KR100566911B1 - 약물 전달체용 음이온기-함유 양친성 블록 공중합체 및 그의 양이온성 약물과의 복합체 - Google Patents
약물 전달체용 음이온기-함유 양친성 블록 공중합체 및 그의 양이온성 약물과의 복합체 Download PDFInfo
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- KR100566911B1 KR100566911B1 KR1020010036203A KR20010036203A KR100566911B1 KR 100566911 B1 KR100566911 B1 KR 100566911B1 KR 1020010036203 A KR1020010036203 A KR 1020010036203A KR 20010036203 A KR20010036203 A KR 20010036203A KR 100566911 B1 KR100566911 B1 KR 100566911B1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/664—Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
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- 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
- A61K47/69—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
- A61K47/6905—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 a colloid or an emulsion
- A61K47/6907—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 a colloid or an emulsion the form being a microemulsion, nanoemulsion or micelle
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- 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
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82B—NANOSTRUCTURES FORMED BY MANIPULATION OF INDIVIDUAL ATOMS, MOLECULES, OR LIMITED COLLECTIONS OF ATOMS OR MOLECULES AS DISCRETE UNITS; MANUFACTURE OR TREATMENT THEREOF
- B82B1/00—Nanostructures formed by manipulation of individual atoms or molecules, or limited collections of atoms or molecules as discrete units
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
Abstract
Description
제조예 | 고분자 | 중량 평균 분자량(달톤) |
1 | mPEG-PLA | 2,000-1,765 |
2 | mPEG-PLGA | 5,000-4,500 |
3 | mPEG-PLDO | 12,000-10,000 |
4 | mPEG-PCL | 12,000-5,000 |
음이온기-함유 A-B 형 블록 공중합체의 합성
실시예 | 고분자 | 중량 평균 분자량(달톤) | |
A | B | ||
1 | mPEG-PLA-O-SO3 -Na+ | 2,000 | 1,765 |
2 | mPEG-PLGA-O-SO3 -Na+ | 5,000 | 4,500 |
3 | mPEG-PLDO-O-SO3 -Na+ | 12,000 | 10,000 |
4 | mPEG-PCL-O-SO3 -Na+ | 12,000 | 5,000 |
실시예 | 고분자 | 중량 평균 분자량(달톤) | |
A | B | ||
5 | mPEG-PLA-O-PO3 2-2Na+ | 2,000 | 1,765 |
6 | mPEG-PLGA-O-PO3 2-2Na+ | 5,000 | 4,500 |
7 | mPEG-PLDO-O-PO3 2-2Na+ | 12,000 | 10,000 |
8 | mPEG-PCL-O-PO3 2-2Na+ | 12,000 | 5,000 |
실시예 10∼12: 카복시기(-COO - Na + )의 도입
실시예 9의 방법에 따라, 제조예 2∼4에서 합성한 고분자와 석시닐 디클로라이드를 반응시켜 카복시기 함유 공중합체를 합성하였다. 실시예 9∼12에서 합성한 고분자를 표 4에 나타내었다.
실시예 | 고분자 | 중량 평균 분자량(달톤) | |
A | B | ||
9 | mPEG-PLA-O-CO(CH2)2COO-Na+ | 2,000 | 1,765 |
10 | mPEG-PLGA-O-CO(CH2)2COO-Na+ | 5,000 | 4,500 |
11 | mPEG-PLDO-O-CO(CH2)2COO-Na+ | 12,000 | 10,000 |
12 | mPEG-PCL-O-CO(CH2)2COO-Na+ | 12,000 | 5,000 |
Claims (12)
- 하기 화학식 1의 블록 공중합체:[화학식 1]C-(L)p-XM상기 식에서,X는 음이온기이고,M은 H+ 또는 양이온기이며,C는 A-B (여기에서, A는 친수성 고분자이고, B는 소수성 고분자이다)이고,L은 -O-, -NH-, -S- 또는 -COO-이며,B의 말단이 -OH, -NH2, -SH 또는 -COOH일 때 p는 0이고, B의 말단이 -OH, -NH2, -SH 및 -COOH가 아닐 때 p는 1이다.
- 제1항에 있어서,A는 폴리알킬렌글리콜, 폴리알킬렌옥사이드, 폴리비닐피롤리돈, 폴리사카라이드, 폴리아크릴아미드, 폴리메타크릴아미드, 폴리비닐알콜 및 그의 유도체로 구성된 그룹으로부터 선택되고,B는 폴리(α-하이드록시산); 폴리에스테르; 폴리우레탄; 폴리카보네이트; 폴리포스파진; 비이온성 측쇄를 갖는 폴리아미노산 및 그들의 유도체; 및 그들의 공중합체로 구성된 그룹으로부터 선택되는 블록 공중합체.
