ES2665687T3 - Agentes de contraste para imágenes de perfusión miocárdica - Google Patents
Agentes de contraste para imágenes de perfusión miocárdica Download PDFInfo
- Publication number
- ES2665687T3 ES2665687T3 ES05723066.6T ES05723066T ES2665687T3 ES 2665687 T3 ES2665687 T3 ES 2665687T3 ES 05723066 T ES05723066 T ES 05723066T ES 2665687 T3 ES2665687 T3 ES 2665687T3
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- cdcl3
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- 239000002872 contrast media Substances 0.000 title abstract description 7
- 238000003384 imaging method Methods 0.000 title abstract description 3
- 230000002107 myocardial effect Effects 0.000 title 1
- 230000010412 perfusion Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
- 239000001257 hydrogen Substances 0.000 abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 4
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 abstract 3
- DMYHGDXADUDKCQ-UHFFFAOYSA-N fenazaquin Chemical compound C1=CC(C(C)(C)C)=CC=C1CCOC1=NC=NC2=CC=CC=C12 DMYHGDXADUDKCQ-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000005663 Pyridaben Substances 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
- 239000000243 solution Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000000047 product Substances 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000003921 oil Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- -1 for example Substances 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 150000002632 lipids Chemical class 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 description 7
- 239000007832 Na2SO4 Substances 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 239000002738 chelating agent Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 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 6
- 239000013058 crude material Substances 0.000 description 5
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- 239000004005 microsphere Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000002356 single layer Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 150000003573 thiols Chemical group 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- MOQOOKGPCBQMCY-UHFFFAOYSA-N acetic acid;hexane Chemical compound CC(O)=O.CCCCCC MOQOOKGPCBQMCY-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- QVDYYQXUNAQSNI-UHFFFAOYSA-N ethyl acetate;pentane Chemical compound CCCCC.CCOC(C)=O QVDYYQXUNAQSNI-UHFFFAOYSA-N 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 239000002502 liposome Substances 0.000 description 2
- HXTBDRDIICYZOO-UHFFFAOYSA-N methyl 4-[4-[tert-butyl(dimethyl)silyl]oxybutyl]benzoate Chemical compound COC(=O)C1=CC=C(CCCCO[Si](C)(C)C(C)(C)C)C=C1 HXTBDRDIICYZOO-UHFFFAOYSA-N 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- MKUWVMRNQOOSAT-UHFFFAOYSA-N methylvinylmethanol Natural products CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- CIDZDYAPPNMBIY-UHFFFAOYSA-N (4-butylphenyl)methanol Chemical compound CCCCC1=CC=C(CO)C=C1 CIDZDYAPPNMBIY-UHFFFAOYSA-N 0.000 description 1
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
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- RXACEEPNTRHYBQ-UHFFFAOYSA-N 2-[[2-[[2-[(2-sulfanylacetyl)amino]acetyl]amino]acetyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)CNC(=O)CNC(=O)CS RXACEEPNTRHYBQ-UHFFFAOYSA-N 0.000 description 1
- WENRDIZICMMGRK-UHFFFAOYSA-N 2-chloro-5-hydroxypyridazin-3-one Chemical compound ClN1N=CC(=CC1=O)O WENRDIZICMMGRK-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
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- VXGBMTQYICXIAD-UHFFFAOYSA-N 2-tert-butyl-5-[[4-[2-[tert-butyl(dimethyl)silyl]oxyethoxymethyl]phenyl]methoxy]-4-chloropyridazin-3-one Chemical compound O=C1N(C(C)(C)C)N=CC(OCC=2C=CC(COCCO[Si](C)(C)C(C)(C)C)=CC=2)=C1Cl VXGBMTQYICXIAD-UHFFFAOYSA-N 0.000 description 1
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- UZASZZZPNICPKS-UHFFFAOYSA-N 2-tert-butyl-5-[[4-[4-[tert-butyl(dimethyl)silyl]oxybutyl]phenyl]methoxy]-4-chloropyridazin-3-one Chemical compound O=C1N(C(C)(C)C)N=CC(OCC=2C=CC(CCCCO[Si](C)(C)C(C)(C)C)=CC=2)=C1Cl UZASZZZPNICPKS-UHFFFAOYSA-N 0.000 description 1
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- 229910006069 SO3H Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
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- WDLRUFUQRNWCPK-UHFFFAOYSA-N Tetraxetan Chemical compound OC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 WDLRUFUQRNWCPK-UHFFFAOYSA-N 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- AKKHSVSWRZCZNC-UHFFFAOYSA-N [4-[4-[tert-butyl(dimethyl)silyl]oxybutyl]phenyl]methanol Chemical compound CC(C)(C)[Si](C)(C)OCCCCC1=CC=C(CO)C=C1 AKKHSVSWRZCZNC-UHFFFAOYSA-N 0.000 description 1
- CQNUVRLDYLUAJS-UHFFFAOYSA-N acetic acid;pentane Chemical compound CC(O)=O.CCCCC CQNUVRLDYLUAJS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
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- 125000002947 alkylene group Chemical group 0.000 description 1
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- 238000013459 approach Methods 0.000 description 1
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- MLWMZTRCXNCAPF-UHFFFAOYSA-N azane;methylarsonic acid Chemical compound [NH4+].C[As](O)([O-])=O MLWMZTRCXNCAPF-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
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- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
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- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
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- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
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- DAFHXTWTKVEOMP-UHFFFAOYSA-N methyl 4-(2-hydroxyethoxymethyl)benzoate Chemical compound COC(=O)C1=CC=C(COCCO)C=C1 DAFHXTWTKVEOMP-UHFFFAOYSA-N 0.000 description 1
- JXKOGZHDDHKQJU-UHFFFAOYSA-N methyl 4-(3-hydroxypropoxy)benzoate Chemical compound COC(=O)C1=CC=C(OCCCO)C=C1 JXKOGZHDDHKQJU-UHFFFAOYSA-N 0.000 description 1
- RFKQUJVVAPULID-UHFFFAOYSA-N methyl 4-(3-oxobutyl)benzoate Chemical compound COC(=O)C1=CC=C(CCC(C)=O)C=C1 RFKQUJVVAPULID-UHFFFAOYSA-N 0.000 description 1
- VBWFYEFYHJRJER-UHFFFAOYSA-N methyl 4-(hydroxymethyl)benzoate Chemical compound COC(=O)C1=CC=C(CO)C=C1 VBWFYEFYHJRJER-UHFFFAOYSA-N 0.000 description 1
- KTQDFUWVLWTECK-UHFFFAOYSA-N methyl 4-[2-[tert-butyl(dimethyl)silyl]oxyethoxymethyl]benzoate Chemical compound COC(=O)C1=CC=C(COCCO[Si](C)(C)C(C)(C)C)C=C1 KTQDFUWVLWTECK-UHFFFAOYSA-N 0.000 description 1
- RVHYKIIJCHCACW-UHFFFAOYSA-N methyl 4-[3-[tert-butyl(dimethyl)silyl]oxypropoxy]benzoate Chemical compound COC(=O)C1=CC=C(OCCCO[Si](C)(C)C(C)(C)C)C=C1 RVHYKIIJCHCACW-UHFFFAOYSA-N 0.000 description 1
- LYWZMGGXPMJKFV-UHFFFAOYSA-N methyl 4-[4-(2-hydroxyethyl)phenyl]-4-oxobutanoate Chemical compound COC(=O)CCC(=O)C1=CC=C(CCO)C=C1 LYWZMGGXPMJKFV-UHFFFAOYSA-N 0.000 description 1
- CZNGTXVOZOWWKM-UHFFFAOYSA-N methyl 4-bromobenzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1 CZNGTXVOZOWWKM-UHFFFAOYSA-N 0.000 description 1
- SRXOJMOGPYFZKC-UHFFFAOYSA-N methyl 4-chloro-4-oxobutanoate Chemical compound COC(=O)CCC(Cl)=O SRXOJMOGPYFZKC-UHFFFAOYSA-N 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229940102859 methylene diphosphonate Drugs 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000002077 nanosphere Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000000816 peptidomimetic Substances 0.000 description 1
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 150000003004 phosphinoxides Chemical class 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
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- Magnetic Resonance Imaging Apparatus (AREA)
- Nuclear Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Ultra Sonic Daignosis Equipment (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| US54486104P | 2004-02-13 | 2004-02-13 | |
| US544861P | 2004-02-13 | ||
| US11/055,498 US7344702B2 (en) | 2004-02-13 | 2005-02-10 | Contrast agents for myocardial perfusion imaging |
| US55498 | 2005-02-10 | ||
| PCT/US2005/004687 WO2005079391A2 (en) | 2004-02-13 | 2005-02-11 | Contrast agents for myocardial perfusion imaging |
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| ES2665687T3 true ES2665687T3 (es) | 2018-04-26 |
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| ES18150652T Expired - Lifetime ES2878171T3 (es) | 2004-02-13 | 2005-02-11 | Agentes de contraste para imagenología de perfusión miocárdica |
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| ES18150652T Expired - Lifetime ES2878171T3 (es) | 2004-02-13 | 2005-02-11 | Agentes de contraste para imagenología de perfusión miocárdica |
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| US7344702B2 (en) * | 2004-02-13 | 2008-03-18 | Bristol-Myers Squibb Pharma Company | Contrast agents for myocardial perfusion imaging |
| US7485283B2 (en) * | 2004-04-28 | 2009-02-03 | Lantheus Medical Imaging | Contrast agents for myocardial perfusion imaging |
| US7824659B2 (en) | 2005-08-10 | 2010-11-02 | Lantheus Medical Imaging, Inc. | Methods of making radiolabeled tracers and precursors thereof |
| JP5368099B2 (ja) * | 2005-10-07 | 2013-12-18 | ゲルベ | ガリウムと錯体形成することが可能なシグナル部分にカップリングされた、生物学的標的の認識のための部分を含んでなる化合物 |
| US8986650B2 (en) | 2005-10-07 | 2015-03-24 | Guerbet | Complex folate-NOTA-Ga68 |
| WO2008009077A2 (en) * | 2006-07-20 | 2008-01-24 | Gilead Sciences, Inc. | 4,6-dl- and 2,4,6-trisubstituted quinazoline derivatives and pharmaceutical compositions useful for treating viral infections |
| WO2008009078A2 (en) | 2006-07-20 | 2008-01-24 | Gilead Sciences, Inc. | 4,6-dl- and 2,4,6-trisubstituted quinazoline derivatives useful for treating viral infections |
| KR20170102580A (ko) | 2006-12-26 | 2017-09-11 | 랜티우스 메디컬 이메징, 인크. | 심장 신경 분포의 영상화를 위한 리간드 |
| WO2008128058A1 (en) * | 2007-04-13 | 2008-10-23 | The Trustees Of The University Of Pennsylvania | New gallium bisaminothiolate complexes for myocardial imaging |
| PT2257315T (pt) * | 2008-02-29 | 2020-01-27 | Lantheus Medical Imaging Inc | Agentes de contraste para aplicações incluindo imagiologia de perfusão |
| AU2015200027B2 (en) * | 2008-02-29 | 2017-01-19 | Lantheus Medical Imaging, Inc. | Contrast agents for applications including perfusion imaging |
| US8934959B2 (en) * | 2008-07-09 | 2015-01-13 | Koninklijke Philips N.V. | Physiological pharmacokinetic analysis for combined molecular MRI and dynamic PET imaging |
| KR20160030589A (ko) | 2009-04-15 | 2016-03-18 | 랜티우스 메디컬 이메징, 인크. | 아스코르브산을 사용한 방사성 약제 조성물의 안정화 |
| JP2012532833A (ja) * | 2009-07-11 | 2012-12-20 | バイエル ファーマ アクチエンゲゼルシャフト | 非極性及び極性脱離基 |
| EP2289889A1 (en) * | 2009-08-18 | 2011-03-02 | Endura S.p.a. | Substituted alkynyl phenoxy compounds and their uses |
| CN101993383A (zh) * | 2009-08-26 | 2011-03-30 | 成都伊诺达博医药科技有限公司 | 决奈达隆关键中间体4-[3-(二丁氨基)丙氧基]苯甲酸甲酯的新合成方法 |
| SG183134A1 (en) | 2010-02-08 | 2012-09-27 | Lantheus Medical Imaging Inc | Methods and apparatus for synthesizing imaging agents, and intermediates thereof |
| KR20170042373A (ko) | 2010-05-11 | 2017-04-18 | 랜티우스 메디컬 이메징, 인크. | 영상화제의 합성 및 사용을 위한 조성물, 방법 및 시스템 |
| CN102038964B (zh) * | 2010-12-30 | 2012-01-25 | 上海师范大学 | 一种非晶态铁钴硼纳米磁共振造影剂材料及其制备方法 |
| TWI568714B (zh) | 2011-09-09 | 2017-02-01 | 藍瑟斯醫學影像公司 | 用於合成及使用造影劑之組合物、方法及系統 |
| AU2011379346B2 (en) * | 2011-10-21 | 2017-08-31 | Lantheus Medical Imaging, Inc. | Compositions comprising ascorbic acid and an imaging agent and related methods |
| MX356258B (es) * | 2011-12-22 | 2018-05-16 | Respiratorius Ab | Agente de contraste para obtener imágenes de la perfusión miocárdica. |
| KR101930124B1 (ko) | 2012-04-10 | 2018-12-17 | 랜티우스 메디컬 이메징, 인크. | 방사성제약 합성 방법 |
| AU2013203000B9 (en) | 2012-08-10 | 2017-02-02 | Lantheus Medical Imaging, Inc. | Compositions, methods, and systems for the synthesis and use of imaging agents |
| US9598399B2 (en) | 2012-08-24 | 2017-03-21 | Hamamatsu Photonics K.K. | Compound suitable for detection of mitochondrial complex-1 |
| KR102233327B1 (ko) * | 2013-12-26 | 2021-03-26 | 스미또모 가가꾸 가부시끼가이샤 | 할로겐 치환 프탈리드의 제조 방법 |
| US9745308B2 (en) | 2014-09-12 | 2017-08-29 | Chiesi Farmaceutici S.P.A. | Pyridazinone derivatives as phoshoinositide 3-kinases inhibitors |
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2012
- 2012-04-09 RU RU2012113613A patent/RU2648358C2/ru active
- 2012-06-21 US US13/529,756 patent/US9161997B2/en active Active
- 2012-11-30 JP JP2012263291A patent/JP5847065B2/ja not_active Expired - Lifetime
-
2013
- 2013-08-22 IL IL228097A patent/IL228097A/en active IP Right Grant
- 2013-08-22 IL IL177275A patent/IL177275A/en active IP Right Grant
-
2014
- 2014-08-25 JP JP2014170803A patent/JP6124848B2/ja not_active Expired - Fee Related
-
2015
- 2015-09-04 US US14/845,320 patent/US9718786B2/en not_active Expired - Lifetime
-
2016
- 2016-01-28 IL IL243840A patent/IL243840A0/en unknown
-
2017
- 2017-04-19 NO NO20170638A patent/NO20170638A1/no not_active Application Discontinuation
- 2017-06-21 US US15/629,068 patent/US10125106B2/en not_active Expired - Lifetime
-
2018
- 2018-09-27 US US16/143,748 patent/US10889550B2/en not_active Expired - Fee Related
-
2020
- 2020-12-04 US US17/111,953 patent/US20210300878A1/en not_active Abandoned
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