CA2745972C - Conjugates comprising nanoparticles coated with platinum containing compounds - Google Patents
Conjugates comprising nanoparticles coated with platinum containing compounds Download PDFInfo
- Publication number
- CA2745972C CA2745972C CA2745972A CA2745972A CA2745972C CA 2745972 C CA2745972 C CA 2745972C CA 2745972 A CA2745972 A CA 2745972A CA 2745972 A CA2745972 A CA 2745972A CA 2745972 C CA2745972 C CA 2745972C
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- CA
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- Prior art keywords
- formula
- linker
- platinum
- conjugate
- conjugates
- Prior art date
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 129
- 239000002105 nanoparticle Substances 0.000 title claims abstract description 70
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 45
- 150000001875 compounds Chemical class 0.000 title claims description 34
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 39
- 239000010931 gold Substances 0.000 claims abstract description 37
- 229910052737 gold Inorganic materials 0.000 claims abstract description 36
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 26
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 claims abstract description 25
- 201000011510 cancer Diseases 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 229910052709 silver Inorganic materials 0.000 claims abstract description 11
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000004332 silver Substances 0.000 claims abstract description 10
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
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- -1 platinum (II) compound Chemical class 0.000 claims description 12
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 238000010255 intramuscular injection Methods 0.000 claims 1
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- 239000000543 intermediate Substances 0.000 description 35
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 33
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- 150000003058 platinum compounds Chemical class 0.000 description 31
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- GWOLZNVIRIHJHB-UHFFFAOYSA-N 11-mercaptoundecanoic acid Chemical compound OC(=O)CCCCCCCCCCS GWOLZNVIRIHJHB-UHFFFAOYSA-N 0.000 description 13
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- 230000002776 aggregation Effects 0.000 description 9
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- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 description 5
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- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 4
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- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 229960002663 thioctic acid Drugs 0.000 description 4
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
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- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 1
- DYAOREPNYXXCOA-UHFFFAOYSA-N 2-sulfanylundecanoic acid Chemical compound CCCCCCCCCC(S)C(O)=O DYAOREPNYXXCOA-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
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- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- 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
- A61K47/6921—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 particulate, a powder, an adsorbate, a bead or a sphere
- A61K47/6923—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 particulate, a powder, an adsorbate, a bead or a sphere the form being an inorganic particle, e.g. ceramic particles, silica particles, ferrite or synsorb
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nanotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medical Informatics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biophysics (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Inorganic Chemistry (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Powder Metallurgy (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08171870 | 2008-12-16 | ||
| EP08171870.2 | 2008-12-16 | ||
| PCT/EP2009/067136 WO2010069941A1 (en) | 2008-12-16 | 2009-12-15 | Conjugates comprising nanoparticles coated with platinum containing compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2745972A1 CA2745972A1 (en) | 2010-06-24 |
