CA2238860C - Stereoisomers of fatty acid analogs for diagnostic imaging - Google Patents
Stereoisomers of fatty acid analogs for diagnostic imaging Download PDFInfo
- Publication number
- CA2238860C CA2238860C CA002238860A CA2238860A CA2238860C CA 2238860 C CA2238860 C CA 2238860C CA 002238860 A CA002238860 A CA 002238860A CA 2238860 A CA2238860 A CA 2238860A CA 2238860 C CA2238860 C CA 2238860C
- Authority
- CA
- Canada
- Prior art keywords
- group
- hydrogen
- agent
- stereoisomer
- substituted
- 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 - Fee Related
Links
- 239000000194 fatty acid Substances 0.000 title claims abstract description 72
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 68
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 68
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 67
- 238000002059 diagnostic imaging Methods 0.000 title description 5
- 239000012216 imaging agent Substances 0.000 claims abstract description 59
- 238000000034 method Methods 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 239000003795 chemical substances by application Substances 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 241000124008 Mammalia Species 0.000 claims description 29
- 125000003107 substituted aryl group Chemical group 0.000 claims description 27
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 21
- 150000004820 halides Chemical class 0.000 claims description 21
- 238000003384 imaging method Methods 0.000 claims description 20
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 20
- -1 keto ester Chemical class 0.000 claims description 19
- ROIMNSWDOJCBFR-UHFFFAOYSA-N 2-iodothiophene Chemical group IC1=CC=CS1 ROIMNSWDOJCBFR-UHFFFAOYSA-N 0.000 claims description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 239000011737 fluorine Substances 0.000 claims description 17
- 150000003141 primary amines Chemical class 0.000 claims description 17
- 150000003335 secondary amines Chemical class 0.000 claims description 17
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 17
- 150000003512 tertiary amines Chemical class 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 238000009825 accumulation Methods 0.000 claims description 12
- 239000003937 drug carrier Substances 0.000 claims description 12
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
- 229930194542 Keto Natural products 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000002738 chelating agent Substances 0.000 claims description 8
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 8
- 230000003902 lesion Effects 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 210000000748 cardiovascular system Anatomy 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- IZCVLYJVVCABBV-UHFFFAOYSA-N 2-hydrazinylpyridine-3-carboxylic acid Chemical compound NNC1=NC=CC=C1C(O)=O IZCVLYJVVCABBV-UHFFFAOYSA-N 0.000 claims description 4
- 206010051290 Central nervous system lesion Diseases 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 231100001011 cardiovascular lesion Toxicity 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 210000004556 brain Anatomy 0.000 claims description 3
- 210000005013 brain tissue Anatomy 0.000 claims description 3
- 150000002527 isonitriles Chemical class 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 33
- 230000006378 damage Effects 0.000 abstract description 7
- 201000010099 disease Diseases 0.000 abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 5
- 238000003759 clinical diagnosis Methods 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 description 22
- 239000012217 radiopharmaceutical Substances 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 12
- 210000001519 tissue Anatomy 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 229940121896 radiopharmaceutical Drugs 0.000 description 7
- 230000002799 radiopharmaceutical effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 6
- 208000027418 Wounds and injury Diseases 0.000 description 5
- 208000014674 injury Diseases 0.000 description 5
- 230000004060 metabolic process Effects 0.000 description 5
- 210000000056 organ Anatomy 0.000 description 5
- 238000002600 positron emission tomography Methods 0.000 description 5
- 238000002603 single-photon emission computed tomography Methods 0.000 description 5
- 102000008100 Human Serum Albumin Human genes 0.000 description 4
