JP2009518511A5 - - Google Patents
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- JP2009518511A5 JP2009518511A5 JP2008544385A JP2008544385A JP2009518511A5 JP 2009518511 A5 JP2009518511 A5 JP 2009518511A5 JP 2008544385 A JP2008544385 A JP 2008544385A JP 2008544385 A JP2008544385 A JP 2008544385A JP 2009518511 A5 JP2009518511 A5 JP 2009518511A5
- Authority
- JP
- Japan
- Prior art keywords
- polymer conjugate
- formula
- polymer
- group
- 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.)
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- 229920000642 polymer Polymers 0.000 claims 64
- 238000000034 method Methods 0.000 claims 21
- 229940079593 drug Drugs 0.000 claims 11
- 239000003814 drug Substances 0.000 claims 11
- -1 N-[(dimethylamino) -1H-1,2,3-triazolo- [4,5-b] pyridin-1-yl-methylene] -N— Methylmethanaminium hexafluorophosphate N-oxide Chemical class 0.000 claims 9
- 239000000376 reactant Substances 0.000 claims 9
- 229910052783 alkali metal Inorganic materials 0.000 claims 8
- 150000001340 alkali metals Chemical class 0.000 claims 8
- 239000003446 ligand Substances 0.000 claims 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 230000003287 optical effect Effects 0.000 claims 7
- 229930012538 Paclitaxel Natural products 0.000 claims 6
- 239000000975 dye Substances 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 229960001592 paclitaxel Drugs 0.000 claims 6
- 239000000243 solution Substances 0.000 claims 6
- 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 claims 6
- 239000002246 antineoplastic agent Substances 0.000 claims 5
- 239000002872 contrast media Substances 0.000 claims 5
- 239000002405 nuclear magnetic resonance imaging agent Substances 0.000 claims 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound 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 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 4
- 229940123237 Taxane Drugs 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims 4
- 239000002243 precursor Substances 0.000 claims 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims 4
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 claims 2
- DVVGIUUJYPYENY-UHFFFAOYSA-N 1-methylpyridin-2-one Chemical compound CN1C=CC=CC1=O DVVGIUUJYPYENY-UHFFFAOYSA-N 0.000 claims 2
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims 2
- 108010020346 Polyglutamic Acid Proteins 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 239000000999 acridine dye Substances 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229940127093 camptothecin Drugs 0.000 claims 2
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 229960000956 coumarin Drugs 0.000 claims 2
- 235000001671 coumarin Nutrition 0.000 claims 2
- 239000007822 coupling agent Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims 2
- 229960003668 docetaxel Drugs 0.000 claims 2
- 229960004679 doxorubicin Drugs 0.000 claims 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000001022 rhodamine dye Substances 0.000 claims 2
- 230000008685 targeting Effects 0.000 claims 2
- 239000001018 xanthene dye Substances 0.000 claims 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N 1,1'-Carbonyldiimidazole Substances C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 239000007821 HATU Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000012317 TBTU Substances 0.000 claims 1
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical group 0.000 claims 1
- 229940041181 antineoplastic drug Drugs 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 claims 1
- 229920000370 gamma-poly(glutamate) polymer Polymers 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- 229920002643 polyglutamic acid Polymers 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 0 *C(CN(CCCC(CC(O*)=O)CC(O*)=O)CCN(CC(*)=O)CC(O)=O)=O Chemical compound *C(CN(CCCC(CC(O*)=O)CC(O*)=O)CCN(CC(*)=O)CC(O)=O)=O 0.000 description 1
- WMPKEOZUDLUWJQ-UHFFFAOYSA-N CC(C)(C)OC(CN(CCN(CC(OC(C)(C)C)=O)CC(OC(C)(C)C)=O)CCN(CC(OC(C)(C)C)=O)CC(OC(C)(C)C)=O)=O Chemical compound CC(C)(C)OC(CN(CCN(CC(OC(C)(C)C)=O)CC(OC(C)(C)C)=O)CCN(CC(OC(C)(C)C)=O)CC(OC(C)(C)C)=O)=O WMPKEOZUDLUWJQ-UHFFFAOYSA-N 0.000 description 1
- SJMDMGHPMLKLHQ-UHFFFAOYSA-N CC(C)(C)OC(CN)=O Chemical compound CC(C)(C)OC(CN)=O SJMDMGHPMLKLHQ-UHFFFAOYSA-N 0.000 description 1
- UVININLYSAHIFI-UHFFFAOYSA-N CC(C)(C)OC(CNCC(O)=O)=O Chemical compound CC(C)(C)OC(CNCC(O)=O)=O UVININLYSAHIFI-UHFFFAOYSA-N 0.000 description 1
- NDYXQRYPCWDSFH-UHFFFAOYSA-N CC(C)(C)[NH+](NC)[O-] Chemical compound CC(C)(C)[NH+](NC)[O-] NDYXQRYPCWDSFH-UHFFFAOYSA-N 0.000 description 1
