ES2898704T3 - Compuestos de platino funcionalizados con monomaleimida para la terapia del cáncer - Google Patents
Compuestos de platino funcionalizados con monomaleimida para la terapia del cáncer Download PDFInfo
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- ES2898704T3 ES2898704T3 ES16822917T ES16822917T ES2898704T3 ES 2898704 T3 ES2898704 T3 ES 2898704T3 ES 16822917 T ES16822917 T ES 16822917T ES 16822917 T ES16822917 T ES 16822917T ES 2898704 T3 ES2898704 T3 ES 2898704T3
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- alkyl
- alkylene
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage
-
- 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
- A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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|---|---|---|---|
| EP15198739 | 2015-12-09 | ||
| PCT/EP2016/080453 WO2017097986A1 (en) | 2015-12-09 | 2016-12-09 | Monomaleimide-functionalized platinum compounds for cancer therapy |
Publications (1)
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|---|---|
| ES2898704T3 true ES2898704T3 (es) | 2022-03-08 |
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| ES16822917T Active ES2898704T3 (es) | 2015-12-09 | 2016-12-09 | Compuestos de platino funcionalizados con monomaleimida para la terapia del cáncer |
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| JP (1) | JP6867652B2 (https=) |
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| AU (1) | AU2016367306B2 (https=) |
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| DK (1) | DK3386997T3 (https=) |
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| HR (1) | HRP20211466T1 (https=) |
| HU (1) | HUE056897T2 (https=) |
| IL (1) | IL259864B (https=) |
| LT (1) | LT3386997T (https=) |
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| PT (1) | PT3386997T (https=) |
| RS (1) | RS62412B1 (https=) |
| SG (1) | SG11201804885TA (https=) |
| SI (1) | SI3386997T1 (https=) |
| SM (1) | SMT202100709T1 (https=) |
| WO (1) | WO2017097986A1 (https=) |
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| EP3797768A1 (en) * | 2014-06-23 | 2021-03-31 | Placon Therapeutics, Inc. | Maleimide-functionalised platinum for use in the treatment of cancer |
| TWI794171B (zh) | 2016-05-11 | 2023-03-01 | 美商滬亞生物國際有限公司 | Ｈｄａｃ抑制劑與ｐｄ-ｌ１抑制劑之組合治療 |
| TWI808055B (zh) | 2016-05-11 | 2023-07-11 | 美商滬亞生物國際有限公司 | Hdac 抑制劑與 pd-1 抑制劑之組合治療 |
| CN109171001A (zh) * | 2018-09-14 | 2019-01-11 | 上海烟草集团有限责任公司 | 草酸钠在降低卷烟烟气中TSNAs释放量中的应用 |
| JP2023508996A (ja) * | 2019-12-31 | 2023-03-06 | キネート バイオファーマ インク． | Ｃｄｋ１２／１３阻害剤を用いる癌の処置 |
| CN114163479B (zh) * | 2020-09-11 | 2025-05-16 | 上海海聚生物科技有限公司 | 一类治疗癌症用的铂类化合物及其制备方法 |
| US20230339997A1 (en) * | 2020-09-11 | 2023-10-26 | Shanghai Haiju Biological Technology Co., Ltd. | Class of platinum compounds for treating cancer, and method for preparation thereof |
| CN114539320B (zh) * | 2020-11-25 | 2026-01-27 | 北京大学 | 辐射激活的四价铂配合物及其用途 |
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| US3773919A (en) | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| CH605550A5 (https=) | 1972-06-08 | 1978-09-29 | Research Corp | |
| US4263428A (en) | 1978-03-24 | 1981-04-21 | The Regents Of The University Of California | Bis-anthracycline nucleic acid function inhibitors and improved method for administering the same |
