JP2002508758A - 生物的に活性な材料 - Google Patents
生物的に活性な材料Info
- Publication number
- JP2002508758A JP2002508758A JP50182699A JP50182699A JP2002508758A JP 2002508758 A JP2002508758 A JP 2002508758A JP 50182699 A JP50182699 A JP 50182699A JP 50182699 A JP50182699 A JP 50182699A JP 2002508758 A JP2002508758 A JP 2002508758A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- dextrin
- drug conjugate
- drug
- conjugate according
- 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.)
- Ceased
Links
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- 229920000642 polymer Polymers 0.000 claims abstract description 46
- 229940079593 drug Drugs 0.000 claims abstract description 44
- 239000000580 polymer-drug conjugate Substances 0.000 claims abstract description 32
- 239000000562 conjugate Substances 0.000 claims abstract description 18
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- 239000005017 polysaccharide Substances 0.000 claims abstract description 7
- 150000004676 glycans Chemical class 0.000 claims abstract description 5
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- 238000000034 method Methods 0.000 claims description 36
- 229960004679 doxorubicin Drugs 0.000 claims description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 26
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- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
- MWWSFMDVAYGXBV-RUELKSSGSA-N Doxorubicin hydrochloride Chemical compound Cl.O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 MWWSFMDVAYGXBV-RUELKSSGSA-N 0.000 claims description 3
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
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- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
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- 239000006166 lysate Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 1
- 229960001924 melphalan Drugs 0.000 description 1
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 1
- 229960001428 mercaptopurine Drugs 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- 229960004857 mitomycin Drugs 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000036457 multidrug resistance Effects 0.000 description 1
- OKPYIWASQZGASP-UHFFFAOYSA-N n-(2-hydroxypropyl)-2-methylprop-2-enamide Chemical compound CC(O)CNC(=O)C(C)=C OKPYIWASQZGASP-UHFFFAOYSA-N 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 230000000242 pagocytic effect Effects 0.000 description 1
- 238000005897 peptide coupling reaction Methods 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920001308 poly(aminoacid) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 235000019423 pullulan Nutrition 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000000163 radioactive labelling Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 1
- RPENMORRBUTCPR-UHFFFAOYSA-M sodium;1-hydroxy-2,5-dioxopyrrolidine-3-sulfonate Chemical compound [Na+].ON1C(=O)CC(S([O-])(=O)=O)C1=O RPENMORRBUTCPR-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 230000002277 temperature effect Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- 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
- A61K47/61—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 the organic macromolecular compound being a polysaccharide or a derivative thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9712100.8A GB9712100D0 (en) | 1997-06-12 | 1997-06-12 | Biologically active materials |
| US5427797P | 1997-07-30 | 1997-07-30 | |
| US60/054,277 | 1997-07-30 | ||
| US9712100.8 | 1997-07-30 | ||
| PCT/GB1998/001567 WO1998056424A1 (en) | 1997-06-12 | 1998-06-12 | Biologically active materials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002508758A true JP2002508758A (ja) | 2002-03-19 |
| JP2002508758A5 JP2002508758A5 (https=) | 2005-12-22 |
Family
ID=26311695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50182699A Ceased JP2002508758A (ja) | 1997-06-12 | 1998-06-12 | 生物的に活性な材料 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6338843B1 (https=) |
| EP (1) | EP0998303B1 (https=) |
| JP (1) | JP2002508758A (https=) |
| AT (1) | ATE317703T1 (https=) |
| AU (1) | AU8025998A (https=) |
| DE (1) | DE69833487T9 (https=) |