- UMVVJNSUIDWYBI-UHFFFAOYSA-N CCCN(CC(OC(C)(C)C)=O)CC(OC(C)(C)C)=O Chemical compound CCCN(CC(OC(C)(C)C)=O)CC(OC(C)(C)C)=O UMVVJNSUIDWYBI-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74229105P | 2005-12-05 | 2005-12-05 | |
| US60/742,291 | 2005-12-05 | ||
| US75791706P | 2006-01-10 | 2006-01-10 | |
| US60/757,917 | 2006-01-10 | ||
| US79073506P | 2006-04-10 | 2006-04-10 | |
| US60/790,735 | 2006-04-10 | ||
| PCT/US2006/045915 WO2007067417A1 (en) | 2005-12-05 | 2006-12-01 | Polyglutamate-amino acid conjugates and methods |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009518511A JP2009518511A (ja) | 2009-05-07 |
| JP2009518511A5 true JP2009518511A5 (https=) | 2010-01-21 |
| JP5237821B2 JP5237821B2 (ja) | 2013-07-17 |
Family
ID=37909775
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008544385A Expired - Fee Related JP5237821B2 (ja) | 2005-12-05 | 2006-12-01 | ポリグルタミン酸−アミノ酸結合体および方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US20070128118A1 (https=) |
| EP (4) | EP2325232A1 (https=) |
| JP (1) | JP5237821B2 (https=) |
| KR (1) | KR20080074207A (https=) |
| CN (2) | CN101321806B (https=) |
| AT (3) | ATE465205T1 (https=) |
| AU (1) | AU2006322254B2 (https=) |
| BR (1) | BRPI0619436A2 (https=) |
| CA (1) | CA2631704A1 (https=) |
| DE (2) | DE602006013893D1 (https=) |
| DK (2) | DK2206736T3 (https=) |
| ES (1) | ES2395461T3 (https=) |
| RU (1) | RU2472812C2 (https=) |
| TW (1) | TW200804461A (https=) |
| WO (1) | WO2007067417A1 (https=) |
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| DE10244847A1 (de) | 2002-09-20 | 2004-04-01 | Ulrich Prof. Dr. Speck | Medizinische Vorrichtung zur Arzneimittelabgabe |
| US9393315B2 (en) | 2011-06-08 | 2016-07-19 | Nitto Denko Corporation | Compounds for targeting drug delivery and enhancing siRNA activity |
| ATE465205T1 (de) | 2005-12-05 | 2010-05-15 | Nitto Denko Corp | Polyglutamat-aminosäure-konjugate und verfahren |
| US9572886B2 (en) | 2005-12-22 | 2017-02-21 | Nitto Denko Corporation | Agent for treating myelofibrosis |
| US8425459B2 (en) | 2006-11-20 | 2013-04-23 | Lutonix, Inc. | Medical device rapid drug releasing coatings comprising a therapeutic agent and a contrast agent |
| US9700704B2 (en) | 2006-11-20 | 2017-07-11 | Lutonix, Inc. | Drug releasing coatings for balloon catheters |
| US8414526B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Medical device rapid drug releasing coatings comprising oils, fatty acids, and/or lipids |
| US8414910B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US8430055B2 (en) | 2008-08-29 | 2013-04-30 | Lutonix, Inc. | Methods and apparatuses for coating balloon catheters |
| US9737640B2 (en) | 2006-11-20 | 2017-08-22 | Lutonix, Inc. | Drug releasing coatings for medical devices |
| US20080276935A1 (en) | 2006-11-20 | 2008-11-13 | Lixiao Wang | Treatment of asthma and chronic obstructive pulmonary disease with anti-proliferate and anti-inflammatory drugs |
| US8414909B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
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| PT2155255E (pt) | 2007-05-09 | 2013-10-15 | Nitto Denko Corp | Composições que incluem um composto hidrofóbico e um conjugado de poliaminoácido |
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| WO2009111271A1 (en) * | 2008-03-06 | 2009-09-11 | Nitto Denko Corporation | Polymer paclitaxel conjugates and methods for treating cancer |
| EP2151249A1 (en) * | 2008-07-28 | 2010-02-10 | Canon Kabushiki Kaisha | PH-sensitive probe comprising polymer and fluorescent dye |
| AU2008359989A1 (en) * | 2008-07-30 | 2010-02-04 | Nitto Denko Corporation | Drug carriers |
| JP5744723B2 (ja) * | 2008-09-12 | 2015-07-08 | 日東電工株式会社 | 線維性疾患のイメージング剤 |
| BRPI0920655A2 (pt) | 2008-10-07 | 2019-07-09 | Rexahn Pharmaceuticals, Inc. | conjugados e hpma-docetaxel ou gencitabina e usos dos mesmos |
| US20100093935A1 (en) * | 2008-10-15 | 2010-04-15 | Nitto Denko Corporation | Method of preparing polyglutamate conjugates |
| KR101721865B1 (ko) | 2009-10-13 | 2017-04-03 | 렉산 파마슈티컬스, 인코포레이티드 | 항암제의 전달을 위한 폴리머 시스템 |
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| CA2969196C (en) * | 2014-12-26 | 2021-04-13 | Nippon Kayaku Kabushiki Kaisha | Pharmaceutical preparation of camptothecin-containing polymer derivative |
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| US20240043615A1 (en) * | 2020-12-04 | 2024-02-08 | The Methodist Hospital System | Amino acid polymer-platinum anticancer drug conjugates |
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2006
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- 2006-12-01 RU RU2008120699/04A patent/RU2472812C2/ru not_active IP Right Cessation
- 2006-12-01 CA CA002631704A patent/CA2631704A1/en not_active Abandoned
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