剤の添加を必要としない親水性モノマー及びマクロマーの例としては、(メタ)アクリレート及び(メタ)アクリルアミドでエンドキャップされたポリエーテルが挙げられる。他の架橋剤は当業者に既知となり、本発明のシリコーンヒドロゲルを作製するために使用され得る。
反応性混合物は、希釈剤、開始剤、UV吸収剤、可視光吸収剤、光互変化合物、医薬品、栄養補助剤、抗菌物質、着色剤、顔料、共重合性染料、非重合性染料、離型剤、及びこれらの組み合わせなどであるがこれらに限定されない、追加成分を含有し得る。
反応性混合物は、振とう又は撹拌などの当該技術分野で既知の方法のいずれかによって形成され、既知の方法によるポリマー物品又はデバイスの形成に使用され得る。反応性成分は、反応性混合物を形成するために、希釈剤をしようするか又は使用しないかのいずれかで一緒に混合される。
ヘイズ:30%以下、又は10%以下
前進動的接触角(Wilhelmyプレート法):100°以下、又は80°以下、又は50°以下
引張弾性率(psi):120以下、又は80~120
酸素透過性(Dk、バーラー):少なくとも80、又は少なくとも100、又は少なくとも150、又は少なくとも200
破断伸び:少なくとも100
リゾチーム取り込み(μg/レンズ):少なくとも100、又は少なくとも150、又は少なくとも500、又は少なくとも700
ポリクオタニウム1(PQ1)取り込み(%):15以下、又は10以下、又は5以下
ここで、本発明のいくつかの実施形態を、以下の実施例にて詳細に記述する。
溶液中の化合物の紫外線可視スペクトルは、Perkin Elmer Lambda 45又はAgilent Cary 6000i、又はOcean Optics QE65 PRO(DH-2000-BAL光源)UV/VIS走査型分光計で測定した。使用前に、機器を少なくとも30分間熱平衡化した。Perkin Elmer機器では、スキャン範囲は200-800nmであり、走査速度は、毎分960nmであり、スリット幅は4nmであり、モードは透過又は吸光度に設定し、ベースライン補正を選択した。Cary機器では、走査範囲は200~800nmであり、走査速度は600nm/分であり、スリット幅は2nmであり、モードは透過又は吸光度であり、ベースライン補正を選択した。Ocean Optics機器では、走査範囲は200~800nmであり、スリット幅は10μmであり、モードは透過又は吸光度であり、ベースライン補正を選択した。自動ゼロ関数を使用してサンプルを分析する前に、ベースライン補正を行った。
L:リットル(複数可)
mL:ミリリットル(複数可)
Equiv.又はeq.:当量
kg:キログラム(複数可)
g:グラム(複数可)
mg:ミリグラム(複数可)
mol:モル(複数可)
mmol:ミリモル(複数可)
Da:ダルトン又はg/モル
kDa:キロダルトン、又は1,000ダルトンに等しい原子質量単位
min:分
μm:マイクロメートル(複数可)
nm:ナノメートル
1N NMR:プロトン核磁気共鳴分光法
UV-VIS:紫外線-可視分光法
TLC:薄層クロマトグラフィー
BC:バック又はベースカーブプラスチック成形型
FC:フロントカーブプラスチック成形型
PP:プロピレンのホモポリマーであるポリプロピレン
TT:水添スチレンブタジエンブロックコポリマーであるTuftec(Asahi Kasei Chemicals)
Z:ポリシクロオレフィン熱可塑性ポリマーであるZeonor(Nippon Zeon Co Ltd)
DMA:N,N-ジメチルアクリルアミド(Jarchem)
HEMA:2-ヒドロキシエチルメタクリレート(Bimax)
PVP K90:ポリ(N-ビニルピロリドン)(ISP Ashland)
TEGDMA:テトラエチレングリコールジメタクリレート(Esstech)
Irgacure又はOmnirad 1870:ビス(2,6-ジメトキシベンゾイル)-2,4,4-トリメチルペンチルホスフィンオキシドと1-ヒドロキシシクロヘキシルフェニルケトンとのブレンド(IGM Resins又はBASF又はCiba Specialty Chemicals)
mPDMS:モノ-n-ブチル末端モノメタクリルオキシプロピル末端ポリジメチルシロキサン(Mn=800~1500ダルトン)(Gelest)
