JP5443159B2 - 部位特異的ドラッグデリバリのためのポリエステルアミドプラットフォーム - Google Patents
部位特異的ドラッグデリバリのためのポリエステルアミドプラットフォーム Download PDFInfo
- Publication number
- JP5443159B2 JP5443159B2 JP2009506531A JP2009506531A JP5443159B2 JP 5443159 B2 JP5443159 B2 JP 5443159B2 JP 2009506531 A JP2009506531 A JP 2009506531A JP 2009506531 A JP2009506531 A JP 2009506531A JP 5443159 B2 JP5443159 B2 JP 5443159B2
- Authority
- JP
- Japan
- Prior art keywords
- pea
- acid
- polymer
- amino
- radicals
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 0 CC(C)(C)N(C(*)C(O*OC(C(*)N(C(*C(C(C)(C)*)=O)=O)O*)=O)=O)*=C Chemical compound CC(C)(C)N(C(*)C(O*OC(C(*)N(C(*C(C(C)(C)*)=O)=O)O*)=O)=O)*=C 0.000 description 3
- ROORDVPLFPIABK-UHFFFAOYSA-N O=C(Oc1ccccc1)Oc1ccccc1 Chemical compound O=C(Oc1ccccc1)Oc1ccccc1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
- A61K31/727—Heparin; Heparan
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—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
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—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
- 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
- A61K47/51—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 non-active ingredient being a modifying agent
- A61K47/56—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 non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—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 non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
- A61K47/593—Polyesters, e.g. PLGA or polylactide-co-glycolide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—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
- 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
- A61K47/51—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 non-active ingredient being a modifying agent
- A61K47/56—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 non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—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 non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
- A61K47/595—Polyamides, e.g. nylon
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—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
- 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
- A61K47/51—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 non-active ingredient being a modifying agent
- A61K47/56—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 non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—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 non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
- A61K47/60—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 non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/12—Polyester-amides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
Description
本発明の実施形態に従って使用できるA群薬剤を構成するジオール−ジアミン類は、一般式(III)を有する化合物である:
B群薬剤を構成する有用なジカルボン酸類は、一般式(IV)1を有する化合物である:
コポリマーである、式(VII)のコ−ポリ−{N,N’−セバコイル−ビス−(L−ロイシン)−1,6−ヘキシレンジエステル}を合成して、本発明の実施において使用することができる:
コポリマーである、式(VIII)のコ−ポリ−{N,N’−セバコイル―ビス―(L−ロイシン)−1,4−ブチレンジエステル}を合成して、本発明の実施において使用することができる:
コポリマーである、式(IX)のコ−ポリ−{N,N’−アジポイル―ビス―(L−ロイシン)−1,4−ブチレンジエステル}を合成して、本発明の実施において使用することができる:
コポリマーである、式(X)のコ−ポリ−{N,N’−アジポイル―ビス―(L−アラニン)−1,4−ブチレンジエステル}を合成して、本発明の実施において使用する:
本発明の治療薬類は、PEAにペンダント基として又は鎖内の基として結合するか、あるいはPEAポリマーと物理的に混合する。前記薬剤は、高分子量の薬剤でであり、それをペンダント基として又は鎖内の基として結合させることもできると認識すべきである。
本発明のポリマーは、A部分(A)、B部分(B)、及びAとBをつなぐ任意の結合(L1)を有するポリマー部分を含むことができる。ポリマーの残部は、薬剤(X)、及びXとポリマーとをつなぐ結合(L2)を含む。このPEA−治療薬の組み合わせは一般に式(XI)で表すことができる:
(i)XはTEMPOであり、及びL2は次のもの:
高分子量の薬剤は、PEAにブロックコポリマーとして結合する。PEA類にポリマーブロックとして組み込むことができる薬剤の例としては、ヘパリン、ヒアルロン酸、及びポリ(エチレングリコール)(PEG)が挙げられるが、これらに限定されない。
PEAとヘパリンのブロックコポリマーは、アミノ末端処理されたPEAをヘパリン−アルデヒド付加物と混合することによって調製する。ヘパリン−アルデヒド付加物の例は、式(XXVI)で表される:
PEAとPEGとのブロックコポリマーは、様々な技術を用いて調製する。一実施形態では、アミノ末端処理されたPEAを、カルボキシル末端処理されたPEA(ネクター社(Nektar Corp.))と、例えばEDC又はDCCの存在下で混合して、式(XXVIII)で表される次の構造物を形成する:
式(XXIV)のPEAは、次の手順に従って調製する:
L−ロイシン―ε―L−リシンベンジルエステル−2TosOHの調製方法
乾燥トリエチレンアミン(61.6ml、0.44モル)を、ビス−(L−ロイシン)−1,6−ヘキシレンジエステルのジ−p−トルエンスルホン酸塩(120.4グラム、0.18モル)と、L−ロイシン−ε―L−リシンベンジルエステルのジ−p−トルエンスルホン酸塩(13.863グラム、0.02モル)と、ジ−p−ニトロフェニルセバシネート(88.88グラム、0.2モル)との乾燥DMC(110ml)中の混合物に加える。この混合物を80℃で12時間攪拌して加熱する。この混合物を、次に室温まで冷却し、エタノール(300ml)で希釈して、水1リットルに流し入れる。ポリマーを分離し、水洗いして、真空乾燥させる。遊離カルボキシル基が、パラジウム触媒による水素化分解によって生じる。エタノール(1200ml)とポリマー(100mg)を、2リットルのフラスコに、パラジウム担持炭素触媒(5グラム)(アルドリッチ(Aldrich))と共に加える。水素をバブリングさせて、混合物全体を24時間攪拌して、パラジウム担持炭素触媒を遠心分離法によって分離して溶液を残す。
式(XIX)で表されるコポリマーは、式(XXIV)で表されるコポリマーを調製するのに用いられる方法と類似した方法において、L−ロイシン−ε―L−リシンHClをL−リシンHClと置き換えることで調製する。理論又は作用機序に束縛されたくはないが、本発明の一実施形態に従って式(XIX)のPEAを調製するための推奨される反応機構を図2に示す。
式(XXII)のPEAは、次の手順に従って調製する:
コ−ポリ−{[N,N’−セバコイル―ビス―(L−ロイシン)−1,4−ブチレンジエステル]−[N,N’−セバコイル―L−リシン−4−カルボキシ−TEMPO無水物]}の調製方法
式(XXV)のPEAは、次の手順に従って調製する:
エストラジオールと3,9−ジエチリデン−2,4,8,10−テトラオキサスピロ−[5,5]−ウンデカン(DETOSU)との複合物の調製方法
L−ロイシン(32.80グラム、0.25モル)と、p−トルエンスルホン酸(104.6グラム、0.55モル)と、1,3−ジヒドロキシアセトン二量体(22.53グラム、0.125モル)と、ベンゼン200mlとを1リットルフラスコに加える。この溶液を80℃で8時間加熱して、縮合物をディーン・スターク・トラップに回収する。固体を溶媒から回転蒸発により分離して、ブフナー漏斗において水(2回、1回1リットル)ですすぎ、そして真空オーブン内で乾燥させる。
アミノ末端処理されたPEA又はカルボキシル末端処理されたPEAの調製方法
PEAの調製に使用されるモノマー類は、アミノ末端鎖と活性化カルボキシ末端鎖とのおよそ50/50の分布を、重合中のいずれかの点で提供する。アミノ末端処理されたPEA類は、生体適合性を有する低分子量の連鎖停止剤である、1,4−ジアミノブタン(プトレシン)を用いて調製し、前記1,4−ジアミノブタンを大過剰で添加することで、重合終了時、又は重合が所望の分子量に達した時に、鎖を全てアミノ基で末端処理する。カルボキシル末端処理されたPEA類は、幾つかの方法で調製する。一つの方法では、ジカルボン酸化合物、例えば、ジ−p−ニトロフェニルセバシネートを過剰のPEAと化合する。この実施形態は扱い易いが、ポリマーの最終分子量を低くするという、潜在的な欠点を有する。別の方法は、アミノ末端鎖と活性化カルボキシル末端鎖との50/50の分布を含有するPEAを、このPEAを薬剤、例えば無水コハク酸と反応させることで更に誘導体化して、アミノ基をカルボキシル基に変換するものである。
ヘパリンをアミノ末端処理されたPEAと結合することによる、PEA−ヘパリン複合物の調製方法
PEA−ヘパリン複合物は、アミノ末端処理されたPEAを、ヘパリンの酸化解裂によって形成されたヘパリン−アルデヒド付加物と結合することで調製する。アミノ末端処理されたPEA(50g)を、DMAC/水(1リットル、40:1)を入れた反応器に窒素下で加える。ヘパリン−アルデヒド付加物(7.5g)とシアノ水素化ホウ素塩(0.2g;3.2ミリモル)とをこの溶液に加えて、60℃で12時間窒素下で加熱して、室温まで冷却し、そしてメタノールに滴下する。PEA−ヘパリン複合物をろ過して、水(1回250ml)で3回洗浄して、真空乾燥させる。
アミノ末端処理されたPEAを用いたPEA−PEG複合物の調製方法
アミノ末端処理されたPEAは、アルデヒド結合/イミン還元、カルボキシル末端処理されたPEGのカルボジイミド結合、及びPEG−マレイミドとアミン末端処理されたPEAとの結合によってペグ化する。
本発明のポリマーは、活性剤とPEAポリマーとの物理的ブレンドである。活性剤は、PEAを溶解するのに用いられる溶媒(単数又は複数)に完全に溶解されてよい。更に、活性剤は、微粒子の懸濁液又は分散液として存在していてよい。水混和性溶媒を使用して、PEAを溶解させる。その結果、活性剤もまた、PEA相中に存在する別の非混和性溶媒相に溶解又は懸濁してもよい。
Claims (2)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/405,976 US8658210B2 (en) | 2006-04-17 | 2006-04-17 | Polyesteramide platform for site specific drug delivery |
US11/405,976 | 2006-04-17 | ||
PCT/US2007/009290 WO2007123872A2 (en) | 2006-04-17 | 2007-04-13 | Polyesteramide platform for site specific drug delivery |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2009536159A JP2009536159A (ja) | 2009-10-08 |
