DE69730961T2 - Verwendung von thexapyrin zur herstellung eines arzneimittels zur verwendung mit einem chemotherapeutikum in der krebs-chemosensibilisierung - Google Patents
Verwendung von thexapyrin zur herstellung eines arzneimittels zur verwendung mit einem chemotherapeutikum in der krebs-chemosensibilisierung Download PDFInfo
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- DE69730961T2 DE69730961T2 DE69730961T DE69730961T DE69730961T2 DE 69730961 T2 DE69730961 T2 DE 69730961T2 DE 69730961 T DE69730961 T DE 69730961T DE 69730961 T DE69730961 T DE 69730961T DE 69730961 T2 DE69730961 T2 DE 69730961T2
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- texaphyrin
- iii
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- metal cation
- chemotherapeutic agent
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
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- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/243—Platinum; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/14—Peptides containing saccharide radicals; Derivatives thereof, e.g. bleomycin, phleomycin, muramylpeptides or vancomycin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
- A61K41/0076—PDT with expanded (metallo)porphyrins, i.e. having more than 20 ring atoms, e.g. texaphyrins, sapphyrins, hexaphyrins, pentaphyrins, porphocyanines
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Inorganic Chemistry (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/591,318 US5776925A (en) | 1996-01-25 | 1996-01-25 | Methods for cancer chemosensitization |
| US591318 | 1996-01-25 | ||
| PCT/US1997/000907 WO1997026915A1 (en) | 1996-01-25 | 1997-01-23 | Use of a thexaphyrin in the preparation of a medicament for use with a chemotherapeutic agent in cancer chemosensitization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69730961D1 DE69730961D1 (de) | 2004-11-04 |
| DE69730961T2 true DE69730961T2 (de) | 2005-11-24 |
Family
ID=24366012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69730961T Expired - Fee Related DE69730961T2 (de) | 1996-01-25 | 1997-01-23 | Verwendung von thexapyrin zur herstellung eines arzneimittels zur verwendung mit einem chemotherapeutikum in der krebs-chemosensibilisierung |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5776925A (OSRAM) |
| EP (1) | EP0912196B9 (OSRAM) |
| JP (1) | JP2000503989A (OSRAM) |
| KR (1) | KR19990082024A (OSRAM) |
| CN (1) | CN1093766C (OSRAM) |
| AT (1) | ATE277637T1 (OSRAM) |
| AU (1) | AU715025B2 (OSRAM) |
| DE (1) | DE69730961T2 (OSRAM) |
| ES (1) | ES2227671T3 (OSRAM) |
| IL (1) | IL125459A0 (OSRAM) |
| NO (1) | NO983429L (OSRAM) |
| NZ (1) | NZ331513A (OSRAM) |
| WO (1) | WO1997026915A1 (OSRAM) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5457183A (en) * | 1989-03-06 | 1995-10-10 | Board Of Regents, The University Of Texas System | Hydroxylated texaphyrins |
| US6200547B1 (en) * | 1994-01-26 | 2001-03-13 | Ferx Incorporated | Magnetically responsive compositions for carrying biologically active substances and methods of production and use |
| US6482436B1 (en) | 1993-01-29 | 2002-11-19 | Ferx Incorporated | Magnetically responsive composition |
| US5969111A (en) * | 1994-04-14 | 1999-10-19 | Board Of Regents, The University Of Texas System | Texaphyrins substituted with imidazole are provided |
| RU2106146C1 (ru) | 1995-07-17 | 1998-03-10 | Институт элементоорганических соединений РАН | Средство для подавления опухолевого роста |
| US6441025B2 (en) * | 1996-03-12 | 2002-08-27 | Pg-Txl Company, L.P. | Water soluble paclitaxel derivatives |
| JPH10279502A (ja) * | 1997-03-31 | 1998-10-20 | Katsuro Tachibana | 光感受性物質の励起方法 |
| US6022526A (en) * | 1997-07-30 | 2000-02-08 | Pharmacyclics, Inc. | Use of texaphyrins in detection of melanin and melanin metabolites diagnostic of melanotic melanoma |
| HK1041209A1 (zh) | 1999-01-13 | 2002-07-05 | Meditech Research Limited | 加強藥物療效的成份及方法 |
| EP2266607A3 (en) | 1999-10-01 | 2011-04-20 | Immunogen, Inc. | Immunoconjugates for treating cancer |
| US20030054977A1 (en) * | 1999-10-12 | 2003-03-20 | Cell Therapeutics, Inc. | Manufacture of polyglutamate-therapeutic agent conjugates |
| EP1227844A2 (en) * | 1999-10-29 | 2002-08-07 | Pharmacyclics, Inc. | Compositions for treating atheroma and neoplastic tissue |
| US7579338B2 (en) * | 1999-10-29 | 2009-08-25 | Pharmacyclics, Inc. | Methods and compositions for treating atheroma, tumors and other neoplastic tissues |
| US20030031676A1 (en) * | 1999-10-29 | 2003-02-13 | Pharmacyclics, Inc. | Conjugate compounds for treating atheroma and other diseases |
| US20020077290A1 (en) * | 2000-03-17 | 2002-06-20 | Rama Bhatt | Polyglutamic acid-camptothecin conjugates and methods of preparation |
| US9066919B2 (en) * | 2000-07-14 | 2015-06-30 | Alchemia Oncology Pty Limited | Hyaluronan as a chemo-sensitizer in the treatment of cancer |
| AUPQ879500A0 (en) | 2000-07-14 | 2000-08-10 | Meditech Research Limited | Hyaluronan as cytotoxic agent, drug presensitizer and chemo-sensitizer in the treatment of disease |
| US7112671B2 (en) * | 2000-08-30 | 2006-09-26 | Pharmacyclics, Inc. | Non-symmetric tripyrranes in the synthesis of novel macrocycles |
| US6638924B2 (en) | 2000-08-30 | 2003-10-28 | Pharmacyclics, Inc. | Metallotexaphyrin derivatives |
| US7449454B2 (en) * | 2000-08-30 | 2008-11-11 | Pharmacyclics, Inc. | Metallotexaphyrin derivatives |
| US20030188326A1 (en) | 2000-11-03 | 2003-10-02 | Dana Farber Cancer Institute | Methods and compositions for the diagnosis of cancer susceptibilities and defective DNA repair mechanisms and treatment thereof |
| US6919327B2 (en) * | 2000-11-17 | 2005-07-19 | Pharmacyclics, Inc. | Texaphyrin coordination compounds and uses thereof |
| IL139975A0 (en) * | 2000-11-29 | 2002-02-10 | Univ Ramot | Anti proliferative drugs |
| US20050013853A1 (en) * | 2000-11-29 | 2005-01-20 | Irit Gil-Ad | Anti-proliferative drugs |
| US6630454B2 (en) | 2001-09-10 | 2003-10-07 | Ramot At Tel-Aviv University Ltd. | Method and pharmaceutical composition for the treatment of cancer |
| AU2000280389A1 (en) | 2001-11-02 | 2003-05-19 | Dana-Farber Cancer Institute | Methods and compositions for the diagnosis of cancer susceptibilities and defective dna repair mechanisms and treatment thereof |
| JP2005511719A (ja) * | 2001-12-13 | 2005-04-28 | ファーマサイクリクス，インコーポレイテッド | 神経性進行に影響を与えるためのプロセス |
| AU2002351382A1 (en) * | 2001-12-13 | 2003-06-23 | Pharmacyclics, Inc. | Combination cancer therapy |
| US6984734B2 (en) | 2002-02-26 | 2006-01-10 | Board Of Regents, The University Of Texas System | Cyclo[n]pyrroles and methods thereto |
| US6723750B2 (en) | 2002-03-15 | 2004-04-20 | Allergan, Inc. | Photodynamic therapy for pre-melanomas |
| US20030224422A1 (en) * | 2002-04-08 | 2003-12-04 | St. Jude Children's Research Hospital, Inc. | Pre-and post therapy gene expression profiling to identify drug targets |
| US20040010218A1 (en) * | 2002-07-11 | 2004-01-15 | Henderson Barbara W. | Photodynamic therapy for the enhancement of vascular permeability to aid in drug delivery to diseased tissues |
| JP2004077714A (ja) * | 2002-08-15 | 2004-03-11 | Fuji Xerox Co Ltd | 光走査装置 |
| US7981928B2 (en) | 2002-09-05 | 2011-07-19 | Nanodynamics, Inc. | Chemotherapy method using x-rays |
| US20080063605A1 (en) * | 2004-05-20 | 2008-03-13 | Wai-Fung Cheong | Method of Enhancing Visualization of Atherosclerotic Plaque |
| JP2006224318A (ja) * | 2005-02-15 | 2006-08-31 | Brother Ind Ltd | インクジェット記録装置 |
| US20060217291A1 (en) * | 2005-03-25 | 2006-09-28 | Ichiro Hirotsu | Radiosensitizer |
| JP4972929B2 (ja) * | 2005-03-25 | 2012-07-11 | ニプロ株式会社 | 放射線増感剤 |
| US8937052B2 (en) * | 2005-07-27 | 2015-01-20 | Alchemia Oncology Pty Limited | Therapeutic protocols using hyaluronan |
| US8319625B2 (en) * | 2005-09-01 | 2012-11-27 | Simplexgrinnell Lp | Fire alarm textual notification related application |
| EP1922077A4 (en) * | 2005-09-07 | 2013-03-06 | Alchemia Oncology Pty Ltd | THERAPEUTIC COMPOSITIONS WITH HYALURON AND THERAPEUTIC ANTIBODIES AND TREATMENT PROCEDURES |
| US20070072838A1 (en) * | 2005-09-26 | 2007-03-29 | Pharmacyclics, Inc. | High-purity texaphyrin metal complexes |
| US20070078119A1 (en) * | 2005-09-30 | 2007-04-05 | Pharmacyclics, Inc. | Storage system for texaphyrin pharmaceutical formulations |
| ES2406929T3 (es) * | 2006-06-26 | 2013-06-10 | The University Of British Columbia | Proteína secretada ácida y rica en cisteína (SPARC) como sensibilizantes quimioterapéuticos |
| US8287839B2 (en) * | 2006-12-04 | 2012-10-16 | Brookhaven Science Associates, Llc | Carboranylporphyrins and uses thereof |
| US8444953B2 (en) * | 2007-03-22 | 2013-05-21 | Brookhaven Science Associates, Llc | Symmetric and asymmetric halogen-containing metallocarboranylporphyrins and uses thereof |
| US20080279781A1 (en) * | 2007-05-10 | 2008-11-13 | Brookhaven Science Associates, Llc | Glycosylated Carboranylporphyrins and Uses Thereof |
| RU2438718C1 (ru) * | 2010-06-18 | 2012-01-10 | Федеральное государственное учреждение "Ростовский научно-исследовательский онкологический институт Федерального агентства по высокотехнологичной медицинской помощи" | Способ лечения сарком мягких тканей |
| TWI445696B (zh) | 2010-11-29 | 2014-07-21 | Univ Nat Yang Ming | 標靶人類胸線核苷酸激酶誘導惡性腫瘤中的ｄｎａ修復毒性 |
| US9662328B2 (en) | 2010-11-29 | 2017-05-30 | National Yang-Ming University | Targeting human thymidylate kinase induces DNA repair toxicity in malignant tumor cells |
| EP3154541A4 (en) | 2014-06-11 | 2017-12-20 | Board of Regents, The University of Texas System | Texaphyrin-pt(iv) conjugates and compositions for use in overcoming platinum resistance |
| US20200078459A1 (en) * | 2016-12-13 | 2020-03-12 | Health Research, Inc. | Near infrared (nir) photodynamic therapy (pdt) in combination with chemotherapy |
| US20250034158A1 (en) | 2020-08-14 | 2025-01-30 | Board Of Regents, The University Of Texas System | Texaphyrin derivatives for manganese chemotherapy, photoacoustic imaging, and photothermal therapy |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5599923A (en) * | 1989-03-06 | 1997-02-04 | Board Of Regents, University Of Tx | Texaphyrin metal complexes having improved functionalization |
| US4935498A (en) * | 1989-03-06 | 1990-06-19 | Board Of Regents, The University Of Texas System | Expanded porphyrins: large porphyrin-like tripyrroledimethine-derived macrocycles |
| US5457183A (en) * | 1989-03-06 | 1995-10-10 | Board Of Regents, The University Of Texas System | Hydroxylated texaphyrins |
| US5252720A (en) * | 1989-03-06 | 1993-10-12 | Board Of Regents, The University Of Texas System | Metal complexes of water soluble texaphyrins |
| US5559207A (en) * | 1989-03-06 | 1996-09-24 | Board Of Regents, University Of Texas | Texaphyrin metal complex mediated ester hydrolysis |
| US5258453A (en) * | 1992-01-21 | 1993-11-02 | University Of Utah | Drug delivery system for the simultaneous delivery of drugs activatable by enzymes and light |
| US5607924A (en) * | 1992-01-21 | 1997-03-04 | Pharmacyclics, Inc. | DNA photocleavage using texaphyrins |
| US5714328A (en) * | 1995-06-07 | 1998-02-03 | Board Of Regents, The University Of Texas System | RNA photocleavage using texaphyrins |
-
1996
- 1996-01-25 US US08/591,318 patent/US5776925A/en not_active Expired - Lifetime
-
1997
- 1997-01-23 CN CN97192481A patent/CN1093766C/zh not_active Expired - Fee Related
- 1997-01-23 AT AT97903873T patent/ATE277637T1/de not_active IP Right Cessation
- 1997-01-23 ES ES97903873T patent/ES2227671T3/es not_active Expired - Lifetime
- 1997-01-23 DE DE69730961T patent/DE69730961T2/de not_active Expired - Fee Related
- 1997-01-23 WO PCT/US1997/000907 patent/WO1997026915A1/en not_active Ceased
- 1997-01-23 NZ NZ331513A patent/NZ331513A/en unknown
- 1997-01-23 JP JP9526941A patent/JP2000503989A/ja active Pending
- 1997-01-23 AU AU18333/97A patent/AU715025B2/en not_active Ceased
- 1997-01-23 EP EP97903873A patent/EP0912196B9/en not_active Expired - Lifetime
- 1997-01-23 KR KR1019980705744A patent/KR19990082024A/ko not_active Ceased
-
1998
- 1998-07-22 IL IL12545998A patent/IL125459A0/xx unknown
- 1998-07-24 NO NO983429A patent/NO983429L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU715025B2 (en) | 2000-01-13 |
| EP0912196B9 (en) | 2005-01-05 |
| AU1833397A (en) | 1997-08-20 |
| NO983429D0 (no) | 1998-07-24 |
| EP0912196B1 (en) | 2004-09-29 |
| IL125459A0 (en) | 1999-03-12 |
| CN1093766C (zh) | 2002-11-06 |
| KR19990082024A (ko) | 1999-11-15 |
| WO1997026915A1 (en) | 1997-07-31 |
| US5776925A (en) | 1998-07-07 |
| HK1018588A1 (en) | 1999-12-30 |
| ATE277637T1 (de) | 2004-10-15 |
| EP0912196A1 (en) | 1999-05-06 |
| ES2227671T3 (es) | 2005-04-01 |
| JP2000503989A (ja) | 2000-04-04 |
| NO983429L (no) | 1998-09-24 |
| DE69730961D1 (de) | 2004-11-04 |
| NZ331513A (en) | 2001-10-26 |
| CN1213313A (zh) | 1999-04-07 |
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