SiMAA:2-プロペン酸、2-メチル-2-ヒドロキシ-3-[3-[1,3,3,3-テトラメチル-1-[(トリメチルシリル)オキシ]ジシロキサニル]プロポキシ]プロピルエステル(Toray)、又は3-(3-(1,1,1,3,5,5,5-ヘプタメチルトリシロキサン-3-イル)プロポキシ)-2-ヒドロキシプロピルメタクリレート
Norbloc:2-(2’-ヒドロキシ-5-メタクリリルオキシエチルフェニル)-2H-ベンゾトリアゾール(Janssen)
RB247:1,4-ビス[2-メタクリルオキシエチルアミノ]-9,10-アントラキノン
TL03光:Phillips TLK 40W/03電球
LED:発光ダイオード
D3O:3,7-ジメチル-3-オクタノール(Vigon)
DIW:脱イオン水
MeOH:メタノール
IPA:イソプロピルアルコール
DMF:N,N-ジメチルホルムアミド
DMSO:ジメチルスルホキシド
DCM又はCH2Cl2:ジクロロメタン又は塩化メチレン
DCE:1,2-ジクロロエタン
CDCl3:重水素クロロホルム
PhOH:フェノール
H2SO4:硫酸
HCl:塩酸
pTsOH:p-トルエンスルホン酸
Ac2O:無水酢酸
Cs2CO3:炭酸セシウム
SOCl2:塩化チオニル
NaH:水素化ナトリウム
CPTP:2-(3-クロロプロポキシ)テトラヒドロ-2H-ピラン
NaI:ヨウ化ナトリウム
ホウ酸塩緩衝パッキング溶液:18.52グラム(300mmol)のホウ酸、3.7グラム(9.7mmol)のホウ酸ナトリウム十水和物、及び28グラム(197mmol)の硫酸ナトリウムを、十分な脱イオン水に溶解させて、2リットルのメスフラスコを満たした。
シアン酢酸メチル(40グラム、0.4037モル)及び25mLのジクロロメタンを、窒素環境下で還流凝縮器を備えた3つ口の500mL丸底フラスコ内において撹拌した。2-アミノエタノール(23.8グラム、0.3897モル、約0.97当量)を添加漏斗を介して溶液に添加した後、温度が上昇し、塩化メチレンが還流し始めた。発熱が止まった後、外部熱を印加して、合計2時間にわたって穏やかな還流を継続した後、薄層クロマトグラフィーによってエタノールアミンは観察されなかった。
77重量パーセントの表1に列記される配合物及び23重量パーセントの希釈剤D3Oで構成される反応性モノマー混合物を調製した。反応性モノマー混合物を、個々に、圧力下でステンレス鋼シリンジを使用して3μmフィルターを通して濾過した。
(1) 式Iの縮合三環式化合物であって、
m、n及びtは、独立して、0、1、2、3、又は4であり、
R1、R2、及びR3は、各出現時において独立して、H、任意選択の置換基、若しくは-Y-Pgであるか、又は2つの隣接するR1、R2、若しくはR3基が、それらが結合している原子と一緒に結合して、-Y-Pgで任意選択的に置換されたシクロアルキル又はアリール環を形成し、
Bは、O、S、N、及びNR6から独立して選択される最大3個のヘテロ原子を任意選択的に有する、芳香族、飽和、又は部分不飽和である5、6又は7員環を表し、R6は、H、C1~C6アルキル、シクロアルキル、ヘテロシクロアルキル、アリール、ヘテロアリール、又はY-Pgであり、
C及びDのうちの一方は、O、S、N、及びNR6から独立して選択される最大3個のヘテロ原子を任意選択的に有する、芳香族、飽和、又は部分不飽和である5、6又は7員環を表し、C及びDのうちの他方は、少なくとも1個の環炭素原子と、O、S、NR6、SO、又はSO2から独立して選択される少なくとも1個のヘテロ基と、を有する6員飽和又は部分不飽和ヘテロシクロアルキル環であり、前記ヘテロシクロアルキル環は、1個の環炭素原子において式=C(EWG)(R7)の基によって置換されており、R7は、EWG又は-C(=O)-T-Y-Pgであり、EWGは、各出現時において独立して電子求引基であり、
各出現時においてPgは、独立して、重合性基であり、
各出現時においてYは、独立して、連結基であり、
各出現時においてTは、独立して、結合、O、又はNR6であり、
前記式Iの化合物は、少なくとも1個のPg基を含有する、化合物。
(2) m、n及びtが、独立して、0又は1である、実施態様1に記載の化合物。
(3) R1が、H、C1~C6アルキル、C1~C6アルコキシ、C1~C6チオアルキル、C3~C7シクロアルキル、アリール、ハロ、ヒドロキシ、アミノ、NR4R5、ベンジル、SO3H、又はSO3Naであり、R4及びR5が、独立して、H又はC1~C6アルキルである、実施態様1又は2に記載の化合物。