| CA2745972C true CA2745972C (en) | 2016-11-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2745972A Active CA2745972C (en) | 2008-12-16 | 2009-12-15 | Conjugates comprising nanoparticles coated with platinum containing compounds |
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| Country | Link |
|---|---|
| US (1) | US9023370B2 (enExample) |
| EP (1) | EP2379114B1 (enExample) |
| JP (1) | JP5873719B2 (enExample) |
| CA (1) | CA2745972C (enExample) |
| CY (1) | CY1115601T1 (enExample) |
| DK (1) | DK2379114T3 (enExample) |
| ES (1) | ES2505890T3 (enExample) |
| HR (1) | HRP20140804T1 (enExample) |
| IL (1) | IL213408A (enExample) |
| PL (1) | PL2379114T3 (enExample) |
| PT (1) | PT2379114E (enExample) |
| SI (1) | SI2379114T1 (enExample) |
| WO (1) | WO2010069941A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0909435D0 (en) * | 2009-06-02 | 2009-07-15 | Univ Strathclyde | Nanoparticle for biomolecule delivery |
| ES2392528B1 (es) * | 2010-12-28 | 2013-10-21 | Endor Nanotechnologies, S.L. | Sistema de liberación de agente terapéutico, composiciones farmacéuticas que lo contienen, su preparación y su uso médico. |
| ITRM20130138A1 (it) | 2013-03-07 | 2014-09-08 | Consiglio Nazionale Ricerche | Assemblato comprendente un assorbitore della luce nel vicino infrarosso legato covalentemente ad un inibitore dell'anidrasi carbonica |
| JP6316011B2 (ja) * | 2014-02-04 | 2018-04-25 | 国立大学法人滋賀医科大学 | 抗癌剤が担持されたナノ粒子 |
| EP3409772B1 (en) * | 2016-01-29 | 2023-06-28 | National University Corporation Hokkaido University | Intracellular substance transport system and use thereof |
| PL236093B1 (pl) | 2017-07-04 | 2020-11-30 | Dominika Szczepaniak | Rozpuszczalne w wodzie kompleksy złota (III), sposób wytwarzania rozpuszczalnych w wodzie kompleksów złota (III) i ich zastosowanie |
| US12364772B2 (en) | 2019-01-08 | 2025-07-22 | Nanonica S.A. | Conjugates comprising nanoparticles coated with platinum derivatives through sulfonyl or phosphonyl-containing linkers |
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|---|---|---|---|---|
| GR851932B (enExample) | 1984-08-14 | 1985-12-13 | Engelhard Corp | |
| JP2866554B2 (ja) | 1992-08-25 | 1999-03-08 | 松下電器産業株式会社 | 情報記録媒体とその製造方法及び情報記録媒体の使用方法 |
| JP2005535604A (ja) | 2002-06-03 | 2005-11-24 | アルニス バイオサイエンシーズ, インコーポレイテッド | 治療剤を含むポリマーナノ物品 |
| WO2006037081A2 (en) * | 2004-09-28 | 2006-04-06 | The Regents Of The University Of California | Nanoparticle radiosensitizers |
| US7601331B2 (en) | 2004-11-10 | 2009-10-13 | National University Of Singapore | NIR-sensitive nanoparticle |
| US20060222595A1 (en) * | 2005-03-31 | 2006-10-05 | Priyabrata Mukherjee | Nanoparticles for therapeutic and diagnostic applications |
| US8785505B2 (en) * | 2005-10-28 | 2014-07-22 | The Regents Of The University Of California | Toxicology and cellular effect of manufactured nanomaterials |
-
2009
- 2009-12-15 PL PL09768395T patent/PL2379114T3/pl unknown
- 2009-12-15 CA CA2745972A patent/CA2745972C/en active Active
- 2009-12-15 WO PCT/EP2009/067136 patent/WO2010069941A1/en not_active Ceased
- 2009-12-15 HR HRP20140804AT patent/HRP20140804T1/hr unknown
- 2009-12-15 DK DK09768395.7T patent/DK2379114T3/da active
- 2009-12-15 US US13/140,347 patent/US9023370B2/en not_active Expired - Fee Related
- 2009-12-15 SI SI200931018T patent/SI2379114T1/sl unknown
- 2009-12-15 ES ES09768395.7T patent/ES2505890T3/es active Active
- 2009-12-15 PT PT97683957T patent/PT2379114E/pt unknown
- 2009-12-15 JP JP2011540141A patent/JP5873719B2/ja not_active Expired - Fee Related
- 2009-12-15 EP EP09768395.7A patent/EP2379114B1/en not_active Not-in-force
-
2011
- 2011-06-06 IL IL213408A patent/IL213408A/en active IP Right Grant
-
2014
- 2014-10-03 CY CY20141100802T patent/CY1115601T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2379114B1 (en) | 2014-07-09 |
| US20110262500A1 (en) | 2011-10-27 |
| SI2379114T1 (sl) | 2014-11-28 |
| US9023370B2 (en) | 2015-05-05 |
| CY1115601T1 (el) | 2017-01-04 |
| JP5873719B2 (ja) | 2016-03-01 |
| IL213408A (en) | 2017-06-29 |
| WO2010069941A1 (en) | 2010-06-24 |
| PT2379114E (pt) | 2014-10-06 |
| CA2745972A1 (en) | 2010-06-24 |
| DK2379114T3 (da) | 2014-09-29 |
| HRP20140804T1 (hr) | 2014-11-07 |
| PL2379114T3 (pl) | 2014-12-31 |
| IL213408A0 (en) | 2011-07-31 |
| ES2505890T3 (es) | 2014-10-10 |
| EP2379114A1 (en) | 2011-10-26 |
| JP2012512149A (ja) | 2012-05-31 |
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