- 제2항에 있어서,A는 폴리에틸렌글리콜, 폴리(에틸렌-코-프로필렌)글리콜, 폴리비닐피롤리돈, 폴리아크릴아미드, 폴리비닐알콜 및 그의 유도체로 구성된 그룹으로부터 선택되고,B는 폴리락트산, 폴리글리콜산, 폴리카프로락톤, 폴리(디옥산-2-온), 및 이들의 공중합체, 폴리언하이드라이드, 폴리오르소에스테르, 폴리포스파진 및 그의 유도체로 구성된 그룹으로부터 선택되는 블록 공중합체.
- 제3항에 있어서,A는 폴리에틸렌글리콜 또는 그의 유도체이고,B는 폴리락트산, 폴리글리콜산, 폴리카프로락톤, 폴리(디옥산-2-온) 및 이들의 공중합체로 구성된 그룹으로부터 선택되는 블록 공중합체.
- 제1항에 있어서, A는 하기 반응식 1에 따라 제조되는 분해성 유도체인 블록 공중합체:[반응식 1]nZ + (n-1)Y → Z-(Y-Z)n-2-Y-Z상기 식에서,Z는 분자량 5,000 달톤 이하의 수용성 고분자이고,Y는 HOOC-(CH2)m-COOH 또는 O=C=N-(CH2)m-N=C=O(여기에서, m은 0∼10의 정수이다)이며,n은 2∼100의 정수이다.
- 제1항 내지 제5항중 어느 한 항에 있어서, A 및 B의 중량 평균 분자량이 각각 100∼100,000 달톤인 블록 공중합체.
- 제1항 내지 제5항중 어느 한 항에 있어서, X는 -SO3 -, -PO3 2-, >PO2 - 또는 -CO-(CH2)z-COO-(여기서, z는 0∼4의 정수이며, X가 >PO2 - 인 경우 두개의 C-(L)p 그룹과 결합된다)인 블록 공중합체.
- 제1항 내지 제5항중 어느 한 항에 있어서, M은 1가 또는 2가의 금속이온인 블록 공중합체.
- 제8항에 있어서, M이 Li+, Na+, K+, Ca2+, Mg2+, Zn2+ 또는 Cu2+인 블록 공중합체.
- 하기 화학식 2의 약물-고분자 복합체:[화학식 2]{C-(L)p-X}q-D상기 식에서,C, L, p 및 X는 각각 제1항에서 정의된 바와 같고,D는 단분자 약물, 펩타이드, 단백질 및 효소로 구성된 그룹으로부터 선택되는 양이온성 약물이며,q는 1 이상의 정수이다.
- 삭제
- 제10항에 있어서, 고분자 미셀, 나노파티클 또는 고분자 젤을 형성하는 복합체.
Priority Applications (18)
Application Number | Priority Date | Filing Date | Title |
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KR1020010036203A KR100566911B1 (ko) | 2001-06-25 | 2001-06-25 | 약물 전달체용 음이온기-함유 양친성 블록 공중합체 및 그의 양이온성 약물과의 복합체 |
US10/104,587 US6890560B2 (en) | 2001-06-25 | 2002-03-21 | Negatively charged amphiphilic block copolymer as drug carrier |
ES02730999T ES2269694T3 (es) | 2001-06-25 | 2002-06-05 | Copolimero de bloque afifilo cargado negativamente como vehiculo para farmacos y complejo del mismo con farmaco cargado positivamente. |
DE60214173T DE60214173T2 (de) | 2001-06-25 | 2002-06-05 | Negativ geladenes amphiphiles blockcopolymer als arzneistoffträger und komplex davon mit postitiv geladenem arzneistoff |
PCT/KR2002/001074 WO2003000778A1 (en) | 2001-06-25 | 2002-06-05 | Negatively charged amphiphilic block copolymer as drug carrier and complex thereof with positively charged drug |
AU2002303027A AU2002303027C1 (en) | 2001-06-25 | 2002-06-05 | Negatively charged amphiphilic block copolymer as drug carrier and complex thereof with positively charged drug |
EP02730999A EP1399501B1 (en) | 2001-06-25 | 2002-06-05 | Negatively charged amphiphilic block copolymer as drug carrier and complex thereof with positively charged drug |
AT02730999T ATE337357T1 (de) | 2001-06-25 | 2002-06-05 | Negativ geladenes amphiphiles blockcopolymer als arzneistoffträger und komplex davon mit postitiv geladenem arzneistoff |
NZ530176A NZ530176A (en) | 2001-06-25 | 2002-06-05 | Negatively charged amphiphilic block copolymer as drug carrier and complex thereof with positively charged drug |
IL15916602A IL159166A0 (en) | 2001-06-25 | 2002-06-05 | Negatively charged amphiphilic block copolymer as drug carrier and complex thereof with positively charged drug |
CNB028127269A CN1226332C (zh) | 2001-06-25 | 2002-06-05 | 作为药物载体的带负电荷的两亲嵌段共聚物及其与带正电荷的药物的配合物 |
CA002449244A CA2449244C (en) | 2001-06-25 | 2002-06-05 | Negatively charged amphiphilic block copolymer as drug carrier and complex thereof with positively charged drug |