(4) R2及びR3が、独立して、H、C1~C6アルキル、C1~C6アルコキシ、C1~C6チオアルキル、C3~C7シクロアルキル、アリール、ハロ、ヒドロキシ、アミノ、NR4R5、ベンジル、SO3H、又はSO3Naであり、R4及びR5が、独立して、H又はC1~C6アルキルである、実施態様1~3のいずれかに記載の化合物。
(5) R6が、H又はC1~C6アルキルである、実施態様1~4のいずれかに記載の化合物。
(7) 各出現時においてYが、独立して、アルキレン、シクロアルキレン、ヘテロシクロアルキレン、アリーレン(例えば、フェニレン)、ヘテロアリーレン、オキサアルキレン、アルキレン-アミド-アルキレン、アルキレン-アミン-アルキレン、又は前述の基のいずれかの組み合わせである、実施態様1~6のいずれかに記載の化合物。
(8) Tが、結合又はNR6である、実施態様1~7のいずれかに記載の化合物。
(9) 各出現時においてEWGが、独立して、シアノ、アミド、エステル、ケト、又はアルデヒドである、実施態様1~8のいずれかに記載の化合物。
(10) Bが、O、S、及びNから選択される1個のヘテロ原子を任意選択的に有する6員芳香環を表す、実施態様1~9のいずれかに記載の化合物。
(12) Cが、少なくとも1個の環炭素原子及び、O、S、NR6、SO、又はSO2から選択される1個のヘテロ基を有する6員の飽和ヘテロシクロアルキル環であり、前記ヘテロシクロアルキル環が、1個の環炭素原子において式=C(EWG)(R7)の基で置換されている、実施態様1~11のいずれかに記載の化合物。
(13) R7が、EWGである、実施態様1~12のいずれかに記載の化合物。
(14) R7が、-C(=O)-T-Y-Pgである、実施態様1~12のいずれかに記載の化合物。
(15) 前記化合物が、1つのY-Pg基を含有する、実施態様1~14のいずれかに記載の化合物。
(17) 2-(2-シアノ-2-(フェナントリジン-6(5H)-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(フェナントリジン-6(5H)-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(1,9-フェナントロリン-2(1H)-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(1,9-フェナントロリン-2(1H)-イリデン)アセトアミド)エチルメタクリレート、
2-(2-(ベンゾ[c][2,6]ナフチリジン-5(6H)-イリデン)-2-シアノアセトアミド)エチルメタクリレート、
2-(2-(ベンゾ[c][2,6]ナフチリジン-5(6H)-イリデン)-2-シアノアセトアミド)エチルメタクリレート、
2-((9-(ジシアノメチレン)-9H-キサンテン-3-イル)オキシ)エチルメタクリレート、
3-(9-(ジシアノメチレン)アクリジン-10(9H)-イル)プロピルメタクリレート、
2-(2-シアノ-2-(4H-チエノ[2,3-b]チオクロメン-4-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(9H-チエノ[3,2-b]チオクロメン-9-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(4H-チエノ[2,3-b]チオクロメン-4-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(9H-チエノ[3,2-b]チオクロメン-9-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(9H-チオキサンテン-9-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(9H-キサンテン-9-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(10-メチルアクリジン-9(10H)-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(10,10-ジオキシド-9H-チオキサンテン-9-イリデン)アセトアミド)エチルメタクリレート、