JP2009536159A5 JP2009536159A5 (ja) | 2010-06-03 |
JP5443159B2 true JP5443159B2 (ja) | 2014-03-19 |
Family
ID=38605110
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009506531A Expired - Fee Related JP5443159B2 (ja) | 2006-04-17 | 2007-04-13 | 部位特異的ドラッグデリバリのためのポリエステルアミドプラットフォーム |
Country Status (4)
Country | Link |
---|---|
US (4) | US8658210B2 (ja) |
EP (1) | EP2010142A2 (ja) |
JP (1) | JP5443159B2 (ja) |
WO (1) | WO2007123872A2 (ja) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7910152B2 (en) * | 2006-02-28 | 2011-03-22 | Advanced Cardiovascular Systems, Inc. | Poly(ester amide)-based drug delivery systems with controlled release rate and morphology |
US8367108B2 (en) * | 2006-09-01 | 2013-02-05 | Bezwada Biomedical, Llc | Functionalized non-phenolic amino acids and absorbable polymers therefrom |
US20080200377A1 (en) * | 2007-02-16 | 2008-08-21 | Trollsas Mikael O | Polymer particles |
US8252361B2 (en) | 2007-06-05 | 2012-08-28 | Abbott Cardiovascular Systems Inc. | Implantable medical devices for local and regional treatment |
JP2011506644A (ja) * | 2007-12-06 | 2011-03-03 | メディバス エルエルシー | オリゴ−エチレングリコールベースのポリマー組成物および使用方法 |
EP2346537B1 (en) * | 2008-09-22 | 2016-11-09 | Tyrx, Inc. | Linear polyesteramides from aminophenolic esters |
CN102186507A (zh) * | 2008-10-15 | 2011-09-14 | 梅迪沃什有限公司 | 可生物降解的脯氨酸基聚合物 |
US9839628B2 (en) | 2009-06-01 | 2017-12-12 | Tyrx, Inc. | Compositions and methods for preventing sternal wound infections |
CN102094066B (zh) * | 2010-12-13 | 2013-07-31 | 华南农业大学 | 一种筛选ε-聚赖氨酸产生菌的方法 |
KR101390589B1 (ko) | 2012-05-30 | 2014-04-30 | 가천대학교 산학협력단 | 다이아민을 포함하는 당뇨병의 예방 또는 치료용 조성물 |
EP2784101A1 (en) * | 2013-03-28 | 2014-10-01 | Nitto Europe N.V | Hydroxyphenyl functionalized poly(ester amide) |
CN104448300B (zh) * | 2014-12-09 | 2017-01-11 | 西安医学院 | 低分子量l-聚谷氨酸-丝裂霉素c及其合成方法和应用 |
US11065337B2 (en) | 2015-12-14 | 2021-07-20 | University of Pittsburgh—of the Commonwealth System of Higher Education | Complex coacervate for controlled release and related methods |
US11298423B2 (en) | 2016-03-04 | 2022-04-12 | University of Pittsburgh—of the Commonwealth System of Higher Education | Protection and delivery of multiple therapeutic proteins |
CN108743972A (zh) * | 2018-06-21 | 2018-11-06 | 东华大学 | 一种氨基酸基聚酯胺胶束、制备方法及其应用 |
CN110652502A (zh) * | 2018-06-28 | 2020-01-07 | 复旦大学 | 一种靶向治疗类风湿关节炎的药物组合物 |
CN113318264A (zh) * | 2021-05-28 | 2021-08-31 | 瑞聚再生(厦门)医学科技有限公司 | 一种可降解聚氨酯生物材料及其制备方法和应用 |
CN115381851B (zh) * | 2022-07-06 | 2023-12-19 | 重庆市妇幼保健院(重庆市妇产科医院、重庆市遗传与生殖研究所) | 一种自组装纳米抗凝、溶栓药物、其制备方法及应用 |
Family Cites Families (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5324519A (en) * | 1989-07-24 | 1994-06-28 | Atrix Laboratories, Inc. | Biodegradable polymer composition |
BR9507313B8 (pt) | 1994-04-08 | 2016-06-07 | Atrix Lab Inc | composição líquida de liberação adequada para a formação de um implante de liberação controlada, sistema polimérico, curativo fílmico microporoso biodegradável, e, precursor de um implante de liberação controlada para a implantação em um indivíduo |
US5684889A (en) * | 1995-04-28 | 1997-11-04 | Sloan-Kettering Institute For Cancer Research | Parametric image representation of imaging agent kinetics |
