ES3009015T3 - Fatty acid derivative labeled with positron-emitting radionuclide - Google Patents
Fatty acid derivative labeled with positron-emitting radionuclide Download PDFInfo
- Publication number
- ES3009015T3 ES3009015T3 ES19837826T ES19837826T ES3009015T3 ES 3009015 T3 ES3009015 T3 ES 3009015T3 ES 19837826 T ES19837826 T ES 19837826T ES 19837826 T ES19837826 T ES 19837826T ES 3009015 T3 ES3009015 T3 ES 3009015T3
- Authority
- ES
- Spain
- Prior art keywords
- fatty acid
- salt
- acid derivative
- compound
- labeled fatty
- 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.)
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- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 70
- 239000000194 fatty acid Substances 0.000 title claims abstract description 70
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 70
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 70
- 150000003839 salts Chemical class 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 56
- 238000002059 diagnostic imaging Methods 0.000 claims abstract description 26
- 208000019622 heart disease Diseases 0.000 claims abstract description 16
- 208000031225 myocardial ischemia Diseases 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 85
- 239000000203 mixture Substances 0.000 claims description 68
- 230000008569 process Effects 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- KRHYYFGTRYWZRS-BJUDXGSMSA-M fluorine-18(1-) Chemical compound [18F-] KRHYYFGTRYWZRS-BJUDXGSMSA-M 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 239000000032 diagnostic agent Substances 0.000 claims description 3
- 229940039227 diagnostic agent Drugs 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 238000002600 positron emission tomography Methods 0.000 abstract description 35
- 210000004165 myocardium Anatomy 0.000 abstract description 14
- 238000003384 imaging method Methods 0.000 abstract description 13
- 239000000700 radioactive tracer Substances 0.000 abstract description 12
- 230000002503 metabolic effect Effects 0.000 abstract description 10
- XLHOLOJPVDSSDQ-AVGIDEFSSA-N 3-[(Z)-3-(18F)fluoranyltetradec-5-enyl]sulfanylpropanoic acid Chemical compound [18F]C(CCSCCC(=O)O)C\C=C/CCCCCCCC XLHOLOJPVDSSDQ-AVGIDEFSSA-N 0.000 abstract description 5
- 238000011002 quantification Methods 0.000 abstract description 3
- 230000001225 therapeutic effect Effects 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 46
- 239000000243 solution Substances 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- -1 [18F]fluoride ions Chemical class 0.000 description 25
- 238000009825 accumulation Methods 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 235000019439 ethyl acetate Nutrition 0.000 description 20
- 239000000126 substance Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000007858 starting material Substances 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- YFSQQMGSLWYHBL-XRQCYVQQSA-N 3-[(z)-14-fluoranyltetradec-5-enyl]sulfanylpropanoic acid Chemical compound OC(=O)CCSCCCC\C=C/CCCCCCCC[18F] YFSQQMGSLWYHBL-XRQCYVQQSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 210000000988 bone and bone Anatomy 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- 241000700159 Rattus Species 0.000 description 13
- 210000002216 heart Anatomy 0.000 description 13
- 238000010898 silica gel chromatography Methods 0.000 description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 125000006239 protecting group Chemical group 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 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 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 208000010125 myocardial infarction Diseases 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 6
- 210000000056 organ Anatomy 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 5
- 238000012879 PET imaging Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000004060 metabolic process Effects 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- QNWRQQSASSIICT-UHFFFAOYSA-N 5-[tert-butyl(dimethyl)silyl]oxy-4-[tert-butyl(diphenyl)silyl]oxypentanal Chemical compound C(C)(C)(C)[Si](OCC(CCC=O)O[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C)(C)C QNWRQQSASSIICT-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- NKGNJIDNCZMBNC-KHPPLWFESA-N methyl 3-[(Z)-3-hydroxytetradec-5-enyl]sulfanylpropanoate Chemical compound OC(CCSCCC(=O)OC)C\C=C/CCCCCCCC NKGNJIDNCZMBNC-KHPPLWFESA-N 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- 230000002285 radioactive effect Effects 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- NPCIWINHUDIWAV-UHFFFAOYSA-N 15-(4-iodophenyl)-3-methylpentadecanoic acid Chemical compound OC(=O)CC(C)CCCCCCCCCCCCC1=CC=C(I)C=C1 NPCIWINHUDIWAV-UHFFFAOYSA-N 0.000 description 3
- KZLMDUNDGBJYQB-AVGIDEFSSA-N 3-[(Z)-2-(18F)fluoranyltetradec-5-enyl]sulfanylpropanoic acid Chemical compound [18F]C(CSCCC(=O)O)CC\C=C/CCCCCCCC KZLMDUNDGBJYQB-AVGIDEFSSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 3
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 3
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000005703 Trimethylamine hydrochloride Substances 0.000 description 3
- 210000004351 coronary vessel Anatomy 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000003983 inhalation anesthetic agent Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229960002725 isoflurane Drugs 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- MBHDJQUJQGWXQD-KHPPLWFESA-N methyl 3-[(Z)-2-hydroxytetradec-5-enyl]sulfanylpropanoate Chemical compound OC(CSCCC(=O)OC)CC\C=C/CCCCCCCC MBHDJQUJQGWXQD-KHPPLWFESA-N 0.000 description 3
- MJGMJBFYWONSDG-KHPPLWFESA-N methyl 3-[(Z)-3-(4-nitrophenyl)sulfonyloxytetradec-5-enyl]sulfanylpropanoate Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)OC(CCSCCC(=O)OC)C\C=C/CCCCCCCC MJGMJBFYWONSDG-KHPPLWFESA-N 0.000 description 3
- NVPCJCNEURVLGA-KHPPLWFESA-N methyl 3-[(Z)-3-bromotetradec-5-enyl]sulfanylpropanoate Chemical compound BrC(CCSCCC(=O)OC)C\C=C/CCCCCCCC NVPCJCNEURVLGA-KHPPLWFESA-N 0.000 description 3
- 230000002107 myocardial effect Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000002603 single-photon emission computed tomography Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000013077 target material Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 3
- 210000003462 vein Anatomy 0.000 description 3
- RDHAZEMTRHXKGT-SEYXRHQNSA-N (Z)-2-[tert-butyl(diphenyl)silyl]oxytetradec-5-en-1-ol Chemical compound [Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC(CO)CC\C=C/CCCCCCCC RDHAZEMTRHXKGT-SEYXRHQNSA-N 0.000 description 2
- CVVMLSUXFCXKEG-QINSGFPZSA-N (Z)-3-[tert-butyl(diphenyl)silyl]oxytetradec-5-en-1-ol Chemical compound [Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC(CCO)C\C=C/CCCCCCCC CVVMLSUXFCXKEG-QINSGFPZSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BHAVPOGLYRBECO-UHFFFAOYSA-N 2-(9-bromononan-4-yloxy)oxane Chemical compound BrCCCCCC(CCC)OC1OCCCC1 BHAVPOGLYRBECO-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- UIDYEXGBCAVMAM-GKTGUEEDSA-N 3-(12-fluoranyldodecylsulfanyl)propanoic acid Chemical compound OC(=O)CCSCCCCCCCCCCCC[18F] UIDYEXGBCAVMAM-GKTGUEEDSA-N 0.000 description 2
- KXUIWEKGABOUNX-HFOCOGKHSA-N 3-[(Z)-11-(18F)fluoranyltetradec-5-enyl]sulfanylpropanoic acid Chemical compound [18F]C(CCCC\C=C/CCCCSCCC(=O)O)CCC KXUIWEKGABOUNX-HFOCOGKHSA-N 0.000 description 2
- ONEIYNABWFFWSI-CLSPLTCCSA-N 3-[(Z)-13-(18F)fluoranyltetradec-5-enyl]sulfanylpropanoic acid Chemical compound [18F]C(CCCCCC\C=C/CCCCSCCC(=O)O)C ONEIYNABWFFWSI-CLSPLTCCSA-N 0.000 description 2
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 2
- QKUXQKVABHFQKT-UHFFFAOYSA-N 5-[tert-butyl(dimethyl)silyl]oxy-4-[tert-butyl(diphenyl)silyl]oxypentan-1-ol Chemical compound [Si](C)(C)(C(C)(C)C)OCC(CCCO)O[Si](C1=CC=CC=C1)(C1=CC=CC=C1)C(C)(C)C QKUXQKVABHFQKT-UHFFFAOYSA-N 0.000 description 2
- KPLOBHKFLFONAI-UHFFFAOYSA-N 9-bromononan-4-ol Chemical compound CCCC(O)CCCCCBr KPLOBHKFLFONAI-UHFFFAOYSA-N 0.000 description 2
- 208000020446 Cardiac disease Diseases 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
- XYMGMZBFGILTIZ-CASUBRPWSA-N [18F]C(CCCSCCC(=O)O)\C=C/CCCCCCCC Chemical compound [18F]C(CCCSCCC(=O)O)\C=C/CCCCCCCC XYMGMZBFGILTIZ-CASUBRPWSA-N 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- YCKRFDGAMUMZLT-BJUDXGSMSA-N fluorine-18 atom Chemical compound [18F] YCKRFDGAMUMZLT-BJUDXGSMSA-N 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000006192 iodination reaction Methods 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 150000004668 long chain fatty acids Chemical class 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- ROMFPAVLPSNRGN-WAYWQWQTSA-N methyl 3-[(Z)-11-(4-methylphenyl)sulfonyloxytetradec-5-enyl]sulfanylpropanoate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)OC(CCCC\C=C/CCCCSCCC(=O)OC)CCC ROMFPAVLPSNRGN-WAYWQWQTSA-N 0.000 description 2
- GDLCYMNOPSSWSU-PLNGDYQASA-N methyl 3-[(Z)-11-(oxan-2-yloxy)tetradec-5-enyl]sulfanylpropanoate Chemical compound O1C(CCCC1)OC(CCCC\C=C/CCCCSCCC(=O)OC)CCC GDLCYMNOPSSWSU-PLNGDYQASA-N 0.000 description 2
- ZZYLORQSLAILPL-ALCCZGGFSA-N methyl 3-[(Z)-13-(4-methylphenyl)sulfonyloxytetradec-5-enyl]sulfanylpropanoate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)OC(CCCCCC\C=C/CCCCSCCC(=O)OC)C ZZYLORQSLAILPL-ALCCZGGFSA-N 0.000 description 2
- SZAQOYYAUBOFCD-YPKPFQOOSA-N methyl 3-[(Z)-2-[tert-butyl(diphenyl)silyl]oxytetradec-5-enyl]sulfanylpropanoate Chemical compound [Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC(CSCCC(=O)OC)CC\C=C/CCCCCCCC SZAQOYYAUBOFCD-YPKPFQOOSA-N 0.000 description 2
- UIXOITYDRSFFGX-KHPPLWFESA-N methyl 3-[(Z)-2-bromotetradec-5-enyl]sulfanylpropanoate Chemical compound BrC(CSCCC(=O)OC)CC\C=C/CCCCCCCC UIXOITYDRSFFGX-KHPPLWFESA-N 0.000 description 2
- QCOINMAGEAJUEK-QXMHVHEDSA-N methyl 3-[(Z)-3-(4-methylphenyl)sulfonyloxytetradec-5-enyl]sulfanylpropanoate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)OC(CCSCCC(=O)OC)C\C=C/CCCCCCCC QCOINMAGEAJUEK-QXMHVHEDSA-N 0.000 description 2
- XYRXHQGCOPBNEL-SSZFMOIBSA-N methyl 3-[(Z)-3-[tert-butyl(diphenyl)silyl]oxytetradec-5-enyl]sulfanylpropanoate Chemical compound [Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC(CCSCCC(=O)OC)C\C=C/CCCCCCCC XYRXHQGCOPBNEL-SSZFMOIBSA-N 0.000 description 2
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- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 239000012929 tonicity agent Substances 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/54—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and unsaturated
-
- 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
-
- 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
- C07B59/001—Acyclic or carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01T—MEASUREMENT OF NUCLEAR OR X-RADIATION
- G01T1/00—Measuring X-radiation, gamma radiation, corpuscular radiation, or cosmic radiation
- G01T1/16—Measuring radiation intensity
- G01T1/161—Applications in the field of nuclear medicine, e.g. in vivo counting
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Veterinary Medicine (AREA)
- Medical Informatics (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Physics & Mathematics (AREA)
- High Energy & Nuclear Physics (AREA)
- Molecular Biology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nuclear Medicine (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018136483 | 2018-07-20 | ||
| PCT/JP2019/028380 WO2020017620A1 (ja) | 2018-07-20 | 2019-07-19 | 陽電子放出核種で標識された脂肪酸誘導体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES3009015T3 true ES3009015T3 (en) | 2025-03-25 |
Family
ID=69164918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES19837826T Active ES3009015T3 (en) | 2018-07-20 | 2019-07-19 | Fatty acid derivative labeled with positron-emitting radionuclide |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US12029797B2 (https=) |
| EP (1) | EP3825302B1 (https=) |
| JP (1) | JP7375755B2 (https=) |
| KR (1) | KR102718221B1 (https=) |
| CN (1) | CN112638868B (https=) |
| AU (1) | AU2019304781B2 (https=) |
| CA (1) | CA3106903A1 (https=) |
| ES (1) | ES3009015T3 (https=) |
| WO (1) | WO2020017620A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES3009015T3 (en) | 2018-07-20 | 2025-03-25 | Astellas Pharma Inc | Fatty acid derivative labeled with positron-emitting radionuclide |
| US20230065079A1 (en) * | 2020-01-17 | 2023-03-02 | Astellas Pharma Inc. | Fatty acid derivative labeled with positron-emitting radionuclide |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2000063216A1 (en) | 1999-04-19 | 2000-10-26 | Duke University | F-18-labeled thia fatty acids and methods of making and using the same |
| CA2522737C (en) * | 2003-04-17 | 2017-06-06 | The General Hospital Corporation | Method for monitoring blood flow and metabolic uptake in tissue with radiolabeled alkanoic acid |
| CN1217924C (zh) | 2003-10-17 | 2005-09-07 | 江苏省原子医学研究所 | 一种氟标记脂肪酸心肌代谢显像剂14(r,s)－氟[18f]－6－硫十七烷酸的纯化方法 |
| CA2760334A1 (en) | 2009-05-04 | 2010-11-11 | Washington University | Pet radiotracers for imaging fatty acid metabolism and storage |
| WO2014179341A1 (en) | 2013-04-29 | 2014-11-06 | Matinas Biopharma, Inc. | Treatment with omega-3 fatty acid compositions |
| WO2015023631A2 (en) | 2013-08-12 | 2015-02-19 | Carolyn Anderson | Fatty acid analogs and their use |
| CN105523977B (zh) | 2016-02-04 | 2017-05-24 | 河南中医学院 | [11c]‑巯甲基脂肪酸的制备方法与应用 |
| ES3009015T3 (en) | 2018-07-20 | 2025-03-25 | Astellas Pharma Inc | Fatty acid derivative labeled with positron-emitting radionuclide |
| US20230065079A1 (en) | 2020-01-17 | 2023-03-02 | Astellas Pharma Inc. | Fatty acid derivative labeled with positron-emitting radionuclide |
-
2019
- 2019-07-19 ES ES19837826T patent/ES3009015T3/es active Active
- 2019-07-19 KR KR1020217001389A patent/KR102718221B1/ko active Active
- 2019-07-19 JP JP2020531374A patent/JP7375755B2/ja active Active
- 2019-07-19 US US17/261,328 patent/US12029797B2/en active Active
- 2019-07-19 EP EP19837826.7A patent/EP3825302B1/en active Active
- 2019-07-19 CN CN201980048149.8A patent/CN112638868B/zh active Active
- 2019-07-19 CA CA3106903A patent/CA3106903A1/en active Pending
- 2019-07-19 AU AU2019304781A patent/AU2019304781B2/en active Active
- 2019-07-19 WO PCT/JP2019/028380 patent/WO2020017620A1/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU2019304781B2 (en) | 2023-12-21 |
| US20210338845A1 (en) | 2021-11-04 |
| CN112638868B (zh) | 2023-06-20 |
| KR102718221B1 (ko) | 2024-10-15 |
| US12029797B2 (en) | 2024-07-09 |
| EP3825302A1 (en) | 2021-05-26 |
| CN112638868A (zh) | 2021-04-09 |
| WO2020017620A1 (ja) | 2020-01-23 |
| EP3825302B1 (en) | 2025-01-08 |
| AU2019304781A1 (en) | 2021-02-11 |
| KR20210032392A (ko) | 2021-03-24 |
| CA3106903A1 (en) | 2020-01-23 |
| JP7375755B2 (ja) | 2023-11-08 |
| EP3825302A4 (en) | 2022-05-04 |
| JPWO2020017620A1 (ja) | 2021-08-02 |
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