N-(2-(2-シアノ-2-(9H-チオキサンテン-9-イリデン)アセトアミド)エチル)メタクリルアミド、
N-(2-(2-シアノ-2-(10-メチルアクリジン-9(10H)イリデン)アセトアミド)エチル)メタクリルアミド、
N-(2-(2-シアノ-2-(9H-キサンテン-9-イリデン)アセトアミド)エチル)アクリルアミド、
2-(2-シアノ-2-(9H-チオキサンテン-9-イリデン)アセトキシ)エチルメタクリレート、
2-(2-シアノ-2-(2-プロポキシ-9H-チオキサンテン-9-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(2-プロポキシ-9H-チオキサンテン-9-イリデン)アセトアミド)エチルメタクリレート、又は
2-(9-(ジシアノメチレン)アクリジン-10(9H)-イル)エチルメタクリレートである、実施態様1に記載の化合物。
(18) 式I-zの化合物ではなく、
(19) 反応性混合物の重合反応生成物である眼科用デバイスであって、前記眼科用デバイスを作製するのに好適なモノマーと、(b)実施態様1~17のいずれかに記載の化合物と、を含む、眼科用デバイス。
(20) 前記デバイスを作製するのに好適な前記モノマーが、親水性成分、疎水性成分、シリコーン含有成分、又はこれらの2つ以上の混合物から選択される、実施態様19に記載の眼科用デバイス。
(22) 眼内レンズ又はソフトコンタクトレンズである、実施態様19~21のいずれかに記載の眼科用デバイス。
(23) 前記デバイスを作製するのに好適な前記モノマーが、親水性成分とシリコーン含有成分との組み合わせである場合、前記反応生成物が、式I-zの化合物以外の式Iの化合物から誘導される繰り返し単位を含み、
(24) ポリマーネットワークと、実施態様1~17のいずれかに記載の化合物から誘導される繰り返し単位を含む非反応性ポリマーと、を含む、眼科用デバイス。
(25) 前記非反応性ポリマーが、アミドモノマー、単官能性ポリアルキレングリコール、又はこれらの組み合わせから誘導される繰り返し単位を更に含む、実施態様24に記載の眼科用デバイス。
(27) ある国に輸入される、実施態様19~26のいずれかに記載の眼科用デバイス。
(28) 前記国がアメリカ合衆国である、実施態様27に記載の眼科用デバイス。
Claims (28)
- 式Iの縮合三環式化合物であって、
m、n及びtは、独立して、0、1、2、3、又は4であり、
R1、R2、及びR3は、各出現時において独立して、H、任意選択の置換基、若しくは-Y-Pgであるか、又は2つの隣接するR1、R2、若しくはR3基が、それらが結合している原子と一緒に結合して、-Y-Pgで任意選択的に置換されたシクロアルキル又はアリール環を形成し、
Bは、O、S、N、及びNR6から独立して選択される最大3個のヘテロ原子を任意選択的に有する、芳香族、飽和、又は部分不飽和である5、6又は7員環を表し、R6は、H、C1~C6アルキル、シクロアルキル、ヘテロシクロアルキル、アリール、ヘテロアリール、又はY-Pgであり、
C及びDのうちの一方は、O、S、N、及びNR6から独立して選択される最大3個のヘテロ原子を任意選択的に有する、芳香族、飽和、又は部分不飽和である5、6又は7員環を表し、C及びDのうちの他方は、少なくとも1個の環炭素原子と、O、S、NR6、SO、又はSO2から独立して選択される少なくとも1個のヘテロ基と、を有する6員飽和又は部分不飽和ヘテロシクロアルキル環であり、前記ヘテロシクロアルキル環は、1個の環炭素原子において式=C(EWG)(R7)の基によって置換されており、R7は、EWG又は-C(=O)-T-Y-Pgであり、EWGは、各出現時において独立して電子求引基であり、
各出現時においてPgは、独立して、重合性基であり、
各出現時においてYは、独立して、連結基であり、
各出現時においてTは、独立して、結合、O、又はNR6であり、
前記式Iの化合物は、少なくとも1個のPg基を含有する、化合物。 - m、n及びtが、独立して、0又は1である、請求項1に記載の化合物。
- R1が、H、C1~C6アルキル、C1~C6アルコキシ、C1~C6チオアルキル、C3~C7シクロアルキル、アリール、ハロ、ヒドロキシ、アミノ、NR4R5、ベンジル、SO3H、又はSO3Naであり、R4及びR5が、独立して、H又はC1~C6アルキルである、請求項1又は2に記載の化合物。
- R2及びR3が、独立して、H、C1~C6アルキル、C1~C6アルコキシ、C1~C6チオアルキル、C3~C7シクロアルキル、アリール、ハロ、ヒドロキシ、アミノ、NR4R5、ベンジル、SO3H、又はSO3Naであり、R4及びR5が、独立して、H又はC1~C6アルキルである、請求項1~3のいずれか一項に記載の化合物。
- R6が、H又はC1~C6アルキルである、請求項1~4のいずれか一項に記載の化合物。
- 各出現時においてPgが、独立して、スチリル、ビニルカーボネート、ビニルエーテル、ビニルカルバメート、N-ビニルラクタム、N-ビニルアミド、(メタ)アクリレート、又は(メタ)アクリルアミドを含む、請求項1~5のいずれか一項に記載の化合物。
- 各出現時においてYが、独立して、アルキレン、シクロアルキレン、ヘテロシクロアルキレン、アリーレン(例えば、フェニレン)、ヘテロアリーレン、オキサアルキレン、アルキレン-アミド-アルキレン、アルキレン-アミン-アルキレン、又は前述の基のいずれかの組み合わせである、請求項1~6のいずれか一項に記載の化合物。
- Tが、結合又はNR6である、請求項1~7のいずれか一項に記載の化合物。
- 各出現時においてEWGが、独立して、シアノ、アミド、エステル、ケト、又はアルデヒドである、請求項1~8のいずれか一項に記載の化合物。
- Bが、O、S、及びNから選択される1個のヘテロ原子を任意選択的に有する6員芳香環を表す、請求項1~9のいずれか一項に記載の化合物。
- Dが、O、S、及びNから選択される1個のヘテロ原子を任意選択的に有する6員芳香環を表す、請求項1~10のいずれか一項に記載の化合物。
- Cが、少なくとも1個の環炭素原子及び、O、S、NR6、SO、又はSO2から選択される1個のヘテロ基を有する6員の飽和ヘテロシクロアルキル環であり、前記ヘテロシクロアルキル環が、1個の環炭素原子において式=C(EWG)(R7)の基で置換されている、請求項1~11のいずれか一項に記載の化合物。
- R7が、EWGである、請求項1~12のいずれか一項に記載の化合物。
- R7が、-C(=O)-T-Y-Pgである、請求項1~12のいずれか一項に記載の化合物。
- 前記化合物が、1つのY-Pg基を含有する、請求項1~14のいずれか一項に記載の化合物。
- 2-(2-シアノ-2-(フェナントリジン-6(5H)-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(フェナントリジン-6(5H)-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(1,9-フェナントロリン-2(1H)-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(1,9-フェナントロリン-2(1H)-イリデン)アセトアミド)エチルメタクリレート、
2-(2-(ベンゾ[c][2,6]ナフチリジン-5(6H)-イリデン)-2-シアノアセトアミド)エチルメタクリレート、
2-(2-(ベンゾ[c][2,6]ナフチリジン-5(6H)-イリデン)-2-シアノアセトアミド)エチルメタクリレート、
2-((9-(ジシアノメチレン)-9H-キサンテン-3-イル)オキシ)エチルメタクリレート、
3-(9-(ジシアノメチレン)アクリジン-10(9H)-イル)プロピルメタクリレート、
2-(2-シアノ-2-(4H-チエノ[2,3-b]チオクロメン-4-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(9H-チエノ[3,2-b]チオクロメン-9-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(4H-チエノ[2,3-b]チオクロメン-4-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(9H-チエノ[3,2-b]チオクロメン-9-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(9H-チオキサンテン-9-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(9H-キサンテン-9-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(10-メチルアクリジン-9(10H)-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(10,10-ジオキシド-9H-チオキサンテン-9-イリデン)アセトアミド)エチルメタクリレート、
N-(2-(2-シアノ-2-(9H-チオキサンテン-9-イリデン)アセトアミド)エチル)メタクリルアミド、
N-(2-(2-シアノ-2-(10-メチルアクリジン-9(10H)イリデン)アセトアミド)エチル)メタクリルアミド、
N-(2-(2-シアノ-2-(9H-キサンテン-9-イリデン)アセトアミド)エチル)アクリルアミド、
2-(2-シアノ-2-(9H-チオキサンテン-9-イリデン)アセトキシ)エチルメタクリレート、
2-(2-シアノ-2-(2-プロポキシ-9H-チオキサンテン-9-イリデン)アセトアミド)エチルメタクリレート、
2-(2-シアノ-2-(2-プロポキシ-9H-チオキサンテン-9-イリデン)アセトアミド)エチルメタクリレート、又は
2-(9-(ジシアノメチレン)アクリジン-10(9H)-イル)エチルメタクリレートである、請求項1に記載の化合物。 - 反応性混合物の重合反応生成物である眼科用デバイスであって、前記眼科用デバイスを作製するのに好適なモノマーと、(b)請求項1~17のいずれか一項に記載の化合物と、を含む、眼科用デバイス。
- 前記デバイスを作製するのに好適な前記モノマーが、親水性成分、疎水性成分、シリコーン含有成分、又はこれらの2つ以上の混合物から選択される、請求項19に記載の眼科用デバイス。
- 従来の(非シリコーン)ヒドロゲル又はシリコーンヒドロゲルである、請求項19又は20に記載の眼科用デバイス。
- 眼内レンズ又はソフトコンタクトレンズである、請求項19~21のいずれか一項に記載の眼科用デバイス。
- ポリマーネットワークと、請求項1~17のいずれか一項に記載の化合物から誘導される繰り返し単位を含む非反応性ポリマーと、を含む、眼科用デバイス。
- 前記非反応性ポリマーが、アミドモノマー、単官能性ポリアルキレングリコール、又はこれらの組み合わせから誘導される繰り返し単位を更に含む、請求項24に記載の眼科用デバイス。
- 前記アミドモノマーが、式H1若しくはH2の非環状アミド、式H3の環状アミド又はこれらの組み合わせであり、
- ある国に輸入される、請求項19~26のいずれか一項に記載の眼科用デバイス。
- 前記国がアメリカ合衆国である、請求項27に記載の眼科用デバイス。
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-
2020
- 2020-05-26 US US16/883,199 patent/US20200407324A1/en active Pending
- 2020-06-11 KR KR1020207034316A patent/KR20220027728A/ko active Search and Examination
- 2020-06-11 EP EP20733038.2A patent/EP3990431A1/en active Pending
- 2020-06-11 WO PCT/IB2020/055485 patent/WO2020261021A1/en active Application Filing
- 2020-06-11 JP JP2020565846A patent/JP2022537849A/ja active Pending
- 2020-06-11 CN CN202080002979.XA patent/CN112449635A/zh active Pending
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WO2020261021A1 (en) | 2020-12-30 |
US20200407324A1 (en) | 2020-12-31 |
KR20220027728A (ko) | 2022-03-08 |
EP3990431A1 (en) | 2022-05-04 |
CN112449635A (zh) | 2021-03-05 |
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