ES2235312T3 (es) | 1997-01-28 | 2005-07-01 | United States Surgical Corporation | Poliesteramida, su preparacion y dispositivos quirurgicos fabricados a partir de la misma. |
US20040009229A1 (en) | 2000-01-05 | 2004-01-15 | Unger Evan Charles | Stabilized nanoparticle formulations of camptotheca derivatives |
US6703040B2 (en) | 2000-01-11 | 2004-03-09 | Intralytix, Inc. | Polymer blends as biodegradable matrices for preparing biocomposites |
US6585716B2 (en) | 2000-04-05 | 2003-07-01 | Biocardia, Inc. | Method of treating the heart |
US20060177416A1 (en) | 2003-10-14 | 2006-08-10 | Medivas, Llc | Polymer particle delivery compositions and methods of use |
US6503538B1 (en) | 2000-08-30 | 2003-01-07 | Cornell Research Foundation, Inc. | Elastomeric functional biodegradable copolyester amides and copolyester urethanes |
US6720007B2 (en) * | 2000-10-25 | 2004-04-13 | Tufts University | Polymeric microspheres |
US20060286063A1 (en) * | 2000-11-06 | 2006-12-21 | Afmedica, Inc. | Combination drug therapy for reducing scar tissue formation |
US20030049320A1 (en) | 2000-12-18 | 2003-03-13 | Wockhardt Limited | Novel in-situ forming controlled release microcarrier delivery system |
US6692466B1 (en) | 2000-12-21 | 2004-02-17 | Advanced Cardiovascular Systems, Inc. | Drug delivery catheter with retractable needle |
TWI353854B (en) | 2002-06-25 | 2011-12-11 | Alza Corp | Short duration depot formulations |
CA2513443A1 (en) | 2003-02-26 | 2004-09-10 | Medivas, Llc | Bioactive stents and methods for use thereof |
US9149440B2 (en) | 2003-09-02 | 2015-10-06 | University Of South Florida | Nanoparticles for drug-delivery |
US7311901B2 (en) | 2003-10-10 | 2007-12-25 | Samyang Corporation | Amphiphilic block copolymer and polymeric composition comprising the same for drug delivery |
US7220816B2 (en) * | 2003-12-16 | 2007-05-22 | Advanced Cardiovascular Systems, Inc. | Biologically absorbable coatings for implantable devices based on poly(ester amides) and methods for fabricating the same |
US7273469B1 (en) | 2003-12-31 | 2007-09-25 | Advanced Cardiovascular Systems, Inc. | Modified needle catheter for directional orientation delivery |
US8685431B2 (en) | 2004-03-16 | 2014-04-01 | Advanced Cardiovascular Systems, Inc. | Biologically absorbable coatings for implantable devices based on copolymers having ester bonds and methods for fabricating the same |
US20050265960A1 (en) * | 2004-05-26 | 2005-12-01 | Pacetti Stephen D | Polymers containing poly(ester amides) and agents for use with medical articles and methods of fabricating the same |
GB0412866D0 (en) | 2004-06-09 | 2004-07-14 | Novartis Ag | Organic compounds |
US20060034889A1 (en) | 2004-08-16 | 2006-02-16 | Macromed, Inc. | Biodegradable diblock copolymers having reverse thermal gelation properties and methods of use thereof |
US7166680B2 (en) * | 2004-10-06 | 2007-01-23 | Advanced Cardiovascular Systems, Inc. | Blends of poly(ester amide) polymers |
US8609123B2 (en) | 2004-11-29 | 2013-12-17 | Advanced Cardiovascular Systems, Inc. | Derivatized poly(ester amide) as a biobeneficial coating |
CA2596011C (en) | 2005-02-17 | 2013-05-14 | Medivas, Llc | Polymer particle delivery compositions and methods of use |
JP5305135B2 (ja) | 2008-08-05 | 2013-10-02 | 株式会社リコー | 潤滑剤薄膜化装置、並びに、これを備える画像形成装置及びプロセスカートリッジ |
