CA2276284C - Analogues radio-iodes d'ethers phospholipidiques et leurs procedes d'utilisation - Google Patents
Analogues radio-iodes d'ethers phospholipidiques et leurs procedes d'utilisation Download PDFInfo
- Publication number
- CA2276284C CA2276284C CA002276284A CA2276284A CA2276284C CA 2276284 C CA2276284 C CA 2276284C CA 002276284 A CA002276284 A CA 002276284A CA 2276284 A CA2276284 A CA 2276284A CA 2276284 C CA2276284 C CA 2276284C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- iodophenyl
- tumor
- phosphocholine
- analogs
- 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.)
- Expired - Lifetime
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- -1 phospholipid ether analogs Chemical class 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims description 17
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- 229940121896 radiopharmaceutical Drugs 0.000 claims description 13
- 230000002799 radiopharmaceutical effect Effects 0.000 claims description 13
- ZOAIEFWMQLYMTF-UHFFFAOYSA-N 18-(4-iodophenyl)octadecyl 2-(trimethylazaniumyl)ethyl phosphate Chemical compound C[N+](C)(C)CCOP([O-])(=O)OCCCCCCCCCCCCCCCCCCC1=CC=C(I)C=C1 ZOAIEFWMQLYMTF-UHFFFAOYSA-N 0.000 claims description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 239000011630 iodine Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
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- XTDZDZDPLJPWGO-UHFFFAOYSA-N 12-(4-iodophenyl)dodecyl 2-(trimethylazaniumyl)ethyl phosphate Chemical compound C[N+](C)(C)CCOP([O-])(=O)OCCCCCCCCCCCCC1=CC=C(I)C=C1 XTDZDZDPLJPWGO-UHFFFAOYSA-N 0.000 description 7
- KNEHKSMZPCBVIJ-UHFFFAOYSA-N 18-(4-iodophenyl)octadecan-1-ol Chemical compound OCCCCCCCCCCCCCCCCCCC1=CC=C(I)C=C1 KNEHKSMZPCBVIJ-UHFFFAOYSA-N 0.000 description 7
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- AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 description 5
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- 150000003904 phospholipids Chemical class 0.000 description 4
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- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 3
- PSUXTZLDBVEZTD-UHFFFAOYSA-N 3-bromopropoxymethylbenzene Chemical compound BrCCCOCC1=CC=CC=C1 PSUXTZLDBVEZTD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 125000001931 aliphatic group Chemical group 0.000 description 3
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
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- OBBCSXFCDPPXOL-UHFFFAOYSA-N misonidazole Chemical compound COCC(O)CN1C=CN=C1[N+]([O-])=O OBBCSXFCDPPXOL-UHFFFAOYSA-N 0.000 description 1
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- HITMISAYDYAKTA-UHFFFAOYSA-N pentadecyl 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCOP([O-])(=O)OCC[N+](C)(C)C HITMISAYDYAKTA-UHFFFAOYSA-N 0.000 description 1
- FNYVZOYSEAGDDE-UHFFFAOYSA-N pentadecyl 4-methylbenzenesulfonate Chemical compound CCCCCCCCCCCCCCCOS(=O)(=O)C1=CC=C(C)C=C1 FNYVZOYSEAGDDE-UHFFFAOYSA-N 0.000 description 1
- 125000002525 phosphocholine group Chemical class OP(=O)(OCC[N+](C)(C)C)O* 0.000 description 1
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- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical group CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
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- 238000011200 topical administration Methods 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 229960001479 tosylchloramide sodium Drugs 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000004654 triazenes Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/094—Esters of phosphoric acids with arylalkanols
-
- 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
- A61K51/0404—Lipids, e.g. triglycerides; Polycationic carriers
- A61K51/0408—Phospholipids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/004—Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, selenium or tellurium
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
L'invention concerne des analogues radio-iodés d'éthers de phospolipidiques qui présentent une importante avidité pour les tumeurs et ont une demi-vie dans le plasma plus longue que les analogues à chaîne plus courte; ils améliorent l'imagerie et le visualisation des lésions néoplasiques et permettent une thérapie cytotoxique du cancer spécifique des tumeurs.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1996/019352 WO1998024480A1 (fr) | 1996-12-04 | 1996-12-04 | Analogues radio-iodes d'ethers phospholipidiques et leurs procedes d'utilisation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2276284A1 CA2276284A1 (fr) | 1998-06-11 |
| CA2276284C true CA2276284C (fr) | 2006-10-10 |
Family
ID=22256241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002276284A Expired - Lifetime CA2276284C (fr) | 1996-12-04 | 1996-12-04 | Analogues radio-iodes d'ethers phospholipidiques et leurs procedes d'utilisation |
Country Status (2)
| Country | Link |
|---|---|
| CA (1) | CA2276284C (fr) |
| WO (1) | WO1998024480A1 (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA06009681A (es) | 2004-03-02 | 2007-03-15 | Cellectar Llc | Analogos de fosfolipido para el diagnostico y tratamiento del cancer. |
| US8540968B2 (en) | 2004-03-02 | 2013-09-24 | Cellectar, Inc. | Phospholipid ether analogs as agents for detecting and locating cancer, and methods thereof |
| KR20080005178A (ko) * | 2004-12-20 | 2008-01-10 | 셀렉타, 엘엘씨 | 암 검출 및 치료용 인지질 에테르 동족체 |
| EP2429591B1 (fr) | 2009-05-11 | 2015-08-26 | Cellectar, Inc. | Composés d'éther de phospholipide fluorescents, compositions et procédés d'utilisation associés |
| US8871181B2 (en) | 2009-05-11 | 2014-10-28 | Cellectar, Inc. | Fluorescent phospholipid ether compounds, compositions, and methods of use |
| WO2010144788A2 (fr) * | 2009-06-12 | 2010-12-16 | Cellectar, Inc. | Composés éther et alkyle phospholipides pour traiter un cancer et pour l'imagerie et la détection de cellules souches cancéreuses |
| JP2013504590A (ja) * | 2009-09-11 | 2013-02-07 | セレクター，インコーポレイティド | 非放射性リン脂質化合物、組成物、及び使用方法 |
| DK3750545T3 (da) | 2014-11-17 | 2024-04-22 | Cellectar Biosciences Inc | Phospholipidetheranaloger som cancermålrettede lægemiddelbærere |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4764358A (en) * | 1985-04-30 | 1988-08-16 | The United States Of America As Represented By The United States Department Of Energy | Radiolabeled dimethyl branched long chain fatty acid for heart imaging |
| DE3663522D1 (en) * | 1985-11-29 | 1989-06-29 | Takeda Chemical Industries Ltd | Phospholipid derivatives, their production and use |
| US4925649A (en) * | 1987-06-12 | 1990-05-15 | The University Of Michigan | Radioiodinated diacylglycerol analogues and methods of use |
| US5030733A (en) * | 1987-07-23 | 1991-07-09 | Hoechst-Roussel Pharmaceticals Incorporated | Hydroxy-, alkoxy- and benzyloxy-substituted phospholipids |
| US5347030A (en) * | 1987-10-23 | 1994-09-13 | The Board Of Regents Of The University Of Michigan | Radioiodinated phospholipid ether analogues and methods of using same |
| US5087721A (en) * | 1987-10-23 | 1992-02-11 | The University Of Michigan | Radioiodinated phosphate esters |
| US4965391A (en) * | 1987-10-23 | 1990-10-23 | The University Of Michigan | Radioiodinated phospholipid ether analogues |
| US5369097A (en) * | 1991-04-25 | 1994-11-29 | The University Of British Columbia | Phosphonates as anti-cancer agents |
-
1996
- 1996-12-04 WO PCT/US1996/019352 patent/WO1998024480A1/fr active Application Filing
- 1996-12-04 CA CA002276284A patent/CA2276284C/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2276284A1 (fr) | 1998-06-11 |
| WO1998024480A1 (fr) | 1998-06-11 |
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