- 108091006905 Human Serum Albumin Proteins 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000002502 liposome Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 206010061216 Infarction Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000003745 diagnosis Methods 0.000 description 3
- 230000007574 infarction Effects 0.000 description 3
- 230000002503 metabolic effect Effects 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 238000009206 nuclear medicine Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 239000008156 Ringer's lactate solution Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 208000029078 coronary artery disease Diseases 0.000 description 2
- 239000002532 enzyme inhibitor Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229940050410 gluconate Drugs 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 208000031225 myocardial ischemia Diseases 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000010412 perfusion Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 230000035899 viability Effects 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- 108010039627 Aprotinin Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000013602 Cardiac Myosins Human genes 0.000 description 1
- 108010051609 Cardiac Myosins Proteins 0.000 description 1
- 208000031229 Cardiomyopathies Diseases 0.000 description 1
- 208000002330 Congenital Heart Defects Diseases 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010019273 Heart disease congenital Diseases 0.000 description 1
- 208000013875 Heart injury Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010048858 Ischaemic cardiomyopathy Diseases 0.000 description 1
- 102000007330 LDL Lipoproteins Human genes 0.000 description 1
- 108010007622 LDL Lipoproteins Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CIYCGMVZIUDZCT-UHFFFAOYSA-N N1=CC=CC=C1.ClC1=CC(=CC=C1)C(=O)OO Chemical compound N1=CC=CC=C1.ClC1=CC(=CC=C1)C(=O)OO CIYCGMVZIUDZCT-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 101710126321 Pancreatic trypsin inhibitor Proteins 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 239000003070 absorption delaying agent Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 206010000891 acute myocardial infarction Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960004210 ammonia n-13 Drugs 0.000 description 1
- QGZKDVFQNNGYKY-BJUDXGSMSA-N ammonia-(13)N Chemical compound [13NH3] QGZKDVFQNNGYKY-BJUDXGSMSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 238000002583 angiography Methods 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000008344 brain blood flow Effects 0.000 description 1
- BPKIGYQJPYCAOW-FFJTTWKXSA-I calcium;potassium;disodium;(2s)-2-hydroxypropanoate;dichloride;dihydroxide;hydrate Chemical compound O.[OH-].[OH-].[Na+].[Na+].[Cl-].[Cl-].[K+].[Ca+2].C[C@H](O)C([O-])=O BPKIGYQJPYCAOW-FFJTTWKXSA-I 0.000 description 1
- BMLSTPRTEKLIPM-UHFFFAOYSA-I calcium;potassium;disodium;hydrogen carbonate;dichloride;dihydroxide;hydrate Chemical compound O.[OH-].[OH-].[Na+].[Na+].[Cl-].[Cl-].[K+].[Ca+2].OC([O-])=O BMLSTPRTEKLIPM-UHFFFAOYSA-I 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000008356 dextrose and sodium chloride injection Substances 0.000 description 1
- 239000008355 dextrose injection Substances 0.000 description 1
- FFYPMLJYZAEMQB-UHFFFAOYSA-N diethyl pyrocarbonate Chemical compound CCOC(=O)OC(=O)OCC FFYPMLJYZAEMQB-UHFFFAOYSA-N 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000004980 dosimetry Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002303 glucose derivatives Chemical class 0.000 description 1
- 230000004153 glucose metabolism Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000005831 heart abnormality Effects 0.000 description 1
- 210000005003 heart tissue Anatomy 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 208000037906 ischaemic injury Diseases 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000010470 malonic ester synthesis reaction Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007102 metabolic function Effects 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 238000002610 neuroimaging Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000002601 radiography Methods 0.000 description 1
- 238000003259 recombinant expression Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008354 sodium chloride injection Substances 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 229940108519 trasylol Drugs 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
- A61K51/0402—Organic compounds carboxylic acid carriers, fatty acids
-
- 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
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physics & Mathematics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Nuclear Medicine (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US786395P | 1995-12-01 | 1995-12-01 | |
| US60/007,863 | 1995-12-01 | ||
| PCT/US1996/019024 WO1997019705A1 (en) | 1995-12-01 | 1996-11-25 | Stereoisomers of fatty acid analogs for diagnostic imaging |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2238860A1 CA2238860A1 (en) | 1997-06-05 |
| CA2238860C true CA2238860C (en) | 2009-01-13 |
Family
ID=21728502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002238860A Expired - Fee Related CA2238860C (en) | 1995-12-01 | 1996-11-25 | Stereoisomers of fatty acid analogs for diagnostic imaging |
Country Status (8)
| Country | Link |
|---|---|
| US (4) | US7005119B2 (enExample) |
| EP (2) | EP0869821B1 (enExample) |
| JP (3) | JP4272259B2 (enExample) |
| AT (2) | ATE353019T1 (enExample) |
| CA (1) | CA2238860C (enExample) |
| DE (1) | DE69636881T2 (enExample) |
| ES (2) | ES2374743T3 (enExample) |
| WO (1) | WO1997019705A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE353019T1 (de) * | 1995-12-01 | 2007-02-15 | Molecular Insight Pharm Inc | Stereoisomere von fettsäureanalogen zur diagnostischen bildgebung |
| US20090117032A1 (en) * | 1998-09-08 | 2009-05-07 | The General Hospital Corporation | Imaging Agents for Early Detection and Monitoring of Cardiovascular Plaque |
| EP0992245A1 (en) * | 1998-09-16 | 2000-04-12 | Goldham Bioglan Pharma GmbH | Radio-contrast agents |
| EP1040825A1 (en) * | 1999-03-11 | 2000-10-04 | K.U. Leuven Research & Development | Means for diagnosing bladder carcinoma |
| DE60030270T2 (de) * | 1999-04-14 | 2007-08-30 | Molecular Insight Pharmaceuticals, Inc., Cambridge | Fettsaure analoge zur diagnose von kranzarterie erkrankungen |
| WO2003084575A1 (en) * | 2002-04-01 | 2003-10-16 | Biostream, Inc. | Pendant fatty acid imaging agents |
| AU2004232297B2 (en) * | 2003-04-17 | 2010-11-04 | The General Hospital Corporation | Method for monitoring blood flow and metabolic uptake in tissue with radiolabeled alkanoic acid |
| JP2012526129A (ja) * | 2009-05-04 | 2012-10-25 | ワシントン・ユニバーシティ | 脂肪酸代謝および貯蔵を画像化するためのｐｅｔ放射性追跡子 |
| DE102010010666A1 (de) * | 2010-03-01 | 2011-09-01 | Sven Reske | Diagnose und Therapie von Krebserkrankungen mittels Fettsäuren |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6802651A (enExample) * | 1968-02-23 | 1969-08-26 | ||
| DE2828623C2 (de) * | 1978-06-29 | 1983-11-17 | Kernforschungsanlage Jülich GmbH, 5170 Jülich | Mit radioaktivem Flour markierte C↓1↓↓6↓-bis C↓1↓↓8↓- Fettsäuren, ein Verfahren zu ihrer Herstellung sowie deren Verwendung |
| DE2947500C2 (de) * | 1979-11-24 | 1984-05-10 | Dutschka, Klaus, 4300 Essen | Radiojodierte ω -Phenylfettsäuren, ihre Herstellung und deren Verwendung zur szintigraphischen Untersuchung des Herzmuskels und der Leber |
| FR2508902B1 (fr) * | 1981-07-02 | 1985-09-06 | Commissariat Energie Atomique | Procede de preparation extemporanee d'un acide gras injectable, marque a l'iode radioactif et preparation de derives iodes utilisables pour la mise en oeuvre de ce procede |
| US4524059A (en) * | 1983-01-28 | 1985-06-18 | The General Hospital Corporation | Fatty acid analogs |
| US4942231A (en) * | 1984-05-24 | 1990-07-17 | Mallinckrodt, Inc. | Method of preparing a chlorinated, brominated, radio-brominated, iodinated and/or radioiodinated aromatic or heteroaromatic compound |
| CA1243329A (en) * | 1985-03-11 | 1988-10-18 | Amersham Int Plc | TECHNETIUM COMPLEXES WITH PROPYLENE-AMINE-OXIMES |
| US4746505A (en) * | 1985-04-26 | 1988-05-24 | President And Fellows Of Harvard College | Technetium radiodiagnostic fatty acids derived from bisamide bisthiol ligands |
| 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 |
| US4877599A (en) | 1986-11-10 | 1989-10-31 | New England Deaconess Hospital Corporation | Detection of vascular disease with labelled antibodies |
| ATE89271T1 (de) * | 1987-11-19 | 1993-05-15 | Univ Vanderbilt | Radiojodhaltige benzamide und verfahren zu ihrer verwendung als radiobildende agenzien. |
| US5242681A (en) * | 1990-03-12 | 1993-09-07 | Research Corporation Technologies, Inc. | Lipophilic contrast agents for diagnostic image analysis |
| US7238340B1 (en) * | 1991-11-27 | 2007-07-03 | Cis Bio International | Monoamine, diamide, thiol-containing metal chelating agents |