US20140105957A1 (en) | 2011-05-02 | 2014-04-17 | Dsm Ip Assets B.V. | Bis-(alpha-amino-diol-diester) containing polyesteramide for ophtamology |
WO2012150265A1 (en) | 2011-05-02 | 2012-11-08 | Dsm Ip Assets B.V. | Fiber comprising a biodegradable polymer |
CA2839526A1 (en) | 2011-06-23 | 2012-12-27 | Dsm Ip Assets B.V. | Micro- or nanoparticles comprising a biodegradable polyesteramide copolymer for use in the delivery of bioactive agents |
-
2006
- 2006-04-17 US US11/405,976 patent/US8658210B2/en not_active Expired - Fee Related
-
2007
- 2007-04-13 JP JP2009506531A patent/JP5443159B2/ja not_active Expired - Fee Related
- 2007-04-13 EP EP07755524A patent/EP2010142A2/en not_active Withdrawn
- 2007-04-13 WO PCT/US2007/009290 patent/WO2007123872A2/en active Application Filing
-
2014
- 2014-01-07 US US14/149,533 patent/US8865148B2/en not_active Expired - Fee Related
- 2014-09-22 US US14/493,197 patent/US9095619B2/en not_active Expired - Fee Related
-
2015
- 2015-06-25 US US14/750,732 patent/US9603943B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US20150010491A1 (en) | 2015-01-08 |
US8865148B2 (en) | 2014-10-21 |
US20140120053A1 (en) | 2014-05-01 |
WO2007123872A3 (en) | 2008-03-13 |
US20070243256A1 (en) | 2007-10-18 |
US20150290336A1 (en) | 2015-10-15 |
US9095619B2 (en) | 2015-08-04 |
US8658210B2 (en) | 2014-02-25 |
JP2009536159A (ja) | 2009-10-08 |
US9603943B2 (en) | 2017-03-28 |
EP2010142A2 (en) | 2009-01-07 |
WO2007123872A2 (en) | 2007-11-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5443159B2 (ja) | 部位特異的ドラッグデリバリのためのポリエステルアミドプラットフォーム | |
US8329157B2 (en) | Polymers containing poly(hydroxyalkanoates) and agents for use with medical articles and methods of fabricating the same | |
US7361726B2 (en) | Poly(hydroxyalkanoate-co-ester amides) and agents for use with medical articles | |
US8808723B2 (en) | Polymers containing poly(ester amides) and agents for use with medical articles and methods of fabricating the same | |
US7214759B2 (en) | Biologically absorbable coatings for implantable devices based on polyesters and methods for fabricating the same | |
US7795467B1 (en) | Bioabsorbable, biobeneficial polyurethanes for use in medical devices | |
CN103619910B (zh) | 用于药物递送的新颖的聚酯酰胺共聚物 | |
JP6135870B2 (ja) | 生分解性ポリマーを含む繊維 | |
CN101543632A (zh) | 一种结构精确的新型两亲性聚合物为载体的抗肿瘤前药及合成方法 | |
US20080014170A1 (en) | Drug delivery polyanhydride composition and method | |
US8603634B2 (en) | End-capped poly(ester amide) copolymers | |
Mahi | Hybrid Arborescent Polypept (o) ides for Biomedical Applications |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100413 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20100413 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20120816 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120925 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20121225 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130107 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130325 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130730 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20131203 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20131219 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |