CA2514307A1 - Improved radiometal complex compositions - Google Patents
Improved radiometal complex compositions Download PDFInfo
- Publication number
- CA2514307A1 CA2514307A1 CA002514307A CA2514307A CA2514307A1 CA 2514307 A1 CA2514307 A1 CA 2514307A1 CA 002514307 A CA002514307 A CA 002514307A CA 2514307 A CA2514307 A CA 2514307A CA 2514307 A1 CA2514307 A1 CA 2514307A1
- Authority
- CA
- Canada
- Prior art keywords
- radioprotectant
- tropane
- conjugate
- biocompatible
- composition
- 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.)
- Abandoned
Links
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- 229940124553 radioprotectant Drugs 0.000 claims abstract description 53
- 239000002738 chelating agent Substances 0.000 claims abstract description 50
- 238000002360 preparation method Methods 0.000 claims abstract description 36
- 239000012217 radiopharmaceutical Substances 0.000 claims abstract description 36
- 229940121896 radiopharmaceutical Drugs 0.000 claims abstract description 35
- 230000002799 radiopharmaceutical effect Effects 0.000 claims abstract description 35
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910052713 technetium Inorganic materials 0.000 claims abstract description 25
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 24
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 15
- 230000007935 neutral effect Effects 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims description 37
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 36
- XLRPYZSEQKXZAA-OCAPTIKFSA-N tropane Chemical compound C1CC[C@H]2CC[C@@H]1N2C XLRPYZSEQKXZAA-OCAPTIKFSA-N 0.000 claims description 36
- 229930004006 tropane Natural products 0.000 claims description 34
- 230000002285 radioactive effect Effects 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 24
- 239000011668 ascorbic acid Substances 0.000 claims description 19
- 235000010323 ascorbic acid Nutrition 0.000 claims description 18
- 229960005070 ascorbic acid Drugs 0.000 claims description 15
- 239000002243 precursor Substances 0.000 claims description 13
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 12
- 150000001768 cations Chemical class 0.000 claims description 12
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 12
- 125000005647 linker group Chemical group 0.000 claims description 11
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims description 10
- 239000003638 chemical reducing agent Substances 0.000 claims description 9
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- OJSLUXYIIKQTPB-KGLIPLIRSA-N (1r,5s)-8-methyl-5-phenyl-8-azabicyclo[3.2.1]octane Chemical compound C1([C@@]23CC[C@@](CCC2)(N3C)[H])=CC=CC=C1 OJSLUXYIIKQTPB-KGLIPLIRSA-N 0.000 claims description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
- 235000010378 sodium ascorbate Nutrition 0.000 claims description 5
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 claims description 5
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- HZLFSOZSLFKJKA-JSXRDJHFSA-N 2-[2-[[(1s,3s,4r,5r)-3-(4-chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octan-4-yl]methyl-(2-sulfanylethyl)amino]ethylamino]ethanethiol Chemical compound C1([C@@H]2[C@H](CN(CCS)CCNCCS)[C@H]3CC[C@@H](C2)N3C)=CC=C(Cl)C=C1 HZLFSOZSLFKJKA-JSXRDJHFSA-N 0.000 description 9
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- 230000001588 bifunctional effect Effects 0.000 description 8
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- 239000002253 acid Substances 0.000 description 7
- 210000004556 brain Anatomy 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 150000003573 thiols Chemical group 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 230000002335 preservative effect Effects 0.000 description 6
- 238000003608 radiolysis reaction Methods 0.000 description 6
- 241000894007 species Species 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
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- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- 238000007254 oxidation reaction Methods 0.000 description 5
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- ITRMROGJSNWFKO-FOCLMDBBSA-N 4,4'-azodibenzenearsonic acid Chemical compound C1=CC([As](O)(=O)O)=CC=C1\N=N\C1=CC=C([As](O)(O)=O)C=C1 ITRMROGJSNWFKO-FOCLMDBBSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0497—Organic compounds conjugates with a carrier being an organic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/12—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by a special physical form, e.g. emulsion, microcapsules, liposomes, characterized by a special physical form, e.g. emulsions, dispersions, microcapsules
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Physics & Mathematics (AREA)
- Pharmacology & Pharmacy (AREA)
- Optics & Photonics (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dispersion Chemistry (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03002809A EP1444990A1 (en) | 2003-02-07 | 2003-02-07 | Improved Radiometal Complex Compositions |
| EP03002809.6 | 2003-02-07 | ||
| PCT/GB2004/000443 WO2004069285A1 (en) | 2003-02-07 | 2004-02-09 | Improved radiometal complex compositions |
Publications (1)
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|---|---|
| CA2514307A1 true CA2514307A1 (en) | 2004-08-19 |
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Family Applications (1)
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|---|---|---|---|
| CA002514307A Abandoned CA2514307A1 (en) | 2003-02-07 | 2004-02-09 | Improved radiometal complex compositions |
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|---|---|
| US (1) | US20070020177A1 (enExample) |
| EP (2) | EP1444990A1 (enExample) |
| JP (2) | JP2006528205A (enExample) |
| KR (1) | KR20050103221A (enExample) |
| CN (1) | CN100548387C (enExample) |
| AT (1) | ATE487498T1 (enExample) |
| AU (1) | AU2004210191B2 (enExample) |
| BR (1) | BRPI0407056A (enExample) |
| CA (1) | CA2514307A1 (enExample) |
| DE (1) | DE602004029983D1 (enExample) |
| ES (1) | ES2355100T3 (enExample) |
| MX (1) | MXPA05008356A (enExample) |
| NO (1) | NO20053754L (enExample) |
| RU (1) | RU2005123799A (enExample) |
| WO (1) | WO2004069285A1 (enExample) |
| ZA (1) | ZA200506728B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1444990A1 (en) * | 2003-02-07 | 2004-08-11 | Amersham plc | Improved Radiometal Complex Compositions |
| US8741261B2 (en) | 2003-12-18 | 2014-06-03 | Ge Healthcare Limited | Methods for carbon isotope labeling synthesis by transition metal-promoted carbonylation via isocyanate using azides and carbon-isotope monoxide |
| WO2006134424A2 (en) * | 2004-12-03 | 2006-12-21 | Ge Healthcare Limited | Method for the use of [11c] carbon monoxide in labeling synthesis of 11c-labelled acids by photo-induced free radical carbonylation |
| GB0428020D0 (en) | 2004-12-22 | 2005-01-26 | Amersham Health As | Stabilisation of radiopharmaceutical precursors |
| WO2006082497A1 (en) * | 2005-02-01 | 2006-08-10 | Ge Healthcare Limited | Method for the use of [11c] carbon monoxide in labeling synthesis of 11c-labelled compounds by thermally induced free radical carbonylation |
| US20060217537A1 (en) * | 2005-03-22 | 2006-09-28 | Bengt Langstrom | Methods for carbon isotope labeling synthesis by transition metal-promoted carbonylation via ketene using diazo compounds and carbon-isotope monoxide |
| WO2006134822A1 (ja) * | 2005-06-14 | 2006-12-21 | Nihon Medi-Physics Co., Ltd. | 放射性画像診断剤 |
| US8273861B2 (en) | 2005-08-31 | 2012-09-25 | Ge Healthcare Limited | Method for the use of [11C] carbon monoxide in labeling synthesis of 11C-labelled ketones by photo-induced free radical carbonylation |
| EP2080526A4 (en) * | 2006-11-09 | 2012-11-07 | Nihon Mediphysics Co Ltd | RADIOACTIVE DIAGNOSTIC IMAGING DAY |
| RU2366434C1 (ru) * | 2007-12-07 | 2009-09-10 | Институт неорганической химии им. А.В. Николаева Сибирского отделения Российской Академии наук | Гексаядерные кластерные комплексы рения на основе радиоактивных изотопов, обладающие противоопухолевыми свойствами |
| GB0922023D0 (en) * | 2009-12-17 | 2010-02-03 | Ge Healthcare Ltd | Preparation of n-monofluoroalkyl compounds |
| US9951324B2 (en) | 2010-02-25 | 2018-04-24 | Purdue Research Foundation | PSMA binding ligand-linker conjugates and methods for using |
| HUE050033T2 (hu) | 2010-07-27 | 2020-11-30 | Serac Healthcare Ltd | Radioaktív gyógyszerkészítmények |
| KR102575825B1 (ko) * | 2012-11-15 | 2023-09-06 | 엔도사이트, 인코포레이티드 | Psma 발현 세포에 의해 야기되는 질병을 치료하기 위한 컨쥬게이트 |
| WO2014126902A1 (en) * | 2013-02-15 | 2014-08-21 | Thomas Jefferson University | Kit for tumor imaging |
| SG11201602249RA (en) | 2013-10-18 | 2016-05-30 | Deutsches Krebsforsch | Labeled inhibitors of prostate specific membrane antigen (psma), their use as imaging agents and pharmaceutical agents for the treatment of prostate cancer |
| EA035171B1 (ru) | 2013-11-14 | 2020-05-08 | Эндосайт, Инк. | Конъюгаты на основе связывающихся с psma лигандов или ингибиторов psma для позитронно-эмиссионной томографии |
| US20150375901A1 (en) * | 2014-06-30 | 2015-12-31 | Karen J. Orlich | Reusable, eco-friendly container for storing and dispensing food and beverage |
| US10188759B2 (en) | 2015-01-07 | 2019-01-29 | Endocyte, Inc. | Conjugates for imaging |
| RU2624237C1 (ru) * | 2016-10-26 | 2017-07-03 | Федеральное государственное бюджетное учреждение "Государственный научный центр Российской Федерации - Федеральный медицинский биофизический центр имени А.И. Бурназяна" | Радиофармацевтическая композиция для радиосиновэктомии и способ ее получения |
| US10610870B2 (en) | 2017-08-21 | 2020-04-07 | Bliss Industries, Llc | Hot and cold forming hammer and method of assembly |
| US10486160B2 (en) | 2017-08-21 | 2019-11-26 | Bliss Industries, Llc | Method of replacing hammers and spacers |
| US10207274B1 (en) | 2017-08-21 | 2019-02-19 | Roger Young | Non-forged hammermill hammer |
| US12138630B2 (en) | 2017-08-21 | 2024-11-12 | Bliss Industries, Llc | Hammermill hammer |
| USD905136S1 (en) | 2018-03-05 | 2020-12-15 | Bliss Industries, Llc | Hammermill hammer |
| US10478824B2 (en) | 2017-08-21 | 2019-11-19 | Bliss Industries, Llc | System and method for installing hammers |
| USD861048S1 (en) | 2017-12-06 | 2019-09-24 | Roger Young | Swing hammer |
| USD839934S1 (en) | 2017-12-06 | 2019-02-05 | Roger Young | Swing hammer |
| USD840447S1 (en) | 2017-12-06 | 2019-02-12 | Roger Young | Swing hammer |
| BR112020020961A2 (pt) | 2018-04-17 | 2021-01-19 | Endocyte, Inc. | Métodos de tratamento de câncer |
| CN120097929A (zh) | 2019-05-20 | 2025-06-06 | 因多塞特股份有限公司 | 制备psma缀合物的方法 |
| WO2022156908A1 (en) * | 2021-01-25 | 2022-07-28 | Vrije Universiteit Brussel | Method for preparing a lyophilized composition |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4364920A (en) * | 1975-04-30 | 1982-12-21 | Medi-Physics, Inc. | Stable diagnostic reagents |
| US4497744A (en) * | 1978-03-31 | 1985-02-05 | Mallinckrodt, Inc. | Gentisic acid salts as radiographic scanning agent stabilizers |
| US4233284A (en) * | 1978-03-31 | 1980-11-11 | The Procter & Gamble Company | Stabilized radiographic scanning agents |
| DE78642T1 (de) * | 1981-10-30 | 1983-10-27 | Amersham International Plc, Amersham, Buckinghamshire | Radiopharmazeutische zubereitung auf grund von technetium-99m und reagenz zur herstellung derselben. |
| US6241963B1 (en) * | 1995-10-19 | 2001-06-05 | The Trustees Of The University Of Pennsylvania | Dopamine and serotonin transporter ligands and imaging agents |
| US6171576B1 (en) | 1995-11-03 | 2001-01-09 | Organix Inc. | Dopamine transporter imaging agent |
| US7105678B2 (en) * | 1995-11-03 | 2006-09-12 | Organix, Inc. | Boat tropanes |
| US5961955A (en) * | 1997-06-03 | 1999-10-05 | Coulter Pharmaceutical, Inc. | Radioprotectant for peptides labeled with radioisotope |
| AU4308001A (en) * | 1999-12-03 | 2001-06-12 | Yale University | Transition metal-cyclopentadienyl-tropane conjugates |
| GB0031592D0 (en) * | 2000-12-28 | 2001-02-07 | Nycomed Amersham Plc | Stabilised radiopharmaceutical compositions |
| FR2833952B1 (fr) | 2001-12-26 | 2004-03-26 | Schering Ag | Derive du tropane, produit de chelation comprenant ce derive de tropane et un metal ou un complexe de metal et radiopharmaceutique |
| EP1444990A1 (en) * | 2003-02-07 | 2004-08-11 | Amersham plc | Improved Radiometal Complex Compositions |
-
2003
- 2003-02-07 EP EP03002809A patent/EP1444990A1/en not_active Withdrawn
-
2004
- 2004-02-09 JP JP2006525001A patent/JP2006528205A/ja active Pending
- 2004-02-09 WO PCT/GB2004/000443 patent/WO2004069285A1/en not_active Ceased
- 2004-02-09 CA CA002514307A patent/CA2514307A1/en not_active Abandoned
- 2004-02-09 RU RU2005123799/15A patent/RU2005123799A/ru not_active Application Discontinuation
- 2004-02-09 BR BR0407056-9A patent/BRPI0407056A/pt not_active IP Right Cessation
- 2004-02-09 CN CNB2004800091645A patent/CN100548387C/zh not_active Expired - Lifetime
- 2004-02-09 AT AT04709267T patent/ATE487498T1/de not_active IP Right Cessation
- 2004-02-09 DE DE602004029983T patent/DE602004029983D1/de not_active Expired - Lifetime
- 2004-02-09 MX MXPA05008356A patent/MXPA05008356A/es unknown
- 2004-02-09 US US10/544,736 patent/US20070020177A1/en not_active Abandoned
- 2004-02-09 KR KR1020057014518A patent/KR20050103221A/ko not_active Withdrawn
- 2004-02-09 AU AU2004210191A patent/AU2004210191B2/en not_active Ceased
- 2004-02-09 EP EP04709267A patent/EP1590007B1/en not_active Expired - Lifetime
- 2004-02-09 ES ES04709267T patent/ES2355100T3/es not_active Expired - Lifetime
-
2005
- 2005-08-05 NO NO20053754A patent/NO20053754L/no not_active Application Discontinuation
- 2005-08-22 ZA ZA200506728A patent/ZA200506728B/en unknown
-
2011
- 2011-03-29 JP JP2011071532A patent/JP2011132258A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| KR20050103221A (ko) | 2005-10-27 |
| NO20053754L (no) | 2005-10-05 |
| WO2004069285A1 (en) | 2004-08-19 |
| ZA200506728B (en) | 2006-10-25 |
| AU2004210191B2 (en) | 2007-08-23 |
| ES2355100T3 (es) | 2011-03-22 |
| JP2006528205A (ja) | 2006-12-14 |
| DE602004029983D1 (de) | 2010-12-23 |
| ATE487498T1 (de) | 2010-11-15 |
| MXPA05008356A (es) | 2006-03-13 |
| CN1767859A (zh) | 2006-05-03 |
| AU2004210191A1 (en) | 2004-08-19 |
| RU2005123799A (ru) | 2006-03-27 |
| EP1590007B1 (en) | 2010-11-10 |
| BRPI0407056A (pt) | 2006-01-17 |
| EP1590007A1 (en) | 2005-11-02 |
| JP2011132258A (ja) | 2011-07-07 |
| EP1444990A1 (en) | 2004-08-11 |
| CN100548387C (zh) | 2009-10-14 |
| NO20053754D0 (no) | 2005-08-05 |
| US20070020177A1 (en) | 2007-01-25 |
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