| EP0052322B1 (de) | 1980-11-10 | 1985-03-27 | Gersonde, Klaus, Prof. Dr. | Verfahren zur Herstellung von Lipid-Vesikeln durch Ultraschallbehandlung, Anwendung des Verfahrens und Vorrichtung zur Durchführung des Verfahrens |
| US4485045A (en) | 1981-07-06 | 1984-11-27 | Research Corporation | Synthetic phosphatidyl cholines useful in forming liposomes |
| DE3374837D1 (en) | 1982-02-17 | 1988-01-21 | Ciba Geigy Ag | Lipids in the aqueous phase |
| DE3218121A1 (de) | 1982-05-14 | 1983-11-17 | Leskovar, Peter, Dr.-Ing., 8000 München | Arzneimittel zur tumorbehandlung |
| EP0102324A3 (de) | 1982-07-29 | 1984-11-07 | Ciba-Geigy Ag | Lipide und Tenside in wässriger Phase |
| US4544545A (en) | 1983-06-20 | 1985-10-01 | Trustees University Of Massachusetts | Liposomes containing modified cholesterol for organ targeting |
| JPS607934A (ja) | 1983-06-29 | 1985-01-16 | Dai Ichi Seiyaku Co Ltd | リポソ−ムの製造方法 |
| HUT35524A (en) | 1983-08-02 | 1985-07-29 | Hoechst Ag | Process for preparing pharmaceutical compositions containing regulatory /regulative/ peptides providing for the retarded release of the active substance |
| DE3483949D1 (de) | 1983-09-26 | 1991-02-21 | Udo Dr Med Ehrenfeld | Mittel und erzeugnis fuer die diagnose und therapie von tumoren sowie zur behandlung von schwaechen der zelligen und humoralen immunabwehr. |
| EP0143949B1 (en) | 1983-11-01 | 1988-10-12 | TERUMO KABUSHIKI KAISHA trading as TERUMO CORPORATION | Pharmaceutical composition containing urokinase |
| CS269719B1 (en) | 1986-12-29 | 1990-05-14 | Kiss Frantisek | Platinum cytostatic |
| US6051256A (en) | 1994-03-07 | 2000-04-18 | Inhale Therapeutic Systems | Dispersible macromolecule compositions and methods for their preparation and use |
| DE19636889A1 (de) | 1996-09-11 | 1998-03-12 | Felix Dr Kratz | Antineoplastisch wirkende Transferrin- und Albuminkonjugate zytostatischer Verbindungen aus der Gruppe der Anthrazykline, Alkylantien, Antimetabolite und Cisplatin-Analoga und diese enthaltende Arzneimittel |
| CN1169520C (zh) | 1997-09-29 | 2004-10-06 | 耐科塔医药公司 | 多孔微粒及其使用方法 |
| CZ302070B6 (cs) | 1998-04-21 | 2010-09-29 | Micromet Ag | Jednoretezcový multifunkcní polypeptid, polynukleotid, vektor obsahující tento polynukleotid, bunka transfekovaná tímto polynukleotidem, prostredek obsahující tento polypeptid, polynukleotid nebo vektor a jejich použití a zpusob identifikace aktiváto |
| DE19926154A1 (de) | 1999-06-09 | 2000-12-14 | Ktb Tumorforschungs Gmbh | Verfahren zur Herstellung einer injizierbaren Arzneimittelzubereitung |
| AUPQ641100A0 (en) | 2000-03-23 | 2000-04-15 | Australia Nuclear Science & Technology Organisation | Methods of synthesis and use of radiolabelled platinum chemotherapeutic ag ents |
| ES2525087T5 (es) | 2000-05-10 | 2018-06-28 | Novartis Ag | Polvos basados en fosfolípidos para administración de fármacos |
| JP2005514393A (ja) | 2001-12-19 | 2005-05-19 | ネクター セラピューティクス | アミノグリコシドの肺への供給 |
| DE10314780A1 (de) | 2003-03-19 | 2004-09-30 | Ktb Tumorforschungsgesellschaft Mbh | Proteinbindende Derivate von Platinkomplexen mit Cyclobutan-1,1-dicarboxylatliganden |
| HRP20050902A2 (en) | 2003-03-31 | 2005-12-31 | Pliva-Lachema A.S. | Pharmaceutical composition containing platinum complex as active substance and method of manufacturing thereof |
| CZ2004945A3 (cs) | 2004-09-08 | 2006-01-11 | Pliva - Lachema A. S. | Farmaceutická kompozice pro rektální nebo vaginální podání, zpusob její prípravy a tato kompozice pro pouzití jako lécivo |