| WO (1) | WO1998056424A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007529554A (ja) * | 2004-03-19 | 2007-10-25 | プロ−ファーマシューティカルズ，インク． | 多価リガンド結合糖質ポリマーを用いた組成物、および該組成物による転移腫瘍の標的療法 |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1191093C (zh) * | 1998-10-30 | 2005-03-02 | 第一制药株式会社 | Dds化合物及其测定方法 |
| EP1198253A2 (en) * | 1999-06-18 | 2002-04-24 | ML Laboratories Plc | Biologically active materials |
| EP1296719A2 (en) * | 2000-07-01 | 2003-04-02 | ML Laboratories Plc | Dextrin - amphotericin conjugates and their methods of preparation |
| DE60131177T2 (de) * | 2000-09-06 | 2008-08-07 | AP Pharma, Inc., Redwood | Abbaubare polyacetal-polymere |
| DE10112825A1 (de) | 2001-03-16 | 2002-10-02 | Fresenius Kabi De Gmbh | HESylierung von Wirkstoffen in wässriger Lösung |
| DE10129369C1 (de) | 2001-06-21 | 2003-03-06 | Fresenius Kabi De Gmbh | Wasserlösliches, einen Aminozucker aufweisendes Antibiotikum in Form eines Pol ysaccharid-Konjugats |
| DE10209821A1 (de) | 2002-03-06 | 2003-09-25 | Biotechnologie Ges Mittelhesse | Kopplung von Proteinen an ein modifiziertes Polysaccharid |
| ITMI20020681A1 (it) * | 2002-03-29 | 2003-09-29 | Acs Dobfar Spa | Procedimento per la produzione di nanoparticelle di paclitaxel ed albumina |
| US7538092B2 (en) | 2002-10-08 | 2009-05-26 | Fresenius Kabi Deutschland Gmbh | Pharmaceutically active oligosaccharide conjugates |
| WO2004081538A2 (en) | 2003-03-13 | 2004-09-23 | Irm, Llc | Compositions and methods of vinyl oxazolone polymerization |
| WO2005014655A2 (en) | 2003-08-08 | 2005-02-17 | Fresenius Kabi Deutschland Gmbh | Conjugates of hydroxyalkyl starch and a protein |
| US11331392B2 (en) | 2014-12-04 | 2022-05-17 | The Trustees Of Columbia University In The City Of New York | Biodegradable thermo-responsive polymers and uses thereof |
| GB2551979A (en) | 2016-06-30 | 2018-01-10 | Rs Arastirma Egitim Danismanlik Llac Sanayi Ticaret Ltd | Cleavable polymer drug conjugates |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1044798B (it) | 1974-10-15 | 1980-04-21 | Ferruti Paolo | Alti polimeri contenenti acido nicotinico processo per la loro preparazione e loro impiego |
| JPS5756500A (en) * | 1980-09-22 | 1982-04-05 | Otsuka Pharmaceut Co Ltd | Novel bufadienolide-type steroid |
| US4496689A (en) * | 1983-12-27 | 1985-01-29 | Miles Laboratories, Inc. | Covalently attached complex of alpha-1-proteinase inhibitor with a water soluble polymer |
| US5554386A (en) | 1986-07-03 | 1996-09-10 | Advanced Magnetics, Inc. | Delivery of therapeutic agents to receptors using polysaccharides |
| US4793986A (en) * | 1987-02-25 | 1988-12-27 | Johnson Matthey, Inc. | Macromolecular platinum antitumor compounds |
| GB9020861D0 (en) | 1990-09-25 | 1990-11-07 | Ml Lab Plc | Pharmaceutical compositions |
| EP0540751A4 (en) | 1991-05-20 | 1994-10-26 | Eisai Co Ltd | Steroid compound combined with polysaccharide |
| GB9217998D0 (en) * | 1992-08-24 | 1992-10-07 | Wellcome Found | Methods of treating cancer |
| WO1995005199A1 (en) | 1993-08-19 | 1995-02-23 | Dextran Products Limited | Pharmaceutical preparation and a process for making same |
-
1998
- 1998-06-12 JP JP50182699A patent/JP2002508758A/ja not_active Ceased
- 1998-06-12 DE DE69833487T patent/DE69833487T9/de not_active Expired - Fee Related
- 1998-06-12 AU AU80259/98A patent/AU8025998A/en not_active Abandoned
- 1998-06-12 EP EP98928427A patent/EP0998303B1/en not_active Expired - Lifetime
- 1998-06-12 WO PCT/GB1998/001567 patent/WO1998056424A1/en not_active Ceased
- 1998-06-12 AT AT98928427T patent/ATE317703T1/de not_active IP Right Cessation
- 1998-06-12 US US09/445,793 patent/US6338843B1/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007529554A (ja) * | 2004-03-19 | 2007-10-25 | プロ−ファーマシューティカルズ，インク． | 多価リガンド結合糖質ポリマーを用いた組成物、および該組成物による転移腫瘍の標的療法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69833487T9 (de) | 2007-03-01 |
| DE69833487D1 (de) | 2006-04-20 |
| EP0998303A1 (en) | 2000-05-10 |
| AU8025998A (en) | 1998-12-30 |
| US6338843B1 (en) | 2002-01-15 |
| ATE317703T1 (de) | 2006-03-15 |
| DE69833487T2 (de) | 2006-10-12 |
| EP0998303B1 (en) | 2006-02-15 |
| WO1998056424A1 (en) | 1998-12-17 |
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