| ATE353019T1 (de) * | 1995-12-01 | 2007-02-15 | Molecular Insight Pharm Inc | Stereoisomere von fettsäureanalogen zur diagnostischen bildgebung |
| EP2324857A1 (en) * | 1997-09-08 | 2011-05-25 | The General Hospital Corporation | Imaging agents for early detection of cardiovascular plaque |
| US7060251B1 (en) * | 1997-09-08 | 2006-06-13 | The General Hospital Corporation | Imaging agents for early detection and monitoring of cardiovascular plaque |
| DE60030270T2 (de) * | 1999-04-14 | 2007-08-30 | Molecular Insight Pharmaceuticals, Inc., Cambridge | Fettsaure analoge zur diagnose von kranzarterie erkrankungen |
| EP1265865A2 (en) * | 2000-03-21 | 2002-12-18 | The Procter & Gamble Company | Difluorobutyric acid derivatives and their use as metalloprotease inhibitors |
| AU2004232297B2 (en) * | 2003-04-17 | 2010-11-04 | The General Hospital Corporation | Method for monitoring blood flow and metabolic uptake in tissue with radiolabeled alkanoic acid |
-
1996
- 1996-11-25 AT AT96941503T patent/ATE353019T1/de not_active IP Right Cessation
- 1996-11-25 DE DE69636881T patent/DE69636881T2/de not_active Expired - Lifetime
- 1996-11-25 JP JP52066997A patent/JP4272259B2/ja not_active Expired - Fee Related
- 1996-11-25 WO PCT/US1996/019024 patent/WO1997019705A1/en not_active Ceased
- 1996-11-25 EP EP96941503A patent/EP0869821B1/en not_active Expired - Lifetime
- 1996-11-25 CA CA002238860A patent/CA2238860C/en not_active Expired - Fee Related
- 1996-11-25 AT AT06025944T patent/ATE526995T1/de not_active IP Right Cessation
- 1996-11-25 ES ES06025944T patent/ES2374743T3/es not_active Expired - Lifetime
- 1996-11-25 ES ES96941503T patent/ES2281906T3/es not_active Expired - Lifetime
- 1996-11-25 EP EP06025944A patent/EP1767224B1/en not_active Expired - Lifetime
-
2003
- 2003-05-05 US US10/429,416 patent/US7005119B2/en not_active Expired - Fee Related
-
2005
- 2005-11-16 US US11/274,505 patent/US7314609B2/en not_active Expired - Fee Related
-
2007
- 2007-01-09 US US11/621,241 patent/US20070128110A1/en not_active Abandoned
-
2008
- 2008-01-16 JP JP2008006447A patent/JP4937144B2/ja not_active Expired - Fee Related
- 2008-04-02 US US12/061,528 patent/US20080247948A1/en not_active Abandoned
-
2011
- 2011-10-24 JP JP2011232673A patent/JP2012036215A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ES2374743T3 (es) | 2012-02-21 |
| US7314609B2 (en) | 2008-01-01 |
| US20080247948A1 (en) | 2008-10-09 |
| ATE353019T1 (de) | 2007-02-15 |
| US7005119B2 (en) | 2006-02-28 |
| HK1102262A1 (en) | 2007-11-09 |
| CA2238860A1 (en) | 1997-06-05 |
| JP4937144B2 (ja) | 2012-05-23 |
| JP2012036215A (ja) | 2012-02-23 |
| EP1767224B1 (en) | 2011-10-05 |
| JP4272259B2 (ja) | 2009-06-03 |
| HK1016494A1 (en) | 1999-11-05 |
| EP0869821A4 (en) | 2002-08-28 |
| JP2000502059A (ja) | 2000-02-22 |
| ATE526995T1 (de) | 2011-10-15 |
| EP0869821A1 (en) | 1998-10-14 |
| EP1767224A2 (en) | 2007-03-28 |
| JP2008201774A (ja) | 2008-09-04 |
| US20030215386A1 (en) | 2003-11-20 |
| EP0869821B1 (en) | 2007-01-31 |
| DE69636881D1 (de) | 2007-03-22 |
| US20070128110A1 (en) | 2007-06-07 |
| WO1997019705A1 (en) | 1997-06-05 |
| EP1767224A3 (en) | 2007-11-28 |
| ES2281906T3 (es) | 2007-10-01 |
| DE69636881T2 (de) | 2007-09-20 |
| US20060078495A1 (en) | 2006-04-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4937144B2 (ja) | 診断用イメージングのための脂肪酸アナログの立体異性体 | |
| US5310536A (en) | Ligands for improving metal chelate formation kinetics | |
| AU2010243678B2 (en) | Labeled molecular imaging agents, methods of making and methods of use | |
| JPH03505094A (ja) | 動脈映像のための合成ペプチド | |
| Basuli et al. | One-pot synthesis and biodistribution of fluorine-18 labeled serum albumin for vascular imaging | |
| EP0869820B1 (en) | Cardiovascular and thrombus imaging agents, methods and kits | |
| WO1997024146A9 (en) | Cardiovascular and thrombus imaging agents, methods and kits | |
| HK1016494B (en) | Stereoisomers of fatty acid analogs for diagnostic imaging | |
| Lu et al. | Design, synthesis, and biological evaluation of a 99m Tc-labeled small-molecule tracer for PD-L1 imaging | |
| HK1102262B (en) | Stereoisomers of fatty acid analogs for diagnostic imaging | |
| KR101389179B1 (ko) | 니트로이미다졸-아미노산 핵 저산소증 조영제 및 그 전구체 | |
| JPH03504011A (ja) | 温血生物における局所エネルギー代謝の定位定量方法とそのための組成物 | |
| JP2012042215A (ja) | 早期膵がんの検出方法 | |
| RU2019141963A (ru) | Новые пса-связывающие агенты и их применение | |
| AU1495601A (en) | Cardiovascular and thrombus imaging agents, methods and kits |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20141125 |