| CZ2004964A3 (cs) | 2004-09-14 | 2006-03-15 | Pliva-Lachema A. S. | Perorální farmaceutická kompozice pro cílený transport komplexu platiny do kolorektální oblasti, zpusob její prípravy a tato kompozice pro pouzití jako lécivo |
| US20060205810A1 (en) | 2004-11-24 | 2006-09-14 | Schering Corporation | Platinum therapeutic combinations |
| CZ300120B6 (cs) | 2006-06-20 | 2009-02-11 | Pliva - Lachema A. S. | Farmaceutická kompozice pro injekcní podání |
| CZ300424B6 (cs) | 2006-06-20 | 2009-05-13 | Pliva - Lachema A. S. | Farmaceutická kompozice pro perorální podání |
| CZ300590B6 (cs) | 2006-06-20 | 2009-06-24 | Pliva - Lachema A. S. | Farmaceutická kompozice pro injekcní podání |
| CN104244718A (zh) | 2011-12-05 | 2014-12-24 | 伊格尼卡生物治疗公司 | 抗体-药物缀合物以及相关化合物、组合物和方法 |
| CN117462693A (zh) * | 2012-02-27 | 2024-01-30 | 阿穆尼克斯运营公司 | Xten缀合组合物和制造其的方法 |
| BR112016006955A2 (pt) * | 2013-10-08 | 2017-08-01 | Atlas Genetics Ltd | compostos de marcação e seu uso em ensaios |
| US10011622B2 (en) | 2013-12-31 | 2018-07-03 | Placon Therapeutics, Inc. | Compounds, compositions, and methods for the treatment of cancers |
| EP3797768A1 (en) * | 2014-06-23 | 2021-03-31 | Placon Therapeutics, Inc. | Maleimide-functionalised platinum for use in the treatment of cancer |
| JP2018518509A (ja) * | 2015-06-23 | 2018-07-12 | プラコン セラピューティクス インコーポレイテッドＰｌａｃｏｎ Ｔｈｅｒａｐｅｕｔｉｃｓ，Ｉｎｃ． | 白金化合物、組成物及びその使用 |
| EP3313392B1 (en) | 2015-06-23 | 2020-09-16 | Placon Therapeutics, Inc. | Platinum compounds, compositions, and uses thereof |
| EP3313527B1 (en) | 2015-06-29 | 2021-02-24 | Case Western Reserve University | Anticancer drug-containing plant virus particles |
| FI3319936T3 (fi) | 2015-07-12 | 2026-03-12 | Hangzhou Dac Biotech Co Ltd | Silloituslinkkereitä soluun sitoutuvien molekyylien konjugoimiseksi |
| US10639378B2 (en) | 2016-06-06 | 2020-05-05 | Genentech, Inc. | Silvestrol antibody-drug conjugates and methods of use |
| WO2018009811A1 (en) | 2016-07-08 | 2018-01-11 | Genentech, Inc. | Use of human epididymis protein 4 (he4) for assessing responsiveness of muc 16-positive cancer treatment |
| WO2018026742A1 (en) | 2016-08-01 | 2018-02-08 | Askgene Pharma Inc. | Novel antibody-albumin-drug conjugates (aadc) and methods for using them |
| CN108164512B (zh) | 2017-12-27 | 2021-05-25 | 沈阳药科大学 | 一类具有生物粘附作用的马来酰亚胺型前药及其在口服药物传递中的应用 |
| CN108187063B (zh) | 2018-01-09 | 2020-09-08 | 沈阳药科大学 | 白蛋白结合型抗肿瘤药-马来酰亚胺分子前药 |
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| HRP20211466T1 (hr) | 2021-12-24 |
| CN108368143A (zh) | 2018-08-03 |
| MX2018006953A (es) | 2019-05-16 |
| US10723748B2 (en) | 2020-07-28 |
| US11572379B2 (en) | 2023-02-07 |
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| EP3386997A1 (en) | 2018-10-17 |
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| US20180354979A1 (en) | 2018-12-13 |
| SMT202100709T1 (it) | 2022-01-10 |
| JP6867652B2 (ja) | 2021-05-12 |
| EP3386997B1 (en) | 2021-06-30 |
| HUE056897T2 (hu) | 2022-03-28 |
| JP2018538292A (ja) | 2018-12-27 |
| MX377528B (es) | 2025-03-10 |
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| IL259864B (en) | 2022-07-01 |
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| AU2016367306B2 (en) | 2021-04-22 |
| CY1124529T1 (el) | 2022-07-22 |
| US20210002313A1 (en) | 2021-01-07 |
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