JP2003507178A JP4154328B2 (ja) | 2001-06-25 | 2002-06-05 | 薬剤キャリヤーとしての陰電荷両親媒性ブロック共重合体および当該共重合体と陽電荷性薬剤との複合体 |
MXPA03011619A MXPA03011619A (es) | 2001-06-25 | 2002-06-05 | Copolimero de bloque anfifilico negativamente cargado como portador de farmaco y complejo del mismo con farmaco positivamente cargado. |
BRPI0210335A BRPI0210335B8 (pt) | 2001-06-25 | 2002-06-05 | copolímero de blocos, e, composição |
ZA2003/09357A ZA200309357B (en) | 2001-06-25 | 2003-12-02 | Negatively charged amphiphilic block copolymer as drug carrier and complex thereof with positively charged drug |
IL159166A IL159166A (en) | 2001-06-25 | 2003-12-03 | Negatively charged amphiphilic copolymer block as a drug carrier and its complex with a positively charged drug |
HK04109869A HK1067950A1 (en) | 2001-06-25 | 2004-12-14 | Negatively charged amphiphilic block copolymer as drug carrier and complex thereof with positively charged drug |
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KR1020010036203A KR100566911B1 (ko) | 2001-06-25 | 2001-06-25 | 약물 전달체용 음이온기-함유 양친성 블록 공중합체 및 그의 양이온성 약물과의 복합체 |
Publications (2)
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KR20030000433A KR20030000433A (ko) | 2003-01-06 |
KR100566911B1 true KR100566911B1 (ko) | 2006-04-03 |
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KR1020010036203A KR100566911B1 (ko) | 2001-06-25 | 2001-06-25 | 약물 전달체용 음이온기-함유 양친성 블록 공중합체 및 그의 양이온성 약물과의 복합체 |
Country Status (17)
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US (1) | US6890560B2 (ko) |
EP (1) | EP1399501B1 (ko) |
JP (1) | JP4154328B2 (ko) |
KR (1) | KR100566911B1 (ko) |
CN (1) | CN1226332C (ko) |
AT (1) | ATE337357T1 (ko) |
AU (1) | AU2002303027C1 (ko) |
BR (1) | BRPI0210335B8 (ko) |
CA (1) | CA2449244C (ko) |
DE (1) | DE60214173T2 (ko) |
ES (1) | ES2269694T3 (ko) |
HK (1) | HK1067950A1 (ko) |
IL (2) | IL159166A0 (ko) |
MX (1) | MXPA03011619A (ko) |
NZ (1) | NZ530176A (ko) |
WO (1) | WO2003000778A1 (ko) |
ZA (1) | ZA200309357B (ko) |
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KR101230598B1 (ko) | 2011-02-28 | 2013-02-15 | 부산대학교 산학협력단 | 페하 응답성을 가지는 히스트딘이 공유결합된 덱스트란과 메톡시폴리에틸렌글리콜 블록공중합체 |
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JP4154328B2 (ja) | 2008-09-24 |
DE60214173T2 (de) | 2007-08-23 |
ATE337357T1 (de) | 2006-09-15 |
EP1399501A1 (en) | 2004-03-24 |
AU2002303027B2 (en) | 2005-06-09 |
DE60214173D1 (de) | 2006-10-05 |
CN1520437A (zh) | 2004-08-11 |
CA2449244C (en) | 2007-10-02 |
ES2269694T3 (es) | 2007-04-01 |
CN1226332C (zh) | 2005-11-09 |
MXPA03011619A (es) | 2004-04-05 |
EP1399501B1 (en) | 2006-08-23 |
ZA200309357B (en) | 2005-05-25 |
BR0210335A (pt) | 2004-07-20 |
NZ530176A (en) | 2005-06-24 |
WO2003000778A1 (en) | 2003-01-03 |
HK1067950A1 (en) | 2005-04-22 |
JP2004530768A (ja) | 2004-10-07 |
BRPI0210335B8 (pt) | 2021-05-25 |
BR0210335B1 (pt) | 2014-06-24 |
IL159166A (en) | 2007-12-03 |
US6890560B2 (en) | 2005-05-10 |
CA2449244A1 (en) | 2003-01-03 |
KR20030000433A (ko) | 2003-01-06 |
US20030017206A1 (en) | 2003-01-23 |
IL159166A0 (en) | 2004-06-01 |
EP1399501A4 (en) | 2005-02-16 |
AU2002303027C1 (en) | 2006-06-01 |
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